#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:33:23 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180044 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/38/7033852.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_7033852
loop_
_publ_author_name
'Kauf, Thomas'
'Rosa, Vitor'
'Fliedel, Christophe'
'Pattacini, Roberto'
'Deibel, Naina'
'Avilés, Teresa'
'Sarkar, Biprajit'
'Braunstein, Pierre'
_publ_section_title
;
 Reactivity of TCNE and TCNQ derivatives of quinonoid zwitterions with
 Cu(i).
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5441
_journal_page_last               5450
_journal_paper_doi               10.1039/c4dt03956d
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C38 H40 Cu N10 O4'
_chemical_formula_sum            'C38 H40 Cu N10 O4'
_chemical_formula_weight         764.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.707(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0282(5)
_cell_length_b                   13.5670(7)
_cell_length_c                   14.6751(5)
_cell_measurement_reflns_used    7685
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     2079.69(16)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12679
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  0.98146
_exptl_absorpt_correction_T_min  0.74761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             798
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.193
_refine_diff_density_rms         0.235
_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     234
_refine_ls_number_reflns         4761
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0753
_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)+(0.1367P)²+1.9359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2349
_reflns_number_gt                3454
_reflns_number_total             4761
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c4dt03956d2.cif
_cod_data_source_block           pbtk101123
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7033850--7033852.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7033852
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.6563(3) 0.9637(3) 0.1816(2) 0.0187(7) Uani 1 1 d . . .
C2 C 0.7153(3) 0.9222(3) 0.2734(2) 0.0198(7) Uani 1 1 d . . .
C3 C 0.8258(3) 0.9698(3) 0.3402(2) 0.0215(8) Uani 1 1 d . . .
C4 C 0.8756(3) 1.0626(3) 0.3070(2) 0.0224(8) Uani 1 1 d . . .
C5 C 0.8233(3) 1.0978(3) 0.2151(2) 0.0226(8) Uani 1 1 d . . .
H5 H 0.8599 1.1540 0.1954 0.027 Uiso 1 1 calc R . .
C6 C 0.7161(3) 1.0518(3) 0.1495(2) 0.0187(7) Uani 1 1 d . . .
C7 C 0.7038(3) 1.1541(3) 0.0125(3) 0.0241(8) Uani 1 1 d . . .
H7A H 0.6836 1.1382 -0.0567 0.029 Uiso 1 1 calc R . .
H7B H 0.7980 1.1592 0.0408 0.029 Uiso 1 1 calc R . .
C8 C 0.6441(6) 1.2520(4) 0.0225(5) 0.0572(16) Uani 1 1 d . B .
H8A H 0.6596 1.2658 0.0915 0.069 Uiso 1 1 calc R . .
H8B H 0.5504 1.2481 -0.0095 0.069 Uiso 1 1 calc R . .
C9 C 0.6975(8) 1.3359(5) -0.0212(7) 0.101(3) Uani 1 1 d . . .
H9A H 0.6554 1.3365 -0.0918 0.122 Uiso 1 1 calc R A 1
H9B H 0.7904 1.3257 -0.0083 0.122 Uiso 1 1 calc R A 1
C10 C 0.6748(18) 1.4391(10) 0.0225(16) 0.101(3) Uani 0.50 1 d P B 1
H10A H 0.5940 1.4371 0.0369 0.152 Uiso 0.50 1 calc PR B 1
H10B H 0.6709 1.4915 -0.0243 0.152 Uiso 0.50 1 calc PR B 1
H10C H 0.7455 1.4522 0.0817 0.152 Uiso 0.50 1 calc PR B 1
C10B C 0.5890(17) 1.4197(10) -0.0534(16) 0.101(3) Uani 0.50 1 d P B 2
H10D H 0.5117 1.3920 -0.0998 0.152 Uiso 0.50 1 calc PR B 2
H10E H 0.6203 1.4745 -0.0832 0.152 Uiso 0.50 1 calc PR B 2
H10F H 0.5691 1.4436 0.0032 0.152 Uiso 0.50 1 calc PR B 2
C11 C 1.0311(4) 1.1975(3) 0.3645(3) 0.0330(10) Uani 1 1 d . . .
H11A H 1.0499 1.1975 0.3029 0.040 Uiso 1 1 calc R . .
H11B H 1.1133 1.2045 0.4172 0.040 Uiso 1 1 calc R . .
C12 C 0.9463(5) 1.2847(4) 0.3662(4) 0.0448(12) Uani 1 1 d . . .
H12A H 0.8635 1.2770 0.3142 0.054 Uiso 1 1 calc R . .
H12B H 0.9287 1.2853 0.4283 0.054 Uiso 1 1 calc R . .
C13 C 1.0055(8) 1.3818(5) 0.3536(7) 0.099(2) Uani 1 1 d . . .
H13A H 1.0228 1.3815 0.2914 0.119 Uiso 1 1 calc R . .
H13B H 1.0884 1.3896 0.4055 0.119 Uiso 1 1 calc R . .
C14 C 0.9197(8) 1.4687(5) 0.3558(8) 0.099(2) Uani 1 1 d . . .
H14A H 0.9620 1.5301 0.3479 0.148 Uiso 1 1 calc R . .
H14B H 0.9033 1.4698 0.4176 0.148 Uiso 1 1 calc R . .
H14C H 0.8384 1.4622 0.3034 0.148 Uiso 1 1 calc R . .
C15 C 0.6600(3) 0.8364(3) 0.3025(2) 0.0220(8) Uani 1 1 d . . .
C16 C 0.5221(4) 0.8297(4) 0.2749(3) 0.0354(10) Uani 1 1 d . . .
C17 C 0.7278(4) 0.7603(3) 0.3563(3) 0.0247(8) Uani 1 1 d . . .
C18 C 0.8615(4) 0.7502(3) 0.3733(3) 0.0286(9) Uani 1 1 d . . .
C19 C 0.6677(4) 0.6821(3) 0.3917(3) 0.0319(9) Uani 1 1 d . . .
N1 N 0.6578(3) 1.0741(2) 0.06012(19) 0.0193(6) Uani 1 1 d . . .
N2 N 0.9725(3) 1.1037(3) 0.3751(2) 0.0296(8) Uani 1 1 d . . .
H2 H 1.0033 1.0723 0.4301 0.036 Uiso 1 1 calc R . .
N3 N 0.4136(4) 0.8223(4) 0.2571(3) 0.0622(14) Uani 1 1 d . . .
N4 N 0.9670(4) 0.7369(3) 0.3826(3) 0.0438(10) Uani 1 1 d . . .
N5 N 0.6228(4) 0.6196(3) 0.4209(3) 0.0477(10) Uani 1 1 d . . .
O1 O 0.5582(2) 0.92625(19) 0.12232(17) 0.0246(6) Uani 1 1 d . . .
O2 O 0.8778(3) 0.9415(2) 0.42245(17) 0.0292(6) Uani 1 1 d . . .
Cu1 Cu 0.5000 1.0000 0.0000 0.0226(2) Uani 1 2 d S . .
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'
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
O1 C1 C2 122.0(3) . .
O1 C1 C6 117.9(3) . .
C2 C1 C6 119.9(3) . .
C1 C2 C15 119.7(3) . .
C1 C2 C3 119.9(3) . .
C15 C2 C3 120.3(3) . .
O2 C3 C2 123.8(3) . .
O2 C3 C4 118.4(3) . .
C2 C3 C4 117.7(3) . .
N2 C4 C5 125.1(3) . .
N2 C4 C3 113.2(3) . .
C5 C4 C3 121.7(3) . .
C4 C5 C6 120.9(3) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
N1 C6 C5 128.4(3) . .
N1 C6 C1 112.1(3) . .
C5 C6 C1 119.5(3) . .
N1 C7 C8 112.1(3) . .
N1 C7 H7A 109.2 . .
C8 C7 H7A 109.2 . .
N1 C7 H7B 109.2 . .
C8 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
C7 C8 C9 112.3(4) . .
C7 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
C7 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.9 . .
C8 C9 C10 111.0(7) . .
C8 C9 C10B 107.6(7) . .
C10 C9 C10B 45.5(9) . .
C8 C9 H9A 109.4 . .
C10 C9 H9A 109.4 . .
C10B C9 H9A 68.4 . .
C8 C9 H9B 109.4 . .
C10 C9 H9B 109.4 . .
C10B C9 H9B 141.4 . .
H9A C9 H9B 108.0 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
C9 C10B H10D 109.5 . .
C9 C10B H10E 109.5 . .
H10D C10B H10E 109.5 . .
C9 C10B H10F 109.5 . .
H10D C10B H10F 109.5 . .
H10E C10B H10F 109.5 . .
N2 C11 C12 112.5(4) . .
N2 C11 H11A 109.1 . .
C12 C11 H11A 109.1 . .
N2 C11 H11B 109.1 . .
C12 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
C13 C12 C11 112.7(4) . .
C13 C12 H12A 109.0 . .
C11 C12 H12A 109.0 . .
C13 C12 H12B 109.0 . .
C11 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
C12 C13 C14 112.2(5) . .
C12 C13 H13A 109.2 . .
C14 C13 H13A 109.2 . .
C12 C13 H13B 109.2 . .
C14 C13 H13B 109.2 . .
H13A C13 H13B 107.9 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C17 C15 C2 125.2(3) . .
C17 C15 C16 116.4(3) . .
C2 C15 C16 118.4(3) . .
N3 C16 C15 176.8(4) . .
C15 C17 C18 121.2(3) . .
C15 C17 C19 122.5(4) . .
C18 C17 C19 116.1(3) . .
N4 C18 C17 175.3(5) . .
N5 C19 C17 178.5(5) . .
C6 N1 C7 121.3(3) . .
C6 N1 Cu1 114.6(2) . .
C7 N1 Cu1 124.0(2) . .
C4 N2 C11 124.3(3) . .
C4 N2 H2 117.8 . .
C11 N2 H2 117.8 . .
C1 O1 Cu1 112.4(2) . .
N1 Cu1 N1 180.0 . 3_675
N1 Cu1 O1 82.40(11) . .
N1 Cu1 O1 97.60(11) 3_675 .
N1 Cu1 O1 97.60(11) . 3_675
N1 Cu1 O1 82.40(11) 3_675 3_675
O1 Cu1 O1 180.00(13) . 3_675
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.257(4) .
C1 C2 1.412(5) .
C1 C6 1.511(5) .
C2 C15 1.440(5) .
C2 C3 1.448(5) .
C3 O2 1.220(4) .
C3 C4 1.515(5) .
C4 N2 1.329(5) .
C4 C5 1.371(5) .
C5 C6 1.409(5) .
C5 H5 0.9500 .
C6 N1 1.298(4) .
C7 N1 1.467(4) .
C7 C8 1.510(6) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.515(7) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.593(17) .
C9 C10B 1.607(15) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C10B H10D 0.9800 .
C10B H10E 0.9800 .
C10B H10F 0.9800 .
C11 N2 1.457(5) .
C11 C12 1.514(7) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.508(8) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.519(10) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C17 1.368(5) .
C15 C16 1.446(5) .
C16 N3 1.144(6) .
C17 C18 1.421(5) .
C17 C19 1.433(6) .
C18 N4 1.141(5) .
C19 N5 1.134(6) .
N1 Cu1 1.958(3) .
N2 H2 0.8800 .
O1 Cu1 1.974(2) .
Cu1 N1 1.958(3) 3_675
Cu1 O1 1.974(2) 3_675
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
N2 H2 O2 0.88 2.15 2.964(4) 153.9 3_776
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_4
O1 C1 C2 C15 -2.3(5) .
C6 C1 C2 C15 -178.0(3) .
O1 C1 C2 C3 -178.2(3) .
C6 C1 C2 C3 6.0(5) .
C1 C2 C3 O2 175.9(4) .
C15 C2 C3 O2 0.0(6) .
C1 C2 C3 C4 -1.2(5) .
C15 C2 C3 C4 -177.1(3) .
O2 C3 C4 N2 -0.9(5) .
C2 C3 C4 N2 176.4(3) .
O2 C3 C4 C5 178.9(4) .
C2 C3 C4 C5 -3.8(6) .
N2 C4 C5 C6 -176.6(4) .
C3 C4 C5 C6 3.6(6) .
C4 C5 C6 N1 -178.1(4) .
C4 C5 C6 C1 1.3(5) .
O1 C1 C6 N1 -2.8(5) .
C2 C1 C6 N1 173.2(3) .
O1 C1 C6 C5 177.8(3) .
C2 C1 C6 C5 -6.3(5) .
N1 C7 C8 C9 176.4(6) .
C7 C8 C9 C10 -158.9(10) .
C7 C8 C9 C10B 152.9(10) .
N2 C11 C12 C13 -179.0(5) .
C11 C12 C13 C14 -179.8(7) .
C1 C2 C15 C17 142.9(4) .
C3 C2 C15 C17 -41.2(5) .
C1 C2 C15 C16 -38.4(5) .
C3 C2 C15 C16 137.5(4) .
C2 C15 C17 C18 -12.4(6) .
C16 C15 C17 C18 168.9(4) .
C2 C15 C17 C19 173.1(4) .
C16 C15 C17 C19 -5.7(6) .
C5 C6 N1 C7 2.6(6) .
C1 C6 N1 C7 -176.9(3) .
C5 C6 N1 Cu1 -173.0(3) .
C1 C6 N1 Cu1 7.5(4) .
C8 C7 N1 C6 -90.2(5) .
C8 C7 N1 Cu1 85.0(4) .
C5 C4 N2 C11 5.3(7) .
C3 C4 N2 C11 -174.9(4) .
C12 C11 N2 C4 72.7(5) .
C2 C1 O1 Cu1 -179.2(3) .
C6 C1 O1 Cu1 -3.4(4) .
C6 N1 Cu1 O1 -7.5(3) .
C7 N1 Cu1 O1 177.0(3) .
C6 N1 Cu1 O1 172.5(3) 3_675
C7 N1 Cu1 O1 -3.0(3) 3_675
C1 O1 Cu1 N1 5.7(3) .
C1 O1 Cu1 N1 -174.3(3) 3_675
