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_7245290
_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, 0.5(H2 O)'
_chemical_formula_sum            'C21 H17 Cl F5 N2 O1.5'
_chemical_formula_weight         451.82
_chemical_melting_point          440.0(10)
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-25
_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                   9.0543(2)
_cell_length_b                   13.0350(2)
_cell_length_c                   34.3367(6)
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.3550
_cell_measurement_theta_min      2.5630
_cell_volume                     4052.51(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.34a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_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    -98.00 -15.00   0.50    1.25    --  -43.55 -19.00  62.00  166
  2  \w   -156.00-129.00   0.50    5.01    --  -97.00-109.00 -55.00   54
  3  \w   -154.00 -94.00   0.50    5.01    --  -97.00-121.00-140.00  120
  4  \w     89.00 173.00   0.50    5.01    --  113.46  19.00-129.00  168
  5  \w   -112.00 -63.00   0.50    1.25    --  -43.55-179.00-150.00   98
  6  \w    -29.00  22.00   0.50    1.25    --   43.55 -19.00 -60.00  102
  7  \w    -54.00 -23.00   0.50    5.01    --  -97.00  45.00-150.00   62
  8  \w    -57.00 -32.00   0.50    5.01    --  -97.00  61.00-150.00   50
  9  \w     41.00  67.00   0.50    5.01    --  113.46 -61.00-150.00   52
 10  \w     41.00  67.00   0.50    5.01    --  113.46 -94.00-120.00   52
 11  \w     52.00 100.00   0.50    5.01    --  113.46 -94.00 -60.00   96
 12  \w     42.00  67.00   0.50    5.01    --  113.46 -61.00  30.00   50
 13  \w     45.00  81.00   0.50    5.01    --  113.46 -94.00 -30.00   72
 14  \w     80.00 105.00   0.50    5.01    --  113.46 -94.00-120.00   50
 15  \w     40.00  68.00   0.50    5.01    --  113.46 -61.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0260127000
_diffrn_orient_matrix_UB_12      -0.0239109000
_diffrn_orient_matrix_UB_13      0.0434209000
_diffrn_orient_matrix_UB_21      -0.1671380000
_diffrn_orient_matrix_UB_22      0.0161505000
_diffrn_orient_matrix_UB_23      -0.0056881000
_diffrn_orient_matrix_UB_31      -0.0180783000
_diffrn_orient_matrix_UB_32      -0.1145903000
_diffrn_orient_matrix_UB_33      -0.0098327000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15075
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.772
_diffrn_reflns_theta_min         2.574
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.34a (Rigaku Oxford Diffraction, 2019)
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    1.481
_exptl_crystal_description       plate
_exptl_crystal_F_000             1848
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: iPrOH'
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 2202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.394(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         7498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0168P)^2^+8.6529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.619
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                6611
_reflns_number_total             7498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00972b3.cif
_cod_data_source_block           exp_2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '439-441' was changed to
'440.0(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_original_formula_sum        'C21 H17 Cl F5 N2 O1.50'
_cod_database_code               7245290
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C21H16Cl1F5N2O1
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 N4(H4), N2(H2)
2.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C30(H30), C13(H13), C16(H16), C15(H15), C9(H9), C19(H19),
 C18(H18), C39(H39), C12(H12), C10(H10), C40(H40), C11(H11), C34(H34), C31(H31),
  C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C42(H42A,H42B,
 H42C)
;
_shelx_res_checksum              89912
_shelx_hkl_checksum              43235
_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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.520