#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103297.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_4103297
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            'C30 H36 N6 O8 S2'
_chemical_formula_weight         672.77
_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                97.1930(10)
_cell_angle_beta                 98.1780(10)
_cell_angle_gamma                92.0110(10)
_cell_formula_units_Z            1
_cell_length_a                   6.0960(4)
_cell_length_b                   7.2875(4)
_cell_length_c                   18.3630(11)
_cell_measurement_reflns_used    5102
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.26
_cell_volume                     799.96(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0256
_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       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14718
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0333
_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)+(0.0459P)²+0.2630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2811
_reflns_number_total             3389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106106d_si_022.cif
_cod_data_source_block           GDS_23
_cod_database_code               4103297
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 0.4396(2) 0.2404(2) 0.42552(8) 0.0225(3) Uani 1 1 d . . .
C2 C 0.8206(2) 0.6517(2) 0.29610(8) 0.0213(3) Uani 1 1 d . . .
C3 C 1.0125(3) 0.6936(2) 0.26773(8) 0.0265(3) Uani 1 1 d . . .
H3 H 1.1321 0.7640 0.2988 0.032 Uiso 1 1 calc R . .
C4 C 1.0312(3) 0.6335(2) 0.19407(9) 0.0281(3) Uani 1 1 d . . .
H4 H 1.1631 0.6619 0.1748 0.034 Uiso 1 1 calc R . .
C5 C 0.8546(3) 0.5314(2) 0.14898(8) 0.0259(3) Uani 1 1 d . . .
C6 C 0.6652(3) 0.4844(2) 0.17814(9) 0.0303(4) Uani 1 1 d . . .
H6 H 0.5473 0.4106 0.1476 0.036 Uiso 1 1 calc R . .
C7 C 0.6480(3) 0.5447(2) 0.25145(9) 0.0275(3) Uani 1 1 d . . .
H7 H 0.5181 0.5129 0.2712 0.033 Uiso 1 1 calc R . .
C8 C 1.0363(3) 0.5224(2) 0.04127(8) 0.0308(4) Uani 1 1 d . . .
H8A H 1.1656 0.4511 0.0574 0.037 Uiso 1 1 calc R . .
H8B H 1.0776 0.6562 0.0549 0.037 Uiso 1 1 calc R . .
N1 N 0.3427(2) 0.07510(18) 0.42579(7) 0.0285(3) Uani 1 1 d . . .
H1A H 0.4225 -0.0232 0.4259 0.034 Uiso 1 1 calc R . .
H1B H 0.1986 0.0635 0.4258 0.034 Uiso 1 1 calc R . .
N2 N 0.6560(2) 0.25603(19) 0.42545(8) 0.0319(3) Uani 1 1 d . . .
H2A H 0.7346 0.1570 0.4256 0.038 Uiso 1 1 calc R . .
H2B H 0.7216 0.3654 0.4253 0.038 Uiso 1 1 calc R . .
N3 N 0.3218(2) 0.39020(18) 0.42330(7) 0.0284(3) Uani 1 1 d . . .
H3A H 0.3881 0.4986 0.4218 0.034 Uiso 1 1 calc R . .
H3B H 0.1775 0.3810 0.4233 0.034 Uiso 1 1 calc R . .
O1 O 0.92147(18) 0.61294(15) 0.43565(6) 0.0285(3) Uani 1 1 d . . .
O2 O 0.89169(17) 0.92418(14) 0.40285(6) 0.0280(3) Uani 1 1 d . . .
O3 O 0.56112(17) 0.72403(14) 0.39488(6) 0.0254(2) Uani 1 1 d . . .
O4 O 0.8497(2) 0.47151(16) 0.07502(6) 0.0337(3) Uani 1 1 d . . .
S1 S 0.79784(6) 0.73411(5) 0.389469(19) 0.01986(11) Uani 1 1 d . . .
C9 C 0.463(3) 0.059(3) 0.2308(10) 0.038(3) Uani 0.573(10) 1 d PU A 1
H9 H 0.5474 0.0718 0.2790 0.046 Uiso 0.573(10) 1 calc PR A 1
C10 C 0.552(4) -0.036(4) 0.1700(11) 0.039(3) Uani 0.573(10) 1 d PU A 1
H10 H 0.6951 -0.0838 0.1787 0.047 Uiso 0.573(10) 1 calc PR A 1
C11 C 0.436(2) -0.060(2) 0.0981(8) 0.036(2) Uani 0.573(10) 1 d PU A 1
H11 H 0.4975 -0.1255 0.0582 0.043 Uiso 0.573(10) 1 calc PR A 1
C12 C 0.2281(15) 0.0136(12) 0.0864(6) 0.0249(15) Uani 0.573(10) 1 d PU A 1
C13 C 0.145(2) 0.108(2) 0.1467(7) 0.034(2) Uani 0.573(10) 1 d PU A 1
H13 H 0.0049 0.1597 0.1375 0.041 Uiso 0.573(10) 1 calc PR A 1
C14 C 0.257(3) 0.131(3) 0.2211(13) 0.042(3) Uani 0.573(10) 1 d PU A 1
H14 H 0.1944 0.1929 0.2613 0.050 Uiso 0.573(10) 1 calc PR A 1
C15 C 0.1043(8) -0.0173(5) 0.0102(3) 0.0361(14) Uani 0.573(10) 1 d PU . 1
H15 H 0.1836 -0.0673 -0.0279 0.043 Uiso 0.573(10) 1 calc PR A 1
C9' C 0.504(4) 0.035(4) 0.2203(12) 0.035(4) Uani 0.427(10) 1 d PU A 2
H9' H 0.6090 0.0315 0.2635 0.042 Uiso 0.427(10) 1 calc PR A 2
C10' C 0.543(6) -0.044(5) 0.1541(15) 0.045(5) Uani 0.427(10) 1 d PU A 2
H10' H 0.6775 -0.1018 0.1483 0.054 Uiso 0.427(10) 1 calc PR A 2
C11' C 0.378(3) -0.037(3) 0.0940(9) 0.031(3) Uani 0.427(10) 1 d PU A 2
H11' H 0.4054 -0.0901 0.0464 0.037 Uiso 0.427(10) 1 calc PR A 2
C12' C 0.174(2) 0.0435(17) 0.0988(7) 0.025(2) Uani 0.427(10) 1 d PU A 2
C13' C 0.141(4) 0.125(3) 0.1674(8) 0.036(3) Uani 0.427(10) 1 d PU A 2
H13' H 0.0073 0.1826 0.1748 0.043 Uiso 0.427(10) 1 calc PR A 2
C14' C 0.310(4) 0.120(4) 0.2246(15) 0.038(4) Uani 0.427(10) 1 d PU A 2
H14' H 0.2894 0.1809 0.2718 0.046 Uiso 0.427(10) 1 calc PR A 2
C15' C 0.0009(9) 0.0410(6) 0.0352(3) 0.0273(17) Uani 0.427(10) 1 d PU . 2
H15' H -0.1274 0.1053 0.0444 0.033 Uiso 0.427(10) 1 calc PRU 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
N2 C1 N1 119.45(14) . .
N2 C1 N3 119.43(14) . .
N1 C1 N3 121.09(14) . .
C3 C2 C7 119.94(14) . .
C3 C2 S1 119.72(11) . .
C7 C2 S1 120.34(11) . .
C2 C3 C4 120.48(14) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C3 C4 C5 119.22(14) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
O4 C5 C6 115.24(14) . .
O4 C5 C4 124.57(14) . .
C6 C5 C4 120.19(14) . .
C7 C6 C5 120.18(15) . .
C7 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C6 C7 C2 119.93(14) . .
C6 C7 H7 120.0 . .
C2 C7 H7 120.0 . .
O4 C8 C8 105.74(16) . 2_765
O4 C8 H8A 110.6 . .
C8 C8 H8A 110.6 2_765 .
O4 C8 H8B 110.6 . .
C8 C8 H8B 110.6 2_765 .
H8A C8 H8B 108.7 . .
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 . .
C5 O4 C8 117.69(12) . .
O1 S1 O2 112.66(7) . .
O1 S1 O3 112.07(6) . .
O2 S1 O3 112.18(6) . .
O1 S1 C2 107.10(7) . .
O2 S1 C2 106.15(7) . .
O3 S1 C2 106.13(7) . .
C14 C9 C10 121(2) . .
C14 C9 H9 119.4 . .
C10 C9 H9 119.4 . .
C11 C10 C9 122(2) . .
C11 C10 H10 118.9 . .
C9 C10 H10 118.9 . .
C10 C11 C12 118.0(16) . .
C10 C11 H11 121.0 . .
C12 C11 H11 121.0 . .
C13 C12 C11 118.9(12) . .
C13 C12 C15 123.5(8) . .
C11 C12 C15 117.5(9) . .
C12 C13 C14 124.4(13) . .
C12 C13 H13 117.8 . .
C14 C13 H13 117.8 . .
C9 C14 C13 115.3(18) . .
C9 C14 H14 122.3 . .
C13 C14 H14 122.3 . .
C15 C15 C12 126.8(6) 2 .
C15 C15 H15 116.6 2 .
C12 C15 H15 116.6 . .
C10' C9' C14' 119(3) . .
C10' C9' H9' 120.7 . .
C14' C9' H9' 120.7 . .
C9' C10' C11' 117(3) . .
C9' C10' H10' 121.4 . .
C11' C10' H10' 121.4 . .
C10' C11' C12' 124(2) . .
C10' C11' H11' 117.8 . .
C12' C11' H11' 117.8 . .
C13' C12' C11' 116.9(16) . .
C13' C12' C15' 120.1(12) . .
C11' C12' C15' 123.0(10) . .
C14' C13' C12' 116.9(19) . .
C14' C13' H13' 121.6 . .
C12' C13' H13' 121.6 . .
C9' C14' C13' 126(2) . .
C9' C14' H14' 117.0 . .
C13' C14' H14' 117.0 . .
C15' C15' C12' 128.4(7) 2 .
C15' C15' H15' 115.8 2 .
C12' C15' H15' 115.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.3203(19) .
C1 N1 1.3237(19) .
C1 N3 1.3293(19) .
C2 C3 1.386(2) .
C2 C7 1.387(2) .
C2 S1 1.7706(14) .
C3 C4 1.391(2) .
C3 H3 0.9500 .
C4 C5 1.391(2) .
C4 H4 0.9500 .
C5 O4 1.3693(18) .
C5 C6 1.389(2) .
C6 C7 1.383(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 O4 1.4298(19) .
C8 C8 1.508(3) 2_765
C8 H8A 0.9900 .
C8 H8B 0.9900 .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
O1 S1 1.4558(11) .
O2 S1 1.4579(11) .
O3 S1 1.4604(10) .
C9 C14 1.375(19) .
C9 C10 1.42(3) .
C9 H9 0.9500 .
C10 C11 1.39(2) .
C10 H10 0.9500 .
C11 C12 1.397(9) .
C11 H11 0.9500 .
C12 C13 1.394(10) .
C12 C15 1.478(12) .
C13 C14 1.43(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C15 1.316(10) 2
C15 H15 0.9500 .
C9' C10' 1.33(3) .
C9' C14' 1.36(2) .
C9' H9' 0.9500 .
C10' C11' 1.39(3) .
C10' H10' 0.9500 .
C11' C12' 1.401(11) .
C11' H11' 0.9500 .
C12' C13' 1.367(13) .
C12' C15' 1.458(16) .
C13' C14' 1.37(3) .
C13' H13' 0.9500 .
C14' H14' 0.9500 .
C15' C15' 1.353(12) 2
C15' H15' 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 2.10 2.9547(16) 163.2 1_545
N1 H1B O2 0.88 2.06 2.8791(17) 154.4 1_445
N2 H2A O2 0.88 2.01 2.8718(17) 167.9 1_545
N2 H2B O1 0.88 2.11 2.9859(17) 170.9 .
N3 H3A O3 0.88 2.07 2.9333(17) 166.6 .
N3 H3B O1 0.88 2.35 2.9975(17) 130.3 1_455
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 1.8(2) . .
S1 C2 C3 C4 -178.58(12) . .
C2 C3 C4 C5 0.3(2) . .
C3 C4 C5 O4 177.07(14) . .
C3 C4 C5 C6 -2.4(2) . .
O4 C5 C6 C7 -177.10(14) . .
C4 C5 C6 C7 2.4(2) . .
C5 C6 C7 C2 -0.3(2) . .
C3 C2 C7 C6 -1.8(2) . .
S1 C2 C7 C6 178.59(12) . .
C6 C5 O4 C8 177.45(14) . .
C4 C5 O4 C8 -2.0(2) . .
C8 C8 O4 C5 -167.25(16) 2_765 .
C3 C2 S1 O1 -79.09(13) . .
C7 C2 S1 O1 100.55(13) . .
C3 C2 S1 O2 41.49(14) . .
C7 C2 S1 O2 -138.87(13) . .
C3 C2 S1 O3 161.03(12) . .
C7 C2 S1 O3 -19.33(14) . .
C14 C9 C10 C11 0(3) . .
C9 C10 C11 C12 1(3) . .
C10 C11 C12 C13 -0.1(19) . .
C10 C11 C12 C15 -178.5(14) . .
C11 C12 C13 C14 -1(2) . .
C15 C12 C13 C14 176.9(15) . .
C10 C9 C14 C13 -1(3) . .
C12 C13 C14 C9 2(3) . .
C13 C12 C15 C15 -8.7(11) . 2
C11 C12 C15 C15 169.7(8) . 2
C14' C9' C10' C11' -2(4) . .
C9' C10' C11' C12' -1(4) . .
C10' C11' C12' C13' 2(3) . .
C10' C11' C12' C15' -177(2) . .
C11' C12' C13' C14' 0(3) . .
C15' C12' C13' C14' 179.1(19) . .
C10' C9' C14' C13' 4(4) . .
C12' C13' C14' C9' -3(4) . .
C13' C12' C15' C15' -176.1(12) . 2
C11' C12' C15' C15' 3.2(16) . 2
