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_7130416
_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         'C7 H5 Cl O2, C8 H10 N2 O'
_chemical_formula_sum            'C15 H15 Cl N2 O3'
_chemical_formula_weight         306.74
_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             2021-06-23
_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                 106.2128(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3651(2)
_cell_length_b                   4.47304(5)
_cell_length_c                   21.7942(3)
_cell_measurement_reflns_used    9567
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      77.2250
_cell_measurement_theta_min      3.1160
_cell_volume                     1438.32(3)
_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 2018/2 (Sheldrick, 2018)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_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      3.00  36.00   0.50    5.00    --   47.95 -54.00  11.00   66
  2  \w     36.00  62.00   0.50   25.00    --  107.75 -54.00  11.00   52
  3  \w     69.00  99.00   0.50   25.00    --  107.75 -77.00   0.00   60
  4  \w     72.00 103.00   0.50   25.00    --  107.75 -77.00  60.00   62
  5  \w     65.00 104.00   0.50   25.00    --  107.75 -94.00   0.00   78
  6  \w     69.00  95.00   0.50   25.00    --  107.75 -94.00 -30.00   52
  7  \w     61.00  87.00   0.50   25.00    --  107.75 -77.00 -90.00   52
  8  \w     66.00  92.00   0.50   25.00    --  107.75 -77.00-150.00   52
  9  \w     44.00  70.00   0.50   25.00    --  107.75 -61.00 -90.00   52
 10  \w     40.00  90.00   0.50   25.00    --  107.75 -77.00 -30.00  100
 11  \w     41.00  70.00   0.50   25.00    --  107.75 -61.00  60.00   58
 12  \w     42.00  71.00   0.50   25.00    --  107.75 -61.00  90.00   58
 13  \w     41.00  67.00   0.50   25.00    --  107.75 -77.00  60.00   52
 14  \w     41.00  66.00   0.50   25.00    --  107.75 -77.00  90.00   50
 15  \w     42.00  91.00   0.50   25.00    --  107.75 -77.00 150.00   98
 16  \w     47.00  72.00   0.50   25.00    --  107.75-125.00 120.00   50
 17  \w     35.00  66.00   0.50   25.00    --  107.75 -94.00 120.00   62
 18  \w     35.00  65.00   0.50   25.00    --  107.75 -77.00   0.00   60
 19  \w     40.00  65.00   0.50   25.00    --  107.75 -94.00 -30.00   50
 20  \w     35.00  60.00   0.50   25.00    --  107.75 -61.00   0.00   50
 21  \w    102.00 133.00   0.50   25.00    --  107.75  30.00 -60.00   62
 22  \w    137.00 163.00   0.50   25.00    --  107.75  30.00 -60.00   52
 23  \w    133.00 159.00   0.50   25.00    --  107.75  61.00 -90.00   52
 24  \w    113.00 152.00   0.50   25.00    --  107.75  45.00-120.00   78
 25  \w     91.00 118.00   0.50   25.00    --  107.75  61.00 -90.00   54
 26  \w    113.00 139.00   0.50   25.00    --  107.75  45.00  60.00   52
 27  \w    141.00 175.00   0.50   25.00    --  107.75  45.00  60.00   68
 28  \w    147.00 175.00   0.50   25.00    --  107.75  77.00  60.00   56
 29  \w    142.00 176.00   0.50   25.00    --  107.75  61.00 120.00   68
 30  \w    127.00 177.00   0.50   25.00    --  107.75  54.00 155.00  100
 31  \w    127.00 153.00   0.50   25.00    --  107.75  45.00 120.00   52
 32  \w    113.00 147.00   0.50   25.00    --  107.75  15.00 120.00   68
 33  \w    105.00 168.00   0.50   25.00    --  107.75  45.00 150.00  126
 34  \w    111.00 136.00   0.50   25.00    --  107.75  61.00 120.00   50
 35  \w     86.00 121.00   0.50   25.00    --  107.75  77.00  60.00   70
 36  \w     76.00 101.00   0.50    5.00    --   47.95  54.00 155.00   50
 37  \w    -18.00  26.00   0.50    5.00    --  -47.95  19.00 -90.00   88
 38  \w    -61.00  25.00   0.50    5.00    --  -47.95  54.00 155.00  172
 39  \w     35.00  60.00   0.50   25.00    --  107.75 -61.00-120.00   50
 40  \w     36.00  62.00   0.50   25.00    --  107.75 -77.00-180.00   52
 41  \w     38.00  64.00   0.50   25.00    --  107.75 -77.00-150.00   52
 42  \w     39.00  69.00   0.50   25.00    --  107.75 -61.00-150.00   60
 43  \w   -111.00 -73.00   0.50    5.00    --  -47.95-125.00 150.00   76
 44  \w   -119.00 -58.00   0.50    5.00    --  -47.95 -54.00  11.00  122
 45  \w   -140.00-115.00   0.50   25.00    --  -86.25 -54.00  11.00   50
 46  \w    -62.00 -37.00   0.50   25.00    --  -86.25  54.00 155.00   50
;
_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      -0.0812127000
_diffrn_orient_matrix_UB_12      0.0245937000
_diffrn_orient_matrix_UB_13      -0.0601497000
_diffrn_orient_matrix_UB_21      0.0536005000
_diffrn_orient_matrix_UB_22      0.2224710000
_diffrn_orient_matrix_UB_23      -0.0293963000
_diffrn_orient_matrix_UB_31      0.0379036000
_diffrn_orient_matrix_UB_32      -0.2616546000
_diffrn_orient_matrix_UB_33      -0.0306402000
_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  0.0223
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.583
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67801
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method 'crystallized from ethylacetate'
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3062
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.2951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2862
_reflns_number_total             3062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02047e2.cif
_cod_data_source_block           H-Et_4Cl-BA
_cod_database_code               7130416
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H15 N2 O3 Cl'
_chemical_oxdiff_usercomment     'redo experiment 42 at 200K'
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.485
_reflns_odcompleteness_completeness 96.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N7(H7), C17(H17), C16(H16), C13(H13), C6(H6), C14(H14), C3(H3), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O20(H20)
;
_olex2_date_sample_submission    2020-12-16
_olex2_exptl_crystal_mounting_method 'mounted on a MiTeGen loop'
_olex2_submission_original_sample_id AA-propyl-H:4ClBA
_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 1.511
_oxdiff_exptl_absorpt_empirical_full_min 0.714