#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/98/2219807.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_2219807
loop_
_publ_author_name
'Ismail, Nor Hadiani'
'Osman, Che Puteh'
'Awang, Khalijah'
'Abdul Malek, Sri Nurestri'
'Ng, Seik Weng'
_publ_section_title
;
 2-Formyl-3-hydroxy-9,10-anthroquinone
;
_journal_coeditor_code           CI2681
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2164
_journal_paper_doi               10.1107/S1600536808032224
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H8 O4'
_chemical_formula_moiety         'C15 H8 O4'
_chemical_formula_sum            'C15 H8 O4'
_chemical_formula_weight         252.21
_chemical_name_systematic
;
2-Formyl-3-hydroxy-9,10-anthroquinone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.250(2)
_cell_angle_beta                 83.214(2)
_cell_angle_gamma                64.692(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9194(2)
_cell_length_b                   8.0650(2)
_cell_length_c                   10.7601(3)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      3.3
_cell_volume                     538.96(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker SMART APEXII area-detector'
_diffrn_measurement_method       ω
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0399
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4946
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.443
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0868
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1778P)²+2.2381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3327
_refine_ls_wR_factor_ref         0.3433
_reflns_number_gt                1880
_reflns_number_total             2419
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2681.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2219807
_cod_database_fobs_code          2219807
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O O1 0.3155(6) 0.6486(5) 0.0888(3) 0.0251(8) Uani d . 1
O O2 0.2501(6) 0.3493(5) 0.0941(3) 0.0242(8) Uani d . 1
H H2 0.2611 0.4345 0.0490 0.029 Uiso calc R 1
O O3 0.2366(5) -0.0898(4) 0.4383(3) 0.0153(7) Uani d . 1
O O4 0.2779(5) 0.4648(4) 0.6688(3) 0.0172(7) Uani d . 1
C C1 0.3060(7) 0.6395(6) 0.2041(4) 0.0178(9) Uani d . 1
H H1 0.3171 0.7336 0.2474 0.021 Uiso calc R 1
C C2 0.2786(7) 0.4901(6) 0.2772(4) 0.0143(9) Uani d . 1
C C3 0.2544(7) 0.3500(6) 0.2187(4) 0.0161(9) Uani d . 1
C C4 0.2356(7) 0.2059(6) 0.2894(4) 0.0152(9) Uani d . 1
H H4 0.2187 0.1116 0.2500 0.018 Uiso calc R 1
C C5 0.2419(6) 0.2016(5) 0.4183(4) 0.0123(8) Uani d . 1
C C6 0.2335(6) 0.0406(5) 0.4916(4) 0.0112(8) Uani d . 1
C C7 0.2285(6) 0.0417(5) 0.6299(4) 0.0112(8) Uani d . 1
C C8 0.2117(7) -0.1043(6) 0.7003(4) 0.0139(8) Uani d . 1
H H8 0.1986 -0.1999 0.6601 0.017 Uiso calc R 1
C C9 0.2144(7) -0.1091(6) 0.8286(4) 0.0179(9) Uani d . 1
H H9 0.2031 -0.2083 0.8766 0.021 Uiso calc R 1
C C10 0.2336(7) 0.0310(6) 0.8883(4) 0.0188(9) Uani d . 1
H H10 0.2353 0.0269 0.9767 0.023 Uiso calc R 1
C C11 0.2503(7) 0.1762(6) 0.8187(4) 0.0173(9) Uani d . 1
H H11 0.2645 0.2709 0.8594 0.021 Uiso calc R 1
C C12 0.2462(6) 0.1835(5) 0.6895(4) 0.0113(8) Uani d . 1
C C13 0.2641(6) 0.3403(6) 0.6165(4) 0.0126(8) Uani d . 1
C C14 0.2621(6) 0.3426(5) 0.4787(4) 0.0120(8) Uani d . 1
C C15 0.2815(7) 0.4851(6) 0.4072(4) 0.0133(8) Uani d . 1
H H15 0.2968 0.5801 0.4468 0.016 Uiso calc R 1
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
C3 O2 H2 120.0
O1 C1 C2 122.8(4)
O1 C1 H1 118.6
C2 C1 H1 118.6
C15 C2 C3 119.7(4)
C15 C2 C1 119.1(4)
C3 C2 C1 121.2(4)
O2 C3 C4 117.9(4)
O2 C3 C2 121.8(4)
C4 C3 C2 120.3(4)
C5 C4 C3 119.2(4)
C5 C4 H4 120.4
C3 C4 H4 120.4
C4 C5 C14 121.2(4)
C4 C5 C6 118.4(4)
C14 C5 C6 120.3(4)
O3 C6 C7 121.3(4)
O3 C6 C5 120.5(4)
C7 C6 C5 118.1(3)
C8 C7 C12 120.1(4)
C8 C7 C6 118.9(4)
C12 C7 C6 121.0(3)
C9 C8 C7 119.7(4)
C9 C8 H8 120.1
C7 C8 H8 120.1
C8 C9 C10 120.4(4)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 120.0(4)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.2(4)
C10 C11 H11 119.9
C12 C11 H11 119.9
C11 C12 C7 119.6(4)
C11 C12 C13 119.4(4)
C7 C12 C13 121.1(3)
O4 C13 C14 121.0(4)
O4 C13 C12 121.0(4)
C14 C13 C12 118.0(3)
C15 C14 C5 119.0(4)
C15 C14 C13 119.7(4)
C5 C14 C13 121.3(4)
C14 C15 C2 120.5(4)
C14 C15 H15 119.8
C2 C15 H15 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.234(5)
O2 C3 1.345(5)
O2 H2 0.84
O3 C6 1.222(5)
O4 C13 1.226(5)
C1 C2 1.464(6)
C1 H1 0.95
C2 C15 1.400(6)
C2 C3 1.407(6)
C3 C4 1.391(6)
C4 C5 1.390(6)
C4 H4 0.95
C5 C14 1.410(6)
C5 C6 1.494(5)
C6 C7 1.485(5)
C7 C8 1.398(5)
C7 C12 1.403(5)
C8 C9 1.380(6)
C8 H8 0.95
C9 C10 1.397(6)
C9 H9 0.95
C10 C11 1.388(6)
C10 H10 0.95
C11 C12 1.391(6)
C11 H11 0.95
C12 C13 1.487(5)
C13 C14 1.483(6)
C14 C15 1.387(6)
C15 H15 0.95
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
_geom_hbond_publ_flag
O2 H2 O1 0.84 2.00 2.635(5) 132 yes
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
O1 C1 C2 C15 176.5(4)
O1 C1 C2 C3 -2.1(7)
C15 C2 C3 O2 179.8(4)
C1 C2 C3 O2 -1.7(7)
C15 C2 C3 C4 -0.7(7)
C1 C2 C3 C4 177.9(4)
O2 C3 C4 C5 179.3(4)
C2 C3 C4 C5 -0.3(7)
C3 C4 C5 C14 1.4(6)
C3 C4 C5 C6 -176.7(4)
C4 C5 C6 O3 5.1(6)
C14 C5 C6 O3 -173.0(4)
C4 C5 C6 C7 -176.8(4)
C14 C5 C6 C7 5.1(6)
O3 C6 C7 C8 -4.6(6)
C5 C6 C7 C8 177.4(4)
O3 C6 C7 C12 173.7(4)
C5 C6 C7 C12 -4.4(6)
C12 C7 C8 C9 -0.5(6)
C6 C7 C8 C9 177.7(4)
C7 C8 C9 C10 0.0(7)
C8 C9 C10 C11 0.0(7)
C9 C10 C11 C12 0.5(7)
C10 C11 C12 C7 -1.0(6)
C10 C11 C12 C13 180.0(4)
C8 C7 C12 C11 1.0(6)
C6 C7 C12 C11 -177.2(4)
C8 C7 C12 C13 -180.0(3)
C6 C7 C12 C13 1.8(6)
C11 C12 C13 O4 -1.5(6)
C7 C12 C13 O4 179.4(4)
C11 C12 C13 C14 179.2(4)
C7 C12 C13 C14 0.2(6)
C4 C5 C14 C15 -1.6(6)
C6 C5 C14 C15 176.4(3)
C4 C5 C14 C13 178.7(4)
C6 C5 C14 C13 -3.2(6)
O4 C13 C14 C15 1.6(6)
C12 C13 C14 C15 -179.1(4)
O4 C13 C14 C5 -178.7(4)
C12 C13 C14 C5 0.6(6)
C5 C14 C15 C2 0.7(6)
C13 C14 C15 C2 -179.6(4)
C3 C2 C15 C14 0.4(6)
C1 C2 C15 C14 -178.1(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8374399
