#------------------------------------------------------------------------------
#$Date: 2023-06-29 15:15:43 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/69/7246943.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246943
loop_
_publ_author_name
'Sood, Ankur'
'Kesavan, Venkitasamy'
_publ_section_title
;
 Synthesis and antibacterial activity of 2-benzylidene-3-oxobutanamide
 derivatives against resistant pathogens
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D3MD00051F
_journal_year                    2023
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.22
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-30 deposited with the CCDC.	2023-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.039(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1110(7)
_cell_length_b                   7.3567(4)
_cell_length_c                   13.9127(8)
_cell_measurement_reflns_used    9477
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      68.08
_cell_measurement_theta_min      4.78
_cell_volume                     1126.05(11)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21157
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         4.780
_diffrn_source                   'micro focus sealed tube'
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0670P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1782
_reflns_number_total             2039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00051f2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7246943
_shelx_shelxl_version_number     2018/3
_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   0.868
_shelx_estimated_absorpt_t_max   0.967
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38404(12) 0.67015(18) 0.39589(10) 0.0493(3) Uani 1 1 d . . . . .
C2 C 0.28770(13) 0.5927(2) 0.33456(11) 0.0560(4) Uani 1 1 d . . . . .
H2 H 0.222688 0.542646 0.360856 0.067 Uiso 1 1 calc R U . . .
C3 C 0.28748(15) 0.5892(2) 0.23549(12) 0.0647(4) Uani 1 1 d . . . . .
H3 H 0.222455 0.537068 0.195612 0.078 Uiso 1 1 calc R U . . .
C4 C 0.38336(17) 0.6628(2) 0.19500(12) 0.0701(5) Uani 1 1 d . . . . .
H4 H 0.382650 0.660824 0.128083 0.084 Uiso 1 1 calc R U . . .
C5 C 0.47940(17) 0.7388(2) 0.25393(13) 0.0721(5) Uani 1 1 d . . . . .
H5 H 0.543953 0.788408 0.226870 0.086 Uiso 1 1 calc R U . . .
C6 C 0.48075(14) 0.7420(2) 0.35346(12) 0.0622(4) Uani 1 1 d . . . . .
H6 H 0.546862 0.792561 0.392775 0.075 Uiso 1 1 calc R U . . .
C7 C 0.39249(11) 0.67946(18) 0.50178(10) 0.0491(3) Uani 1 1 d . . . . .
H7 H 0.467792 0.716791 0.533282 0.059 Uiso 1 1 calc R U . . .
C8 C 0.31031(11) 0.64341(17) 0.56097(9) 0.0446(3) Uani 1 1 d . . . . .
C9 C 0.33767(12) 0.65810(19) 0.66824(10) 0.0519(3) Uani 1 1 d . . . . .
C10 C 0.45176(16) 0.7480(2) 0.71488(12) 0.0705(5) Uani 1 1 d . . . . .
H10A H 0.452563 0.751024 0.783948 0.106 Uiso 1 1 calc R U . . .
H10B H 0.455141 0.869832 0.690717 0.106 Uiso 1 1 calc R U . . .
H10C H 0.520846 0.680777 0.699916 0.106 Uiso 1 1 calc R U . . .
C11 C 0.18140(11) 0.58350(17) 0.52760(9) 0.0433(3) Uani 1 1 d . . . . .
O1 O 0.26404(10) 0.59751(17) 0.71708(8) 0.0696(3) Uani 1 1 d . . . . .
O2 O 0.15507(9) 0.42096(12) 0.51671(7) 0.0554(3) Uani 1 1 d . . . . .
O3 O 0.20586(15) 0.06633(16) 0.57798(9) 0.0828(4) Uani 1 1 d D . . . .
H3A H 0.203(2) 0.172(3) 0.5578(19) 0.124 Uiso 1 1 d D U . . .
H3B H 0.211(3) 0.075(4) 0.6397(13) 0.124 Uiso 1 1 d D U . . .
N1 N 0.10114(11) 0.71555(17) 0.51210(9) 0.0521(3) Uani 1 1 d . . . . .
H1A H 0.1216(16) 0.827(3) 0.5215(12) 0.062 Uiso 1 1 d . U . . .
H1B H 0.0243(16) 0.688(2) 0.4994(12) 0.062 Uiso 1 1 d . U . . .
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'
O O 0.0492 0.0322 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.72(14) . . ?
C2 C1 C7 124.79(12) . . ?
C6 C1 C7 117.48(13) . . ?
C3 C2 C1 120.89(13) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.42(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.70(15) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.29(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.96(15) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 131.00(12) . . ?
C8 C7 H7 114.5 . . ?
C1 C7 H7 114.5 . . ?
C7 C8 C9 122.85(12) . . ?
C7 C8 C11 124.65(12) . . ?
C9 C8 C11 112.50(11) . . ?
O1 C9 C8 118.35(12) . . ?
O1 C9 C10 120.96(14) . . ?
C8 C9 C10 120.69(13) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N1 123.44(12) . . ?
O2 C11 C8 121.26(11) . . ?
N1 C11 C8 115.29(11) . . ?
H3A O3 H3B 105(2) . . ?
C11 N1 H1A 121.5(12) . . ?
C11 N1 H1B 119.0(12) . . ?
H1A N1 H1B 119.0(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.394(2) . ?
C1 C6 1.3999(19) . ?
C1 C7 1.4647(19) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.3388(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.4848(19) . ?
C8 C11 1.5084(17) . ?
C9 O1 1.2186(17) . ?
C9 C10 1.495(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.2353(15) . ?
C11 N1 1.3159(17) . ?
O3 H3A 0.828(17) . ?
O3 H3B 0.855(17) . ?
N1 H1A 0.855(19) . ?
N1 H1B 0.871(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O2 0.828(17) 1.968(18) 2.7780(15) 166(3) . yes
O3 H3B O1 0.855(17) 1.980(17) 2.8332(17) 176(3) 2_546 yes
N1 H1A O3 0.855(19) 2.10(2) 2.9249(18) 163.3(16) 1_565 yes
N1 H1B O2 0.871(18) 2.131(18) 2.9923(16) 169.9(16) 3_566 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.8(2) . . . . ?
C7 C1 C2 C3 -179.75(13) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C7 C1 C6 C5 -179.81(14) . . . . ?
C2 C1 C7 C8 -10.1(2) . . . . ?
C6 C1 C7 C8 170.90(14) . . . . ?
C1 C7 C8 C9 178.82(13) . . . . ?
C1 C7 C8 C11 -1.0(2) . . . . ?
C7 C8 C9 O1 -169.34(13) . . . . ?
C11 C8 C9 O1 10.46(18) . . . . ?
C7 C8 C9 C10 11.7(2) . . . . ?
C11 C8 C9 C10 -168.49(12) . . . . ?
C7 C8 C11 O2 89.30(17) . . . . ?
C9 C8 C11 O2 -90.49(15) . . . . ?
C7 C8 C11 N1 -91.14(16) . . . . ?
C9 C8 C11 N1 89.06(14) . . . . ?
