#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103288.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_4103288
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            'C26 H32 N6 O8 S4'
_chemical_formula_weight         684.82
_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                94.606(2)
_cell_angle_beta                 99.461(2)
_cell_angle_gamma                91.746(2)
_cell_formula_units_Z            1
_cell_length_a                   6.0857(8)
_cell_length_b                   7.2198(10)
_cell_length_c                   18.138(3)
_cell_measurement_reflns_used    2899
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.29
_cell_volume                     782.8(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      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0372
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10656
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0376
_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)+(0.0487P)²+0.3870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                2632
_reflns_number_total             3242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106106d_si_013.cif
_cod_data_source_block           GDS_14
_cod_original_cell_volume        782.79(18)
_cod_database_code               4103288
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5657(3) 0.7485(3) 0.07568(11) 0.0221(5) Uani 1 1 d . . .
N1 N 0.6625(3) 0.9149(3) 0.07517(11) 0.0279(4) Uani 1 1 d . . .
H1A H 0.5820 1.0141 0.0738 0.033 Uiso 1 1 calc R . .
H1B H 0.8074 0.9262 0.0762 0.033 Uiso 1 1 calc R . .
N2 N 0.6832(3) 0.5973(3) 0.07871(11) 0.0288(4) Uani 1 1 d . . .
H2A H 0.6163 0.4879 0.0797 0.035 Uiso 1 1 calc R . .
H2B H 0.8282 0.6061 0.0797 0.035 Uiso 1 1 calc R . .
N3 N 0.3481(3) 0.7338(3) 0.07415(12) 0.0305(5) Uani 1 1 d . . .
H3A H 0.2692 0.8340 0.0728 0.037 Uiso 1 1 calc R . .
H3B H 0.2820 0.6238 0.0745 0.037 Uiso 1 1 calc R . .
C2 C 0.1803(3) 0.3358(3) 0.20466(11) 0.0203(4) Uani 1 1 d . . .
C3 C 0.3513(4) 0.4468(3) 0.24845(12) 0.0263(5) Uani 1 1 d . . .
H3 H 0.4804 0.4802 0.2285 0.032 Uiso 1 1 calc R . .
C4 C 0.3323(4) 0.5081(3) 0.32120(13) 0.0288(5) Uani 1 1 d . . .
H4 H 0.4480 0.5853 0.3512 0.035 Uiso 1 1 calc R . .
C5 C 0.1445(4) 0.4572(3) 0.35071(12) 0.0252(5) Uani 1 1 d . . .
C6 C -0.0278(4) 0.3493(3) 0.30664(13) 0.0275(5) Uani 1 1 d . . .
H6 H -0.1576 0.3167 0.3264 0.033 Uiso 1 1 calc R . .
C7 C -0.0090(4) 0.2895(3) 0.23343(12) 0.0252(5) Uani 1 1 d . . .
H7 H -0.1270 0.2162 0.2028 0.030 Uiso 1 1 calc R . .
C8 C -0.0276(4) 0.4564(3) 0.46026(12) 0.0297(5) Uani 1 1 d . . .
H8A H -0.0323 0.3190 0.4593 0.036 Uiso 1 1 calc R . .
H8B H -0.1738 0.4959 0.4355 0.036 Uiso 1 1 calc R . .
O4 O 0.1468(3) 0.5206(2) 0.42376(9) 0.0339(4) Uani 1 1 d . . .
S1 S 0.20454(8) 0.25319(7) 0.11187(3) 0.01906(15) Uani 1 1 d . . .
O1 O 0.4425(2) 0.2622(2) 0.10806(8) 0.0243(3) Uani 1 1 d . . .
O2 O 0.0802(2) 0.3762(2) 0.06222(8) 0.0278(4) Uani 1 1 d . . .
O3 O 0.1120(2) 0.0627(2) 0.10081(9) 0.0277(4) Uani 1 1 d . . .
S2 S 0.8058(7) 0.8868(6) 0.39534(14) 0.0430(4) Uani 0.726(2) 1 d P A 1
C9 C 0.7667(10) 0.8758(7) 0.2967(2) 0.0325(10) Uani 0.726(2) 1 d P A 1
H9 H 0.8673 0.8299 0.2655 0.039 Uiso 0.726(2) 1 calc PR A 1
C10 C 0.5640(17) 0.9460(15) 0.2741(8) 0.0415(17) Uani 0.726(2) 1 d PD A 1
H10 H 0.5144 0.9589 0.2223 0.050 Uiso 0.726(2) 1 calc PR A 1
C11 C 0.4013(8) 1.0100(7) 0.3372(3) 0.0272(11) Uani 0.726(2) 1 d PD A 1
H11 H 0.2536 1.0521 0.3317 0.033 Uiso 0.726(2) 1 calc PR A 1
C12 C 0.5502(7) 0.9815(6) 0.3980(3) 0.0295(9) Uani 0.726(2) 1 d P A 1
C13 C 0.4582(6) 1.0219(5) 0.4656(2) 0.0355(8) Uani 0.726(2) 1 d P . 1
H13 H 0.3238 1.0867 0.4605 0.043 Uiso 0.726(2) 1 calc PR A 1
S2' S 0.4531(8) 1.0049(7) 0.3292(3) 0.0430(4) Uani 0.274(2) 1 d P A 2
C9' C 0.596(5) 0.931(4) 0.266(2) 0.0325(10) Uani 0.274(2) 1 d P A 2
H9' H 0.5678 0.9262 0.2133 0.039 Uiso 0.274(2) 1 calc PR A 2
C10' C 0.784(3) 0.875(3) 0.3192(8) 0.0415(17) Uani 0.274(2) 1 d PD A 2
H10' H 0.9019 0.8229 0.2971 0.050 Uiso 0.274(2) 1 calc PR A 2
C11' C 0.819(6) 0.888(5) 0.4021(12) 0.0272(11) Uani 0.274(2) 1 d PD A 2
H11' H 0.9417 0.8592 0.4383 0.033 Uiso 0.274(2) 1 calc PR A 2
C12' C 0.623(2) 0.952(2) 0.4088(9) 0.0295(9) Uani 0.274(2) 1 d P A 2
C13' C 0.5905(18) 0.9740(13) 0.4869(6) 0.0355(8) Uani 0.274(2) 1 d P . 2
H13' H 0.7141 0.9480 0.5234 0.043 Uiso 0.274(2) 1 calc PR A 2
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
_geom_angle_site_symmetry_3
N3 C1 N1 119.25(19) . .
N3 C1 N2 119.5(2) . .
N1 C1 N2 121.2(2) . .
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 . .
C7 C2 C3 120.1(2) . .
C7 C2 S1 119.88(16) . .
C3 C2 S1 120.00(16) . .
C4 C3 C2 119.6(2) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 120.2(2) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
O4 C5 C6 124.6(2) . .
O4 C5 C4 115.21(19) . .
C6 C5 C4 120.2(2) . .
C5 C6 C7 119.3(2) . .
C5 C6 H6 120.3 . .
C7 C6 H6 120.3 . .
C2 C7 C6 120.5(2) . .
C2 C7 H7 119.8 . .
C6 C7 H7 119.8 . .
O4 C8 C8 105.3(2) . 2_566
O4 C8 H8A 110.7 . .
C8 C8 H8A 110.7 2_566 .
O4 C8 H8B 110.7 . .
C8 C8 H8B 110.7 2_566 .
H8A C8 H8B 108.8 . .
C5 O4 C8 118.23(17) . .
O2 S1 O3 112.89(10) . .
O2 S1 O1 112.05(9) . .
O3 S1 O1 111.95(9) . .
O2 S1 C2 106.83(9) . .
O3 S1 C2 106.30(9) . .
O1 S1 C2 106.28(9) . .
C12 S2 C9 92.4(3) . .
C10 C9 S2 106.5(7) . .
C10 C9 H9 126.8 . .
S2 C9 H9 126.8 . .
C9 C10 C11 120.2(11) . .
C9 C10 H10 119.9 . .
C11 C10 H10 119.9 . .
C12 C11 C10 96.1(6) . .
C12 C11 H11 132.0 . .
C10 C11 H11 132.0 . .
C11 C12 C13 110.8(3) . .
C11 C12 S2 124.6(4) . .
C13 C12 S2 124.4(3) . .
C13 C13 C12 127.0(5) 2_676 .
C13 C13 H13 116.5 2_676 .
C12 C13 H13 116.5 . .
C9' S2' C12' 100.3(15) . .
C9' S2' C10' 39.5(15) . .
C12' S2' C10' 60.9(7) . .
C10' C9' S2' 96(3) . .
C10' C9' H9' 132.1 . .
S2' C9' H9' 132.1 . .
C9' C10' C11' 129(3) . .
C9' C10' S2' 44.8(14) . .
C11' C10' S2' 84.7(17) . .
C9' C10' H10' 115.3 . .
C11' C10' H10' 115.3 . .
S2' C10' H10' 160.0 . .
C12' C11' C10' 96(2) . .
C12' C11' H11' 131.9 . .
C10' C11' H11' 131.9 . .
C11' C12' C13' 112.2(14) . .
C11' C12' S2' 117.9(16) . .
C13' C12' S2' 129.8(10) . .
C13' C13' C12' 127.8(13) 2_676 .
C13' C13' H13' 116.1 2_676 .
C12' C13' H13' 116.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N3 1.321(3) .
C1 N1 1.323(3) .
C1 N2 1.323(3) .
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 C7 1.383(3) .
C2 C3 1.390(3) .
C2 S1 1.771(2) .
C3 C4 1.382(3) .
C3 H3 0.9500 .
C4 C5 1.391(3) .
C4 H4 0.9500 .
C5 O4 1.364(3) .
C5 C6 1.386(3) .
C6 C7 1.387(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 O4 1.425(3) .
C8 C8 1.507(4) 2_566
C8 H8A 0.9900 .
C8 H8B 0.9900 .
S1 O2 1.4552(15) .
S1 O3 1.4561(15) .
S1 O1 1.4611(15) .
S2 C12 1.724(6) .
S2 C9 1.760(4) .
C9 C10 1.361(11) .
C9 H9 0.9500 .
C10 C11 1.680(8) .
C10 H10 0.9500 .
C11 C12 1.341(6) .
C11 H11 0.9500 .
C12 C13 1.442(6) .
C13 C13 1.336(7) 2_676
C13 H13 0.9500 .
S2' C9' 1.61(2) .
S2' C12' 1.711(14) .
S2' C10' 2.28(2) .
C9' C10' 1.45(4) .
C9' H9' 0.9500 .
C10' C11' 1.479(18) .
C10' H10' 0.9500 .
C11' C12' 1.31(4) .
C11' H11' 0.9500 .
C12' C13' 1.46(2) .
C13' C13' 1.32(2) 2_676
C13' H13' 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 O1 0.88 2.10 2.944(2) 160.8 1_565
N1 H1B O3 0.88 2.04 2.857(2) 154.4 1_665
N2 H2A O1 0.88 2.06 2.920(2) 165.2 .
N2 H2B O2 0.88 2.33 2.978(2) 130.4 1_655
N3 H3A O3 0.88 2.01 2.862(2) 164.0 1_565
N3 H3B O2 0.88 2.11 2.985(2) 170.4 .
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
C7 C2 C3 C4 1.0(3) . .
S1 C2 C3 C4 -178.98(17) . .
C2 C3 C4 C5 0.8(3) . .
C3 C4 C5 O4 177.9(2) . .
C3 C4 C5 C6 -1.9(3) . .
O4 C5 C6 C7 -178.5(2) . .
C4 C5 C6 C7 1.4(3) . .
C3 C2 C7 C6 -1.6(3) . .
S1 C2 C7 C6 178.38(17) . .
C5 C6 C7 C2 0.4(3) . .
C6 C5 O4 C8 7.0(3) . .
C4 C5 O4 C8 -172.9(2) . .
C8 C8 O4 C5 177.6(2) 2_566 .
C7 C2 S1 O2 81.32(19) . .
C3 C2 S1 O2 -98.72(19) . .
C7 C2 S1 O3 -39.47(19) . .
C3 C2 S1 O3 140.49(18) . .
C7 C2 S1 O1 -158.88(17) . .
C3 C2 S1 O1 21.1(2) . .
C12 S2 C9 C10 0.4(7) . .
S2 C9 C10 C11 -3.5(11) . .
C9 C10 C11 C12 5.3(10) . .
C10 C11 C12 C13 -178.9(5) . .
C10 C11 C12 S2 -5.1(7) . .
C9 S2 C12 C11 3.6(6) . .
C9 S2 C12 C13 176.6(4) . .
C11 C12 C13 C13 167.0(5) . 2_676
S2 C12 C13 C13 -6.8(8) . 2_676
C12' S2' C9' C10' -3(2) . .
S2' C9' C10' C11' 0(4) . .
C12' S2' C10' C9' 177(2) . .
C9' S2' C10' C11' 180(3) . .
C12' S2' C10' C11' -3.2(18) . .
C9' C10' C11' C12' 4(4) . .
S2' C10' C11' C12' 4(2) . .
C10' C11' C12' C13' 177.1(16) . .
C10' C11' C12' S2' -6(3) . .
C9' S2' C12' C11' 6(3) . .
C10' S2' C12' C11' 4(2) . .
C9' S2' C12' C13' -177.2(17) . .
C10' S2' C12' C13' -179.1(17) . .
C11' C12' C13' C13' -176(2) . 2_676
S2' C12' C13' C13' 7(2) . 2_676
