#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:07:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180169 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/65/7106582.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7106582
loop_
_publ_author_name
'Christopher J. Borman'
'Radu Custelcean'
'Ben P. Hay'
'Nathan L. Bill'
'Jonathan L. Sessler'
'Bruce A. Moyer'
_publ_section_title
;
 Supramolecular Organization of Calix[4]pyrrole with a
 Methyl-trialkylammonium Anion Exchanger Leads to Remarkable Reversal of
 Selectivity for Sulfate Extraction vs Nitrate
;
_journal_name_full               'Chem. Commun.'
_journal_page_first              7611
_journal_paper_doi               10.1039/c1cc12060c
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C42 H65 Cl4 N6 O6 S'
_chemical_formula_weight         923.86
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6011(7)
_cell_length_b                   20.9725(15)
_cell_length_c                   11.2587(8)
_cell_measurement_temperature    173(2)
_cell_volume                     2502.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15435
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_correction_T_min  0.8645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             982
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         2.415
_refine_diff_density_min         -1.352
_refine_diff_density_rms         0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.684
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.684
_refine_ls_R_factor_all          0.1829
_refine_ls_R_factor_gt           0.1469
_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/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4100
_refine_ls_wR_factor_ref         0.4435
_reflns_number_gt                4292
_reflns_number_total             6353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12060c.txt
_cod_data_source_block           c:\docume~1\radu\mydocu~1\x-ray\343\343s
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               7106582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.0678(3) 0.06302(12) 0.3455(3) 0.1225(12) Uani 1 1 d . . .
S1 S 0.21525(13) 0.2500 0.53878(11) 0.0264(4) Uani 1 2 d S . .
O1 O 0.0926(5) 0.2500 0.4815(4) 0.075(2) Uani 1 2 d S . .
N1 N 1.1620(3) 0.13602(16) 0.8160(3) 0.0265(8) Uani 1 1 d . . .
H5 H 1.1772 0.1597 0.7536 0.032 Uiso 1 1 calc R . .
C1 C 1.2529(4) 0.1143(2) 0.8983(4) 0.0293(9) Uani 1 1 d . . .
Cl2 Cl -0.2786(4) 0.08373(19) 0.1870(5) 0.187(2) Uani 1 1 d . . .
O2 O 0.2892(5) 0.1948(2) 0.5065(4) 0.0667(14) Uani 1 1 d . . .
N2 N 0.9422(4) 0.2500 0.7622(4) 0.0242(10) Uani 1 2 d S . .
H2 H 1.0130 0.2500 0.7232 0.029 Uiso 1 2 calc SR . .
C2 C 1.1910(5) 0.0782(2) 0.9798(5) 0.0384(11) Uani 1 1 d . . .
H14 H 1.2289 0.0565 1.0457 0.046 Uiso 1 1 calc R . .
O3 O 0.2001(4) 0.2500 0.6716(3) 0.0272(9) Uani 1 2 d S . .
N3 N 1.3815(4) 0.2500 0.8738(4) 0.0229(10) Uani 1 2 d S . .
H7 H 1.3376 0.2500 0.8063 0.028 Uiso 1 2 calc SR . .
C3 C 1.0605(4) 0.0791(2) 0.9488(5) 0.0349(11) Uani 1 1 d . . .
H22 H 0.9956 0.0585 0.9908 0.042 Uiso 1 1 calc R . .
O4 O 0.4043(12) 0.1206(6) 0.3475(11) 0.196(5) Uiso 1 1 d . . .
N4 N 0.0974(5) 0.2500 0.1619(4) 0.0305(12) Uani 1 2 d S . .
C4 C 1.0445(4) 0.1147(2) 0.8476(4) 0.0286(9) Uani 1 1 d . . .
N5 N 0.6421(6) 0.2500 0.4695(6) 0.098(4) Uani 1 2 d S . .
C5 C 0.9272(4) 0.1290(2) 0.7726(4) 0.0327(10) Uani 1 1 d . . .
C6 C 0.8795(4) 0.1962(2) 0.7966(4) 0.0261(9) Uani 1 1 d . . .
C7 C 0.7770(4) 0.2160(2) 0.8572(4) 0.0329(10) Uani 1 1 d . . .
H16 H 0.7164 0.1893 0.8930 0.039 Uiso 1 1 calc R . .
C8 C 1.4856(4) 0.2171(3) 1.0326(4) 0.0412(12) Uani 1 1 d . . .
H24 H 1.5245 0.1906 1.0915 0.049 Uiso 1 1 calc R . .
C9 C 1.4205(4) 0.1965(2) 0.9338(4) 0.0276(9) Uani 1 1 d . . .
C10 C 1.3914(4) 0.1295(2) 0.8880(4) 0.0319(10) Uani 1 1 d . . .
C11 C 0.9540(5) 0.1216(3) 0.6390(5) 0.0417(12) Uani 1 1 d . . .
H20A H 1.0174 0.1529 0.6162 0.063 Uiso 1 1 calc R . .
H20B H 0.8759 0.1286 0.5921 0.063 Uiso 1 1 calc R . .
H20C H 0.9856 0.0785 0.6240 0.063 Uiso 1 1 calc R . .
C12 C 0.8242(5) 0.0813(2) 0.8079(6) 0.0459(13) Uani 1 1 d . . .
H23A H 0.8538 0.0377 0.7943 0.069 Uiso 1 1 calc R . .
H23B H 0.7474 0.0891 0.7596 0.069 Uiso 1 1 calc R . .
H23C H 0.8060 0.0868 0.8921 0.069 Uiso 1 1 calc R . .
C13 C 1.4317(4) 0.1237(2) 0.7569(4) 0.0356(11) Uani 1 1 d . . .
H18A H 1.4145 0.0803 0.7282 0.053 Uiso 1 1 calc R . .
H18B H 1.5221 0.1327 0.7521 0.053 Uiso 1 1 calc R . .
H18C H 1.3839 0.1543 0.7078 0.053 Uiso 1 1 calc R . .
C14 C 1.4685(5) 0.0807(3) 0.9621(6) 0.0544(16) Uani 1 1 d . . .
H25A H 1.4486 0.0853 1.0462 0.082 Uiso 1 1 calc R . .
H25B H 1.5588 0.0884 0.9521 0.082 Uiso 1 1 calc R . .
H25C H 1.4473 0.0375 0.9353 0.082 Uiso 1 1 calc R . .
C15 C 0.0942(8) 0.2500 0.0281(6) 0.0443(18) Uani 1 2 d S . .
H15A H 0.1807 0.2500 -0.0005 0.066 Uiso 1 2 calc SR . .
H15B H 0.0499 0.2882 -0.0011 0.066 Uiso 0.50 1 calc PR . .
H15C H 0.0499 0.2118 -0.0011 0.066 Uiso 0.50 1 calc PR . .
C16 C 0.035(2) 0.1921(8) 0.2146(11) 0.090(6) Uani 0.50 1 d P . .
C16A C 0.176(2) 0.1934(9) 0.2060(11) 0.084(6) Uani 0.50 1 d P . .
C17 C 0.2301(16) 0.2500 0.1969(17) 0.077(7) Uani 0.50 2 d SP . .
C17A C -0.0320(19) 0.2500 0.197(2) 0.082(7) Uani 0.50 2 d SP . .
C18 C 0.5703(9) 0.2500 0.3544(8) 0.104(5) Uani 1 2 d S . .
H27A H 0.4796 0.2500 0.3692 0.156 Uiso 1 2 calc SR . .
H27B H 0.5919 0.2118 0.3091 0.156 Uiso 0.50 1 calc PR . .
H27C H 0.5919 0.2882 0.3091 0.156 Uiso 0.50 1 calc PR . .
C19 C 0.7814(7) 0.2500 0.4524(9) 0.066(3) Uani 1 2 d S . .
H26A H 0.8255 0.2500 0.5301 0.099 Uiso 1 2 calc SR . .
H26B H 0.8051 0.2882 0.4080 0.099 Uiso 0.50 1 calc PR . .
H26C H 0.8051 0.2118 0.4080 0.099 Uiso 0.50 1 calc PR . .
C20 C 0.6077(17) 0.1989(7) 0.5401(15) 0.172(6) Uiso 1 1 d . . .
H6A H 0.5162 0.1994 0.5498 0.258 Uiso 1 1 calc R . .
H6B H 0.6505 0.2025 0.6182 0.258 Uiso 1 1 calc R . .
H6C H 0.6323 0.1589 0.5022 0.258 Uiso 1 1 calc R . .
C21 C 0.3609(11) 0.0637(5) 0.3219(10) 0.108(3) Uiso 1 1 d . . .
H4A H 0.4301 0.0352 0.2979 0.130 Uiso 1 1 calc R . .
H4B H 0.2970 0.0659 0.2562 0.130 Uiso 1 1 calc R . .
C22 C 0.3018(14) 0.0394(7) 0.4347(14) 0.153(5) Uiso 1 1 d . . .
H7A H 0.2721 -0.0044 0.4224 0.229 Uiso 1 1 calc R . .
H7B H 0.2305 0.0668 0.4546 0.229 Uiso 1 1 calc R . .
H7C H 0.3649 0.0403 0.5000 0.229 Uiso 1 1 calc R . .
C23 C -0.1846(8) 0.0318(5) 0.2651(8) 0.089(3) Uani 1 1 d . . .
H5A H -0.2385 0.0070 0.3187 0.106 Uiso 1 1 calc R . .
H5B H -0.1482 0.0014 0.2082 0.106 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 112.1(2) . 4_565 ?
O1 S1 O2 112.1(2) . . ?
O2 S1 O2 106.0(5) 4_565 . ?
O1 S1 O3 109.0(3) . . ?
O2 S1 O3 108.76(19) 4_565 . ?
O2 S1 O3 108.76(19) . . ?
C4 N1 C1 109.6(4) . . ?
C2 C1 N1 106.9(4) . . ?
C2 C1 C10 130.8(4) . . ?
N1 C1 C10 122.3(4) . . ?
C6 N2 C6 110.8(5) . 4_565 ?
C1 C2 C3 108.1(4) . . ?
C9 N3 C9 110.3(5) 4_565 . ?
C4 C3 C2 108.0(4) . . ?
C17A N4 C17 148.1(14) . . ?
C17A N4 C15 106.4(12) . . ?
C17 N4 C15 105.5(9) . . ?
C17A N4 C16 57.2(10) . 4_565 ?
C17 N4 C16 109.1(10) . 4_565 ?
C15 N4 C16 113.2(6) . 4_565 ?
C17A N4 C16 57.2(10) . . ?
C17 N4 C16 109.1(10) . . ?
C15 N4 C16 113.2(6) . . ?
C16 N4 C16 106.6(16) 4_565 . ?
C17A N4 C16A 115.1(10) . 4_565 ?
C17 N4 C16A 52.9(9) . 4_565 ?
C15 N4 C16A 108.8(6) . 4_565 ?
C16 N4 C16A 59.3(11) 4_565 4_565 ?
C16 N4 C16A 137.6(8) . 4_565 ?
C17A N4 C16A 115.1(10) . . ?
C17 N4 C16A 52.9(9) . . ?
C15 N4 C16A 108.8(6) . . ?
C16 N4 C16A 137.6(8) 4_565 . ?
C16 N4 C16A 59.3(11) . . ?
C16A N4 C16A 102.4(17) 4_565 . ?
C3 C4 N1 107.4(4) . . ?
C3 C4 C5 130.8(4) . . ?
N1 C4 C5 121.7(4) . . ?
C20 N5 C20 100.9(15) . 4_565 ?
C20 N5 C18 111.3(8) . . ?
C20 N5 C18 111.3(8) 4_565 . ?
C20 N5 C19 110.5(8) . . ?
C20 N5 C19 110.5(8) 4_565 . ?
C18 N5 C19 111.9(7) . . ?
C4 C5 C6 110.9(3) . . ?
C4 C5 C12 107.7(4) . . ?
C6 C5 C12 108.2(4) . . ?
C4 C5 C11 110.6(4) . . ?
C6 C5 C11 109.7(4) . . ?
C12 C5 C11 109.6(4) . . ?
C7 C6 N2 106.8(4) . . ?
C7 C6 C5 130.1(4) . . ?
N2 C6 C5 123.0(4) . . ?
C6 C7 C7 107.8(3) . 4_565 ?
C9 C8 C8 108.4(3) . 4_565 ?
C8 C9 N3 106.4(4) . . ?
C8 C9 C10 131.3(4) . . ?
N3 C9 C10 122.3(4) . . ?
C1 C10 C9 110.9(4) . . ?
C1 C10 C14 108.7(4) . . ?
C9 C10 C14 109.2(4) . . ?
C1 C10 C13 110.5(4) . . ?
C9 C10 C13 109.6(3) . . ?
C14 C10 C13 107.8(4) . . ?
C17A C16 C16A 118.0(14) . . ?
C17A C16 N4 58.8(10) . . ?
C16A C16 N4 60.7(9) . . ?
C17 C16A C16 117.2(14) . . ?
C17 C16A N4 60.7(10) . . ?
C16 C16A N4 60.1(9) . . ?
C16A C17 C16A 127(2) . 4_565 ?
C16A C17 N4 66.4(10) . . ?
C16A C17 N4 66.4(10) 4_565 . ?
C16 C17A C16 118(2) 4_565 . ?
C16 C17A N4 64.1(10) 4_565 . ?
C16 C17A N4 64.1(10) . . ?
O4 C21 C22 105.8(11) . . ?
Cl1 C23 Cl2 116.7(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C23 1.648(9) . ?
S1 O1 1.435(5) . ?
S1 O2 1.450(4) 4_565 ?
S1 O2 1.450(4) . ?
S1 O3 1.509(4) . ?
N1 C4 1.379(5) . ?
N1 C1 1.395(5) . ?
C1 C2 1.370(6) . ?
C1 C10 1.510(6) . ?
Cl2 C23 1.703(9) . ?
N2 C6 1.372(5) . ?
N2 C6 1.372(5) 4_565 ?
C2 C3 1.417(7) . ?
N3 C9 1.367(5) 4_565 ?
N3 C9 1.367(5) . ?
C3 C4 1.369(7) . ?
O4 C21 1.308(14) . ?
N4 C17A 1.440(19) . ?
N4 C17 1.450(18) . ?
N4 C15 1.505(7) . ?
N4 C16 1.515(13) 4_565 ?
N4 C16 1.515(13) . ?
N4 C16A 1.524(14) 4_565 ?
N4 C16A 1.524(13) . ?
C4 C5 1.514(6) . ?
N5 C20 1.389(16) . ?
N5 C20 1.389(16) 4_565 ?
N5 C18 1.483(10) . ?
N5 C19 1.495(10) . ?
C5 C6 1.523(6) . ?
C5 C12 1.541(6) . ?
C5 C11 1.546(7) . ?
C6 C7 1.364(6) . ?
C7 C7 1.426(10) 4_565 ?
C8 C9 1.363(6) . ?
C8 C8 1.382(11) 4_565 ?
C9 C10 1.525(7) . ?
C10 C14 1.541(6) . ?
C10 C13 1.553(7) . ?
C16 C17A 1.42(2) . ?
C16 C16A 1.50(3) . ?
C16A C17 1.33(2) . ?
C17 C16A 1.33(2) 4_565 ?
C17A C16 1.42(2) 4_565 ?
C21 C22 1.519(18) . ?
