#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:52:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178409 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/30/4023007.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_4023007
loop_
_publ_author_name
'Joe B. Gilroy'
'Steve D. J. McKinnon'
'Pierre Kennepohl'
'Mark S. Zsombor'
'Michael J. Ferguson'
'Laurence K. Thompson'
'Robin G. Hicks'
_publ_section_title
;
 Probing Electronic Communication in Stable Benzene-Bridged
 Verdazyl Diradicals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8062
_journal_page_last               8069
_journal_paper_doi               10.1021/jo7014449
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C22 H32 N8 O2'
_chemical_formula_sum            'C22 H32 N8 O2'
_chemical_formula_weight         440.56
_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                 112.993(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.760(6)
_cell_length_b                   5.9051(12)
_cell_length_c                   16.435(3)
_cell_measurement_reflns_used    2271
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.55
_cell_volume                     2390.7(8)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7844
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0589
_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)+(0.0544P)²+5.1563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1661
_reflns_number_gt                1546
_reflns_number_total             2160
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo7014449-File002.cif
_cod_data_source_block           vic0606
_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      'C 2/c'
_cod_database_code               4023007
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 0.29516(9) 0.4490(4) 0.09513(14) 0.0446(6) Uani 1 1 d .
N11 N 0.37070(10) 0.2278(4) 0.13431(15) 0.0343(6) Uani 1 1 d .
N12 N 0.41279(10) 0.1374(4) 0.11753(15) 0.0346(6) Uani 1 1 d .
N13 N 0.33657(9) 0.4049(4) -0.00189(15) 0.0300(6) Uani 1 1 d .
N14 N 0.37852(9) 0.3260(4) -0.02145(15) 0.0303(6) Uani 1 1 d .
C1 C 0.45803(11) 0.0942(5) 0.01941(17) 0.0271(7) Uani 1 1 d .
C2 C 0.47699(11) 0.2028(5) -0.03819(18) 0.0305(7) Uani 1 1 d .
H2 H 0.4611 0.3422 -0.0647 0.037 Uiso 1 1 calc R
C3 C 0.48142(11) -0.1104(5) 0.05720(19) 0.0316(7) Uani 1 1 d .
H3 H 0.4687 -0.1869 0.0963 0.038 Uiso 1 1 calc R
C11 C 0.41372(11) 0.1940(5) 0.03985(17) 0.0283(7) Uani 1 1 d .
C12 C 0.33159(12) 0.3668(5) 0.07735(19) 0.0319(7) Uani 1 1 d .
C13 C 0.37223(13) 0.1759(6) 0.22326(19) 0.0380(8) Uani 1 1 d .
H13 H 0.3387 0.2387 0.2277 0.046 Uiso 1 1 calc R
C14 C 0.42107(15) 0.2910(6) 0.2921(2) 0.0492(9) Uani 1 1 d .
H14A H 0.4191 0.4544 0.2807 0.059 Uiso 1 1 calc R
H14B H 0.4544 0.2300 0.2891 0.059 Uiso 1 1 calc R
H14C H 0.4213 0.2632 0.3510 0.059 Uiso 1 1 calc R
C15 C 0.37300(15) -0.0770(6) 0.2369(2) 0.0493(9) Uani 1 1 d .
H15A H 0.3409 -0.1448 0.1911 0.059 Uiso 1 1 calc R
H15B H 0.3728 -0.1094 0.2952 0.059 Uiso 1 1 calc R
H15C H 0.4058 -0.1411 0.2332 0.059 Uiso 1 1 calc R
C16 C 0.29745(11) 0.5542(5) -0.06857(19) 0.0325(7) Uani 1 1 d .
H16 H 0.2640 0.5643 -0.0556 0.039 Uiso 1 1 calc R
C17 C 0.28184(13) 0.4536(6) -0.1598(2) 0.0429(8) Uani 1 1 d .
H17A H 0.2664 0.3025 -0.1614 0.051 Uiso 1 1 calc R
H17B H 0.3141 0.4421 -0.1739 0.051 Uiso 1 1 calc R
H17C H 0.2549 0.5511 -0.2034 0.051 Uiso 1 1 calc R
C18 C 0.32122(14) 0.7886(6) -0.0611(2) 0.0495(9) Uani 1 1 d .
H18A H 0.3305 0.8461 -0.0010 0.059 Uiso 1 1 calc R
H18B H 0.2946 0.8894 -0.1035 0.059 Uiso 1 1 calc R
H18C H 0.3540 0.7825 -0.0738 0.059 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'
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
N12 N11 C12 124.4(2) .
N12 N11 C13 114.3(2) .
C12 N11 C13 121.2(2) .
C11 N12 N11 114.9(2) .
N14 N13 C12 124.0(2) .
N14 N13 C16 116.1(2) .
C12 N13 C16 119.8(2) .
C11 N14 N13 115.2(2) .
C3 C1 C2 118.9(3) .
C3 C1 C11 120.5(3) .
C2 C1 C11 120.6(3) .
C3 C2 C1 120.8(3) 5_655
C2 C3 C1 120.3(3) 5_655
N12 C11 N14 127.0(2) .
N12 C11 C1 115.9(2) .
N14 C11 C1 117.1(2) .
O1 C12 N11 122.8(3) .
O1 C12 N13 122.8(3) .
N11 C12 N13 114.4(2) .
N11 C13 C15 110.2(3) .
N11 C13 C14 109.2(3) .
C15 C13 C14 112.1(3) .
N13 C16 C18 109.5(2) .
N13 C16 C17 110.1(2) .
C18 C16 C17 112.7(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.222(3) .
N11 N12 1.368(3) .
N11 C12 1.371(4) .
N11 C13 1.478(4) .
N12 C11 1.329(4) .
N13 N14 1.365(3) .
N13 C12 1.378(4) .
N13 C16 1.476(3) .
N14 C11 1.330(4) .
C1 C3 1.390(4) .
C1 C2 1.393(4) .
C1 C11 1.475(4) .
C2 C3 1.381(4) 5_655
C3 C2 1.381(4) 5_655
C13 C15 1.509(5) .
C13 C14 1.515(5) .
C16 C18 1.508(5) .
C16 C17 1.512(4) .
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
C12 N11 N12 C11 0.0(4) .
C13 N11 N12 C11 -176.1(3) .
C12 N13 N14 C11 4.2(4) .
C16 N13 N14 C11 179.2(2) .
C3 C1 C2 C3 -0.4(5) 5_655
C11 C1 C2 C3 179.7(3) 5_655
C2 C1 C3 C2 0.4(5) 5_655
C11 C1 C3 C2 -179.8(3) 5_655
N11 N12 C11 N14 -0.2(4) .
N11 N12 C11 C1 -178.6(2) .
N13 N14 C11 N12 -1.8(4) .
N13 N14 C11 C1 176.6(2) .
C3 C1 C11 N12 26.4(4) .
C2 C1 C11 N12 -153.8(3) .
C3 C1 C11 N14 -152.2(3) .
C2 C1 C11 N14 27.6(4) .
N12 N11 C12 O1 -178.3(3) .
C13 N11 C12 O1 -2.4(5) .
N12 N11 C12 N13 2.1(4) .
C13 N11 C12 N13 178.0(3) .
N14 N13 C12 O1 176.1(3) .
C16 N13 C12 O1 1.2(4) .
N14 N13 C12 N11 -4.3(4) .
C16 N13 C12 N11 -179.2(3) .
N12 N11 C13 C15 -57.3(4) .
C12 N11 C13 C15 126.5(3) .
N12 N11 C13 C14 66.2(3) .
C12 N11 C13 C14 -110.0(3) .
N14 N13 C16 C18 -78.2(3) .
C12 N13 C16 C18 97.0(3) .
N14 N13 C16 C17 46.2(3) .
C12 N13 C16 C17 -138.6(3) .
