Steric influence on solvate formation – a comparison of resorcylic acid and two brominated derivatives
Edkins, Katharina; Tweedy, Jane; Fung, Stephanie; Edkins, Robert M.; CrystEngComm  (2022) –; doi:10.1039/D1CE01592C

data_7244286
_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 H5 Br O4, 0.5(C4 H8 O)'
_chemical_formula_sum            'C9 H9 Br O4.5'
_chemical_formula_weight         269.07
_chemical_name_systematic
'5-bromo-resorcylic acid 2-butanone hemisolvate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                97.214(4)
_cell_angle_beta                 91.367(3)
_cell_angle_gamma                98.717(4)
_cell_formula_units_Z            4
_cell_length_a                   4.9186(7)
_cell_length_b                   14.079(2)
_cell_length_c                   14.695(2)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    120
_cell_measurement_theta_max      23.55
_cell_measurement_theta_min      2.30
_cell_volume                     996.9(2)
_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  'olex2.refine (Bourhis et al., 2015)'
_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 0.9925
_diffrn_measured_fraction_theta_max 0.9925
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1417
_diffrn_reflns_av_unetI/netI     0.1487
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17196
_diffrn_reflns_theta_full        26.8118
_diffrn_reflns_theta_max         26.81
_diffrn_reflns_theta_min         2.80
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.114
_exptl_absorpt_correction_T_max  0.9379
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1118 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.6322.
The \l/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    1.7926
_exptl_crystal_description       prism
_exptl_crystal_F_000             535.2321
_exptl_crystal_recrystallization_method 'crystallised from butanone solution'
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.054
_refine_diff_density_max         1.9541
_refine_diff_density_min         -1.6888
_refine_diff_density_rms         0.4464
_refine_ls_d_res_high            0.7878
_refine_ls_d_res_low             7.2824
_refine_ls_goodness_of_fit_ref   1.0368
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0368
_refine_ls_R_factor_all          0.1426
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.0035
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0076P)^2^+2.1741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2467
_reflns_number_total             4245
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           KE061
_cod_database_code               7244286
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3S(H3Sa,H3Sb)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7a), C4(H4a), C14(H14), C11(H11)
2.c Idealised Me refined as rotating group:
 C1S(H1Sa,H1Sb,H1Sc), C4S(H4Sa,H4Sb,H4Sc)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O8(H8), O1(H1), O7(H7), O5(H5)
;
_olex2_exptl_crystal_mounting_method
'crystal soaked in perfluoro polyether oil and mounted on MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'