#------------------------------------------------------------------------------
#$Date: 2019-11-28 15:41:09 +0100 (jue 28 de nov de 2019) $
#$Revision: 244122 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/83/7238342.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_7238342
loop_
_publ_author_name
'Bailey, Andrew James'
'Horton, Peter Neil'
'Grossel, Martin Christopher'
_publ_section_title
;
 Self-assembly into infinite tapes by 2,7-disubstituted-1,8-naphthyridines
 in the solid state
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4074
_journal_paper_doi               10.1039/C0CE00243G
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C10 H10 N2'
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20
_chemical_name_systematic
;
2,7-dimethyl-1,8-naphthyridine
;
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.4667(6)
_cell_length_b                   19.3913(10)
_cell_length_c                   6.3165(3)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1649.47(14)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5363
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9693
_exptl_absorpt_correction_T_min  0.8588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Clear Colourless'
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.228
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0574
_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)+(0.0772P)²+0.2908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                439
_reflns_number_total             518
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ce00243g.txt
_cod_data_source_block           4
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               7238342
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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 0.01022(12) 0.44076(7) 0.8045(2) 0.0224(6) Uani 1 1 d .
C5 C 0.0000 0.5000 0.4652(5) 0.0214(7) Uani 1 2 d S
C3 C 0.02122(17) 0.37777(11) 0.4762(4) 0.0259(6) Uani 1 1 d .
H3 H 0.0287 0.3353 0.4098 0.031 Uiso 1 1 calc R
C7 C 0.02681(15) 0.31676(10) 0.8292(4) 0.0283(6) Uani 1 1 d .
H7A H 0.0387 0.3282 0.9748 0.043 Uiso 1 1 calc R
H7B H 0.0805 0.2890 0.7770 0.043 Uiso 1 1 calc R
H7C H -0.0343 0.2915 0.8178 0.043 Uiso 1 1 calc R
C6 C 0.0000 0.5000 0.6893(4) 0.0188(8) Uani 1 2 d S
C2 C 0.01971(16) 0.38157(10) 0.7012(3) 0.0221(7) Uani 1 1 d .
C4 C 0.01180(14) 0.43603(9) 0.3582(3) 0.0233(6) Uani 1 1 d .
H4 H 0.0130 0.4341 0.2111 0.028 Uiso 1 1 calc R
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 0.0263(11) 0.0210(12) 0.0199(11) 0.0014(7) 0.0019(8) -0.0005(7)
C5 0.0210(16) 0.0252(19) 0.0182(16) 0.000 0.000 -0.0006(12)
C3 0.0269(15) 0.0245(13) 0.0262(12) -0.0061(9) 0.0010(10) -0.0003(9)
C7 0.0335(11) 0.0217(11) 0.0298(12) 0.0034(9) 0.0018(11) 0.0003(8)
C6 0.0200(17) 0.0203(19) 0.0160(18) 0.000 0.000 -0.0003(11)
C2 0.0221(14) 0.0211(14) 0.0232(15) 0.0022(9) 0.0003(9) -0.0001(8)
C4 0.0238(12) 0.0285(12) 0.0175(12) -0.0017(10) 0.0009(9) 0.0007(8)
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 0.0000 '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 0.0000 '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
C2 N1 C6 118.34(16) . .
C6 C5 C4 118.39(14) . .
C6 C5 C4 118.39(14) . 2_565
C4 C5 C4 123.2(3) . 2_565
C4 C3 C2 120.22(19) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C6 N1 115.6(2) 2_565 .
N1 C6 C5 122.18(10) 2_565 .
N1 C6 C5 122.18(10) . .
N1 C2 C3 122.51(19) . .
N1 C2 C7 117.82(15) . .
C3 C2 C7 119.66(19) . .
C3 C4 C5 118.3(2) . .
C3 C4 H4 120.8 . .
C5 C4 H4 120.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.327(2) .
N1 C6 1.367(2) .
C5 C6 1.416(4) .
C5 C4 1.421(2) .
C5 C4 1.421(2) 2_565
C3 C4 1.359(3) .
C3 C2 1.423(3) .
C3 H3 0.9300 .
C7 C2 1.497(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C6 N1 1.367(2) 2_565
C4 H4 0.9300 .
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
C2 N1 C6 N1 179.53(19) . 2_565
C2 N1 C6 C5 -0.47(19) . .
C4 C5 C6 N1 179.53(14) . 2_565
C4 C5 C6 N1 -0.47(14) 2_565 2_565
C4 C5 C6 N1 -0.47(14) . .
C4 C5 C6 N1 179.53(14) 2_565 .
C6 N1 C2 C3 1.0(3) . .
C6 N1 C2 C7 -177.64(14) . .
C4 C3 C2 N1 -0.6(4) . .
C4 C3 C2 C7 178.01(17) . .
C2 C3 C4 C5 -0.3(3) . .
C6 C5 C4 C3 0.8(2) . .
C4 C5 C4 C3 -179.2(2) 2_565 .
