#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111777.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7111777
loop_
_publ_author_name
'Waynant, Kristopher V.'
'White, James D.'
'Zakharov, Lev'
_publ_section_title
;
 Synthesis and structural characterization of a fused bispyrone and
 preparation of the first metal bispyrylium complexes
;
_journal_issue                   29
_journal_name_full               'Chemical Communications'
_journal_page_first              5304
_journal_page_last               5306
_journal_paper_doi               10.1039/c0cc01291b
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C22 H24 Cl2 Ni O18'
_chemical_formula_weight         706.02
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 95.849(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.412(2)
_cell_length_b                   14.508(4)
_cell_length_c                   13.476(4)
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.96
_cell_measurement_theta_min      2.81
_cell_volume                     1441.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9624
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.8796
_exptl_absorpt_correction_T_min  0.7592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            light-green
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3129
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0504P)²+1.0341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2595
_reflns_number_total             3129
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC01291Bsup1.cif
_cod_data_source_block           jw46
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7111777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Ni1 Ni 0.0000 0.5000 0.0000 0.02849(15) Uani 1 2 d S . .
Cl1 Cl 0.20478(11) 0.34631(6) 0.32635(5) 0.0489(2) Uani 1 1 d D . .
O1 O 0.1503(2) 0.38695(11) -0.01935(13) 0.0329(4) Uani 1 1 d . . .
O2 O -0.1631(2) 0.42878(11) 0.08309(13) 0.0345(4) Uani 1 1 d . . .
O3 O 0.0600(3) 0.12322(12) 0.05950(15) 0.0367(4) Uani 1 1 d . . .
O4 O -0.1684(2) 0.15473(11) 0.14059(13) 0.0322(4) Uani 1 1 d . . .
O5 O 0.1681(3) 0.53158(15) 0.12844(16) 0.0399(5) Uani 1 1 d . . .
O6 O 0.0910(4) 0.42142(19) 0.28830(19) 0.0745(8) Uani 1 1 d D A .
O7 O 0.1665(4) 0.3289(2) 0.42745(19) 0.0632(8) Uani 0.851(3) 1 d PD A 1
O8 O 0.1663(6) 0.2640(3) 0.2718(3) 0.1031(15) Uani 0.851(3) 1 d PD A 1
O9 O 0.3906(4) 0.3688(2) 0.3287(3) 0.0806(11) Uani 0.851(3) 1 d PD A 1
O7A O 0.287(2) 0.3319(13) 0.2323(10) 0.0632(8) Uani 0.149(3) 1 d PD A 2
O8A O 0.303(4) 0.3684(17) 0.4107(17) 0.1031(15) Uani 0.149(3) 1 d PD A 2
O9A O 0.083(2) 0.2702(13) 0.3181(19) 0.0806(11) Uani 0.149(3) 1 d PD A 2
C1 C 0.2855(6) 0.0603(2) -0.0301(4) 0.0616(11) Uani 1 1 d . . .
C2 C 0.1968(4) 0.14485(17) 0.0015(2) 0.0364(6) Uani 1 1 d . . .
C3 C 0.2292(4) 0.23228(17) -0.0218(2) 0.0319(6) Uani 1 1 d . . .
C4 C 0.1188(3) 0.30685(16) 0.00624(18) 0.0278(5) Uani 1 1 d . . .
C5 C -0.0301(3) 0.28117(15) 0.06351(17) 0.0254(5) Uani 1 1 d . . .
C6 C -0.0454(3) 0.19047(16) 0.08651(17) 0.0270(5) Uani 1 1 d . . .
C7 C -0.1606(3) 0.34391(16) 0.09967(18) 0.0285(5) Uani 1 1 d . . .
C8 C -0.2935(4) 0.30262(18) 0.15612(19) 0.0337(6) Uani 1 1 d . . .
C9 C -0.2960(4) 0.21208(17) 0.17495(19) 0.0326(6) Uani 1 1 d . . .
C10 C -0.4222(5) 0.1590(2) 0.2306(3) 0.0449(8) Uani 1 1 d . . .
C11 C 0.3618(5) 0.5419(3) 0.1316(3) 0.0591(9) Uani 1 1 d . . .
H1A H 0.381(6) 0.076(3) -0.060(3) 0.071(12) Uiso 1 1 d . . .
H1B H 0.318(7) 0.023(3) 0.027(4) 0.099(16) Uiso 1 1 d . . .
H1C H 0.206(7) 0.025(3) -0.078(4) 0.097(16) Uiso 1 1 d . . .
H3 H 0.318(5) 0.243(2) -0.059(2) 0.052(9) Uiso 1 1 d . . .
H5 H 0.148(5) 0.499(2) 0.166(3) 0.037(10) Uiso 1 1 d . . .
H8 H -0.375(4) 0.340(2) 0.182(2) 0.045(8) Uiso 1 1 d . . .
H10A H -0.507(5) 0.194(3) 0.252(3) 0.061(11) Uiso 1 1 d . . .
H10B H -0.476(5) 0.116(3) 0.186(3) 0.068(11) Uiso 1 1 d . . .
H10C H -0.355(5) 0.131(2) 0.288(3) 0.058(10) Uiso 1 1 d . . .
H11A H 0.391(6) 0.599(3) 0.105(3) 0.091(15) Uiso 1 1 d . . .
H11B H 0.417(6) 0.546(3) 0.197(4) 0.097(15) Uiso 1 1 d . . .
H11C H 0.408(8) 0.493(4) 0.098(5) 0.13(2) Uiso 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 0.0000 0.0000 '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'
Cl Cl 0.1484 0.1585 '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'
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
O1 Ni1 O1 180.00(10) 3_565 .
O1 Ni1 O2 88.55(7) 3_565 .
O1 Ni1 O2 91.45(7) . .
O1 Ni1 O2 91.45(7) 3_565 3_565
O1 Ni1 O2 88.55(7) . 3_565
O2 Ni1 O2 180.00(8) . 3_565
O1 Ni1 O5 89.70(8) 3_565 3_565
O1 Ni1 O5 90.30(8) . 3_565
O2 Ni1 O5 90.40(9) . 3_565
O2 Ni1 O5 89.60(9) 3_565 3_565
O1 Ni1 O5 90.30(8) 3_565 .
O1 Ni1 O5 89.70(8) . .
O2 Ni1 O5 89.60(9) . .
O2 Ni1 O5 90.40(9) 3_565 .
O5 Ni1 O5 180.0 3_565 .
O8A Cl1 O9 58.4(15) . .
O8A Cl1 O8 135.5(10) . .
O9 Cl1 O8 110.6(3) . .
O8A Cl1 O9A 122.9(17) . .
O9 Cl1 O9A 142.2(8) . .
O8 Cl1 O9A 38.0(9) . .
O8A Cl1 O6 111.9(10) . .
O9 Cl1 O6 111.56(19) . .
O8 Cl1 O6 112.0(2) . .
O9A Cl1 O6 102.4(9) . .
O8A Cl1 O7 51.4(15) . .
O9 Cl1 O7 107.7(2) . .
O8 Cl1 O7 107.1(3) . .
O9A Cl1 O7 75.8(10) . .
O6 Cl1 O7 107.72(15) . .
O8A Cl1 O7A 122.1(16) . .
O9 Cl1 O7A 64.2(7) . .
O8 Cl1 O7A 61.0(8) . .
O9A Cl1 O7A 97.9(12) . .
O6 Cl1 O7A 94.5(6) . .
O7 Cl1 O7A 157.6(6) . .
C4 O1 Ni1 127.19(16) . .
C7 O2 Ni1 127.25(16) . .
C6 O3 C2 118.49(19) . .
C6 O4 C9 118.83(19) . .
C11 O5 Ni1 124.0(2) . .
C11 O5 H5 109(3) . .
Ni1 O5 H5 107(3) . .
C2 C1 H1A 109(3) . .
C2 C1 H1B 109(3) . .
H1A C1 H1B 112(4) . .
C2 C1 H1C 112(3) . .
H1A C1 H1C 107(4) . .
H1B C1 H1C 109(4) . .
C3 C2 O3 120.7(2) . .
C3 C2 C1 128.8(3) . .
O3 C2 C1 110.5(2) . .
C2 C3 C4 122.4(2) . .
C2 C3 H3 118(2) . .
C4 C3 H3 120(2) . .
O1 C4 C3 120.4(2) . .
O1 C4 C5 124.1(2) . .
C3 C4 C5 115.5(2) . .
C6 C5 C7 117.2(2) . .
C6 C5 C4 116.9(2) . .
C7 C5 C4 125.8(2) . .
O3 C6 O4 108.7(2) . .
O3 C6 C5 125.8(2) . .
O4 C6 C5 125.5(2) . .
O2 C7 C8 120.5(2) . .
O2 C7 C5 123.8(2) . .
C8 C7 C5 115.7(2) . .
C9 C8 C7 122.2(2) . .
C9 C8 H8 119.6(19) . .
C7 C8 H8 118.1(19) . .
C8 C9 O4 120.5(2) . .
C8 C9 C10 129.1(3) . .
O4 C9 C10 110.4(2) . .
C9 C10 H10A 112(2) . .
C9 C10 H10B 106(2) . .
H10A C10 H10B 109(3) . .
C9 C10 H10C 109(2) . .
H10A C10 H10C 108(3) . .
H10B C10 H10C 113(3) . .
O5 C11 H11A 111(3) . .
O5 C11 H11B 112(3) . .
H11A C11 H11B 102(4) . .
O5 C11 H11C 109(4) . .
H11A C11 H11C 112(4) . .
H11B C11 H11C 111(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 2.0143(17) 3_565
Ni1 O1 2.0143(17) .
Ni1 O2 2.0146(17) .
Ni1 O2 2.0146(17) 3_565
Ni1 O5 2.078(2) 3_565
Ni1 O5 2.078(2) .
Cl1 O8A 1.325(14) .
Cl1 O9 1.412(3) .
Cl1 O8 1.416(4) .
Cl1 O9A 1.423(16) .
Cl1 O6 1.440(2) .
Cl1 O7 1.442(3) .
Cl1 O7A 1.476(13) .
O1 C4 1.241(3) .
O2 C7 1.251(3) .
O3 C6 1.324(3) .
O3 C2 1.378(3) .
O4 C6 1.329(3) .
O4 C9 1.375(3) .
O5 C11 1.440(4) .
O5 H5 0.73(3) .
C1 C2 1.475(4) .
C1 H1A 0.88(4) .
C1 H1B 0.95(5) .
C1 H1C 0.97(5) .
C2 C3 1.334(4) .
C3 C4 1.430(3) .
C3 H3 0.88(3) .
C4 C5 1.458(3) .
C5 C6 1.359(3) .
C5 C7 1.448(3) .
C7 C8 1.435(4) .
C8 C9 1.338(4) .
C8 H8 0.91(3) .
C9 C10 1.474(4) .
C10 H10A 0.87(4) .
C10 H10B 0.92(4) .
C10 H10C 0.97(4) .
C11 H11A 0.93(5) .
C11 H11B 0.94(5) .
C11 H11C 0.93(6) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5 O6 0.73(3) 2.07(3) 2.788(3) 172(3)
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_site_symmetry_1
O1 Ni1 O1 C4 176(68) 3_565
O2 Ni1 O1 C4 7.0(2) .
O2 Ni1 O1 C4 -173.0(2) 3_565
O5 Ni1 O1 C4 -83.4(2) 3_565
O5 Ni1 O1 C4 96.6(2) .
O1 Ni1 O2 C7 174.2(2) 3_565
O1 Ni1 O2 C7 -5.8(2) .
O2 Ni1 O2 C7 18(100) 3_565
O5 Ni1 O2 C7 84.5(2) 3_565
O5 Ni1 O2 C7 -95.5(2) .
O1 Ni1 O5 C11 -124.7(3) 3_565
O1 Ni1 O5 C11 55.3(3) .
O2 Ni1 O5 C11 146.8(3) .
O2 Ni1 O5 C11 -33.2(3) 3_565
O5 Ni1 O5 C11 36(13) 3_565
C6 O3 C2 C3 4.0(4) .
C6 O3 C2 C1 -173.7(3) .
O3 C2 C3 C4 -4.0(4) .
C1 C2 C3 C4 173.3(4) .
Ni1 O1 C4 C3 173.68(18) .
Ni1 O1 C4 C5 -5.1(3) .
C2 C3 C4 O1 -177.9(3) .
C2 C3 C4 C5 1.0(4) .
O1 C4 C5 C6 -179.4(2) .
C3 C4 C5 C6 1.8(3) .
O1 C4 C5 C7 -0.7(4) .
C3 C4 C5 C7 -179.6(2) .
C2 O3 C6 O4 179.3(2) .
C2 O3 C6 C5 -1.1(4) .
C9 O4 C6 O3 -178.5(2) .
C9 O4 C6 C5 1.9(4) .
C7 C5 C6 O3 179.4(2) .
C4 C5 C6 O3 -1.8(4) .
C7 C5 C6 O4 -1.0(4) .
C4 C5 C6 O4 177.8(2) .
Ni1 O2 C7 C8 -176.37(18) .
Ni1 O2 C7 C5 2.6(4) .
C6 C5 C7 O2 -179.3(2) .
C4 C5 C7 O2 2.1(4) .
C6 C5 C7 C8 -0.2(3) .
C4 C5 C7 C8 -178.9(2) .
O2 C7 C8 C9 179.6(3) .
C5 C7 C8 C9 0.6(4) .
C7 C8 C9 O4 0.3(4) .
C7 C8 C9 C10 -179.6(3) .
C6 O4 C9 C8 -1.5(4) .
C6 O4 C9 C10 178.4(2) .
