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_7130250
_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_formula_moiety         'C14 H23 F5'
_chemical_formula_sum            'C14 H23 F5'
_chemical_formula_weight         286.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 101.86(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   5.5262(16)
_cell_length_b                   70.03(3)
_cell_length_c                   11.417(4)
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    173
_cell_measurement_theta_max      67.9860
_cell_measurement_theta_min      3.8170
_cell_volume                     4324(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.931
_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   15.00   0.00 -30.00   0.00    --   400
  2  \w    -72.00   1.00   0.50   15.00    --  -30.00 -72.00 -90.00  146
  3  \w   -113.00 -71.00   0.50   15.00    --  -30.00 180.00 -45.00   84
  4  \f      0.00 200.00   0.50   15.00   0.00 -67.00   0.00    --   400
  5  \w    -85.00 -13.00   0.50   15.00    --  -67.00  72.00  90.00  144
  6  \w   -133.00 -93.00   0.50   15.00    --  -67.00 180.00   0.00   80
  7  \w    -85.00 -12.00   0.50   15.00    --  -67.00  72.00 -90.00  146
  8  \w   -126.00 -86.00   0.50   15.00    --  -67.00 180.00-180.00   80
  9  \f      0.00 200.00   0.50   15.00 -25.00-110.00   0.00    --   400
 10  \w   -128.00 -20.00   0.50   15.00    -- -110.00  72.00-135.00  216
 11  \w   -128.00 -20.00   0.50   15.00    -- -110.00  72.00  45.00  216
 12  \w   -115.00 -20.00   0.50   15.00    -- -110.00  72.00 -45.00  190
 13  \w   -113.00 -23.00   0.50   15.00    -- -110.00  72.00 135.00  180
 14  \w   -141.00 -46.00   0.50   15.00    -- -110.00 180.00 -90.00  190
 15  \w   -141.00 -46.00   0.50   15.00    -- -110.00 180.00-180.00  190
 16  \w   -141.00 -59.00   0.50   15.00    -- -110.00 180.00  90.00  164
 17  \w   -141.00 -55.00   0.50   15.00    -- -110.00 180.00   0.00  172
 18  \w   -141.00 -59.00   0.50   15.00    -- -110.00 180.00  45.00  164
 19  \w   -141.00 -78.00   0.50   15.00    -- -110.00 180.00 -45.00  126
 20  \w   -140.00 -77.00   0.50   15.00    -- -110.00 180.00-135.00  126
 21  \w   -140.00 -56.00   0.50   15.00    -- -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      -0.1096811000
_diffrn_orient_matrix_UB_12      -0.0134887000
_diffrn_orient_matrix_UB_13      0.0822686000
_diffrn_orient_matrix_UB_21      -0.0206674000
_diffrn_orient_matrix_UB_22      -0.0159851000
_diffrn_orient_matrix_UB_23      -0.0946320000
_diffrn_orient_matrix_UB_31      0.2614275000
_diffrn_orient_matrix_UB_32      -0.0068903000
_diffrn_orient_matrix_UB_33      0.0575283000
_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  0.3923
_diffrn_reflns_av_unetI/netI     0.2023
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       83
_diffrn_reflns_limit_k_min       -84
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            45738
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.198
_diffrn_reflns_theta_min         2.524
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    1.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58998
_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    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             1824
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.0057(7)
_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   1.438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         8073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.438
_refine_ls_R_factor_all          0.3485
_refine_ls_R_factor_gt           0.1646
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3423
_refine_ls_wR_factor_ref         0.4235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2053
_reflns_number_total             8073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03010a2.cif
_cod_data_source_block           8
_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      P21/n
_cod_database_code               7130250
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.894
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
  C46(H46)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C13(H13A,H13B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
  C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C47(H47A,
 H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B),
 C52(H52A,H52B), C53(H53A,H53B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              87455
_shelx_hkl_checksum              6435