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#$Date: 2020-03-05 01:36:37 +0200 (Thu, 05 Mar 2020) $
#$Revision: 248823 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/58/7125840.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_7125840
loop_
_publ_author_name
'Vrána, Jan'
'Samsonov, Maksim A.'
'Němec, Vlastimil'
'R°uŽička, Aleš'
_publ_section_title
;
 Access to the most sterically crowded anilines via non-catalysed C-C
 coupling reactions.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2487
_journal_page_last               2490
_journal_paper_doi               10.1039/c9cc09497k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C43 H49 Cl2 N O2'
_chemical_formula_weight         682.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-09-30 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.680(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0461(4)
_cell_length_b                   25.3743(11)
_cell_length_c                   9.3223(5)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.35
_cell_volume                     1881.48(16)
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            45673
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.351
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.7561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          1.514
_exptl_crystal_size_mid          0.808
_exptl_crystal_size_min          0.548
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4789
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0653
_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)+(0.0673P)²+1.4983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3812
_reflns_number_total             4789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09497k2.cif
_cod_data_source_block           jvr190108N1
_cod_depositor_comments
'Adding full bibliography for 7125838--7125846.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7125840
_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   0.743
_shelx_estimated_absorpt_t_max   0.894
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.878
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
O1 O -0.11174(15) 0.35435(5) 1.56451(14) 0.0260(3) Uani 1 1 d . . . . .
N1 N -0.2020(3) 0.250000 1.6590(2) 0.0236(5) Uani 1 2 d S T P . .
H1 H -0.177(3) 0.2784(8) 1.704(2) 0.020(5) Uiso 1 1 d . . . . .
C1 C -0.2950(3) 0.250000 1.5231(2) 0.0181(4) Uani 1 2 d S T P . .
C2 C -0.3394(2) 0.29834(7) 1.45033(17) 0.0186(3) Uani 1 1 d . . . . .
C3 C -0.4093(2) 0.29697(7) 1.30444(18) 0.0225(4) Uani 1 1 d . . . . .
H3 H -0.435020 0.329205 1.254128 0.027 Uiso 1 1 calc R U . . .
C4 C -0.4422(3) 0.250000 1.2309(3) 0.0246(5) Uani 1 2 d S T P . .
H4 H -0.487120 0.250000 1.130629 0.030 Uiso 1 2 calc R U P . .
C5 C -0.2925(2) 0.35068(7) 1.52815(18) 0.0210(3) Uani 1 1 d . . . . .
C6 C -0.0192(2) 0.33957(8) 1.4527(2) 0.0322(4) Uani 1 1 d . . . . .
H6A H 0.098019 0.350824 1.478713 0.048 Uiso 1 1 calc R U . . .
H6B H -0.068227 0.356486 1.361600 0.048 Uiso 1 1 calc R U . . .
H6C H -0.023410 0.301203 1.440685 0.048 Uiso 1 1 calc R U . . .
C7 C -0.3608(2) 0.39991(7) 1.44174(18) 0.0219(4) Uani 1 1 d . . . . .
C8 C -0.5319(2) 0.40464(8) 1.3874(2) 0.0268(4) Uani 1 1 d . . . . .
H8 H -0.605772 0.376376 1.399940 0.032 Uiso 1 1 calc R U . . .
C9 C -0.5958(2) 0.44984(8) 1.3154(2) 0.0295(4) Uani 1 1 d . . . . .
C10 C -0.4875(3) 0.49135(7) 1.3002(2) 0.0296(4) Uani 1 1 d . . . . .
H10 H -0.530507 0.522502 1.251572 0.036 Uiso 1 1 calc R U . . .
C11 C -0.3180(3) 0.48821(7) 1.3544(2) 0.0282(4) Uani 1 1 d . . . . .
C12 C -0.2563(2) 0.44219(7) 1.42568(19) 0.0246(4) Uani 1 1 d . . . . .
H12 H -0.140174 0.439848 1.463892 0.030 Uiso 1 1 calc R U . . .
C13 C -0.7795(3) 0.45409(10) 1.2541(3) 0.0463(6) Uani 1 1 d . . . . .
H13A H -0.801459 0.488521 1.207481 0.070 Uiso 1 1 calc R U . . .
H13B H -0.809447 0.426123 1.182405 0.070 Uiso 1 1 calc R U . . .
H13C H -0.847021 0.450402 1.332670 0.070 Uiso 1 1 calc R U . . .
C14 C -0.2022(3) 0.53332(8) 1.3351(3) 0.0404(5) Uani 1 1 d . . . . .
H14A H -0.087582 0.524397 1.379931 0.061 Uiso 1 1 calc R U . . .
H14B H -0.203957 0.540006 1.231335 0.061 Uiso 1 1 calc R U . . .
H14C H -0.239644 0.564951 1.381388 0.061 Uiso 1 1 calc R U . . .
C15 C -0.3571(2) 0.35563(7) 1.67497(19) 0.0255(4) Uani 1 1 d . . . . .
C16 C -0.5138(3) 0.33607(8) 1.6936(2) 0.0320(4) Uani 1 1 d . . . . .
H16 H -0.577439 0.316288 1.617978 0.038 Uiso 1 1 calc R U . . .
C17 C -0.5791(3) 0.34512(10) 1.8224(2) 0.0459(6) Uani 1 1 d . . . . .
C18 C -0.4836(4) 0.37321(11) 1.9317(2) 0.0544(8) Uani 1 1 d . . . . .
H18 H -0.527412 0.379737 2.019080 0.065 Uiso 1 1 calc R U . . .
C19 C -0.3252(4) 0.39223(10) 1.9174(2) 0.0522(7) Uani 1 1 d . . . . .
C20 C -0.2632(3) 0.38369(8) 1.7871(2) 0.0374(5) Uani 1 1 d . . . . .
H20 H -0.156064 0.397167 1.775099 0.045 Uiso 1 1 calc R U . . .
C21 C -0.7512(4) 0.32556(13) 1.8394(3) 0.0676(9) Uani 1 1 d . . . . .
H21A H -0.744997 0.305835 1.930439 0.101 Uiso 1 1 calc R U . . .
H21B H -0.793457 0.302473 1.757765 0.101 Uiso 1 1 calc R U . . .
H21C H -0.827309 0.355621 1.841147 0.101 Uiso 1 1 calc R U . . .
C22 C -0.2226(6) 0.42321(14) 2.0372(3) 0.0840(12) Uani 1 1 d . . . . .
H22A H -0.267965 0.459008 2.039075 0.126 Uiso 1 1 calc R U . . .
H22B H -0.105553 0.424833 2.020051 0.126 Uiso 1 1 calc R U . . .
H22C H -0.227711 0.405937 2.130476 0.126 Uiso 1 1 calc R U . . .
Cl2S Cl 0.1522(6) 0.26683(16) 1.1974(5) 0.0377(9) Uani 0.25 1 d D U P A -1
C1S C -0.0493(14) 0.2794(5) 1.0943(19) 0.041(3) Uani 0.25 1 d D U P A -1
H1SA H -0.132143 0.290864 1.156307 0.049 Uiso 0.25 1 calc R U P A -1
H1SB H -0.043545 0.305739 1.016858 0.049 Uiso 0.25 1 calc R U P A -1
Cl1S Cl -0.0934(9) 0.2154(4) 1.0230(11) 0.0602(14) Uani 0.25 1 d D U P A -1
C1S' C -0.0655(14) 0.2700(5) 1.1193(17) 0.041(3) Uani 0.25 1 d D U P B -2
H1SC H -0.129143 0.270648 1.202307 0.049 Uiso 0.25 1 calc R U P B -2
H1SD H -0.106455 0.300245 1.056645 0.049 Uiso 0.25 1 calc R U P B -2
Cl1' Cl 0.1456(8) 0.2840(2) 1.1910(7) 0.0602(14) Uani 0.25 1 d D U P B -2
Cl2' Cl -0.1291(6) 0.2129(3) 1.0197(7) 0.0388(9) Uani 0.25 1 d D U P B -2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C6 O1 C5 115.57(14) . .
C1 N1 H1 120.9(14) . .
C1 N1 H1 120.9(14) . 4_565
H1 N1 H1 118(3) . 4_565
N1 C1 C2 120.28(10) . 4_565
N1 C1 C2 120.28(10) . .
C2 C1 C2 119.3(2) 4_565 .
C3 C2 C1 118.72(16) . .
C3 C2 C5 121.23(15) . .
C1 C2 C5 119.72(14) . .
C4 C3 C2 121.72(17) . .
C4 C3 H3 119.1 . .
C2 C3 H3 119.1 . .
C3 C4 C3 119.4(2) . 4_565
C3 C4 H4 120.3 . .
C3 C4 H4 120.3 4_565 .
O1 C5 C2 109.49(13) . .
O1 C5 C15 104.41(14) . .
C2 C5 C15 113.52(14) . .
O1 C5 C7 109.70(14) . .
C2 C5 C7 114.32(14) . .
C15 C5 C7 104.87(13) . .
O1 C6 H6A 109.5 . .
O1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
O1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C12 C7 C8 118.35(16) . .
C12 C7 C5 120.63(15) . .
C8 C7 C5 120.84(16) . .
C9 C8 C7 121.24(18) . .
C9 C8 H8 119.4 . .
C7 C8 H8 119.4 . .
C8 C9 C10 118.97(18) . .
C8 C9 C13 120.88(19) . .
C10 C9 C13 120.16(18) . .
C11 C10 C9 121.21(17) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C10 C11 C12 118.85(18) . .
C10 C11 C14 120.44(18) . .
C12 C11 C14 120.71(18) . .
C7 C12 C11 121.35(17) . .
C7 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C20 C15 C16 119.27(19) . .
C20 C15 C5 119.47(18) . .
C16 C15 C5 121.06(16) . .
C15 C16 C17 120.9(2) . .
C15 C16 H16 119.6 . .
C17 C16 H16 119.6 . .
C18 C17 C16 118.6(2) . .
C18 C17 C21 120.9(2) . .
C16 C17 C21 120.5(3) . .
C17 C18 C19 121.8(2) . .
C17 C18 H18 119.1 . .
C19 C18 H18 119.1 . .
C18 C19 C20 118.8(2) . .
C18 C19 C22 121.2(3) . .
C20 C19 C22 119.9(3) . .
C15 C20 C19 120.6(2) . .
C15 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C17 C21 H21A 109.5 . .
C17 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C17 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
Cl1S C1S Cl2S 98.8(6) . .
Cl1S C1S H1SA 112.0 . .
Cl2S C1S H1SA 112.0 . .
Cl1S C1S H1SB 112.0 . .
Cl2S C1S H1SB 112.0 . .
H1SA C1S H1SB 109.7 . .
Cl2' C1S' Cl1' 123.6(8) . .
Cl2' C1S' H1SC 106.4 . .
Cl1' C1S' H1SC 106.4 . .
Cl2' C1S' H1SD 106.4 . .
Cl1' C1S' H1SD 106.4 . .
H1SC C1S' H1SD 106.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.420(2) .
O1 C5 1.446(2) .
N1 C1 1.370(3) .
N1 H1 0.84(2) .
N1 H1 0.84(2) 4_565
C1 C2 1.421(2) 4_565
C1 C2 1.421(2) .
C2 C3 1.392(2) .
C2 C5 1.533(2) .
C3 C4 1.381(2) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 C15 1.541(2) .
C5 C7 1.542(2) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C12 1.385(3) .
C7 C8 1.398(3) .
C8 C9 1.388(3) .
C8 H8 0.9500 .
C9 C10 1.388(3) .
C9 C13 1.506(3) .
C10 C11 1.383(3) .
C10 H10 0.9500 .
C11 C12 1.397(3) .
C11 C14 1.504(3) .
C12 H12 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C20 1.390(3) .
C15 C16 1.390(3) .
C16 C17 1.400(3) .
C16 H16 0.9500 .
C17 C18 1.378(4) .
C17 C21 1.502(4) .
C18 C19 1.388(4) .
C18 H18 0.9500 .
C19 C20 1.397(3) .
C19 C22 1.506(4) .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
Cl2S C1S 1.784(9) .
C1S Cl1S 1.769(8) .
C1S H1SA 0.9900 .
C1S H1SB 0.9900 .
C1S' Cl2' 1.755(8) .
C1S' Cl1' 1.765(8) .
C1S' H1SC 0.9900 .
C1S' H1SD 0.9900 .
