#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/22/4332213.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_4332213
loop_
_publ_author_name
'Tretyakov, Eugene'
'Fokin, Sergei'
'Romanenko, Galina'
'Ikorskii, Vladimir'
'Vasilevsky, Sergei'
'Ovcharenko, Victor'
_publ_section_title
;
 2D and 3D Cu(hfac)2Complexes with Nitronyl Nitroxide Biradicals
;
_journal_issue                   9
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3671
_journal_page_last               3678
_journal_paper_doi               10.1021/ic060132e
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C10.5 H15 N4 O2'
_chemical_formula_weight         229.27
_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                 120.148(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.435(3)
_cell_length_b                   8.7585(10)
_cell_length_c                   13.474(2)
_cell_measurement_temperature    568(2)
_cell_volume                     2391.5(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      568(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0936
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4933
_diffrn_reflns_theta_full        23.22
_diffrn_reflns_theta_max         23.22
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.091
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0012(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.679
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.679
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0394
_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)+(0.1621P)²+0.5706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1508
_reflns_number_total             1710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic060132esup1.cif
_cod_data_source_block           L4
_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_cell_volume        2391.6(6)
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C10.50 H15 N4 O2'
_cod_database_code               4332213
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
O1 O 0.46901(5) 0.76800(14) 0.91515(9) 0.0603(4) Uani 1 1 d .
N1 N 0.41507(6) 0.83484(15) 0.89365(11) 0.0462(4) Uani 1 1 d .
C1 C 0.38276(8) 0.95222(19) 0.80052(14) 0.0527(5) Uani 1 1 d .
C2 C 0.35135(15) 0.8645(3) 0.68710(17) 0.0820(8) Uani 1 1 d .
H3 H 0.3299(13) 0.936(3) 0.627(2) 0.084(6) Uiso 1 1 d .
H2 H 0.3884(14) 0.816(3) 0.684(2) 0.105(8) Uiso 1 1 d .
H1 H 0.3150(15) 0.788(3) 0.677(2) 0.116(10) Uiso 1 1 d .
C3 C 0.43539(13) 1.0623(3) 0.8100(3) 0.0845(8) Uani 1 1 d .
H6 H 0.4627(16) 1.014(3) 0.792(3) 0.118(10) Uiso 1 1 d .
H5 H 0.4628(15) 1.106(3) 0.894(3) 0.122(10) Uiso 1 1 d .
H4 H 0.4139(13) 1.142(3) 0.757(2) 0.102(8) Uiso 1 1 d .
C4 C 0.33146(8) 1.02153(17) 0.82913(14) 0.0504(5) Uani 1 1 d .
C5 C 0.35628(13) 1.1631(2) 0.9051(2) 0.0717(6) Uani 1 1 d .
H9 H 0.4040(13) 1.144(2) 0.976(2) 0.091(7) Uiso 1 1 d .
H8 H 0.3592(11) 1.243(3) 0.863(2) 0.080(6) Uiso 1 1 d .
H7 H 0.3245(11) 1.189(2) 0.9272(17) 0.070(5) Uiso 1 1 d .
C6 C 0.26299(11) 1.0504(3) 0.7272(2) 0.0742(6) Uani 1 1 d .
H10 H 0.2647(11) 1.131(3) 0.680(2) 0.082(6) Uiso 1 1 d .
H11 H 0.2461(13) 0.952(3) 0.681(2) 0.096(7) Uiso 1 1 d .
H12 H 0.2332(14) 1.080(3) 0.753(2) 0.098(8) Uiso 1 1 d .
N2 N 0.32757(6) 0.89767(13) 0.90261(11) 0.0453(4) Uani 1 1 d .
O2 O 0.28389(6) 0.89834(13) 0.93254(11) 0.0627(4) Uani 1 1 d .
C7 C 0.37936(7) 0.80144(16) 0.94286(12) 0.0402(4) Uani 1 1 d .
C8 C 0.39537(7) 0.68580(16) 1.02890(11) 0.0398(4) Uani 1 1 d .
C9 C 0.35937(8) 0.64078(18) 1.08207(13) 0.0480(5) Uani 1 1 d .
H13 H 0.3175(10) 0.6718(19) 1.0655(15) 0.051(4) Uiso 1 1 d .
N3 N 0.39162(6) 0.53787(16) 1.16318(11) 0.0508(4) Uani 1 1 d .
N4 N 0.44856(6) 0.51453(13) 1.16197(10) 0.0416(4) Uani 1 1 d .
C10 C 0.5000 0.4205(2) 1.2500 0.0443(6) Uani 1 2 d S
H14 H 0.5209(8) 0.3636(18) 1.2161(14) 0.048(4) Uiso 1 1 d .
C11 C 0.45244(8) 0.60008(16) 1.08335(12) 0.0419(4) Uani 1 1 d .
H15 H 0.4890(9) 0.5975(16) 1.0753(14) 0.045(4) 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'
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
O1 N1 C7 125.32(12) .
O1 N1 C1 121.74(11) .
C7 N1 C1 112.74(12) .
N1 C1 C3 108.49(15) .
N1 C1 C2 106.21(15) .
C3 C1 C2 111.4(2) .
N1 C1 C4 100.84(11) .
C3 C1 C4 115.26(18) .
C2 C1 C4 113.52(16) .
N2 C4 C6 109.26(15) .
N2 C4 C5 105.90(14) .
C6 C4 C5 110.18(17) .
N2 C4 C1 101.04(11) .
C6 C4 C1 115.87(17) .
C5 C4 C1 113.65(15) .
O2 N2 C7 125.40(12) .
O2 N2 C4 121.96(11) .
C7 N2 C4 112.12(12) .
N1 C7 N2 108.99(12) .
N1 C7 C8 125.38(13) .
N2 C7 C8 125.58(13) .
C11 C8 C9 104.20(13) .
C11 C8 C7 126.99(13) .
C9 C8 C7 128.70(14) .
N3 C9 C8 111.80(14) .
C9 N3 N4 104.46(12) .
C11 N4 N3 112.54(12) .
C11 N4 C10 127.36(11) .
N3 N4 C10 119.60(10) .
N4 C10 N4 110.75(16) 2_657
N4 C11 C8 107.00(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.2871(16) .
N1 C7 1.3354(19) .
N1 C1 1.500(2) .
C1 C3 1.520(3) .
C1 C2 1.529(3) .
C1 C4 1.558(2) .
C4 N2 1.502(2) .
C4 C6 1.520(3) .
C4 C5 1.525(3) .
N2 O2 1.2748(17) .
N2 C7 1.3476(18) .
C7 C8 1.440(2) .
C8 C11 1.380(2) .
C8 C9 1.410(2) .
C9 N3 1.322(2) .
N3 N4 1.3582(18) .
N4 C11 1.3375(19) .
N4 C10 1.4500(17) .
C10 N4 1.4500(17) 2_657
