#------------------------------------------------------------------------------
#$Date: 2025-03-15 01:31:40 +0200 (Sat, 15 Mar 2025) $
#$Revision: 298450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/01/7250113.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_7250113
loop_
_publ_author_name
'Pan, Ziqi'
'Zhang, Menglong'
'Hou, Xinyu'
'Yang, Huiwen'
'Rong, Hua'
'Song, Haibin'
'Zhang, Yong'
'Chen, Wei'
'Wu, Songgu'
_publ_section_title
;
 Improvement of humidity stability of ethyl gallate by cocrystal strategy
 and study of dissolution behavior of the cocrystal
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00174A
_journal_year                    2025
_chemical_formula_moiety         'C9 H10 O5, C4 H6 N2'
_chemical_formula_sum            'C13 H16 N2 O5'
_chemical_formula_weight         280.28
_chemical_name_systematic        EG-2MIE
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-20 deposited with the CCDC.	2025-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                110.381(2)
_cell_angle_beta                 91.880(2)
_cell_angle_gamma                94.517(2)
_cell_formula_units_Z            4
_cell_length_a                   8.51680(10)
_cell_length_b                   11.7510(2)
_cell_length_c                   14.3094(3)
_cell_measurement_reflns_used    17180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.8120
_cell_measurement_theta_min      4.0670
_cell_volume                     1335.49(4)
_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 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  94.00   0.50    0.50    --    5.00  57.00 150.00  238
  2  ω    -79.00  41.00   0.50    0.50    --  -48.80  57.00  30.00  240
  3  ω   -138.00 -11.00   0.50    0.50    --  -48.80 -30.00-110.06  254
  4  ω    -82.00  41.00   0.50    0.50    --  -48.80  38.00 -90.00  246
  5  ω    -83.00  41.00   0.50    0.50    --  -48.80  72.00  90.00  248
  6  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00-150.00  246
  7  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -57.00  30.00  238
  8  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 120.00  246
  9  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  246
 10  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00-180.00  246
 11  ω   -199.00 -75.00   0.50    0.50    -- -110.00 -36.00 -20.96  248
 12  ω   -199.00 -77.00   0.50    0.50    -- -110.00 -38.00  60.00  244
 13  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00   0.00  246
 14  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -50.00-108.10  238
 15  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -49.00-175.79  238
 16  ω   -199.00 -78.00   0.50    0.50    -- -110.00 -65.00  97.74  242
 17  ω   -140.00 -21.00   0.50    0.50    -- -110.00  57.00 -90.00  238
 18  ω   -144.00 -21.00   0.50    0.50    -- -110.00  72.00 -60.00  246
 19  ω   -199.00 -77.00   0.50    0.50    -- -110.00 -38.00 150.00  244
 20  ω   -107.00 -81.00   0.50    0.50    -- -110.00  72.00 -90.00   52
 21  ω    -94.00 -49.00   0.50    0.50    -- -110.00  72.00  30.00   90
 22  ω   -141.00 -22.00   0.50    0.50    -- -110.00  72.00  90.00  238
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23140
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.042
_diffrn_reflns_theta_min         4.032
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68565
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0069(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         5544
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0755P)²+0.5465P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5296
_reflns_number_total             5544
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00174a2.cif
_cod_data_source_block           EG-2MIE
_cod_database_code               7250113
_shelxl_version_number           2013-2
_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   0.853
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H9-H5
 2.15 with sigma of 0.01
 H4-H10
 2.15 with sigma of 0.01
 N2-C2 \\sim N5-C30
 with sigma of 0.02
 N2-C4 \\sim N5-C28
 with sigma of 0.02
 N1-C2 \\sim N6-C30
 with sigma of 0.02
 N1-C3 \\sim N6-C29
 with sigma of 0.02
 C2-C1 \\sim C30-C27
 with sigma of 0.02
 C3-C4 \\sim C29-C28
 with sigma of 0.02
 N2-N1 \\sim N5-N6
 with sigma of 0.04
 N2-C3 \\sim N5-C29
 with sigma of 0.04
 N2-C1 \\sim N5-C27
 with sigma of 0.04
 N1-C4 \\sim N6-C28
 with sigma of 0.04
 N1-C1 \\sim N6-C27
 with sigma of 0.04
 C2-C3 \\sim C30-C29
 with sigma of 0.04
 C2-C4 \\sim C30-C28
 with sigma of 0.04
3. Others
 Sof(N5)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(N6)=Sof(C30)=Sof(C27)=
 Sof(H27A)=Sof(H27B)=Sof(H27C)=1-FVAR(1)
 Sof(N2)=Sof(N1)=Sof(C2)=Sof(C3)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(C1)=Sof(H1A)=
 Sof(H1B)=Sof(H1C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C22(H22), C17(H17), C26(H26), C8(H8A), C7(H7), C3(H3B), C4(H4A),
 C28(H28), C29(H29)
4.c Tetrahedral OH refined with riding coordinates:
 O9(H9)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C5(H5A,H5B,H5C), C1(H1A,H1B,H1C),
 C27(H27A,H27B,H27C)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O9 O 0.56757(11) 0.65831(8) 0.79831(7) 0.0217(2) Uani 1 1 d . . . . .
H9 H 0.5800 0.6275 0.8411 0.033 Uiso 1 1 calc DR U . . .
O4 O 0.48611(11) 0.35694(8) 0.71065(7) 0.0221(2) Uani 1 1 d . . . . .
H4 H 0.4419 0.3455 0.6559 0.033 Uiso 1 1 calc DR U . . .
O5 O 0.77610(13) 0.49519(9) 0.73739(8) 0.0262(2) Uani 1 1 d . . . . .
O10 O 0.27879(13) 0.51992(8) 0.73724(8) 0.0261(2) Uani 1 1 d . . . . .
O6 O 0.03263(11) 1.00833(8) 0.88358(8) 0.0263(2) Uani 1 1 d . . . . .
O1 O 1.02168(12) 0.00791(9) 0.63105(8) 0.0283(2) Uani 1 1 d . . . . .
O7 O -0.12533(12) 0.83289(9) 0.82731(8) 0.0311(2) Uani 1 1 d . . . . .
O3 O 0.47919(12) 0.10418(9) 0.65599(9) 0.0316(3) Uani 1 1 d . . . . .
O8 O 0.57745(12) 0.90899(9) 0.88554(9) 0.0325(3) Uani 1 1 d . . . . .
O2 O 1.18041(12) 0.18206(9) 0.66945(9) 0.0346(3) Uani 1 1 d . . . . .
N4 N 0.66345(14) 0.62520(11) 0.96580(8) 0.0256(3) Uani 1 1 d . . . . .
N3 N 0.65542(15) 0.62166(11) 1.11534(9) 0.0271(3) Uani 1 1 d . . . . .
C15 C 0.43389(15) 0.71168(11) 0.81089(9) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.28540(16) 0.64396(11) 0.78068(9) 0.0204(3) Uani 1 1 d . . . . .
C13 C 0.29915(16) 0.89652(12) 0.86786(10) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.3035 0.9810 0.8967 0.028 Uiso 1 1 calc R U . . .
C24 C 0.61951(16) 0.30368(12) 0.69824(9) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.43662(16) 0.83921(12) 0.85508(10) 0.0230(3) Uani 1 1 d . . . . .
C25 C 0.76861(16) 0.37131(11) 0.71130(9) 0.0207(3) Uani 1 1 d . . . . .
C22 C 0.75672(16) 0.11959(12) 0.65715(10) 0.0237(3) Uani 1 1 d . . . . .
H22 H 0.7529 0.0352 0.6385 0.028 Uiso 1 1 calc R U . . .
C23 C 0.61870(16) 0.17610(12) 0.67067(10) 0.0228(3) Uani 1 1 d . . . . .
C20 C 1.04906(16) 0.12880(12) 0.65777(10) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.3779(2) 0.29411(16) 0.51770(11) 0.0289(4) Uani 0.816(4) 1 d D . P A 1
C6 C 0.60147(17) 0.67433(12) 1.05375(10) 0.0256(3) Uani 1 1 d . . . . .
C11 C 0.00576(16) 0.88675(12) 0.84853(9) 0.0216(3) Uani 1 1 d . . . . .
C17 C 0.14615(15) 0.69989(12) 0.79429(10) 0.0216(3) Uani 1 1 d . . . . .
H17 H 0.0491 0.6536 0.7751 0.026 Uiso 1 1 calc R U . . .
C21 C 0.90156(16) 0.18914(12) 0.67153(9) 0.0216(3) Uani 1 1 d . . . . .
C26 C 0.90819(16) 0.31593(12) 0.69896(9) 0.0221(3) Uani 1 1 d . . . . .
H26 H 1.0049 0.3625 0.7088 0.026 Uiso 1 1 calc R U . . .
N1 N 0.3526(2) 0.28604(17) 0.36565(12) 0.0299(4) Uani 0.816(4) 1 d D . P A 1
C10 C -0.10286(16) 1.07793(12) 0.89272(10) 0.0248(3) Uani 1 1 d . . . . .
H10A H -0.1729 1.0626 0.9400 0.030 Uiso 1 1 calc R U . . .
H10B H -0.1612 1.0563 0.8286 0.030 Uiso 1 1 calc R U . . .
C8 C 0.75476(18) 0.53649(13) 1.06554(11) 0.0290(3) Uani 1 1 d . . . . .
H8A H 0.8084 0.4870 1.0915 0.035 Uiso 1 1 calc R U . . .
C7 C 0.75933(18) 0.53862(13) 0.97202(10) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.8165 0.4906 0.9212 0.034 Uiso 1 1 calc R U . . .
C9 C -0.03696(18) 1.20989(13) 0.92926(12) 0.0312(3) Uani 1 1 d . . . . .
H9A H 0.0371 1.2223 0.8838 0.047 Uiso 1 1 calc R U . . .
H9B H 0.0154 1.2309 0.9943 0.047 Uiso 1 1 calc R U . . .
H9C H -0.1214 1.2605 0.9330 0.047 Uiso 1 1 calc R U . . .
C18 C 1.0893(2) -0.19503(13) 0.58017(12) 0.0351(3) Uani 1 1 d . . . . .
H18A H 1.0248 -0.2141 0.5194 0.053 Uiso 1 1 calc R U . . .
H18B H 1.0265 -0.2084 0.6305 0.053 Uiso 1 1 calc R U . . .
H18C H 1.1741 -0.2465 0.5684 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4913(2) 0.77056(15) 1.07908(13) 0.0367(4) Uani 1 1 d . . . . .
H5A H 0.5412 0.8429 1.1297 0.055 Uiso 1 1 calc R U . . .
H5B H 0.3977 0.7426 1.1035 0.055 Uiso 1 1 calc R U . . .
H5C H 0.4635 0.7885 1.0205 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3305(3) 0.3543(2) 0.45970(16) 0.0296(5) Uani 0.816(4) 1 d D . P A 1
C3 C 0.4150(3) 0.18100(17) 0.36377(17) 0.0314(5) Uani 0.816(4) 1 d D . P A 1
H3B H 0.4411 0.1184 0.3075 0.038 Uiso 0.816(4) 1 calc R U P A 1
C4 C 0.4309(2) 0.18616(17) 0.45913(16) 0.0304(4) Uani 0.816(4) 1 d D . P A 1
H4A H 0.4703 0.1277 0.4812 0.036 Uiso 0.816(4) 1 calc R U P A 1
C1 C 0.2648(4) 0.4736(2) 0.4923(2) 0.0488(6) Uani 0.816(4) 1 d D . P A 1
H1A H 0.1636 0.4659 0.5183 0.073 Uiso 0.816(4) 1 calc R U P A 1
H1B H 0.2531 0.5003 0.4364 0.073 Uiso 0.816(4) 1 calc R U P A 1
H1C H 0.3349 0.5323 0.5434 0.073 Uiso 0.816(4) 1 calc R U P A 1
N5 N 0.3045(9) 0.3520(8) 0.3833(5) 0.033(2) Uani 0.184(4) 1 d D . P A 2
C28 C 0.2060(11) 0.4364(8) 0.4353(7) 0.032(2) Uani 0.184(4) 1 d D . P A 2
H28 H 0.1419 0.4802 0.4094 0.039 Uiso 0.184(4) 1 calc R U P A 2
C29 C 0.2208(11) 0.4431(10) 0.5322(7) 0.038(2) Uani 0.184(4) 1 d D . P A 2
H29 H 0.1736 0.4952 0.5863 0.045 Uiso 0.184(4) 1 calc R U P A 2
N6 N 0.3220(9) 0.3554(8) 0.5334(5) 0.034(2) Uani 0.184(4) 1 d D . P A 2
C30 C 0.3731(12) 0.3054(9) 0.4432(8) 0.035(3) Uani 0.184(4) 1 d D . P A 2
C27 C 0.4847(16) 0.2086(9) 0.4161(8) 0.043(3) Uani 0.184(4) 1 d D . P A 2
H27A H 0.4262 0.1299 0.3970 0.065 Uiso 0.184(4) 1 calc R U P A 2
H27B H 0.5561 0.2201 0.4727 0.065 Uiso 0.184(4) 1 calc R U P A 2
H27C H 0.5434 0.2139 0.3614 0.065 Uiso 0.184(4) 1 calc R U P A 2
C12 C 0.15389(15) 0.82696(12) 0.83731(9) 0.0211(3) Uani 1 1 d . . . . .
C19 C 1.15597(17) -0.06343(13) 0.61490(11) 0.0287(3) Uani 1 1 d . . . . .
H19A H 1.2214 -0.0426 0.6764 0.034 Uiso 1 1 calc R U . . .
H19B H 1.2195 -0.0483 0.5646 0.034 Uiso 1 1 calc R U . . .
H3A H 0.621(3) 0.639(2) 1.1756(17) 0.051(6) Uiso 1 1 d . . . . .
H1 H 0.345(3) 0.310(2) 0.3139(19) 0.059(7) Uiso 1 1 d . . . . .
H10 H 0.352(4) 0.5111(19) 0.742(2) 0.088(11) Uiso 1 1 d D . . . .
H5 H 0.701(3) 0.502(2) 0.7308(16) 0.064(9) Uiso 1 1 d D . . . .
H3 H 0.395(3) 0.144(2) 0.6630(17) 0.054(6) Uiso 1 1 d . . . . .
H8 H 0.655(3) 0.868(2) 0.8682(17) 0.053(6) Uiso 1 1 d . . . . .
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
C15 O9 H9 109.5 . . ?
C24 O4 H4 109.5 . . ?
C25 O5 H5 100(2) . . ?
C16 O10 H10 101(2) . . ?
C11 O6 C10 117.51(10) . . ?
C20 O1 C19 118.14(11) . . ?
C23 O3 H3 114.4(16) . . ?
C14 O8 H8 112.3(17) . . ?
C6 N4 C7 108.70(12) . . ?
C6 N3 C8 109.01(12) . . ?
C6 N3 H3A 120.5(14) . . ?
C8 N3 H3A 130.2(14) . . ?
O9 C15 C16 121.87(11) . . ?
O9 C15 C14 120.57(12) . . ?
C14 C15 C16 117.55(12) . . ?
O10 C16 C15 118.97(11) . . ?
O10 C16 C17 119.31(12) . . ?
C17 C16 C15 121.72(11) . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.64(12) . . ?
C12 C13 H13 120.2 . . ?
O4 C24 C25 121.97(11) . . ?
O4 C24 C23 121.21(12) . . ?
C23 C24 C25 116.82(12) . . ?
O8 C14 C15 119.85(12) . . ?
O8 C14 C13 118.68(12) . . ?
C13 C14 C15 121.47(12) . . ?
O5 C25 C24 119.23(12) . . ?
O5 C25 C26 118.71(12) . . ?
C26 C25 C24 122.06(11) . . ?
C23 C22 H22 120.1 . . ?
C23 C22 C21 119.90(12) . . ?
C21 C22 H22 120.1 . . ?
O3 C23 C24 120.39(12) . . ?
O3 C23 C22 117.88(11) . . ?
C22 C23 C24 121.73(12) . . ?
O1 C20 C21 112.04(11) . . ?
O2 C20 O1 123.53(12) . . ?
O2 C20 C21 124.43(12) . . ?
C2 N2 C4 109.35(18) . . ?
N4 C6 C5 126.29(13) . . ?
N3 C6 N4 108.16(12) . . ?
N3 C6 C5 125.55(13) . . ?
O6 C11 C12 112.05(11) . . ?
O7 C11 O6 123.39(12) . . ?
O7 C11 C12 124.55(12) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C12 119.00(12) . . ?
C12 C17 H17 120.5 . . ?
C22 C21 C20 119.88(12) . . ?
C22 C21 C26 120.39(12) . . ?
C26 C21 C20 119.73(12) . . ?
C25 C26 C21 119.09(12) . . ?
C25 C26 H26 120.5 . . ?
C21 C26 H26 120.5 . . ?
C2 N1 C3 109.66(19) . . ?
C2 N1 H1 124.9(16) . . ?
C3 N1 H1 124.6(16) . . ?
O6 C10 H10A 110.6 . . ?
O6 C10 H10B 110.6 . . ?
O6 C10 C9 105.71(11) . . ?
H10A C10 H10B 108.7 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
N3 C8 H8A 126.6 . . ?
C7 C8 N3 106.90(12) . . ?
C7 C8 H8A 126.6 . . ?
N4 C7 H7 126.4 . . ?
C8 C7 N4 107.23(12) . . ?
C8 C7 H7 126.4 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C2 C1 127.0(2) . . ?
N1 C2 N2 107.1(2) . . ?
N1 C2 C1 125.9(2) . . ?
N1 C3 H3B 126.6 . . ?
C4 C3 N1 106.79(17) . . ?
C4 C3 H3B 126.6 . . ?
N2 C4 H4A 126.4 . . ?
C3 C4 N2 107.10(17) . . ?
C3 C4 H4A 126.4 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C28 N5 H1 143.5(17) . . ?
C30 N5 C28 110.1(8) . . ?
C30 N5 H1 106.4(17) . . ?
N5 C28 H28 126.7 . . ?
C29 C28 N5 106.6(7) . . ?
C29 C28 H28 126.7 . . ?
C28 C29 H29 127.2 . . ?
C28 C29 N6 105.6(7) . . ?
N6 C29 H29 127.2 . . ?
C30 N6 C29 109.3(8) . . ?
N5 C30 N6 108.2(9) . . ?
N5 C30 C27 127.2(10) . . ?
N6 C30 C27 124.5(9) . . ?
C30 C27 H27A 109.5 . . ?
C30 C27 H27B 109.5 . . ?
C30 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13 C12 C11 120.44(11) . . ?
C13 C12 C17 120.61(12) . . ?
C17 C12 C11 118.95(12) . . ?
O1 C19 C18 106.19(12) . . ?
O1 C19 H19A 110.5 . . ?
O1 C19 H19B 110.5 . . ?
C18 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
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
O9 H9 0.8200 . ?
O9 C15 1.3301(16) . ?
O4 H4 0.8200 . ?
O4 C24 1.3274(16) . ?
O5 C25 1.3668(15) . ?
O5 H5 0.66(2) . ?
O10 C16 1.3667(15) . ?
O10 H10 0.64(3) . ?
O6 C11 1.3369(15) . ?
O6 C10 1.4496(15) . ?
O1 C20 1.3351(16) . ?
O1 C19 1.4484(16) . ?
O7 C11 1.2132(17) . ?
O3 C23 1.3682(16) . ?
O3 H3 0.88(2) . ?
O8 C14 1.3648(16) . ?
O8 H8 0.84(2) . ?
O2 C20 1.2147(17) . ?
N4 C6 1.3348(18) . ?
N4 C7 1.3781(18) . ?
N3 C6 1.3300(18) . ?
N3 C8 1.3790(19) . ?
N3 H3A 0.88(2) . ?
C15 C16 1.4091(18) . ?
C15 C14 1.4071(18) . ?
C16 C17 1.3875(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3821(19) . ?
C13 C12 1.3950(18) . ?
C24 C25 1.4145(18) . ?
C24 C23 1.4106(18) . ?
C25 C26 1.3869(18) . ?
C22 H22 0.9300 . ?
C22 C23 1.3815(19) . ?
C22 C21 1.3926(19) . ?
C20 C21 1.4761(18) . ?
N2 C2 1.336(3) . ?
N2 C4 1.375(3) . ?
C6 C5 1.482(2) . ?
C11 C12 1.4783(18) . ?
C17 H17 0.9300 . ?
C17 C12 1.3980(18) . ?
C21 C26 1.3982(18) . ?
C26 H26 0.9300 . ?
N1 C2 1.334(3) . ?
N1 C3 1.374(3) . ?
N1 H1 0.89(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.5073(19) . ?
C8 H8A 0.9300 . ?
C8 C7 1.349(2) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C19 1.506(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C2 C1 1.477(3) . ?
C3 H3B 0.9300 . ?
C3 C4 1.346(3) . ?
C4 H4A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N5 C28 1.378(10) . ?
N5 C30 1.312(12) . ?
N5 H1 1.03(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.361(10) . ?
C29 H29 0.9300 . ?
C29 N6 1.399(11) . ?
N6 C30 1.322(12) . ?
C30 C27 1.494(11) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
O9 C15 C16 O10 0.01(18) . . . . ?
O9 C15 C16 C17 179.73(11) . . . . ?
O9 C15 C14 O8 -0.12(19) . . . . ?
O9 C15 C14 C13 179.31(11) . . . . ?
O4 C24 C25 O5 -0.06(18) . . . . ?
O4 C24 C25 C26 179.61(11) . . . . ?
O4 C24 C23 O3 0.05(19) . . . . ?
O4 C24 C23 C22 179.73(12) . . . . ?
O5 C25 C26 C21 -179.51(11) . . . . ?
O10 C16 C17 C12 -178.99(11) . . . . ?
O6 C11 C12 C13 3.85(18) . . . . ?
O6 C11 C12 C17 -175.21(11) . . . . ?
O1 C20 C21 C22 0.43(18) . . . . ?
O1 C20 C21 C26 -179.57(11) . . . . ?
O7 C11 C12 C13 -177.17(13) . . . . ?
O7 C11 C12 C17 3.8(2) . . . . ?
O2 C20 C21 C22 -179.37(13) . . . . ?
O2 C20 C21 C26 0.6(2) . . . . ?
N3 C8 C7 N4 0.23(17) . . . . ?
C15 C16 C17 C12 1.30(19) . . . . ?
C16 C15 C14 O8 -179.92(12) . . . . ?
C16 C15 C14 C13 -0.49(19) . . . . ?
C16 C17 C12 C13 -1.19(19) . . . . ?
C16 C17 C12 C11 177.87(11) . . . . ?
C24 C25 C26 C21 0.82(19) . . . . ?
C14 C15 C16 O10 179.81(11) . . . . ?
C14 C15 C16 C17 -0.47(19) . . . . ?
C14 C13 C12 C11 -178.79(12) . . . . ?
C14 C13 C12 C17 0.3(2) . . . . ?
C25 C24 C23 O3 -179.59(12) . . . . ?
C25 C24 C23 C22 0.09(19) . . . . ?
C22 C21 C26 C25 -0.21(19) . . . . ?
C23 C24 C25 O5 179.58(11) . . . . ?
C23 C24 C25 C26 -0.75(19) . . . . ?
C23 C22 C21 C20 179.57(12) . . . . ?
C23 C22 C21 C26 -0.4(2) . . . . ?
C20 O1 C19 C18 -176.76(12) . . . . ?
C20 C21 C26 C25 179.79(11) . . . . ?
C6 N4 C7 C8 -0.21(17) . . . . ?
C6 N3 C8 C7 -0.16(17) . . . . ?
C11 O6 C10 C9 -177.65(11) . . . . ?
C21 C22 C23 O3 -179.82(12) . . . . ?
C21 C22 C23 C24 0.5(2) . . . . ?
N1 C3 C4 N2 0.1(2) . . . . ?
C10 O6 C11 O7 -2.37(19) . . . . ?
C10 O6 C11 C12 176.62(10) . . . . ?
C8 N3 C6 N4 0.03(16) . . . . ?
C8 N3 C6 C5 179.86(14) . . . . ?
C7 N4 C6 N3 0.11(16) . . . . ?
C7 N4 C6 C5 -179.72(14) . . . . ?
C2 N2 C4 C3 -0.1(2) . . . . ?
C2 N1 C3 C4 0.0(2) . . . . ?
C3 N1 C2 N2 0.0(3) . . . . ?
C3 N1 C2 C1 -179.7(2) . . . . ?
C4 N2 C2 N1 0.0(2) . . . . ?
C4 N2 C2 C1 179.7(2) . . . . ?
N5 C28 C29 N6 -3.6(11) . . . . ?
C28 N5 C30 N6 0.6(11) . . . . ?
C28 N5 C30 C27 178.2(11) . . . . ?
C28 C29 N6 C30 4.2(12) . . . . ?
C29 N6 C30 N5 -3.0(12) . . . . ?
C29 N6 C30 C27 179.4(10) . . . . ?
C30 N5 C28 C29 2.0(11) . . . . ?
C12 C13 C14 O8 -179.97(12) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C19 O1 C20 O2 -0.2(2) . . . . ?
C19 O1 C20 C21 -179.99(11) . . . . ?
