#------------------------------------------------------------------------------
#$Date: 2017-10-13 13:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201982 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/38/4503803.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_4503803
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_absolute_configuration unk
_chemical_formula_moiety         'C14 H8 O4'
_chemical_formula_sum            'C14 H8 O4'
_chemical_formula_weight         240.20
_chemical_name_common            dihyanthraquin_P41_LT
_chemical_name_systematic        dihyanthraquin_P41_LT
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7230(3)
_cell_length_b                   5.7230(3)
_cell_length_c                   30.923(2)
_cell_measurement_reflns_used    70
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_volume                     1012.81(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        DENZO
_computing_molecular_graphics    'maXus, Zortep'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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     0.71070
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            1370
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         4.43
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   HKL2000
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.064
_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     163
_refine_ls_number_reflns         1370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0676
_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)+(0.1076P)²+0.3522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1799
_reflns_number_gt                1000
_reflns_number_total             1370
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg8005212_si_001.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_cell_volume        1012.81(11)
_cod_database_code               4503803
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
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_calc_flag
_atom_site_refinement_flags
C1 C 0.8785(9) -0.3439(10) 0.2609(2) 0.0268(13) Uani 1 d .
C2 C 0.9097(9) -0.1654(10) 0.2277(2) 0.0248(12) Uani 1 d .
C3 C 1.0979(10) -0.1745(9) 0.1987(2) 0.0281(13) Uani 1 d .
C4 C 1.1177(10) -0.0021(10) 0.1668(2) 0.0328(14) Uani 1 d .
H4 H 1.2475 -0.0055 0.1476 0.039 Uiso 1 calc R
C5 C 0.9540(10) 0.1718(10) 0.1625(2) 0.0337(14) Uani 1 d .
H5 H 0.9679 0.2838 0.1399 0.040 Uiso 1 calc R
C6 C 0.7619(10) 0.1835(10) 0.1922(2) 0.0366(16) Uani 1 d .
H6 H 0.6501 0.3057 0.1901 0.044 Uiso 1 calc R
C7 C 0.7415(10) 0.0141(11) 0.2240(2) 0.0322(13) Uani 1 d .
C8 C 0.5451(9) 0.0361(9) 0.2549(2) 0.0283(14) Uani 1 d .
C9 C 0.5247(10) -0.1421(10) 0.2900(2) 0.0308(13) Uani 1 d .
C10 C 0.3460(11) -0.1322(12) 0.3199(2) 0.0386(16) Uani 1 d .
H10 H 0.2369 -0.0073 0.3188 0.046 Uiso 1 calc R
C11 C 0.3241(10) -0.3033(11) 0.3515(2) 0.0332(15) Uani 1 d .
H11 H 0.2025 -0.2915 0.3723 0.040 Uiso 1 calc R
C12 C 0.4777(11) -0.4918(11) 0.3531(3) 0.0372(15) Uani 1 d .
H12 H 0.4571 -0.6119 0.3740 0.045 Uiso 1 calc R
C13 C 0.6613(11) -0.5019(10) 0.3239(2) 0.0314(15) Uani 1 d .
C14 C 0.6858(11) -0.3294(9) 0.2919(2) 0.0283(13) Uani 1 d .
O1 O 1.0234(7) -0.5066(7) 0.2631(5) 0.0343(10) Uani 1 d .
O2 O 0.4057(7) 0.1998(7) 0.25303(18) 0.0391(12) Uani 1 d .
O3 O 1.2660(7) -0.3391(8) 0.2010(5) 0.0368(11) Uani 1 d .
H3 H 1.2503 -0.4160 0.2240 0.055 Uiso 1 calc R
O4 O 0.8072(7) -0.6820(7) 0.32768(18) 0.0360(11) Uani 1 d .
H4A H 0.9121 -0.6719 0.3088 0.054 Uiso 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.018(3) 0.041(4) 0.021(3) -0.005(3) -0.004(2) 0.007(2)
C2 0.021(3) 0.030(3) 0.024(3) -0.007(2) -0.005(2) -0.009(2)
C3 0.029(3) 0.026(3) 0.030(3) -0.010(3) -0.006(3) -0.004(3)
C4 0.027(3) 0.039(4) 0.032(3) 0.002(3) 0.002(3) -0.008(3)
C5 0.028(3) 0.045(4) 0.029(3) 0.001(3) -0.001(3) -0.006(3)
C6 0.027(3) 0.029(3) 0.054(5) 0.002(3) -0.005(3) 0.003(3)
C7 0.030(3) 0.041(4) 0.025(3) -0.007(3) -0.001(3) -0.005(3)
C8 0.025(3) 0.020(3) 0.040(4) -0.002(3) -0.010(3) 0.001(2)
C9 0.030(3) 0.034(3) 0.029(3) 0.003(3) -0.009(3) -0.002(3)
C10 0.030(3) 0.050(4) 0.036(4) -0.007(3) -0.006(3) -0.003(3)
C11 0.028(3) 0.037(4) 0.035(4) -0.014(3) 0.004(3) -0.005(3)
C12 0.051(4) 0.029(3) 0.032(4) -0.009(3) -0.003(3) -0.011(3)
C13 0.047(4) 0.024(3) 0.023(3) 0.000(3) -0.010(3) -0.008(3)
C14 0.038(3) 0.022(3) 0.026(3) -0.004(2) -0.004(3) -0.008(2)
O1 0.034(2) 0.035(2) 0.034(2) 0.0017(19) -0.0026(19) 0.0063(18)
O2 0.037(2) 0.035(2) 0.046(3) -0.003(2) -0.010(2) 0.014(2)
O3 0.029(2) 0.047(3) 0.035(2) -0.008(2) 0.0044(19) 0.008(2)
O4 0.042(3) 0.028(2) 0.039(3) 0.003(2) -0.010(2) 0.0048(19)
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 0 -1 2.1870
0 0 -1 0.3740
0 0 1 0.5400
0 -1 -1 2.1870
1 0 -1 2.1870
0 1 -1 2.1870
-1 -1 -1 3.1500
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 118.7(5)
O1 C1 C14 120.4(5)
C2 C1 C14 120.9(4)
C3 C2 C7 120.0(6)
C3 C2 C1 121.1(5)
C7 C2 C1 118.9(5)
O3 C3 C4 118.1(5)
O3 C3 C2 122.8(5)
C4 C3 C2 119.1(6)
C5 C4 C3 121.5(5)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 119.6(6)
C4 C5 H5 120.2
C6 C5 H5 120.2
C7 C6 C5 119.2(5)
C7 C6 H6 120.4
C5 C6 H6 120.4
C6 C7 C2 120.5(6)
C6 C7 C8 117.5(5)
C2 C7 C8 121.8(5)
O2 C8 C7 121.8(6)
O2 C8 C9 120.2(6)
C7 C8 C9 118.0(5)
C10 C9 C14 119.1(6)
C10 C9 C8 121.1(5)
C14 C9 C8 119.8(5)
C9 C10 C11 120.6(6)
C9 C10 H10 119.7
C11 C10 H10 119.7
C10 C11 C12 120.9(6)
C10 C11 H11 119.5
C12 C11 H11 119.5
C13 C12 C11 119.1(6)
C13 C12 H12 120.4
C11 C12 H12 120.4
O4 C13 C12 116.7(5)
O4 C13 C14 123.0(5)
C12 C13 C14 120.3(6)
C13 C14 C9 119.8(5)
C13 C14 C1 119.8(5)
C9 C14 C1 120.4(5)
C3 O3 H3 109.5
C13 O4 H4A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.249(6)
C1 C2 1.458(8)
C1 C14 1.465(8)
C2 C3 1.402(8)
C2 C7 1.412(7)
C3 O3 1.348(7)
C3 C4 1.402(8)
C4 C5 1.373(8)
C4 H4 0.9500
C5 C6 1.435(9)
C5 H5 0.9500
C6 C7 1.386(9)
C6 H6 0.9500
C7 C8 1.480(9)
C8 O2 1.232(6)
C8 C9 1.494(8)
C9 C10 1.379(8)
C9 C14 1.415(8)
C10 C11 1.390(9)
C10 H10 0.9500
C11 C12 1.393(9)
C11 H11 0.9500
C12 C13 1.388(9)
C12 H12 0.9500
C13 O4 1.331(7)
C13 C14 1.404(8)
O3 H3 0.8400
O4 H4A 0.8400
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2845
