#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:12:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178425 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/46/4024622.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_4024622
loop_
_publ_author_name
'Satoko Hayashi'
'Takashi Nakamoto'
'Mao Minoura'
'Waro Nakanishi'
_publ_section_title
;
Evidence for Effective p(Z)-π(Ar) Conjugations (Z = S, Se, and Te, as
Well as Z = O) in 9-(Arylchalcogenyl)triptycenes: Experimental and
Theoretical Investigations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4763
_journal_page_last               4771
_journal_paper_doi               10.1021/jo900488r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C26 H17 N O3'
_chemical_formula_weight         391.41
_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                 103.7440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5872(6)
_cell_length_b                   13.3959(7)
_cell_length_c                   12.7941(7)
_cell_measurement_reflns_used    5421
_cell_measurement_temperature    233
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.46
_cell_volume                     1929.05(18)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      233
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10492
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9571
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0138(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0380
_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)+(0.0579P)²+0.3852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                3662
_reflns_number_total             4322
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900488r_si_003.cif
_cod_data_source_block           1j
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4024622
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 0.24020(9) 0.15977(8) 0.06029(9) 0.0290(2) Uani 1 1 d . . .
C2 C 0.31710(9) 0.10305(8) 0.15570(9) 0.0312(2) Uani 1 1 d . . .
C3 C 0.38624(10) 0.02014(9) 0.14932(11) 0.0373(3) Uani 1 1 d . . .
H3A H 0.3872 -0.0081 0.0831 0.045 Uiso 1 1 calc R . .
C4 C 0.45457(12) -0.01999(10) 0.24482(12) 0.0482(3) Uani 1 1 d . . .
H4A H 0.5012 -0.0760 0.2422 0.058 Uiso 1 1 calc R . .
C5 C 0.45383(13) 0.02213(12) 0.34269(12) 0.0530(4) Uani 1 1 d . . .
H5A H 0.5005 -0.0054 0.4054 0.064 Uiso 1 1 calc R . .
C6 C 0.38402(12) 0.10548(11) 0.34891(11) 0.0457(3) Uani 1 1 d . . .
H6A H 0.3836 0.1337 0.4152 0.055 Uiso 1 1 calc R . .
C7 C 0.31531(10) 0.14568(9) 0.25509(9) 0.0345(3) Uani 1 1 d . . .
C8 C 0.23590(10) 0.23775(9) 0.24496(9) 0.0350(3) Uani 1 1 d . . .
H8A H 0.2342 0.2674 0.3146 0.042 Uiso 1 1 calc R . .
C9 C 0.28431(10) 0.30847(9) 0.17246(9) 0.0330(2) Uani 1 1 d . . .
C10 C 0.32765(11) 0.40366(9) 0.19970(11) 0.0425(3) Uani 1 1 d . . .
H10A H 0.3246 0.4312 0.2657 0.051 Uiso 1 1 calc R . .
C11 C 0.37574(12) 0.45759(10) 0.12748(13) 0.0493(3) Uani 1 1 d . . .
H11A H 0.4034 0.5222 0.1445 0.059 Uiso 1 1 calc R . .
C12 C 0.38260(11) 0.41574(10) 0.03060(12) 0.0457(3) Uani 1 1 d . . .
H12A H 0.4155 0.4523 -0.0169 0.055 Uiso 1 1 calc R . .
C13 C 0.34090(10) 0.31958(9) 0.00307(10) 0.0359(3) Uani 1 1 d . . .
H13A H 0.3475 0.2911 -0.0616 0.043 Uiso 1 1 calc R . .
C14 C 0.28943(9) 0.26685(8) 0.07333(9) 0.0299(2) Uani 1 1 d . . .
C15 C 0.11529(10) 0.16187(8) 0.08140(9) 0.0313(2) Uani 1 1 d . . .
C16 C 0.01251(11) 0.12292(9) 0.01589(11) 0.0388(3) Uani 1 1 d . . .
H16A H 0.0133 0.0959 -0.0509 0.047 Uiso 1 1 calc R . .
C17 C -0.09207(11) 0.12491(10) 0.05164(13) 0.0472(3) Uani 1 1 d . . .
H17A H -0.1618 0.0993 0.0083 0.057 Uiso 1 1 calc R . .
C18 C -0.09281(11) 0.16458(10) 0.15094(12) 0.0472(3) Uani 1 1 d . . .
H18A H -0.1629 0.1645 0.1743 0.057 Uiso 1 1 calc R . .
C19 C 0.00983(11) 0.20467(10) 0.21652(11) 0.0412(3) Uani 1 1 d . . .
H19A H 0.0085 0.2321 0.2830 0.049 Uiso 1 1 calc R . .
C20 C 0.11428(10) 0.20330(8) 0.18152(10) 0.0337(3) Uani 1 1 d . . .
C21 C 0.20513(10) 0.14399(9) -0.13595(9) 0.0332(3) Uani 1 1 d . . .
C22 C 0.24228(12) 0.08994(10) -0.21537(10) 0.0413(3) Uani 1 1 d . . .
H22A H 0.2876 0.0324 -0.1972 0.050 Uiso 1 1 calc R . .
C23 C 0.21176(12) 0.12183(11) -0.32071(11) 0.0465(3) Uani 1 1 d . . .
H23A H 0.2366 0.0867 -0.3741 0.056 Uiso 1 1 calc R . .
C24 C 0.14356(11) 0.20705(11) -0.34553(10) 0.0421(3) Uani 1 1 d . . .
C25 C 0.10178(11) 0.25915(10) -0.26878(10) 0.0398(3) Uani 1 1 d . . .
H25A H 0.0541 0.3152 -0.2880 0.048 Uiso 1 1 calc R . .
C26 C 0.13189(10) 0.22686(9) -0.16305(10) 0.0367(3) Uani 1 1 d . . .
H26A H 0.1034 0.2603 -0.1106 0.044 Uiso 1 1 calc R . .
O1 O 0.24864(7) 0.10784(6) -0.03449(6) 0.0356(2) Uani 1 1 d . . .
N1 N 0.11867(12) 0.24505(12) -0.45523(10) 0.0565(3) Uani 1 1 d . . .
O2 O 0.14712(13) 0.19362(12) -0.52417(9) 0.0837(4) Uani 1 1 d . . .
O3 O 0.07193(12) 0.32688(11) -0.47411(10) 0.0758(4) 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'
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
O1 C1 C2 107.00(9) . . ?
O1 C1 C15 114.71(9) . . ?
C2 C1 C15 105.28(9) . . ?
O1 C1 C14 116.75(9) . . ?
C2 C1 C14 104.22(8) . . ?
C15 C1 C14 107.75(8) . . ?
C3 C2 C7 121.03(11) . . ?
C3 C2 C1 125.94(11) . . ?
C7 C2 C1 113.00(10) . . ?
C2 C3 C4 118.26(12) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 120.93(12) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 120.69(12) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C7 C6 C5 119.05(13) . . ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C7 C2 120.04(12) . . ?
C6 C7 C8 126.87(11) . . ?
C2 C7 C8 113.06(10) . . ?
C9 C8 C20 107.00(9) . . ?
C9 C8 C7 104.64(9) . . ?
C20 C8 C7 105.29(9) . . ?
C9 C8 H8A 113.1 . . ?
C20 C8 H8A 113.1 . . ?
C7 C8 H8A 113.1 . . ?
C10 C9 C14 120.27(11) . . ?
C10 C9 C8 125.71(11) . . ?
C14 C9 C8 113.90(10) . . ?
C9 C10 C11 119.36(12) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 120.26(12) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 120.86(12) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C12 119.02(12) . . ?
C14 C13 H13A 120.5 . . ?
C12 C13 H13A 120.5 . . ?
C13 C14 C9 120.17(11) . . ?
C13 C14 C1 127.67(10) . . ?
C9 C14 C1 112.05(9) . . ?
C16 C15 C20 120.70(11) . . ?
C16 C15 C1 126.73(11) . . ?
C20 C15 C1 112.46(10) . . ?
C15 C16 C17 118.94(12) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C18 C17 C16 120.40(12) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C17 C18 C19 120.88(12) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C20 C19 C18 119.15(12) . . ?
C20 C19 H19A 120.4 . . ?
C18 C19 H19A 120.4 . . ?
C19 C20 C15 119.93(11) . . ?
C19 C20 C8 126.35(11) . . ?
C15 C20 C8 113.62(10) . . ?
O1 C21 C26 125.88(10) . . ?
O1 C21 C22 113.58(11) . . ?
C26 C21 C22 120.53(11) . . ?
C23 C22 C21 119.95(13) . . ?
C23 C22 H22A 120.0 . . ?
C21 C22 H22A 120.0 . . ?
C22 C23 C24 118.74(12) . . ?
C22 C23 H23A 120.6 . . ?
C24 C23 H23A 120.6 . . ?
C23 C24 C25 122.10(12) . . ?
C23 C24 N1 118.81(12) . . ?
C25 C24 N1 119.05(13) . . ?
C26 C25 C24 119.15(12) . . ?
C26 C25 H25A 120.4 . . ?
C24 C25 H25A 120.4 . . ?
C25 C26 C21 119.37(11) . . ?
C25 C26 H26A 120.3 . . ?
C21 C26 H26A 120.3 . . ?
C21 O1 C1 123.57(9) . . ?
O2 N1 O3 123.04(14) . . ?
O2 N1 C24 118.17(15) . . ?
O3 N1 C24 118.78(13) . . ?
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 O1 1.4214(13) . ?
C1 C2 1.5311(15) . ?
C1 C15 1.5343(15) . ?
C1 C14 1.5381(15) . ?
C2 C3 1.3832(16) . ?
C2 C7 1.3986(16) . ?
C3 C4 1.3961(18) . ?
C3 H3A 0.9300 . ?
C4 C5 1.375(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.3823(17) . ?
C6 H6A 0.9300 . ?
C7 C8 1.5257(16) . ?
C8 C9 1.5230(16) . ?
C8 C20 1.5213(16) . ?
C8 H8A 0.9800 . ?
C9 C10 1.3844(17) . ?
C9 C14 1.3995(16) . ?
C10 C11 1.390(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.380(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.3914(18) . ?
C12 H12A 0.9300 . ?
C13 C14 1.3848(16) . ?
C13 H13A 0.9300 . ?
C15 C16 1.3852(16) . ?
C15 C20 1.3987(16) . ?
C16 C17 1.3934(19) . ?
C16 H16A 0.9300 . ?
C17 C18 1.379(2) . ?
C17 H17A 0.9300 . ?
C18 C19 1.390(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.3867(16) . ?
C19 H19A 0.9300 . ?
C21 O1 1.3649(14) . ?
C21 C26 1.3904(17) . ?
C21 C22 1.3963(16) . ?
C22 C23 1.3775(19) . ?
C22 H22A 0.9300 . ?
C23 C24 1.382(2) . ?
C23 H23A 0.9300 . ?
C24 C25 1.3826(18) . ?
C24 N1 1.4559(17) . ?
C25 C26 1.3836(17) . ?
C25 H25A 0.9300 . ?
C26 H26A 0.9300 . ?
N1 O2 1.2246(18) . ?
N1 O3 1.2212(19) . ?
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
O1 C1 C2 C3 3.11(15) . . . . ?
C15 C1 C2 C3 125.57(11) . . . . ?
C14 C1 C2 C3 -121.15(11) . . . . ?
O1 C1 C2 C7 -179.06(9) . . . . ?
C15 C1 C2 C7 -56.60(12) . . . . ?
C14 C1 C2 C7 56.68(12) . . . . ?
C7 C2 C3 C4 -0.11(17) . . . . ?
C1 C2 C3 C4 177.57(11) . . . . ?
C2 C3 C4 C5 -0.41(19) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
C5 C6 C7 C2 -0.40(19) . . . . ?
C5 C6 C7 C8 -178.32(12) . . . . ?
C3 C2 C7 C6 0.51(17) . . . . ?
C1 C2 C7 C6 -177.44(11) . . . . ?
C3 C2 C7 C8 178.71(10) . . . . ?
C1 C2 C7 C8 0.75(14) . . . . ?
C6 C7 C8 C9 121.13(13) . . . . ?
C2 C7 C8 C9 -56.92(12) . . . . ?
C6 C7 C8 C20 -126.26(13) . . . . ?
C2 C7 C8 C20 55.70(12) . . . . ?
C20 C8 C9 C10 127.97(12) . . . . ?
C7 C8 C9 C10 -120.64(12) . . . . ?
C20 C8 C9 C14 -55.97(12) . . . . ?
C7 C8 C9 C14 55.43(12) . . . . ?
C14 C9 C10 C11 0.30(18) . . . . ?
C8 C9 C10 C11 176.13(12) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 1.56(19) . . . . ?
C12 C13 C14 C9 -2.69(17) . . . . ?
C12 C13 C14 C1 -178.63(11) . . . . ?
C10 C9 C14 C13 1.79(17) . . . . ?
C8 C9 C14 C13 -174.51(10) . . . . ?
C10 C9 C14 C1 178.31(10) . . . . ?
C8 C9 C14 C1 2.01(13) . . . . ?
O1 C1 C14 C13 0.38(16) . . . . ?
C2 C1 C14 C13 118.12(12) . . . . ?
C15 C1 C14 C13 -130.37(12) . . . . ?
O1 C1 C14 C9 -175.82(9) . . . . ?
C2 C1 C14 C9 -58.08(11) . . . . ?
C15 C1 C14 C9 53.42(12) . . . . ?
O1 C1 C15 C16 -3.10(16) . . . . ?
C2 C1 C15 C16 -120.44(12) . . . . ?
C14 C1 C15 C16 128.78(12) . . . . ?
O1 C1 C15 C20 172.92(9) . . . . ?
C2 C1 C15 C20 55.57(11) . . . . ?
C14 C1 C15 C20 -55.21(12) . . . . ?
C20 C15 C16 C17 -0.48(17) . . . . ?
C1 C15 C16 C17 175.23(11) . . . . ?
C15 C16 C17 C18 -0.36(19) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C17 C18 C19 C20 -0.81(19) . . . . ?
C18 C19 C20 C15 -0.03(18) . . . . ?
C18 C19 C20 C8 -176.00(11) . . . . ?
C16 C15 C20 C19 0.68(17) . . . . ?
C1 C15 C20 C19 -175.61(10) . . . . ?
C16 C15 C20 C8 177.14(10) . . . . ?
C1 C15 C20 C8 0.85(13) . . . . ?
C9 C8 C20 C19 -129.61(12) . . . . ?
C7 C8 C20 C19 119.45(12) . . . . ?
C9 C8 C20 C15 54.20(12) . . . . ?
C7 C8 C20 C15 -56.74(12) . . . . ?
O1 C21 C22 C23 -175.67(11) . . . . ?
C26 C21 C22 C23 3.59(18) . . . . ?
C21 C22 C23 C24 -0.52(19) . . . . ?
C22 C23 C24 C25 -2.25(19) . . . . ?
C22 C23 C24 N1 175.47(11) . . . . ?
C23 C24 C25 C26 1.93(18) . . . . ?
N1 C24 C25 C26 -175.78(11) . . . . ?
C24 C25 C26 C21 1.17(18) . . . . ?
O1 C21 C26 C25 175.26(11) . . . . ?
C22 C21 C26 C25 -3.91(18) . . . . ?
C26 C21 O1 C1 -10.46(17) . . . . ?
C22 C21 O1 C1 168.76(10) . . . . ?
C2 C1 O1 C21 -170.63(9) . . . . ?
C15 C1 O1 C21 73.02(13) . . . . ?
C14 C1 O1 C21 -54.41(13) . . . . ?
C23 C24 N1 O2 8.53(19) . . . . ?
C25 C24 N1 O2 -173.68(13) . . . . ?
C23 C24 N1 O3 -170.59(13) . . . . ?
C25 C24 N1 O3 7.20(18) . . . . ?
