#------------------------------------------------------------------------------
#$Date: 2022-01-26 01:37:51 +0200 (Wed, 26 Jan 2022) $
#$Revision: 272229 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/42/7244292.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244292
loop_
_publ_author_name
'Edkins, Katharina'
'Tweedy, Jane'
'Fung, Stephanie'
'Edkins, Robert M.'
_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         'C3 H7 N O, C7 H6 O4'
_chemical_formula_sum            'C10 H13 N O5'
_chemical_formula_weight         227.21
_chemical_name_systematic        'resorcylic acid DMF 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     direct
_audit_creation_date             2021-06-17
_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                 96.322(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.320(4)
_cell_length_b                   24.910(7)
_cell_length_c                   7.009(2)
_cell_measurement_reflns_used    2498
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.950
_cell_measurement_theta_min      1.663
_cell_volume                     2137.9(11)
_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    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  Synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.4234
_diffrn_reflns_av_unetI/netI     0.1886
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            32606
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.950
_diffrn_reflns_theta_min         1.663
_diffrn_source                   Synchrotron
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0634P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2140
_refine_ls_wR_factor_ref         0.2537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2360
_reflns_number_total             5627
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01592c2.cif
_cod_data_source_block           RA_DMF
_cod_original_cell_volume        2137.8(11)
_cod_database_code               7244292
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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:
 C17(H17), C15(H15), C18(H18), C29(H29), C20(H20), C24(H24), C27(H27),
 C0AA(H0AA)
2.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O7(H7), O8(H8), O6(H6), O9(H9), O10(H10)
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1AA O 0.49485(17) 0.79131(8) 0.7677(2) 0.0395(5) Uani 1 1 d . . . . .
N12 N 0.5050(2) 0.88250(10) 0.7740(3) 0.0347(6) Uani 1 1 d . . . . .
C17 C 0.5399(2) 0.83438(12) 0.8242(3) 0.0341(7) Uani 1 1 d . . . . .
H17 H 0.604686 0.831925 0.910651 0.041 Uiso 1 1 calc R U . . .
C31 C 0.4052(2) 0.89020(13) 0.6440(4) 0.0404(8) Uani 1 1 d . . . . .
H31A H 0.375782 0.855169 0.600923 0.061 Uiso 1 1 calc R U . . .
H31B H 0.421714 0.911262 0.532667 0.061 Uiso 1 1 calc R U . . .
H31C H 0.351268 0.909338 0.711236 0.061 Uiso 1 1 calc R U . . .
C32 C 0.5637(3) 0.93022(12) 0.8432(4) 0.0431(8) Uani 1 1 d . . . . .
H32A H 0.519646 0.950447 0.926636 0.065 Uiso 1 1 calc R U . . .
H32B H 0.578133 0.952644 0.733907 0.065 Uiso 1 1 calc R U . . .
H32C H 0.633061 0.919880 0.915909 0.065 Uiso 1 1 calc R U . . .
O2 O 0.21728(16) 0.50953(8) 0.5093(2) 0.0359(5) Uani 1 1 d . . . . .
O4 O 0.36648(16) 0.57541(8) 0.6606(3) 0.0363(5) Uani 1 1 d . . . . .
H4 H 0.338800 0.545587 0.627166 0.055 Uiso 1 1 calc R U . . .
O7 O 0.29747(18) 0.76193(8) 0.5598(3) 0.0400(5) Uani 1 1 d . . . . .
H7 H 0.361791 0.764090 0.613156 0.060 Uiso 1 1 calc R U . . .
O8 O 0.06536(16) 0.54394(8) 0.3490(3) 0.0368(5) Uani 1 1 d . . . . .
H8 H 0.053383 0.511461 0.322185 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1951(2) 0.60394(12) 0.4889(3) 0.0312(7) Uani 1 1 d . . . . .
C15 C 0.1306(2) 0.64760(12) 0.4171(3) 0.0328(7) Uani 1 1 d . . . . .
H15 H 0.061166 0.640697 0.348368 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1622(2) 0.54877(12) 0.4519(3) 0.0313(7) Uani 1 1 d . . . . .
C18 C 0.3328(2) 0.66806(12) 0.6192(3) 0.0330(7) Uani 1 1 d . . . . .
H18 H 0.400953 0.675385 0.691684 0.040 Uiso 1 1 calc R U . . .
C21 C 0.2680(2) 0.71010(12) 0.5429(3) 0.0327(7) Uani 1 1 d . . . . .
C25 C 0.2985(2) 0.61551(12) 0.5903(3) 0.0310(7) Uani 1 1 d . . . . .
C29 C 0.1643(2) 0.69933(12) 0.4428(3) 0.0343(7) Uani 1 1 d . . . . .
H29 H 0.118518 0.728000 0.393910 0.041 Uiso 1 1 calc R U . . .
O0AA O 0.71774(17) 0.72913(9) 1.0323(2) 0.0384(5) Uani 1 1 d . . . . .
O6 O 0.84929(18) 0.65936(9) 1.2084(3) 0.0422(6) Uani 1 1 d . . . . .
H6 H 0.823615 0.689868 1.179080 0.063 Uiso 1 1 calc R U . . .
O9 O 0.80129(17) 0.47678(8) 1.0164(3) 0.0406(5) Uani 1 1 d . . . . .
H9 H 0.858605 0.473344 1.092212 0.061 Uiso 1 1 calc R U . . .
O10 O 0.58210(16) 0.69911(8) 0.8181(3) 0.0390(5) Uani 1 1 d . . . . .
H10 H 0.570292 0.732174 0.804386 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7021(2) 0.63574(12) 0.9653(3) 0.0309(7) Uani 1 1 d . . . . .
C19 C 0.7719(2) 0.52921(12) 1.0060(3) 0.0315(7) Uani 1 1 d . . . . .
C20 C 0.6474(2) 0.59427(12) 0.8587(3) 0.0324(7) Uani 1 1 d . . . . .
H20 H 0.585196 0.602745 0.771351 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7930(2) 0.62134(12) 1.0969(3) 0.0327(7) Uani 1 1 d . . . . .
C24 C 0.8266(2) 0.56910(12) 1.1179(3) 0.0337(7) Uani 1 1 d . . . . .
H24 H 0.886966 0.560074 1.208343 0.040 Uiso 1 1 calc R U . . .
C26 C 0.6695(2) 0.69156(12) 0.9426(3) 0.0339(7) Uani 1 1 d . . . . .
C27 C 0.6806(2) 0.54256(12) 0.8767(3) 0.0370(7) Uani 1 1 d . . . . .
H27 H 0.642190 0.515342 0.802060 0.044 Uiso 1 1 calc R U . . .
N2 N 0.0248(2) 0.36053(10) 0.2256(3) 0.0333(6) Uani 1 1 d . . . . .
O3 O -0.00170(16) 0.45053(8) 0.2295(2) 0.0349(5) Uani 1 1 d . . . . .
C0AA C 0.0503(2) 0.40928(12) 0.2844(3) 0.0335(7) Uani 1 1 d . . . . .
H0AA H 0.112817 0.413585 0.375236 0.040 Uiso 1 1 calc R U . . .
C5 C 0.0867(2) 0.31402(12) 0.3016(4) 0.0422(8) Uani 1 1 d . . . . .
H5A H 0.117102 0.295253 0.196727 0.063 Uiso 1 1 calc R U . . .
H5B H 0.038364 0.289697 0.362658 0.063 Uiso 1 1 calc R U . . .
H5C H 0.146209 0.325795 0.396706 0.063 Uiso 1 1 calc R U . . .
C6 C -0.0709(2) 0.35022(13) 0.0874(4) 0.0404(8) Uani 1 1 d . . . . .
H6A H -0.131807 0.338352 0.155909 0.061 Uiso 1 1 calc R U . . .
H6B H -0.053515 0.322186 -0.002504 0.061 Uiso 1 1 calc R U . . .
H6C H -0.091436 0.383225 0.016319 0.061 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N12 C31 121.1(2) . . ?
C17 N12 C32 121.7(2) . . ?
C32 N12 C31 117.2(2) . . ?
O1AA C17 N12 125.4(3) . . ?
O1AA C17 H17 117.3 . . ?
N12 C17 H17 117.3 . . ?
N12 C31 H31A 109.5 . . ?
N12 C31 H31B 109.5 . . ?
N12 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N12 C32 H32A 109.5 . . ?
N12 C32 H32B 109.5 . . ?
N12 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 O4 H4 109.5 . . ?
C21 O7 H7 109.5 . . ?
C16 O8 H8 109.5 . . ?
C15 C14 C16 122.3(2) . . ?
C15 C14 C25 117.6(3) . . ?
C25 C14 C16 120.0(2) . . ?
C14 C15 H15 118.9 . . ?
C29 C15 C14 122.2(3) . . ?
C29 C15 H15 118.9 . . ?
O2 C16 O8 122.3(3) . . ?
O2 C16 C14 124.2(2) . . ?
O8 C16 C14 113.5(2) . . ?
C21 C18 H18 119.9 . . ?
C25 C18 H18 119.9 . . ?
C25 C18 C21 120.3(3) . . ?
O7 C21 C18 123.6(3) . . ?
O7 C21 C29 116.5(3) . . ?
C18 C21 C29 119.9(3) . . ?
O4 C25 C14 121.0(3) . . ?
O4 C25 C18 118.4(2) . . ?
C18 C25 C14 120.6(3) . . ?
C15 C29 C21 119.4(3) . . ?
C15 C29 H29 120.3 . . ?
C21 C29 H29 120.3 . . ?
C22 O6 H6 109.5 . . ?
C19 O9 H9 109.5 . . ?
C26 O10 H10 109.5 . . ?
C20 C11 C22 117.4(3) . . ?
C20 C11 C26 122.4(2) . . ?
C22 C11 C26 120.2(3) . . ?
O9 C19 C24 123.2(2) . . ?
O9 C19 C27 117.0(3) . . ?
C24 C19 C27 119.8(3) . . ?
C11 C20 H20 119.1 . . ?
C27 C20 C11 121.9(2) . . ?
C27 C20 H20 119.1 . . ?
O6 C22 C11 120.8(3) . . ?
O6 C22 C24 118.0(2) . . ?
C24 C22 C11 121.2(3) . . ?
C19 C24 H24 120.1 . . ?
C22 C24 C19 119.8(3) . . ?
C22 C24 H24 120.1 . . ?
O0AA C26 O10 122.4(3) . . ?
O0AA C26 C11 123.7(2) . . ?
O10 C26 C11 113.8(2) . . ?
C19 C27 H27 120.1 . . ?
C20 C27 C19 119.9(3) . . ?
C20 C27 H27 120.1 . . ?
C0AA N2 C5 121.7(2) . . ?
C0AA N2 C6 121.2(2) . . ?
C5 N2 C6 117.0(2) . . ?
N2 C0AA H0AA 117.7 . . ?
O3 C0AA N2 124.7(2) . . ?
O3 C0AA H0AA 117.7 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1AA C17 1.252(3) . ?
N12 C17 1.308(4) . ?
N12 C31 1.460(3) . ?
N12 C32 1.447(3) . ?
C17 H17 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O2 C16 1.232(3) . ?
O4 H4 0.8400 . ?
O4 C25 1.361(3) . ?
O7 H7 0.8400 . ?
O7 C21 1.343(4) . ?
O8 H8 0.8400 . ?
O8 C16 1.330(3) . ?
C14 C15 1.407(4) . ?
C14 C16 1.448(4) . ?
C14 C25 1.418(4) . ?
C15 H15 0.9500 . ?
C15 C29 1.360(4) . ?
C18 H18 0.9500 . ?
C18 C21 1.388(4) . ?
C18 C25 1.384(4) . ?
C21 C29 1.414(4) . ?
C29 H29 0.9500 . ?
O0AA C26 1.242(3) . ?
O6 H6 0.8400 . ?
O6 C22 1.367(3) . ?
O9 H9 0.8400 . ?
O9 C19 1.355(4) . ?
O10 H10 0.8400 . ?
O10 C26 1.323(3) . ?
C11 C20 1.403(4) . ?
C11 C22 1.417(4) . ?
C11 C26 1.451(4) . ?
C19 C24 1.393(4) . ?
C19 C27 1.405(4) . ?
C20 H20 0.9500 . ?
C20 C27 1.353(4) . ?
C22 C24 1.368(4) . ?
C24 H24 0.9500 . ?
C27 H27 0.9500 . ?
N2 C0AA 1.309(4) . ?
N2 C5 1.455(3) . ?
N2 C6 1.464(3) . ?
O3 C0AA 1.249(3) . ?
C0AA H0AA 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 N12 C17 O1AA 0.9(4) . . . . ?
C32 N12 C17 O1AA -178.6(3) . . . . ?
O7 C21 C29 C15 178.6(2) . . . . ?
C14 C15 C29 C21 0.8(4) . . . . ?
C15 C14 C16 O2 178.7(2) . . . . ?
C15 C14 C16 O8 -1.5(4) . . . . ?
C15 C14 C25 O4 -178.6(2) . . . . ?
C15 C14 C25 C18 1.0(4) . . . . ?
C16 C14 C15 C29 -176.2(2) . . . . ?
C16 C14 C25 O4 -2.5(4) . . . . ?
C16 C14 C25 C18 177.1(2) . . . . ?
C18 C21 C29 C15 -2.1(4) . . . . ?
C21 C18 C25 O4 177.2(2) . . . . ?
C21 C18 C25 C14 -2.4(4) . . . . ?
C25 C14 C15 C29 -0.2(4) . . . . ?
C25 C14 C16 O2 2.7(4) . . . . ?
C25 C14 C16 O8 -177.5(2) . . . . ?
C25 C18 C21 O7 -177.8(2) . . . . ?
C25 C18 C21 C29 3.0(4) . . . . ?
O6 C22 C24 C19 -179.6(2) . . . . ?
O9 C19 C24 C22 178.9(3) . . . . ?
O9 C19 C27 C20 -179.6(3) . . . . ?
C11 C20 C27 C19 0.4(4) . . . . ?
C11 C22 C24 C19 1.0(4) . . . . ?
C20 C11 C22 O6 -178.8(2) . . . . ?
C20 C11 C22 C24 0.6(4) . . . . ?
C20 C11 C26 O0AA -178.5(3) . . . . ?
C20 C11 C26 O10 2.1(4) . . . . ?
C22 C11 C20 C27 -1.3(4) . . . . ?
C22 C11 C26 O0AA 0.7(4) . . . . ?
C22 C11 C26 O10 -178.7(3) . . . . ?
C24 C19 C27 C20 1.2(4) . . . . ?
C26 C11 C20 C27 177.9(3) . . . . ?
C26 C11 C22 O6 2.0(4) . . . . ?
C26 C11 C22 C24 -178.7(3) . . . . ?
C27 C19 C24 C22 -2.0(4) . . . . ?
C5 N2 C0AA O3 -177.5(3) . . . . ?
C6 N2 C0AA O3 -0.7(4) . . . . ?
