#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:11:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180172 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/68/7106823.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_7106823
loop_
_publ_author_name
'Andrew F. Kyle'
'Pavol Jakubec'
'Dane M. Cockfield'
'Ed Cleator'
'John Skidmore'
'Darren J. Dixon'
_publ_section_title
;
 Total synthesis of (--)-nakadomarin A
;
_journal_name_full               Chem.Commun.
_journal_page_first              10037
_journal_page_last               10039
_journal_paper_doi               10.1039/c1cc13665h
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H20 N2 O7'
_chemical_formula_sum            'C16 H20 N2 O7'
_chemical_formula_weight         352.34
_chemical_melting_point          ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             10-11-04
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 96.0302(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0669(2)
_cell_length_b                   15.7455(4)
_cell_length_c                   12.0613(3)
_cell_measurement_reflns_used    3777
_cell_measurement_temperature    123
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     1712.38(7)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15585
_diffrn_reflns_theta_full        26.646
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         5.099
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.44
_refine_ls_extinction_coef       770(60)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9620
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     91
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.0226392
_refine_ls_shift/su_mean         0.0005859
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + ( 0.04P)² + 0.19P]
,where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0978
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0978
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2716
_reflns_number_total             4032
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.97
_oxford_diffrn_Wilson_scale      5.65
_oxford_refine_ls_r_factor_ref   0.0794
_oxford_refine_ls_scale          0.4375(9)
_oxford_reflns_number_all        4032
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 009DJD10
_cod_data_source_file            c1cc13665h.txt
_cod_data_source_block           12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               7106823
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S) H ( 52,X'S)
RIDE C ( 9,X'S) H ( 93,X'S) H ( 92,X'S) H ( 91,X'S)
RIDE C ( 11,X'S) H ( 111,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S)
RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S)
RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) H ( 243,X'S)
RIDE C ( 25,X'S) H ( 253,X'S) H ( 252,X'S) H ( 251,X'S)
RIDE C ( 29,X'S) H ( 291,X'S)
RIDE C ( 30,X'S) H ( 301,X'S) H ( 302,X'S)
RIDE C ( 35,X'S) H ( 353,X'S) H ( 352,X'S) H ( 351,X'S)
RIDE C ( 36,X'S) H ( 361,X'S)
RIDE C ( 42,X'S) H ( 421,X'S) H ( 422,X'S)
RIDE C ( 46,X'S) H ( 461,X'S) H ( 462,X'S)
RIDE C ( 49,X'S) H ( 491,X'S) H ( 492,X'S) H ( 493,X'S)
RIDE C ( 50,X'S) H ( 503,X'S) H ( 502,X'S) H ( 501,X'S)
RIDE C ( 380,X'S) H (3801,X'S)
RIDE C ( 381,X'S) H (3811,X'S)
RIDE C ( 391,X'S) H (3911,X'S)
RIDE C ( 400,X'S) H (4001,X'S)
RIDE C ( 410,X'S) H (4101,X'S)
RIDE C ( 411,X'S) H (4111,X'S)
RIDE C(370,X'S,U'S) C(371,X'S,U'S)
EQUIVALENCE PART(1001,OCC) PART(1002,OCC)
WEIGHT -1 PART(1001,OCC)
END
;
_iucr_refine_instruction_details_restraints
;
SAME C(370) C(380) O(390) C(400) C(410) AND C(371) C(411) O(401) C(391) C(381)
DELU 0.01 C(370) C(380) O(390) C(400) C(410) AND
CONT C(371) C(411) O(401) C(391) C(381)
SIMU 0.01 C(370) C(380) O(390) C(400) C(410) AND
CONT C(371) C(411) O(401) C(391) C(381)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.4200(2) 0.78721(15) 0.25368(16) 0.0335 1.0000 Uani . . . . . .
C2 C 0.4287(3) 0.7929(2) 0.3551(2) 0.0265 1.0000 Uani . . . . . .
N3 N 0.4977(3) 0.73968(16) 0.4304(2) 0.0298 1.0000 Uani . . . . . .
C4 C 0.4886(3) 0.7625(2) 0.5468(2) 0.0324 1.0000 Uani . . . . . .
C5 C 0.4313(4) 0.8538(2) 0.5411(2) 0.0332 1.0000 Uani . . . . . .
C6 C 0.3576(3) 0.8646(2) 0.4201(2) 0.0290 1.0000 Uani . . . . . .
C7 C 0.3967(4) 0.9463(2) 0.3611(3) 0.0328 1.0000 Uani . . . . . .
O8 O 0.5393(3) 0.96688(15) 0.38930(19) 0.0406 1.0000 Uani . . . . . .
C9 C 0.5978(4) 1.0378(2) 0.3302(3) 0.0471 1.0000 Uani . . . . . .
O10 O 0.3139(3) 0.98427(16) 0.29416(19) 0.0434 1.0000 Uani . . . . . .
C11 C 0.1868(3) 0.8528(2) 0.4037(2) 0.0303 1.0000 Uani . . . . . .
C12 C 0.1419(3) 0.7643(2) 0.4330(2) 0.0287 1.0000 Uani . . . . . .
C13 C 0.0951(4) 0.7356(2) 0.5295(3) 0.0348 1.0000 Uani . . . . . .
O14 O 0.0694(3) 0.64996(16) 0.52418(19) 0.0421 1.0000 Uani . . . . . .
C15 C 0.1010(4) 0.6254(2) 0.4210(3) 0.0365 1.0000 Uani . . . . . .
C16 C 0.1458(4) 0.6915(2) 0.3637(3) 0.0396 1.0000 Uani . . . . . .
C17 C 0.1107(3) 0.9208(2) 0.4679(3) 0.0334 1.0000 Uani . . . . . .
N18 N -0.0533(3) 0.91959(19) 0.4348(2) 0.0375 1.0000 Uani . . . . . .
O19 O -0.0974(3) 0.9171(2) 0.33607(18) 0.0576 1.0000 Uani . . . . . .
O20 O -0.1349(3) 0.92115(19) 0.50922(19) 0.0472 1.0000 Uani . . . . . .
C21 C 0.6474(4) 0.7423(3) 0.5932(3) 0.0418 1.0000 Uani . . . . . .
O22 O 0.6800(3) 0.66721(18) 0.53183(18) 0.0488 1.0000 Uani . . . . . .
C23 C 0.6171(4) 0.6777(2) 0.4170(3) 0.0390 1.0000 Uani . . . . . .
C24 C 0.5552(5) 0.5932(3) 0.3776(3) 0.0578 1.0000 Uani . . . . . .
C25 C 0.7292(4) 0.7135(3) 0.3468(3) 0.0548 1.0000 Uani . . . . . .
O26 O 0.8686(2) 0.36604(15) 0.25733(16) 0.0391 1.0000 Uani . . . . . .
C27 C 0.8709(3) 0.3575(2) 0.1555(2) 0.0301 1.0000 Uani . . . . . .
N28 N 0.9317(3) 0.41015(17) 0.08660(19) 0.0306 1.0000 Uani . . . . . .
C29 C 0.9181(4) 0.3837(2) -0.0307(2) 0.0342 1.0000 Uani . . . . . .
C30 C 0.8591(4) 0.2922(2) -0.0276(2) 0.0350 1.0000 Uani . . . . . .
C31 C 0.7977(3) 0.2834(2) 0.0873(2) 0.0299 1.0000 Uani . . . . . .
C32 C 0.8484(4) 0.2018(2) 0.1492(3) 0.0349 1.0000 Uani . . . . . .
O33 O 0.7694(3) 0.15573(17) 0.1949(2) 0.0525 1.0000 Uani . . . . . .
O34 O 0.9938(2) 0.19109(16) 0.14880(19) 0.0411 1.0000 Uani . . . . . .
C35 C 1.0585(4) 0.1166(2) 0.2065(3) 0.0442 1.0000 Uani . . . . . .
C36 C 0.6267(4) 0.2924(2) 0.0870(3) 0.0340 1.0000 Uani . . . . . .
C42 C 0.5471(4) 0.2266(2) 0.0107(3) 0.0410 1.0000 Uani . . . . . .
N43 N 0.3861(3) 0.2203(2) 0.0297(3) 0.0458 1.0000 Uani . . . . . .
O44 O 0.2970(3) 0.2097(2) -0.0506(2) 0.0648 1.0000 Uani . . . . . .
O45 O 0.3528(3) 0.2268(3) 0.1229(2) 0.1025 1.0000 Uani . . . . . .
C46 C 1.0748(4) 0.4008(3) -0.0558(3) 0.0462 1.0000 Uani . . . . . .
O47 O 1.1094(3) 0.47872(18) 0.00390(19) 0.0531 1.0000 Uani . . . . . .
C48 C 1.0472(4) 0.4759(2) 0.1084(3) 0.0396 1.0000 Uani . . . . . .
C49 C 0.9789(5) 0.5615(2) 0.1266(3) 0.0581 1.0000 Uani . . . . . .
C50 C 1.1633(4) 0.4494(3) 0.2018(3) 0.0533 1.0000 Uani . . . . . .
H41 H 0.4192 0.7254 0.5797 0.0382 1.0000 Uiso R . . . . .
H51 H 0.5106 0.8945 0.5569 0.0405 1.0000 Uiso R . . . . .
H52 H 0.3632 0.8627 0.5935 0.0400 1.0000 Uiso R . . . . .
H93 H 0.6807 1.0614 0.3762 0.0715 1.0000 Uiso R . . . . .
H92 H 0.5204 1.0787 0.3119 0.0710 1.0000 Uiso R . . . . .
H91 H 0.6331 1.0160 0.2627 0.0716 1.0000 Uiso R . . . . .
H111 H 0.1544 0.8609 0.3236 0.0353 1.0000 Uiso R . . . . .
H131 H 0.0815 0.7681 0.5916 0.0424 1.0000 Uiso R . . . . .
H151 H 0.0925 0.5688 0.3981 0.0442 1.0000 Uiso R . . . . .
H161 H 0.1747 0.6888 0.2908 0.0468 1.0000 Uiso R . . . . .
H171 H 0.1455 0.9765 0.4465 0.0410 1.0000 Uiso R . . . . .
H172 H 0.1277 0.9124 0.5467 0.0408 1.0000 Uiso R . . . . .
H211 H 0.7142 0.7886 0.5790 0.0500 1.0000 Uiso R . . . . .
H212 H 0.6555 0.7283 0.6733 0.0498 1.0000 Uiso R . . . . .
H241 H 0.6348 0.5526 0.3821 0.0850 1.0000 Uiso R . . . . .
H242 H 0.4806 0.5754 0.4256 0.0847 1.0000 Uiso R . . . . .
H243 H 0.5104 0.5974 0.2989 0.0840 1.0000 Uiso R . . . . .
H253 H 0.8074 0.6715 0.3472 0.0809 1.0000 Uiso R . . . . .
H252 H 0.7687 0.7669 0.3774 0.0808 1.0000 Uiso R . . . . .
H251 H 0.6832 0.7222 0.2720 0.0799 1.0000 Uiso R . . . . .
H291 H 0.8468 0.4210 -0.0754 0.0406 1.0000 Uiso R . . . . .
H301 H 0.9393 0.2520 -0.0328 0.0421 1.0000 Uiso R . . . . .
H302 H 0.7837 0.2824 -0.0884 0.0415 1.0000 Uiso R . . . . .
H353 H 1.1583 0.1119 0.1856 0.0667 1.0000 Uiso R . . . . .
H352 H 1.0613 0.1239 0.2856 0.0671 1.0000 Uiso R . . . . .
H351 H 1.0022 0.0673 0.1834 0.0675 1.0000 Uiso R . . . . .
H361 H 0.6034 0.2794 0.1623 0.0402 1.0000 Uiso R . . . . .
H421 H 0.5563 0.2419 -0.0660 0.0493 1.0000 Uiso R . . . . .
H422 H 0.5928 0.1711 0.0269 0.0494 1.0000 Uiso R . . . . .
H461 H 1.0858 0.4089 -0.1345 0.0549 1.0000 Uiso R . . . . .
H462 H 1.1416 0.3554 -0.0285 0.0547 1.0000 Uiso R . . . . .
H491 H 1.0556 0.6043 0.1323 0.0857 1.0000 Uiso R . . . . .
H492 H 0.9057 0.5749 0.0653 0.0851 1.0000 Uiso R . . . . .
H493 H 0.9330 0.5616 0.1965 0.0858 1.0000 Uiso R . . . . .
H503 H 1.2359 0.4942 0.2141 0.0797 1.0000 Uiso R . . . . .
H502 H 1.2097 0.3981 0.1829 0.0798 1.0000 Uiso R . . . . .
H501 H 1.1152 0.4395 0.2686 0.0793 1.0000 Uiso R . . . . .
C380 C 0.5398(11) 0.4420(4) 0.1310(3) 0.0363 0.607(14) Uani D . P 1 2 .
C381 C 0.5780(18) 0.4492(5) 0.1385(6) 0.0416 0.393(14) Uani D . P 1 1 .
O390 O 0.4860(8) 0.5133(3) 0.0756(6) 0.0424 0.607(14) Uani D . P 1 2 .
C391 C 0.535(2) 0.5200(5) 0.0822(12) 0.0427 0.393(14) Uani D . P 1 1 .
C400 C 0.4619(15) 0.4941(5) -0.0346(7) 0.0508 0.607(14) Uani D . P 1 2 .
O401 O 0.5107(13) 0.5003(5) -0.0280(9) 0.0419 0.393(14) Uani D . P 1 1 .
C410 C 0.5121(13) 0.4151(5) -0.0495(4) 0.0459 0.607(14) Uani D . P 1 2 .
C411 C 0.5479(16) 0.4172(6) -0.0400(5) 0.0415 0.393(14) Uani D . P 1 1 .
C370 C 0.5688(4) 0.38152(16) 0.0573(2) 0.0353 0.607(14) Uani D . P 1 2 .
C371 C 0.5738(4) 0.38027(16) 0.0611(2) 0.0352 0.393(14) Uani D . P 1 1 .
H3801 H 0.5482 0.4347 0.2103 0.0414 0.607(14) Uiso R . P 1 2 .
H3811 H 0.6099 0.4467 0.2160 0.0500 0.393(14) Uiso R . P 1 1 .
H3911 H 0.5193 0.5732 0.1128 0.0509 0.393(14) Uiso R . P 1 1 .
H4001 H 0.4125 0.5295 -0.0895 0.0521 0.607(14) Uiso R . P 1 2 .
H4101 H 0.5061 0.3866 -0.1167 0.0484 0.607(14) Uiso R . P 1 2 .
H4111 H 0.5602 0.3914 -0.1077 0.0512 0.393(14) Uiso R . P 1 1 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 127.5(3) yes
O1 . C2 . C6 . 124.9(3) yes
N3 . C2 . C6 . 107.6(2) yes
C2 . N3 . C4 . 115.3(2) yes
C2 . N3 . C23 . 129.3(3) yes
C4 . N3 . C23 . 112.5(2) yes
N3 . C4 . C5 . 104.0(2) yes
N3 . C4 . C21 . 98.9(2) yes
C5 . C4 . C21 . 121.1(3) yes
N3 . C4 . H41 . 110.4 no
C5 . C4 . H41 . 110.6 no
C21 . C4 . H41 . 110.6 no
C4 . C5 . C6 . 104.8(2) yes
C4 . C5 . H51 . 111.8 no
C6 . C5 . H51 . 110.5 no
C4 . C5 . H52 . 110.7 no
C6 . C5 . H52 . 111.7 no
H51 . C5 . H52 . 107.3 no
C5 . C6 . C2 . 103.6(2) yes
C5 . C6 . C7 . 115.6(2) yes
C2 . C6 . C7 . 104.4(2) yes
C5 . C6 . C11 . 115.6(2) yes
C2 . C6 . C11 . 108.1(2) yes
C7 . C6 . C11 . 108.6(2) yes
C6 . C7 . O8 . 110.5(3) yes
C6 . C7 . O10 . 124.9(3) yes
O8 . C7 . O10 . 124.5(3) yes
C7 . O8 . C9 . 116.9(2) yes
O8 . C9 . H93 . 108.5 no
O8 . C9 . H92 . 109.4 no
H93 . C9 . H92 . 112.4 no
O8 . C9 . H91 . 108.1 no
H93 . C9 . H91 . 108.4 no
H92 . C9 . H91 . 110.0 no
C6 . C11 . C12 . 111.8(3) yes
C6 . C11 . C17 . 110.4(2) yes
C12 . C11 . C17 . 112.5(3) yes
C6 . C11 . H111 . 107.5 no
C12 . C11 . H111 . 106.8 no
C17 . C11 . H111 . 107.6 no
C11 . C12 . C13 . 128.8(3) yes
C11 . C12 . C16 . 125.8(3) yes
C13 . C12 . C16 . 105.4(3) yes
C12 . C13 . O14 . 110.8(3) yes
C12 . C13 . H131 . 126.1 no
O14 . C13 . H131 . 123.1 no
C13 . O14 . C15 . 105.8(3) yes
O14 . C15 . C16 . 110.8(3) yes
O14 . C15 . H151 . 121.5 no
C16 . C15 . H151 . 127.7 no
C12 . C16 . C15 . 107.3(3) yes
C12 . C16 . H161 . 127.6 no
C15 . C16 . H161 . 125.1 no
C11 . C17 . N18 . 110.1(2) yes
C11 . C17 . H171 . 108.7 no
N18 . C17 . H171 . 106.2 no
C11 . C17 . H172 . 112.0 no
N18 . C17 . H172 . 108.4 no
H171 . C17 . H172 . 111.3 no
C17 . N18 . O19 . 118.4(3) yes
C17 . N18 . O20 . 117.7(2) yes
O19 . N18 . O20 . 123.9(3) yes
C4 . C21 . O22 . 102.7(3) yes
C4 . C21 . H211 . 111.2 no
O22 . C21 . H211 . 111.0 no
C4 . C21 . H212 . 112.2 no
O22 . C21 . H212 . 108.8 no
H211 . C21 . H212 . 110.8 no
C21 . O22 . C23 . 108.4(2) yes
N3 . C23 . O22 . 100.9(2) yes
N3 . C23 . C24 . 111.5(3) yes
O22 . C23 . C24 . 107.3(3) yes
N3 . C23 . C25 . 111.2(3) yes
O22 . C23 . C25 . 111.1(3) yes
C24 . C23 . C25 . 114.0(3) yes
C23 . C24 . H241 . 108.5 no
C23 . C24 . H242 . 109.0 no
H241 . C24 . H242 . 109.7 no
C23 . C24 . H243 . 110.1 no
H241 . C24 . H243 . 109.2 no
H242 . C24 . H243 . 110.2 no
C23 . C25 . H253 . 106.3 no
C23 . C25 . H252 . 110.8 no
H253 . C25 . H252 . 110.4 no
C23 . C25 . H251 . 109.2 no
H253 . C25 . H251 . 110.3 no
H252 . C25 . H251 . 109.7 no
O26 . C27 . N28 . 127.0(3) yes
O26 . C27 . C31 . 124.2(3) yes
N28 . C27 . C31 . 108.8(2) yes
C27 . N28 . C29 . 115.2(3) yes
C27 . N28 . C48 . 131.1(2) yes
C29 . N28 . C48 . 110.9(2) yes
N28 . C29 . C30 . 103.7(2) yes
N28 . C29 . C46 . 99.1(2) yes
C30 . C29 . C46 . 120.6(3) yes
N28 . C29 . H291 . 110.0 no
C30 . C29 . H291 . 111.0 no
C46 . C29 . H291 . 111.1 no
C29 . C30 . C31 . 105.3(2) yes
C29 . C30 . H301 . 110.1 no
C31 . C30 . H301 . 109.9 no
C29 . C30 . H302 . 110.8 no
C31 . C30 . H302 . 111.8 no
H301 . C30 . H302 . 108.9 no
C27 . C31 . C30 . 103.6(2) yes
C27 . C31 . C32 . 106.6(2) yes
C30 . C31 . C32 . 113.1(3) yes
C27 . C31 . C36 . 107.8(3) yes
C30 . C31 . C36 . 116.1(2) yes
C32 . C31 . C36 . 109.0(3) yes
C31 . C32 . O33 . 124.8(3) yes
C31 . C32 . O34 . 110.6(3) yes
O33 . C32 . O34 . 124.5(3) yes
C32 . O34 . C35 . 116.8(3) yes
O34 . C35 . H353 . 106.2 no
O34 . C35 . H352 . 110.3 no
H353 . C35 . H352 . 109.8 no
O34 . C35 . H351 . 109.9 no
H353 . C35 . H351 . 110.3 no
H352 . C35 . H351 . 110.3 no
C31 . C36 . C42 . 110.4(3) yes
C31 . C36 . H361 . 106.9 no
C42 . C36 . H361 . 106.6 no
C31 . C36 . C371 . 112.6(3) yes
C42 . C36 . C371 . 112.7(3) yes
H361 . C36 . C371 . 107.2 no
C31 . C36 . C42 . 110.4(3) yes
C31 . C36 . H361 . 106.9 no
C42 . C36 . H361 . 106.6 no
C31 . C36 . C370 . 113.7(3) yes
C42 . C36 . C370 . 110.8(3) yes
H361 . C36 . C370 . 108.0 no
C36 . C42 . N43 . 111.1(3) yes
C36 . C42 . H421 . 109.0 no
N43 . C42 . H421 . 110.1 no
C36 . C42 . H422 . 108.9 no
N43 . C42 . H422 . 107.9 no
H421 . C42 . H422 . 109.7 no
C42 . N43 . O44 . 117.7(3) yes
C42 . N43 . O45 . 118.7(3) yes
O44 . N43 . O45 . 123.5(3) yes
C29 . C46 . O47 . 102.2(3) yes
C29 . C46 . H461 . 114.5 no
O47 . C46 . H461 . 109.7 no
C29 . C46 . H462 . 111.6 no
O47 . C46 . H462 . 111.2 no
H461 . C46 . H462 . 107.6 no
C46 . O47 . C48 . 109.2(2) yes
N28 . C48 . O47 . 101.6(2) yes
N28 . C48 . C49 . 111.0(3) yes
O47 . C48 . C49 . 107.8(3) yes
N28 . C48 . C50 . 111.3(3) yes
O47 . C48 . C50 . 110.7(3) yes
C49 . C48 . C50 . 113.7(3) yes
C48 . C49 . H491 . 109.3 no
C48 . C49 . H492 . 110.1 no
H491 . C49 . H492 . 109.7 no
C48 . C49 . H493 . 110.1 no
H491 . C49 . H493 . 107.8 no
H492 . C49 . H493 . 109.9 no
C48 . C50 . H503 . 108.8 no
C48 . C50 . H502 . 110.3 no
H503 . C50 . H502 . 110.2 no
C48 . C50 . H501 . 108.9 no
H503 . C50 . H501 . 110.4 no
H502 . C50 . H501 . 108.2 no
O390 . C380 . C370 . 110.00(9) yes
O390 . C380 . H3801 . 124.9 no
C370 . C380 . H3801 . 124.9 no
C391 . C381 . C371 . 108.29(9) yes
C391 . C381 . H3811 . 125.1 no
C371 . C381 . H3811 . 126.6 no
C380 . O390 . C400 . 107.95(9) yes
C381 . C391 . O401 . 108.24(9) yes
C381 . C391 . H3911 . 126.4 no
O401 . C391 . H3911 . 125.3 no
O390 . C400 . C410 . 108.34(9) yes
O390 . C400 . H4001 . 125.0 no
C410 . C400 . H4001 . 126.6 no
C391 . O401 . C411 . 107.87(9) yes
C400 . C410 . C370 . 108.35(9) yes
C400 . C410 . H4101 . 125.4 no
C370 . C410 . H4101 . 126.2 no
O401 . C411 . C371 . 109.85(10) yes
O401 . C411 . H4111 . 124.5 no
C371 . C411 . H4111 . 125.5 no
C36 . C370 . C410 . 129.0(3) yes
C36 . C370 . C380 . 125.5(3) yes
C410 . C370 . C380 . 104.77(9) yes
C36 . C371 . C381 . 125.7(4) yes
C36 . C371 . C411 . 127.8(4) yes
C381 . C371 . C411 . 104.67(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.221(3) yes
C2 . N3 . 1.341(4) yes
C2 . C6 . 1.552(4) yes
N3 . C4 . 1.460(4) yes
N3 . C23 . 1.479(4) yes
C4 . C5 . 1.528(5) yes
C4 . C21 . 1.522(4) yes
C4 . H41 . 0.973 no
C5 . C6 . 1.549(4) yes
C5 . H51 . 0.967 no
C5 . H52 . 0.939 no
C6 . C7 . 1.529(4) yes
C6 . C11 . 1.552(4) yes
C7 . O8 . 1.342(4) yes
C7 . O10 . 1.202(4) yes
O8 . C9 . 1.454(4) yes
C9 . H93 . 0.962 no
C9 . H92 . 0.961 no
C9 . H91 . 0.968 no
C11 . C12 . 1.504(4) yes
C11 . C17 . 1.528(5) yes
C11 . H111 . 0.987 no
C12 . C13 . 1.357(4) yes
C12 . C16 . 1.421(5) yes
C13 . O14 . 1.368(4) yes
C13 . H131 . 0.927 no
O14 . C15 . 1.363(4) yes
C15 . C16 . 1.337(5) yes
C15 . H151 . 0.932 no
C16 . H161 . 0.944 no
C17 . N18 . 1.499(4) yes
C17 . H171 . 0.976 no
C17 . H172 . 0.956 no
N18 . O19 . 1.216(3) yes
N18 . O20 . 1.222(3) yes
C21 . O22 . 1.441(4) yes
C21 . H211 . 0.974 no
C21 . H212 . 0.987 no
O22 . C23 . 1.451(4) yes
C23 . C24 . 1.502(5) yes
C23 . C25 . 1.499(5) yes
C24 . H241 . 0.961 no
C24 . H242 . 0.977 no
C24 . H243 . 0.995 no
C25 . H253 . 0.968 no
C25 . H252 . 0.972 no
C25 . H251 . 0.964 no
O26 . C27 . 1.238(3) yes
C27 . N28 . 1.333(4) yes
C27 . C31 . 1.538(4) yes
N28 . C29 . 1.467(4) yes
N28 . C48 . 1.477(4) yes
C29 . C30 . 1.538(5) yes
C29 . C46 . 1.508(5) yes
C29 . H291 . 0.990 no
C30 . C31 . 1.553(4) yes
C30 . H301 . 0.971 no
C30 . H302 . 0.961 no
C31 . C32 . 1.532(5) yes
C31 . C36 . 1.557(4) yes
C32 . O33 . 1.194(4) yes
C32 . O34 . 1.330(4) yes
O34 . C35 . 1.455(4) yes
C35 . H353 . 0.967 no
C35 . H352 . 0.959 no
C35 . H351 . 0.954 no
C36 . C42 . 1.517(5) yes
C36 . H361 . 0.976 no
C36 . C371 . 1.486(4) yes
C36 . C42 . 1.517(5) yes
C36 . H361 . 0.976 no
C36 . C370 . 1.527(4) yes
C42 . N43 . 1.505(5) yes
C42 . H421 . 0.968 no
C42 . H422 . 0.979 no
N43 . O44 . 1.205(4) yes
N43 . O45 . 1.199(4) yes
C46 . O47 . 1.440(4) yes
C46 . H461 . 0.973 no
C46 . H462 . 0.972 no
O47 . C48 . 1.435(4) yes
C48 . C49 . 1.509(5) yes
C48 . C50 . 1.517(5) yes
C49 . H491 . 0.965 no
C49 . H492 . 0.964 no
C49 . H493 . 0.979 no
C50 . H503 . 0.966 no
C50 . H502 . 0.951 no
C50 . H501 . 0.969 no
C380 . O390 . 1.368(5) yes
C380 . C370 . 1.348(5) yes
C380 . H3801 . 0.959 no
C381 . C391 . 1.343(7) yes
C381 . C371 . 1.429(7) yes
C381 . H3811 . 0.950 no
O390 . C400 . 1.358(6) yes
C391 . O401 . 1.360(7) yes
C391 . H3911 . 0.931 no
C400 . C410 . 1.344(5) yes
C400 . H4001 . 0.942 no
O401 . C411 . 1.363(6) yes
C410 . C370 . 1.437(6) yes
C410 . H4101 . 0.923 no
C411 . C371 . 1.349(7) yes
C411 . H4111 . 0.929 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H131 . O26 2_656 160 0.93 2.39 3.281(6) yes
C15 . H151 . O20 2_546 136 0.93 2.59 3.330(6) yes
C17 . H172 . O26 2_656 168 0.96 2.47 3.410(6) yes
C21 . H212 . O45 2_656 166 0.99 2.47 3.433(6) yes
C30 . H302 . O1 2_645 169 0.96 2.57 3.520(6) yes
C42 . H421 . O1 2_645 177 0.97 2.40 3.372(6) yes
C46 . H461 . O19 2_645 174 0.97 2.45 3.417(6) yes
C50 . H501 . O26 . 120 0.97 2.51 3.112(6) yes
C410 . H4101 . O1 2_645 157 0.92 2.42 3.289(6) yes
C411 . H4101 . O1 2_645 141.1(11) 1.076(12) 2.421(6) 3.328(6) yes
C410 . H4111 . O1 2_645 152.1(16) 0.941(14) 2.427(8) 3.289(6) yes
C411 . H4111 . O1 2_645 163 0.93 2.43 3.328(6) yes
