#------------------------------------------------------------------------------
#$Date: 2020-10-17 04:06:41 +0300 (Sat, 17 Oct 2020) $
#$Revision: 258437 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/93/1559367.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_1559367
loop_
_publ_author_name
'Wang, Yidong'
'Zhu, Jin'
'Guo, Rui'
'Lindberg, Haley'
'Wang, Yiming'
_publ_section_title
;
 Iron-Catalyzed α-C--H functionalization of π-Bonds:
 Cross-Dehydrogenative Coupling and Mechanistic Insights
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC05091A
_journal_year                    2020
_chemical_formula_sum            'C29 H24'
_chemical_formula_weight         372.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-04-12 deposited with the CCDC.	2020-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.350(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6092(4)
_cell_length_b                   24.7359(10)
_cell_length_c                   9.7874(4)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.150
_cell_measurement_theta_min      3.074
_cell_volume                     2084.68(15)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13085
_diffrn_reflns_point_group_measured_fraction_full 0.97
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.574
_diffrn_source                   'Bruker X8 Prospector Ultra IMuS'
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0366
_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)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3093
_reflns_number_total             3689
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05091a2.cif
_cod_data_source_block           Yidong1_a
_cod_original_cell_volume        2084.67(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1559367
_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   0.915
_shelx_estimated_absorpt_t_max   0.980
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.15400(15) 0.37839(5) 0.40502(14) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.27125(14) 0.35338(5) 0.47186(14) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.41572(14) 0.32159(5) 0.54275(14) 0.0227(3) Uani 1 1 d . . . . .
H3A H 0.385076 0.282834 0.540300 0.027 Uiso 1 1 calc R U . . .
C4 C 0.50122(16) 0.32641(6) 0.44298(15) 0.0294(3) Uani 1 1 d . . . . .
H4A H 0.597697 0.305451 0.488710 0.044 Uiso 1 1 calc R U . . .
H4B H 0.434977 0.312411 0.340784 0.044 Uiso 1 1 calc R U . . .
H4C H 0.525572 0.364464 0.435724 0.044 Uiso 1 1 calc R U . . .
C5 C -0.04642(15) 0.42372(5) 0.17783(15) 0.0276(3) Uani 1 1 d . . . . .
H5A H 0.000093 0.409655 0.117573 0.033 Uiso 1 1 calc R U . . .
C6 C -0.17549(15) 0.45695(6) 0.11178(16) 0.0317(3) Uani 1 1 d . . . . .
H6A H -0.216889 0.465673 0.006518 0.038 Uiso 1 1 calc R U . . .
C7 C -0.24420(16) 0.47743(6) 0.19839(17) 0.0370(4) Uani 1 1 d . . . . .
H7A H -0.332380 0.500350 0.153010 0.044 Uiso 1 1 calc R U . . .
C8 C -0.18404(17) 0.46443(7) 0.35157(17) 0.0399(4) Uani 1 1 d . . . . .
H8A H -0.231589 0.478352 0.411057 0.048 Uiso 1 1 calc R U . . .
C9 C -0.05505(16) 0.43128(6) 0.41874(16) 0.0315(3) Uani 1 1 d . . . . .
H9A H -0.014761 0.422512 0.523899 0.038 Uiso 1 1 calc R U . . .
C10 C 0.01571(14) 0.41078(5) 0.33292(15) 0.0241(3) Uani 1 1 d . . . . .
C11 C 0.51909(13) 0.33681(5) 0.71464(14) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.29676(14) 0.30261(5) 0.76971(15) 0.0256(3) Uani 1 1 d . . . . .
H12A H 0.268226 0.278522 0.685961 0.031 Uiso 1 1 calc R U . . .
C13 C 0.21291(16) 0.30231(6) 0.85431(16) 0.0321(3) Uani 1 1 d . . . . .
H13A H 0.127802 0.278219 0.827595 0.039 Uiso 1 1 calc R U . . .
C14 C 0.25216(16) 0.33676(6) 0.97705(16) 0.0341(3) Uani 1 1 d . . . . .
H14A H 0.193665 0.336956 1.033853 0.041 Uiso 1 1 calc R U . . .
C15 C 0.37830(16) 0.37106(6) 1.01603(16) 0.0328(3) Uani 1 1 d . . . . .
H15A H 0.407595 0.394535 1.101154 0.039 Uiso 1 1 calc R U . . .
C16 C 0.46151(15) 0.37122(5) 0.93166(14) 0.0260(3) Uani 1 1 d . . . . .
H16A H 0.547876 0.394862 0.960371 0.031 Uiso 1 1 calc R U . . .
C17 C 0.42208(14) 0.33755(5) 0.80514(14) 0.0207(3) Uani 1 1 d . . . . .
C18 C 0.50291(15) 0.43949(5) 0.69369(14) 0.0243(3) Uani 1 1 d . . . . .
H18A H 0.399714 0.436668 0.682293 0.029 Uiso 1 1 calc R U . . .
C19 C 0.56232(16) 0.49004(6) 0.68730(15) 0.0306(3) Uani 1 1 d . . . . .
H19A H 0.499819 0.521326 0.672177 0.037 Uiso 1 1 calc R U . . .
C20 C 0.71157(16) 0.49517(6) 0.70275(15) 0.0341(3) Uani 1 1 d . . . . .
H20A H 0.752582 0.529825 0.699411 0.041 Uiso 1 1 calc R U . . .
C21 C 0.80085(16) 0.44920(6) 0.72319(16) 0.0342(3) Uani 1 1 d . . . . .
H21A H 0.903526 0.452351 0.733326 0.041 Uiso 1 1 calc R U . . .
C22 C 0.74135(15) 0.39832(6) 0.72902(15) 0.0284(3) Uani 1 1 d . . . . .
H22A H 0.803579 0.367131 0.741656 0.034 Uiso 1 1 calc R U . . .
C23 C 0.59194(14) 0.39254(5) 0.71660(13) 0.0216(3) Uani 1 1 d . . . . .
C24 C 0.76385(15) 0.30437(5) 0.93900(15) 0.0281(3) Uani 1 1 d . . . . .
H24A H 0.762857 0.337723 0.986676 0.034 Uiso 1 1 calc R U . . .
C25 C 0.88137(15) 0.26744(6) 1.01577(16) 0.0325(3) Uani 1 1 d . . . . .
H25A H 0.960501 0.275987 1.114340 0.039 Uiso 1 1 calc R U . . .
C26 C 0.88434(16) 0.21825(6) 0.95003(16) 0.0323(3) Uani 1 1 d . . . . .
H26A H 0.965182 0.193011 1.002377 0.039 Uiso 1 1 calc R U . . .
C27 C 0.76769(16) 0.20640(6) 0.80680(16) 0.0306(3) Uani 1 1 d . . . . .
H27A H 0.767491 0.172458 0.761303 0.037 Uiso 1 1 calc R U . . .
C28 C 0.65087(15) 0.24356(5) 0.72881(15) 0.0260(3) Uani 1 1 d . . . . .
H28A H 0.572364 0.234798 0.630097 0.031 Uiso 1 1 calc R U . . .
C29 C 0.64678(14) 0.29357(5) 0.79290(14) 0.0221(3) Uani 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 0.0181 0.0091 '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'
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 C10 176.30(14) . . ?
C1 C2 C3 175.53(13) . . ?
C2 C3 C4 108.51(10) . . ?
C2 C3 C11 113.04(10) . . ?
C4 C3 C11 113.55(10) . . ?
C2 C3 H3A 107.1 . . ?
C4 C3 H3A 107.1 . . ?
C11 C3 H3A 107.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 120.28(13) . . ?
C6 C5 H5A 119.9 . . ?
C10 C5 H5A 119.9 . . ?
C7 C6 C5 120.27(13) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C8 119.72(13) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C9 120.49(14) . . ?
C7 C8 H8A 119.8 . . ?
C9 C8 H8A 119.8 . . ?
C8 C9 C10 120.26(13) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C5 118.98(12) . . ?
C9 C10 C1 119.96(12) . . ?
C5 C10 C1 121.03(12) . . ?
C23 C11 C17 111.61(10) . . ?
C23 C11 C29 110.81(10) . . ?
C17 C11 C29 105.76(9) . . ?
C23 C11 C3 107.15(10) . . ?
C17 C11 C3 111.14(9) . . ?
C29 C11 C3 110.42(10) . . ?
C13 C12 C17 121.36(12) . . ?
C13 C12 H12A 119.3 . . ?
C17 C12 H12A 119.3 . . ?
C14 C13 C12 120.57(13) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 118.97(13) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C16 C15 C14 120.30(13) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 C17 121.78(12) . . ?
C15 C16 H16A 119.1 . . ?
C17 C16 H16A 119.1 . . ?
C12 C17 C16 117.00(12) . . ?
C12 C17 C11 121.60(11) . . ?
C16 C17 C11 121.31(11) . . ?
C19 C18 C23 121.35(13) . . ?
C19 C18 H18A 119.3 . . ?
C23 C18 H18A 119.3 . . ?
C20 C19 C18 120.43(13) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 119.18(13) . . ?
C19 C20 H20A 120.4 . . ?
C21 C20 H20A 120.4 . . ?
C20 C21 C22 120.56(13) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C23 C22 C21 120.97(13) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C18 117.49(12) . . ?
C22 C23 C11 122.49(11) . . ?
C18 C23 C11 119.84(11) . . ?
C25 C24 C29 121.38(12) . . ?
C25 C24 H24A 119.3 . . ?
C29 C24 H24A 119.3 . . ?
C26 C25 C24 120.52(13) . . ?
C26 C25 H25A 119.7 . . ?
C24 C25 H25A 119.7 . . ?
C25 C26 C27 118.91(12) . . ?
C25 C26 H26A 120.5 . . ?
C27 C26 H26A 120.5 . . ?
C26 C27 C28 120.72(13) . . ?
C26 C27 H27A 119.6 . . ?
C28 C27 H27A 119.6 . . ?
C27 C28 C29 121.13(12) . . ?
C27 C28 H28A 119.4 . . ?
C29 C28 H28A 119.4 . . ?
C28 C29 C24 117.32(12) . . ?
C28 C29 C11 124.31(11) . . ?
C24 C29 C11 118.35(11) . . ?
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 1.1941(18) . ?
C1 C10 1.4399(18) . ?
C2 C3 1.4738(17) . ?
C3 C4 1.5346(17) . ?
C3 C11 1.5733(17) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.3856(19) . ?
C5 C10 1.3994(18) . ?
C5 H5A 0.9500 . ?
C6 C7 1.381(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3899(19) . ?
C9 H9A 0.9500 . ?
C11 C23 1.5425(16) . ?
C11 C17 1.5449(17) . ?
C11 C29 1.5499(16) . ?
C12 C13 1.388(2) . ?
C12 C17 1.3952(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.387(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3811(19) . ?
C15 H15A 0.9500 . ?
C16 C17 1.3980(18) . ?
C16 H16A 0.9500 . ?
C18 C19 1.3876(18) . ?
C18 C23 1.4001(18) . ?
C18 H18A 0.9500 . ?
C19 C20 1.380(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.385(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3938(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3934(18) . ?
C22 H22A 0.9500 . ?
C24 C25 1.3861(18) . ?
C24 C29 1.3977(18) . ?
C24 H24A 0.9500 . ?
C25 C26 1.382(2) . ?
C25 H25A 0.9500 . ?
C26 C27 1.383(2) . ?
C26 H26A 0.9500 . ?
C27 C28 1.3882(18) . ?
C27 H27A 0.9500 . ?
C28 C29 1.3953(17) . ?
C28 H28A 0.9500 . ?
