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_7219023
_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
'2(C36 H40 O12), 8.6(H2 O), C6 H16 N, Cl, 3(O)'
_chemical_formula_sum            'C78 H113.2 Cl N O35.6'
_chemical_formula_weight         1669.94
_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             2014-08-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2014-11-07 deposited with the CCDC.
2014-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                102.6693(14)
_cell_angle_beta                 92.3148(13)
_cell_angle_gamma                102.5625(14)
_cell_formula_units_Z            1
_cell_length_a                   11.48122(17)
_cell_length_b                   11.7421(2)
_cell_length_c                   17.0131(3)
_cell_measurement_reflns_used    22953
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.3310
_cell_measurement_theta_min      3.9340
_cell_volume                     2174.81(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -69.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -64.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.1176  -77.0000   30.0000 55

  3 omega  -48.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -45.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega -112.00  -66.00   1.0000    5.0000
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  6 omega  -47.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega  -89.00   -4.00   1.0000    5.0000
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  8 omega  -42.00  -10.00   1.0000    5.0000
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  9 omega   20.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   10.00   51.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   13.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   10.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega   13.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   58.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   13.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   57.00   83.00   1.0000    5.0000
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 17 omega   49.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   82.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   79.00  178.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   58.00  115.00   1.0000   20.0000
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 21 omega   83.00  156.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 22 omega  116.00  170.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 23 omega  109.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 24 omega   79.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega   31.00   88.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 26 omega  140.00  172.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 27 omega   50.00  143.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega   79.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 29 omega  117.00  177.00   1.0000   20.0000
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 30 omega   79.00  107.00   1.0000   20.0000
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 31 omega   79.00  107.00   1.0000   20.0000
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 32 omega   84.00  115.00   1.0000   20.0000
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 33 omega  130.00  178.00   1.0000   20.0000
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 34 omega  115.00  172.00   1.0000   20.0000
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 35 omega   86.00  176.00   1.0000   20.0000
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 36 omega  144.00  176.00   1.0000   20.0000
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 37 omega   83.00  137.00   1.0000   20.0000
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 38 omega   83.00  109.00   1.0000   20.0000
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 39 omega   79.00  105.00   1.0000   20.0000
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 40 omega   84.00  164.00   1.0000   20.0000
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    -      112.0000   61.0000  -30.0000 80

 41 omega   53.00  109.00   1.0000   20.0000
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 42 omega   79.00  107.00   1.0000   20.0000
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 43 omega   91.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 44 omega   79.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 45 omega   83.00  177.00   1.0000   20.0000
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    -      112.0000   61.0000 -180.0000 94

 46 omega   83.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 47 omega   72.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 48 omega  122.00  147.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 25

 49 omega  116.00  174.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega   83.00  134.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega   42.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 52 omega   79.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 53 omega   83.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 54 omega   83.00  151.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 55 omega   79.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 56 omega   83.00  160.00   1.0000   20.0000
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 57 omega   83.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 27

 58 omega  130.00  156.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 59 omega   83.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 60 omega   42.00   99.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 61 omega   79.00  177.00   1.0000   20.0000
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 62 omega   79.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
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 63 omega   48.00   81.00   1.0000   20.0000
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 64 omega   51.00   77.00   1.0000   20.0000
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;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1220228000
_diffrn_orient_matrix_UB_12      -0.0145601000
_diffrn_orient_matrix_UB_13      -0.0298444000
_diffrn_orient_matrix_UB_21      -0.0638130000
_diffrn_orient_matrix_UB_22      -0.1101861000
_diffrn_orient_matrix_UB_23      -0.0666428000
_diffrn_orient_matrix_UB_31      -0.0100027000
_diffrn_orient_matrix_UB_32      0.0822237000
_diffrn_orient_matrix_UB_33      -0.0579338000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42658
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.639
_diffrn_reflns_theta_min         1.825
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85217
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             890
_exptl_crystal_size_max          0.1924
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.0726
_refine_diff_density_max         1.672
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         9085
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      1.398
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0871
_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^)+(0.1531P)^2^+3.4013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2544
_refine_ls_wR_factor_ref         0.2596
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8267
_reflns_number_total             9085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ce01927j2.cif
_cod_data_source_block           5b@3
_cod_depositor_comments
'Adding full bibliography for 7219020--7219025.cif.'
_cod_original_cell_volume        2174.82(6)
_cod_original_formula_sum        'C78 H113.20 Cl N O35.60'
_cod_database_code               7219023
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C80 H80 N8 O3'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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, All N(H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C41-C42
 1.54 with sigma of 0.02
 C39-C41
 2.2 with sigma of 0.02
 N1-C41
 1.45 with sigma of 0.02
 N1-C42
 2.6 with sigma of 0.02
 O14A-H14A = O14A-H14B = O16B-H16C = O16B-H16D = O16A-H16A = O16A-H16B
 0.84 with sigma of 0.001
 H14A-H14B = H16C-H16D = H16A-H16B
 1.4 with sigma of 0.01
 H7-H8 = H7-H1_$1
 2.1 with sigma of 0.001
 C37-C38 \\sim C39-C40 \\sim C41-C42 \\sim C43-C44
 with sigma of 0.02
 N1-C37 \\sim N1-C39 \\sim N1-C41 \\sim N1-C43
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O17B) \\sim Ueq, Uanis(O16B) \\sim Ueq, Uanis(O18C) \\sim Ueq: with sigma
of 0.002 and sigma for terminal atoms of 0.004
Uanis(O18B) \\sim Ueq, Uanis(O17A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C41) \\sim Ueq, Uanis(C44) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C42) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(O17A) \\sim Ueq, Uanis(O18A)
\\sim Ueq, Uanis(O17B) \\sim Ueq, Uanis(O17B) \\sim Ueq, Uanis(O18) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C38) = Uanis(C44)
4. Others
 Fixed Sof: O13A(0.6) H13A(0.6) H13B(0.6) O14A(0.6) H14A(0.6) H14B(0.6)
 O13B(0.4) H13C(0.4) H13D(0.4) O14B(0.4) H14C(0.4) H14D(0.4) O16A(0.6)
 H16A(0.6) H16B(0.6) O16B(0.4) H16C(0.4) H16D(0.4) C37(0.5) H37A(0.5) H37B(0.5)
 C38(0.5) H38A(0.5) H38B(0.5) H38C(0.5) C39(0.3) H39A(0.3) H39B(0.3) C40(0.3)
 H40A(0.3) H40B(0.3) H40C(0.3) C41(0.2) H41A(0.2) H41B(0.2) C42(0.2) H42A(0.2)
 H42B(0.2) H42C(0.2) C43(0.5) H43A(0.5) H43B(0.5) C44(0.5) H44A(0.5) H44B(0.5)
 H44C(0.5) H41C(0.3) H39C(0.2) O18A(0.15) O17A(0.1) O17B(0.15) O18B(0.1)
 O18(0.3) H18D(0.3) H18E(0.3) O18C(0.75) O17C(0.75)
5.a Riding coordinates:
 O3(H3), O4(H4), O5(H5), O9(H9), O10(H10), O13A(H13A,H13B), O13B(H13C,H13D),
 O14B(H14C,H14D), O15(H15A,H15B), O16A(H16A,H16B), O16B(H16C,H16D), N1(H41C),
 N1(H39C), O18(H18D,H18E)
5.b Ternary CH refined with riding coordinates:
 C7(H7A), C16(H16), C25(H25), C34(H34)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B), C26(H26A,H26B), C35(H35A,H35B), C37(H37A,H37B),
 C39(H39A,H39B), C41(H41A,H41B), C43(H43A,H43B)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4A), C15(H15), C24(H24), C33(H33)
5.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C), C36(H36A,H36B,
 H36C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C42(H42A,H42B,H42C), C44(H44A,
 H44B,H44C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O6(H6), O7(H7), O8(H8), O11(H11), O12(H12)
;
_olex2_submission_special_instructions 'No special instructions were received'