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_1571373
_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      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   mixed
_audit_creation_date             2023-12-02
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.95360(10)
_cell_length_b                   11.24500(10)
_cell_length_c                   30.6382(5)
_cell_measurement_reflns_used    9082
_cell_measurement_temperature    285(12)
_cell_measurement_theta_max      67.9200
_cell_measurement_theta_min      2.8500
_cell_volume                     1362.12(4)
_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_temperature      285(12)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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    -78.00   4.00   0.50    2.00    --  -40.58 104.00-170.00  164
  2  \w     18.00  78.00   0.50    2.00    --   40.58-104.00  88.00  120
  3  \w    -82.00 -12.00   0.50    8.00    --  -82.50 104.00-170.00  140
  4  \w    105.00 167.00   0.50    8.00    --   96.35 104.00-170.00  124
  5  \w     26.00 108.00   0.50    8.00    --   96.35-104.00  88.00  164
  6  \w    -67.00  28.00   0.50    2.00    --  -40.58  77.00 150.00  190
  7  \w    -31.00  30.00   0.50    2.00    --  -40.58  25.00 150.00  122
  8  \w    -43.00  26.00   0.50    2.00    --  -40.58  38.00   0.00  138
  9  \w   -109.00 -14.00   0.50    2.00    --  -40.58 -77.00 -30.00  190
 10  \w    -25.00  43.00   0.50    2.00    --   40.58 -38.00 -30.00  136
 11  \w     18.00  78.00   0.50    2.00    --   40.58-104.00 -90.00  120
 12  \w    -68.00 -14.00   0.50    8.00    --  -82.50  59.00-180.00  108
 13  \w   -153.00 -78.00   0.50    8.00    --  -82.50 -87.00 150.00  150
 14  \w    -57.00 -16.00   0.50    8.00    --  -82.50  50.00  90.00   82
 15  \w   -153.00 -83.00   0.50    8.00    --  -82.50-104.00  88.00  140
 16  \w    -47.00 -15.00   0.50    8.00    --  -82.50  42.00  60.00   64
 17  \w     44.00 127.00   0.50    8.00    --   96.35-145.00 -60.00  166
 18  \w     28.00  68.00   0.50    8.00    --   96.35 -59.00 150.00   80
 19  \w     99.00 160.00   0.50    8.00    --   96.35 117.00 120.00  122
 20  \w     28.00  68.00   0.50    8.00    --   96.35 -59.00   0.00   80
 21  \w     30.00  57.00   0.50    8.00    --   96.35 -50.00 -30.00   54
 22  \w     30.00  57.00   0.50    8.00    --   96.35 -50.00  90.00   54
 23  \w     83.00 164.00   0.50    8.00    --   96.35  33.00-180.00  162
 24  \w     28.00  68.00   0.50    8.00    --   96.35 -59.00  60.00   80
 25  \w     28.00 105.00   0.50    8.00    --   96.35 -77.00 -30.00  154
 26  \w     30.00  57.00   0.50    8.00    --   96.35 -50.00 120.00   54
 27  \w     30.00  57.00   0.50    8.00    --   96.35 -50.00  60.00   54
 28  \w     23.00 106.00   0.50    8.00    --   96.35 -96.00 150.00  166
 29  \w     99.00 160.00   0.50    8.00    --   96.35 117.00 150.00  122
 30  \w     29.00  83.00   0.50    8.00    --   96.35 -68.00  30.00  108
 31  \w     29.00  83.00   0.50    8.00    --   96.35 -68.00  60.00  108
 32  \w     28.00  68.00   0.50    8.00    --   96.35 -59.00 -30.00   80
 33  \w     99.00 160.00   0.50    8.00    --   96.35 117.00  30.00  122
 34  \w    105.00 170.00   0.50    8.00    --   96.35  96.00  90.00  130
 35  \w   -107.00 -25.00   0.50    2.00    --  -40.58 -38.00  30.00  164
 36  \w    -24.00  35.00   0.50    2.00    --  -40.58  12.00-120.00  118
 37  \w   -108.00 -17.00   0.50    2.00    --  -40.58 -64.00   0.00  182
 38  \w   -107.00 -21.00   0.50    2.00    --  -40.58 -50.00-150.00  172
 39  \w   -109.00 -14.00   0.50    2.00    --  -40.58 -77.00 -60.00  190
 40  \w   -109.00 -14.00   0.50    2.00    --  -40.58 -77.00-180.00  190
 41  \w     14.00 109.00   0.50    2.00    --   40.58  77.00  60.00  190
 42  \w     14.00 109.00   0.50    2.00    --   40.58  77.00 120.00  190
 43  \w     14.00 109.00   0.50    2.00    --   40.58  77.00-150.00  190
;
_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  0.0407
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13435
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.020
_diffrn_reflns_theta_min         2.885
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33516
_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    1.401
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     246
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0804P)^2^+0.0742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                2200
_reflns_number_total             2404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06462j7.cif
_cod_data_source_block           test1_CCDC1
_cod_database_code               1571373
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.573
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C00A-C00G \\sim C2-C4
 with sigma of 0.02
 C00A-C00H \\sim C2-C5
 with sigma of 0.02
 C00C-C00I \\sim C7-C6
 with sigma of 0.02
 C00G-H00G \\sim C4-H4
 with sigma of 0.02
 C00G-C00J \\sim C4-C00K
 with sigma of 0.02
 C00H-H00A \\sim C5-H5A
 with sigma of 0.02
 C00H-H00D \\sim C5-H5B
 with sigma of 0.02
 C00H-H00H \\sim C5-H5C
 with sigma of 0.02
 C00I-H00I \\sim C6-H6
 with sigma of 0.02
 C00I-C00J \\sim C6-C00K
 with sigma of 0.02
 C00J-C1 \\sim C00K-C1A
 with sigma of 0.02
 O001-C00A \\sim O001-C2
 with sigma of 0.04
 O001-C00C \\sim O001-C7
 with sigma of 0.04
 C00A-C00C \\sim C2-C7
 with sigma of 0.04
 C00A-H00G \\sim C2-H4
 with sigma of 0.04
 C00A-H00A \\sim C2-H5A
 with sigma of 0.04
 C00A-H00D \\sim C2-H5B
 with sigma of 0.04
 C00A-H00H \\sim C2-H5C
 with sigma of 0.04
 C00A-C00J \\sim C2-C00K
 with sigma of 0.04
 C00C-H00I \\sim C7-H6
 with sigma of 0.04
 C00C-C00J \\sim C7-C00K
 with sigma of 0.04
 C00G-C00H \\sim C4-C5
 with sigma of 0.04
 C00G-C00I \\sim C4-C6
 with sigma of 0.04
 C00G-C1 \\sim C4-C1A
 with sigma of 0.04
 H00G-C00J \\sim H4-C00K
 with sigma of 0.04
 H00A-H00D \\sim H5A-H5B
 with sigma of 0.04
 H00A-H00H \\sim H5A-H5C
 with sigma of 0.04
 H00D-H00H \\sim H5B-H5C
 with sigma of 0.04
 C00I-C1 \\sim C6-C1A
 with sigma of 0.04
 H00I-C00J \\sim H6-C00K
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O2 \\sim O4 \\sim O1 \\sim O3: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.008 within 2A
C009: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 2A
4. Rigid body (RIGU) restrains
 O001, C005, C009, O002, C006, C00A, C00C, C008, C00B, C00G, C00H, C00I, C00E,
 C00F, C00J, C00D, C1, N003, O004, O007
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C7, C4, C5, C6, C00K, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C00A(0.5) C00C(0.5) H00C(0.5) C00G(0.5) H00G(0.5) C00H(0.5)
 H00A(0.5) H00D(0.5) H00H(0.5) C00I(0.5) H00I(0.5) C00J(0.5) C1(0.5) H1AA(0.25)
 H1AB(0.25) H1BC(0.25) H1BD(0.25) C2(0.5) C7(0.5) H7(0.5) C4(0.5) H4(0.5)
 C5(0.5) H5A(0.5) H5B(0.5) H5C(0.5) C6(0.5) H6(0.5) C00K(0.5) C1A(0.5)
 H1AC(0.25) H1AD(0.25) H1AE(0.25) H1AF(0.25) O4(0.25) H4A(0.25) O2(0.25)
 H2(0.25) O3(0.25) H3(0.25) O1(0.25) H1(0.25)
6.a Riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1A(H1AC,H1AD), C1A(H1AE,H1AF), O4(H4A), O2(H2),
  O3(H3)
6.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G),
 C00I(H00I), C7(H7), C4(H4), C6(H6)
6.c Idealised Me refined as rotating group:
 C00H(H00A,H00D,H00H), C5(H5A,H5B,H5C)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
;