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_7244281
_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, C3 H7 N O'
_chemical_formula_sum            'C10 H12 Br N O5'
_chemical_formula_weight         306.12
_chemical_name_systematic        '5-bromo-resorcylic acid DMF 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             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                 111.328(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.8995(4)
_cell_length_b                   17.2454(6)
_cell_length_c                   13.5191(5)
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    120
_cell_measurement_theta_max      27.3570
_cell_measurement_theta_min      2.0030
_cell_volume                     2367.10(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -15.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9531   19.0000  -90.0000 105

  2 omega  -11.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3281 -100.0000   90.0000 35

  3 omega  -11.00   52.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9531 -100.0000  -30.0000 63

  4 omega  -89.00  -53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3281 -178.0000    0.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0098221000
_diffrn_orient_matrix_UB_12      -0.0104763000
_diffrn_orient_matrix_UB_13      -0.0530589000
_diffrn_orient_matrix_UB_21      0.0013862000
_diffrn_orient_matrix_UB_22      -0.0398054000
_diffrn_orient_matrix_UB_23      0.0137764000
_diffrn_orient_matrix_UB_31      -0.0691130000
_diffrn_orient_matrix_UB_32      0.0006806000
_diffrn_orient_matrix_UB_33      -0.0128981000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10853
_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         26.000
_diffrn_reflns_theta_min         2.002
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.483
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_preparation       'Cut from a larger crystal'
_exptl_crystal_recrystallization_method
'crystallised by slow cooling from DMF solution'
_exptl_crystal_size_max          0.2688
_exptl_crystal_size_mid          0.2063
_exptl_crystal_size_min          0.1449
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0278P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3500
_reflns_number_total             4656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           ke047
_cod_database_code               7244281
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C104(H10A), C1S(H1S), C4(H4A), C101(H10B), C107(H107), C8(H7)
2.b Idealised Me refined as rotating group:
 C3S(H3SA,H3SB,H3SC), C102(H10C,H10D,H10E), C2S(H2SA,H2SB,H2SC), C10(H10F,H10G,
 H10H)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O104(H104), O103(H103), O1(H101), O3(H3), O5(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-03
_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'