#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024028.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_4024028
loop_
_publ_author_name
'Ahmad Basheer'
'Hiroshi Yamataka'
'Salai Cheettu Ammal'
'Zvi Rappoport'
_publ_section_title
;
 Enols of Substituted Cyanomalonamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5297
_journal_page_last               5312
_journal_paper_doi               10.1021/jo070877h
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   18.987(4)
_cell_length_b                   24.295(5)
_cell_length_c                   9.2123(15)
_cell_measurement_reflns_used    3122
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.72
_cell_volume                     4249.6(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6739
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         2.60
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1459
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0405
_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)+(0.0521P)²+3.9798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                1394
_reflns_number_total             1459
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070877hsi20070426_015450.cif
_cod_data_source_block           bashir3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4024028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12232(8) 0.24636(7) 0.89781(17) 0.0193(4) Uani 1 1 d . . .
O2 O -0.03890(9) 0.24653(8) 0.91983(19) 0.0250(4) Uani 1 1 d . . .
N1 N 0.12835(10) 0.26799(8) 0.6568(2) 0.0171(4) Uani 1 1 d . . .
H1N1 H 0.1088(13) 0.2634(10) 0.574(3) 0.013(6) Uiso 1 1 d . . .
N2 N 0.04202(12) 0.11688(10) 0.8906(3) 0.0296(5) Uani 1 1 d . . .
N3 N -0.07015(12) 0.25896(9) 0.6860(2) 0.0220(5) Uani 1 1 d . . .
H1N3 H -0.0587(14) 0.2546(11) 0.604(4) 0.021(8) Uiso 1 1 d . . .
C1 C 0.10160(12) 0.24234(9) 0.7746(3) 0.0159(5) Uani 1 1 d . . .
C2 C 0.03583(12) 0.20726(10) 0.7389(2) 0.0168(5) Uani 1 1 d . . .
H2 H 0.0332 0.1990 0.6326 0.020 Uiso 1 1 calc R . .
C3 C -0.02937(13) 0.23993(11) 0.7895(3) 0.0189(5) Uani 1 1 d . . .
C4 C 0.03944(12) 0.15631(11) 0.8243(3) 0.0210(5) Uani 1 1 d . . .
C5 C -0.13337(14) 0.29022(13) 0.7173(3) 0.0302(6) Uani 1 1 d . . .
H51 H -0.1724 0.2649 0.7364 0.045 Uiso 1 1 calc R . .
H52 H -0.1450 0.3135 0.6338 0.045 Uiso 1 1 calc R . .
H53 H -0.1254 0.3134 0.8028 0.045 Uiso 1 1 calc R . .
C6 C 0.18684(12) 0.30394(9) 0.6525(3) 0.0157(5) Uani 1 1 d . . .
C7 C 0.22619(12) 0.31811(10) 0.7739(3) 0.0179(5) Uani 1 1 d . . .
H7 H 0.2144 0.3036 0.8666 0.022 Uiso 1 1 calc R . .
C8 C 0.28247(12) 0.35344(10) 0.7587(3) 0.0203(5) Uani 1 1 d . . .
H8 H 0.3092 0.3636 0.8416 0.024 Uiso 1 1 calc R . .
C9 C 0.30043(13) 0.37429(10) 0.6241(3) 0.0244(6) Uani 1 1 d . . .
H9 H 0.3397 0.3983 0.6149 0.029 Uiso 1 1 calc R . .
C10 C 0.26157(14) 0.36043(11) 0.5035(3) 0.0244(6) Uani 1 1 d . . .
H10 H 0.2739 0.3749 0.4112 0.029 Uiso 1 1 calc R . .
C11 C 0.20448(13) 0.32530(11) 0.5167(3) 0.0214(5) Uani 1 1 d . . .
H11 H 0.1774 0.3158 0.4337 0.026 Uiso 1 1 calc R . .
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
C1 N1 C6 127.1(2) . . ?
C1 N1 H1N1 119.5(18) . . ?
C6 N1 H1N1 113.4(17) . . ?
C3 N3 C5 121.9(2) . . ?
C3 N3 H1N3 119(2) . . ?
C5 N3 H1N3 119(2) . . ?
O1 C1 N1 126.6(2) . . ?
O1 C1 C2 120.6(2) . . ?
N1 C1 C2 112.8(2) . . ?
C4 C2 C3 107.97(19) . . ?
C4 C2 C1 108.22(19) . . ?
C3 C2 C1 107.45(19) . . ?
C4 C2 H2 111.0 . . ?
C3 C2 H2 111.0 . . ?
C1 C2 H2 111.0 . . ?
O2 C3 N3 125.4(3) . . ?
O2 C3 C2 118.9(2) . . ?
N3 C3 C2 115.8(2) . . ?
N2 C4 C2 179.8(3) . . ?
N3 C5 H51 109.5 . . ?
N3 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
N3 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
C7 C6 C11 120.1(2) . . ?
C7 C6 N1 123.6(2) . . ?
C11 C6 N1 116.3(2) . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
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 C1 1.205(3) . ?
O2 C3 1.224(3) . ?
N1 C1 1.351(3) . ?
N1 C6 1.413(3) . ?
N1 H1N1 0.85(3) . ?
N2 C4 1.137(3) . ?
N3 C3 1.312(3) . ?
N3 C5 1.449(3) . ?
N3 H1N3 0.79(3) . ?
C1 C2 1.547(3) . ?
C2 C4 1.469(3) . ?
C2 C3 1.543(3) . ?
C2 H2 1.0000 . ?
C5 H51 0.9800 . ?
C5 H52 0.9800 . ?
C5 H53 0.9800 . ?
C6 C7 1.388(3) . ?
C6 C11 1.395(3) . ?
C7 C8 1.378(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
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_site_symmetry_A
N3 H1N3 O1 0.79(3) 2.25(3) 2.837(3) 131(3) 6_554
N1 H1N1 O2 0.85(3) 1.96(3) 2.788(3) 163(3) 6_554
