#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/20/47/7204767.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_7204767
loop_
_publ_author_name
'Alshahateet, Solhe F.'
'Nakano, Kazunori'
'Bishop, Roger'
'Craig, Donald C.'
'Harris, Kenneth D. M.'
'Scudder, Marcia L.'
_publ_section_title
;
 Co-crystalline hydrogen bonded solids based on the alcohol?carboxylic
 acid?alcohol supramolecular motif
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              5
_journal_paper_doi               10.1039/b313956e
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         'C13 H22 O2, C7 H6 O2'
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.4
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_type_scat_source
'International Tables for X-ray Crystallography, Vol. IV'
_audit_creation_method           'RAELSPUB and manual entry'
_cell_angle_alpha                90
_cell_angle_beta                 94.96(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.596(5)
_cell_length_b                   9.766(4)
_cell_length_c                   35.351(11)
_cell_measurement_reflns_used    10
_cell_measurement_temperature    294
_cell_measurement_theta_max      22
_cell_measurement_theta_min      19
_cell_volume                     3644(3)
_computing_cell_refinement       'CAD4 Version 5.0, 1989'
_computing_data_collection       'CAD4 Version 5.0, 1989'
_computing_data_reduction        'Local program'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'
_computing_structure_refinement  'RAELS, (Rae, 1989)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3165
_diffrn_reflns_theta_max         65
_diffrn_standards_decay_%        14
_diffrn_standards_interval_time  30min
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.21
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1440.0
_exptl_crystal_size_rad          0.1
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.26
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1621
_refine_ls_R_factor_gt           0.098
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.159
_reflns_number_gt                1621
_reflns_number_total             3119
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b313956e.txt
_cod_data_source_block           DRB208
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7204767
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x,-y,1/2+z
3 -x,-y,-z
4 -x,y,1/2-z
5 1/2+x,1/2+y,z
6 1/2+x,1/2-y,1/2+z
7 1/2-x,1/2-y,-z
8 1/2-x,1/2+y,1/2-z
loop_
_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_type_symbol
_atom_site_occupancy
O1 0.1950(3) 0.1489(4) 0.6357(1) 0.0688(9) Uani O 1.0
O2 0.4520(4) 0.6182(4) 0.6512(1) 0.073(1) Uani O 1.0
C1 0.3347(6) 0.3618(7) 0.7190(2) 0.073(1) Uani C 1.0
C2 0.2312(5) 0.2990(6) 0.6915(2) 0.065(1) Uani C 1.0
C3 0.2892(5) 0.1949(6) 0.6655(2) 0.0619(9) Uani C 1.0
C4 0.3995(5) 0.2560(6) 0.6444(2) 0.065(1) Uani C 1.0
C5 0.4902(5) 0.3358(6) 0.6724(2) 0.068(1) Uani C 1.0
C6 0.4274(5) 0.4413(6) 0.6967(2) 0.0647(9) Uani C 1.0
C7 0.3610(5) 0.5608(6) 0.6748(2) 0.0644(9) Uani C 1.0
C8 0.2411(5) 0.5130(6) 0.6493(2) 0.0679(9) Uani C 1.0
C9 0.1589(5) 0.4173(6) 0.6713(2) 0.070(1) Uani C 1.0
C10 0.3322(6) 0.0688(7) 0.6884(2) 0.080(2) Uani C 1.0
C11 0.3241(6) 0.6694(7) 0.7026(2) 0.083(2) Uani C 1.0
C12 0.3613(6) 0.3384(7) 0.6091(2) 0.074(1) Uani C 1.0
C13 0.2644(6) 0.4580(7) 0.6104(2) 0.077(1) Uani C 1.0
O1Ba 0.1572(6) 0.6562(5) 0.3871(2) 0.103(2) Uani O 1.0
O2Ba 0.2402(5) 0.4894(5) 0.4243(1) 0.090(2) Uani O 1.0
C1Ba 0.1172(5) 0.6563(5) 0.4525(2) 0.072(2) Uani C 1.0
C2Ba 0.0316(6) 0.7609(7) 0.4486(2) 0.097(2) Uani C 1.0
C3Ba -0.0225(7) 0.8146(8) 0.4795(3) 0.130(2) Uani C 1.0
C4Ba 0.0113(6) 0.7610(7) 0.5146(2) 0.120(3) Uani C 1.0
C5Ba 0.0968(7) 0.6563(8) 0.5194(2) 0.105(3) Uani C 1.0
C6Ba 0.1491(6) 0.6049(7) 0.4879(2) 0.089(2) Uani C 1.0
C7Ba 0.1703(6) 0.6058(7) 0.4182(2) 0.072(2) Uani C 1.0
H1O1 0.1046 0.1384 0.6413 0.076 Uani H 1.0
H1O2 0.4127 0.6997 0.6377 0.085 Uani H 1.0
H1C1 0.3810 0.2872 0.7338 0.086 Uani H 1.0
H2C1 0.2954 0.4252 0.7368 0.087 Uani H 1.0
HC2 0.1711 0.2489 0.7069 0.078 Uani H 1.0
HC4 0.4488 0.1760 0.6359 0.078 Uani H 1.0
H1C5 0.5523 0.3850 0.6575 0.076 Uani H 1.0
H2C5 0.5362 0.2684 0.6899 0.082 Uani H 1.0
HC6 0.4944 0.4804 0.7153 0.077 Uani H 1.0
HC8 0.1890 0.5975 0.6443 0.084 Uani H 1.0
H1C9 0.0915 0.3777 0.6529 0.078 Uani H 1.0
H2C9 0.1188 0.4728 0.6907 0.085 Uani H 1.0
H1C10 0.3700 0.0011 0.6714 0.089 Uani H 1.0
H2C10 0.3970 0.0958 0.7093 0.090 Uani H 1.0
H3C10 0.2578 0.0265 0.6995 0.088 Uani H 1.0
H1C11 0.2810 0.7469 0.6882 0.094 Uani H 1.0
H2C11 0.2652 0.6288 0.7201 0.091 Uani H 1.0
H3C11 0.4019 0.7041 0.7176 0.089 Uani H 1.0
H1C12 0.3247 0.2722 0.5896 0.086 Uani H 1.0
H2C12 0.4408 0.3788 0.6006 0.086 Uani H 1.0
H1C13 0.1814 0.4250 0.5981 0.088 Uani H 1.0
H2C13 0.2958 0.5356 0.5953 0.092 Uani H 1.0
H1O2Ba 0.2646 0.4373 0.4017 0.090 Uani H 1.0
HC2Ba 0.0074 0.7994 0.4227 0.119 Uani H 1.0
HC3Ba -0.0851 0.8912 0.4762 0.185 Uani H 1.0
HC4Ba -0.0272 0.7991 0.5372 0.151 Uani H 1.0
HC5Ba 0.1210 0.6177 0.5452 0.133 Uani H 1.0
HC6Ba 0.2117 0.5283 0.4911 0.115 Uani H 1.0
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 109.6(5) 1_555 1_555 1_555 no
C1 C2 C3 110.0(5) 1_555 1_555 1_555 no
C1 C2 C9 107.3(5) 1_555 1_555 1_555 no
C3 C2 C9 115.5(5) 1_555 1_555 1_555 no
O1 C3 C2 110.6(4) 1_555 1_555 1_555 no
O1 C3 C4 105.4(5) 1_555 1_555 1_555 no
O1 C3 C10 106.8(5) 1_555 1_555 1_555 no
C2 C3 C4 112.9(5) 1_555 1_555 1_555 no
C2 C3 C10 109.7(5) 1_555 1_555 1_555 no
C4 C3 C10 111.2(5) 1_555 1_555 1_555 no
C3 C4 C5 109.8(5) 1_555 1_555 1_555 no
C3 C4 C12 116.2(5) 1_555 1_555 1_555 no
C5 C4 C12 111.8(5) 1_555 1_555 1_555 no
C4 C5 C6 115.3(4) 1_555 1_555 1_555 no
C1 C6 C5 106.1(5) 1_555 1_555 1_555 no
C1 C6 C7 111.1(4) 1_555 1_555 1_555 no
C5 C6 C7 115.6(5) 1_555 1_555 1_555 no
O2 C7 C6 106.7(4) 1_555 1_555 1_555 no
O2 C7 C8 109.4(5) 1_555 1_555 1_555 no
O2 C7 C11 109.0(5) 1_555 1_555 1_555 no
C6 C7 C8 112.1(5) 1_555 1_555 1_555 no
C6 C7 C11 109.8(5) 1_555 1_555 1_555 no
C8 C7 C11 109.8(5) 1_555 1_555 1_555 no
C7 C8 C9 111.0(5) 1_555 1_555 1_555 no
C7 C8 C13 116.2(5) 1_555 1_555 1_555 no
C9 C8 C13 112.8(5) 1_555 1_555 1_555 no
C2 C9 C8 114.5(4) 1_555 1_555 1_555 no
C4 C12 C13 120.4(6) 1_555 1_555 1_555 no
C8 C13 C12 116.8(6) 1_555 1_555 1_555 no
C2Ba C1Ba C6Ba 118.5(7) 1_555 1_555 1_555 no
C2Ba C1Ba C7Ba 117.9(6) 1_555 1_555 1_555 no
C6Ba C1Ba C7Ba 123.6(6) 1_555 1_555 1_555 no
C1Ba C2Ba C3Ba 121.5(6) 1_555 1_555 1_555 no
C2Ba C3Ba C4Ba 118.7(7) 1_555 1_555 1_555 no
C3Ba C4Ba C5Ba 121.2(9) 1_555 1_555 1_555 no
C4Ba C5Ba C6Ba 118.7(7) 1_555 1_555 1_555 no
C1Ba C6Ba C5Ba 121.5(6) 1_555 1_555 1_555 no
O1Ba C7Ba O2Ba 120.3(7) 1_555 1_555 1_555 no
O1Ba C7Ba C1Ba 126.6(6) 1_555 1_555 1_555 no
O2Ba C7Ba C1Ba 113.0(7) 1_555 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.458(7) 1_555 1_555 no
O2 C7 1.443(7) 1_555 1_555 no
C1 C2 1.529(8) 1_555 1_555 no
C1 C6 1.524(8) 1_555 1_555 no
C2 C3 1.534(8) 1_555 1_555 no
C2 C9 1.529(9) 1_555 1_555 no
C3 C4 1.559(8) 1_555 1_555 no
C3 C10 1.520(9) 1_555 1_555 no
C4 C5 1.532(9) 1_555 1_555 no
C4 C12 1.510(9) 1_555 1_555 no
C5 C6 1.529(8) 1_555 1_555 no
C6 C7 1.536(8) 1_555 1_555 no
C7 C8 1.565(8) 1_555 1_555 no
C7 C11 1.518(8) 1_555 1_555 no
C8 C9 1.533(9) 1_555 1_555 no
C8 C13 1.517(9) 1_555 1_555 no
C12 C13 1.559(9) 1_555 1_555 no
O1Ba C7Ba 1.199(8) 1_555 1_555 no
O2Ba C7Ba 1.364(8) 1_555 1_555 no
C1Ba C2Ba 1.365(6) 1_555 1_555 no
C1Ba C6Ba 1.365(6) 1_555 1_555 no
C1Ba C7Ba 1.466(10) 1_555 1_555 no
C2Ba C3Ba 1.380(8) 1_555 1_555 no
C3Ba C4Ba 1.367(7) 1_555 1_555 no
C4Ba C5Ba 1.367(7) 1_555 1_555 no
C5Ba C6Ba 1.380(8) 1_555 1_555 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195514
