Self-templated synthesis of an orthoformate in,in-cryptand and its bridgehead inversion by dynamic covalent exchange
Löw, Henrik; Mena-Osteritz, Elena; von Delius, Max; Chemical Communications  (2019) –; doi:10.1039/C9CC05968G

data_7124116
_publ_section_title
;
 Self-templated synthesis of an orthoformate in,in-cryptand and its
 bridgehead inversion by dynamic covalent exchange
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05968G
_journal_year                    2019
_chemical_formula_moiety         'C14 H26 O9'
_chemical_formula_sum            'C14 H26 O9'
_chemical_formula_weight         338.35
_chemical_name_systematic
(2,5,8,10,13,16,17,20,23-nonaoxabicyclo[7.7.7]tricosane)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-30 deposited with the CCDC.    2019-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.530(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9352(5)
_cell_length_b                   8.20386(19)
_cell_length_c                   14.9002(4)
_cell_measurement_reflns_used    5494
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.9010
_cell_measurement_theta_min      5.9820
_cell_volume                     1673.86(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00  11.00   1.00    1.00    --  -43.00  57.00   0.00   80
  2  \w    -81.00 -55.00   1.00    1.00    --  -43.00 125.00-180.00   26
  3  \w   -118.00 -10.00   1.00    1.00    --  -43.00 -77.00-150.00  108
  4  \w     15.00  40.00   1.00    1.00    --   43.00 -99.00-180.00   25
  5  \w     44.00 124.00   1.00    1.00    --  107.13 -61.00-120.00   80
  6  \w     78.00 120.00   1.00    1.00    --  107.13-125.00 -60.00   42
  7  \w     84.00 110.00   1.00    1.00    --  107.13-125.00  90.00   26
  8  \w     76.00 138.00   1.00    1.00    --  107.13 -77.00 120.00   62
  9  \w     71.00 161.00   1.00    1.00    --  107.13  15.00 -30.00   90
 10  \w    150.00 175.00   1.00    1.00    --  107.13  45.00 -90.00   25
 11  \w     91.00 178.00   1.00    1.00    --  107.13  61.00-150.00   87
 12  \w     85.00 114.00   1.00    1.00    --  107.13  45.00 -90.00   29
 13  \w     36.00 131.00   1.00    1.00    --  107.13 -45.00  60.00   95
 14  \w     35.00 109.00   1.00    1.00    --  107.13 -95.00  90.00   74
 15  \w     26.00  82.00   1.00    1.00    --   43.00-125.00 120.00   56
 16  \w     96.00 176.00   1.00    1.00    --  107.13 125.00 150.00   80
 17  \w     96.00 136.00   1.00    1.00    --  107.13 125.00 120.00   40
 18  \w   -123.00 -80.00   1.00    1.00    --  -43.00 -99.00 -30.00   43
 19  \w   -121.00 -83.00   1.00    1.00    --  -43.00 -99.00 -90.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0763446000
_diffrn_orient_matrix_UB_12      -0.0958864000
_diffrn_orient_matrix_UB_13      -0.0851446000
_diffrn_orient_matrix_UB_21      0.0425014000
_diffrn_orient_matrix_UB_22      -0.1612700000
_diffrn_orient_matrix_UB_23      0.0527053000
_diffrn_orient_matrix_UB_31      -0.0708834000
_diffrn_orient_matrix_UB_32      0.0066191000
_diffrn_orient_matrix_UB_33      0.0518747000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.086
_diffrn_reflns_theta_min         5.975
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_preparation       'Di-ethyl ether solution'
_exptl_crystal_recrystallization_method 'Solvent layering'
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0015(2)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0548P)^2^+0.2988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2862
_reflns_number_total             3329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05968g2.cif
_cod_data_source_block           hlo17112
_cod_original_cell_volume        1673.87(9)
_cod_database_code               7124116
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 H26 O9'
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.811
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B)
;
_olex2_date_sample_data_collection 2017-12-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.490
_oxdiff_exptl_absorpt_empirical_full_min 0.625