Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: the effect of size and charge concentration
Beyeh, N. K.; Pan, F.; Valkonen, A.; Rissanen, K.; CrystEngComm 17 (2015) 1182–; doi:10.1039/C4CE01927J

data_7219025
_publ_section_title
;
 Encapsulation of secondary and tertiary ammonium salts by resorcinarenes
 and pyrogallarenes: the effect of size and charge concentration
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1182
_journal_paper_doi               10.1039/C4CE01927J
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety
'C36 H40 O8, 3(C H4 O) 2(H2 O) C6 H16 N2, 2(Cl)'
_chemical_formula_sum            'C45 H72 Cl2 N2 O13'
_chemical_formula_weight         919.97
_chemical_name_systematic
;
 ?
;
_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   mixed
_audit_creation_date             2014-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-11-07 deposited with the CCDC.
2014-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                94.3636(17)
_cell_angle_beta                 101.9147(18)
_cell_angle_gamma                97.3470(18)
_cell_formula_units_Z            2
_cell_length_a                   11.5090(3)
_cell_length_b                   11.5275(2)
_cell_length_c                   18.1749(4)
_cell_measurement_reflns_used    21152
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.0750
_cell_measurement_theta_min      3.8670
_cell_volume                     2326.86(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0618862000
_diffrn_orient_matrix_UB_12      0.1002129000
_diffrn_orient_matrix_UB_13      -0.0362789000
_diffrn_orient_matrix_UB_21      -0.0261607000
_diffrn_orient_matrix_UB_22      -0.0791198000
_diffrn_orient_matrix_UB_23      -0.0754676000
_diffrn_orient_matrix_UB_31      -0.1209967000
_diffrn_orient_matrix_UB_32      0.0454812000
_diffrn_orient_matrix_UB_33      -0.0239998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24223
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.748
_diffrn_reflns_theta_min         3.888
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       brick
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.2083
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.1033
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         24223
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      3.079
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0981P)^2^+0.9142P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1638
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20623
_reflns_number_total             24223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ce01927j2.cif
_cod_data_source_block           5c@1
_cod_depositor_comments
'Adding full bibliography for 7219020--7219025.cif.'
_cod_database_code               7219025
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C40 H52 F6 N2 O8 P1 '
_diffrn_oxdiff_twin_integration_method simultaneous
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups, All O(H,H)
  groups
2. Shared sites
{O9A, O9B}
3. Restrained distances
 H9AA-O4
 2 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(Cl3A) \\sim Ueq, Uanis(Cl3D) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O12C) \\sim Ueq, Uanis(O12D) \\sim Ueq, Uanis(Cl3A) \\sim Ueq,
Uanis(Cl3B) \\sim Ueq, Uanis(Cl3C) \\sim Ueq, Uanis(O12E) \\sim Ueq,
Uanis(O12F) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O9A) = Uanis(O9B)
5. Others
 Fixed Sof: Cl3A(0.15) N2A(0.3) H2A(0.3) H40A(0.3) H40B(0.3) H40C(0.3)
 H40D(0.7) H40E(0.7) H40F(0.7) H41A(0.3) H41B(0.3) H41C(0.7) H41D(0.7)
 C42B(0.3) H42A(0.3) H42B(0.3) O9B(0.25) H9BA(0.25) C43A(0.75) H43D(0.75)
 H43E(0.75) H43F(0.75) O9A(0.75) H9AA(0.75) C43B(0.25) H43A(0.25) H43B(0.25)
 H43C(0.25) Cl3B(0.35) Cl3C(0.35) C42A(0.7) H42C(0.7) H42D(0.7) N2B(0.7)
 H2B(0.7) O12A(0.3) H12A(0.3) H12B(0.3) Cl3D(0.15) O12D(0.2) O12B(0.5)
 O12E(0.6) O12C(0.15) O12F(0.1) O12G(0.15)
6.a Free rotating group:
 O12A(H12A,H12B)
6.b Ternary CH refined with riding coordinates:
 C7(H7), C25(H25), C34(H34), C16(H16), N1(H1A), N2A(H2A), N2B(H2B)
6.c Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C17(H17A,H17B), C8(H8A,H8B), C35(H35A,H35B), C37(H37A,H37B),
 C39(H39A,H39B), C41(H41A,H41B), C41(H41C,H41D), C42B(H42A,H42B), C42A(H42C,
 H42D)
6.d Me refined with riding coordinates:
 C40(H40A,H40B,H40C), C40(H40D,H40E,H40F)
6.e Aromatic/amide H refined with riding coordinates:
 C24(H24), C6(H6A), C33(H33), C15(H15), C21(H21), C12(H12), C3(H3A), C30(H30)
6.f Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C9(H9A,H9B,H9C), C27(H27A,H27B,H27C), C36(H36A,H36B,
 H36C), C38(H38A,H38B,H38C), C43A(H43D,H43E,H43F), C44(H44A,H44B,H44C),
 C45(H45A,H45B,H45C), C43B(H43A,H43B,H43C)
6.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O1(H1), O8(H8), O4(H4), O3(H3), O7(H7A), O11(H11), O9B(H9BA),
 O10(H10), O9A(H9AA)
;