#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2009013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009013
loop_
_publ_author_name
'Linden, A.'
'Moya Argilagos, D.'
'Heimgartner, H.'
'Garc\'ia Trimi\~no, M. I.'
'Mac\'ias Cabrera, A.'
_publ_section_title
;
 `Push--pull' effects in nitroethenamines
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1692
_journal_page_last               1698
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C16 H20 N4 O3 S '
_chemical_formula_sum            'C16 H20 N4 O3 S'
_chemical_formula_weight         348.42
_chemical_melting_point          447.8(3)
_chemical_name_systematic
' N-cinnamoyl-3,3-bis(dimethylamino)-2-nitrothioacrylamide'
_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'
_cell_angle_alpha                90
_cell_angle_beta                 108.930(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9391(8)
_cell_length_b                   14.4523(13)
_cell_length_c                   10.7398(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173.0(10)
_cell_measurement_theta_max      19.0
_cell_measurement_theta_min      15.5
_cell_volume                     1752.9(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure
Corporation, 1991)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173.0(10)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Rigaku AFC-5R'
_diffrn_measurement_method       '\w/2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode generator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_sigmaI/netI    0.091
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5354
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        insignificant
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         5107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.120
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.0973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.140
_reflns_number_gt                3051
_reflns_number_total             5107
_reflns_threshold_expression     'I > 2\s(I)'
_[local]_cod_data_source_file    fg1546.cif
_[local]_cod_data_source_block   2b
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_[local]_cod_chemical_formula_sum_orig 'C16 H20 N4 O3 S '
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '447.5-448' was changed to '447.8(3)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1752.9(2)
_cod_database_code               2009013
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S 0.91169(5) 0.61074(5) 0.07821(5) 0.03102(15) Uani d . 1 S
O1 0.95094(14) 0.59980(13) 0.51437(14) 0.0322(4) Uani d . 1 O
O2 1.13434(13) 0.64297(12) 0.54911(14) 0.0328(4) Uani d . 1 O
O3 0.67444(14) 0.53242(14) 0.07644(15) 0.0422(5) Uani d . 1 O
N1 0.82205(14) 0.56343(13) 0.27155(17) 0.0228(4) Uani d . 1 N
H1 0.840(2) 0.560(2) 0.355(3) 0.043(8) Uiso d . 1 H
N2 1.03352(15) 0.62288(13) 0.47047(16) 0.0229(4) Uani d . 1 N
N3 1.14537(14) 0.75012(13) 0.31705(16) 0.0215(3) Uani d . 1 N
N4 1.19165(14) 0.60043(13) 0.27263(16) 0.0224(4) Uani d . 1 N
C1 0.91323(16) 0.59872(14) 0.23329(19) 0.0199(4) Uani d . 1 C
C2 1.01678(16) 0.62646(13) 0.33722(18) 0.0188(4) Uani d . 1 C
C3 1.12158(16) 0.66079(14) 0.30580(18) 0.0188(4) Uani d . 1 C
C4 0.71102(17) 0.53102(15) 0.1957(2) 0.0228(4) Uani d . 1 C
C5 0.64440(17) 0.49040(15) 0.2772(2) 0.0233(4) Uani d . 1 C
H5 0.6759 0.4934 0.3704 0.028 Uiso calc R 1 H
C6 0.54028(17) 0.44961(15) 0.2195(2) 0.0229(4) Uani d . 1 C
H6 0.5081 0.4565 0.1267 0.028 Uiso calc R 1 H
C7 0.46934(17) 0.39539(14) 0.2822(2) 0.0219(4) Uani d . 1 C
C8 0.37090(18) 0.34795(15) 0.2005(2) 0.0256(4) Uani d . 1 C
H8 0.3502 0.3540 0.1076 0.031 Uiso calc R 1 H
C9 0.30287(19) 0.29208(16) 0.2531(2) 0.0308(5) Uani d . 1 C
H9 0.2371 0.2593 0.1963 0.037 Uiso calc R 1 H
C10 0.3307(2) 0.28411(18) 0.3877(3) 0.0361(6) Uani d . 1 C
H10 0.2839 0.2462 0.4237 0.043 Uiso calc R 1 H
C11 0.4276(2) 0.3316(2) 0.4707(2) 0.0387(6) Uani d . 1 C
H11 0.4463 0.3265 0.5634 0.046 Uiso calc R 1 H
C12 0.49703(19) 0.38652(17) 0.4189(2) 0.0304(5) Uani d . 1 C
H12 0.5636 0.4182 0.4763 0.037 Uiso calc R 1 H
C13 1.05432(19) 0.81778(16) 0.3213(2) 0.0284(5) Uani d . 1 C
H131 0.9766 0.7968 0.2640 0.043 Uiso calc R 1 H
H132 1.0726 0.8781 0.2908 0.043 Uiso calc R 1 H
H133 1.0532 0.8234 0.4118 0.043 Uiso calc R 1 H
C14 1.26580(18) 0.78734(16) 0.3470(2) 0.0294(5) Uani d . 1 C
H141 1.3236 0.7385 0.3857 0.044 Uiso calc R 1 H
H142 1.2770 0.8387 0.4095 0.044 Uiso calc R 1 H
H143 1.2771 0.8096 0.2657 0.044 Uiso calc R 1 H
C15 1.2572(2) 0.62330(18) 0.1824(2) 0.0316(5) Uani d . 1 C
H151 1.2331 0.6846 0.1441 0.047 Uiso calc R 1 H
H152 1.2400 0.5771 0.1119 0.047 Uiso calc R 1 H
H153 1.3423 0.6235 0.2308 0.047 Uiso calc R 1 H
C16 1.1807(2) 0.50097(16) 0.2917(2) 0.0304(5) Uani d . 1 C
H161 1.1393 0.4909 0.3559 0.046 Uiso calc R 1 H
H162 1.2597 0.4732 0.3244 0.046 Uiso calc R 1 H
H163 1.1356 0.4723 0.2077 0.046 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0222(2) 0.0528(4) 0.0181(2) -0.0039(3) 0.00649(19) 0.0023(2)
O1 0.0310(8) 0.0470(10) 0.0234(7) -0.0149(7) 0.0157(6) -0.0052(7)
O2 0.0261(8) 0.0477(10) 0.0195(7) -0.0107(7) 0.0004(6) 0.0009(7)
O3 0.0285(8) 0.0674(13) 0.0252(8) -0.0202(9) 0.0011(7) 0.0061(8)
N1 0.0185(8) 0.0309(10) 0.0197(8) -0.0034(7) 0.0072(7) 0.0014(7)
N2 0.0211(8) 0.0284(10) 0.0194(8) -0.0042(7) 0.0067(7) 0.0000(7)
N3 0.0199(8) 0.0221(8) 0.0235(8) -0.0018(7) 0.0083(7) 0.0020(7)
N4 0.0188(8) 0.0270(9) 0.0231(8) 0.0008(7) 0.0092(6) 0.0027(7)
C1 0.0167(8) 0.0221(10) 0.0212(9) 0.0002(8) 0.0063(7) 0.0012(8)
C2 0.0171(8) 0.0215(10) 0.0188(8) -0.0018(7) 0.0072(7) 0.0003(8)
C3 0.0153(8) 0.0240(10) 0.0159(8) -0.0013(7) 0.0034(7) 0.0035(8)
C4 0.0175(9) 0.0253(11) 0.0244(9) -0.0012(8) 0.0054(8) 0.0015(8)
C5 0.0199(9) 0.0277(11) 0.0238(9) 0.0006(8) 0.0089(8) 0.0026(8)
C6 0.0207(9) 0.0248(11) 0.0230(9) -0.0004(8) 0.0067(8) 0.0022(8)
C7 0.0178(8) 0.0210(10) 0.0270(10) 0.0012(8) 0.0071(7) 0.0028(8)
C8 0.0241(10) 0.0252(11) 0.0276(10) -0.0012(9) 0.0085(8) -0.0018(9)
C9 0.0247(10) 0.0241(11) 0.0407(13) -0.0069(9) 0.0068(9) 0.0002(10)
C10 0.0270(11) 0.0366(14) 0.0442(14) -0.0057(10) 0.0107(10) 0.0162(11)
C11 0.0307(12) 0.0530(17) 0.0300(11) -0.0044(11) 0.0064(10) 0.0156(12)
C12 0.0219(10) 0.0378(13) 0.0283(11) -0.0045(9) 0.0035(8) 0.0060(10)
C13 0.0320(11) 0.0255(11) 0.0296(11) 0.0034(9) 0.0126(9) 0.0031(9)
C14 0.0236(10) 0.0305(12) 0.0334(12) -0.0078(9) 0.0082(9) 0.0014(10)
C15 0.0283(11) 0.0408(14) 0.0327(11) 0.0010(10) 0.0196(9) 0.0023(10)
C16 0.0284(11) 0.0263(11) 0.0392(12) 0.0038(9) 0.0147(10) 0.0021(10)
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 for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
S S 0.1246 0.1234
; International Tables for Crystallography (1992).
Vol.C, Tables 4.2.6.8 and 6.1.1.4
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 4 1
1 4 0
-1 4 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C4 130.02(18) yes
C1 N1 H1 112.2(18) ?
C4 N1 H1 117.8(18) ?
O2 N2 O1 120.04(16) ?
O2 N2 C2 118.16(16) ?
O1 N2 C2 121.80(16) ?
C3 N3 C14 123.00(17) ?
C3 N3 C13 120.87(17) ?
C14 N3 C13 115.43(18) ?
C3 N4 C16 120.80(17) ?
C3 N4 C15 122.95(18) ?
C16 N4 C15 113.88(18) ?
N1 C1 C2 115.95(17) yes
N1 C1 S 125.54(15) yes
C2 C1 S 118.50(14) ?
N2 C2 C1 126.67(17) yes
N2 C2 C3 113.54(16) ?
C1 C2 C3 119.77(16) ?
N3 C3 N4 121.95(17) yes
N3 C3 C2 118.63(17) ?
N4 C3 C2 119.36(18) ?
O3 C4 N1 124.14(19) yes
O3 C4 C5 123.53(19) ?
N1 C4 C5 112.27(17) ?
C6 C5 C4 119.96(19) ?
C6 C5 H5 120.0 ?
C4 C5 H5 120.0 ?
C5 C6 C7 127.83(19) yes
C5 C6 H6 116.1 ?
C7 C6 H6 116.1 ?
C8 C7 C12 118.50(19) ?
C8 C7 C6 117.85(18) ?
C12 C7 C6 123.62(18) yes
C9 C8 C7 120.9(2) ?
C9 C8 H8 119.6 ?
C7 C8 H8 119.6 ?
C10 C9 C8 120.1(2) ?
C10 C9 H9 120.0 ?
C8 C9 H9 120.0 ?
C9 C10 C11 119.9(2) ?
C9 C10 H10 120.1 ?
C11 C10 H10 120.1 ?
C12 C11 C10 120.4(2) ?
C12 C11 H11 119.8 ?
C10 C11 H11 119.8 ?
C11 C12 C7 120.2(2) ?
C11 C12 H12 119.9 ?
C7 C12 H12 119.9 ?
N3 C13 H131 109.5 ?
N3 C13 H132 109.5 ?
H131 C13 H132 109.5 ?
N3 C13 H133 109.5 ?
H131 C13 H133 109.5 ?
H132 C13 H133 109.5 ?
N3 C14 H141 109.5 ?
N3 C14 H142 109.5 ?
H141 C14 H142 109.5 ?
N3 C14 H143 109.5 ?
H141 C14 H143 109.5 ?
H142 C14 H143 109.5 ?
N4 C15 H151 109.5 ?
N4 C15 H152 109.5 ?
H151 C15 H152 109.5 ?
N4 C15 H153 109.5 ?
H151 C15 H153 109.5 ?
H152 C15 H153 109.5 ?
N4 C16 H161 109.5 ?
N4 C16 H162 109.5 ?
H161 C16 H162 109.5 ?
N4 C16 H163 109.5 ?
H161 C16 H163 109.5 ?
H162 C16 H163 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 1.669(2) yes
O1 N2 1.268(2) ?
O2 N2 1.260(2) ?
O3 C4 1.211(2) ?
N1 C1 1.380(2) yes
N1 C4 1.393(3) yes
N1 H1 0.85(3) ?
N2 C2 1.380(2) yes
N3 C3 1.319(3) yes
N3 C14 1.470(3) ?
N3 C13 1.474(3) ?
N4 C3 1.335(3) yes
N4 C16 1.464(3) ?
N4 C15 1.468(2) ?
C1 C2 1.428(3) yes
C2 C3 1.483(2) yes
C4 C5 1.482(3) yes
C5 C6 1.333(3) yes
C5 H5 0.9500 ?
C6 C7 1.467(3) ?
C6 H6 0.9500 ?
C7 C8 1.397(3) ?
C7 C12 1.403(3) ?
C8 C9 1.389(3) ?
C8 H8 0.9500 ?
C9 C10 1.379(3) ?
C9 H9 0.9500 ?
C10 C11 1.391(3) ?
C10 H10 0.9500 ?
C11 C12 1.388(3) ?
C11 H11 0.9500 ?
C12 H12 0.9500 ?
C13 H131 0.9800 ?
C13 H132 0.9800 ?
C13 H133 0.9800 ?
C14 H141 0.9800 ?
C14 H142 0.9800 ?
C14 H143 0.9800 ?
C15 H151 0.9800 ?
C15 H152 0.9800 ?
C15 H153 0.9800 ?
C16 H161 0.9800 ?
C16 H162 0.9800 ?
C16 H163 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 0.85(3) 1.88(3) 2.616(2) 144(3) yes
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_publ_flag
C4 N1 C1 C2 179.8(2) yes
C4 N1 C1 S -0.5(3) ?
O2 N2 C2 C1 174.14(19) ?
O1 N2 C2 C1 -5.6(3) ?
O2 N2 C2 C3 -4.1(3) yes
O1 N2 C2 C3 176.24(18) ?
N1 C1 C2 N2 -1.2(3) ?
S C1 C2 N2 179.06(17) yes
N1 C1 C2 C3 176.93(18) yes
S C1 C2 C3 -2.8(3) ?
C14 N3 C3 N4 -25.2(3) ?
C13 N3 C3 N4 164.81(18) ?
C14 N3 C3 C2 151.91(18) ?
C13 N3 C3 C2 -18.1(3) yes
C16 N4 C3 N3 164.92(19) ?
C15 N4 C3 N3 -33.6(3) ?
C16 N4 C3 C2 -12.1(3) yes
C15 N4 C3 C2 149.33(19) ?
N2 C2 C3 N3 -75.3(2) yes
C1 C2 C3 N3 106.4(2) yes
N2 C2 C3 N4 101.9(2) yes
C1 C2 C3 N4 -76.5(2) yes
C1 N1 C4 O3 -3.0(4) ?
C1 N1 C4 C5 174.3(2) yes
O3 C4 C5 C6 2.6(3) ?
N1 C4 C5 C6 -174.8(2) yes
C4 C5 C6 C7 171.3(2) yes
C5 C6 C7 C8 -171.1(2) yes
C5 C6 C7 C12 7.0(4) ?
C12 C7 C8 C9 -1.0(3) ?
C6 C7 C8 C9 177.2(2) ?
C7 C8 C9 C10 1.2(3) ?
C8 C9 C10 C11 -0.4(4) ?
C9 C10 C11 C12 -0.5(4) ?
C10 C11 C12 C7 0.7(4) ?
C8 C7 C12 C11 0.0(3) ?
C6 C7 C12 C11 -178.0(2) ?