#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/29/2212929.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_2212929
loop_
_publ_author_name
'Elsinghorst, Paul Wilhelm'
'Nieger, Martin'
'Gütschow, Michael'
_publ_section_title
;
 6,9-Dichloro-1,2,3,4-tetrahydroacridine
;
_journal_coeditor_code           HK2214
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1818
_journal_page_last               o1820
_journal_paper_doi               10.1107/S1600536807011701
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H11 Cl2 N'
_chemical_formula_moiety         'C13 H11 Cl2 N'
_chemical_formula_sum            'C13 H11 Cl2 N'
_chemical_formula_weight         252.13
_chemical_melting_point          92
_chemical_name_systematic
;
6,9-Dichloro-1,2,3,4-tetrahydroacridine
;
_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           SHELXL97
_cell_angle_alpha                108.603(5)
_cell_angle_beta                 95.617(5)
_cell_angle_gamma                116.885(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4050(6)
_cell_length_b                   9.0451(7)
_cell_length_c                   9.0962(9)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     560.07(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and SHELXTL (Sheldrick,
2001)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'rotation in φ and ω (2°)'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4104
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1913
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0321
_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)+(0.0347P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                1461
_reflns_number_total             1913
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2214.cif
_cod_data_source_block           I
_cod_database_code               2212929
_cod_database_fobs_code          2212929
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
C C1 0.3587(3) 0.4058(2) 0.1762(2) 0.0267(5) Uani d . 1
H H1A 0.4229 0.3414 0.1935 0.032 Uiso calc R 1
H H1B 0.4023 0.4531 0.0947 0.032 Uiso calc R 1
C C2 0.1494(3) 0.2722(3) 0.1116(2) 0.0343(5) Uani d . 1
H H2A 0.0865 0.3307 0.0777 0.041 Uiso calc R 1
H H2B 0.1230 0.1652 0.0153 0.041 Uiso calc R 1
C C3 0.0733(3) 0.2112(2) 0.2379(2) 0.0345(5) Uani d . 1
H H3A 0.1349 0.1510 0.2705 0.041 Uiso calc R 1
H H3B -0.0617 0.1215 0.1914 0.041 Uiso calc R 1
C C4 0.1048(3) 0.3706(2) 0.3862(2) 0.0307(5) Uani d . 1
H H4A 0.0037 0.3956 0.3650 0.037 Uiso calc R 1
H H4B 0.0949 0.3346 0.4784 0.037 Uiso calc R 1
C C4a 0.2888(3) 0.5437(2) 0.4353(2) 0.0231(5) Uani d . 1
N N5 0.3253(2) 0.67479(19) 0.57594(17) 0.0246(4) Uani d . 1
C C5a 0.4840(3) 0.8393(2) 0.6240(2) 0.0218(5) Uani d . 1
C C5 0.5197(3) 0.9786(2) 0.7731(2) 0.0248(5) Uani d . 1
H H5 0.4355 0.9557 0.8367 0.030 Uiso calc R 1
C C6 0.6754(3) 1.1458(2) 0.8248(2) 0.0235(5) Uani d . 1
Cl Cl6 0.71861(7) 1.31684(6) 1.00867(5) 0.03320(17) Uani d . 1
C C7 0.8037(3) 1.1857(2) 0.7345(2) 0.0261(5) Uani d . 1
H H7 0.9112 1.3034 0.7731 0.031 Uiso calc R 1
C C8 0.7716(3) 1.0529(2) 0.5904(2) 0.0262(5) Uani d . 1
H H8 0.8572 1.0791 0.5284 0.031 Uiso calc R 1
C C8a 0.6132(3) 0.8772(2) 0.5325(2) 0.0218(5) Uani d . 1
C C9 0.5683(3) 0.7286(2) 0.3856(2) 0.0240(5) Uani d . 1
Cl Cl9 0.72615(7) 0.76319(6) 0.27128(5) 0.03354(17) Uani d . 1
C C9a 0.4097(3) 0.5630(2) 0.3336(2) 0.0218(5) Uani d . 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
_geom_angle_publ_flag
C9a C1 C2 111.88(17) y
C9a C1 H1A 109.2 ?
C2 C1 H1A 109.2 ?
C9a C1 H1B 109.2 ?
C2 C1 H1B 109.2 ?
H1A C1 H1B 107.9 ?
C3 C2 C1 111.18(16) y
C3 C2 H2A 109.4 ?
C1 C2 H2A 109.4 ?
C3 C2 H2B 109.4 ?
C1 C2 H2B 109.4 ?
H2A C2 H2B 108.0 ?
C2 C3 C4 111.34(15) y
C2 C3 H3A 109.4 ?
C4 C3 H3A 109.4 ?
C2 C3 H3B 109.4 ?
C4 C3 H3B 109.4 ?
H3A C3 H3B 108.0 ?
C4a C4 C3 115.26(17) y
C4a C4 H4A 108.5 ?
C3 C4 H4A 108.5 ?
C4a C4 H4B 108.5 ?
C3 C4 H4B 108.5 ?
H4A C4 H4B 107.5 ?
N5 C4a C9a 123.74(17) ?
N5 C4a C4 114.87(17) ?
C9a C4a C4 121.37(16) y
C4a N5 C5a 118.32(17) ?
N5 C5a C5 117.69(17) ?
N5 C5a C8a 123.46(17) ?
C5 C5a C8a 118.84(17) ?
C6 C5 C5a 119.65(18) ?
C6 C5 H5 120.2 ?
C5a C5 H5 120.2 ?
C5 C6 C7 122.07(17) ?
C5 C6 Cl6 119.40(16) ?
C7 C6 Cl6 118.52(15) ?
C8 C7 C6 119.07(18) ?
C8 C7 H7 120.5 ?
C6 C7 H7 120.5 ?
C7 C8 C8a 120.95(19) ?
C7 C8 H8 119.5 ?
C8a C8 H8 119.5 ?
C8 C8a C5a 119.40(17) ?
C8 C8a C9 125.42(19) ?
C5a C8a C9 115.18(17) ?
C9a C9 C8a 122.65(18) ?
C9a C9 Cl9 119.78(15) ?
C8a C9 Cl9 117.57(15) ?
C9 C9a C4a 116.59(17) ?
C9 C9a C1 123.07(18) ?
C4a C9a C1 120.34(17) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C9a 1.511(2) y
C1 C2 1.524(3) y
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 C3 1.504(3) y
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C4 1.521(2) y
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C4a 1.507(3) y
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C4a N5 1.327(2) ?
C4a C9a 1.431(3) y
N5 C5a 1.363(2) ?
C5a C5 1.416(2) ?
C5a C8a 1.419(3) ?
C5 C6 1.363(3) ?
C5 H5 0.9500 ?
C6 C7 1.406(3) ?
C6 Cl6 1.7449(19) ?
C7 C8 1.366(3) ?
C7 H7 0.9500 ?
C8 C8a 1.410(3) ?
C8 H8 0.9500 ?
C8a C9 1.426(2) ?
C9 C9a 1.365(2) ?
C9 Cl9 1.744(2) ?
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_publ_flag
C9a C1 C2 C3 -53.1(2) y
C1 C2 C3 C4 61.0(2) y
C2 C3 C4 C4a -38.5(2) y
C3 C4 C4a N5 -171.80(15) ?
C3 C4 C4a C9a 9.8(3) y
C9a C4a N5 C5a 2.3(3) ?
C4 C4a N5 C5a -176.06(15) ?
C4a N5 C5a C5 179.05(15) ?
C4a N5 C5a C8a -0.7(3) ?
N5 C5a C5 C6 -179.23(16) ?
C8a C5a C5 C6 0.6(3) ?
C5a C5 C6 C7 0.1(3) ?
C5a C5 C6 Cl6 -179.97(13) ?
C5 C6 C7 C8 -0.1(3) ?
Cl6 C6 C7 C8 179.92(13) ?
C6 C7 C8 C8a -0.5(3) ?
C7 C8 C8a C5a 1.1(3) ?
C7 C8 C8a C9 -178.94(17) ?
N5 C5a C8a C8 178.66(16) ?
C5 C5a C8a C8 -1.1(3) ?
N5 C5a C8a C9 -1.3(3) ?
C5 C5a C8a C9 178.91(14) ?
C8 C8a C9 C9a -178.02(17) ?
C5a C8a C9 C9a 2.0(3) ?
C8 C8a C9 Cl9 2.6(2) ?
C5a C8a C9 Cl9 -177.41(13) ?
C8a C9 C9a C4a -0.6(3) ?
Cl9 C9 C9a C4a 178.74(13) ?
C8a C9 C9a C1 178.59(16) ?
Cl9 C9 C9a C1 -2.0(2) ?
N5 C4a C9a C9 -1.6(3) ?
C4 C4a C9a C9 176.60(16) ?
N5 C4a C9a C1 179.13(16) ?
C4 C4a C9a C1 -2.6(3) y
C2 C1 C9a C9 -155.22(17) ?
C2 C1 C9a C4a 24.0(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 190432
