Crystal property engineering using molecular-supramolecular equivalence: mechanical property alteration in hydrogen bonded systems.
Mondal, Saikat; Reddy, C. Malla; Saha, Subhankar; Chemical science 15 (2024) 3578–3587; doi:10.1039/d3sc06462j

data_1571371
_publ_section_title
;
 Crystal property engineering using molecular-supramolecular equivalence:
 mechanical property alteration in hydrogen bonded systems.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              3578
_journal_page_last               3587
_journal_paper_doi               10.1039/d3sc06462j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C14 H10 Br0.1 N0.9 O4.8'
_chemical_formula_sum            'C14 H10 Br0.1 N0.9 O4.8'
_chemical_formula_weight         275.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-12-02 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.0056(2)
_cell_length_b                   11.2133(4)
_cell_length_c                   28.6053(11)
_cell_measurement_reflns_used    3636
_cell_measurement_temperature    288(15)
_cell_measurement_theta_max      60.3020
_cell_measurement_theta_min      3.9110
_cell_volume                     1284.84(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_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    -75.00  24.00   0.50    5.59    --  -40.58  99.00 -55.00  198
  2  \w   -111.00 -26.00   0.50    5.59    --  -40.58 -25.00 -17.00  170
  3  \w    -31.00  30.00   0.50    5.59    --  -40.58  25.00 146.00  122
  4  \w    -29.00  31.00   0.50    5.59    --   40.58 -25.00 -17.00  120
  5  \w     37.00  93.00   0.50    5.59    --   40.58-130.00 125.00  112
  6  \w     26.00 111.00   0.50    5.59    --   40.58  25.00 146.00  170
  7  \w   -155.00 -85.00   0.50   22.50    --  -82.50 -99.00-161.00  140
  8  \w   -153.00 -68.00   0.50   22.50    --  -82.50 -25.00 -17.00  170
  9  \w   -150.00 -63.00   0.50   22.50    --  -82.50-140.00 -48.00  174
 10  \w    -90.00 -17.00   0.50   22.50    --  -82.50 130.00-162.00  146
 11  \w    107.00 169.00   0.50   22.50    --   96.35  99.00 -55.00  124
 12  \w     84.00 164.00   0.50   22.50    --   96.35 140.00  10.00  160
 13  \w     91.00 162.00   0.50   22.50    --   96.35 130.00-162.00  142
 14  \w     24.00 107.00   0.50   22.50    --   96.35 -99.00-161.00  166
 15  \w     81.00 167.00   0.50   22.50    --   96.35  25.00 146.00  172
 16  \w   -108.00 -17.00   0.50    5.59    --  -40.58 -64.00 120.00  182
 17  \w     -2.00  75.00   0.50    5.59    --   40.58 -99.00-161.00  154
 18  \w    -35.00  24.00   0.50    5.59    --   40.58 -12.00-120.00  118
 19  \w    -47.00 -15.00   0.50   22.50    --  -82.50  42.00-180.00   64
 20  \w    -47.00 -15.00   0.50   22.50    --  -82.50  42.00  90.00   64
 21  \w     30.00  57.00   0.50   22.50    --   96.35 -50.00-120.00   54
 22  \w     30.00  57.00   0.50   22.50    --   96.35 -50.00  30.00   54
 23  \w     30.00  57.00   0.50   22.50    --   96.35 -50.00 -30.00   54
 24  \w     28.00  68.00   0.50   22.50    --   96.35 -59.00  30.00   80
 25  \w     28.00  68.00   0.50   22.50    --   96.35 -59.00   0.00   80
 26  \w     28.00  68.00   0.50   22.50    --   96.35 -59.00-180.00   80
 27  \w     28.00  68.00   0.50   22.50    --   96.35 -59.00-120.00   80
 28  \w     29.00  83.00   0.50   22.50    --   96.35 -68.00 -30.00  108
 29  \w   -108.00 -17.00   0.50    5.59    --  -40.58 -64.00  60.00  182
 30  \w   -109.00 -14.00   0.50    5.59    --  -40.58 -77.00-150.00  190
 31  \w    -43.00  26.00   0.50    5.59    --  -40.58  38.00-120.00  138
 32  \w   -107.00 -25.00   0.50    5.59    --  -40.58 -38.00-120.00  164
 33  \w   -108.00 -17.00   0.50    5.59    --  -40.58 -64.00 -30.00  182
 34  \w   -109.00 -14.00   0.50    5.59    --  -40.58 -77.00  30.00  190
 35  \w     14.00 109.00   0.50    5.59    --   40.58  77.00-150.00  190
 36  \w     14.00 109.00   0.50    5.59    --   40.58  77.00 150.00  190
 37  \w   -150.00 -90.00   0.50   22.50    --  -82.50 -42.00  60.00  120
 38  \w   -150.00 -66.00   0.50   22.50    --  -82.50 -42.00 -60.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10778
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.100
_diffrn_reflns_theta_min         3.090
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.425
_exptl_crystal_description       needle
_exptl_crystal_F_000             569
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 519 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0686P)^2^+0.2168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.505
_reflns_Friedel_fraction_full    0.786
_reflns_Friedel_fraction_max     0.780
_reflns_number_gt                1760
_reflns_number_total             2128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06462j7.cif
_cod_data_source_block           test2
_cod_original_formula_sum        'C14 H10 Br0.10 N0.90 O4.80'
_cod_database_code               1571371
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.571
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: O1(0.9) O2(0.9) H1bc(0.4) H1bd(0.4) H1ce(0.25) H1cf(0.25)
 H1aa(0.35) H1ab(0.35) O4(0.4) O5(0.3) O3(0.3) N2(0.9) Br2(0.1)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1bc,H1bd), C1(H1ce,H1cf), C1(H1aa,H1ab)
3.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00H(H00H)
;
_shelx_res_checksum              56270
_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
;