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_7158924
_publ_section_title
;
 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         'C48 H44 N4 O10'
_chemical_formula_sum            'C48 H44 N4 O10'
_chemical_formula_weight         836.87
_chemical_name_systematic        macrocycle
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   47.0846(12)
_cell_length_b                   47.0846(12)
_cell_length_c                   10.6294(5)
_cell_measurement_reflns_used    6913
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.07
_cell_measurement_theta_min      2.160
_cell_volume                     20407.8(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0633
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            39894
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        22.522
_diffrn_reflns_theta_max         22.522
_diffrn_reflns_theta_min         1.730
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.5945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0888 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.7982.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       prism
_exptl_crystal_F_000             7920
_exptl_crystal_preparation
'Macrocyclization with substituted bisformylphenol and substituted o-phenylene diamine.,Luminescent'
_exptl_crystal_recrystallization_method 'Slow evaporation from DCM.'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         5932
_refine_ls_number_restraints     894
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0731P)^2^+61.2522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1556
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4343
_reflns_number_total             5932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01511k2.cif
_cod_data_source_block           mm509_sq
_cod_original_cell_volume        20407.8(14)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7158924
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.058) H5(0.052) H6(0.054) H8(0.062) H1A(0.088) H1B(0.088)
 H1C(0.088) H2A(0.058) H2B(0.058) H3A(0.068) H3B(0.068) H3C(0.068) H4A(0.047)
 H4B(0.047) H7(0.042) H10(0.043) H11(0.044) H13(0.046) H14(0.051) H15(0.049)
 H19(0.043) H20(0.046) H21(0.047) H24(0.042) H26(0.044) H29(0.04) H31(0.037)
 H33(0.044) H34(0.049) H35(0.048) H39(0.052) H40(0.054) H41(0.051) H44(0.044)
 H45A(0.05) H45B(0.05) H46A(0.077) H46B(0.077) H46C(0.077) H47A(0.068)
 H47B(0.068) H48B(0.128) H48A(0.128) H48C(0.128)
 Fixed X: H3(0.28078) H5(0.149115) H6(0.134105) H8(0.257725) H1A(0.404621)
 H1B(0.430453) H1C(0.422027) H2A(0.368471) H2B(0.375984) H3A(0.48855)
 H3B(0.493735) H3C(0.48441) H4A(0.441052) H4B(0.437226) H7(0.387331)
 H10(0.3358) H11(0.353891) H13(0.342187) H14(0.307258) H15(0.254255)
 H19(0.26709) H20(0.256602) H21(0.204056) H24(0.145989) H26(0.092753)
 H29(0.033551) H31(0.054741) H33(0.053226) H34(0.077892) H35(0.133621)
 H39(0.152013) H40(0.181531) H41(0.237409) H44(0.28816) H45A(-0.042561) H45B(-
 0.016965) H46A(-0.026383) H46B(0.011387) H46C(-0.012748) H47A(0.069914)
 H47B(0.054717) H48B(0.020745) H48A(0.037558) H48C(0.006775)
 Fixed Y: H3(0.261913) H5(0.165188) H6(0.215593) H8(0.289734) H1A(0.494944)
 H1B(0.484209) H1C(0.483905) H2A(0.440433) H2B(0.441215) H3A(0.407424)
 H3B(0.390366) H3C(0.418502) H4A(0.355621) H4B(0.365713) H7(0.326741)
 H10(0.388628) H11(0.276413) H13(0.218885) H14(0.163234) H15(0.144151)
 H19(0.203165) H20(0.214453) H21(0.202001) H24(0.18021) H26(0.138224)
 H29(0.16481) H31(0.163531) H33(0.17342) H34(0.200872) H35(0.241037)
 H39(0.290058) H40(0.334959) H41(0.355944) H44(0.356711) H45A(0.129107)
 H45B(0.136169) H46A(0.180581) H46B(0.192105) H46C(0.185514) H47A(0.12962)
 H47B(0.0951) H48B(0.109249) H48A(0.087404) H48C(0.074612)
 Fixed Z: H3(0.442056) H5(0.5764) H6(0.501125) H8(0.278207) H1A(0.352868)
 H1B(0.309612) H1C(0.455635) H2A(0.420952) H2B(0.273003) H3A(0.370458)
 H3B(0.49168) H3C(0.508383) H4A(0.399661) H4B(0.540708) H7(0.406076)
 H10(0.353079) H11(0.33907) H13(0.331239) H14(0.361212) H15(0.43841)
 H19(0.676721) H20(0.876746) H21(0.933853) H24(0.882046) H26(0.921659)
 H29(0.640234) H31(0.449861) H33(0.224918) H34(0.040467) H35(0.041454)
 H39(0.34533) H40(0.477085) H41(0.507456) H44(0.459322) H45A(0.789457)
 H45B(0.678375) H46A(0.704527) H46B(0.729239) H46C(0.845459) H47A(1.117897)
 H47B(1.045564) H48B(1.234476) H48A(1.257934) H48C(1.165251)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2020-11-16
_olex2_date_sample_submission    2020-11-16
_olex2_exptl_crystal_mounting_method
'Mounted to a mylar loop using parafin oil.'
_olex2_submission_original_sample_id 'mac OC2'
_olex2_submission_special_instructions 'No special instructions were received'