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_7244288
_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, C4 H8 O'
_chemical_formula_sum            'C11 H13 Br O5'
_chemical_formula_weight         305.13
_chemical_name_systematic        '5-bromo-resorcylic acid THF 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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.448(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8148(4)
_cell_length_b                   15.5203(12)
_cell_length_c                   15.6723(12)
_cell_measurement_reflns_used    7743
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.149
_cell_measurement_theta_min      2.616
_cell_volume                     1163.74(16)
_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 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_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  0.1354
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25375
_diffrn_reflns_theta_full        27.2001
_diffrn_reflns_theta_max         27.20
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.539
_exptl_absorpt_correction_T_max  0.8939
_exptl_absorpt_correction_T_min  0.2738
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1736 before and 0.0957 after correction.
The Ratio of minimum to maximum transmission is 0.3063.
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    1.7414
_exptl_crystal_description       prism
_exptl_crystal_F_000             615.2619
_exptl_crystal_recrystallization_method
'Crystallised from THF by slow cooling'
_exptl_crystal_size_max          0.802
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.064
_refine_diff_density_max         1.8443
_refine_diff_density_min         -1.2476
_refine_diff_density_rms         0.2599
_refine_ls_d_res_high            0.7774
_refine_ls_d_res_low             7.7866
_refine_ls_goodness_of_fit_ref   0.9714
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.9666
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1442
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                1975
_reflns_number_total             2578
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           KE048
_cod_database_code               7244288
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3s) \\sim Ueq, Uanis(C2s) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C5s) \\sim Ueq, Uanis(C4s) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(C14a)=Sof(C2s)=Sof(C4s)=Sof(H6sd)=Sof(H6sc)=Sof(H1sd)=Sof(H1sc)=Sof(H4sb)=
 Sof(H4sa)=Sof(H2sa)=Sof(H2sb)=1-FVAR(1)
 Sof(C3s)=Sof(C5s)=Sof(H3sa)=Sof(H3sb)=Sof(H6sa)=Sof(H6sb)=Sof(H1sb)=Sof(H1sa)=
 Sof(H5sb)=Sof(H5sa)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3s(H3sa,H3sb), C6s(H6sd,H6sc), C6s(H6sa,H6sb), C1s(H1sb,H1sa), C1s(H1sd,
 H1sc), C4s(H4sb,H4sa), C5s(H5sb,H5sa), C2s(H2sa,H2sb)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4a), C7(H7)
4.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O1(H1)
;
_olex2_exptl_crystal_mounting_method
'Crystal soaked in perfluoro polyether oil and mounted onto MiTeGen sample holder directly into the pre-cooled cryostream'
_olex2_submission_special_instructions 'No special instructions were received'