#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/64/2206497.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_2206497
loop_
_publ_author_name
'Anilkumar, Haleyur G.'
'Yathirajan, Hemmige S.'
'Nagaraja, Padmarajaiah'
'Bolte, Michael'
_publ_section_title
;
 (2-Chloroanilino)acetophenone
;
_journal_coeditor_code           NC6038
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2551
_journal_page_last               o2552
_journal_paper_doi               10.1107/S1600536805022051
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H12 Cl N O'
_chemical_formula_moiety         'C14 H12 Cl N O'
_chemical_formula_sum            'C14 H12 Cl N O'
_chemical_formula_weight         245.70
_chemical_name_systematic
;
(2-Chloroanilino)acetophenone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.363(4)
_cell_length_b                   5.2852(14)
_cell_length_c                   12.509(2)
_cell_measurement_reflns_used    7972
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.6
_cell_measurement_theta_min      2.8
_cell_volume                     1214.0(5)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics
;
PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991)
;
_computing_publication_material  'SHELXL97 and PLATON'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS-II two-circle'
_diffrn_measurement_method       ω
_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  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3857
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9453
_exptl_absorpt_correction_T_min  0.9086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.304
_refine_ls_extinction_coef       0.044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1169
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0500
_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)+(0.096P)²+0.1628P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                986
_reflns_number_total             1169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc6038.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2206497
_cod_database_fobs_code          2206497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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_type_symbol
Cl1 0.32805(7) 0.2392(3) 0.71688(14) 0.0573(5) Uani d . 1 Cl
O1 0.4946(2) 0.8954(7) 0.6996(3) 0.0553(10) Uani d . 1 O
N1 0.4228(2) 0.5632(8) 0.5793(4) 0.0472(10) Uani d . 1 N
H1 0.423(3) 0.579(9) 0.645(5) 0.034(13) Uiso d . 1 H
C1 0.4717(3) 0.7342(9) 0.5258(4) 0.0433(11) Uani d . 1 C
H1A 0.4443 0.8350 0.4726 0.052 Uiso calc R 1 H
H1B 0.5094 0.6360 0.4873 0.052 Uiso calc R 1 H
C2 0.5077(2) 0.9093(9) 0.6049(4) 0.0419(11) Uani d . 1 C
C11 0.3844(3) 0.3807(9) 0.5253(4) 0.0425(11) Uani d . 1 C
C12 0.3371(2) 0.2114(10) 0.5794(5) 0.0438(11) Uani d . 1 C
C13 0.2980(3) 0.0253(10) 0.5259(4) 0.0497(12) Uani d . 1 C
H13 0.2669 -0.0851 0.5648 0.060 Uiso calc R 1 H
C14 0.3042(3) 0.0003(11) 0.4165(5) 0.0514(12) Uani d . 1 C
H14 0.2774 -0.1263 0.3796 0.062 Uiso calc R 1 H
C15 0.3505(3) 0.1639(10) 0.3605(4) 0.0491(12) Uani d . 1 C
H15 0.3556 0.1468 0.2852 0.059 Uiso calc R 1 H
C16 0.3893(3) 0.3518(10) 0.4144(4) 0.0469(12) Uani d . 1 C
H16 0.4197 0.4629 0.3748 0.056 Uiso calc R 1 H
C21 0.5610(3) 1.1005(9) 0.5606(4) 0.0416(11) Uani d . 1 C
C22 0.5754(3) 1.1142(10) 0.4518(4) 0.0462(12) Uani d . 1 C
H22 0.5512 1.0045 0.4032 0.055 Uiso calc R 1 H
C23 0.6261(3) 1.2916(10) 0.4144(5) 0.0490(12) Uani d . 1 C
H23 0.6365 1.3011 0.3401 0.059 Uiso calc R 1 H
C24 0.6613(3) 1.4537(10) 0.4849(5) 0.0512(13) Uani d . 1 C
H24 0.6953 1.5739 0.4587 0.061 Uiso calc R 1 H
C25 0.6468(3) 1.4406(10) 0.5927(4) 0.0491(12) Uani d . 1 C
H25 0.6709 1.5514 0.6409 0.059 Uiso calc R 1 H
C26 0.5962(3) 1.2627(9) 0.6316(4) 0.0466(11) Uani d . 1 C
H26 0.5861 1.2533 0.7060 0.056 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0554(7) 0.0669(8) 0.0495(7) -0.0078(6) 0.0089(6) 0.0006(6)
O1 0.050(2) 0.072(2) 0.043(2) -0.0103(18) 0.0018(16) -0.0006(17)
N1 0.048(2) 0.047(2) 0.046(2) -0.0053(19) 0.0016(19) -0.0024(19)
C1 0.038(2) 0.044(3) 0.048(3) -0.003(2) 0.000(2) 0.002(2)
C2 0.033(2) 0.042(3) 0.050(3) 0.001(2) 0.001(2) 0.001(2)
C11 0.036(2) 0.042(3) 0.049(3) 0.002(2) -0.002(2) 0.002(2)
C12 0.035(2) 0.047(3) 0.050(3) 0.001(2) 0.002(2) 0.004(2)
C13 0.037(3) 0.049(3) 0.063(3) -0.005(2) 0.001(2) 0.002(3)
C14 0.038(2) 0.052(3) 0.064(3) 0.000(2) -0.007(2) 0.000(2)
C15 0.047(3) 0.054(3) 0.046(3) 0.004(3) -0.003(2) 0.003(2)
C16 0.041(3) 0.047(3) 0.053(3) -0.002(2) -0.002(2) 0.003(2)
C21 0.032(2) 0.042(3) 0.050(3) 0.0016(19) -0.0004(19) -0.001(2)
C22 0.039(2) 0.050(3) 0.050(3) -0.001(2) 0.000(2) 0.002(2)
C23 0.040(3) 0.056(3) 0.051(3) -0.001(2) 0.004(2) 0.000(2)
C24 0.042(3) 0.043(3) 0.068(4) -0.001(2) 0.001(2) 0.000(2)
C25 0.043(2) 0.043(3) 0.061(3) 0.002(2) -0.007(2) -0.005(2)
C26 0.043(3) 0.049(3) 0.049(3) 0.000(2) -0.004(2) -0.002(2)
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
C11 N1 C1 122.2(4)
C11 N1 H1 124(3)
C1 N1 H1 113(3)
N1 C1 C2 110.7(4)
N1 C1 H1A 109.5
C2 C1 H1A 109.5
N1 C1 H1B 109.5
C2 C1 H1B 109.5
H1A C1 H1B 108.1
O1 C2 C1 121.1(5)
O1 C2 C21 121.9(4)
C1 C2 C21 117.0(4)
N1 C11 C16 122.2(5)
N1 C11 C12 121.5(5)
C16 C11 C12 116.3(5)
C13 C12 C11 122.2(5)
C13 C12 Cl1 119.2(4)
C11 C12 Cl1 118.6(4)
C14 C13 C12 120.2(5)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 119.2(5)
C13 C14 H14 120.4
C15 C14 H14 120.4
C16 C15 C14 120.4(5)
C16 C15 H15 119.8
C14 C15 H15 119.8
C15 C16 C11 121.7(5)
C15 C16 H16 119.2
C11 C16 H16 119.2
C22 C21 C26 120.2(5)
C22 C21 C2 121.2(4)
C26 C21 C2 118.6(4)
C21 C22 C23 119.3(5)
C21 C22 H22 120.4
C23 C22 H22 120.4
C24 C23 C22 120.6(5)
C24 C23 H23 119.7
C22 C23 H23 119.7
C25 C24 C23 120.1(5)
C25 C24 H24 119.9
C23 C24 H24 119.9
C24 C25 C26 120.0(5)
C24 C25 H25 120.0
C26 C25 H25 120.0
C21 C26 C25 119.8(5)
C21 C26 H26 120.1
C25 C26 H26 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 1.734(6) y
O1 C2 1.210(6) y
N1 C11 1.372(7) y
N1 C1 1.439(6) y
N1 H1 0.82(6) ?
C1 C2 1.508(7) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 C21 1.511(6) ?
C11 C16 1.398(7) ?
C11 C12 1.419(7) ?
C12 C13 1.390(8) ?
C13 C14 1.380(8) ?
C13 H13 0.9500 ?
C14 C15 1.401(8) ?
C14 H14 0.9500 ?
C15 C16 1.396(7) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C21 C22 1.389(7) ?
C21 C26 1.393(7) ?
C22 C23 1.402(7) ?
C22 H22 0.9500 ?
C23 C24 1.389(8) ?
C23 H23 0.9500 ?
C24 C25 1.376(8) ?
C24 H24 0.9500 ?
C25 C26 1.408(8) ?
C25 H25 0.9500 ?
C26 H26 0.9500 ?
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
C11 N1 C1 C2 -178.5(4) y
N1 C1 C2 O1 0.3(7) ?
N1 C1 C2 C21 179.9(4) ?
C1 N1 C11 C16 -1.2(7) ?
C1 N1 C11 C12 179.2(4) ?
N1 C11 C12 C13 -179.8(5) ?
C16 C11 C12 C13 0.5(7) ?
N1 C11 C12 Cl1 0.1(6) ?
C16 C11 C12 Cl1 -179.5(4) ?
C11 C12 C13 C14 -0.2(8) ?
Cl1 C12 C13 C14 179.8(4) ?
C12 C13 C14 C15 0.3(8) ?
C13 C14 C15 C16 -0.8(8) ?
C14 C15 C16 C11 1.2(8) ?
N1 C11 C16 C15 179.4(5) ?
C12 C11 C16 C15 -1.0(7) ?
O1 C2 C21 C22 -179.9(5) ?
C1 C2 C21 C22 0.4(6) ?
O1 C2 C21 C26 0.7(7) ?
C1 C2 C21 C26 -178.9(5) ?
C26 C21 C22 C23 0.4(7) ?
C2 C21 C22 C23 -178.9(4) ?
C21 C22 C23 C24 -0.5(7) ?
C22 C23 C24 C25 0.3(7) ?
C23 C24 C25 C26 -0.1(7) ?
C22 C21 C26 C25 -0.2(7) ?
C2 C21 C26 C25 179.2(4) ?
C24 C25 C26 C21 0.0(7) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 689466
