#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:58:17 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180458 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/27/7212718.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_7212718
loop_
_publ_author_name
'Jacobs, Ayesha'
'Nassimbeni, Luigi R.'
'Ramon, Gaëlle'
'Sebogisi, Baganetsi K.'
_publ_section_title
;
 Inclusion compounds of hydroxynaphthoic acids: co-crystal vs. salt
 formation
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              3065
_journal_paper_doi               10.1039/c004458j
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         C11H8O3.0.5(C4H8O2)
_chemical_formula_sum            'C13 H8 O4'
_chemical_formula_weight         228.19
_chemical_name_systematic
;
6-hydroxy-2-naphthoic acid 1,4-dioxane solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 96.3190(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4451(4)
_cell_length_b                   5.9568(3)
_cell_length_c                   24.7267(13)
_cell_measurement_reflns_used    'All data'
_cell_measurement_temperature    173(2)
_cell_volume                     1089.94(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9402
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1179P)²+0.3795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1781
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                2229
_reflns_number_total             2692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c004458j.txt
_cod_data_source_block           c:\H1DIOX
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7212718
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 0.4514(2) 0.4064(2) 0.06760(5) 0.0412(4) Uani 1 1 d .
C1 C 0.46189(19) 0.5827(3) 0.17063(6) 0.0246(3) Uani 1 1 d .
H1 H 0.4093 0.4391 0.1633 0.030 Uiso 1 1 calc R
H11 H 0.446(4) 0.376(6) 0.0337(13) 0.076(9) Uiso 1 1 d .
O2 O 0.57038(19) 0.7174(2) 0.03591(5) 0.0405(4) Uani 1 1 d .
C2 C 0.52872(19) 0.7013(3) 0.12943(6) 0.0260(3) Uani 1 1 d .
O3 O 0.50691(19) 0.9499(2) 0.37910(5) 0.0385(3) Uani 1 1 d .
C3 C 0.6058(2) 0.9171(3) 0.13997(6) 0.0284(4) Uani 1 1 d .
H3 H 0.6509 0.9992 0.1114 0.034 Uiso 1 1 calc R
C4 C 0.6155(2) 1.0070(3) 0.19093(6) 0.0270(3) Uani 1 1 d .
H4 H 0.6674 1.1515 0.1974 0.032 Uiso 1 1 calc R
C5 C 0.55946(19) 0.9781(3) 0.28767(6) 0.0254(3) Uani 1 1 d .
H5 H 0.6115 1.1220 0.2951 0.031 Uiso 1 1 calc R
C6 C 0.4942(2) 0.8576(3) 0.32867(6) 0.0275(3) Uani 1 1 d .
C7 C 0.4152(2) 0.6430(3) 0.31812(6) 0.0287(4) Uani 1 1 d .
H7 H 0.3695 0.5615 0.3467 0.034 Uiso 1 1 calc R
C8 C 0.40469(19) 0.5531(3) 0.26688(6) 0.0253(3) Uani 1 1 d .
H8 H 0.3523 0.4089 0.2602 0.030 Uiso 1 1 calc R
C9 C 0.47080(18) 0.6724(3) 0.22375(6) 0.0227(3) Uani 1 1 d .
C10 C 0.54923(18) 0.8885(2) 0.23447(6) 0.0228(3) Uani 1 1 d .
C11 C 0.5201(2) 0.6088(3) 0.07376(6) 0.0294(4) Uani 1 1 d .
H12 H 0.473(4) 0.864(5) 0.3987(11) 0.058(8) Uiso 1 1 d .
O1G O 0.44893(19) 0.6679(2) 0.46194(6) 0.0458(4) Uani 1 1 d .
C2G C 0.3598(5) 0.4568(5) 0.46183(13) 0.0956(14) Uani 1 1 d .
C3G C 0.5436(5) 0.7203(6) 0.51657(15) 0.0358(7) Uani 0.50 1 d P
C4G C 0.6301(5) 0.6624(7) 0.49185(15) 0.0424(9) Uani 0.50 1 d P
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C9 120.64(14) . .
C1 C2 C3 120.04(14) . .
C1 C2 C11 121.03(14) . .
C3 C2 C11 118.93(14) . .
C4 C3 C2 120.28(14) . .
C3 C4 C10 121.17(14) . .
C6 C5 C10 120.12(14) . .
O3 C6 C5 118.15(15) . .
O3 C6 C7 121.31(15) . .
C5 C6 C7 120.54(14) . .
C8 C7 C6 120.17(14) . .
C7 C8 C9 120.79(14) . .
C1 C9 C8 121.77(14) . .
C1 C9 C10 119.38(13) . .
C8 C9 C10 118.85(13) . .
C5 C10 C4 121.98(14) . .
C5 C10 C9 119.53(13) . .
C4 C10 C9 118.49(13) . .
O2 C11 O1 122.85(15) . .
O2 C11 C2 121.84(15) . .
O1 C11 C2 115.29(14) . .
C2G O1G C4G 112.6(2) . .
C2G O1G C3G 111.2(2) . .
C4G O1G C3G 39.5(2) . .
C4G C2G C3G 43.4(2) 3_666 3_666
C4G C2G O1G 118.9(3) 3_666 .
C3G C2G O1G 117.5(3) 3_666 .
C4G C3G C2G 67.7(4) . 3_666
C4G C3G O1G 69.1(3) . .
C2G C3G O1G 111.9(3) 3_666 .
C3G C4G C2G 68.9(4) . 3_666
C3G C4G O1G 71.4(3) . .
C2G C4G O1G 113.8(3) 3_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.312(2) .
C1 C2 1.377(2) .
C1 C9 1.413(2) .
O2 C11 1.229(2) .
C2 C3 1.420(2) .
C2 C11 1.478(2) .
O3 C6 1.3569(19) .
C3 C4 1.364(2) .
C4 C10 1.421(2) .
C5 C6 1.374(2) .
C5 C10 1.414(2) .
C6 C7 1.419(2) .
C7 C8 1.370(2) .
C8 C9 1.414(2) .
C9 C10 1.426(2) .
O1G C2G 1.421(3) .
O1G C4G 1.466(4) .
O1G C3G 1.487(4) .
C2G C4G 1.343(4) 3_666
C2G C3G 1.353(5) 3_666
C3G C4G 0.997(5) .
C3G C2G 1.353(5) 3_666
C4G C2G 1.343(4) 3_666
