N-Alkyl ammonium resorcinarene salts: multivalent halogen-bonded deep-cavity cavitands
Beyeh, N. Kodiah; Valkonen, Arto; Bhowmik, Sandip; Pan, Fangfang; Rissanen, K.; Organic Chemistry Frontiers 2 (2015) 340–; doi:10.1039/C4QO00326H

data_1553064
_publ_section_title
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 &#x000D; N-Alkyl ammonium resorcinarene salts: multivalent halogen-bonded
 deep-cavity cavitands
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              340
_journal_paper_doi               10.1039/C4QO00326H
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         '4(Br), C2 H4 Cl2, C68 H104 N4 O8, C2 H6 O'
_chemical_formula_sum            'C72 H114 Br4 Cl2 N4 O9'
_chemical_formula_weight         1570.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-01
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_audit_update_record
;
2014-12-11 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.3371(3)
_cell_length_b                   23.5232(2)
_cell_length_c                   27.0473(3)
_cell_measurement_reflns_used    22210
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.1270
_cell_measurement_theta_min      3.1350
_cell_volume                     14848.0(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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9760
_diffrn_measurement_details
;
  1 omega  -49.00   20.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000   60.0000 69

  2 omega  -47.00   20.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  120.0000 67

  3 omega   53.00   96.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676 -125.0000   90.0000 43

  4 omega   28.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676 -125.0000 -120.0000 35

  5 omega   27.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.3676 -125.0000 -180.0000 28

  6 omega   39.00   73.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 34

  7 omega   43.00   79.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 36

  8 omega   41.00   75.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 34

  9 omega   45.00   71.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 26

 10 omega  137.00  178.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   90.0000 41

 11 omega   44.00   84.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 40

 12 omega   48.00   88.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 40

 13 omega  108.00  165.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -150.0000 57

 14 omega   31.00  163.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -150.0000 132
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0068254000
_diffrn_orient_matrix_UB_12      -0.0531740000
_diffrn_orient_matrix_UB_13      -0.0327604000
_diffrn_orient_matrix_UB_21      0.0131785000
_diffrn_orient_matrix_UB_22      0.0359757000
_diffrn_orient_matrix_UB_23      -0.0462174000
_diffrn_orient_matrix_UB_31      0.0642903000
_diffrn_orient_matrix_UB_32      -0.0130167000
_diffrn_orient_matrix_UB_33      0.0060655000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            55172
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         76.75
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.753
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             6560
_exptl_crystal_size_max          0.1791
_exptl_crystal_size_mid          0.1233
_exptl_crystal_size_min          0.1089
_refine_diff_density_max         2.038
_refine_diff_density_min         -1.152
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     864
_refine_ls_number_reflns         12047
_refine_ls_number_restraints     61
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+21.2397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2411
_reflns_number_gt                9727
_reflns_number_total             12047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4qo00326h2.cif
_cod_data_source_block           EtOH_C2Cl2@3
_cod_database_code               1553064
_chemical_oxdiff_formula         'C60 H60 O8 N4 Cl4'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C71-C72
 1.5 with sigma of 0.02
 C71-Cl1A = C72-Cl2A = C71-Cl1B = C72-Cl2B
 1.7 with sigma of 0.02
 H4-H5
 2.1 with sigma of 0.02
 C71-Cl1A \\sim C71-Cl1B \\sim C72-Cl2A \\sim C72-Cl2B
 with sigma of 0.01
 C16-C17A \\sim C16-C17B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17A) \\sim Ueq, Uanis(C17B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(Cl2A) \\sim Ueq, Uanis(Cl1B) \\sim Ueq, Uanis(Cl2B) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Others
 Sof(Cl1B)=1-FVAR(1)
 Sof(Cl1A)=FVAR(1)
 Sof(Cl2B)=Sof(H72C)=Sof(H72D)=1-FVAR(2)
 Sof(Cl2A)=Sof(H72A)=Sof(H72B)=FVAR(2)
 Sof(H16C)=Sof(H16D)=Sof(C17B)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(3)
 Sof(H16A)=Sof(H16B)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=FVAR(3)
5.a Riding coordinates:
 O8(H8)
5.b Ternary CH refined with riding coordinates:
 C8(H8A), C14(H14), C25(H25), C31(H31), C42(H42), C48(H48), C59(H59), C65(H65)
5.c Secondary CH2 refined with riding coordinates:
 C71(H71A,H71B), C72(H72A,H72B), C72(H72C,H72D), N1(H1A,H1B), N2(H2A,H2B),
 N3(H3A,H3B), N4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B),
 C16(H16C,H16D), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B),
  C29(H29A,H29B), C30(H30A,H30B), C32(H32A,H32B), C33(H33A,H33B), C41(H41A,
 H41B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B),
 C47(H47A,H47B), C49(H49A,H49B), C50(H50A,H50B), C58(H58A,H58B), C60(H60A,H60B),
  C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C66(H66A,
 H66B), C67(H67A,H67B), C70(H70A,H70B)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4C), C23(H23), C40(H40), C57(H57)
5.e Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C17B(H17D,H17E,H17F), C34(H34A,H34B,H34C), C51(H51A,
 H51B,H51C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6), O7(H7), O9(H9)
;