#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/65/2236565.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_2236565
loop_
_publ_author_name
'Aydın, Abdullah'
'Akkurt, Mehmet'
'Gul, Halise Inci'
'Mete, Ebru'
'Sahin, Ertan'
_publ_section_title
;
 N-[2-(4-Methylbenzoyl)ethyl]propan-2-aminium chloride
;
_journal_coeditor_code           QM2078
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2706
_journal_page_last               o2707
_journal_paper_doi               10.1107/S1600536812035271
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H20 N O +, Cl -'
_chemical_formula_moiety         'C13 H20 N O +, Cl -'
_chemical_formula_sum            'C13 H20 Cl N O'
_chemical_formula_weight         241.75
_chemical_name_systematic
;
N-[2-(4-Methylbenzoyl)ethyl]propan-2-aminium chloride
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.362(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.786(5)
_cell_length_b                   7.511(5)
_cell_length_c                   23.365(5)
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.4676
_cell_measurement_theta_min      2.6274
_cell_volume                     1360.4(13)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26900
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.176
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0485
_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)+(0.0681P)²+0.2172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1506
_reflns_number_gt                2007
_reflns_number_total             2800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2078.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236565
_cod_database_fobs_code          2236565
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.7123(2) 0.2422(3) 0.57107(8) 0.0903(8) Uani d . 1.000
N N1 0.7916(2) 0.0622(2) 0.74056(7) 0.0555(6) Uani d . 1.000
C C1 1.2949(3) 0.1740(3) 0.53020(10) 0.0722(9) Uani d . 1.000
C C2 1.2627(3) 0.2488(3) 0.47633(10) 0.0653(8) Uani d . 1.000
C C3 1.0947(3) 0.2961(3) 0.45820(9) 0.0680(9) Uani d . 1.000
C C4 0.9644(3) 0.2737(3) 0.49337(9) 0.0659(8) Uani d . 1.000
C C5 0.9974(3) 0.2024(3) 0.54815(9) 0.0563(7) Uani d . 1.000
C C6 1.1652(3) 0.1501(3) 0.56544(10) 0.0658(8) Uani d . 1.000
C C7 0.8564(3) 0.1895(3) 0.58624(9) 0.0616(8) Uani d . 1.000
C C8 0.8956(3) 0.1133(3) 0.64590(9) 0.0623(8) Uani d . 1.000
C C9 0.7524(3) 0.1489(3) 0.68361(9) 0.0606(8) Uani d . 1.000
C C10 0.6625(3) 0.0981(3) 0.78362(9) 0.0611(8) Uani d . 1.000
C C11 0.6888(4) 0.2830(4) 0.80850(12) 0.0807(10) Uani d . 1.000
C C12 0.6811(4) -0.0436(4) 0.82927(12) 0.0864(10) Uani d . 1.000
C C13 1.4074(4) 0.2830(5) 0.43891(12) 0.0913(11) Uani d . 1.000
Cl Cl1 1.17234(7) 0.15576(7) 0.78840(2) 0.0665(2) Uani d . 1.000
H H1 1.40660 0.13910 0.54290 0.0870 Uiso c R 1.000
H H3 1.06950 0.34370 0.42160 0.0820 Uiso c R 1.000
H H4 0.85250 0.30690 0.48030 0.0790 Uiso c R 1.000
H H6 1.19010 0.09810 0.60140 0.0790 Uiso c R 1.000
H H8A 0.91290 -0.01420 0.64310 0.0750 Uiso c R 1.000
H H8B 1.00180 0.16520 0.66350 0.0750 Uiso c R 1.000
H H9A 0.73980 0.27620 0.68870 0.0730 Uiso c R 1.000
H H9B 0.64450 0.10290 0.66530 0.0730 Uiso c R 1.000
H H10 0.54610 0.09070 0.76380 0.0730 Uiso c R 1.000
H H11A 0.59650 0.31080 0.83150 0.1210 Uiso c R 1.000
H H11B 0.68980 0.36790 0.77780 0.1210 Uiso c R 1.000
H H11C 0.79670 0.28780 0.83190 0.1210 Uiso c R 1.000
H H12A 0.66880 -0.15880 0.81160 0.1290 Uiso c R 1.000
H H12B 0.59360 -0.02790 0.85520 0.1290 Uiso c R 1.000
H H12C 0.79290 -0.03440 0.85020 0.1290 Uiso c R 1.000
H H13A 1.43820 0.40670 0.44090 0.1370 Uiso c R 1.000
H H13B 1.37010 0.25180 0.39990 0.1370 Uiso c R 1.000
H H13C 1.50570 0.21210 0.45220 0.1370 Uiso c R 1.000
H H14A 0.89610 0.09920 0.75560 0.0670 Uiso c R 1.000
H H14B 0.79790 -0.05620 0.73520 0.0670 Uiso c R 1.000
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'
Cl Cl 0.1484 0.1585 ' 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'
O O 0.0106 0.0060 ' 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 N1 C10 115.08(16) no
H14A N1 H14B 107.00 no
C9 N1 H14B 109.00 no
C10 N1 H14A 109.00 no
C9 N1 H14A 108.00 no
C10 N1 H14B 108.00 no
C2 C1 C6 121.3(2) no
C1 C2 C13 121.0(2) no
C1 C2 C3 118.0(2) no
C3 C2 C13 120.9(2) no
C2 C3 C4 121.0(2) no
C3 C4 C5 121.0(2) no
C6 C5 C7 122.5(2) no
C4 C5 C7 119.7(2) no
C4 C5 C6 117.7(2) no
C1 C6 C5 120.9(2) no
O1 C7 C5 121.5(2) no
C5 C7 C8 118.8(2) no
O1 C7 C8 119.7(2) no
C7 C8 C9 112.03(19) no
N1 C9 C8 110.12(18) no
N1 C10 C12 108.65(19) no
C11 C10 C12 112.1(2) no
N1 C10 C11 110.19(19) no
C2 C1 H1 119.00 no
C6 C1 H1 119.00 no
C2 C3 H3 119.00 no
C4 C3 H3 119.00 no
C3 C4 H4 119.00 no
C5 C4 H4 120.00 no
C1 C6 H6 120.00 no
C5 C6 H6 120.00 no
C7 C8 H8A 109.00 no
C7 C8 H8B 109.00 no
C9 C8 H8A 109.00 no
C9 C8 H8B 109.00 no
H8A C8 H8B 108.00 no
N1 C9 H9A 110.00 no
N1 C9 H9B 110.00 no
C8 C9 H9A 110.00 no
C8 C9 H9B 110.00 no
H9A C9 H9B 108.00 no
N1 C10 H10 109.00 no
C11 C10 H10 109.00 no
C12 C10 H10 109.00 no
C10 C11 H11A 109.00 no
C10 C11 H11B 109.00 no
C10 C11 H11C 109.00 no
H11A C11 H11B 109.00 no
H11A C11 H11C 110.00 no
H11B C11 H11C 109.00 no
C10 C12 H12A 109.00 no
C10 C12 H12B 109.00 no
C10 C12 H12C 109.00 no
H12A C12 H12B 110.00 no
H12A C12 H12C 109.00 no
H12B C12 H12C 109.00 no
C2 C13 H13A 109.00 no
C2 C13 H13B 109.00 no
C2 C13 H13C 109.00 no
H13A C13 H13B 110.00 no
H13A C13 H13C 109.00 no
H13B C13 H13C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.211(3) no
N1 C9 1.487(3) no
N1 C10 1.511(3) no
N1 H14B 0.9000 no
N1 H14A 0.9000 no
C1 C6 1.373(3) no
C1 C2 1.380(3) no
C2 C3 1.383(3) no
C2 C13 1.511(4) no
C3 C4 1.374(3) no
C4 C5 1.389(3) no
C5 C7 1.480(3) no
C5 C6 1.388(3) no
C7 C8 1.511(3) no
C8 C9 1.508(3) no
C10 C12 1.504(4) no
C10 C11 1.512(4) no
C1 H1 0.9300 no
C3 H3 0.9300 no
C4 H4 0.9300 no
C6 H6 0.9300 no
C8 H8A 0.9700 no
C8 H8B 0.9700 no
C9 H9A 0.9700 no
C9 H9B 0.9700 no
C10 H10 0.9800 no
C11 H11A 0.9600 no
C11 H11B 0.9600 no
C11 H11C 0.9600 no
C12 H12A 0.9600 no
C12 H12B 0.9600 no
C12 H12C 0.9600 no
C13 H13A 0.9600 no
C13 H13B 0.9600 no
C13 H13C 0.9600 no
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
N1 H14A Cl1 . 0.90 2.26 3.148(3) 172 yes
N1 H14B Cl1 2_746 0.90 2.25 3.145(3) 173 yes
C1 H1 O1 1_655 0.93 2.53 3.340(4) 146 yes
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 N1 C10 C11 -76.7(2) no
C9 N1 C10 C12 160.08(19) no
C10 N1 C9 C8 176.31(17) no
C6 C1 C2 C3 -1.3(3) no
C6 C1 C2 C13 177.0(2) no
C2 C1 C6 C5 -0.7(4) no
C13 C2 C3 C4 -176.6(2) no
C1 C2 C3 C4 1.7(3) no
C2 C3 C4 C5 -0.2(3) no
C3 C4 C5 C6 -1.8(3) no
C3 C4 C5 C7 176.5(2) no
C4 C5 C6 C1 2.2(3) no
C7 C5 C6 C1 -176.0(2) no
C6 C5 C7 C8 -1.2(3) no
C4 C5 C7 O1 -1.1(3) no
C4 C5 C7 C8 -179.4(2) no
C6 C5 C7 O1 177.1(2) no
O1 C7 C8 C9 -11.9(3) no
C5 C7 C8 C9 166.46(19) no
C7 C8 C9 N1 176.54(17) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658144
