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_4129460
_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
'C52 H80 N4 O8, 1.4(C4 F8 I2), 0.75(C16 O8), 4(Br)'
_chemical_formula_sum            'C69.6 H80 Br4 F11.2 I2.8 N4 O14'
_chemical_formula_weight         2084.33
_space_group_crystal_system      tetragonal
_space_group_IT_number           130
_space_group_name_Hall           '-P 4a 2ac'
_space_group_name_H-M_alt        'P 4/n c c :2'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5404(7)
_cell_length_b                   17.5404(7)
_cell_length_c                   29.3347(8)
_cell_measurement_reflns_used    8370
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.7070
_cell_measurement_theta_min      3.5420
_cell_volume                     9025.3(6)
_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      N~2~
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -38.00   -1.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000  -30.0000 37

  2 omega  -89.00   -9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  125.0000 -180.0000 80

  3 omega  -45.00   -9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  125.0000  -30.0000 36

  4 omega   56.00  133.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  150.0000 77

  5 omega   32.00  106.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 74

  6 omega   39.00   80.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -120.0000 41

  7 omega   48.00   84.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 36

  8 omega  111.00  144.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000  -90.0000 33

  9 omega -114.00  -14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -57.0000 -150.0000 100

 10 omega -114.00  -14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -57.0000  -30.0000 100

 11 omega   59.00  143.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -150.0000 84
;
_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      0.0638240000
_diffrn_orient_matrix_UB_12      -0.0594856000
_diffrn_orient_matrix_UB_13      -0.0060140000
_diffrn_orient_matrix_UB_21      -0.0030655000
_diffrn_orient_matrix_UB_22      0.0114778000
_diffrn_orient_matrix_UB_23      -0.0520474000
_diffrn_orient_matrix_UB_31      0.0602016000
_diffrn_orient_matrix_UB_32      0.0636205000
_diffrn_orient_matrix_UB_33      0.0037605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            29957
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.728
_diffrn_reflns_theta_min         3.013
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.371
_exptl_absorpt_correction_T_max  0.366
_exptl_absorpt_correction_T_min  0.106
_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    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             4107
_exptl_crystal_size_max          0.2357
_exptl_crystal_size_mid          0.2081
_exptl_crystal_size_min          0.1062
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       0.00008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4004
_refine_ls_number_restraints     163
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.1213
_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^)+(0.1090P)^2^+83.3972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3027
_refine_ls_wR_factor_ref         0.3226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2832
_reflns_number_total             4004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06590_si_007.cif
_cod_data_source_block           6@3a-5_2
_cod_original_cell_volume        9025.3(7)
_cod_original_sg_symbol_H-M      'P 4/n c c'
_cod_original_formula_sum        'C69.60 H80 Br4 F11.20 I2.80 N4 O14'
_cod_database_code               4129460
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C50 H50 O8 N4 Br4 I2 F8'
_reflns_odcompleteness_completeness 99.91
_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 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
 C19-C19_$1
 1.52 with sigma of 0.02
 C1A-C1A_$1
 1.52 with sigma of 0.02
 H2-O1_$3
 1.8 with sigma of 0.02
 H2_$4-H1
 2 with sigma of 0.02
 C23-O16 = O16-C21
 1.45 with sigma of 0.02
 C21-C20
 1.52 with sigma of 0.02
 C23-C22
 1.52 with sigma of 0.02
 O1B-C20
 1.45 with sigma of 0.02
 C14B-C15B = C14-C15
 1.54 with sigma of 0.02
 I1-C14
 2.1 with sigma of 0.02
 C19_$2-O4 \\sim O4-C1A
 with sigma of 0.02
 F2-C14 \\sim C14-F1
 with sigma of 0.02
 F7-C15 \\sim C15-F3
 with sigma of 0.02
 F1B-C14B \\sim C14B-F4
 with sigma of 0.02
 F4-C14B \\sim C14B-F1B \\sim F1-C14 \\sim C14-F2
 with sigma of 0.02
 F4-F1B \\sim F1-F2
 with sigma of 0.02
 F4B-C15B \\sim C15B-F3
 with sigma of 0.02
 C17-O3 \\sim O3-C18 \\sim C19-O4 \\sim O4-C1A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F3B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C19) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C15B) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F7) \\sim Ueq,
Uanis(F4B) \\sim Ueq, Uanis(C14B) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(F1B)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(F2) \\sim Ueq,
Uanis(C14) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C13B)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(O1B) = Uanis(C22) = Uanis(C23) = Uanis(O16) = Uanis(C21) = Uanis(C20)
Uanis(F7) = Uanis(F3) = Uanis(F1) = Uanis(F2) = Uanis(F1B) = Uanis(F4) =
Uanis(F3B) = Uanis(F4B)
Uanis(C14B) = Uanis(C15B) = Uanis(C14) = Uanis(C15)
4. Others
 Fixed Sof: H12A(0.6) H12B(0.6) H12C(0.4) H12D(0.4) C13(0.6) H13A(0.6)
 H13B(0.6) H13C(0.6) C13B(0.4) H13D(0.4) H13E(0.4) H13F(0.4) C14(0.3) C15(0.3)
 F1(0.3) F2(0.3) F3(0.3) F7(0.3) I1(0.3) C14B(0.4) C15B(0.4) F1B(0.4) F3B(0.4)
 F4(0.4) F4B(0.4) I1B(0.4) C22(0.25) C23(0.25) C21(0.25) C17(0.5) C18(0.5)
 O3(0.5) C19(0.5) C1A(0.5) O4(0.5) C20(0.25) O1B(0.25)
5.a Ternary CH refined with riding coordinates:
 C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C12(H12C,H12D), N1(H1A,
 H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'