#------------------------------------------------------------------------------
#$Date: 2020-07-25 04:18:22 +0300 (Sat, 25 Jul 2020) $
#$Revision: 254567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558663.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_1558663
loop_
_publ_author_name
'Liu, Lei'
'Lee, Wes'
'Youshaw, Cassandra R.'
'Yuan, Mingbin'
'Geherty, Michael B.'
'Zavalij, Peter Y.'
'gutierrez, osvaldo'
_publ_section_title
;
 Fe-Catalyzed Three-Component Dicarbofunctionalization of Unactivated
 Alkenes with Alkyl Halides and Grignard Reagents
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02127J
_journal_year                    2020
_chemical_formula_moiety         'C22 H28 O'
_chemical_formula_sum            'C22 H28 O'
_chemical_formula_weight         308.44
_chemical_name_common
cis-3-([1,1?-biphenyl]-4-ylmethyl)-4-neopentyltetrahydrofuran
_chemical_name_systematic        LL-2
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL & ZCIF'
_audit_update_record
;
2020-04-14 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                96.1247(13)
_cell_angle_beta                 90.4111(13)
_cell_angle_gamma                99.2413(14)
_cell_formula_units_Z            2
_cell_length_a                   6.1587(5)
_cell_length_b                   9.3173(8)
_cell_length_c                   15.9930(13)
_cell_measurement_reflns_used    7583
_cell_measurement_temperature    149(2)
_cell_measurement_theta_max      31.9
_cell_measurement_theta_min      2.2
_cell_volume                     900.36(13)
_computing_cell_refinement       'Apex2, Saint (Bruker, 2012)'
_computing_data_collection       'Apex2 (Bruker, 2012)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'Olex2 (Dolomanov, 2009)'
_computing_publication_material  'Apex2, SHELXL, Platon (Spek, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015c)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      149(2)
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.1263299
_diffrn_orient_matrix_UB_12      0.0823452
_diffrn_orient_matrix_UB_13      0.0008779
_diffrn_orient_matrix_UB_21      -0.0105570
_diffrn_orient_matrix_UB_22      0.0194048
_diffrn_orient_matrix_UB_23      0.0624301
_diffrn_orient_matrix_UB_31      0.1049195
_diffrn_orient_matrix_UB_32      -0.0693520
_diffrn_orient_matrix_UB_33      0.0076685
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16141
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.243
_diffrn_reflns_theta_min         2.228
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0487
_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)+(0.0090P)²+0.4940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4876
_reflns_number_total             5721
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02127j2.cif
_cod_data_source_block           UM3392
_cod_database_code               1558663
_shelx_shelxl_version_number     2017/1
_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   0.971
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.90557(18) 0.30670(12) 0.40180(8) 0.0309(2) Uani 1 1 d . . . . .
H1 H 1.020(2) 0.3360(15) 0.3635(9) 0.036(4) Uiso 1 1 d . . . . .
C2 C 0.9239(2) 0.19593(13) 0.45189(8) 0.0356(3) Uani 1 1 d . . . . .
H2 H 1.053(2) 0.1510(16) 0.4482(9) 0.044(4) Uiso 1 1 d . . . . .
C3 C 0.7576(2) 0.15282(13) 0.50630(8) 0.0344(2) Uani 1 1 d . . . . .
H3 H 0.772(2) 0.0775(16) 0.5415(9) 0.041(4) Uiso 1 1 d . . . . .
C4 C 0.5720(2) 0.21983(12) 0.51016(7) 0.0311(2) Uani 1 1 d . . . . .
H4 H 0.455(2) 0.1899(15) 0.5484(9) 0.037(4) Uiso 1 1 d . . . . .
C5 C 0.55184(18) 0.32929(11) 0.45924(7) 0.0267(2) Uani 1 1 d . . . . .
H5 H 0.423(2) 0.3752(14) 0.4614(8) 0.030(3) Uiso 1 1 d . . . . .
C6 C 0.71947(17) 0.37532(10) 0.40466(6) 0.02432(19) Uani 1 1 d . . . . .
C7 C 0.70076(16) 0.49314(10) 0.35059(6) 0.02387(19) Uani 1 1 d . . . . .
C8 C 0.50485(17) 0.49796(11) 0.30752(7) 0.0274(2) Uani 1 1 d . . . . .
H8 H 0.379(2) 0.4222(15) 0.3123(8) 0.033(3) Uiso 1 1 d . . . . .
C9 C 0.48860(18) 0.60703(12) 0.25576(7) 0.0286(2) Uani 1 1 d . . . . .
H9 H 0.351(2) 0.6066(15) 0.2256(9) 0.037(4) Uiso 1 1 d . . . . .
C10 C 0.66799(18) 0.71526(11) 0.24551(7) 0.0262(2) Uani 1 1 d . . . . .
C11 C 0.86389(18) 0.71085(12) 0.28881(7) 0.0293(2) Uani 1 1 d . . . . .
H11 H 0.992(2) 0.7838(15) 0.2823(8) 0.034(4) Uiso 1 1 d . . . . .
C12 C 0.88104(18) 0.60196(11) 0.34038(7) 0.0279(2) Uani 1 1 d . . . . .
H12 H 1.015(2) 0.6007(14) 0.3701(8) 0.033(3) Uiso 1 1 d . . . . .
C13 C 0.6516(2) 0.83642(12) 0.19089(7) 0.0298(2) Uani 1 1 d . . . . .
H13A H 0.515(2) 0.8114(16) 0.1550(9) 0.040(4) Uiso 1 1 d . . . . .
H13B H 0.776(2) 0.8434(15) 0.1532(9) 0.038(4) Uiso 1 1 d . . . . .
C14 C 0.65342(18) 0.98502(11) 0.24311(7) 0.0259(2) Uani 1 1 d . . . . .
H14 H 0.790(2) 1.0076(14) 0.2795(8) 0.032(3) Uiso 1 1 d . . . . .
C15 C 0.4477(2) 0.98622(13) 0.29471(8) 0.0340(2) Uani 1 1 d . . . . .
H15A H 0.392(2) 0.8921(15) 0.3154(9) 0.035(4) Uiso 1 1 d . . . . .
H15B H 0.473(2) 1.0654(17) 0.3444(10) 0.045(4) Uiso 1 1 d . . . . .
O16 O 0.28179(15) 1.01528(12) 0.23833(7) 0.0516(3) Uani 1 1 d . . . . .
C17 C 0.38802(19) 1.10093(15) 0.17699(9) 0.0359(3) Uani 1 1 d . . . . .
H17A H 0.338(3) 1.1951(18) 0.1817(10) 0.050(4) Uiso 1 1 d . . . . .
H17B H 0.340(3) 1.0504(17) 0.1208(10) 0.051(4) Uiso 1 1 d . . . . .
C18 C 0.63748(17) 1.11407(11) 0.19093(7) 0.0266(2) Uani 1 1 d . . . . .
H18 H 0.697(2) 1.2102(15) 0.2283(8) 0.032(3) Uiso 1 1 d . . . . .
C19 C 0.77595(19) 1.11699(12) 0.11221(7) 0.0281(2) Uani 1 1 d . . . . .
H19A H 0.694(2) 1.0377(16) 0.0673(9) 0.039(4) Uiso 1 1 d . . . . .
H19B H 0.928(2) 1.0879(15) 0.1276(9) 0.039(4) Uiso 1 1 d . . . . .
C20 C 0.82833(18) 1.26323(11) 0.07353(7) 0.0270(2) Uani 1 1 d . . . . .
C21 C 0.6197(2) 1.31716(16) 0.04621(9) 0.0398(3) Uani 1 1 d . . . . .
H21A H 0.657(3) 1.3998(18) 0.0129(10) 0.050(4) Uiso 1 1 d . . . . .
H21B H 0.535(3) 1.3484(16) 0.0943(10) 0.045(4) Uiso 1 1 d . . . . .
H21C H 0.520(3) 1.2391(18) 0.0098(10) 0.051(4) Uiso 1 1 d . . . . .
C22 C 0.9626(2) 1.38142(13) 0.13476(9) 0.0374(3) Uani 1 1 d . . . . .
H22A H 1.012(2) 1.4627(16) 0.1056(9) 0.040(4) Uiso 1 1 d . . . . .
H22B H 1.101(3) 1.3488(18) 0.1542(11) 0.059(5) Uiso 1 1 d . . . . .
H22C H 0.875(3) 1.4120(18) 0.1862(11) 0.058(5) Uiso 1 1 d . . . . .
C23 C 0.9667(3) 1.23430(15) -0.00444(9) 0.0408(3) Uani 1 1 d . . . . .
H23A H 1.105(3) 1.1905(18) 0.0120(10) 0.057(5) Uiso 1 1 d . . . . .
H23B H 1.017(3) 1.3297(19) -0.0319(11) 0.061(5) Uiso 1 1 d . . . . .
H23C H 0.878(3) 1.1614(19) -0.0447(11) 0.057(5) Uiso 1 1 d . . . . .
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.88(11) . . ?
C2 C1 H1 120.4(8) . . ?
C6 C1 H1 118.7(8) . . ?
C3 C2 C1 120.16(11) . . ?
C3 C2 H2 121.1(9) . . ?
C1 C2 H2 118.8(9) . . ?
C4 C3 C2 119.79(11) . . ?
C4 C3 H3 120.3(9) . . ?
C2 C3 H3 119.9(9) . . ?
C3 C4 C5 120.15(11) . . ?
C3 C4 H4 119.9(8) . . ?
C5 C4 H4 119.9(8) . . ?
C4 C5 C6 120.78(10) . . ?
C4 C5 H5 120.3(8) . . ?
C6 C5 H5 118.9(8) . . ?
C1 C6 C5 118.22(10) . . ?
C1 C6 C7 120.52(9) . . ?
C5 C6 C7 121.26(9) . . ?
C8 C7 C12 117.88(9) . . ?
C8 C7 C6 121.24(9) . . ?
C12 C7 C6 120.88(9) . . ?
C9 C8 C7 121.18(10) . . ?
C9 C8 H8 119.4(8) . . ?
C7 C8 H8 119.4(8) . . ?
C8 C9 C10 120.97(10) . . ?
C8 C9 H9 119.5(8) . . ?
C10 C9 H9 119.6(8) . . ?
C9 C10 C11 117.90(10) . . ?
C9 C10 C13 121.61(10) . . ?
C11 C10 C13 120.47(10) . . ?
C12 C11 C10 121.33(10) . . ?
C12 C11 H11 119.0(8) . . ?
C10 C11 H11 119.7(8) . . ?
C11 C12 C7 120.74(10) . . ?
C11 C12 H12 120.5(8) . . ?
C7 C12 H12 118.7(8) . . ?
C10 C13 C14 112.26(9) . . ?
C10 C13 H13A 109.9(8) . . ?
C14 C13 H13A 109.5(8) . . ?
C10 C13 H13B 108.4(8) . . ?
C14 C13 H13B 109.3(8) . . ?
H13A C13 H13B 107.3(11) . . ?
C15 C14 C13 111.55(9) . . ?
C15 C14 C18 100.23(9) . . ?
C13 C14 C18 114.90(9) . . ?
C15 C14 H14 111.7(8) . . ?
C13 C14 H14 108.5(8) . . ?
C18 C14 H14 109.8(8) . . ?
O16 C15 C14 105.60(9) . . ?
O16 C15 H15A 106.8(8) . . ?
C14 C15 H15A 113.9(8) . . ?
O16 C15 H15B 110.4(8) . . ?
C14 C15 H15B 111.0(9) . . ?
H15A C15 H15B 109.0(11) . . ?
C17 O16 C15 108.12(9) . . ?
O16 C17 C18 108.04(10) . . ?
O16 C17 H17A 109.2(9) . . ?
C18 C17 H17A 113.0(9) . . ?
O16 C17 H17B 107.7(9) . . ?
C18 C17 H17B 111.7(9) . . ?
H17A C17 H17B 107.2(13) . . ?
C19 C18 C17 116.31(10) . . ?
C19 C18 C14 115.10(9) . . ?
C17 C18 C14 101.96(9) . . ?
C19 C18 H18 105.5(7) . . ?
C17 C18 H18 109.9(7) . . ?
C14 C18 H18 107.9(7) . . ?
C18 C19 C20 117.67(9) . . ?
C18 C19 H19A 106.9(8) . . ?
C20 C19 H19A 109.0(8) . . ?
C18 C19 H19B 107.5(8) . . ?
C20 C19 H19B 106.5(8) . . ?
H19A C19 H19B 108.9(11) . . ?
C22 C20 C21 109.19(10) . . ?
C22 C20 C23 108.71(10) . . ?
C21 C20 C23 108.93(10) . . ?
C22 C20 C19 111.31(9) . . ?
C21 C20 C19 112.07(9) . . ?
C23 C20 C19 106.53(9) . . ?
C20 C21 H21A 110.6(9) . . ?
C20 C21 H21B 111.9(9) . . ?
H21A C21 H21B 108.3(13) . . ?
C20 C21 H21C 111.7(9) . . ?
H21A C21 H21C 106.7(13) . . ?
H21B C21 H21C 107.4(13) . . ?
C20 C22 H22A 108.3(9) . . ?
C20 C22 H22B 111.0(10) . . ?
H22A C22 H22B 104.8(13) . . ?
C20 C22 H22C 112.6(10) . . ?
H22A C22 H22C 110.3(13) . . ?
H22B C22 H22C 109.5(13) . . ?
C20 C23 H23A 110.3(9) . . ?
C20 C23 H23B 111.2(10) . . ?
H23A C23 H23B 109.2(13) . . ?
C20 C23 H23C 108.6(10) . . ?
H23A C23 H23C 107.3(13) . . ?
H23B C23 H23C 110.2(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3901(16) . ?
C1 C6 1.3980(15) . ?
C1 H1 0.961(14) . ?
C2 C3 1.3869(18) . ?
C2 H2 0.958(15) . ?
C3 C4 1.3864(17) . ?
C3 H3 0.959(15) . ?
C4 C5 1.3911(15) . ?
C4 H4 0.974(14) . ?
C5 C6 1.4008(14) . ?
C5 H5 0.960(13) . ?
C6 C7 1.4859(14) . ?
C7 C8 1.3944(15) . ?
C7 C12 1.4014(14) . ?
C8 C9 1.3924(15) . ?
C8 H8 0.971(14) . ?
C9 C10 1.3944(15) . ?
C9 H9 0.971(14) . ?
C10 C11 1.3953(15) . ?
C10 C13 1.5144(15) . ?
C11 C12 1.3901(15) . ?
C11 H11 0.968(14) . ?
C12 H12 0.952(14) . ?
C13 C14 1.5371(15) . ?
C13 H13A 0.998(15) . ?
C13 H13B 0.977(15) . ?
C14 C15 1.5177(15) . ?
C14 C18 1.5499(14) . ?
C14 H14 1.001(13) . ?
C15 O16 1.4347(16) . ?
C15 H15A 0.982(14) . ?
C15 H15B 1.018(16) . ?
O16 C17 1.4268(15) . ?
C17 C18 1.5342(16) . ?
C17 H17A 0.971(16) . ?
C17 H17B 0.990(16) . ?
C18 C19 1.5260(15) . ?
C18 H18 1.034(13) . ?
C19 C20 1.5443(14) . ?
C19 H19A 1.037(15) . ?
C19 H19B 1.049(14) . ?
C20 C22 1.5235(17) . ?
C20 C21 1.5298(16) . ?
C20 C23 1.5397(17) . ?
C21 H21A 0.980(16) . ?
C21 H21B 0.977(16) . ?
C21 H21C 1.002(17) . ?
C22 H22A 0.942(15) . ?
C22 H22B 1.009(18) . ?
C22 H22C 1.028(18) . ?
C23 H23A 1.043(17) . ?
C23 H23B 1.038(18) . ?
C23 H23C 0.978(18) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.63(19) . . . . ?
C1 C2 C3 C4 0.47(19) . . . . ?
C2 C3 C4 C5 0.44(18) . . . . ?
C3 C4 C5 C6 -1.20(17) . . . . ?
C2 C1 C6 C5 -0.12(17) . . . . ?
C2 C1 C6 C7 -179.70(11) . . . . ?
C4 C5 C6 C1 1.03(16) . . . . ?
C4 C5 C6 C7 -179.39(10) . . . . ?
C1 C6 C7 C8 136.43(11) . . . . ?
C5 C6 C7 C8 -43.14(15) . . . . ?
C1 C6 C7 C12 -42.66(15) . . . . ?
C5 C6 C7 C12 137.77(11) . . . . ?
C12 C7 C8 C9 0.20(16) . . . . ?
C6 C7 C8 C9 -178.92(10) . . . . ?
C7 C8 C9 C10 -0.14(17) . . . . ?
C8 C9 C10 C11 -0.08(16) . . . . ?
C8 C9 C10 C13 -178.71(10) . . . . ?
C9 C10 C11 C12 0.25(16) . . . . ?
C13 C10 C11 C12 178.89(10) . . . . ?
C10 C11 C12 C7 -0.19(17) . . . . ?
C8 C7 C12 C11 -0.03(16) . . . . ?
C6 C7 C12 C11 179.08(10) . . . . ?
C9 C10 C13 C14 108.15(12) . . . . ?
C11 C10 C13 C14 -70.45(13) . . . . ?
C10 C13 C14 C15 -66.89(12) . . . . ?
C10 C13 C14 C18 179.90(9) . . . . ?
C13 C14 C15 O16 -82.28(11) . . . . ?
C18 C14 C15 O16 39.82(11) . . . . ?
C14 C15 O16 C17 -29.15(13) . . . . ?
C15 O16 C17 C18 5.58(14) . . . . ?
O16 C17 C18 C19 145.30(11) . . . . ?
O16 C17 C18 C14 19.25(13) . . . . ?
C15 C14 C18 C19 -161.56(10) . . . . ?
C13 C14 C18 C19 -41.87(13) . . . . ?
C15 C14 C18 C17 -34.73(11) . . . . ?
C13 C14 C18 C17 84.97(11) . . . . ?
C17 C18 C19 C20 80.09(13) . . . . ?
C14 C18 C19 C20 -160.77(9) . . . . ?
C18 C19 C20 C22 62.07(13) . . . . ?
C18 C19 C20 C21 -60.53(14) . . . . ?
C18 C19 C20 C23 -179.57(10) . . . . ?
