#------------------------------------------------------------------------------
#$Date: 2021-09-03 22:46:08 +0300 (Fri, 03 Sep 2021) $
#$Revision: 268425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/89/4518996.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_4518996
loop_
_publ_author_name
'Kolluru, Srinivas'
'Singh, Manvendra'
'Gaskins, Bryce'
'Boskovic, Zarko'
_publ_section_title
;
 Nickel-Catalyzed Annulations of ortho-Haloarylimines
;
_journal_issue                   16
_journal_name_full               'ACS Catalysis'
_journal_page_first              10351
_journal_page_last               10361
_journal_paper_doi               10.1021/acscatal.1c03092
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C20 H20 Br2 N2 Ni'
_chemical_formula_weight         506.91
_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
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-09-21 deposited with the CCDC.	2021-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.236(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0595(2)
_cell_length_b                   30.6742(7)
_cell_length_c                   8.6369(2)
_cell_measurement_reflns_used    3735
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.40
_cell_measurement_theta_min      5.72
_cell_volume                     1976.41(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      200(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15254
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         70.408
_diffrn_reflns_theta_min         2.881
_exptl_absorpt_coefficient_mu    6.176
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5841
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0410
_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)+(0.0657P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2904
_reflns_number_total             3553
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c03092_si_005.cif
_cod_data_source_block           q78k
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1976.41(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518996
_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   0.861
_shelx_estimated_absorpt_t_max   0.941
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
Br1 Br 0.10258(6) 0.42895(2) 0.34864(5) 0.03608(14) Uani 1 1 d . . . . .
Br2 Br 0.39876(7) 0.31500(2) 0.31451(5) 0.04237(15) Uani 1 1 d . . . . .
Ni1 Ni 0.31393(9) 0.37172(2) 0.45613(7) 0.02750(17) Uani 1 1 d . . . . .
N1 N 0.5330(5) 0.40647(10) 0.5714(4) 0.0287(7) Uani 1 1 d . . . . .
N2 N 0.2223(5) 0.33792(10) 0.6037(4) 0.0290(7) Uani 1 1 d . . . . .
C1 C 0.6671(6) 0.41067(15) 0.4915(5) 0.0404(10) Uani 1 1 d . . . . .
H1A H 0.613046 0.425162 0.381216 0.048 Uiso 1 1 calc R U . . .
H1AB H 0.711889 0.381636 0.475631 0.048 Uiso 1 1 calc R U . . .
C2 C 0.8188(7) 0.43827(19) 0.6115(6) 0.0513(12) Uani 1 1 d . . . . .
H2A H 0.858939 0.460474 0.550074 0.062 Uiso 1 1 calc R U . . .
H2AB H 0.922401 0.419823 0.677217 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7359(7) 0.45977(17) 0.7250(6) 0.0485(12) Uani 1 1 d . . . . .
H3A H 0.818098 0.458305 0.843890 0.058 Uiso 1 1 calc R U . . .
H3AB H 0.705126 0.490630 0.693615 0.058 Uiso 1 1 calc R U . . .
C4 C 0.5704(6) 0.43293(12) 0.6938(5) 0.0307(8) Uani 1 1 d . . . . .
C5 C 0.4579(5) 0.43743(12) 0.7943(4) 0.0287(8) Uani 1 1 d . . . . .
C6 C 0.3623(6) 0.47569(13) 0.7845(5) 0.0346(8) Uani 1 1 d . . . . .
H6 H 0.373476 0.498985 0.716569 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2508(6) 0.48034(14) 0.8725(5) 0.0388(9) Uani 1 1 d . . . . .
H7 H 0.183860 0.506362 0.863601 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2385(6) 0.44645(15) 0.9738(5) 0.0386(9) Uani 1 1 d . . . . .
H8 H 0.162427 0.449310 1.034478 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3365(6) 0.40821(14) 0.9875(5) 0.0359(9) Uani 1 1 d . . . . .
H9 H 0.326841 0.385265 1.057518 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4481(6) 0.40349(12) 0.8995(4) 0.0296(8) Uani 1 1 d . . . . .
C11 C 0.5617(6) 0.36386(13) 0.9196(4) 0.0311(8) Uani 1 1 d . . . . .
C12 C 0.7463(6) 0.36698(15) 1.0186(5) 0.0390(9) Uani 1 1 d . . . . .
H12 H 0.795992 0.393990 1.068681 0.047 Uiso 1 1 calc R U . . .
C13 C 0.8553(7) 0.33050(17) 1.0426(5) 0.0453(10) Uani 1 1 d . . . . .
H13 H 0.979117 0.332782 1.110727 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7879(7) 0.29134(14) 0.9703(5) 0.0417(10) Uani 1 1 d . . . . .
H14 H 0.864242 0.266748 0.986193 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6056(7) 0.28808(14) 0.8729(5) 0.0401(10) Uani 1 1 d . . . . .
H15 H 0.557533 0.260880 0.823597 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4929(6) 0.32386(13) 0.8468(4) 0.0325(8) Uani 1 1 d . . . . .
C17 C 0.2992(6) 0.31898(12) 0.7440(4) 0.0303(8) Uani 1 1 d . . . . .
C18 C 0.1764(7) 0.29067(16) 0.7953(5) 0.0447(11) Uani 1 1 d . . . . .
H18A H 0.183135 0.298239 0.908942 0.054 Uiso 1 1 calc R U . . .
H18B H 0.205860 0.259422 0.792523 0.054 Uiso 1 1 calc R U . . .
C19 C -0.0067(8) 0.3010(2) 0.6649(7) 0.0624(16) Uani 1 1 d . . . . .
H19A H -0.077271 0.318771 0.713882 0.075 Uiso 1 1 calc R U . . .
H19B H -0.073659 0.273911 0.618433 0.075 Uiso 1 1 calc R U . . .
C20 C 0.0294(6) 0.32641(14) 0.5302(5) 0.0382(9) Uani 1 1 d . . . . .
H20A H 0.002988 0.308338 0.428699 0.046 Uiso 1 1 calc R U . . .
H20B H -0.045416 0.353038 0.499786 0.046 Uiso 1 1 calc R U . . .
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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
N1 Ni1 N2 115.80(13) . . ?
N1 Ni1 Br2 106.16(10) . . ?
N2 Ni1 Br2 101.39(9) . . ?
N1 Ni1 Br1 99.78(10) . . ?
N2 Ni1 Br1 104.49(10) . . ?
Br2 Ni1 Br1 130.12(3) . . ?
C4 N1 C1 110.1(3) . . ?
C4 N1 Ni1 130.2(3) . . ?
C1 N1 Ni1 118.6(2) . . ?
C17 N2 C20 110.7(3) . . ?
C17 N2 Ni1 133.0(3) . . ?
C20 N2 Ni1 115.7(2) . . ?
N1 C1 C2 105.6(3) . . ?
N1 C1 H1A 110.6 . . ?
C2 C1 H1A 110.6 . . ?
N1 C1 H1AB 110.6 . . ?
C2 C1 H1AB 110.6 . . ?
H1A C1 H1AB 108.8 . . ?
C1 C2 C3 104.0(4) . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2AB 111.0 . . ?
C3 C2 H2AB 111.0 . . ?
H2A C2 H2AB 109.0 . . ?
C4 C3 C2 102.8(4) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3AB 111.2 . . ?
C2 C3 H3AB 111.2 . . ?
H3A C3 H3AB 109.1 . . ?
N1 C4 C5 122.7(4) . . ?
N1 C4 C3 114.4(4) . . ?
C5 C4 C3 122.9(3) . . ?
C6 C5 C10 120.1(4) . . ?
C6 C5 C4 119.5(3) . . ?
C10 C5 C4 120.5(4) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 119.0(4) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 118.9(4) . . ?
C9 C10 C11 121.2(3) . . ?
C5 C10 C11 119.8(3) . . ?
C16 C11 C12 118.8(4) . . ?
C16 C11 C10 122.9(4) . . ?
C12 C11 C10 118.4(4) . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 121.3(5) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 119.0(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 119.9(4) . . ?
C15 C16 C17 119.6(4) . . ?
C11 C16 C17 120.5(4) . . ?
N2 C17 C16 123.2(3) . . ?
N2 C17 C18 113.9(4) . . ?
C16 C17 C18 122.9(3) . . ?
C17 C18 C19 103.0(3) . . ?
C17 C18 H18A 111.2 . . ?
C19 C18 H18A 111.2 . . ?
C17 C18 H18B 111.2 . . ?
C19 C18 H18B 111.2 . . ?
H18A C18 H18B 109.1 . . ?
C18 C19 C20 105.2(4) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N2 C20 C19 105.6(4) . . ?
N2 C20 H20A 110.6 . . ?
C19 C20 H20A 110.6 . . ?
N2 C20 H20B 110.6 . . ?
C19 C20 H20B 110.6 . . ?
H20A C20 H20B 108.8 . . ?
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
Br1 Ni1 2.3766(8) . ?
Br2 Ni1 2.3715(7) . ?
Ni1 N1 1.979(3) . ?
Ni1 N2 1.990(3) . ?
N1 C4 1.275(5) . ?
N1 C1 1.492(5) . ?
N2 C17 1.273(5) . ?
N2 C20 1.482(5) . ?
C1 C2 1.526(6) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.529(6) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.503(6) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.480(5) . ?
C5 C6 1.388(6) . ?
C5 C10 1.403(5) . ?
C6 C7 1.387(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.492(6) . ?
C11 C16 1.394(6) . ?
C11 C12 1.411(6) . ?
C12 C13 1.389(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.368(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.483(6) . ?
C17 C18 1.504(5) . ?
C18 C19 1.513(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
