#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:36:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180147 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/44/7104447.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_7104447
loop_
_publ_author_name
'Navale, Tushar S'
'Zhai, Linyi'
'Lindeman, Sergey V'
'Rathore, Rajendra'
_publ_section_title
;
 Octamethoxydibenzochrysene: isolation and X-ray crystallographic
 characterization of a twisted polyaromatic cation radical.
;
_journal_issue                   20
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2857
_journal_page_last               2859
_journal_paper_doi               10.1039/b903133b
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C43 H46 Cl2 N4 O8'
_chemical_formula_weight         817.74
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.7180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   31.6750(8)
_cell_length_b                   7.3983(2)
_cell_length_c                   18.0078(4)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      61
_cell_measurement_theta_min      3
_cell_volume                     4041.60(17)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v2.0-2 (Bruker, 2005)'
_computing_data_reduction        'TWINABS v1.05 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)'
_computing_structure_solution    'XS/SHELXTL v6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6231
_diffrn_reflns_theta_full        62.57
_diffrn_reflns_theta_max         62.57
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  0.8609
_exptl_absorpt_correction_T_min  0.6440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS. Program for empirical absorption correction of
area-detector data. University of Goetingen. Germany.
Sheldrick, G. M. 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0817
_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)+(0.1494P)²+12.3856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2344
_refine_ls_wR_factor_ref         0.2397
_reflns_number_gt                2485
_reflns_number_total             3114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b903133b.txt
_cod_data_source_block           raj2z
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7104447
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
O1 O 0.65092(9) 0.0309(4) 0.18714(16) 0.0196(7) Uani 1 1 d . . .
O2 O 0.61187(8) 0.0784(3) 0.04231(13) 0.0210(6) Uani 1 1 d . . .
O3 O 0.34846(11) 0.4991(3) 0.03656(18) 0.0235(9) Uani 1 1 d . . .
O4 O 0.38515(8) 0.4336(4) -0.07103(13) 0.0203(6) Uani 1 1 d . . .
C1 C 0.47670(12) 0.2680(4) 0.2381(2) 0.0164(8) Uani 1 1 d . . .
C11 C 0.54544(11) 0.2275(4) 0.20279(19) 0.0168(8) Uani 1 1 d . . .
C12 C 0.58874(11) 0.1564(5) 0.22445(19) 0.0171(8) Uani 1 1 d . . .
H12 H 0.6038 0.1425 0.2780 0.021 Uiso 1 1 calc R . .
C13 C 0.60953(11) 0.1070(5) 0.1707(2) 0.0182(8) Uani 1 1 d . . .
C14 C 0.58742(11) 0.1260(5) 0.09038(19) 0.0176(8) Uani 1 1 d . . .
C15 C 0.54443(11) 0.1855(4) 0.06804(19) 0.0165(8) Uani 1 1 d . . .
H15 H 0.5292 0.1940 0.0144 0.020 Uiso 1 1 calc R . .
C16 C 0.52229(11) 0.2345(4) 0.12326(19) 0.0156(8) Uani 1 1 d . . .
C17 C 0.67257(18) -0.0043(6) 0.2678(3) 0.0341(14) Uani 1 1 d . . .
C18 C 0.59245(14) 0.1055(6) -0.0388(2) 0.0216(8) Uani 1 1 d . . .
C21 C 0.45381(11) 0.3050(4) 0.15784(19) 0.0162(8) Uani 1 1 d . . .
C22 C 0.41049(11) 0.3763(5) 0.13612(19) 0.0177(8) Uani 1 1 d . . .
H22 H 0.3959 0.3937 0.1748 0.021 Uiso 1 1 calc R . .
C23 C 0.38907(11) 0.4210(4) 0.06088(19) 0.0169(8) Uani 1 1 d . . .
C24 C 0.41014(11) 0.3931(5) 0.00224(19) 0.0175(8) Uani 1 1 d . . .
C25 C 0.45328(11) 0.3345(4) 0.02240(18) 0.0170(8) Uani 1 1 d . . .
H25 H 0.4678 0.3220 -0.0167 0.020 Uiso 1 1 calc R . .
C26 C 0.47651(11) 0.2925(4) 0.10045(19) 0.0164(8) Uani 1 1 d . . .
C27 C 0.32658(15) 0.5317(7) 0.0942(3) 0.0231(9) Uani 1 1 d . . .
C28 C 0.40299(13) 0.3859(5) -0.1329(2) 0.0211(8) Uani 1 1 d . . .
H17A H 0.6825(19) 0.110(8) 0.295(3) 0.062(17) Uiso 1 1 d . . .
H17B H 0.6522(14) -0.077(6) 0.291(2) 0.026(10) Uiso 1 1 d . . .
H17C H 0.7022(18) -0.070(8) 0.269(3) 0.055(14) Uiso 1 1 d . . .
H18A H 0.5851(14) 0.236(6) -0.053(2) 0.033(11) Uiso 1 1 d . . .
H18B H 0.6144(15) 0.080(6) -0.060(2) 0.030(11) Uiso 1 1 d . . .
H18C H 0.5680(19) 0.038(7) -0.056(3) 0.038(13) Uiso 1 1 d . . .
H27A H 0.3195(15) 0.425(7) 0.121(3) 0.035(12) Uiso 1 1 d . . .
H27B H 0.2999(13) 0.593(5) 0.068(2) 0.017(9) Uiso 1 1 d . . .
H27C H 0.3426(16) 0.626(7) 0.131(3) 0.045(13) Uiso 1 1 d . . .
H28A H 0.4148(13) 0.249(6) -0.128(2) 0.021(10) Uiso 1 1 d . . .
H28B H 0.3799(14) 0.408(6) -0.177(3) 0.030(11) Uiso 1 1 d . . .
H28C H 0.4288(15) 0.463(6) -0.131(2) 0.019(10) Uiso 1 1 d . . .
N1S N 0.29120(15) 0.9774(5) 0.5434(3) 0.0389(11) Uani 1 1 d . . .
C1S C 0.29191(12) 0.9066(5) 0.4884(2) 0.0254(9) Uani 1 1 d . . .
C2S C 0.29351(15) 0.8180(6) 0.4177(2) 0.0273(9) Uani 1 1 d . . .
H2A H 0.2664(13) 0.822(5) 0.381(2) 0.058(18) Uiso 1 1 d . . .
H2B H 0.316(2) 0.869(8) 0.405(3) 0.065(17) Uiso 1 1 d . . .
H2C H 0.3010(19) 0.699(9) 0.423(3) 0.059(16) Uiso 1 1 d . . .
N2S N 0.70859(15) 0.5062(5) 0.7498(3) 0.0384(13) Uani 1 1 d . . .
C3S C 0.70956(12) 0.5869(5) 0.6953(2) 0.0262(9) Uani 1 1 d . . .
C4S C 0.71225(15) 0.6886(6) 0.6276(2) 0.0283(9) Uani 1 1 d . . .
H4A H 0.6863(17) 0.699(6) 0.598(3) 0.035(13) Uiso 1 1 d . . .
H4B H 0.7344(15) 0.629(6) 0.601(3) 0.038(12) Uiso 1 1 d . . .
H4C H 0.719(2) 0.802(10) 0.637(4) 0.09(2) Uiso 1 1 d . . .
Cl1 Cl 0.54735(11) 0.7625(4) 0.27085(17) 0.0685(9) Uani 0.50 1 d P . .
C5S C 0.5057(8) 0.759(2) 0.2173(14) 0.030(4) Uiso 0.25 1 d P . .
Cl2 Cl 0.50396(13) 0.7611(5) 0.1725(2) 0.0814(11) Uani 0.50 1 d P . .
C6S C 0.4855(11) 0.772(3) 0.2125(17) 0.058(7) Uiso 0.25 1 d P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C13 O1 C17 116.0(3) . . ?
C14 O2 C18 117.2(3) . . ?
C23 O3 C27 116.7(3) . . ?
C24 O4 C28 116.8(3) . . ?
C1 C1 C21 118.9(4) 2_655 . ?
C1 C1 C11 117.2(4) 2_655 2_655 ?
C21 C1 C11 124.0(3) . 2_655 ?
C16 C11 C12 118.3(3) . . ?
C16 C11 C1 120.9(3) . 2_655 ?
C12 C11 C1 120.3(3) . 2_655 ?
C13 C12 C11 122.0(3) . . ?
C12 C13 O1 125.4(3) . . ?
C12 C13 C14 119.8(3) . . ?
O1 C13 C14 114.7(3) . . ?
O2 C14 C15 126.3(3) . . ?
O2 C14 C13 114.7(3) . . ?
C15 C14 C13 119.0(3) . . ?
C14 C15 C16 121.6(3) . . ?
C11 C16 C15 119.0(3) . . ?
C11 C16 C26 118.9(3) . . ?
C15 C16 C26 122.1(3) . . ?
C22 C21 C26 118.4(3) . . ?
C22 C21 C1 121.0(3) . . ?
C26 C21 C1 120.1(3) . . ?
C23 C22 C21 121.9(3) . . ?
O3 C23 C22 125.0(3) . . ?
O3 C23 C24 115.2(3) . . ?
C22 C23 C24 119.7(3) . . ?
O4 C24 C25 125.4(3) . . ?
O4 C24 C23 115.0(3) . . ?
C25 C24 C23 119.5(3) . . ?
C24 C25 C26 121.4(3) . . ?
C25 C26 C21 118.6(3) . . ?
C25 C26 C16 122.3(3) . . ?
C21 C26 C16 119.1(3) . . ?
N1S C1S C2S 178.8(5) . . ?
N2S C3S C4S 178.2(4) . . ?
C6S Cl1 C5S 56.0(12) 2_655 . ?
C6S Cl1 C5S 8.7(18) 2_655 2_655 ?
C5S Cl1 C5S 48.3(17) . 2_655 ?
C6S Cl1 Cl2 77.3(14) 2_655 . ?
C5S Cl1 Cl2 21.4(10) . . ?
C5S Cl1 Cl2 69.7(8) 2_655 . ?
C6S Cl1 C6S 46(2) 2_655 . ?
C5S Cl1 C6S 10.7(15) . . ?
C5S Cl1 C6S 38.1(10) 2_655 . ?
Cl2 Cl1 C6S 31.8(9) . . ?
C6S Cl1 Cl2 13.2(14) 2_655 2_655 ?
C5S Cl1 Cl2 68.6(11) . 2_655 ?
C5S Cl1 Cl2 20.3(7) 2_655 2_655 ?
Cl2 Cl1 Cl2 90.0(2) . 2_655 ?
C6S Cl1 Cl2 58.3(9) . 2_655 ?
C6S C5S Cl2 95(4) . . ?
C6S C5S C6S 93(5) . 2_655 ?
Cl2 C5S C6S 170(4) . 2_655 ?
C6S C5S C5S 66(4) . 2_655 ?
Cl2 C5S C5S 161(4) . 2_655 ?
C6S C5S C5S 28.1(16) 2_655 2_655 ?
C6S C5S Cl1 145(5) . . ?
Cl2 C5S Cl1 119(3) . . ?
C6S C5S Cl1 53(2) 2_655 . ?
C5S C5S Cl1 80(2) 2_655 . ?
C6S C5S Cl1 16(4) . 2_655 ?
Cl2 C5S Cl1 110(2) . 2_655 ?
C6S C5S Cl1 79(2) 2_655 2_655 ?
C5S C5S Cl1 51.4(17) 2_655 2_655 ?
Cl1 C5S Cl1 131.7(17) . 2_655 ?
C6S C5S Cl2 73(4) . 2_655 ?
Cl2 C5S Cl2 168(2) . 2_655 ?
C6S C5S Cl2 21(2) 2_655 2_655 ?
C5S C5S Cl2 7.1(14) 2_655 2_655 ?
Cl1 C5S Cl2 73.2(10) . 2_655 ?
Cl1 C5S Cl2 58.5(7) 2_655 2_655 ?
C5S Cl2 C6S 36.5(17) . . ?
C5S Cl2 Cl1 39.9(18) . . ?
C6S Cl2 Cl1 76.0(18) . . ?
C5S Cl2 C6S 6(2) . 2_655 ?
C6S Cl2 C6S 41(3) . 2_655 ?
Cl1 Cl2 C6S 34.6(9) . 2_655 ?
C5S Cl2 C5S 12(2) . 2_655 ?
C6S Cl2 C5S 25(2) . 2_655 ?
Cl1 Cl2 C5S 51.8(6) . 2_655 ?
C6S Cl2 C5S 17.4(8) 2_655 2_655 ?
C5S Cl2 Cl1 50.2(18) . 2_655 ?
C6S Cl2 Cl1 14.7(17) . 2_655 ?
Cl1 Cl2 Cl1 90.0(2) . 2_655 ?
C6S Cl2 Cl1 55.5(10) 2_655 2_655 ?
C5S Cl2 Cl1 38.2(6) 2_655 2_655 ?
C5S C6S Cl2 49(3) . . ?
C5S C6S Cl1 155(5) . 2_655 ?
Cl2 C6S Cl1 152(3) . 2_655 ?
C5S C6S C5S 86(5) . 2_655 ?
Cl2 C6S C5S 134(4) . 2_655 ?
Cl1 C6S C5S 71(2) 2_655 2_655 ?
C5S C6S C6S 61(4) . 2_655 ?
Cl2 C6S C6S 109(4) . 2_655 ?
Cl1 C6S C6S 98(3) 2_655 2_655 ?
C5S C6S C6S 26.6(16) 2_655 2_655 ?
C5S C6S Cl1 24(3) . . ?
Cl2 C6S Cl1 72.3(19) . . ?
Cl1 C6S Cl1 134(2) 2_655 . ?
C5S C6S Cl1 63(2) 2_655 . ?
C6S C6S Cl1 37(2) 2_655 . ?
C5S C6S Cl2 90(4) . 2_655 ?
Cl2 C6S Cl2 138(3) . 2_655 ?
Cl1 C6S Cl2 68.0(14) 2_655 2_655 ?
C5S C6S Cl2 4.1(15) 2_655 2_655 ?
C6S C6S Cl2 29.8(19) 2_655 2_655 ?
Cl1 C6S Cl2 66.2(9) . 2_655 ?
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
O1 C13 1.378(4) . ?
O1 C17 1.441(6) . ?
O2 C14 1.363(4) . ?
O2 C18 1.426(4) . ?
O3 C23 1.362(5) . ?
O3 C27 1.426(5) . ?
O4 C24 1.363(4) . ?
O4 C28 1.432(4) . ?
C1 C1 1.414(7) 2_655 ?
C1 C21 1.445(5) . ?
C1 C11 1.464(5) 2_655 ?
C11 C16 1.410(5) . ?
C11 C12 1.415(5) . ?
C11 C1 1.464(5) 2_655 ?
C12 C13 1.367(5) . ?
C13 C14 1.421(5) . ?
C14 C15 1.377(5) . ?
C15 C16 1.419(5) . ?
C16 C26 1.453(5) . ?
C21 C22 1.416(5) . ?
C21 C26 1.422(5) . ?
C22 C23 1.370(5) . ?
C23 C24 1.417(5) . ?
C24 C25 1.379(5) . ?
C25 C26 1.421(5) . ?
N1S C1S 1.126(6) . ?
C1S C2S 1.447(6) . ?
N2S C3S 1.156(6) . ?
C3S C4S 1.457(6) . ?
Cl1 C6S 1.17(3) 2_655 ?
Cl1 C5S 1.39(2) . ?
Cl1 C5S 1.75(3) 2_655 ?
Cl1 Cl2 1.904(5) . ?
Cl1 C6S 1.94(3) . ?
Cl1 Cl2 2.153(5) 2_655 ?
C5S C6S 0.63(3) . ?
C5S Cl2 0.79(2) . ?
C5S C6S 1.22(3) 2_655 ?
C5S C5S 1.33(5) 2_655 ?
C5S Cl1 1.75(3) 2_655 ?
C5S Cl2 2.09(3) 2_655 ?
Cl2 C6S 1.05(3) . ?
Cl2 C6S 2.00(3) 2_655 ?
Cl2 C5S 2.09(3) 2_655 ?
Cl2 Cl1 2.153(5) 2_655 ?
C6S Cl1 1.17(3) 2_655 ?
C6S C5S 1.22(3) 2_655 ?
C6S C6S 1.40(6) 2_655 ?
C6S Cl2 2.00(3) 2_655 ?
