Understanding the driving force for the molecular recognition of S6-corona[3]arene[3]pyridazine toward organic ammonium cations
Zhao, Meng-Yao; Guo, Qing-Hui; Wang, Mei-Xiang; Organic Chemistry Frontiers 5 (2018) 760–; doi:10.1039/C7QO00900C

data_1553935
_publ_section_title
;
 Understanding the driving force for the molecular recognition of
 S6-corona[3]arene[3]pyridazine toward organic ammonium cations
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              760
_journal_paper_doi               10.1039/C7QO00900C
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety
'C57 H54 N6 O12 S6, F6 P, 0.5(C12 H12 N2), C2 H3 N'
_chemical_formula_sum            'C65 H63 F6 N8 O12 P S6'
_chemical_formula_weight         1485.56
_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_method           SHELXL-2014/7
_audit_update_record
;
2017-10-03 deposited with the CCDC.
2017-11-15 downloaded from the CCDC.
;
_cell_angle_alpha                65.700(12)
_cell_angle_beta                 71.841(16)
_cell_angle_gamma                79.491(18)
_cell_formula_units_Z            2
_cell_length_a                   14.180(2)
_cell_length_b                   16.430(3)
_cell_length_c                   16.973(2)
_cell_measurement_reflns_used    8167
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4807
_cell_measurement_theta_min      1.3648
_cell_volume                     3417.8(10)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40572
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.200
_diffrn_reflns_theta_max         25.200
_diffrn_reflns_theta_min         1.751
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             1540
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.039
_refine_diff_density_max         1.215
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1038
_refine_ls_number_reflns         12278
_refine_ls_number_restraints     479
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.1783
_refine_ls_R_factor_gt           0.1451
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1227P)^2^+12.9819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3200
_refine_ls_wR_factor_ref         0.3417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9245
_reflns_number_total             12278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00900c2.cif
_cod_data_source_block           mx5363a
_cod_database_code               1553935
_olex2_refinement_description
;
1. 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
2. Restrained distances
 N9-C62 = N8-C69
 1.31 with sigma of 0.01
 N9-C63 = N8-C64
 1.47 with sigma of 0.01
 N9-C58 = C60-C59 = C61-C60 = C62-C61 = N9-C62 = C59-C58 = N8-C65 = C66-C65 =
 C67-C66 = C68-C67 = C69-C68
 1.39 with sigma of 0.01
 C28A-C27A
 1.54 with sigma of 0.01
 O3A-C10A
 1.2 with sigma of 0.01
 C12A-C11A = C12-C11
 1.54 with sigma of 0.01
 O4A-C10A
 1.35 with sigma of 0.01
 O4A-C11A
 1.45 with sigma of 0.01
 C5-C10A
 1.51 with sigma of 0.01
 O4A-O3A
 2.3 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C65 \\sim N9 \\sim C58 \\sim C62 \\sim C63 \\sim C59 \\sim C69 \\sim C61 \\sim
C64 \\sim C60 \\sim N8 \\sim C68 \\sim C67 \\sim C66: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04
O6 \\sim C27 \\sim C28 \\sim O6A \\sim C28A \\sim C27A \\sim O5 \\sim O5A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C12 \\sim C11A \\sim O4A \\sim C10A \\sim O3A \\sim C10 \\sim O3 \\sim O4 \\sim
C11 \\sim C12A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
Uanis(C65) \\sim Ueq, Uanis(N9) \\sim Ueq, Uanis(C58) \\sim Ueq, Uanis(C62)
\\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C69) \\sim Ueq,
Uanis(C61) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(N8)
\\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C66) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C69) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O6) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(O6A)
\\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(O5) \\sim Ueq,
Uanis(O5A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C10) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C12A)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11A) \\sim Ueq,
Uanis(O4A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(O3A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(F3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O6A)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=Sof(C27A)=Sof(H27C)=
 Sof(H27D)=Sof(O5A)=1-FVAR(1)
 Sof(O5)=Sof(O6)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=FVAR(1)
 Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C10A)=Sof(O3A)=Sof(O4A)=Sof(C11A)=
 Sof(H11C)=Sof(H11D)=1-FVAR(2)
 Sof(O3)=Sof(O4)=Sof(C10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12D)=
 Sof(H12E)=Sof(H12F)=FVAR(2)
 Fixed Sof: N9(0.5) N8(0.5) C58(0.5) C59(0.5) H59(0.5) C60(0.5) H60(0.5)
 C61(0.5) H61(0.5) C62(0.5) H62(0.5) C63(0.5) H63A(0.5) H63B(0.5) C64(0.5)
 H64A(0.5) H64B(0.5) C65(0.5) H65(0.5) C66(0.5) H66(0.5) C67(0.5) H67(0.5)
 C68(0.5) H68(0.5) C69(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B),
 C27(H27A,H27B), C30(H30A,H30B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
  C46(H46A,H46B), C49(H49A,H49B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,
 H55B), C63(H63A,H63B), C64(H64A,H64B), C27A(H27C,H27D), C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C22(H22), C25(H25), C40(H40), C43(H43), C59(H59), C60(H60),
 C61(H61), C62(H62), C65(H65), C66(H66), C67(H67), C68(H68)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12A(H12A,H12B,H12C), C31(H31A,H31B,H31C), C47(H47A,H47B,
 H47C), C50(H50A,H50B,H50C), C70(H70A,H70B,H70C), C28(H28A,H28B,H28C),
 C28A(H28D,H28E,H28F), C12(H12D,H12E,H12F)
;
_shelx_res_checksum              10194
_shelx_hkl_checksum              7014
_shelx_shelxl_version_number     2014/7