#------------------------------------------------------------------------------
#$Date: 2023-12-07 13:51:21 +0200 (Thu, 07 Dec 2023) $
#$Revision: 288147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022872.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_2022872
loop_
_publ_author_name
'Mohamed-Ezzat, Reham A'
'Kariuki, Benson M.'
'Srour, Aladdin M.'
_publ_section_title
;
 Synthesis, crystal structure and in vitro anti-proliferative
 activity of 2-[(4-acetyl-phen-yl)carbamo-yl]phenyl acetate.
;
_journal_coeditor_code           DJ2060
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              999
_journal_page_last               1002
_journal_paper_doi               10.1107/S2056989023008526
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C17 H15 N O4'
_chemical_formula_moiety         'C17 H15 N O4'
_chemical_formula_sum            'C17 H15 N O4'
_chemical_formula_weight         297.30
_chemical_name_systematic
;
2-[(4-Acetylphenyl)carbamoyl]phenyl acetate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 110.380(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6286(5)
_cell_length_b                   8.6913(4)
_cell_length_c                   15.8180(7)
_cell_measurement_reflns_used    5304
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      76.1740
_cell_measurement_theta_min      4.0800
_cell_volume                     1498.62(13)
_computing_cell_refinement
;
CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)
;
_computing_data_collection
;
CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)
;
_computing_data_reduction
;
CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)
;
_computing_structure_refinement
;
SHELXL2019/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Agilant SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17065
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.927
_diffrn_reflns_theta_min         4.113
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.390
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2019)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0761P)²+0.1892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                2612
_reflns_number_total             3141
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2060sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022872.cif.'
_cod_original_cell_volume        1498.62(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022872
_cod_database_fobs_code          2022872
_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.
;
_shelx_estimated_absorpt_t_min   0.769
_shelx_estimated_absorpt_t_max   0.905
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C C1 0.5388(2) 0.1466(3) 0.63141(13) 0.0868(6) Uani d 1 . .
H H1A 0.587598 0.105244 0.689002 0.130 Uiso calc 1 . .
H H1B 0.498487 0.064212 0.591739 0.130 Uiso calc 1 . .
H H1C 0.478372 0.215398 0.638833 0.130 Uiso calc 1 . .
C C2 0.61923(14) 0.23211(19) 0.59205(9) 0.0576(4) Uani d 1 . .
C C3 0.56774(12) 0.29253(17) 0.49855(9) 0.0505(3) Uani d 1 . .
C C4 0.64622(13) 0.36063(19) 0.46058(10) 0.0587(4) Uani d 1 . .
H H4 0.728942 0.370691 0.495050 0.070 Uiso calc 1 . .
C C5 0.60455(13) 0.41363(19) 0.37314(10) 0.0589(4) Uani d 1 . .
H H5 0.658915 0.457351 0.348638 0.071 Uiso calc 1 . .
C C6 0.48068(12) 0.40141(16) 0.32165(8) 0.0490(3) Uani d 1 . .
C C7 0.40109(13) 0.3340(2) 0.35836(10) 0.0624(4) Uani d 1 . .
H H7 0.318208 0.325327 0.324040 0.075 Uiso calc 1 . .
C C8 0.44443(13) 0.2795(2) 0.44606(10) 0.0619(4) Uani d 1 . .
H H8 0.390386 0.233633 0.470096 0.074 Uiso calc 1 . .
C C9 0.48064(13) 0.56038(17) 0.19145(9) 0.0539(3) Uani d 1 . .
C C10 0.41025(12) 0.58347(17) 0.09278(9) 0.0512(3) Uani d 1 . .
C C11 0.38681(13) 0.73080(17) 0.05690(10) 0.0532(3) Uani d 1 . .
C C12 0.32771(14) 0.7548(2) -0.03390(11) 0.0629(4) Uani d 1 . .
H H12 0.311768 0.854402 -0.056485 0.075 Uiso calc 1 . .
C C13 0.29218(15) 0.6303(2) -0.09134(10) 0.0668(4) Uani d 1 . .
H H13 0.252995 0.646157 -0.152872 0.080 Uiso calc 1 . .
C C14 0.31454(15) 0.4827(2) -0.05786(10) 0.0634(4) Uani d 1 . .
H H14 0.291076 0.398867 -0.096645 0.076 Uiso calc 1 . .
C C15 0.37213(14) 0.45989(19) 0.03382(10) 0.0574(4) Uani d 1 . .
H H15 0.385567 0.360130 0.056397 0.069 Uiso calc 1 . .
C C16 0.52387(15) 0.93013(18) 0.12475(11) 0.0606(4) Uani d 1 . .
C C17 0.5436(2) 1.0612(2) 0.18968(14) 0.0858(6) Uani d 1 . .
H H17A 0.559486 1.021628 0.249346 0.129 Uiso calc 1 . .
H H17B 0.471610 1.124674 0.172543 0.129 Uiso calc 1 . .
H H17C 0.612495 1.121222 0.188800 0.129 Uiso calc 1 . .
N N1 0.43273(11) 0.45087(15) 0.23117(7) 0.0547(3) Uani d 1 . .
H H1 0.366161 0.407257 0.197490 0.066 Uiso calc 1 . .
O O1 0.72755(11) 0.25066(17) 0.63648(8) 0.0776(4) Uani d 1 . .
O O2 0.57285(12) 0.63430(15) 0.23103(8) 0.0745(4) Uani d 1 . .
O O3 0.41633(10) 0.85821(13) 0.11491(8) 0.0629(3) Uani d 1 . .
O O4 0.58982(12) 0.89231(15) 0.08529(9) 0.0739(3) Uani d 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C3 . . 120.27(15) ?
O1 C2 C1 . . 119.83(14) ?
C3 C2 C1 . . 119.89(14) ?
C4 C3 C8 . . 118.28(12) ?
C4 C3 C2 . . 118.95(13) ?
C8 C3 C2 . . 122.74(14) ?
C5 C4 C3 . . 121.56(13) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 119.58(14) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C7 C6 C5 . . 119.67(13) ?
C7 C6 N1 . . 118.01(12) ?
C5 C6 N1 . . 122.28(13) ?
C6 C7 C8 . . 120.17(13) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C7 C8 C3 . . 120.73(14) ?
C7 C8 H8 . . 119.6 ?
C3 C8 H8 . . 119.6 ?
O2 C9 N1 . . 124.00(13) ?
O2 C9 C10 . . 121.78(13) ?
N1 C9 C10 . . 114.22(12) ?
C11 C10 C15 . . 117.84(13) ?
C11 C10 C9 . . 120.41(13) ?
C15 C10 C9 . . 121.66(13) ?
C12 C11 C10 . . 121.50(14) ?
C12 C11 O3 . . 118.87(14) ?
C10 C11 O3 . . 119.49(12) ?
C11 C12 C13 . . 119.64(15) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C14 C13 C12 . . 120.25(14) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 119.59(15) ?
C13 C14 H14 . . 120.2 ?
C15 C14 H14 . . 120.2 ?
C14 C15 C10 . . 121.16(15) ?
C14 C15 H15 . . 119.4 ?
C10 C15 H15 . . 119.4 ?
O4 C16 O3 . . 123.25(16) ?
O4 C16 C17 . . 126.61(17) ?
O3 C16 C17 . . 110.13(15) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C9 N1 C6 . . 126.92(12) ?
C9 N1 H1 . . 116.5 ?
C6 N1 H1 . . 116.5 ?
C16 O3 C11 . . 116.38(12) ?
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
C1 C2 . 1.490(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O1 . 1.221(2) ?
C2 C3 . 1.4848(18) ?
C3 C4 . 1.388(2) ?
C3 C8 . 1.3890(19) ?
C4 C5 . 1.3759(19) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3902(19) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.382(2) ?
C6 N1 . 1.4101(16) ?
C7 C8 . 1.384(2) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 O2 . 1.2194(18) ?
C9 N1 . 1.3619(19) ?
C9 C10 . 1.5022(18) ?
C10 C11 . 1.389(2) ?
C10 C15 . 1.390(2) ?
C11 C12 . 1.375(2) ?
C11 O3 . 1.4024(18) ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.378(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.384(2) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 O4 . 1.191(2) ?
C16 O3 . 1.358(2) ?
C16 C17 . 1.497(3) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
N1 H1 . 0.8600 ?
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
C5 H5 O2 . 0.93 2.35 2.8792(19) 115.7 yes
C12 H12 O4 3_675 0.93 2.59 3.396(2) 144.7 yes
N1 H1 O1 4_565 0.86 2.08 2.9181(16) 164.3 yes
C8 H8 Cg1 2_545 0.93 3.20 4.0960(15) 163.8 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C2 C3 C4 . . . . 4.4(2) ?
C1 C2 C3 C4 . . . . -174.76(17) ?
O1 C2 C3 C8 . . . . -177.69(16) ?
C1 C2 C3 C8 . . . . 3.1(2) ?
C8 C3 C4 C5 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . 177.60(15) ?
C3 C4 C5 C6 . . . . 1.1(3) ?
C4 C5 C6 C7 . . . . -1.0(2) ?
C4 C5 C6 N1 . . . . -178.77(15) ?
C5 C6 C7 C8 . . . . 0.2(3) ?
N1 C6 C7 C8 . . . . 178.10(15) ?
C6 C7 C8 C3 . . . . 0.5(3) ?
C4 C3 C8 C7 . . . . -0.4(3) ?
C2 C3 C8 C7 . . . . -178.31(16) ?
O2 C9 C10 C11 . . . . -43.7(2) ?
N1 C9 C10 C11 . . . . 136.62(15) ?
O2 C9 C10 C15 . . . . 132.97(18) ?
N1 C9 C10 C15 . . . . -46.7(2) ?
C15 C10 C11 C12 . . . . 0.1(2) ?
C9 C10 C11 C12 . . . . 176.85(13) ?
C15 C10 C11 O3 . . . . 175.68(13) ?
C9 C10 C11 O3 . . . . -7.6(2) ?
C10 C11 C12 C13 . . . . -1.0(2) ?
O3 C11 C12 C13 . . . . -176.59(14) ?
C11 C12 C13 C14 . . . . 0.7(2) ?
C12 C13 C14 C15 . . . . 0.4(3) ?
C13 C14 C15 C10 . . . . -1.3(2) ?
C11 C10 C15 C14 . . . . 1.1(2) ?
C9 C10 C15 C14 . . . . -175.65(14) ?
O2 C9 N1 C6 . . . . -1.7(3) ?
C10 C9 N1 C6 . . . . 178.01(13) ?
C7 C6 N1 C9 . . . . 156.85(16) ?
C5 C6 N1 C9 . . . . -25.3(2) ?
O4 C16 O3 C11 . . . . 2.0(2) ?
C17 C16 O3 C11 . . . . -178.92(13) ?
C12 C11 O3 C16 . . . . -85.66(17) ?
C10 C11 O3 C16 . . . . 98.63(16) ?
