#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/68/2016823.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_2016823
loop_
_publ_author_name
'Allouchi, Hassan'
'Bravic, Georges'
'Lahrahar, Nacer'
'Desvergne, Jean-Pierre'
'Bouas-Laurent, Henri'
_publ_section_title
;
 2,3-Diethoxy-9,10-anthraquinone
;
_journal_coeditor_code           DN3097
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o620
_journal_page_last               o622
_journal_paper_doi               10.1107/S0108270108034227
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H16 O4'
_chemical_formula_moiety         'C18 H16 O4'
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.30
_chemical_melting_point          445
_chemical_name_common            'synthesized at ISM'
_chemical_name_systematic
;
2,3-diethoxy-9,10-anthraquinone
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 117.8090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.8007(3)
_cell_length_b                   6.8163(2)
_cell_length_c                   13.9992(3)
_cell_measurement_reflns_used    2934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2
_cell_volume                     1502.42(6)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2003)
;
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       CCD
_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  0.015
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3353
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         4.18
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0486
_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)+(0.0912P)²+0.1475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                1376
_reflns_number_total             1835
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3097.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2016823
_cod_database_fobs_code          2016823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_type_symbol
_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
C C1 0.17213(10) 0.0000 0.44422(13) 0.0528(4) Uani d S 1
H H1 0.1137 0.0000 0.4191 0.063 Uiso calc SR 1
C C2 0.22587(10) 0.0000 0.55355(12) 0.0507(4) Uani d S 1
O O2 0.20059(7) 0.0000 0.63146(9) 0.0611(4) Uani d S 1
C C3 0.31442(10) 0.0000 0.59182(12) 0.0498(4) Uani d S 1
O O3 0.36107(7) 0.0000 0.70053(8) 0.0622(4) Uani d S 1
C C4 0.34706(10) 0.0000 0.51911(12) 0.0512(4) Uani d S 1
H H4 0.4055 0.0000 0.5442 0.061 Uiso calc SR 1
C C5 0.29888(13) 0.0000 0.13948(15) 0.0712(5) Uani d S 1
H H5 0.3572 0.0000 0.1635 0.085 Uiso calc SR 1
C C5a 0.29184(10) 0.0000 0.40798(12) 0.0479(4) Uani d S 1
C C6 0.24355(15) 0.0000 0.02997(15) 0.0794(6) Uani d S 1
H H6 0.2649 0.0000 -0.0193 0.095 Uiso calc SR 1
C C6a 0.20454(10) 0.0000 0.37048(12) 0.0494(4) Uani d S 1
C C7 0.15788(16) 0.0000 -0.00623(15) 0.0847(7) Uani d S 1
H H7 0.1209 0.0000 -0.0800 0.102 Uiso calc SR 1
C C8 0.12629(14) 0.0000 0.06676(15) 0.0798(6) Uani d S 1
H H8 0.0679 0.0000 0.0418 0.096 Uiso calc SR 1
C C9 0.14435(11) 0.0000 0.25381(13) 0.0573(4) Uani d S 1
O O9 0.06755(8) 0.0000 0.22070(10) 0.0790(5) Uani d S 1
C C9a 0.18047(11) 0.0000 0.17694(13) 0.0579(4) Uani d S 1
C C10 0.32791(10) 0.0000 0.33156(13) 0.0546(4) Uani d S 1
O O10 0.40435(8) 0.0000 0.36335(10) 0.0758(4) Uani d S 1
C C10a 0.26744(11) 0.0000 0.21405(12) 0.0550(4) Uani d S 1
C C21 0.11112(11) 0.0000 0.59751(14) 0.0616(5) Uani d S 1
H H21A 0.0846 -0.1156 0.5545 0.074 Uiso calc PR 0.50
H H21B 0.0846 0.1156 0.5545 0.074 Uiso calc PR 0.50
C C22 0.10190(13) 0.0000 0.69965(16) 0.0741(6) Uani d S 1
H H22A 0.0447 -0.0342 0.6825 0.111 Uiso calc PR 0.50
H H22B 0.1148 0.1282 0.7317 0.111 Uiso calc PR 0.50
H H22C 0.1404 -0.0940 0.7496 0.111 Uiso calc PR 0.50
C C31 0.45175(11) 0.0000 0.74686(13) 0.0670(5) Uani d S 1
H H31A 0.4712 0.1156 0.7245 0.080 Uiso calc PR 0.50
H H31B 0.4712 -0.1156 0.7245 0.080 Uiso calc PR 0.50
C C32 0.48472(13) 0.0000 0.86741(14) 0.0849(7) Uani d S 1
H H32A 0.5438 -0.0349 0.9024 0.127 Uiso calc PR 0.50
H H32B 0.4534 -0.0935 0.8861 0.127 Uiso calc PR 0.50
H H32C 0.4780 0.1284 0.8905 0.127 Uiso calc PR 0.50
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'
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
C2 C1 C6a 120.62(14)
C2 C1 H1 119.7
C6a C1 H1 119.7
O2 C2 C1 125.01(14)
O2 C2 C3 115.17(13)
C1 C2 C3 119.82(13)
C2 O2 C21 117.78(12)
O3 C3 C4 125.35(14)
O3 C3 C2 114.76(12)
C4 C3 C2 119.89(13)
C3 O3 C31 118.73(12)
C3 C4 C5a 119.87(14)
C3 C4 H4 120.1
C5a C4 H4 120.1
C6 C5 C10a 120.17(18)
C6 C5 H5 119.9
C10a C5 H5 119.9
C6a C5a C4 120.12(14)
C6a C5a C10 120.80(14)
C4 C5a C10 119.08(14)
C7 C6 C5 120.44(17)
C7 C6 H6 119.8
C5 C6 H6 119.8
C5a C6a C1 119.69(14)
C5a C6a C9 121.63(14)
C1 C6a C9 118.69(14)
C6 C7 C8 119.80(17)
C6 C7 H7 120.1
C8 C7 H7 120.1
C7 C8 C9a 120.8(2)
C7 C8 H8 119.6
C9a C8 H8 119.6
O9 C9 C6a 121.70(15)
O9 C9 C9a 120.65(15)
C6a C9 C9a 117.64(15)
C10a C9a C8 119.56(16)
C10a C9a C9 120.87(14)
C8 C9a C9 119.56(17)
O10 C10 C5a 121.49(14)
O10 C10 C10a 120.83(14)
C5a C10 C10a 117.68(14)
C9a C10a C5 119.19(15)
C9a C10a C10 121.37(13)
C5 C10a C10 119.44(16)
O2 C21 C22 106.26(14)
O2 C21 H21A 110.5
C22 C21 H21A 110.5
O2 C21 H21B 110.5
C22 C21 H21B 110.5
H21A C21 H21B 108.7
C21 C22 H22A 109.5
C21 C22 H22B 109.5
H22A C22 H22B 109.5
C21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
O3 C31 C32 105.97(14)
O3 C31 H31A 110.5
C32 C31 H31A 110.5
O3 C31 H31B 110.5
C32 C31 H31B 110.5
H31A C31 H31B 108.7
C31 C32 H32A 109.5
C31 C32 H32B 109.5
H32A C32 H32B 109.5
C31 C32 H32C 109.5
H32A C32 H32C 109.5
H32B C32 H32C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.375(2)
C1 C6a 1.398(2)
C1 H1 0.9300
C2 O2 1.3602(18)
C2 C3 1.408(2)
O2 C21 1.4339(19)
C3 O3 1.3515(18)
C3 C4 1.388(2)
O3 C31 1.432(2)
C4 C5a 1.400(2)
C4 H4 0.9300
C5 C6 1.382(3)
C5 C10a 1.396(2)
C5 H5 0.9300
C5a C6a 1.389(2)
C5a C10 1.482(2)
C6 C7 1.364(3)
C6 H6 0.9300
C6a C9 1.477(2)
C7 C8 1.377(3)
C7 H7 0.9300
C8 C9a 1.386(2)
C8 H8 0.9300
C9 O9 1.222(2)
C9 C9a 1.489(2)
C9a C10a 1.384(2)
C10 O10 1.2186(19)
C10 C10a 1.487(2)
C21 C22 1.513(2)
C21 H21A 0.9700
C21 H21B 0.9700
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C31 C32 1.506(2)
C31 H31A 0.9700
C31 H31B 0.9700
C32 H32A 0.9600
C32 H32B 0.9600
C32 H32C 0.9600
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
C6a C1 C2 O2 180.0
C6a C1 C2 C3 0.0
C1 C2 O2 C21 0.0
C3 C2 O2 C21 180.0
O2 C2 C3 O3 0.0
C1 C2 C3 O3 180.0
O2 C2 C3 C4 180.0
C1 C2 C3 C4 0.0
C4 C3 O3 C31 0.0
C2 C3 O3 C31 180.0
O3 C3 C4 C5a 180.0
C2 C3 C4 C5a 0.0
C3 C4 C5a C6a 0.0
C3 C4 C5a C10 180.0
C10a C5 C6 C7 0.0
C4 C5a C6a C1 0.0
C10 C5a C6a C1 180.0
C4 C5a C6a C9 180.0
C10 C5a C6a C9 0.0
C2 C1 C6a C5a 0.0
C2 C1 C6a C9 180.0
C5 C6 C7 C8 0.0
C6 C7 C8 C9a 0.0
C5a C6a C9 O9 180.0
C1 C6a C9 O9 0.0
C5a C6a C9 C9a 0.0
C1 C6a C9 C9a 180.0
C7 C8 C9a C10a 0.0
C7 C8 C9a C9 180.0
O9 C9 C9a C10a 180.0
C6a C9 C9a C10a 0.0
O9 C9 C9a C8 0.0
C6a C9 C9a C8 180.0
C6a C5a C10 O10 180.0
C4 C5a C10 O10 0.0
C6a C5a C10 C10a 0.0
C4 C5a C10 C10a 180.0
C8 C9a C10a C5 0.0
C9 C9a C10a C5 180.0
C8 C9a C10a C10 180.0
C9 C9a C10a C10 0.0
C6 C5 C10a C9a 0.0
C6 C5 C10a C10 180.0
O10 C10 C10a C9a 180.0
C5a C10 C10a C9a 0.0
O10 C10 C10a C5 0.0
C5a C10 C10a C5 180.0
C2 O2 C21 C22 180.0
C3 O3 C31 C32 180.0
