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_7130413
_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, C9 H10 O2'
_chemical_formula_sum            'C17 H19 Br N2 O3'
_chemical_formula_weight         379.25
_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             2021-06-21
_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                97.664(3)
_cell_angle_beta                 93.157(5)
_cell_angle_gamma                91.561(4)
_cell_formula_units_Z            2
_cell_length_a                   4.7003(3)
_cell_length_b                   12.7927(5)
_cell_length_c                   14.1635(6)
_cell_measurement_reflns_used    4204
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.9120
_cell_measurement_theta_min      3.1430
_cell_volume                     842.24(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     36.00  70.00   0.50    0.05    --   47.70  63.00 129.00   68
  2  \w     88.00 117.00   0.50    0.05    --   47.70  63.00 129.00   58
  3  \w    102.00 139.00   0.50    0.14    --  107.74 125.00 -60.00   74
  4  \w     42.00 118.00   0.50    0.05    --   47.70  57.00 -60.00  152
  5  \w     39.00  65.00   0.50    0.05    --   47.70 -63.00  -7.00   52
  6  \w     -7.00  32.00   0.50    0.05    --   47.70 -63.00  -7.00   78
  7  \w     40.00  74.00   0.50    0.14    --  107.74 -99.00 120.00   68
  8  \w     84.00 111.00   0.50    0.14    --  107.74-125.00 150.00   54
  9  \w     35.00  61.00   0.50    0.14    --  107.74-125.00 150.00   52
 10  \w     64.00 103.00   0.50    0.14    --  107.74-125.00  90.00   78
 11  \w     81.00 106.00   0.50    0.14    --  107.74 -99.00 120.00   50
 12  \w     81.00 106.00   0.50    0.14    --  107.74 -99.00  60.00   50
 13  \w     65.00 111.00   0.50    0.14    --  107.74-125.00   0.00   92
 14  \w     38.00 104.00   0.50    0.14    --  107.74 -99.00 -30.00  132
 15  \w     35.00  99.00   0.50    0.14    --  107.74 -99.00-150.00  128
 16  \w     36.00  82.00   0.50    0.14    --  107.74 -99.00-180.00   92
 17  \w     39.00 100.00   0.50    0.14    --  107.74 -77.00-150.00  122
 18  \w     78.00 103.00   0.50    0.14    --  107.74 -77.00-120.00   50
 19  \w     49.00  75.00   0.50    0.14    --  107.74 -77.00-120.00   52
 20  \w     38.00  64.00   0.50    0.14    --  107.74 -57.00-120.00   52
 21  \w     79.00 104.00   0.50    0.14    --  107.74 -77.00 -30.00   50
 22  \w     35.00  63.00   0.50    0.14    --  107.74 -57.00 -30.00   56
 23  \w     35.00  60.00   0.50    0.14    --  107.74 -63.00  -7.00   50
 24  \w     37.00  62.00   0.50    0.14    --  107.74 -57.00 150.00   50
 25  \w    113.00 178.00   0.50    0.14    --  107.74  38.00  30.00  130
 26  \w     93.00 165.00   0.50    0.14    --  107.74  57.00  60.00  144
 27  \w     92.00 176.00   0.50    0.14    --  107.74  63.00 129.00  168
 28  \w    111.00 162.00   0.50    0.14    --  107.74  38.00 -60.00  102
 29  \w    -26.00  25.00   0.50    0.05    --  -47.70  19.00 120.00  102
 30  \w    -16.00  25.00   0.50    0.05    --  -47.70  63.00 129.00   82
 31  \w    -62.00 -30.00   0.50    0.05    --  -47.70  63.00 129.00   64
 32  \w    -68.00 -43.00   0.50    0.14    --  -86.25  63.00 129.00   50
 33  \w    -62.00 -16.00   0.50    0.14    --  -86.25  57.00 120.00   92
 34  \w    -43.00 -18.00   0.50    0.14    --  -86.25  38.00  60.00   50
 35  \w    -66.00 -22.00   0.50    0.14    --  -86.25  57.00 -60.00   88
 36  \w    -43.00 -18.00   0.50    0.14    --  -86.25  38.00-120.00   50
 37  \w    -39.00 -14.00   0.50    0.14    --  -86.25  38.00-150.00   50
 38  \w    -67.00 -30.00   0.50    0.05    --  -47.70 -63.00  -7.00   74
 39  \w   -122.00 -80.00   0.50    0.14    --  -86.25 -63.00  -7.00   84
 40  \w   -113.00 -83.00   0.50    0.05    --  -47.70 -63.00  -7.00   60
 41  \w   -140.00 -94.00   0.50    0.14    --  -86.25 -99.00  90.00   92
;
_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      -0.0325501000
_diffrn_orient_matrix_UB_12      0.1057571000
_diffrn_orient_matrix_UB_13      -0.0396366000
_diffrn_orient_matrix_UB_21      -0.2423556000
_diffrn_orient_matrix_UB_22      -0.0499786000
_diffrn_orient_matrix_UB_23      -0.0707108000
_diffrn_orient_matrix_UB_31      -0.2192885000
_diffrn_orient_matrix_UB_32      0.0331743000
_diffrn_orient_matrix_UB_33      0.0742735000
_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  0.0650
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9084
_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         77.194
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.467
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_preparation       'grown from 1:1 mixture'
_exptl_crystal_recrystallization_method 'crystallized from methanol'
_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.078
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0560
_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/[\s^2^(Fo^2^)+(0.1064P)^2^+0.1332P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3072
_reflns_number_total             3358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           Br-Et_35M-BA
_cod_database_code               7130413
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H19 Br1 N2 O3'
_shelx_estimated_absorpt_t_max   0.774
_shelx_estimated_absorpt_t_min   0.161
_reflns_odcompleteness_completeness 99.44
_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
 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), C18(H18), C5(H5), C6(H6), C3(H3), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C12(H12A,H12B,H12C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O21(H21)
;
_shelx_res_checksum              74351
_shelx_hkl_checksum              82921
_olex2_date_sample_completion    2020-12-13
_olex2_date_sample_data_collection 2020-12-12
_olex2_date_sample_submission    2020-12-10
_olex2_exptl_crystal_mounting_method 'mounted on a glass fibre'
_olex2_submission_original_sample_id AA-Br-propyl-3,5-dimethyl-BA
_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 2.045
_oxdiff_exptl_absorpt_empirical_full_min 0.524