#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/45/2014505.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2014505
loop_
_publ_author_name
'Masci, Bernardo'
'Thuéry, Pierre'
_publ_section_title
8,19-Dimethyl-8,19-dihydro-8,19-ethanoanthra[2'',3'':2,3;6'',7'':2',3']di-1,4-dioxino[5,6-b;5',6'-b']diquinoxaline
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o836
_journal_page_last               o838
_journal_paper_doi               10.1107/S010827010402462X
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C34 H22 N4 O4'
_chemical_formula_moiety         'C34 H22 N4 O4'
_chemical_formula_sum            'C34 H22 N4 O4'
_chemical_formula_weight         550.56
_chemical_name_systematic
;
8,19-Dimethyl-8,19-dihydro-8,19-ethanoanthra[2',3':2,3;6',7':2,3]di-1,4-
dioxino[5,6-b;5,6-b]diquinoxaline
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.788(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.055(2)
_cell_length_b                   6.6734(12)
_cell_length_c                   14.523(2)
_cell_measurement_reflns_used    9551
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.14
_cell_volume                     2516.4(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  'SHELXTL and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       φ
_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  0.0748
_diffrn_reflns_av_sigmaI/netI    0.1090
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9551
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1473
_refine_ls_R_factor_gt           0.0641
_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)+(0.0584P)²+0.367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1674
_reflns_number_gt                1196
_reflns_number_total             2358
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1027.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2014505
_cod_database_fobs_code          2014505
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.18017(8) 0.0978(4) -0.13949(14) 0.0266(6) Uani d . 1 . . O
O2 0.12149(8) 0.0796(4) 0.01815(14) 0.0269(6) Uani d . 1 . . O
N1 0.25173(10) 0.0208(4) -0.04899(18) 0.0233(7) Uani d . 1 . . N
N2 0.19321(11) -0.0049(4) 0.10649(18) 0.0259(7) Uani d . 1 . . N
C1 0.12763(12) 0.1411(5) -0.1456(2) 0.0233(8) Uani d . 1 . . C
C2 0.09975(13) 0.1362(5) -0.0690(2) 0.0235(8) Uani d . 1 . . C
C3 0.04854(13) 0.1963(5) -0.0763(2) 0.0257(9) Uani d . 1 . . C
H3 0.0295 0.1912 -0.0250 0.031 Uiso calc R 1 . . H
C4 0.02583(12) 0.2639(5) -0.1603(2) 0.0245(8) Uani d . 1 . . C
C5 0.05467(12) 0.2651(6) -0.2383(2) 0.0254(8) Uani d . 1 . . C
C6 0.10527(13) 0.2014(5) -0.2309(2) 0.0240(8) Uani d . 1 . . C
H6 0.1241 0.1991 -0.2826 0.029 Uiso calc R 1 . . H
C7 0.20290(13) 0.0527(5) -0.0539(2) 0.0231(8) Uani d . 1 . . C
C8 0.17349(13) 0.0409(5) 0.0257(2) 0.0221(8) Uani d . 1 . . C
C9 0.24545(13) -0.0446(6) 0.1144(2) 0.0242(8) Uani d . 1 . . C
C10 0.27463(13) -0.0305(5) 0.0368(2) 0.0229(8) Uani d . 1 . . C
C11 0.32778(13) -0.0722(5) 0.0461(2) 0.0252(8) Uani d . 1 . . C
H11 0.3470 -0.0623 -0.0048 0.030 Uiso calc R 1 . . H
C12 0.35105(14) -0.1274(6) 0.1305(2) 0.0282(9) Uani d . 1 . . C
H12 0.3861 -0.1558 0.1365 0.034 Uiso calc R 1 . . H
C13 0.32222(14) -0.1415(6) 0.2084(2) 0.0291(9) Uani d . 1 . . C
H13 0.3384 -0.1785 0.2654 0.035 Uiso calc R 1 . . H
C14 0.27052(13) -0.1009(6) 0.2004(2) 0.0279(9) Uani d . 1 . . C
H14 0.2518 -0.1105 0.2520 0.034 Uiso calc R 1 . . H
C15 -0.02690(13) 0.3620(6) -0.1770(2) 0.0259(9) Uani d . 1 . . C
C16 -0.01518(14) 0.5816(6) -0.2062(2) 0.0303(9) Uani d . 1 . . C
H16A -0.0472 0.6543 -0.2188 0.036 Uiso calc R 1 . . H
H16B 0.0049 0.6489 -0.1561 0.036 Uiso calc R 1 . . H
C17 -0.05871(13) 0.3620(6) -0.0928(2) 0.0293(9) Uani d . 1 . . C
H17A -0.0659 0.2264 -0.0759 0.044 Uiso calc R 1 . . H
H17B -0.0905 0.4320 -0.1077 0.044 Uiso calc R 1 . . H
H17C -0.0396 0.4276 -0.0420 0.044 Uiso calc R 1 . . H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C1 . . 116.9(3) ?
C8 O2 C2 . . 116.5(3) ?
C7 N1 C10 . . 116.3(3) ?
C8 N2 C9 . . 116.1(3) ?
C2 C1 C6 . . 121.2(3) ?
C2 C1 O1 . . 121.6(3) ?
C6 C1 O1 . . 117.0(3) ?
C1 C2 C3 . . 119.9(3) ?
C1 C2 O2 . . 122.5(3) ?
C3 C2 O2 . . 117.5(3) ?
C4 C3 C2 . . 119.9(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 119.4(3) ?
C3 C4 C15 . . 126.3(3) yes
C5 C4 C15 . . 113.9(3) yes
C6 C5 C4 . . 120.4(3) ?
C6 C5 C15 . 2_554 125.5(3) yes
C4 C5 C15 . 2_554 113.8(3) yes
C5 C6 C1 . . 119.1(3) ?
C5 C6 H6 . . 120.5 ?
C1 C6 H6 . . 120.5 ?
N1 C7 O1 . . 116.1(3) ?
N1 C7 C8 . . 122.4(3) ?
O1 C7 C8 . . 121.5(3) ?
N2 C8 O2 . . 115.8(3) ?
N2 C8 C7 . . 123.4(3) ?
O2 C8 C7 . . 120.8(3) ?
N2 C9 C14 . . 120.3(3) ?
N2 C9 C10 . . 120.8(3) ?
C14 C9 C10 . . 118.9(3) ?
N1 C10 C11 . . 118.9(3) ?
N1 C10 C9 . . 121.0(3) ?
C11 C10 C9 . . 120.1(3) ?
C12 C11 C10 . . 119.8(3) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 120.6(3) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C14 C13 C12 . . 120.3(3) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C9 . . 120.5(3) ?
C13 C14 H14 . . 119.8 ?
C9 C14 H14 . . 119.8 ?
C4 C15 C5 . 2_554 107.9(3) yes
C5 C15 C17 2_554 . 113.2(3) ?
C4 C15 C17 . . 114.5(3) ?
C4 C15 C16 . . 104.6(3) yes
C5 C15 C16 2_554 . 105.6(3) yes
C17 C15 C16 . . 110.3(3) ?
C16 C16 C15 2_554 . 110.31(17) yes
C16 C16 H16A 2_554 . 109.6 ?
C15 C16 H16A . . 109.6 ?
C16 C16 H16B 2_554 . 109.6 ?
C15 C16 H16B . . 109.6 ?
H16A C16 H16B . . 108.1 ?
C15 C17 H17A . . 109.5 ?
C15 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C15 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.395(4) yes
O1 C7 . 1.364(4) yes
O2 C2 . 1.395(4) yes
O2 C8 . 1.375(4) yes
N1 C7 . 1.286(4) yes
N1 C10 . 1.380(4) yes
N2 C8 . 1.278(4) yes
N2 C9 . 1.382(4) yes
C1 C2 . 1.379(4) yes
C2 C3 . 1.389(4) yes
C3 C4 . 1.386(5) yes
C3 H3 . 0.9300 ?
C4 C5 . 1.410(5) yes
C5 C6 . 1.381(4) yes
C6 C1 . 1.385(4) yes
C4 C15 . 1.523(4) yes
C5 C15 2_554 1.519(4) yes
C6 H6 . 0.9300 ?
C7 C8 . 1.442(5) yes
C9 C10 . 1.413(5) yes
C10 C11 . 1.408(4) yes
C11 C12 . 1.372(4) yes
C11 H11 . 0.9300 ?
C12 C13 . 1.413(5) yes
C12 H12 . 0.9300 ?
C13 C14 . 1.370(5) yes
C14 C9 . 1.412(4) yes
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C5 2_554 1.519(4) ?
C15 C16 . 1.563(5) yes
C15 C17 . 1.533(5) yes
C16 C16 2_554 1.553(7) yes
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
