#------------------------------------------------------------------------------
#$Date: 2022-01-19 01:32:53 +0200 (Wed, 19 Jan 2022) $
#$Revision: 272111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/42/7244246.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_7244246
loop_
_publ_author_name
'Yamashita, Yutaro'
'Tashiro, Shohei'
'Shionoya, Mitsuhiko'
_publ_section_title
;
 Orientational isomerisation of guest molecules in equilibrium in a
 tubular host crystal formed via halogen and hydrogen bonding
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01654G
_journal_year                    2022
_chemical_formula_moiety         'Br, C7 H8 Br2 N, C0.5 H Cl'
_chemical_formula_sum            'C7.5 H9 Br3 Cl N'
_chemical_formula_weight         388.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-11-24
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-26 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.3030(2)
_cell_length_b                   11.39340(10)
_cell_length_c                   8.87830(10)
_cell_measurement_reflns_used    5038
_cell_measurement_temperature    183
_cell_measurement_theta_max      71.4930
_cell_measurement_theta_min      3.8020
_cell_volume                     2357.19(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      183
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  85.00   0.50    0.50    --    0.00  77.00 -60.00  238
  2  ω      8.00  33.00   0.50    0.50    --    0.00  57.00 -90.00   50
  3  ω     53.00 119.00   0.50    0.50    --   95.70 -82.00-180.00  132
  4  ω     90.00 121.00   0.50    0.50    --   95.70 -30.00   0.00   62
  5  ω     56.00  84.00   0.50    0.50    --   95.70 -61.00-180.00   56
  6  ω      7.00  52.00   0.50    0.50    --   95.70 -61.00-180.00   90
  7  ω     23.00  76.00   0.50    0.50    --   95.70 -30.00   0.00  106
  8  ω     88.00 116.00   0.50    0.50    --   95.70 -61.00-180.00   56
  9  ω     16.00 126.00   0.50    0.50    --   95.70 -30.00-120.00  220
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0650691000
_diffrn_orient_matrix_UB_12      0.0218026000
_diffrn_orient_matrix_UB_13      -0.0118176000
_diffrn_orient_matrix_UB_21      -0.0102425000
_diffrn_orient_matrix_UB_22      -0.1329939000
_diffrn_orient_matrix_UB_23      -0.0158422000
_diffrn_orient_matrix_UB_31      -0.0054656000
_diffrn_orient_matrix_UB_32      -0.0107282000
_diffrn_orient_matrix_UB_33      0.1724520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.059
_diffrn_reflns_theta_min         3.794
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    14.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.189
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.086
_refine_diff_density_min         -1.263
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0446
_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)+(0.0716P)²+8.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2126
_reflns_number_total             2273
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01654g2.cif
_cod_data_source_block           DCM_183K
_cod_original_formula_sum        'C7.50 H9 Br3 Cl N'
_cod_database_code               7244246
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         CHNBrCl
_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   0.672
_shelx_estimated_absorpt_t_min   0.161
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Others
 Sof(C1GB)=Sof(H1GC)=Sof(H1GD)=0.5*(1-FVAR(2))
 Sof(C1GA)=Sof(H1GA)=Sof(H1GB)=0.5*FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B), C1GA(H1GA,H1GB), C1GB(H1GC,H1GD)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C3(H3)
;
_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.653
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
Br3 Br 0.40860(2) 0.36882(4) 1.13769(6) 0.02966(19) Uani 1 1 d . . . . .
Br2 Br 0.44724(2) 0.82885(4) 0.60523(6) 0.0327(2) Uani 1 1 d . . . . .
Br1 Br 0.23881(2) 0.42360(6) 0.53958(8) 0.0483(2) Uani 1 1 d . . . . .
Cl1G Cl 0.31148(10) 0.7656(3) 0.3105(5) 0.1296(14) Uani 1 1 d . . . . .
N1 N 0.40922(18) 0.4558(4) 0.7968(5) 0.0307(9) Uani 1 1 d . . . . .
H1 H 0.412695 0.430422 0.890040 0.037 Uiso 1 1 calc R . . . .
C5 C 0.4410(2) 0.5814(4) 0.6022(5) 0.0252(10) Uani 1 1 d . . . . .
C4 C 0.4461(2) 0.5371(4) 0.7468(5) 0.0266(10) Uani 1 1 d . . . . .
H4 H 0.475854 0.564523 0.810839 0.032 Uiso 1 1 calc R . . . .
C2 C 0.3608(2) 0.4494(4) 0.5634(5) 0.0278(10) Uani 1 1 d . . . . .
C6 C 0.3978(2) 0.5355(4) 0.5106(5) 0.0265(9) Uani 1 1 d . . . . .
H6 H 0.393680 0.563670 0.410506 0.032 Uiso 1 1 calc R . . . .
C7 C 0.4802(2) 0.6760(4) 0.5492(6) 0.0299(10) Uani 1 1 d . . . . .
H7A H 0.484875 0.671341 0.438561 0.036 Uiso 1 1 calc R . . . .
H7B H 0.518496 0.666636 0.596251 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3674(2) 0.4116(4) 0.7110(6) 0.0304(10) Uani 1 1 d . . . . .
H3 H 0.342112 0.354078 0.751101 0.036 Uiso 1 1 calc R . . . .
C1 C 0.3160(2) 0.3940(6) 0.4650(7) 0.0417(13) Uani 1 1 d . . . . .
H1A H 0.322677 0.308271 0.460447 0.050 Uiso 1 1 calc R . . . .
H1B H 0.319552 0.425599 0.361524 0.050 Uiso 1 1 calc R . . . .
C1GA C 0.250000 0.750000 0.392(3) 0.076(9) Uani 0.50(3) 2 d S T P A 1
H1GA H 0.254175 0.681090 0.458679 0.091 Uiso 0.248(16) 1 calc R . . A 1
H1GB H 0.245825 0.818909 0.458679 0.091 Uiso 0.248(16) 1 calc R . . A 1
C1GB C 0.250000 0.750000 0.232(3) 0.107(13) Uani 0.50(3) 2 d S T P A 2
H1GC H 0.245830 0.818836 0.164857 0.128 Uiso 0.252(16) 1 calc R . . A 2
H1GD H 0.254170 0.681163 0.164858 0.128 Uiso 0.252(16) 1 calc R . . 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
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
C4 N1 H1 118.7 . . ?
C3 N1 H1 118.7 . . ?
C3 N1 C4 122.6(4) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 C7 120.3(4) . . ?
C6 C5 C7 122.0(4) . . ?
N1 C4 C5 120.4(4) . . ?
N1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C2 C3 118.0(4) . . ?
C6 C2 C1 122.2(5) . . ?
C3 C2 C1 119.8(5) . . ?
C5 C6 H6 119.4 . . ?
C2 C6 C5 121.1(5) . . ?
C2 C6 H6 119.4 . . ?
Br2 C7 H7A 109.9 . . ?
Br2 C7 H7B 109.9 . . ?
C5 C7 Br2 108.7(3) . . ?
C5 C7 H7A 109.9 . . ?
C5 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C3 C2 120.2(4) . . ?
N1 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
Br1 C1 H1A 109.3 . . ?
Br1 C1 H1B 109.3 . . ?
C2 C1 Br1 111.8(4) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
Cl1G C1GA Cl1G 127.0(18) 2_565 . ?
Cl1G C1GA H1GA 105.6 2_565 . ?
Cl1G C1GA H1GA 105.6 . . ?
Cl1G C1GA H1GB 105.6 2_565 . ?
Cl1G C1GA H1GB 105.6 . . ?
H1GA C1GA H1GB 106.1 . . ?
Cl1G C1GB Cl1G 128.4(18) 2_565 . ?
Cl1G C1GB H1GC 105.2 2_565 . ?
Cl1G C1GB H1GC 105.2 . . ?
Cl1G C1GB H1GD 105.2 2_565 . ?
Cl1G C1GB H1GD 105.2 . . ?
H1GC C1GB H1GD 105.9 . . ?
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
Br2 C7 1.967(5) . ?
Br1 C1 1.946(6) . ?
Cl1G C1GA 1.613(13) . ?
Cl1G C1GB 1.603(13) . ?
N1 H1 0.8800 . ?
N1 C4 1.339(6) . ?
N1 C3 1.336(7) . ?
C5 C4 1.384(7) . ?
C5 C6 1.396(7) . ?
C5 C7 1.490(7) . ?
C4 H4 0.9500 . ?
C2 C6 1.388(7) . ?
C2 C3 1.388(7) . ?
C2 C1 1.500(7) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C3 H3 0.9500 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1GA H1GA 0.9900 . ?
C1GA H1GB 0.9900 . ?
C1GB H1GC 0.9900 . ?
C1GB H1GD 0.9900 . ?
