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_7158926
_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, 2(C2 H3 N)'
_chemical_formula_sum            'C52 H50 N6 O10'
_chemical_formula_weight         918.98
_chemical_name_systematic        macrocycle
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.0998(7)
_cell_length_b                   18.8164(7)
_cell_length_c                   29.2275(11)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    90
_cell_measurement_theta_max      55.873
_cell_measurement_theta_min      3.024
_cell_volume                     9404.1(6)
_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      90
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            53777
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        56.100
_diffrn_reflns_theta_max         56.100
_diffrn_reflns_theta_min         3.024
_diffrn_source_current           0.59
_diffrn_source_power             0.0264792
_diffrn_source_voltage           44.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.6127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0965 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8158.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             3872
_exptl_crystal_preparation
'Reaction of bisaldehyde and diamine in MeCN.,Luminescent'
_exptl_crystal_recrystallization_method
'Grown from reaction mixture through slow evaporation.'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         6127
_refine_ls_number_restraints     990
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0772P)^2^+9.6494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4655
_reflns_number_total             6127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01511k2.cif
_cod_data_source_block           mm523
_cod_database_code               7158926
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.785
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.05) H4(0.043) H7(0.043) H8(0.048) H1A(0.126) H1B(0.126)
 H1C(0.126) H2A(0.067) H2B(0.067) H3A(0.112) H3B(0.112) H3C(0.112) H4A(0.056)
 H4B(0.056) H7A(0.033) H10(0.039) H11(0.031) H13(0.035) H14(0.036) H15(0.034)
 H19(0.035) H20(0.04) H21(0.037) H24(0.031) H26(0.031) H29(0.031) H31A(0.036)
 H31B(0.036) H32A(0.053) H32B(0.053) H32C(0.053) H33A(0.041) H33B(0.041)
 H34A(0.061) H34B(0.061) H34C(0.061) H35(0.034) H37(0.035) H38(0.036)
 H39(0.035) H43(0.033) H44(0.036) H45(0.035) H48(0.035) H49A(0.059) H49B(0.059)
 H49C(0.059) H51A(0.208) H51B(0.208) H51C(0.208) H53A(0.208) H53B(0.208)
 H53C(0.208)
 Fixed X: H3(0.324689) H4(0.378664) H7(0.337102) H8(0.319133) H1A(0.366113)
 H1B(0.347404) H1C(0.403197) H2A(0.484112) H2B(0.493221) H3A(0.410091)
 H3B(0.468615) H3C(0.376611) H4A(0.355253) H4B(0.447559) H7A(0.402902)
 H10(0.430221) H11(0.378545) H13(0.341099) H14(0.305609) H15(0.303476)
 H19(0.476151) H20(0.587018) H21(0.573352) H24(0.493987) H26(0.410327)
 H29(0.349688) H31A(0.472335) H31B(0.381) H32A(0.450721) H32B(0.393797)
 H32C(0.485159) H33A(0.366677) H33B(0.339977) H34A(0.498336) H34B(0.459384)
 H34C(0.47127) H35(0.335493) H37(0.301493) H38(0.267434) H39(0.264847)
 H43(0.423246) H44(0.534998) H45(0.545912) H48(0.492194) H49A(0.289779)
 H49B(0.274669) H49C(0.265086) H51A(0.694624) H51B(0.764935) H51C(0.782876)
 H53A(0.760557) H53B(0.691418) H53C(0.780431)
 Fixed Y: H3(0.39557) H4(0.477362) H7(0.134299) H8(0.222704) H1A(0.53522)
 H1B(0.604118) H1C(0.543177) H2A(0.631927) H2B(0.569414) H3A(0.91125)
 H3B(0.875885) H3C(0.877081) H4A(0.797736) H4B(0.796962) H7A(0.693409)
 H10(0.522037) H11(0.653904) H13(0.674318) H14(0.633861) H15(0.510839)
 H19(0.449116) H20(0.379583) H21(0.257314) H24(0.151157) H26(0.079415) H29(-
 0.086006) H31A(0.022921) H31B(0.02707) H32A(-0.019853) H32B(-0.079775) H32C(-
 0.081574) H33A(-0.246209) H33B(-0.189125) H34A(-0.213978) H34B(-0.241014)
 H34C(-0.157752) H35(-0.04266) H37(-0.057155) H38(-0.011429) H39(0.112221)
 H43(0.145189) H44(0.194573) H45(0.317261) H48(0.434776) H49A(0.280479)
 H49B(0.363853) H49C(0.311343) H51A(0.251874) H51B(0.26861) H51C(0.252386)
 H53A(0.192404) H53B(0.21986) H53C(0.226832)
 Fixed Z: H3(0.770313) H4(0.690096) H7(0.652193) H8(0.567079) H1A(0.933053)
 H1B(0.963233) H1C(0.983064) H2A(0.959914) H2B(0.923205) H3A(0.803234)
 H3B(0.839391) H3C(0.849392) H4A(0.787736) H4B(0.777178) H7A(0.753358)
 H10(0.867706) H11(0.689835) H13(0.61126) H14(0.539746) H15(0.525009)
 H19(0.573695) H20(0.559527) H21(0.549537) H24(0.541842) H26(0.47991)
 H29(0.593385) H31A(0.420934) H31B(0.40807) H32A(0.345563) H32B(0.36558)
 H32C(0.377394) H33A(0.533992) H33B(0.571506) H34A(0.546068) H34B(0.592713)
 H34C(0.583976) H35(0.656484) H37(0.737341) H38(0.808318) H39(0.818844)
 H43(0.79164) H44(0.824032) H45(0.831269) H48(0.824594) H49A(0.683928)
 H49B(0.6777) H49C(0.634995) H51A(0.616193) H51B(0.650686) H51C(0.597971)
 H53A(0.567111) H53B(0.599506) H53C(0.61581)
;
_olex2_exptl_crystal_mounting_method
'Mounted onto a mylar loop using parafin oil.'
_olex2_submission_original_sample_id OC2-MeCN
_olex2_submission_special_instructions 'No special instructions were received'