Unexpected triaxial preferences in some all-syn 1,3,5-trifluorocyclohexanes
O'Hagan, David; Yu, Cihang; Cormanich, Rodrigo A.; Slawin, Alexandra; Cordes, David Bradford; Piscelli, Bruno A.; Al-Maharik, Nawaf; Chemical Communications  (2022) –; doi:10.1039/D2CC05058G

data_7130900
_publ_section_title
;
 Unexpected triaxial preferences in some all-syn
 1,3,5-trifluorocyclohexanes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05058G
_journal_year                    2022
_chemical_formula_moiety         'C11 H18 F3 N O2'
_chemical_formula_sum            'C11 H18 F3 N O2'
_chemical_formula_weight         253.26
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-08-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-19 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.696(4)
_cell_angle_beta                 96.546(5)
_cell_angle_gamma                98.362(5)
_cell_formula_units_Z            4
_cell_length_a                   6.2763(4)
_cell_length_b                   9.5541(4)
_cell_length_c                   21.1552(10)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.7310
_cell_measurement_theta_min      4.9220
_cell_volume                     1238.20(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_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    'SIR2011  (Burla et al.,  2007)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f      0.00 200.00   0.50   10.00   0.00 -30.00   0.00    --   400
  2  \w    -72.00   1.00   0.50   10.00    --  -30.00 -72.00 -90.00  146
  3  \w   -113.00 -71.00   0.50   10.00    --  -30.00 180.00 -45.00   84
  4  \f      0.00 200.00   0.50   10.00   0.00 -67.00   0.00    --   400
  5  \w    -85.00 -13.00   0.50   10.00    --  -67.00  72.00  90.00  144
  6  \w   -133.00 -93.00   0.50   10.00    --  -67.00 180.00   0.00   80
  7  \w    -85.00 -12.00   0.50   10.00    --  -67.00  72.00 -90.00  146
  8  \w   -126.00 -86.00   0.50   10.00    --  -67.00 180.00-180.00   80
  9  \f      0.00 200.00   0.50   10.00 -25.00-110.00   0.00    --   400
 10  \w   -128.00 -20.00   0.50   10.00    -- -110.00  72.00-135.00  216
 11  \w   -128.00 -20.00   0.50   10.00    -- -110.00  72.00  45.00  216
 12  \w   -115.00 -20.00   0.50   10.00    -- -110.00  72.00 -45.00  190
 13  \w   -113.00 -23.00   0.50   10.00    -- -110.00  72.00 135.00  180
 14  \w   -141.00 -46.00   0.50   10.00    -- -110.00 180.00 -90.00  190
 15  \w   -141.00 -46.00   0.50   10.00    -- -110.00 180.00-180.00  190
 16  \w   -141.00 -59.00   0.50   10.00    -- -110.00 180.00  90.00  164
 17  \w   -141.00 -55.00   0.50   10.00    -- -110.00 180.00   0.00  172
 18  \w   -141.00 -59.00   0.50   10.00    -- -110.00 180.00  45.00  164
 19  \w   -141.00 -78.00   0.50   10.00    -- -110.00 180.00 -45.00  126
 20  \w   -140.00 -77.00   0.50   10.00    -- -110.00 180.00-135.00  126
 21  \w   -140.00 -56.00   0.50   10.00    -- -110.00 180.00 135.00  168
;
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1551216000
_diffrn_orient_matrix_UB_12      0.0984653000
_diffrn_orient_matrix_UB_13      0.0532045000
_diffrn_orient_matrix_UB_21      0.0474240000
_diffrn_orient_matrix_UB_22      0.1090514000
_diffrn_orient_matrix_UB_23      -0.0475748000
_diffrn_orient_matrix_UB_31      -0.1905372000
_diffrn_orient_matrix_UB_32      0.0731322000
_diffrn_orient_matrix_UB_33      0.0188270000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25453
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.117
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
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    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone/dichloromethane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         8795
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0774P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4680
_reflns_number_total             8795
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 16.8755\% 
 around [-0.34 -0.91 0.24] (reciprocal) or [-0.71 -0.70 -0.02] (direct)
;
_cod_data_source_file            d2cc05058g2.cif
_cod_data_source_block           10
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7130900
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4988(11)
 0.5012(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N7-H7 = N27-H27
 0.98 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6), C21(H21), C22(H22), C24(H24), C26(H26)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C23(H23A,H23B), C25(H25A,H25B)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              93595
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2