#------------------------------------------------------------------------------
#$Date: 2020-03-05 00:36:37 +0100 (jue 05 de mar de 2020) $
#$Revision: 248823 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/58/7125844.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_7125844
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            'C45 H37 Cl2 N'
_chemical_formula_weight         662.65
_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                 106.074(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7550(4)
_cell_length_b                   20.6545(11)
_cell_length_c                   9.7582(5)
_cell_measurement_reflns_used    7463
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.39
_cell_volume                     1695.59(15)
_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    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0783
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23655
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.385
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.8371
_exptl_absorpt_correction_T_min  0.7886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       stick
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.158
_refine_diff_density_max         0.812
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+1.8447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1433
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09497k2.cif
_cod_data_source_block           jvr181015N1
_cod_depositor_comments
'Adding full bibliography for 7125838--7125846.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7125844
_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   0.919
_shelx_estimated_absorpt_t_max   0.965
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.942
;
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
Cl1 Cl 0.1344(9) 0.250000 0.5241(6) 0.0647(14) Uani 0.5 2 d DS T P A 1
Cl2 Cl 0.2652(4) 0.250000 0.8363(3) 0.0564(6) Uani 0.5 2 d DS TU P A 1
C1S C 0.3117(15) 0.250000 0.6698(9) 0.048(4) Uani 0.5 2 d DS TU P A 1
H1SA H 0.375908 0.211211 0.663543 0.058 Uiso 0.25 1 calc R U P A 1
H1SB H 0.375908 0.288789 0.663543 0.058 Uiso 0.25 1 calc R U P A 1
Cl1' Cl 0.1652(10) 0.2715(6) 0.5395(7) 0.0647(14) Uani 0.25 1 d D . P B -2
Cl2' Cl 0.2764(5) 0.27563(18) 0.8393(4) 0.0564(6) Uani 0.25 1 d D U P B -2
C1S' C 0.2950(17) 0.2302(6) 0.6890(11) 0.037(3) Uani 0.25 1 d D U P B -2
H1SC H 0.260824 0.184759 0.694122 0.045 Uiso 0.25 1 calc R U P B -2
H1SD H 0.406023 0.230549 0.682977 0.045 Uiso 0.25 1 calc R U P B -2
N1 N 0.4719(3) 0.250000 0.4062(3) 0.0175(5) Uani 1 2 d S T P . .
C1 C 0.5862(3) 0.250000 0.3314(3) 0.0145(5) Uani 1 2 d S T P . .
C2 C 0.6468(2) 0.30975(9) 0.29657(19) 0.0144(4) Uani 1 1 d . . . . .
C3 C 0.7714(2) 0.30787(10) 0.2334(2) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.815088 0.347376 0.211537 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8328(3) 0.250000 0.2018(3) 0.0226(6) Uani 1 2 d S T P . .
H4 H 0.917438 0.249999 0.158355 0.027 Uiso 1 2 calc R U P . .
C5 C 0.5886(2) 0.37461(9) 0.3442(2) 0.0146(4) Uani 1 1 d . . . . .
C6 C 0.6296(2) 0.37107(9) 0.5102(2) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.5273(3) 0.38818(11) 0.5899(2) 0.0240(5) Uani 1 1 d . . . . .
H7 H 0.424212 0.403990 0.542896 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5736(3) 0.38252(12) 0.7388(2) 0.0306(5) Uani 1 1 d . . . . .
H8 H 0.502368 0.395258 0.791697 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7214(3) 0.35868(12) 0.8093(2) 0.0335(6) Uani 1 1 d . . . . .
H9 H 0.751616 0.354112 0.910093 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8260(3) 0.34134(11) 0.7310(2) 0.0292(5) Uani 1 1 d . . . . .
H10 H 0.928640 0.325123 0.778175 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7798(3) 0.34784(11) 0.5837(2) 0.0239(5) Uani 1 1 d . . . . .
H11 H 0.852401 0.336170 0.531358 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6732(2) 0.43371(9) 0.2992(2) 0.0160(4) Uani 1 1 d . . . . .
C13 C 0.7682(2) 0.47620(10) 0.3965(2) 0.0196(4) Uani 1 1 d . . . . .
H13 H 0.789292 0.467840 0.495738 0.023 Uiso 1 1 calc R U . . .
C14 C 0.8332(2) 0.53101(10) 0.3506(2) 0.0246(5) Uani 1 1 d . . . . .
H14 H 0.897376 0.559676 0.418863 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8052(2) 0.54394(10) 0.2074(3) 0.0260(5) Uani 1 1 d . . . . .
H15 H 0.850046 0.581179 0.176452 0.031 Uiso 1 1 calc R U . . .
C16 C 0.7101(2) 0.50165(11) 0.1081(2) 0.0240(5) Uani 1 1 d . . . . .
H16 H 0.690688 0.509906 0.009025 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6441(2) 0.44786(10) 0.1535(2) 0.0193(4) Uani 1 1 d . . . . .
H17 H 0.577798 0.419928 0.084937 0.023 Uiso 1 1 calc R U . . .
C18 C 0.4096(2) 0.38715(9) 0.2710(2) 0.0164(4) Uani 1 1 d . . . . .
C19 C 0.3172(2) 0.34591(10) 0.1680(2) 0.0203(4) Uani 1 1 d . . . . .
H19 H 0.363156 0.307591 0.142924 0.024 Uiso 1 1 calc R U . . .
C20 C 0.1582(2) 0.36008(11) 0.1011(2) 0.0246(5) Uani 1 1 d . . . . .
H20 H 0.096313 0.330709 0.033163 0.030 Uiso 1 1 calc R U . . .
C21 C 0.0900(2) 0.41623(12) 0.1326(2) 0.0263(5) Uani 1 1 d . . . . .
H21 H -0.018654 0.425440 0.087648 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1821(2) 0.45925(11) 0.2311(2) 0.0253(5) Uani 1 1 d . . . . .
H22 H 0.137175 0.498622 0.252094 0.030 Uiso 1 1 calc R U . . .
C23 C 0.3395(2) 0.44458(10) 0.2984(2) 0.0209(4) Uani 1 1 d . . . . .
H23 H 0.401340 0.474459 0.365136 0.025 Uiso 1 1 calc R U . . .
H1 H 0.423(3) 0.2861(12) 0.408(3) 0.030(7) 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'
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'
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
Cl2 C1S Cl1 110.9(6) . .
Cl2 C1S H1SA 109.5 . .
Cl1 C1S H1SA 109.5 . .
Cl2 C1S H1SB 109.5 . .
Cl1 C1S H1SB 109.5 . .
H1SA C1S H1SB 108.0 . .
Cl2' C1S' Cl1' 103.6(6) . .
Cl2' C1S' H1SC 111.0 . .
Cl1' C1S' H1SC 111.0 . .
Cl2' C1S' H1SD 111.0 . .
Cl1' C1S' H1SD 111.0 . .
H1SC C1S' H1SD 109.0 . .
H1SA C1S' H1SB 81.8 4_565 4_565
C1 N1 H1 116.4(17) . .
C1 N1 H1 116.4(17) . 4_565
H1 N1 H1 119(3) . 4_565
N1 C1 C2 119.73(12) . 4_565
N1 C1 C2 119.72(12) . .
C2 C1 C2 120.5(2) 4_565 .
C3 C2 C1 118.14(18) . .
C3 C2 C5 121.26(17) . .
C1 C2 C5 120.21(16) . .
C4 C3 C2 121.58(19) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C3 C4 C3 120.0(3) . 4_565
C3 C4 H4 120.0 . .
C3 C4 H4 120.0 4_565 .
C2 C5 C12 111.90(15) . .
C2 C5 C18 112.33(15) . .
C12 C5 C18 103.79(15) . .
C2 C5 C6 105.68(15) . .
C12 C5 C6 109.87(15) . .
C18 C5 C6 113.41(15) . .
C7 C6 C11 117.56(18) . .
C7 C6 C5 124.90(17) . .
C11 C6 C5 117.53(17) . .
C6 C7 C8 121.0(2) . .
C6 C7 H7 119.5 . .
C8 C7 H7 119.5 . .
C9 C8 C7 120.6(2) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C8 C9 C10 119.2(2) . .
C8 C9 H9 120.4 . .
C10 C9 H9 120.4 . .
C11 C10 C9 119.8(2) . .
C11 C10 H10 120.1 . .
C9 C10 H10 120.1 . .
C10 C11 C6 121.9(2) . .
C10 C11 H11 119.1 . .
C6 C11 H11 119.1 . .
C13 C12 C17 117.88(18) . .
C13 C12 C5 123.07(17) . .
C17 C12 C5 118.89(17) . .
C12 C13 C14 120.91(19) . .
C12 C13 H13 119.5 . .
C14 C13 H13 119.5 . .
C15 C14 C13 120.6(2) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C14 C15 C16 119.17(19) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C17 C16 C15 120.23(19) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C16 C17 C12 121.17(19) . .
C16 C17 H17 119.4 . .
C12 C17 H17 119.4 . .
C19 C18 C23 117.41(18) . .
C19 C18 C5 122.67(17) . .
C23 C18 C5 119.66(17) . .
C18 C19 C20 120.92(19) . .
C18 C19 H19 119.5 . .
C20 C19 H19 119.5 . .
C21 C20 C19 120.7(2) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
C20 C21 C22 119.21(19) . .
C20 C21 H21 120.4 . .
C22 C21 H21 120.4 . .
C23 C22 C21 119.9(2) . .
C23 C22 H22 120.1 . .
C21 C22 H22 120.1 . .
C22 C23 C18 121.81(19) . .
C22 C23 H23 119.1 . .
C18 C23 H23 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1S 1.791(9) .
Cl2 C1S 1.781(8) .
C1S H1SA 0.9900 .
C1S H1SB 0.9900 .
Cl1' C1S' 1.797(9) .
Cl2' C1S' 1.787(9) .
C1S' H1SC 0.9900 .
C1S' H1SD 0.9900 .
N1 C1 1.392(3) .
N1 H1 0.86(2) .
N1 H1 0.86(2) 4_565
C1 C2 1.421(2) 4_565
C1 C2 1.421(2) .
C2 C3 1.394(3) .
C2 C5 1.550(3) .
C3 C4 1.380(2) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C5 C12 1.553(3) .
C5 C18 1.554(2) .
C5 C6 1.561(3) .
C6 C7 1.385(3) .
C6 C11 1.397(3) .
C7 C8 1.401(3) .
C7 H7 0.9500 .
C8 C9 1.377(3) .
C8 H8 0.9500 .
C9 C10 1.392(4) .
C9 H9 0.9500 .
C10 C11 1.387(3) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.388(3) .
C12 C17 1.403(3) .
C13 C14 1.395(3) .
C13 H13 0.9500 .
C14 C15 1.377(3) .
C14 H14 0.9500 .
C15 C16 1.395(3) .
C15 H15 0.9500 .
C16 C17 1.381(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
C18 C19 1.393(3) .
C18 C23 1.395(3) .
C19 C20 1.395(3) .
C19 H19 0.9500 .
C20 C21 1.377(3) .
C20 H20 0.9500 .
C21 C22 1.390(3) .
C21 H21 0.9500 .
C22 C23 1.386(3) .
C22 H22 0.9500 .
C23 H23 0.9500 .
