Reversible On/Off Conformational Switching of Pentafluorobenzoyl Amide Triggered by Acid Vapor and Sublimation
Yamasaki, Ryu; Harada, Misuzu; Ito, Ai; Fukuda, Kazuo; Matsumoto, Shota; Karasawa, Satoru; Okamoto, Iwao; CrystEngComm  (2022) –; doi:10.1039/D2CE00972B

data_7245291
_publ_section_title
;
 Reversible On/Off Conformational Switching of Pentafluorobenzoyl Amide
 Triggered by Acid Vapor and Sublimation
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00972B
_journal_year                    2022
_chemical_formula_moiety         'Cl, C21 H16 F5 N2 O'
_chemical_formula_sum            'C21 H16 Cl F5 N2 O'
_chemical_formula_weight         442.81
_chemical_melting_point          436.0(10)
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-03 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1986(3)
_cell_length_b                   9.3685(3)
_cell_length_c                   32.0246(9)
_cell_measurement_reflns_used    8823
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.1700
_cell_measurement_theta_min      2.7770
_cell_volume                     3959.88(19)
_computing_cell_refinement       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_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     -3.00  25.00   0.50    0.06    --   48.95 -19.00  30.00   56
  2  \w    -20.00  24.00   0.50    0.06    --   48.95 -19.00-150.00   88
  3  \w     89.00 116.00   0.50    0.06    --   48.95 125.00 -30.00   54
  4  \w    135.00 175.00   0.50    0.24    --  107.74  86.00 -16.00   80
  5  \w    -69.00 -43.00   0.50    0.24    --  -97.00  57.00 -90.00   52
  6  \w    -70.00 -45.00   0.50    0.24    --  -97.00  57.00-150.00   50
  7  \w    -69.00 -37.00   0.50    0.24    --  -97.00  57.00-180.00   64
  8  \w    -62.00 -26.00   0.50    0.24    --  -97.00  57.00   0.00   72
  9  \w    -70.00 -25.00   0.50    0.24    --  -97.00  57.00 150.00   90
 10  \w    -51.00 -26.00   0.50    0.24    --  -97.00  40.00 150.00   50
 11  \w   -164.00 -99.00   0.50    0.24    --  -97.00 -40.00  -3.00  130
 12  \w   -153.00-127.00   0.50    0.24    --  -97.00-108.00 138.00   52
 13  \w   -120.00 -51.00   0.50    0.06    --  -48.95 -40.00  -3.00  138
 14  \w    -96.00 -24.00   0.50    0.24    --  -97.00 125.00-150.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0163736000
_diffrn_orient_matrix_UB_12      0.0366247000
_diffrn_orient_matrix_UB_13      0.0464442000
_diffrn_orient_matrix_UB_21      -0.0565179000
_diffrn_orient_matrix_UB_22      -0.1422279000
_diffrn_orient_matrix_UB_23      0.0061236000
_diffrn_orient_matrix_UB_31      0.1008007000
_diffrn_orient_matrix_UB_32      -0.0738293000
_diffrn_orient_matrix_UB_33      0.0110198000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            15262
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.512
_diffrn_reflns_theta_min         2.760
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     225
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0457P)^2^+1.8568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3448
_reflns_number_total             3865
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00972b3.cif
_cod_data_source_block           ai518-211119-3ry13a-ca
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '435-437' was changed to
'436.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7245291
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H16ClF5N2O
_shelx_estimated_absorpt_t_max   0.758
_shelx_estimated_absorpt_t_min   0.548
_reflns_odcompleteness_completeness 99.98
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C19 \\sim C17 \\sim C1 \\sim C9 \\sim C7: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
C4 \\sim C20 \\sim C14 \\sim C18 \\sim C6 \\sim C8: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
C12 \\sim C21 \\sim C13 \\sim C2 \\sim C5 \\sim C11: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
3. Rigid body (RIGU) restrains
 C16, C19, C17, C1, C9, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C20, C14, C18, F1, C6, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C21, C13, C2, C5, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 N2(H2)
4.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C11(H11), C13(H13), C7(H7), C2(H2A), C17(H17), C9(H9), C19(H19),
 C5(H5)
4.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              71074
_shelx_hkl_checksum              60825
_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 2.008
_oxdiff_exptl_absorpt_empirical_full_min 0.523