#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:28:27 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179247 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/67/4316714.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_4316714
loop_
_publ_author_name
'Martin M. Kimani'
'Julia L. Brumaghim'
'Don VanDerveer'
_publ_section_title
;
 Probing the Antioxidant Action of Selenium and Sulfur Using
 Cu(I)-Chalcogenone Tris(pyrazolyl)methane and -borate Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9200
_journal_page_last               9211
_journal_paper_doi               10.1021/ic100668b
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C20 H30 B Cu N8 Se'
_chemical_formula_sum            'C20 H30 B Cu N8 Se'
_chemical_formula_weight         535.83
_chemical_properties_physical    'air-sensitive, moisture-sensitive'
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 92.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.3319(17)
_cell_length_b                   11.771(2)
_cell_length_c                   12.082(2)
_cell_measurement_reflns_used    9538
_cell_measurement_temperature    168.15
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      3.02
_cell_volume                     1184.2(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC,2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC,2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC,2006)'
_computing_molecular_graphics    'SHELXTL 6.10 (Sheldrick,2008)'
_computing_publication_material  'SHELXTL 6.10 (Sheldrick,2008)'
_computing_structure_refinement  'SHELXTL 6.10 (Sheldrick,2008)'
_computing_structure_solution    'SHELXTL 6.10 (Sheldrick,2008)'
_diffrn_ambient_temperature      168.15
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku, AFC8S diffractometer'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9538
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.483
_exptl_absorpt_correction_T_max  0.6111
_exptl_absorpt_correction_T_min  0.4684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB, CrystalClear'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method 'ether into methanol/dichloromethane '
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0383
_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)+(0.0537P)²+1.3941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                2136
_reflns_number_total             2494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100668b_si_003_4.cif
_cod_data_source_block           Tp*Cu(dmise)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4316714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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 0.32586(6) 0.2500 0.36031(4) 0.02444(16) Uani 1 2 d S . .
Se1 Se 0.20396(5) 0.2500 0.53083(4) 0.03067(15) Uani 1 2 d S . .
N1 N 0.4503(3) 0.1584(2) 0.6791(2) 0.0279(5) Uani 1 1 d . . .
N2 N 0.5562(4) 0.2500 0.3102(3) 0.0236(7) Uani 1 2 d S . .
N3 N 0.2563(3) 0.1254(2) 0.2412(2) 0.0240(5) Uani 1 1 d . . .
N4 N 0.3156(3) 0.1437(2) 0.1380(2) 0.0241(5) Uani 1 1 d . . .
N5 N 0.5712(4) 0.2500 0.1972(3) 0.0231(7) Uani 1 2 d S . .
C1 C 0.3768(5) 0.2500 0.6332(3) 0.0239(8) Uani 1 2 d S . .
C2 C 0.4138(4) 0.0399(3) 0.6525(3) 0.0390(8) Uani 1 1 d . . .
H2A H 0.3606 0.0357 0.5807 0.059 Uiso 1 1 calc R . .
H2B H 0.3450 0.0092 0.7071 0.059 Uiso 1 1 calc R . .
H2C H 0.5117 -0.0031 0.6521 0.059 Uiso 1 1 calc R . .
C3 C 0.5711(4) 0.1932(3) 0.7531(3) 0.0336(7) Uani 1 1 d . . .
H3A H 0.6395 0.1463 0.7951 0.040 Uiso 1 1 calc R . .
C4 C 0.7340(6) 0.2500 0.4773(4) 0.0370(11) Uani 1 2 d S . .
H4A H 0.6321 0.2500 0.5120 0.055 Uiso 1 2 calc SR . .
H4B H 0.7934 0.3166 0.4995 0.055 Uiso 0.50 1 calc PR . .
H4C H 0.7934 0.1834 0.4995 0.055 Uiso 0.50 1 calc PR . .
C5 C 0.7074(5) 0.2500 0.3541(4) 0.0263(9) Uani 1 2 d S . .
C6 C 0.8172(5) 0.2500 0.2720(4) 0.0300(9) Uani 1 2 d S . .
H6A H 0.9285 0.2500 0.2811 0.036 Uiso 1 2 calc SR . .
C7 C 0.7283(5) 0.2500 0.1727(4) 0.0255(8) Uani 1 2 d S . .
C8 C 0.7863(6) 0.2500 0.0569(4) 0.0349(10) Uani 1 2 d S . .
H8A H 0.6958 0.2500 0.0054 0.052 Uiso 1 2 calc SR . .
H8B H 0.8501 0.1834 0.0455 0.052 Uiso 0.50 1 calc PR . .
H8C H 0.8501 0.3166 0.0455 0.052 Uiso 0.50 1 calc PR . .
C9 C 0.0655(4) -0.0041(3) 0.3276(3) 0.0343(7) Uani 1 1 d . . .
H9A H 0.1179 0.0227 0.3948 0.051 Uiso 1 1 calc R . .
H9B H 0.0662 -0.0856 0.3269 0.051 Uiso 1 1 calc R . .
H9C H -0.0434 0.0226 0.3238 0.051 Uiso 1 1 calc R . .
C10 C 0.1519(3) 0.0394(2) 0.2309(2) 0.0242(6) Uani 1 1 d . . .
C11 C 0.1429(4) 0.0024(3) 0.1203(3) 0.0290(6) Uani 1 1 d . . .
H11A H 0.0789 -0.0558 0.0911 0.035 Uiso 1 1 calc R . .
C12 C 0.2482(3) 0.0697(3) 0.0636(2) 0.0246(6) Uani 1 1 d . . .
C13 C 0.2874(4) 0.0691(3) -0.0557(3) 0.0341(7) Uani 1 1 d . . .
H13A H 0.3995 0.0527 -0.0626 0.051 Uiso 1 1 calc R . .
H13B H 0.2637 0.1422 -0.0875 0.051 Uiso 1 1 calc R . .
H13C H 0.2244 0.0121 -0.0939 0.051 Uiso 1 1 calc R . .
B1 B 0.4220(6) 0.2500 0.1178(4) 0.0261(10) Uani 1 2 d S . .
H1 H 0.4560 0.2500 0.0410 0.031 Uiso 1 2 calc SR . .
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'
B B 0.0013 0.0007 '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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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
N2 Cu1 N3 92.05(10) . . ?
N2 Cu1 N3 92.05(10) . 4_565 ?
N3 Cu1 N3 87.53(13) . 4_565 ?
N2 Cu1 Se1 135.23(10) . . ?
N3 Cu1 Se1 118.86(7) . . ?
N3 Cu1 Se1 118.86(7) 4_565 . ?
C1 Se1 Cu1 103.63(13) . . ?
C1 N1 C3 109.7(3) . . ?
C1 N1 C2 125.8(3) . . ?
C3 N1 C2 124.4(3) . . ?
C5 N2 N5 105.9(3) . . ?
C5 N2 Cu1 139.5(3) . . ?
N5 N2 Cu1 114.6(2) . . ?
C10 N3 N4 106.7(2) . . ?
C10 N3 Cu1 138.4(2) . . ?
N4 N3 Cu1 114.10(17) . . ?
C12 N4 N3 110.2(2) . . ?
C12 N4 B1 129.4(3) . . ?
N3 N4 B1 119.6(3) . . ?
C7 N5 N2 109.9(3) . . ?
C7 N5 B1 128.9(4) . . ?
N2 N5 B1 121.1(3) . . ?
N1 C1 N1 106.1(3) 4_565 . ?
N1 C1 Se1 126.92(17) 4_565 . ?
N1 C1 Se1 126.92(18) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C3 N1 107.21(18) 4_565 . ?
C3 C3 H3A 126.4 4_565 . ?
N1 C3 H3A 126.4 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 110.6(4) . . ?
N2 C5 C4 119.6(4) . . ?
C6 C5 C4 129.8(4) . . ?
C5 C6 C7 106.0(4) . . ?
C5 C6 H6A 127.0 . . ?
C7 C6 H6A 127.0 . . ?
N5 C7 C6 107.5(4) . . ?
N5 C7 C8 123.6(4) . . ?
C6 C7 C8 128.9(4) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 109.6(3) . . ?
N3 C10 C9 121.3(3) . . ?
C11 C10 C9 129.1(3) . . ?
C12 C11 C10 106.3(3) . . ?
C12 C11 H11A 126.8 . . ?
C10 C11 H11A 126.8 . . ?
N4 C12 C11 107.1(3) . . ?
N4 C12 C13 122.9(3) . . ?
C11 C12 C13 130.0(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 . . ?
N5 B1 N4 110.7(2) . 4_565 ?
N5 B1 N4 110.7(2) . . ?
N4 B1 N4 106.8(3) 4_565 . ?
N5 B1 H1 109.5 . . ?
N4 B1 H1 109.5 4_565 . ?
N4 B1 H1 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 N2 2.033(4) . ?
Cu1 N3 2.120(2) . ?
Cu1 N3 2.120(2) 4_565 ?
Cu1 Se1 2.3299(9) . ?
Se1 C1 1.864(4) . ?
N1 C1 1.349(3) . ?
N1 C3 1.384(4) . ?
N1 C2 1.462(4) . ?
N2 C5 1.349(5) . ?
N2 N5 1.376(5) . ?
N3 C10 1.338(4) . ?
N3 N4 1.376(3) . ?
N4 C12 1.359(4) . ?
N4 B1 1.557(4) . ?
N5 C7 1.352(5) . ?
N5 B1 1.542(6) . ?
C1 N1 1.349(3) 4_565 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C3 1.337(7) 4_565 ?
C3 H3A 0.9300 . ?
C4 C5 1.496(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.374(6) . ?
C6 C7 1.387(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.497(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.486(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.405(4) . ?
C11 C12 1.383(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.489(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
B1 N4 1.557(4) 4_565 ?
B1 H1 0.9800 . ?
