##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2009-05-13
_journal_date_accepted     2009-06-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      7
_journal_page_first     o1719
_journal_page_last     o1719
_journal_paper_category     QO
_journal_coeditor_code     YA2097
_publ_contact_author_name
; 'Sun jie'
;
_publ_contact_author_address
; College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No.5 Nanjing,
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     sunjie5516@126.com
_publ_contact_author_fax     '86 25 ?'
_publ_contact_author_phone     '86 25 83587440'
_publ_section_title
;
2-Chloro-N,N-diphenylacetamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Shao, Shuai'
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Sun, Jie'
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Chloro-N,N-diphenylacetamide
;
_chemical_name_common     '2-chloro-N,N-diphenylacetamide'
_chemical_formula_moiety     'C14 H12 Cl N O'
_chemical_formula_sum     'C14 H12 Cl N O'
_chemical_formula_iupac     'C14 H12 Cl N O'
_chemical_formula_weight     245.70
_chemical_melting_point     393
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    x,y,z
    1/2-x,-y,1/2+z
    1/2+x,1/2-y,-z
    -x,1/2+y,1/2-z
_cell_length_a     6.4350(13)
_cell_length_b     12.799(3)
_cell_length_c     14.944(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1230.8(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.0
_cell_measurement_theta_max     13.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.326
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.29
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.917
_exptl_absorpt_correction_T_max     0.971
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2519
_diffrn_reflns_av_R_equivalents     0.064
_diffrn_reflns_av_sigmaI/netI     0.051
_diffrn_reflns_theta_min     2.1
_diffrn_reflns_theta_max     25.3
_diffrn_reflns_theta_full     25.3
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     1
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2231
_reflns_number_gt     1842
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.058
_refine_ls_R_factor_gt     0.045
_refine_ls_wR_factor_gt     0.104
_refine_ls_wR_factor_ref     0.112
_refine_ls_goodness_of_fit_ref     1.00
_refine_ls_restrained_S_all     1.00
_refine_ls_number_reflns     2231
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'calc w=1/[σ²(Fo²)+(0.065P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.18
_refine_diff_density_min     -0.21
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 912 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.14(9)
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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo,1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl 0.97222(13) 0.79305(6) 0.11836(6) 0.0621(3) Uani d . 1 . .
    O O 1.0050(3) 0.63002(15) -0.01779(12) 0.0490(5) Uani d . 1 . .
    N N 1.2460(3) 0.52988(16) 0.05137(14) 0.0354(5) Uani d . 1 . .
    C C1 1.6477(5) 0.4811(2) 0.2686(2) 0.0543(8) Uani d . 1 . .
    H H1A 1.7359 0.4711 0.3172 0.065 Uiso calc R 1 . .
    C C2 1.4544(5) 0.4359(2) 0.26845(19) 0.0514(8) Uani d . 1 . .
    H H2A 1.4111 0.3956 0.3167 0.062 Uiso calc R 1 . .
    C C3 1.3243(5) 0.4509(2) 0.19570(17) 0.0410(7) Uani d . 1 . .
    H H3A 1.1943 0.4193 0.1943 0.049 Uiso calc R 1 . .
    C C4 1.3879(4) 0.51270(19) 0.12568(16) 0.0343(6) Uani d . 1 . .
    C C5 1.5827(5) 0.5572(2) 0.1258(2) 0.0485(7) Uani d . 1 . .
    H H5A 1.6263 0.5978 0.0777 0.058 Uiso calc R 1 . .
    C C6 1.7120(5) 0.5409(3) 0.1976(2) 0.0596(9) Uani d . 1 . .
    H H6A 1.8439 0.5706 0.1981 0.072 Uiso calc R 1 . .
    C C7 1.1939(8) 0.2816(3) -0.1312(2) 0.0726(12) Uani d . 1 . .
    H H7A 1.1834 0.2270 -0.1719 0.087 Uiso calc R 1 . .
    C C8 1.0262(7) 0.3081(3) -0.0781(3) 0.0695(11) Uani d . 1 . .
    H H8A 0.9034 0.2702 -0.0825 0.083 Uiso calc R 1 . .
    C C9 1.0392(5) 0.3908(2) -0.0181(2) 0.0527(8) Uani d . 1 . .
    H H9A 0.9261 0.4090 0.0174 0.063 Uiso calc R 1 . .
    C C10 1.2238(5) 0.4453(2) -0.01240(17) 0.0381(7) Uani d . 1 . .
    C C11 1.3920(5) 0.4182(2) -0.06415(18) 0.0500(8) Uani d . 1 . .
    H H11A 1.5165 0.4546 -0.0594 0.060 Uiso calc R 1 . .
    C C12 1.3728(7) 0.3355(3) -0.1236(2) 0.0626(9) Uani d . 1 . .
    H H12A 1.4858 0.3170 -0.1590 0.075 Uiso calc R 1 . .
    C C13 1.1327(4) 0.6186(2) 0.04201(16) 0.0341(6) Uani d . 1 . .
    C C14 1.1818(4) 0.7040(2) 0.10923(18) 0.0410(6) Uani d . 1 . .
    H H14A 1.3058 0.7412 0.0905 0.049 Uiso calc R 1 . .
    H H14B 1.2092 0.6729 0.1672 0.049 Uiso calc R 1 . .
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
    Cl 0.0602(5) 0.0518(5) 0.0743(6) 0.0188(4) -0.0070(4) -0.0153(4)
    O 0.0505(12) 0.0557(12) 0.0409(10) 0.0128(10) -0.0121(10) -0.0018(9)
    N 0.0378(12) 0.0378(12) 0.0306(11) 0.0016(11) -0.0061(10) -0.0002(10)
    C1 0.055(2) 0.063(2) 0.0450(17) 0.0191(17) -0.0191(17) -0.0039(16)
    C2 0.066(2) 0.0570(18) 0.0315(15) 0.0058(16) -0.0011(15) 0.0079(13)
    C3 0.0404(16) 0.0448(15) 0.0377(15) -0.0018(13) 0.0028(13) 0.0058(13)
    C4 0.0360(14) 0.0374(13) 0.0295(13) 0.0037(11) -0.0034(12) -0.0008(11)
    C5 0.0403(16) 0.0593(18) 0.0459(17) -0.0076(13) -0.0032(14) 0.0137(15)
    C6 0.0380(18) 0.078(2) 0.063(2) -0.0050(16) -0.0138(17) -0.0025(19)
    C7 0.122(4) 0.0484(19) 0.047(2) 0.006(2) -0.023(2) -0.0115(16)
    C8 0.086(3) 0.0488(19) 0.073(2) -0.020(2) -0.029(2) 0.0012(17)
    C9 0.057(2) 0.0487(17) 0.0525(17) -0.0111(16) -0.0092(16) 0.0001(15)
    C10 0.0508(17) 0.0327(14) 0.0307(14) 0.0016(13) -0.0058(13) 0.0035(11)
    C11 0.060(2) 0.0472(17) 0.0429(16) 0.0021(15) 0.0058(16) -0.0007(14)
    C12 0.086(3) 0.0569(19) 0.0447(18) 0.012(2) 0.000(2) -0.0085(16)
    C13 0.0329(14) 0.0406(14) 0.0288(13) 0.0003(12) 0.0009(12) 0.0045(11)
    C14 0.0385(14) 0.0403(15) 0.0443(15) 0.0026(12) 0.0001(13) -0.0028(13)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    Cl C14 . 1.771(3) ?
    O C13 . 1.223(3) ?
    N C13 . 1.357(3) ?
    N C10 . 1.449(3) ?
    N C4 . 1.454(3) ?
    C1 C2 . 1.372(5) ?
    C1 C6 . 1.372(5) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.386(4) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.374(4) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.377(4) ?
    C5 C6 . 1.374(4) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 C12 . 1.347(6) ?
    C7 C8 . 1.382(6) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.390(5) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.380(4) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.375(4) ?
    C11 C12 . 1.386(4) ?
    C11 H11A . 0.9300 ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.518(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C13 N C10 . . 120.3(2) ?
    C13 N C4 . . 122.9(2) ?
    C10 N C4 . . 116.8(2) ?
    C2 C1 C6 . . 120.5(3) ?
    C2 C1 H1A . . 119.8 ?
    C6 C1 H1A . . 119.8 ?
    C1 C2 C3 . . 119.4(3) ?
    C1 C2 H2A . . 120.3 ?
    C3 C2 H2A . . 120.3 ?
    C4 C3 C2 . . 119.8(3) ?
    C4 C3 H3A . . 120.1 ?
    C2 C3 H3A . . 120.1 ?
    C3 C4 C5 . . 120.6(3) ?
    C3 C4 N . . 118.8(2) ?
    C5 C4 N . . 120.7(2) ?
    C6 C5 C4 . . 119.3(3) ?
    C6 C5 H5A . . 120.3 ?
    C4 C5 H5A . . 120.3 ?
    C1 C6 C5 . . 120.4(3) ?
    C1 C6 H6A . . 119.8 ?
    C5 C6 H6A . . 119.8 ?
    C12 C7 C8 . . 119.6(3) ?
    C12 C7 H7A . . 120.2 ?
    C8 C7 H7A . . 120.2 ?
    C7 C8 C9 . . 120.7(3) ?
    C7 C8 H8A . . 119.7 ?
    C9 C8 H8A . . 119.7 ?
    C10 C9 C8 . . 118.5(3) ?
    C10 C9 H9A . . 120.8 ?
    C8 C9 H9A . . 120.8 ?
    C11 C10 C9 . . 121.0(3) ?
    C11 C10 N . . 118.7(3) ?
    C9 C10 N . . 120.2(3) ?
    C10 C11 C12 . . 118.9(3) ?
    C10 C11 H11A . . 120.6 ?
    C12 C11 H11A . . 120.6 ?
    C7 C12 C11 . . 121.4(4) ?
    C7 C12 H12A . . 119.3 ?
    C11 C12 H12A . . 119.3 ?
    O C13 N . . 122.4(2) ?
    O C13 C14 . . 122.5(2) ?
    N C13 C14 . . 115.0(2) ?
    C13 C14 Cl . . 110.84(19) ?
    C13 C14 H14A . . 109.5 ?
    Cl C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    Cl C14 H14B . . 109.5 ?
    H14A C14 H14B . . 108.1 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 0.2(5) ?
    C1 C2 C3 C4 . . . . -1.6(4) ?
    C2 C3 C4 C5 . . . . 2.1(4) ?
    C2 C3 C4 N . . . . -178.1(2) ?
    C13 N C4 C3 . . . . 100.9(3) ?
    C10 N C4 C3 . . . . -77.0(3) ?
    C13 N C4 C5 . . . . -79.4(3) ?
    C10 N C4 C5 . . . . 102.8(3) ?
    C3 C4 C5 C6 . . . . -1.3(4) ?
    N C4 C5 C6 . . . . 179.0(3) ?
    C2 C1 C6 C5 . . . . 0.7(5) ?
    C4 C5 C6 C1 . . . . -0.1(5) ?
    C12 C7 C8 C9 . . . . 1.1(5) ?
    C7 C8 C9 C10 . . . . -0.4(5) ?
    C8 C9 C10 C11 . . . . -0.6(4) ?
    C8 C9 C10 N . . . . -178.0(3) ?
    C13 N C10 C11 . . . . 116.2(3) ?
    C4 N C10 C11 . . . . -65.9(3) ?
    C13 N C10 C9 . . . . -66.3(3) ?
    C4 N C10 C9 . . . . 111.6(3) ?
    C9 C10 C11 C12 . . . . 0.9(4) ?
    N C10 C11 C12 . . . . 178.4(2) ?
    C8 C7 C12 C11 . . . . -0.7(5) ?
    C10 C11 C12 C7 . . . . -0.2(5) ?
    C10 N C13 O . . . . 2.1(4) ?
    C4 N C13 O . . . . -175.7(2) ?
    C10 N C13 C14 . . . . -175.8(2) ?
    C4 N C13 C14 . . . . 6.4(4) ?
    O C13 C14 Cl . . . . 23.3(3) ?
    N C13 C14 Cl . . . . -158.8(2) ?
