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_1553063
_publ_section_title
;
 &#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), C64 H88 N4 O8, 2(C6 F4 I2), C0.5 Cl1.5, C0.24 H0.24 Cl0.72'
_chemical_formula_sum            'C77 H89 Br4 Cl3 F8 I4 N4 O8'
_chemical_formula_weight         2284.11
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_audit_update_record
;
2014-12-11 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.4165(3)
_cell_length_b                   18.4165(3)
_cell_length_c                   27.9044(7)
_cell_measurement_reflns_used    4011
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      61.8190
_cell_measurement_theta_min      3.9620
_cell_volume                     9464.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega   -2.00   60.00   0.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -180.0000 124

  2 omega   14.00   85.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.4688  -30.0000    0.0000 142

  3 omega   94.00  137.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.4688  125.0000    0.0000 86

  4 omega   72.00  143.00   0.5000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       83.4688   45.0000  150.0000 142
;
_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      0.0025905000
_diffrn_orient_matrix_UB_12      0.0425069000
_diffrn_orient_matrix_UB_13      0.0475234000
_diffrn_orient_matrix_UB_21      -0.0639993000
_diffrn_orient_matrix_UB_22      0.0473255000
_diffrn_orient_matrix_UB_23      -0.0168931000
_diffrn_orient_matrix_UB_31      -0.0538472000
_diffrn_orient_matrix_UB_32      -0.0543224000
_diffrn_orient_matrix_UB_33      0.0224088000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12644
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        62.500
_diffrn_reflns_theta_max         62.445
_diffrn_reflns_theta_min         3.167
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.643
_exptl_absorpt_correction_T_max  0.664
_exptl_absorpt_correction_T_min  0.294
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       plate
_exptl_crystal_F_000             4472
_exptl_crystal_size_max          0.1932
_exptl_crystal_size_mid          0.0837
_exptl_crystal_size_min          0.0327
_refine_diff_density_max         1.206
_refine_diff_density_min         -1.074
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.1053
_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^)+(0.1700P)^2^+45.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3000
_refine_ls_wR_factor_ref         0.3286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2462
_reflns_number_total             3713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00326h2.cif
_cod_data_source_block           CHCl3@1(5)4
_cod_original_cell_volume        9464.3(4)
_cod_original_sg_symbol_H-M      'P 4/n c c'
_cod_database_code               1553063
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C76 H96 Br4 N4 O8 F8 I4'
_reflns_odcompleteness_completeness 95.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.94
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H11 of C11, H6 of C6, H7 of C7, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H21 of C21, All O(H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim F18 \\sim F19: within 1.7A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C20 \\sim Cl1 \\sim Cl2: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(Cl3) \\sim Ueq, Uanis(Cl4) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of 0.02 and sigma for terminal
atoms of 0.04
4. Others
 Fixed Sof: Br1(0.6) Br1B(0.4) Cl1(0.125) Cl2(0.25) C20(0.125) Cl3(0.09)
 Cl4(0.09) C21(0.06) H21(0.06)
5.a Riding coordinates:
 O2(H2), C21(H21)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
5.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B)
5.d Me refined with riding coordinates:
 C9(H9A,H9B,H9C)
5.e Aromatic/amide H refined with riding coordinates:
 C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'