#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:19:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178778 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/32/4103287.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_4103287
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            'C44 H44 N8 O6 S8'
_chemical_formula_weight         1037.35
_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                 91.220(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.573(2)
_cell_length_b                   11.721(4)
_cell_length_c                   28.831(9)
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.24
_cell_volume                     2558.5(14)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5225
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.8122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.953
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5225
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0685
_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)+(0.0927P)²+4.8135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1877
_refine_ls_wR_factor_ref         0.1961
_reflns_number_gt                4185
_reflns_number_total             5225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja106106d_si_012.cif
_cod_data_source_block           GDS_13
_cod_original_cell_volume        2558.7(14)
_cod_database_code               4103287
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5133(4) 0.0112(3) 0.24518(12) 0.0359(7) Uani 1 1 d . . .
N1 N 0.3618(4) -0.0417(3) 0.25360(11) 0.0425(7) Uani 1 1 d . . .
H1A H 0.3628 -0.1118 0.2645 0.051 Uiso 1 1 calc R . .
H1B H 0.2608 -0.0065 0.2483 0.051 Uiso 1 1 calc R . .
N2 N 0.5117(4) 0.1165(3) 0.22816(12) 0.0456(8) Uani 1 1 d . . .
H2A H 0.6118 0.1511 0.2222 0.055 Uiso 1 1 calc R . .
H2B H 0.4106 0.1516 0.2228 0.055 Uiso 1 1 calc R . .
N3 N 0.6650(4) -0.0419(3) 0.25324(12) 0.0447(8) Uani 1 1 d . . .
H3A H 0.7653 -0.0075 0.2473 0.054 Uiso 1 1 calc R . .
H3B H 0.6656 -0.1117 0.2645 0.054 Uiso 1 1 calc R . .
C2 C 0.0045(4) 0.1252(3) 0.14801(12) 0.0335(7) Uani 1 1 d . . .
C3 C 0.0857(5) 0.0252(3) 0.13262(13) 0.0403(8) Uani 1 1 d . . .
H3 H 0.1422 -0.0246 0.1543 0.048 Uiso 1 1 calc R . .
C4 C 0.0837(5) -0.0009(3) 0.08607(14) 0.0427(8) Uani 1 1 d . . .
H4 H 0.1388 -0.0686 0.0755 0.051 Uiso 1 1 calc R . .
C5 C 0.0003(4) 0.0726(3) 0.05435(13) 0.0385(8) Uani 1 1 d . . .
C6 C -0.0745(5) 0.1742(3) 0.06924(14) 0.0424(8) Uani 1 1 d . . .
H6 H -0.1252 0.2258 0.0473 0.051 Uiso 1 1 calc R . .
C7 C -0.0750(4) 0.1998(3) 0.11613(14) 0.0402(8) Uani 1 1 d . . .
H7 H -0.1292 0.2680 0.1266 0.048 Uiso 1 1 calc R . .
N4 N -0.0162(4) 0.0510(2) 0.00541(12) 0.0425(7) Uani 1 1 d . . .
S1 S 0.00973(10) 0.15842(7) 0.20791(3) 0.0349(2) Uani 1 1 d . . .
O1 O 0.0126(3) 0.0497(2) 0.23273(9) 0.0415(6) Uani 1 1 d . . .
O2 O -0.1496(3) 0.2245(2) 0.21665(9) 0.0408(6) Uani 1 1 d . . .
O3 O 0.1704(3) 0.2244(2) 0.21676(9) 0.0409(6) Uani 1 1 d . . .
S2 S 0.60168(15) 0.43935(9) 0.07251(4) 0.0577(3) Uani 1 1 d . . .
C8 C 0.5780(5) 0.4563(3) 0.13074(16) 0.0527(10) Uani 1 1 d . . .
H8 H 0.6233 0.5199 0.1476 0.063 Uiso 1 1 calc R . .
C9 C 0.4872(5) 0.3692(3) 0.15056(15) 0.0482(9) Uani 1 1 d U . .
H9 H 0.4620 0.3656 0.1827 0.058 Uiso 1 1 calc R . .
C10 C 0.4317(4) 0.2800(2) 0.11624(12) 0.0295(6) Uani 1 1 d U . .
H10 H 0.3670 0.2128 0.1230 0.035 Uiso 1 1 calc R . .
C11 C 0.4917(5) 0.3124(3) 0.07190(13) 0.0409(7) Uani 1 1 d U . .
C12 C 0.4661(5) 0.2434(3) 0.02939(16) 0.0484(9) Uani 1 1 d . . .
H12 H 0.3968 0.1762 0.0318 0.058 Uiso 1 1 calc R . .
C13 C 0.5313(5) 0.2671(3) -0.01165(15) 0.0486(9) Uani 1 1 d . . .
H13 H 0.6001 0.3346 -0.0138 0.058 Uiso 1 1 calc R . .
S3 S 0.40785(15) 0.06936(9) -0.05621(4) 0.0594(3) Uani 1 1 d . . .
C14 C 0.5086(5) 0.2005(3) -0.05384(15) 0.0456(9) Uani 1 1 d . . .
C15 C 0.5594(5) 0.2367(3) -0.09582(14) 0.0452(9) Uani 1 1 d . . .
H15 H 0.6180 0.3069 -0.1013 0.054 Uiso 1 1 calc R . .
C16 C 0.5118(6) 0.1523(4) -0.13235(17) 0.0614(11) Uani 1 1 d . . .
H16 H 0.5364 0.1618 -0.1643 0.074 Uiso 1 1 calc R . .
C17 C 0.4290(6) 0.0601(4) -0.11459(18) 0.0628(12) Uani 1 1 d . . .
H17 H 0.3875 -0.0025 -0.1327 0.075 Uiso 1 1 calc R . .
S4 S 0.5898(5) 0.1827(3) 0.43611(14) 0.0732(11) Uani 0.621(4) 1 d PD A 1
C18 C 0.5424(18) 0.1994(10) 0.3765(3) 0.061(3) Uani 0.621(4) 1 d PD A 1
H18 H 0.5792 0.2604 0.3572 0.074 Uiso 0.621(4) 1 calc PR A 1
C19 C 0.4407(15) 0.1061(9) 0.3630(6) 0.074(3) Uani 0.621(4) 1 d PD A 1
H19 H 0.4017 0.0991 0.3316 0.089 Uiso 0.621(4) 1 calc PR A 1
C20 C 0.390(2) 0.0134(14) 0.3985(5) 0.067(4) Uani 0.621(4) 1 d PD A 1
H20 H 0.3234 -0.0548 0.3946 0.080 Uiso 0.621(4) 1 calc PR A 1
C21 C 0.4701(17) 0.0591(10) 0.4371(4) 0.049(2) Uani 0.621(4) 1 d PD A 1
C22 C 0.4579(8) -0.0082(6) 0.4787(3) 0.0490(16) Uani 0.621(4) 1 d PD . 1
H22 H 0.3818 -0.0725 0.4766 0.059 Uiso 0.621(4) 1 calc PR A 1
S4' S 0.4092(13) 0.0237(7) 0.3931(3) 0.0732(11) Uani 0.379(4) 1 d PD A 2
C18' C 0.470(3) 0.1365(16) 0.3598(9) 0.061(3) Uani 0.379(4) 1 d PD A 2
H18' H 0.4475 0.1452 0.3275 0.074 Uiso 0.379(4) 1 calc PR A 2
C19' C 0.558(4) 0.212(3) 0.3882(7) 0.074(3) Uani 0.379(4) 1 d PD A 2
H19' H 0.6189 0.2752 0.3754 0.089 Uiso 0.379(4) 1 calc PR A 2
C20' C 0.556(3) 0.1951(16) 0.4377(8) 0.067(4) Uani 0.379(4) 1 d PD A 2
H20' H 0.5836 0.2493 0.4613 0.080 Uiso 0.379(4) 1 calc PR A 2
C21' C 0.506(3) 0.0821(18) 0.4435(6) 0.049(2) Uani 0.379(4) 1 d PD A 2
C22' C 0.5281(15) 0.0441(11) 0.4928(5) 0.0490(16) Uani 0.379(4) 1 d PD . 2
H22' H 0.5904 0.0927 0.5138 0.059 Uiso 0.379(4) 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
N3 C1 N2 120.2(3) .
N3 C1 N1 119.8(3) .
N2 C1 N1 120.0(3) .
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(3) .
C7 C2 S1 120.3(3) .
C3 C2 S1 119.5(3) .
C4 C3 C2 120.0(3) .
C4 C3 H3 120.0 .
C2 C3 H3 120.0 .
C3 C4 C5 119.8(3) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
C6 C5 C4 120.5(4) .
C6 C5 N4 115.2(3) .
C4 C5 N4 124.3(3) .
C7 C6 C5 119.8(3) .
C7 C6 H6 120.1 .
C5 C6 H6 120.1 .
C6 C7 C2 119.8(3) .
C6 C7 H7 120.1 .
C2 C7 H7 120.1 .
N4 N4 C5 113.4(4) 3
O3 S1 O2 112.19(14) .
O3 S1 O1 111.88(15) .
O2 S1 O1 112.45(15) .
O3 S1 C2 106.76(15) .
O2 S1 C2 106.48(15) .
O1 S1 C2 106.59(15) .
C8 S2 C11 92.9(2) .
C9 C8 S2 113.0(3) .
C9 C8 H8 123.5 .
S2 C8 H8 123.5 .
C8 C9 C10 112.6(4) .
C8 C9 H9 123.7 .
C10 C9 H9 123.7 .
C11 C10 C9 108.6(3) .
C11 C10 H10 125.7 .
C9 C10 H10 125.7 .
C10 C11 C12 124.2(3) .
C10 C11 S2 113.0(3) .
C12 C11 S2 122.8(3) .
C13 C12 C11 125.6(4) .
C13 C12 H12 117.2 .
C11 C12 H12 117.2 .
C12 C13 C14 126.7(4) .
C12 C13 H13 116.7 .
C14 C13 H13 116.7 .
C17 S3 C14 92.6(2) .
C15 C14 C13 123.6(4) .
C15 C14 S3 112.4(3) .
C13 C14 S3 124.0(3) .
C14 C15 C16 111.0(4) .
C14 C15 H15 124.5 .
C16 C15 H15 124.5 .
C17 C16 C15 111.8(4) .
C17 C16 H16 124.1 .
C15 C16 H16 124.1 .
C16 C17 S3 112.2(4) .
C16 C17 H17 123.9 .
S3 C17 H17 123.9 .
C21 S4 C18 90.8(6) .
C19 C18 S4 106.6(11) .
C19 C18 H18 126.7 .
S4 C18 H18 126.7 .
C18 C19 C20 120.9(14) .
C18 C19 H19 119.6 .
C20 C19 H19 119.6 .
C21 C20 C19 98.7(12) .
C21 C20 H20 130.6 .
C19 C20 H20 130.6 .
C20 C21 C22 115.4(9) .
C20 C21 S4 122.9(10) .
C22 C21 S4 121.5(6) .
C22 C22 C21 128.7(9) 3_656
C22 C22 H22 115.6 3_656
C21 C22 H22 115.6 .
C18' S4' C21' 93.0(13) .
C19' C18' S4' 107(2) .
C19' C18' H18' 126.3 .
S4' C18' H18' 126.3 .
C18' C19' C20' 119(3) .
C18' C19' H19' 120.5 .
C20' C19' H19' 120.5 .
C21' C20' C19' 105(2) .
C21' C20' H20' 127.5 .
C19' C20' H20' 127.5 .
C20' C21' C22' 111.8(15) .
C20' C21' S4' 112.6(15) .
C22' C21' S4' 135.2(13) .
C22' C22' C21' 123.6(17) 3_656
C22' C22' H22' 118.2 3_656
C21' C22' H22' 118.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N3 1.323(4) .
C1 N2 1.328(4) .
C1 N1 1.331(4) .
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 1.396(5) .
C2 C3 1.400(4) .
C2 S1 1.770(4) .
C3 C4 1.376(5) .
C3 H3 0.9500 .
C4 C5 1.397(5) .
C4 H4 0.9500 .
C5 C6 1.391(5) .
C5 N4 1.436(5) .
C6 C7 1.385(5) .
C6 H6 0.9500 .
C7 H7 0.9500 .
N4 N4 1.260(6) 3
S1 O3 1.459(2) .
S1 O2 1.461(2) .
S1 O1 1.462(3) .
S2 C8 1.704(5) .
S2 C11 1.705(4) .
C8 C9 1.364(6) .
C8 H8 0.9500 .
C9 C10 1.493(5) .
C9 H9 0.9500 .
C10 C11 1.418(5) .
C10 H10 0.9500 .
C11 C12 1.478(6) .
C12 C13 1.321(6) .
C12 H12 0.9500 .
C13 C14 1.452(6) .
C13 H13 0.9500 .
S3 C17 1.698(5) .
S3 C14 1.717(4) .
C14 C15 1.346(6) .
C15 C16 1.483(6) .
C15 H15 0.9500 .
C16 C17 1.356(7) .
C16 H16 0.9500 .
C17 H17 0.9500 .
S4 C21 1.710(8) .
S4 C18 1.760(9) .
C18 C19 1.388(11) .
C18 H18 0.9500 .
C19 C20 1.546(15) .
C19 H19 0.9500 .
C20 C21 1.367(13) .
C20 H20 0.9500 .
C21 C22 1.438(11) .
C22 C22 1.387(16) 3_656
C22 H22 0.9500 .
S4' C18' 1.704(14) .
S4' C21' 1.751(14) .
C18' C19' 1.369(16) .
C18' H18' 0.9500 .
C19' C20' 1.444(18) .
C19' H19' 0.9500 .
C20' C21' 1.390(17) .
C20' H20' 0.9500 .
C21' C22' 1.496(16) .
C22' C22' 1.19(3) 3_656
C22' H22' 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 H1B O1 0.88 2.03 2.905(4) 170.8 .
N1 H1A O3 0.88 2.01 2.884(4) 170.9 2_545
N2 H2B O3 0.88 2.01 2.890(4) 174.0 .
N2 H2A O2 0.88 2.01 2.886(4) 172.8 1_655
N3 H3A O1 0.88 2.04 2.915(4) 171.9 1_655
N3 H3B O2 0.88 2.00 2.875(4) 173.1 2_545
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 -1.5(5) .
S1 C2 C3 C4 -179.4(3) .
C2 C3 C4 C5 -0.1(5) .
C3 C4 C5 C6 2.6(5) .
C3 C4 C5 N4 -177.1(3) .
C4 C5 C6 C7 -3.5(5) .
N4 C5 C6 C7 176.2(3) .
C5 C6 C7 C2 1.9(5) .
C3 C2 C7 C6 0.5(5) .
S1 C2 C7 C6 178.5(3) .
C6 C5 N4 N4 -164.9(4) 3
C4 C5 N4 N4 14.8(6) 3
C7 C2 S1 O3 -88.9(3) .
C3 C2 S1 O3 89.1(3) .
C7 C2 S1 O2 31.2(3) .
C3 C2 S1 O2 -150.9(3) .
C7 C2 S1 O1 151.4(3) .
C3 C2 S1 O1 -30.7(3) .
C11 S2 C8 C9 -0.6(3) .
S2 C8 C9 C10 0.3(4) .
C8 C9 C10 C11 0.2(4) .
C9 C10 C11 C12 178.1(3) .
C9 C10 C11 S2 -0.6(3) .
C8 S2 C11 C10 0.7(3) .
C8 S2 C11 C12 -178.1(3) .
C10 C11 C12 C13 -174.8(4) .
S2 C11 C12 C13 3.9(5) .
C11 C12 C13 C14 179.8(3) .
C12 C13 C14 C15 171.2(4) .
C12 C13 C14 S3 -6.6(6) .
C17 S3 C14 C15 -0.7(3) .
C17 S3 C14 C13 177.3(3) .
C13 C14 C15 C16 -177.5(3) .
S3 C14 C15 C16 0.5(4) .
C14 C15 C16 C17 0.1(5) .
C15 C16 C17 S3 -0.6(5) .
C14 S3 C17 C16 0.8(4) .
C21 S4 C18 C19 -1.0(9) .
S4 C18 C19 C20 0.3(14) .
C18 C19 C20 C21 0.8(17) .
C19 C20 C21 C22 -177.5(11) .
C19 C20 C21 S4 -1.7(18) .
C18 S4 C21 C20 1.9(15) .
C18 S4 C21 C22 177.3(12) .
C20 C21 C22 C22 171.5(12) 3_656
S4 C21 C22 C22 -4.3(19) 3_656
C21' S4' C18' C19' -0.6(19) .
S4' C18' C19' C20' -10(3) .
C18' C19' C20' C21' 18(3) .
C19' C20' C21' C22' 170(2) .
C19' C20' C21' S4' -17(3) .
C18' S4' C21' C20' 11(2) .
C18' S4' C21' C22' -178(3) .
C20' C21' C22' C22' 169.8(19) 3_656
S4' C21' C22' C22' -2(4) 3_656
