Mechanistic study on the structure–property relationship of flexible organic crystals
Zhao, Hongtu; Zhang, Xiunan; Chen, Kui; Wu, Wenbo; Li, Shuyu; Wang, Ting; Huang, Xin; Wang, Na; Zhou, Lina; Hao, Hongxun; CrystEngComm 25 (2023) 2600–2606; doi:10.1039/D3CE00108C

data_7246524
_publ_section_title
;
 Mechanistic study on the structure--property relationship of flexible
 organic crystals
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              2600
_journal_page_last               2606
_journal_paper_doi               10.1039/D3CE00108C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C17 H14 F6 N2 O'
_chemical_formula_sum            'C17 H14 F6 N2 O'
_chemical_formula_weight         376.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-10 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                78.810(9)
_cell_angle_beta                 83.660(11)
_cell_angle_gamma                88.872(11)
_cell_formula_units_Z            2
_cell_length_a                   4.9857(8)
_cell_length_b                   10.6861(12)
_cell_length_c                   16.2064(17)
_cell_measurement_reflns_used    2147
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      32.6490
_cell_measurement_theta_min      3.8470
_cell_volume                     841.84(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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   -115.00  65.00   1.00   25.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  65.00   1.00   25.00    --  -25.00  45.00  90.00  180
  3  \w   -115.00  65.00   1.00   25.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0383164000
_diffrn_orient_matrix_UB_12      0.0021071000
_diffrn_orient_matrix_UB_13      0.0431785000
_diffrn_orient_matrix_UB_21      -0.0075495000
_diffrn_orient_matrix_UB_22      0.0674845000
_diffrn_orient_matrix_UB_23      -0.0104582000
_diffrn_orient_matrix_UB_31      -0.1377136000
_diffrn_orient_matrix_UB_32      -0.0044178000
_diffrn_orient_matrix_UB_33      -0.0063699000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8169
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.530
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.15(4)
_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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.260
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0764
_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^)+(0.1039P)^2^+0.1512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1901
_refine_ls_wR_factor_ref         0.2494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1351
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00108c6.cif
_cod_data_source_block           r20221019c
_cod_depositor_comments
'Adding full bibliography for 7246522--7246525.cif.'
_cod_database_code               7246524
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F4-C17 \\sim F4A-C17 \\sim F5-C17 \\sim F5A-C17 \\sim F6-C17 \\sim F6A-C17
 with sigma of 0.01
 F4-F5 \\sim F4-F6 \\sim F5-F6 \\sim F4A-F5A \\sim F4A-F6A \\sim F5A-F6A
 with sigma of 0.01
 F1-C16 \\sim F1A-C16 \\sim F2-C16 \\sim F2A-C16 \\sim F3-C16 \\sim F3A-C16
 with sigma of 0.01
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F4 \\sim F5 \\sim F6 \\sim F1A \\sim F2A \\sim F3A \\sim F4A \\sim F5A \\sim
F6A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F1A \\sim F2A \\sim F3A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F1A) \\sim
Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F4A) \\sim Ueq,
Uanis(F5A) \\sim Ueq, Uanis(F6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C15(H15)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              44806
_shelx_hkl_checksum              72931
_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 1.833
_oxdiff_exptl_absorpt_empirical_full_min 0.741