Self-assembled orthoester cryptands: orthoester scope, post-functionalization, kinetic locking and tunable degradation kinetics.
Löw, Henrik; Mena-Osteritz, Elena; von Delius, Max; Chemical science 9 (2018) 4785–4793; doi:10.1039/c8sc01750f

data_1549320
_publ_section_title
;
 Self-assembled orthoester cryptands: orthoester scope,
 post-functionalization, kinetic locking and tunable degradation kinetics.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              4785
_journal_page_last               4793
_journal_paper_doi               10.1039/c8sc01750f
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C22 H42 Na O9, C32 H12 B F24'
_chemical_formula_sum            'C54 H54 B F24 Na O9'
_chemical_formula_weight         1336.77
_chemical_name_systematic
'(1,9-dibutyl-2,5,8,10,13,16,17,20,23-nonaoxabicyclo[7.7.7]tricosane)-sodium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-05 deposited with the CCDC.
2018-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                93.798(13)
_cell_angle_beta                 107.540(12)
_cell_angle_gamma                104.457(8)
_cell_formula_units_Z            2
_cell_length_a                   12.434(4)
_cell_length_b                   12.984(5)
_cell_length_c                   20.025(7)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.16
_cell_volume                     2949.7(18)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.1265
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            119640
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         2.096
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0892 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.9342.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1364
_exptl_crystal_preparation       'Chloroform solution'
_exptl_crystal_recrystallization_method
'Solvent layering of hexane over chloroform solution'
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0104(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     973
_refine_ls_number_reflns         10400
_refine_ls_number_restraints     512
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0595P)^2^+1.7806P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8651
_reflns_number_total             10400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01750f2.cif
_cod_data_source_block           hl17071_0m
_cod_depositor_comments
'Adding full bibliography for 1549313--1549320.cif.'
_cod_database_code               1549320
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.971
_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
 F00X-F00V \\sim F00X-F01D \\sim F00W-F01C
 with sigma of 0.04
 C46-F00X \\sim C46-F00U \\sim C46-F00W \\sim C46-F00V \\sim C46-F01C \\sim
C46-F01D \\sim C46-C15
 with sigma of 0.02
 F00R-F012 \\sim F00R-F01B \\sim F012-F01B \\sim F9AA-F0BA \\sim F0-F0BA
 with sigma of 0.04
 C48-F00R \\sim C48-F012 \\sim C48-F01B \\sim C48-C16 \\sim C48-F9AA \\sim
C48-F0 \\sim C48-F0BA
 with sigma of 0.02
 F00H-F00K \\sim F00H-F00Q \\sim F00K-F00Q \\sim F6AA-F7AA \\sim F7AA-F8AA
 with sigma of 0.04
 C29-F00H \\sim C29-F00K \\sim C29-F00Q \\sim C29-C21 \\sim C29-F6AA \\sim
C29-F7AA \\sim C29-F8AA
 with sigma of 0.02
 F00S-F00O \\sim F0AA-F2AA
 with sigma of 0.04
 C43-F1AA \\sim C43-F00S \\sim C43-F00P \\sim C43-F0AA \\sim C43-F00O \\sim
C43-F2AA \\sim C43-C10
 with sigma of 0.02
 F4AA-F3AA \\sim F5AA-F3AA \\sim F00N-F00I \\sim F00N-F00M \\sim F00I-F00M
 with sigma of 0.04
 C39-F4AA \\sim C39-F5AA \\sim C39-F00N \\sim C39-F00I \\sim C39-F00M \\sim
C39-F3AA \\sim C39-C11
 with sigma of 0.02
 F3BA-F1BA \\sim F1BA-F2BA \\sim F00T-F00F \\sim F00T-F00L \\sim F00F-F00L
 with sigma of 0.04
 C50-F3BA \\sim C50-F1BA \\sim C50-F00T \\sim C50-F00F \\sim C50-F00L \\sim
C50-C9 \\sim C50-F2BA
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C15, C46, F00W, F01C, F00U
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15, C46, F00V, F00X, F01D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10, C43, F00O, F00P, F00S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10, C43, F0AA, F2AA, F1AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, C29, F00H, F00Q, F00K
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C48, F012, F01B, F00R
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C39, F00N, F00M, F00I
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, C29, F6AA, F7AA, F8AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C48, F9AA, F0BA, F0
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, C39, F4AA, F3AA, F5AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9, C50, F00F, F00L, F00T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9, C50, F1BA, F2BA, F3BA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F00V)=Sof(F00X)=Sof(F01D)=1-FVAR(1)
 Sof(F00U)=Sof(F00W)=Sof(F01C)=FVAR(1)
 Sof(F0AA)=Sof(F1AA)=Sof(F2AA)=1-FVAR(2)
 Sof(F00O)=Sof(F00P)=Sof(F00S)=FVAR(2)
 Sof(F3AA)=Sof(F4AA)=Sof(F5AA)=1-FVAR(3)
 Sof(F00I)=Sof(F00M)=Sof(F00N)=FVAR(3)
 Sof(F6AA)=Sof(F7AA)=Sof(F8AA)=1-FVAR(4)
 Sof(F00H)=Sof(F00K)=Sof(F00Q)=FVAR(4)
 Sof(F9AA)=Sof(F0)=Sof(F0BA)=1-FVAR(5)
 Sof(F00R)=Sof(F012)=Sof(F01B)=FVAR(5)
 Sof(F1BA)=Sof(F2BA)=Sof(F3BA)=1-FVAR(6)
 Sof(F00F)=Sof(F00L)=Sof(F00T)=FVAR(6)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C31(H31A,
 H31B), C33(H33A,H33B), C35(H35A,H35B), C37(H37A,H37B), C38(H38A,H38B),
 C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C44(H44A,H44B), C45(H45A,H45B),
  C47(H47A,H47B), C49(H49A,H49B), C51(H51A,H51B), C52(H52A,H52B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C8(H8), C12(H12), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C25(H25), C26(H26)
5.c Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C54(H54A,H54B,H54C)
;
_olex2_exptl_crystal_mounting_method Glowing
_olex2_submission_special_instructions 'No special instructions were received'