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_7244294
_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 H4 Br2 O4, C4 H8 O'
_chemical_formula_sum            'C11 H12 Br2 O5'
_chemical_formula_weight         384.03
_chemical_name_systematic        '3,5-dibromo-resorcylic acid THF 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             2021-06-16
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.1838(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9275(3)
_cell_length_b                   16.6356(9)
_cell_length_c                   15.8268(8)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.45
_cell_volume                     1287.17(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution
'olex2.solve 1.3-alpha (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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19514
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.777
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.307
_exptl_absorpt_correction_T_max  0.2997
_exptl_absorpt_correction_T_min  0.1246
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1122 before and 0.0665 after correction.
The Ratio of minimum to maximum transmission is 0.4157.
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    1.982
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_preparation       'cut from a larger crystal'
_exptl_crystal_recrystallization_method
'crystallised from THF by fast cooling'
_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.342
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0156P)^2^+0.5415P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0470
_refine_ls_wR_factor_ref         0.0491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2405
_reflns_number_total             2740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           ke033
_cod_database_code               7244294
_shelx_shelxl_version_number     2018/3
_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 O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O6A) = Uanis(O6)
3. Others
 Sof(H11)=Sof(O6A)=Sof(H6A)=1-FVAR(1)
 Sof(O6)=Sof(H6)=Sof(H7)=FVAR(1)
 Sof(C18A)=Sof(H18C)=Sof(H18D)=1-FVAR(2)
 Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C18A(H18C,H18D)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11)
4.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O6(H6), O6A(H6A)
;
_olex2_exptl_crystal_mounting_method
'Crystal coated in perfluoro polyether oil and mounted on a MiTeGen sample holder directly into the cold cryostream'
_olex2_submission_original_sample_id 'BRA THF FC'
_olex2_submission_special_instructions 'No special instructions were received'