#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103299.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_4103299
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            'C56 H62 N8 O6 S2'
_chemical_formula_weight         1007.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 90.7480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7072(6)
_cell_length_b                   29.840(2)
_cell_length_c                   11.4574(9)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.71
_cell_volume                     2634.8(3)
_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 0.998
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            42199
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         0.68
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0320
_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)+(0.0415P)²+1.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                4931
_reflns_number_total             5434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106106d_si_024.cif
_cod_data_source_block           GDS_25
_cod_original_cell_volume        2634.8(4)
_cod_database_code               4103299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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 0.94526(4) 0.205936(9) 0.89625(2) 0.01521(8) Uani 1 1 d .
C1 C 0.93888(15) 0.25856(4) 0.24917(10) 0.0165(2) Uani 1 1 d .
C3 C 0.89839(15) 0.12703(4) 1.01346(10) 0.0178(2) Uani 1 1 d .
H3 H 0.8375 0.1445 1.0689 0.021 Uiso 1 1 calc R
C26 C 0.45794(15) 1.05091(4) 0.60765(11) 0.0201(3) Uani 1 1 d .
H26 H 0.4259 1.0270 0.5569 0.024 Uiso 1 1 calc R
C19 C 0.56153(16) 0.90547(4) 0.91515(11) 0.0220(3) Uani 1 1 d .
H19 H 0.5966 0.9269 0.9721 0.026 Uiso 1 1 calc R
C18 C 0.47100(15) 0.91954(4) 0.81570(11) 0.0202(3) Uani 1 1 d .
C7 C 1.05519(16) 0.12223(4) 0.83165(11) 0.0189(2) Uani 1 1 d .
H7 H 1.1005 0.1363 0.7642 0.023 Uiso 1 1 calc R
C16 C 0.46207(17) 0.84248(5) 0.74970(12) 0.0253(3) Uani 1 1 d .
H16 H 0.4285 0.8210 0.6925 0.030 Uiso 1 1 calc R
C6 C 1.07807(16) 0.07656(4) 0.84959(11) 0.0207(3) Uani 1 1 d .
H6 H 1.1399 0.0592 0.7944 0.025 Uiso 1 1 calc R
C24 C 0.59200(16) 1.07685(4) 0.78424(11) 0.0230(3) Uani 1 1 d .
H24 H 0.6516 1.0711 0.8558 0.028 Uiso 1 1 calc R
C27 C 0.41606(16) 1.09448(4) 0.57669(11) 0.0234(3) Uani 1 1 d .
H27 H 0.3549 1.1003 0.5058 0.028 Uiso 1 1 calc R
C20 C 0.60121(16) 0.86049(4) 0.93196(12) 0.0237(3) Uani 1 1 d .
H20 H 0.6628 0.8513 1.0003 0.028 Uiso 1 1 calc R
C15 C 0.55128(16) 0.82895(4) 0.84953(12) 0.0243(3) Uani 1 1 d .
H15 H 0.5780 0.7982 0.8613 0.029 Uiso 1 1 calc R
C4 C 0.92135(15) 0.08160(4) 1.03115(10) 0.0183(2) Uani 1 1 d .
H4 H 0.8770 0.0677 1.0991 0.022 Uiso 1 1 calc R
C12 C 1.03810(16) 0.07422(4) 0.34605(11) 0.0210(3) Uani 1 1 d .
H12 H 1.0650 0.0522 0.2891 0.025 Uiso 1 1 calc R
C17 C 0.42184(16) 0.88746(4) 0.73328(11) 0.0229(3) Uani 1 1 d .
H17 H 0.3600 0.8965 0.6649 0.028 Uiso 1 1 calc R
C25 C 0.54619(15) 1.04131(4) 0.71168(11) 0.0183(2) Uani 1 1 d .
C2 C 0.96517(14) 0.14715(4) 0.91362(10) 0.0154(2) Uani 1 1 d .
C14 C 0.92159(15) 0.01235(4) 0.47315(11) 0.0214(3) Uani 1 1 d .
H14A H 0.8873 -0.0026 0.3992 0.026 Uiso 1 1 calc R
H14B H 0.8227 0.0102 0.5271 0.026 Uiso 1 1 calc R
C22 C 0.46375(17) 1.12953(4) 0.64965(13) 0.0265(3) Uani 1 1 d .
H22 H 0.4363 1.1595 0.6287 0.032 Uiso 1 1 calc R
C13 C 1.07887(17) 0.11872(5) 0.32529(12) 0.0257(3) Uani 1 1 d .
H13 H 1.1343 0.1270 0.2550 0.031 Uiso 1 1 calc R
C21 C 0.43201(16) 0.96850(4) 0.79607(12) 0.0236(3) Uani 1 1 d .
H21A H 0.4011 0.9825 0.8713 0.028 Uiso 1 1 calc R
H21B H 0.3309 0.9714 0.7424 0.028 Uiso 1 1 calc R
C5 C 1.01025(15) 0.05625(4) 0.94857(10) 0.0178(2) Uani 1 1 d .
C23 C 0.55158(18) 1.12067(5) 0.75324(13) 0.0281(3) Uani 1 1 d .
H23 H 0.5844 1.1447 0.8034 0.034 Uiso 1 1 calc R
C9 C 0.95618(18) 0.13885(5) 0.50953(12) 0.0279(3) Uani 1 1 d .
H9 H 0.9268 0.1610 0.5654 0.033 Uiso 1 1 calc R
C11 C 0.95838(15) 0.06117(4) 0.44895(11) 0.0185(2) Uani 1 1 d .
C8 C 1.03848(18) 0.15110(4) 0.40748(13) 0.0280(3) Uani 1 1 d .
H8 H 1.0671 0.1816 0.3939 0.034 Uiso 1 1 calc R
C28 C 0.58756(16) 0.99340(4) 0.74422(12) 0.0221(3) Uani 1 1 d .
H28A H 0.6845 0.9932 0.8017 0.027 Uiso 1 1 calc R
H28B H 0.6265 0.9772 0.6738 0.027 Uiso 1 1 calc R
C10 C 0.91663(16) 0.09411(4) 0.53020(11) 0.0226(3) Uani 1 1 d .
H10 H 0.8606 0.0859 0.6004 0.027 Uiso 1 1 calc R
N4 N 1.03675(14) 0.00893(4) 0.95763(9) 0.0207(2) Uani 1 1 d .
N3 N 0.93589(13) 0.27180(3) 0.35974(9) 0.0189(2) Uani 1 1 d .
H3A H 0.8360 0.2762 0.3943 0.023 Uiso 1 1 calc R
H3B H 1.0338 0.2762 0.3985 0.023 Uiso 1 1 calc R
N1 N 1.08939(13) 0.25197(4) 0.19682(9) 0.0211(2) Uani 1 1 d .
H1A H 1.0912 0.2433 0.1235 0.025 Uiso 1 1 calc R
H1B H 1.1874 0.2563 0.2355 0.025 Uiso 1 1 calc R
N2 N 0.79154(13) 0.25197(4) 0.19056(9) 0.0206(2) Uani 1 1 d .
H2A H 0.7938 0.2433 0.1172 0.025 Uiso 1 1 calc R
H2B H 0.6916 0.2563 0.2250 0.025 Uiso 1 1 calc R
O2 O 1.09629(11) 0.22525(3) 0.95661(7) 0.01962(19) Uani 1 1 d .
O3 O 0.78358(11) 0.21871(3) 0.95238(7) 0.01885(18) Uani 1 1 d .
O1 O 0.94539(11) 0.21533(3) 0.77153(7) 0.01949(19) Uani 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_1
_geom_angle_site_symmetry_3
O1 S1 O3 113.16(5) . .
O1 S1 O2 112.14(5) . .
O3 S1 O2 111.52(5) . .
O1 S1 C2 107.43(5) . .
O3 S1 C2 106.39(5) . .
O2 S1 C2 105.64(5) . .
N2 C1 N1 119.79(11) . .
N2 C1 N3 120.12(11) . .
N1 C1 N3 120.09(11) . .
C4 C3 C2 119.61(11) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C27 C26 C25 121.43(12) . .
C27 C26 H26 119.3 . .
C25 C26 H26 119.3 . .
C20 C19 C18 120.76(12) . .
C20 C19 H19 119.6 . .
C18 C19 H19 119.6 . .
C19 C18 C17 118.43(12) . .
C19 C18 C21 120.71(12) . .
C17 C18 C21 120.83(11) . .
C6 C7 C2 119.22(11) . .
C6 C7 H7 120.4 . .
C2 C7 H7 120.4 . .
C15 C16 C17 120.00(13) . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C7 C6 C5 119.93(11) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C23 C24 C25 120.71(12) . .
C23 C24 H24 119.6 . .
C25 C24 H24 119.6 . .
C26 C27 C22 119.68(12) . .
C26 C27 H27 120.2 . .
C22 C27 H27 120.2 . .
C15 C20 C19 120.22(12) . .
C15 C20 H20 119.9 . .
C19 C20 H20 119.9 . .
C20 C15 C16 119.69(12) . .
C20 C15 H15 120.2 . .
C16 C15 H15 120.2 . .
C3 C4 C5 119.65(11) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C13 C12 C11 121.13(12) . .
C13 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
C16 C17 C18 120.89(12) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C24 C25 C26 118.14(11) . .
C24 C25 C28 121.55(12) . .
C26 C25 C28 120.31(11) . .
C7 C2 C3 121.07(11) . .
C7 C2 S1 119.79(9) . .
C3 C2 S1 119.03(9) . .
C11 C14 C14 112.80(12) . 3_756
C11 C14 H14A 109.0 . .
C14 C14 H14A 109.0 3_756 .
C11 C14 H14B 109.0 . .
C14 C14 H14B 109.0 3_756 .
H14A C14 H14B 107.8 . .
C23 C22 C27 119.73(12) . .
C23 C22 H22 120.1 . .
C27 C22 H22 120.1 . .
C12 C13 C8 119.83(12) . .
C12 C13 H13 120.1 . .
C8 C13 H13 120.1 . .
C18 C21 C28 111.80(10) . .
C18 C21 H21A 109.3 . .
C28 C21 H21A 109.3 . .
C18 C21 H21B 109.3 . .
C28 C21 H21B 109.3 . .
H21A C21 H21B 107.9 . .
C6 C5 C4 120.51(11) . .
C6 C5 N4 115.71(11) . .
C4 C5 N4 123.78(11) . .
C22 C23 C24 120.31(12) . .
C22 C23 H23 119.8 . .
C24 C23 H23 119.8 . .
C8 C9 C10 120.04(13) . .
C8 C9 H9 120.0 . .
C10 C9 H9 120.0 . .
C12 C11 C10 118.46(12) . .
C12 C11 C14 120.74(11) . .
C10 C11 C14 120.78(11) . .
C9 C8 C13 119.86(13) . .
C9 C8 H8 120.1 . .
C13 C8 H8 120.1 . .
C25 C28 C21 112.95(10) . .
C25 C28 H28A 109.0 . .
C21 C28 H28A 109.0 . .
C25 C28 H28B 109.0 . .
C21 C28 H28B 109.0 . .
H28A C28 H28B 107.8 . .
C9 C10 C11 120.67(12) . .
C9 C10 H10 119.7 . .
C11 C10 H10 119.7 . .
N4 N4 C5 114.31(13) 3_757 .
C1 N3 H3A 120.0 . .
C1 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O1 1.4562(9) .
S1 O3 1.4603(9) .
S1 O2 1.4643(9) .
S1 C2 1.7720(12) .
C1 N2 1.3264(15) .
C1 N1 1.3275(15) .
C1 N3 1.3275(16) .
C3 C4 1.3820(17) .
C3 C2 1.3961(16) .
C3 H3 0.9500 .
C26 C27 1.3845(18) .
C26 C25 1.3943(17) .
C26 H26 0.9500 .
C19 C20 1.3895(18) .
C19 C18 1.3930(18) .
C19 H19 0.9500 .
C18 C17 1.3937(18) .
C18 C21 1.5079(17) .
C7 C6 1.3890(17) .
C7 C2 1.3904(17) .
C7 H7 0.9500 .
C16 C15 1.3868(19) .
C16 C17 1.3899(19) .
C16 H16 0.9500 .
C6 C5 1.3937(17) .
C6 H6 0.9500 .
C24 C23 1.3892(19) .
C24 C25 1.3904(18) .
C24 H24 0.9500 .
C27 C22 1.3857(19) .
C27 H27 0.9500 .
C20 C15 1.384(2) .
C20 H20 0.9500 .
C15 H15 0.9500 .
C4 C5 1.3977(17) .
C4 H4 0.9500 .
C12 C13 1.3860(19) .
C12 C11 1.3921(17) .
C12 H12 0.9500 .
C17 H17 0.9500 .
C25 C28 1.5103(17) .
C14 C11 1.5104(17) .
C14 C14 1.537(2) 3_756
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C22 C23 1.384(2) .
C22 H22 0.9500 .
C13 C8 1.387(2) .
C13 H13 0.9500 .
C21 C28 1.5366(17) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C5 N4 1.4301(16) .
C23 H23 0.9500 .
C9 C8 1.387(2) .
C9 C10 1.3903(19) .
C9 H9 0.9500 .
C11 C10 1.3944(18) .
C8 H8 0.9500 .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C10 H10 0.9500 .
N4 N4 1.250(2) 3_757
N3 H3A 0.8800 .
N3 H3B 0.8800 .
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
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
N3 H3A O2 0.88 1.99 2.8577(13) 168.4 4_565
N3 H3B O3 0.88 2.02 2.8833(13) 166.6 4_665
N1 H1A O2 0.88 1.99 2.8665(14) 178.5 1_554
N1 H1B O1 0.88 2.20 3.0251(13) 157.0 4_665
N2 H2B O1 0.88 2.15 2.9991(13) 161.7 4_565
N2 H2A O3 0.88 2.03 2.9037(13) 174.8 1_554
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
C20 C19 C18 C17 -0.27(18) . .
C20 C19 C18 C21 -178.43(11) . .
C2 C7 C6 C5 0.35(18) . .
C25 C26 C27 C22 0.59(19) . .
C18 C19 C20 C15 0.13(19) . .
C19 C20 C15 C16 0.29(19) . .
C17 C16 C15 C20 -0.6(2) . .
C2 C3 C4 C5 -0.37(17) . .
C15 C16 C17 C18 0.43(19) . .
C19 C18 C17 C16 -0.01(18) . .
C21 C18 C17 C16 178.14(11) . .
C23 C24 C25 C26 -0.37(19) . .
C23 C24 C25 C28 -179.48(12) . .
C27 C26 C25 C24 -0.15(18) . .
C27 C26 C25 C28 178.97(11) . .
C6 C7 C2 C3 0.26(18) . .
C6 C7 C2 S1 176.48(9) . .
C4 C3 C2 C7 -0.25(17) . .
C4 C3 C2 S1 -176.50(9) . .
O1 S1 C2 C7 30.22(11) . .
O3 S1 C2 C7 151.69(9) . .
O2 S1 C2 C7 -89.66(10) . .
O1 S1 C2 C3 -153.48(9) . .
O3 S1 C2 C3 -32.01(10) . .
O2 S1 C2 C3 86.64(10) . .
C26 C27 C22 C23 -0.5(2) . .
C11 C12 C13 C8 -0.64(19) . .
C19 C18 C21 C28 81.89(15) . .
C17 C18 C21 C28 -96.22(14) . .
C7 C6 C5 C4 -0.97(18) . .
C7 C6 C5 N4 178.44(11) . .
C3 C4 C5 C6 0.98(18) . .
C3 C4 C5 N4 -178.37(11) . .
C27 C22 C23 C24 0.0(2) . .
C25 C24 C23 C22 0.4(2) . .
C13 C12 C11 C10 1.38(18) . .
C13 C12 C11 C14 -177.29(11) . .
C14 C14 C11 C12 84.32(17) 3_756 .
C14 C14 C11 C10 -94.32(17) 3_756 .
C10 C9 C8 C13 1.0(2) . .
C12 C13 C8 C9 -0.6(2) . .
C24 C25 C28 C21 99.32(14) . .
C26 C25 C28 C21 -79.77(15) . .
C18 C21 C28 C25 173.88(11) . .
C8 C9 C10 C11 -0.2(2) . .
C12 C11 C10 C9 -0.95(18) . .
C14 C11 C10 C9 177.72(11) . .
C6 C5 N4 N4 -174.76(13) . 3_757
C4 C5 N4 N4 4.6(2) . 3_757
