Noncooperative guest binding by metal-free [2 + 2] Schiff-base macrocycles
Chaudhry, Mohammad T.; Patrick, Brian O.; Akine, Shigehisa; MacLachlan, Mark J.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01511K

data_7158925
_publ_section_title
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 Noncooperative guest binding by metal-free [2 + 2] Schiff-base
 macrocycles
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01511K
_journal_year                    2022
_chemical_formula_moiety         'C14 H10 O5'
_chemical_formula_sum            'C14 H10 O5'
_chemical_formula_weight         258.22
_chemical_name_systematic        'diformyl diphenol ether'
_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     dual
_audit_creation_date             2021-12-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-04-18 deposited with the CCDC.	2022-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.923(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2993(15)
_cell_length_b                   14.0697(18)
_cell_length_c                   7.3760(10)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.517
_cell_measurement_theta_min      2.343
_cell_volume                     1147.3(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 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 CCD 6000 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            34340
_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         30.536
_diffrn_reflns_theta_min         1.842
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_target            Mo
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0632 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.9575.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method 'Slow evaporation from DCM and Hexanes'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0387
_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/[\s^2^(Fo^2^)+(0.0487P)^2^+0.5477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2870
_reflns_number_total             3519
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01511k2.cif
_cod_data_source_block           mm491
_cod_database_code               7158925
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C9(H9), C3(H3), C1(H1), C11(H11), C10(H10), C13(H13)
1.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_olex2_exptl_crystal_mounting_method
'Mounted using parafin oil and a mylar loop'
_olex2_submission_original_sample_id 'diformyl diphenol ether'
_olex2_submission_special_instructions 'No special instructions were received'