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_4129465
_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
'C68 H112 N4 O8, 1.25(C4 H8 O2), 1.5(C4 F8 I2), C H4 O, 4(Br)'
_chemical_formula_sum            'C80 H126 Br4 F12 I3 N4 O11.5'
_chemical_formula_weight         2256.18
_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   geom
_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                63.822(4)
_cell_angle_beta                 88.730(3)
_cell_angle_gamma                74.389(3)
_cell_formula_units_Z            2
_cell_length_a                   12.2852(4)
_cell_length_b                   20.8278(8)
_cell_length_c                   22.1139(10)
_cell_measurement_reflns_used    7608
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.1260
_cell_measurement_theta_min      3.8520
_cell_volume                     4860.0(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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega -110.00   -9.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -77.0000  -90.0000 101

  2 omega  -32.00   11.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000 -180.0000 43

  3 omega  -96.00   -2.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  125.0000   30.0000 94

  4 omega -116.00  -29.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -37.0000  150.0000 87

  5 omega    1.00   43.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       41.6513  -99.0000   30.0000 42

  6 omega   27.00  145.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -15.0000  150.0000 118

  7 omega   90.00  116.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000   30.0000 26

  8 omega   43.00   84.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -61.0000 -180.0000 41

  9 omega   57.00  121.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000 -120.0000 64

 10 omega   31.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000    0.0000 59

 11 omega   94.00  173.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  125.0000   90.0000 79

 12 omega   44.00  131.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -77.0000   60.0000 87

 13 omega   48.00   75.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  120.0000 27

 14 omega   29.00   88.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000   60.0000 59

 15 omega  121.00  177.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  125.0000   30.0000 56

 16 omega  109.00  134.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -61.0000 -180.0000 25

 17 omega   41.00  108.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000   30.0000 67

 18 omega   37.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  -60.0000 54

 19 omega   89.00  142.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   77.0000  150.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1126454000
_diffrn_orient_matrix_UB_12      -0.0456727000
_diffrn_orient_matrix_UB_13      0.0466564000
_diffrn_orient_matrix_UB_21      -0.0472773000
_diffrn_orient_matrix_UB_22      0.0277564000
_diffrn_orient_matrix_UB_23      0.0520523000
_diffrn_orient_matrix_UB_31      -0.0473579000
_diffrn_orient_matrix_UB_32      -0.0674987000
_diffrn_orient_matrix_UB_33      0.0348698000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35787
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.661
_diffrn_reflns_theta_min         3.759
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.154
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.542
_exptl_crystal_description       plate
_exptl_crystal_F_000             2266
_exptl_crystal_size_max          0.1511
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.0369
_refine_diff_density_max         1.177
_refine_diff_density_min         -1.892
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1063
_refine_ls_number_reflns         18966
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0697
_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^)+(0.0649P)^2^+1.7636P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.2061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11390
_reflns_number_total             18966
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06590_si_004.cif
_cod_data_source_block           6-MeOH@2-5_1.5
_cod_original_formula_sum        'C80 H126 Br4 F12 I3 N4 O11.50'
_cod_database_code               4129465
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C80 H160 Br4 F8 I2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2. Restrained distances
 C80-C79_$1
 1.52 with sigma of 0.02
 C79-C80_$1
 1.52 with sigma of 0.02
 O12-C80
 1.42 with sigma of 0.02
 O12-C79
 1.42 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F11) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
4. Others
 Fixed Sof: C79(0.5) H79A(0.5) H79B(0.5) C80(0.5) H80A(0.5) H80B(0.5) O12(0.5)
5.a Ternary CH refined with riding coordinates:
 C14(H14), C31(H31), C48(H48), C65(H65)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C15(H15A,H15B), C16(H16A,H16B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C32(H32A,
 H32B), C33(H33A,H33B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C49(H49A,H49B), C50(H50A,H50B),
  C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B), C61(H61A,H61B), C62(H62A,
 H62B), C63(H63A,H63B), C66(H66A,H66B), C67(H67A,H67B), N1(H1A,H1B), N2(H2A,
 H2B), N3(H3A,H3B), N4(H4A,H4B), C75(H75A,H75B), C76(H76A,H76B), C77(H77A,H77B),
  C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C23(H23), C40(H40), C57(H57)
5.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C), C30(H30A,H30B,H30C), C34(H34A,H34B,
 H34C), C47(H47A,H47B,H47C), C51(H51A,H51B,H51C), C64(H64A,H64B,H64C), C68(H68A,
 H68B,H68C), C110(H11C,H11D,H11E)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6A), O7(H7), O8(H8), O9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'