#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/96/2009627.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_2009627
loop_
_publ_author_name
'Barlow, M. G.'
'Pritchard, R. G.'
'Sibous, L.'
'Tipping, A. E.'
_publ_section_title
;
 1,7-Dichloro-9-azatricyclo[4.3.1.0^3,7^]decan-8-one, a hydrolysed
 Diels--Alder cycloaddition product from the reaction of
 3,5,6-trichloro-1,2,4-triazine with hexa-1,5-diene
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              550
_journal_page_last               551
_journal_paper_doi               10.1107/S0108270193010960
_journal_volume                  50
_journal_year                    1994
_chemical_formula_structural     ' C~9~ H~11~ N O Cl~2~ '
_chemical_formula_sum            'C9 H11 Cl2 N O'
_chemical_formula_weight         220.10
_chemical_name_systematic
;
1,7-Dichloro-9-azatricyclo[4.3.1.0^3,7^]decan-8-one
;
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.58(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4.0
_cell_length_a                   6.241(2)
_cell_length_b                   12.296(3)
_cell_length_c                   12.758(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      16.4
_cell_volume                     974.4(5)
_computing_cell_refinement       'P3/PC Diffractometer Program'
_computing_data_collection
'P3/PC Diffractometer Program (Siemens, 1989)'
_computing_data_reduction
'PROCESS TEXSAN (Molecular Structure Corporation, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'FINISH TEXSAN'
_computing_structure_refinement  'LS TEXSAN'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device       'Nicolet R3m/V'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2143
_diffrn_reflns_theta_max         26.1107
_diffrn_reflns_theta_min         1.0
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.6248
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       needle
_exptl_crystal_F_000             456.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         -0.47541
_refine_diff_density_min         0.34210
_refine_ls_extinction_coef       8.4E-6(9)
_refine_ls_extinction_method     Zachariasen_type_2_Gaussian_isotropic
_refine_ls_goodness_of_fit_obs   2.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1539
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0478
_refine_ls_shift/esd_max         0.0517
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0602
_reflns_number_observed          1539
_reflns_number_total             2143
_reflns_observed_criterion       'I > 2\s(I)'
_cod_data_source_file            hu1063.cif
_cod_data_source_block           S044
_cod_original_cell_volume        974.4(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2009627
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Cl(1) 0.6428(2) 0.02121(8) 0.22216(7) 0.0829
Cl(2) 0.66470(10) 0.30510(7) 0.61098(6) 0.0657
O(1) 0.9358(3) 0.11710(10) 0.57930(10) 0.0454
N(9) 0.7948(4) 0.0778(2) 0.4134(2) 0.0452
C(1) 0.6300(4) 0.1117(2) 0.3303(2) 0.0416
C(2) 0.4131(5) 0.1046(3) 0.3745(2) 0.0490
C(3) 0.4108(4) 0.1847(2) 0.4671(2) 0.0440
C(4) 0.2855(5) 0.2891(3) 0.4350(3) 0.0571
C(5) 0.4461(5) 0.3638(3) 0.3877(3) 0.0514
C(6) 0.6595(4) 0.3008(2) 0.3960(2) 0.0375
C(7) 0.6423(4) 0.2273(2) 0.4928(2) 0.0366
C(8) 0.8083(4) 0.1358(2) 0.5020(2) 0.0348
C(10) 0.6787(5) 0.2272(2) 0.2998(2) 0.0417
H(2A) 0.301(5) 0.125(2) 0.323(3) 0.056(8)
H(2B) 0.390(5) 0.028(3) 0.397(2) 0.057(9)
H(3) 0.359(5) 0.151(3) 0.529(3) 0.052(8)
H(4A) 0.160(5) 0.267(2) 0.386(2) 0.055(8)
H(4B) 0.221(6) 0.322(3) 0.494(3) 0.070(10)
H(5A) 0.474(6) 0.428(3) 0.421(3) 0.067(10)
H(5B) 0.401(5) 0.380(3) 0.321(3) 0.058(9)
H(6) 0.776(5) 0.343(2) 0.407(2) 0.042(7)
H(9) 0.870(5) 0.021(2) 0.410(2) 0.049(8)
H(10A) 0.586(5) 0.248(2) 0.248(2) 0.047(8)
H(10B) 0.816(6) 0.228(3) 0.279(2) 0.063(10)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 'International Tables'
H 0.000 0.000 'International Tables'
N 0.004 0.003 'International Tables'
O 0.008 0.006 'International Tables'
Cl 0.132 0.159 'International Tables'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 6 2
1 0 7
-3 4 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) N(9) C(8) 116.4(2) yes
Cl(1) C(1) N(9) 107.6(2) ?
Cl(1) C(1) C(2) 111.1(2) ?
Cl(1) C(1) C(10) 111.3(2) ?
N(9) C(1) C(2) 107.6(2) yes
N(9) C(1) C(10) 108.0(2) yes
C(2) C(1) C(10) 111.0(2) yes
C(1) C(2) C(3) 108.9(2) ?
C(2) C(3) C(4) 111.9(2) ?
C(2) C(3) C(7) 107.6(2) ?
C(4) C(3) C(7) 102.4(2) ?
C(3) C(4) C(5) 105.7(2) ?
C(4) C(5) C(6) 105.6(2) ?
C(5) C(6) C(7) 102.9(2) ?
C(5) C(6) C(10) 112.1(2) ?
C(7) C(6) C(10) 108.1(2) ?
Cl(2) C(7) C(3) 110.9(2) ?
Cl(2) C(7) C(6) 110.9(2) ?
Cl(2) C(7) C(8) 109.5(2) ?
C(3) C(7) C(6) 99.5(2) yes
C(3) C(7) C(8) 112.4(2) yes
C(6) C(7) C(8) 113.2(2) yes
O(1) C(8) N(9) 124.3(2) ?
O(1) C(8) C(7) 125.6(2) ?
N(9) C(8) C(7) 110.1(2) ?
C(1) C(10) C(6) 108.3(2) ?
C(1) N(9) H(9) 124(2) ?
C(8) N(9) H(9) 120(2) ?
C(1) C(2) H(2A) 110(2) ?
C(1) C(2) H(2B) 109(2) ?
C(3) C(2) H(2A) 108(2) ?
C(3) C(2) H(2B) 111(2) ?
H(2A) C(2) H(2B) 110(3) ?
C(2) C(3) H(3) 112(2) ?
C(4) C(3) H(3) 112(2) ?
C(7) C(3) H(3) 111(2) ?
C(3) C(4) H(4A) 107(2) ?
C(3) C(4) H(4B) 112(2) ?
C(5) C(4) H(4A) 115(2) ?
C(5) C(4) H(4B) 113(2) ?
H(4A) C(4) H(4B) 104(3) ?
C(4) C(5) H(5A) 116(2) ?
C(4) C(5) H(5B) 111(2) ?
C(6) C(5) H(5A) 106(2) ?
C(6) C(5) H(5B) 112(2) ?
H(5A) C(5) H(5B) 106(3) ?
C(5) C(6) H(6) 114(2) ?
C(7) C(6) H(6) 110(2) ?
C(10) C(6) H(6) 110(2) ?
C(1) C(10) H(10A) 109(2) ?
C(1) C(10) H(10B) 108(2) ?
C(6) C(10) H(10A) 110(2) ?
C(6) C(10) H(10B) 112(2) ?
H(10A) C(10) H(10B) 110(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl(1) C(1) . . 1.780(3) yes
Cl(2) C(7) . . 1.780(3) yes
O(1) C(8) . . 1.227(3) yes
N(9) C(1) . . 1.465(3) yes
N(9) C(8) . . 1.332(3) yes
C(1) C(2) . . 1.519(4) yes
C(1) C(10) . . 1.511(4) yes
C(2) C(3) . . 1.540(4) yes
C(3) C(4) . . 1.538(4) yes
C(3) C(7) . . 1.542(4) yes
C(4) C(5) . . 1.526(5) yes
C(5) C(6) . . 1.535(4) yes
C(6) C(7) . . 1.542(3) yes
C(6) C(10) . . 1.540(4) yes
C(7) C(8) . . 1.526(3) yes
N(9) H(9) . . 0.84(3) ?
C(2) H(2A) . . 0.95(3) ?
C(2) H(2B) . . 1.00(3) ?
C(3) H(3) . . 0.97(3) ?
C(4) H(4A) . . 0.99(3) ?
C(4) H(4B) . . 0.97(4) ?
C(5) H(5A) . . 0.90(4) ?
C(5) H(5B) . . 0.90(3) ?
C(6) H(6) . . 0.90(3) ?
C(10) H(10A) . . 0.87(3) ?
C(10) H(10B) . . 0.92(4) ?
