#------------------------------------------------------------------------------
#$Date: 2024-05-05 05:15:24 +0300 (Sun, 05 May 2024) $
#$Revision: 291594 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248347.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_7248347
loop_
_publ_author_name
'Bracken, Matthew L.'
'Fernandes, Manuel A.'
'Mathura, Sadhna'
_publ_section_title
;
 Bilirubin and its crystal forms
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2136
_journal_page_last               2142
_journal_paper_doi               10.1039/D4CE00123K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '1(C33 H36 N4 O6), 0.25[]'
_chemical_formula_sum            'C33 H36 N4 O6'
_chemical_formula_weight         584.66
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-06 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                98.973(3)
_cell_angle_beta                 104.421(3)
_cell_angle_gamma                111.029(3)
_cell_formula_units_Z            4
_cell_length_a                   11.8077(10)
_cell_length_b                   15.0220(12)
_cell_length_c                   19.3471(17)
_cell_measurement_reflns_used    7142
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      18.42
_cell_measurement_theta_min      2.26
_cell_volume                     2985.8(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2197
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            161376
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.621
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1055 before and 0.0770 after correction.
The Ratio of minimum to maximum transmission is 0.8279.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       Block
_exptl_crystal_F_000             1240
_exptl_crystal_recrystallization_method
'Vapour diffusion of diethyl ether into pyridine'
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     808
_refine_ls_number_reflns         10506
_refine_ls_number_restraints     213
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1867
_refine_ls_R_factor_gt           0.0948
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1243P)²+3.8292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4945
_reflns_number_total             10506
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00123k3.cif
_cod_data_source_block           Form2_23mbb_sadnah16_ns16_bilpyether
_cod_depositor_comments
'Adding full bibliography for 7248346--7248347.cif.'
_cod_database_code               7248347
_shelx_shelxl_version_number     2018/3
_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   0.995
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C65-C66 \\sim C64-C66B \\sim C35-C34 \\sim C40-C34B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
C39 \\sim C36 \\sim C37 \\sim C35 \\sim C34: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C38 \\sim C37 \\sim C36 \\sim C40 \\sim C34B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C60 \\sim C61 \\sim C62 \\sim C64 \\sim C66B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C61 \\sim C62 \\sim C63 \\sim C65 \\sim C66: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
C5 \\sim C4 \\sim C3 \\sim C6: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 C39, C36, C37, C35, C34
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C38, C37, C36, C40, C34B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C60, C61, C62, C64, C66B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C61, C62, C63, C65, C66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5, C4, C3, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(H40)=Sof(H64)=Sof(H65A)=Sof(H65B)=Sof(H65C)=
 Sof(C34B)=Sof(H34C)=Sof(H34D)=Sof(C66B)=Sof(H66C)=Sof(H66D)=1-FVAR(1)
 Sof(H35)=Sof(H40A)=Sof(H40B)=Sof(H40C)=Sof(H64A)=Sof(H64B)=Sof(H64C)=Sof(H65)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C66)=Sof(H66A)=Sof(H66B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C22(H22A,H22B), C23(H23A,
 H23B), C47(H47A,H47B), C48(H48A,H48B), C50(H50A,H50B), C55(H55A,H55B),
 C56(H56A,H56B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3A), N4(H4), C2(H2A), C8(H8A), C26(H26), C31(H31), N5(H5),
  N6(H6), N7(H7), N8(H8), C35(H35), C40(H40), C41(H41), C59(H59), C64(H64),
 C65(H65)
6.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B), C32(H32A,H32B), C34(H34A,H34B), C66(H66A,H66B), C34B(H34C,H34D),
 C66B(H66C,H66D)
6.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C33(H33A,H33B,
 H33C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C46(H46A,H46B,H46C), C58(H58A,
 H58B,H58C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6A), O9(H9), O12(H12)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
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
O4 O 0.8657(5) 1.1015(3) 0.2052(3) 0.0852(13) Uani 1 1 d . . . . .
O5 O 0.2585(4) 0.4968(3) 0.1404(2) 0.0694(10) Uani 1 1 d . . . . .
O3 O 0.0795(4) 0.4260(3) 0.0424(2) 0.0768(11) Uani 1 1 d . . . . .
H3 H 0.119542 0.395311 0.027298 0.115 Uiso 1 1 calc R U . . .
O1 O 0.1831(5) 0.3263(3) -0.0229(3) 0.0879(13) Uani 1 1 d . . . . .
O2 O 0.7448(4) 0.9230(3) 0.2948(2) 0.0771(12) Uani 1 1 d . . . . .
O6 O 0.9419(4) 0.9983(4) 0.2891(4) 0.1108(17) Uani 1 1 d . . . . .
H6A H 0.906961 1.028101 0.264065 0.166 Uiso 1 1 calc R U . . .
N1 N 0.6529(5) 1.0072(3) 0.1860(3) 0.0721(14) Uani 1 1 d . . . . .
H1 H 0.665919 0.970594 0.215847 0.087 Uiso 1 1 calc R U . . .
N2 N 0.4761(4) 0.8238(3) 0.2173(3) 0.0640(12) Uani 1 1 d . . . . .
H2 H 0.560153 0.857009 0.231590 0.077 Uiso 1 1 calc R U . . .
N3 N 0.5323(4) 0.5974(4) 0.2002(3) 0.0686(13) Uani 1 1 d . . . . .
H3A H 0.450567 0.567419 0.172777 0.082 Uiso 1 1 calc R U . . .
N4 N 0.3853(5) 0.4233(4) 0.0580(3) 0.0768(14) Uani 1 1 d . . . . .
H4 H 0.364657 0.459659 0.088613 0.092 Uiso 1 1 calc R U . . .
C1 C 0.8701(7) 1.2450(5) 0.1094(4) 0.095(2) Uani 1 1 d . . . . .
H1A H 0.924426 1.232478 0.148285 0.114 Uiso 1 1 calc R U . . .
H1B H 0.906283 1.294070 0.086160 0.114 Uiso 1 1 calc R U . . .
C2 C 0.7507(8) 1.1967(5) 0.0888(4) 0.090(2) Uani 1 1 d . . . . .
H2A H 0.699764 1.211414 0.049815 0.108 Uiso 1 1 calc R U . . .
C3 C 0.6830(7) 1.1189(4) 0.1203(3) 0.0766(17) Uani 1 1 d . U . . .
C4 C 0.5558(7) 1.0726(4) 0.1032(4) 0.0785(17) Uani 1 1 d . U . . .
C5 C 0.5297(6) 0.9968(4) 0.1443(3) 0.0679(15) Uani 1 1 d . U . . .
C6 C 0.7482(7) 1.0799(5) 0.1746(4) 0.0784(17) Uani 1 1 d . U . . .
C7 C 0.4503(7) 1.0913(4) 0.0513(3) 0.0797(18) Uani 1 1 d . . . . .
H7A H 0.446312 1.069807 -0.000131 0.120 Uiso 1 1 calc R U . . .
H7B H 0.470038 1.162152 0.064209 0.120 Uiso 1 1 calc R U . . .
H7C H 0.367266 1.053799 0.056523 0.120 Uiso 1 1 calc R U . . .
C8 C 0.4179(6) 0.9284(4) 0.1392(3) 0.0731(17) Uani 1 1 d . . . . .
H8A H 0.345467 0.934191 0.108920 0.088 Uiso 1 1 calc R U . . .
C9 C 0.3866(6) 0.8471(4) 0.1714(3) 0.0680(15) Uani 1 1 d . . . . .
C10 C 0.2652(5) 0.7788(4) 0.1625(3) 0.0657(15) Uani 1 1 d . . . . .
C11 C 0.2813(5) 0.7103(4) 0.2035(3) 0.0623(14) Uani 1 1 d . . . . .
C12 C 0.4126(5) 0.7411(4) 0.2365(3) 0.0627(14) Uani 1 1 d . . . . .
C13 C 0.1408(6) 0.7762(5) 0.1174(4) 0.0828(19) Uani 1 1 d . . . . .
H13A H 0.151516 0.843695 0.116159 0.124 Uiso 1 1 calc R U . . .
H13B H 0.074687 0.748300 0.139721 0.124 Uiso 1 1 calc R U . . .
H13C H 0.114514 0.735040 0.066803 0.124 Uiso 1 1 calc R U . . .
C14 C 0.1745(5) 0.6258(4) 0.2123(3) 0.0678(15) Uani 1 1 d . . . . .
H14A H 0.121364 0.652607 0.233467 0.081 Uiso 1 1 calc R U . . .
H14B H 0.212647 0.595930 0.248405 0.081 Uiso 1 1 calc R U . . .
C15 C 0.0863(5) 0.5440(4) 0.1405(3) 0.0707(16) Uani 1 1 d . . . . .
H15A H 0.012751 0.496914 0.150652 0.085 Uiso 1 1 calc R U . . .
H15B H 0.051524 0.574188 0.103325 0.085 Uiso 1 1 calc R U . . .
C16 C 0.1513(6) 0.4876(4) 0.1081(3) 0.0624(14) Uani 1 1 d . . . . .
C17 C 0.4884(5) 0.7038(4) 0.2902(3) 0.0638(15) Uani 1 1 d . . . . .
H17A H 0.537609 0.756771 0.337344 0.077 Uiso 1 1 calc R U . . .
H17B H 0.427532 0.646810 0.300952 0.077 Uiso 1 1 calc R U . . .
C18 C 0.5803(5) 0.6721(5) 0.2628(4) 0.0705(17) Uani 1 1 d . . . . .
C19 C 0.7129(5) 0.7029(5) 0.2900(4) 0.0740(18) Uani 1 1 d . . . . .
C20 C 0.7424(6) 0.6409(5) 0.2410(4) 0.0809(19) Uani 1 1 d . . . . .
C21 C 0.6294(6) 0.5739(5) 0.1843(4) 0.0791(19) Uani 1 1 d . . . . .
C22 C 0.8030(6) 0.7824(5) 0.3599(4) 0.093(2) Uani 1 1 d . . . . .
H22A H 0.845846 0.752272 0.393668 0.111 Uiso 1 1 calc R U . . .
H22B H 0.751418 0.806756 0.384481 0.111 Uiso 1 1 calc R U . . .
C23 C 0.9076(6) 0.8722(6) 0.3504(5) 0.101(2) Uani 1 1 d . . . . .
H23A H 0.968160 0.914718 0.400002 0.121 Uiso 1 1 calc R U . . .
H23B H 0.956590 0.848208 0.323323 0.121 Uiso 1 1 calc R U . . .
C24 C 0.8553(7) 0.9332(5) 0.3095(4) 0.0835(19) Uani 1 1 d . . . . .
C25 C 0.8761(6) 0.6470(6) 0.2481(5) 0.097(2) Uani 1 1 d . . . . .
H25A H 0.908512 0.682164 0.213701 0.145 Uiso 1 1 calc R U . . .
H25B H 0.872435 0.579985 0.236285 0.145 Uiso 1 1 calc R U . . .
H25C H 0.933765 0.682894 0.299027 0.145 Uiso 1 1 calc R U . . .
C26 C 0.6143(7) 0.4998(6) 0.1219(4) 0.080(2) Uani 1 1 d . . . . .
H26 H 0.692609 0.496984 0.119896 0.097 Uiso 1 1 calc R U . . .
C27 C 0.5108(7) 0.4342(5) 0.0662(4) 0.0762(18) Uani 1 1 d . . . . .
C28 C 0.4983(8) 0.3596(5) 0.0035(4) 0.082(2) Uani 1 1 d . . . . .
C29 C 0.3736(8) 0.3084(6) -0.0376(4) 0.086(2) Uani 1 1 d . . . . .
C30 C 0.2991(8) 0.3495(5) -0.0029(4) 0.0775(18) Uani 1 1 d . . . . .
C31 C 0.6023(10) 0.3431(7) -0.0166(6) 0.117(3) Uani 1 1 d . . . . .
H31 H 0.572012 0.281716 -0.052607 0.140 Uiso 1 1 calc R U . . .
C32 C 0.7123(11) 0.3869(8) 0.0010(7) 0.149(4) Uani 1 1 d . . . . .
H32A H 0.753553 0.449577 0.036824 0.178 Uiso 1 1 calc R U . . .
H32B H 0.761503 0.360401 -0.020373 0.178 Uiso 1 1 calc R U . . .
C33 C 0.3088(9) 0.2237(6) -0.1074(4) 0.114(3) Uani 1 1 d . . . . .
H33A H 0.349694 0.241459 -0.144502 0.171 Uiso 1 1 calc R U . . .
H33B H 0.217566 0.209988 -0.126834 0.171 Uiso 1 1 calc R U . . .
H33C H 0.317231 0.164518 -0.096038 0.171 Uiso 1 1 calc R U . . .
O10 O 0.2944(4) 0.5323(3) 0.3745(2) 0.0721(11) Uani 1 1 d . . . . .
O11 O 0.8003(4) 0.2157(3) 0.3292(2) 0.0715(11) Uani 1 1 d . . . . .
O9 O 0.9749(4) 0.2375(3) 0.4191(2) 0.0750(11) Uani 1 1 d . . . . .
H9 H 0.927353 0.181168 0.420523 0.113 Uiso 1 1 calc R U . . .
O7 O 0.8479(4) 0.0806(3) 0.4548(2) 0.0873(13) Uani 1 1 d . . . . .
O8 O 0.3864(4) 0.4025(3) 0.2493(2) 0.0672(10) Uani 1 1 d . . . . .
O12 O 0.1924(4) 0.3806(3) 0.2567(2) 0.0716(11) Uani 1 1 d . . . . .
H12 H 0.235563 0.431407 0.292694 0.107 Uiso 1 1 calc R U . . .
N5 N 0.4972(4) 0.5382(3) 0.3917(3) 0.0644(12) Uani 1 1 d . . . . .
H5 H 0.479149 0.496897 0.348801 0.077 Uiso 1 1 calc R U . . .
N6 N 0.6487(4) 0.4402(3) 0.3274(2) 0.0579(11) Uani 1 1 d . . . . .
H6 H 0.566476 0.427260 0.316675 0.070 Uiso 1 1 calc R U . . .
N7 N 0.5363(4) 0.1738(3) 0.2815(2) 0.0584(11) Uani 1 1 d . . . . .
H7 H 0.615845 0.186294 0.306908 0.070 Uiso 1 1 calc R U . . .
N8 N 0.6546(5) 0.0715(3) 0.3843(3) 0.0711(13) Uani 1 1 d . . . . .
H8 H 0.685735 0.119957 0.364634 0.085 Uiso 1 1 calc R U . . .
C35 C 0.7091(7) 0.7064(5) 0.5772(4) 0.0811(18) Uani 1 1 d D U . . .
H35A H 0.680086 0.746871 0.607153 0.122 Uiso 0.543(9) 1 calc R U P A 2
H35B H 0.782936 0.749830 0.566084 0.122 Uiso 0.543(9) 1 calc R U P A 2
H35C H 0.734255 0.663280 0.604736 0.122 Uiso 0.543(9) 1 calc R U P A 2
H35 H 0.795172 0.720877 0.579088 0.097 Uiso 0.457(9) 1 calc R U P A 1
C36 C 0.6026(6) 0.6447(4) 0.5066(3) 0.0672(14) Uani 1 1 d . U . . .
C37 C 0.4780(6) 0.6313(4) 0.4882(3) 0.0672(14) Uani 1 1 d . U . . .
C38 C 0.4101(6) 0.5632(4) 0.4141(4) 0.0662(15) Uani 1 1 d . U . . .
C39 C 0.6194(6) 0.5863(4) 0.4453(3) 0.0640(15) Uani 1 1 d . U . . .
C40 C 0.4162(8) 0.6745(5) 0.5317(4) 0.092(2) Uani 1 1 d D U . . .
H40A H 0.383601 0.631070 0.561714 0.137 Uiso 0.457(9) 1 calc R U P A 1
H40B H 0.344583 0.681670 0.498193 0.137 Uiso 0.457(9) 1 calc R U P A 1
H40C H 0.478880 0.739741 0.564324 0.137 Uiso 0.457(9) 1 calc R U P A 1
H40 H 0.473421 0.716859 0.579068 0.110 Uiso 0.543(9) 1 calc R U P A 2
C41 C 0.7280(5) 0.5790(4) 0.4411(3) 0.0607(14) Uani 1 1 d . . . . .
H41 H 0.804013 0.623019 0.480650 0.073 Uiso 1 1 calc R U . . .
C42 C 0.7462(5) 0.5155(4) 0.3863(3) 0.0599(14) Uani 1 1 d . . . . .
C43 C 0.8606(5) 0.5108(4) 0.3828(3) 0.0591(14) Uani 1 1 d . . . . .
C44 C 0.8290(5) 0.4301(4) 0.3221(3) 0.0594(14) Uani 1 1 d . . . . .
C45 C 0.6971(5) 0.3894(4) 0.2887(3) 0.0555(13) Uani 1 1 d . . . . .
C46 C 0.9932(5) 0.5817(4) 0.4310(3) 0.0713(16) Uani 1 1 d . . . . .
H46A H 0.991572 0.643756 0.454398 0.107 Uiso 1 1 calc R U . . .
H46B H 1.049798 0.594958 0.400893 0.107 Uiso 1 1 calc R U . . .
H46C H 1.025343 0.552942 0.469431 0.107 Uiso 1 1 calc R U . . .
C47 C 0.9221(5) 0.3976(4) 0.2977(3) 0.0661(15) Uani 1 1 d . . . . .
H47A H 0.985472 0.454483 0.288350 0.079 Uiso 1 1 calc R U . . .
H47B H 0.874535 0.345333 0.250082 0.079 Uiso 1 1 calc R U . . .
C48 C 0.9955(5) 0.3575(4) 0.3527(3) 0.0656(15) Uani 1 1 d . . . . .
H48A H 1.061391 0.345890 0.334250 0.079 Uiso 1 1 calc R U . . .
H48B H 1.040865 0.408718 0.400921 0.079 Uiso 1 1 calc R U . . .
C49 C 0.9122(6) 0.2634(4) 0.3650(3) 0.0619(14) Uani 1 1 d . . . . .
C50 C 0.6063(5) 0.3071(4) 0.2202(3) 0.0569(13) Uani 1 1 d . . . . .
H50A H 0.656514 0.278393 0.197704 0.068 Uiso 1 1 calc R U . . .
H50B H 0.565297 0.335377 0.183921 0.068 Uiso 1 1 calc R U . . .
C51 C 0.5021(5) 0.2248(4) 0.2341(3) 0.0576(13) Uani 1 1 d . . . . .
C52 C 0.3700(5) 0.1855(4) 0.2053(3) 0.0632(15) Uani 1 1 d . . . . .
C53 C 0.3234(5) 0.1067(4) 0.2370(4) 0.0681(16) Uani 1 1 d . . . . .
C54 C 0.4269(5) 0.0990(4) 0.2842(3) 0.0621(14) Uani 1 1 d . . . . .
C55 C 0.2914(6) 0.2158(5) 0.1476(3) 0.0737(17) Uani 1 1 d . . . . .
H55A H 0.238397 0.157195 0.104344 0.088 Uiso 1 1 calc R U . . .
H55B H 0.351198 0.265935 0.130764 0.088 Uiso 1 1 calc R U . . .
C56 C 0.2031(5) 0.2578(4) 0.1705(3) 0.0719(16) Uani 1 1 d . . . . .
H56A H 0.150168 0.267238 0.126188 0.086 Uiso 1 1 calc R U . . .
H56B H 0.144080 0.208547 0.188244 0.086 Uiso 1 1 calc R U . . .
C57 C 0.2705(6) 0.3539(4) 0.2295(3) 0.0623(14) Uani 1 1 d . . . . .
C58 C 0.1842(6) 0.0400(5) 0.2232(4) 0.095(2) Uani 1 1 d . . . . .
H58A H 0.148918 0.073664 0.253731 0.142 Uiso 1 1 calc R U . . .
H58B H 0.178791 -0.021647 0.236060 0.142 Uiso 1 1 calc R U . . .
H58C H 0.134721 0.024641 0.170667 0.142 Uiso 1 1 calc R U . . .
C59 C 0.4262(6) 0.0297(4) 0.3260(3) 0.0674(16) Uani 1 1 d . . . . .
H59 H 0.342981 -0.014316 0.323255 0.081 Uiso 1 1 calc R U . . .
C60 C 0.5225(6) 0.0155(4) 0.3687(3) 0.0657(15) Uani 1 1 d . U . . .
C61 C 0.5190(7) -0.0548(4) 0.4138(3) 0.0737(16) Uani 1 1 d . U . . .
C62 C 0.6406(7) -0.0384(4) 0.4529(4) 0.0795(17) Uani 1 1 d . U . . .
C63 C 0.7287(7) 0.0423(4) 0.4331(4) 0.0749(17) Uani 1 1 d . U . . .
C64 C 0.3998(8) -0.1315(5) 0.4170(4) 0.096(2) Uani 1 1 d D U . . .
H64A H 0.332373 -0.106940 0.410314 0.145 Uiso 0.457(9) 1 calc R U P A 1
H64B H 0.417245 -0.145901 0.465253 0.145 Uiso 0.457(9) 1 calc R U P A 1
H64C H 0.371202 -0.192071 0.377505 0.145 Uiso 0.457(9) 1 calc R U P A 1
H64 H 0.412698 -0.150359 0.461963 0.116 Uiso 0.543(9) 1 calc R U P A 2
C65 C 0.6860(9) -0.0888(5) 0.5065(5) 0.102(2) Uani 1 1 d D U . . .
H65A H 0.740297 -0.117080 0.489242 0.154 Uiso 0.543(9) 1 calc R U P A 2
H65B H 0.611899 -0.141820 0.510543 0.154 Uiso 0.543(9) 1 calc R U P A 2
H65C H 0.735954 -0.040740 0.555121 0.154 Uiso 0.543(9) 1 calc R U P A 2
H65 H 0.624295 -0.135649 0.521055 0.123 Uiso 0.457(9) 1 calc R U P A 1
C34 C 0.6901(15) 0.7377(10) 0.6303(6) 0.076(4) Uani 0.457(9) 1 d D U P A 1
H34A H 0.604614 0.723977 0.629279 0.091 Uiso 0.457(9) 1 calc R U P A 1
H34B H 0.760263 0.776888 0.674391 0.091 Uiso 0.457(9) 1 calc R U P A 1
C66 C 0.7939(12) -0.0737(12) 0.5317(10) 0.134(8) Uani 0.457(9) 1 d D U P A 1
H66A H 0.857433 -0.027162 0.517970 0.161 Uiso 0.457(9) 1 calc R U P A 1
H66B H 0.818153 -0.107938 0.565875 0.161 Uiso 0.457(9) 1 calc R U P A 1
C34B C 0.3120(10) 0.6680(9) 0.5205(7) 0.082(4) Uani 0.543(9) 1 d D U P A 2
H34C H 0.247141 0.627364 0.474724 0.098 Uiso 0.543(9) 1 calc R U P A 2
H34D H 0.291533 0.703200 0.557220 0.098 Uiso 0.543(9) 1 calc R U P A 2
C66B C 0.2946(11) -0.1734(10) 0.3770(7) 0.103(5) Uani 0.543(9) 1 d D U P A 2
H66C H 0.270669 -0.160389 0.330275 0.124 Uiso 0.543(9) 1 calc R U P A 2
H66D H 0.232365 -0.220793 0.390938 0.124 Uiso 0.543(9) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5.00 -5.00 -1.00 0.0670
-4.00 -1.00 -1.00 0.0680
-3.00 2.00 -1.00 0.0690
-2.00 -1.00 3.00 0.0470
-2.00 5.00 0.00 0.0460
-1.00 -2.00 5.00 0.0270
-1.00 -3.00 4.00 0.0340
-1.00 -1.00 5.00 0.0270
0.00 -3.00 5.00 0.0280
0.00 0.00 1.00 0.0450
0.00 3.00 -5.00 0.0130
0.00 1.00 -3.00 0.0130
1.00 -5.00 -3.00 0.0740
1.00 -3.00 -1.00 0.0830
1.00 -5.00 1.00 0.0730
1.00 1.00 -4.00 0.0190
1.00 -2.00 5.00 0.0440
1.00 3.00 -5.00 0.0090
2.00 0.00 -5.00 0.0460
3.00 3.00 -5.00 0.0360
4.00 -3.00 1.00 0.0710
4.00 1.00 4.00 0.0550
4.00 3.00 5.00 0.0530
5.00 0.00 4.00 0.0600
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
C16 O3 H3 109.5 . . ?
C24 O6 H6A 109.5 . . ?
C5 N1 H1 124.0 . . ?
C6 N1 H1 124.0 . . ?
C6 N1 C5 112.0(6) . . ?
C9 N2 H2 125.6 . . ?
C12 N2 H2 125.6 . . ?
C12 N2 C9 108.8(5) . . ?
C18 N3 H3A 124.3 . . ?
C18 N3 C21 111.4(5) . . ?
C21 N3 H3A 124.3 . . ?
C27 N4 H4 124.2 . . ?
C30 N4 H4 124.2 . . ?
C30 N4 C27 111.5(6) . . ?
H1A C1 H1B 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 H2A 117.4 . . ?
C1 C2 C3 125.2(8) . . ?
C3 C2 H2A 117.4 . . ?
C4 C3 C2 125.8(7) . . ?
C4 C3 C6 110.3(6) . . ?
C6 C3 C2 123.9(7) . . ?
C3 C4 C5 107.8(6) . . ?
C3 C4 C7 128.5(6) . . ?
C5 C4 C7 123.7(6) . . ?
N1 C5 C4 104.6(5) . . ?
C8 C5 N1 126.7(6) . . ?
C8 C5 C4 128.4(6) . . ?
O4 C6 N1 123.2(7) . . ?
O4 C6 C3 131.5(6) . . ?
N1 C6 C3 105.3(6) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 114.4 . . ?
C5 C8 C9 131.3(6) . . ?
C9 C8 H8A 114.4 . . ?
N2 C9 C8 124.6(6) . . ?
C10 C9 N2 108.5(5) . . ?
C10 C9 C8 126.9(6) . . ?
C9 C10 C11 107.0(5) . . ?
C9 C10 C13 126.3(6) . . ?
C11 C10 C13 126.6(5) . . ?
C10 C11 C14 125.5(5) . . ?
C12 C11 C10 106.8(5) . . ?
C12 C11 C14 127.6(5) . . ?
N2 C12 C11 108.9(5) . . ?
N2 C12 C17 119.3(5) . . ?
C11 C12 C17 131.7(5) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 108.5 . . ?
C11 C14 H14B 108.5 . . ?
C11 C14 C15 115.0(5) . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.0(5) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
O5 C16 O3 123.8(6) . . ?
O5 C16 C15 122.9(6) . . ?
O3 C16 C15 113.3(5) . . ?
C12 C17 H17A 108.7 . . ?
C12 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C12 114.1(5) . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
N3 C18 C17 118.6(5) . . ?
N3 C18 C19 108.4(6) . . ?
C19 C18 C17 133.1(7) . . ?
C18 C19 C20 106.2(6) . . ?
C18 C19 C22 125.7(7) . . ?
C20 C19 C22 128.0(6) . . ?
C19 C20 C25 125.4(7) . . ?
C21 C20 C19 109.6(6) . . ?
C21 C20 C25 125.1(7) . . ?
N3 C21 C26 126.8(6) . . ?
C20 C21 N3 104.5(7) . . ?
C20 C21 C26 128.7(6) . . ?
C19 C22 H22A 108.3 . . ?
C19 C22 H22B 108.3 . . ?
C19 C22 C23 116.0(6) . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
C22 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.5(6) . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
O2 C24 O6 123.2(6) . . ?
O2 C24 C23 123.8(6) . . ?
O6 C24 C23 113.0(6) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 C26 H26 114.1 . . ?
C27 C26 C21 131.9(6) . . ?
C27 C26 H26 114.1 . . ?
N4 C27 C28 104.9(6) . . ?
C26 C27 N4 124.4(7) . . ?
C26 C27 C28 130.7(7) . . ?
C27 C28 C31 127.2(8) . . ?
C29 C28 C27 109.5(6) . . ?
C29 C28 C31 123.2(8) . . ?
C28 C29 C30 107.7(7) . . ?
C28 C29 C33 130.9(7) . . ?
C30 C29 C33 121.4(8) . . ?
O1 C30 N4 124.2(6) . . ?
O1 C30 C29 129.4(7) . . ?
N4 C30 C29 106.4(7) . . ?
C28 C31 H31 112.4 . . ?
C32 C31 C28 135.2(12) . . ?
C32 C31 H31 112.4 . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C49 O9 H9 109.5 . . ?
C57 O12 H12 109.5 . . ?
C38 N5 H5 124.3 . . ?
C38 N5 C39 111.4(5) . . ?
C39 N5 H5 124.3 . . ?
C42 N6 H6 124.7 . . ?
C45 N6 H6 124.7 . . ?
C45 N6 C42 110.5(5) . . ?
C51 N7 H7 124.9 . . ?
C51 N7 C54 110.1(5) . . ?
C54 N7 H7 124.9 . . ?
C60 N8 H8 123.8 . . ?
C63 N8 H8 123.8 . . ?
C63 N8 C60 112.4(5) . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C36 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C36 C35 H35C 109.5 . . ?
C36 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
C34 C35 C36 122.1(10) . . ?
C37 C36 C35 127.7(6) . . ?
C37 C36 C39 109.0(6) . . ?
C39 C36 C35 123.3(6) . . ?
C36 C37 C38 107.7(5) . . ?
C36 C37 C40 128.8(6) . . ?
C38 C37 C40 123.5(6) . . ?
O10 C38 N5 123.4(6) . . ?
O10 C38 C37 129.6(6) . . ?
N5 C38 C37 107.0(6) . . ?
N5 C39 C36 104.9(5) . . ?
C41 C39 N5 127.1(5) . . ?
C41 C39 C36 127.9(6) . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
C37 C40 H40 113.2 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C34B C40 C37 133.5(10) . . ?
C34B C40 H40 113.2 . . ?
C39 C41 H41 115.1 . . ?
C39 C41 C42 129.8(6) . . ?
C42 C41 H41 115.1 . . ?
N6 C42 C41 125.1(5) . . ?
N6 C42 C43 106.2(5) . . ?
C43 C42 C41 128.5(5) . . ?
C42 C43 C44 107.8(5) . . ?
C42 C43 C46 126.3(5) . . ?
C44 C43 C46 125.8(5) . . ?
C43 C44 C47 126.1(5) . . ?
C45 C44 C43 107.0(5) . . ?
C45 C44 C47 126.9(5) . . ?
N6 C45 C44 108.4(5) . . ?
N6 C45 C50 118.5(5) . . ?
C44 C45 C50 133.0(5) . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C44 C47 H47A 108.5 . . ?
C44 C47 H47B 108.5 . . ?
C44 C47 C48 115.3(5) . . ?
H47A C47 H47B 107.5 . . ?
C48 C47 H47A 108.5 . . ?
C48 C47 H47B 108.5 . . ?
C47 C48 H48A 108.7 . . ?
C47 C48 H48B 108.7 . . ?
H48A C48 H48B 107.6 . . ?
C49 C48 C47 114.3(5) . . ?
C49 C48 H48A 108.7 . . ?
C49 C48 H48B 108.7 . . ?
O11 C49 O9 123.3(5) . . ?
O11 C49 C48 123.9(6) . . ?
O9 C49 C48 112.8(5) . . ?
C45 C50 H50A 108.7 . . ?
C45 C50 H50B 108.7 . . ?
C45 C50 C51 114.2(4) . . ?
H50A C50 H50B 107.6 . . ?
C51 C50 H50A 108.7 . . ?
C51 C50 H50B 108.7 . . ?
N7 C51 C50 119.1(5) . . ?
N7 C51 C52 108.7(5) . . ?
C52 C51 C50 132.2(5) . . ?
C51 C52 C53 106.5(5) . . ?
C51 C52 C55 126.5(5) . . ?
C53 C52 C55 126.9(5) . . ?
C52 C53 C58 127.0(6) . . ?
C54 C53 C52 109.0(5) . . ?
C54 C53 C58 124.0(6) . . ?
N7 C54 C59 125.6(5) . . ?
C53 C54 N7 105.7(5) . . ?
C53 C54 C59 128.7(5) . . ?
C52 C55 H55A 108.1 . . ?
C52 C55 H55B 108.1 . . ?
C52 C55 C56 116.9(5) . . ?
H55A C55 H55B 107.3 . . ?
C56 C55 H55A 108.1 . . ?
C56 C55 H55B 108.1 . . ?
C55 C56 H56A 108.6 . . ?
C55 C56 H56B 108.6 . . ?
H56A C56 H56B 107.6 . . ?
C57 C56 C55 114.7(5) . . ?
C57 C56 H56A 108.6 . . ?
C57 C56 H56B 108.6 . . ?
O8 C57 O12 124.1(5) . . ?
O8 C57 C56 122.6(5) . . ?
O12 C57 C56 113.4(5) . . ?
C53 C58 H58A 109.5 . . ?
C53 C58 H58B 109.5 . . ?
C53 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C54 C59 H59 114.5 . . ?
C60 C59 C54 131.1(5) . . ?
C60 C59 H59 114.5 . . ?
N8 C60 C61 103.7(5) . . ?
C59 C60 N8 126.4(5) . . ?
C59 C60 C61 129.8(6) . . ?
C60 C61 C64 125.0(7) . . ?
C62 C61 C60 109.8(5) . . ?
C62 C61 C64 125.3(6) . . ?
C61 C62 C63 107.6(6) . . ?
C61 C62 C65 129.8(6) . . ?
C63 C62 C65 122.6(7) . . ?
O7 C63 N8 123.9(6) . . ?
O7 C63 C62 129.6(6) . . ?
N8 C63 C62 106.6(6) . . ?
C61 C64 H64A 109.5 . . ?
C61 C64 H64B 109.5 . . ?
C61 C64 H64C 109.5 . . ?
C61 C64 H64 112.7 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C66B C64 C61 134.5(10) . . ?
C66B C64 H64 112.7 . . ?
C62 C65 H65A 109.5 . . ?
C62 C65 H65B 109.5 . . ?
C62 C65 H65C 109.5 . . ?
C62 C65 H65 118.4 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C66 C65 C62 123.2(11) . . ?
C66 C65 H65 118.4 . . ?
C35 C34 H34A 120.0 . . ?
C35 C34 H34B 120.0 . . ?
H34A C34 H34B 120.0 . . ?
C65 C66 H66A 120.0 . . ?
C65 C66 H66B 120.0 . . ?
H66A C66 H66B 120.0 . . ?
C40 C34B H34C 120.0 . . ?
C40 C34B H34D 120.0 . . ?
H34C C34B H34D 120.0 . . ?
C64 C66B H66C 120.0 . . ?
C64 C66B H66D 120.0 . . ?
H66C C66B H66D 120.0 . . ?
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
O4 C6 1.260(8) . ?
O5 C16 1.211(6) . ?
O3 H3 0.8400 . ?
O3 C16 1.313(7) . ?
O1 C30 1.224(8) . ?
O2 C24 1.211(7) . ?
O6 H6A 0.8400 . ?
O6 C24 1.328(7) . ?
N1 H1 0.8800 . ?
N1 C5 1.416(7) . ?
N1 C6 1.350(8) . ?
N2 H2 0.8800 . ?
N2 C9 1.386(7) . ?
N2 C12 1.364(7) . ?
N3 H3A 0.8800 . ?
N3 C18 1.352(8) . ?
N3 C21 1.402(8) . ?
N4 H4 0.8800 . ?
N4 C27 1.396(8) . ?
N4 C30 1.356(8) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C1 C2 1.252(9) . ?
C2 H2A 0.9500 . ?
C2 C3 1.473(9) . ?
C3 C4 1.335(9) . ?
C3 C6 1.467(9) . ?
C4 C5 1.475(9) . ?
C4 C7 1.535(9) . ?
C5 C8 1.319(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9500 . ?
C8 C9 1.430(8) . ?
C9 C10 1.379(8) . ?
C10 C11 1.430(8) . ?
C10 C13 1.493(8) . ?
C11 C12 1.388(7) . ?
C11 C14 1.501(7) . ?
C12 C17 1.508(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.534(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.497(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.504(8) . ?
C18 C19 1.391(8) . ?
C19 C20 1.417(9) . ?
C19 C22 1.502(10) . ?
C20 C21 1.399(10) . ?
C20 C25 1.518(8) . ?
C21 C26 1.437(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.540(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.495(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26 0.9500 . ?
C26 C27 1.332(9) . ?
C27 C28 1.455(10) . ?
C28 C29 1.344(10) . ?
C28 C31 1.465(10) . ?
C29 C30 1.469(9) . ?
C29 C33 1.509(11) . ?
C31 H31 0.9500 . ?
C31 C32 1.154(11) . ?
C32 H32A 0.9500 . ?
C32 H32B 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
O10 C38 1.258(7) . ?
O11 C49 1.204(6) . ?
O9 H9 0.8400 . ?
O9 C49 1.320(7) . ?
O7 C63 1.240(7) . ?
O8 C57 1.220(6) . ?
O12 H12 0.8400 . ?
O12 C57 1.315(7) . ?
N5 H5 0.8800 . ?
N5 C38 1.356(7) . ?
N5 C39 1.397(7) . ?
N6 H6 0.8800 . ?
N6 C42 1.384(7) . ?
N6 C45 1.348(6) . ?
N7 H7 0.8800 . ?
N7 C51 1.360(7) . ?
N7 C54 1.394(6) . ?
N8 H8 0.8800 . ?
N8 C60 1.406(7) . ?
N8 C63 1.357(8) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 H35 0.9500 . ?
C35 C36 1.489(9) . ?
C35 C34 1.168(8) . ?
C36 C37 1.355(8) . ?
C36 C39 1.461(8) . ?
C37 C38 1.458(9) . ?
C37 C40 1.462(9) . ?
C39 C41 1.346(8) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C40 H40 0.9500 . ?
C40 C34B 1.159(8) . ?
C41 H41 0.9500 . ?
C41 C42 1.423(8) . ?
C42 C43 1.396(8) . ?
C43 C44 1.414(8) . ?
C43 C46 1.490(7) . ?
C44 C45 1.382(7) . ?
C44 C47 1.498(8) . ?
C45 C50 1.505(7) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.536(8) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.499(7) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.512(7) . ?
C51 C52 1.377(7) . ?
C52 C53 1.418(8) . ?
C52 C55 1.504(8) . ?
C53 C54 1.385(8) . ?
C53 C58 1.514(8) . ?
C54 C59 1.413(8) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C55 C56 1.515(8) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C56 C57 1.494(8) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59 0.9500 . ?
C59 C60 1.335(8) . ?
C60 C61 1.468(8) . ?
C61 C62 1.356(9) . ?
C61 C64 1.487(9) . ?
C62 C63 1.462(9) . ?
C62 C65 1.481(9) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C64 H64 0.9500 . ?
C64 C66B 1.160(8) . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C65 H65 0.9500 . ?
C65 C66 1.166(8) . ?
C34 H34A 0.9500 . ?
C34 H34B 0.9500 . ?
C66 H66A 0.9500 . ?
C66 H66B 0.9500 . ?
C34B H34C 0.9500 . ?
C34B H34D 0.9500 . ?
C66B H66C 0.9500 . ?
C66B H66D 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.84 1.79 2.614(6) 168.4 . yes
O6 H6A O4 0.84 1.80 2.629(7) 166.7 . yes
N1 H1 O2 0.88 1.96 2.809(7) 162.9 . yes
N2 H2 O2 0.88 1.99 2.842(6) 161.4 . yes
N3 H3A O5 0.88 2.00 2.857(6) 162.6 . yes
N4 H4 O5 0.88 1.96 2.797(6) 158.6 . yes
O9 H9 O7 0.84 1.79 2.601(6) 161.5 . yes
O12 H12 O10 0.84 1.80 2.623(6) 166.9 . yes
N5 H5 O8 0.88 1.97 2.827(6) 162.7 . yes
N6 H6 O8 0.88 2.06 2.888(6) 155.5 . yes
N7 H7 O11 0.88 1.98 2.819(6) 159.8 . yes
N8 H8 O11 0.88 1.93 2.784(6) 161.7 . yes
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
N1 C5 C8 C9 -0.8(11) . . . . ?
N2 C9 C10 C11 -1.0(7) . . . . ?
N2 C9 C10 C13 -180.0(6) . . . . ?
N2 C12 C17 C18 -62.8(7) . . . . ?
N3 C18 C19 C20 -1.3(6) . . . . ?
N3 C18 C19 C22 -178.2(5) . . . . ?
N3 C21 C26 C27 -2.5(11) . . . . ?
N4 C27 C28 C29 -0.5(7) . . . . ?
N4 C27 C28 C31 176.3(6) . . . . ?
C1 C2 C3 C4 174.2(7) . . . . ?
C1 C2 C3 C6 -7.3(11) . . . . ?
C2 C3 C4 C5 176.8(6) . . . . ?
C2 C3 C4 C7 -3.5(11) . . . . ?
C2 C3 C6 O4 0.8(11) . . . . ?
C2 C3 C6 N1 -176.8(5) . . . . ?
C3 C4 C5 N1 1.2(6) . . . . ?
C3 C4 C5 C8 -173.6(6) . . . . ?
C4 C3 C6 O4 179.6(6) . . . . ?
C4 C3 C6 N1 1.9(7) . . . . ?
C4 C5 C8 C9 172.8(6) . . . . ?
C5 N1 C6 O4 -179.1(6) . . . . ?
C5 N1 C6 C3 -1.1(6) . . . . ?
C5 C8 C9 N2 -0.2(11) . . . . ?
C5 C8 C9 C10 -179.9(6) . . . . ?
C6 N1 C5 C4 0.1(6) . . . . ?
C6 N1 C5 C8 174.9(6) . . . . ?
C6 C3 C4 C5 -1.9(7) . . . . ?
C6 C3 C4 C7 177.8(6) . . . . ?
C7 C4 C5 N1 -178.5(5) . . . . ?
C7 C4 C5 C8 6.7(10) . . . . ?
C8 C9 C10 C11 178.7(6) . . . . ?
C8 C9 C10 C13 -0.3(10) . . . . ?
C9 N2 C12 C11 -0.3(6) . . . . ?
C9 N2 C12 C17 -176.3(5) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C9 C10 C11 C14 177.2(5) . . . . ?
C10 C11 C12 N2 -0.3(6) . . . . ?
C10 C11 C12 C17 175.0(6) . . . . ?
C10 C11 C14 C15 65.5(8) . . . . ?
C11 C12 C17 C18 122.3(7) . . . . ?
C11 C14 C15 C16 66.2(7) . . . . ?
C12 N2 C9 C8 -178.9(6) . . . . ?
C12 N2 C9 C10 0.8(7) . . . . ?
C12 C11 C14 C15 -118.9(7) . . . . ?
C12 C17 C18 N3 -60.8(7) . . . . ?
C12 C17 C18 C19 120.9(7) . . . . ?
C13 C10 C11 C12 179.8(6) . . . . ?
C13 C10 C11 C14 -3.8(10) . . . . ?
C14 C11 C12 N2 -176.6(5) . . . . ?
C14 C11 C12 C17 -1.3(10) . . . . ?
C14 C15 C16 O5 9.1(8) . . . . ?
C14 C15 C16 O3 -172.3(5) . . . . ?
C17 C18 C19 C20 177.1(6) . . . . ?
C17 C18 C19 C22 0.2(10) . . . . ?
C18 N3 C21 C20 -1.2(6) . . . . ?
C18 N3 C21 C26 -179.0(6) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C18 C19 C20 C25 179.8(5) . . . . ?
C18 C19 C22 C23 -119.2(7) . . . . ?
C19 C20 C21 N3 0.4(6) . . . . ?
C19 C20 C21 C26 178.1(6) . . . . ?
C19 C22 C23 C24 66.5(9) . . . . ?
C20 C19 C22 C23 64.6(9) . . . . ?
C20 C21 C26 C27 -179.8(7) . . . . ?
C21 N3 C18 C17 -177.1(5) . . . . ?
C21 N3 C18 C19 1.6(7) . . . . ?
C21 C26 C27 N4 -1.2(11) . . . . ?
C21 C26 C27 C28 -179.8(6) . . . . ?
C22 C19 C20 C21 177.4(6) . . . . ?
C22 C19 C20 C25 -3.4(10) . . . . ?
C22 C23 C24 O2 10.5(11) . . . . ?
C22 C23 C24 O6 -167.8(7) . . . . ?
C25 C20 C21 N3 -178.9(5) . . . . ?
C25 C20 C21 C26 -1.1(10) . . . . ?
C26 C27 C28 C29 178.4(7) . . . . ?
C26 C27 C28 C31 -4.8(11) . . . . ?
C27 N4 C30 O1 -178.8(6) . . . . ?
C27 N4 C30 C29 0.1(7) . . . . ?
C27 C28 C29 C30 0.6(7) . . . . ?
C27 C28 C29 C33 -179.6(6) . . . . ?
C27 C28 C31 C32 -13.2(17) . . . . ?
C28 C29 C30 O1 178.4(7) . . . . ?
C28 C29 C30 N4 -0.5(7) . . . . ?
C29 C28 C31 C32 163.2(12) . . . . ?
C30 N4 C27 C26 -178.8(6) . . . . ?
C30 N4 C27 C28 0.2(7) . . . . ?
C31 C28 C29 C30 -176.4(6) . . . . ?
C31 C28 C29 C33 3.5(12) . . . . ?
C33 C29 C30 O1 -1.4(11) . . . . ?
C33 C29 C30 N4 179.7(6) . . . . ?
N5 C39 C41 C42 -6.8(10) . . . . ?
N6 C42 C43 C44 -1.5(6) . . . . ?
N6 C42 C43 C46 174.9(5) . . . . ?
N6 C45 C50 C51 -59.7(6) . . . . ?
N7 C51 C52 C53 -0.3(6) . . . . ?
N7 C51 C52 C55 -176.5(5) . . . . ?
N7 C54 C59 C60 -2.9(10) . . . . ?
N8 C60 C61 C62 0.9(7) . . . . ?
N8 C60 C61 C64 -180.0(6) . . . . ?
C35 C36 C37 C38 -178.9(5) . . . . ?
C35 C36 C37 C40 1.0(10) . . . . ?
C35 C36 C39 N5 178.4(5) . . . . ?
C35 C36 C39 C41 -0.9(9) . . . . ?
C36 C37 C38 O10 -177.8(6) . . . . ?
C36 C37 C38 N5 0.5(6) . . . . ?
C36 C37 C40 C34B 179.5(11) . . . . ?
C36 C39 C41 C42 172.4(5) . . . . ?
C37 C36 C39 N5 -0.8(6) . . . . ?
C37 C36 C39 C41 179.9(5) . . . . ?
C38 N5 C39 C36 1.1(6) . . . . ?
C38 N5 C39 C41 -179.6(5) . . . . ?
C38 C37 C40 C34B -0.6(15) . . . . ?
C39 N5 C38 O10 177.4(5) . . . . ?
C39 N5 C38 C37 -1.0(6) . . . . ?
C39 C36 C37 C38 0.2(6) . . . . ?
C39 C36 C37 C40 -179.9(6) . . . . ?
C39 C41 C42 N6 -5.7(9) . . . . ?
C39 C41 C42 C43 178.8(6) . . . . ?
C40 C37 C38 O10 2.3(9) . . . . ?
C40 C37 C38 N5 -179.5(5) . . . . ?
C41 C42 C43 C44 174.7(5) . . . . ?
C41 C42 C43 C46 -8.9(9) . . . . ?
C42 N6 C45 C44 0.4(6) . . . . ?
C42 N6 C45 C50 -177.3(4) . . . . ?
C42 C43 C44 C45 1.8(6) . . . . ?
C42 C43 C44 C47 -179.9(5) . . . . ?
C43 C44 C45 N6 -1.4(6) . . . . ?
C43 C44 C45 C50 176.0(5) . . . . ?
C43 C44 C47 C48 65.8(7) . . . . ?
C44 C45 C50 C51 123.2(6) . . . . ?
C44 C47 C48 C49 65.2(7) . . . . ?
C45 N6 C42 C41 -175.7(5) . . . . ?
C45 N6 C42 C43 0.7(6) . . . . ?
C45 C44 C47 C48 -116.2(6) . . . . ?
C45 C50 C51 N7 -59.5(7) . . . . ?
C45 C50 C51 C52 122.8(6) . . . . ?
C46 C43 C44 C45 -174.6(5) . . . . ?
C46 C43 C44 C47 3.7(9) . . . . ?
C47 C44 C45 N6 -179.7(5) . . . . ?
C47 C44 C45 C50 -2.4(9) . . . . ?
C47 C48 C49 O11 8.4(8) . . . . ?
C47 C48 C49 O9 -172.0(5) . . . . ?
C50 C51 C52 C53 177.6(5) . . . . ?
C50 C51 C52 C55 1.4(10) . . . . ?
C51 N7 C54 C53 -0.8(6) . . . . ?
C51 N7 C54 C59 178.0(5) . . . . ?
C51 C52 C53 C54 -0.2(7) . . . . ?
C51 C52 C53 C58 179.9(6) . . . . ?
C51 C52 C55 C56 -117.9(6) . . . . ?
C52 C53 C54 N7 0.6(6) . . . . ?
C52 C53 C54 C59 -178.2(6) . . . . ?
C52 C55 C56 C57 64.8(7) . . . . ?
C53 C52 C55 C56 66.7(8) . . . . ?
C53 C54 C59 C60 175.7(6) . . . . ?
C54 N7 C51 C50 -177.5(4) . . . . ?
C54 N7 C51 C52 0.7(6) . . . . ?
C54 C59 C60 N8 2.0(11) . . . . ?
C54 C59 C60 C61 177.4(6) . . . . ?
C55 C52 C53 C54 176.0(5) . . . . ?
C55 C52 C53 C58 -3.9(10) . . . . ?
C55 C56 C57 O8 11.2(9) . . . . ?
C55 C56 C57 O12 -169.7(5) . . . . ?
C58 C53 C54 N7 -179.5(5) . . . . ?
C58 C53 C54 C59 1.7(10) . . . . ?
C59 C60 C61 C62 -175.3(6) . . . . ?
C59 C60 C61 C64 3.9(10) . . . . ?
C60 N8 C63 O7 179.8(6) . . . . ?
C60 N8 C63 C62 -0.9(7) . . . . ?
C60 C61 C62 C63 -1.4(7) . . . . ?
C60 C61 C62 C65 178.9(7) . . . . ?
C60 C61 C64 C66B 25.0(17) . . . . ?
C61 C62 C63 O7 -179.3(7) . . . . ?
C61 C62 C63 N8 1.4(7) . . . . ?
C61 C62 C65 C66 172.9(14) . . . . ?
C62 C61 C64 C66B -156.0(13) . . . . ?
C63 N8 C60 C59 176.4(6) . . . . ?
C63 N8 C60 C61 0.0(7) . . . . ?
C63 C62 C65 C66 -6.7(17) . . . . ?
C64 C61 C62 C63 179.4(6) . . . . ?
C64 C61 C62 C65 -0.2(12) . . . . ?
C65 C62 C63 O7 0.4(11) . . . . ?
C65 C62 C63 N8 -178.9(6) . . . . ?
C34 C35 C36 C37 13.4(13) . . . . ?
C34 C35 C36 C39 -165.6(10) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 136.3 41.7 ?
