#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/45/2014599.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_2014599
loop_
_publ_author_name
'Youssif Ebead'
'Artur Sikorski'
'Karol Krzymiński'
'Lis, Tadeusz'
'Jerzy Błażejowski'
_publ_section_title
;
 9-(2-Chloroethylamino)acridine monohydrate and its precursor
 9-phenoxyacridine
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o85
_journal_page_last               o87
_journal_paper_doi               10.1107/S0108270104025156
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H13 Cl N2, H2 O'
_chemical_formula_moiety         'C15 H13 Cl N2, H2 O'
_chemical_formula_sum            'C15 H15 Cl N2 O'
_chemical_formula_weight         274.74
_chemical_name_systematic
;
9-(2-chloroethylamino)acridine monohydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 107.20(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.052(3)
_cell_length_b                   11.330(2)
_cell_length_c                   17.283(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_cell_volume                     2628.6(10)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma Diffraction, 1989)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5227
_diffrn_reflns_theta_full        81.14
_diffrn_reflns_theta_max         81.14
_diffrn_reflns_theta_min         5.11
_diffrn_standards_decay_%        2.48
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.510
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.373
_refine_ls_extinction_coef       0.00079(10)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0538P)²+2.9481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                1793
_reflns_number_total             2909
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            av1203.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2014599
_cod_database_fobs_code          2014599
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y, z-1/2'
'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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.3630(2) 0.1946(2) 0.43440(14) 0.0478(6) Uani d . 1 . . C
H1 0.348(2) 0.193(2) 0.3781(18) 0.053(8) Uiso d . 1 . . H
C2 0.3817(2) 0.0902(2) 0.47443(16) 0.0540(7) Uani d . 1 . . C
H2 0.381(2) 0.020(3) 0.4454(19) 0.068(10) Uiso d . 1 . . H
C3 0.4086(2) 0.0873(2) 0.55918(16) 0.0510(7) Uani d . 1 . . C
H3 0.422(2) 0.012(3) 0.588(2) 0.070(10) Uiso d . 1 . . H
C4 0.4179(2) 0.1889(2) 0.60156(14) 0.0455(6) Uani d . 1 . . C
H4 0.438(2) 0.189(2) 0.6606(18) 0.050(7) Uiso d . 1 . . H
C5 0.4175(2) 0.6046(2) 0.62351(15) 0.0482(6) Uani d . 1 . . C
H5 0.439(2) 0.591(3) 0.681(2) 0.066(9) Uiso d . 1 . . H
C6 0.4042(2) 0.7146(2) 0.59147(18) 0.0548(7) Uani d . 1 . . C
H6 0.415(3) 0.779(3) 0.625(2) 0.081(11) Uiso d . 1 . . H
C7 0.3730(2) 0.7301(3) 0.50762(18) 0.0544(7) Uani d . 1 . . C
H7 0.358(3) 0.806(3) 0.484(2) 0.088(12) Uiso d . 1 . . H
C8 0.3558(2) 0.6354(2) 0.45724(15) 0.0446(6) Uani d . 1 . . C
H8 0.3310(19) 0.648(2) 0.3994(16) 0.044(7) Uiso d . 1 . . H
C9 0.35264(17) 0.41649(19) 0.43715(12) 0.0343(5) Uani d . 1 . . C
N10 0.41450(16) 0.39637(18) 0.60992(11) 0.0409(5) Uani d . 1 . . N
C11 0.36840(17) 0.3039(2) 0.47552(12) 0.0341(5) Uani d . 1 . . C
C12 0.39901(17) 0.3003(2) 0.56203(13) 0.0361(5) Uani d . 1 . . C
C13 0.36966(16) 0.5183(2) 0.48793(13) 0.0338(5) Uani d . 1 . . C
C14 0.40056(18) 0.5032(2) 0.57327(13) 0.0367(5) Uani d . 1 . . C
N15 0.32497(17) 0.43216(19) 0.35597(11) 0.0422(5) Uani d . 1 . . N
H15 0.333(2) 0.499(3) 0.3391(18) 0.051(8) Uiso d . 1 . . H
C16 0.2696(2) 0.3541(2) 0.29262(14) 0.0465(6) Uani d . 1 . . C
H16A 0.228(2) 0.304(2) 0.3142(17) 0.051(8) Uiso d . 1 . . H
H16B 0.311(3) 0.307(3) 0.271(2) 0.071(10) Uiso d . 1 . . H
C17 0.2099(2) 0.4234(3) 0.22029(15) 0.0522(7) Uani d . 1 . . C
H17A 0.249(2) 0.475(3) 0.1963(19) 0.058(8) Uiso d . 1 . . H
H17B 0.175(2) 0.372(3) 0.1778(19) 0.062(9) Uiso d . 1 . . H
Cl18 0.12332(6) 0.51965(8) 0.24439(5) 0.0699(3) Uani d . 1 . . Cl
O19 0.38779(12) 0.63302(15) 0.26947(9) 0.0491(4) Uani d . 1 . . O
H19A 0.397(3) 0.609(4) 0.217(2) 0.096(12) Uiso d . 1 . . H
H19B 0.451(3) 0.628(3) 0.301(2) 0.082(11) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C9 N15 H15 117(2) yes
C9 N15 C16 129.2(2) yes
C11 C9 C13 117.6(2) yes
C11 C9 N15 123.9(2) yes
C12 N10 C14 117.4(2) yes
C13 C9 N15 118.5(2) yes
N15 C16 C17 110.7(2) yes
C16 C17 Cl18 112.2(2) yes
C2 C1 C11 122.2(2) ?
C2 C1 H1 117.6(17) ?
C11 C1 H1 120.2(17) ?
C1 C2 C3 120.3(2) ?
C1 C2 H2 120(2) ?
C3 C2 H2 120(2) ?
C4 C3 C2 120.0(2) ?
C4 C3 H3 120(2) ?
C2 C3 H3 120(2) ?
C3 C4 C12 121.4(2) ?
C3 C4 H4 121.2(16) ?
C12 C4 H4 117.4(16) ?
C6 C5 C14 121.2(2) ?
C6 C5 H5 122.3(19) ?
C14 C5 H5 116.5(19) ?
C5 C6 C7 120.2(3) ?
C5 C6 H6 120(2) ?
C7 C6 H6 120(2) ?
C8 C7 C6 120.5(3) ?
C8 C7 H7 118(2) ?
C6 C7 H7 121(2) ?
C7 C8 C13 121.3(2) ?
C7 C8 H8 118.9(16) ?
C13 C8 H8 119.7(16) ?
C1 C11 C9 124.78(19) ?
C1 C11 C12 117.0(2) ?
C9 C11 C12 118.0(2) ?
N10 C12 C4 116.7(2) ?
N10 C12 C11 124.4(2) ?
C4 C12 C11 118.9(2) ?
C14 C13 C8 117.9(2) ?
C14 C13 C9 119.0(2) ?
C8 C13 C9 123.1(2) ?
N10 C14 C5 117.6(2) ?
N10 C14 C13 123.5(2) ?
C5 C14 C13 118.9(2) ?
C16 N15 H15 113(2) ?
N15 C16 H16A 108.7(17) ?
C17 C16 H16A 112.1(17) ?
N15 C16 H16B 113(2) ?
C17 C16 H16B 103(2) ?
H16A C16 H16B 109(3) ?
C16 C17 H17A 115.2(19) ?
Cl18 C17 H17A 103.7(18) ?
C16 C17 H17B 110.9(19) ?
Cl18 C17 H17B 108.9(19) ?
H17A C17 H17B 105(3) ?
H19A O19 H19B 100(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C9 C11 . 1.425(3) yes
C9 C13 . 1.427(3) yes
C9 N15 . 1.352(3) yes
N10 C12 . 1.345(3) yes
N10 C14 . 1.353(3) yes
N15 H15 . 0.84(3) ?
N15 C16 . 1.443(3) yes
C16 C17 . 1.504(3) yes
C17 Cl18 . 1.773(3) yes
C1 C2 . 1.357(4) ?
C1 C11 . 1.418(3) ?
C1 H1 . 0.93(3) ?
C2 C3 . 1.401(4) ?
C2 H2 . 0.94(3) ?
C3 C4 . 1.350(4) ?
C3 H3 . 0.98(3) ?
C4 C12 . 1.422(3) ?
C4 H4 . 0.98(3) ?
C5 C6 . 1.354(4) ?
C5 C14 . 1.417(3) ?
C5 H5 . 0.96(3) ?
C6 C7 . 1.395(4) ?
C6 H6 . 0.92(4) ?
C7 C8 . 1.358(4) ?
C7 H7 . 0.94(4) ?
C8 C13 . 1.420(3) ?
C8 H8 . 0.97(3) ?
C11 C12 . 1.429(3) ?
C13 C14 . 1.419(3) ?
C16 H16A . 0.97(3) ?
C16 H16B . 0.94(4) ?
C17 H17A . 0.98(3) ?
C17 H17B . 0.95(3) ?
O19 H19A . 1.00(4) ?
O19 H19B . 0.90(4) ?
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
_geom_hbond_publ_flag
N15 H15 O19 1_555 0.84(3) 2.21(3) 2.996(3) 157(3) y
O19 H19A N10 7_565 1.00(4) 1.93(4) 2.908(3) 166(3) y
O19 H19B N10 3_666 0.90(4) 2.07(4) 2.957(3) 169(3) y
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
C9 N15 H15 C16 -172(2) yes
C9 N15 C16 C17 149.7(3) yes
C11 C9 C13 C14 -0.4(3) yes
C11 C9 N15 H15 -163(2) yes
C11 C9 N15 C16 26.9(4) yes
C12 N10 C14 C13 0.8(3) yes
N15 C16 C17 Cl18 -59.9(3) yes
C11 C1 C2 C3 -0.8(5) ?
C1 C2 C3 C4 -1.3(5) ?
C2 C3 C4 C12 1.3(5) ?
C14 C5 C6 C7 0.2(5) ?
C5 C6 C7 C8 -0.2(5) ?
C6 C7 C8 C13 -0.5(5) ?
C2 C1 C11 C9 178.0(3) ?
C2 C1 C11 C12 2.7(4) ?
N15 C9 C11 C1 3.9(4) ?
C13 C9 C11 C1 -174.5(2) ?
N15 C9 C11 C12 179.1(2) ?
C13 C9 C11 C12 0.7(3) ?
C14 N10 C12 C4 177.5(2) ?
C14 N10 C12 C11 -0.4(3) ?
C3 C4 C12 N10 -177.3(3) ?
C3 C4 C12 C11 0.7(4) ?
C1 C11 C12 N10 175.2(2) ?
C9 C11 C12 N10 -0.3(3) ?
C1 C11 C12 C4 -2.6(3) ?
C9 C11 C12 C4 -178.2(2) ?
C7 C8 C13 C14 1.0(4) ?
C7 C8 C13 C9 -179.9(3) ?
N15 C9 C13 C14 -178.8(2) ?
N15 C9 C13 C8 2.1(3) ?
C11 C9 C13 C8 -179.5(2) ?
C12 N10 C14 C5 -179.5(2) ?
C6 C5 C14 N10 -179.3(3) ?
C6 C5 C14 C13 0.4(4) ?
C8 C13 C14 N10 178.7(2) ?
C9 C13 C14 N10 -0.4(4) ?
C8 C13 C14 C5 -0.9(3) ?
C9 C13 C14 C5 179.9(2) ?
C13 C9 N15 C16 -154.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133978
