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_7219024
_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         'C40 H48 O8, C2 H8 N, Cl, O H2, 2(C H4 O)'
_chemical_formula_sum            'C44 H66 Cl N O11'
_chemical_formula_weight         820.42
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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            4
_cell_length_a                   22.4355(13)
_cell_length_b                   12.3522(6)
_cell_length_c                   15.3459(7)
_cell_measurement_reflns_used    4354
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.3530
_cell_measurement_theta_min      2.1120
_cell_volume                     4252.8(4)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_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, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0150695000
_diffrn_orient_matrix_UB_12      -0.0502546000
_diffrn_orient_matrix_UB_13      0.0042090000
_diffrn_orient_matrix_UB_21      -0.0254587000
_diffrn_orient_matrix_UB_22      -0.0224830000
_diffrn_orient_matrix_UB_23      0.0205454000
_diffrn_orient_matrix_UB_31      -0.0111485000
_diffrn_orient_matrix_UB_32      -0.0163358000
_diffrn_orient_matrix_UB_33      -0.0411853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1348
_diffrn_reflns_av_unetI/netI     0.1119
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            52560
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         1.815
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44487
_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.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       plate
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_platon_squeeze_details
;
Summary and Remarks : N = NOTE, W = WARNING, E = ERROR

N: DISORDERED structure - ATOMS with Pop. .LT. 1.0 are not moved or as a group.
N: Number of moved primary input atoms: ..................................  117
N: Number of modified (= # ) ATOM labels .................................    4
N: Total Potential Solvent Accessible Void Vol ..................   667.4 Ang^3
N: Electron Count / Cell =    147 - To be included in D(calc), F000 & Mol.Wght.

;
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         7694
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0793
_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^)+(0.0642P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1652
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5414
_reflns_number_total             7694
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ce01927j2.cif
_cod_data_source_block           4a@2
_cod_depositor_comments
'Adding full bibliography for 7219020--7219025.cif.'
_cod_database_code               7219024
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C53 H39 N9 O7 Ru1'
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,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
2. Uiso/Uaniso restraints and constraints
Uanis(N1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(H42D)=Sof(H42E)=Sof(H42F)=Sof(N1B)=
 Sof(H1BA)=Sof(H1BB)=1-FVAR(1)
 Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(H42A)=
 Sof(H42B)=Sof(H42C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C38(H38), C28(H28), C8(H8A), C18(H18)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C39(H39A,H39B), C19(H19A,H19B), C29(H29A,H29B), N1A(H1AA,H1AB),
 N1B(H1BA,H1BB)
4.c Me refined with riding coordinates:
 C41(H41A,H41B,H41C), C41(H41D,H41E,H41F), C42(H42A,H42B,H42C), C42(H42D,H42E,
 H42F)
4.d Aromatic/amide H refined with riding coordinates:
 C36(H36), C6(H6A), C16(H16), C26(H26)
4.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C7(H7A,H7B,H7C), C30(H30A,H30B,H30C), C20(H20A,H20B,
 H20C), C37(H37A,H37B,H37C), C40(H40A,H40B,H40C), C27(H27A,H27B,H27C), C17(H17A,
 H17B,H17C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O8(H8), O3(H3), O1(H1), O6(H6), O7(H7), O4(H4), O5(H5)
;