Guest recognition enhanced by lateral interactions
Jiao, Tianyu; Cai, Kang; Liu, Zhichang; Wu, Guangcheng; Shen, Libo; Cheng, Chuyang; Feng, Yuanning; Stern, Charlotte L.; Stoddart, J. Fraser; Li, Hao; Chemical Science  (2019) –; doi:10.1039/C9SC00591A

data_1550926
_publ_section_title
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 Guest recognition enhanced by lateral interactions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00591A
_journal_year                    2019
_chemical_formula_moiety
'C78 H60 N12, 2(C17 H10 O), 5.5(F6 P), C2 H3 N, 0.5(Br)'
_chemical_formula_sum            'C114 H83 Br0.5 F33 N13 O2 P5.5'
_chemical_formula_weight         2504.22
_chemical_name_systematic        AzaEx2Cage-Pycho
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.3248(15)
_cell_length_b                   42.161(3)
_cell_length_c                   24.1600(16)
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      53.815
_cell_measurement_theta_min      3.640
_cell_volume                     27833(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 V2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.564
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'MX optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1356
_diffrn_reflns_av_unetI/netI     0.1648
_diffrn_reflns_Laue_measured_fraction_full 0.564
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34207
_diffrn_reflns_point_group_measured_fraction_full 0.564
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.433
_diffrn_reflns_theta_min         2.657
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    1.634
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.5117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0993 before and 0.0585 after correction. The Ratio of minimum to maximum transmission is 0.6814. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       needle
_exptl_crystal_F_000             10168
_exptl_crystal_recrystallization_method
'The material was recrystallised from --- by as supplied'
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1532
_refine_ls_number_reflns         14398
_refine_ls_number_restraints     1404
_refine_ls_restrained_S_all      1.223
_refine_ls_R_factor_all          0.2586
_refine_ls_R_factor_gt           0.1608
_refine_ls_shift/su_max          0.005
_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          0.3936
_refine_ls_wR_factor_ref         0.4438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6012
_reflns_number_total             14398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00591a2.cif
_cod_data_source_block           cx1196
_cod_original_cell_volume        27834(3)
_cod_original_formula_sum        'C114 H83 Br0.50 F33 N13 O2 P5.50'
_cod_database_code               1550926
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.535
_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
 C96-C103
 1.4 with sigma of 0.02
 O2-C96
 1.2 with sigma of 0.02
 O2-C103
 2.4 with sigma of 0.02
 C111-C102 \\sim C100-C112 \\sim C101-C98 \\sim C107-C106
 with sigma of 0.01
 C97-C105 \\sim C100-C103 \\sim C99-C110 \\sim C108-C98 \\sim C93_$1-C82_$1
\\sim C94_$1-C83_$1 ~
 C85_$1-C87_$1 \\sim C88_$1-C80_$1
 with sigma of 0.01
 C52-C3 \\sim C55-C2 \\sim C4-C1 \\sim C76-C29 \\sim C28-C25 \\sim C31-C30
 with sigma of 0.02
 C89-C80 \\sim C81-C80 \\sim C82-C81 \\sim C92-C82 \\sim C92-C91 \\sim C91-C89
 with sigma of 0.01
3. Rigid bond restraints
 O1, C79, C80, C81, C82, C83, C84, C85, C86, C87, C88, C89, C90, C91, C92, C93,
  C94, C95
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2, C96, C97, C98, C99, C100, C101, C102, C103, C104, C105, C106, C107, C108,
 C109, C110, C111, C112
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1 \\sim C79 \\sim C80 \\sim C81 \\sim C82 \\sim C83 \\sim C84 \\sim C85 \\sim
C86 \\sim C87 \\sim C88 \\sim C89 \\sim C90 \\sim C91 \\sim C92 \\sim C93 \\sim
C94 \\sim C95: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
O2 \\sim C96 \\sim C97 \\sim C98 \\sim C99 \\sim C100 \\sim C101 \\sim C102
\\sim C103 \\sim C104 \\sim C105 \\sim C106 \\sim C107 \\sim C108 \\sim C109
\\sim C110 \\sim C111 \\sim C112: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C105) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C96) \\sim Ueq, Uanis(C103)
\\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C101) \\sim Ueq,
Uanis(C100) \\sim Ueq, Uanis(C106) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(C99)
\\sim Ueq, Uanis(C97) \\sim Ueq, Uanis(C107) \\sim Ueq, Uanis(C111) \\sim Ueq,
Uanis(C98) \\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C110) \\sim Ueq, Uanis(C109)
\\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
Uanis(O1) \\sim Ueq, Uanis(C79) \\sim Ueq, Uanis(C80) \\sim Ueq, Uanis(C81)
\\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C88) \\sim Ueq,
Uanis(C91) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C87) \\sim Ueq, Uanis(C90)
\\sim Ueq, Uanis(C93) \\sim Ueq, Uanis(C86) \\sim Ueq, Uanis(C95) \\sim Ueq,
Uanis(C94) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C84)
\\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
5. Rigid body (RIGU) restrains
 N1, N2, N3, N4, N5, N6, N7, N8, N9, N10, N11, N12, C1, C2, C3, C4, C5, C6, C7,
  C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23,
 C24, C25, C26, C27, C28, C29, C30, C31, C32, C33, C34, C35, C36, C37, C38, C39,
  C40, C41, C42, C43, C44, C45, C46, C47, C48, C49, C50, C51, C52, C53, C54,
 C55, C56, C57, C58, C59, C60, C61, C62, C63, C64, C65, C66, C67, C68, C69, C70,
  C71, C72, C73, C74, C75, C76, C77, C78
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: Br1(0.125) Br2(0.125) Br3(0.125) Br4(0.125)
7.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B), C37(H37A,H37B), C48(H48A,H48B), C61(H61A,
 H61B), C72(H72A,H72B)
7.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26), C27(H27),
  C32(H32), C33(H33), C35(H35), C36(H36), C38(H38), C39(H39), C41(H41),
 C42(H42), C44(H44), C45(H45), C46(H46), C47(H47), C50(H50), C51(H51), C53(H53),
  C54(H54), C56(H56), C57(H57), C59(H59), C60(H60), C62(H62), C63(H63),
 C65(H65), C66(H66), C68(H68), C69(H69), C70(H70), C71(H71), C74(H74), C75(H75),
  C77(H77), C78(H78), C79(H79), C81(H81), C82(H82), C83(H83), C84(H84),
 C85(H85), C87(H87), C88(H88), C93(H93), C94(H94), C96(H96), C97(H97), C98(H98),
  C99(H99), C100(H100), C104(H104), C105(H105), C108(H108), C109(H109),
 C110(H110)
7.c Fitted hexagon refined as free rotating group:
 C101(C102,C103,C104,C105,C106), C107(C108,C109,C110,C111,C112)
7.d Idealised Me refined as rotating group:
 C148(H14A,H14B,H14C)
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_smtbx_masks_special_details
;
The solvent masking procedure as implemented in Olex2 was used to remove the
electronic contribution of solvent molecules from the refinement.  As the exact
solvent content is not known, only the atoms used in the refinement model are
reported in the formula here.

Total solvent accessible volume / cell = 7066.1 Ang^3^ [25.4%]
Total electron count / cell = 1815.8
;
_shelx_res_checksum              69549
_shelx_fab_checksum              35501
_olex2_date_sample_data_collection 2018-02-07
_olex2_date_sample_submission    2018-01-26
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id cx1196
_olex2_submission_special_instructions 'No special instructions were received'