#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:32:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180186 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/82/7108279.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_7108279
loop_
_publ_author_name
'Jun Zhang'
'Xiaolong Su'
'Jun Fu'
'Xinke Qin'
'Meixin Zhao'
'Min Shi'
_publ_section_title
;
 Tailor-made synthesis of various backbone-substituted imidazolinium salts
 by triflic anhydride mediated intramolecular cyclisation
;
_journal_name_full               Chem.Commun.
_journal_page_first              9192
_journal_paper_doi               10.1039/c2cc34952c
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H28 N2 S2'
_chemical_formula_weight         444.63
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   10.0291(10)
_cell_length_b                   15.1285(15)
_cell_length_c                   15.5536(15)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.19
_cell_measurement_theta_min      2.42
_cell_volume                     2359.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21311
_diffrn_reflns_theta_full        29.24
_diffrn_reflns_theta_max         29.24
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.9352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         6400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0303
_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)+(0.0517P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                5931
_reflns_number_total             6400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc34952c.txt
_cod_data_source_block           mo_dm12279_0m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7108279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
S1 S 0.71774(4) 0.60901(2) 0.23853(2) 0.03133(8) Uani 1 1 d .
S2 S 0.67652(5) 0.41136(3) 0.22051(2) 0.04014(10) Uani 1 1 d .
N1 N 0.74231(10) 0.47564(7) 0.42592(6) 0.0218(2) Uani 1 1 d .
N2 N 0.53349(10) 0.51259(7) 0.39977(6) 0.0211(2) Uani 1 1 d .
C1 C 0.68398(12) 0.50765(8) 0.27302(7) 0.0227(2) Uani 1 1 d .
C2 C 0.65356(12) 0.49932(8) 0.36657(7) 0.0203(2) Uani 1 1 d .
C3 C 0.68121(13) 0.47698(9) 0.51207(8) 0.0248(2) Uani 1 1 d .
H3A H 0.7170 0.5263 0.5470 0.030 Uiso 1 1 calc R
H3B H 0.6972 0.4206 0.5427 0.030 Uiso 1 1 calc R
C4 C 0.53156(12) 0.49013(8) 0.49346(7) 0.0211(2) Uani 1 1 d .
H4 H 0.4850 0.4322 0.5010 0.025 Uiso 1 1 calc R
C5 C 0.45769(13) 0.55967(9) 0.54471(8) 0.0229(2) Uani 1 1 d .
C6 C 0.52209(15) 0.62977(10) 0.58488(10) 0.0321(3) Uani 1 1 d .
H6 H 0.6166 0.6334 0.5839 0.039 Uiso 1 1 calc R
C7 C 0.4477(2) 0.69458(11) 0.62658(10) 0.0411(4) Uani 1 1 d .
H7 H 0.4922 0.7417 0.6549 0.049 Uiso 1 1 calc R
C8 C 0.31107(19) 0.69121(11) 0.62726(10) 0.0428(4) Uani 1 1 d .
H8 H 0.2613 0.7367 0.6545 0.051 Uiso 1 1 calc R
C9 C 0.24624(16) 0.62149(12) 0.58823(10) 0.0405(4) Uani 1 1 d .
H9 H 0.1516 0.6186 0.5892 0.049 Uiso 1 1 calc R
C10 C 0.31918(14) 0.55532(10) 0.54741(9) 0.0300(3) Uani 1 1 d .
H10 H 0.2742 0.5070 0.5213 0.036 Uiso 1 1 calc R
C11 C 0.93899(16) 0.57150(10) 0.44128(11) 0.0369(3) Uani 1 1 d .
H11A H 0.8891 0.6179 0.4113 0.055 Uiso 1 1 calc R
H11B H 1.0340 0.5767 0.4273 0.055 Uiso 1 1 calc R
H11C H 0.9266 0.5781 0.5035 0.055 Uiso 1 1 calc R
C12 C 0.88803(12) 0.48092(9) 0.41292(8) 0.0250(3) Uani 1 1 d .
H12 H 0.9050 0.4756 0.3498 0.030 Uiso 1 1 calc R
C13 C 0.96030(12) 0.40495(9) 0.45672(8) 0.0251(2) Uani 1 1 d .
C14 C 1.00501(15) 0.33419(10) 0.40739(9) 0.0322(3) Uani 1 1 d .
H14 H 0.9847 0.3322 0.3478 0.039 Uiso 1 1 calc R
C15 C 1.07920(18) 0.26615(11) 0.44433(11) 0.0402(3) Uani 1 1 d .
H15 H 1.1101 0.2185 0.4098 0.048 Uiso 1 1 calc R
C16 C 1.10766(16) 0.26811(11) 0.53113(11) 0.0391(4) Uani 1 1 d .
H16 H 1.1591 0.2222 0.5563 0.047 Uiso 1 1 calc R
C17 C 1.06114(17) 0.33712(12) 0.58147(10) 0.0394(4) Uani 1 1 d .
H17 H 1.0786 0.3376 0.6415 0.047 Uiso 1 1 calc R
C18 C 0.98899(15) 0.40561(11) 0.54432(9) 0.0339(3) Uani 1 1 d .
H18 H 0.9590 0.4533 0.5790 0.041 Uiso 1 1 calc R
C19 C 0.41594(12) 0.53712(9) 0.35230(7) 0.0215(2) Uani 1 1 d .
C20 C 0.38695(12) 0.62695(9) 0.34087(8) 0.0238(2) Uani 1 1 d .
C21 C 0.27257(14) 0.64828(9) 0.29373(8) 0.0275(3) Uani 1 1 d .
H21 H 0.2515 0.7087 0.2843 0.033 Uiso 1 1 calc R
C22 C 0.18946(13) 0.58396(10) 0.26055(8) 0.0303(3) Uani 1 1 d .
C23 C 0.21818(13) 0.49568(10) 0.27647(9) 0.0306(3) Uani 1 1 d .
H23 H 0.1590 0.4515 0.2557 0.037 Uiso 1 1 calc R
C24 C 0.33126(13) 0.47009(9) 0.32207(8) 0.0255(2) Uani 1 1 d .
C25 C 0.36044(16) 0.37379(10) 0.33839(11) 0.0352(3) Uani 1 1 d .
H25A H 0.3430 0.3600 0.3989 0.053 Uiso 1 1 calc R
H25B H 0.4541 0.3615 0.3251 0.053 Uiso 1 1 calc R
H25C H 0.3031 0.3373 0.3018 0.053 Uiso 1 1 calc R
C26 C 0.07165(17) 0.60955(14) 0.20578(11) 0.0457(4) Uani 1 1 d .
H26A H 0.0205 0.6559 0.2349 0.069 Uiso 1 1 calc R
H26B H 0.0146 0.5578 0.1967 0.069 Uiso 1 1 calc R
H26C H 0.1032 0.6316 0.1501 0.069 Uiso 1 1 calc R
C27 C 0.47077(15) 0.70060(9) 0.37710(10) 0.0324(3) Uani 1 1 d .
H27A H 0.4251 0.7269 0.4266 0.049 Uiso 1 1 calc R
H27B H 0.4845 0.7459 0.3329 0.049 Uiso 1 1 calc R
H27C H 0.5572 0.6770 0.3954 0.049 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 0.0000 0.0000 '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'
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
C2 N1 C3 110.41(10)
C2 N1 C12 123.49(11)
C3 N1 C12 122.34(10)
C2 N2 C19 125.68(10)
C2 N2 C4 110.89(10)
C19 N2 C4 123.18(10)
C2 C1 S1 115.78(9)
C2 C1 S2 113.19(9)
S1 C1 S2 131.02(7)
N2 C2 N1 112.21(10)
N2 C2 C1 123.56(11)
N1 C2 C1 124.20(11)
N1 C3 C4 103.64(9)
N1 C3 H3A 111.0
C4 C3 H3A 111.0
N1 C3 H3B 111.0
C4 C3 H3B 111.0
H3A C3 H3B 109.0
N2 C4 C5 111.18(10)
N2 C4 C3 101.51(9)
C5 C4 C3 117.86(11)
N2 C4 H4 108.6
C5 C4 H4 108.6
C3 C4 H4 108.6
C6 C5 C10 119.10(13)
C6 C5 C4 122.66(12)
C10 C5 C4 118.15(12)
C5 C6 C7 119.86(15)
C5 C6 H6 120.1
C7 C6 H6 120.1
C8 C7 C6 120.85(15)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 119.73(14)
C7 C8 H8 120.1
C9 C8 H8 120.1
C8 C9 C10 120.16(15)
C8 C9 H9 119.9
C10 C9 H9 119.9
C5 C10 C9 120.27(14)
C5 C10 H10 119.9
C9 C10 H10 119.9
C12 C11 H11A 109.5
C12 C11 H11B 109.5
H11A C11 H11B 109.5
C12 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N1 C12 C13 111.68(11)
N1 C12 C11 109.87(12)
C13 C12 C11 112.92(11)
N1 C12 H12 107.4
C13 C12 H12 107.4
C11 C12 H12 107.4
C14 C13 C18 118.58(13)
C14 C13 C12 119.24(12)
C18 C13 C12 122.12(13)
C13 C14 C15 120.86(14)
C13 C14 H14 119.6
C15 C14 H14 119.6
C16 C15 C14 119.85(15)
C16 C15 H15 120.1
C14 C15 H15 120.1
C15 C16 C17 119.94(14)
C15 C16 H16 120.0
C17 C16 H16 120.0
C16 C17 C18 120.14(14)
C16 C17 H17 119.9
C18 C17 H17 119.9
C17 C18 C13 120.61(15)
C17 C18 H18 119.7
C13 C18 H18 119.7
C20 C19 C24 122.18(12)
C20 C19 N2 119.02(11)
C24 C19 N2 118.75(11)
C21 C20 C19 117.42(12)
C21 C20 C27 118.90(12)
C19 C20 C27 123.68(12)
C22 C21 C20 121.87(13)
C22 C21 H21 119.1
C20 C21 H21 119.1
C21 C22 C23 119.06(12)
C21 C22 C26 120.21(14)
C23 C22 C26 120.70(14)
C22 C23 C24 121.82(13)
C22 C23 H23 119.1
C24 C23 H23 119.1
C23 C24 C19 117.54(12)
C23 C24 C25 120.83(12)
C19 C24 C25 121.63(12)
C24 C25 H25A 109.5
C24 C25 H25B 109.5
H25A C25 H25B 109.5
C24 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
C22 C26 H26A 109.5
C22 C26 H26B 109.5
H26A C26 H26B 109.5
C22 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
C20 C27 H27A 109.5
C20 C27 H27B 109.5
H27A C27 H27B 109.5
C20 C27 H27C 109.5
H27A C27 H27C 109.5
H27B C27 H27C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6595(13)
S2 C1 1.6717(13)
N1 C2 1.3313(15)
N1 C3 1.4735(15)
N1 C12 1.4776(16)
N2 C2 1.3255(16)
N2 C19 1.4397(16)
N2 C4 1.4964(15)
C1 C2 1.4920(16)
C3 C4 1.5415(17)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.5136(17)
C4 H4 1.0000
C5 C6 1.3901(19)
C5 C10 1.3914(19)
C6 C7 1.392(2)
C6 H6 0.9500
C7 C8 1.372(3)
C7 H7 0.9500
C8 C9 1.380(2)
C8 H8 0.9500
C9 C10 1.393(2)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.528(2)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.5199(18)
C12 H12 1.0000
C13 C14 1.391(2)
C13 C18 1.3926(18)
C14 C15 1.394(2)
C14 H14 0.9500
C15 C16 1.380(2)
C15 H15 0.9500
C16 C17 1.386(2)
C16 H16 0.9500
C17 C18 1.390(2)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.4010(18)
C19 C24 1.4038(18)
C20 C21 1.3991(18)
C20 C27 1.5053(19)
C21 C22 1.381(2)
C21 H21 0.9500
C22 C23 1.389(2)
C22 C26 1.5071(19)
C23 C24 1.3926(18)
C23 H23 0.9500
C24 C25 1.5075(19)
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
C26 H26A 0.9800
C26 H26B 0.9800
C26 H26C 0.9800
C27 H27A 0.9800
C27 H27B 0.9800
C27 H27C 0.9800
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
C19 N2 C2 N1 -178.80(11)
C4 N2 C2 N1 -4.34(15)
C19 N2 C2 C1 -0.40(19)
C4 N2 C2 C1 174.05(11)
C3 N1 C2 N2 -3.65(15)
C12 N1 C2 N2 -162.19(12)
C3 N1 C2 C1 177.97(11)
C12 N1 C2 C1 19.42(19)
S1 C1 C2 N2 84.71(14)
S2 C1 C2 N2 -94.79(13)
S1 C1 C2 N1 -97.08(13)
S2 C1 C2 N1 83.41(14)
C2 N1 C3 C4 9.55(14)
C12 N1 C3 C4 168.39(12)
C2 N2 C4 C5 135.96(11)
C19 N2 C4 C5 -49.42(15)
C2 N2 C4 C3 9.77(13)
C19 N2 C4 C3 -175.61(11)
N1 C3 C4 N2 -10.97(12)
N1 C3 C4 C5 -132.62(11)
N2 C4 C5 C6 -94.64(14)
C3 C4 C5 C6 21.91(18)
N2 C4 C5 C10 81.80(14)
C3 C4 C5 C10 -161.66(12)
C10 C5 C6 C7 -0.4(2)
C4 C5 C6 C7 176.01(13)
C5 C6 C7 C8 -1.2(2)
C6 C7 C8 C9 1.8(3)
C7 C8 C9 C10 -0.8(2)
C6 C5 C10 C9 1.4(2)
C4 C5 C10 C9 -175.14(12)
C8 C9 C10 C5 -0.9(2)
C2 N1 C12 C13 -144.27(12)
C3 N1 C12 C13 59.66(16)
C2 N1 C12 C11 89.63(15)
C3 N1 C12 C11 -66.44(15)
N1 C12 C13 C14 102.26(14)
C11 C12 C13 C14 -133.32(14)
N1 C12 C13 C18 -80.83(16)
C11 C12 C13 C18 43.59(18)
C18 C13 C14 C15 -1.2(2)
C12 C13 C14 C15 175.79(14)
C13 C14 C15 C16 0.8(3)
C14 C15 C16 C17 0.7(3)
C15 C16 C17 C18 -1.8(3)
C16 C17 C18 C13 1.3(3)
C14 C13 C18 C17 0.2(2)
C12 C13 C18 C17 -176.72(14)
C2 N2 C19 C20 -90.25(15)
C4 N2 C19 C20 95.94(14)
C2 N2 C19 C24 92.35(16)
C4 N2 C19 C24 -81.46(15)
C24 C19 C20 C21 -3.27(19)
N2 C19 C20 C21 179.42(11)
C24 C19 C20 C27 176.05(13)
N2 C19 C20 C27 -1.26(19)
C19 C20 C21 C22 1.00(19)
C27 C20 C21 C22 -178.35(13)
C20 C21 C22 C23 1.8(2)
C20 C21 C22 C26 -176.44(13)
C21 C22 C23 C24 -2.6(2)
C26 C22 C23 C24 175.70(13)
C22 C23 C24 C19 0.4(2)
C22 C23 C24 C25 -179.87(14)
C20 C19 C24 C23 2.59(19)
N2 C19 C24 C23 179.90(11)
C20 C19 C24 C25 -177.13(13)
N2 C19 C24 C25 0.18(19)
