#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/45/7054581.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_7054581
loop_
_publ_author_name
'Mačková, Michaela'
'Mikšátko, Jiří'
'Budka, Jan'
'Eigner, Václav'
'Cuřínová, Petra'
'Lhoták, Pavel'
_publ_section_title
;
 Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized
 in the 1,3-alternate conformation
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              1382
_journal_paper_doi               10.1039/C4NJ01956C
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C36 H20.00 N4 O12 S4'
_chemical_formula_sum            'C36 H20 N4 O12 S4'
_chemical_formula_weight         828.84
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2014-11-26 deposited with the CCDC.
2014-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.953(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2845(12)
_cell_length_b                   18.1827(17)
_cell_length_c                   18.8706(19)
_cell_measurement_reflns_used    15913
_cell_measurement_temperature    180
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     3722.8(7)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.111
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            41863
_diffrn_reflns_theta_full        73.144
_diffrn_reflns_theta_max         76.994
_diffrn_reflns_theta_min         4.746
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.75
_refine_ls_extinction_coef       42(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9798
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3857
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.1094
_refine_ls_shift/su_max          0.0035863
_refine_ls_shift/su_mean         0.0005259
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.247E+04 0.388E+04 0.223E+04 843. 160. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2180
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2180
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3203
_reflns_number_total             3857
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   4.55
_oxford_diffrn_Wilson_scale      0.15
_oxford_refine_ls_r_factor_ref   0.1203
_oxford_refine_ls_scale          2.47(5)
_oxford_reflns_number_all        3857
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c4nj01956c1.cif
_cod_data_source_block           4f
_cod_depositor_comments
'Adding full bibliography for 7054576--7054583.cif.'
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_original_formula_sum        'C36 H20.00 N4 O12 S4'
_cod_database_code               7054581
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
EQUIVALENCE PART(1001, OCC) PART(1002, OCC) 
WEIGHT -1 PART(1002, OCC) 
CONT EXTPARAM 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   ( 121,X'S) H   (1212,X'S) H   (1211,X'S) 
RIDE C   ( 123,X'S) H   (1231,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.440000 , 0.050000 = O(20) TO C(21) 
DISTANCE 1.460000 , 0.050000 = C(21) TO C(22) 
DISTANCE 1.160000 , 0.050000 = C(22) TO C(23) 
ANGLE 109.000000 , 1.000000 = O(20) TO C(21) TO C(22) 
DISTANCE 2.620000 , 0.050000 = C(21) TO C(23) 
DISTANCE 1.440000 , 0.050000 = O(20) TO C(121) 
DISTANCE 1.460000 , 0.050000 = C(121) TO C(122) 
DISTANCE 1.160000 , 0.050000 = C(122) TO C(123) 
ANGLE 109.000000 , 1.000000 = O(20) TO C(121) TO C(122) 
DISTANCE 2.620000 , 0.050000 = C(121) TO C(123) 
U(IJ)'S  0.0, 0.001000 = C(21) TO C(121) 
END                                                                             
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7013(5) 0.2869(4) 0.6840(3) 0.0503 1.0000 Uani . . . . .
S2 S 0.69073(16) 0.34722(12) 0.60818(9) 0.0648 1.0000 Uani . . . . .
C3 C 0.5693(5) 0.4071(4) 0.6125(3) 0.0453 1.0000 Uani . . . . .
C4 C 0.4696(6) 0.4156(4) 0.5506(3) 0.0484 1.0000 Uani . . . . .
C5 C 0.3827(6) 0.4679(4) 0.5525(3) 0.0516 1.0000 Uani . . . . .
C6 C 0.3882(6) 0.5120(4) 0.6125(3) 0.0581 1.0000 Uani . . . . .
C7 C 0.4879(6) 0.5037(4) 0.6756(3) 0.0516 1.0000 Uani . . . . .
S8 S 0.5000 0.56435(14) 0.7500 0.0744 1.0000 Uani S T . . .
S9 S 0.5000 0.12914(12) 0.7500 0.0579 1.0000 Uani S T . . .
C10 C 0.6193(5) 0.1909(3) 0.7456(3) 0.0436 1.0000 Uani . . . . .
C11 C 0.7284(5) 0.1900(3) 0.8012(3) 0.0464 1.0000 Uani . . . . .
C12 C 0.8230(5) 0.2372(4) 0.7970(3) 0.0477 1.0000 Uani . . . . .
C13 C 0.8108(5) 0.2859(4) 0.7413(3) 0.0505 1.0000 Uani . . . . .
C14 C 0.5777(5) 0.4515(3) 0.6749(3) 0.0469 1.0000 Uani . . . . .
C15 C 0.6069(5) 0.2387(3) 0.6856(3) 0.0453 1.0000 Uani . . . . .
O16 O 0.6736(4) 0.4416(2) 0.7367(2) 0.0540 1.0000 Uani . . . . .
C17 C 0.7788(7) 0.4869(5) 0.7398(4) 0.0874 1.0000 Uani . . . . .
C18 C 0.8721(7) 0.4734(5) 0.8085(4) 0.0774 1.0000 Uani . . . . .
C19 C 0.9484(8) 0.4589(6) 0.8621(5) 0.1110 1.0000 Uani . . . . .
O20 O 0.5021(4) 0.2380(3) 0.6283(2) 0.0548 1.0000 Uani D . . . .
C21 C 0.5069(11) 0.1833(12) 0.5713(15) 0.0805 0.794(10) Uani D U P 1 1
C22 C 0.3929(10) 0.1867(6) 0.5121(5) 0.0762 0.794(10) Uani D . P 1 1
C23 C 0.2972(11) 0.1889(8) 0.4626(6) 0.1048 0.794(10) Uani D . P 1 1
N24 N 0.2767(6) 0.4785(4) 0.4869(3) 0.0715 1.0000 Uani . . . . .
O25 O 0.2750(5) 0.4454(3) 0.4310(2) 0.0800 1.0000 Uani . . . . .
O26 O 0.1951(6) 0.5205(5) 0.4930(3) 0.1202 1.0000 Uani . . . . .
N27 N 0.9409(5) 0.2318(4) 0.8544(3) 0.0620 1.0000 Uani . . . . .
O28 O 0.9596(6) 0.1778(4) 0.8947(3) 0.1011 1.0000 Uani . . . . .
O29 O 1.0163(5) 0.2814(4) 0.8585(3) 0.0894 1.0000 Uani . . . . .
C121 C 0.498(4) 0.180(5) 0.578(6) 0.0805 0.206(10) Uani D U P 1 2
C122 C 0.617(3) 0.1754(15) 0.5624(15) 0.0443 0.206(10) Uani D . P 1 2
C123 C 0.710(3) 0.171(2) 0.5481(18) 0.0692 0.206(10) Uani D . P 1 2
H111 H 0.7379 0.1585 0.8416 0.0536 1.0000 Uiso R . . . .
H131 H 0.8743 0.3188 0.7416 0.0594 1.0000 Uiso R . . . .
H171 H 0.7539 0.5382 0.7368 0.1022 1.0000 Uiso R . . . .
H172 H 0.8119 0.4744 0.6981 0.1021 1.0000 Uiso R . . . .
H191 H 1.0073 0.4508 0.9076 0.1293 1.0000 Uiso R . . . .
H61 H 0.3253 0.5463 0.6110 0.0691 1.0000 Uiso R . . . .
H41 H 0.4611 0.3867 0.5078 0.0559 1.0000 Uiso R . . . .
H212 H 0.5185 0.1353 0.5920 0.0877 0.794(10) Uiso R . P 1 1
H211 H 0.5734 0.1950 0.5516 0.0877 0.794(10) Uiso R . P 1 1
H231 H 0.2227 0.1906 0.4240 0.1176 0.794(10) Uiso R . P 1 1
H1212 H 0.5006 0.1372 0.6073 0.0876 0.206(10) Uiso R . P 1 2
H1211 H 0.4262 0.1791 0.5376 0.0876 0.206(10) Uiso R . P 1 2
H1231 H 0.7881 0.1675 0.5384 0.0980 0.206(10) Uiso R . P 1 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
S2 . C1 C13 118.5(5) yes
S2 . C1 C15 121.6(5) yes
C13 . C1 C15 119.8(6) yes
C1 . S2 C3 102.9(3) yes
S2 . C3 C4 119.2(5) yes
S2 . C3 C14 121.1(4) yes
C4 . C3 C14 119.4(6) yes
C3 . C4 C5 118.3(6) yes
C3 . C4 H41 121.6 no
C5 . C4 H41 120.1 no
C4 . C5 C6 123.7(5) yes
C4 . C5 N24 119.2(6) yes
C6 . C5 N24 117.1(6) yes
C5 . C6 C7 118.6(7) yes
C5 . C6 H61 120.0 no
C7 . C6 H61 121.4 no
C6 . C7 S8 118.5(5) yes
C6 . C7 C14 118.8(6) yes
S8 . C7 C14 122.6(4) yes
C7 5_656 S8 C7 102.4(4) yes
C10 5_656 S9 C10 101.4(4) yes
S9 . C10 C11 119.2(5) yes
S9 . C10 C15 121.4(5) yes
C11 . C10 C15 119.3(6) yes
C10 . C11 C12 119.3(6) yes
C10 . C11 H111 120.2 no
C12 . C11 H111 120.5 no
C11 . C12 C13 122.3(6) yes
C11 . C12 N27 118.1(6) yes
C13 . C12 N27 119.6(6) yes
C1 . C13 C12 119.2(6) yes
C1 . C13 H131 120.7 no
C12 . C13 H131 120.1 no
C3 . C14 C7 121.1(5) yes
C3 . C14 O16 119.5(6) yes
C7 . C14 O16 119.3(6) yes
C10 . C15 C1 120.1(5) yes
C10 . C15 O20 120.3(6) yes
C1 . C15 O20 119.5(5) yes
C14 . O16 C17 114.2(5) yes
O16 . C17 C18 109.2(6) yes
O16 . C17 H171 109.1 no
C18 . C17 H171 110.0 no
O16 . C17 H172 109.1 no
C18 . C17 H172 109.4 no
H171 . C17 H172 109.9 no
C17 . C18 C19 176.3(12) yes
C18 . C19 H191 174.7 no
C15 . O20 C21 112.7(8) yes
C15 . O20 C121 114(4) yes
O20 . C21 C22 109.2(9) yes
O20 . C21 H212 110.4 no
C22 . C21 H212 110.3 no
O20 . C21 H211 109.0 no
C22 . C21 H211 108.4 no
H212 . C21 H211 109.5 no
C21 . C22 C23 179.4(13) yes
C22 . C23 H231 179.9 no
C5 . N24 O25 118.7(7) yes
C5 . N24 O26 117.3(6) yes
O25 . N24 O26 124.0(6) yes
C12 . N27 O28 118.5(7) yes
C12 . N27 O29 118.0(6) yes
O28 . N27 O29 123.5(6) yes
O20 . C121 C122 108.7(10) yes
O20 . C121 H1212 103.5 no
C122 . C121 H1212 100.8 no
O20 . C121 H1211 114.7 no
C122 . C121 H1211 117.8 no
H1212 . C121 H1211 109.5 no
C121 . C122 C123 178(4) yes
C122 . C123 H1231 177.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 S2 . 1.782(6) yes
C1 C13 . 1.400(8) yes
C1 C15 . 1.386(9) yes
S2 C3 . 1.770(7) yes
C3 C4 . 1.390(7) yes
C3 C14 . 1.409(9) yes
C4 C5 . 1.374(9) yes
C4 H41 . 0.946 no
C5 C6 . 1.374(9) yes
C5 N24 . 1.479(7) yes
C6 C7 . 1.404(8) yes
C6 H61 . 0.939 no
C7 S8 . 1.761(6) yes
C7 C14 . 1.391(9) yes
S9 C10 5_656 1.772(6) yes
S9 C10 . 1.772(6) yes
C10 C11 . 1.381(8) yes
C10 C15 . 1.404(8) yes
C11 C12 . 1.388(9) yes
C11 H111 . 0.937 no
C12 C13 . 1.352(8) yes
C12 N27 . 1.470(8) yes
C13 H131 . 0.932 no
C14 O16 . 1.368(6) yes
C15 O20 . 1.365(7) yes
O16 C17 . 1.433(8) yes
C17 C18 . 1.449(9) yes
C17 H171 . 0.972 no
C17 H172 . 0.986 no
C18 C19 . 1.164(10) yes
C19 H191 . 0.943 no
O20 C21 . 1.477(13) yes
O20 C121 . 1.41(3) yes
C21 C22 . 1.46(2) yes
C21 H212 . 0.950 no
C21 H211 . 0.950 no
C22 C23 . 1.219(13) yes
C23 H231 . 0.950 no
N24 O25 . 1.210(8) yes
N24 O26 . 1.225(9) yes
N27 O28 . 1.224(8) yes
N27 O29 . 1.228(8) yes
C121 C122 . 1.45(3) yes
C121 H1212 . 0.950 no
C121 H1211 . 0.950 no
C122 C123 . 1.16(3) yes
C123 H1231 . 0.950 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 H111 O25 8_555 167 0.937 2.490 3.410(7) yes
C19 H191 O26 6_665 151 0.943 2.342 3.20(2) yes
C4 H41 O28 8_454 173 0.946 2.433 3.372(9) yes
