#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:50:59 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179734 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/30/7003006.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7003006
loop_
_publ_author_name
'Chen, Zhen-Feng'
'Tan, Ming-Xiong'
'Liu, Li-Min'
'Liu, Yan-Cheng'
'Wang, Heng-Shan'
'Yang, Bin'
'Peng, Yan'
'Liu, Hua-Gang'
'Liang, Hong'
'Orvig, Chris'
_publ_section_title
;
 Cytotoxicity of the traditional chinese medicine (TCM) plumbagin in
 its copper chemistry
;
_journal_issue                   48
_journal_name_full               'Dalton Transactions'
_journal_page_first              10824
_journal_page_last               10833
_journal_paper_doi               10.1039/b910133k
_journal_year                    2009
_chemical_formula_sum            'C22 H18 Cu O8'
_chemical_formula_weight         473.90
_chemical_name_systematic
;
?
;
_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                 109.319(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.576(4)
_cell_length_b                   10.0549(18)
_cell_length_c                   9.3266(17)
_cell_measurement_reflns_used    757
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.10
_cell_measurement_theta_min      2.26
_cell_volume                     1909.4(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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4662
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.195
_exptl_absorpt_correction_T_max  0.8718
_exptl_absorpt_correction_T_min  0.7339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0499
_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)+(0.0821P)²+1.6913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1594
_reflns_number_gt                1084
_reflns_number_total             1684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b910133k.txt
_cod_data_source_block           xb1734
_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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7003006
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_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
Cu1 Cu 1.0000 0.0000 1.0000 0.0515(4) Uani 1 2 d S . .
O1 O 0.96439(15) 0.1524(3) 0.8791(3) 0.0526(9) Uani 1 1 d . . .
O2 O 0.94837(15) -0.1193(3) 0.8532(3) 0.0529(9) Uani 1 1 d . . .
O3 O 0.77708(18) 0.2160(4) 0.3402(4) 0.0766(11) Uani 1 1 d . . .
C1 C 0.9203(2) 0.1574(5) 0.7486(5) 0.0481(12) Uani 1 1 d . . .
C2 C 0.9037(2) 0.2890(5) 0.6847(6) 0.0538(13) Uani 1 1 d . . .
H2 H 0.9255 0.3619 0.7402 0.065 Uiso 1 1 calc R . .
C3 C 0.8579(3) 0.3103(5) 0.5481(6) 0.0564(13) Uani 1 1 d . . .
C4 C 0.8222(2) 0.1962(6) 0.4604(5) 0.0534(13) Uani 1 1 d . . .
C5 C 0.8402(2) 0.0612(5) 0.5179(5) 0.0460(12) Uani 1 1 d . . .
C6 C 0.8100(2) -0.0456(6) 0.4340(6) 0.0563(14) Uani 1 1 d . . .
H6 H 0.7783 -0.0319 0.3395 0.068 Uiso 1 1 calc R . .
C7 C 0.8257(2) -0.1745(6) 0.4866(6) 0.0587(14) Uani 1 1 d . . .
H7 H 0.8050 -0.2465 0.4274 0.070 Uiso 1 1 calc R . .
C8 C 0.8724(2) -0.1950(6) 0.6281(6) 0.0569(13) Uani 1 1 d . . .
H8 H 0.8822 -0.2816 0.6634 0.068 Uiso 1 1 calc R . .
C9 C 0.9053(2) -0.0889(5) 0.7200(5) 0.0488(12) Uani 1 1 d . . .
C10 C 0.8896(2) 0.0431(5) 0.6650(5) 0.0465(12) Uani 1 1 d . . .
C11 C 0.8416(3) 0.4468(6) 0.4809(7) 0.0726(17) Uani 1 1 d . . .
H11A H 0.7989 0.4724 0.4822 0.109 Uiso 1 1 calc R . .
H11B H 0.8417 0.4462 0.3781 0.109 Uiso 1 1 calc R . .
H11C H 0.8738 0.5091 0.5395 0.109 Uiso 1 1 calc R . .
O4 O 1.0139(2) 0.4062(4) 1.1164(4) 0.0799(12) Uani 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'
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
_geom_angle_publ_flag
O2 Cu1 O2 180.000(1) . 5_757 ?
O2 Cu1 O1 86.79(14) . 5_757 ?
O2 Cu1 O1 93.21(14) 5_757 5_757 ?
O2 Cu1 O1 93.21(14) . . ?
O2 Cu1 O1 86.79(14) 5_757 . ?
O1 Cu1 O1 180.000(1) 5_757 . ?
C1 O1 Cu1 128.6(3) . . ?
C9 O2 Cu1 126.9(3) . . ?
O1 C1 C10 123.8(5) . . ?
O1 C1 C2 115.8(5) . . ?
C10 C1 C2 120.4(4) . . ?
C3 C2 C1 122.6(5) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 119.2(5) . . ?
C2 C3 C11 122.5(5) . . ?
C4 C3 C11 118.3(5) . . ?
O3 C4 C5 121.1(5) . . ?
O3 C4 C3 119.4(5) . . ?
C5 C4 C3 119.5(4) . . ?
C6 C5 C10 120.6(5) . . ?
C6 C5 C4 120.2(4) . . ?
C10 C5 C4 119.2(5) . . ?
C5 C6 C7 121.3(5) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 122.0(5) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
O2 C9 C8 117.1(5) . . ?
O2 C9 C10 124.4(4) . . ?
C8 C9 C10 118.5(4) . . ?
C9 C10 C1 122.9(4) . . ?
C9 C10 C5 118.2(5) . . ?
C1 C10 C5 118.8(5) . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.883(3) . ?
Cu1 O2 1.883(3) 5_757 ?
Cu1 O1 1.907(3) 5_757 ?
Cu1 O1 1.907(3) . ?
O1 C1 1.274(5) . ?
O2 C9 1.318(5) . ?
O3 C4 1.233(6) . ?
C1 C10 1.423(7) . ?
C1 C2 1.447(7) . ?
C2 C3 1.345(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.470(7) . ?
C3 C11 1.502(7) . ?
C4 C5 1.464(7) . ?
C5 C6 1.362(7) . ?
C5 C10 1.443(6) . ?
C6 C7 1.387(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.423(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C1 1.5(4) . . . . ?
O2 Cu1 O1 C1 -178.5(4) 5_757 . . . ?
O1 Cu1 O2 C9 179.9(4) 5_757 . . . ?
O1 Cu1 O2 C9 -0.1(4) . . . . ?
Cu1 O1 C1 C10 -1.7(7) . . . . ?
Cu1 O1 C1 C2 -179.7(3) . . . . ?
O1 C1 C2 C3 -179.8(4) . . . . ?
C10 C1 C2 C3 2.1(7) . . . . ?
C1 C2 C3 C4 1.2(8) . . . . ?
C1 C2 C3 C11 -178.9(5) . . . . ?
C2 C3 C4 O3 175.0(5) . . . . ?
C11 C3 C4 O3 -4.9(7) . . . . ?
C2 C3 C4 C5 -4.5(7) . . . . ?
C11 C3 C4 C5 175.7(5) . . . . ?
O3 C4 C5 C6 4.2(7) . . . . ?
C3 C4 C5 C6 -176.4(4) . . . . ?
O3 C4 C5 C10 -174.9(4) . . . . ?
C3 C4 C5 C10 4.5(6) . . . . ?
C10 C5 C6 C7 -0.1(7) . . . . ?
C4 C5 C6 C7 -179.2(5) . . . . ?
C5 C6 C7 C8 0.8(8) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
Cu1 O2 C9 C8 179.8(3) . . . . ?
Cu1 O2 C9 C10 -1.1(6) . . . . ?
C7 C8 C9 O2 179.4(4) . . . . ?
C7 C8 C9 C10 0.3(7) . . . . ?
O2 C9 C10 C1 1.3(7) . . . . ?
C8 C9 C10 C1 -179.6(4) . . . . ?
O2 C9 C10 C5 -178.7(4) . . . . ?
C8 C9 C10 C5 0.4(6) . . . . ?
O1 C1 C10 C9 0.2(7) . . . . ?
C2 C1 C10 C9 178.1(4) . . . . ?
O1 C1 C10 C5 -179.9(4) . . . . ?
C2 C1 C10 C5 -1.9(7) . . . . ?
C6 C5 C10 C9 -0.5(7) . . . . ?
C4 C5 C10 C9 178.6(4) . . . . ?
C6 C5 C10 C1 179.6(4) . . . . ?
C4 C5 C10 C1 -1.3(6) . . . . ?
