#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/56/4025668.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_4025668
loop_
_publ_author_name
'Motonori Watanabe'
'Kenta Goto'
'Masahiko Shibahara'
'Teruo Shinmyozu'
_publ_section_title
;
 Synthesis, Structure, and Electronic and Photophysical Properties of Two-
 and Three-Layered [3.3]Paracyclophane-Based Donor-Acceptor Systems(1)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6104
_journal_page_last               6114
_journal_paper_doi               10.1021/jo100688m
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C30 H32 N2 S'
_chemical_formula_weight         452.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           41
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.208(4)
_cell_length_b                   16.936(2)
_cell_length_c                   13.147(3)
_cell_measurement_reflns_used    23144
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.08
_cell_volume                     4722.1(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23275
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.903
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.45(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0720
_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)+(0.1493P)²+6.3637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2054
_reflns_number_gt                5173
_reflns_number_total             5361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100688m_si_004.cif
_cod_data_source_block           3ba
_cod_original_cell_volume        4722.1(16)
_cod_database_code               4025668
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, 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 0.70591(14) 0.15345(16) 0.2837(2) 0.0255(6) Uani 1 1 d . . .
H1 H 0.6904(16) 0.101(2) 0.251(3) 0.016(8) Uiso 1 1 d . . .
H2 H 0.7025(16) 0.144(2) 0.355(3) 0.013(7) Uiso 1 1 d . . .
C2 C 0.77534(14) 0.16637(18) 0.2536(3) 0.0301(7) Uani 1 1 d . . .
H3 H 0.801(2) 0.120(3) 0.278(4) 0.041(11) Uiso 1 1 d . . .
H4 H 0.7920(18) 0.214(2) 0.294(3) 0.024(9) Uiso 1 1 d . . .
C3 C 0.78917(17) 0.17250(19) 0.1389(3) 0.0355(7) Uani 1 1 d . . .
H5 H 0.772(3) 0.117(3) 0.102(4) 0.055(14) Uiso 1 1 d . . .
H6 H 0.834(3) 0.169(4) 0.150(5) 0.08(2) Uiso 1 1 d . . .
C4 C 0.76016(15) 0.24363(18) 0.0876(2) 0.0293(6) Uani 1 1 d . . .
C5 C 0.77599(14) 0.32139(18) 0.1211(2) 0.0269(6) Uani 1 1 d . . .
C6 C 0.74044(14) 0.38928(16) 0.0862(2) 0.0256(6) Uani 1 1 d . . .
C7 C 0.69050(15) 0.38125(19) 0.0149(2) 0.0287(6) Uani 1 1 d . . .
C8 C 0.68137(15) 0.3072(2) -0.0230(2) 0.0326(7) Uani 1 1 d . . .
H7 H 0.645(2) 0.299(3) -0.082(4) 0.041(11) Uiso 1 1 d . . .
C9 C 0.71498(16) 0.23995(19) 0.0137(3) 0.0328(7) Uani 1 1 d . . .
H8 H 0.705(3) 0.184(4) -0.020(6) 0.079(19) Uiso 1 1 d . . .
C10 C 0.64719(17) 0.4496(2) -0.0080(3) 0.0378(7) Uani 1 1 d . . .
H9 H 0.6724 0.4929 -0.0382 0.045 Uiso 1 1 calc R . .
H10 H 0.6160 0.4326 -0.0596 0.045 Uiso 1 1 calc R . .
C11 C 0.6125(3) 0.4813(3) 0.0817(5) 0.0715(15) Uani 1 1 d . . .
H11 H 0.6446 0.5028 0.1289 0.086 Uiso 1 1 calc R . .
H12 H 0.5874 0.5268 0.0573 0.086 Uiso 1 1 calc R . .
C12 C 0.5695(2) 0.4312(2) 0.1436(4) 0.0489(11) Uani 1 1 d . . .
H13 H 0.5348 0.4129 0.0991 0.059 Uiso 1 1 calc R . .
H14 H 0.5505 0.4647 0.1972 0.059 Uiso 1 1 calc R . .
C13 C 0.59857(14) 0.35960(18) 0.1941(3) 0.0318(7) Uani 1 1 d . . .
C14 C 0.58261(13) 0.2845(2) 0.1571(3) 0.0304(6) Uani 1 1 d . . .
H15 H 0.5535(18) 0.291(2) 0.113(3) 0.018(8) Uiso 1 1 d . . .
C15 C 0.61158(13) 0.21596(16) 0.1919(2) 0.0241(5) Uani 1 1 d . . .
C16 C 0.66275(13) 0.22264(16) 0.2585(2) 0.0211(5) Uani 1 1 d . . .
C17 C 0.67433(13) 0.29584(16) 0.3032(2) 0.0223(5) Uani 1 1 d . . .
H16 H 0.709(2) 0.303(2) 0.346(3) 0.030(10) Uiso 1 1 d . . .
C18 C 0.64066(14) 0.36439(17) 0.2764(2) 0.0266(6) Uani 1 1 d . . .
C19 C 0.58635(16) 0.1368(2) 0.1553(3) 0.0330(7) Uani 1 1 d . . .
H17 H 0.622(3) 0.107(4) 0.132(5) 0.072(18) Uiso 1 1 d . . .
H18 H 0.5504(18) 0.142(2) 0.102(3) 0.024(9) Uiso 1 1 d . . .
C20 C 0.55624(17) 0.0857(2) 0.2397(3) 0.0377(8) Uani 1 1 d . . .
H19 H 0.545(3) 0.042(4) 0.199(6) 0.081(18) Uiso 1 1 d . . .
H20 H 0.580(2) 0.087(3) 0.299(4) 0.046(12) Uiso 1 1 d . . .
C21 C 0.49502(18) 0.1169(3) 0.2882(4) 0.0467(10) Uani 1 1 d . . .
H21 H 0.470(3) 0.119(3) 0.244(5) 0.061(17) Uiso 1 1 d . . .
H22 H 0.475(2) 0.070(2) 0.326(3) 0.028(10) Uiso 1 1 d . . .
C22 C 0.50334(15) 0.1915(2) 0.3497(3) 0.0337(7) Uani 1 1 d . . .
C23 C 0.47166(16) 0.2607(3) 0.3266(3) 0.0424(8) Uani 1 1 d . . .
H23 H 0.439(2) 0.264(2) 0.268(3) 0.033(10) Uiso 1 1 d . . .
C24 C 0.48806(17) 0.3314(2) 0.3727(3) 0.0438(9) Uani 1 1 d . . .
H24 H 0.4654 0.3779 0.3556 0.053 Uiso 1 1 calc R . .
C25 C 0.53612(17) 0.3360(2) 0.4422(3) 0.0379(8) Uani 1 1 d . . .
C26 C 0.56293(16) 0.2653(2) 0.4752(3) 0.0332(7) Uani 1 1 d . . .
H25 H 0.5932(19) 0.266(2) 0.517(3) 0.024(9) Uiso 1 1 d . . .
C27 C 0.54677(15) 0.1949(2) 0.4306(3) 0.0334(7) Uani 1 1 d . . .
H26 H 0.5709(15) 0.147(2) 0.450(2) 0.013(7) Uiso 1 1 d . . .
C28 C 0.5638(2) 0.4148(2) 0.4791(4) 0.0519(10) Uani 1 1 d . . .
H27 H 0.5290 0.4458 0.5097 0.062 Uiso 1 1 calc R . .
H28 H 0.5942 0.4031 0.5341 0.062 Uiso 1 1 calc R . .
C29 C 0.5950(3) 0.4644(3) 0.4060(5) 0.0685(13) Uani 1 1 d . . .
H29 H 0.6099 0.5114 0.4439 0.082 Uiso 1 1 calc R . .
H30 H 0.5619 0.4832 0.3588 0.082 Uiso 1 1 calc R . .
C30 C 0.64946(19) 0.43810(18) 0.3406(3) 0.0402(8) Uani 1 1 d . . .
H31 H 0.6863 0.4294 0.3856 0.048 Uiso 1 1 calc R . .
H32 H 0.6603 0.4822 0.2943 0.048 Uiso 1 1 calc R . .
N1 N 0.82055(12) 0.33903(16) 0.1900(2) 0.0322(6) Uani 1 1 d . . .
N2 N 0.76014(13) 0.45724(16) 0.1293(2) 0.0319(6) Uani 1 1 d . . .
S1 S 0.81679(4) 0.43397(4) 0.20632(8) 0.0353(2) 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'
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
_geom_angle_publ_flag
C16 C1 C2 114.1(2) . . ?
C3 C2 C1 116.3(3) . . ?
C4 C3 C2 114.4(3) . . ?
C9 C4 C5 115.2(3) . . ?
C9 C4 C3 124.5(3) . . ?
C5 C4 C3 120.1(3) . . ?
N1 C5 C4 125.3(3) . . ?
N1 C5 C6 113.8(3) . . ?
C4 C5 C6 120.8(3) . . ?
N2 C6 C7 126.1(3) . . ?
N2 C6 C5 112.5(3) . . ?
C7 C6 C5 121.4(3) . . ?
C8 C7 C6 115.8(3) . . ?
C8 C7 C10 123.2(3) . . ?
C6 C7 C10 120.8(3) . . ?
C7 C8 C9 122.7(3) . . ?
C4 C9 C8 123.6(3) . . ?
C11 C10 C7 114.8(3) . . ?
C12 C11 C10 122.0(5) . . ?
C11 C12 C13 116.5(3) . . ?
C14 C13 C18 118.2(3) . . ?
C14 C13 C12 118.4(3) . . ?
C18 C13 C12 123.4(3) . . ?
C15 C14 C13 122.4(3) . . ?
C14 C15 C16 118.7(3) . . ?
C14 C15 C19 118.5(3) . . ?
C16 C15 C19 122.8(3) . . ?
C17 C16 C15 118.2(2) . . ?
C17 C16 C1 119.1(3) . . ?
C15 C16 C1 122.7(2) . . ?
C16 C17 C18 122.6(3) . . ?
C13 C18 C17 117.8(3) . . ?
C13 C18 C30 123.6(3) . . ?
C17 C18 C30 118.5(3) . . ?
C15 C19 C20 114.4(3) . . ?
C21 C20 C19 117.0(4) . . ?
C22 C21 C20 114.2(3) . . ?
C23 C22 C27 116.6(3) . . ?
C23 C22 C21 122.3(4) . . ?
C27 C22 C21 121.0(4) . . ?
C22 C23 C24 120.9(4) . . ?
C25 C24 C23 121.8(3) . . ?
C24 C25 C26 117.5(3) . . ?
C24 C25 C28 122.9(4) . . ?
C26 C25 C28 119.5(4) . . ?
C27 C26 C25 120.8(3) . . ?
C26 C27 C22 121.4(3) . . ?
C29 C28 C25 118.2(4) . . ?
C28 C29 C30 124.2(4) . . ?
C29 C30 C18 117.8(4) . . ?
C5 N1 S1 106.0(2) . . ?
C6 N2 S1 106.5(2) . . ?
N2 S1 N1 101.21(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C16 1.524(4) . ?
C1 C2 1.540(4) . ?
C2 C3 1.540(5) . ?
C3 C4 1.511(5) . ?
C4 C9 1.367(5) . ?
C4 C5 1.429(4) . ?
C5 N1 1.342(4) . ?
C5 C6 1.450(4) . ?
C6 N2 1.349(4) . ?
C6 C7 1.421(4) . ?
C7 C8 1.363(5) . ?
C7 C10 1.508(5) . ?
C8 C9 1.428(5) . ?
C10 C11 1.489(7) . ?
C11 C12 1.489(7) . ?
C12 C13 1.514(4) . ?
C13 C14 1.403(5) . ?
C13 C18 1.406(5) . ?
C14 C15 1.391(4) . ?
C15 C16 1.399(4) . ?
C15 C19 1.521(4) . ?
C16 C17 1.394(4) . ?
C17 C18 1.408(4) . ?
C18 C30 1.518(4) . ?
C19 C20 1.545(5) . ?
C20 C21 1.540(5) . ?
C21 C22 1.510(5) . ?
C22 C23 1.386(5) . ?
C22 C27 1.409(5) . ?
C23 C24 1.386(6) . ?
C24 C25 1.372(6) . ?
C25 C26 1.395(5) . ?
C25 C28 1.536(5) . ?
C26 C27 1.372(5) . ?
C28 C29 1.438(7) . ?
C29 C30 1.507(7) . ?
N1 S1 1.624(3) . ?
N2 S1 1.620(3) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C1 C2 C3 -66.1(4) . . . . ?
C1 C2 C3 C4 65.0(4) . . . . ?
C2 C3 C4 C9 -115.8(4) . . . . ?
C2 C3 C4 C5 59.3(4) . . . . ?
C9 C4 C5 N1 -177.3(3) . . . . ?
C3 C4 C5 N1 7.2(4) . . . . ?
C9 C4 C5 C6 6.9(4) . . . . ?
C3 C4 C5 C6 -168.6(3) . . . . ?
N1 C5 C6 N2 0.9(4) . . . . ?
C4 C5 C6 N2 177.1(3) . . . . ?
N1 C5 C6 C7 -178.7(3) . . . . ?
C4 C5 C6 C7 -2.5(4) . . . . ?
N2 C6 C7 C8 176.2(3) . . . . ?
C5 C6 C7 C8 -4.2(4) . . . . ?
N2 C6 C7 C10 -9.5(5) . . . . ?
C5 C6 C7 C10 170.0(3) . . . . ?
C6 C7 C8 C9 6.3(4) . . . . ?
C10 C7 C8 C9 -167.8(3) . . . . ?
C5 C4 C9 C8 -5.1(4) . . . . ?
C3 C4 C9 C8 170.2(3) . . . . ?
C7 C8 C9 C4 -1.7(5) . . . . ?
C8 C7 C10 C11 115.0(4) . . . . ?
C6 C7 C10 C11 -58.8(5) . . . . ?
C7 C10 C11 C12 -59.1(6) . . . . ?
C10 C11 C12 C13 60.1(7) . . . . ?
C11 C12 C13 C14 -109.5(5) . . . . ?
C11 C12 C13 C18 70.7(5) . . . . ?
C18 C13 C14 C15 -6.7(4) . . . . ?
C12 C13 C14 C15 173.5(3) . . . . ?
C13 C14 C15 C16 -6.6(4) . . . . ?
C13 C14 C15 C19 173.7(3) . . . . ?
C14 C15 C16 C17 12.9(4) . . . . ?
C19 C15 C16 C17 -167.4(3) . . . . ?
C14 C15 C16 C1 -167.1(3) . . . . ?
C19 C15 C16 C1 12.6(4) . . . . ?
C2 C1 C16 C17 -61.1(4) . . . . ?
C2 C1 C16 C15 118.9(3) . . . . ?
C15 C16 C17 C18 -6.4(4) . . . . ?
C1 C16 C17 C18 173.6(3) . . . . ?
C14 C13 C18 C17 13.0(4) . . . . ?
C12 C13 C18 C17 -167.2(3) . . . . ?
C14 C13 C18 C30 -164.1(3) . . . . ?
C12 C13 C18 C30 15.6(5) . . . . ?
C16 C17 C18 C13 -6.8(4) . . . . ?
C16 C17 C18 C30 170.5(3) . . . . ?
C14 C15 C19 C20 -113.9(3) . . . . ?
C16 C15 C19 C20 66.4(4) . . . . ?
C15 C19 C20 C21 66.5(4) . . . . ?
C19 C20 C21 C22 -66.9(5) . . . . ?
C20 C21 C22 C23 120.4(4) . . . . ?
C20 C21 C22 C27 -56.1(5) . . . . ?
C27 C22 C23 C24 7.8(5) . . . . ?
C21 C22 C23 C24 -168.8(3) . . . . ?
C22 C23 C24 C25 0.3(6) . . . . ?
C23 C24 C25 C26 -8.1(5) . . . . ?
C23 C24 C25 C28 167.9(3) . . . . ?
C24 C25 C26 C27 7.5(5) . . . . ?
C28 C25 C26 C27 -168.6(3) . . . . ?
C25 C26 C27 C22 0.7(5) . . . . ?
C23 C22 C27 C26 -8.3(5) . . . . ?
C21 C22 C27 C26 168.3(3) . . . . ?
C24 C25 C28 C29 -63.8(6) . . . . ?
C26 C25 C28 C29 112.1(5) . . . . ?
C25 C28 C29 C30 -55.8(8) . . . . ?
C28 C29 C30 C18 54.3(7) . . . . ?
C13 C18 C30 C29 67.0(5) . . . . ?
C17 C18 C30 C29 -110.1(4) . . . . ?
C4 C5 N1 S1 -176.5(2) . . . . ?
C6 C5 N1 S1 -0.5(3) . . . . ?
C7 C6 N2 S1 178.7(3) . . . . ?
C5 C6 N2 S1 -0.9(3) . . . . ?
C6 N2 S1 N1 0.6(2) . . . . ?
C5 N1 S1 N2 0.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659264
