#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:47:55 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179674 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/26/4512698.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_4512698
loop_
_publ_author_name
'Berryman, Orion B.'
'Johnson, 2nd, Charles A'
'Vonnegut, Chris L.'
'Fajardo, Kevin A.'
'Zakharov, Lev N.'
'Johnson, Darren W.'
'Haley, Michael M.'
_publ_section_title
;
 Solid-State Examination of Conformationally Diverse Sulfonamide Receptors
 Based on Bis(2-anilinoethynyl)pyridine, -Bipyridine, and -Thiophene.
;
_journal_issue                   3
_journal_name_full               'Crystal growth & design'
_journal_page_first              1502
_journal_page_last               1511
_journal_paper_doi               10.1021/cg5018856
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C48 H46 N4 O4 S2'
_chemical_formula_weight         807.01
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                101.699(7)
_cell_angle_beta                 97.680(7)
_cell_angle_gamma                95.720(6)
_cell_formula_units_Z            1
_cell_length_a                   7.960(3)
_cell_length_b                   10.860(4)
_cell_length_c                   12.852(4)
_cell_measurement_reflns_used    1673
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      52.81
_cell_measurement_theta_min      5.01
_cell_volume                     1068.9(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0765
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7795
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3745
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                2499
_reflns_number_total             3745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5018856_si_002.cif
_cod_data_source_block           ob102
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4512691--4512698.cif.

 Adding full bibliography for 4512691--4512698.cif.
;
_cod_original_cell_volume        1068.9(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4512698
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.40673(11) 1.00667(9) 0.16028(7) 0.0399(3) Uani 1 1 d .
O1 O 0.3212(3) 1.0028(2) 0.05394(17) 0.0437(6) Uani 1 1 d .
O2 O 0.3404(3) 1.0705(2) 0.25102(18) 0.0489(7) Uani 1 1 d .
N1 N 0.9655(3) 0.6579(2) 0.05896(19) 0.0291(6) Uani 1 1 d .
N2 N 0.5989(3) 1.0767(3) 0.1645(2) 0.0350(7) Uani 1 1 d .
C1 C 0.4617(6) 0.4640(4) 0.1989(4) 0.0758(14) Uani 1 1 d .
H1C H 0.4040 0.4453 0.2577 0.114 Uiso 1 1 calc R
H1D H 0.5827 0.4531 0.2136 0.114 Uiso 1 1 calc R
H1E H 0.4080 0.4060 0.1312 0.114 Uiso 1 1 calc R
C2 C 0.4468(5) 0.5991(4) 0.1898(3) 0.0538(11) Uani 1 1 d .
C3 C 0.3627(5) 0.6769(4) 0.2573(3) 0.0598(12) Uani 1 1 d .
H3A H 0.3109 0.6441 0.3101 0.072 Uiso 1 1 calc R
C4 C 0.5188(5) 0.6487(4) 0.1122(3) 0.0599(12) Uani 1 1 d .
H4A H 0.5789 0.5973 0.0650 0.072 Uiso 1 1 calc R
C5 C 0.5045(5) 0.7719(4) 0.1026(3) 0.0518(10) Uani 1 1 d .
H5A H 0.5520 0.8038 0.0479 0.062 Uiso 1 1 calc R
C6 C 0.3506(5) 0.8011(4) 0.2511(3) 0.0527(10) Uani 1 1 d .
H6A H 0.2943 0.8533 0.3003 0.063 Uiso 1 1 calc R
C7 C 0.4212(4) 0.8488(3) 0.1726(3) 0.0402(9) Uani 1 1 d .
C8 C 0.7216(4) 1.1144(3) 0.2589(2) 0.0302(7) Uani 1 1 d .
C9 C 0.6990(4) 1.2122(3) 0.3415(3) 0.0392(9) Uani 1 1 d .
H9A H 0.5954 1.2488 0.3377 0.047 Uiso 1 1 calc R
C10 C 0.8263(4) 1.2571(3) 0.4295(3) 0.0402(9) Uani 1 1 d .
H10A H 0.8062 1.3218 0.4866 0.048 Uiso 1 1 calc R
C11 C 0.9830(4) 1.2103(3) 0.4369(2) 0.0329(8) Uani 1 1 d .
C12 C 1.0024(4) 1.1116(3) 0.3544(2) 0.0313(8) Uani 1 1 d .
H12A H 1.1071 1.0765 0.3577 0.038 Uiso 1 1 calc R
C13 C 0.8744(4) 1.0617(3) 0.2665(2) 0.0266(7) Uani 1 1 d .
C14 C 1.1326(5) 1.2656(3) 0.5281(3) 0.0438(9) Uani 1 1 d .
C15 C 1.2605(6) 1.3470(4) 0.4861(4) 0.0816(15) Uani 1 1 d .
H15A H 1.3572 1.3832 0.5435 0.122 Uiso 1 1 calc R
H15B H 1.2060 1.4157 0.4622 0.122 Uiso 1 1 calc R
H15C H 1.3016 1.2951 0.4254 0.122 Uiso 1 1 calc R
C16 C 1.0773(7) 1.3462(7) 0.6229(4) 0.167(4) Uani 1 1 d .
H16A H 1.1766 1.3792 0.6790 0.250 Uiso 1 1 calc R
H16B H 0.9930 1.2951 0.6510 0.250 Uiso 1 1 calc R
H16C H 1.0259 1.4171 0.6009 0.250 Uiso 1 1 calc R
C17 C 1.2219(8) 1.1620(5) 0.5628(4) 0.128(3) Uani 1 1 d .
H17A H 1.3168 1.1992 0.6210 0.191 Uiso 1 1 calc R
H17B H 1.2662 1.1136 0.5017 0.191 Uiso 1 1 calc R
H17C H 1.1409 1.1053 0.5883 0.191 Uiso 1 1 calc R
C18 C 0.9026(4) 0.9585(3) 0.1835(2) 0.0294(7) Uani 1 1 d .
C19 C 0.9269(4) 0.8727(3) 0.1151(2) 0.0302(8) Uani 1 1 d .
C20 C 0.9541(4) 0.7696(3) 0.0309(2) 0.0302(7) Uani 1 1 d .
C21 C 0.9682(4) 0.7881(3) -0.0712(3) 0.0355(8) Uani 1 1 d .
H21A H 0.9580 0.8685 -0.0880 0.043 Uiso 1 1 calc R
C22 C 0.9974(4) 0.6876(3) -0.1477(3) 0.0388(9) Uani 1 1 d .
H22A H 1.0068 0.6971 -0.2186 0.047 Uiso 1 1 calc R
C23 C 1.0127(4) 0.5733(3) -0.1200(2) 0.0352(8) Uani 1 1 d .
H23A H 1.0354 0.5030 -0.1711 0.042 Uiso 1 1 calc R
C24 C 0.9947(4) 0.5613(3) -0.0161(2) 0.0283(7) Uani 1 1 d .
H1N H 0.631(4) 1.048(3) 0.105(3) 0.039(10) Uiso 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 0.0033 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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_3
O2 S1 O1 119.56(15) .
O2 S1 N2 107.69(15) .
O1 S1 N2 104.76(15) .
O2 S1 C7 108.20(16) .
O1 S1 C7 107.85(15) .
N2 S1 C7 108.33(15) .
C24 N1 C20 117.3(3) .
C8 N2 S1 124.1(2) .
C8 N2 H1N 119(2) .
S1 N2 H1N 108(2) .
C2 C1 H1C 109.5 .
C2 C1 H1D 109.5 .
H1C C1 H1D 109.5 .
C2 C1 H1E 109.5 .
H1C C1 H1E 109.5 .
H1D C1 H1E 109.5 .
C3 C2 C4 117.7(4) .
C3 C2 C1 121.7(4) .
C4 C2 C1 120.6(4) .
C2 C3 C6 122.4(4) .
C2 C3 H3A 118.8 .
C6 C3 H3A 118.8 .
C5 C4 C2 121.0(4) .
C5 C4 H4A 119.5 .
C2 C4 H4A 119.5 .
C7 C5 C4 120.1(4) .
C7 C5 H5A 119.9 .
C4 C5 H5A 119.9 .
C3 C6 C7 119.3(4) .
C3 C6 H6A 120.4 .
C7 C6 H6A 120.4 .
C6 C7 C5 119.6(4) .
C6 C7 S1 121.0(3) .
C5 C7 S1 119.5(3) .
C9 C8 C13 118.8(3) .
C9 C8 N2 120.4(3) .
C13 C8 N2 120.5(3) .
C10 C9 C8 120.4(3) .
C10 C9 H9A 119.8 .
C8 C9 H9A 119.8 .
C9 C10 C11 122.0(3) .
C9 C10 H10A 119.0 .
C11 C10 H10A 119.0 .
C12 C11 C10 116.6(3) .
C12 C11 C14 119.9(3) .
C10 C11 C14 123.4(3) .
C11 C12 C13 122.6(3) .
C11 C12 H12A 118.7 .
C13 C12 H12A 118.7 .
C12 C13 C8 119.4(3) .
C12 C13 C18 119.8(3) .
C8 C13 C18 120.7(3) .
C16 C14 C17 109.7(4) .
C16 C14 C15 108.2(4) .
C17 C14 C15 107.3(4) .
C16 C14 C11 112.4(3) .
C17 C14 C11 110.7(3) .
C15 C14 C11 108.4(3) .
C14 C15 H15A 109.5 .
C14 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C14 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C14 C16 H16A 109.5 .
C14 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C14 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C14 C17 H17A 109.5 .
C14 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C14 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C19 C18 C13 179.5(4) .
C18 C19 C20 178.9(3) .
N1 C20 C21 123.4(3) .
N1 C20 C19 115.7(3) .
C21 C20 C19 120.9(3) .
C22 C21 C20 118.5(3) .
C22 C21 H21A 120.7 .
C20 C21 H21A 120.7 .
C23 C22 C21 119.0(3) .
C23 C22 H22A 120.5 .
C21 C22 H22A 120.5 .
C22 C23 C24 119.3(3) .
C22 C23 H23A 120.4 .
C24 C23 H23A 120.4 .
N1 C24 C23 122.5(3) .
N1 C24 C24 116.5(3) 2_765
C23 C24 C24 121.0(3) 2_765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.424(2) .
S1 O1 1.434(2) .
S1 N2 1.628(3) .
S1 C7 1.767(4) .
N1 C24 1.335(4) .
N1 C20 1.342(4) .
N2 C8 1.412(4) .
N2 H1N 0.84(3) .
C1 C2 1.510(6) .
C1 H1C 0.9800 .
C1 H1D 0.9800 .
C1 H1E 0.9800 .
C2 C3 1.373(5) .
C2 C4 1.386(5) .
C3 C6 1.379(5) .
C3 H3A 0.9500 .
C4 C5 1.383(5) .
C4 H4A 0.9500 .
C5 C7 1.382(5) .
C5 H5A 0.9500 .
C6 C7 1.380(5) .
C6 H6A 0.9500 .
C8 C9 1.386(4) .
C8 C13 1.395(4) .
C9 C10 1.384(4) .
C9 H9A 0.9500 .
C10 C11 1.392(4) .
C10 H10A 0.9500 .
C11 C12 1.383(4) .
C11 C14 1.533(4) .
C12 C13 1.393(4) .
C12 H12A 0.9500 .
C13 C18 1.440(4) .
C14 C16 1.494(5) .
C14 C17 1.500(6) .
C14 C15 1.507(5) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 C19 1.195(4) .
C19 C20 1.447(4) .
C20 C21 1.384(4) .
C21 C22 1.374(4) .
C21 H21A 0.9500 .
C22 C23 1.371(4) .
C22 H22A 0.9500 .
C23 C24 1.392(4) .
C23 H23A 0.9500 .
C24 C24 1.480(6) 2_765
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
N2 H1N O1 0.84(3) 2.11(3) 2.939(4) 170(3) 2_675
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_4
O2 S1 N2 C8 43.8(3) .
O1 S1 N2 C8 172.1(3) .
C7 S1 N2 C8 -73.0(3) .
C4 C2 C3 C6 -1.0(6) .
C1 C2 C3 C6 178.9(4) .
C3 C2 C4 C5 -0.7(6) .
C1 C2 C4 C5 179.4(4) .
C2 C4 C5 C7 1.7(6) .
C2 C3 C6 C7 1.8(6) .
C3 C6 C7 C5 -0.8(5) .
C3 C6 C7 S1 179.2(3) .
C4 C5 C7 C6 -0.9(5) .
C4 C5 C7 S1 179.1(3) .
O2 S1 C7 C6 9.1(3) .
O1 S1 C7 C6 -121.5(3) .
N2 S1 C7 C6 125.6(3) .
O2 S1 C7 C5 -170.9(3) .
O1 S1 C7 C5 58.5(3) .
N2 S1 C7 C5 -54.4(3) .
S1 N2 C8 C9 -68.5(4) .
S1 N2 C8 C13 117.3(3) .
C13 C8 C9 C10 0.4(5) .
N2 C8 C9 C10 -173.9(3) .
C8 C9 C10 C11 2.6(5) .
C9 C10 C11 C12 -3.3(5) .
C9 C10 C11 C14 174.4(3) .
C10 C11 C12 C13 1.1(5) .
C14 C11 C12 C13 -176.6(3) .
C11 C12 C13 C8 1.7(5) .
C11 C12 C13 C18 -179.7(3) .
C9 C8 C13 C12 -2.4(5) .
N2 C8 C13 C12 171.8(3) .
C9 C8 C13 C18 179.0(3) .
N2 C8 C13 C18 -6.7(5) .
C12 C11 C14 C16 -165.2(4) .
C10 C11 C14 C16 17.3(6) .
C12 C11 C14 C17 -42.1(5) .
C10 C11 C14 C17 140.3(4) .
C12 C11 C14 C15 75.4(4) .
C10 C11 C14 C15 -102.2(4) .
C12 C13 C18 C19 23(50) .
C8 C13 C18 C19 -158(100) .
C13 C18 C19 C20 -174(100) .
C24 N1 C20 C21 1.1(4) .
C24 N1 C20 C19 -178.4(3) .
C18 C19 C20 N1 -141(19) .
C18 C19 C20 C21 39(19) .
N1 C20 C21 C22 -0.8(5) .
C19 C20 C21 C22 178.7(3) .
C20 C21 C22 C23 -0.5(5) .
C21 C22 C23 C24 1.4(5) .
C20 N1 C24 C23 -0.1(4) .
C20 N1 C24 C24 -179.5(3) 2_765
C22 C23 C24 N1 -1.1(5) .
C22 C23 C24 C24 178.2(4) 2_765
