#------------------------------------------------------------------------------
#$Date: 2019-11-04 01:47:10 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222080 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/90/4129056.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4129056
loop_
_publ_author_name
'Li, Jie'
'Ren, Qianyi'
'Cheng, Xinyi'
'Karaghiosoff, Konstantin'
'Knochel, Paul'
_publ_section_title
;
 Chromium(II)-Catalyzed Diastereoselective and Chemoselective
 Csp²-Csp³ Cross-Couplings Using Organomagnesium
 Reagents.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b08586
_journal_year                    2019
_chemical_formula_moiety         'C18 H19 F'
_chemical_formula_sum            'C18 H19 F'
_chemical_formula_weight         254.33
_chemical_name_systematic
;
1-fluoro-3-((1r,4r)-4-phenylcyclohexyl)benzene
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 110.896(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5416(3)
_cell_length_b                   18.2648(8)
_cell_length_c                   7.2069(4)
_cell_measurement_reflns_used    3009
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      31.6760
_cell_measurement_theta_min      3.7490
_cell_volume                     681.48(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11473
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0450
_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/[σ²(Fo²)+(0.0522P)²+0.2062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1421
_reflns_number_total             1689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b08586_si_003.cif
_cod_data_source_block           test1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4129056
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C7 C 0.8385(2) 0.06012(6) 0.87830(16) 0.0250(3) Uani 1 1 d . . . . .
H7 H 0.7413(14) 0.07249(19) 0.9656(13) 0.030 Uiso 1 1 calc R U . . .
C8 C 1.1264(2) 0.07071(7) 0.99971(18) 0.0302(3) Uani 1 1 d . . . . .
H8A H 1.2288(11) 0.06022(12) 0.9145(9) 0.036 Uiso 1 1 calc R U . . .
H8B H 1.1578(4) 0.1225(5) 1.0439(5) 0.036 Uiso 1 1 calc R U . . .
C9 C 0.7841(2) -0.02050(6) 0.81886(17) 0.0299(3) Uani 1 1 d . . . . .
H9A H 0.596(2) -0.02732(10) 0.7470(8) 0.036 Uiso 1 1 calc R U . . .
H9B H 0.8748(10) -0.03417(16) 0.7272(10) 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7444(2) 0.11060(6) 0.69998(16) 0.0249(3) Uani 1 1 d . . . . .
C1 C 0.5684(3) 0.20569(7) 0.37188(18) 0.0339(3) Uani 1 1 d . . . . .
H1 H 0.5102 0.2379 0.2613 0.041 Uiso 1 1 calc R U . A 1
C5 C 0.8590(2) 0.11054(6) 0.55629(17) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.9983 0.0782 0.5689 0.034 Uiso 1 1 calc R U . B 1
C3 C 0.5403(2) 0.15886(7) 0.67602(19) 0.0300(3) Uani 1 1 d . . . . .
H3 H 0.4594 0.1598 0.7721 0.036 Uiso 1 1 calc R U . C 1
C6A C 0.7700(3) 0.15759(7) 0.39507(18) 0.0332(3) Uani 0.396(2) 1 d . . P D 1
F1A F 0.8557(4) 0.15729(11) 0.2563(3) 0.0395(6) Uani 0.396(2) 1 d . . P D 1
C2A C 0.4540(2) 0.20555(7) 0.5137(2) 0.0345(3) Uani 0.396(2) 1 d . . P D 1
H2A H 0.3144 0.2379 0.5000 0.041 Uiso 0.396(2) 1 calc R U P D 1
C2B C 0.4540(2) 0.20555(7) 0.5137(2) 0.0345(3) Uani 0.104(2) 1 d . . P D 2
F1B F 0.2845(15) 0.2528(4) 0.5132(11) 0.042(2) Uani 0.104(2) 1 d . . P D 2
C6B C 0.7700(3) 0.15759(7) 0.39507(18) 0.0332(3) Uani 0.104(2) 1 d . . P D 2
H6B H 0.8494 0.1568 0.2981 0.040 Uiso 0.104(2) 1 calc R U P D 2
C2C C 0.4540(2) 0.20555(7) 0.5137(2) 0.0345(3) Uani 0.5 1 d . . P D 3
H2C H 0.3144 0.2379 0.5000 0.041 Uiso 0.5 1 calc R U P D 3
C6C C 0.7700(3) 0.15759(7) 0.39507(18) 0.0332(3) Uani 0.5 1 d . . P D 3
H6C H 0.8494 0.1568 0.2981 0.040 Uiso 0.5 1 calc R U P D 3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C4 C7 C9 111.94(9) .
C4 C7 C8 112.35(9) .
C9 C7 C8 109.97(9) .
C4 C7 H7 107.4 .
C9 C7 H7 107.4 .
C8 C7 H7 107.4 .
C9 C8 C7 111.52(10) 3_757
C9 C8 H8A 109.3 3_757
C7 C8 H8A 109.3 .
C9 C8 H8B 109.3 3_757
C7 C8 H8B 109.3 .
H8A C8 H8B 108.0 .
C8 C9 C7 111.46(9) 3_757
C8 C9 H9A 109.3 3_757
C7 C9 H9A 109.3 .
C8 C9 H9B 109.3 3_757
C7 C9 H9B 109.3 .
H9A C9 H9B 108.0 .
C5 C4 C3 118.18(11) .
C5 C4 C7 121.29(10) .
C3 C4 C7 120.53(11) .
C2A C1 C6A 118.24(11) .
C2A C1 H1 120.9 .
C6A C1 H1 120.9 .
C6A C5 C4 120.10(11) .
C6A C5 H5 119.9 .
C4 C5 H5 119.9 .
C2A C3 C4 120.88(12) .
C2A C3 H3 119.6 .
C4 C3 H3 119.6 .
F1A C6A C1 115.25(14) .
F1A C6A C5 122.97(15) .
C1 C6A C5 121.69(12) .
C1 C2A C3 120.91(12) .
C1 C2A H2A 119.5 .
C3 C2A H2A 119.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 C4 1.5151(15) .
C7 C9 1.5332(16) .
C7 C8 1.5337(16) .
C7 H7 0.989(14) .
C8 C9 1.5277(16) 3_757
C8 H8A 0.993(10) .
C8 H8B 0.993(10) .
C9 C8 1.5278(16) 3_757
C9 H9A 0.994(11) .
C9 H9B 0.994(11) .
C4 C5 1.3946(17) .
C4 C3 1.3950(16) .
C1 C2A 1.3818(19) .
C1 C6A 1.3834(19) .
C1 H1 0.9500 .
C5 C6A 1.3867(17) .
C5 H5 0.9500 .
C3 C2A 1.3874(17) .
C3 H3 0.9500 .
C6A F1A 1.251(2) .
C2A H2A 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C4 C7 C8 C9 178.78(10) 3_757
C9 C7 C8 C9 -55.83(15) 3_757
C4 C7 C9 C8 -178.58(10) 3_757
C8 C7 C9 C8 55.80(15) 3_757
C9 C7 C4 C5 -67.30(14) .
C8 C7 C4 C5 57.01(14) .
C9 C7 C4 C3 113.03(12) .
C8 C7 C4 C3 -122.67(12) .
C3 C4 C5 C6A 0.02(17) .
C7 C4 C5 C6A -179.66(10) .
C5 C4 C3 C2A -0.06(17) .
C7 C4 C3 C2A 179.63(11) .
C2A C1 C6A F1A 176.07(15) .
C2A C1 C6A C5 -0.56(19) .
C4 C5 C6A F1A -176.07(15) .
C4 C5 C6A C1 0.29(18) .
C6A C1 C2A C3 0.52(18) .
C4 C3 C2A C1 -0.22(18) .
