Evaluating structure-property relationship in a new family of mechanically flexible co-crystals
Abeysekera, Amila M.; Averkiev, Boris B.; Sinha, Abhijeet Shekhar; Aakeröy, Christer; Chemical Communications  (2022) –; doi:10.1039/D2CC02047E

data_7130415
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -108.00 -61.00   0.50   17.73    --  -43.05-147.00 103.00   94
  2  \w    -83.00 -14.00   0.50   17.73    --  -43.05 124.00 -12.00  138
  3  \w     41.00  66.00   0.50   17.73    --   43.05-124.00 -90.00   50
  4  \w     78.00 103.00   0.50   17.73    --   43.05-147.00 103.00   50
  5  \w   -134.00 -76.00   0.50   70.93    --  -90.25-124.00 -90.00  116
  6  \w    -87.00 -62.00   0.50   70.93    --  -90.25 147.00 153.00   50
  7  \w    100.00 126.00   0.50   70.93    --  111.75 147.00 153.00   52
  8  \w     98.00 124.00   0.50   70.93    --  111.75 124.00 -12.00   52
  9  \w     78.00 111.00   0.50   70.93    --  111.75-124.00 -90.00   66
 10  \w     73.00 126.00   0.50   70.93    --  111.75-147.00 103.00  106
 11  \w   -118.00 -85.00   0.50   17.73    --  -43.05-178.00-180.00   66
 12  \w    -38.00  33.00   0.50   17.73    --  -43.05  38.00 120.00  142
 13  \w    -17.00  26.00   0.50   17.73    --   43.05 -19.00 150.00   86
 14  \w    -36.00  25.00   0.50   17.73    --   43.05 -19.00 -90.00  122
 15  \w     84.00 112.00   0.50   70.93    --  111.75-125.00 -60.00   56
 16  \w     92.00 118.00   0.50   70.93    --  111.75  77.00 -30.00   52
 17  \w    126.00 178.00   0.50   70.93    --  111.75  77.00  60.00  104
 18  \w     80.00 105.00   0.50   70.93    --  111.75 -94.00 -60.00   50
 19  \w     99.00 124.00   0.50   70.93    --  111.75 125.00-120.00   50
 20  \w     47.00  83.00   0.50   70.93    --  111.75 -77.00 -60.00   72
 21  \w    103.00 128.00   0.50   70.93    --  111.75  45.00-120.00   50
 22  \w     70.00 103.00   0.50   70.93    --  111.75 -77.00  30.00   66
 23  \w     39.00  65.00   0.50   70.93    --  111.75 -59.00 -15.46   52
 24  \w     82.00 108.00   0.50   70.93    --  111.75-110.00 -56.09   52
 25  \w     73.00  99.00   0.50   70.93    --  111.75 -94.00-150.00   52
 26  \w     73.00 100.00   0.50   70.93    --  111.75 -77.00 -30.00   54
 27  \w     78.00 104.00   0.50   70.93    --  111.75 -94.00 -30.00   52
 28  \w     70.00 102.00   0.50   70.93    --  111.75  15.00   0.00   64
 29  \w    118.00 178.00   0.50   70.93    --  111.75  15.00   0.00  120
 30  \w     42.00  70.00   0.50   70.93    --  111.75 -61.00-180.00   56
 31  \w     45.00  70.00   0.50   70.93    --  111.75 -61.00 150.00   50
 32  \w    122.00 155.00   0.50   70.93    --  111.75  45.00-150.00   66
 33  \w    153.00 178.00   0.50   70.93    --  111.75  77.00 -30.00   50
 34  \w    130.00 173.00   0.50   70.93    --  111.75  45.00-120.00   86
 35  \w     41.00  99.00   0.50   70.93    --  111.75 -94.00 -83.65  116
 36  \w     70.00 104.00   0.50   70.93    --  111.75 -77.00  90.00   68
 37  \w     42.00  67.00   0.50   70.93    --  111.75 -96.00 -62.29   50
 38  \w     46.00  86.00   0.50   70.93    --  111.75-125.00  60.00   80
 39  \w     97.00 122.00   0.50   70.93    --  111.75  77.00  60.00   50
 40  \w    108.00 140.00   0.50   70.93    --  111.75  61.00  30.00   64
 41  \w    111.00 137.00   0.50   70.93    --  111.75  61.00  60.00   52
 42  \w    139.00 165.00   0.50   70.93    --  111.75 136.00  74.49   52
 43  \w     97.00 123.00   0.50   70.93    --  111.75  74.00-104.15   52
 44  \w    148.00 177.00   0.50   70.93    --  111.75  74.00-104.15   58
 45  \w    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       '\w 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/[\s^2^(Fo^2^)+(0.0665P)^2^+0.7429P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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