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#$Date: 2022-01-26 01:37:51 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272229 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/42/7244289.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_7244289
loop_
_publ_author_name
'Edkins, Katharina'
'Tweedy, Jane'
'Fung, Stephanie'
'Edkins, Robert M.'
_publ_section_title
;
 Steric influence on solvate formation -- a comparison of resorcylic acid
 and two brominated derivatives
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01592C
_journal_year                    2022
_chemical_formula_moiety         'C7 H6 O4, C2 H4 O2'
_chemical_formula_sum            'C9 H10 O6'
_chemical_formula_weight         214.17
_chemical_name_systematic        'Resorcylic acid acetic acid solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.898(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.6177(5)
_cell_length_b                   17.933(2)
_cell_length_c                   11.6033(15)
_cell_measurement_reflns_used    4022
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      2.89
_cell_volume                     946.56(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16041
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.271
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0879 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.9155. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method
'Crystallised by slow cooling from acetic acid'
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.118
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0447P)²+0.2996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1387
_reflns_number_total             1868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           ke064
_cod_original_cell_volume        946.6(2)
_cod_database_code               7244289
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4A), C6(H6)
2.b Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O3(H3), O1S(H1S)
;
_olex2_exptl_crystal_mounting_method
'Crystal soaked in perfluroo polyether oil and mounted on MiTeGen sample holders directly into the pre-cooled cryostream.'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5415(3) 0.81390(7) 0.11497(11) 0.0202(3) Uani 1 1 d . . . . .
H1 H 0.6028 0.8547 0.1402 0.030 Uiso 1 1 calc GR . . . .
O4 O -0.2374(3) 0.55612(6) -0.13546(11) 0.0197(3) Uani 1 1 d . . . . .
H4 H -0.3889 0.5637 -0.1823 0.030 Uiso 1 1 calc GR . . . .
O3 O -0.2362(3) 0.82045(7) -0.13089(11) 0.0209(3) Uani 1 1 d . . . . .
H3 H -0.1492 0.8557 -0.0955 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.1832(3) 0.88533(7) 0.01750(11) 0.0190(3) Uani 1 1 d . . . . .
O2S O 0.7574(3) 0.94224(7) 0.20189(11) 0.0181(3) Uani 1 1 d . . . . .
O1S O 0.3734(3) 1.01198(7) 0.12390(11) 0.0184(3) Uani 1 1 d . . . . .
H1S H 0.3204 0.9725 0.0911 0.028 Uiso 1 1 calc GR . . . .
C2 C 0.1526(4) 0.75409(10) -0.00590(15) 0.0143(4) Uani 1 1 d . . . . .
C7 C 0.2686(4) 0.68408(10) 0.03161(15) 0.0156(4) Uani 1 1 d . . . . .
H7 H 0.4384 0.6819 0.0877 0.019 Uiso 1 1 calc R . . . .
C4 C -0.2351(4) 0.69022(10) -0.13626(15) 0.0151(4) Uani 1 1 d . . . . .
H4A H -0.4027 0.6918 -0.1936 0.018 Uiso 1 1 calc R . . . .
C1 C 0.2918(4) 0.82264(10) 0.04231(15) 0.0146(4) Uani 1 1 d . . . . .
C3 C -0.1046(4) 0.75592(10) -0.09058(15) 0.0137(4) Uani 1 1 d . . . . .
C5 C -0.1155(4) 0.62231(10) -0.09634(15) 0.0145(4) Uani 1 1 d . . . . .
C1S C 0.6256(4) 1.00209(10) 0.19425(15) 0.0151(4) Uani 1 1 d . . . . .
C2S C 0.7376(4) 1.06823(10) 0.26551(16) 0.0192(4) Uani 1 1 d . . . . .
H2SA H 0.7032 1.0617 0.3442 0.029 Uiso 1 1 calc GR . . . .
H2SB H 0.6372 1.1121 0.2323 0.029 Uiso 1 1 calc GR . . . .
H2SC H 0.9447 1.0735 0.2660 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.1395(4) 0.61892(10) -0.01190(16) 0.0171(4) Uani 1 1 d . . . . .
H6 H 0.2200 0.5732 0.0143 0.020 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_
_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
_geom_angle_publ_flag
C7 C2 C1 121.12(16) . . ?
C7 C2 C3 117.97(16) . . ?
C3 C2 C1 120.91(16) . . ?
C6 C7 C2 122.02(16) . . ?
C5 C4 C3 119.85(15) . . ?
O1 C1 C2 115.25(15) . . ?
O2 C1 O1 121.98(16) . . ?
O2 C1 C2 122.77(15) . . ?
O3 C3 C2 122.49(16) . . ?
O3 C3 C4 117.05(15) . . ?
C4 C3 C2 120.46(16) . . ?
O4 C5 C4 122.61(15) . . ?
O4 C5 C6 116.55(15) . . ?
C4 C5 C6 120.83(16) . . ?
O2S C1S O1S 122.51(16) . . ?
O2S C1S C2S 122.39(16) . . ?
O1S C1S C2S 115.09(15) . . ?
C7 C6 C5 118.86(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.316(2) . ?
O4 C5 1.358(2) . ?
O3 C3 1.353(2) . ?
O2 C1 1.244(2) . ?
O2S C1S 1.229(2) . ?
O1S C1S 1.314(2) . ?
C2 C7 1.404(2) . ?
C2 C1 1.454(2) . ?
C2 C3 1.406(2) . ?
C7 C6 1.368(2) . ?
C4 C3 1.387(2) . ?
C4 C5 1.384(2) . ?
C5 C6 1.398(2) . ?
C1S C2S 1.487(2) . ?
