#------------------------------------------------------------------------------
#$Date: 2022-07-27 00:55:19 +0300 (Wed, 27 Jul 2022) $
#$Revision: 276944 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/04/7130415.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_7130415
loop_
_publ_author_name
'Abeysekera, Amila M.'
'Averkiev, Boris B.'
'Sinha, Abhijeet Shekhar'
'Aakeröy, Christer'
_publ_section_title
;
 Evaluating structure-property relationship in a new family of
 mechanically flexible co-crystals
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02047E
_journal_year                    2022
_chemical_formula_moiety         'C8 H9 Br N2 O, C7 H6 O2'
_chemical_formula_sum            'C15 H15 Br N2 O3'
_chemical_formula_weight         351.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-02-14 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.928(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0457(6)
_cell_length_b                   4.9964(3)
_cell_length_c                   21.3687(7)
_cell_measurement_reflns_used    4526
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      76.3290
_cell_measurement_theta_min      3.7220
_cell_volume                     1499.41(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.111a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -61.00   0.50   17.73    --  -43.05-147.00 103.00   94
  2  ω    -83.00 -14.00   0.50   17.73    --  -43.05 124.00 -12.00  138
  3  ω     41.00  66.00   0.50   17.73    --   43.05-124.00 -90.00   50
  4  ω     78.00 103.00   0.50   17.73    --   43.05-147.00 103.00   50
  5  ω   -134.00 -76.00   0.50   70.93    --  -90.25-124.00 -90.00  116
  6  ω    -87.00 -62.00   0.50   70.93    --  -90.25 147.00 153.00   50
  7  ω    100.00 126.00   0.50   70.93    --  111.75 147.00 153.00   52
  8  ω     98.00 124.00   0.50   70.93    --  111.75 124.00 -12.00   52
  9  ω     78.00 111.00   0.50   70.93    --  111.75-124.00 -90.00   66
 10  ω     73.00 126.00   0.50   70.93    --  111.75-147.00 103.00  106
 11  ω   -118.00 -85.00   0.50   17.73    --  -43.05-178.00-180.00   66
 12  ω    -38.00  33.00   0.50   17.73    --  -43.05  38.00 120.00  142
 13  ω    -17.00  26.00   0.50   17.73    --   43.05 -19.00 150.00   86
 14  ω    -36.00  25.00   0.50   17.73    --   43.05 -19.00 -90.00  122
 15  ω     84.00 112.00   0.50   70.93    --  111.75-125.00 -60.00   56
 16  ω     92.00 118.00   0.50   70.93    --  111.75  77.00 -30.00   52
 17  ω    126.00 178.00   0.50   70.93    --  111.75  77.00  60.00  104
 18  ω     80.00 105.00   0.50   70.93    --  111.75 -94.00 -60.00   50
 19  ω     99.00 124.00   0.50   70.93    --  111.75 125.00-120.00   50
 20  ω     47.00  83.00   0.50   70.93    --  111.75 -77.00 -60.00   72
 21  ω    103.00 128.00   0.50   70.93    --  111.75  45.00-120.00   50
 22  ω     70.00 103.00   0.50   70.93    --  111.75 -77.00  30.00   66
 23  ω     39.00  65.00   0.50   70.93    --  111.75 -59.00 -15.46   52
 24  ω     82.00 108.00   0.50   70.93    --  111.75-110.00 -56.09   52
 25  ω     73.00  99.00   0.50   70.93    --  111.75 -94.00-150.00   52
 26  ω     73.00 100.00   0.50   70.93    --  111.75 -77.00 -30.00   54
 27  ω     78.00 104.00   0.50   70.93    --  111.75 -94.00 -30.00   52
 28  ω     70.00 102.00   0.50   70.93    --  111.75  15.00   0.00   64
 29  ω    118.00 178.00   0.50   70.93    --  111.75  15.00   0.00  120
 30  ω     42.00  70.00   0.50   70.93    --  111.75 -61.00-180.00   56
 31  ω     45.00  70.00   0.50   70.93    --  111.75 -61.00 150.00   50
 32  ω    122.00 155.00   0.50   70.93    --  111.75  45.00-150.00   66
 33  ω    153.00 178.00   0.50   70.93    --  111.75  77.00 -30.00   50
 34  ω    130.00 173.00   0.50   70.93    --  111.75  45.00-120.00   86
 35  ω     41.00  99.00   0.50   70.93    --  111.75 -94.00 -83.65  116
 36  ω     70.00 104.00   0.50   70.93    --  111.75 -77.00  90.00   68
 37  ω     42.00  67.00   0.50   70.93    --  111.75 -96.00 -62.29   50
 38  ω     46.00  86.00   0.50   70.93    --  111.75-125.00  60.00   80
 39  ω     97.00 122.00   0.50   70.93    --  111.75  77.00  60.00   50
 40  ω    108.00 140.00   0.50   70.93    --  111.75  61.00  30.00   64
 41  ω    111.00 137.00   0.50   70.93    --  111.75  61.00  60.00   52
 42  ω    139.00 165.00   0.50   70.93    --  111.75 136.00  74.49   52
 43  ω     97.00 123.00   0.50   70.93    --  111.75  74.00-104.15   52
 44  ω    148.00 177.00   0.50   70.93    --  111.75  74.00-104.15   58
 45  ω    131.00 158.00   0.50   70.93    --  111.75 124.00 -12.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0775407000
_diffrn_orient_matrix_UB_12      -0.1887418000
_diffrn_orient_matrix_UB_13      -0.0263798000
_diffrn_orient_matrix_UB_21      -0.0647415000
_diffrn_orient_matrix_UB_22      0.2425319000
_diffrn_orient_matrix_UB_23      -0.0138196000
_diffrn_orient_matrix_UB_31      0.0428466000
_diffrn_orient_matrix_UB_32      0.0249692000
_diffrn_orient_matrix_UB_33      -0.0656438000
_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  0.0524
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.353
_diffrn_reflns_theta_min         3.738
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.846
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
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    1.556
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method 'crystallized from ethyl acetate'
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0441
_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)+(0.0665P)²+0.7429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2338
_reflns_number_total             3137
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           Br-Et_BA
_cod_database_code               7130415
_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   0.924
_shelx_estimated_absorpt_t_min   0.681
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C3(H3), C18(H18), C14(H14), C6(H6), C17(H17), C5(H5), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_olex2_date_sample_data_collection 2021-06-23
_olex2_date_sample_submission    2021-06-23
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_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 2.357
_oxdiff_exptl_absorpt_empirical_full_min 0.574
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br7 Br 0.13950(3) 0.02579(10) 0.47917(2) 0.06556(18) Uani 1 1 d . . . . .
O20 O 0.51574(15) 0.4117(5) 0.71762(11) 0.0527(5) Uani 1 1 d . . . . .
O21 O 0.36738(16) 0.5356(5) 0.69247(10) 0.0523(5) Uani 1 1 d . . . . .
H21 H 0.372538 0.413050 0.665820 0.078 Uiso 1 1 calc R U . . .
O10 O 0.59424(18) -0.3595(6) 0.58272(11) 0.0608(6) Uani 1 1 d . . . . .
N8 N 0.5106(2) -0.0062(5) 0.62128(12) 0.0497(6) Uani 1 1 d . . . . .
H8 H 0.513616 0.122369 0.649399 0.060 Uiso 1 1 calc R U . . .
N2 N 0.36194(19) 0.1630(6) 0.60223(12) 0.0501(6) Uani 1 1 d . . . . .
C13 C 0.4428(2) 0.7546(7) 0.77699(13) 0.0441(6) Uani 1 1 d . . . . .
C19 C 0.4463(2) 0.5503(7) 0.72645(14) 0.0450(7) Uani 1 1 d . . . . .
C1 C 0.4275(2) -0.0177(6) 0.58570(14) 0.0463(7) Uani 1 1 d . . . . .
C4 C 0.2582(2) -0.0026(7) 0.52239(14) 0.0496(7) Uani 1 1 d . . . . .
C3 C 0.2790(2) 0.1697(8) 0.57069(14) 0.0527(7) Uani 1 1 d . . . . .
H3 H 0.232675 0.298576 0.582154 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5889(2) -0.1694(7) 0.61833(14) 0.0494(7) Uani 1 1 d . . . . .
C18 C 0.3648(2) 0.9247(7) 0.78281(14) 0.0479(7) Uani 1 1 d . . . . .
H18 H 0.312450 0.911842 0.754249 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5189(2) 0.7739(7) 0.81939(15) 0.0521(7) Uani 1 1 d . . . . .
H14 H 0.572082 0.657915 0.815661 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4102(3) -0.2027(7) 0.53750(14) 0.0532(8) Uani 1 1 d . . . . .
H6 H 0.456628 -0.332957 0.527167 0.064 Uiso 1 1 calc R U . . .
C17 C 0.3640(2) 1.1130(8) 0.83060(15) 0.0519(7) Uani 1 1 d . . . . .
H17 H 0.311186 1.230238 0.834586 0.062 Uiso 1 1 calc R U . . .
C5 C 0.3247(3) -0.1915(8) 0.50558(14) 0.0535(8) Uani 1 1 d . . . . .
H5 H 0.311454 -0.312498 0.472267 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6686(2) -0.0887(8) 0.66251(16) 0.0566(8) Uani 1 1 d . . . . .
H11A H 0.701984 0.067779 0.644809 0.068 Uiso 1 1 calc R U . . .
H11B H 0.641021 -0.032895 0.702807 0.068 Uiso 1 1 calc R U . . .
C16 C 0.4403(3) 1.1300(8) 0.87255(15) 0.0560(8) Uani 1 1 d . . . . .
H16 H 0.439470 1.258518 0.905312 0.067 Uiso 1 1 calc R U . . .
C15 C 0.5170(3) 0.9614(8) 0.86680(16) 0.0585(9) Uani 1 1 d . . . . .
H15 H 0.569047 0.973945 0.895615 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7399(3) -0.3082(9) 0.67469(19) 0.0649(9) Uani 1 1 d . . . . .
H12A H 0.764572 -0.372903 0.634802 0.097 Uiso 1 1 calc R U . . .
H12B H 0.709033 -0.456046 0.696649 0.097 Uiso 1 1 calc R U . . .
H12C H 0.792595 -0.238657 0.700555 0.097 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
C9 N8 C1 128.3(3) . . ?
C3 N2 C1 118.7(3) . . ?
C18 C13 C19 121.2(3) . . ?
C14 C13 C19 119.0(3) . . ?
C14 C13 C18 119.7(3) . . ?
O20 C19 O21 123.6(3) . . ?
O20 C19 C13 122.7(3) . . ?
O21 C19 C13 113.6(3) . . ?
N8 C1 C6 124.4(3) . . ?
N2 C1 N8 113.8(3) . . ?
N2 C1 C6 121.7(3) . . ?
C3 C4 Br7 119.5(3) . . ?
C3 C4 C5 119.3(3) . . ?
C5 C4 Br7 121.2(2) . . ?
N2 C3 C4 122.4(3) . . ?
O10 C9 N8 123.3(3) . . ?
O10 C9 C11 123.1(3) . . ?
N8 C9 C11 113.6(3) . . ?
C17 C18 C13 119.6(3) . . ?
C15 C14 C13 120.1(3) . . ?
C5 C6 C1 118.5(3) . . ?
C16 C17 C18 120.1(3) . . ?
C6 C5 C4 119.3(3) . . ?
C12 C11 C9 113.5(3) . . ?
C15 C16 C17 120.2(3) . . ?
C16 C15 C14 120.4(3) . . ?
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
Br7 C4 1.899(3) . ?
O20 C19 1.213(4) . ?
O21 C19 1.317(4) . ?
O10 C9 1.220(4) . ?
N8 C1 1.385(4) . ?
N8 C9 1.372(4) . ?
N2 C1 1.341(4) . ?
N2 C3 1.337(4) . ?
C13 C19 1.487(4) . ?
C13 C18 1.394(5) . ?
C13 C14 1.393(4) . ?
C1 C6 1.402(5) . ?
C4 C3 1.372(5) . ?
C4 C5 1.379(5) . ?
C9 C11 1.507(5) . ?
C18 C17 1.389(5) . ?
C14 C15 1.380(5) . ?
C6 C5 1.372(5) . ?
C17 C16 1.389(5) . ?
C11 C12 1.505(5) . ?
C16 C15 1.375(5) . ?
