#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:11:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180172 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/68/7106845.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_7106845
loop_
_publ_author_name
'Jean-Manuel Raimundo'
'Zhongrui Chen'
'Olivier Siri'
_publ_section_title
;
 A new approach to inherent chirality through the N/S ratio and/or the
 position in mixed heterocalix[4]arenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              10410
_journal_paper_doi               10.1039/c1cc13390j
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H26 N6 O10 S4'
_chemical_formula_sum            'C28 H26 N6 O10 S4'
_chemical_formula_weight         734.79
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-02-08T11:08:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.044(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4209(6)
_cell_length_b                   9.2343(3)
_cell_length_c                   14.7501(4)
_cell_measurement_reflns_used    22018
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      1.69
_cell_measurement_wavelength     0.71073
_cell_volume                     3284.94(16)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.068
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22018
_diffrn_reflns_theta_full        28.64
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.114
_refine_ls_R_factor_gt           0.0736
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1575P)²+4.6592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.279
_reflns_number_gt                2822
_reflns_number_total             4060
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc13390j.txt
_cod_data_source_block           sc55
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7106845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
S1 S 1.14085(4) 0.22531(12) 0.92386(6) 0.0551(3) Uani 1 1 d . . .
S2 S 1.22047(6) -0.1532(3) 1.14011(11) 0.1126(8) Uani 1 1 d . . .
O2 O 0.95388(14) 0.4521(4) 1.17431(19) 0.0808(10) Uani 1 1 d . . .
O3 O 1.14309(14) 0.4523(4) 1.1812(2) 0.0788(10) Uani 1 1 d . . .
O1 O 0.89666(13) 0.3533(4) 1.0689(2) 0.0747(9) Uani 1 1 d . . .
N1 N 1.07121(13) 0.2267(3) 0.57350(17) 0.0452(7) Uani 1 1 d . . .
H1N H 1.1002 0.2493 0.5501 0.054 Uiso 1 1 calc R . .
N2 N 0.94349(14) 0.3843(3) 1.10318(18) 0.0482(7) Uani 1 1 d . . .
C2 C 0.98069(14) 0.2668(3) 0.9711(2) 0.0399(7) Uani 1 1 d . . .
C6 C 1.08228(15) 0.2701(3) 0.9738(2) 0.0407(7) Uani 1 1 d . . .
N3 N 1.14124(14) 0.3859(4) 1.10924(19) 0.0530(8) Uani 1 1 d . . .
C3 C 0.98917(14) 0.3414(3) 1.0564(2) 0.0399(7) Uani 1 1 d . . .
C12 C 1.09774(14) 0.2171(4) 0.7410(2) 0.0434(7) Uani 1 1 d . . .
H12 H 1.1038 0.3165 0.7414 0.052 Uiso 1 1 calc R . .
C5 C 1.08751(14) 0.3453(3) 1.0591(2) 0.0417(7) Uani 1 1 d . . .
O4 O 1.18310(14) 0.3508(5) 1.0787(2) 0.0859(11) Uani 1 1 d . . .
C11 C 1.07732(14) 0.1467(4) 0.6597(2) 0.0415(7) Uani 1 1 d . . .
O5 O 1.18086(15) -0.1983(7) 1.0571(3) 0.125(2) Uani 1 1 d . . .
C1 C 1.02883(14) 0.2345(4) 0.9335(2) 0.0418(7) Uani 1 1 d . . .
H1 H 1.0244 0.1858 0.8777 0.05 Uiso 1 1 calc R . .
C7 C 1.10913(14) 0.1381(4) 0.8219(2) 0.0443(7) Uani 1 1 d . . .
C4 C 1.04160(15) 0.3802(3) 1.0980(2) 0.0428(7) Uani 1 1 d . . .
H4 H 1.046 0.4307 1.1532 0.051 Uiso 1 1 calc R . .
C8 C 1.0997(2) -0.0088(4) 0.8224(2) 0.0580(10) Uani 1 1 d . . .
H8 H 1.1083 -0.0614 0.8765 0.07 Uiso 1 1 calc R . .
C9 C 1.0772(2) -0.0780(4) 0.7415(3) 0.0700(13) Uani 1 1 d . . .
H9 H 1.069 -0.1763 0.7419 0.084 Uiso 1 1 calc R . .
C10 C 1.0670(2) -0.0006(4) 0.6601(2) 0.0589(10) Uani 1 1 d . . .
H10 H 1.0531 -0.0478 0.6056 0.071 Uiso 1 1 calc R . .
C13 C 1.2654(3) -0.0229(8) 1.0998(6) 0.118(2) Uani 1 1 d . . .
H13A H 1.2455 0.0659 1.0853 0.177 Uiso 1 1 calc R . .
H13B H 1.2781 -0.0595 1.0458 0.177 Uiso 1 1 calc R . .
H13C H 1.2967 -0.0054 1.1467 0.177 Uiso 1 1 calc R . .
C14 C 1.2715(4) -0.2943(10) 1.1600(6) 0.143(3) Uani 1 1 d . . .
H14A H 1.2552 -0.3791 1.1823 0.214 Uiso 1 1 calc R . .
H14B H 1.302 -0.2624 1.2047 0.214 Uiso 1 1 calc R . .
H14C H 1.2846 -0.3167 1.1036 0.214 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 0 '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'
O O 0.0106 0.006 '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'
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
C6 S1 C7 100.75(16) . . ?
O5 S2 C13 105.5(3) . . ?
O5 S2 C14 106.0(4) . . ?
C13 S2 C14 95.5(4) . . ?
C2 N1 C11 120.7(3) 2_756 . ?
C2 N1 H1N 119.6 2_756 . ?
C11 N1 H1N 119.6 . . ?
O1 N2 O2 122.6(3) . . ?
O1 N2 C3 118.8(3) . . ?
O2 N2 C3 118.6(3) . . ?
N1 C2 C1 121.0(3) 2_756 . ?
N1 C2 C3 123.1(3) 2_756 . ?
C1 C2 C3 115.9(3) . . ?
C1 C6 C5 116.2(3) . . ?
C1 C6 S1 122.5(2) . . ?
C5 C6 S1 121.2(3) . . ?
O3 N3 O4 122.3(3) . . ?
O3 N3 C5 118.7(3) . . ?
O4 N3 C5 119.0(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 N2 116.5(3) . . ?
C2 C3 N2 122.4(3) . . ?
C11 C12 C7 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 N3 117.3(3) . . ?
C6 C5 N3 121.6(3) . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 N1 120.6(3) . . ?
C12 C11 N1 119.4(3) . . ?
C6 C1 C2 124.7(3) . . ?
C6 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C8 C7 C12 120.7(3) . . ?
C8 C7 S1 119.7(3) . . ?
C12 C7 S1 119.5(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
S2 C13 H13A 109.5 . . ?
S2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S2 C14 H14A 109.5 . . ?
S2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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
S1 C6 1.759(3) . ?
S1 C7 1.773(3) . ?
S2 O5 1.496(4) . ?
S2 C13 1.792(8) . ?
S2 C14 1.795(9) . ?
O2 N2 1.214(4) . ?
O3 N3 1.221(4) . ?
O1 N2 1.210(4) . ?
N1 C2 1.384(4) 2_756 ?
N1 C11 1.458(4) . ?
N1 H1N 0.86 . ?
N2 C3 1.456(4) . ?
C2 N1 1.383(4) 2_756 ?
C2 C1 1.408(5) . ?
C2 C3 1.421(4) . ?
C6 C1 1.386(5) . ?
C6 C5 1.425(4) . ?
N3 O4 1.224(5) . ?
N3 C5 1.450(4) . ?
C3 C4 1.377(5) . ?
C12 C11 1.387(4) . ?
C12 C7 1.389(4) . ?
C12 H12 0.93 . ?
C5 C4 1.375(5) . ?
C11 C10 1.384(5) . ?
C1 H1 0.93 . ?
C7 C8 1.377(5) . ?
C4 H4 0.93 . ?
C8 C9 1.388(5) . ?
C8 H8 0.93 . ?
C9 C10 1.386(5) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
