#------------------------------------------------------------------------------
#$Date: 2017-03-02 19:20:33 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192782 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/29/4312932.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_4312932
loop_
_publ_author_name
'Dirk Walther'
'Stefan Liesicke'
'Lars Böttcher'
'Reinald Fischer'
'Helmar Görls'
'Gavin Vaughan'
_publ_contact_author
;
         Dirk Walther
         Friedrich-Schiller-Universität Jena
         Institut für Anorganische und Analytische Chemie
         August-Bebel-Str. 2
         D-07743 Jena
         Germany
;
_publ_contact_author_email       'cdw@rz.uni-jena.de.de '
_publ_contact_author_fax         '03641 9-48102 '
_publ_contact_author_phone       '03641 9-48110 '
_publ_section_title
;
 Metal Complexes with 2,3-Bis(diphenylphosphino)-1,4-diazadiene Ligands:
 Synthesis, Structures, and an Intramolecular Metal-Mediated [4 + 2]
 Cycloaddition Employing a Benzene Ring as a Dienophile
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              625
_journal_page_last               632
_journal_paper_doi               10.1021/ic020534w
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C44 H42 Br2 N2 Ni P2'
_chemical_formula_weight         879.27
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 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                 108.304(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3600(3)
_cell_length_b                   11.0980(1)
_cell_length_c                   17.9282(2)
_cell_measurement_temperature    120(2)
_cell_volume                     3846.01(8)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device_type  'SMART - Bruker'
_diffrn_measurement_method       phi-scan
_diffrn_radiation_monochromator  SI<111>
_diffrn_radiation_source         'synchrotron - ESRF'
_diffrn_radiation_wavelength     0.45085
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25156
_diffrn_reflns_theta_full        14.51
_diffrn_reflns_theta_max         14.51
_diffrn_reflns_theta_min         7.20
_exptl_absorpt_coefficient_mu    1.442
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9165
_exptl_absorpt_correction_type   ?semi-empirical
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.221(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    rigid-group
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         4692
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0184
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0366P)²+0.2422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0498
_refine_ls_wR_factor_ref         0.0500
_reflns_number_gt                4654
_reflns_number_total             4692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic020534w_5.cif
_cod_data_source_block           FO1402
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_publ_contact_autor' replaced with '_publ_contact_author'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4998 2017-03-02 13:24:31Z antanas 
;
_cod_database_code               4312932
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni -0.346796(14) -2.06429(3) 0.165785(15) 0.01820(9) Uani 1 1 d . . .
Br1 Br -0.308599(13) -2.24477(2) 0.129925(14) 0.02735(9) Uani 1 1 d . . .
Br2 Br -0.458962(12) -2.07867(2) 0.077530(12) 0.03125(10) Uani 1 1 d . . .
P1 P -0.24437(3) -2.03155(6) 0.24139(3) 0.01812(14) Uani 1 1 d . . .
P2 P -0.37755(3) -1.89763(6) 0.20553(3) 0.01660(14) Uani 1 1 d . . .
N1 N -0.18303(10) -1.85490(19) 0.34771(11) 0.0203(4) Uani 1 1 d . . .
N2 N -0.31116(10) -1.76151(17) 0.34429(12) 0.0169(4) Uani 1 1 d . . .
C1 C -0.24465(12) -1.9000(2) 0.29888(13) 0.0186(5) Uani 1 1 d . . .
C2 C -0.30715(11) -1.8438(2) 0.28924(13) 0.0169(5) Uani 1 1 d . . .
C3 C -0.18700(12) -1.7841(2) 0.40359(14) 0.0208(5) Uani 1 1 d . . .
C4 C -0.25447(12) -1.7728(2) 0.42202(13) 0.0196(5) Uani 1 1 d . . .
C5 C -0.25581(13) -1.6668(2) 0.47277(13) 0.0225(5) Uani 1 1 d . . .
H5A H -0.2989 -1.6432 0.4783 0.027 Uiso 1 1 calc R . .
C6 C -0.19952(14) -1.6036(2) 0.51072(14) 0.0253(5) Uani 1 1 d . . .
C7 C -0.13332(12) -1.6326(2) 0.49896(13) 0.0248(5) Uani 1 1 d . . .
H7A H -0.0935 -1.5888 0.5283 0.030 Uiso 1 1 calc R . .
C8 C -0.12586(12) -1.7175(2) 0.44912(14) 0.0231(5) Uani 1 1 d . . .
C9 C -0.26493(13) -1.8898(2) 0.46317(14) 0.0227(5) Uani 1 1 d . . .
H9A H -0.2280 -1.8976 0.5135 0.034 Uiso 1 1 calc R . .
H9B H -0.2636 -1.9590 0.4297 0.034 Uiso 1 1 calc R . .
H9C H -0.3099 -1.8872 0.4724 0.034 Uiso 1 1 calc R . .
C10 C -0.20178(15) -1.5051(3) 0.56692(14) 0.0307(6) Uani 1 1 d . . .
H10A H -0.2492 -1.4959 0.5684 0.046 Uiso 1 1 calc R . .
H10B H -0.1865 -1.4293 0.5496 0.046 Uiso 1 1 calc R . .
H10C H -0.1711 -1.5255 0.6195 0.046 Uiso 1 1 calc R . .
C11 C -0.05924(14) -1.7456(2) 0.43567(17) 0.0308(6) Uani 1 1 d . . .
H11A H -0.0225 -1.6956 0.4703 0.046 Uiso 1 1 calc R . .
H11B H -0.0631 -1.7287 0.3808 0.046 Uiso 1 1 calc R . .
H11C H -0.0481 -1.8309 0.4470 0.046 Uiso 1 1 calc R . .
C12 C -0.34934(11) -1.6503(2) 0.32309(12) 0.0170(5) Uani 1 1 d . . .
C13 C -0.32678(13) -1.5623(2) 0.28099(13) 0.0207(5) Uani 1 1 d . . .
C14 C -0.36495(13) -1.4571(2) 0.26037(14) 0.0253(5) Uani 1 1 d . . .
H14A H -0.3503 -1.3976 0.2309 0.030 Uiso 1 1 calc R . .
C15 C -0.42376(14) -1.4363(2) 0.28141(15) 0.0271(6) Uani 1 1 d . . .
C16 C -0.44451(12) -1.5238(2) 0.32385(14) 0.0250(6) Uani 1 1 d . . .
H16A H -0.4851 -1.5107 0.3381 0.030 Uiso 1 1 calc R . .
C17 C -0.40786(12) -1.6305(2) 0.34645(13) 0.0197(5) Uani 1 1 d . . .
C18 C -0.26316(15) -1.5790(2) 0.25660(17) 0.0272(6) Uani 1 1 d . . .
H18A H -0.2561 -1.5075 0.2279 0.041 Uiso 1 1 calc R . .
H18B H -0.2690 -1.6500 0.2226 0.041 Uiso 1 1 calc R . .
H18C H -0.2229 -1.5905 0.3034 0.041 Uiso 1 1 calc R . .
C19 C -0.46328(18) -1.3198(3) 0.2601(2) 0.0442(7) Uani 1 1 d . . .
H19A H -0.4412 -1.2689 0.2302 0.066 Uiso 1 1 calc R . .
H19B H -0.4633 -1.2778 0.3082 0.066 Uiso 1 1 calc R . .
H19C H -0.5110 -1.3370 0.2281 0.066 Uiso 1 1 calc R . .
C20 C -0.43165(13) -1.7178(3) 0.39683(15) 0.0263(5) Uani 1 1 d . . .
H20A H -0.4011 -1.7883 0.4080 0.039 Uiso 1 1 calc R . .
H20B H -0.4791 -1.7434 0.3690 0.039 Uiso 1 1 calc R . .
H20C H -0.4302 -1.6786 0.4463 0.039 Uiso 1 1 calc R . .
C21 C -0.20389(13) -2.1431(2) 0.31537(12) 0.0207(5) Uani 1 1 d . . .
C22 C -0.24463(15) -2.2319(2) 0.33387(15) 0.0260(6) Uani 1 1 d . . .
H22A H -0.2927 -2.2359 0.3062 0.031 Uiso 1 1 calc R . .
C23 C -0.21470(15) -2.3144(3) 0.39286(15) 0.0314(6) Uani 1 1 d . . .
H23A H -0.2423 -2.3754 0.4053 0.038 Uiso 1 1 calc R . .
C24 C -0.14513(14) -2.3083(3) 0.43342(14) 0.0291(6) Uani 1 1 d . . .
H24A H -0.1246 -2.3658 0.4732 0.035 Uiso 1 1 calc R . .
C25 C -0.10504(14) -2.2184(3) 0.41626(15) 0.0303(6) Uani 1 1 d . . .
H25A H -0.0572 -2.2134 0.4450 0.036 Uiso 1 1 calc R . .
C26 C -0.13424(13) -2.1361(3) 0.35756(14) 0.0270(6) Uani 1 1 d . . .
H26A H -0.1065 -2.0744 0.3461 0.032 Uiso 1 1 calc R . .
C27 C -0.18361(11) -1.9981(2) 0.18853(13) 0.0224(5) Uani 1 1 d . . .
C28 C -0.14402(13) -2.0893(2) 0.17014(15) 0.0249(6) Uani 1 1 d . . .
H28A H -0.1456 -2.1691 0.1886 0.030 Uiso 1 1 calc R . .
C29 C -0.10220(14) -2.0609(3) 0.12419(15) 0.0301(6) Uani 1 1 d . . .
H29A H -0.0741 -2.1216 0.1123 0.036 Uiso 1 1 calc R . .
C30 C -0.10111(15) -1.9475(3) 0.09627(17) 0.0359(6) Uani 1 1 d . . .
H30A H -0.0734 -1.9301 0.0638 0.043 Uiso 1 1 calc R . .
C31 C -0.13981(16) -1.8578(3) 0.11467(18) 0.0423(7) Uani 1 1 d . . .
H31A H -0.1384 -1.7783 0.0955 0.051 Uiso 1 1 calc R . .
C32 C -0.18106(15) -1.8836(3) 0.16134(16) 0.0315(6) Uani 1 1 d . . .
H32A H -0.2076 -1.8214 0.1744 0.038 Uiso 1 1 calc R . .
C33 C -0.39386(12) -1.7816(2) 0.13047(13) 0.0208(5) Uani 1 1 d . . .
C34 C -0.36467(12) -1.8000(3) 0.07087(14) 0.0262(5) Uani 1 1 d . . .
H34A H -0.3433 -1.8749 0.0672 0.031 Uiso 1 1 calc R . .
C35 C -0.36666(14) -1.7100(3) 0.01705(16) 0.0343(6) Uani 1 1 d . . .
H35A H -0.3469 -1.7230 -0.0237 0.041 Uiso 1 1 calc R . .
C36 C -0.39748(15) -1.6010(3) 0.02267(17) 0.0347(7) Uani 1 1 d . . .
H36A H -0.3975 -1.5381 -0.0133 0.042 Uiso 1 1 calc R . .
C37 C -0.42821(14) -1.5827(2) 0.08014(16) 0.0297(6) Uani 1 1 d . . .
H37A H -0.4505 -1.5083 0.0827 0.036 Uiso 1 1 calc R . .
C38 C -0.42673(12) -1.6726(2) 0.13415(13) 0.0228(5) Uani 1 1 d . . .
H38A H -0.4481 -1.6600 0.1736 0.027 Uiso 1 1 calc R . .
C39 C -0.44775(12) -1.9171(2) 0.24547(14) 0.0191(5) Uani 1 1 d . . .
C40 C -0.51449(13) -1.8743(3) 0.21321(15) 0.0270(5) Uani 1 1 d . . .
H40A H -0.5261 -1.8263 0.1670 0.032 Uiso 1 1 calc R . .
C41 C -0.56407(15) -1.9012(3) 0.24820(19) 0.0355(7) Uani 1 1 d . . .
H41A H -0.6097 -1.8708 0.2260 0.043 Uiso 1 1 calc R . .
C42 C -0.54850(15) -1.9719(3) 0.31519(17) 0.0339(7) Uani 1 1 d . . .
H42A H -0.5830 -1.9900 0.3388 0.041 Uiso 1 1 calc R . .
C43 C -0.48229(14) -2.0154(3) 0.34697(16) 0.0308(6) Uani 1 1 d . . .
H43A H -0.4710 -2.0641 0.3928 0.037 Uiso 1 1 calc R . .
C44 C -0.43256(13) -1.9888(2) 0.31284(14) 0.0252(5) Uani 1 1 d . . .
H44A H -0.3870 -2.0195 0.3353 0.030 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 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0667 0.0580 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3147 0.7232 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1811 1.6452 '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
P1 Ni P2 88.35(2) . . ?
P1 Ni Br1 88.69(2) . . ?
P2 Ni Br1 176.65(2) . . ?
P1 Ni Br2 173.68(2) . . ?
P2 Ni Br2 87.633(19) . . ?
Br1 Ni Br2 95.451(14) . . ?
C1 P1 C21 102.65(11) . . ?
C1 P1 C27 105.06(12) . . ?
C21 P1 C27 107.08(11) . . ?
C1 P1 Ni 109.04(8) . . ?
C21 P1 Ni 118.56(9) . . ?
C27 P1 Ni 113.17(8) . . ?
C39 P2 C2 103.25(10) . . ?
C39 P2 C33 113.35(11) . . ?
C2 P2 C33 106.96(10) . . ?
C39 P2 Ni 112.29(8) . . ?
C2 P2 Ni 108.69(8) . . ?
C33 P2 Ni 111.70(9) . . ?
C3 N1 C1 116.5(2) . . ?
C2 N2 C12 122.04(19) . . ?
C2 N2 C4 114.17(19) . . ?
C12 N2 C4 120.41(18) . . ?
N1 C1 C2 122.3(2) . . ?
N1 C1 P1 119.71(18) . . ?
C2 C1 P1 117.85(18) . . ?
N2 C2 C1 118.3(2) . . ?
N2 C2 P2 127.22(17) . . ?
C1 C2 P2 114.31(18) . . ?
N1 C3 C8 119.4(2) . . ?
N1 C3 C4 120.0(2) . . ?
C8 C3 C4 120.6(2) . . ?
C5 C4 N2 110.0(2) . . ?
C5 C4 C3 112.9(2) . . ?
N2 C4 C3 106.75(18) . . ?
C5 C4 C9 109.92(19) . . ?
N2 C4 C9 109.35(19) . . ?
C3 C4 C9 107.8(2) . . ?
C6 C5 C4 123.2(2) . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 C10 121.6(3) . . ?
C7 C6 C10 118.8(2) . . ?
C8 C7 C6 123.6(2) . . ?
C7 C8 C3 118.3(2) . . ?
C7 C8 C11 123.9(2) . . ?
C3 C8 C11 117.8(2) . . ?
C13 C12 C17 120.4(2) . . ?
C13 C12 N2 119.9(2) . . ?
C17 C12 N2 119.6(2) . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 C18 119.2(2) . . ?
C12 C13 C18 122.0(2) . . ?
C15 C14 C13 121.9(2) . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 C19 120.8(3) . . ?
C14 C15 C19 120.9(3) . . ?
C15 C16 C17 122.1(2) . . ?
C16 C17 C12 118.4(2) . . ?
C16 C17 C20 118.6(2) . . ?
C12 C17 C20 122.9(2) . . ?
C26 C21 C22 119.6(2) . . ?
C26 C21 P1 120.9(2) . . ?
C22 C21 P1 119.31(19) . . ?
C23 C22 C21 119.8(3) . . ?
C24 C23 C22 120.2(3) . . ?
C23 C24 C25 120.0(2) . . ?
C26 C25 C24 120.3(3) . . ?
C25 C26 C21 120.1(3) . . ?
C32 C27 C28 120.0(2) . . ?
C32 C27 P1 118.93(19) . . ?
C28 C27 P1 120.9(2) . . ?
C27 C28 C29 118.7(2) . . ?
C30 C29 C28 120.7(3) . . ?
C29 C30 C31 120.5(3) . . ?
C30 C31 C32 119.8(3) . . ?
C27 C32 C31 120.2(3) . . ?
C34 C33 C38 119.4(2) . . ?
C34 C33 P2 116.2(2) . . ?
C38 C33 P2 123.99(19) . . ?
C35 C34 C33 120.3(3) . . ?
C34 C35 C36 119.8(3) . . ?
C37 C36 C35 120.4(3) . . ?
C38 C37 C36 120.2(3) . . ?
C37 C38 C33 119.8(2) . . ?
C40 C39 C44 118.6(2) . . ?
C40 C39 P2 126.2(2) . . ?
C44 C39 P2 115.09(18) . . ?
C41 C40 C39 119.9(3) . . ?
C40 C41 C42 121.1(3) . . ?
C43 C42 C41 119.1(2) . . ?
C44 C43 C42 120.3(3) . . ?
C43 C44 C39 121.0(2) . . ?
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
Ni P1 2.1314(6) . ?
Ni P2 2.1449(7) . ?
Ni Br1 2.3118(4) . ?
Ni Br2 2.3398(3) . ?
P1 C1 1.788(2) . ?
P1 C21 1.812(2) . ?
P1 C27 1.817(2) . ?
P2 C39 1.802(2) . ?
P2 C2 1.820(2) . ?
P2 C33 1.816(2) . ?
N1 C3 1.295(4) . ?
N1 C1 1.379(3) . ?
N2 C2 1.366(3) . ?
N2 C12 1.444(3) . ?
N2 C4 1.510(3) . ?
C1 C2 1.379(4) . ?
C3 C8 1.458(4) . ?
C3 C4 1.516(4) . ?
C4 C5 1.493(4) . ?
C4 C9 1.541(4) . ?
C5 C6 1.334(4) . ?
C6 C7 1.464(4) . ?
C6 C10 1.497(4) . ?
C7 C8 1.339(4) . ?
C8 C11 1.483(4) . ?
C12 C13 1.398(4) . ?
C12 C17 1.399(3) . ?
C13 C14 1.387(4) . ?
C13 C18 1.503(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.379(4) . ?
C15 C19 1.507(4) . ?
C16 C17 1.391(4) . ?
C17 C20 1.505(4) . ?
C21 C26 1.384(4) . ?
C21 C22 1.394(4) . ?
C22 C23 1.387(4) . ?
C23 C24 1.376(4) . ?
C24 C25 1.383(5) . ?
C25 C26 1.380(4) . ?
C27 C32 1.368(4) . ?
C27 C28 1.396(4) . ?
C28 C29 1.394(4) . ?
C29 C30 1.357(5) . ?
C30 C31 1.373(5) . ?
C31 C32 1.389(4) . ?
C33 C34 1.391(4) . ?
C33 C38 1.395(4) . ?
C34 C35 1.381(4) . ?
C35 C36 1.381(5) . ?
C36 C37 1.378(5) . ?
C37 C38 1.383(4) . ?
C39 C40 1.383(4) . ?
C39 C44 1.397(4) . ?
C40 C41 1.378(4) . ?
C41 C42 1.385(5) . ?
C42 C43 1.376(5) . ?
C43 C44 1.370(4) . ?
