#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/93/2209357.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_2209357
loop_
_publ_author_name
'Chen, Zi-Lu'
'Zhang, Yu-Zhen'
'Liang, Fu-Pei'
_publ_section_title
;
 Dichloro(1,10-phenanthroline)(benzene-1,2-diamine)nickel(II) methanol
 solvate
;
_journal_coeditor_code           XU2035
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1296
_journal_page_last               m1297
_journal_paper_doi               10.1107/S1600536806016746
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Ni Cl2 (C6 H8 N2) (C12 H8 N2)], C H4 O'
_chemical_formula_moiety         'C18 H16 Cl2 N4 Ni, C H4 O'
_chemical_formula_sum            'C19 H20 Cl2 N4 Ni O'
_chemical_formula_weight         450.00
_chemical_name_systematic
;
Dichloro(1,10-phenanthroline)(1,2-phenylenediamine)nickel(II) methanol
solvate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 126.313(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.898(4)
_cell_length_b                   18.246(5)
_cell_length_c                   10.015(3)
_cell_measurement_reflns_used    1518
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.2
_cell_volume                     2046.4(10)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.034
_diffrn_reflns_av_sigmaI/netI    0.038
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5191
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  0.819
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1998)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.28
_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     132
_refine_ls_number_reflns         1794
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.073
_refine_ls_R_factor_gt           0.041
_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)+(0.0592P)²+1.4849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.100
_refine_ls_wR_factor_ref         0.119
_reflns_number_gt                1204
_reflns_number_total             1794
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2035.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209357
_cod_database_fobs_code          2209357
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'
'-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_type_symbol
_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
Ni Ni1 1.0000 0.79607(3) 0.2500 0.0341(2) Uani d S 1
Cl Cl1 1.16502(8) 0.79501(5) 0.22243(11) 0.0440(3) Uani d . 1
N N1 0.9278(3) 0.71044(15) 0.0798(3) 0.0389(8) Uani d . 1
H H1A 0.8476 0.7138 0.0143 0.047 Uiso calc R 1
H H1B 0.9529 0.7137 0.0152 0.047 Uiso calc R 1
N N2 0.9180(2) 0.88323(17) 0.0857(3) 0.0361(7) Uani d . 1
C C1 0.9634(3) 0.6406(2) 0.1641(4) 0.0367(9) Uani d . 1
C C2 0.9282(4) 0.5754(2) 0.0794(5) 0.0484(11) Uani d . 1
H H2 0.8798 0.5755 -0.0358 0.058 Uiso calc R 1
C C3 0.9642(4) 0.5093(2) 0.1646(5) 0.0583(12) Uani d . 1
H H3 0.9402 0.4652 0.1066 0.070 Uiso calc R 1
C C4 0.8353(3) 0.8819(2) -0.0781(4) 0.0430(10) Uani d . 1
H H4 0.8082 0.8370 -0.1321 0.052 Uiso calc R 1
C C5 0.7883(4) 0.9464(2) -0.1704(5) 0.0497(11) Uani d . 1
H H5 0.7305 0.9438 -0.2844 0.060 Uiso calc R 1
C C6 0.8260(4) 1.0124(2) -0.0957(5) 0.0483(11) Uani d . 1
H H6 0.7950 1.0552 -0.1579 0.058 Uiso calc R 1
C C7 0.9128(3) 1.0160(2) 0.0774(5) 0.0400(9) Uani d . 1
C C8 0.9559(3) 0.94956(18) 0.1619(4) 0.0337(8) Uani d . 1
C C9 0.9586(4) 1.0828(2) 0.1664(5) 0.0516(11) Uani d . 1
H H9 0.9315 1.1271 0.1096 0.062 Uiso calc R 1
O O1 0.8895(10) 0.3280(5) 0.0372(14) 0.158(5) Uani d PD 0.50
H H1 0.8709 0.2936 -0.0266 0.190 Uiso d PR 0.50
C C10 0.9358(9) 0.3003(4) 0.1984(12) 0.061(3) Uani d PD 0.50
H H101 0.9130 0.3329 0.2506 0.073 Uiso d PR 0.50
H H102 1.0215 0.2967 0.2652 0.073 Uiso d PR 0.50
H H103 0.9031 0.2526 0.1894 0.073 Uiso d PR 0.50
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Ni1 0.0311(4) 0.0298(4) 0.0258(4) 0.000 0.0084(3) 0.000
Cl1 0.0350(5) 0.0487(6) 0.0372(5) 0.0033(4) 0.0154(4) 0.0045(4)
N1 0.0367(17) 0.0379(18) 0.0289(16) 0.0018(14) 0.0122(14) 0.0012(13)
N2 0.0329(16) 0.0351(17) 0.0305(16) 0.0014(13) 0.0134(14) 0.0020(13)
C1 0.0317(19) 0.040(2) 0.0307(18) -0.0017(16) 0.0141(16) -0.0009(16)
C2 0.050(2) 0.042(2) 0.043(2) -0.0028(19) 0.022(2) -0.0065(19)
C3 0.069(3) 0.038(2) 0.057(2) -0.005(2) 0.032(2) -0.006(2)
C4 0.035(2) 0.046(2) 0.032(2) 0.0002(18) 0.0105(17) -0.0024(17)
C5 0.041(2) 0.057(3) 0.034(2) 0.002(2) 0.0130(19) 0.0091(19)
C6 0.047(2) 0.047(3) 0.046(2) 0.011(2) 0.025(2) 0.017(2)
C7 0.039(2) 0.036(2) 0.044(2) 0.0034(17) 0.0241(19) 0.0035(17)
C8 0.0305(19) 0.032(2) 0.0373(19) 0.0004(15) 0.0192(16) 0.0011(15)
C9 0.060(3) 0.033(2) 0.059(2) 0.0044(19) 0.033(2) 0.0068(19)
O1 0.179(11) 0.097(8) 0.182(11) -0.031(7) 0.098(9) -0.067(8)
C10 0.107(7) 0.050(5) 0.061(6) -0.030(5) 0.069(6) -0.024(5)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N2 Ni1 N2 2_755 . 80.06(16)
N2 Ni1 N1 2_755 . 175.02(12)
N2 Ni1 N1 . . 98.86(11)
N2 Ni1 N1 2_755 2_755 98.86(11)
N2 Ni1 N1 . 2_755 175.02(12)
N1 Ni1 N1 . 2_755 82.64(16)
N2 Ni1 Cl1 2_755 2_755 91.60(9)
N2 Ni1 Cl1 . 2_755 89.09(9)
N1 Ni1 Cl1 . 2_755 93.25(10)
N1 Ni1 Cl1 2_755 2_755 86.08(10)
N2 Ni1 Cl1 2_755 . 89.09(9)
N2 Ni1 Cl1 . . 91.60(9)
N1 Ni1 Cl1 . . 86.08(10)
N1 Ni1 Cl1 2_755 . 93.25(10)
Cl1 Ni1 Cl1 2_755 . 179.10(6)
C1 N1 Ni1 . . 110.6(2)
C1 N1 H1A . . 109.5
Ni1 N1 H1A . . 109.5
C1 N1 H1B . . 109.5
Ni1 N1 H1B . . 109.5
H1A N1 H1B . . 108.1
C4 N2 C8 . . 118.1(3)
C4 N2 Ni1 . . 129.0(3)
C8 N2 Ni1 . . 112.9(2)
C2 C1 C1 . 2_755 119.8(2)
C2 C1 N1 . . 122.0(3)
C1 C1 N1 2_755 . 118.10(17)
C1 C2 C3 . . 120.5(4)
C1 C2 H2 . . 119.7
C3 C2 H2 . . 119.7
C3 C3 C2 2_755 . 119.6(2)
C3 C3 H3 2_755 . 120.2
C2 C3 H3 . . 120.2
N2 C4 C5 . . 121.6(4)
N2 C4 H4 . . 119.2
C5 C4 H4 . . 119.2
C6 C5 C4 . . 120.6(4)
C6 C5 H5 . . 119.7
C4 C5 H5 . . 119.7
C5 C6 C7 . . 119.4(4)
C5 C6 H6 . . 120.3
C7 C6 H6 . . 120.3
C8 C7 C6 . . 116.9(3)
C8 C7 C9 . . 119.6(3)
C6 C7 C9 . . 123.5(4)
N2 C8 C7 . . 123.3(3)
N2 C8 C8 . 2_755 117.08(19)
C7 C8 C8 . 2_755 119.6(2)
C9 C9 C7 2_755 . 120.8(2)
C9 C9 H9 2_755 . 119.6
C7 C9 H9 . . 119.6
C10 O1 H1 . . 109.4
O1 C10 C10 . 2_755 110.4(10)
O1 C10 H101 . . 108.8
C10 C10 H101 2_755 . 106.1
O1 C10 H102 . . 110.7
H101 C10 H102 . . 109.5
O1 C10 H103 . . 110.0
C10 C10 H103 2_755 . 112.6
H101 C10 H103 . . 108.7
H102 C10 H103 . . 109.0
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
Ni1 N2 2_755 2.077(3) ?
Ni1 N1 . 2.080(3) y
Ni1 N2 . 2.077(3) y
Ni1 N1 2_755 2.080(3) ?
Ni1 Cl1 2_755 2.4671(12) ?
Ni1 Cl1 . 2.4671(12) y
N1 C1 . 1.444(4) ?
N1 H1A . 0.9000 ?
N1 H1B . 0.9000 ?
N2 C4 . 1.334(4) ?
N2 C8 . 1.359(4) ?
C1 C2 . 1.372(5) ?
C1 C1 2_755 1.387(7) ?
C2 C3 . 1.389(5) ?
C2 H2 . 0.9300 ?
C3 C3 2_755 1.379(8) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.396(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.350(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.410(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.394(5) ?
C7 C9 . 1.418(5) ?
C8 C8 2_755 1.434(7) ?
C9 C9 2_755 1.359(8) ?
C9 H9 . 0.9300 ?
O1 C10 . 1.430(12) ?
O1 H1 . 0.8200 ?
C10 C10 2_755 1.44(2) ?
C10 H101 . 0.9615 ?
C10 H102 . 0.9624 ?
C10 H103 . 0.9612 ?
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
N1 H1A Cl1 8_465 0.90 2.49 3.267(3) 144 y
O1 H1 Cl1 5_765 0.82 2.36 3.168(10) 171 y
