#------------------------------------------------------------------------------
#$Date: 2023-09-13 00:55:12 +0300 (Wed, 13 Sep 2023) $
#$Revision: 286303 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132117.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_7132117
loop_
_publ_author_name
'Liu, Rai-Shung'
'Kshirsagar, Akshay Suresh'
'More, Sayaji Arjun'
_publ_section_title
;
 Stereo- and Regiocontrol in Intermolecular [2+2] Cycloadditions between
 Diarylketenes and Allenamides to Access Substituted
 α-Methylenecyclobutanones.
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03979J
_journal_year                    2023
_chemical_formula_moiety         'C21 H18 Br N O4'
_chemical_formula_sum            'C21 H18 Br N O4'
_chemical_formula_weight         428.27
_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             2022-04-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-11 deposited with the CCDC.	2023-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.770(2)
_cell_angle_beta                 98.537(2)
_cell_angle_gamma                96.489(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5723(2)
_cell_length_b                   10.1918(3)
_cell_length_c                   10.7219(3)
_cell_measurement_reflns_used    6642
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7370
_cell_measurement_theta_min      4.1790
_cell_volume                     919.34(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -40.00   0.50    0.10    --  -76.01 -15.00  60.00  122
  2  ω    -91.00 -65.00   0.50    0.10    --  -76.01 111.00  30.00   52
  3  ω    -88.00 -62.00   0.50    0.10    --  -76.01 111.00 -30.00   52
  4  ω    -56.00 -28.00   0.50    0.10    --  -76.01 111.00 -30.00   56
  5  ω    -54.00 -28.00   0.50    0.10    --  -76.01 111.00  30.00   52
  6  ω     80.00 106.00   0.50    0.10    --   56.31  15.00  30.00   52
  7  ω     59.00 120.00   0.50    0.10    --   69.43  15.00  90.00  122
  8  ω     43.00  91.00   0.50    0.10    --   76.52  15.00  60.00   96
  9  ω     59.00 134.00   0.50    0.10    --   84.37  15.00 150.00  150
 10  ω     45.00  75.00   0.50    0.10    --   56.31  15.00  30.00   60
 11  ω     52.00  77.00   0.50    0.10    --   84.37  15.00 120.00   50
 12  ω     47.00 122.00   0.50    0.10    --   76.52  15.00 -30.00  150
 13  ω     45.00 108.00   0.50    0.10    --   76.52  15.00 -90.00  126
 14  ω     63.00 134.00   0.50    0.10    --   84.37  15.00-150.00  142
 15  ω     45.00  88.00   0.50    0.10    --   84.37 -95.00 -90.00   86
 16  ω     66.00  92.00   0.50    0.10    --   76.52-111.00 -90.00   52
 17  ω     27.00  52.00   0.50    0.10    --   69.43 -95.00 -30.00   50
 18  ω     15.00  40.00   0.50    0.10    --   56.31 -95.00 -60.00   50
 19  ω     28.00  59.00   0.50    0.10    --   69.43 -95.00-180.00   62
 20  ω     37.00  62.00   0.50    0.10    --   76.52 -95.00-120.00   50
 21  ω     37.00  63.00   0.50    0.10    --   76.52 -95.00 -60.00   52
 22  ω     15.00  40.00   0.50    0.10    --   56.31 -95.00-120.00   50
 23  ω     15.00  41.00   0.50    0.10    --   56.31 -95.00 -90.00   52
 24  ω     46.00  92.00   0.50    0.10    --   84.37 -95.00  30.00   92
 25  ω     46.00  91.00   0.50    0.10    --   84.37 -95.00  60.00   90
 26  ω     19.00  53.00   0.50    0.10    --   56.31-125.00 150.00   68
 27  ω     35.00  92.00   0.50    0.10    --   80.00-101.00 174.41  114
 28  ω     37.00  92.00   0.50    0.10    --   76.52-111.00 150.00  110
 29  ω     47.00  92.00   0.50    0.10    --   84.37 -95.00  90.00   90
 30  ω     43.00  92.00   0.50    0.10    --   84.37 -95.00   0.00   98
 31  ω     51.00  92.00   0.50    0.10    --   84.37 -95.00 -30.00   82
 32  ω     66.00  92.00   0.50    0.10    --   84.37 -95.00 -60.00   52
 33  ω     42.00  89.00   0.50    0.10    --   84.37 -95.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1121300000
_diffrn_orient_matrix_UB_12      0.0400353000
_diffrn_orient_matrix_UB_13      0.1246685000
_diffrn_orient_matrix_UB_21      0.0996603000
_diffrn_orient_matrix_UB_22      -0.1119381000
_diffrn_orient_matrix_UB_23      -0.0250885000
_diffrn_orient_matrix_UB_31      0.1048511000
_diffrn_orient_matrix_UB_32      0.0952131000
_diffrn_orient_matrix_UB_33      -0.0706293000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10098
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.961
_diffrn_reflns_theta_min         4.174
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0296
_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)+(0.0304P)²+0.7277P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0743
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3203
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc03979j2.cif
_cod_data_source_block           220428lt_auto
_cod_database_code               7132117
_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   0.880
_shelx_estimated_absorpt_t_min   0.853
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.880
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
Br27 Br 0.49489(3) 0.22405(2) 0.64796(2) 0.03273(9) Uani 1 1 d . . . . .
C1 C 0.4224(2) 0.6134(2) 0.71523(18) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.4039(3) 0.4760(2) 0.70342(19) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.309573 0.426689 0.721259 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5245(3) 0.4113(2) 0.66531(19) 0.0236(5) Uani 1 1 d . . . . .
C4 C 0.6639(3) 0.4795(2) 0.6402(2) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.746384 0.433711 0.616524 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6809(3) 0.6166(2) 0.6504(2) 0.0271(5) Uani 1 1 d . . . . .
H5 H 0.775596 0.665134 0.632466 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5617(2) 0.6837(2) 0.6864(2) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.574434 0.777605 0.691446 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2935(2) 0.68867(19) 0.75476(19) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.1778(2) 0.6097(2) 0.8314(2) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.2286(2) 0.7003(2) 0.9451(2) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.3457(2) 0.7849(2) 0.87786(19) 0.0176(4) Uani 1 1 d . . . . .
H10 H 0.310559 0.874090 0.862677 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2108(2) 0.7526(2) 0.64093(19) 0.0183(4) Uani 1 1 d . . . . .
C12 C 0.0878(2) 0.6781(2) 0.5591(2) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.050517 0.591290 0.579708 0.024 Uiso 1 1 calc R U . . .
C13 C 0.0201(3) 0.7292(2) 0.4487(2) 0.0228(4) Uani 1 1 d . . . . .
H13 H -0.063973 0.677719 0.394576 0.027 Uiso 1 1 calc R U . . .
C14 C 0.0746(2) 0.8559(2) 0.41653(19) 0.0204(4) Uani 1 1 d . . . . .
C15 C 0.1939(2) 0.9327(2) 0.4986(2) 0.0207(4) Uani 1 1 d . . . . .
H15 H 0.229274 1.020279 0.479097 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2608(2) 0.8799(2) 0.60962(19) 0.0200(4) Uani 1 1 d . . . . .
H16 H 0.342482 0.932331 0.665137 0.024 Uiso 1 1 calc R U . . .
C18 C 0.0654(3) 1.0190(2) 0.2612(2) 0.0281(5) Uani 1 1 d . . . . .
H18A H 0.007445 1.033726 0.177941 0.042 Uiso 1 1 calc R U . . .
H18B H 0.178223 1.017706 0.255404 0.042 Uiso 1 1 calc R U . . .
H18C H 0.053439 1.090409 0.321157 0.042 Uiso 1 1 calc R U . . .
C20 C 0.5832(3) 0.7001(2) 1.0145(2) 0.0238(5) Uani 1 1 d . . . . .
H20A H 0.583951 0.615974 0.966119 0.029 Uiso 1 1 calc R U . . .
H20B H 0.529227 0.682431 1.088804 0.029 Uiso 1 1 calc R U . . .
C21 C 0.7494(3) 0.7704(3) 1.0529(3) 0.0463(8) Uani 1 1 d . . . . .
H21A H 0.774665 0.782078 1.146044 0.056 Uiso 1 1 calc R U . . .
H21B H 0.828168 0.718387 1.022384 0.056 Uiso 1 1 calc R U . . .
C23 C 0.6093(2) 0.9073(2) 0.92809(19) 0.0208(4) Uani 1 1 d . . . . .
C26 C 0.1876(3) 0.7030(2) 1.0594(2) 0.0284(5) Uani 1 1 d . . . . .
H26A H 0.110351 0.636627 1.080792 0.034 Uiso 1 1 calc R U . . .
H26B H 0.235481 0.771258 1.119919 0.034 Uiso 1 1 calc R U . . .
N19 N 0.5092(2) 0.79654(16) 0.93605(16) 0.0183(4) Uani 1 1 d . . . . .
O17 O 0.00275(18) 0.89519(15) 0.30388(14) 0.0259(3) Uani 1 1 d . . . . .
O22 O 0.75340(18) 0.89712(16) 0.99677(15) 0.0273(3) Uani 1 1 d . . . . .
O24 O 0.58171(18) 1.00330(15) 0.86875(14) 0.0252(3) Uani 1 1 d . . . . .
O25 O 0.08325(19) 0.51113(15) 0.80733(15) 0.0279(4) 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 0.0181 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 C1 C6 119.04(19) . . ?
C2 C1 C7 121.51(18) . . ?
C6 C1 C7 119.42(18) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.48(19) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 Br27 118.56(17) . . ?
C4 C3 Br27 119.60(17) . . ?
C4 C3 C2 121.8(2) . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C7 C8 115.15(17) . . ?
C1 C7 C10 115.56(16) . . ?
C1 C7 C11 109.59(16) . . ?
C8 C7 C10 86.56(14) . . ?
C11 C7 C8 113.90(17) . . ?
C11 C7 C10 114.65(16) . . ?
C9 C8 C7 92.52(16) . . ?
O25 C8 C7 133.47(19) . . ?
O25 C8 C9 134.0(2) . . ?
C8 C9 C10 91.53(16) . . ?
C26 C9 C8 133.3(2) . . ?
C26 C9 C10 135.2(2) . . ?
C7 C10 H10 110.8 . . ?
C9 C10 C7 89.39(15) . . ?
C9 C10 H10 110.8 . . ?
N19 C10 C7 117.68(16) . . ?
N19 C10 C9 115.74(17) . . ?
N19 C10 H10 110.8 . . ?
C12 C11 C7 119.38(18) . . ?
C16 C11 C7 122.14(18) . . ?
C16 C11 C12 118.30(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.27(19) . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.55(19) . . ?
O17 C14 C13 115.49(19) . . ?
O17 C14 C15 124.96(19) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.47(19) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C15 121.52(19) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O17 C18 H18A 109.5 . . ?
O17 C18 H18B 109.5 . . ?
O17 C18 H18C 109.5 . . ?
H20A C20 H20B 109.3 . . ?
C21 C20 H20A 111.5 . . ?
C21 C20 H20B 111.5 . . ?
N19 C20 H20A 111.5 . . ?
N19 C20 H20B 111.5 . . ?
N19 C20 C21 101.32(17) . . ?
C20 C21 H21A 110.3 . . ?
C20 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
O22 C21 C20 106.98(19) . . ?
O22 C21 H21A 110.3 . . ?
O22 C21 H21B 110.3 . . ?
N19 C23 O22 110.03(18) . . ?
O24 C23 N19 127.4(2) . . ?
O24 C23 O22 122.54(19) . . ?
C9 C26 H26A 120.0 . . ?
C9 C26 H26B 120.0 . . ?
H26A C26 H26B 120.0 . . ?
C10 N19 C20 125.99(16) . . ?
C23 N19 C10 121.33(17) . . ?
C23 N19 C20 112.56(17) . . ?
C14 O17 C18 117.37(17) . . ?
C23 O22 C21 109.10(17) . . ?
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
Br27 C3 1.896(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.402(3) . ?
C1 C7 1.517(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.552(3) . ?
C7 C10 1.597(3) . ?
C7 C11 1.521(3) . ?
C8 C9 1.488(3) . ?
C8 O25 1.212(3) . ?
C9 C10 1.525(3) . ?
C9 C26 1.324(3) . ?
C10 H10 1.0000 . ?
C10 N19 1.437(3) . ?
C11 C12 1.400(3) . ?
C11 C16 1.387(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(3) . ?
C14 C15 1.393(3) . ?
C14 O17 1.365(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(3) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 O17 1.430(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.513(3) . ?
C20 N19 1.452(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 O22 1.441(3) . ?
C23 N19 1.352(3) . ?
C23 O22 1.357(3) . ?
C23 O24 1.210(3) . ?
C26 H26A 0.9500 . ?
C26 H26B 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
Br27 C3 C4 C5 178.32(17) . . . . ?
C1 C2 C3 Br27 -179.20(15) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C7 C8 C9 116.52(18) . . . . ?
C1 C7 C8 O25 -63.0(3) . . . . ?
C1 C7 C10 C9 -116.14(18) . . . . ?
C1 C7 C10 N19 2.9(3) . . . . ?
C1 C7 C11 C12 83.8(2) . . . . ?
C1 C7 C11 C16 -91.3(2) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C2 C1 C7 C8 24.0(3) . . . . ?
C2 C1 C7 C10 122.6(2) . . . . ?
C2 C1 C7 C11 -106.0(2) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C6 C1 C7 C8 -157.89(18) . . . . ?
C6 C1 C7 C10 -59.2(2) . . . . ?
C6 C1 C7 C11 72.2(2) . . . . ?
C7 C1 C2 C3 179.16(18) . . . . ?
C7 C1 C6 C5 179.83(19) . . . . ?
C7 C8 C9 C10 0.18(16) . . . . ?
C7 C8 C9 C26 -179.0(3) . . . . ?
C7 C10 N19 C20 -76.5(3) . . . . ?
C7 C10 N19 C23 107.8(2) . . . . ?
C7 C11 C12 C13 -174.04(19) . . . . ?
C7 C11 C16 C15 173.77(19) . . . . ?
C8 C7 C10 C9 0.17(15) . . . . ?
C8 C7 C10 N19 119.17(18) . . . . ?
C8 C7 C11 C12 -46.8(2) . . . . ?
C8 C7 C11 C16 138.1(2) . . . . ?
C8 C9 C10 C7 -0.17(16) . . . . ?
C8 C9 C10 N19 -120.88(18) . . . . ?
C9 C10 N19 C20 27.4(3) . . . . ?
C9 C10 N19 C23 -148.34(19) . . . . ?
C10 C7 C8 C9 -0.17(16) . . . . ?
C10 C7 C8 O25 -179.7(3) . . . . ?
C10 C7 C11 C12 -144.38(18) . . . . ?
C10 C7 C11 C16 40.5(3) . . . . ?
C11 C7 C8 C9 -115.66(18) . . . . ?
C11 C7 C8 O25 64.8(3) . . . . ?
C11 C7 C10 C9 114.93(18) . . . . ?
C11 C7 C10 N19 -126.06(19) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C11 C16 C15 -1.4(3) . . . . ?
C12 C13 C14 C15 -2.4(3) . . . . ?
C12 C13 C14 O17 178.14(19) . . . . ?
C13 C14 C15 C16 2.2(3) . . . . ?
C13 C14 O17 C18 -174.00(19) . . . . ?
C14 C15 C16 C11 -0.4(3) . . . . ?
C15 C14 O17 C18 6.5(3) . . . . ?
C16 C11 C12 C13 1.2(3) . . . . ?
C20 C21 O22 C23 -1.2(3) . . . . ?
C21 C20 N19 C10 -176.8(2) . . . . ?
C21 C20 N19 C23 -0.7(3) . . . . ?
C26 C9 C10 C7 179.0(3) . . . . ?
C26 C9 C10 N19 58.3(3) . . . . ?
N19 C20 C21 O22 1.1(3) . . . . ?
N19 C23 O22 C21 0.7(3) . . . . ?
O17 C14 C15 C16 -178.33(19) . . . . ?
O22 C23 N19 C10 176.29(17) . . . . ?
O22 C23 N19 C20 0.0(2) . . . . ?
O24 C23 N19 C10 -4.6(3) . . . . ?
O24 C23 N19 C20 179.1(2) . . . . ?
O24 C23 O22 C21 -178.4(2) . . . . ?
O25 C8 C9 C10 179.7(3) . . . . ?
O25 C8 C9 C26 0.5(5) . . . . ?
