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_7158922
_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
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-30
_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                73.211(5)
_cell_angle_beta                 84.095(5)
_cell_angle_gamma                68.074(5)
_cell_formula_units_Z            8
_cell_length_a                   15.399(3)
_cell_length_b                   20.418(4)
_cell_length_c                   37.681(7)
_cell_measurement_reflns_used    9405
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.21
_cell_volume                     10522(4)
_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  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.1023
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            102692
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.047
_diffrn_reflns_theta_min         1.117
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5618
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.7538.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_description       blade
_exptl_crystal_F_000             3520
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.284
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2357
_refine_ls_number_reflns         34037
_refine_ls_number_restraints     1146
_refine_ls_restrained_S_all      1.280
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.1225
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3404
_refine_ls_wR_factor_ref         0.3706
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20763
_reflns_number_total             34037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01511k2.cif
_cod_data_source_block           mm497_sq_sq_sq_sq_sq
_cod_original_cell_volume        10522(3)
_cod_database_code               7158922
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7876(14)
 0.2124(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C190-C189 = C206-C205
 1.54 with sigma of 0.01
 C209-C208 \\sim C192-C191
 with sigma of 0.01
 C190-C189 \\sim C206-C205
 with sigma of 0.01
 O39-C203 \\sim O204-C185 \\sim O39-C189 \\sim O204-C205
 with sigma of 0.01
 O40-C191 \\sim O41-C208 \\sim O41-C186 \\sim O40-C200
 with sigma of 0.01
 O41-C185 \\sim O41-C187
 with sigma of 0.01
 N16-C183 \\sim N200-C201 \\sim N13-C188 \\sim N13-C207
 with sigma of 0.01
 O39-C189 \\sim O204-C205 \\sim O40-C191 \\sim O41-C208
 with sigma of 0.01
 O204-C203 \\sim O39-C185 \\sim O41-C200 \\sim O40-C186
 with sigma of 0.01
 N16-C182 \\sim N200-C199
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C190 \\sim C206: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C189 \\sim C205: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
O204 \\sim C205 \\sim C206: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C178 \\sim C179 \\sim C180 \\sim C181 \\sim C194 \\sim C195 \\sim C196 \\sim
C197: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
2A
C183 \\sim C184 \\sim C185 \\sim C186 \\sim C187 \\sim H187 \\sim C188 \\sim
C200 \\sim C201 \\sim C202 \\sim C203 \\sim C204 \\sim H204 \\sim C207: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
O40 \\sim O41: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
O39 \\sim C189 \\sim C190: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O29 \\sim O30 \\sim C135 \\sim C136 \\sim H136 \\sim C137 \\sim C138 \\sim C139
\\sim H139 \\sim C140 \\sim C141 \\sim H14A \\sim H14B \\sim C142 \\sim H14C
\\sim H14D \\sim H14E \\sim C143 \\sim H14F \\sim H14G \\sim C144 \\sim H14H
\\sim H14I \\sim H14J: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O39 \\sim O40 \\sim O41 \\sim O204 \\sim C183 \\sim C184 \\sim H184 \\sim C185
\\sim C186 \\sim C187 \\sim H187 \\sim C188 \\sim C189 \\sim H18A \\sim H18B
\\sim C190 \\sim H19A \\sim H19B \\sim H19C \\sim H199 \\sim C200 \\sim C201
\\sim C202 \\sim H202 \\sim C203 \\sim C204 \\sim H204 \\sim C205 \\sim H20A
\\sim H20B \\sim C206 \\sim H20C \\sim H20D \\sim H20E \\sim C207: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C191) = Uanis(C208)
Uanis(C178) = Uanis(C194)
Uanis(C207) = Uanis(C188)
Uanis(C204) = Uanis(C187)
Uanis(N200) = Uanis(N16)
Uanis(O204) = Uanis(O39)
Uanis(C200) = Uanis(C186)
Uanis(C185) = Uanis(C203)
Uanis(C201) = Uanis(C183)
Uanis(O41) = Uanis(O40)
Uanis(O38) = Uanis(O38A)
5. Rigid body (RIGU) restrains
 O39, O204, C189, C190, C205, C206
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O39, O40, O41, O204, N16, N200, C183, C184, C185, C186, C187, C188, C200,
 C201, C202, C203, C204, C207
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O40, O41, C191, C192, C208, C209
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O37, O38, H38, O38A, C176, C177, C178, C179, C180, C181, C182, C193, C194,
 C195, C196, C197, C198, C199
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O38A)=Sof(H38A)=Sof(O41)=Sof(O204)=Sof(N200)=Sof(C193)=Sof(C194)=
 Sof(H194)=Sof(C195)=Sof(H195)=Sof(C196)=Sof(H196)=Sof(C197)=Sof(C198)=
 Sof(C199)=Sof(H199)=Sof(C201)=Sof(C202)=Sof(H202)=Sof(C203)=Sof(C200)=
 Sof(C204)=Sof(H204)=Sof(C207)=Sof(C205)=Sof(H20A)=Sof(H20B)=Sof(C206)=
 Sof(H20C)=Sof(H20D)=Sof(H20E)=Sof(C208)=Sof(H20F)=Sof(H20G)=Sof(C209)=
 Sof(H20H)=Sof(H20I)=Sof(H20J)=1-FVAR(1)
 Sof(O38)=Sof(H38)=Sof(O39)=Sof(O40)=Sof(N16)=Sof(C176)=Sof(C177)=Sof(C178)=
 Sof(H178)=Sof(C179)=Sof(H179)=Sof(C180)=Sof(H180)=Sof(C181)=Sof(C182)=
 Sof(H182)=Sof(C183)=Sof(C184)=Sof(H184)=Sof(C185)=Sof(C186)=Sof(C187)=
 Sof(H187)=Sof(C188)=Sof(C189)=Sof(H18A)=Sof(H18B)=Sof(C190)=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=Sof(C191)=Sof(H19D)=Sof(H19E)=Sof(C192)=Sof(H19F)=
 Sof(H19G)=Sof(H19H)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C45(H45A,H45B), C47(H47A,H47B), C69(H69A,
 H69B), C71(H71A,H71B), C93(H93A,H93B), C95(H95A,H95B), C117(H11B,H11C),
 C119(H11G,H11H), C141(H14A,H14B), C143(H14F,H14G), C165(H16A,H16B), C167(H16F,
 H16G), C189(H18A,H18B), C191(H19D,H19E), C205(H20A,H20B), C208(H20F,H20G)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3A), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C14(H14),
 C16(H16), C19(H19), C25(H25), C27(H27), C28(H28), C29(H29), C34(H34), C35(H35),
  C36(H36A), C38(H38B), C40(H40), C43(H43), C49(H49), C51(H51), C52(H52),
 C53(H53), C58(H58), C59(H59), C60(H60), C62(H62), C64(H64), C67(H67), C73(H73),
  C75(H75), C76(H76), C77(H77), C82(H82), C83(H83), C84(H84), C86(H86),
 C88(H88), C91(H91), C97(H97), C99(H99), C100(H100), C101(H101), C106(H106),
 C107(H107), C108(H108), C110(H110), C112(H112), C115(H115), C121(H121),
 C123(H123), C124(H124), C125(H125), C130(H130), C131(H131), C132(H132),
 C134(H134), C136(H136), C139(H139), C145(H145), C147(H147), C148(H148),
 C149(H149), C154(H154), C155(H155), C156(H156), C158(H158), C160(H160),
 C163(H163), C169(H169), C171(H171), C172(H172), C173(H173), C178(H178),
 C179(H179), C180(H180), C182(H182), C184(H184), C187(H187), C194(H194),
 C195(H195), C196(H196), C199(H199), C202(H202), C204(H204)
7.c Fitted hexagon refined as free rotating group:
 C176(C177,C178,C179,C180,C181), C183(C184,C185,C186,C187,C188), C201(C202,
 C203,C200,C204,C207)
7.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C46(H46A,H46B,H46C), C48(H48A,H48B,
 H48C), C70(H70A,H70B,H70C), C72(H72A,H72B,H72C), C94(H94A,H94B,H94C), C96(H96A,
 H96B,H96C), C118(H11D,H11E,H11F), C120(H12A,H12B,H12C), C142(H14C,H14D,H14E),
 C144(H14H,H14I,H14J), C166(H16C,H16D,H16E), C168(H16H,H16I,H16J), C190(H19A,
 H19B,H19C), C192(H19F,H19G,H19H), C206(H20C,H20D,H20E), C209(H20H,H20I,H20J)
7.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O6(H6), O8(H8), O11(H11A), O13(H13), O16(H16K), O18(H18),
 O21(H21), O23(H23), O26(H26), O28(H28A), O31(H31), O33(H33), O36(H36),
 O38(H38), O38A(H38A)
;
_shelx_res_checksum              64221
_shelx_hkl_checksum              89854
_shelx_fab_checksum              23283
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'