#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200437.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2200437
loop_
_publ_author_name
'Fontaine, Frédéric-Georges'
_publ_section_title
;
 cis-Bis(2,2-bipyridine)dichloronickel(II) methanol solvate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m270
_journal_page_last               m271
_journal_paper_doi               10.1107/S1600536801007838
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '[Ni Cl2 (C10 H8 N2)2], C1 H4 O1'
_chemical_formula_moiety         'C20 H16 Cl2 N4 Ni1, C1 H4 O1'
_chemical_formula_sum            'C21 H20 Cl2 N4 Ni O'
_chemical_formula_weight         474.020
_chemical_name_systematic
;
cis-Bis(2,2-bipyridine)dichloronickel(II) methanol solvate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.455(3)
_cell_length_b                   13.830(4)
_cell_length_c                   28.548(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      20.00
_cell_volume                     4128(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRC-2 and NRC-2A (Ahmed et al., 1973)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXL96
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  .073
_diffrn_reflns_av_sigmaI/netI    .089
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            22288
_diffrn_reflns_theta_full        69.87
_diffrn_reflns_theta_max         69.87
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        'no decay, variation 0.0'
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    3.903
_exptl_absorpt_correction_T_max  .593
_exptl_absorpt_correction_T_min  .432
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(ABSORP in NRCVAX; Gabe et al., 1989)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1952.0
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .23
_exptl_crystal_size_min          .16
_refine_diff_density_max         .31
_refine_diff_density_min         -.65
_refine_ls_extinction_coef       .00066(5)
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   .79
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .79
_refine_ls_restrained_S_obs      1.01
_refine_ls_R_factor_all          .088
_refine_ls_R_factor_gt           .047
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.04P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .112
_refine_ls_wR_factor_ref         .101
_reflns_number_gt                2054
_reflns_number_total             3908
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6029.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2200437
_cod_database_fobs_code          2200437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Ni .14225(6) .39332(5) .38102(2) .0470(2) Uani d . 1 . Ni
Cl1 .28217(11) .26123(7) .36335(4) .0605(3) Uani d . 1 . Cl
Cl2 .29823(10) .47056(8) .43132(4) .0577(3) Uani d . 1 . Cl
N1 .2053(3) .4614(2) .32013(12) .0471(9) Uani d . 1 . N
N2 .0161(3) .3383(2) .33035(13) .0501(9) Uani d . 1 . N
C1 .3009(4) .5259(3) .31710(18) .0573(12) Uani d . 1 . C
H1 .3350 .5512 .3446 .069 Uiso calc R 1 . H
C2 .3506(4) .5561(3) .27465(19) .0651(14) Uani d . 1 . C
H2 .4182 .5998 .2737 .078 Uiso calc R 1 . H
C3 .2991(5) .5209(3) .23441(19) .0650(14) Uani d . 1 . C
H3 .3321 .5399 .2056 .078 Uiso calc R 1 . H
C4 .1980(4) .4573(3) .23634(17) .0584(12) Uani d . 1 . C
H4 .1599 .4343 .2091 .070 Uiso calc R 1 . H
C5 .1548(4) .4286(3) .27983(17) .0485(11) Uani d . 1 . C
C6 .0469(4) .3582(3) .28575(17) .0490(11) Uani d . 1 . C
C7 -.0171(4) .3162(3) .24814(18) .0579(12) Uani d . 1 . C
H7 .0078 .3294 .2175 .069 Uiso calc R 1 . H
C8 -.1182(4) .2547(3) .2571(2) .0669(14) Uani d . 1 . C
H8 -.1625 .2257 .2325 .080 Uiso calc R 1 . H
C9 -.1520(4) .2370(3) .30239(18) .0655(14) Uani d . 1 . C
H9 -.2209 .1968 .3091 .079 Uiso calc R 1 . H
C10 -.0836(4) .2789(3) .33783(18) .0599(13) Uani d . 1 . C
H10 -.1073 .2656 .3686 .072 Uiso calc R 1 . H
N3 .0100(3) .4972(2) .40138(12) .0476(9) Uani d . 1 . N
N4 .0490(3) .3248(2) .43582(12) .0473(9) Uani d . 1 . N
C11 -.0042(4) .5849(3) .38084(16) .0526(11) Uani d . 1 . C
H11 .0460 .6004 .3550 .063 Uiso calc R 1 . H
C12 -.0910(4) .6517(3) .39726(18) .0613(14) Uani d . 1 . C
H12 -.0989 .7116 .3827 .074 Uiso calc R 1 . H
C13 -.1652(4) .6296(3) .43496(18) .0641(14) Uani d . 1 . C
H13 -.2248 .6740 .4460 .077 Uiso calc R 1 . H
C14 -.1515(4) .5405(3) .45685(17) .0566(12) Uani d . 1 . C
H14 -.2004 .5246 .4830 .068 Uiso calc R 1 . H
C15 -.0625(4) .4757(3) .43855(15) .0459(10) Uani d . 1 . C
C16 -.0420(4) .3774(3) .45807(15) .0472(11) Uani d . 1 . C
C17 -.1105(4) .3419(3) .49582(16) .0570(12) Uani d . 1 . C
H17 -.1710 .3802 .5108 .068 Uiso calc R 1 . H
C18 -.0872(4) .2482(4) .51086(17) .0638(14) Uani d . 1 . C
H18 -.1318 .2226 .5362 .077 Uiso calc R 1 . H
C19 .0029(5) .1934(3) .48768(17) .0632(14) Uani d . 1 . C
H19 .0186 .1299 .4968 .076 Uiso calc R 1 . H
C20 .0697(4) .2334(3) .45087(16) .0557(12) Uani d . 1 . C
H20 .1313 .1962 .4358 .067 Uiso calc R 1 . H
O1 .5478(3) .3869(3) .36236(13) .0820(11) Uani d . 1 . O
H1A .4736 .3835 .3716 .123 Uiso calc R 1 . H
C21 .6168(5) .4483(5) .3914(2) .110(2) Uani d . 1 . C
H21A .5642 .5023 .4001 .165 Uiso calc R 1 . H
H21B .6912 .4711 .3751 .165 Uiso calc R 1 . H
H21C .6425 .4139 .4190 .165 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Ni Ni -3.0029 .5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .3639 .7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 '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_publ_flag
N4 Ni N3 78.00(14) y
N4 Ni N1 170.07(14) y
N3 Ni N1 97.58(13) y
N4 Ni N2 93.37(14) y
N3 Ni N2 91.44(13) y
N1 Ni N2 77.75(14) y
N4 Ni Cl1 95.58(10) y
N3 Ni Cl1 173.48(10) y
N1 Ni Cl1 88.60(10) y
N2 Ni Cl1 87.84(10) y
N4 Ni Cl2 94.06(10) y
N3 Ni Cl2 88.70(10) y
N1 Ni Cl2 94.73(11) y
N2 Ni Cl2 172.43(11) y
Cl1 Ni Cl2 92.87(5) y
C1 N1 C5 117.5(4) n
C1 N1 Ni 126.1(3) n
C5 N1 Ni 115.9(3) n
C6 N2 C10 117.6(4) n
C6 N2 Ni 115.3(3) n
C10 N2 Ni 126.8(3) n
N1 C1 C2 122.5(5) n
N1 C1 H1 118.7 ?
C2 C1 H1 118.7 ?
C3 C2 C1 118.9(4) n
C3 C2 H2 120.6 ?
C1 C2 H2 120.6 ?
C2 C3 C4 120.0(5) n
C2 C3 H3 120.0 ?
C4 C3 H3 120.0 ?
C3 C4 C5 118.1(5) n
C3 C4 H4 120.9 ?
C5 C4 H4 120.9 ?
N1 C5 C4 123.0(4) n
N1 C5 C6 114.7(4) n
C4 C5 C6 122.3(4) n
N2 C6 C7 122.0(4) n
N2 C6 C5 114.9(4) n
C7 C6 C5 123.1(4) n
C8 C7 C6 118.9(5) n
C8 C7 H7 120.5 ?
C6 C7 H7 120.5 ?
C9 C8 C7 118.9(5) n
C9 C8 H8 120.5 ?
C7 C8 H8 120.5 ?
C8 C9 C10 119.4(5) n
C8 C9 H9 120.3 ?
C10 C9 H9 120.3 ?
N2 C10 C9 123.1(5) n
N2 C10 H10 118.4 ?
C9 C10 H10 118.4 ?
C15 N3 C11 118.7(4) n
C15 N3 Ni 116.5(3) n
C11 N3 Ni 124.8(3) n
C20 N4 C16 117.7(4) n
C20 N4 Ni 126.3(3) n
C16 N4 Ni 115.9(3) n
N3 C11 C12 121.7(4) n
N3 C11 H11 119.2 ?
C12 C11 H11 119.2 ?
C13 C12 C11 119.6(4) n
C13 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
C12 C13 C14 119.7(4) n
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
C13 C14 C15 118.1(4) n
C13 C14 H14 121.0 ?
C15 C14 H14 121.0 ?
N3 C15 C14 122.2(4) n
N3 C15 C16 114.8(4) n
C14 C15 C16 123.0(4) n
N4 C16 C17 122.5(4) n
N4 C16 C15 114.7(4) n
C17 C16 C15 122.9(4) n
C16 C17 C18 118.8(5) n
C16 C17 H17 120.6 ?
C18 C17 H17 120.6 ?
C19 C18 C17 119.0(5) n
C19 C18 H18 120.5 ?
C17 C18 H18 120.5 ?
C20 C19 C18 119.5(5) n
C20 C19 H19 120.3 ?
C18 C19 H19 120.3 ?
N4 C20 C19 122.5(4) n
N4 C20 H20 118.8 ?
C19 C20 H20 118.8 ?
C21 O1 H1A 109.5 ?
O1 C21 H21A 109.5 ?
O1 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O1 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni N4 . 2.073(3) y
Ni N3 . 2.077(3) y
Ni N1 . 2.084(3) y
Ni N2 . 2.100(4) y
Ni Cl1 . 2.3940(13) y
Ni Cl2 . 2.4213(13) y
N1 C1 . 1.342(5) n
N1 C5 . 1.344(5) n
N2 C6 . 1.342(5) n
N2 C10 . 1.344(5) n
C1 C2 . 1.384(6) n
C1 H1 . .9300 ?
C2 C3 . 1.359(6) n
C2 H2 . .9300 ?
C3 C4 . 1.376(6) n
C3 H3 . .9300 ?
C4 C5 . 1.380(6) n
C4 H4 . .9300 ?
C5 C6 . 1.500(5) n
C6 C7 . 1.392(6) n
C7 C8 . 1.380(6) n
C7 H7 . .9300 ?
C8 C9 . 1.364(6) n
C8 H8 . .9300 ?
C9 C10 . 1.368(6) n
C9 H9 . .9300 ?
C10 H10 . .9300 ?
N3 C15 . 1.338(5) n
N3 C11 . 1.356(5) n
N4 C20 . 1.351(5) n
N4 C16 . 1.357(5) n
C11 C12 . 1.377(5) n
C11 H11 . .9300 ?
C12 C13 . 1.361(6) n
C12 H12 . .9300 ?
C13 C14 . 1.389(6) n
C13 H13 . .9300 ?
C14 C15 . 1.394(5) n
C14 H14 . .9300 ?
C15 C16 . 1.484(5) n
C16 C17 . 1.384(5) n
C17 C18 . 1.387(6) n
C17 H17 . .9300 ?
C18 C19 . 1.378(6) n
C18 H18 . .9300 ?
C19 C20 . 1.378(6) n
C19 H19 . .9300 ?
C20 H20 . .9300 ?
O1 C21 . 1.388(5) n
O1 H1A . .8200 ?
C21 H21A . .9600 ?
C21 H21B . .9600 ?
C21 H21C . .9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1A Cl1 1_555 .82 2.63 3.276(3) 136.6 y
O1 H1A Cl2 1_555 .82 2.78 3.467(3) 142.8 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
N3 Ni N1 C1 88.3(3) n
N2 Ni N1 C1 178.2(3) n
Cl1 Ni N1 C1 -93.8(3) n
Cl2 Ni N1 C1 -1.0(3) n
N3 Ni N1 C5 -99.9(3) n
N2 Ni N1 C5 -10.1(3) n
Cl1 Ni N1 C5 78.0(3) n
Cl2 Ni N1 C5 170.7(3) n
N4 Ni N2 C6 -174.3(3) n
N3 Ni N2 C6 107.6(3) n
N1 Ni N2 C6 10.2(3) n
Cl1 Ni N2 C6 -78.9(3) n
N4 Ni N2 C10 -.9(4) n
N3 Ni N2 C10 -79.0(4) n
N1 Ni N2 C10 -176.4(4) n
Cl1 Ni N2 C10 94.5(3) n
C5 N1 C1 C2 -2.3(6) n
Ni N1 C1 C2 169.3(3) n
N1 C1 C2 C3 1.5(7) n
C1 C2 C3 C4 .8(7) n
C2 C3 C4 C5 -2.2(7) n
C1 N1 C5 C4 .8(6) n
Ni N1 C5 C4 -171.6(3) n
C1 N1 C5 C6 -178.9(3) n
Ni N1 C5 C6 8.6(4) n
C3 C4 C5 N1 1.4(6) n
C3 C4 C5 C6 -178.9(4) n
C10 N2 C6 C7 -2.8(6) n
Ni N2 C6 C7 171.3(3) n
C10 N2 C6 C5 177.2(3) n
Ni N2 C6 C5 -8.8(4) n
N1 C5 C6 N2 .2(5) n
C4 C5 C6 N2 -179.6(4) n
N1 C5 C6 C7 -179.8(4) n
C4 C5 C6 C7 .4(6) n
N2 C6 C7 C8 2.1(6) n
C5 C6 C7 C8 -177.8(4) n
C6 C7 C8 C9 .0(7) n
C7 C8 C9 C10 -1.3(7) n
C6 N2 C10 C9 1.4(6) n
Ni N2 C10 C9 -171.9(3) n
C8 C9 C10 N2 .6(7) n
N4 Ni N3 C15 3.2(3) n
N1 Ni N3 C15 174.2(3) n
N2 Ni N3 C15 96.3(3) n
Cl2 Ni N3 C15 -91.2(3) n
N4 Ni N3 C11 -179.2(4) n
N1 Ni N3 C11 -8.2(4) n
N2 Ni N3 C11 -86.1(3) n
Cl2 Ni N3 C11 86.4(3) n
N3 Ni N4 C20 176.9(4) n
N2 Ni N4 C20 86.1(4) n
Cl2 Ni N4 C20 -95.3(3) n
N3 Ni N4 C16 -2.5(3) n
N2 Ni N4 C16 -93.2(3) n
Cl1 Ni N4 C16 178.6(3) n
Cl2 Ni N4 C16 85.3(3) n
C15 N3 C11 C12 -.1(6) n
Ni N3 C11 C12 -177.7(3) n
N3 C11 C12 C13 -.2(7) n
C11 C12 C13 C14 .8(7) n
C12 C13 C14 C15 -1.1(7) n
C11 N3 C15 C14 -.2(6) n
Ni N3 C15 C14 177.6(3) n
C11 N3 C15 C16 178.9(3) n
Ni N3 C15 C16 -3.3(5) n
C13 C14 C15 N3 .8(6) n
C13 C14 C15 C16 -178.2(4) n
C20 N4 C16 C17 1.8(6) n
Ni N4 C16 C17 -178.8(3) n
C20 N4 C16 C15 -177.9(4) n
Ni N4 C16 C15 1.5(4) n
N3 C15 C16 N4 1.2(5) n
C14 C15 C16 N4 -179.7(4) n
N3 C15 C16 C17 -178.5(4) n
C14 C15 C16 C17 .6(7) n
N4 C16 C17 C18 -1.5(7) n
C15 C16 C17 C18 178.2(4) n
C16 C17 C18 C19 -.2(7) n
C17 C18 C19 C20 1.4(7) n
C16 N4 C20 C19 -.5(6) n
Ni N4 C20 C19 -179.9(3) n
C18 C19 C20 N4 -1.1(7) n
