#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/42/2204251.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2204251
loop_
_publ_author_name
'Yudong, Shen'
'Haiqiang, Wu'
'Xianzhang, Bu'
'Lianquan, Gu'
_publ_section_title
;
 2-Amino-7-chloro-1,8-naphthyridine
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1641
_journal_page_last               o1642
_journal_paper_doi               10.1107/S1600536804020884
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C8 H6 Cl N3'
_chemical_formula_moiety         'C8 H6 Cl N3'
_chemical_formula_sum            'C8 H6 Cl N3'
_chemical_formula_weight         179.61
_chemical_melting_point          .452E-305
_chemical_name_systematic
;
2-amino-7-chloro-1,8-naphthyridine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.012(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.906(7)
_cell_length_b                   12.538(13)
_cell_length_c                   9.099(9)
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.77
_cell_volume                     787.7(14)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker,1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4791
_diffrn_reflns_theta_full        27.22
_diffrn_reflns_theta_max         27.22
_diffrn_reflns_theta_min         2.77
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.8661
_exptl_absorpt_correction_T_min  0.8164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0357
_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)+(0.0589P)²+0.2069P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                1498
_reflns_number_total             1749
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6272.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204251
_cod_database_fobs_code          2204251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_type_symbol
Cl1 1.14367(7) 0.81937(4) 0.55480(5) 0.06047(19) Uani d . 1 Cl
N1 0.92935(19) 0.66304(10) 0.45997(13) 0.0409(3) Uani d . 1 N
N2 0.71727(17) 0.52888(10) 0.39707(13) 0.0406(3) Uani d . 1 N
C2 1.2349(2) 0.68261(13) 0.33712(19) 0.0507(4) Uani d . 1 C
H2 1.3502 0.7204 0.3293 0.061 Uiso calc R 1 H
N3 0.5031(2) 0.39486(12) 0.34545(16) 0.0556(4) Uani d . 1 N
H3A 0.4302 0.4187 0.4137 0.067 Uiso calc R 1 H
H3B 0.4684 0.3396 0.2956 0.067 Uiso calc R 1 H
C5 0.8888(2) 0.57736(11) 0.37248(14) 0.0368(3) Uani d . 1 C
C1 1.0958(2) 0.71003(13) 0.44037(16) 0.0434(3) Uani d . 1 C
C4 1.0192(2) 0.54205(12) 0.26415(15) 0.0399(3) Uani d . 1 C
C8 0.6709(2) 0.44386(13) 0.31670(16) 0.0425(3) Uani d . 1 C
C3 1.1932(2) 0.59769(14) 0.24847(18) 0.0484(4) Uani d . 1 C
H3 1.2805 0.5767 0.1774 0.058 Uiso calc R 1 H
C6 0.9629(2) 0.45210(13) 0.17916(16) 0.0465(4) Uani d . 1 C
H6 1.0436 0.4267 0.1063 0.056 Uiso calc R 1 H
C7 0.7931(3) 0.40338(14) 0.20357(17) 0.0477(4) Uani d . 1 C
H7 0.7554 0.3444 0.1481 0.057 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0608(3) 0.0563(3) 0.0647(3) -0.01606(19) 0.0119(2) -0.01139(19)
N1 0.0409(6) 0.0425(7) 0.0395(6) 0.0004(5) 0.0062(5) 0.0014(5)
N2 0.0381(6) 0.0451(7) 0.0387(6) 0.0002(5) 0.0059(5) -0.0019(5)
C2 0.0427(8) 0.0528(9) 0.0571(9) -0.0042(7) 0.0129(7) 0.0069(7)
N3 0.0478(7) 0.0600(9) 0.0593(8) -0.0114(7) 0.0097(6) -0.0190(7)
C5 0.0371(7) 0.0403(7) 0.0331(6) 0.0045(5) 0.0043(5) 0.0057(5)
C1 0.0453(8) 0.0423(8) 0.0428(7) -0.0013(6) 0.0054(6) 0.0040(6)
C4 0.0416(7) 0.0427(8) 0.0358(7) 0.0075(6) 0.0076(5) 0.0068(6)
C8 0.0419(8) 0.0468(8) 0.0388(7) 0.0017(6) 0.0020(6) -0.0003(6)
C3 0.0464(8) 0.0525(9) 0.0469(8) 0.0044(7) 0.0178(7) 0.0060(7)
C6 0.0540(9) 0.0485(9) 0.0375(7) 0.0104(7) 0.0121(6) 0.0007(6)
C7 0.0564(9) 0.0463(9) 0.0405(8) 0.0022(7) 0.0047(6) -0.0066(6)
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
C1 N1 C5 116.60(13)
C8 N2 C5 118.18(12)
C3 C2 C1 116.66(15)
C3 C2 H2 121.7
C1 C2 H2 121.7
C8 N3 H3A 120.0
C8 N3 H3B 120.0
H3A N3 H3B 120.0
N2 C5 N1 115.39(12)
N2 C5 C4 122.91(14)
N1 C5 C4 121.70(14)
N1 C1 C2 126.68(16)
N1 C1 Cl1 115.45(12)
C2 C1 Cl1 117.87(13)
C3 C4 C5 118.20(15)
C3 C4 C6 124.69(14)
C5 C4 C6 117.11(14)
N2 C8 N3 117.42(14)
N2 C8 C7 122.66(15)
N3 C8 C7 119.92(15)
C2 C3 C4 120.14(14)
C2 C3 H3 119.9
C4 C3 H3 119.9
C7 C6 C4 120.22(14)
C7 C6 H6 119.9
C4 C6 H6 119.9
C6 C7 C8 118.91(16)
C6 C7 H7 120.5
C8 C7 H7 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.749(2) ?
N1 C1 1.307(2) yes
N1 C5 1.363(2) yes
N2 C8 1.329(2) yes
N2 C5 1.354(2) yes
C2 C3 1.363(3) yes
C2 C1 1.399(2) yes
C2 H2 0.9300 ?
N3 C8 1.342(2) ?
N3 H3A 0.8600 ?
N3 H3B 0.8600 ?
C5 C4 1.418(2) yes
C4 C3 1.398(2) yes
C4 C6 1.418(2) yes
C8 C7 1.435(2) yes
C3 H3 0.9300 ?
C6 C7 1.344(3) yes
C6 H6 0.9300 ?
C7 H7 0.9300 ?
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
N3 H3A N2 3_666 0.86 2.12 2.974(3) 172
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
C8 N2 C5 N1 -178.99(13)
C8 N2 C5 C4 0.7(2)
C1 N1 C5 N2 178.74(13)
C1 N1 C5 C4 -1.0(2)
C5 N1 C1 C2 1.2(2)
C5 N1 C1 Cl1 -179.78(10)
C3 C2 C1 N1 -0.5(3)
C3 C2 C1 Cl1 -179.43(12)
N2 C5 C4 C3 -179.67(13)
N1 C5 C4 C3 0.0(2)
N2 C5 C4 C6 0.3(2)
N1 C5 C4 C6 179.98(13)
C5 N2 C8 N3 178.06(14)
C5 N2 C8 C7 -1.4(2)
C1 C2 C3 C4 -0.6(2)
C5 C4 C3 C2 0.8(2)
C6 C4 C3 C2 -179.18(15)
C3 C4 C6 C7 179.37(15)
C5 C4 C6 C7 -0.6(2)
C4 C6 C7 C8 -0.1(2)
N2 C8 C7 C6 1.1(2)
N3 C8 C7 C6 -178.33(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 76834
