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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/1/54/30/1543095.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_1543095
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                101.755(4)
_cell_angle_beta                 103.383(5)
_cell_angle_gamma                98.623(4)
_cell_formula_units_Z            1
_cell_length_a                   8.4474(5)
_cell_length_b                   8.6414(4)
_cell_length_c                   10.5047(6)
_cell_measurement_reflns_used    4050
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      75.7860
_cell_measurement_theta_min      4.4460
_cell_volume                     714.54(7)
_computing_cell_refinement
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_collection
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction
;
  CrysAlisPro, Agilent Technologies,
;
_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 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_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 0.996
_diffrn_measured_fraction_theta_max 0.979
_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  0.0170
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6264
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.143
_diffrn_reflns_theta_min         4.466
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.098
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.36.28
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.323
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.323
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0328
_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)+(0.04P)²+0.1P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2716
_reflns_number_total             2933
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6sc01011c2.cif
_cod_data_source_block           1_kaj14pt1
_cod_depositor_comments
'Adding full bibliography for 1543095--1543098.cif.'
_cod_database_code               1543095
_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.
;
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 0.29452(12) -0.06415(12) 0.12002(10) 0.0289(2) Uani 1 1 d . .
O2 O 0.33645(13) 0.32176(12) 0.24828(10) 0.0303(2) Uani 1 1 d . .
N1 N 0.29731(14) -0.13141(13) 0.41787(11) 0.0228(2) Uani 1 1 d . .
H1N H 0.300(2) -0.113(2) 0.501(2) 0.030(4) Uiso 1 1 d . .
N2 N 0.30268(14) 0.24257(13) 0.53642(11) 0.0226(2) Uani 1 1 d . .
H2N H 0.304(2) 0.190(2) 0.5991(19) 0.027(4) Uiso 1 1 d . .
C1 C 0.30419(14) -0.00487(14) 0.36485(12) 0.0190(2) Uani 1 1 d . .
C2 C 0.30629(15) 0.02109(15) 0.23144(13) 0.0214(3) Uani 1 1 d . .
C3 C 0.32123(15) 0.19906(15) 0.28939(13) 0.0215(3) Uani 1 1 d . .
C4 C 0.31074(14) 0.16085(14) 0.41786(13) 0.0192(2) Uani 1 1 d . .
C5 C 0.29037(17) 0.41286(15) 0.56327(14) 0.0259(3) Uani 1 1 d . .
H5A H 0.2458 0.4407 0.4769 0.031 Uiso 1 1 calc R U
H5B H 0.4025 0.4817 0.6070 0.031 Uiso 1 1 calc R U
C6 C 0.17789(16) 0.44560(15) 0.65395(13) 0.0225(3) Uani 1 1 d . .
C7 C 0.23561(17) 0.56652(16) 0.77301(15) 0.0289(3) Uani 1 1 d . .
H7 H 0.3458 0.6284 0.7972 0.035 Uiso 1 1 calc R U
C8 C 0.13260(19) 0.59743(18) 0.85701(15) 0.0342(3) Uani 1 1 d . .
H8 H 0.1727 0.6801 0.9386 0.041 Uiso 1 1 calc R U
C9 C -0.02851(18) 0.50791(17) 0.82194(14) 0.0284(3) Uani 1 1 d . .
H9 H -0.0984 0.5297 0.8795 0.034 Uiso 1 1 calc R U
C10 C -0.08860(16) 0.38602(14) 0.70262(13) 0.0220(3) Uani 1 1 d . .
C11 C 0.01555(16) 0.35568(15) 0.61950(13) 0.0226(3) Uani 1 1 d . .
H11 H -0.0243 0.2726 0.5382 0.027 Uiso 1 1 calc R U
C12 C -0.26793(16) 0.29578(15) 0.66510(14) 0.0253(3) Uani 1 1 d . .
H12A H -0.3010 0.2916 0.7490 0.030 Uiso 1 1 calc R U
H12B H -0.3398 0.3569 0.6156 0.030 Uiso 1 1 calc R U
S1 S 0.31176(4) 0.01174(4) 0.83345(3) 0.02669(11) Uani 1 1 d . .
O3 O 0.31246(15) 0.01246(13) 0.68923(10) 0.0356(3) Uani 1 1 d . .
C13 C 0.3889(2) 0.21646(19) 0.92736(15) 0.0362(3) Uani 1 1 d . .
H13A H 0.3747 0.2279 1.0186 0.054 Uiso 1 1 calc R U
H13B H 0.3273 0.2865 0.8821 0.054 Uiso 1 1 calc R U
H13C H 0.5073 0.2476 0.9331 0.054 Uiso 1 1 calc R U
C14 C 0.0998(2) 0.0011(3) 0.8349(2) 0.0516(5) Uani 1 1 d . .
H14A H 0.0914 0.0132 0.9278 0.077 Uiso 1 1 calc R U
H14B H 0.0331 -0.1037 0.7788 0.077 Uiso 1 1 calc R U
H14C H 0.0585 0.0878 0.7989 0.077 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 121.74(11) . 2_556
C1 N1 H1N 116.7(12) . .
C12 N1 H1N 121.3(12) 2_556 .
C4 N2 C5 122.60(12) . .
C4 N2 H2N 116.9(12) . .
C5 N2 H2N 120.5(12) . .
N1 C1 C4 132.92(12) . .
N1 C1 C2 135.29(11) . .
C4 C1 C2 91.79(10) . .
O1 C2 C1 136.17(12) . .
O1 C2 C3 135.45(13) . .
C1 C2 C3 88.33(10) . .
O2 C3 C4 135.87(12) . .
O2 C3 C2 136.18(12) . .
C4 C3 C2 87.95(10) . .
N2 C4 C1 132.29(12) . .
N2 C4 C3 135.82(12) . .
C1 C4 C3 91.83(10) . .
N2 C5 C6 110.67(11) . .
N2 C5 H5A 109.5 . .
C6 C5 H5A 109.5 . .
N2 C5 H5B 109.5 . .
C6 C5 H5B 109.5 . .
H5A C5 H5B 108.1 . .
C7 C6 C11 119.30(12) . .
C7 C6 C5 119.90(12) . .
C11 C6 C5 120.81(11) . .
C6 C7 C8 120.21(13) . .
C6 C7 H7 119.9 . .
C8 C7 H7 119.9 . .
C9 C8 C7 120.15(13) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C10 120.41(13) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C11 C10 C9 119.01(12) . .
C11 C10 C12 122.24(11) . .
C9 C10 C12 118.70(12) . .
C10 C11 C6 120.93(12) . .
C10 C11 H11 119.5 . .
C6 C11 H11 119.5 . .
N1 C12 C10 113.84(10) 2_556 .
N1 C12 H12A 108.8 2_556 .
C10 C12 H12A 108.8 . .
N1 C12 H12B 108.8 2_556 .
C10 C12 H12B 108.8 . .
H12A C12 H12B 107.7 . .
O3 S1 C13 105.23(7) . .
O3 S1 C14 104.76(8) . .
C13 S1 C14 97.45(10) . .
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 1.2228(16) .
O2 C3 1.2242(17) .
N1 C1 1.3242(17) .
N1 C12 1.4590(16) 2_556
N1 H1N 0.85(2) .
N2 C4 1.3228(17) .
N2 C5 1.4650(16) .
N2 H2N 0.872(19) .
C1 C4 1.4146(16) .
C1 C2 1.4674(17) .
C2 C3 1.5088(17) .
C3 C4 1.4718(17) .
C5 C6 1.5099(17) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.3879(18) .
C6 C11 1.3970(18) .
C7 C8 1.391(2) .
C7 H7 0.9500 .
C8 C9 1.386(2) .
C8 H8 0.9500 .
C9 C10 1.3947(18) .
C9 H9 0.9500 .
C10 C11 1.3917(18) .
C10 C12 1.5174(17) .
C11 H11 0.9500 .
C12 N1 1.4589(16) 2_556
C12 H12A 0.9900 .
C12 H12B 0.9900 .
S1 O3 1.5177(10) .
S1 C13 1.7813(16) .
S1 C14 1.7826(17) .
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 O3 0.85(2) 2.02(2) 2.8332(15) 158.9(17) .
N2 H2N O3 0.872(19) 1.962(19) 2.7975(16) 160.0(17) .
C5 H5B O2 0.99 2.52 3.4942(17) 169.4 2_666
C12 H12A O1 0.99 2.62 3.3306(17) 128.9 2_556
C13 H13A O2 0.98 2.50 3.4572(18) 167.0 1_556
C13 H13C O1 0.98 2.55 3.2457(19) 128.1 2_656
C14 H14A O1 0.98 2.60 3.268(2) 125.5 1_556
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 171.21(12) 2_556 .
C12 N1 C1 C2 -8.0(2) 2_556 .
N1 C1 C2 O1 4.4(3) . .
C4 C1 C2 O1 -175.05(15) . .
N1 C1 C2 C3 -178.15(14) . .
C4 C1 C2 C3 2.43(9) . .
O1 C2 C3 O2 -5.2(3) . .
C1 C2 C3 O2 177.26(16) . .
O1 C2 C3 C4 175.18(15) . .
C1 C2 C3 C4 -2.34(9) . .
C5 N2 C4 C1 -171.74(12) . .
C5 N2 C4 C3 4.6(2) . .
N1 C1 C4 N2 -4.5(2) . .
C2 C1 C4 N2 174.97(13) . .
N1 C1 C4 C3 178.07(13) . .
C2 C1 C4 C3 -2.49(9) . .
O2 C3 C4 N2 5.5(3) . .
C2 C3 C4 N2 -174.89(14) . .
O2 C3 C4 C1 -177.18(15) . .
C2 C3 C4 C1 2.43(9) . .
C4 N2 C5 C6 142.83(12) . .
N2 C5 C6 C7 125.34(13) . .
N2 C5 C6 C11 -54.77(17) . .
C11 C6 C7 C8 0.1(2) . .
C5 C6 C7 C8 179.95(14) . .
C6 C7 C8 C9 -0.2(2) . .
C7 C8 C9 C10 0.2(2) . .
C8 C9 C10 C11 0.0(2) . .
C8 C9 C10 C12 -177.42(13) . .
C9 C10 C11 C6 -0.2(2) . .
C12 C10 C11 C6 177.17(12) . .
C7 C6 C11 C10 0.1(2) . .
C5 C6 C11 C10 -179.74(12) . .
C11 C10 C12 N1 30.13(18) . 2_556
C9 C10 C12 N1 -152.50(13) . 2_556
