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_1571372
_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         'C15 H13 N O5'
_chemical_formula_sum            'C15 H13 N O5'
_chemical_formula_weight         287.26
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-02 deposited with the CCDC.	2024-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                93.1440(10)
_cell_angle_beta                 97.3620(10)
_cell_angle_gamma                94.0610(10)
_cell_formula_units_Z            2
_cell_length_a                   6.97940(10)
_cell_length_b                   7.62590(10)
_cell_length_c                   12.34710(10)
_cell_measurement_reflns_used    11089
_cell_measurement_temperature    100.01(12)
_cell_measurement_theta_max      68.0380
_cell_measurement_theta_min      3.6020
_cell_volume                     648.752(14)
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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     28.00 105.00   0.50    0.20    --   96.35 -77.00 -60.00  154
  2  \w     29.00  83.00   0.50    0.20    --   96.35 -68.00-150.00  108
  3  \w     41.00 100.00   0.50    0.20    --   40.58-138.00-180.00  118
  4  \w     41.00 100.00   0.50    0.20    --   40.58-138.00-120.00  118
  5  \w     -2.00  75.00   0.50    0.20    --   40.58 -99.00 -44.00  154
  6  \w     28.00  68.00   0.50    0.20    --   96.35 -59.00  30.00   80
  7  \w     30.00  57.00   0.50    0.20    --   96.35 -50.00   0.00   54
  8  \w     29.00  83.00   0.50    0.20    --   96.35 -68.00 -30.00  108
  9  \w     30.00  57.00   0.50    0.20    --   96.35 -50.00-120.00   54
 10  \w     30.00  57.00   0.50    0.20    --   96.35 -50.00 -90.00   54
 11  \w     30.00  57.00   0.50    0.20    --   96.35 -50.00 -60.00   54
 12  \w     30.00  57.00   0.50    0.20    --   96.35 -50.00 -30.00   54
 13  \w    -35.00  24.00   0.50    0.20    --   40.58 -12.00-150.00  118
 14  \w    -35.00  24.00   0.50    0.20    --   40.58 -12.00 -30.00  118
 15  \w     29.00  83.00   0.50    0.20    --   96.35 -68.00  90.00  108
 16  \w     30.00  57.00   0.50    0.20    --   96.35 -50.00 120.00   54
 17  \w     23.00 106.00   0.50    0.20    --   96.35 -96.00  60.00  166
 18  \w     33.00 110.00   0.50    0.20    --   96.35-117.00 120.00  154
 19  \w     24.00 107.00   0.50    0.20    --   96.35 -99.00 -44.00  166
 20  \w     23.00 106.00   0.50    0.20    --   96.35 -96.00 -90.00  166
 21  \w     33.00 110.00   0.50    0.20    --   96.35-117.00-120.00  154
 22  \w     33.00 110.00   0.50    0.20    --   96.35-117.00-150.00  154
 23  \w     23.00 106.00   0.50    0.20    --   96.35 -96.00 150.00  166
 24  \w    -64.00  27.00   0.50    0.20    --  -40.58  64.00 -90.00  182
 25  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00-180.00   64
 26  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00-150.00   64
 27  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00-120.00   64
 28  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -90.00   64
 29  \w    -47.00 -15.00   0.50    0.20    --  -82.50  42.00 -60.00   64
 30  \w    -43.00  26.00   0.50    0.20    --  -40.58  38.00  30.00  138
 31  \w    -43.00  26.00   0.50    0.20    --  -40.58  38.00  90.00  138
 32  \w    -81.00 -10.00   0.50    0.20    --  -82.50  99.00  61.00  142
 33  \w    -75.00  24.00   0.50    0.20    --  -40.58  99.00  61.00  198
 34  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00 -30.00  190
 35  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00 -60.00  190
 36  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00   0.00  190
 37  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  30.00  190
 38  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  60.00  190
 39  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00 150.00  190
 40  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00 120.00  190
 41  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00  90.00  190
 42  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-120.00  190
 43  \w   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-180.00  190
 44  \w   -151.00 -68.00   0.50    0.20    --  -82.50 -77.00-120.00  166
 45  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00-180.00  192
 46  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -90.00  192
 47  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00 -30.00  192
 48  \w   -151.00 -55.00   0.50    0.20    --  -82.50 -77.00  60.00  192
 49  \w   -150.00 -58.00   0.50    0.20    --  -82.50 -68.00  90.00  184
 50  \w   -153.00 -68.00   0.50    0.20    --  -82.50 -25.00   0.00  170
 51  \w   -155.00 -85.00   0.50    0.20    --  -82.50 -99.00 -44.00  140
 52  \w     14.00 109.00   0.50    0.20    --   40.58  77.00 -60.00  190
 53  \w     14.00 109.00   0.50    0.20    --   40.58  77.00-120.00  190
 54  \w     22.00 107.00   0.50    0.20    --   40.58  50.00-180.00  170
 55  \w     22.00 107.00   0.50    0.20    --   40.58  50.00 -60.00  170
 56  \w     81.00 167.00   0.50    0.20    --   96.35  25.00  30.00  172
 57  \w     72.00 164.00   0.50    0.20    --   96.35  68.00 150.00  184
 58  \w     70.00 165.00   0.50    0.20    --   96.35  77.00 120.00  190
 59  \w     70.00 165.00   0.50    0.20    --   96.35  77.00   0.00  190
 60  \w     72.00 164.00   0.50    0.20    --   96.35  68.00 -30.00  184
 61  \w     77.00 163.00   0.50    0.20    --   96.35  50.00 -60.00  172
 62  \w     77.00 163.00   0.50    0.20    --   96.35  50.00-120.00  172
 63  \w     77.00 163.00   0.50    0.20    --   96.35  50.00-150.00  172
 64  \w     83.00 164.00   0.50    0.20    --   96.35  33.00-180.00  162
 65  \w     83.00 164.00   0.50    0.20    --   96.35  33.00  90.00  162
 66  \w     77.00 163.00   0.50    0.20    --   96.35  50.00 120.00  172
 67  \w     99.00 160.00   0.50    0.20    --   96.35 117.00  30.00  122
 68  \w    105.00 170.00   0.50    0.20    --   96.35  96.00  90.00  130
 69  \w    107.00 169.00   0.50    0.20    --   96.35  99.00  61.00  124
 70  \w     99.00 160.00   0.50    0.20    --   96.35 117.00 -60.00  122
 71  \w    105.00 170.00   0.50    0.20    --   96.35  96.00-120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0582928000
_diffrn_orient_matrix_UB_12      -0.0790744000
_diffrn_orient_matrix_UB_13      -0.1181317000
_diffrn_orient_matrix_UB_21      0.2150367000
_diffrn_orient_matrix_UB_22      0.0075580000
_diffrn_orient_matrix_UB_23      -0.0173659000
_diffrn_orient_matrix_UB_31      0.0143120000
_diffrn_orient_matrix_UB_32      -0.1867583000
_diffrn_orient_matrix_UB_33      0.0404636000
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11974
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.180
_diffrn_reflns_theta_min         3.617
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66709
_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    1.471
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.60(12)
_refine_ls_extinction_coef       0.023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4101
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0345
_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^)+(0.0735P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0927
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.751
_reflns_Friedel_fraction_max     0.743
_reflns_number_gt                4081
_reflns_number_total             4101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06462j7.cif
_cod_data_source_block           test1
_cod_database_code               1571372
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.912
_shelx_estimated_absorpt_t_min   0.651
_reflns_odcompleteness_completeness 99.96
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00Q(H00H,H00I), C015(H01A,H01B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J), C00L(H00L),
 C00N(H00N), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T), C00X(H00X),
 C00Y(H00Y), C013(H013)
2.c Idealised Me refined as rotating group:
 C00Z(H00A,H00B,H00C), C016(H01C,H01D,H01E)
;
_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 1.419
_oxdiff_exptl_absorpt_empirical_full_min 0.753