#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:35:55 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257874 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/94/7059468.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_7059468
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         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.29
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-25
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_audit_update_record
;
2019-04-25 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.083(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6907(12)
_cell_length_b                   4.2138(3)
_cell_length_c                   19.6741(12)
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.2773
_cell_measurement_theta_min      3.5756
_cell_volume                     1347.79(16)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8155
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   21.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -      -17.0272  -99.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   88.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   -5.00   92.00   1.0000   28.0800
omega____ theta____ kappa____ phi______ frames
    -       19.8397   37.0000  120.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0296594000
_diffrn_orient_matrix_UB_12      -0.0012378000
_diffrn_orient_matrix_UB_13      -0.0321325000
_diffrn_orient_matrix_UB_21      0.0320120000
_diffrn_orient_matrix_UB_22      -0.0063792000
_diffrn_orient_matrix_UB_23      -0.0182922000
_diffrn_orient_matrix_UB_31      -0.0009832000
_diffrn_orient_matrix_UB_32      -0.1682706000
_diffrn_orient_matrix_UB_33      0.0009128000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5482
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.34
_diffrn_reflns_theta_min         3.64
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87493
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3467
_exptl_crystal_description       block
_exptl_crystal_F_000             576.3374
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.2338
_refine_diff_density_min         -0.2078
_refine_diff_density_rms         0.0436
_refine_ls_d_res_high            0.7252
_refine_ls_d_res_low             5.6043
_refine_ls_goodness_of_fit_ref   1.0538
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0538
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.0011
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0505P)²+0.2617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -22
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              -14
_reflns_number_gt                2553
_reflns_number_total             3011
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0nj00231c3.cif
_cod_data_source_block           HSP-AHP-II-85-AS
_cod_depositor_comments
;Adding full bibliography for 7059467--7059468.cif.

 Adding full bibliography for 7059467--7059468.cif.
;
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7059468
_chemical_oxdiff_formula         'C12 H20 N1 O2'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 298K, 0.86 0.44 0.24'
_reflns_odcompleteness_completeness 99.43
_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 Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C5(H5), C11(H11), C12(H12), N2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C15(H15a,H15b,H15c)
;
_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+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
O2 O 0.79791(5) 0.8039(2) 0.22044(4) 0.0429(2) Uani 1.000000 .
O3 O 0.88973(5) 0.5477(2) 0.17236(4) 0.0405(2) Uani 1.000000 .
N2 N 0.67348(6) 1.1410(3) 0.12496(5) 0.0364(2) Uani 1.000000 .
C10 C 0.78423(7) 1.1149(3) -0.05731(6) 0.0359(3) Uani 1.000000 .
H10 H 0.81748(7) 1.2223(3) -0.02010(6) 0.0431(3) Uiso 1.000000 R
C13 C 0.76429(8) 0.8808(3) -0.17121(6) 0.0433(3) Uani 1.000000 .
H13 H 0.78434(8) 0.8303(3) -0.21028(6) 0.0519(4) Uiso 1.000000 R
O4 O 0.88880(6) 1.1364(3) -0.12594(6) 0.0573(3) Uani 1.000000 .
O1 O 0.55108(6) 1.4176(3) 0.11237(5) 0.0562(3) Uani 1.000000 .
C3 C 0.71862(7) 1.0126(3) 0.08105(6) 0.0314(3) Uani 1.000000 .
C6 C 0.82332(7) 0.7314(3) 0.16962(6) 0.0324(3) Uani 1.000000 .
C9 C 0.70495(7) 1.0196(3) -0.05371(6) 0.0334(3) Uani 1.000000 .
C4 C 0.67401(7) 1.0973(3) 0.00899(6) 0.0336(3) Uani 1.000000 .
C14 C 0.81298(8) 1.0485(3) -0.11664(6) 0.0383(3) Uani 1.000000 .
C5 C 0.78640(7) 0.8305(3) 0.09810(6) 0.0345(3) Uani 1.000000 .
H5 H 0.81106(7) 0.7642(3) 0.06262(6) 0.0414(3) Uiso 1.000000 R
C11 C 0.65538(8) 0.8599(3) -0.10945(6) 0.0409(3) Uani 1.000000 .
H11 H 0.60212(8) 0.8011(3) -0.10786(6) 0.0491(4) Uiso 1.000000 R
C0aa C 0.60279(7) 1.2851(3) 0.08747(6) 0.0396(3) Uani 1.000000 .
C7 C 0.93085(8) 0.4340(3) 0.24163(6) 0.0399(3) Uani 1.000000 .
H7a H 0.94500(8) 0.6112(3) 0.27357(6) 0.0479(4) Uiso 1.000000 R
H7b H 0.89493(8) 0.2920(3) 0.25972(6) 0.0479(4) Uiso 1.000000 R
C8 C 1.00690(8) 0.2627(4) 0.23440(8) 0.0533(4) Uani 1.000000 .
H8a H 0.99231(10) 0.0931(17) 0.2014(4) 0.0800(6) Uiso 1.000000 GR
H8b H 1.0430(3) 0.4078(7) 0.2184(6) 0.0800(6) Uiso 1.000000 GR
H8c H 1.0343(4) 0.177(2) 0.27885(15) 0.0800(6) Uiso 1.000000 GR
C1 C 0.60482(7) 1.2474(3) 0.01312(6) 0.0407(3) Uani 1.000000 .
C12 C 0.68625(9) 0.7890(4) -0.16761(7) 0.0462(3) Uani 1.000000 .
H12 H 0.65372(9) 0.6779(4) -0.20461(7) 0.0555(4) Uiso 1.000000 R
C15 C 0.94071(9) 1.3159(4) -0.07301(9) 0.0585(4) Uani 1.000000 .
H15a H 0.9917(3) 1.358(2) -0.0861(3) 0.0878(6) Uiso 1.000000 GR
H15b H 0.9143(3) 1.5130(13) -0.0669(4) 0.0878(6) Uiso 1.000000 GR
H15c H 0.9513(6) 1.1987(13) -0.03007(18) 0.0878(6) Uiso 1.000000 GR
H2 H 0.68746(6) 1.1325(3) 0.16976(5) 0.0437(3) Uiso 1.000000 R
H1 H 0.56445(7) 1.3170(3) -0.02462(6) 0.0488(4) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C7 O3 C6 115.83(9) . . ?
C0aa N2 C3 111.07(9) . . ?
C14 C10 C9 119.71(11) . . ?
C12 C13 C14 120.00(11) . . ?
C15 O4 C14 118.49(11) . . ?
C4 C3 N2 106.03(10) . . ?
C5 C3 N2 128.00(10) . . ?
C5 C3 C4 125.86(10) . . ?
O3 C6 O2 123.56(10) . . ?
C5 C6 O2 124.90(11) . . ?
C5 C6 O3 111.54(9) . . ?
C4 C9 C10 119.44(10) . . ?
C11 C9 C10 120.01(11) . . ?
C11 C9 C4 120.53(11) . . ?
C9 C4 C3 123.23(10) . . ?
C1 C4 C3 108.00(10) . . ?
C1 C4 C9 128.77(11) . . ?
C13 C14 C10 120.08(11) . . ?
O4 C14 C10 124.31(12) . . ?
O4 C14 C13 115.61(11) . . ?
C6 C5 C3 123.36(10) . . ?
C12 C11 C9 119.25(12) . . ?
O1 C0aa N2 125.65(11) . . ?
C1 C0aa N2 105.82(10) . . ?
C1 C0aa O1 128.53(12) . . ?
C8 C7 O3 107.42(10) . . ?
C0aa C1 C4 108.95(10) . . ?
C11 C12 C13 120.91(12) . . ?
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
O2 C6 1.2103(14) . ?
O3 C6 1.3429(14) . ?
O3 C7 1.4612(14) . ?
N2 C3 1.3789(14) . ?
N2 C0aa 1.3823(16) . ?
C10 C9 1.3999(16) . ?
C10 C14 1.3873(16) . ?
C13 C14 1.3846(18) . ?
C13 C12 1.3759(19) . ?
O4 C14 1.3700(15) . ?
O4 C15 1.4137(19) . ?
O1 C0aa 1.2198(15) . ?
C3 C4 1.4879(15) . ?
C3 C5 1.3449(16) . ?
C6 C5 1.4634(16) . ?
C9 C4 1.4780(15) . ?
C9 C11 1.3890(17) . ?
C4 C1 1.3351(17) . ?
C11 C12 1.3897(18) . ?
C0aa C1 1.4793(17) . ?
C7 C8 1.4946(18) . ?
