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_7244290
_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, C5 H12 O'
_chemical_formula_sum            'C12 H16 Br2 O5'
_chemical_formula_weight         400.07
_chemical_name_systematic
'3,5-dibromo-resorcylic acid pentanol solvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 93.5848(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1238(4)
_cell_length_b                   24.7317(15)
_cell_length_c                   7.2459(4)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.51
_cell_volume                     1452.96(14)
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            21736
_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         25.998
_diffrn_reflns_theta_min         2.512
_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    5.591
_exptl_absorpt_correction_T_max  0.6449
_exptl_absorpt_correction_T_min  0.2455
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1163 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.3807.
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    1.829
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_preparation       'cut from a larger crystal'
_exptl_crystal_recrystallization_method
'crystallised by slow cooling from pentanol solution'
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0163P)^2^+1.8096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0568
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2526
_reflns_number_total             2841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           ke037
_cod_database_code               7244290
_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 C(H,H,H,H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Sof(H1SA)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=Sof(C1SA)=Sof(H1SD)=Sof(H1SE)=
 Sof(C2SA)=Sof(H2SC)=Sof(H2SD)=Sof(C3SA)=Sof(H3SC)=Sof(H3SD)=Sof(C4SA)=
 Sof(H4SC)=Sof(H4SD)=1-FVAR(1)
 Sof(H1S)=Sof(C3SB)=Sof(H3SA)=Sof(H3SB)=Sof(H5SD)=Sof(H5SE)=Sof(H5SF)=
 Sof(C4SB)=Sof(H4SA)=Sof(H4SB)=Sof(C1SB)=Sof(H1SB)=Sof(H1SC)=Sof(C2SB)=
 Sof(H2SA)=Sof(H2SB)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C3SB(H3SA,H3SB), C4SB(H4SA,H4SB), C1SB(H1SB,H1SC), C2SB(H2SA,H2SB), C1SA(H1SD,
 H1SE), C2SA(H2SC,H2SD), C3SA(H3SC,H3SD), C4SA(H4SC,H4SD)
3.b Me refined with riding coordinates:
 C5S(H5SA,H5SB,H5SC), C5S(H5SD,H5SE,H5SF)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
3.d Tetrahedral OH refined with riding coordinates:
 O1S(H1S), O1S(H1SA)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O3(H3)
;
_olex2_exptl_crystal_mounting_method
'crystal coated in perfluoro polyether oil and mounted on a MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'