#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/80/2228005.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_2228005
loop_
_publ_author_name
'Vennila, K. N.'
'Prabha, K.'
'Manoj, M.'
'Prasad, K.J. Rajendra'
'Velmurugan, D.'
_publ_section_title
;
 7-(2-Chlorophenyl)-2,6,9-trimethyldibenzo[b,h][1,6]naphthyridine
;
_journal_coeditor_code           SU2198
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2426
_journal_page_last               o2427
_journal_paper_doi               10.1107/S1600536810030576
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C25 H19 Cl N2'
_chemical_formula_sum            'C25 H19 Cl N2'
_chemical_formula_weight         382.87
_chemical_name_common
;
7-(2-Chlorophenyl)-2,6,9-trimethyldibenzo[b,h][1,6]naphthyridine
;
_chemical_name_systematic
;
12-(2-chlorophenyl)-2,7,11-trimethyl-5,10-diazatetraphene
;
_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                93.755(3)
_cell_angle_beta                 103.099(3)
_cell_angle_gamma                102.074(3)
_cell_formula_units_Z            2
_cell_length_a                   6.5575(4)
_cell_length_b                   10.6538(7)
_cell_length_c                   14.3522(9)
_cell_measurement_reflns_used    4797
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      1.5
_cell_volume                     948.25(11)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ 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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17317
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.47
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0462
_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)+(0.0694P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                3514
_reflns_number_total             4771
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2198.cif
_cod_data_source_block           I
_cod_original_cell_volume        948.25(10)
_cod_database_code               2228005
_cod_database_fobs_code          2228005
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.22259(9) 0.49217(5) 0.41457(4) 0.0809(2) Uani d . 1 . .
C C9 0.1060(2) 0.63949(13) 0.20011(10) 0.0345(3) Uani d . 1 . .
C C14 -0.0361(2) 0.61889(13) 0.25997(11) 0.0354(3) Uani d . 1 . .
N N11 0.1756(2) 0.87266(11) 0.24184(9) 0.0396(3) Uani d . 1 . .
C C10 0.2149(2) 0.77063(13) 0.19709(10) 0.0353(3) Uani d . 1 . .
C C13 -0.0816(2) 0.72702(14) 0.30668(11) 0.0371(3) Uani d . 1 . .
C C6 0.3810(2) 0.79371(14) 0.14465(10) 0.0367(3) Uani d . 1 . .
C C1 0.4188(2) 0.68758(14) 0.09475(11) 0.0382(3) Uani d . 1 . .
C C12 0.0265(2) 0.85236(14) 0.29330(11) 0.0379(3) Uani d . 1 . .
N N7 0.2977(2) 0.56271(12) 0.09035(9) 0.0405(3) Uani d . 1 . .
C C5 0.5087(3) 0.91727(15) 0.14455(12) 0.0427(3) Uani d . 1 . .
H H5 0.4829 0.9885 0.1770 0.051 Uiso calc R 1 . .
C C21 -0.1424(2) 0.48827(13) 0.28004(11) 0.0383(3) Uani d . 1 . .
C C15 -0.2299(3) 0.71701(15) 0.36619(12) 0.0426(3) Uani d . 1 . .
H H15 -0.2983 0.6356 0.3770 0.051 Uiso calc R 1 . .
C C2 0.5826(3) 0.70513(17) 0.04574(13) 0.0478(4) Uani d . 1 . .
H H2 0.6075 0.6347 0.0119 0.057 Uiso calc R 1 . .
C C18 -0.0219(3) 0.96186(15) 0.33756(12) 0.0459(4) Uani d . 1 . .
H H18 0.0465 1.0444 0.3289 0.055 Uiso calc R 1 . .
C C8 0.1537(2) 0.53873(14) 0.13957(11) 0.0376(3) Uani d . 1 . .
C C16 -0.2740(3) 0.82394(16) 0.40769(12) 0.0435(4) Uani d . 1 . .
C C4 0.6710(3) 0.93469(16) 0.09730(12) 0.0463(4) Uani d . 1 . .
C C26 -0.0401(3) 0.42446(15) 0.35054(12) 0.0450(4) Uani d . 1 . .
C C17 -0.1666(3) 0.94743(16) 0.39226(12) 0.0471(4) Uani d . 1 . .
H H17 -0.1960 1.0206 0.4204 0.057 Uiso calc R 1 . .
C C22 -0.3525(3) 0.42820(16) 0.23021(15) 0.0529(4) Uani d . 1 . .
H H22 -0.4273 0.4693 0.1833 0.063 Uiso calc R 1 . .
C C3 0.7064(3) 0.82702(17) 0.04798(13) 0.0512(4) Uani d . 1 . .
H H3 0.8162 0.8381 0.0160 0.061 Uiso calc R 1 . .
C C23 -0.4512(3) 0.30820(18) 0.24972(17) 0.0622(5) Uani d . 1 . .
H H23 -0.5900 0.2684 0.2146 0.075 Uiso calc R 1 . .
C C19 0.0335(3) 0.39954(15) 0.12548(14) 0.0502(4) Uani d . 1 . .
H H19A 0.0790 0.3520 0.0779 0.075 Uiso calc R 1 . .
H H19B -0.1181 0.3942 0.1043 0.075 Uiso calc R 1 . .
H H19C 0.0630 0.3635 0.1853 0.075 Uiso calc R 1 . .
C C25 -0.1401(3) 0.30526(16) 0.37131(14) 0.0563(5) Uani d . 1 . .
H H25 -0.0683 0.2646 0.4195 0.068 Uiso calc R 1 . .
C C24 -0.3463(3) 0.24775(17) 0.32009(15) 0.0583(5) Uani d . 1 . .
H H24 -0.4144 0.1676 0.3334 0.070 Uiso calc R 1 . .
C C20 0.8124(3) 1.06674(18) 0.10020(15) 0.0613(5) Uani d . 1 . .
H H20A 0.9161 1.0606 0.0635 0.092 Uiso calc PR 0.50 . .
H H20B 0.8857 1.0999 0.1658 0.092 Uiso calc PR 0.50 . .
H H20C 0.7254 1.1239 0.0732 0.092 Uiso calc PR 0.50 . .
H H20D 0.7687 1.1290 0.1382 0.092 Uiso calc PR 0.50 . .
H H20E 0.7992 1.0897 0.0359 0.092 Uiso calc PR 0.50 . .
H H20F 0.9594 1.0657 0.1284 0.092 Uiso calc PR 0.50 . .
C C27 -0.4337(3) 0.81378(19) 0.46916(15) 0.0603(5) Uani d . 1 . .
H H27A -0.5716 0.8179 0.4303 0.090 Uiso calc R 1 . .
H H27B -0.3858 0.8839 0.5203 0.090 Uiso calc R 1 . .
H H27C -0.4454 0.7331 0.4960 0.090 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 C9 C10 . . 117.59(12) ?
C14 C9 C8 . . 125.62(13) ?
C10 C9 C8 . . 116.79(13) ?
C9 C14 C13 . . 118.93(13) ?
C9 C14 C21 . . 124.24(12) ?
C13 C14 C21 . . 116.82(13) ?
C10 N11 C12 . . 118.23(12) ?
N11 C10 C9 . . 123.65(13) ?
N11 C10 C6 . . 117.60(13) ?
C9 C10 C6 . . 118.73(12) ?
C14 C13 C12 . . 118.07(13) ?
C14 C13 C15 . . 123.54(13) ?
C12 C13 C15 . . 118.39(13) ?
C1 C6 C5 . . 119.07(14) ?
C1 C6 C10 . . 118.10(13) ?
C5 C6 C10 . . 122.80(14) ?
N7 C1 C6 . . 122.51(13) ?
N7 C1 C2 . . 117.55(13) ?
C6 C1 C2 . . 119.94(14) ?
N11 C12 C18 . . 118.06(13) ?
N11 C12 C13 . . 123.19(13) ?
C18 C12 C13 . . 118.73(14) ?
C8 N7 C1 . . 120.50(13) ?
C4 C5 C6 . . 121.15(15) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C26 C21 C22 . . 117.31(14) ?
C26 C21 C14 . . 121.67(14) ?
C22 C21 C14 . . 120.98(14) ?
C16 C15 C13 . . 121.68(15) ?
C16 C15 H15 . . 119.2 ?
C13 C15 H15 . . 119.2 ?
C3 C2 C1 . . 119.59(15) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C17 C18 C12 . . 120.70(15) ?
C17 C18 H18 . . 119.6 ?
C12 C18 H18 . . 119.6 ?
N7 C8 C9 . . 122.88(13) ?
N7 C8 C19 . . 114.02(13) ?
C9 C8 C19 . . 123.05(13) ?
C15 C16 C17 . . 118.83(15) ?
C15 C16 C27 . . 121.87(15) ?
C17 C16 C27 . . 119.31(14) ?
C5 C4 C3 . . 118.82(15) ?
C5 C4 C20 . . 120.96(16) ?
C3 C4 C20 . . 120.20(15) ?
C21 C26 C25 . . 121.90(16) ?
C21 C26 Cl1 . . 119.98(12) ?
C25 C26 Cl1 . . 118.11(14) ?
C18 C17 C16 . . 121.65(14) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C23 C22 C21 . . 120.83(17) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C2 C3 C4 . . 121.42(15) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C24 C23 C22 . . 120.50(18) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C8 C19 H19A . . 109.5 ?
C8 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C8 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C24 C25 C26 . . 119.42(17) ?
C24 C25 H25 . . 120.3 ?
C26 C25 H25 . . 120.3 ?
C23 C24 C25 . . 120.02(16) ?
C23 C24 H24 . . 120.0 ?
C25 C24 H24 . . 120.0 ?
C4 C20 H20A . . 109.5 ?
C4 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C4 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C4 C20 H20D . . 109.5 ?
H20A C20 H20D . . 141.1 ?
H20B C20 H20D . . 56.3 ?
H20C C20 H20D . . 56.3 ?
C4 C20 H20E . . 109.5 ?
H20A C20 H20E . . 56.3 ?
H20B C20 H20E . . 141.1 ?
H20C C20 H20E . . 56.3 ?
H20D C20 H20E . . 109.5 ?
C4 C20 H20F . . 109.5 ?
H20A C20 H20F . . 56.3 ?
H20B C20 H20F . . 56.3 ?
H20C C20 H20F . . 141.1 ?
H20D C20 H20F . . 109.5 ?
H20E C20 H20F . . 109.5 ?
C16 C27 H27A . . 109.5 ?
C16 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C16 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C26 . 1.7342(18) ?
C9 C14 . 1.399(2) ?
C9 C10 . 1.4381(19) ?
C9 C8 . 1.465(2) ?
C14 C13 . 1.414(2) ?
C14 C21 . 1.4978(19) ?
N11 C10 . 1.3272(18) ?
N11 C12 . 1.3449(19) ?
C10 C6 . 1.448(2) ?
C13 C12 . 1.422(2) ?
C13 C15 . 1.425(2) ?
C6 C1 . 1.395(2) ?
C6 C5 . 1.405(2) ?
C1 N7 . 1.3888(19) ?
C1 C2 . 1.399(2) ?
C12 C18 . 1.419(2) ?
N7 C8 . 1.2966(19) ?
C5 C4 . 1.374(2) ?
C5 H5 . 0.9300 ?
C21 C26 . 1.382(2) ?
C21 C22 . 1.394(2) ?
C15 C16 . 1.365(2) ?
C15 H15 . 0.9300 ?
C2 C3 . 1.374(2) ?
C2 H2 . 0.9300 ?
C18 C17 . 1.353(2) ?
C18 H18 . 0.9300 ?
C8 C19 . 1.504(2) ?
C16 C17 . 1.413(2) ?
C16 C27 . 1.507(2) ?
C4 C3 . 1.397(2) ?
C4 C20 . 1.507(2) ?
C26 C25 . 1.386(2) ?
C17 H17 . 0.9300 ?
C22 C23 . 1.384(2) ?
C22 H22 . 0.9300 ?
C3 H3 . 0.9300 ?
C23 C24 . 1.365(3) ?
C23 H23 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C25 C24 . 1.374(3) ?
C25 H25 . 0.9300 ?
C24 H24 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C20 H20D . 0.9600 ?
C20 H20E . 0.9600 ?
C20 H20F . 0.9600 ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C22 H22 N7 1_455 0.93 2.42 3.318(2) 162
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C9 C14 C13 . . . . 6.1(2) ?
C8 C9 C14 C13 . . . . -173.70(13) ?
C10 C9 C14 C21 . . . . -172.70(13) ?
C8 C9 C14 C21 . . . . 7.5(2) ?
C12 N11 C10 C9 . . . . 0.4(2) ?
C12 N11 C10 C6 . . . . -177.97(13) ?
C14 C9 C10 N11 . . . . -5.4(2) ?
C8 C9 C10 N11 . . . . 174.47(13) ?
C14 C9 C10 C6 . . . . 172.95(13) ?
C8 C9 C10 C6 . . . . -7.2(2) ?
C9 C14 C13 C12 . . . . -2.4(2) ?
C21 C14 C13 C12 . . . . 176.51(13) ?
C9 C14 C13 C15 . . . . 177.54(14) ?
C21 C14 C13 C15 . . . . -3.6(2) ?
N11 C10 C6 C1 . . . . -177.95(13) ?
C9 C10 C6 C1 . . . . 3.6(2) ?
N11 C10 C6 C5 . . . . 4.1(2) ?
C9 C10 C6 C5 . . . . -174.35(14) ?
C5 C6 C1 N7 . . . . -179.11(14) ?
C10 C6 C1 N7 . . . . 2.8(2) ?
C5 C6 C1 C2 . . . . 0.1(2) ?
C10 C6 C1 C2 . . . . -177.91(14) ?
C10 N11 C12 C18 . . . . -177.28(14) ?
C10 N11 C12 C13 . . . . 3.8(2) ?
C14 C13 C12 N11 . . . . -2.8(2) ?
C15 C13 C12 N11 . . . . 177.25(14) ?
C14 C13 C12 C18 . . . . 178.29(14) ?
C15 C13 C12 C18 . . . . -1.6(2) ?
C6 C1 N7 C8 . . . . -5.5(2) ?
C2 C1 N7 C8 . . . . 175.23(15) ?
C1 C6 C5 C4 . . . . -0.8(2) ?
C10 C6 C5 C4 . . . . 177.17(14) ?
C9 C14 C21 C26 . . . . 83.9(2) ?
C13 C14 C21 C26 . . . . -94.89(17) ?
C9 C14 C21 C22 . . . . -98.31(19) ?
C13 C14 C21 C22 . . . . 82.85(19) ?
C14 C13 C15 C16 . . . . -178.02(15) ?
C12 C13 C15 C16 . . . . 1.9(2) ?
N7 C1 C2 C3 . . . . 179.93(16) ?
C6 C1 C2 C3 . . . . 0.6(3) ?
N11 C12 C18 C17 . . . . -178.30(15) ?
C13 C12 C18 C17 . . . . 0.6(2) ?
C1 N7 C8 C9 . . . . 1.4(2) ?
C1 N7 C8 C19 . . . . 178.83(14) ?
C14 C9 C8 N7 . . . . -175.27(14) ?
C10 C9 C8 N7 . . . . 4.9(2) ?
C14 C9 C8 C19 . . . . 7.5(2) ?
C10 C9 C8 C19 . . . . -172.28(14) ?
C13 C15 C16 C17 . . . . -1.1(2) ?
C13 C15 C16 C27 . . . . 178.85(16) ?
C6 C5 C4 C3 . . . . 0.6(3) ?
C6 C5 C4 C20 . . . . -177.91(16) ?
C22 C21 C26 C25 . . . . 0.3(2) ?
C14 C21 C26 C25 . . . . 178.09(15) ?
C22 C21 C26 Cl1 . . . . 179.19(13) ?
C14 C21 C26 Cl1 . . . . -3.0(2) ?
C12 C18 C17 C16 . . . . 0.2(3) ?
C15 C16 C17 C18 . . . . 0.0(3) ?
C27 C16 C17 C18 . . . . -179.91(17) ?
C26 C21 C22 C23 . . . . -1.4(3) ?
C14 C21 C22 C23 . . . . -179.24(16) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C5 C4 C3 C2 . . . . 0.2(3) ?
C20 C4 C3 C2 . . . . 178.72(18) ?
C21 C22 C23 C24 . . . . 1.7(3) ?
C21 C26 C25 C24 . . . . 0.6(3) ?
Cl1 C26 C25 C24 . . . . -178.38(14) ?
C22 C23 C24 C25 . . . . -0.9(3) ?
C26 C25 C24 C23 . . . . -0.3(3) ?
