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_7219021
_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(C40 H48 O8), 2(C H4 O), C3 H10 N, 4(H2 O), Cl'
_chemical_formula_sum            'C85 H122 Cl N O22'
_chemical_formula_weight         1545.28
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           48
_space_group_name_Hall           '-P 2ab 2bc'
_space_group_name_H-M_alt        'P n n n'
_symmetry_space_group_name_Hall  '-P 2ab 2bc'
_symmetry_space_group_name_H-M   'P n n n :2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-05-07
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6722(4)
_cell_length_b                   15.1699(5)
_cell_length_c                   22.9465(11)
_cell_measurement_reflns_used    3695
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.3220
_cell_measurement_theta_min      2.2550
_cell_volume                     4411.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      173.15
_diffrn_detector_area_resol_mean 32.0214
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -93.00  -68.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.8607 -178.0000  120.0000 25

  2 omega   -7.00   86.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6419   77.0000 -150.0000 93

  3 omega   12.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6419   37.0000    0.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0050857000
_diffrn_orient_matrix_UB_12      -0.0362233000
_diffrn_orient_matrix_UB_13      0.0193102000
_diffrn_orient_matrix_UB_21      0.0020723000
_diffrn_orient_matrix_UB_22      0.0291932000
_diffrn_orient_matrix_UB_23      0.0241378000
_diffrn_orient_matrix_UB_31      -0.0557122000
_diffrn_orient_matrix_UB_32      0.0044102000
_diffrn_orient_matrix_UB_33      -0.0008374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12721
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_min         1.836
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.2729
_exptl_crystal_size_min          0.1837
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4003
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0626
_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^)+(0.1142P)^2^+2.2983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2050
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3009
_reflns_number_total             4003
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ce01927j2.cif
_cod_data_source_block           5a@2
_cod_depositor_comments
'Adding full bibliography for 7219020--7219025.cif.'
_cod_original_cell_volume        4411.2(3)
_cod_database_code               7219021
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C48 H72 N12 O6'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C22A-C23A = C22A-C24A = C23A-C24A = C22B-C23B = C22B-C24B = C23B-C24B
 2.4 with sigma of 0.04
 N1A-C22A = N1A-C23A = N1A-C24A = N1B-C22B = N1B-C23B = N1B-C24B
 1.5 with sigma of 0.02
 H4B-H15 = H3B-H15
 2.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Uiso(N1B)=Uiso(N1A)=0.8*FVAR(2)
 Uiso(C22B)=Uiso(C23B)=Uiso(C24B)=Uiso(C22A)=Uiso(C23A)=Uiso(C24A)=FVAR(1)
 Fixed Sof: H2A(0.5) H2B(0.5) H3A(0.5) H3B(0.5) H4B(0.5) H4A(0.5) O9(0.5)
 H9(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) N1B(0.125) H1BA(0.125)
 C22B(0.125) H22A(0.125) H22B(0.125) H22C(0.125) C23B(0.125) H23A(0.125)
 H23B(0.125) H23C(0.125) C24B(0.125) H24A(0.125) H24B(0.125) H24C(0.125)
 N1A(0.125) H1AB(0.125) C22A(0.125) H22D(0.125) H22E(0.125) H22F(0.125)
 C23A(0.125) H23D(0.125) H23E(0.125) H23F(0.125) C24A(0.125) H24D(0.125)
 H24E(0.125) H24F(0.125) O8(0.5) H8A(0.5) H8B(0.5) Cl3(0.05) O5(0.5) H5A(0.5)
 H5B(0.5) Cl2(0.1) Cl1(0.1) H1BB(0.5) H1AA(0.5)
5.a Riding coordinates:
 O2(H2B), O4(H4A), C22B(H22A,H22B,H22C), C22A(H22D,H22E,H22F), C23A(H23D,H23E,
 H23F)
5.b Free rotating group:
 O8(H8A,H8B), O5(H5A,H5B)
5.c Ternary CH refined with riding coordinates:
 C5(H5), C15(H15), N1B(H1BA), N1A(H1AB)
5.d Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C16(H16A,H16B)
5.e Aromatic/amide H refined with riding coordinates:
 C14(H14), C20(H20)
5.f Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C17(H17A,H17B,H17C),
 C21(H21A,H21B,H21C), C23B(H23A,H23B,H23C), C24B(H24A,H24B,H24C), C24A(H24D,
 H24E,H24F)
5.g Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O3(H3A), O3(H3B), O4(H4B), O9(H9), O1(H1BB), O1(H1AA)
;