#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:04:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178593 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/04/4070483.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_4070483
loop_
_publ_author_name
'Higgs, Andrew T.'
'Zinn, Paul J.'
'Simmons, Sarah J.'
'Sanford, Melanie S.'
_publ_section_title
;
 Oxidatively Induced Carbon−Halogen Bond-Forming Reactions at
 Nickel
;
_journal_issue                   21
_journal_name_full               Organometallics
_journal_page_first              6142
_journal_paper_doi               10.1021/om900849m
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C17 H15 Br N2 Ni'
_chemical_formula_sum            'C17 H15 Br N2 Ni'
_chemical_formula_weight         385.93
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8906(9)
_cell_length_b                   16.2569(13)
_cell_length_c                   8.5031(7)
_cell_measurement_reflns_used    9791
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      2.75
_cell_volume                     1505.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      85(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            36778
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    3.936
_exptl_absorpt_correction_T_max  0.4924
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2.10) Bruker/Siemens area
  detector absorption and other corrections, University of
  Gottingen, Germany 2003.
;
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0162
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0237P)²+0.3791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0422
_refine_ls_wR_factor_ref         0.0423
_reflns_number_gt                3718
_reflns_number_total             3769
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900849m_si_002.cif
_cod_data_source_block           ah192
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4070483
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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
Br1 Br 0.855254(13) 1.061069(7) 0.834578(16) 0.01725(4) Uani 1 1 d .
Ni2 Ni 0.756058(17) 0.943077(10) 0.72114(2) 0.01251(5) Uani 1 1 d .
N1 N 0.77216(11) 0.87151(7) 0.89910(16) 0.0145(2) Uani 1 1 d .
N2 N 0.73974(11) 1.00473(7) 0.53395(16) 0.0140(2) Uani 1 1 d .
C1 C 0.84654(14) 0.88293(10) 1.0236(2) 0.0188(3) Uani 1 1 d .
H1A H 0.9002 0.9290 1.0238 0.023 Uiso 1 1 calc R
C2 C 0.84798(15) 0.83028(10) 1.1515(2) 0.0215(3) Uani 1 1 d .
H2A H 0.9026 0.8396 1.2367 0.026 Uiso 1 1 calc R
C3 C 0.76834(16) 0.76369(10) 1.15314(19) 0.0209(3) Uani 1 1 d .
H3A H 0.7652 0.7279 1.2414 0.025 Uiso 1 1 calc R
C4 C 0.69347(16) 0.75025(10) 1.0240(2) 0.0191(3) Uani 1 1 d .
H4A H 0.6395 0.7044 1.0222 0.023 Uiso 1 1 calc R
C5 C 0.69757(13) 0.80406(9) 0.89715(18) 0.0152(3) Uani 1 1 d .
C6 C 0.63017(13) 0.79609(9) 0.74938(18) 0.0159(3) Uani 1 1 d .
C7 C 0.54352(13) 0.73440(9) 0.7193(2) 0.0194(3) Uani 1 1 d .
H7A H 0.5246 0.6948 0.7977 0.023 Uiso 1 1 calc R
C8 C 0.48572(15) 0.73165(10) 0.5743(2) 0.0237(3) Uani 1 1 d .
H8A H 0.4257 0.6907 0.5532 0.028 Uiso 1 1 calc R
C9 C 0.51605(16) 0.78910(10) 0.4603(2) 0.0251(3) Uani 1 1 d .
H9A H 0.4788 0.7859 0.3594 0.030 Uiso 1 1 calc R
C10 C 0.60071(16) 0.85167(9) 0.4917(2) 0.0210(3) Uani 1 1 d .
H10A H 0.6195 0.8908 0.4122 0.025 Uiso 1 1 calc R
C11 C 0.65770(13) 0.85746(9) 0.63763(19) 0.0154(3) Uani 1 1 d .
C12 C 0.83408(14) 1.00067(9) 0.43127(18) 0.0169(3) Uani 1 1 d .
H12A H 0.9036 0.9682 0.4578 0.020 Uiso 1 1 calc R
C13 C 0.83361(16) 1.04177(11) 0.2893(2) 0.0210(3) Uani 1 1 d .
H13A H 0.9014 1.0376 0.2195 0.025 Uiso 1 1 calc R
C14 C 0.73238(16) 1.08927(10) 0.25045(19) 0.0232(3) Uani 1 1 d .
H14A H 0.7289 1.1177 0.1530 0.028 Uiso 1 1 calc R
C15 C 0.63648(14) 1.09429(10) 0.3568(2) 0.0212(3) Uani 1 1 d .
H15A H 0.5665 1.1268 0.3327 0.025 Uiso 1 1 calc R
C16 C 0.64208(14) 1.05200(9) 0.4990(2) 0.0174(3) Uani 1 1 d .
C17 C 0.54033(15) 1.05638(10) 0.6169(2) 0.0245(4) Uani 1 1 d .
H17A H 0.4937 1.0049 0.6152 0.037 Uiso 1 1 calc R
H17B H 0.4858 1.1023 0.5907 0.037 Uiso 1 1 calc R
H17C H 0.5749 1.0649 0.7221 0.037 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
N2 Ni2 C11 91.19(6)
N2 Ni2 N1 174.66(5)
C11 Ni2 N1 84.36(6)
N2 Ni2 Br1 87.54(4)
C11 Ni2 Br1 172.27(4)
N1 Ni2 Br1 97.27(4)
C1 N1 C5 118.60(13)
C1 N1 Ni2 126.32(11)
C5 N1 Ni2 115.06(10)
C16 N2 C12 119.13(14)
C16 N2 Ni2 124.29(12)
C12 N2 Ni2 116.57(10)
N1 C1 C2 122.65(15)
C1 C2 C3 118.93(15)
C4 C3 C2 118.89(15)
C3 C4 C5 119.81(15)
N1 C5 C4 121.03(15)
N1 C5 C6 112.39(13)
C4 C5 C6 126.56(14)
C7 C6 C11 121.80(14)
C7 C6 C5 123.99(14)
C11 C6 C5 114.20(13)
C8 C7 C6 119.46(15)
C7 C8 C9 119.51(14)
C8 C9 C10 120.90(16)
C11 C10 C9 120.92(15)
C10 C11 C6 117.29(14)
C10 C11 Ni2 129.54(12)
C6 C11 Ni2 112.80(11)
N2 C12 C13 122.64(14)
C12 C13 C14 118.78(15)
C15 C14 C13 118.51(15)
C14 C15 C16 120.36(15)
N2 C16 C15 120.56(16)
N2 C16 C17 117.70(16)
C15 C16 C17 121.74(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 Ni2 2.4035(3)
Ni2 N2 1.8894(13)
Ni2 C11 1.8944(15)
Ni2 N1 1.9168(13)
N1 C1 1.346(2)
N1 C5 1.3647(19)
N2 C16 1.3453(19)
N2 C12 1.3499(19)
C1 C2 1.384(2)
C2 C3 1.387(2)
C3 C4 1.385(2)
C4 C5 1.390(2)
C5 C6 1.461(2)
C6 C7 1.401(2)
C6 C11 1.410(2)
C7 C8 1.385(2)
C8 C9 1.386(2)
C9 C10 1.399(2)
C10 C11 1.391(2)
C12 C13 1.380(2)
C13 C14 1.386(3)
C14 C15 1.384(2)
C15 C16 1.392(2)
C16 C17 1.496(2)
