#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022980.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_4022980
loop_
_publ_author_name
'Jonathan H. Chong'
'Mark J. MacLachlan'
_publ_section_title
;
 Synthesis and Structural Investigation of New Triptycene-Based
 Ligands: En Route to Shape-Persistent Dendrimers and Macrocycles
 with Large Free Volume
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8683
_journal_page_last               8690
_journal_paper_doi               10.1021/jo701297q
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C29 H18.5 N7.5'
_chemical_formula_weight         472.01
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 93.173(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.050(4)
_cell_length_b                   8.5056(8)
_cell_length_c                   17.790(3)
_cell_measurement_reflns_used    15671
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.182
_cell_measurement_theta_min      2.293
_cell_volume                     4539.9(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34041
_diffrn_reflns_theta_full        23.82
_diffrn_reflns_theta_max         23.82
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0397
_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)+(0.0583P)²+1.2766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                2331
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701297q-File006.cif
_cod_data_source_block           mm024
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C29 H18.50 N7.50'
_cod_database_code               4022980
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N3 N 0.40845(6) 0.8555(2) 0.84769(11) 0.0306(5) Uani 1 1 d .
N4 N 0.38933(6) 1.0866(2) 0.73548(12) 0.0351(5) Uani 1 1 d .
N2 N 0.47307(6) 0.4382(2) 0.39426(11) 0.0323(5) Uani 1 1 d .
N5 N 0.22215(6) 0.2293(2) 0.62196(11) 0.0325(5) Uani 1 1 d .
N1 N 0.48527(6) 0.1905(2) 0.50104(12) 0.0333(5) Uani 1 1 d .
C11 C 0.39635(7) 0.8144(2) 0.77504(12) 0.0233(5) Uani 1 1 d .
N6 N 0.20311(6) 0.4607(2) 0.50892(11) 0.0339(5) Uani 1 1 d .
C12 C 0.38718(7) 0.9296(2) 0.71876(13) 0.0246(5) Uani 1 1 d .
C3 C 0.45594(7) 0.3101(2) 0.51143(13) 0.0255(5) Uani 1 1 d .
C7 C 0.40178(7) 0.4260(2) 0.58747(12) 0.0217(5) Uani 1 1 d .
C14 C 0.37463(7) 0.8831(2) 0.64439(14) 0.0256(6) Uani 1 1 d .
C15 C 0.38015(6) 0.6107(2) 0.68435(12) 0.0215(5) Uani 1 1 d .
C9 C 0.41084(8) 1.0075(3) 0.86169(15) 0.0358(6) Uani 1 1 d .
C19 C 0.25302(7) 0.3373(2) 0.60292(12) 0.0263(6) Uani 1 1 d .
C8 C 0.39360(7) 0.5438(2) 0.53165(12) 0.0229(5) Uani 1 1 d .
C5 C 0.43181(7) 0.3096(2) 0.57696(13) 0.0242(5) Uani 1 1 d .
C20 C 0.24371(7) 0.4522(2) 0.54650(12) 0.0254(6) Uani 1 1 d .
C10 C 0.40098(9) 1.1214(3) 0.80602(15) 0.0391(7) Uani 1 1 d .
C16 C 0.37102(7) 0.7266(2) 0.62717(12) 0.0227(5) Uani 1 1 d .
C13 C 0.39254(7) 0.6531(3) 0.75615(13) 0.0226(5) Uani 1 1 d .
C4 C 0.44935(7) 0.4316(2) 0.45769(13) 0.0254(6) Uani 1 1 d .
C22 C 0.27679(7) 0.5603(3) 0.52815(13) 0.0256(6) Uani 1 1 d .
C21 C 0.29518(7) 0.3313(2) 0.64012(13) 0.0246(5) Uani 1 1 d .
C24 C 0.31725(7) 0.5531(2) 0.56491(12) 0.0230(5) Uani 1 1 d .
C23 C 0.32641(7) 0.4371(2) 0.62166(12) 0.0218(5) Uani 1 1 d .
C2 C 0.50106(8) 0.3214(3) 0.38659(16) 0.0363(6) Uani 1 1 d .
C6 C 0.41718(7) 0.5482(3) 0.46880(13) 0.0257(6) Uani 1 1 d .
C30 C 0.5000 0.3107(5) 0.7500 0.0669(13) Uani 1 2 d S
H30A H 0.5172 0.3483 0.7934 0.100 Uiso 0.50 1 calc PR
H30B H 0.4699 0.3483 0.7515 0.100 Uiso 0.50 1 calc PR
H30C H 0.5128 0.3483 0.7051 0.100 Uiso 0.50 1 calc PR
C17 C 0.18371(8) 0.2393(3) 0.58369(15) 0.0355(6) Uani 1 1 d .
C18 C 0.17445(9) 0.3540(3) 0.52846(15) 0.0367(6) Uani 1 1 d .
C28 C 0.26207(11) 0.8751(5) 0.6865(2) 0.0585(9) Uani 1 1 d .
C29 C 0.5000 0.1361(7) 0.7500 0.0625(12) Uani 1 2 d S
C1 C 0.50662(8) 0.1977(3) 0.43885(15) 0.0374(6) Uani 1 1 d .
N8 N 0.17996(11) 0.8322(5) 0.65099(17) 0.1072(13) Uani 1 1 d .
N7 N 0.5000 0.0014(5) 0.7500 0.0877(14) Uani 1 2 d S
C27 C 0.21619(11) 0.8490(4) 0.66722(17) 0.0640(9) Uani 1 1 d .
C25 C 0.37348(7) 0.4443(2) 0.65481(13) 0.0222(5) Uani 1 1 d .
C26 C 0.35697(7) 0.6568(2) 0.55122(13) 0.0240(5) Uani 1 1 d .
H14 H 0.3694(6) 0.966(2) 0.6061(11) 0.020(5) Uiso 1 1 d .
H6 H 0.4122(7) 0.630(3) 0.4323(12) 0.028(6) Uiso 1 1 d .
H21 H 0.3011(6) 0.253(2) 0.6769(12) 0.020(5) Uiso 1 1 d .
H13 H 0.3980(6) 0.578(2) 0.7948(12) 0.021(6) Uiso 1 1 d .
H17 H 0.1611(8) 0.161(3) 0.5965(12) 0.036(6) Uiso 1 1 d .
H5 H 0.4379(7) 0.227(3) 0.6156(12) 0.029(6) Uiso 1 1 d .
H22 H 0.2704(7) 0.639(2) 0.4905(12) 0.025(6) Uiso 1 1 d .
H2 H 0.5179(8) 0.323(2) 0.3401(14) 0.038(7) Uiso 1 1 d .
H18 H 0.1443(8) 0.358(3) 0.5000(14) 0.043(7) Uiso 1 1 d .
H10 H 0.4029(7) 1.236(3) 0.8194(13) 0.045(7) Uiso 1 1 d .
H9 H 0.4195(7) 1.040(2) 0.9188(14) 0.038(6) Uiso 1 1 d .
H1 H 0.5289(8) 0.105(3) 0.4276(14) 0.050(7) Uiso 1 1 d .
H25 H 0.3787(6) 0.365(2) 0.6920(11) 0.009(5) Uiso 1 1 d .
H26 H 0.3504(6) 0.733(2) 0.5116(12) 0.021(5) Uiso 1 1 d .
H28C H 0.2663(10) 0.956(4) 0.724(2) 0.080(12) Uiso 1 1 d .
H28B H 0.2728(12) 0.781(5) 0.708(2) 0.105(14) Uiso 1 1 d .
H28A H 0.2780(12) 0.906(4) 0.644(2) 0.109(14) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N3 C11 116.0(2)
C10 N4 C12 115.7(2)
C2 N2 C4 114.8(2)
C17 N5 C19 114.8(2)
C1 N1 C3 115.4(2)
N3 C11 C13 119.1(2)
N3 C11 C12 121.42(19)
C13 C11 C12 119.5(2)
C18 N6 C20 114.7(2)
N4 C12 C14 118.9(2)
N4 C12 C11 121.1(2)
C14 C12 C11 119.97(19)
N1 C3 C5 118.5(2)
N1 C3 C4 121.4(2)
C5 C3 C4 120.2(2)
C5 C7 C8 120.5(2)
C5 C7 C25 126.1(2)
C8 C7 C25 113.36(18)
C16 C14 C12 119.7(2)
C13 C15 C16 121.11(19)
C13 C15 C25 126.61(19)
C16 C15 C25 112.27(19)
N3 C9 C10 122.4(2)
N5 C19 C21 118.0(2)
N5 C19 C20 122.1(2)
C21 C19 C20 119.9(2)
C6 C8 C7 121.1(2)
C6 C8 C26 126.2(2)
C7 C8 C26 112.69(19)
C7 C5 C3 119.3(2)
N6 C20 C22 118.5(2)
N6 C20 C19 121.4(2)
C22 C20 C19 120.1(2)
N4 C10 C9 123.4(2)
C14 C16 C15 120.0(2)
C14 C16 C26 126.5(2)
C15 C16 C26 113.40(18)
C15 C13 C11 119.6(2)
N2 C4 C6 118.7(2)
N2 C4 C3 121.8(2)
C6 C4 C3 119.5(2)
C24 C22 C20 119.2(2)
C23 C21 C19 118.9(2)
C22 C24 C23 120.5(2)
C22 C24 C26 126.3(2)
C23 C24 C26 113.16(18)
C21 C23 C24 121.5(2)
C21 C23 C25 125.6(2)
C24 C23 C25 112.92(18)
N2 C2 C1 123.3(2)
C8 C6 C4 119.4(2)
N5 C17 C18 123.0(2)
N6 C18 C17 124.0(2)
N7 C29 C30 180.000(3)
N1 C1 C2 123.2(2)
N8 C27 C28 178.1(4)
C23 C25 C7 104.04(18)
C23 C25 C15 106.10(16)
C7 C25 C15 107.49(16)
C16 C26 C24 105.55(18)
C16 C26 C8 106.45(17)
C24 C26 C8 104.85(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N3 C9 1.317(3)
N3 C11 1.369(3)
N4 C10 1.318(3)
N4 C12 1.369(3)
N2 C2 1.314(3)
N2 C4 1.369(3)
N5 C17 1.311(3)
N5 C19 1.362(3)
N1 C1 1.311(3)
N1 C3 1.365(3)
C11 C13 1.415(3)
C11 C12 1.417(3)
N6 C18 1.311(3)
N6 C20 1.360(3)
C12 C14 1.412(3)
C3 C5 1.407(3)
C3 C4 1.414(3)
C7 C5 1.359(3)
C7 C8 1.423(3)
C7 C25 1.515(3)
C14 C16 1.369(3)
C15 C13 1.359(3)
C15 C16 1.432(3)
C15 C25 1.519(3)
C9 C10 1.405(3)
C19 C21 1.397(3)
C19 C20 1.418(3)
C8 C6 1.357(3)
C8 C26 1.516(3)
C20 C22 1.406(3)
C16 C26 1.514(3)
C4 C6 1.407(3)
C22 C24 1.350(3)
C21 C23 1.353(3)
C24 C23 1.428(3)
C24 C26 1.515(3)
C23 C25 1.503(3)
C2 C1 1.408(3)
C30 C29 1.485(7)
C17 C18 1.401(4)
C28 C27 1.419(5)
C29 N7 1.145(5)
N8 C27 1.120(4)
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
C9 N3 C11 C13 -179.2(2)
C9 N3 C11 C12 0.2(3)
C10 N4 C12 C14 179.6(2)
C10 N4 C12 C11 1.0(3)
N3 C11 C12 N4 -1.2(3)
C13 C11 C12 N4 178.19(19)
N3 C11 C12 C14 -179.8(2)
C13 C11 C12 C14 -0.4(3)
C1 N1 C3 C5 179.9(2)
C1 N1 C3 C4 0.4(3)
N4 C12 C14 C16 -178.1(2)
C11 C12 C14 C16 0.5(3)
C11 N3 C9 C10 0.9(3)
C17 N5 C19 C21 -178.5(2)
C17 N5 C19 C20 0.6(3)
C5 C7 C8 C6 -3.7(3)
C25 C7 C8 C6 177.67(19)
C5 C7 C8 C26 176.27(18)
C25 C7 C8 C26 -2.4(2)
C8 C7 C5 C3 2.3(3)
C25 C7 C5 C3 -179.29(19)
N1 C3 C5 C7 -178.62(19)
C4 C3 C5 C7 0.8(3)
C18 N6 C20 C22 178.8(2)
C18 N6 C20 C19 -1.0(3)
N5 C19 C20 N6 0.5(3)
C21 C19 C20 N6 179.6(2)
N5 C19 C20 C22 -179.30(19)
C21 C19 C20 C22 -0.2(3)
C12 N4 C10 C9 0.1(4)
N3 C9 C10 N4 -1.2(4)
C12 C14 C16 C15 -0.3(3)
C12 C14 C16 C26 178.4(2)
C13 C15 C16 C14 -0.1(3)
C25 C15 C16 C14 178.89(19)
C13 C15 C16 C26 -179.01(19)
C25 C15 C16 C26 0.0(2)
C16 C15 C13 C11 0.3(3)
C25 C15 C13 C11 -178.58(19)
N3 C11 C13 C15 179.40(19)
C12 C11 C13 C15 0.0(3)
C2 N2 C4 C6 -177.2(2)
C2 N2 C4 C3 1.9(3)
N1 C3 C4 N2 -2.3(3)
C5 C3 C4 N2 178.24(19)
N1 C3 C4 C6 176.8(2)
C5 C3 C4 C6 -2.6(3)
N6 C20 C22 C24 -179.9(2)
C19 C20 C22 C24 -0.1(3)
N5 C19 C21 C23 179.60(19)
C20 C19 C21 C23 0.5(3)
C20 C22 C24 C23 0.1(3)
C20 C22 C24 C26 178.38(19)
C19 C21 C23 C24 -0.5(3)
C19 C21 C23 C25 -178.5(2)
C22 C24 C23 C21 0.2(3)
C26 C24 C23 C21 -178.32(19)
C22 C24 C23 C25 178.44(19)
C26 C24 C23 C25 -0.1(2)
C4 N2 C2 C1 0.2(3)
C7 C8 C6 C4 1.9(3)
C26 C8 C6 C4 -178.10(19)
N2 C4 C6 C8 -179.59(19)
C3 C4 C6 C8 1.2(3)
C19 N5 C17 C18 -1.3(3)
C20 N6 C18 C17 0.4(3)
N5 C17 C18 N6 0.9(4)
C3 N1 C1 C2 1.6(3)
N2 C2 C1 N1 -2.1(4)
C21 C23 C25 C7 121.2(2)
C24 C23 C25 C7 -56.9(2)
C21 C23 C25 C15 -125.5(2)
C24 C23 C25 C15 56.3(2)
C5 C7 C25 C23 -119.9(2)
C8 C7 C25 C23 58.6(2)
C5 C7 C25 C15 127.9(2)
C8 C7 C25 C15 -53.6(2)
C13 C15 C25 C23 122.7(2)
C16 C15 C25 C23 -56.2(2)
C13 C15 C25 C7 -126.4(2)
C16 C15 C25 C7 54.6(2)
C14 C16 C26 C24 -123.2(2)
C15 C16 C26 C24 55.6(2)
C14 C16 C26 C8 125.7(2)
C15 C16 C26 C8 -55.5(2)
C22 C24 C26 C16 125.9(2)
C23 C24 C26 C16 -55.7(2)
C22 C24 C26 C8 -121.9(2)
C23 C24 C26 C8 56.5(2)
C6 C8 C26 C16 -123.3(2)
C7 C8 C26 C16 56.8(2)
C6 C8 C26 C24 125.2(2)
C7 C8 C26 C24 -54.8(2)
