#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:39:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180231 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/17/7111779.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_7111779
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 Cu O18'
_chemical_formula_weight         682.80
_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                 95.359(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9449(10)
_cell_length_b                   12.6414(13)
_cell_length_c                   10.4593(11)
_cell_measurement_reflns_used    8778
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.53
_cell_volume                     1309.2(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex 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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14330
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.8405
_exptl_absorpt_correction_T_min  0.7148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            light-blue
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             694
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0238
_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)+(0.0426P)²+0.4673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                2707
_reflns_number_total             2858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC01291Bsup1.cif
_cod_data_source_block           jw41
_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               7111779
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
Cu1 Cu 0.0000 0.5000 0.5000 0.02471(9) Uani 1 2 d S
Cl1 Cl 0.92585(4) 0.18584(3) 0.23069(3) 0.02848(10) Uani 1 1 d .
O1 O 0.16446(10) 0.58265(9) 0.50432(10) 0.0316(2) Uani 1 1 d .
O2 O 0.03631(11) 0.47309(9) 0.69818(11) 0.0314(2) Uani 1 1 d .
O3 O 0.13870(11) 0.47540(9) 0.89226(11) 0.0299(2) Uani 1 1 d .
O4 O 0.44999(10) 0.65681(8) 0.79470(10) 0.0286(2) Uani 1 1 d .
O5 O 0.11682(15) 0.36234(11) 0.45820(13) 0.0424(3) Uani 1 1 d .
O6 O 0.99628(13) 0.09097(10) 0.20393(14) 0.0493(3) Uani 1 1 d .
O7 O 0.98452(13) 0.27586(9) 0.17356(12) 0.0425(3) Uani 1 1 d .
O8 O 0.93096(13) 0.20162(10) 0.36829(11) 0.0428(3) Uani 1 1 d .
O9 O 0.78483(12) 0.17753(10) 0.18373(13) 0.0432(3) Uani 1 1 d .
C1 C 0.58625(16) 0.75273(14) 0.66217(18) 0.0354(3) Uani 1 1 d .
C2 C 0.46071(15) 0.69016(11) 0.67169(16) 0.0286(3) Uani 1 1 d .
C3 C 0.36647(15) 0.66601(12) 0.57551(16) 0.0304(3) Uani 1 1 d .
C4 C 0.25004(14) 0.60354(11) 0.59663(14) 0.0271(3) Uani 1 1 d .
C5 C 0.24295(13) 0.56942(11) 0.72764(14) 0.0249(3) Uani 1 1 d .
C6 C 0.13444(15) 0.50487(11) 0.76640(16) 0.0267(3) Uani 1 1 d .
C7 C 0.34366(13) 0.59793(11) 0.82094(14) 0.0256(3) Uani 1 1 d .
C8 C 0.34245(15) 0.56621(12) 0.95034(15) 0.0284(3) Uani 1 1 d .
C9 C 0.24078(16) 0.50474(11) 0.98236(16) 0.0291(3) Uani 1 1 d .
C10 C 0.22412(19) 0.45957(16) 1.11022(17) 0.0396(4) Uani 1 1 d .
H1A H 0.595(2) 0.8064(16) 0.730(2) 0.045(6) Uiso 1 1 d .
H1B H 0.662(2) 0.7061(17) 0.676(2) 0.050(6) Uiso 1 1 d .
H1C H 0.584(2) 0.7860(17) 0.583(2) 0.046(6) Uiso 1 1 d .
H3 H 0.3744(19) 0.6873(15) 0.4958(19) 0.036(5) Uiso 1 1 d .
H5A H 0.069(3) 0.316(2) 0.437(2) 0.056(7) Uiso 1 1 d .
H5B H 0.167(3) 0.3473(19) 0.514(2) 0.054(7) Uiso 1 1 d .
H8 H 0.410(2) 0.5862(15) 1.0066(19) 0.039(5) Uiso 1 1 d .
H10A H 0.232(2) 0.385(2) 1.104(2) 0.058(6) Uiso 1 1 d .
H10B H 0.137(3) 0.481(2) 1.134(3) 0.073(8) Uiso 1 1 d .
H10C H 0.294(2) 0.4829(16) 1.171(2) 0.043(6) 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'
Cu Cu 0.3201 1.2651 '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 Cu1 O1 180.00(6) 3_566 .
O1 Cu1 O2 89.85(4) 3_566 3_566
O1 Cu1 O2 90.15(4) . 3_566
O1 Cu1 O2 90.15(4) 3_566 .
O1 Cu1 O2 89.85(4) . .
O2 Cu1 O2 180.0 3_566 .
O1 Cu1 O5 88.30(5) 3_566 3_566
O1 Cu1 O5 91.70(5) . 3_566
O2 Cu1 O5 91.33(5) 3_566 3_566
O2 Cu1 O5 88.67(5) . 3_566
O1 Cu1 O5 91.70(5) 3_566 .
O1 Cu1 O5 88.30(5) . .
O2 Cu1 O5 88.67(5) 3_566 .
O2 Cu1 O5 91.33(5) . .
O5 Cu1 O5 180.0 3_566 .
O6 Cl1 O7 110.99(8) . .
O6 Cl1 O9 110.49(8) . .
O7 Cl1 O9 109.60(8) . .
O6 Cl1 O8 109.73(8) . .
O7 Cl1 O8 109.06(8) . .
O9 Cl1 O8 106.88(8) . .
C4 O1 Cu1 129.95(10) . .
C6 O2 Cu1 125.31(10) . .
C6 O3 C9 122.93(12) . .
C7 O4 C2 119.70(12) . .
Cu1 O5 H5A 109.9(18) . .
Cu1 O5 H5B 112.2(18) . .
H5A O5 H5B 112(3) . .
C2 C1 H1A 110.0(12) . .
C2 C1 H1B 108.3(13) . .
H1A C1 H1B 107.4(18) . .
C2 C1 H1C 110.4(13) . .
H1A C1 H1C 108.8(17) . .
H1B C1 H1C 111.9(18) . .
C3 C2 O4 121.60(13) . .
C3 C2 C1 126.92(15) . .
O4 C2 C1 111.48(13) . .
C2 C3 C4 121.71(15) . .
C2 C3 H3 121.2(13) . .
C4 C3 H3 117.1(13) . .
O1 C4 C3 119.77(14) . .
O1 C4 C5 125.29(13) . .
C3 C4 C5 114.94(13) . .
C7 C5 C6 117.54(14) . .
C7 C5 C4 119.77(13) . .
C6 C5 C4 122.69(13) . .
O2 C6 O3 115.12(13) . .
O2 C6 C5 126.89(15) . .
O3 C6 C5 117.99(13) . .
O4 C7 C5 122.28(13) . .
O4 C7 C8 115.50(12) . .
C5 C7 C8 122.21(13) . .
C9 C8 C7 118.51(14) . .
C9 C8 H8 122.7(12) . .
C7 C8 H8 118.7(12) . .
C8 C9 O3 120.80(14) . .
C8 C9 C10 126.89(15) . .
O3 C9 C10 112.30(14) . .
C9 C10 H10A 107.6(14) . .
C9 C10 H10B 107.5(17) . .
H10A C10 H10B 113(2) . .
C9 C10 H10C 110.3(13) . .
H10A C10 H10C 107.3(19) . .
H10B C10 H10C 111(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9377(10) 3_566
Cu1 O1 1.9377(10) .
Cu1 O2 2.0983(11) 3_566
Cu1 O2 2.0983(11) .
Cu1 O5 2.1596(14) 3_566
Cu1 O5 2.1596(14) .
Cl1 O6 1.4296(12) .
Cl1 O7 1.4345(12) .
Cl1 O9 1.4458(12) .
Cl1 O8 1.4491(13) .
O1 C4 1.2541(18) .
O2 C6 1.2218(19) .
O3 C6 1.365(2) .
O3 C9 1.3702(19) .
O4 C7 1.3424(17) .
O4 C2 1.3674(19) .
O5 H5A 0.78(3) .
O5 H5B 0.76(3) .
C1 C2 1.489(2) .
C1 H1A 0.98(2) .
C1 H1B 0.95(2) .
C1 H1C 0.93(2) .
C2 C3 1.344(2) .
C3 C4 1.436(2) .
C3 H3 0.89(2) .
C4 C5 1.445(2) .
C5 C7 1.3793(19) .
C5 C6 1.441(2) .
C7 C8 1.413(2) .
C8 C9 1.342(2) .
C8 H8 0.89(2) .
C9 C10 1.478(2) .
C10 H10A 0.95(3) .
C10 H10B 0.96(3) .
C10 H10C 0.94(2) .
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 H5A O8 0.78(3) 2.07(3) 2.847(2) 175(3) 1_455
O5 H5B O9 0.76(3) 2.06(3) 2.8061(19) 170(3) 4_566
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 Cu1 O1 C4 17(47) 3_566
O2 Cu1 O1 C4 -179.07(13) 3_566
O2 Cu1 O1 C4 0.93(13) .
O5 Cu1 O1 C4 89.60(13) 3_566
O5 Cu1 O1 C4 -90.40(13) .
O1 Cu1 O2 C6 178.50(12) 3_566
O1 Cu1 O2 C6 -1.50(12) .
O2 Cu1 O2 C6 -99(100) 3_566
O5 Cu1 O2 C6 -93.21(13) 3_566
O5 Cu1 O2 C6 86.79(13) .
C7 O4 C2 C3 0.4(2) .
C7 O4 C2 C1 -179.10(13) .
O4 C2 C3 C4 -0.3(2) .
C1 C2 C3 C4 179.14(15) .
Cu1 O1 C4 C3 179.05(10) .
Cu1 O1 C4 C5 -0.8(2) .
C2 C3 C4 O1 -179.93(14) .
C2 C3 C4 C5 0.0(2) .
O1 C4 C5 C7 -179.83(13) .
C3 C4 C5 C7 0.28(19) .
O1 C4 C5 C6 0.8(2) .
C3 C4 C5 C6 -179.07(13) .
Cu1 O2 C6 O3 -178.34(9) .
Cu1 O2 C6 C5 2.0(2) .
C9 O3 C6 O2 -179.44(13) .
C9 O3 C6 C5 0.2(2) .
C7 C5 C6 O2 179.08(14) .
C4 C5 C6 O2 -1.6(2) .
C7 C5 C6 O3 -0.53(19) .
C4 C5 C6 O3 178.84(12) .
C2 O4 C7 C5 -0.2(2) .
C2 O4 C7 C8 179.22(12) .
C6 C5 C7 O4 179.20(12) .
C4 C5 C7 O4 -0.2(2) .
C6 C5 C7 C8 -0.2(2) .
C4 C5 C7 C8 -179.55(13) .
O4 C7 C8 C9 -178.21(13) .
C5 C7 C8 C9 1.2(2) .
C7 C8 C9 O3 -1.5(2) .
C7 C8 C9 C10 177.18(15) .
C6 O3 C9 C8 0.9(2) .
C6 O3 C9 C10 -178.02(14) .
