Janus faced fluorocyclohexanes for supramolecular assembly: Synthesis and solid state structures of equatorial mono-, di- and tri alkylated cyclohexanes and with tri-axial C-F bonds to impart polarity.
Poskin, Thomas J.; Piscelli, Bruno A.; Yoshida, Keigo; Cordes, David Bradford; Slawin, Alexandra; Cormanich, Rodrigo A.; Yamada, Shigeyuki; O'Hagan, David; Chemical Communications  (2022) –; doi:10.1039/D2CC03010A

data_7130253
_publ_section_title
;
 Janus faced fluorocyclohexanes for supramolecular assembly: Synthesis and
 solid state structures of equatorial mono-, di- and tri alkylated
 cyclohexanes and with tri-axial C-F bonds to impart polarity.
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03010A
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H57 F3 O3'
_chemical_formula_sum            'C33 H57 F3 O3'
_chemical_formula_weight         558.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-05-23 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.937(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.1482(8)
_cell_length_b                   4.7110(2)
_cell_length_c                   19.5670(9)
_cell_measurement_reflns_used    12655
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.7910
_cell_measurement_theta_min      2.6660
_cell_volume                     1559.39(15)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_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    5.00   0.00 -30.00   0.00    --   400
  2  \w    -72.00   1.00   0.50    5.00    --  -30.00 -72.00 -90.00  146
  3  \w   -111.00 -69.00   0.50    5.00    --  -30.00 180.00 -45.00   84
  4  \f      0.00 200.00   0.50    5.00   0.00 -67.00   0.00    --   400
  5  \w    -83.00 -11.00   0.50    5.00    --  -67.00  72.00  90.00  144
  6  \w   -133.00 -93.00   0.50    5.00    --  -67.00 180.00   0.00   80
  7  \w    -83.00 -10.00   0.50    5.00    --  -67.00  72.00 -90.00  146
  8  \w   -126.00 -86.00   0.50    5.00    --  -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   -126.00 -20.00   0.50   10.00    -- -110.00  72.00-135.00  212
 11  \w   -126.00 -20.00   0.50   10.00    -- -110.00  72.00  45.00  212
 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      0.0408198000
_diffrn_orient_matrix_UB_12      0.2625624000
_diffrn_orient_matrix_UB_13      0.0496718000
_diffrn_orient_matrix_UB_21      -0.0630529000
_diffrn_orient_matrix_UB_22      0.1930027000
_diffrn_orient_matrix_UB_23      -0.0615958000
_diffrn_orient_matrix_UB_31      -0.0515182000
_diffrn_orient_matrix_UB_32      -0.0282157000
_diffrn_orient_matrix_UB_33      0.0409340000
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15777
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         2.556
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41069
_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    1.190
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/pentane'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 1904 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0786
_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^)+(0.1763P)^2^+0.0445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2025
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    0.863
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                5037
_reflns_number_total             5314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03010a2.cif
_cod_data_source_block           16f
_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_cell_volume        1559.39(14)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7130253
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.706
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C21(H21), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
  C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B)
;
_shelx_res_checksum              15891
_shelx_hkl_checksum              88524