#------------------------------------------------------------------------------
#$Date: 2016-01-06 11:27:47 +0100 (Wed 06 de Jan de 2016) $
#$Revision: 173594 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/17/4031747.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_4031747
loop_
_publ_author_name
'Gunasekar, Ramachandran'
'Thamaraiselvi, Pichandi'
'Rathore, Ravindranath S.'
'Sathiyanarayanan, Kulathu Iyer'
'Easwaramoorthi, Shanmugam'
_publ_section_title
;
 Tuning the Electronic Properties of 2-Cyano-3-phenylacrylamide
 Derivatives.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12351
_journal_page_last               12358
_journal_paper_doi               10.1021/acs.joc.5b02226
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C20 H10 Cl2 N4 O2'
_chemical_formula_weight         409.22
_chemical_melting_point          460
_chemical_name_common            2-cyano-3-(4-cholorophenyl)acrylamide
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.972(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.9514(8)
_cell_length_b                   3.8752(3)
_cell_length_c                   21.5656(16)
_cell_measurement_temperature    293(2)
_cell_volume                     913.99(12)
_computing_cell_refinement       'APEXII (Bruker, 2012)'
_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2012)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 & PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9526
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0434
_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)+(0.0632P)²+0.6530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                1700
_reflns_number_total             2146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02226_si_002.cif
_cod_data_source_block           ccn
_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/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4031747.cif.
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4031747
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.32781(19) 0.3810(6) 0.15171(10) 0.0344(5) Uani 1 1 d .
C2 C 0.3299(2) 0.5379(6) 0.09467(10) 0.0381(5) Uani 1 1 d .
H2 H 0.2580 0.5744 0.0707 0.046 Uiso 1 1 calc R
C3 C 0.4406(2) 0.6397(6) 0.07376(10) 0.0359(5) Uani 1 1 d .
H3 H 0.4430 0.7477 0.0353 0.043 Uiso 1 1 calc R
C4 C 0.54982(19) 0.5849(5) 0.10886(10) 0.0312(4) Uani 1 1 d .
C5 C 0.5440(2) 0.4267(6) 0.16653(10) 0.0367(5) Uani 1 1 d .
H5 H 0.6154 0.3887 0.1908 0.044 Uiso 1 1 calc R
C6 C 0.4332(2) 0.3257(6) 0.18807(10) 0.0377(5) Uani 1 1 d .
H6 H 0.4295 0.2213 0.2268 0.045 Uiso 1 1 calc R
C7 C 0.6612(2) 0.6992(6) 0.08134(10) 0.0337(5) Uani 1 1 d .
H7 H 0.6478 0.8125 0.0436 0.040 Uiso 1 1 calc R
C8 C 0.7791(2) 0.6729(6) 0.09978(10) 0.0343(5) Uani 1 1 d .
C9 C 0.8245(2) 0.5127(7) 0.15602(11) 0.0424(6) Uani 1 1 d .
C11 C 0.8717(2) 0.8139(6) 0.05756(11) 0.0364(5) Uani 1 1 d .
N1 N 0.8677(2) 0.3862(8) 0.19916(12) 0.0668(8) Uani 1 1 d .
N2 N 0.98849(19) 0.7671(7) 0.07451(10) 0.0525(6) Uani 1 1 d .
H2A H 1.0444 0.8448 0.0517 0.063 Uiso 1 1 calc R
H2B H 1.0084 0.6591 0.1084 0.063 Uiso 1 1 calc R
O1 O 0.83854(15) 0.9655(5) 0.00991(8) 0.0521(5) Uani 1 1 d .
Cl1 Cl 0.18844(5) 0.25209(17) 0.17852(3) 0.0473(2) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0259(10) 0.0371(11) 0.0409(12) -0.0055(9) 0.0078(9) -0.0023(9)
C2 0.0254(11) 0.0487(13) 0.0398(12) -0.0003(10) -0.0005(9) 0.0014(9)
C3 0.0306(11) 0.0429(12) 0.0343(11) 0.0040(9) 0.0030(9) 0.0015(9)
C4 0.0249(10) 0.0348(11) 0.0339(10) -0.0019(8) 0.0024(8) -0.0007(8)
C5 0.0253(11) 0.0497(13) 0.0348(11) 0.0019(9) -0.0009(8) -0.0009(9)
C6 0.0335(12) 0.0458(13) 0.0342(11) 0.0048(9) 0.0051(9) -0.0017(10)
C7 0.0306(11) 0.0377(11) 0.0331(11) 0.0023(8) 0.0039(8) -0.0028(9)
C8 0.0281(11) 0.0390(11) 0.0360(11) 0.0008(9) 0.0040(9) -0.0034(9)
C9 0.0281(11) 0.0546(14) 0.0446(13) 0.0055(11) 0.0033(10) -0.0056(10)
C11 0.0273(11) 0.0426(12) 0.0394(12) 0.0008(9) 0.0037(9) -0.0055(9)
N1 0.0433(14) 0.097(2) 0.0588(15) 0.0284(14) -0.0061(11) -0.0022(14)
N2 0.0263(10) 0.0806(17) 0.0507(13) 0.0203(11) 0.0020(9) -0.0043(10)
O1 0.0293(9) 0.0751(13) 0.0522(11) 0.0229(9) 0.0040(7) -0.0057(9)
Cl1 0.0289(3) 0.0564(4) 0.0574(4) 0.0017(3) 0.0106(3) -0.0069(2)
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.7(2)
C2 C1 Cl1 118.85(17)
C6 C1 Cl1 119.41(17)
C3 C2 C1 118.5(2)
C2 C3 C4 121.6(2)
C5 C4 C3 118.24(19)
C5 C4 C7 125.3(2)
C3 C4 C7 116.44(19)
C6 C5 C4 120.6(2)
C1 C6 C5 119.3(2)
C8 C7 C4 132.4(2)
C7 C8 C9 125.0(2)
C7 C8 C11 117.7(2)
C9 C8 C11 117.22(19)
N1 C9 C8 175.6(3)
O1 C11 N2 122.6(2)
O1 C11 C8 120.3(2)
N2 C11 C8 117.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.374(3)
C1 C6 1.378(3)
C1 Cl1 1.733(2)
C2 C3 1.372(3)
C3 C4 1.398(3)
C4 C5 1.391(3)
C4 C7 1.453(3)
C5 C6 1.379(3)
C7 C8 1.336(3)
C8 C9 1.428(3)
C8 C11 1.501(3)
C9 N1 1.133(3)
C11 O1 1.223(3)
C11 N2 1.324(3)
