Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures.
Pan, Fangfang; Beyeh, Ngong Kodiah; Rissanen, Kari; Journal of the American Chemical Society 137 (2015) 10406–10413; doi:10.1021/jacs.5b06590

data_4129462
_publ_section_title
;
 Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene
 Bromides: From Dimeric Dumbbell to Capsular Architectures.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10406
_journal_page_last               10413
_journal_paper_doi               10.1021/jacs.5b06590
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety
'8(Br), 5(C4 F8 I2), 2(C72 H88 N4 O8), 3(C4 H8 O2), H2 O'
_chemical_formula_sum            'C176 H202 Br8 F40 I10 N8 O23'
_chemical_formula_weight         5465.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                85.882(3)
_cell_angle_beta                 82.900(3)
_cell_angle_gamma                80.848(3)
_cell_formula_units_Z            1
_cell_length_a                   15.6129(7)
_cell_length_b                   17.9004(5)
_cell_length_c                   18.7393(6)
_cell_measurement_reflns_used    9153
_cell_measurement_temperature    123.00(2)
_cell_measurement_theta_max      75.8390
_cell_measurement_theta_min      3.9250
_cell_volume                     5123.6(3)
_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)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.00(2)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -95.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676  125.0000 -120.0000 93

  2 omega  -49.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676   37.0000 -120.0000 83

  3 omega -116.00   -8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676  -77.0000  120.0000 108

  4 omega -113.00  -13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8676  -57.0000    0.0000 100

  5 omega   40.00   98.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 58

  6 omega   42.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 57

  7 omega   29.00  109.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 80

  8 omega   36.00  116.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 80

  9 omega   92.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 86

 10 omega   59.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 32

 11 omega   40.00  141.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -90.0000 101

 12 omega   41.00  116.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   90.0000 75

 13 omega   59.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -30.0000 119
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0997377000
_diffrn_orient_matrix_UB_12      0.0146253000
_diffrn_orient_matrix_UB_13      -0.0013770000
_diffrn_orient_matrix_UB_21      -0.0035677000
_diffrn_orient_matrix_UB_22      -0.0849206000
_diffrn_orient_matrix_UB_23      0.0176409000
_diffrn_orient_matrix_UB_31      -0.0126489000
_diffrn_orient_matrix_UB_32      0.0139743000
_diffrn_orient_matrix_UB_33      0.0810541000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29344
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.745
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.553
_exptl_absorpt_correction_T_max  0.634
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_description       block
_exptl_crystal_F_000             2668
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.1413
_exptl_crystal_size_min          0.071
_refine_diff_density_max         4.677
_refine_diff_density_min         -3.223
_refine_diff_density_rms         0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1255
_refine_ls_number_reflns         18008
_refine_ls_number_restraints     160
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0970
_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^)+(0.1704P)^2^+56.1560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2765
_refine_ls_wR_factor_ref         0.2961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13733
_reflns_number_total             18008
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06590_si_002.cif
_cod_data_source_block           6@1-5_2
_cod_database_code               4129462
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C80 H80 O8 N4 I2 F8'
_reflns_odcompleteness_completeness 98.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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, All O(H,H) groups
2. Restrained distances
 C70-C71A = C70-C71B = C71A-C72A = C71B-C72B
 1.52 with sigma of 0.02
 O12-C87 = O12-C90
 1.42 with sigma of 0.02
 O13-C88 = O13-C89
 1.42 with sigma of 0.02
 C87-C88 = C89-C90
 1.52 with sigma of 0.02
 O9-C76 \\sim O9-C73
 with sigma of 0.02
 O9-C76 \\sim O9-C73 \\sim O10-C75 \\sim O10-C74
 with sigma of 0.02
 C73-C74 \\sim C75-C76
 with sigma of 0.02
 C77-F1 \\sim C77-F2 \\sim C78-F3 \\sim C78-F4 \\sim C79-F5 \\sim C79-F6 \\sim
C80-F7 \\sim C80-F8
 with sigma of 0.02
 C81-F9 \\sim C81-F10 \\sim C82-F11 \\sim C82-F12 \\sim C83-F13 \\sim C83-F14
\\sim C84-F15 \\sim C84-F16
 with sigma of 0.02
 C77-C78 \\sim C78-C79 \\sim C79-C80 \\sim C81-C82 \\sim C82-C83 \\sim C83-C84
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C87 \\sim C88: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C83 \\sim C84: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C71A) \\sim Ueq, Uanis(C72A) \\sim Ueq, Uanis(C89) \\sim Ueq, Uanis(F15)
\\sim Ueq, Uanis(F10) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C88) \\sim Ueq, Uanis(C90) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(F17) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F18) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H70C)=Sof(H70D)=Sof(C71B)=Sof(H71C)=Sof(H71D)=Sof(C72B)=Sof(H72D)=
 Sof(H72E)=Sof(H72F)=1-FVAR(1)
 Sof(H70A)=Sof(H70B)=Sof(C71A)=Sof(H71A)=Sof(H71B)=Sof(C72A)=Sof(H72A)=
 Sof(H72B)=Sof(H72C)=FVAR(1)
 Fixed Sof: O11(0.5) H11A(0.5) H11B(0.5) O12(0.5) O13(0.5) C87(0.5) H87A(0.5)
 H87B(0.5) C88(0.5) H88A(0.5) H88B(0.5) C89(0.5) H89A(0.5) H89B(0.5) C90(0.5)
 H90A(0.5) H90B(0.5)
5.a Riding coordinates:
 O3(H3), O8(H8), O11(H11A,H11B)
5.b Ternary CH refined with riding coordinates:
 C15(H15), C33(H33), C51(H51), C69(H69)
5.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B),
 C16(H16A,H16B), C17(H17A,H17B), C25(H25A,H25B), C26(H26A,H26B), C34(H34A,H34B),
  C35(H35A,H35B), C43(H43A,H43B), C44(H44A,H44B), C52(H52A,H52B), C53(H53A,
 H53B), C61(H61A,H61B), C62(H62A,H62B), C70(H70A,H70B), C70(H70C,H70D),
 C71A(H71A,H71B), C71B(H71C,H71D), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,
 H75B), C76(H76A,H76B), C87(H87A,H87B), C88(H88A,H88B), C89(H89A,H89B),
 C90(H90A,H90B)
5.d Aromatic/amide H refined with riding coordinates:
 C6(H6A), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C24(H24), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32), C42(H42), C46(H46), C47(H47),
 C48(H48), C49(H49), C50(H50), C60(H60), C64(H64), C65(H65), C66(H66), C67(H67),
  C68(H68)
5.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C), C54(H54A,H54B,H54C), C72A(H72A,H72B,
 H72C), C72B(H72D,H72E,H72F)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4), O5(H5), O6(H6), O7(H7)
;
_olex2_submission_special_instructions 'No special instructions were received'