#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178455 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/76/4027617.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_4027617
loop_
_publ_author_name
'Peng-Fei Li'
'Chuan-Feng Chen'
_publ_section_title
;
 Synthesis, Structures, and Solid State Self-Assemblies of Formyl and
 Acetyl Substituted Triptycenes and Their Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9250
_journal_page_last               9259
_journal_paper_doi               10.1021/jo301820v
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H12 N2'
_chemical_formula_sum            'C22 H12 N2'
_chemical_formula_weight         304.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            4
_cell_length_a                   13.333(3)
_cell_length_b                   8.0402(16)
_cell_length_c                   14.989(3)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4642
_cell_measurement_theta_min      1.3586
_cell_volume                     1606.8(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5619
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0655
_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)+(0.0406P)²+0.7947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                1725
_reflns_number_total             1832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301820v_si_003.cif
_cod_data_source_block           a
_cod_database_code               4027617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.28177(17) 0.5304(3) 0.43955(13) 0.0668(6) Uani 1 1 d .
C1 C 0.53024(15) -0.3368(2) 0.71246(15) 0.0451(5) Uani 1 1 d .
H1 H 0.5508 -0.4395 0.6869 0.054 Uiso 1 1 calc R
C2 C 0.56117(14) -0.1882(2) 0.67423(14) 0.0370(5) Uani 1 1 d .
H2 H 0.6024 -0.1885 0.6225 0.044 Uiso 1 1 calc R
C3 C 0.53113(12) -0.0397(2) 0.71239(11) 0.0295(4) Uani 1 1 d .
C4 C 0.55923(12) 0.1344(2) 0.68085(11) 0.0276(4) Uani 1 1 d .
H4 H 0.6048 0.1344 0.6279 0.033 Uiso 1 1 calc R
C5 C 0.45990(12) 0.2225(2) 0.66382(11) 0.0269(4) Uani 1 1 d .
C6 C 0.43060(14) 0.2989(2) 0.58579(12) 0.0319(4) Uani 1 1 d .
H6 H 0.4738 0.3007 0.5354 0.038 Uiso 1 1 calc R
C7 C 0.33571(14) 0.3739(2) 0.58220(12) 0.0353(4) Uani 1 1 d .
C8 C 0.27183(14) 0.3702(2) 0.65501(13) 0.0369(4) Uani 1 1 d .
H8 H 0.2073 0.4199 0.6512 0.044 Uiso 1 1 calc R
C9 C 0.30202(13) 0.2938(2) 0.73355(12) 0.0331(4) Uani 1 1 d .
H9 H 0.2586 0.2913 0.7838 0.040 Uiso 1 1 calc R
C10 C 0.39597(12) 0.2212(2) 0.73808(11) 0.0271(4) Uani 1 1 d .
C11 C 0.30552(16) 0.4602(3) 0.50227(14) 0.0464(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0674(14) 0.0816(16) 0.0514(11) 0.0183(11) -0.0076(10) 0.0235(12)
C1 0.0367(11) 0.0284(9) 0.0702(15) -0.0097(9) -0.0144(9) 0.0047(7)
C2 0.0295(9) 0.0359(10) 0.0454(11) -0.0083(9) -0.0080(8) 0.0058(7)
C3 0.0227(8) 0.0301(9) 0.0358(9) -0.0021(7) -0.0063(7) 0.0007(6)
C4 0.0233(8) 0.0328(9) 0.0266(8) -0.0003(7) 0.0012(6) 0.0016(6)
C5 0.0249(8) 0.0259(8) 0.0298(8) -0.0031(7) -0.0020(6) -0.0004(6)
C6 0.0324(9) 0.0350(10) 0.0282(8) -0.0011(7) -0.0029(7) 0.0011(7)
C7 0.0373(10) 0.0358(10) 0.0329(9) -0.0005(8) -0.0091(8) 0.0059(8)
C8 0.0289(9) 0.0398(10) 0.0420(10) -0.0058(9) -0.0062(8) 0.0110(8)
C9 0.0247(8) 0.0395(10) 0.0350(10) -0.0068(8) -0.0008(7) 0.0027(7)
C10 0.0243(8) 0.0270(8) 0.0299(9) -0.0039(7) -0.0026(6) -0.0015(6)
C11 0.0429(11) 0.0543(13) 0.0421(11) 0.0016(10) -0.0080(9) 0.0131(9)
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'
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
C1 C1 C2 120.57(12) 3_656 .
C1 C1 H1 119.7 3_656 .
C2 C1 H1 119.7 . .
C3 C2 C1 119.11(19) . .
C3 C2 H2 120.4 . .
C1 C2 H2 120.4 . .
C2 C3 C3 120.31(11) . 3_656
C2 C3 C4 126.40(16) . .
C3 C3 C4 113.30(9) 3_656 .
C10 C4 C5 105.16(13) 3_656 .
C10 C4 C3 105.63(14) 3_656 .
C5 C4 C3 105.39(13) . .
C10 C4 H4 113.3 3_656 .
C5 C4 H4 113.3 . .
C3 C4 H4 113.3 . .
C6 C5 C10 120.34(16) . .
C6 C5 C4 126.59(15) . .
C10 C5 C4 113.07(14) . .
C5 C6 C7 118.69(16) . .
C5 C6 H6 120.7 . .
C7 C6 H6 120.7 . .
C8 C7 C6 121.01(17) . .
C8 C7 C11 119.59(17) . .
C6 C7 C11 119.39(18) . .
C7 C8 C9 119.99(16) . .
C7 C8 H8 120.0 . .
C9 C8 H8 120.0 . .
C10 C9 C8 119.41(17) . .
C10 C9 H9 120.3 . .
C8 C9 H9 120.3 . .
C9 C10 C5 120.54(16) . .
C9 C10 C4 125.97(16) . 3_656
C5 C10 C4 113.49(15) . 3_656
N1 C11 C7 179.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.141(3) .
C1 C1 1.384(4) 3_656
C1 C2 1.388(3) .
C1 H1 0.9500 .
C2 C3 1.383(2) .
C2 H2 0.9500 .
C3 C3 1.400(3) 3_656
C3 C4 1.524(2) .
C4 C10 1.523(2) 3_656
C4 C5 1.523(2) .
C4 H4 1.0000 .
C5 C6 1.377(2) .
C5 C10 1.402(2) .
C6 C7 1.403(2) .
C6 H6 0.9500 .
C7 C8 1.385(3) .
C7 C11 1.442(3) .
C8 C9 1.387(3) .
C8 H8 0.9500 .
C9 C10 1.384(2) .
C9 H9 0.9500 .
C10 C4 1.523(2) 3_656
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
C1 C1 C2 C3 0.3(3) 3_656 .
C1 C2 C3 C3 -1.2(3) . 3_656
C1 C2 C3 C4 178.77(17) . .
C2 C3 C4 C10 -125.65(18) . 3_656
C3 C3 C4 C10 54.3(2) 3_656 3_656
C2 C3 C4 C5 123.32(18) . .
C3 C3 C4 C5 -56.7(2) 3_656 .
C10 C4 C5 C6 123.58(18) 3_656 .
C3 C4 C5 C6 -125.07(18) . .
C10 C4 C5 C10 -56.21(16) 3_656 .
C3 C4 C5 C10 55.15(18) . .
C10 C5 C6 C7 -0.4(3) . .
C4 C5 C6 C7 179.87(16) . .
C5 C6 C7 C8 -0.8(3) . .
C5 C6 C7 C11 177.50(17) . .
C6 C7 C8 C9 1.1(3) . .
C11 C7 C8 C9 -177.15(18) . .
C7 C8 C9 C10 -0.3(3) . .
C8 C9 C10 C5 -0.8(3) . .
C8 C9 C10 C4 179.30(16) . 3_656
C6 C5 C10 C9 1.2(3) . .
C4 C5 C10 C9 -179.05(15) . .
C6 C5 C10 C4 -178.94(15) . 3_656
C4 C5 C10 C4 0.86(19) . 3_656
C8 C7 C11 N1 71(16) . .
C6 C7 C11 N1 -107(16) . .
