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_1571370
_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_absolute_configuration unk
_chemical_formula_moiety         'C14 H11 N O5'
_chemical_formula_sum            'C14 H11 N O5'
_chemical_formula_weight         273.247
_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'
_symmetry_Int_Tables_number      19
_audit_creation_date             2022-05-17
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2022.05.04 svn.r4f934e98 for OlexSys, GUI svn.r6444)
;
_audit_update_record
;
2023-06-13 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                   4.00906(4)
_cell_length_b                   11.18764(10)
_cell_length_c                   28.5930(2)
_cell_measurement_reflns_used    11002
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8980
_cell_measurement_theta_min      3.0790
_cell_volume                     1282.451(19)
_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 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9965
_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    -31.00  30.00   0.50    0.50    --  -40.33  25.00  60.00  122
  2  \w    -31.00  30.00   0.50    0.50    --  -40.33  25.00   0.00  122
  3  \w    -47.00 -15.00   0.50    5.00    --  -82.50  42.00-150.00   64
  4  \w    -85.00 -11.00   0.50    0.50    --  -40.33 123.00-162.00  148
  5  \w     14.00 109.00   0.50    0.50    --   40.33  77.00-180.00  190
  6  \w     96.00 163.00   0.50    5.00    --   96.67 123.00-162.00  134
  7  \w     82.00 167.00   0.50    5.00    --   96.67  25.00   0.00  170
  8  \w     99.00 164.00   0.50    5.00    --   96.67 117.00  60.00  130
  9  \w     81.00 164.00   0.50    5.00    --   96.67 145.00 150.00  166
 10  \w     83.00 164.00   0.50    5.00    --   96.67  33.00  30.00  162
 11  \w     75.00 130.00   0.50    5.00    --   96.67  59.00-120.00  110
 12  \w     71.00 170.00   0.50    5.00    --   96.67  17.00 -30.00  198
 13  \w     47.00 107.00   0.50    0.50    --   40.33-150.00 -45.00  120
 14  \w     28.00 105.00   0.50    5.00    --   96.67 -77.00 -30.00  154
 15  \w     32.00 111.00   0.50    5.00    --   96.67-123.00 117.00  158
 16  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00  90.00   54
 17  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 120.00   54
 18  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 150.00   54
 19  \w     28.00 105.00   0.50    5.00    --   96.67 -77.00  90.00  154
 20  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 -60.00   54
 21  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00 -90.00   54
 22  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00-120.00   54
 23  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00-150.00   54
 24  \w     30.00  57.00   0.50    5.00    --   96.67 -50.00-180.00   54
 25  \w     29.00  83.00   0.50    5.00    --   96.67 -68.00-180.00  108
 26  \w     17.00 108.00   0.50    0.50    --   40.33  64.00 -90.00  182
 27  \w     14.00 109.00   0.50    0.50    --   40.33  77.00-150.00  190
 28  \w    -26.00  57.00   0.50    0.50    --   40.33 -50.00-120.00  166
 29  \w    -35.00  24.00   0.50    0.50    --   40.33 -12.00-150.00  118
 30  \w    -30.00  31.00   0.50    0.50    --   40.33 -25.00  90.00  122
 31  \w    -27.00  64.00   0.50    0.50    --   40.33 -64.00  90.00  182
 32  \w     14.00 109.00   0.50    0.50    --   40.33  77.00 150.00  190
 33  \w   -104.00 -25.00   0.50    0.50    --  -40.33 150.00  -0.00  158
 34  \w   -107.00 -21.00   0.50    0.50    --  -40.33 -50.00  30.00  172
 35  \w   -107.00 -21.00   0.50    0.50    --  -40.33 -50.00  60.00  172
 36  \w   -108.00 -55.00   0.50    0.50    --  -40.33-150.00 -45.00  106
 37  \w   -109.00 -13.00   0.50    0.50    --  -40.33 -77.00 -30.00  192
 38  \w   -108.00 -17.00   0.50    0.50    --  -40.33 -64.00 -90.00  182
 39  \w   -109.00 -13.00   0.50    0.50    --  -40.33 -77.00   0.00  192
 40  \w   -109.00 -13.00   0.50    0.50    --  -40.33 -77.00 150.00  192
 41  \w   -109.00 -13.00   0.50    0.50    --  -40.33 -77.00  30.00  192
 42  \w   -149.00 -74.00   0.50    5.00    --  -82.50-123.00 117.00  150
 43  \w   -160.00 -36.00   0.50    5.00    --  -82.50  -8.00 120.00  248
 44  \w   -150.00 -69.00   0.50    5.00    --  -82.50 -33.00-120.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.9986
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12951
_diffrn_reflns_point_group_measured_fraction_full 0.9957
_diffrn_reflns_point_group_measured_fraction_max 0.9923
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65225
_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    1.415
_exptl_crystal_description       needle
_exptl_crystal_F_000             570.255
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1454
_refine_diff_density_min         -0.1762
_refine_diff_density_rms         0.0406
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.09(6)
_refine_ls_d_res_high            0.8300
_refine_ls_d_res_low             14.2965
_refine_ls_goodness_of_fit_ref   1.1213
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2328
_refine_ls_number_restraints     184
_refine_ls_restrained_S_all      1.0747
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+0.1243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.986
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              34
_reflns_limit_l_min              -33
_reflns_number_gt                2192
_reflns_number_total             2328
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3sc06462j7.cif
_cod_data_source_block           suvsa1_rt_1
_cod_original_cell_volume        1282.45(2)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1571370
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O001-C005 \\sim O001-C0
 with sigma of 0.02
 H00F-C00G \\sim H2a-C3
 with sigma of 0.04
 C005-C00E \\sim C0-C1
 with sigma of 0.02
 C005-C00F \\sim C0-C2
 with sigma of 0.02
 C00E-H00I \\sim C1-H00J
 with sigma of 0.04
 C00E-H00E \\sim C1-H1
 with sigma of 0.02
 C00H-H00I \\sim C5-H00J
 with sigma of 0.04
 C00E-C00I \\sim C1-C00J
 with sigma of 0.02
 C00F-H00F \\sim C2-H2a
 with sigma of 0.02
 C00F-C00G \\sim C2-C3
 with sigma of 0.02
 C00F-H00G \\sim C2-H3
 with sigma of 0.04
 C00G-H00G \\sim C3-H3
 with sigma of 0.02
 C00G-C4 \\sim C3-C4A
 with sigma of 0.04
 C00G-C00H \\sim C3-C5
 with sigma of 0.02
 C00H-C00I \\sim C5-C00J
 with sigma of 0.02
 C00I-C4 \\sim C00J-C4A
 with sigma of 0.04
 C00H-C4 \\sim C5-C4A
 with sigma of 0.02
 C00I-H00I \\sim C00J-H00J
 with sigma of 0.02
 O2-C4 \\sim O2AB-C4A
 with sigma of 0.02
 C00E-C00H \\sim C1-C5
 with sigma of 0.04
 H00E-C00I \\sim H1-C00J
 with sigma of 0.04
 C00F-C00H \\sim C2-C5
 with sigma of 0.04
 C00G-C00I \\sim C3-C00J
 with sigma of 0.04
 H00G-C00H \\sim H3-C5
 with sigma of 0.04
 C00H-O2 \\sim C5-O2AB
 with sigma of 0.04
 O001-C00E \\sim O001-C1
 with sigma of 0.04
 O001-C00F \\sim O001-C2
 with sigma of 0.04
 C005-H00E \\sim C0-H1
 with sigma of 0.04
 C005-H00F \\sim C0-H2a
 with sigma of 0.04
 C005-C00G \\sim C0-C3
 with sigma of 0.04
 C005-C00I \\sim C0-C00J
 with sigma of 0.04
 C00E-C00F \\sim C1-C2
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C4 \\sim C4A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(O2) \\sim Ueq, Uanis(O2AB) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C4)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C0, C5, O2AB, C1, C00J, C2, C4A, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C005, C00I, C00E, O2, C00H, C00F, C4, C00G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C005(0.3) C00E(0.3) H00E(0.3) C00I(0.3) H00I(0.3) C00H(0.3)
 C00G(0.3) H00G(0.3) C00F(0.3) H00F(0.3) C4(0.3) H4a(0.3) H4b(0.3) C0(0.7)
 C1(0.7) H1(0.7) C2(0.7) H2a(0.7) C3(0.7) H3(0.7) C5(0.7) C00J(0.7) H00J(0.7)
 O2AB(0.3) C4A(0.7) H4Ad(0.35) H4Ac(0.35) H4Aa(0.35) H4Ab(0.35) H2AB(0.3)
 H2(0.3) H2(0.25) O2(0.25) O2AA(0.45) H2AA(0.45)
6.a Riding coordinates:
 C4A(H4Ad,H4Ac), C4A(H4Aa,H4Ab), O2(H2), O2AA(H2AA)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b)
6.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00G(H00G), C00F(H00F), C009(H009), C00B(H00B),
 C00C(H00C), C00D(H00D), C1(H1), C2(H2a), C3(H3), C00J(H00J)
6.d Fitted hexagon refined as free rotating group:
 C005(C00E,C00I,C00H,C00G,C00F)
6.e Idealised tetrahedral OH refined as rotating group:
 O2AB(H2AB)
;
_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
;