#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/16/7031643.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_7031643
loop_
_publ_author_name
'Kumar, Amit'
'Pandey, Rampal'
'Gupta, Rakesh Kumar'
'Dubey, Mrigendra'
'Pandey, Daya Shankar'
_publ_section_title
;
 Novel tetranuclear copper |2 + 4| cubanes resulting from unprecedented
 C-O bond formation cum dearomatization.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13169
_journal_page_last               13173
_journal_paper_doi               10.1039/c4dt01887g
_journal_volume                  43
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_compound_source        Synthesized
_chemical_formula_moiety         'C28 H38 Cu N4 O2'
_chemical_formula_sum            'C28 H38 Cu N4 O2'
_chemical_formula_weight         526.16
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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                 98.023(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5908(3)
_cell_length_b                   11.6711(3)
_cell_length_c                   17.6727(3)
_cell_measurement_temperature    292(2)
_cell_volume                     2775.80(11)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       'Bruker APEX II (kappa 4)'
_computing_data_reduction        SHELXL
_computing_molecular_graphics    wingx
_computing_publication_material  wingx
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXL
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24468
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.8873
_exptl_absorpt_correction_T_min  0.7917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sortav (Blessing 1995)'
_exptl_crystal_colour            Black
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0000
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         4230
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1115P)²+0.5258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1755
_reflns_number_gt                3207
_reflns_number_total             4230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt01887g2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7031640--7031645.cif.'
_cod_original_sg_symbol_Hall     ' -C 2yc'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7031643
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
Cu1 Cu 0.5000 0.42593(4) 0.2500 0.0388(2) Uani 1 2 d S
O1 O 0.61182(15) 0.4581(2) 0.20005(13) 0.0480(5) Uani 1 1 d .
N1 N 0.41636(16) 0.3873(3) 0.15329(14) 0.0443(5) Uani 1 1 d .
N3 N 0.1016(3) 0.2164(4) 0.1989(3) 0.0991(14) Uani 1 1 d .
H3A H 0.1306 0.1566 0.2197 0.119 Uiso 1 1 d RD
H3B H 0.0380 0.2219 0.1940 0.119 Uiso 1 1 d RD
C1 C 0.2607(2) 0.4900(3) 0.1222(2) 0.0571(8) Uani 1 1 d .
C2 C 0.3096(2) 0.3912(3) 0.14981(17) 0.0454(6) Uani 1 1 d .
C3 C 0.2593(2) 0.2992(3) 0.1758(2) 0.0532(8) Uani 1 1 d DU
C4 C 0.1541(3) 0.3064(4) 0.1703(2) 0.0653(10) Uani 1 1 d DU
C5 C 0.1048(3) 0.4046(4) 0.1407(3) 0.0711(11) Uani 1 1 d .
C6 C 0.1573(3) 0.4930(4) 0.1183(2) 0.0706(11) Uani 1 1 d .
H6 H 0.1235 0.5586 0.0994 0.085 Uiso 1 1 calc R
C7 C 0.3157(3) 0.1976(4) 0.2115(3) 0.0774(11) Uani 1 1 d .
H7A H 0.2698 0.1421 0.2262 0.116 Uiso 1 1 calc RD
H7B H 0.3597 0.2219 0.2559 0.116 Uiso 1 1 calc R
H7C H 0.3537 0.1638 0.1754 0.116 Uiso 1 1 calc R
C8 C -0.0111(3) 0.4213(6) 0.1272(4) 0.124(3) Uani 1 1 d .
H8A H -0.0426 0.3546 0.1446 0.185 Uiso 1 1 calc RD
H8B H -0.0330 0.4324 0.0737 0.185 Uiso 1 1 calc R
H8C H -0.0284 0.4872 0.1551 0.185 Uiso 1 1 calc R
C9 C 0.3165(4) 0.5929(4) 0.0996(3) 0.0822(13) Uani 1 1 d .
H9A H 0.2719 0.6421 0.0676 0.123 Uiso 1 1 calc R
H9B H 0.3690 0.5683 0.0722 0.123 Uiso 1 1 calc R
H9C H 0.3443 0.6339 0.1447 0.123 Uiso 1 1 calc R
C10 C 0.4536(2) 0.3531(3) 0.09242(18) 0.0509(7) Uani 1 1 d .
C11 C 0.5569(2) 0.3542(3) 0.0879(2) 0.0572(8) Uani 1 1 d .
H11 H 0.5783 0.3146 0.0475 0.069 Uiso 1 1 calc R
C12 C 0.6277(2) 0.4083(3) 0.13758(19) 0.0466(7) Uani 1 1 d .
C13 C 0.7337(3) 0.4159(4) 0.1218(3) 0.0673(11) Uani 1 1 d .
H13A H 0.7779 0.4004 0.1680 0.101 Uiso 1 1 calc R
H13B H 0.7463 0.4914 0.1040 0.101 Uiso 1 1 calc R
H13C H 0.7444 0.3607 0.0835 0.101 Uiso 1 1 calc R
C14 C 0.3873(3) 0.3078(5) 0.0232(2) 0.0803(14) Uani 1 1 d .
H14A H 0.3201 0.3037 0.0340 0.121 Uiso 1 1 calc R
H14B H 0.4092 0.2326 0.0110 0.121 Uiso 1 1 calc R
H14C H 0.3905 0.3581 -0.0194 0.121 Uiso 1 1 calc R
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'
Cu Cu 0.3201 1.2651 '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'
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 157.18(16) 2_655 .
O1 Cu1 N1 92.54(9) 2_655 2_655
O1 Cu1 N1 92.65(9) . 2_655
O1 Cu1 N1 92.65(9) 2_655 .
O1 Cu1 N1 92.54(9) . .
N1 Cu1 N1 153.52(18) 2_655 .
C12 O1 Cu1 123.2(2) . .
C10 N1 C2 118.3(2) . .
C10 N1 Cu1 122.6(2) . .
C2 N1 Cu1 119.00(18) . .
C4 N3 H3A 122.4 . .
C4 N3 H3B 117.5 . .
H3A N3 H3B 120.1 . .
C2 C1 C6 117.9(4) . .
C2 C1 C9 121.5(3) . .
C6 C1 C9 120.6(4) . .
C3 C2 C1 121.9(3) . .
C3 C2 N1 120.1(3) . .
C1 C2 N1 118.0(3) . .
C2 C3 C4 118.0(4) . .
C2 C3 C7 120.3(3) . .
C4 C3 C7 121.7(3) . .
C5 C4 N3 120.6(4) . .
C5 C4 C3 120.1(3) . .
N3 C4 C3 119.2(4) . .
C6 C5 C4 119.7(3) . .
C6 C5 C8 114.9(5) . .
C4 C5 C8 125.4(4) . .
C5 C6 C1 122.5(4) . .
C5 C6 H6 118.8 . .
C1 C6 H6 118.8 . .
C3 C7 H7A 109.5 . .
C3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C1 C9 H9A 109.5 . .
C1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N1 C10 C11 122.8(3) . .
N1 C10 C14 121.0(3) . .
C11 C10 C14 116.2(3) . .
C12 C11 C10 125.7(3) . .
C12 C11 H11 117.2 . .
C10 C11 H11 117.2 . .
O1 C12 C11 124.9(3) . .
O1 C12 C13 114.1(3) . .
C11 C12 C13 121.0(3) . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.898(2) 2_655
Cu1 O1 1.898(2) .
Cu1 N1 1.968(2) 2_655
Cu1 N1 1.968(2) .
O1 C12 1.292(4) .
N1 C10 1.313(4) .
N1 C2 1.445(3) .
N3 C4 1.404(6) .
N3 H3A 0.8579 .
N3 H3B 0.8598 .
C1 C2 1.386(5) .
C1 C6 1.397(5) .
C1 C9 1.504(6) .
C2 C3 1.384(5) .
C3 C4 1.422(5) .
C3 C7 1.503(6) .
C4 C5 1.392(7) .
C5 C6 1.345(7) .
C5 C8 1.572(6) .
C6 H6 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C11 1.417(4) .
C10 C14 1.510(5) .
C11 C12 1.363(5) .
C11 H11 0.9300 .
C12 C13 1.508(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 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
O1 Cu1 O1 C12 -132.9(3) 2_655
N1 Cu1 O1 C12 124.1(3) 2_655
N1 Cu1 O1 C12 -29.9(3) .
O1 Cu1 N1 C10 -178.4(3) 2_655
O1 Cu1 N1 C10 23.9(3) .
N1 Cu1 N1 C10 -77.3(3) 2_655
O1 Cu1 N1 C2 -1.5(3) 2_655
O1 Cu1 N1 C2 -159.3(3) .
N1 Cu1 N1 C2 99.6(2) 2_655
C6 C1 C2 C3 -2.5(5) .
C9 C1 C2 C3 175.3(4) .
C6 C1 C2 N1 179.4(3) .
C9 C1 C2 N1 -2.7(5) .
C10 N1 C2 C3 94.7(4) .
Cu1 N1 C2 C3 -82.3(3) .
C10 N1 C2 C1 -87.2(4) .
Cu1 N1 C2 C1 95.8(3) .
C1 C2 C3 C4 2.7(5) .
N1 C2 C3 C4 -179.3(3) .
C1 C2 C3 C7 -174.7(3) .
N1 C2 C3 C7 3.3(5) .
C2 C3 C4 C5 -1.0(5) .
C7 C3 C4 C5 176.4(4) .
C2 C3 C4 N3 -177.5(3) .
C7 C3 C4 N3 -0.1(6) .
N3 C4 C5 C6 175.6(4) .
C3 C4 C5 C6 -0.8(6) .
N3 C4 C5 C8 -7.2(7) .
C3 C4 C5 C8 176.4(5) .
C4 C5 C6 C1 1.1(6) .
C8 C5 C6 C1 -176.4(4) .
C2 C1 C6 C5 0.6(6) .
C9 C1 C6 C5 -177.3(4) .
C2 N1 C10 C11 175.2(3) .
Cu1 N1 C10 C11 -7.9(5) .
C2 N1 C10 C14 -5.9(5) .
Cu1 N1 C10 C14 170.9(3) .
N1 C10 C11 C12 -12.7(6) .
C14 C10 C11 C12 168.4(4) .
Cu1 O1 C12 C11 20.2(5) .
Cu1 O1 C12 C13 -160.8(2) .
C10 C11 C12 O1 6.5(6) .
C10 C11 C12 C13 -172.4(4) .
