#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/60/2206039.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_2206039
loop_
_publ_author_name
'Senju, Takatoshi'
'Hoki, Tomonori'
'Mizuguchi, Jin'
_publ_section_title
;
 The triclinic form of
 2,9-dichloro-5,12-dihydroquino[2,3-b]acridine-7,14-dithione
 dimethylacetamide disolvate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1930
_journal_page_last               o1932
_journal_paper_doi               10.1107/S1600536805016636
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H10 Cl2 N2 S2 , 2C4 H9 N O'
_chemical_formula_moiety         'C20 H10 Cl2 N2 S2 , 2C4 H9 N O'
_chemical_formula_sum            'C28 H28 Cl2 N4 O2 S2'
_chemical_formula_weight         587.58
_chemical_name_systematic
;
2,9-dichloro-5,12-dihydroquino[2,3-b]acridine-
7,14-dithione dimethylacetamide disolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                104.32(2)
_cell_angle_beta                 96.91(2)
_cell_angle_gamma                107.369(18)
_cell_formula_units_Z            1
_cell_length_a                   7.156(2)
_cell_length_b                   8.941(3)
_cell_length_c                   11.487(4)
_cell_measurement_reflns_used    5253
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.0
_cell_measurement_theta_min      4.1
_cell_volume                     664.5(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.892
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-F imaging-plate'
_diffrn_measurement_method       '72 frames, Δ ω = 10°'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5955
_diffrn_reflns_theta_full        68.11
_diffrn_reflns_theta_max         68.11
_exptl_absorpt_coefficient_mu    3.951
_exptl_absorpt_correction_T_max  0.729
_exptl_absorpt_correction_T_min  0.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             306.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2164
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1319P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2165
_reflns_number_gt                1551
_reflns_number_total             2164
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ob6520.cif
_cod_data_source_block           I
_cod_database_code               2206039
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +x,+y,+z
2 -x,-y,-z
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
Cl1 -0.05006(15) 0.06167(11) -0.16885(10) 0.0425(4) Uani d . 1 . . Cl
S1 0.11519(16) 0.63783(12) -0.28496(10) 0.0454(4) Uani d . 1 . . S
O1 0.6372(4) 0.8346(4) 0.3447(3) 0.0475(8) Uani d . 1 . . O
N1 0.4336(4) 0.7451(4) 0.1031(3) 0.0299(8) Uani d . 1 . . N
H1N 0.4894 0.7667 0.1807 0.036 Uiso calc R 1 . . H
C1 0.1058(5) 0.3828(4) -0.1471(4) 0.0336(10) Uani d . 1 . . C
H1 0.0390 0.3525 -0.2305 0.040 Uiso calc R 1 . . H
C2 0.0910(5) 0.2668(4) -0.0882(4) 0.0331(9) Uani d . 1 . . C
C3 0.1858(6) 0.3040(5) 0.0335(4) 0.0376(10) Uani d . 1 . . C
H3 0.1731 0.2199 0.0720 0.045 Uiso calc R 1 . . H
C4 0.2984(5) 0.4645(4) 0.0974(4) 0.0328(9) Uani d . 1 . . C
H4 0.3628 0.4919 0.1809 0.039 Uiso calc R 1 . . H
C5 0.3185(5) 0.5890(4) 0.0389(4) 0.0303(9) Uani d . 1 . . C
C6 0.2213(5) 0.5492(4) -0.0838(4) 0.0302(9) Uani d . 1 . . C
C7 0.2383(5) 0.6751(4) -0.1460(4) 0.0336(10) Uani d . 1 . . C
C8 0.3711(5) 0.8413(4) -0.0718(4) 0.0297(9) Uani d . 1 . . C
C9 0.4662(5) 0.8708(5) 0.0513(4) 0.0305(9) Uani d . 1 . . C
C10 0.4063(5) 0.9725(4) -0.1203(4) 0.0320(9) Uani d . 1 . . C
H10 0.3420 0.9549 -0.2023 0.038 Uiso calc R 1 . . H
C11 0.8909(6) 0.7842(6) 0.4931(5) 0.0612(14) Uani d . 1 . . C
H11A 0.9666 0.7607 0.5591 0.092 Uiso calc PR 0.623(13) A 1 H
H11B 0.9578 0.8971 0.4930 0.092 Uiso calc PR 0.623(13) A 1 H
H11C 0.8842 0.7078 0.4139 0.092 Uiso calc PR 0.623(13) A 1 H
H11D 0.8766 0.7589 0.5706 0.092 Uiso calc PR 0.377(13) A 2 H
H11E 1.0036 0.8864 0.5089 0.092 Uiso calc PR 0.377(13) A 2 H
H11F 0.9158 0.6944 0.4360 0.092 Uiso calc PR 0.377(13) A 2 H
C12 0.6031(6) 0.7082(5) 0.6163(4) 0.0446(11) Uani d . 1 . . C
H12A 0.7111 0.6936 0.6685 0.067 Uiso calc PR 0.623(13) A 1 H
H12B 0.4920 0.6035 0.5826 0.067 Uiso calc PR 0.623(13) A 1 H
H12C 0.5562 0.7905 0.6653 0.067 Uiso calc PR 0.623(13) A 1 H
H12D 0.4832 0.6798 0.6509 0.067 Uiso calc PR 0.377(13) A 2 H
H12E 0.7107 0.7990 0.6776 0.067 Uiso calc PR 0.377(13) A 2 H
H12F 0.6461 0.6125 0.5937 0.067 Uiso calc PR 0.377(13) A 2 H
C13 0.3557(6) 0.7754(6) 0.4540(5) 0.0582(14) Uani d . 1 . . C
H13A 0.3423 0.7413 0.5282 0.087 Uiso calc PR 0.623(13) A 1 H
H13B 0.2556 0.6927 0.3837 0.087 Uiso calc PR 0.623(13) A 1 H
H13C 0.3349 0.8812 0.4655 0.087 Uiso calc PR 0.623(13) A 1 H
H13D 0.2581 0.7417 0.5037 0.087 Uiso calc PR 0.377(13) A 2 H
H13E 0.3046 0.7053 0.3686 0.087 Uiso calc PR 0.377(13) A 2 H
H13F 0.3777 0.8900 0.4571 0.087 Uiso calc PR 0.377(13) A 2 H
N2 0.6791(10) 0.7641(6) 0.5140(6) 0.0385(19) Uiso d P 0.623(13) A 1 N
C14 0.5668(11) 0.7929(8) 0.4295(7) 0.041(2) Uiso d P 0.623(13) A 1 C
N3 0.5569(15) 0.7585(10) 0.5055(9) 0.031(3) Uiso d P 0.377(13) A 2 N
C15 0.6937(17) 0.8049(12) 0.4354(11) 0.032(3) Uiso d P 0.377(13) A 2 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.333 0.557
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.364 0.702
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, 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
C5 N1 C9 . . 122.2(3) yes
C5 N1 H1N . . 118.9 no
C9 N1 H1N . . 118.9 no
C2 C1 C6 . . 119.8(4) yes
C2 C1 H1 . . 120.1 no
C6 C1 H1 . . 120.1 no
C1 C2 C3 . . 122.5(4) yes
C1 C2 Cl1 . . 118.9(3) yes
C3 C2 Cl1 . . 118.5(3) yes
C4 C3 C2 . . 119.0(4) yes
C4 C3 H3 . . 120.5 no
C2 C3 H3 . . 120.5 no
C3 C4 C5 . . 120.2(4) yes
C3 C4 H4 . . 119.9 no
C5 C4 H4 . . 119.9 no
N1 C5 C6 . . 121.1(3) yes
N1 C5 C4 . . 118.9(4) yes
C6 C5 C4 . . 120.0(4) yes
C5 C6 C1 . . 118.5(4) yes
C5 C6 C7 . . 121.2(3) yes
C1 C6 C7 . . 120.3(4) yes
C6 C7 C8 . . 114.8(4) yes
C6 C7 S1 . . 123.1(3) yes
C8 C7 S1 . . 122.1(3) yes
C10 C8 C9 . . 118.4(4) yes
C10 C8 C7 . . 121.1(4) yes
C9 C8 C7 . . 120.5(3) yes
N1 C9 C10 . 2_675 119.6(4) yes
N1 C9 C8 . . 120.2(4) yes
C10 C9 C8 2_675 . 120.2(3) yes
C8 C10 C9 . 2_675 121.4(4) yes
C8 C10 H10 . . 119.3 no
C9 C10 H10 2_675 . 119.3 no
N2 C11 H11A . . 109.5 no
N2 C11 H11B . . 109.5 no
H11A C11 H11B . . 109.5 no
N2 C11 H11C . . 109.5 no
H11A C11 H11C . . 109.5 no
H11B C11 H11C . . 109.5 no
C15 C11 H11D . . 109.5 no
C15 C11 H11E . . 109.5 no
H11D C11 H11E . . 109.5 no
C15 C11 H11F . . 109.5 no
H11D C11 H11F . . 109.5 no
H11E C11 H11F . . 109.5 no
N2 C12 H12A . . 109.5 no
N2 C12 H12B . . 109.5 no
H12A C12 H12B . . 109.5 no
N2 C12 H12C . . 109.5 no
H12A C12 H12C . . 109.5 no
H12B C12 H12C . . 109.5 no
N3 C12 H12D . . 109.5 no
N3 C12 H12E . . 109.5 no
H12D C12 H12E . . 109.5 no
N3 C12 H12F . . 109.5 no
H12D C12 H12F . . 109.5 no
H12E C12 H12F . . 109.5 no
C14 C13 H13A . . 109.5 no
C14 C13 H13B . . 109.5 no
H13A C13 H13B . . 109.5 no
C14 C13 H13C . . 109.5 no
H13A C13 H13C . . 109.5 no
H13B C13 H13C . . 109.5 no
N3 C13 H13D . . 109.5 no
N3 C13 H13E . . 109.5 no
H13D C13 H13E . . 109.5 no
N3 C13 H13F . . 109.5 no
H13D C13 H13F . . 109.5 no
H13E C13 H13F . . 109.5 no
C14 N2 C12 . . 122.8(7) no
C14 N2 C11 . . 113.6(6) no
C12 N2 C11 . . 123.5(5) no
O1 C14 N2 . . 119.8(7) no
O1 C14 C13 . . 127.5(7) no
N2 C14 C13 . . 112.6(7) no
C15 N3 C12 . . 123.8(9) no
C15 N3 C13 . . 109.5(8) no
C12 N3 C13 . . 126.6(7) no
O1 C15 N3 . . 118.0(10) no
O1 C15 C11 . . 135.3(10) no
N3 C15 C11 . . 106.2(9) no
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
Cl1 C2 . 1.752(4) yes
S1 C7 . 1.630(4) yes
O1 C15 . 1.191(11) yes
O1 C14 . 1.236(8) yes
N1 C5 . 1.352(5) yes
N1 C9 . 1.370(4) yes
N1 H1N . 0.8800 no
C1 C2 . 1.358(5) yes
C1 C6 . 1.418(5) yes
C1 H1 . 0.9500 no
C2 C3 . 1.390(6) yes
C3 C4 . 1.376(5) yes
C3 H3 . 0.9500 no
C4 C5 . 1.417(5) yes
C4 H4 . 0.9500 no
C5 C6 . 1.402(6) yes
C6 C7 . 1.459(5) yes
C7 C8 . 1.475(5) yes
C8 C10 . 1.389(5) yes
C8 C9 . 1.417(6) yes
C9 C10 2_675 1.392(5) yes
C10 H10 . 0.9500 no
C11 N2 . 1.527(7) no
C11 C15 . 1.568(12) no
C11 H11A . 0.9800 no
C11 H11B . 0.9800 no
C11 H11C . 0.9800 no
C11 H11D . 0.9800 no
C11 H11E . 0.9800 no
C11 H11F . 0.9800 no
C12 N3 . 1.485(10) no
C12 N2 . 1.487(7) no
C12 H12A . 0.9800 no
C12 H12B . 0.9800 no
C12 H12C . 0.9800 no
C12 H12D . 0.9800 no
C12 H12E . 0.9800 no
C12 H12F . 0.9800 no
C13 C14 . 1.539(8) no
C13 N3 . 1.554(10) no
C13 H13A . 0.9800 no
C13 H13B . 0.9800 no
C13 H13C . 0.9800 no
C13 H13D . 0.9800 no
C13 H13E . 0.9800 no
C13 H13F . 0.9800 no
N2 C14 . 1.309(12) no
N3 C15 . 1.376(18) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O1 0.88 1.90 2.774(4) 173
