#------------------------------------------------------------------------------
#$Date: 2019-11-28 18:27:50 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244279 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/86/7238669.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_7238669
loop_
_publ_author_name
'Dudley, Timothy J.'
'Beck, Jennifer E.'
'Santos, Earl E. P.'
'Johnston, Kathryn A.'
'Kassel, William S.'
'Dougherty, William G.'
'Boyko, Walter J.'
'Zubris, Deanna L.'
_publ_section_title
;
 Conformational analysis via calculations and NMR spectroscopy for isomers
 of the mono(imino)pyridine ligand, 2-{(2,6-Me2-C6H3)NC(i-Pr)}C5H4N
;
_journal_issue                   15
_journal_name_full               'RSC Advances'
_journal_page_first              6237
_journal_paper_doi               10.1039/c2ra20688a
_journal_volume                  2
_journal_year                    2012
_chemical_formula_sum            'C17 H20 Br2 N2 Ni'
_chemical_formula_weight         470.88
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1735(8)
_cell_length_b                   10.4551(7)
_cell_length_c                   14.3322(9)
_cell_measurement_reflns_used    6507
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.07
_cell_measurement_theta_min      2.43
_cell_volume                     1793.3(2)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17630
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         33.27
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    5.536
_exptl_absorpt_correction_T_max  0.6658
_exptl_absorpt_correction_T_min  0.4040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0198P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0606
_reflns_number_gt                4895
_reflns_number_total             6803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra20688a.txt
_cod_data_source_block           zubr018
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7238669
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ni1 Ni 0.03921(2) 1.06385(3) 0.120254(17) 0.01182(6) Uani 1 1 d .
Br1 Br 0.043688(17) 1.13765(2) -0.046800(13) 0.01475(5) Uani 1 1 d .
Br2 Br 0.224070(17) 1.14027(2) 0.182987(14) 0.02027(6) Uani 1 1 d .
N1 N 0.01995(13) 0.99152(17) 0.24789(11) 0.0129(3) Uani 1 1 d .
N2 N -0.08522(13) 1.17701(17) 0.15109(11) 0.0124(3) Uani 1 1 d .
C1 C -0.06596(16) 1.0422(2) 0.28395(13) 0.0132(4) Uani 1 1 d .
C2 C -0.09683(17) 0.9901(2) 0.36456(13) 0.0160(4) Uani 1 1 d .
H2A H -0.1585 1.0241 0.3886 0.019 Uiso 1 1 calc R
C3 C -0.03643(17) 0.8876(2) 0.40959(14) 0.0174(4) Uani 1 1 d .
H3A H -0.0565 0.8510 0.4648 0.021 Uiso 1 1 calc R
C4 C 0.05284(17) 0.8390(2) 0.37380(14) 0.0166(4) Uani 1 1 d .
H4A H 0.0963 0.7704 0.4045 0.020 Uiso 1 1 calc R
C5 C 0.07725(17) 0.8936(2) 0.29161(14) 0.0160(4) Uani 1 1 d .
H5A H 0.1374 0.8595 0.2656 0.019 Uiso 1 1 calc R
C6 C -0.11972(16) 1.1539(2) 0.22925(13) 0.0133(4) Uani 1 1 d .
C7 C -0.20775(18) 1.2337(2) 0.26430(15) 0.0190(5) Uani 1 1 d .
H7A H -0.2211 1.3101 0.2217 0.023 Uiso 1 1 calc R
C8 C -0.1715(2) 1.2853(2) 0.36587(16) 0.0266(5) Uani 1 1 d .
H8A H -0.0939 1.3146 0.3746 0.040 Uiso 1 1 calc R
H8B H -0.1778 1.2171 0.4115 0.040 Uiso 1 1 calc R
H8C H -0.2199 1.3569 0.3761 0.040 Uiso 1 1 calc R
C9 C -0.31898(18) 1.1608(2) 0.25180(16) 0.0262(5) Uani 1 1 d .
H9A H -0.3430 1.1381 0.1848 0.039 Uiso 1 1 calc R
H9B H -0.3758 1.2151 0.2723 0.039 Uiso 1 1 calc R
H9C H -0.3091 1.0828 0.2903 0.039 Uiso 1 1 calc R
C10 C -0.12537(16) 1.2856(2) 0.09244(13) 0.0138(4) Uani 1 1 d .
C11 C -0.07185(17) 1.4035(2) 0.11365(14) 0.0170(4) Uani 1 1 d .
C12 C -0.10577(19) 1.5056(2) 0.05234(16) 0.0226(5) Uani 1 1 d .
H12A H -0.0711 1.5867 0.0651 0.027 Uiso 1 1 calc R
C13 C -0.18880(19) 1.4907(3) -0.02647(16) 0.0255(5) Uani 1 1 d .
H13A H -0.2108 1.5613 -0.0674 0.031 Uiso 1 1 calc R
C14 C -0.24010(18) 1.3730(2) -0.04606(14) 0.0230(5) Uani 1 1 d .
H14A H -0.2972 1.3638 -0.1005 0.028 Uiso 1 1 calc R
C15 C -0.20925(17) 1.2682(2) 0.01278(13) 0.0166(4) Uani 1 1 d .
C16 C 0.01932(19) 1.4212(2) 0.19853(15) 0.0230(5) Uani 1 1 d .
H16A H 0.0534 1.5057 0.1957 0.034 Uiso 1 1 calc R
H16B H 0.0762 1.3549 0.1988 0.034 Uiso 1 1 calc R
H16C H -0.0122 1.4147 0.2566 0.034 Uiso 1 1 calc R
C17 C -0.26504(18) 1.1403(2) -0.01036(15) 0.0242(5) Uani 1 1 d .
H17A H -0.2983 1.1373 -0.0780 0.036 Uiso 1 1 calc R
H17B H -0.3236 1.1285 0.0275 0.036 Uiso 1 1 calc R
H17C H -0.2094 1.0720 0.0043 0.036 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N1 Ni1 N2 78.91(6) . .
N1 Ni1 Br2 92.37(5) . .
N2 Ni1 Br2 114.16(5) . .
N1 Ni1 Br1 87.77(5) . 3_575
N2 Ni1 Br1 108.93(5) . 3_575
Br2 Ni1 Br1 136.093(13) . 3_575
N1 Ni1 Br1 173.25(5) . .
N2 Ni1 Br1 100.05(5) . .
Br2 Ni1 Br1 94.122(11) . .
Br1 Ni1 Br1 86.269(11) 3_575 .
Ni1 Br1 Ni1 93.731(11) 3_575 .
C5 N1 C1 119.72(16) . .
C5 N1 Ni1 125.01(13) . .
C1 N1 Ni1 114.95(13) . .
C6 N2 C10 121.62(17) . .
C6 N2 Ni1 116.99(14) . .
C10 N2 Ni1 121.15(11) . .
N1 C1 C2 120.56(18) . .
N1 C1 C6 113.62(16) . .
C2 C1 C6 125.82(17) . .
C1 C2 C3 119.19(18) . .
C4 C3 C2 119.76(18) . .
C3 C4 C5 118.00(19) . .
N1 C5 C4 122.73(18) . .
N2 C6 C1 115.02(17) . .
N2 C6 C7 123.18(18) . .
C1 C6 C7 121.80(16) . .
C6 C7 C9 110.48(19) . .
C6 C7 C8 114.16(18) . .
C9 C7 C8 112.20(17) . .
C15 C10 C11 122.2(2) . .
C15 C10 N2 119.48(19) . .
C11 C10 N2 118.11(18) . .
C12 C11 C10 117.6(2) . .
C12 C11 C16 120.4(2) . .
C10 C11 C16 121.99(19) . .
C13 C12 C11 121.1(2) . .
C12 C13 C14 120.1(2) . .
C13 C14 C15 121.0(2) . .
C10 C15 C14 117.9(2) . .
C10 C15 C17 121.8(2) . .
C14 C15 C17 120.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 2.0323(16) .
Ni1 N2 2.0334(16) .
Ni1 Br2 2.4022(3) .
Ni1 Br1 2.4851(4) 3_575
Ni1 Br1 2.5256(3) .
Br1 Ni1 2.4851(4) 3_575
N1 C5 1.330(3) .
N1 C1 1.356(2) .
N2 C6 1.289(2) .
N2 C10 1.444(3) .
C1 C2 1.390(3) .
C1 C6 1.490(3) .
C2 C3 1.390(3) .
C3 C4 1.380(3) .
C4 C5 1.389(3) .
C6 C7 1.515(3) .
C7 C9 1.535(3) .
C7 C8 1.539(3) .
C10 C15 1.397(3) .
C10 C11 1.402(3) .
C11 C12 1.396(3) .
C11 C16 1.501(3) .
C12 C13 1.380(3) .
C13 C14 1.385(4) .
C14 C15 1.392(3) .
C15 C17 1.509(3) .
