#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/90/2009013.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, Anthony'
'Moya Argilagos, Dally'
'Heimgartner, Heinz'
'García Trimiño, María I.'
'Macías Cabrera, Arturo'
_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_paper_doi               10.1107/S0108270199006861
_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       'ω/2θ 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      ?
_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/[σ²(Fo²)+(0.0547P)²+0.0973P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            fg1546.cif
_cod_data_source_block           2b
_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 1646 2011-03-28 12:23:43Z adriana 

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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1752.9(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C16 H20 N4 O3 S '
_cod_database_code               2009013
_cod_database_fobs_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S .91169(5) .61074(5) .07821(5) .03102(15) Uani d . 1 . . S
O1 .95094(14) .59980(13) .51437(14) .0322(4) Uani d . 1 . . O
O2 1.13434(13) .64297(12) .54911(14) .0328(4) Uani d . 1 . . O
O3 .67444(14) .53242(14) .07644(15) .0422(5) Uani d . 1 . . O
N1 .82205(14) .56343(13) .27155(17) .0228(4) Uani d . 1 . . N
H1 .840(2) .560(2) .355(3) .043(8) Uiso d . 1 . . H
N2 1.03352(15) .62288(13) .47047(16) .0229(4) Uani d . 1 . . N
N3 1.14537(14) .75012(13) .31705(16) .0215(3) Uani d . 1 . . N
N4 1.19165(14) .60043(13) .27263(16) .0224(4) Uani d . 1 . . N
C1 .91323(16) .59872(14) .23329(19) .0199(4) Uani d . 1 . . C
C2 1.01678(16) .62646(13) .33722(18) .0188(4) Uani d . 1 . . C
C3 1.12158(16) .66079(14) .30580(18) .0188(4) Uani d . 1 . . C
C4 .71102(17) .53102(15) .1957(2) .0228(4) Uani d . 1 . . C
C5 .64440(17) .49040(15) .2772(2) .0233(4) Uani d . 1 . . C
H5 .6759 .4934 .3704 .028 Uiso calc R 1 . . H
C6 .54028(17) .44961(15) .2195(2) .0229(4) Uani d . 1 . . C
H6 .5081 .4565 .1267 .028 Uiso calc R 1 . . H
C7 .46934(17) .39539(14) .2822(2) .0219(4) Uani d . 1 . . C
C8 .37090(18) .34795(15) .2005(2) .0256(4) Uani d . 1 . . C
H8 .3502 .3540 .1076 .031 Uiso calc R 1 . . H
C9 .30287(19) .29208(16) .2531(2) .0308(5) Uani d . 1 . . C
H9 .2371 .2593 .1963 .037 Uiso calc R 1 . . H
C10 .3307(2) .28411(18) .3877(3) .0361(6) Uani d . 1 . . C
H10 .2839 .2462 .4237 .043 Uiso calc R 1 . . H
C11 .4276(2) .3316(2) .4707(2) .0387(6) Uani d . 1 . . C
H11 .4463 .3265 .5634 .046 Uiso calc R 1 . . H
C12 .49703(19) .38652(17) .4189(2) .0304(5) Uani d . 1 . . C
H12 .5636 .4182 .4763 .037 Uiso calc R 1 . . H
C13 1.05432(19) .81778(16) .3213(2) .0284(5) Uani d . 1 . . C
H131 .9766 .7968 .2640 .043 Uiso calc R 1 . . H
H132 1.0726 .8781 .2908 .043 Uiso calc R 1 . . H
H133 1.0532 .8234 .4118 .043 Uiso calc R 1 . . H
C14 1.26580(18) .78734(16) .3470(2) .0294(5) Uani d . 1 . . C
H141 1.3236 .7385 .3857 .044 Uiso calc R 1 . . H
H142 1.2770 .8387 .4095 .044 Uiso calc R 1 . . H
H143 1.2771 .8096 .2657 .044 Uiso calc R 1 . . H
C15 1.2572(2) .62330(18) .1824(2) .0316(5) Uani d . 1 . . C
H151 1.2331 .6846 .1441 .047 Uiso calc R 1 . . H
H152 1.2400 .5771 .1119 .047 Uiso calc R 1 . . H
H153 1.3423 .6235 .2308 .047 Uiso calc R 1 . . H
C16 1.1807(2) .50097(16) .2917(2) .0304(5) Uani d . 1 . . C
H161 1.1393 .4909 .3559 .046 Uiso calc R 1 . . H
H162 1.2597 .4732 .3244 .046 Uiso calc R 1 . . H
H163 1.1356 .4723 .2077 .046 Uiso calc R 1 . . H
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_site_symmetry_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 . .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 . .9500 ?
C6 C7 . 1.467(3) ?
C6 H6 . .9500 ?
C7 C8 . 1.397(3) ?
C7 C12 . 1.403(3) ?
C8 C9 . 1.389(3) ?
C8 H8 . .9500 ?
C9 C10 . 1.379(3) ?
C9 H9 . .9500 ?
C10 C11 . 1.391(3) ?
C10 H10 . .9500 ?
C11 C12 . 1.388(3) ?
C11 H11 . .9500 ?
C12 H12 . .9500 ?
C13 H131 . .9800 ?
C13 H132 . .9800 ?
C13 H133 . .9800 ?
C14 H141 . .9800 ?
C14 H142 . .9800 ?
C14 H143 . .9800 ?
C15 H151 . .9800 ?
C15 H152 . .9800 ?
C15 H153 . .9800 ?
C16 H161 . .9800 ?
C16 H162 . .9800 ?
C16 H163 . .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) ?
