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#$Date: 2022-11-30 11:27:15 +0200 (Wed, 30 Nov 2022) $
#$Revision: 279648 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106308.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_8106308
loop_
_publ_author_name
'Jia, Guo-Kai'
'Chen, Xiao-Ming'
'He, Fu-Lin'
'Chen, Xiu-Wen'
'Wang, Zong-Cheng'
_publ_section_title
;
 Crystal structure of 2-(3,4-dimethylphenyl)-1,8-naphthyridine, C16H14N2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              819
_journal_page_last               820
_journal_paper_doi               10.1515/ncrs-2018-0031
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C16 H14 N2 '
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29
_chemical_name_systematic
;
2-(3,4-dimethylphenyl)-1,8-naphthyridine
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.449(8)
_cell_length_b                   10.548(14)
_cell_length_c                   17.84(2)
_cell_measurement_reflns_used    2042
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      2.24
_cell_volume                     1214(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013) '
_computing_data_collection       'SAINT v8.34A (Bruker, 2013) '
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013) '
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) '
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) '
_computing_structure_refinement  'XL (Sheldrick, 2008) '
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990) '
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       φ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10765
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
ADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1112 before and 0.0446 after correction.
The Ratio of minimum to maximum transmission is 0.9230.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(4)
_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     165
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0406
_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)+(0.0469P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0933
_cod_data_source_file            suppl_ncrs-2018-0031_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1213(3)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C16 H14 N2 '
_cod_database_code               8106308
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 'x+1/2, -y+1/2, -z'
3 '-x, y+1/2, -z+1/2'
4 '-x+1/2, -y, 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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N -0.0273(2) -0.80067(16) -0.11350(10) 0.0559(4) Uani 1 d . . .
N2 N 0.0449(3) -0.65154(17) -0.20386(10) 0.0688(5) Uani 1 d . . .
C1 C 0.1687(4) -1.2625(2) 0.11848(14) 0.0781(7) Uani 1 d . . .
H1A H 0.1812 -1.2338 0.1693 0.117 Uiso 1 calc . . GR
H1B H 0.3028 -1.2861 0.0998 0.117 Uiso 1 calc . . GR
H1C H 0.0778 -1.3345 0.1166 0.117 Uiso 1 calc . . GR
C2 C 0.0809(3) -1.15737(18) 0.07076(12) 0.0597(5) Uani 1 d . . .
C3 C -0.1196(3) -1.11146(18) 0.08247(12) 0.0600(5) Uani 1 d . . .
C4 C -0.1931(3) -1.01494(18) 0.03748(12) 0.0587(5) Uani 1 d . . .
H4 H -0.3259 -0.9840 0.0463 0.070 Uiso 1 calc . . R
C5 C -0.0777(3) -0.96187(18) -0.02032(11) 0.0529(5) Uani 1 d . . .
C6 C -0.1613(3) -0.86172(18) -0.07048(11) 0.0524(5) Uani 1 d . . .
C7 C -0.1014(3) -0.70983(18) -0.16082(11) 0.0549(5) Uani 1 d . . .
C8 C -0.3138(3) -0.67853(18) -0.16533(12) 0.0575(5) Uani 1 d . . .
C9 C -0.3727(4) -0.5812(2) -0.21463(13) 0.0716(6) Uani 1 d . . .
H9 H -0.5113 -0.5576 -0.2185 0.086 Uiso 1 calc . . R
C10 C -0.2273(4) -0.5219(2) -0.25650(14) 0.0765(6) Uani 1 d . . .
H10 H -0.2631 -0.4566 -0.2891 0.092 Uiso 1 calc . . R
C11 C -0.0207(4) -0.5620(2) -0.24929(14) 0.0749(6) Uani 1 d . . .
H11 H 0.0778 -0.5220 -0.2791 0.090 Uiso 1 calc . . R
C12 C -0.3765(3) -0.8368(2) -0.07332(13) 0.0647(6) Uani 1 d . . .
H12 H -0.4666 -0.8824 -0.0428 0.078 Uiso 1 calc . . R
C13 C -0.4521(3) -0.7474(2) -0.12003(14) 0.0680(6) Uani 1 d . . .
H13 H -0.5939 -0.7315 -0.1222 0.082 Uiso 1 calc . . R
C14 C 0.1989(3) -1.10362(19) 0.01422(12) 0.0638(6) Uani 1 d . . .
H14 H 0.3334 -1.1326 0.0064 0.077 Uiso 1 calc . . R
C15 C 0.1221(3) -1.00794(19) -0.03096(12) 0.0609(6) Uani 1 d . . .
H15 H 0.2047 -0.9742 -0.0687 0.073 Uiso 1 calc . . R
C16 C -0.2536(4) -1.1658(2) 0.14321(13) 0.0800(7) Uani 1 d . . .
H16A H -0.3844 -1.1223 0.1439 0.120 Uiso 1 calc . . GR
H16B H -0.1860 -1.1555 0.1908 0.120 Uiso 1 calc . . GR
H16C H -0.2764 -1.2543 0.1338 0.120 Uiso 1 calc . . GR
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 0.000 0.000
;
International Tables Vol C Tables 4.2.6.8 and 6.1.1.4
;
N N 0.006 0.003
;
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
C6 N1 C7 118.20(18) . .
C11 N2 C7 116.7(2) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
C3 C2 C1 121.2(2) . .
C14 C2 C1 120.4(2) . .
C14 C2 C3 118.4(2) . .
C2 C3 C16 120.6(2) . .
C4 C3 C2 119.1(2) . .
C4 C3 C16 120.3(2) . .
C3 C4 H4 118.5 . .
C3 C4 C5 123.0(2) . .
C5 C4 H4 118.5 . .
C4 C5 C6 122.64(19) . .
C4 C5 C15 117.18(19) . .
C15 C5 C6 120.17(17) . .
N1 C6 C5 117.31(17) . .
N1 C6 C12 122.0(2) . .
C12 C6 C5 120.66(18) . .
N1 C7 C8 122.67(19) . .
N2 C7 N1 115.0(2) . .
N2 C7 C8 122.3(2) . .
C9 C8 C7 118.0(2) . .
C9 C8 C13 124.5(2) . .
C13 C8 C7 117.5(2) . .
C8 C9 H9 120.1 . .
C10 C9 C8 119.8(2) . .
C10 C9 H9 120.1 . .
C9 C10 H10 121.0 . .
C9 C10 C11 117.9(2) . .
C11 C10 H10 121.0 . .
N2 C11 C10 125.3(2) . .
N2 C11 H11 117.3 . .
C10 C11 H11 117.3 . .
C6 C12 H12 119.8 . .
C13 C12 C6 120.5(2) . .
C13 C12 H12 119.8 . .
C8 C13 H13 120.4 . .
C12 C13 C8 119.1(2) . .
C12 C13 H13 120.4 . .
C2 C14 H14 119.1 . .
C15 C14 C2 121.7(2) . .
C15 C14 H14 119.1 . .
C5 C15 H15 119.7 . .
C14 C15 C5 120.5(2) . .
C14 C15 H15 119.7 . .
C3 C16 H16A 109.5 . .
C3 C16 H16B 109.5 . .
C3 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.323(3) .
N1 C7 1.364(3) .
N2 C7 1.363(3) .
N2 C11 1.314(3) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 C2 1.508(3) .
C2 C3 1.396(3) .
C2 C14 1.385(3) .
C3 C4 1.380(3) .
C3 C16 1.500(3) .
C4 H4 0.9300 .
C4 C5 1.389(3) .
C5 C6 1.486(3) .
C5 C15 1.390(3) .
C6 C12 1.413(3) .
C7 C8 1.411(3) .
C8 C9 1.404(3) .
C8 C13 1.406(3) .
C9 H9 0.9300 .
C9 C10 1.352(3) .
C10 H10 0.9300 .
C10 C11 1.404(4) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C12 C13 1.350(3) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C14 C15 1.383(3) .
C15 H15 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
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
N1 C6 C12 C13 -0.9(3) . . . .
N1 C7 C8 C9 178.42(17) . . . .
N1 C7 C8 C13 -1.7(3) . . . .
N2 C7 C8 C9 -1.9(3) . . . .
N2 C7 C8 C13 178.06(19) . . . .
C1 C2 C3 C4 179.88(18) . . . .
C1 C2 C3 C16 0.1(3) . . . .
C1 C2 C14 C15 179.34(18) . . . .
C2 C3 C4 C5 1.1(3) . . . .
C2 C14 C15 C5 0.5(3) . . . .
C3 C2 C14 C15 -0.9(3) . . . .
C3 C4 C5 C6 177.39(17) . . . .
C3 C4 C5 C15 -1.5(3) . . . .
C4 C5 C6 N1 166.99(18) . . . .
C4 C5 C6 C12 -15.1(3) . . . .
C4 C5 C15 C14 0.7(3) . . . .
C5 C6 C12 C13 -178.73(18) . . . .
C6 N1 C7 N2 -179.51(17) . . . .
C6 N1 C7 C8 0.2(3) . . . .
C6 C5 C15 C14 -178.23(17) . . . .
C6 C12 C13 C8 -0.6(3) . . . .
C7 N1 C6 C5 178.94(16) . . . .
C7 N1 C6 C12 1.1(3) . . . .
C7 N2 C11 C10 0.3(3) . . . .
C7 C8 C9 C10 0.8(3) . . . .
C7 C8 C13 C12 1.8(3) . . . .
C8 C9 C10 C11 0.7(3) . . . .
C9 C8 C13 C12 -178.32(19) . . . .
C9 C10 C11 N2 -1.4(4) . . . .
C11 N2 C7 N1 -178.95(17) . . . .
C11 N2 C7 C8 1.3(3) . . . .
C13 C8 C9 C10 -179.1(2) . . . .
C14 C2 C3 C4 0.2(3) . . . .
C14 C2 C3 C16 -179.66(18) . . . .
C15 C5 C6 N1 -14.2(3) . . . .
C15 C5 C6 C12 163.74(19) . . . .
C16 C3 C4 C5 -179.10(18) . . . .
