Ammonium Complexes of Orthoester Cryptands Are Inherently Dynamic and Adaptive.
Wang, Xiang; Shyshov, Oleksandr; Hanževački, Marko; Jäger, Christof M; von Delius, Max; Journal of the American Chemical Society 141 (2019) 8868–8876; doi:10.1021/jacs.9b01350

data_4127597
_publ_section_title
;
 Ammonium Complexes of Orthoester Cryptands Are Inherently Dynamic and
 Adaptive.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8868
_journal_page_last               8876
_journal_paper_doi               10.1021/jacs.9b01350
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C10 H19 O5.5, C16 H6 B0.5 F12, H1.5 N0.5'
_chemical_formula_sum            'C26 H26.5 B0.5 F12 N0.5 O5.5'
_chemical_formula_weight         667.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 137.02(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.92(2)
_cell_length_b                   8.848(8)
_cell_length_c                   19.069(16)
_cell_measurement_reflns_used    3422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.85
_cell_measurement_theta_min      2.53
_cell_volume                     2866(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.723
_diffrn_measured_fraction_theta_max 0.723
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.723
_diffrn_reflns_Laue_measured_fraction_max 0.723
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6961
_diffrn_reflns_point_group_measured_fraction_full 0.710
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_theta_full        23.389
_diffrn_reflns_theta_max         23.389
_diffrn_reflns_theta_min         2.139
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.5768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0742 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.7746.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colouress
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       needl
_exptl_crystal_F_000             1362
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     343
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0661P)^2^+3.6011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.696
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                2551
_reflns_number_total             2981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01350_si_002.cif
_cod_data_source_block           xw17084_0ma_a
_cod_original_formula_sum        'C26 H26.50 B0.50 F12 N0.50 O5.50'
_cod_database_code               4127597
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F8AA-F4 \\sim F8AA-F3 \\sim F4A-F8AB \\sim F3A-F8AB
 with sigma of 0.04
 C20-F8AA \\sim C20-F4A \\sim C20-F3A \\sim C20-F4 \\sim C20-F3 \\sim C20-F8AB
\\sim C20-C12
 with sigma of 0.02
 C22-O \\sim C22-C23
 with sigma of 0.02
 O-O4AA \\sim O-O2AA \\sim O-C14 \\sim O4AA-C14 \\sim O2AA-C14
 with sigma of 0.04
 C11-O \\sim C11-O4AA \\sim C11-O2AA \\sim C11-C14
 with sigma of 0.02
 C23-C22 \\sim C23-O1A
 with sigma of 0.02
 O0AA-C25 \\sim O0AA-C27
 with sigma of 0.02
 O2AA-C11 \\sim O2AA-C24 \\sim O2AA-C26
 with sigma of 0.02
 O1A-C23 \\sim O1B-C23
 with sigma of 0.02
 C16-O1A \\sim C16-O1B
 with sigma of 0.04
3. Rigid bond restraints
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 C18, C19, C20, C21, C22, B3BA, O, O4AA, O2AA, O1AA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6, C3, C1, C13, C10, C18, C5, C15, C9, C12, C7, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1A, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim B3BA \\sim O \\sim O4AA
\\sim O2AA \\sim O1AA: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C15 \\sim C9 \\sim C12 \\sim C7 \\sim C2 \\sim C5 \\sim C3 \\sim C1 \\sim C13
\\sim C10 \\sim C18 \\sim C6: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
O1A \\sim C16: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 C12, C20, F8AA, F4, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C20, F3A, F4A, F8AB
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, O1A, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O0AA, O2AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C23, O1A, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C23, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2AA, C24, C25, O0AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2AA, C26, C27, O0AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F8AB)=Sof(F3A)=Sof(F4A)=1-FVAR(1)
 Sof(F8AA)=Sof(F3)=Sof(F4)=FVAR(1)
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=1-FVAR(2)
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=Sof(H25B)=FVAR(2)
 Sof(H23C)=Sof(H23D)=Sof(O1B)=Sof(H28C)=Sof(H28D)=1-FVAR(3)
 Sof(O1A)=Sof(H23A)=Sof(H23B)=Sof(H28A)=Sof(H28B)=FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,
 H23B), C23(H23C,H23D), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B), C28(H28C,H28D)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C13(H13), C18(H18)
7.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'