#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/44/7154435.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_7154435
loop_
_publ_author_name
'Khajuria, Rajni'
'Kannaboina, Prakash'
'Kapoor, Kamal K.'
'Gupta, Annah'
'Raina, Gaurav'
'Jassal, Amanpreet Kaur'
'Rana, Love Karan'
'Hundal, Maninder S.'
'Das, Parthasarathi'
_publ_section_title
;
 Divergent synthesis of 4,6-diarylated pyridin-2(1H)-ones from chalcones:
 novel access to 2,4,6-triaryl pyridines.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5944
_journal_page_last               5954
_journal_paper_doi               10.1039/c5ob00545k
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C17 H14 N2 O3'
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_audit_update_record
;
2014-10-15 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.024(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.617(8)
_cell_length_b                   5.565(3)
_cell_length_c                   18.620(10)
_cell_measurement_reflns_used    932
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.36
_cell_measurement_theta_min      2.24
_cell_volume                     1489.3(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Sir-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1068
_diffrn_reflns_av_sigmaI/netI    0.1274
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11286
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.1994
_refine_ls_R_factor_gt           0.0891
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2575
_refine_ls_wR_factor_ref         0.3334
_reflns_number_gt                1051
_reflns_number_total             2972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00545k2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154430--7154435.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154435
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
C1 C 0.1107(4) 1.2820(10) 0.4139(4) 0.0640(16) Uani 1 1 d .
C2 C 0.0525(6) 1.145(2) 0.3625(6) 0.168(5) Uani 1 1 d .
H2 H 0.0739 1.0027 0.3494 0.202 Uiso 1 1 calc R
C3 C -0.0396(7) 1.200(3) 0.3262(6) 0.210(8) Uani 1 1 d .
H3 H -0.0773 1.0914 0.2894 0.252 Uiso 1 1 calc R
C4 C -0.0770(6) 1.383(3) 0.3384(10) 0.205(8) Uani 1 1 d .
H4 H -0.1406 1.4122 0.3139 0.246 Uiso 1 1 calc R
C5 C -0.0215(9) 1.528(3) 0.3872(16) 0.348(15) Uani 1 1 d .
H5 H -0.0444 1.6742 0.3960 0.418 Uiso 1 1 calc R
C6 C 0.0758(7) 1.4740(19) 0.4299(11) 0.257(10) Uani 1 1 d .
H6 H 0.1131 1.5778 0.4686 0.308 Uiso 1 1 calc R
C7 C 0.2365(3) 1.0431(10) 0.5174(3) 0.0621(16) Uani 1 1 d .
H7 H 0.1916 0.9979 0.5359 0.075 Uiso 1 1 calc R
C8 C 0.2138(4) 1.2407(11) 0.4572(3) 0.0713(18) Uani 1 1 d .
H8 H 0.2393 1.3894 0.4858 0.086 Uiso 1 1 calc R
C9 C 0.2651(3) 1.1945(10) 0.4077(3) 0.0618(16) Uani 1 1 d .
H9 H 0.2342 1.0567 0.3751 0.074 Uiso 1 1 calc R
C10 C 0.3655(3) 1.1219(9) 0.4490(3) 0.0520(14) Uani 1 1 d .
C11 C 0.3176(3) 0.9320(9) 0.5446(3) 0.0501(13) Uani 1 1 d .
C12 C 0.3472(3) 0.7511(9) 0.6075(3) 0.0471(13) Uani 1 1 d .
C13 C 0.4064(3) 0.5626(9) 0.6087(3) 0.0561(14) Uani 1 1 d .
H13 H 0.4297 0.5499 0.5698 0.067 Uiso 1 1 calc R
C14 C 0.4302(4) 0.3952(10) 0.6678(3) 0.0621(15) Uani 1 1 d .
H14 H 0.4692 0.2687 0.6678 0.075 Uiso 1 1 calc R
C15 C 0.3987(4) 0.4091(11) 0.7259(3) 0.0682(16) Uani 1 1 d .
H15 H 0.4153 0.2921 0.7647 0.082 Uiso 1 1 calc R
C16 C 0.3423(4) 0.5959(11) 0.7276(3) 0.0677(16) Uani 1 1 d .
H16 H 0.3213 0.6080 0.7678 0.081 Uiso 1 1 calc R
C17 C 0.3168(3) 0.7671(10) 0.6685(3) 0.0594(15) Uani 1 1 d .
H17 H 0.2788 0.8945 0.6698 0.071 Uiso 1 1 calc R
O1 O 0.4234(2) 1.1769(7) 0.4222(2) 0.0696(12) Uani 1 1 d .
O2 O 0.2792(4) 1.5941(8) 0.3796(3) 0.1002(17) Uani 1 1 d .
O3 O 0.2330(3) 1.3447(8) 0.2842(3) 0.0885(14) Uani 1 1 d .
N1 N 0.3829(3) 0.9882(8) 0.5120(2) 0.0505(12) Uani 1 1 d D
H1A H 0.4365(19) 0.928(8) 0.533(3) 0.061 Uiso 1 1 d D
N2 N 0.2579(3) 1.3947(10) 0.3522(3) 0.0616(13) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 '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
C6 C1 C2 115.2(8)
C6 C1 C8 117.6(8)
C2 C1 C8 127.3(7)
C1 C2 C3 122.8(11)
C1 C2 H2 118.6
C3 C2 H2 118.6
C4 C3 C2 125.0(14)
C4 C3 H3 117.5
C2 C3 H3 117.5
C3 C4 C5 114.5(11)
C3 C4 H4 122.8
C5 C4 H4 122.8
C4 C5 C6 122.7(13)
C4 C5 H5 118.7
C6 C5 H5 118.7
C1 C6 C5 119.7(12)
C1 C6 H6 120.2
C5 C6 H6 120.2
C11 C7 C8 122.5(4)
C11 C7 H7 118.7
C8 C7 H7 118.7
C9 C8 C1 115.1(5)
C9 C8 C7 108.2(4)
C1 C8 C7 113.5(4)
C9 C8 H8 106.5
C1 C8 H8 106.5
C7 C8 H8 106.5
C8 C9 N2 113.1(4)
C8 C9 C10 116.3(4)
N2 C9 C10 109.6(4)
C8 C9 H9 105.6
N2 C9 H9 105.6
C10 C9 H9 105.6
O1 C10 N1 124.8(4)
O1 C10 C9 120.7(4)
N1 C10 C9 114.5(4)
C7 C11 N1 118.5(5)
C7 C11 C12 125.5(4)
N1 C11 C12 116.0(4)
C13 C12 C17 118.1(5)
C13 C12 C11 121.8(4)
C17 C12 C11 120.2(4)
C14 C13 C12 119.5(5)
C14 C13 H13 120.3
C12 C13 H13 120.3
C15 C14 C13 122.1(5)
C15 C14 H14 119.0
C13 C14 H14 119.0
C14 C15 C16 119.9(5)
C14 C15 H15 120.1
C16 C15 H15 120.1
C15 C16 C17 119.4(5)
C15 C16 H16 120.3
C17 C16 H16 120.3
C16 C17 C12 121.1(5)
C16 C17 H17 119.4
C12 C17 H17 119.4
C10 N1 C11 125.0(4)
C10 N1 H1A 117(3)
C11 N1 H1A 118(3)
O3 N2 O2 125.2(5)
O3 N2 C9 117.5(5)
O2 N2 C9 117.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.286(10)
C1 C2 1.281(10)
C1 C8 1.509(8)
C2 C3 1.363(14)
C2 H2 0.9300
C3 C4 1.240(18)
C3 H3 0.9300
C4 C5 1.27(2)
C4 H4 0.9300
C5 C6 1.445(17)
C5 H5 0.9300
C6 H6 0.9300
C7 C11 1.319(6)
C7 C8 1.510(7)
C7 H7 0.9300
C8 C9 1.462(6)
C8 H8 0.9800
C9 N2 1.493(6)
C9 C10 1.506(7)
C9 H9 0.9800
C10 O1 1.231(5)
C10 N1 1.325(6)
C11 N1 1.410(6)
C11 C12 1.475(7)
C12 C13 1.393(7)
C12 C17 1.395(6)
C13 C14 1.378(7)
C13 H13 0.9300
C14 C15 1.356(7)
C14 H14 0.9300
C15 C16 1.371(8)
C15 H15 0.9300
C16 C17 1.390(7)
C16 H16 0.9300
C17 H17 0.9300
O2 N2 1.212(6)
O3 N2 1.204(5)
N1 H1A 0.84(4)
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
C6 C1 C2 C3 1.0(17)
C8 C1 C2 C3 -179.5(9)
C1 C2 C3 C4 0(2)
C2 C3 C4 C5 2(3)
C3 C4 C5 C6 -5(3)
C2 C1 C6 C5 -4(2)
C8 C1 C6 C5 176.9(14)
C4 C5 C6 C1 6(3)
C6 C1 C8 C9 -126.9(10)
C2 C1 C8 C9 53.5(10)
C6 C1 C8 C7 107.7(10)
C2 C1 C8 C7 -71.8(9)
C11 C7 C8 C9 30.7(8)
C11 C7 C8 C1 159.7(5)
C1 C8 C9 N2 59.3(7)
C7 C8 C9 N2 -172.6(5)
C1 C8 C9 C10 -172.5(5)
C7 C8 C9 C10 -44.4(7)
C8 C9 C10 O1 -148.5(5)
N2 C9 C10 O1 -18.6(7)
C8 C9 C10 N1 34.7(7)
N2 C9 C10 N1 164.6(5)
C8 C7 C11 N1 -4.7(8)
C8 C7 C11 C12 175.0(5)
C7 C11 C12 C13 147.7(5)
N1 C11 C12 C13 -32.6(7)
C7 C11 C12 C17 -33.1(8)
N1 C11 C12 C17 146.7(5)
C17 C12 C13 C14 2.2(7)
C11 C12 C13 C14 -178.5(4)
C12 C13 C14 C15 -0.8(8)
C13 C14 C15 C16 -0.9(8)
C14 C15 C16 C17 1.1(8)
C15 C16 C17 C12 0.4(8)
C13 C12 C17 C16 -2.1(7)
C11 C12 C17 C16 178.7(5)
O1 C10 N1 C11 177.6(5)
C9 C10 N1 C11 -5.8(7)
C7 C11 N1 C10 -9.2(8)
C12 C11 N1 C10 171.0(5)
C8 C9 N2 O3 -127.1(5)
C10 C9 N2 O3 101.3(6)
C8 C9 N2 O2 54.2(7)
C10 C9 N2 O2 -77.4(6)
