#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:21:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178779 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/33/4103303.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_4103303
loop_
_publ_author_name
'Airon C. Soegiarto'
'Angiolina Comotti'
'Michael D. Ward'
_publ_section_title
;
 Controlled Orientation of Polyconjugated Guest Molecules in Tunable Host
 Cavities
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14603
_journal_page_last               14616
_journal_paper_doi               10.1021/ja106106d
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C20 H24 N8 O6 S6'
_chemical_formula_weight         664.83
_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           SHELXL-97
_cell_angle_alpha                91.838(3)
_cell_angle_beta                 95.848(3)
_cell_angle_gamma                96.074(3)
_cell_formula_units_Z            1
_cell_length_a                   6.2754(13)
_cell_length_b                   7.1880(15)
_cell_length_c                   15.396(3)
_cell_measurement_reflns_used    8381
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.66
_cell_volume                     686.3(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20051
_diffrn_reflns_theta_full        26.56
_diffrn_reflns_theta_max         26.56
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_correction_T_min  0.8094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0584
_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)+(0.0643P)²+3.1009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1765
_reflns_number_gt                2398
_reflns_number_total             2850
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106106d_si_028.cif
_cod_data_source_block           GDS_29
_cod_original_cell_volume        686.4(2)
_cod_database_code               4103303
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
C1 C 0.9425(6) 0.2493(6) 0.4104(3) 0.0178(8) Uani 1 1 d .
N1 N 0.8520(5) 0.0756(5) 0.4147(2) 0.0198(8) Uani 1 1 d .
H1A H 0.7126 0.0539 0.4184 0.024 Uiso 1 1 calc R
H1B H 0.9311 -0.0184 0.4139 0.024 Uiso 1 1 calc R
N2 N 0.8251(6) 0.3934(5) 0.4115(2) 0.0201(8) Uani 1 1 d .
H2A H 0.6856 0.3735 0.4152 0.024 Uiso 1 1 calc R
H2B H 0.8872 0.5083 0.4086 0.024 Uiso 1 1 calc R
N3 N 1.1530(6) 0.2800(5) 0.4011(3) 0.0225(8) Uani 1 1 d .
H3A H 1.2299 0.1849 0.3979 0.027 Uiso 1 1 calc R
H3B H 1.2144 0.3951 0.3981 0.027 Uiso 1 1 calc R
C2 C 0.3401(6) 0.6941(6) 0.2650(3) 0.0163(8) Uani 1 1 d .
C3 C 0.1609(6) 0.6267(7) 0.2078(3) 0.0220(9) Uani 1 1 d .
H3 H 0.0209 0.6205 0.2266 0.026 Uiso 1 1 calc R
C4 C 0.1869(7) 0.5681(7) 0.1227(3) 0.0230(9) Uani 1 1 d .
H4 H 0.0648 0.5238 0.0831 0.028 Uiso 1 1 calc R
C5 C 0.3939(6) 0.5751(6) 0.0962(3) 0.0182(8) Uani 1 1 d .
C6 C 0.5734(6) 0.6468(6) 0.1538(3) 0.0183(8) Uani 1 1 d .
H6 H 0.7133 0.6562 0.1348 0.022 Uiso 1 1 calc R
C7 C 0.5472(6) 0.7036(6) 0.2378(3) 0.0186(8) Uani 1 1 d .
H7 H 0.6692 0.7492 0.2773 0.022 Uiso 1 1 calc R
N4 N 0.4057(6) 0.5095(5) 0.0086(2) 0.0195(7) Uani 1 1 d .
S1 S 0.30884(15) 0.77128(14) 0.37284(7) 0.0158(3) Uani 1 1 d .
O1 O 0.4289(5) 0.6528(4) 0.43087(19) 0.0204(6) Uani 1 1 d .
O2 O 0.0764(4) 0.7466(4) 0.38081(19) 0.0181(6) Uani 1 1 d .
O3 O 0.3971(4) 0.9678(4) 0.3822(2) 0.0194(6) Uani 1 1 d .
S2 S 0.37940(17) 0.09562(16) 0.12166(7) 0.0221(3) Uani 1 1 d .
S3 S 0.82082(17) 0.07498(17) 0.07192(8) 0.0260(3) Uani 1 1 d .
C8 C 0.5404(7) 0.0364(6) 0.0400(3) 0.0205(9) Uani 1 1 d .
C9 C 0.5958(8) 0.1824(7) 0.1973(3) 0.0270(10) Uani 1 1 d .
H9 H 0.5732 0.2348 0.2527 0.032 Uiso 1 1 calc R
C10 C 0.7934(7) 0.1727(7) 0.1749(3) 0.0281(10) Uani 1 1 d .
H10 H 0.9166 0.2178 0.2138 0.034 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'
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_1
N1 C1 N2 120.8(4) .
N1 C1 N3 119.4(4) .
N2 C1 N3 119.7(4) .
C1 N1 H1A 120.0 .
C1 N1 H1B 120.0 .
H1A N1 H1B 120.0 .
C1 N2 H2A 120.0 .
C1 N2 H2B 120.0 .
H2A N2 H2B 120.0 .
C1 N3 H3A 120.0 .
C1 N3 H3B 120.0 .
H3A N3 H3B 120.0 .
C3 C2 C7 120.5(4) .
C3 C2 S1 120.3(3) .
C7 C2 S1 119.2(3) .
C2 C3 C4 119.9(4) .
C2 C3 H3 120.1 .
C4 C3 H3 120.1 .
C3 C4 C5 119.5(4) .
C3 C4 H4 120.2 .
C5 C4 H4 120.2 .
C4 C5 C6 120.2(4) .
C4 C5 N4 115.7(4) .
C6 C5 N4 124.1(4) .
C7 C6 C5 120.1(4) .
C7 C6 H6 120.0 .
C5 C6 H6 120.0 .
C6 C7 C2 119.8(4) .
C6 C7 H7 120.1 .
C2 C7 H7 120.1 .
N4 N4 C5 113.7(4) 2_665
O3 S1 O1 112.52(18) .
O3 S1 O2 111.98(17) .
O1 S1 O2 112.57(18) .
O3 S1 C2 106.71(19) .
O1 S1 C2 106.19(18) .
O2 S1 C2 106.30(18) .
C9 S2 C8 95.0(2) .
C10 S3 C8 94.5(2) .
C8 C8 S2 123.6(4) 2_655
C8 C8 S3 122.0(5) 2_655
S2 C8 S3 114.4(2) .
C10 C9 S2 117.6(4) .
C10 C9 H9 121.2 .
S2 C9 H9 121.2 .
C9 C10 S3 118.3(4) .
C9 C10 H10 120.9 .
S3 C10 H10 120.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.323(6) .
C1 N2 1.333(5) .
C1 N3 1.339(5) .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
C2 C3 1.389(6) .
C2 C7 1.401(6) .
C2 S1 1.771(4) .
C3 C4 1.393(6) .
C3 H3 0.9500 .
C4 C5 1.398(6) .
C4 H4 0.9500 .
C5 C6 1.402(6) .
C5 N4 1.427(6) .
C6 C7 1.375(6) .
C6 H6 0.9500 .
C7 H7 0.9500 .
N4 N4 1.259(7) 2_665
S1 O3 1.459(3) .
S1 O1 1.462(3) .
S1 O2 1.469(3) .
S2 C9 1.744(5) .
S2 C8 1.760(4) .
S3 C10 1.745(5) .
S3 C8 1.768(4) .
C8 C8 1.351(9) 2_655
C9 C10 1.329(7) .
C9 H9 0.9500 .
C10 H10 0.9500 .
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 H1A O3 0.88 2.03 2.866(4) 159.1 1_545
N1 H1B O2 0.88 2.08 2.936(4) 165.5 1_645
N2 H2A O1 0.88 2.55 3.044(5) 116.1 2_666
N2 H2B O2 0.88 2.06 2.922(5) 165.9 1_655
N3 H3A O3 0.88 1.99 2.871(5) 176.2 1_645
N3 H3B O1 0.88 2.18 3.028(5) 160.5 1_655
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
C7 C2 C3 C4 -0.1(7) .
S1 C2 C3 C4 179.3(3) .
C2 C3 C4 C5 1.0(7) .
C3 C4 C5 C6 -2.3(7) .
C3 C4 C5 N4 179.0(4) .
C4 C5 C6 C7 2.6(6) .
N4 C5 C6 C7 -178.8(4) .
C5 C6 C7 C2 -1.7(6) .
C3 C2 C7 C6 0.4(6) .
S1 C2 C7 C6 -179.0(3) .
C4 C5 N4 N4 -169.5(5) 2_665
C6 C5 N4 N4 11.8(7) 2_665
C3 C2 S1 O3 -119.9(4) .
C7 C2 S1 O3 59.5(4) .
C3 C2 S1 O1 119.8(4) .
C7 C2 S1 O1 -60.8(4) .
C3 C2 S1 O2 -0.3(4) .
C7 C2 S1 O2 179.1(3) .
C9 S2 C8 C8 -177.9(6) 2_655
C9 S2 C8 S3 3.4(3) .
C10 S3 C8 C8 177.9(5) 2_655
C10 S3 C8 S2 -3.4(3) .
C8 S2 C9 C10 -2.2(4) .
S2 C9 C10 S3 0.2(6) .
C8 S3 C10 C9 2.0(5) .
