#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/38/4503807.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_4503807
loop_
_publ_author_name
'Rohl, Andrew L.'
'Moret, Massimo'
'Kaminsky, Werner'
'Claborn, Kacey'
'McKinnon, Joshua J.'
'Kahr, Bart'
_publ_section_title
;
 Hirshfeld Surfaces Identify Inadequacies in Computations of
 Intermolecular Interactions in Crystals: Pentamorphic
 1,8-Dihydroxyanthraquinone
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4517
_journal_paper_doi               10.1021/cg8005212
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C14 H8 O4'
_chemical_formula_sum            'C14 H8 O4'
_chemical_formula_weight         240.20
_chemical_name_common            dihyanthraquin_P21/n_LT
_chemical_name_systematic        dihyanthraquin_P21/n_LT
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.634(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2930(5)
_cell_length_b                   9.5001(7)
_cell_length_c                   14.7208(11)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     1019.50(13)
_computing_cell_refinement       SAINT
_computing_data_collection       'Bruker Smart CCD'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON, SCHAKAL99'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      110(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8737
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1294P)²+0.2359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1826
_reflns_number_gt                1422
_reflns_number_total             1800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg8005212_si_005.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4503807
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.2280(2) 0.15965(15) 0.14323(9) 0.0231(4) Uani 1 1 d .
O2 O 0.2965(2) -0.18781(17) -0.14358(9) 0.0279(5) Uani 1 1 d .
O3 O 0.1155(2) -0.04631(16) 0.24121(10) 0.0292(5) Uani 1 1 d .
H3 H 0.1621 0.0333 0.2325 0.044 Uiso 1 1 calc R
O4 O 0.3462(2) 0.36956(15) 0.04839(10) 0.0296(5) Uani 1 1 d .
H4 H 0.3143 0.3278 0.0957 0.044 Uiso 1 1 calc R
C1 C 0.2724(3) -0.1073(2) -0.07985(13) 0.0185(5) Uani 1 1 d .
C2 C 0.2001(2) -0.1595(2) 0.00713(12) 0.0164(5) Uani 1 1 d .
C3 C 0.1865(3) -0.0682(2) 0.08244(13) 0.0157(5) Uani 1 1 d .
C4 C 0.2392(3) 0.0807(2) 0.07546(13) 0.0165(5) Uani 1 1 d .
C5 C 0.3038(2) 0.1348(2) -0.01066(13) 0.0172(5) Uani 1 1 d .
C6 C 0.3168(2) 0.0453(2) -0.08753(13) 0.0179(5) Uani 1 1 d .
C7 C 0.1234(3) -0.1228(2) 0.16498(13) 0.0173(5) Uani 1 1 d .
C8 C 0.0683(3) -0.2638(2) 0.16988(13) 0.0204(5) Uani 1 1 d .
H8 H 0.0207 -0.2996 0.2246 0.025 Uiso 1 1 calc R
C9 C 0.0831(3) -0.3502(2) 0.09578(14) 0.0225(5) Uani 1 1 d .
H9 H 0.0467 -0.4459 0.1000 0.027 Uiso 1 1 calc R
C10 C 0.1507(3) -0.2997(2) 0.01453(14) 0.0202(5) Uani 1 1 d .
H10 H 0.1630 -0.3614 -0.0358 0.024 Uiso 1 1 calc R
C11 C 0.3521(3) 0.2780(2) -0.01990(14) 0.0203(5) Uani 1 1 d .
C12 C 0.4096(3) 0.3283(2) -0.10365(14) 0.0245(5) Uani 1 1 d .
H12 H 0.4425 0.4245 -0.1098 0.029 Uiso 1 1 calc R
C13 C 0.4189(3) 0.2399(3) -0.17692(14) 0.0257(6) Uani 1 1 d .
H13 H 0.4572 0.2757 -0.2336 0.031 Uiso 1 1 calc R
C14 C 0.3729(3) 0.0981(2) -0.16941(13) 0.0218(5) Uani 1 1 d .
H14 H 0.3801 0.0379 -0.2207 0.026 Uiso 1 1 calc R
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 0 1.8160
-1 0 -1 1.6260
-1 0 1 1.5900
0 -1 -1 1.3160
0 0 -1 1.4280
0 0 1 1.4280
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O3 H3 109.5
C11 O4 H4 109.5
O2 C1 C2 120.92(19)
O2 C1 C6 120.81(18)
C2 C1 C6 118.27(17)
C10 C2 C3 120.30(18)
C10 C2 C1 119.25(18)
C3 C2 C1 120.43(18)
C7 C3 C2 118.83(18)
C7 C3 C4 120.41(18)
C2 C3 C4 120.75(18)
O1 C4 C5 120.75(18)
O1 C4 C3 119.82(18)
C5 C4 C3 119.42(18)
C11 C5 C6 118.50(18)
C11 C5 C4 120.70(19)
C6 C5 C4 120.79(18)
C14 C6 C5 120.43(19)
C14 C6 C1 119.41(18)
C5 C6 C1 120.15(18)
O3 C7 C8 117.14(17)
O3 C7 C3 123.05(18)
C8 C7 C3 119.79(18)
C9 C8 C7 120.14(18)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 121.00(19)
C8 C9 H9 119.5
C10 C9 H9 119.5
C2 C10 C9 119.86(19)
C2 C10 H10 120.1
C9 C10 H10 120.1
O4 C11 C12 117.41(18)
O4 C11 C5 122.88(18)
C12 C11 C5 119.7(2)
C13 C12 C11 120.5(2)
C13 C12 H12 119.7
C11 C12 H12 119.7
C12 C13 C14 120.82(19)
C12 C13 H13 119.6
C14 C13 H13 119.6
C6 C14 C13 120.0(2)
C6 C14 H14 120.0
C13 C14 H14 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.252(2)
O2 C1 1.227(2)
O3 C7 1.339(2)
O3 H3 0.8400
O4 C11 1.331(2)
O4 H4 0.8400
C1 C2 1.484(3)
C1 C6 1.490(3)
C2 C10 1.385(3)
C2 C3 1.413(3)
C3 C7 1.410(3)
C3 C4 1.470(3)
C4 C5 1.459(3)
C5 C11 1.413(3)
C5 C6 1.421(3)
C6 C14 1.379(3)
C7 C8 1.401(3)
C8 C9 1.372(3)
C8 H8 0.9500
C9 C10 1.392(3)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.397(3)
C12 C13 1.370(3)
C12 H12 0.9500
C13 C14 1.393(3)
C13 H13 0.9500
C14 H14 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2845
2 PubChem 2950
