#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:23:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180076 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/22/7052266.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_7052266
loop_
_publ_author_name
'Ragaini, Fabio'
'Gasperini, Michela'
'Parma, Paolo'
'Gallo, Emma'
'Casati, Nicola'
'Macchi, Piero'
_publ_section_title
;
 Stability-inducing strain: application to the synthesis of alkyl-BIAN
 ligands (alkyl-BIAN = bis(alkyl)acenaphthenequinonediimine)
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1046
_journal_paper_doi               10.1039/b602257j
_journal_volume                  30
_journal_year                    2006
_chemical_formula_sum            'C33 H38 Br2 Cl2 N2 Ni'
_chemical_formula_weight         752.08
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2005-07-18T16:19:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                103.925(2)
_cell_angle_beta                 108.377(2)
_cell_angle_gamma                108.885(2)
_cell_formula_units_Z            2
_cell_length_a                   11.3215(10)
_cell_length_b                   11.7432(11)
_cell_length_c                   13.7576(12)
_cell_measurement_temperature    150(2)
_cell_volume                     1518.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13979
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    3.474
_exptl_absorpt_correction_T_max  0.6449
_exptl_absorpt_correction_T_min  0.6421
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             764
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²+6.6412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.108
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                3001
_reflns_number_total             4360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b602257j.txt
_cod_data_source_block           fr11
_cod_database_code               7052266
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5459(6) 0.2296(6) 0.1320(5) 0.0125(15) Uani 1 1 d . . .
C2 C 0.4632(7) 0.2461(6) 0.0289(5) 0.0148(16) Uani 1 1 d . . .
C3 C 0.5038(7) 0.1951(6) -0.0592(5) 0.0147(15) Uani 1 1 d . . .
C4 C 0.4678(7) 0.1829(6) -0.1673(6) 0.0208(17) Uani 1 1 d . . .
H4 H 0.3997 0.2061 -0.2022 0.025 Uiso 1 1 calc R . .
C5 C 0.5356(8) 0.1344(7) -0.2248(6) 0.0291(19) Uani 1 1 d . . .
H5 H 0.5124 0.1277 -0.2978 0.035 Uiso 1 1 calc R . .
C6 C 0.6348(8) 0.0969(7) -0.1766(6) 0.0265(18) Uani 1 1 d . . .
H6 H 0.6774 0.0658 -0.2172 0.032 Uiso 1 1 calc R . .
C8 C 0.7753(8) 0.0734(7) -0.0057(6) 0.0248(18) Uani 1 1 d . . .
H8 H 0.8229 0.0407 -0.0398 0.03 Uiso 1 1 calc R . .
C9 C 0.8051(7) 0.0904(7) 0.1027(6) 0.0219(17) Uani 1 1 d . . .
H9 H 0.8735 0.0695 0.141 0.026 Uiso 1 1 calc R . .
C10 C 0.7348(7) 0.1388(6) 0.1580(6) 0.0185(16) Uani 1 1 d . . .
H10 H 0.7567 0.1492 0.2316 0.022 Uiso 1 1 calc R . .
C11 C 0.6334(7) 0.1705(6) 0.1019(6) 0.0151(16) Uani 1 1 d . . .
C12 C 0.6044(7) 0.1543(6) -0.0096(6) 0.0165(16) Uani 1 1 d . . .
C7 C 0.6729(7) 0.1050(6) -0.0664(6) 0.0180(16) Uani 1 1 d . . .
C101 C 0.6047(6) 0.2455(6) 0.3178(5) 0.0128(15) Uani 1 1 d . . .
H101 H 0.6061 0.161 0.2909 0.015 Uiso 1 1 calc R . .
C102 C 0.7562(7) 0.3497(7) 0.3849(6) 0.0193(16) Uani 1 1 d . . .
H102 H 0.8017 0.3583 0.3354 0.023 Uiso 1 1 calc R . .
C103 C 0.5321(7) 0.2398(7) 0.3951(5) 0.0166(16) Uani 1 1 d . . .
H103 H 0.4343 0.1784 0.3522 0.02 Uiso 1 1 calc R . .
C104 C 0.8262(7) 0.2990(8) 0.4692(6) 0.0267(19) Uani 1 1 d . . .
H10A H 0.8189 0.2145 0.4304 0.032 Uiso 1 1 calc R . .
H10B H 0.9235 0.3585 0.5117 0.032 Uiso 1 1 calc R . .
C105 C 0.6035(7) 0.1915(7) 0.4804(6) 0.0228(17) Uani 1 1 d . . .
H10C H 0.5587 0.1833 0.5296 0.027 Uiso 1 1 calc R . .
H10D H 0.5958 0.1065 0.4425 0.027 Uiso 1 1 calc R . .
C106 C 0.5452(7) 0.3737(7) 0.4582(5) 0.0196(17) Uani 1 1 d . . .
H10E H 0.5 0.4057 0.4059 0.024 Uiso 1 1 calc R . .
H10F H 0.4997 0.3657 0.5069 0.024 Uiso 1 1 calc R . .
C107 C 0.7679(7) 0.4820(7) 0.4479(6) 0.0237(18) Uani 1 1 d . . .
H10G H 0.7249 0.5151 0.3956 0.028 Uiso 1 1 calc R . .
H10H H 0.8645 0.5432 0.4906 0.028 Uiso 1 1 calc R . .
C108 C 0.6969(7) 0.4699(7) 0.5260(6) 0.0226(17) Uani 1 1 d . . .
H108 H 0.7039 0.5552 0.565 0.027 Uiso 1 1 calc R . .
C109 C 0.7555(7) 0.2877(7) 0.5475(6) 0.0247(18) Uani 1 1 d . . .
H109 H 0.8003 0.2553 0.6006 0.03 Uiso 1 1 calc R . .
C110 C 0.7681(8) 0.4208(7) 0.6113(6) 0.0279(19) Uani 1 1 d . . .
H11A H 0.8646 0.4818 0.6551 0.033 Uiso 1 1 calc R . .
H11B H 0.724 0.4128 0.661 0.033 Uiso 1 1 calc R . .
C201 C 0.3123(7) 0.3292(6) -0.0597(5) 0.0142(15) Uani 1 1 d . . .
H201 H 0.3746 0.3507 -0.0952 0.017 Uiso 1 1 calc R . .
C202 C 0.2826(7) 0.4478(6) -0.0218(6) 0.0176(16) Uani 1 1 d . . .
H202 H 0.3673 0.5223 0.0362 0.021 Uiso 1 1 calc R . .
C203 C 0.1775(7) 0.2123(7) -0.1465(6) 0.0203(17) Uani 1 1 d . . .
H203 H 0.1954 0.1359 -0.1677 0.024 Uiso 1 1 calc R . .
C204 C 0.1687(7) 0.4144(7) 0.0204(6) 0.0220(17) Uani 1 1 d . . .
H20A H 0.201 0.3941 0.0854 0.026 Uiso 1 1 calc R . .
H20B H 0.1501 0.4894 0.0418 0.026 Uiso 1 1 calc R . .
C205 C 0.0682(7) 0.1823(7) -0.1018(6) 0.0229(18) Uani 1 1 d . . .
H20C H 0.1008 0.1601 -0.0381 0.027 Uiso 1 1 calc R . .
H20D H -0.0159 0.1081 -0.1582 0.027 Uiso 1 1 calc R . .
C206 C 0.2285(7) 0.4798(7) -0.1247(6) 0.0209(17) Uani 1 1 d . . .
H20E H 0.2104 0.5552 -0.1042 0.025 Uiso 1 1 calc R . .
H20F H 0.2982 0.5007 -0.1525 0.025 Uiso 1 1 calc R . .
C207 C 0.1252(7) 0.2460(7) -0.2487(6) 0.0263(18) Uani 1 1 d . . .
H20G H 0.1942 0.265 -0.2774 0.032 Uiso 1 1 calc R . .
H20H H 0.0413 0.1725 -0.3064 0.032 Uiso 1 1 calc R . .
C208 C 0.0964(7) 0.3644(7) -0.2149(6) 0.0227(18) Uani 1 1 d . . .
H208 H 0.0634 0.3865 -0.2795 0.027 Uiso 1 1 calc R . .
C209 C 0.0374(7) 0.2998(7) -0.0681(6) 0.0219(17) Uani 1 1 d . . .
H209 H -0.0331 0.2793 -0.0399 0.026 Uiso 1 1 calc R . .
C210 C -0.0149(7) 0.3326(8) -0.1711(6) 0.0292(19) Uani 1 1 d . . .
H21A H -0.0991 0.2591 -0.2283 0.035 Uiso 1 1 calc R . .
H21B H -0.0354 0.4068 -0.1515 0.035 Uiso 1 1 calc R . .
N1 N 0.5301(5) 0.2683(5) 0.2193(4) 0.0115(12) Uani 1 1 d . . .
N2 N 0.3829(5) 0.3010(5) 0.0367(4) 0.0132(12) Uani 1 1 d . . .
Ni1 Ni 0.39182(9) 0.34586(8) 0.19200(7) 0.0122(2) Uani 1 1 d . . .
Br1 Br 0.19583(8) 0.20439(8) 0.19898(7) 0.0316(2) Uani 1 1 d . . .
Br2 Br 0.51039(9) 0.57388(8) 0.27127(7) 0.0333(2) Uani 1 1 d . . .
C1S C 0.2031(8) 0.1672(7) 0.4595(7) 0.0313(19) Uani 1 1 d . . .
H1S1 H 0.2318 0.194 0.4061 0.038 Uiso 1 1 calc R . .
H1S2 H 0.2528 0.2414 0.5296 0.038 Uiso 1 1 calc R . .
Cl1 Cl 0.0260(2) 0.1220(2) 0.4146(2) 0.0552(7) Uani 1 1 d . . .
Cl2 Cl 0.2471(2) 0.0421(2) 0.4763(2) 0.0595(8) Uani 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 0 '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'
Cl Cl 0.1484 0.1585 '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 C1 C11 135.0(6) . . ?
N1 C1 C2 118.5(6) . . ?
C11 C1 C2 106.5(6) . . ?
N2 C2 C3 135.3(6) . . ?
N2 C2 C1 117.7(6) . . ?
C3 C2 C1 106.9(5) . . ?
C4 C3 C12 119.2(6) . . ?
C4 C3 C2 135.2(6) . . ?
C12 C3 C2 105.6(6) . . ?
C3 C4 C5 118.9(7) . . ?
C6 C5 C4 122.2(7) . . ?
C5 C6 C7 120.9(7) . . ?
C9 C8 C7 120.8(7) . . ?
C8 C9 C10 121.8(7) . . ?
C11 C10 C9 119.5(7) . . ?
C10 C11 C12 118.3(6) . . ?
C10 C11 C1 135.1(6) . . ?
C12 C11 C1 106.4(6) . . ?
C11 C12 C7 122.9(6) . . ?
C11 C12 C3 114.6(6) . . ?
C7 C12 C3 122.5(6) . . ?
C6 C7 C8 126.9(7) . . ?
C6 C7 C12 116.3(6) . . ?
C8 C7 C12 116.7(6) . . ?
N1 C101 C103 112.4(5) . . ?
N1 C101 C102 112.2(5) . . ?
C103 C101 C102 109.2(5) . . ?
C107 C102 C104 108.9(6) . . ?
C107 C102 C101 112.5(6) . . ?
C104 C102 C101 105.8(6) . . ?
C106 C103 C101 112.5(6) . . ?
C106 C103 C105 108.2(5) . . ?
C101 C103 C105 106.9(5) . . ?
C109 C104 C102 109.4(5) . . ?
C109 C105 C103 109.6(6) . . ?
C108 C106 C103 110.2(5) . . ?
C102 C107 C108 110.4(6) . . ?
C106 C108 C107 109.2(6) . . ?
C106 C108 C110 109.7(6) . . ?
C107 C108 C110 109.5(6) . . ?
C105 C109 C110 109.9(6) . . ?
C105 C109 C104 109.5(6) . . ?
C110 C109 C104 110.7(6) . . ?
C109 C110 C108 108.0(6) . . ?
N2 C201 C203 112.5(5) . . ?
N2 C201 C202 111.1(5) . . ?
C203 C201 C202 109.4(5) . . ?
C206 C202 C201 106.8(5) . . ?
C206 C202 C204 108.3(5) . . ?
C201 C202 C204 110.9(5) . . ?
C205 C203 C201 111.2(6) . . ?
C205 C203 C207 109.6(6) . . ?
C201 C203 C207 107.8(5) . . ?
C209 C204 C202 110.9(6) . . ?
C203 C205 C209 110.7(6) . . ?
C208 C206 C202 110.5(6) . . ?
C208 C207 C203 109.0(6) . . ?
C206 C208 C207 109.7(6) . . ?
C206 C208 C210 109.5(6) . . ?
C207 C208 C210 109.5(6) . . ?
C204 C209 C205 109.0(6) . . ?
C204 C209 C210 109.5(6) . . ?
C205 C209 C210 108.4(6) . . ?
C208 C210 C209 109.6(6) . . ?
C1 N1 C101 118.5(5) . . ?
C1 N1 Ni1 109.8(4) . . ?
C101 N1 Ni1 131.6(4) . . ?
C2 N2 C201 118.1(6) . . ?
C2 N2 Ni1 109.5(4) . . ?
C201 N2 Ni1 132.2(4) . . ?
N2 Ni1 N1 84.4(2) . . ?
N2 Ni1 Br2 103.39(15) . . ?
N1 Ni1 Br2 109.45(15) . . ?
N2 Ni1 Br1 113.06(15) . . ?
N1 Ni1 Br1 106.41(15) . . ?
Br2 Ni1 Br1 130.52(5) . . ?
Cl2 C1S Cl1 112.7(4) . . ?
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
C1 N1 1.267(8) . ?
C1 C11 1.483(9) . ?
C1 C2 1.530(9) . ?
C2 N2 1.289(8) . ?
C2 C3 1.490(9) . ?
C3 C4 1.369(9) . ?
C3 C12 1.419(9) . ?
C4 C5 1.410(10) . ?
C5 C6 1.373(10) . ?
C6 C7 1.409(10) . ?
C8 C9 1.369(10) . ?
C8 C7 1.413(10) . ?
C9 C10 1.415(9) . ?
C10 C11 1.382(9) . ?
C11 C12 1.413(9) . ?
C12 C7 1.415(9) . ?
C101 N1 1.489(8) . ?
C101 C103 1.536(9) . ?
C101 C102 1.547(9) . ?
C102 C107 1.526(10) . ?
C102 C104 1.545(9) . ?
C103 C106 1.536(9) . ?
C103 C105 1.540(9) . ?
C104 C109 1.537(10) . ?
C105 C109 1.526(10) . ?
C106 C108 1.524(10) . ?
C107 C108 1.539(10) . ?
C108 C110 1.546(9) . ?
C109 C110 1.532(10) . ?
C201 N2 1.490(8) . ?
C201 C203 1.531(9) . ?
C201 C202 1.546(9) . ?
C202 C206 1.542(9) . ?
C202 C204 1.552(9) . ?
C203 C205 1.528(10) . ?
C203 C207 1.543(9) . ?
C204 C209 1.509(10) . ?
C205 C209 1.531(10) . ?
C206 C208 1.524(10) . ?
C207 C208 1.528(10) . ?
C208 C210 1.541(10) . ?
C209 C210 1.546(10) . ?
N1 Ni1 2.035(5) . ?
N2 Ni1 2.035(5) . ?
Ni1 Br2 2.3464(12) . ?
Ni1 Br1 2.3489(12) . ?
C1S Cl2 1.739(7) . ?
C1S Cl1 1.748(8) . ?
