#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003650.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_2003650
loop_
_publ_author_name
'Mague, J. T.'
'De, D.'
'Krogstad, D. J.'
_publ_section_title
;
 An Intermediate for Chloroquine Analogs:
 (E)-2-(4,7-Dichloro-2-quinolinyl)-3-(dimethylamino)-2-propenal
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1423
_journal_page_last               1425
_journal_paper_doi               10.1107/S0108270195000151
_journal_volume                  51
_journal_year                    1995
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C14 H12 Cl2 N2 O1'
_chemical_formula_sum            'C14 H12 Cl2 N2 O'
_chemical_formula_weight         295.17
_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_type_scat_source           IntTabIV
_cell_angle_alpha                97.84(1)
_cell_angle_beta                 104.36(1)
_cell_angle_gamma                115.03(1)
_cell_formula_units_Z            2
_cell_length_a                   8.2796(9)
_cell_length_b                   8.644(1)
_cell_length_c                   11.336(1)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293
_cell_measurement_theta_max      16.91
_cell_measurement_theta_min      11.01
_cell_volume                     684.70(16)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_structure_refinement  MolEN
_computing_structure_solution
;SIR88 (Burla, Camalli, Cascarano, Giocavazzo, Polidori, Spagna & Veterbo,
 1989)
;
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2581
_diffrn_reflns_theta_max         25.0
_diffrn_standards_decay_%        -1.8
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.46
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_description       'triclinic prism'
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.05
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.56
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_number_parameters     220
_refine_ls_number_reflns         1567
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         0.05
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.049
_reflns_number_observed          1567
_reflns_number_total             2389
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            cr1173.cif
_cod_data_source_block           cr1173a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        684.7(2)
_cod_original_formula_sum        'C14 H12 Cl2 N2 O1'
_cod_database_code               2003650
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
Cl(1) .8660(1) .11070(9) .90276(8) 5.47(2)
Cl(2) .2690(1) -.4944(1) 1.15541(7) 6.59(2)
O .2894(3) -.0432(2) .5232(2) 5.51(6)
N(1) .2823(2) -.3673(2) .7351(2) 3.07(5)
N(2) .1830(3) -.6411(2) .4559(2) 3.48(5)
C(1) .3795(3) -.3151(3) .8621(2) 3.15(6)
C(2) .2911(3) -.4167(3) .9369(2) 3.83(7)
C(3) .3795(4) -.3694(3) 1.0639(2) 4.16(7)
C(4) .5585(4) -.2198(4) 1.1235(3) 4.83(8)
C(5) .6465(4) -.1231(3) 1.0535(3) 4.38(7)
C(6) .5621(3) -.1658(3) .9213(2) 3.22(6)
C(7) .6409(3) -.0712(3) .8402(3) 3.44(6)
C(8) .5458(3) -.1209(3) .7147(2) 3.28(6)
C(9) .3644(3) -.2733(3) .6635(2) 2.81(5)
C(10) .2586(3) -.3275(3) .5265(2) 2.99(5)
C(11) .2310(3) -.1989(3) .4704(3) 4.10(7)
C(12) .1719(3) -.4958(3) .4451(2) 3.09(5)
C(13) .3110(4) -.6496(3) .5651(3) 4.86(7)
C(14) .0656(4) -.8036(4) .3523(3) 5.06(8)
H(2) .172(3) -.519(3) .893(2) 4.4(6)
H(4) .608(4) -.194(3) 1.209(2) 5.5(7)
H(5) .766(4) -.026(3) 1.096(3) 6.4(8)
H(8) .591(3) -.063(3) .657(2) 4.3(6)
H(11) .148(3) -.251(3) .377(2) 5.5(7)
H(12) .093(3) -.510(3) .361(2) 3.2(5)
H(13a) .336(3) -.739(3) .548(2) 5.0(6)
H(13b) .253(4) -.665(4) .626(3) 7.7(9)
H(13c) .432(4) -.536(4) .597(3) 7.0(8)
H(14a) -.000(5) -.782(5) .281(4) 11(1)
H(14b) -.020(4) -.884(4) .374(3) 8.0(9)
H(14c) .127(4) -.853(4) .328(3) 9(1)
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(9) C(10) C(11) 118.5(2) yes
C(9) C(10) C(12) 126.7(2) yes
C(11) C(10) C(12) 114.7(2) yes
C(10) C(11) O 126.9(3) yes
C(10) C(12) N(2) 132.6(2) yes
C(12) N(2) C(13) 123.7(2) yes
C(12) N(2) C(14) 119.6(3) yes
C(13) N(2) C(14) 116.7(3) yes
C(1) N(1) C(9) 118.0(2) no
N(1) C(1) C(2) 117.4(2) no
N(1) C(1) C(6) 123.5(2) no
C(2) C(1) C(6) 119.1(2) no
C(1) C(2) C(3) 120.0(3) no
C(1) C(2) H(2) 116(2) no
C(3) C(2) H(2) 124(2) no
Cl(2) C(3) C(2) 119.7(3) no
Cl(2) C(3) C(4) 119.1(2) no
C(2) C(3) C(4) 121.2(3) no
C(3) C(4) C(5) 119.7(3) no
C(3) C(4) H(4) 116(2) no
C(5) C(4) H(4) 124(2) no
C(4) C(5) C(6) 121.7(3) no
C(4) C(5) H(5) 118(2) no
C(6) C(5) H(5) 121(2) no
C(1) C(6) C(5) 118.2(3) no
C(1) C(6) C(7) 115.8(2) no
C(5) C(6) C(7) 126(3) no
Cl(1) C(7) C(6) 119.4(2) no
Cl(1) C(7) C(8) 119.3(2) no
C(6) C(7) C(8) 121.3(2) no
C(7) C(8) C(9) 119(3) no
C(7) C(8) H(8) 125(2) no
C(9) C(8) H(8) 116(2) no
N(1) C(9) C(8) 122.4(2) no
N(1) C(9) C(10) 118.2(2) no
C(8) C(9) C(10) 119.4(2) no
O C(11) H(11) 120(3) no
C(10) C(11) H(11) 113(2) no
N(2) C(12) H(12) 112(2) no
C(10) C(12) H(12) 115(2) no
N(2) C(13) H(13a) 113(2) no
N(2) C(13) H(13b) 107(3) no
N(2) C(13) H(13c) 109(2) no
H(13a) C(13) H(13b) 109(3) no
H(13a) C(13) H(13c) 109(3) no
H(13b) C(13) H(13c) 110(3) no
N(2) C(14) H(14a) 111(3) no
N(2) C(14) H(14b) 111(3) no
N(2) C(14) H(14c) 114(3) no
H(14a) C(14) H(14b) 107(4) no
H(14a) C(14) H(14c) 108(4) no
H(14b) C(14) H(14c) 105(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(9) C(10) 1.476(3) yes
C(10) C(11) 1.425(4) yes
C(11) O 1.220(4) yes
C(10) C(12) 1.380(4) yes
C(12) N(2) 1.318(3) yes
C(13) N(2) 1.450(4) yes
C(14) N(2) 1.458(4) yes
Cl(1) C(7) 1.735(3) no
Cl(2) C(3) 1.738(3) no
N(1) C(1) 1.365(3) no
N(1) C(9) 1.329(3) no
C(1) C(2) 1.411(4) no
C(1) C(6) 1.418(4) no
C(2) C(3) 1.356(4) no
C(2) H(2) .95(3) no
C(3) C(4) 1.403(5) no
C(4) C(5) 1.346(5) no
C(4) H(4) .91(3) no
C(5) C(6) 1.409(4) no
C(5) H(5) .93(4) no
C(6) C(7) 1.410(4) no
C(7) C(8) 1.349(4) no
C(8) C(9) 1.419(4) no
C(8) H(8) .93(3) no
C(11) H(11) 1.02(3) no
C(12) H(12) .97(3) no
C(13) H(13a) .89(3) no
C(13) H(13b) .93(4) no
C(13) H(13c) 1.00(4) no
C(14) H(14a) .94(5) no
C(14) H(14b) .87(4) no
C(14) H(14c) .86(5) no
