#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512728.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_4512728
loop_
_publ_author_name
'Tamboli, Majid I.'
'Bahadur, Vir'
'Gonnade, Rajesh G.'
'Shashidhar, Mysore S.'
_publ_section_title
;
 Cocrystallization of 2,3-Dihydroxynaphthalene with Itspara-,meta-,
 andortho-Ditoluates: Insight into Cocrystal Formation and Clues for the
 Construction of Supramolecular Assemblies Capable of Intermolecular Acyl
 Group Transfer Reactivity
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1226
_journal_paper_doi               10.1021/cg501620g
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C18 H14 O3'
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.8212(9)
_cell_length_b                   7.5692(6)
_cell_length_c                   30.657(2)
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    145(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.66
_cell_volume                     2743.1(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      145(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II 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  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10873
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs,(bruker 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         2404
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0931
_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)+(0.0594P)²+8.2840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1959
_refine_ls_wR_factor_ref         0.2074
_reflns_number_gt                1871
_reflns_number_total             2404
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501620g_si_002.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4512727--4512728.cif.
;
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               4512728
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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 0.6978(3) -0.0684(5) 0.37396(9) 0.0324(8) Uani 1 1 d .
H1 H 0.7616 -0.1171 0.3730 0.049 Uiso 1 1 calc R
O2 O 0.4892(2) 0.0740(4) 0.36698(8) 0.0236(7) Uani 1 1 d .
O3 O 0.6044(2) 0.2808(4) 0.39613(9) 0.0297(8) Uani 1 1 d .
C1 C 0.7221(3) -0.0661(6) 0.29585(14) 0.0236(10) Uani 1 1 d .
C2 C 0.6637(3) -0.0276(5) 0.33298(13) 0.0217(9) Uani 1 1 d .
C3 C 0.5568(3) 0.0577(6) 0.32942(13) 0.0220(9) Uani 1 1 d .
C4 C 0.5120(3) 0.1019(5) 0.29039(13) 0.0216(9) Uani 1 1 d .
H4 H 0.4409 0.1604 0.2892 0.026 Uiso 1 1 calc R
C5 C 0.5701(3) 0.0618(5) 0.25118(14) 0.0221(9) Uani 1 1 d .
C6 C 0.5239(4) 0.0998(6) 0.20956(14) 0.0265(10) Uani 1 1 d .
C7 C 0.5811(4) 0.0527(6) 0.17266(15) 0.0315(11) Uani 1 1 d .
C8 C 0.6858(4) -0.0360(7) 0.17538(15) 0.0337(12) Uani 1 1 d .
C9 C 0.7324(4) -0.0724(6) 0.21497(14) 0.0282(10) Uani 1 1 d .
H9 H 0.8035 -0.1305 0.2163 0.034 Uiso 1 1 calc R
C10 C 0.6765(3) -0.0252(5) 0.25427(13) 0.0215(9) Uani 1 1 d .
C11 C 0.5246(3) 0.1819(5) 0.39935(13) 0.0219(9) Uani 1 1 d .
C12 C 0.4522(3) 0.1649(5) 0.43872(13) 0.0201(9) Uani 1 1 d .
C13 C 0.4899(4) 0.2407(6) 0.47755(13) 0.0223(9) Uani 1 1 d .
C14 C 0.4278(4) 0.2252(5) 0.51605(14) 0.0224(10) Uani 1 1 d .
C15 C 0.3264(4) 0.1328(6) 0.51441(14) 0.0268(10) Uani 1 1 d .
C16 C 0.2880(4) 0.0578(7) 0.47586(15) 0.0316(11) Uani 1 1 d .
C17 C 0.3507(3) 0.0723(6) 0.43808(14) 0.0260(10) Uani 1 1 d .
H17 H 0.3247 0.0194 0.4118 0.031 Uiso 1 1 calc R
C18 C 0.4688(5) 0.3068(7) 0.55772(16) 0.0334(12) Uani 1 1 d .
H2 H 0.721(3) -0.054(6) 0.1485(14) 0.024(11) Uiso 1 1 d .
H5 H 0.795(4) -0.129(6) 0.2986(12) 0.024(11) Uiso 1 1 d .
H6 H 0.280(4) 0.117(6) 0.5411(14) 0.030(12) Uiso 1 1 d .
H7 H 0.553(4) 0.073(6) 0.1448(15) 0.034(13) Uiso 1 1 d .
H8 H 0.444(4) 0.168(6) 0.2077(14) 0.033(13) Uiso 1 1 d .
H10 H 0.472(5) 0.229(8) 0.5812(18) 0.058(17) Uiso 1 1 d .
H11 H 0.559(4) 0.285(7) 0.4799(15) 0.039(15) Uiso 1 1 d .
H12 H 0.549(7) 0.345(11) 0.556(2) 0.11(3) Uiso 1 1 d .
H14 H 0.417(6) 0.392(10) 0.567(2) 0.09(2) Uiso 1 1 d .
H16 H 0.217(4) 0.004(6) 0.4750(13) 0.028(12) Uiso 1 1 d .
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 O1 H1 109.5
C11 O2 C3 118.6(3)
C2 C1 C10 120.8(4)
C2 C1 H5 118(2)
C10 C1 H5 121(2)
O1 C2 C1 125.1(4)
O1 C2 C3 116.0(4)
C1 C2 C3 118.8(4)
C4 C3 O2 118.8(4)
C4 C3 C2 121.9(4)
O2 C3 C2 118.8(4)
C3 C4 C5 120.6(4)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 122.3(4)
C6 C5 C10 119.6(4)
C4 C5 C10 118.1(4)
C7 C6 C5 120.2(4)
C7 C6 H8 121(2)
C5 C6 H8 119(2)
C6 C7 C8 120.6(4)
C6 C7 H7 123(3)
C8 C7 H7 117(3)
C9 C8 C7 120.3(4)
C9 C8 H2 125(3)
C7 C8 H2 114(3)
C8 C9 C10 121.2(4)
C8 C9 H9 119.4
C10 C9 H9 119.4
C1 C10 C9 122.1(4)
C1 C10 C5 119.8(4)
C9 C10 C5 118.1(4)
O3 C11 O2 123.7(4)
O3 C11 C12 124.7(4)
O2 C11 C12 111.5(3)
C17 C12 C13 119.7(4)
C17 C12 C11 122.0(4)
C13 C12 C11 118.3(4)
C12 C13 C14 121.3(4)
C12 C13 H11 121(3)
C14 C13 H11 117(3)
C15 C14 C13 117.8(4)
C15 C14 C18 121.2(4)
C13 C14 C18 121.0(4)
C16 C15 C14 121.3(4)
C16 C15 H6 118(3)
C14 C15 H6 121(3)
C17 C16 C15 120.5(4)
C17 C16 H16 120(3)
C15 C16 H16 120(3)
C16 C17 C12 119.5(4)
C16 C17 H17 120.3
C12 C17 H17 120.3
C14 C18 H10 114(4)
C14 C18 H12 112(4)
H10 C18 H12 101(5)
C14 C18 H14 110(4)
H10 C18 H14 102(5)
H12 C18 H14 117(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.355(5)
O1 H1 0.8400
O2 C11 1.352(5)
O2 C3 1.407(5)
O3 C11 1.209(5)
C1 C2 1.362(6)
C1 C10 1.418(6)
C1 H5 0.99(4)
C2 C3 1.424(6)
C3 C4 1.351(6)
C4 C5 1.417(6)
C4 H4 0.9500
C5 C6 1.417(6)
C5 C10 1.423(6)
C6 C7 1.365(6)
C6 H8 1.08(5)
C7 C8 1.410(7)
C7 H7 0.93(4)
C8 C9 1.361(6)
C8 H2 0.93(4)
C9 C10 1.420(6)
C9 H9 0.9500
C11 C12 1.485(6)
C12 C17 1.390(6)
C12 C13 1.395(6)
C13 C14 1.395(6)
C13 H11 0.88(5)
C14 C15 1.388(6)
C14 C18 1.500(6)
C15 C16 1.388(6)
C15 H6 0.99(4)
C16 C17 1.380(6)
C16 H16 0.93(5)
C17 H17 0.9500
C18 H10 0.93(6)
C18 H12 1.00(8)
C18 H14 0.94(8)
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
C10 C1 C2 O1 176.9(4)
C10 C1 C2 C3 -1.2(6)
C11 O2 C3 C4 -120.6(4)
C11 O2 C3 C2 68.1(5)
O1 C2 C3 C4 -178.5(4)
C1 C2 C3 C4 -0.3(6)
O1 C2 C3 O2 -7.6(6)
C1 C2 C3 O2 170.7(4)
O2 C3 C4 C5 -170.0(4)
C2 C3 C4 C5 1.0(6)
C3 C4 C5 C6 177.5(4)
C3 C4 C5 C10 -0.2(6)
C4 C5 C6 C7 -177.5(4)
C10 C5 C6 C7 0.2(6)
C5 C6 C7 C8 0.8(7)
C6 C7 C8 C9 -1.5(7)
C7 C8 C9 C10 1.1(7)
C2 C1 C10 C9 -176.5(4)
C2 C1 C10 C5 1.8(6)
C8 C9 C10 C1 178.3(4)
C8 C9 C10 C5 -0.1(6)
C6 C5 C10 C1 -178.9(4)
C4 C5 C10 C1 -1.1(5)
C6 C5 C10 C9 -0.6(5)
C4 C5 C10 C9 177.2(4)
C3 O2 C11 O3 8.6(6)
C3 O2 C11 C12 -172.2(3)
O3 C11 C12 C17 168.7(4)
O2 C11 C12 C17 -10.5(5)
O3 C11 C12 C13 -13.1(6)
O2 C11 C12 C13 167.7(3)
C17 C12 C13 C14 0.1(6)
C11 C12 C13 C14 -178.1(4)
C12 C13 C14 C15 -0.5(6)
C12 C13 C14 C18 180.0(4)
C13 C14 C15 C16 0.2(6)
C18 C14 C15 C16 179.7(4)
C14 C15 C16 C17 0.5(7)
C15 C16 C17 C12 -0.9(7)
C13 C12 C17 C16 0.5(6)
C11 C12 C17 C16 178.7(4)
