#------------------------------------------------------------------------------
#$Date: 2025-11-29 23:09:52 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303942 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/07/7160748.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_7160748
loop_
_publ_author_name
'Ge, Shanliang'
'Wang, Zhongjie'
'Wang, Yan'
'Luo, Hui'
'He, Yu'
'Yang, Qinqin'
'Yang, Jinhui'
_publ_section_title
;
 Green synthesis of aryl amides via recyclable
 Et₃N/H₂O-promoted C-Cl activation in water.
;
_journal_issue                   39
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8986
_journal_page_last               8992
_journal_paper_doi               10.1039/d5ob01047k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-09-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2024-11-04 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.092(3)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.8328(11)
_cell_length_b                   13.8246(11)
_cell_length_c                   20.3995(18)
_cell_measurement_reflns_used    3989
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.82
_cell_measurement_theta_min      2.31
_cell_volume                     3901.1(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0886
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25777
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.174
_diffrn_reflns_theta_max         25.174
_diffrn_reflns_theta_min         2.083
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6911
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0689 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.9274.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6762
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1564
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0530P)²+1.5742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1610
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3476
_reflns_number_total             6762
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01047k2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7160748.cif.'
_cod_database_code               7160748
_shelx_shelxl_version_number     2014/7
_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   0.994
_shelx_estimated_absorpt_t_min   0.991
_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
2.a Riding coordinates:
 C40(H40A,H40B,H40C)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C18(H18A,H18B), C19(H19A,H19B), C28(H28A,H28B),
 C29(H29A,H29B), C38(H38A,H38B), C39(H39A,H39B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C14(H14), C13(H13),
 C12(H12), C11(H11), C25(H25), C24(H24), C23(H23), C22(H22), C21(H21), C35(H35),
  C34(H34), C33(H33), C32(H32), C31(H31), N1(H1A), N2(H2A), N3(H3A), N4(H4A)
2.d Fitted hexagon refined as free rotating group:
 C6(C1,C2,C3,C4,C5), C15(C14,C13,C12,C11,C16), C26(C25,C24,C23,C22,C21),
 C36(C35,C34,C33,C32,C31)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.6910(3) 0.2245(3) 0.5994(2) 0.0597(16) Uani 1 1 d G . . . .
C1 C 0.7839(3) 0.1876(3) 0.6064(2) 0.0683(18) Uani 1 1 d G . . . .
H1 H 0.7950 0.1350 0.6338 0.082 Uiso 1 1 calc R U . . .
C2 C 0.8603(3) 0.2294(4) 0.5724(3) 0.088(2) Uani 1 1 d G . . . .
H2 H 0.9225 0.2047 0.5771 0.106 Uiso 1 1 calc R U . . .
C3 C 0.8438(4) 0.3081(4) 0.5315(3) 0.099(3) Uani 1 1 d G . . . .
H3 H 0.8949 0.3360 0.5088 0.118 Uiso 1 1 calc R U . . .
C4 C 0.7509(5) 0.3450(3) 0.5245(2) 0.097(3) Uani 1 1 d G . . . .
H4 H 0.7398 0.3976 0.4971 0.116 Uiso 1 1 calc R U . . .
C5 C 0.6745(3) 0.3032(3) 0.5584(2) 0.079(2) Uani 1 1 d G . . . .
H5 H 0.6123 0.3279 0.5537 0.095 Uiso 1 1 calc R U . . .
C7 C 0.6065(5) 0.1852(5) 0.6343(3) 0.0662(18) Uani 1 1 d . . . . .
C8 C 0.5384(5) 0.0497(5) 0.6991(4) 0.080(2) Uani 1 1 d . . . . .
H8A H 0.4965 0.0992 0.7172 0.096 Uiso 1 1 calc R U . . .
H8B H 0.5673 0.0150 0.7355 0.096 Uiso 1 1 calc R U . . .
C9 C 0.4792(6) -0.0184(6) 0.6602(4) 0.096(2) Uani 1 1 d . . . . .
H9A H 0.5203 -0.0698 0.6437 0.116 Uiso 1 1 calc R U . . .
H9B H 0.4521 0.0154 0.6228 0.116 Uiso 1 1 calc R U . . .
C10 C 0.3969(7) -0.0629(7) 0.7003(5) 0.138(4) Uani 1 1 d . . . . .
H10A H 0.3523 -0.0947 0.6714 0.207 Uiso 1 1 calc R U . . .
H10B H 0.3639 -0.0128 0.7240 0.207 Uiso 1 1 calc R U . . .
H10C H 0.4230 -0.1091 0.7307 0.207 Uiso 1 1 calc R U . . .
C15 C 0.1803(3) 0.3110(4) 0.5594(2) 0.084(2) Uani 1 1 d G . . . .
H15 H 0.1556 0.3732 0.5555 0.100 Uiso 1 1 calc R U . . .
C14 C 0.1384(3) 0.2352(5) 0.5248(2) 0.095(3) Uani 1 1 d G . . . .
H14 H 0.0856 0.2468 0.4976 0.114 Uiso 1 1 calc R U . . .
C13 C 0.1754(4) 0.1421(4) 0.5306(2) 0.102(3) Uani 1 1 d G . . . .
H13 H 0.1473 0.0915 0.5074 0.122 Uiso 1 1 calc R U . . .
C12 C 0.2544(4) 0.1248(3) 0.5712(3) 0.089(2) Uani 1 1 d G . . . .
H12 H 0.2791 0.0625 0.5751 0.107 Uiso 1 1 calc R U . . .
C11 C 0.2963(3) 0.2005(3) 0.6059(2) 0.0691(18) Uani 1 1 d G . . . .
H11 H 0.3491 0.1889 0.6330 0.083 Uiso 1 1 calc R U . . .
C16 C 0.2593(3) 0.2936(3) 0.6000(2) 0.0580(17) Uani 1 1 d G . . . .
C17 C 0.3016(5) 0.3778(5) 0.6365(3) 0.0676(19) Uani 1 1 d . . . . .
C18 C 0.4375(6) 0.4444(5) 0.6984(4) 0.084(2) Uani 1 1 d . . . . .
H18A H 0.4744 0.4146 0.7335 0.101 Uiso 1 1 calc R U . . .
H18B H 0.3886 0.4851 0.7184 0.101 Uiso 1 1 calc R U . . .
C19 C 0.5036(6) 0.5067(6) 0.6591(4) 0.100(3) Uani 1 1 d . . . . .
H19A H 0.5522 0.4662 0.6386 0.120 Uiso 1 1 calc R U . . .
H19B H 0.4668 0.5377 0.6245 0.120 Uiso 1 1 calc R U . . .
C20 C 0.5531(7) 0.5827(7) 0.6989(5) 0.128(3) Uani 1 1 d . . . . .
H20A H 0.5896 0.6242 0.6705 0.192 Uiso 1 1 calc R U . . .
H20B H 0.5958 0.5525 0.7299 0.192 Uiso 1 1 calc R U . . .
H20C H 0.5056 0.6202 0.7219 0.192 Uiso 1 1 calc R U . . .
C26 C 0.5098(3) 0.5417(3) 0.4005(2) 0.0556(16) Uani 1 1 d G . . . .
C25 C 0.4310(3) 0.5584(3) 0.4411(2) 0.085(2) Uani 1 1 d G . . . .
H25 H 0.4064 0.6207 0.4456 0.102 Uiso 1 1 calc R U . . .
C24 C 0.3891(3) 0.4821(5) 0.4752(2) 0.094(2) Uani 1 1 d G . . . .
H24 H 0.3364 0.4933 0.5024 0.112 Uiso 1 1 calc R U . . .
C23 C 0.4260(4) 0.3891(4) 0.4686(2) 0.091(2) Uani 1 1 d G . . . .
H23 H 0.3979 0.3381 0.4914 0.109 Uiso 1 1 calc R U . . .
C22 C 0.5047(4) 0.3724(3) 0.4279(3) 0.084(2) Uani 1 1 d G . . . .
H22 H 0.5294 0.3101 0.4235 0.100 Uiso 1 1 calc R U . . .
C21 C 0.5467(3) 0.4487(3) 0.3939(2) 0.0705(19) Uani 1 1 d G . . . .
H21 H 0.5994 0.4375 0.3667 0.085 Uiso 1 1 calc R U . . .
C27 C 0.5510(5) 0.6268(5) 0.3645(3) 0.0662(18) Uani 1 1 d . . . . .
C28 C 0.6824(5) 0.6946(5) 0.2999(4) 0.080(2) Uani 1 1 d . . . . .
H28A H 0.6325 0.7355 0.2812 0.095 Uiso 1 1 calc R U . . .
H28B H 0.7183 0.6660 0.2640 0.095 Uiso 1 1 calc R U . . .
C29 C 0.7506(5) 0.7570(6) 0.3405(4) 0.089(2) Uani 1 1 d . . . . .
H29A H 0.8023 0.7168 0.3576 0.106 Uiso 1 1 calc R U . . .
H29B H 0.7155 0.7835 0.3775 0.106 Uiso 1 1 calc R U . . .
C30 C 0.7937(7) 0.8386(7) 0.3016(4) 0.122(3) Uani 1 1 d . . . . .
H30A H 0.8393 0.8131 0.2706 0.184 Uiso 1 1 calc R U . . .
H30B H 0.8261 0.8826 0.3307 0.184 Uiso 1 1 calc R U . . .
H30C H 0.7433 0.8722 0.2786 0.184 Uiso 1 1 calc R U . . .
C36 C 0.4400(3) 0.9738(3) 0.3990(2) 0.0613(17) Uani 1 1 d G . . . .
C35 C 0.5335(3) 0.9382(3) 0.3928(2) 0.0691(18) Uani 1 1 d G . . . .
H35 H 0.5457 0.8856 0.3656 0.083 Uiso 1 1 calc R U . . .
C34 C 0.6089(3) 0.9812(4) 0.4273(3) 0.089(2) Uani 1 1 d G . . . .
H34 H 0.6714 0.9574 0.4232 0.107 Uiso 1 1 calc R U . . .
C33 C 0.5907(4) 1.0598(4) 0.4679(3) 0.101(3) Uani 1 1 d G . . . .
H33 H 0.6411 1.0886 0.4910 0.122 Uiso 1 1 calc R U . . .
C32 C 0.4972(5) 1.0954(3) 0.4741(2) 0.101(3) Uani 1 1 d G . . . .
H32 H 0.4850 1.1480 0.5013 0.121 Uiso 1 1 calc R U . . .
C31 C 0.4218(4) 1.0524(3) 0.4396(3) 0.088(2) Uani 1 1 d G . . . .
H31 H 0.3592 1.0762 0.4438 0.106 Uiso 1 1 calc R U . . .
C37 C 0.3565(5) 0.9319(5) 0.3635(3) 0.0665(19) Uani 1 1 d . . . . .
C38 C 0.2902(5) 0.7959(6) 0.2999(4) 0.089(2) Uani 1 1 d . . . . .
H38A H 0.3204 0.7589 0.2651 0.107 Uiso 1 1 calc R U . . .
H38B H 0.2499 0.8449 0.2795 0.107 Uiso 1 1 calc R U . . .
C39 C 0.2273(6) 0.7297(6) 0.3394(4) 0.100(3) Uani 1 1 d . . . . .
H39A H 0.1973 0.7664 0.3744 0.120 Uiso 1 1 calc R U . . .
H39B H 0.2674 0.6802 0.3594 0.120 Uiso 1 1 calc R U . . .
C40 C 0.1487(7) 0.6811(6) 0.2989(5) 0.123(3) Uani 1 1 d . . . . .
H40A H 0.1788 0.6425 0.2656 0.185 Uiso 1 1 d R U . . .
H40B H 0.1090 0.7297 0.2787 0.185 Uiso 1 1 d R U . . .
H40C H 0.1093 0.6406 0.3262 0.185 Uiso 1 1 d R U . . .
N1 N 0.6139(4) 0.0957(4) 0.6620(3) 0.0682(15) Uani 1 1 d . . . . .
H1A H 0.6673 0.0647 0.6570 0.082 Uiso 1 1 calc R U . . .
N2 N 0.3896(4) 0.3691(4) 0.6614(3) 0.0691(15) Uani 1 1 d . . . . .
H2A H 0.4200 0.3156 0.6551 0.083 Uiso 1 1 calc R U . . .
N3 N 0.6370(4) 0.6180(4) 0.3374(3) 0.0678(15) Uani 1 1 d . . . . .
H3A H 0.6676 0.5643 0.3422 0.081 Uiso 1 1 calc R U . . .
N4 N 0.3648(4) 0.8433(4) 0.3377(3) 0.0680(15) Uani 1 1 d . . . . .
H4A H 0.4181 0.8126 0.3441 0.082 Uiso 1 1 calc R U . . .
O1 O 0.5311(4) 0.2310(3) 0.6392(3) 0.1104(19) Uani 1 1 d . . . . .
O2 O 0.2554(3) 0.4539(3) 0.6435(3) 0.1103(19) Uani 1 1 d . . . . .
O3 O 0.5043(3) 0.7031(3) 0.3600(3) 0.1031(18) Uani 1 1 d . . . . .
O4 O 0.2800(4) 0.9772(4) 0.3566(3) 0.1034(18) Uani 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
C1 C6 C5 120.0 . . ?
C1 C6 C7 123.3(4) . . ?
C5 C6 C7 116.7(4) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
N1 C7 C6 118.4(5) . . ?
O1 C7 C6 121.7(6) . . ?
O1 C7 N1 119.9(7) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
N1 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
N1 C8 C9 113.7(6) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.3(7) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C16 C11 C12 120.0 . . ?
C16 C11 H11 120.0 . . ?
C15 C16 C17 117.9(4) . . ?
C11 C16 C15 120.0 . . ?
C11 C16 C17 122.1(4) . . ?
N2 C17 C16 118.5(6) . . ?
O2 C17 C16 120.9(6) . . ?
O2 C17 N2 120.6(7) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
N2 C18 H18A 108.6 . . ?
N2 C18 H18B 108.6 . . ?
N2 C18 C19 114.5(6) . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.2(7) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 C27 117.4(4) . . ?
C21 C26 C27 122.6(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C26 C21 H21 120.0 . . ?
C22 C21 C26 120.0 . . ?
C22 C21 H21 120.0 . . ?
N3 C27 C26 118.5(6) . . ?
O3 C27 C26 120.3(6) . . ?
O3 C27 N3 121.2(7) . . ?
H28A C28 H28B 107.7 . . ?
C29 C28 H28A 108.9 . . ?
C29 C28 H28B 108.9 . . ?
N3 C28 H28A 108.9 . . ?
N3 C28 H28B 108.9 . . ?
N3 C28 C29 113.3(6) . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
C28 C29 C30 112.6(6) . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 C37 122.9(4) . . ?
C31 C36 C37 117.1(4) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C34 H34 120.0 . . ?
C35 C34 C33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C33 H33 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C33 C32 C31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C36 C31 H31 120.0 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 H31 120.0 . . ?
N4 C37 C36 118.9(5) . . ?
O4 C37 C36 121.7(6) . . ?
O4 C37 N4 119.4(7) . . ?
H38A C38 H38B 107.7 . . ?
C39 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
N4 C38 H38A 108.8 . . ?
N4 C38 H38B 108.8 . . ?
N4 C38 C39 113.9(7) . . ?
C38 C39 H39A 109.0 . . ?
C38 C39 H39B 109.0 . . ?
C38 C39 C40 113.1(7) . . ?
H39A C39 H39B 107.8 . . ?
C40 C39 H39A 109.0 . . ?
C40 C39 H39B 109.0 . . ?
C39 C40 H40A 108.7 . . ?
C39 C40 H40B 109.4 . . ?
C39 C40 H40C 110.4 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C7 N1 C8 124.4(5) . . ?
C7 N1 H1A 117.8 . . ?
C8 N1 H1A 117.8 . . ?
C17 N2 C18 123.6(6) . . ?
C17 N2 H2A 118.2 . . ?
C18 N2 H2A 118.2 . . ?
C27 N3 C28 123.1(5) . . ?
C27 N3 H3A 118.4 . . ?
C28 N3 H3A 118.4 . . ?
C37 N4 C38 124.3(6) . . ?
C37 N4 H4A 117.8 . . ?
C38 N4 H4A 117.8 . . ?
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
C6 C1 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.474(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.3900 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C7 N1 1.364(8) . ?
C7 O1 1.225(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.478(10) . ?
C8 N1 1.439(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.532(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C15 C16 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C16 1.3900 . ?
C16 C17 1.501(8) . ?
C17 N2 1.323(7) . ?
C17 O2 1.239(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.492(10) . ?
C18 N2 1.447(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.493(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C26 C25 1.3900 . ?
C26 C21 1.3900 . ?
C26 C27 1.500(8) . ?
C25 H25 0.9300 . ?
C25 C24 1.3900 . ?
C24 H24 0.9300 . ?
C24 C23 1.3900 . ?
C23 H23 0.9300 . ?
C23 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C21 H21 0.9300 . ?
C27 N3 1.318(8) . ?
C27 O3 1.240(7) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.523(10) . ?
C28 N3 1.450(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.503(10) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C36 C35 1.3900 . ?
C36 C31 1.3900 . ?
C36 C37 1.480(8) . ?
C35 H35 0.9300 . ?
C35 C34 1.3900 . ?
C34 H34 0.9300 . ?
C34 C33 1.3900 . ?
C33 H33 0.9300 . ?
C33 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C31 1.3900 . ?
C31 H31 0.9300 . ?
C37 N4 1.338(8) . ?
C37 O4 1.238(7) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.499(10) . ?
C38 N4 1.445(9) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.521(10) . ?
C40 H40A 0.9601 . ?
C40 H40B 0.9599 . ?
C40 H40C 0.9601 . ?
N1 H1A 0.8600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
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
C6 C1 C2 C3 0.0 . . . . ?
C6 C7 N1 C8 178.2(6) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 N1 -16.4(7) . . . . ?
C1 C6 C7 O1 163.2(5) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C5 C6 C1 C2 0.0 . . . . ?
C5 C6 C7 N1 164.5(4) . . . . ?
C5 C6 C7 O1 -15.9(8) . . . . ?
C7 C6 C1 C2 -179.1(5) . . . . ?
C7 C6 C5 C4 179.2(5) . . . . ?
C9 C8 N1 C7 96.7(8) . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C15 C16 C17 N2 -162.8(4) . . . . ?
C15 C16 C17 O2 17.4(8) . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C14 C15 C16 C17 -179.8(4) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C13 C12 C11 C16 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C12 C11 C16 C17 179.8(5) . . . . ?
C11 C16 C17 N2 17.4(7) . . . . ?
C11 C16 C17 O2 -162.4(5) . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C16 C17 N2 C18 -178.9(6) . . . . ?
C19 C18 N2 C17 -95.8(8) . . . . ?
C26 C25 C24 C23 0.0 . . . . ?
C26 C27 N3 C28 178.2(5) . . . . ?
C25 C26 C21 C22 0.0 . . . . ?
C25 C26 C27 N3 165.3(4) . . . . ?
C25 C26 C27 O3 -15.3(7) . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C23 C22 C21 C26 0.0 . . . . ?
C21 C26 C25 C24 0.0 . . . . ?
C21 C26 C27 N3 -15.4(7) . . . . ?
C21 C26 C27 O3 164.0(5) . . . . ?
C27 C26 C25 C24 179.3(4) . . . . ?
C27 C26 C21 C22 -179.2(5) . . . . ?
C29 C28 N3 C27 94.7(7) . . . . ?
C36 C35 C34 C33 0.0 . . . . ?
C36 C37 N4 C38 -177.5(6) . . . . ?
C35 C36 C31 C32 0.0 . . . . ?
C35 C36 C37 N4 17.2(7) . . . . ?
C35 C36 C37 O4 -162.0(5) . . . . ?
C35 C34 C33 C32 0.0 . . . . ?
C34 C33 C32 C31 0.0 . . . . ?
C33 C32 C31 C36 0.0 . . . . ?
C31 C36 C35 C34 0.0 . . . . ?
C31 C36 C37 N4 -163.1(4) . . . . ?
C31 C36 C37 O4 17.7(8) . . . . ?
C37 C36 C35 C34 179.6(5) . . . . ?
C37 C36 C31 C32 -179.7(5) . . . . ?
C39 C38 N4 C37 -95.3(8) . . . . ?
N1 C8 C9 C10 -177.6(7) . . . . ?
N2 C18 C19 C20 -179.1(7) . . . . ?
N3 C28 C29 C30 -177.5(7) . . . . ?
N4 C38 C39 C40 179.5(7) . . . . ?
O1 C7 N1 C8 -1.5(10) . . . . ?
O2 C17 N2 C18 0.9(10) . . . . ?
O3 C27 N3 C28 -1.2(10) . . . . ?
O4 C37 N4 C38 1.7(10) . . . . ?
