#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022978.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_4022978
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            'C22 H14 N2'
_chemical_formula_weight         306.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.642(11)
_cell_angle_beta                 77.243(11)
_cell_angle_gamma                61.931(8)
_cell_formula_units_Z            2
_cell_length_a                   8.0472(2)
_cell_length_b                   8.87180(10)
_cell_length_c                   12.4711(8)
_cell_measurement_reflns_used    3878
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.65
_cell_volume                     752.72(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.857
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6811
_diffrn_reflns_theta_full        27.85
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8033
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0468
_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)+(0.0535P)²+0.2162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2580
_reflns_number_total             3092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701297q-File004.cif
_cod_data_source_block           mm006
_cod_database_code               4022978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 -0.28491(17) 0.62235(16) 0.44590(11) 0.0233(3) Uani 1 1 d .
N2 N -0.17949(18) 0.28207(16) 0.57613(10) 0.0231(3) Uani 1 1 d .
C1 C 0.45610(19) 0.29208(18) 0.19096(12) 0.0190(3) Uani 1 1 d .
C2 C 0.5805(2) 0.36733(19) 0.16111(12) 0.0224(3) Uani 1 1 d .
H2 H 0.5444 0.4800 0.1158 0.027 Uiso 1 1 calc R
C3 C 0.7597(2) 0.2754(2) 0.19841(13) 0.0260(3) Uani 1 1 d .
H3 H 0.8461 0.3258 0.1782 0.031 Uiso 1 1 calc R
C4 C 0.8125(2) 0.1109(2) 0.26493(13) 0.0251(3) Uani 1 1 d .
H4 H 0.9348 0.0496 0.2898 0.030 Uiso 1 1 calc R
C5 C 0.68741(19) 0.03523(18) 0.29536(12) 0.0212(3) Uani 1 1 d .
H5 H 0.7230 -0.0767 0.3416 0.025 Uiso 1 1 calc R
C6 C 0.50994(19) 0.12570(17) 0.25719(11) 0.0180(3) Uani 1 1 d .
C7 C 0.35697(19) 0.06190(17) 0.28168(12) 0.0178(3) Uani 1 1 d .
H7 H 0.3973 -0.0577 0.3281 0.021 Uiso 1 1 calc R
C8 C 0.25496(19) 0.37244(17) 0.15919(11) 0.0184(3) Uani 1 1 d .
H8 H 0.2162 0.4914 0.1119 0.022 Uiso 1 1 calc R
C9 C 0.24828(18) 0.24300(18) 0.10233(12) 0.0186(3) Uani 1 1 d .
C10 C 0.1937(2) 0.27671(19) -0.00257(12) 0.0237(3) Uani 1 1 d .
H10 H 0.1583 0.3892 -0.0481 0.028 Uiso 1 1 calc R
C11 C 0.1911(2) 0.1439(2) -0.04054(13) 0.0298(4) Uani 1 1 d .
H11 H 0.1527 0.1663 -0.1121 0.036 Uiso 1 1 calc R
C12 C 0.2440(2) -0.0208(2) 0.02504(13) 0.0287(4) Uani 1 1 d .
H12 H 0.2416 -0.1104 -0.0018 0.034 Uiso 1 1 calc R
C13 C 0.3004(2) -0.05515(19) 0.12971(13) 0.0233(3) Uani 1 1 d .
H13 H 0.3373 -0.1682 0.1745 0.028 Uiso 1 1 calc R
C14 C 0.30263(18) 0.07628(18) 0.16850(12) 0.0186(3) Uani 1 1 d .
C15 C 0.18369(18) 0.19893(17) 0.33689(11) 0.0165(3) Uani 1 1 d .
C16 C 0.12790(19) 0.36945(17) 0.27021(11) 0.0166(3) Uani 1 1 d .
C17 C -0.02415(19) 0.50806(17) 0.30699(12) 0.0188(3) Uani 1 1 d .
H17 H -0.0586 0.6216 0.2632 0.023 Uiso 1 1 calc R
C18 C -0.13083(19) 0.48175(17) 0.41112(12) 0.0181(3) Uani 1 1 d .
C19 C -0.07678(19) 0.31199(17) 0.47656(11) 0.0177(3) Uani 1 1 d .
C20 C 0.08477(19) 0.17030(17) 0.43772(11) 0.0174(3) Uani 1 1 d .
H20 H 0.1237 0.0565 0.4816 0.021 Uiso 1 1 calc R
C21 C -0.3790(2) 0.5893(2) 0.54278(13) 0.0253(3) Uani 1 1 d .
H21 H -0.4859 0.6832 0.5707 0.030 Uiso 1 1 calc R
C22 C -0.3270(2) 0.4200(2) 0.60648(13) 0.0268(3) Uani 1 1 d .
H22 H -0.4024 0.4047 0.6749 0.032 Uiso 1 1 calc R
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
C21 N1 C18 115.82(13)
C22 N2 C19 115.67(13)
C2 C1 C6 120.35(13)
C2 C1 C8 126.70(13)
C6 C1 C8 112.95(12)
C1 C2 C3 119.14(14)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 120.50(14)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.45(13)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 119.09(14)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 120.45(13)
C5 C6 C7 125.92(13)
C1 C6 C7 113.62(12)
C15 C7 C14 105.07(11)
C15 C7 C6 105.47(11)
C14 C7 C6 106.32(11)
C15 C7 H7 113.1
C14 C7 H7 113.1
C6 C7 H7 113.1
C9 C8 C1 106.20(10)
C9 C8 C16 105.27(11)
C1 C8 C16 105.47(11)
C9 C8 H8 113.1
C1 C8 H8 113.1
C16 C8 H8 113.1
C10 C9 C14 120.17(13)
C10 C9 C8 126.72(13)
C14 C9 C8 113.10(12)
C9 C10 C11 119.19(14)
C9 C10 H10 120.4
C11 C10 H10 120.4
C12 C11 C10 120.67(14)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 120.21(14)
C11 C12 H12 119.9
C13 C12 H12 119.9
C14 C13 C12 119.59(14)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C9 120.17(13)
C13 C14 C7 126.40(13)
C9 C14 C7 113.42(12)
C20 C15 C16 121.04(12)
C20 C15 C7 126.28(12)
C16 C15 C7 112.67(12)
C17 C16 C15 120.57(13)
C17 C16 C8 126.74(13)
C15 C16 C8 112.69(11)
C16 C17 C18 119.57(13)
C16 C17 H17 120.2
C18 C17 H17 120.2
N1 C18 C19 121.50(13)
N1 C18 C17 118.71(13)
C19 C18 C17 119.79(12)
N2 C19 C20 119.30(13)
N2 C19 C18 121.08(12)
C20 C19 C18 119.61(13)
C15 C20 C19 119.40(13)
C15 C20 H20 120.3
C19 C20 H20 120.3
N1 C21 C22 122.49(13)
N1 C21 H21 118.8
C22 C21 H21 118.8
N2 C22 C21 123.41(14)
N2 C22 H22 118.3
C21 C22 H22 118.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C21 1.318(2)
N1 C18 1.3694(18)
N2 C22 1.3151(19)
N2 C19 1.3690(18)
C1 C2 1.385(2)
C1 C6 1.3997(19)
C1 C8 1.5273(19)
C2 C3 1.396(2)
C2 H2 0.9500
C3 C4 1.389(2)
C3 H3 0.9500
C4 C5 1.393(2)
C4 H4 0.9500
C5 C6 1.3891(19)
C5 H5 0.9500
C6 C7 1.5255(19)
C7 C15 1.5234(18)
C7 C14 1.5245(19)
C7 H7 1.0000
C8 C9 1.5267(19)
C8 C16 1.5310(18)
C8 H8 1.0000
C9 C10 1.385(2)
C9 C14 1.4014(19)
C10 C11 1.391(2)
C10 H10 0.9500
C11 C12 1.386(2)
C11 H11 0.9500
C12 C13 1.387(2)
C12 H12 0.9500
C13 C14 1.3842(19)
C13 H13 0.9500
C15 C20 1.3632(19)
C15 C16 1.4287(18)
C16 C17 1.3619(19)
C17 C18 1.419(2)
C17 H17 0.9500
C18 C19 1.4187(19)
C19 C20 1.4182(19)
C20 H20 0.9500
C21 C22 1.409(2)
C21 H21 0.9500
C22 H22 0.9500
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
C6 C1 C2 C3 -0.3(2)
C8 C1 C2 C3 179.50(13)
C1 C2 C3 C4 -0.2(2)
C2 C3 C4 C5 0.0(2)
C3 C4 C5 C6 0.7(2)
C4 C5 C6 C1 -1.3(2)
C4 C5 C6 C7 179.54(12)
C2 C1 C6 C5 1.1(2)
C8 C1 C6 C5 -178.75(12)
C2 C1 C6 C7 -179.64(12)
C8 C1 C6 C7 0.52(16)
C5 C6 C7 C15 122.49(14)
C1 C6 C7 C15 -56.72(15)
C5 C6 C7 C14 -126.27(14)
C1 C6 C7 C14 54.51(14)
C2 C1 C8 C9 124.66(14)
C6 C1 C8 C9 -55.50(14)
C2 C1 C8 C16 -123.94(14)
C6 C1 C8 C16 55.90(14)
C1 C8 C9 C10 -125.39(14)
C16 C8 C9 C10 123.07(14)
C1 C8 C9 C14 55.44(14)
C16 C8 C9 C14 -56.11(14)
C14 C9 C10 C11 0.8(2)
C8 C9 C10 C11 -178.29(13)
C9 C10 C11 C12 -0.6(2)
C10 C11 C12 C13 0.0(2)
C11 C12 C13 C14 0.3(2)
C12 C13 C14 C9 0.0(2)
C12 C13 C14 C7 178.83(14)
C10 C9 C14 C13 -0.6(2)
C8 C9 C14 C13 178.69(12)
C10 C9 C14 C7 -179.56(12)
C8 C9 C14 C7 -0.32(16)
C15 C7 C14 C13 -121.98(14)
C6 C7 C14 C13 126.52(14)
C15 C7 C14 C9 56.96(15)
C6 C7 C14 C9 -54.55(14)
C14 C7 C15 C20 122.57(14)
C6 C7 C15 C20 -125.32(14)
C14 C7 C15 C16 -56.54(14)
C6 C7 C15 C16 55.58(14)
C20 C15 C16 C17 1.1(2)
C7 C15 C16 C17 -179.76(12)
C20 C15 C16 C8 -178.70(12)
C7 C15 C16 C8 0.46(16)
C9 C8 C16 C17 -123.98(14)
C1 C8 C16 C17 123.96(15)
C9 C8 C16 C15 55.78(14)
C1 C8 C16 C15 -56.28(14)
C15 C16 C17 C18 -1.7(2)
C8 C16 C17 C18 178.05(13)
C21 N1 C18 C19 -0.4(2)
C21 N1 C18 C17 179.46(13)
C16 C17 C18 N1 -179.04(13)
C16 C17 C18 C19 0.8(2)
C22 N2 C19 C20 179.90(13)
C22 N2 C19 C18 -0.9(2)
N1 C18 C19 N2 1.4(2)
C17 C18 C19 N2 -178.50(13)
N1 C18 C19 C20 -179.48(13)
C17 C18 C19 C20 0.7(2)
C16 C15 C20 C19 0.4(2)
C7 C15 C20 C19 -178.61(12)
N2 C19 C20 C15 177.90(12)
C18 C19 C20 C15 -1.3(2)
C18 N1 C21 C22 -0.9(2)
C19 N2 C22 C21 -0.3(2)
N1 C21 C22 N2 1.3(2)
