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#$Date: 2016-08-07 10:53:59 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185108 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/30/1543096.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_1543096
loop_
_publ_author_name
'Qin, Lei'
'Hartley, Anna'
'Turner, Peter'
'Elmes, Robert B. P.'
'Jolliffe, Katrina A.'
_publ_section_title
;
 Macrocyclic squaramides: anion receptors with high sulfate binding
 affinity and selectivity in aqueous media
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4563
_journal_paper_doi               10.1039/C6SC01011C
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C28 H32 N4 O6 S2'
_chemical_formula_weight         584.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                73.717(2)
_cell_angle_beta                 84.157(2)
_cell_angle_gamma                69.545(2)
_cell_formula_units_Z            1
_cell_length_a                   8.4511(2)
_cell_length_b                   8.5911(2)
_cell_length_c                   10.8922(2)
_cell_measurement_reflns_used    26314
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      76.28
_cell_measurement_theta_min      2.57
_cell_volume                     711.23(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31d (release 11-02-2014 CrysAlis171 .NET)
(compiled Feb 11 2014,18:09:27)
;
_computing_molecular_graphics
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hï?1/2bschle,C.B., et al., 2011) 
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(1)
_diffrn_crystal_treatment
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26314
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.274
_diffrn_reflns_theta_min         4.228
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.108
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.37.35
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.308
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0357
_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/[σ²(Fo²)+(0.03P)²+0.3P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2896
_reflns_number_total             2962
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6sc01011c2.cif
_cod_data_source_block           3_kaj14mm_s1360
_cod_depositor_comments
'Adding full bibliography for 1543095--1543098.cif.'
_cod_database_code               1543096
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.743
_shelx_estimated_absorpt_t_max   0.866
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.69329(14) -0.41901(13) 0.54331(10) 0.0291(2) Uani 1 1 d . .
O2 O 0.79195(14) -0.07012(14) 0.40866(11) 0.0323(3) Uani 1 1 d . .
N1 N 0.33947(16) -0.24816(16) 0.39421(11) 0.0231(3) Uani 1 1 d . .
H1N H 0.352(2) -0.354(3) 0.4284(18) 0.032(5) Uiso 1 1 d . .
N2 N 0.42320(16) 0.11257(15) 0.27087(11) 0.0221(2) Uani 1 1 d . .
H2N H 0.329(3) 0.135(2) 0.2434(18) 0.029(5) Uiso 1 1 d . .
C1 C 0.46622(18) -0.19364(17) 0.40220(12) 0.0206(3) Uani 1 1 d . .
C2 C 0.62545(18) -0.27606(17) 0.47038(12) 0.0223(3) Uani 1 1 d . .
C3 C 0.67054(18) -0.11599(18) 0.41006(13) 0.0228(3) Uani 1 1 d . .
C4 C 0.50338(17) -0.03968(17) 0.34675(12) 0.0201(3) Uani 1 1 d . .
C5 C 0.50891(19) 0.23767(17) 0.21265(13) 0.0233(3) Uani 1 1 d . .
H5A H 0.6024 0.2197 0.2686 0.028 Uiso 1 1 calc R U
H5B H 0.4283 0.3557 0.2047 0.028 Uiso 1 1 calc R U
C6 C 0.57831(17) 0.21930(17) 0.08199(13) 0.0205(3) Uani 1 1 d . .
C7 C 0.73165(19) 0.09396(19) 0.06935(14) 0.0278(3) Uani 1 1 d . .
H7 H 0.7953 0.0212 0.1435 0.033 Uiso 1 1 calc R U
C8 C 0.79295(19) 0.0738(2) -0.05024(14) 0.0273(3) Uani 1 1 d . .
H8 H 0.8964 -0.0148 -0.0569 0.033 Uiso 1 1 calc R U
C9 C 0.70470(17) 0.18173(17) -0.16046(13) 0.0201(3) Uani 1 1 d . .
C10 C 0.55005(19) 0.30540(18) -0.14767(13) 0.0242(3) Uani 1 1 d . .
H10 H 0.4870 0.3789 -0.2219 0.029 Uiso 1 1 calc R U
C11 C 0.48669(18) 0.32272(18) -0.02757(14) 0.0240(3) Uani 1 1 d . .
H11 H 0.3796 0.4062 -0.0204 0.029 Uiso 1 1 calc R U
C12 C 0.78162(18) 0.16225(18) -0.28989(13) 0.0234(3) Uani 1 1 d . .
H12A H 0.8750 0.2101 -0.3079 0.028 Uiso 1 1 calc R U
H12B H 0.8302 0.0382 -0.2863 0.028 Uiso 1 1 calc R U
S1 S -0.05660(5) 0.39395(5) 0.19015(4) 0.02892(12) Uani 1 1 d . .
O3 O 0.10240(15) 0.27700(15) 0.14628(10) 0.0337(3) Uani 1 1 d . .
C13 C -0.0736(3) 0.3048(3) 0.35548(19) 0.0574(6) Uani 1 1 d . .
H13A H -0.1765 0.3773 0.3888 0.086 Uiso 1 1 calc R U
H13B H -0.0788 0.1887 0.3704 0.086 Uiso 1 1 calc R U
H13C H 0.0250 0.2987 0.3992 0.086 Uiso 1 1 calc R U
C14 C -0.0123(3) 0.5789(3) 0.1967(2) 0.0540(5) Uani 1 1 d . .
H14A H -0.1134 0.6598 0.2251 0.081 Uiso 1 1 calc R U
H14B H 0.0799 0.5445 0.2570 0.081 Uiso 1 1 calc R U
H14C H 0.0210 0.6345 0.1115 0.081 Uiso 1 1 calc R U
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'
O O 0.0492 0.0322 '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
C1 N1 C12 121.26(12) . 2_655
C1 N1 H1N 118.0(13) . .
C12 N1 H1N 115.5(13) 2_655 .
C4 N2 C5 121.70(13) . .
C4 N2 H2N 121.6(13) . .
C5 N2 H2N 115.8(13) . .
N1 C1 C4 135.22(13) . .
N1 C1 C2 132.48(13) . .
C4 C1 C2 92.28(11) . .
O1 C2 C1 134.31(13) . .
O1 C2 C3 136.73(14) . .
C1 C2 C3 88.93(11) . .
O2 C3 C4 135.52(13) . .
O2 C3 C2 136.84(14) . .
C4 C3 C2 87.58(11) . .
N2 C4 C1 135.39(14) . .
N2 C4 C3 133.44(13) . .
C1 C4 C3 91.17(11) . .
N2 C5 C6 111.00(11) . .
N2 C5 H5A 109.4 . .
C6 C5 H5A 109.4 . .
N2 C5 H5B 109.4 . .
C6 C5 H5B 109.4 . .
H5A C5 H5B 108.0 . .
C11 C6 C7 118.60(13) . .
C11 C6 C5 120.60(12) . .
C7 C6 C5 120.75(12) . .
C8 C7 C6 120.76(13) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C9 120.74(13) . .
C7 C8 H8 119.6 . .
C9 C8 H8 119.6 . .
C10 C9 C8 118.44(13) . .
C10 C9 C12 122.54(12) . .
C8 C9 C12 119.01(12) . .
C11 C10 C9 120.74(13) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C6 C11 C10 120.64(13) . .
C6 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
N1 C12 C9 113.26(11) 2_655 .
N1 C12 H12A 108.9 2_655 .
C9 C12 H12A 108.9 . .
N1 C12 H12B 108.9 2_655 .
C9 C12 H12B 108.9 . .
H12A C12 H12B 107.7 . .
O3 S1 C13 106.41(8) . .
O3 S1 C14 106.49(9) . .
C13 S1 C14 98.61(12) . .
S1 C13 H13A 109.5 . .
S1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
S1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
S1 C14 H14A 109.5 . .
S1 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
S1 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
O1 C2 1.2335(17) .
O2 C3 1.2183(18) .
N1 C1 1.3293(19) .
N1 C12 1.4566(18) 2_655
N1 H1N 0.86(2) .
N2 C4 1.3196(18) .
N2 C5 1.4663(17) .
N2 H2N 0.82(2) .
C1 C4 1.4200(18) .
C1 C2 1.451(2) .
C2 C3 1.5088(19) .
C3 C4 1.483(2) .
C5 C6 1.5118(18) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C11 1.3877(19) .
C6 C7 1.389(2) .
C7 C8 1.386(2) .
C7 H7 0.9500 .
C8 C9 1.390(2) .
C8 H8 0.9500 .
C9 C10 1.390(2) .
C9 C12 1.5192(19) .
C10 C11 1.390(2) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 N1 1.4565(18) 2_655
C12 H12A 0.9900 .
C12 H12B 0.9900 .
S1 O3 1.4961(11) .
S1 C13 1.761(2) .
S1 C14 1.7762(19) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.86(2) 2.05(2) 2.8530(16) 156.4(18) 2_646
N2 H2N O3 0.82(2) 2.08(2) 2.8608(17) 159.6(18) .
C5 H5A O2 0.99 2.58 3.2749(18) 126.9 .
C12 H12B O3 0.99 2.60 3.4734(18) 147.0 2_655
C13 H13A O1 0.98 2.65 3.512(2) 146.6 1_465
C13 H13C O2 0.98 2.62 3.364(3) 133.0 2_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C12 N1 C1 C4 17.0(2) 2_655 .
C12 N1 C1 C2 -160.48(13) 2_655 .
N1 C1 C2 O1 -1.4(3) . .
C4 C1 C2 O1 -179.66(16) . .
N1 C1 C2 C3 176.75(15) . .
C4 C1 C2 C3 -1.47(10) . .
O1 C2 C3 O2 2.2(3) . .
C1 C2 C3 O2 -175.96(18) . .
O1 C2 C3 C4 179.52(17) . .
C1 C2 C3 C4 1.41(10) . .
C5 N2 C4 C1 -169.60(14) . .
C5 N2 C4 C3 11.7(2) . .
N1 C1 C4 N2 4.3(3) . .
C2 C1 C4 N2 -177.60(16) . .
N1 C1 C4 C3 -176.64(15) . .
C2 C1 C4 C3 1.49(10) . .
O2 C3 C4 N2 -4.9(3) . .
C2 C3 C4 N2 177.69(15) . .
O2 C3 C4 C1 175.99(17) . .
C2 C3 C4 C1 -1.44(10) . .
C4 N2 C5 C6 92.38(15) . .
N2 C5 C6 C11 95.55(15) . .
N2 C5 C6 C7 -81.76(17) . .
C11 C6 C7 C8 0.7(2) . .
C5 C6 C7 C8 178.09(14) . .
C6 C7 C8 C9 1.9(2) . .
C7 C8 C9 C10 -2.8(2) . .
C7 C8 C9 C12 176.28(13) . .
C8 C9 C10 C11 1.2(2) . .
C12 C9 C10 C11 -177.86(13) . .
C7 C6 C11 C10 -2.3(2) . .
C5 C6 C11 C10 -179.71(13) . .
C9 C10 C11 C6 1.4(2) . .
C10 C9 C12 N1 -16.49(19) . 2_655
C8 C9 C12 N1 164.49(13) . 2_655
