##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-2013
_database_code_depnum_ccdc_archive     'CCDC 1443109'
_chemical_name_systematic
;
N-(4-Acetylphenyl)-2-chloroacetamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H10 Cl N O2'
_chemical_formula_sum     'C10 H10 Cl N O2'
_chemical_formula_iupac     'C10 H10 Cl N O2'
_chemical_formula_weight     211.64
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     4.17130(10)
_cell_length_b     14.7792(4)
_cell_length_c     16.1755(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     997.19(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9297
_cell_measurement_theta_min     2.52
_cell_measurement_theta_max     27.90
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.410
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     440
_exptl_absorpt_coefficient_mu     0.355
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.890
_exptl_absorpt_correction_T_max     0.905
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21908
_diffrn_reflns_av_R_equivalents     0.0253
_diffrn_reflns_theta_min     1.866
_diffrn_reflns_theta_max     28.349
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -4
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -19
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_refine_special_details     ?
_reflns_number_total     2489
_reflns_number_gt     2189
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0457
_refine_ls_R_factor_gt     0.0380
_refine_ls_wR_factor_gt     0.1000
_refine_ls_wR_factor_ref     0.1060
_refine_ls_goodness_of_fit_ref     1.051
_refine_ls_restrained_S_all     1.051
_refine_ls_number_reflns     2489
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0511P)²+0.2203P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.336
_refine_diff_density_min     -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons & Flack, 2004)
;
_refine_ls_abs_structure_Flack     0.033(14)
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
;
SMART (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.3090(7) 0.91692(14) 0.79553(12) 0.0734(7) Uani d 1 . .
    C C2 0.0351(7) 0.97312(17) 0.67865(17) 0.0565(6) Uani d 1 . .
    H H2A 0.0171 1.0268 0.7117 0.085 Uiso calc 1 . .
    H H2B -0.1749 0.9531 0.6626 0.085 Uiso calc 1 . .
    H H2C 0.1594 0.9860 0.6301 0.085 Uiso calc 1 . .
    C C3 0.1961(7) 0.90065(16) 0.72759(14) 0.0485(6) Uani d 1 . .
    C C4 0.2230(6) 0.80791(16) 0.69210(13) 0.0430(5) Uani d 1 . .
    C C5 0.3856(7) 0.74153(17) 0.73672(14) 0.0513(6) Uani d 1 . .
    H H5 0.4769 0.7560 0.7875 0.062 Uiso calc 1 . .
    C C6 0.4122(7) 0.65528(16) 0.70661(14) 0.0504(6) Uani d 1 . .
    H H6 0.5211 0.6118 0.7372 0.061 Uiso calc 1 . .
    C C7 0.2774(6) 0.63189(15) 0.63035(13) 0.0424(5) Uani d 1 . .
    C C8 0.1178(7) 0.69802(16) 0.58504(13) 0.0478(5) Uani d 1 . .
    H H8 0.0278 0.6838 0.5341 0.057 Uiso calc 1 . .
    C C9 0.0933(7) 0.78470(17) 0.61582(13) 0.0471(5) Uani d 1 . .
    H H9 -0.0123 0.8286 0.5849 0.056 Uiso calc 1 . .
    N N10 0.3136(6) 0.54170(14) 0.60441(12) 0.0480(5) Uani d 1 . .
    H H10 0.413(8) 0.509(2) 0.6343(19) 0.055(8) Uiso d 1 . .
    C C11 0.1741(7) 0.50007(17) 0.53897(15) 0.0492(6) Uani d 1 . .
    O O12 -0.0027(7) 0.53651(14) 0.49073(13) 0.0762(7) Uani d 1 . .
    C C13 0.2641(9) 0.40081(19) 0.53398(18) 0.0658(8) Uani d 1 . .
    H H13A 0.1811 0.3697 0.5823 0.079 Uiso calc 1 . .
    H H13B 0.4958 0.3953 0.5347 0.079 Uiso calc 1 . .
    Cl Cl14 0.1160(3) 0.34854(5) 0.44531(5) 0.0852(3) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O1 C3 . 1.219(3) y
    C2 C3 . 1.492(4) ?
    C2 H2A . 0.9600 ?
    C2 H2B . 0.9600 ?
    C2 H2C . 0.9600 ?
    C3 C4 . 1.490(3) ?
    C4 C9 . 1.390(3) ?
    C4 C5 . 1.394(3) ?
    C5 C6 . 1.369(4) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.399(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.391(3) ?
    C7 N10 . 1.405(3) ?
    C8 C9 . 1.378(3) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    N10 C11 . 1.356(3) ?
    N10 H10 . 0.80(3) ?
    C11 O12 . 1.201(3) y
    C11 C13 . 1.516(4) ?
    C13 Cl14 . 1.742(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 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
    C3 C2 H2A . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    C3 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    O1 C3 C4 . . 120.0(2) ?
    O1 C3 C2 . . 120.7(2) ?
    C4 C3 C2 . . 119.3(2) y
    C9 C4 C5 . . 118.4(2) ?
    C9 C4 C3 . . 122.6(2) ?
    C5 C4 C3 . . 119.0(2) ?
    C6 C5 C4 . . 120.7(2) ?
    C6 C5 H5 . . 119.7 ?
    C4 C5 H5 . . 119.7 ?
    C5 C6 C7 . . 120.7(2) ?
    C5 C6 H6 . . 119.6 ?
    C7 C6 H6 . . 119.6 ?
    C8 C7 C6 . . 118.9(2) ?
    C8 C7 N10 . . 124.1(2) ?
    C6 C7 N10 . . 117.0(2) ?
    C9 C8 C7 . . 119.9(2) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C8 C9 C4 . . 121.4(2) ?
    C8 C9 H9 . . 119.3 ?
    C4 C9 H9 . . 119.3 ?
    C11 N10 C7 . . 128.1(2) ?
    C11 N10 H10 . . 115(2) ?
    C7 N10 H10 . . 117(2) ?
    O12 C11 N10 . . 124.6(2) ?
    O12 C11 C13 . . 123.4(2) ?
    N10 C11 C13 . . 112.0(2) y
    C11 C13 Cl14 . . 112.6(2) ?
    C11 C13 H13A . . 109.1 ?
    Cl14 C13 H13A . . 109.1 ?
    C11 C13 H13B . . 109.1 ?
    Cl14 C13 H13B . . 109.1 ?
    H13A C13 H13B . . 107.8 ?
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
    C2 H2C O12 4_566 0.96 2.43 3.353(3) 161
    C8 H8 O12 . 0.93 2.29 2.877(3) 121
    N10 H10 O1 3_646 0.80(3) 2.11(3) 2.915(3) 176(3)
    C8 H8 Cg1 4_466 0.93 3.650 4.434(3) 144
_shelxl_version_number         .2013
data_II
_audit_creation_method     SHELXL-2013
_database_code_depnum_ccdc_archive     'CCDC 1443110'
_chemical_name_systematic
;
2-(4-Acetylanilino)-2-oxoethyl cinnamate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H17 N O4'
_chemical_formula_sum     'C19 H17 N O4'
_chemical_formula_iupac     'C19 H17 N O4'
_chemical_formula_weight     323.33
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P c a 21'
_space_group_name_Hall     'P 2c -2ac'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y, z'
    '-x+1/2, y, z+1/2'
_cell_length_a     9.7969(15)
_cell_length_b     17.594(3)
_cell_length_c     9.6425(15)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1662.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2290
_cell_measurement_theta_min     3.11
_cell_measurement_theta_max     19.40
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.292
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
_exptl_absorpt_correction_T_min     0.975
_exptl_absorpt_correction_T_max     0.995
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13763
_diffrn_reflns_av_R_equivalents     0.0444
_diffrn_reflns_theta_min     2.315
_diffrn_reflns_theta_max     28.309
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
;
_reflns_number_total     3879
_reflns_number_gt     1781
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1528
_refine_ls_R_factor_gt     0.0568
_refine_ls_wR_factor_gt     0.0921
_refine_ls_wR_factor_ref     0.1194
_refine_ls_goodness_of_fit_ref     0.986
_refine_ls_restrained_S_all     0.986
_refine_ls_number_reflns     3879
_refine_ls_number_parameters     222
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.111
_refine_diff_density_min     -0.122
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
SMART (Bruker, 2012)
;
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.8574(4) 0.3135(2) 0.4874(4) 0.1302(15) Uani d 1 . .
    C C2 0.7449(7) 0.2863(2) 0.4653(5) 0.0888(15) Uani d 1 . .
    C C3 0.7323(5) 0.2206(2) 0.3704(4) 0.0643(11) Uani d 1 . .
    C C4 0.6205(6) 0.3195(3) 0.5314(6) 0.1145(19) Uani d 1 . .
    H H4A 0.6472 0.3529 0.6052 0.172 Uiso calc 1 . .
    H H4B 0.5646 0.2794 0.5679 0.172 Uiso calc 1 . .
    H H4C 0.5697 0.3476 0.4634 0.172 Uiso calc 1 . .
    C C5 0.8482(4) 0.1850(3) 0.3212(6) 0.0826(14) Uani d 1 . .
    H H5 0.9328 0.2024 0.3512 0.099 Uiso calc 1 . .
    C C6 0.8442(4) 0.1257(2) 0.2308(5) 0.0741(13) Uani d 1 . .
    H H6 0.9247 0.1026 0.2015 0.089 Uiso calc 1 . .
    C C7 0.7192(3) 0.0999(2) 0.1828(4) 0.0538(10) Uani d 1 . .
    C C8 0.6030(4) 0.1343(2) 0.2313(5) 0.0738(13) Uani d 1 . .
    H H8 0.5182 0.1172 0.2013 0.089 Uiso calc 1 . .
    C C9 0.6099(4) 0.1936(2) 0.3230(5) 0.0820(13) Uani d 1 . .
    H H9 0.5295 0.2160 0.3538 0.098 Uiso calc 1 . .
    N N10 0.7033(3) 0.04028(18) 0.0870(3) 0.0569(9) Uani d 1 . .
    H H10 0.620(4) 0.025(2) 0.062(5) 0.100(17) Uiso d 1 . .
    C C11 0.7993(4) -0.0064(2) 0.0340(5) 0.0635(11) Uani d 1 . .
    O O12 0.9198(2) -0.00278(15) 0.0659(4) 0.0964(11) Uani d 1 . .
    C C13 0.7502(5) -0.0647(2) -0.0685(4) 0.0723(12) Uani d 1 . .
    H H13A 0.6513 -0.0672 -0.0666 0.087 Uiso calc 1 . .
    H H13B 0.7783 -0.0504 -0.1613 0.087 Uiso calc 1 . .
    O O14 0.8069(3) -0.13785(15) -0.0332(3) 0.0743(8) Uani d 1 . .
    C C15 0.7484(4) -0.1718(2) 0.0733(5) 0.0594(10) Uani d 1 . .
    O O16 0.6561(3) -0.14411(17) 0.1369(4) 0.0918(10) Uani d 1 . .
    C C17 0.8134(4) -0.2450(2) 0.1080(5) 0.0630(10) Uani d 1 . .
    H H17 0.8902 -0.2609 0.0592 0.076 Uiso calc 1 . .
    C C18 0.7634(4) -0.2880(2) 0.2077(4) 0.0654(11) Uani d 1 . .
    H H18 0.6871 -0.2690 0.2535 0.078 Uiso calc 1 . .
    C C19 0.8132(4) -0.3621(2) 0.2553(4) 0.0614(11) Uani d 1 . .
    C C20 0.9287(4) -0.3959(2) 0.1999(5) 0.0751(12) Uani d 1 . .
    H H20 0.9788 -0.3709 0.1318 0.090 Uiso calc 1 . .
    C C21 0.9695(5) -0.4671(3) 0.2463(6) 0.0895(14) Uani d 1 . .
    H H21 1.0464 -0.4901 0.2082 0.107 Uiso calc 1 . .
    C C22 0.8971(6) -0.5038(3) 0.3482(6) 0.0905(15) Uani d 1 . .
    H H22 0.9246 -0.5516 0.3783 0.109 Uiso calc 1 . .
    C C23 0.7852(5) -0.4703(3) 0.4052(5) 0.0920(16) Uani d 1 . .
    H H23 0.7373 -0.4946 0.4755 0.110 Uiso calc 1 . .
    C C24 0.7430(5) -0.3997(2) 0.3580(5) 0.0786(14) Uani d 1 . .
    H H24 0.6658 -0.3773 0.3965 0.094 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O1 C2 . 1.221(5) y
    C2 C3 . 1.478(6) y
    C2 C4 . 1.495(7) ?
    C3 C9 . 1.369(5) ?
    C3 C5 . 1.380(6) ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 C6 . 1.361(6) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.385(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.372(5) ?
    C7 N10 . 1.406(5) ?
    C8 C9 . 1.369(5) ?
    C8 H8 . 0.9300 ?
    C9 H9 . 0.9300 ?
    N10 C11 . 1.350(4) ?
    N10 H10 . 0.89(4) ?
    C11 O12 . 1.221(4) y
    C11 C13 . 1.502(6) ?
    C13 O14 . 1.443(4) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    O14 C15 . 1.319(5) ?
    C15 O16 . 1.196(4) y
    C15 C17 . 1.475(5) ?
    C17 C18 . 1.319(5) y
    C17 H17 . 0.9300 ?
    C18 C19 . 1.465(5) ?
    C18 H18 . 0.9300 ?
    C19 C24 . 1.375(5) ?
    C19 C20 . 1.385(5) ?
    C20 C21 . 1.390(5) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.372(6) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.361(6) ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.386(6) ?
    C23 H23 . 0.9300 ?
    C24 H24 . 0.9300 ?
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
    O1 C2 C3 . . 119.4(6) ?
    O1 C2 C4 . . 120.5(5) ?
    C3 C2 C4 . . 120.1(5) y
    C9 C3 C5 . . 116.6(4) ?
    C9 C3 C2 . . 123.5(5) ?
    C5 C3 C2 . . 119.9(5) ?
    C2 C4 H4A . . 109.5 ?
    C2 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C2 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    C6 C5 C3 . . 123.0(4) ?
    C6 C5 H5 . . 118.5 ?
    C3 C5 H5 . . 118.5 ?
    C5 C6 C7 . . 119.4(4) ?
    C5 C6 H6 . . 120.3 ?
    C7 C6 H6 . . 120.3 ?
    C8 C7 C6 . . 118.4(4) ?
    C8 C7 N10 . . 117.5(3) ?
    C6 C7 N10 . . 124.2(4) ?
    C9 C8 C7 . . 121.1(4) ?
    C9 C8 H8 . . 119.5 ?
    C7 C8 H8 . . 119.5 ?
    C8 C9 C3 . . 121.6(4) ?
    C8 C9 H9 . . 119.2 ?
    C3 C9 H9 . . 119.2 ?
    C11 N10 C7 . . 128.7(3) ?
    C11 N10 H10 . . 111(3) ?
    C7 N10 H10 . . 120(3) ?
    O12 C11 N10 . . 123.1(4) ?
    O12 C11 C13 . . 120.8(4) ?
    N10 C11 C13 . . 116.1(4) y
    O14 C13 C11 . . 109.3(3) ?
    O14 C13 H13A . . 109.8 ?
    C11 C13 H13A . . 109.8 ?
    O14 C13 H13B . . 109.8 ?
    C11 C13 H13B . . 109.8 ?
    H13A C13 H13B . . 108.3 ?
    C15 O14 C13 . . 114.8(3) ?
    O16 C15 O14 . . 122.9(4) ?
    O16 C15 C17 . . 124.4(4) ?
    O14 C15 C17 . . 112.6(4) y
    C18 C17 C15 . . 120.4(4) y
    C18 C17 H17 . . 119.8 ?
    C15 C17 H17 . . 119.8 ?
    C17 C18 C19 . . 128.0(4) ?
    C17 C18 H18 . . 116.0 ?
    C19 C18 H18 . . 116.0 ?
    C24 C19 C20 . . 118.7(4) ?
    C24 C19 C18 . . 119.1(4) ?
    C20 C19 C18 . . 122.2(4) ?
    C19 C20 C21 . . 119.9(4) ?
    C19 C20 H20 . . 120.1 ?
    C21 C20 H20 . . 120.1 ?
    C22 C21 C20 . . 120.4(4) ?
    C22 C21 H21 . . 119.8 ?
    C20 C21 H21 . . 119.8 ?
    C23 C22 C21 . . 120.1(4) ?
    C23 C22 H22 . . 119.9 ?
    C21 C22 H22 . . 119.9 ?
    C22 C23 C24 . . 119.8(5) ?
    C22 C23 H23 . . 120.1 ?
    C24 C23 H23 . . 120.1 ?
    C19 C24 C23 . . 121.2(4) ?
    C19 C24 H24 . . 119.4 ?
    C23 C24 H24 . . 119.4 ?
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
    C6 H6 O12 . 0.93 2.27 2.860(6) 121
    C6 H6 O16 3 0.93 2.46 3.203(5) 137
    C8 H8 O12 3_455 0.93 2.59 3.335(5) 138
    N10 H10 O12 3_455 0.89(4) 2.00(4) 2.862(4) 162(4)
    C4 H4C Cg2 3_455 0.96 3.010 3.948(6) 160
_shelxl_version_number         .2013
data_global
_journal_date_recd_electronic     2015-10-22
_journal_date_accepted     2015-12-17
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      2
_journal_page_first     94
_journal_page_last     98
_journal_paper_category     FA
_journal_paper_doi     10.1107/S205322961502433X
_journal_coeditor_code     CU3092
_publ_contact_author_name     'Sung Kwon Kang'
_publ_contact_author_address
;
Department of Chemistry,
Chungnam National University,
Daejeon 305-764,
Republic of Korea
;
_publ_contact_author_email
;
skkang@cnu.ac.kr
;
_publ_contact_author_fax     '82 (42)8218896'
_publ_contact_author_phone     '82(42)8216552'
_publ_section_title
;
Synthesis and crystal structures of the potential
tyrosinase inhibitors
N-(4-acetylphenyl)-2-chloroacetamide
and 2-(4-acetylanilino)-2-oxoethyl cinnamate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ashraf, Zaman' .
;
Department of Biology, College of Natural Sciences, Kongju National University,
Gongju 314-701, Republic of Korea
Department of Chemistry, Allama Iqbal Open University, Islamabad 44000,
Pakistan
;
    'Kim, Daeyoung' .
;
Department of Chemistry,
Chungnam National University,
Daejeon 305-764,
Republic of Korea
;
    'Seo, Sung-Yum' .
;
Department of Biology, College of Natural Sciences, Kongju National University,
Gongju 314-701, Republic of Korea
;
    'Kang, Sung Kwon' .
;
Department of Chemistry,
Chungnam National University,
Daejeon 305-764,
Republic of Korea
;
_publ_section_synopsis
;
Substituted benzoic acid and cinnamic acid esters are of interest as tyrosinase
inhibitors. In the amide-based derivative
N-(4-acetylphenyl)-2-chloroacetamide, the N---(C=O)---C plane of
the acetamide group are almost coplanar. Instead of esterification, a cheaper
and more efficient synthetic method has been developed for the preparation of
2-(4-acetylanilino)-2-oxoethyl cinnamate, in which the acetamide and cinnamate
groups are almost planar. N---H...O, C---H...O and C---H...π interactions
link molecules of both compounds into a three-dimensional network.
[OK?]
;
