#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:51:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180158 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/54/7105490.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_7105490
loop_
_publ_author_name
'Yong, Guo-Ping'
'Li, Chong-Fu'
'Li, Ying-Zhou'
'Luo, Shi-Wei'
_publ_section_title
;
 New zwitterionic radical salts: dimers in solution and unusual
 magnetic and luminescent properties in the solid state
;
_journal_issue                   18
_journal_name_full               'Chemical Communications'
_journal_page_first              3194
_journal_page_last               3196
_journal_paper_doi               10.1039/b923730e
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C14 H16 Cl2 N4 O11'
_chemical_formula_weight         487.20
_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                 100.94(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.774(6)
_cell_length_b                   10.523(2)
_cell_length_c                   13.389(3)
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.2327
_cell_measurement_theta_min      3.0972
_cell_volume                     3842.0(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Gemini S Ultra'
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15053
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.58
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.9031
_exptl_absorpt_correction_T_min  0.8670
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.835
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         6291
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0962
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2887
_refine_ls_wR_factor_ref         0.3191
_reflns_number_gt                3028
_reflns_number_total             6291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b923730e.txt
_cod_data_source_block           2
_cod_original_cell_volume        3842.0(13)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7105490
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.00480(4) 0.22247(10) 0.46564(7) 0.0533(3) Uani 1 1 d . . .
O4 O 0.00158(16) 0.1483(5) 0.5538(3) 0.0961(13) Uani 1 1 d . . .
O3 O -0.0267(2) 0.1723(5) 0.3821(4) 0.133(2) Uani 1 1 d . . .
O5 O 0.05497(19) 0.2150(5) 0.4576(5) 0.137(2) Uani 1 1 d . . .
Cl2 Cl 0.18665(4) 0.11961(10) 0.38001(9) 0.0628(4) Uani 1 1 d D . .
N3 N 0.10475(11) -0.4215(3) 0.4027(2) 0.0410(6) Uani 1 1 d . . .
C8 C 0.12944(13) -0.3843(3) 0.4984(2) 0.0403(7) Uani 1 1 d . . .
N2 N 0.17583(12) -0.4105(3) 0.6703(2) 0.0444(7) Uani 1 1 d . . .
N1 N 0.18001(11) -0.6162(3) 0.6897(2) 0.0449(7) Uani 1 1 d . . .
O1 O 0.14712(11) -0.1779(3) 0.5736(2) 0.0579(7) Uani 1 1 d . . .
C7 C 0.15142(12) -0.4657(4) 0.5798(2) 0.0403(7) Uani 1 1 d . . .
N4 N 0.10203(13) -0.2140(3) 0.4063(2) 0.0485(7) Uani 1 1 d . . .
C1 C 0.19310(13) -0.5036(4) 0.7378(3) 0.0429(8) Uani 1 1 d . . .
C14 C 0.12688(14) -0.2526(4) 0.4986(3) 0.0441(8) Uani 1 1 d . . .
C13 C 0.08839(13) -0.3171(4) 0.3477(3) 0.0449(8) Uani 1 1 d . . .
C6 C 0.15448(14) -0.5929(4) 0.5932(3) 0.0454(8) Uani 1 1 d . . .
H6A H 0.1416 -0.6540 0.5453 0.054 Uiso 1 1 calc R . .
C2 C 0.21972(16) -0.4996(5) 0.8376(3) 0.0575(10) Uani 1 1 d . . .
H2A H 0.2290 -0.4230 0.8702 0.069 Uiso 1 1 calc R . .
C9 C 0.09651(15) -0.5427(4) 0.3614(3) 0.0514(9) Uani 1 1 d . . .
H9A H 0.1080 -0.6148 0.3985 0.062 Uiso 1 1 calc R . .
C5 C 0.19165(16) -0.7300(4) 0.7392(3) 0.0572(10) Uani 1 1 d . . .
H5A H 0.1822 -0.8062 0.7060 0.069 Uiso 1 1 calc R . .
C12 C 0.06221(14) -0.3250(5) 0.2468(3) 0.0538(10) Uani 1 1 d . . .
H12A H 0.0512 -0.2527 0.2095 0.065 Uiso 1 1 calc R . .
C10 C 0.07041(16) -0.5511(5) 0.2627(3) 0.0584(10) Uani 1 1 d . . .
H10A H 0.0639 -0.6309 0.2334 0.070 Uiso 1 1 calc R . .
C3 C 0.23139(16) -0.6126(5) 0.8845(3) 0.0649(12) Uani 1 1 d . . .
H3A H 0.2495 -0.6139 0.9505 0.078 Uiso 1 1 calc R . .
C11 C 0.05379(15) -0.4443(5) 0.2063(3) 0.0572(11) Uani 1 1 d . . .
H11A H 0.0367 -0.4536 0.1399 0.069 Uiso 1 1 calc R . .
C4 C 0.21619(17) -0.7309(5) 0.8339(4) 0.0653(12) Uani 1 1 d . . .
H4A H 0.2237 -0.8076 0.8678 0.078 Uiso 1 1 calc R . .
O7 O 0.1679(4) 0.0029(6) 0.3365(10) 0.303(7) Uani 1 1 d DU . .
O8 O 0.2350(3) 0.0797(15) 0.4220(8) 0.316(9) Uani 1 1 d DU . .
O11 O 0.10715(16) 0.9692(4) 0.0930(4) 0.1010(14) Uani 1 1 d . . .
O10 O 0.0578(2) -0.0066(4) 0.3004(3) 0.1052(14) Uani 1 1 d . . .
O6 O 0.1666(4) 0.1649(9) 0.4553(9) 0.274(6) Uani 1 1 d DU . .
O2 O -0.0083(2) 0.3477(4) 0.4795(3) 0.1068(15) Uani 1 1 d . . .
H02 H 0.1012(14) -0.138(4) 0.384(3) 0.042(10) Uiso 1 1 d . . .
O9 O 0.1983(4) 0.2120(8) 0.3109(7) 0.219(4) Uiso 1 1 d D . .
H01 H 0.1825(17) -0.340(5) 0.688(3) 0.058(14) 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'
Cl Cl 0.1484 0.1585 '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
O3 Cl1 O2 109.1(3) . . ?
O3 Cl1 O5 113.3(4) . . ?
O2 Cl1 O5 110.4(3) . . ?
O3 Cl1 O4 109.2(3) . . ?
O2 Cl1 O4 110.3(3) . . ?
O5 Cl1 O4 104.4(3) . . ?
O6 Cl2 O7 116.6(7) . . ?
O6 Cl2 O8 107.9(7) . . ?
O7 Cl2 O8 98.8(7) . . ?
O6 Cl2 O9 115.3(6) . . ?
O7 Cl2 O9 115.9(6) . . ?
O8 Cl2 O9 98.3(6) . . ?
C13 N3 C8 109.2(3) . . ?
C13 N3 C9 121.1(3) . . ?
C8 N3 C9 129.7(3) . . ?
C14 C8 N3 105.4(3) . . ?
C14 C8 C7 127.8(3) . . ?
N3 C8 C7 126.8(3) . . ?
C1 N2 C7 109.3(3) . . ?
C1 N1 C6 109.4(3) . . ?
C1 N1 C5 120.7(3) . . ?
C6 N1 C5 129.9(3) . . ?
C6 C7 N2 106.8(3) . . ?
C6 C7 C8 134.6(3) . . ?
N2 C7 C8 118.6(3) . . ?
C13 N4 C14 109.0(3) . . ?
N2 C1 N1 106.5(3) . . ?
N2 C1 C2 132.1(4) . . ?
N1 C1 C2 121.5(4) . . ?
O1 C14 N4 125.9(3) . . ?
O1 C14 C8 125.7(3) . . ?
N4 C14 C8 108.4(3) . . ?
N4 C13 N3 108.0(3) . . ?
N4 C13 C12 129.9(4) . . ?
N3 C13 C12 122.1(4) . . ?
C7 C6 N1 108.1(3) . . ?
C3 C2 C1 116.9(4) . . ?
C10 C9 N3 117.0(4) . . ?
C4 C5 N1 120.0(4) . . ?
C11 C12 C13 116.9(4) . . ?
C11 C10 C9 122.0(4) . . ?
C2 C3 C4 121.1(4) . . ?
C12 C11 C10 120.9(4) . . ?
C5 C4 C3 119.8(4) . . ?
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
Cl1 O3 1.387(4) . ?
Cl1 O2 1.389(4) . ?
Cl1 O5 1.420(5) . ?
Cl1 O4 1.433(4) . ?
Cl2 O6 1.329(6) . ?
Cl2 O7 1.416(6) . ?
Cl2 O8 1.418(6) . ?
Cl2 O9 1.421(7) . ?
N3 C13 1.352(5) . ?
N3 C8 1.391(4) . ?
N3 C9 1.392(5) . ?
C8 C14 1.388(5) . ?
C8 C7 1.429(5) . ?
N2 C1 1.357(5) . ?
N2 C7 1.398(5) . ?
N1 C1 1.365(5) . ?
N1 C6 1.373(5) . ?
N1 C5 1.377(5) . ?
O1 C14 1.315(5) . ?
C7 C6 1.351(5) . ?
N4 C13 1.350(5) . ?
N4 C14 1.358(5) . ?
C1 C2 1.400(5) . ?
C13 C12 1.410(5) . ?
C2 C3 1.355(7) . ?
C9 C10 1.385(6) . ?
C5 C4 1.320(7) . ?
C12 C11 1.370(6) . ?
C10 C11 1.383(7) . ?
C3 C4 1.442(8) . ?
