#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:46:28 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/96/7249682.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249682
loop_
_publ_author_name
'Shi, Linlin'
'Guo, Zhiqiang'
'Luo, Xiaofang'
'Hou, Lingli'
'Wu, Hongchang'
'De, Ruiyu'
'Huang, Xin'
'Wang, Ting'
'Hao, Hongxun'
'Wang, Na'
'Zhou, Lina'
_publ_section_title
;
 Chiral resolution of dl-leucine via salifying tartaric acid derivatives
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              155
_journal_page_last               163
_journal_paper_doi               10.1039/D4CE01043D
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety
'C6 H14 N O2, C20 H17 O8, 0.357(C H4 O), 0.75(H2 O)'
_chemical_formula_sum            'C26.36 H33.93 N O11.11'
_chemical_formula_weight         542.48
_chemical_name_systematic
'L-leucinium D-di-p-toluoyltartrate methanol solvate hydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-09-27 deposited with the CCDC.	2024-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.200(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8758(3)
_cell_length_b                   13.8581(3)
_cell_length_c                   27.1887(6)
_cell_measurement_reflns_used    15578
_cell_measurement_temperature    138.15
_cell_measurement_theta_max      77.4360
_cell_measurement_theta_min      2.9180
_cell_volume                     5744.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      138.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  41.00   0.50    0.50    --  -48.80  72.00  30.00  248
  2  ω   -138.00 -17.00   0.50    0.50    --  -48.80 -45.00 -80.75  242
  3  ω    -79.00  41.00   0.50    0.50    --  -48.80  57.00 -30.00  240
  4  ω   -199.00 -78.00   0.50    2.50    -- -110.00 -42.00 -68.10  242
  5  ω   -199.00 -80.00   0.50    2.50    -- -110.00 -50.00-140.79  238
  6  ω   -144.00 -21.00   0.50    2.50    -- -110.00  72.00-120.00  246
  7  ω   -199.00 -79.00   0.50    2.50    -- -110.00 -44.00 -41.20  240
  8  ω   -144.00 -21.00   0.50    2.50    -- -110.00  72.00 -90.00  246
  9  ω    -81.00 -36.00   0.50    2.50    -- -110.00  72.00  30.00   90
 10  ω   -106.00 -62.00   0.50    2.50    -- -110.00  72.00-150.00   88
 11  ω   -129.00 -43.00   0.50    2.50    -- -110.00  72.00 150.00  172
 12  ω   -159.00-114.00   0.50    2.50    -- -110.00 -64.00 -84.32   90
 13  ω   -108.00 -82.00   0.50    2.50    -- -110.00 -64.00 -84.32   52
 14  ω   -142.00 -25.00   0.50    2.50    -- -110.00  72.00-180.00  234
 15  ω    -93.00 -52.00   0.50    2.50    -- -110.00  72.00 -60.00   82
 16  ω    -58.00 -21.00   0.50    2.50    -- -110.00  57.00-120.00   74
 17  ω   -114.00 -87.00   0.50    2.50    -- -110.00  72.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0459934000
_diffrn_orient_matrix_UB_12      0.0974022000
_diffrn_orient_matrix_UB_13      0.0013555000
_diffrn_orient_matrix_UB_21      -0.0814738000
_diffrn_orient_matrix_UB_22      -0.0533031000
_diffrn_orient_matrix_UB_23      0.0062486000
_diffrn_orient_matrix_UB_31      0.0381015000
_diffrn_orient_matrix_UB_32      0.0035847000
_diffrn_orient_matrix_UB_33      0.0587170000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27976
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.104
_diffrn_reflns_theta_min         2.920
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       prism
_exptl_crystal_F_000             2303
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 3944 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(7)
_refine_ls_extinction_coef       0.00050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         10936
_refine_ls_number_restraints     52
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1234P)²+2.2650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1832
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                9977
_reflns_number_total             10936
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01043d2.cif
_cod_data_source_block           p20240514d
_cod_depositor_comments
'Adding full bibliography for 7249682--7249683.cif.'
_cod_database_code               7249682
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 97.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C12-C10 = C12A-C10
 1.54 with sigma of 0.01
 C4A-C6A = C4A-C5A = C3A-C4A = C2A-C3A
 1.54 with sigma of 0.01
 C3A-C6A = C3A-C5A = C6A-C5A
 2.52 with sigma of 0.01
 C53-O21
 1.45 with sigma of 0.01
 O1A-C1A = O2A-C1A
 1.24 with sigma of 0.01
 C1-C2 = C1A-C2A
 1.5 with sigma of 0.01
 C12-C11 \\sim C12A-C11 \\sim C9-C11 \\sim C9-C12 \\sim C9-C12A
 with sigma of 0.01
 O1-C2 \\sim O2-C2 \\sim O1A-C2A \\sim O2A-C2A
 with sigma of 0.01
 N1-C2 \\sim N1A-C2A
 with sigma of 0.01
3. Restrained planarity
 O1, O2, C1, C2
 with sigma of 0.01
 O1A, O2A, C1A, C2A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C12 \\sim C12A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
Uanis(C12) \\sim Ueq, Uanis(C12A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2
Uanis(C6A) = Uanis(C6)
Uanis(C5A) = Uanis(C5)
Uanis(O1) = Uanis(C1A)
Uanis(O2A) = Uanis(O1) = Uanis(C1A)
Uanis(N1A) = Uanis(N1)
5. Others
 Sof(H10A)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H10)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
 Sof(O21)=Sof(H21)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(2)
 Fixed Sof: O1(0.7) H1(0.7) O2(0.7) N1(0.7) H1A(0.7) H1B(0.7) H1C(0.7) C1(0.7)
 C2(0.7) H2(0.7) C3(0.7) H3A(0.7) H3B(0.7) C4(0.7) H4(0.7) C5(0.7) H5A(0.7)
 H5B(0.7) H5C(0.7) C6(0.7) H6A(0.7) H6B(0.7) H6C(0.7) O1A(0.3) H1AA(0.3)
 O2A(0.3) N1A(0.3) H1AB(0.3) H1AC(0.3) H1AD(0.3) C1A(0.3) C2A(0.3) H2AA(0.3)
 C3A(0.3) H3AA(0.3) H3AB(0.3) C4A(0.3) H4A(0.3) C5A(0.3) H5AA(0.3) H5AB(0.3)
 H5AC(0.3) C6A(0.3) H6AA(0.3) H6AB(0.3) H6AC(0.3) H23A(0.5) H23B(0.5)
6.a Riding coordinates:
 O22(H22A,H22B), O1(H1), O1A(H1AA), O23(H23A,H23B)
6.b Ternary CH refined with riding coordinates:
 C8(H8A), C10(H10), C10(H10A), C14(H14), C15(H15), C34(H34), C35(H35), C2(H2),
 C4(H4), C2A(H2AA), C4A(H4A)
6.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C3(H3A,H3B), C3A(H3AA,H3AB)
6.d Me refined with riding coordinates:
 C6A(H6AA,H6AB,H6AC)
6.e Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23), C27(H27), C28(H28), C30(H30),
 C31(H31), C39(H39), C40(H40), C42(H42), C43(H43), C47(H47), C48(H48), C50(H50),
  C51(H51)
6.f Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C), C32(H32A,H32B,
 H32C), C44(H44A,H44B,H44C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), N1(H1A,
 H1B,H1C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), N1A(H1AB,H1AC,
 H1AD), C5A(H5AA,H5AB,H5AC), C12A(H12D,H12E,H12F)
6.g Idealised tetrahedral OH refined as rotating group:
 O3(H3), O8(H8), O13(H13), O21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.713
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.7898(4) 0.8452(3) 0.58308(18) 0.1044(16) Uani 1 1 d . . . . .
H3 H 0.793657 0.901972 0.573174 0.157 Uiso 1 1 calc R U . . .
O4 O 0.6633(3) 0.7972(4) 0.5330(2) 0.118(2) Uani 1 1 d . . . . .
O5 O 1.27694(16) 0.4412(2) 0.40986(11) 0.0500(6) Uani 1 1 d . . . . .
O6 O 1.35447(18) 0.5627(3) 0.45514(13) 0.0644(9) Uani 1 1 d . . . . .
O7 O 1.6090(2) 0.3954(3) 0.45505(13) 0.0664(9) Uani 1 1 d . . . . .
O8 O 1.63673(16) 0.5105(2) 0.40403(11) 0.0519(6) Uani 1 1 d . . . . .
H8 H 1.688905 0.491609 0.414899 0.078 Uiso 1 1 calc R U . . .
O9 O 1.41378(16) 0.39220(19) 0.37514(9) 0.0423(5) Uani 1 1 d . . . . .
O10 O 1.3795(2) 0.2562(2) 0.41139(11) 0.0561(7) Uani 1 1 d . . . . .
O11 O 1.47324(15) 0.57573(19) 0.38046(9) 0.0429(5) Uani 1 1 d . . . . .
O12 O 1.55535(18) 0.6994(2) 0.42290(11) 0.0550(6) Uani 1 1 d . . . . .
O13 O 1.13758(16) 0.5136(2) 0.41292(10) 0.0489(6) Uani 1 1 d . . . . .
H13 H 1.186695 0.487103 0.417204 0.073 Uiso 1 1 calc R U . . .
O14 O 1.10838(17) 0.3832(2) 0.45427(11) 0.0520(6) Uani 1 1 d . . . . .
O15 O 0.84826(17) 0.5446(2) 0.45749(11) 0.0540(7) Uani 1 1 d . . . . .
O16 O 0.77432(16) 0.4316(2) 0.40446(12) 0.0578(7) Uani 1 1 d . . . . .
O17 O 0.96637(15) 0.5467(2) 0.37562(9) 0.0448(5) Uani 1 1 d . . . . .
O18 O 1.0086(2) 0.6918(2) 0.41093(13) 0.0651(8) Uani 1 1 d . . . . .
O19 O 0.91600(16) 0.3627(2) 0.38489(10) 0.0454(6) Uani 1 1 d . . . . .
O20 O 0.8735(3) 0.2451(3) 0.43008(13) 0.0703(9) Uani 1 1 d . . . . .
O21 O 0.7120(7) 0.9567(5) 0.6259(3) 0.120(3) Uani 0.714(11) 1 d D . P . .
H21 H 0.687069 0.996655 0.603311 0.180 Uiso 0.714(11) 1 calc R U P . .
O22 O 1.4869(4) 0.0440(7) 0.4310(4) 0.157(3) Uani 1 1 d . . . . .
H22A H 1.490245 -0.015858 0.438225 0.235 Uiso 1 1 d R U . . .
H22B H 1.452905 0.066792 0.447375 0.235 Uiso 1 1 d R U . . .
N2 N 0.7322(2) 0.6585(2) 0.48849(12) 0.0441(6) Uani 1 1 d . . . . .
H2A H 0.688123 0.688029 0.464510 0.053 Uiso 1 1 calc R U . . .
H2B H 0.709174 0.622869 0.509712 0.053 Uiso 1 1 calc R U . . .
H2C H 0.762512 0.619169 0.472693 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7413(4) 0.7945(4) 0.5454(2) 0.0727(13) Uani 1 1 d . . . . .
C8 C 0.7922(3) 0.7324(3) 0.51871(16) 0.0551(9) Uani 1 1 d . . . . .
H8A H 0.836603 0.696986 0.546116 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8429(4) 0.7846(4) 0.4866(2) 0.0740(13) Uani 1 1 d D . . . .
H9A H 0.880271 0.834037 0.508598 0.089 Uiso 1 1 calc R U . . .
H9B H 0.882630 0.737272 0.477379 0.089 Uiso 1 1 calc R U . . .
C10 C 0.7915(6) 0.8334(5) 0.4383(3) 0.098(2) Uani 1 1 d D . . . .
H10 H 0.758150 0.782666 0.414547 0.118 Uiso 0.658(17) 1 calc R U P A 1
H10A H 0.837513 0.873666 0.429415 0.05(4) Uiso 0.342(17) 1 calc R . P A 2
C11 C 0.7298(8) 0.9057(9) 0.4446(4) 0.166(5) Uani 1 1 d D . . . .
H11A H 0.680802 0.874191 0.453625 0.249 Uiso 1 1 calc R U . . .
H11B H 0.707489 0.941543 0.412562 0.249 Uiso 1 1 calc R U . . .
H11C H 0.759130 0.950269 0.472026 0.249 Uiso 1 1 calc R U . . .
C13 C 1.3476(2) 0.4872(3) 0.42990(13) 0.0436(7) Uani 1 1 d . . . . .
C14 C 1.4313(2) 0.4423(3) 0.42382(13) 0.0416(7) Uani 1 1 d . . . . .
H14 H 1.453623 0.394585 0.452057 0.050 Uiso 1 1 calc R U . . .
C15 C 1.5023(2) 0.5155(3) 0.42544(13) 0.0408(7) Uani 1 1 d . . . . .
H15 H 1.509287 0.556899 0.456458 0.049 Uiso 1 1 calc R U . . .
C16 C 1.5902(2) 0.4682(3) 0.42852(13) 0.0428(7) Uani 1 1 d . . . . .
C17 C 1.3850(2) 0.3000(3) 0.37385(15) 0.0455(8) Uani 1 1 d . . . . .
C18 C 1.3601(2) 0.2619(3) 0.32094(15) 0.0477(8) Uani 1 1 d . . . . .
C19 C 1.3580(3) 0.3184(4) 0.27861(17) 0.0627(11) Uani 1 1 d . . . . .
H19 H 1.373862 0.384563 0.283135 0.075 Uiso 1 1 calc R U . . .
C20 C 1.3331(4) 0.2798(4) 0.23008(18) 0.0712(13) Uani 1 1 d . . . . .
H20 H 1.331603 0.319968 0.201525 0.085 Uiso 1 1 calc R U . . .
C21 C 1.3102(3) 0.1827(4) 0.22208(19) 0.0660(12) Uani 1 1 d . . . . .
C22 C 1.3121(4) 0.1265(4) 0.2645(2) 0.0705(13) Uani 1 1 d . . . . .
H22 H 1.296148 0.060355 0.259944 0.085 Uiso 1 1 calc R U . . .
C23 C 1.3368(3) 0.1650(4) 0.31336(19) 0.0618(10) Uani 1 1 d . . . . .
H23 H 1.337908 0.125069 0.341937 0.074 Uiso 1 1 calc R U . . .
C24 C 1.2806(4) 0.1420(5) 0.1687(2) 0.0853(17) Uani 1 1 d . . . . .
H24A H 1.227702 0.175921 0.149110 0.128 Uiso 1 1 calc R U . . .
H24B H 1.267570 0.073101 0.170380 0.128 Uiso 1 1 calc R U . . .
H24C H 1.327195 0.150304 0.151839 0.128 Uiso 1 1 calc R U . . .
C25 C 1.5081(2) 0.6654(3) 0.38364(15) 0.0464(8) Uani 1 1 d . . . . .
C26 C 1.4799(2) 0.7176(3) 0.33436(16) 0.0523(9) Uani 1 1 d . . . . .
C27 C 1.5071(5) 0.8127(4) 0.3325(3) 0.0886(19) Uani 1 1 d . . . . .
H27 H 1.542115 0.842855 0.362731 0.106 Uiso 1 1 calc R U . . .
C28 C 1.4833(5) 0.8638(5) 0.2867(3) 0.098(2) Uani 1 1 d . . . . .
H28 H 1.503781 0.928013 0.285735 0.118 Uiso 1 1 calc R U . . .
C29 C 1.4302(3) 0.8226(5) 0.2423(2) 0.0742(15) Uani 1 1 d . . . . .
C30 C 1.4032(3) 0.7296(5) 0.24486(19) 0.0706(13) Uani 1 1 d . . . . .
H30 H 1.367334 0.699850 0.214801 0.085 Uiso 1 1 calc R U . . .
C31 C 1.4268(3) 0.6772(4) 0.29015(17) 0.0606(10) Uani 1 1 d . . . . .
H31 H 1.406229 0.612999 0.290719 0.073 Uiso 1 1 calc R U . . .
C32 C 1.4049(5) 0.8801(6) 0.1928(3) 0.097(2) Uani 1 1 d . . . . .
H32A H 1.404198 0.949019 0.200668 0.146 Uiso 1 1 calc R U . . .
H32B H 1.346457 0.860177 0.172138 0.146 Uiso 1 1 calc R U . . .
H32C H 1.447651 0.868153 0.173513 0.146 Uiso 1 1 calc R U . . .
C33 C 1.0880(2) 0.4590(3) 0.43141(13) 0.0422(7) Uani 1 1 d . . . . .
C34 C 0.9969(2) 0.5008(3) 0.42490(12) 0.0408(7) Uani 1 1 d . . . . .
H34 H 1.000478 0.550369 0.452118 0.049 Uiso 1 1 calc R U . . .
C35 C 0.9292(2) 0.4255(3) 0.42843(13) 0.0411(7) Uani 1 1 d . . . . .
H35 H 0.952921 0.386736 0.460315 0.049 Uiso 1 1 calc R U . . .
C36 C 0.8437(2) 0.4725(3) 0.43053(13) 0.0419(7) Uani 1 1 d . . . . .
C37 C 0.9804(2) 0.6427(3) 0.37349(16) 0.0503(8) Uani 1 1 d . . . . .
C38 C 0.9568(3) 0.6772(3) 0.32016(17) 0.0551(9) Uani 1 1 d . . . . .
C39 C 0.9605(4) 0.7764(4) 0.3116(2) 0.0758(14) Uani 1 1 d . . . . .
H39 H 0.977115 0.820029 0.339565 0.091 Uiso 1 1 calc R U . . .
C40 C 0.9392(4) 0.8110(5) 0.2608(3) 0.0872(18) Uani 1 1 d . . . . .
H40 H 0.941072 0.878422 0.254913 0.105 Uiso 1 1 calc R U . . .
C41 C 0.9160(3) 0.7497(5) 0.2197(2) 0.0803(18) Uani 1 1 d . . . . .
C42 C 0.9119(4) 0.6519(5) 0.2285(2) 0.0787(15) Uani 1 1 d . . . . .
H42 H 0.894799 0.608736 0.200282 0.094 Uiso 1 1 calc R U . . .
C43 C 0.9328(3) 0.6157(4) 0.27844(18) 0.0669(12) Uani 1 1 d . . . . .
H43 H 0.930508 0.548126 0.283828 0.080 Uiso 1 1 calc R U . . .
C44 C 0.8923(4) 0.7894(7) 0.1653(3) 0.110(3) Uani 1 1 d . . . . .
H44A H 0.828491 0.797014 0.152551 0.165 Uiso 1 1 calc R U . . .
H44B H 0.912443 0.744545 0.143133 0.165 Uiso 1 1 calc R U . . .
H44C H 0.920587 0.852238 0.165212 0.165 Uiso 1 1 calc R U . . .
C45 C 0.8825(3) 0.2743(3) 0.38990(17) 0.0527(9) Uani 1 1 d . . . . .
C46 C 0.8594(3) 0.2207(4) 0.34067(18) 0.0580(10) Uani 1 1 d . . . . .
C47 C 0.8325(4) 0.1246(4) 0.3410(2) 0.0753(14) Uani 1 1 d . . . . .
H47 H 0.828912 0.095799 0.372074 0.090 Uiso 1 1 calc R U . . .
C48 C 0.8112(4) 0.0718(5) 0.2965(3) 0.0887(18) Uani 1 1 d . . . . .
H48 H 0.793749 0.006440 0.297436 0.106 Uiso 1 1 calc R U . . .
C49 C 0.8144(4) 0.1107(5) 0.2514(3) 0.0856(18) Uani 1 1 d . . . . .
C50 C 0.8424(5) 0.2069(6) 0.2510(3) 0.100(2) Uani 1 1 d . . . . .
H50 H 0.846434 0.234985 0.219898 0.120 Uiso 1 1 calc R U . . .
C51 C 0.8642(4) 0.2608(5) 0.2954(2) 0.0813(16) Uani 1 1 d . . . . .
H51 H 0.882430 0.325964 0.294641 0.098 Uiso 1 1 calc R U . . .
C52 C 0.7880(5) 0.0536(7) 0.2016(3) 0.118(3) Uani 1 1 d . . . . .
H52A H 0.839331 0.019742 0.196831 0.177 Uiso 1 1 calc R U . . .
H52B H 0.764873 0.097744 0.172839 0.177 Uiso 1 1 calc R U . . .
H52C H 0.742691 0.006434 0.203046 0.177 Uiso 1 1 calc R U . . .
C53 C 0.6547(6) 0.9124(7) 0.6419(3) 0.085(3) Uani 0.714(11) 1 d D . P . .
H53A H 0.626084 0.863449 0.616822 0.127 Uiso 0.714(11) 1 calc R U P . .
H53B H 0.610763 0.958510 0.646622 0.127 Uiso 0.714(11) 1 calc R U P . .
H53C H 0.683093 0.881166 0.674700 0.127 Uiso 0.714(11) 1 calc R U P . .
O1 O 1.3679(4) 0.1433(5) 0.5390(3) 0.0912(16) Uani 0.7 1 d D . P B 1
H1 H 1.412915 0.111025 0.544781 0.137 Uiso 0.7 1 d R U P B 1
O2 O 1.3351(3) 0.0639(4) 0.4657(2) 0.0724(13) Uani 0.7 1 d D . P B 1
N1 N 1.2658(8) 0.2832(5) 0.4790(3) 0.0399(13) Uani 0.7 1 d D . P B 1
H1A H 1.219037 0.323931 0.471939 0.048 Uiso 0.7 1 calc R U P B 1
H1B H 1.294316 0.289129 0.454356 0.048 Uiso 0.7 1 calc R U P B 1
H1C H 1.303098 0.298289 0.510020 0.048 Uiso 0.7 1 calc R U P B 1
C1 C 1.3175(4) 0.1229(4) 0.4932(3) 0.0679(18) Uani 0.7 1 d D . P B 1
C2 C 1.2352(4) 0.1833(4) 0.4799(3) 0.0571(18) Uani 0.7 1 d D . P B 1
H2 H 1.202501 0.175433 0.506242 0.069 Uiso 0.7 1 calc R U P B 1
C3 C 1.1742(5) 0.1628(6) 0.4252(3) 0.0624(15) Uani 0.7 1 d . . P B 1
H3A H 1.131574 0.216316 0.414749 0.075 Uiso 0.7 1 calc R U P B 1
H3B H 1.209833 0.159992 0.400644 0.075 Uiso 0.7 1 calc R U P B 1
C4 C 1.1254(5) 0.0693(7) 0.4235(3) 0.0686(17) Uani 0.7 1 d . . P B 1
H4 H 1.168430 0.016658 0.437594 0.082 Uiso 0.7 1 calc R U P B 1
C5 C 1.0573(6) 0.0720(8) 0.4533(5) 0.095(3) Uani 0.7 1 d . . P B 1
H5A H 1.020828 0.013813 0.445691 0.143 Uiso 0.7 1 calc R U P B 1
H5B H 1.020136 0.129201 0.443260 0.143 Uiso 0.7 1 calc R U P B 1
H5C H 1.086887 0.074678 0.490069 0.143 Uiso 0.7 1 calc R U P B 1
C6 C 1.0762(7) 0.0458(10) 0.3669(5) 0.101(3) Uani 0.7 1 d . . P B 1
H6A H 1.035823 -0.008205 0.365785 0.151 Uiso 0.7 1 calc R U P B 1
H6B H 1.118780 0.028136 0.348353 0.151 Uiso 0.7 1 calc R U P B 1
H6C H 1.042940 0.102544 0.350754 0.151 Uiso 0.7 1 calc R U P B 1
C12 C 0.8588(10) 0.8788(13) 0.4133(7) 0.185(9) Uani 0.658(17) 1 d D U P A 1
H12A H 0.836059 0.875205 0.375910 0.277 Uiso 0.658(17) 1 calc R U P A 1
H12B H 0.914388 0.843456 0.424357 0.277 Uiso 0.658(17) 1 calc R U P A 1
H12C H 0.868600 0.946493 0.423770 0.277 Uiso 0.658(17) 1 calc R U P A 1
O1A O 1.3393(14) 0.0682(11) 0.5585(5) 0.121(7) Uani 0.3 1 d D U P C 2
H1AA H 1.368586 0.079007 0.588013 0.182 Uiso 0.3 1 d R U P C 2
O2A O 1.4098(8) 0.1768(12) 0.5215(6) 0.0912(16) Uani 0.3 1 d D . P C 2
N1A N 1.260(2) 0.2864(12) 0.4896(10) 0.0399(13) Uani 0.3 1 d D . P C 2
H1AB H 1.205697 0.313190 0.481801 0.048 Uiso 0.3 1 calc R U P C 2
H1AC H 1.281670 0.290389 0.461968 0.048 Uiso 0.3 1 calc R U P C 2
H1AD H 1.296362 0.318539 0.516453 0.048 Uiso 0.3 1 calc R U P C 2
C1A C 1.3430(11) 0.1394(10) 0.5302(4) 0.0912(16) Uani 0.3 1 d D . P C 2
C2A C 1.2548(9) 0.1845(11) 0.5035(6) 0.074(7) Uani 0.3 1 d D . P C 2
H2AA H 1.215429 0.178974 0.526382 0.089 Uiso 0.3 1 calc R U P C 2
C3A C 1.2214(8) 0.1130(13) 0.4568(6) 0.069(4) Uani 0.3 1 d D . P C 2
H3AA H 1.260361 0.118704 0.434120 0.083 Uiso 0.3 1 calc R U P C 2
H3AB H 1.225958 0.046052 0.469912 0.083 Uiso 0.3 1 calc R U P C 2
C4A C 1.1259(9) 0.1318(15) 0.4248(6) 0.070(4) Uani 0.3 1 d D . P C 2
H4A H 1.122442 0.199731 0.411961 0.084 Uiso 0.3 1 calc R U P C 2
C5A C 1.0633(12) 0.1227(19) 0.4578(10) 0.095(3) Uani 0.3 1 d D . P C 2
H5AA H 1.062925 0.183154 0.476433 0.143 Uiso 0.3 1 calc R U P C 2
H5AB H 1.082623 0.069852 0.482366 0.143 Uiso 0.3 1 calc R U P C 2
H5AC H 1.004109 0.109075 0.436010 0.143 Uiso 0.3 1 calc R U P C 2
C6A C 1.1017(15) 0.065(3) 0.3784(9) 0.101(3) Uani 0.3 1 d D . P C 2
H6AA H 1.143874 0.073726 0.358359 0.151 Uiso 0.3 1 calc R U P C 2
H6AB H 1.103165 -0.002010 0.389849 0.151 Uiso 0.3 1 calc R U P C 2
H6AC H 1.042650 0.080891 0.357021 0.151 Uiso 0.3 1 calc R U P C 2
C12A C 0.7642(11) 0.7690(11) 0.3936(4) 0.093(7) Uani 0.342(17) 1 d D U P A 2
H12D H 0.762014 0.805431 0.362388 0.139 Uiso 0.342(17) 1 calc R U P A 2
H12E H 0.705987 0.742626 0.391377 0.139 Uiso 0.342(17) 1 calc R U P A 2
H12F H 0.806439 0.716039 0.397338 0.139 Uiso 0.342(17) 1 calc R U P A 2
O23 O 0.500000 0.8871(7) 0.500000 0.161(5) Uani 1 2 d S T P . .
H23A H 0.543820 0.849528 0.504450 0.242 Uiso 0.5 1 d R U P . .
H23B H 0.456180 0.849528 0.495550 0.242 Uiso 0.5 1 d R U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O3 H3 109.5 . . ?
C16 O8 H8 109.5 . . ?
C17 O9 C14 116.9(3) . . ?
C25 O11 C15 116.6(3) . . ?
C33 O13 H13 109.5 . . ?
C37 O17 C34 117.2(3) . . ?
C45 O19 C35 115.8(3) . . ?
C53 O21 H21 109.5 . . ?
H22A O22 H22B 104.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
O3 C7 C8 114.3(6) . . ?
O4 C7 O3 123.0(6) . . ?
O4 C7 C8 122.7(5) . . ?
N2 C8 C7 108.4(4) . . ?
N2 C8 H8A 106.5 . . ?
N2 C8 C9 111.8(4) . . ?
C7 C8 H8A 106.5 . . ?
C7 C8 C9 116.5(4) . . ?
C9 C8 H8A 106.5 . . ?
C8 C9 H9A 107.8 . . ?
C8 C9 H9B 107.8 . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 C8 118.1(5) . . ?
C10 C9 H9A 107.8 . . ?
C10 C9 H9B 107.8 . . ?
C9 C10 H10 108.0 . . ?
C9 C10 H10A 102.0 . . ?
C9 C10 C12 107.1(8) . . ?
C11 C10 C9 115.3(6) . . ?
C11 C10 H10 108.0 . . ?
C11 C10 H10A 102.0 . . ?
C11 C10 C12 110.2(7) . . ?
C11 C10 C12A 117.7(9) . . ?
C12 C10 H10 108.0 . . ?
C12A C10 C9 114.4(7) . . ?
C12A C10 H10A 102.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C13 C14 116.3(3) . . ?
O6 C13 O5 126.2(3) . . ?
O6 C13 C14 117.5(3) . . ?
O9 C14 C13 110.1(3) . . ?
O9 C14 H14 108.7 . . ?
O9 C14 C15 107.5(3) . . ?
C13 C14 H14 108.7 . . ?
C15 C14 C13 113.0(3) . . ?
C15 C14 H14 108.7 . . ?
O11 C15 C14 107.7(3) . . ?
O11 C15 H15 108.5 . . ?
O11 C15 C16 111.5(3) . . ?
C14 C15 H15 108.5 . . ?
C14 C15 C16 112.2(3) . . ?
C16 C15 H15 108.5 . . ?
O7 C16 O8 127.3(3) . . ?
O7 C16 C15 117.1(3) . . ?
O8 C16 C15 115.6(3) . . ?
O9 C17 C18 111.0(3) . . ?
O10 C17 O9 123.7(4) . . ?
O10 C17 C18 125.3(4) . . ?
C19 C18 C17 123.0(4) . . ?
C19 C18 C23 118.6(4) . . ?
C23 C18 C17 118.5(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(5) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.1(5) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C24 120.7(5) . . ?
C22 C21 C20 117.9(4) . . ?
C22 C21 C24 121.4(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.2(5) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.4(5) . . ?
C22 C23 H23 119.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O11 C25 C26 112.1(3) . . ?
O12 C25 O11 123.6(4) . . ?
O12 C25 C26 124.2(4) . . ?
C27 C26 C25 118.5(4) . . ?
C31 C26 C25 123.3(4) . . ?
C31 C26 C27 118.2(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.3(6) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.1(5) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 C32 120.1(6) . . ?
C30 C29 C28 117.8(5) . . ?
C30 C29 C32 122.1(6) . . ?
C29 C30 H30 119.1 . . ?
C29 C30 C31 121.9(5) . . ?
C31 C30 H30 119.1 . . ?
C26 C31 C30 120.6(5) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O13 C33 C34 113.3(3) . . ?
O14 C33 O13 126.9(3) . . ?
O14 C33 C34 119.7(3) . . ?
O17 C34 C33 109.8(3) . . ?
O17 C34 H34 108.7 . . ?
O17 C34 C35 107.5(3) . . ?
C33 C34 H34 108.7 . . ?
C35 C34 C33 113.4(3) . . ?
C35 C34 H34 108.7 . . ?
O19 C35 C34 107.9(3) . . ?
O19 C35 H35 108.8 . . ?
O19 C35 C36 111.3(3) . . ?
C34 C35 H35 108.8 . . ?
C34 C35 C36 111.3(3) . . ?
C36 C35 H35 108.8 . . ?
O15 C36 O16 126.5(3) . . ?
O15 C36 C35 117.7(3) . . ?
O16 C36 C35 115.8(3) . . ?
O17 C37 C38 111.2(4) . . ?
O18 C37 O17 123.2(4) . . ?
O18 C37 C38 125.6(4) . . ?
C39 C38 C37 118.2(5) . . ?
C43 C38 C37 122.9(4) . . ?
C43 C38 C39 118.9(5) . . ?
C38 C39 H39 120.4 . . ?
C38 C39 C40 119.2(6) . . ?
C40 C39 H39 120.4 . . ?
C39 C40 H40 119.2 . . ?
C41 C40 C39 121.6(6) . . ?
C41 C40 H40 119.2 . . ?
C40 C41 C42 118.9(5) . . ?
C40 C41 C44 120.4(7) . . ?
C42 C41 C44 120.7(7) . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.6(6) . . ?
C43 C42 H42 119.7 . . ?
C38 C43 C42 120.8(6) . . ?
C38 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C41 C44 H44A 109.5 . . ?
C41 C44 H44B 109.5 . . ?
C41 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O19 C45 C46 111.5(4) . . ?
O20 C45 O19 122.7(4) . . ?
O20 C45 C46 125.9(4) . . ?
C47 C46 C45 118.0(5) . . ?
C51 C46 C45 123.0(4) . . ?
C51 C46 C47 119.0(5) . . ?
C46 C47 H47 119.9 . . ?
C48 C47 C46 120.1(6) . . ?
C48 C47 H47 119.9 . . ?
C47 C48 H48 119.2 . . ?
C49 C48 C47 121.6(6) . . ?
C49 C48 H48 119.2 . . ?
C48 C49 C50 118.4(5) . . ?
C48 C49 C52 121.9(7) . . ?
C50 C49 C52 119.7(7) . . ?
C49 C50 H50 119.7 . . ?
C51 C50 C49 120.6(7) . . ?
C51 C50 H50 119.7 . . ?
C46 C51 C50 120.1(6) . . ?
C46 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C49 C52 H52A 109.5 . . ?
C49 C52 H52B 109.5 . . ?
C49 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O21 C53 H53A 109.5 . . ?
O21 C53 H53B 109.5 . . ?
O21 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C1 O1 H1 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
O1 C1 C2 111.6(6) . . ?
O2 C1 O1 123.8(7) . . ?
O2 C1 C2 124.6(7) . . ?
N1 C2 C1 104.9(6) . . ?
N1 C2 H2 110.8 . . ?
N1 C2 C3 106.0(7) . . ?
C1 C2 H2 110.8 . . ?
C1 C2 C3 113.2(6) . . ?
C3 C2 H2 110.8 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.3(6) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C5 113.5(8) . . ?
C3 C4 C6 108.9(8) . . ?
C5 C4 H4 109.0 . . ?
C5 C4 C6 107.3(8) . . ?
C6 C4 H4 109.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1A O1A H1AA 110.1 . . ?
H1AB N1A H1AC 109.5 . . ?
H1AB N1A H1AD 109.5 . . ?
H1AC N1A H1AD 109.5 . . ?
C2A N1A H1AB 109.5 . . ?
C2A N1A H1AC 109.5 . . ?
C2A N1A H1AD 109.5 . . ?
O1A C1A C2A 114.8(12) . . ?
O2A C1A O1A 128.3(17) . . ?
O2A C1A C2A 116.9(12) . . ?
N1A C2A C1A 113.9(17) . . ?
N1A C2A H2AA 108.9 . . ?
N1A C2A C3A 115.2(16) . . ?
C1A C2A H2AA 108.9 . . ?
C1A C2A C3A 100.6(9) . . ?
C3A C2A H2AA 108.9 . . ?
C2A C3A H3AA 108.8 . . ?
C2A C3A H3AB 108.8 . . ?
H3AA C3A H3AB 107.7 . . ?
C4A C3A C2A 113.7(12) . . ?
C4A C3A H3AA 108.8 . . ?
C4A C3A H3AB 108.8 . . ?
C3A C4A H4A 107.7 . . ?
C5A C4A C3A 110.8(11) . . ?
C5A C4A H4A 107.7 . . ?
C5A C4A C6A 112.6(12) . . ?
C6A C4A C3A 110.1(11) . . ?
C6A C4A H4A 107.7 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C10 C12A H12D 109.5 . . ?
C10 C12A H12E 109.5 . . ?
C10 C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
H23A O23 H23B 104.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3 0.8400 . ?
O3 C7 1.302(7) . ?
O4 C7 1.190(8) . ?
O5 C13 1.273(5) . ?
O6 C13 1.240(5) . ?
O7 C16 1.228(5) . ?
O8 H8 0.8400 . ?
O8 C16 1.268(5) . ?
O9 C14 1.451(4) . ?
O9 C17 1.354(5) . ?
O10 C17 1.212(5) . ?
O11 C15 1.446(4) . ?
O11 C25 1.353(5) . ?
O12 C25 1.216(5) . ?
O13 H13 0.8400 . ?
O13 C33 1.290(4) . ?
O14 C33 1.218(5) . ?
O15 C36 1.230(5) . ?
O16 C36 1.265(5) . ?
O17 C34 1.440(4) . ?
O17 C37 1.354(5) . ?
O18 C37 1.202(5) . ?
O19 C35 1.437(4) . ?
O19 C45 1.358(5) . ?
O20 C45 1.210(6) . ?
O21 H21 0.8400 . ?
O21 C53 1.270(10) . ?
O22 H22A 0.8503 . ?
O22 H22B 0.8496 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C8 1.481(5) . ?
C7 C8 1.498(7) . ?
C8 H8A 1.0000 . ?
C8 C9 1.525(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.500(9) . ?
C10 H10 1.0000 . ?
C10 H10A 1.0000 . ?
C10 C11 1.446(12) . ?
C10 C12 1.551(10) . ?
C10 C12A 1.471(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.517(5) . ?
C14 H14 1.0000 . ?
C14 C15 1.508(5) . ?
C15 H15 1.0000 . ?
C15 C16 1.522(4) . ?
C17 C18 1.479(5) . ?
C18 C19 1.385(6) . ?
C18 C23 1.393(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.375(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.395(8) . ?
C21 C22 1.385(8) . ?
C21 C24 1.505(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(7) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.478(5) . ?
C26 C27 1.393(7) . ?
C26 C31 1.379(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(8) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(9) . ?
C29 C30 1.366(8) . ?
C29 C32 1.519(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(6) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.522(4) . ?
C34 H34 1.0000 . ?
C34 C35 1.520(5) . ?
C35 H35 1.0000 . ?
C35 C36 1.521(5) . ?
C37 C38 1.473(6) . ?
C38 C39 1.398(7) . ?
C38 C43 1.385(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.410(8) . ?
C40 H40 0.9500 . ?
C40 C41 1.368(10) . ?
C41 C42 1.382(10) . ?
C41 C44 1.525(7) . ?
C42 H42 0.9500 . ?
C42 C43 1.398(7) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 C46 1.484(6) . ?
C46 C47 1.400(8) . ?
C46 C51 1.371(8) . ?
C47 H47 0.9500 . ?
C47 C48 1.372(8) . ?
C48 H48 0.9500 . ?
C48 C49 1.354(11) . ?
C49 C50 1.406(11) . ?
C49 C52 1.524(8) . ?
C50 H50 0.9500 . ?
C50 C51 1.379(8) . ?
C51 H51 0.9500 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
O1 H1 0.8200 . ?
O1 C1 1.308(10) . ?
O2 C1 1.194(9) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.470(8) . ?
C1 C2 1.509(8) . ?
C2 H2 1.0000 . ?
C2 C3 1.557(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.504(11) . ?
C4 H4 1.0000 . ?
C4 C5 1.521(13) . ?
C4 C6 1.555(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1A H1AA 0.8200 . ?
O1A C1A 1.263(13) . ?
O2A C1A 1.260(12) . ?
N1A H1AB 0.9100 . ?
N1A H1AC 0.9100 . ?
N1A H1AD 0.9100 . ?
N1A C2A 1.470(13) . ?
C1A C2A 1.520(12) . ?
C2A H2AA 1.0000 . ?
C2A C3A 1.582(12) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.545(12) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.518(12) . ?
C4A C6A 1.525(13) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
O23 H23A 0.8499 . ?
O23 H23B 0.8499 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C7 C8 N2 162.9(4) . . . . ?
O3 C7 C8 C9 -70.0(6) . . . . ?
O4 C7 C8 N2 -17.2(8) . . . . ?
O4 C7 C8 C9 109.9(7) . . . . ?
O5 C13 C14 O9 33.3(4) . . . . ?
O5 C13 C14 C15 153.5(3) . . . . ?
O6 C13 C14 O9 -149.1(3) . . . . ?
O6 C13 C14 C15 -28.9(4) . . . . ?
O9 C14 C15 O11 55.0(3) . . . . ?
O9 C14 C15 C16 -68.1(3) . . . . ?
O9 C17 C18 C19 -6.7(5) . . . . ?
O9 C17 C18 C23 174.0(4) . . . . ?
O10 C17 C18 C19 172.3(4) . . . . ?
O10 C17 C18 C23 -7.0(6) . . . . ?
O11 C15 C16 O7 -158.8(3) . . . . ?
O11 C15 C16 O8 22.8(4) . . . . ?
O11 C25 C26 C27 176.8(5) . . . . ?
O11 C25 C26 C31 -2.2(6) . . . . ?
O12 C25 C26 C27 -1.6(7) . . . . ?
O12 C25 C26 C31 179.4(4) . . . . ?
O13 C33 C34 O17 39.0(4) . . . . ?
O13 C33 C34 C35 159.3(3) . . . . ?
O14 C33 C34 O17 -144.0(3) . . . . ?
O14 C33 C34 C35 -23.6(5) . . . . ?
O17 C34 C35 O19 54.6(3) . . . . ?
O17 C34 C35 C36 -67.8(3) . . . . ?
O17 C37 C38 C39 174.7(4) . . . . ?
O17 C37 C38 C43 -6.5(5) . . . . ?
O18 C37 C38 C39 -5.5(6) . . . . ?
O18 C37 C38 C43 173.4(4) . . . . ?
O19 C35 C36 O15 -162.2(3) . . . . ?
O19 C35 C36 O16 18.7(5) . . . . ?
O19 C45 C46 C47 173.6(4) . . . . ?
O19 C45 C46 C51 -5.8(6) . . . . ?
O20 C45 C46 C47 -6.4(7) . . . . ?
O20 C45 C46 C51 174.2(5) . . . . ?
N2 C8 C9 C10 56.1(6) . . . . ?
C7 C8 C9 C10 -69.3(7) . . . . ?
C8 C9 C10 C11 57.8(9) . . . . ?
C8 C9 C10 C12 -179.2(9) . . . . ?
C8 C9 C10 C12A -83.5(10) . . . . ?
C13 C14 C15 O11 -66.8(3) . . . . ?
C13 C14 C15 C16 170.2(3) . . . . ?
C14 O9 C17 O10 -5.6(5) . . . . ?
C14 O9 C17 C18 173.4(3) . . . . ?
C14 C15 C16 O7 -37.9(5) . . . . ?
C14 C15 C16 O8 143.7(3) . . . . ?
C15 O11 C25 O12 -6.6(5) . . . . ?
C15 O11 C25 C26 175.1(3) . . . . ?
C17 O9 C14 C13 -85.5(4) . . . . ?
C17 O9 C14 C15 151.0(3) . . . . ?
C17 C18 C19 C20 -179.0(4) . . . . ?
C17 C18 C23 C22 179.2(4) . . . . ?
C18 C19 C20 C21 -0.6(8) . . . . ?
C19 C18 C23 C22 -0.1(7) . . . . ?
C19 C20 C21 C22 0.8(8) . . . . ?
C19 C20 C21 C24 178.2(5) . . . . ?
C20 C21 C22 C23 -0.6(8) . . . . ?
C21 C22 C23 C18 0.3(8) . . . . ?
C23 C18 C19 C20 0.2(7) . . . . ?
C24 C21 C22 C23 -178.0(5) . . . . ?
C25 O11 C15 C14 155.1(3) . . . . ?
C25 O11 C15 C16 -81.4(4) . . . . ?
C25 C26 C27 C28 178.8(6) . . . . ?
C25 C26 C31 C30 -179.4(4) . . . . ?
C26 C27 C28 C29 1.9(12) . . . . ?
C27 C26 C31 C30 1.6(8) . . . . ?
C27 C28 C29 C30 -1.1(11) . . . . ?
C27 C28 C29 C32 179.8(7) . . . . ?
C28 C29 C30 C31 0.6(9) . . . . ?
C29 C30 C31 C26 -0.9(8) . . . . ?
C31 C26 C27 C28 -2.1(10) . . . . ?
C32 C29 C30 C31 179.7(6) . . . . ?
C33 C34 C35 O19 -67.0(3) . . . . ?
C33 C34 C35 C36 170.6(3) . . . . ?
C34 O17 C37 O18 -7.6(5) . . . . ?
C34 O17 C37 C38 172.3(3) . . . . ?
C34 C35 C36 O15 -41.8(4) . . . . ?
C34 C35 C36 O16 139.1(3) . . . . ?
C35 O19 C45 O20 -8.2(5) . . . . ?
C35 O19 C45 C46 171.8(3) . . . . ?
C37 O17 C34 C33 -94.2(4) . . . . ?
C37 O17 C34 C35 141.9(3) . . . . ?
C37 C38 C39 C40 179.2(5) . . . . ?
C37 C38 C43 C42 -179.3(4) . . . . ?
C38 C39 C40 C41 -0.7(9) . . . . ?
C39 C38 C43 C42 -0.4(7) . . . . ?
C39 C40 C41 C42 1.1(9) . . . . ?
C39 C40 C41 C44 179.2(5) . . . . ?
C40 C41 C42 C43 -1.2(8) . . . . ?
C41 C42 C43 C38 0.9(8) . . . . ?
C43 C38 C39 C40 0.4(8) . . . . ?
C44 C41 C42 C43 -179.3(5) . . . . ?
C45 O19 C35 C34 158.2(3) . . . . ?
C45 O19 C35 C36 -79.4(4) . . . . ?
C45 C46 C47 C48 -179.5(5) . . . . ?
C45 C46 C51 C50 179.5(6) . . . . ?
C46 C47 C48 C49 -0.9(9) . . . . ?
C47 C46 C51 C50 0.1(9) . . . . ?
C47 C48 C49 C50 1.6(10) . . . . ?
C47 C48 C49 C52 -178.0(6) . . . . ?
C48 C49 C50 C51 -1.5(11) . . . . ?
C49 C50 C51 C46 0.7(11) . . . . ?
C51 C46 C47 C48 0.0(8) . . . . ?
C52 C49 C50 C51 178.1(7) . . . . ?
O1 C1 C2 N1 63.6(6) . . . . ?
O1 C1 C2 C3 178.7(6) . . . . ?
O2 C1 C2 N1 -116.2(6) . . . . ?
O2 C1 C2 C3 -1.1(6) . . . . ?
N1 C2 C3 C4 -169.7(6) . . . . ?
C1 C2 C3 C4 75.8(7) . . . . ?
C2 C3 C4 C5 68.6(9) . . . . ?
C2 C3 C4 C6 -172.1(7) . . . . ?
O1A C1A C2A N1A 155.1(14) . . . . ?
O1A C1A C2A C3A -81.1(12) . . . . ?
O2A C1A C2A N1A -25.0(15) . . . . ?
O2A C1A C2A C3A 98.8(12) . . . . ?
N1A C2A C3A C4A -64(2) . . . . ?
C1A C2A C3A C4A 172.8(14) . . . . ?
C2A C3A C4A C5A -59(2) . . . . ?
C2A C3A C4A C6A 175.5(19) . . . . ?
