#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:39:38 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111781.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_7111781
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            'C20 H20 Cl2 Ni O18'
_chemical_formula_weight         677.97
_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                 95.348(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.952(3)
_cell_length_b                   12.636(3)
_cell_length_c                   10.439(3)
_cell_measurement_reflns_used    3869
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.54
_cell_volume                     1307.0(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12556
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    1.033
_exptl_absorpt_correction_T_max  0.9127
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0295
_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)+(0.0379P)²+0.4549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                2441
_reflns_number_total             2852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC01291Bsup1.cif
_cod_data_source_block           jw42
_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               7111781
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
Ni1 Ni 0.0000 0.5000 0.5000 0.02290(11) Uani 1 2 d S
Cl1 Cl 0.42578(5) 0.68571(4) 0.73049(5) 0.02996(13) Uani 1 1 d .
O1 O 0.16431(13) 0.41743(11) 0.50433(13) 0.0329(3) Uani 1 1 d .
O2 O 0.03623(14) 0.52700(11) 0.69827(14) 0.0330(3) Uani 1 1 d .
O3 O 0.13854(14) 0.52468(11) 0.89255(13) 0.0317(3) Uani 1 1 d .
O4 O 0.44977(13) 0.34326(11) 0.79493(13) 0.0297(3) Uani 1 1 d .
O5 O 0.11717(18) 0.63772(14) 0.45810(16) 0.0446(4) Uani 1 1 d .
O6 O 0.43082(17) 0.70114(13) 0.86797(15) 0.0451(4) Uani 1 1 d .
O7 O 0.28520(16) 0.67761(13) 0.68318(16) 0.0451(4) Uani 1 1 d .
O8 O 0.49589(17) 0.59111(13) 0.70377(18) 0.0513(4) Uani 1 1 d .
O9 O 0.48430(16) 0.77560(12) 0.67377(16) 0.0444(4) Uani 1 1 d .
C1 C 0.5857(2) 0.24731(19) 0.6624(2) 0.0371(5) Uani 1 1 d .
C2 C 0.46022(19) 0.30995(15) 0.6712(2) 0.0293(4) Uani 1 1 d .
C3 C 0.3659(2) 0.33430(17) 0.5759(2) 0.0309(4) Uani 1 1 d .
C4 C 0.25057(19) 0.39644(15) 0.59689(19) 0.0282(4) Uani 1 1 d .
C5 C 0.24295(18) 0.43063(15) 0.72773(18) 0.0263(4) Uani 1 1 d .
C6 C 0.13449(19) 0.49494(15) 0.7665(2) 0.0281(4) Uani 1 1 d .
C7 C 0.34332(18) 0.40213(15) 0.82119(19) 0.0268(4) Uani 1 1 d .
C8 C 0.3418(2) 0.43400(16) 0.9504(2) 0.0294(4) Uani 1 1 d .
C9 C 0.2411(2) 0.49537(15) 0.9828(2) 0.0310(4) Uani 1 1 d .
C10 C 0.2243(3) 0.5403(2) 1.1105(2) 0.0418(5) Uani 1 1 d .
H1A H 0.593(3) 0.191(2) 0.731(3) 0.054(8) Uiso 1 1 d .
H1B H 0.664(3) 0.294(2) 0.681(3) 0.059(8) Uiso 1 1 d .
H1C H 0.582(3) 0.214(2) 0.575(3) 0.051(7) Uiso 1 1 d .
H3 H 0.374(2) 0.3113(17) 0.498(2) 0.035(6) Uiso 1 1 d .
H5A H 0.181(4) 0.661(3) 0.525(4) 0.102(12) Uiso 1 1 d .
H5B H 0.067(3) 0.687(3) 0.437(3) 0.074(11) Uiso 1 1 d .
H8 H 0.408(2) 0.4123(18) 1.008(2) 0.037(6) Uiso 1 1 d .
H10A H 0.295(4) 0.518(2) 1.173(3) 0.073(10) Uiso 1 1 d .
H10B H 0.135(4) 0.521(3) 1.136(3) 0.094(12) Uiso 1 1 d .
H10C H 0.231(3) 0.617(2) 1.102(2) 0.061(8) 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'
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'
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(8) . 3_566
O1 Ni1 O2 90.15(5) . 3_566
O1 Ni1 O2 89.85(6) 3_566 3_566
O1 Ni1 O2 89.85(6) . .
O1 Ni1 O2 90.15(5) 3_566 .
O2 Ni1 O2 180.0 3_566 .
O1 Ni1 O5 91.82(7) . 3_566
O1 Ni1 O5 88.18(7) 3_566 3_566
O2 Ni1 O5 91.28(6) 3_566 3_566
O2 Ni1 O5 88.72(6) . 3_566
O1 Ni1 O5 88.18(7) . .
O1 Ni1 O5 91.82(7) 3_566 .
O2 Ni1 O5 88.72(6) 3_566 .
O2 Ni1 O5 91.28(6) . .
O5 Ni1 O5 180.0 3_566 .
O8 Cl1 O9 111.08(10) . .
O8 Cl1 O7 110.51(10) . .
O9 Cl1 O7 109.51(10) . .
O8 Cl1 O6 109.60(10) . .
O9 Cl1 O6 109.05(10) . .
O7 Cl1 O6 106.99(10) . .
C4 O1 Ni1 130.17(13) . .
C6 O2 Ni1 125.15(14) . .
C6 O3 C9 122.67(16) . .
C7 O4 C2 119.51(15) . .
Ni1 O5 H5A 116(2) . .
Ni1 O5 H5B 110(2) . .
H5A O5 H5B 109(3) . .
C2 C1 H1A 109.8(15) . .
C2 C1 H1B 108.6(16) . .
H1A C1 H1B 106(2) . .
C2 C1 H1C 108.5(15) . .
H1A C1 H1C 110(2) . .
H1B C1 H1C 113(2) . .
C3 C2 O4 121.36(18) . .
C3 C2 C1 127.6(2) . .
O4 C2 C1 111.06(17) . .
C2 C3 C4 122.1(2) . .
C2 C3 H3 119.9(15) . .
C4 C3 H3 118.1(15) . .
O1 C4 C3 119.95(19) . .
O1 C4 C5 124.86(18) . .
C3 C4 C5 115.19(17) . .
C7 C5 C6 117.49(18) . .
C7 C5 C4 119.61(17) . .
C6 C5 C4 122.90(17) . .
O2 C6 O3 114.85(17) . .
O2 C6 C5 127.04(19) . .
O3 C6 C5 118.11(17) . .
O4 C7 C5 122.26(18) . .
O4 C7 C8 115.63(17) . .
C5 C7 C8 122.10(18) . .
C9 C8 C7 118.93(18) . .
C9 C8 H8 122.3(14) . .
C7 C8 H8 118.8(14) . .
C8 C9 O3 120.67(19) . .
C8 C9 C10 127.2(2) . .
O3 C9 C10 112.11(18) . .
C9 C10 H10A 111.2(19) . .
C9 C10 H10B 109(2) . .
H10A C10 H10B 112(3) . .
C9 C10 H10C 106.8(16) . .
H10A C10 H10C 107(2) . .
H10B C10 H10C 110(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 O1 1.9366(14) .
Ni1 O1 1.9366(14) 3_566
Ni1 O2 2.0955(15) 3_566
Ni1 O2 2.0955(15) .
Ni1 O5 2.1621(18) 3_566
Ni1 O5 2.1621(18) .
Cl1 O8 1.4247(16) .
Cl1 O9 1.4298(16) .
Cl1 O7 1.4432(16) .
Cl1 O6 1.4446(16) .
O1 C4 1.259(2) .
O2 C6 1.224(2) .
O3 C6 1.365(3) .
O3 C9 1.374(2) .
O4 C7 1.343(2) .
O4 C2 1.371(2) .
O5 H5A 0.95(4) .
O5 H5B 0.82(3) .
C1 C2 1.489(3) .
C1 H1A 1.01(3) .
C1 H1B 0.98(3) .
C1 H1C 1.00(3) .
C2 C3 1.339(3) .
C3 C4 1.425(3) .
C3 H3 0.88(2) .
C4 C5 1.441(3) .
C5 C7 1.377(3) .
C5 C6 1.439(3) .
C7 C8 1.409(3) .
C8 C9 1.335(3) .
C8 H8 0.89(2) .
C9 C10 1.474(3) .
C10 H10A 0.96(4) .
C10 H10B 0.98(4) .
C10 H10C 0.97(3) .
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
_geom_hbond_site_symmetry_A
O5 H5B O6 0.82(3) 2.04(3) 2.854(3) 173(3) 4_575
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 28(100) 3_566
O2 Ni1 O1 C4 178.96(17) 3_566
O2 Ni1 O1 C4 -1.04(17) .
O5 Ni1 O1 C4 -89.75(17) 3_566
O5 Ni1 O1 C4 90.25(17) .
O1 Ni1 O2 C6 1.35(16) .
O1 Ni1 O2 C6 -178.65(16) 3_566
O2 Ni1 O2 C6 -74(89) 3_566
O5 Ni1 O2 C6 93.18(17) 3_566
O5 Ni1 O2 C6 -86.82(17) .
C7 O4 C2 C3 -0.4(3) .
C7 O4 C2 C1 179.24(17) .
O4 C2 C3 C4 0.5(3) .
C1 C2 C3 C4 -179.1(2) .
Ni1 O1 C4 C3 -179.13(14) .
Ni1 O1 C4 C5 1.1(3) .
C2 C3 C4 O1 -179.97(19) .
C2 C3 C4 C5 -0.1(3) .
O1 C4 C5 C7 179.61(18) .
C3 C4 C5 C7 -0.2(3) .
O1 C4 C5 C6 -0.9(3) .
C3 C4 C5 C6 179.28(18) .
Ni1 O2 C6 O3 178.32(11) .
Ni1 O2 C6 C5 -1.7(3) .
C9 O3 C6 O2 179.68(17) .
C9 O3 C6 C5 -0.3(3) .
C7 C5 C6 O2 -179.14(19) .
C4 C5 C6 O2 1.4(3) .
C7 C5 C6 O3 0.8(3) .
C4 C5 C6 O3 -178.70(17) .
C2 O4 C7 C5 0.1(3) .
C2 O4 C7 C8 -179.18(16) .
C6 C5 C7 O4 -179.26(17) .
C4 C5 C7 O4 0.3(3) .
C6 C5 C7 C8 -0.1(3) .
C4 C5 C7 C8 179.44(17) .
O4 C7 C8 C9 178.00(17) .
C5 C7 C8 C9 -1.2(3) .
C7 C8 C9 O3 1.8(3) .
C7 C8 C9 C10 -177.3(2) .
C6 O3 C9 C8 -1.1(3) .
C6 O3 C9 C10 178.18(19) .
