#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:35:55 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257874 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059467.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_7059467
loop_
_publ_author_name
'Surya Prakash Rao, H.'
'Padder, Ashiq Hussain'
_publ_section_title
;
 Blaise reaction: synthesis, skeletal diversification of C(4) substituted
 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester
 on the reactivity of the nitriles
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9010
_journal_page_last               9017
_journal_paper_doi               10.1039/D0NJ00231C
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-03-27
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2019-03-26 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.173(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.920(3)
_cell_length_b                   5.4308(6)
_cell_length_c                   18.988(2)
_cell_measurement_reflns_used    1406
_cell_measurement_temperature    295
_cell_measurement_theta_max      29.1191
_cell_measurement_theta_min      3.8301
_cell_volume                     2602.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   48.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   57.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   25.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397  -99.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   56.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3397   19.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00  -20.00   1.0000   65.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0585  -21.0000   10.0000 34
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0006552000
_diffrn_orient_matrix_UB_12      -0.0079075000
_diffrn_orient_matrix_UB_13      -0.0370103000
_diffrn_orient_matrix_UB_21      -0.0264265000
_diffrn_orient_matrix_UB_22      -0.0450249000
_diffrn_orient_matrix_UB_23      -0.0081901000
_diffrn_orient_matrix_UB_31      -0.0096816000
_diffrn_orient_matrix_UB_32      0.1224220000
_diffrn_orient_matrix_UB_33      -0.0053443000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6451
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.18
_diffrn_reflns_theta_min         3.84
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0615
_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)+(0.0819P)²+0.9382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1904
_reflns_number_gt                1786
_reflns_number_total             3012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj00231c3.cif
_cod_data_source_block           hsp-ahp-i-272-s
_cod_depositor_comments
;Adding full bibliography for 7059467--7059468.cif.

 Adding full bibliography for 7059467--7059468.cif.
;
_cod_original_cell_volume        2602.5(6)
_cod_database_code               7059467
_chemical_oxdiff_formula         'C19 H15 O3 N'
_chemical_oxdiff_usercomment     ' COLOURLESS PLATE, 295K, 0.42 0.40 0.05'
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.20264(6) 0.8586(3) 0.19855(8) 0.0661(5) Uani 1 d . . .
N2 N 0.22654(6) 1.1426(3) 0.32632(9) 0.0559(5) Uani 1 d . . .
H2 H 0.2404 1.0183 0.3095 0.067 Uiso 1 calc . . R
C3 C 0.18053(8) 1.2529(4) 0.29034(11) 0.0514(5) Uani 1 d . . .
C4 C 0.16254(8) 0.9822(4) 0.18413(11) 0.0563(5) Uani 1 d . . .
C5 C 0.16975(8) 1.4728(4) 0.33401(11) 0.0538(5) Uani 1 d . . .
H5 H 0.1767 1.6220 0.3087 0.065 Uiso 1 calc . . R
O6 O 0.12374(6) 0.9435(4) 0.12573(9) 0.0824(6) Uani 1 d . . .
C7 C 0.15011(8) 1.1833(4) 0.22657(11) 0.0579(6) Uani 1 d . . .
H7 H 0.1190 1.2707 0.2087 0.070 Uiso 1 calc . . R
C9 C 0.11349(8) 1.4865(4) 0.34291(11) 0.0536(5) Uani 1 d . . .
C10 C 0.21287(9) 1.4528(5) 0.40412(12) 0.0636(6) Uani 1 d . . .
H10A H 0.2324 1.6061 0.4140 0.076 Uiso 1 calc . . R
H10B H 0.1973 1.4151 0.4447 0.076 Uiso 1 calc . . R
C11 C 0.24852(9) 1.2497(5) 0.39201(12) 0.0621(6) Uani 1 d . . .
C12 C 0.00988(10) 1.5117(5) 0.35978(15) 0.0800(8) Uani 1 d . . .
H12 H -0.0245 1.5217 0.3666 0.096 Uiso 1 calc . . R
C13 C 0.07994(10) 1.6708(4) 0.31172(14) 0.0729(7) Uani 1 d . . .
H13 H 0.0921 1.7905 0.2844 0.088 Uiso 1 calc . . R
C14 C 0.09363(10) 1.3121(5) 0.38139(17) 0.0863(9) Uani 1 d . . .
H14 H 0.1152 1.1824 0.4023 0.104 Uiso 1 calc . . R
C15 C 0.02814(10) 1.6823(5) 0.32012(16) 0.0842(8) Uani 1 d . . .
H15 H 0.0060 1.8086 0.2982 0.101 Uiso 1 calc . . R
C16 C 0.04239(11) 1.3250(6) 0.38971(19) 0.0967(10) Uani 1 d . . .
H16 H 0.0298 1.2041 0.4162 0.116 Uiso 1 calc . . R
C17 C 0.13196(11) 0.7535(7) 0.07599(18) 0.1057(11) Uani 1 d . . .
H17A H 0.1480 0.8251 0.0393 0.127 Uiso 1 calc . . R
H17B H 0.1561 0.6303 0.1020 0.127 Uiso 1 calc . . R
C1 C 0.08445(15) 0.6425(9) 0.0431(3) 0.164(2) Uani 1 d . . .
H1A H 0.0910 0.5136 0.0116 0.247 Uiso 1 calc . . GR
H1B H 0.0612 0.7628 0.0154 0.247 Uiso 1 calc . . GR
H1C H 0.0682 0.5742 0.0794 0.247 Uiso 1 calc . . GR
O2 O 0.28927(7) 1.1841(4) 0.43162(9) 0.0917(7) Uani 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 0.0033 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'
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
C3 N2 H2 123.2 . . ?
C3 N2 C11 113.64(19) . . ?
C11 N2 H2 123.2 . . ?
N2 C3 C5 108.65(17) . . ?
C7 C3 N2 126.4(2) . . ?
C7 C3 C5 124.9(2) . . ?
O1 C4 O6 123.0(2) . . ?
O1 C4 C7 125.7(2) . . ?
O6 C4 C7 111.30(19) . . ?
C3 C5 H5 107.8 . . ?
C3 C5 C10 103.31(17) . . ?
C9 C5 C3 113.82(17) . . ?
C9 C5 H5 107.8 . . ?
C9 C5 C10 115.98(17) . . ?
C10 C5 H5 107.8 . . ?
C4 O6 C17 117.4(2) . . ?
C3 C7 C4 124.1(2) . . ?
C3 C7 H7 118.0 . . ?
C4 C7 H7 118.0 . . ?
C13 C9 C5 121.53(19) . . ?
C14 C9 C5 121.2(2) . . ?
C14 C9 C13 117.3(2) . . ?
C5 C10 H10A 110.6 . . ?
C5 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 C5 105.85(18) . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
N2 C11 C10 108.01(19) . . ?
O2 C11 N2 124.4(2) . . ?
O2 C11 C10 127.6(2) . . ?
C15 C12 H12 120.5 . . ?
C15 C12 C16 119.0(2) . . ?
C16 C12 H12 120.5 . . ?
C9 C13 H13 119.4 . . ?
C9 C13 C15 121.2(2) . . ?
C15 C13 H13 119.4 . . ?
C9 C14 H14 119.4 . . ?
C9 C14 C16 121.2(2) . . ?
C16 C14 H14 119.4 . . ?
C12 C15 C13 120.4(2) . . ?
C12 C15 H15 119.8 . . ?
C13 C15 H15 119.8 . . ?
C12 C16 C14 120.9(3) . . ?
C12 C16 H16 119.5 . . ?
C14 C16 H16 119.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
C1 C17 O6 110.9(2) . . ?
C1 C17 H17A 109.5 . . ?
C1 C17 H17B 109.5 . . ?
C17 C1 H1A 109.5 . . ?
C17 C1 H1B 109.5 . . ?
C17 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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
O1 C4 1.215(2) . ?
N2 H2 0.8600 . ?
N2 C3 1.370(3) . ?
N2 C11 1.376(3) . ?
C3 C5 1.516(3) . ?
C3 C7 1.340(3) . ?
C4 O6 1.333(2) . ?
C4 C7 1.437(3) . ?
C5 H5 0.9800 . ?
C5 C9 1.508(3) . ?
C5 C10 1.535(3) . ?
O6 C17 1.447(3) . ?
C7 H7 0.9300 . ?
C9 C13 1.369(3) . ?
C9 C14 1.367(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.490(3) . ?
C11 O2 1.202(3) . ?
C12 H12 0.9300 . ?
C12 C15 1.346(4) . ?
C12 C16 1.358(4) . ?
C13 H13 0.9300 . ?
C13 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C14 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C1 1.386(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 O6 C17 -3.5(4) . . . . ?
O1 C4 C7 C3 -3.6(4) . . . . ?
N2 C3 C5 C9 -133.00(18) . . . . ?
N2 C3 C5 C10 -6.4(2) . . . . ?
N2 C3 C7 C4 -2.2(3) . . . . ?
C3 N2 C11 C10 1.9(3) . . . . ?
C3 N2 C11 O2 -178.7(2) . . . . ?
C3 C5 C9 C13 -113.1(2) . . . . ?
C3 C5 C9 C14 65.6(3) . . . . ?
C3 C5 C10 C11 7.2(2) . . . . ?
C4 O6 C17 C1 148.1(4) . . . . ?
C5 C3 C7 C4 176.47(19) . . . . ?
C5 C9 C13 C15 180.0(2) . . . . ?
C5 C9 C14 C16 179.8(3) . . . . ?
C5 C10 C11 N2 -5.9(2) . . . . ?
C5 C10 C11 O2 174.8(3) . . . . ?
O6 C4 C7 C3 175.8(2) . . . . ?
C7 C3 C5 C9 48.1(3) . . . . ?
C7 C3 C5 C10 174.7(2) . . . . ?
C7 C4 O6 C17 177.1(2) . . . . ?
C9 C5 C10 C11 132.5(2) . . . . ?
C9 C13 C15 C12 0.4(4) . . . . ?
C9 C14 C16 C12 0.1(5) . . . . ?
C10 C5 C9 C13 127.2(2) . . . . ?
C10 C5 C9 C14 -54.1(3) . . . . ?
C11 N2 C3 C5 3.0(2) . . . . ?
C11 N2 C3 C7 -178.1(2) . . . . ?
C13 C9 C14 C16 -1.4(4) . . . . ?
C14 C9 C13 C15 1.2(4) . . . . ?
C15 C12 C16 C14 1.6(5) . . . . ?
C16 C12 C15 C13 -1.8(5) . . . . ?
