#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:59:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178454 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/75/4027544.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_4027544
loop_
_publ_author_name
'Mahendra P. Sonawane'
'Kristof Van Hecke'
'Jeroen Jacobs'
'Joice Thomas'
'Luc Van Meervelt'
'Wim Dehaen'
'Wim Van Rossom'
_publ_section_title
;
 Synthetic and Structural Exploration of
 [24]Tetrathiacalix[2]arene[2]pyrimidines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8444
_journal_page_last               8450
_journal_paper_doi               10.1021/jo301321w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C46 H48 N4 S6'
_chemical_formula_sum            'C46 H48 N4 S6'
_chemical_formula_weight         849.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0414(6)
_cell_length_b                   8.2503(3)
_cell_length_c                   33.9040(12)
_cell_measurement_temperature    100(2)
_cell_volume                     4207.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'crossed G\"obel mirrors'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            33545
_diffrn_reflns_theta_full        71.49
_diffrn_reflns_theta_max         71.49
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    3.297
_exptl_absorpt_correction_T_max  0.610
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0652
_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)+(0.1072P)²+4.4366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                3449
_reflns_number_total             4065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301321w_si_001_2.cif
_cod_data_source_block           wim154
_cod_database_code               4027544
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
C1 C 0.10588(19) 0.7427(4) 0.49989(8) 0.0155(6) Uani 1 1 d .
C2 C 0.1174(2) 0.9922(3) 0.47312(9) 0.0165(6) Uani 1 1 d .
C3 C 0.03456(19) 0.8102(4) 0.43999(8) 0.0166(6) Uani 1 1 d .
C4 C 0.04965(19) 0.6961(4) 0.46910(9) 0.0169(6) Uani 1 1 d .
H4 H 0.0232 0.5916 0.4682 0.020 Uiso 1 1 calc R
C5 C 0.1230(2) 1.2983(4) 0.43769(9) 0.0215(6) Uani 1 1 d .
H5A H 0.0583 1.2787 0.4354 0.026 Uiso 1 1 calc R
H5B H 0.1313 1.4152 0.4430 0.026 Uiso 1 1 calc R
C6 C 0.1651(2) 1.2605(4) 0.39848(9) 0.0199(6) Uani 1 1 d .
C7 C 0.2527(2) 1.2063(4) 0.39457(10) 0.0271(7) Uani 1 1 d .
H7 H 0.2874 1.1871 0.4175 0.033 Uiso 1 1 calc R
C8 C 0.2894(3) 1.1803(5) 0.35782(12) 0.0337(8) Uani 1 1 d .
H8 H 0.3493 1.1448 0.3556 0.040 Uiso 1 1 calc R
C9 C 0.2389(3) 1.2060(5) 0.32423(11) 0.0379(9) Uani 1 1 d .
H9 H 0.2641 1.1868 0.2990 0.045 Uiso 1 1 calc R
C10 C 0.1520(3) 1.2594(5) 0.32735(11) 0.0375(9) Uani 1 1 d .
H10 H 0.1176 1.2776 0.3043 0.045 Uiso 1 1 calc R
C11 C 0.1151(2) 1.2864(4) 0.36432(11) 0.0295(7) Uani 1 1 d .
H11 H 0.0554 1.3228 0.3664 0.035 Uiso 1 1 calc R
C12 C 0.21095(19) 0.6977(4) 0.56761(8) 0.0163(6) Uani 1 1 d .
H12A H 0.2599 0.6233 0.5749 0.020 Uiso 1 1 calc R
H12B H 0.2373 0.7914 0.5536 0.020 Uiso 1 1 calc R
C13 C 0.16553(19) 0.7567(4) 0.60456(9) 0.0168(6) Uani 1 1 d .
C14 C 0.1735(2) 0.6692(4) 0.63961(9) 0.0180(6) Uani 1 1 d .
H14 H 0.2096 0.5747 0.6403 0.022 Uiso 1 1 calc R
C15 C 0.12880(19) 0.7191(4) 0.67386(9) 0.0176(6) Uani 1 1 d .
C16 C 0.07900(19) 0.8615(4) 0.67223(8) 0.0177(6) Uani 1 1 d .
H16 H 0.0508 0.9001 0.6955 0.021 Uiso 1 1 calc R
C17 C 0.06964(19) 0.9488(4) 0.63707(9) 0.0175(6) Uani 1 1 d .
C18 C 0.1130(2) 0.8959(4) 0.60344(8) 0.0172(6) Uani 1 1 d .
H18 H 0.1069 0.9547 0.5795 0.021 Uiso 1 1 calc R
C19 C 0.1356(2) 0.6144(4) 0.71124(9) 0.0202(6) Uani 1 1 d .
C20 C 0.0956(2) 0.4467(4) 0.70209(10) 0.0290(7) Uani 1 1 d .
H20A H 0.0968 0.3798 0.7260 0.044 Uiso 1 1 calc R
H20B H 0.1307 0.3941 0.6814 0.044 Uiso 1 1 calc R
H20C H 0.0341 0.4596 0.6931 0.044 Uiso 1 1 calc R
C21 C 0.0843(2) 0.6879(5) 0.74618(9) 0.0290(8) Uani 1 1 d .
H21A H 0.1079 0.7961 0.7520 0.043 Uiso 1 1 calc R
H21B H 0.0913 0.6183 0.7694 0.043 Uiso 1 1 calc R
H21C H 0.0211 0.6963 0.7394 0.043 Uiso 1 1 calc R
C22 C 0.2342(2) 0.5949(4) 0.72317(9) 0.0238(7) Uani 1 1 d .
H22A H 0.2603 0.7020 0.7279 0.036 Uiso 1 1 calc R
H22B H 0.2667 0.5405 0.7019 0.036 Uiso 1 1 calc R
H22C H 0.2381 0.5298 0.7473 0.036 Uiso 1 1 calc R
C23 C 0.0067(2) 1.0925(4) 0.63652(8) 0.0181(6) Uani 1 1 d .
H23A H 0.0067 1.1420 0.6631 0.022 Uiso 1 1 calc R
H23B H -0.0541 1.0515 0.6315 0.022 Uiso 1 1 calc R
N1 N 0.13950(17) 0.8913(3) 0.50250(7) 0.0169(5) Uani 1 1 d .
N2 N 0.06768(16) 0.9614(3) 0.44140(7) 0.0162(5) Uani 1 1 d .
S1 S 0.13456(5) 0.59285(8) 0.53458(2) 0.0171(2) Uani 1 1 d .
S2 S 0.16349(5) 1.18643(9) 0.47987(2) 0.0207(2) Uani 1 1 d .
S3 S -0.03056(5) 0.74994(9) 0.39914(2) 0.0190(2) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
N1 C1 C4 122.3(3) . .
N1 C1 S1 120.7(2) . .
C4 C1 S1 117.0(2) . .
N2 C2 N1 128.3(3) . .
N2 C2 S2 119.9(2) . .
N1 C2 S2 111.8(2) . .
N2 C3 C4 123.0(3) . .
N2 C3 S3 119.6(2) . .
C4 C3 S3 117.3(2) . .
C3 C4 C1 116.5(3) . .
C3 C4 H4 121.8 . .
C1 C4 H4 121.8 . .
C6 C5 S2 116.9(2) . .
C6 C5 H5A 108.1 . .
S2 C5 H5A 108.1 . .
C6 C5 H5B 108.1 . .
S2 C5 H5B 108.1 . .
H5A C5 H5B 107.3 . .
C11 C6 C7 118.5(3) . .
C11 C6 C5 118.3(3) . .
C7 C6 C5 123.1(3) . .
C8 C7 C6 120.8(3) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C9 119.9(4) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C10 C9 C8 120.3(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 119.8(3) . .
C9 C10 H10 120.1 . .
C11 C10 H10 120.1 . .
C10 C11 C6 120.6(3) . .
C10 C11 H11 119.7 . .
C6 C11 H11 119.7 . .
C13 C12 S1 112.2(2) . .
C13 C12 H12A 109.2 . .
S1 C12 H12A 109.2 . .
C13 C12 H12B 109.2 . .
S1 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C18 C13 C14 119.9(3) . .
C18 C13 C12 120.0(3) . .
C14 C13 C12 120.1(3) . .
C13 C14 C15 120.8(3) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C16 C15 C14 118.2(3) . .
C16 C15 C19 122.8(3) . .
C14 C15 C19 119.0(3) . .
C15 C16 C17 121.4(3) . .
C15 C16 H16 119.3 . .
C17 C16 H16 119.3 . .
C18 C17 C16 119.5(3) . .
C18 C17 C23 122.0(3) . .
C16 C17 C23 118.4(3) . .
C17 C18 C13 120.3(3) . .
C17 C18 H18 119.9 . .
C13 C18 H18 119.9 . .
C15 C19 C21 112.4(3) . .
C15 C19 C20 108.2(3) . .
C21 C19 C20 108.3(3) . .
C15 C19 C22 109.7(2) . .
C21 C19 C22 108.7(3) . .
C20 C19 C22 109.5(3) . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C19 C21 H21A 109.5 . .
C19 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C19 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C17 C23 S3 116.5(2) . 5_576
C17 C23 H23A 108.2 . .
S3 C23 H23A 108.2 5_576 .
C17 C23 H23B 108.2 . .
S3 C23 H23B 108.2 5_576 .
H23A C23 H23B 107.3 . .
C1 N1 C2 115.4(3) . .
C2 N2 C3 114.4(3) . .
C1 S1 C12 103.39(14) . .
C2 S2 C5 103.24(15) . .
C3 S3 C23 102.22(14) . 5_576
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.329(4) .
C1 C4 1.397(4) .
C1 S1 1.760(3) .
C2 N2 1.334(4) .
C2 N1 1.340(4) .
C2 S2 1.761(3) .
C3 N2 1.344(4) .
C3 C4 1.382(4) .
C3 S3 1.767(3) .
C4 H4 0.9500 .
C5 C6 1.505(4) .
C5 S2 1.807(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C11 1.397(5) .
C6 C7 1.398(5) .
C7 C8 1.380(5) .
C7 H7 0.9500 .
C8 C9 1.385(6) .
C8 H8 0.9500 .
C9 C10 1.384(7) .
C9 H9 0.9500 .
C10 C11 1.388(6) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C13 1.507(4) .
C12 S1 1.823(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C18 1.395(4) .
C13 C14 1.396(4) .
C14 C15 1.403(4) .
C14 H14 0.9500 .
C15 C16 1.395(4) .
C15 C19 1.537(4) .
C16 C17 1.400(4) .
C16 H16 0.9500 .
C17 C18 1.384(4) .
C17 C23 1.517(4) .
C18 H18 0.9500 .
C19 C21 1.538(4) .
C19 C20 1.540(5) .
C19 C22 1.546(4) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 S3 1.811(3) 5_576
C23 H23A 0.9900 .
C23 H23B 0.9900 .
S3 C23 1.811(3) 5_576
