#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:53:26 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/97/1559765.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_1559765
loop_
_publ_author_name
'Millward, Makenzie J.'
'Ellis, Emily'
'Ward, John W.'
'Clayden, Jonathan'
_publ_section_title
;
 Hydantoin-bridged medium ring scaffolds by migratory insertion of
 urea-tethered nitrile anions into aromatic C-N bonds.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              2091
_journal_page_last               2096
_journal_paper_doi               10.1039/d0sc06188c
_journal_volume                  12
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H19 N3 O'
_chemical_formula_sum            'C15 H19 N3 O'
_chemical_formula_weight         257.33
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   22.0392(6)
_cell_length_b                   22.0392(6)
_cell_length_c                   7.1184(2)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.898
_cell_measurement_theta_min      2.824
_cell_volume                     2994.36(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22901
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         1.848
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0897 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.8678. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM:Et2O'
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.234
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         7518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0444
_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)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0905
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                6127
_reflns_number_total             7518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06188c2.cif
_cod_data_source_block           testh1
_cod_depositor_comments
;Adding full bibliography for 1559758--1559767.cif.

 Adding full bibliography for 1559758--1559767.cif.
;
_cod_original_cell_volume        2994.36(18)
_cod_database_code               1559765
_shelx_shelxl_version_number     2017/1
_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   0.981
_shelx_estimated_absorpt_t_min   0.968
_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
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C31(H31A,H31B), C32(H32A,H32B),
 C33(H33A,H33B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C25(H25), C26(H26), C27(H27),
 C28(H28), C40(H40), C41(H41), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
O1 O 0.24540(14) 0.07713(13) 0.5564(3) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.20341(16) 0.02602(16) 0.2653(4) 0.0167(7) Uani 1 1 d . . . . .
N2 N 0.29261(16) 0.13514(16) 0.2788(4) 0.0153(7) Uani 1 1 d . . . . .
N3 N 0.18668(18) 0.00504(17) -0.0578(4) 0.0224(8) Uani 1 1 d . . . . .
C1 C 0.1347(2) -0.0295(2) 0.3280(5) 0.0242(10) Uani 1 1 d . . . . .
H1A H 0.140043 -0.050055 0.445978 0.029 Uiso 1 1 calc R . . . .
H1B H 0.114619 -0.066960 0.231971 0.029 Uiso 1 1 calc R . . . .
C2 C 0.0843(2) -0.0016(2) 0.3610(6) 0.0302(10) Uani 1 1 d . . . . .
H2A H 0.094336 0.021344 0.485597 0.036 Uiso 1 1 calc R . . . .
H2B H 0.035795 -0.041693 0.363727 0.036 Uiso 1 1 calc R . . . .
C3 C 0.0891(2) 0.0515(2) 0.2098(6) 0.0279(10) Uani 1 1 d . . . . .
H3A H 0.098907 0.037411 0.086464 0.034 Uiso 1 1 calc R . . . .
H3B H 0.043177 0.049111 0.200911 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1465(2) 0.1283(2) 0.2509(5) 0.0230(9) Uani 1 1 d . . . . .
H4A H 0.123643 0.152664 0.308607 0.028 Uiso 1 1 calc R . . . .
H4B H 0.179167 0.127619 0.345110 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1893(2) 0.1714(2) 0.0824(5) 0.0185(8) Uani 1 1 d . . . . .
C6 C 0.24776(19) 0.16996(19) 0.0029(5) 0.0152(8) Uani 1 1 d . . . . .
C7 C 0.27559(19) 0.12309(19) 0.0766(5) 0.0144(8) Uani 1 1 d . . . . .
C8 C 0.2180(2) 0.0461(2) 0.0776(5) 0.0177(8) Uani 1 1 d . . . . .
C9 C 0.24805(19) 0.0805(2) 0.3846(5) 0.0157(8) Uani 1 1 d . . . . .
C10 C 0.1691(2) 0.2165(2) 0.0042(5) 0.0233(9) Uani 1 1 d . . . . .
H10 H 0.130139 0.217925 0.056427 0.028 Uiso 1 1 calc R . . . .
C11 C 0.2040(2) 0.2596(2) -0.1477(5) 0.0243(9) Uani 1 1 d . . . . .
H11 H 0.188421 0.289131 -0.199694 0.029 Uiso 1 1 calc R . . . .
C12 C 0.2613(2) 0.2591(2) -0.2220(5) 0.0243(9) Uani 1 1 d . . . . .
H12 H 0.286308 0.289154 -0.323802 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2823(2) 0.2145(2) -0.1474(5) 0.0191(8) Uani 1 1 d . . . . .
H13 H 0.321701 0.214255 -0.200641 0.023 Uiso 1 1 calc R . . . .
C14 C 0.3390(2) 0.1296(2) -0.0306(5) 0.0189(9) Uani 1 1 d . . . . .
H14A H 0.377574 0.178115 -0.024848 0.028 Uiso 1 1 calc GR . . . .
H14B H 0.326031 0.116056 -0.162038 0.028 Uiso 1 1 calc GR . . . .
H14C H 0.353796 0.098607 0.026616 0.028 Uiso 1 1 calc GR . . . .
C15 C 0.3355(2) 0.2052(2) 0.3557(5) 0.0192(9) Uani 1 1 d . . . . .
H15A H 0.377184 0.231555 0.277076 0.029 Uiso 1 1 calc GR . . . .
H15B H 0.349908 0.201852 0.483764 0.029 Uiso 1 1 calc GR . . . .
H15C H 0.308367 0.229348 0.358048 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.46454(14) 0.36564(13) 0.4810(3) 0.0217(6) Uani 1 1 d . . . . .
N4 N 0.47625(16) 0.32386(15) 0.7695(4) 0.0157(7) Uani 1 1 d . . . . .
N5 N 0.47001(16) 0.42173(16) 0.7594(4) 0.0152(7) Uani 1 1 d . . . . .
N6 N 0.48676(17) 0.30973(17) 1.0926(4) 0.0200(7) Uani 1 1 d . . . . .
C16 C 0.5064(2) 0.2826(2) 0.6988(5) 0.0202(9) Uani 1 1 d . . . . .
H16A H 0.479148 0.255032 0.588659 0.024 Uiso 1 1 calc R . . . .
H16B H 0.503099 0.249323 0.797139 0.024 Uiso 1 1 calc R . . . .
C17 C 0.5832(2) 0.3289(2) 0.6418(5) 0.0214(9) Uani 1 1 d . . . . .
H17A H 0.585069 0.350852 0.518956 0.026 Uiso 1 1 calc R . . . .
H17B H 0.604484 0.298911 0.625079 0.026 Uiso 1 1 calc R . . . .
C18 C 0.6273(2) 0.3869(2) 0.7839(5) 0.0201(9) Uani 1 1 d . . . . .
H18A H 0.676658 0.398016 0.774378 0.024 Uiso 1 1 calc R . . . .
H18B H 0.610708 0.368878 0.912155 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6247(2) 0.45581(19) 0.7562(5) 0.0170(8) Uani 1 1 d . . . . .
H19A H 0.668081 0.490535 0.691403 0.020 Uiso 1 1 calc R . . . .
H19B H 0.584710 0.445791 0.673317 0.020 Uiso 1 1 calc R . . . .
C20 C 0.61750(19) 0.48811(19) 0.9378(5) 0.0142(8) Uani 1 1 d . . . . .
C21 C 0.55424(18) 0.47132(18) 1.0298(5) 0.0136(8) Uani 1 1 d . . . . .
C22 C 0.48207(18) 0.41414(19) 0.9591(5) 0.0146(8) Uani 1 1 d . . . . .
C23 C 0.48166(18) 0.34426(19) 0.9566(5) 0.0151(8) Uani 1 1 d . . . . .
C24 C 0.46957(19) 0.37087(19) 0.6528(5) 0.0160(8) Uani 1 1 d . . . . .
C25 C 0.6804(2) 0.53864(19) 1.0191(5) 0.0178(8) Uani 1 1 d . . . . .
H25 H 0.723218 0.550722 0.957497 0.021 Uiso 1 1 calc R . . . .
C26 C 0.6825(2) 0.57176(19) 1.1867(5) 0.0187(9) Uani 1 1 d . . . . .
H26 H 0.726096 0.606043 1.238245 0.022 Uiso 1 1 calc R . . . .
C27 C 0.6208(2) 0.55445(19) 1.2775(5) 0.0182(9) Uani 1 1 d . . . . .
H27 H 0.621445 0.576213 1.393285 0.022 Uiso 1 1 calc R . . . .
C28 C 0.5580(2) 0.50519(19) 1.1990(5) 0.0167(8) Uani 1 1 d . . . . .
H28 H 0.515652 0.493903 1.262272 0.020 Uiso 1 1 calc R . . . .
C29 C 0.41971(19) 0.4067(2) 1.0733(5) 0.0190(8) Uani 1 1 d . . . . .
H29A H 0.419891 0.451289 1.071826 0.028 Uiso 1 1 calc GR . . . .
H29B H 0.423410 0.394188 1.203141 0.028 Uiso 1 1 calc GR . . . .
H29C H 0.375968 0.369989 1.017780 0.028 Uiso 1 1 calc GR . . . .
C30 C 0.4793(2) 0.48619(19) 0.6803(5) 0.0196(9) Uani 1 1 d . . . . .
H30A H 0.461278 0.507633 0.768040 0.029 Uiso 1 1 calc GR . . . .
H30B H 0.453787 0.476196 0.561187 0.029 Uiso 1 1 calc GR . . . .
H30C H 0.529299 0.518469 0.657901 0.029 Uiso 1 1 calc GR . . . .
O3 O 0.54098(14) 0.64260(14) 0.4905(3) 0.0212(6) Uani 1 1 d . . . . .
N7 N 0.48681(15) 0.61875(16) 0.1996(4) 0.0156(7) Uani 1 1 d . . . . .
N8 N 0.60072(16) 0.69453(15) 0.2171(4) 0.0152(7) Uani 1 1 d . . . . .
N9 N 0.46384(17) 0.61416(17) -0.1223(5) 0.0183(7) Uani 1 1 d . . . . .
C31 C 0.41516(19) 0.5920(2) 0.2681(5) 0.0195(9) Uani 1 1 d . . . . .
H31A H 0.406570 0.560393 0.376142 0.023 Uiso 1 1 calc R . . . .
H31B H 0.381598 0.564358 0.167513 0.023 Uiso 1 1 calc R . . . .
C32 C 0.4026(2) 0.6511(2) 0.3284(5) 0.0222(9) Uani 1 1 d . . . . .
H32A H 0.424980 0.669070 0.452078 0.027 Uiso 1 1 calc R . . . .
H32B H 0.351577 0.632194 0.343735 0.027 Uiso 1 1 calc R . . . .
C33 C 0.4313(2) 0.7124(2) 0.1875(5) 0.0205(9) Uani 1 1 d . . . . .
H33A H 0.403010 0.735696 0.196635 0.025 Uiso 1 1 calc R . . . .
H33B H 0.425731 0.693309 0.058714 0.025 Uiso 1 1 calc R . . . .
C34 C 0.5101(2) 0.7682(2) 0.2193(5) 0.0195(9) Uani 1 1 d . . . . .
H34A H 0.512368 0.808667 0.286110 0.023 Uiso 1 1 calc R . . . .
H34B H 0.531073 0.747625 0.302493 0.023 Uiso 1 1 calc R . . . .
C35 C 0.55474(19) 0.79509(19) 0.0413(5) 0.0185(8) Uani 1 1 d . . . . .
C36 C 0.59120(19) 0.76531(19) -0.0465(5) 0.0167(8) Uani 1 1 d . . . . .
C37 C 0.58395(19) 0.69500(19) 0.0166(5) 0.0151(8) Uani 1 1 d . . . . .
C38 C 0.5062(2) 0.63928(19) 0.0148(5) 0.0160(8) Uani 1 1 d . . . . .
C39 C 0.54403(19) 0.65197(19) 0.3202(5) 0.0160(8) Uani 1 1 d . . . . .
C40 C 0.5606(2) 0.8558(2) -0.0377(6) 0.0250(9) Uani 1 1 d . . . . .
H40 H 0.536426 0.876376 0.020146 0.030 Uiso 1 1 calc R . . . .
C41 C 0.6000(2) 0.8871(2) -0.1957(6) 0.0270(10) Uani 1 1 d . . . . .
H41 H 0.601652 0.927769 -0.246849 0.032 Uiso 1 1 calc R . . . .
C42 C 0.6367(2) 0.8592(2) -0.2784(6) 0.0282(10) Uani 1 1 d . . . . .
H42 H 0.664815 0.880910 -0.386027 0.034 Uiso 1 1 calc R . . . .
C43 C 0.6325(2) 0.7989(2) -0.2036(5) 0.0223(9) Uani 1 1 d . . . . .
H43 H 0.658392 0.779989 -0.260887 0.027 Uiso 1 1 calc R . . . .
C44 C 0.62552(19) 0.6702(2) -0.1026(5) 0.0179(8) Uani 1 1 d . . . . .
H44A H 0.675637 0.704497 -0.093907 0.027 Uiso 1 1 calc GR . . . .
H44B H 0.610444 0.665484 -0.233878 0.027 Uiso 1 1 calc GR . . . .
H44C H 0.617004 0.624742 -0.055955 0.027 Uiso 1 1 calc GR . . . .
C45 C 0.6692(2) 0.7389(2) 0.2986(5) 0.0223(9) Uani 1 1 d . . . . .
H45A H 0.704258 0.733017 0.229041 0.033 Uiso 1 1 calc GR . . . .
H45B H 0.668861 0.725739 0.430272 0.033 Uiso 1 1 calc GR . . . .
H45C H 0.680710 0.787925 0.291746 0.033 Uiso 1 1 calc GR . . . .
H9 H 0.484(2) 0.631(2) -0.226(5) 0.017(11) Uiso 1 1 d . . . . .
H6 H 0.491(2) 0.333(2) 1.202(5) 0.028(12) Uiso 1 1 d . . . . .
H3 H 0.203(2) 0.024(2) -0.170(6) 0.023(11) 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 0.0033 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_
_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
C8 N1 C1 122.4(3) . . ?
C8 N1 C9 111.0(3) . . ?
C9 N1 C1 121.6(3) . . ?
C9 N2 C7 112.3(3) . . ?
C9 N2 C15 122.5(3) . . ?
C15 N2 C7 121.9(3) . . ?
C8 N3 H3 114(3) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.6(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.9(3) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.8(3) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C6 C5 C4 125.8(3) . . ?
C10 C5 C4 116.0(3) . . ?
C10 C5 C6 118.2(3) . . ?
C5 C6 C7 123.4(3) . . ?
C13 C6 C5 118.2(3) . . ?
C13 C6 C7 118.4(3) . . ?
N2 C7 C6 111.3(3) . . ?
N2 C7 C8 101.0(3) . . ?
N2 C7 C14 109.3(3) . . ?
C6 C7 C14 114.8(3) . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 C14 108.5(3) . . ?
N1 C8 C7 106.8(3) . . ?
N3 C8 N1 123.1(3) . . ?
N3 C8 C7 130.1(3) . . ?
O1 C9 N1 124.3(3) . . ?
O1 C9 N2 127.3(3) . . ?
N2 C9 N1 108.4(3) . . ?
C5 C10 H10 118.9 . . ?
C11 C10 C5 122.2(4) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C6 C13 H13 118.8 . . ?
C12 C13 C6 122.4(4) . . ?
C12 C13 H13 118.8 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 N4 C16 122.7(3) . . ?
C23 N4 C24 110.8(3) . . ?
C24 N4 C16 120.6(3) . . ?
C24 N5 C22 112.1(3) . . ?
C24 N5 C30 122.4(3) . . ?
C30 N5 C22 123.0(3) . . ?
C23 N6 H6 109(3) . . ?
N4 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
N4 C16 C17 111.9(3) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C16 C17 C18 114.1(3) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.2(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.3(3) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C21 C20 C19 126.3(3) . . ?
C25 C20 C19 115.5(3) . . ?
C25 C20 C21 118.2(3) . . ?
C20 C21 C22 122.9(3) . . ?
C28 C21 C20 118.3(3) . . ?
C28 C21 C22 118.7(3) . . ?
N5 C22 C21 113.2(3) . . ?
N5 C22 C23 101.1(3) . . ?
N5 C22 C29 108.7(3) . . ?
C23 C22 C21 108.1(3) . . ?
C29 C22 C21 114.7(3) . . ?
C29 C22 C23 110.1(3) . . ?
N4 C23 C22 106.9(3) . . ?
N6 C23 N4 123.7(3) . . ?
N6 C23 C22 129.3(3) . . ?
O2 C24 N4 124.2(3) . . ?
O2 C24 N5 126.9(3) . . ?
N5 C24 N4 108.8(3) . . ?
C20 C25 H25 118.8 . . ?
C26 C25 C20 122.3(4) . . ?
C26 C25 H25 118.8 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.3(3) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
C28 C27 H27 120.3 . . ?
C21 C28 H28 118.8 . . ?
C27 C28 C21 122.5(4) . . ?
C27 C28 H28 118.8 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N5 C30 H30A 109.5 . . ?
N5 C30 H30B 109.5 . . ?
N5 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C38 N7 C31 122.8(3) . . ?
C38 N7 C39 111.2(3) . . ?
C39 N7 C31 121.1(3) . . ?
C39 N8 C37 112.6(3) . . ?
C39 N8 C45 122.9(3) . . ?
C45 N8 C37 124.3(3) . . ?
C38 N9 H9 111(3) . . ?
N7 C31 H31A 109.3 . . ?
N7 C31 H31B 109.3 . . ?
N7 C31 C32 111.7(3) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C31 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C31 C32 C33 113.2(3) . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C32 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C32 C33 C34 113.8(3) . . ?
H33A C33 H33B 107.7 . . ?
C34 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C33 C34 H34A 108.4 . . ?
C33 C34 H34B 108.4 . . ?
H34A C34 H34B 107.5 . . ?
C35 C34 C33 115.6(3) . . ?
C35 C34 H34A 108.4 . . ?
C35 C34 H34B 108.4 . . ?
C36 C35 C34 126.3(3) . . ?
C40 C35 C34 116.0(3) . . ?
C40 C35 C36 117.7(3) . . ?
C35 C36 C37 122.7(3) . . ?
C43 C36 C35 118.7(3) . . ?
C43 C36 C37 118.5(3) . . ?
N8 C37 C36 112.8(3) . . ?
N8 C37 C38 100.7(3) . . ?
N8 C37 C44 109.6(3) . . ?
C38 C37 C36 108.4(3) . . ?
C38 C37 C44 109.7(3) . . ?
C44 C37 C36 114.6(3) . . ?
N7 C38 C37 107.0(3) . . ?
N9 C38 N7 123.1(3) . . ?
N9 C38 C37 129.8(3) . . ?
O3 C39 N7 124.2(3) . . ?
O3 C39 N8 127.7(3) . . ?
N8 C39 N7 108.1(3) . . ?
C35 C40 H40 118.5 . . ?
C41 C40 C35 123.0(4) . . ?
C41 C40 H40 118.5 . . ?
C40 C41 H41 120.3 . . ?
C42 C41 C40 119.4(4) . . ?
C42 C41 H41 120.3 . . ?
C41 C42 H42 120.3 . . ?
C41 C42 C43 119.5(4) . . ?
C43 C42 H42 120.3 . . ?
C36 C43 H43 119.1 . . ?
C42 C43 C36 121.8(4) . . ?
C42 C43 H43 119.1 . . ?
C37 C44 H44A 109.5 . . ?
C37 C44 H44B 109.5 . . ?
C37 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N8 C45 H45A 109.5 . . ?
N8 C45 H45B 109.5 . . ?
N8 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
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
O1 C9 1.224(4) . ?
N1 C1 1.462(5) . ?
N1 C8 1.393(4) . ?
N1 C9 1.396(5) . ?
N2 C7 1.477(4) . ?
N2 C9 1.342(5) . ?
N2 C15 1.455(5) . ?
N3 C8 1.265(5) . ?
N3 H3 0.89(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.530(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.553(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.553(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.528(5) . ?
C5 C6 1.422(5) . ?
C5 C10 1.394(5) . ?
C6 C7 1.534(5) . ?
C6 C13 1.393(5) . ?
C7 C8 1.529(5) . ?
C7 C14 1.535(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C24 1.228(4) . ?
N4 C16 1.459(5) . ?
N4 C23 1.392(4) . ?
N4 C24 1.392(5) . ?
N5 C22 1.471(4) . ?
N5 C24 1.350(4) . ?
N5 C30 1.444(4) . ?
N6 C23 1.270(5) . ?
N6 H6 0.91(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.536(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.561(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.522(5) . ?
C20 C21 1.412(5) . ?
C20 C25 1.398(5) . ?
C21 C22 1.539(5) . ?
C21 C28 1.397(5) . ?
C22 C23 1.536(5) . ?
C22 C29 1.534(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.376(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(5) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O3 C39 1.226(4) . ?
N7 C31 1.466(5) . ?
N7 C38 1.387(4) . ?
N7 C39 1.393(5) . ?
N8 C37 1.476(4) . ?
N8 C39 1.345(4) . ?
N8 C45 1.447(5) . ?
N9 C38 1.271(5) . ?
N9 H9 0.85(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.524(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.541(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.562(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.530(5) . ?
C35 C36 1.412(5) . ?
C35 C40 1.396(5) . ?
C36 C37 1.543(5) . ?
C36 C43 1.398(5) . ?
C37 C38 1.529(5) . ?
C37 C44 1.536(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.376(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.371(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.393(6) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
