#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:13:26 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233241 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/57/7235708.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_7235708
loop_
_publ_author_name
'Rai, Sunil K.'
'Khanam, Shaziya'
'Khanna, Ranjana S.'
'Tewari, Ashish K.'
_publ_section_title
;
 Cascade synthesis of 2-pyridones using acrylamides and ketones
;
_journal_issue                   83
_journal_name_full               'RSC Adv.'
_journal_page_first              44141
_journal_paper_doi               10.1039/C4RA06619G
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_chemical_melting_point          531.15
_chemical_name_systematic
; 
 6-ethyl-2-oxo-4-phenyl-1,2-dihydropyridine-3-carbonitrile 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.378(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3809(6)
_cell_length_b                   8.0626(6)
_cell_length_c                   19.9265(12)
_cell_measurement_temperature    293(2)
_cell_volume                     1173.16(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_method       'ω scans'
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5083
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0683
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0729P)²+0.4762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1581
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                1537
_reflns_number_total             2686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra06619g2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235708
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
HN1 H -0.120(4) 0.920(3) 0.0251(15) 0.064(8) Uiso 1 1 d .
C7 C 0.0004(3) 0.8743(3) 0.20932(12) 0.0422(6) Uani 1 1 d .
C11 C 0.1280(3) 0.9366(3) 0.17143(12) 0.0430(6) Uani 1 1 d .
O1 O 0.1943(2) 1.0083(3) 0.06212(8) 0.0602(6) Uani 1 1 d .
N1 N -0.0848(3) 0.8997(3) 0.07137(11) 0.0506(6) Uani 1 1 d .
C12 C 0.3026(3) 0.9996(3) 0.20138(12) 0.0479(6) Uani 1 1 d .
C8 C -0.1721(3) 0.8247(3) 0.17535(13) 0.0512(7) Uani 1 1 d .
H8 H -0.2587 0.7816 0.2002 0.061 Uiso 1 1 calc R
C10 C 0.0874(3) 0.9518(3) 0.09914(12) 0.0473(6) Uani 1 1 d .
C6 C 0.0389(3) 0.8607(3) 0.28439(12) 0.0436(6) Uani 1 1 d .
C1 C 0.2001(4) 0.7908(3) 0.31661(13) 0.0524(7) Uani 1 1 d .
H1 H 0.2876 0.7528 0.2911 0.063 Uiso 1 1 calc R
C9 C -0.2137(4) 0.8390(4) 0.10700(13) 0.0533(7) Uani 1 1 d .
C5 C -0.0922(4) 0.9148(4) 0.32320(14) 0.0596(8) Uani 1 1 d .
H5 H -0.2020 0.9600 0.3022 0.072 Uiso 1 1 calc R
N2 N 0.4415(3) 1.0518(4) 0.22456(12) 0.0692(7) Uani 1 1 d .
C2 C 0.2308(5) 0.7775(4) 0.38617(15) 0.0688(9) Uani 1 1 d .
H2 H 0.3391 0.7305 0.4077 0.083 Uiso 1 1 calc R
C4 C -0.0584(5) 0.9011(4) 0.39244(15) 0.0751(10) Uani 1 1 d .
H4 H -0.1454 0.9382 0.4183 0.090 Uiso 1 1 calc R
C3 C 0.1014(5) 0.8336(5) 0.42394(15) 0.0788(10) Uani 1 1 d .
H3 H 0.1228 0.8255 0.4710 0.095 Uiso 1 1 calc R
C13 C -0.3943(4) 0.7935(5) 0.06578(16) 0.0824(11) Uani 1 1 d .
H13A H -0.4661 0.8941 0.0573 0.099 Uiso 1 1 calc R
H13B H -0.3702 0.7525 0.0222 0.099 Uiso 1 1 calc R
C14 C -0.5064(5) 0.6706(5) 0.0945(2) 0.0929(12) Uani 1 1 d .
H14A H -0.6138 0.6473 0.0626 0.139 Uiso 1 1 calc R
H14B H -0.5421 0.7133 0.1356 0.139 Uiso 1 1 calc R
H14C H -0.4371 0.5706 0.1042 0.139 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 C7 C8 118.7(2)
C11 C7 C6 122.0(2)
C8 C7 C6 119.3(2)
C7 C11 C10 121.3(2)
C7 C11 C12 123.0(2)
C10 C11 C12 115.6(2)
C9 N1 C10 125.2(2)
C9 N1 HN1 117.3(17)
C10 N1 HN1 117.1(17)
N2 C12 C11 179.0(3)
C9 C8 C7 120.9(2)
C9 C8 H8 119.5
C7 C8 H8 119.5
O1 C10 N1 120.2(2)
O1 C10 C11 124.8(2)
N1 C10 C11 115.1(2)
C1 C6 C5 119.3(2)
C1 C6 C7 121.5(2)
C5 C6 C7 119.3(2)
C2 C1 C6 120.2(3)
C2 C1 H1 119.9
C6 C1 H1 119.9
N1 C9 C8 118.8(2)
N1 C9 C13 115.7(2)
C8 C9 C13 125.4(2)
C4 C5 C6 119.6(3)
C4 C5 H5 120.2
C6 C5 H5 120.2
C1 C2 C3 120.0(3)
C1 C2 H2 120.0
C3 C2 H2 120.0
C3 C4 C5 120.9(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C3 C2 120.1(3)
C4 C3 H3 120.0
C2 C3 H3 120.0
C14 C13 C9 117.3(3)
C14 C13 H13A 108.0
C9 C13 H13A 108.0
C14 C13 H13B 108.0
C9 C13 H13B 108.0
H13A C13 H13B 107.2
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 C11 1.384(3)
C7 C8 1.410(3)
C7 C6 1.486(3)
C11 C10 1.433(3)
C11 C12 1.433(3)
O1 C10 1.243(3)
N1 C9 1.359(3)
N1 C10 1.376(3)
N1 HN1 0.93(3)
C12 N2 1.142(3)
C8 C9 1.357(4)
C8 H8 0.9300
C6 C1 1.386(3)
C6 C5 1.394(4)
C1 C2 1.376(4)
C1 H1 0.9300
C9 C13 1.506(4)
C5 C4 1.370(4)
C5 H5 0.9300
C2 C3 1.376(5)
C2 H2 0.9300
C4 C3 1.366(5)
C4 H4 0.9300
C3 H3 0.9300
C13 C14 1.460(4)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
C8 C7 C11 C10 0.3(4)
C6 C7 C11 C10 -178.8(2)
C8 C7 C11 C12 176.1(2)
C6 C7 C11 C12 -3.0(4)
C7 C11 C12 N2 -138(17)
C10 C11 C12 N2 38(17)
C11 C7 C8 C9 -0.7(4)
C6 C7 C8 C9 178.5(2)
C9 N1 C10 O1 -178.7(3)
C9 N1 C10 C11 0.8(4)
C7 C11 C10 O1 179.1(2)
C12 C11 C10 O1 3.1(4)
C7 C11 C10 N1 -0.3(4)
C12 C11 C10 N1 -176.4(2)
C11 C7 C6 C1 -48.1(3)
C8 C7 C6 C1 132.8(3)
C11 C7 C6 C5 133.8(3)
C8 C7 C6 C5 -45.2(3)
C5 C6 C1 C2 -1.0(4)
C7 C6 C1 C2 -179.0(2)
C10 N1 C9 C8 -1.2(4)
C10 N1 C9 C13 178.6(3)
C7 C8 C9 N1 1.0(4)
C7 C8 C9 C13 -178.6(3)
C1 C6 C5 C4 1.3(4)
C7 C6 C5 C4 179.3(3)
C6 C1 C2 C3 0.0(4)
C6 C5 C4 C3 -0.6(5)
C5 C4 C3 C2 -0.3(5)
C1 C2 C3 C4 0.6(5)
N1 C9 C13 C14 155.8(3)
C8 C9 C13 C14 -24.5(5)
