#------------------------------------------------------------------------------
#$Date: 2025-04-05 07:23:33 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160268.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_7160268
loop_
_publ_author_name
'Hopkins, Scarlet L.'
'Clarke, Kristen T.'
'Clegg, Jack K.'
'Gee, William J.'
_publ_section_title
;
 One-pot synthesis of azepine spiro[4.6]-γ-lactams by a
 Hantzsch-type reaction.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              614
_journal_page_last               618
_journal_paper_doi               10.1039/d4ob01719f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C27 H15 Br N2 O3, 1[H2O]'
_chemical_formula_sum            'C27 H17 Br N2 O4'
_chemical_formula_weight         513.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-11 deposited with the CCDC.	2024-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.100(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5296(5)
_cell_length_b                   20.1852(13)
_cell_length_c                   12.1204(8)
_cell_measurement_reflns_used    5298
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      67.406
_cell_measurement_theta_min      4.381
_cell_volume                     2369.5(3)
_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      150.00
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  BrukerD8
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1503
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33994
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        50.431
_diffrn_reflns_theta_max         50.431
_diffrn_reflns_theta_min         4.381
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1632 before and 0.0979 after correction.
The Ratio of minimum to maximum transmission is 0.7421.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark violet'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.001
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1309P)²+6.5801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1962
_refine_ls_wR_factor_ref         0.2098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1921
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01719f2.cif
_cod_data_source_block           cu_dwg24jc04
_cod_depositor_comments
'Adding full bibliography for 7160265--7160271.cif.'
_cod_database_code               7160268
_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   0.997
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C25(H25), C24(H24), C5(H5), C6(H6), C17(H17), C18(H18),
 C19(H19), C20(H20), C8(H8), C27(H27), C26(H26)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.10541(12) 0.58516(5) 0.25651(11) 0.0755(6) Uani 1 1 d . . . . .
O3 O 0.6173(5) 0.3698(3) 0.4190(5) 0.0432(14) Uani 1 1 d . . . . .
O2 O 0.1986(5) 0.3290(2) 0.6709(4) 0.0326(12) Uani 1 1 d . . . . .
O1 O -0.0127(5) 0.2450(3) 0.4813(4) 0.0354(13) Uani 1 1 d . . . . .
N1 N -0.1021(6) 0.3497(3) 0.4338(6) 0.0371(16) Uani 1 1 d . . . . .
H1 H -0.175786 0.344268 0.450175 0.044 Uiso 1 1 calc R U . . .
N2 N 0.1406(6) 0.3133(3) 0.2125(5) 0.0330(15) Uani 1 1 d . . . . .
H2 H 0.087504 0.318633 0.136133 0.040 Uiso 1 1 calc R U . . .
C25 C 0.4664(10) 0.4035(4) 0.0286(8) 0.051(2) Uani 1 1 d . . . . .
H25 H 0.514957 0.421631 -0.015938 0.061 Uiso 1 1 calc R U . . .
C24 C 0.5351(9) 0.3949(4) 0.1496(7) 0.045(2) Uani 1 1 d . . . . .
H24 H 0.630141 0.405586 0.189443 0.054 Uiso 1 1 calc R U . . .
C22 C 0.4579(8) 0.3695(4) 0.2119(7) 0.036(2) Uani 1 1 d . . . . .
C21 C 0.5041(9) 0.3583(4) 0.3440(8) 0.040(2) Uani 1 1 d . . . . .
C11 C 0.3769(7) 0.3334(3) 0.3592(7) 0.0323(19) Uani 1 1 d . . . . .
C12 C 0.3643(7) 0.3219(3) 0.4705(7) 0.0309(18) Uani 1 1 d . . . . .
C13 C 0.2444(7) 0.3223(3) 0.4909(7) 0.0297(18) Uani 1 1 d . . . . .
C4 C 0.0990(7) 0.3294(3) 0.4006(6) 0.0289(18) Uani 1 1 d . . . . .
C3 C 0.0494(7) 0.3999(3) 0.3698(6) 0.0303(18) Uani 1 1 d . . . . .
C2 C -0.0716(8) 0.4093(4) 0.3903(6) 0.0340(19) Uani 1 1 d . . . . .
C5 C -0.1379(8) 0.4681(4) 0.3721(7) 0.039(2) Uani 1 1 d . . . . .
H5 H -0.219123 0.473317 0.387572 0.046 Uiso 1 1 calc R U . . .
C6 C -0.0855(8) 0.5196(4) 0.3311(7) 0.044(2) Uani 1 1 d . . . . .
H6 H -0.131159 0.561264 0.317074 0.052 Uiso 1 1 calc R U . . .
C14 C 0.2780(8) 0.3222(3) 0.6204(7) 0.0320(18) Uani 1 1 d . . . . .
C15 C 0.4301(7) 0.3133(3) 0.6800(7) 0.0320(19) Uani 1 1 d . . . . .
C17 C 0.5136(8) 0.3045(4) 0.7987(7) 0.039(2) Uani 1 1 d . . . . .
H17 H 0.476653 0.307025 0.858630 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6504(8) 0.2920(4) 0.8292(7) 0.042(2) Uani 1 1 d . . . . .
H18 H 0.710559 0.287486 0.911186 0.050 Uiso 1 1 calc R U . . .
C19 C 0.7009(9) 0.2860(4) 0.7417(8) 0.046(2) Uani 1 1 d . . . . .
H19 H 0.795597 0.275190 0.764568 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6207(8) 0.2949(4) 0.6222(7) 0.040(2) Uani 1 1 d . . . . .
H20 H 0.658103 0.290318 0.562885 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4825(8) 0.3108(4) 0.5916(7) 0.0337(19) Uani 1 1 d . . . . .
C8 C 0.1046(8) 0.4523(4) 0.3313(7) 0.037(2) Uani 1 1 d . . . . .
H8 H 0.188532 0.447625 0.320052 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0344(8) 0.5122(4) 0.3094(7) 0.042(2) Uani 1 1 d . . . . .
C1 C -0.0092(7) 0.3018(4) 0.4482(6) 0.0322(19) Uani 1 1 d . . . . .
C9 C 0.0745(7) 0.2863(4) 0.2867(7) 0.0335(19) Uani 1 1 d . . . . .
H9A H 0.110209 0.241095 0.312231 0.040 Uiso 1 1 calc R U . . .
H9B H -0.026002 0.282875 0.238697 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2703(8) 0.3310(3) 0.2448(7) 0.0311(18) Uani 1 1 d . . . . .
C23 C 0.3217(8) 0.3534(4) 0.1532(7) 0.036(2) Uani 1 1 d . . . . .
C27 C 0.2541(8) 0.3618(4) 0.0308(7) 0.037(2) Uani 1 1 d . . . . .
H27 H 0.159291 0.350648 -0.009512 0.044 Uiso 1 1 calc R U . . .
C26 C 0.3292(9) 0.3869(4) -0.0311(8) 0.045(2) Uani 1 1 d . . . . .
H26 H 0.285886 0.392812 -0.115484 0.054 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 123.0 . . ?
C1 N1 H1 123.0 . . ?
C1 N1 C2 114.0(6) . . ?
C9 N2 H2 116.0 . . ?
C10 N2 H2 116.0 . . ?
C10 N2 C9 128.0(6) . . ?
C24 C25 H25 118.8 . . ?
C24 C25 C26 122.4(7) . . ?
C26 C25 H25 118.8 . . ?
C25 C24 H24 121.7 . . ?
C25 C24 C22 116.7(8) . . ?
C22 C24 H24 121.7 . . ?
C24 C22 C21 128.1(7) . . ?
C23 C22 C24 121.1(7) . . ?
C23 C22 C21 110.8(6) . . ?
O3 C21 C22 126.1(7) . . ?
O3 C21 C11 129.4(7) . . ?
C22 C21 C11 104.5(7) . . ?
C12 C11 C21 125.9(7) . . ?
C10 C11 C21 107.2(6) . . ?
C10 C11 C12 126.5(6) . . ?
C11 C12 C16 126.3(6) . . ?
C13 C12 C11 126.9(7) . . ?
C13 C12 C16 106.7(6) . . ?
C12 C13 C4 127.9(6) . . ?
C12 C13 C14 109.8(6) . . ?
C14 C13 C4 122.0(6) . . ?
C13 C4 C3 115.2(6) . . ?
C13 C4 C1 112.2(6) . . ?
C13 C4 C9 111.0(5) . . ?
C3 C4 C1 101.3(6) . . ?
C3 C4 C9 112.6(6) . . ?
C9 C4 C1 103.6(5) . . ?
C2 C3 C4 109.6(6) . . ?
C8 C3 C4 131.1(6) . . ?
C8 C3 C2 119.3(7) . . ?
N1 C2 C3 107.9(6) . . ?
C5 C2 N1 129.5(7) . . ?
C5 C2 C3 122.6(7) . . ?
C2 C5 H5 120.9 . . ?
C2 C5 C6 118.2(7) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 120.9(7) . . ?
C7 C6 H6 119.5 . . ?
O2 C14 C13 127.6(7) . . ?
O2 C14 C15 126.0(7) . . ?
C13 C14 C15 106.4(6) . . ?
C17 C15 C14 130.5(6) . . ?
C17 C15 C16 121.4(7) . . ?
C16 C15 C14 108.0(6) . . ?
C15 C17 H17 120.6 . . ?
C18 C17 C15 118.8(7) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.9(8) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 118.6 . . ?
C18 C19 C20 122.9(7) . . ?
C20 C19 H19 118.6 . . ?
C19 C20 H20 121.4 . . ?
C19 C20 C16 117.2(7) . . ?
C16 C20 H20 121.4 . . ?
C15 C16 C12 108.5(6) . . ?
C15 C16 C20 119.6(7) . . ?
C20 C16 C12 131.7(7) . . ?
C3 C8 H8 121.0 . . ?
C3 C8 C7 118.1(7) . . ?
C7 C8 H8 121.0 . . ?
C6 C7 Br1 119.5(6) . . ?
C8 C7 Br1 119.7(6) . . ?
C8 C7 C6 120.8(7) . . ?
O1 C1 N1 127.4(6) . . ?
O1 C1 C4 125.2(7) . . ?
N1 C1 C4 107.1(7) . . ?
N2 C9 C4 112.8(6) . . ?
N2 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C4 C9 H9A 109.0 . . ?
C4 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C11 129.8(7) . . ?
N2 C10 C23 120.1(7) . . ?
C11 C10 C23 110.1(6) . . ?
C22 C23 C10 107.4(7) . . ?
C22 C23 C27 121.6(7) . . ?
C27 C23 C10 131.0(7) . . ?
C23 C27 H27 121.2 . . ?
C26 C27 C23 117.7(7) . . ?
C26 C27 H27 121.2 . . ?
C25 C26 C27 120.6(8) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.875(7) . ?
O3 C21 1.205(10) . ?
O2 C14 1.222(8) . ?
O1 C1 1.219(9) . ?
N1 H1 0.8800 . ?
N1 C2 1.401(10) . ?
N1 C1 1.338(10) . ?
N2 H2 0.8800 . ?
N2 C9 1.443(9) . ?
N2 C10 1.313(9) . ?
C25 H25 0.9500 . ?
C25 C24 1.368(12) . ?
C25 C26 1.380(12) . ?
C24 H24 0.9500 . ?
C24 C22 1.405(11) . ?
C22 C21 1.496(12) . ?
C22 C23 1.367(11) . ?
C21 C11 1.509(11) . ?
C11 C12 1.424(10) . ?
C11 C10 1.401(11) . ?
C12 C13 1.379(9) . ?
C12 C16 1.524(10) . ?
C13 C4 1.499(10) . ?
C13 C14 1.466(11) . ?
C4 C3 1.510(10) . ?
C4 C1 1.568(10) . ?
C4 C9 1.565(10) . ?
C3 C2 1.403(10) . ?
C3 C8 1.374(10) . ?
C2 C5 1.350(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.359(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(11) . ?
C14 C15 1.487(10) . ?
C15 C17 1.372(11) . ?
C15 C16 1.385(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.363(11) . ?
C18 H18 0.9500 . ?
C18 C19 1.365(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.372(11) . ?
C20 H20 0.9500 . ?
C20 C16 1.391(10) . ?
C8 H8 0.9500 . ?
C8 C7 1.388(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C23 1.485(10) . ?
C23 C27 1.382(11) . ?
C27 H27 0.9500 . ?
C27 C26 1.382(10) . ?
C26 H26 0.9500 . ?
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
O3 C21 C11 C12 3.9(12) . . . . ?
O3 C21 C11 C10 177.5(8) . . . . ?
O2 C14 C15 C17 6.9(12) . . . . ?
O2 C14 C15 C16 -176.9(7) . . . . ?
N1 C2 C5 C6 178.5(7) . . . . ?
N2 C10 C23 C22 179.0(6) . . . . ?
N2 C10 C23 C27 2.0(12) . . . . ?
C25 C24 C22 C21 -176.7(7) . . . . ?
C25 C24 C22 C23 1.0(12) . . . . ?
C24 C25 C26 C27 1.4(13) . . . . ?
C24 C22 C21 O3 0.2(13) . . . . ?
C24 C22 C21 C11 177.6(7) . . . . ?
C24 C22 C23 C10 -177.7(7) . . . . ?
C24 C22 C23 C27 -0.4(12) . . . . ?
C22 C21 C11 C12 -173.3(7) . . . . ?
C22 C21 C11 C10 0.2(8) . . . . ?
C22 C23 C27 C26 0.2(11) . . . . ?
C21 C22 C23 C10 0.4(8) . . . . ?
C21 C22 C23 C27 177.7(7) . . . . ?
C21 C11 C12 C13 155.2(7) . . . . ?
C21 C11 C12 C16 -21.0(11) . . . . ?
C21 C11 C10 N2 -179.1(7) . . . . ?
C21 C11 C10 C23 0.0(8) . . . . ?
C11 C12 C13 C4 5.3(11) . . . . ?
C11 C12 C13 C14 -168.2(6) . . . . ?
C11 C12 C16 C15 169.5(7) . . . . ?
C11 C12 C16 C20 -15.7(12) . . . . ?
C11 C10 C23 C22 -0.2(8) . . . . ?
C11 C10 C23 C27 -177.2(8) . . . . ?
C12 C11 C10 N2 -5.6(12) . . . . ?
C12 C11 C10 C23 173.5(7) . . . . ?
C12 C13 C4 C3 -86.1(8) . . . . ?
C12 C13 C4 C1 158.7(7) . . . . ?
C12 C13 C4 C9 43.3(9) . . . . ?
C12 C13 C14 O2 172.0(6) . . . . ?
C12 C13 C14 C15 -6.8(7) . . . . ?
C13 C12 C16 C15 -7.3(8) . . . . ?
C13 C12 C16 C20 167.5(8) . . . . ?
C13 C4 C3 C2 -124.2(6) . . . . ?
C13 C4 C3 C8 53.6(10) . . . . ?
C13 C4 C1 O1 -58.6(9) . . . . ?
C13 C4 C1 N1 127.5(6) . . . . ?
C13 C4 C9 N2 -73.0(8) . . . . ?
C13 C14 C15 C17 -174.2(7) . . . . ?
C13 C14 C15 C16 2.0(7) . . . . ?
C4 C13 C14 O2 -1.9(11) . . . . ?
C4 C13 C14 C15 179.2(6) . . . . ?
C4 C3 C2 N1 0.8(8) . . . . ?
C4 C3 C2 C5 179.0(7) . . . . ?
C4 C3 C8 C7 179.8(7) . . . . ?
C3 C4 C1 O1 178.0(7) . . . . ?
C3 C4 C1 N1 4.1(7) . . . . ?
C3 C4 C9 N2 57.8(8) . . . . ?
C3 C2 C5 C6 0.8(11) . . . . ?
C3 C8 C7 Br1 -179.9(5) . . . . ?
C3 C8 C7 C6 2.8(12) . . . . ?
C2 N1 C1 O1 -177.8(7) . . . . ?
C2 N1 C1 C4 -4.1(8) . . . . ?
C2 C3 C8 C7 -2.6(11) . . . . ?
C2 C5 C6 C7 -0.6(11) . . . . ?
C5 C6 C7 Br1 -178.5(6) . . . . ?
C5 C6 C7 C8 -1.2(12) . . . . ?
C14 C13 C4 C3 86.7(8) . . . . ?
C14 C13 C4 C1 -28.5(9) . . . . ?
C14 C13 C4 C9 -143.9(6) . . . . ?
C14 C15 C17 C18 174.7(7) . . . . ?
C14 C15 C16 C12 3.1(8) . . . . ?
C14 C15 C16 C20 -172.4(6) . . . . ?
C15 C17 C18 C19 -2.5(11) . . . . ?
C17 C15 C16 C12 179.7(7) . . . . ?
C17 C15 C16 C20 4.2(11) . . . . ?
C17 C18 C19 C20 3.0(12) . . . . ?
C18 C19 C20 C16 0.1(12) . . . . ?
C19 C20 C16 C12 -177.9(7) . . . . ?
C19 C20 C16 C15 -3.6(11) . . . . ?
C16 C12 C13 C4 -177.9(6) . . . . ?
C16 C12 C13 C14 8.6(7) . . . . ?
C16 C15 C17 C18 -1.1(11) . . . . ?
C8 C3 C2 N1 -177.3(7) . . . . ?
C8 C3 C2 C5 0.9(11) . . . . ?
C1 N1 C2 C3 2.2(8) . . . . ?
C1 N1 C2 C5 -175.8(7) . . . . ?
C1 C4 C3 C2 -2.9(7) . . . . ?
C1 C4 C3 C8 174.9(7) . . . . ?
C1 C4 C9 N2 166.4(6) . . . . ?
C9 N2 C10 C11 -5.4(12) . . . . ?
C9 N2 C10 C23 175.6(6) . . . . ?
C9 C4 C3 C2 107.1(7) . . . . ?
C9 C4 C3 C8 -75.1(9) . . . . ?
C9 C4 C1 O1 61.2(9) . . . . ?
C9 C4 C1 N1 -112.7(6) . . . . ?
C10 N2 C9 C4 52.3(9) . . . . ?
C10 C11 C12 C13 -17.1(11) . . . . ?
C10 C11 C12 C16 166.7(7) . . . . ?
C10 C23 C27 C26 176.8(7) . . . . ?
C23 C22 C21 O3 -177.8(7) . . . . ?
C23 C22 C21 C11 -0.4(8) . . . . ?
C23 C27 C26 C25 -0.7(12) . . . . ?
C26 C25 C24 C22 -1.5(13) . . . . ?
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 -0.490 0.000 -0.990 258.9 14.0 '2 H2O'
2 -0.787 0.500 -0.787 258.9 14.0 '2 H2O'
