#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024031.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_4024031
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         'C12 H13 N3 O3'
_chemical_formula_sum            'C12 H13 N3 O3'
_chemical_formula_weight         247.25
_chemical_name_systematic
; 
 ? 
;
_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'
_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                 102.068(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.235(5)
_cell_length_b                   5.3898(16)
_cell_length_c                   12.383(4)
_cell_measurement_reflns_used    2421
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.28
_cell_volume                     1190.1(6)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10680
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.1012
_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)+(0.0499P)²+2.3034P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1942
_refine_ls_wR_factor_ref         0.1977
_reflns_number_gt                1932
_reflns_number_total             2105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070877hsi20070426_015603.cif
_cod_data_source_block           bashirm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024031
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_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
C1 C 0.2939(2) 0.4213(8) 0.8558(3) 0.0314(9) Uani 1 1 d . . .
C2 C 0.3537(2) 0.2533(8) 0.8668(3) 0.0318(9) Uani 1 1 d . . .
C3 C 0.3597(2) 0.0956(7) 0.7752(3) 0.0306(9) Uani 1 1 d . . .
C4 C 0.4071(2) 0.2318(8) 0.9672(3) 0.0332(9) Uani 1 1 d . . .
C5 C 0.4183(3) -0.2478(8) 0.6986(3) 0.0440(11) Uani 1 1 d . . .
H5A H 0.3706 -0.3196 0.6661 0.066 Uiso 1 1 calc R . .
H5B H 0.4530 -0.3772 0.7279 0.066 Uiso 1 1 calc R . .
H5C H 0.4371 -0.1571 0.6434 0.066 Uiso 1 1 calc R . .
C6 C 0.2207(2) 0.7251(8) 0.9371(3) 0.0331(9) Uani 1 1 d . . .
C7 C 0.1893(3) 0.7470(10) 1.0293(3) 0.0484(12) Uani 1 1 d . . .
H7 H 0.2053 0.6432 1.0897 0.058 Uiso 1 1 calc R . .
C8 C 0.1350(3) 0.9193(10) 1.0324(4) 0.0511(13) Uani 1 1 d . . .
H8 H 0.1147 0.9316 1.0950 0.061 Uiso 1 1 calc R . .
C9 C 0.1100(2) 1.0749(8) 0.9448(4) 0.0413(10) Uani 1 1 d . . .
C10 C 0.1408(2) 1.0518(8) 0.8526(3) 0.0415(11) Uani 1 1 d . . .
H10 H 0.1241 1.1533 0.7917 0.050 Uiso 1 1 calc R . .
C11 C 0.1959(2) 0.8801(8) 0.8501(3) 0.0385(10) Uani 1 1 d . . .
H11 H 0.2167 0.8692 0.7879 0.046 Uiso 1 1 calc R . .
C12 C 0.0292(3) 1.4043(10) 0.8682(4) 0.0633(15) Uani 1 1 d . . .
H12A H 0.0702 1.4996 0.8525 0.095 Uiso 1 1 calc R . .
H12B H -0.0073 1.5141 0.8881 0.095 Uiso 1 1 calc R . .
H12C H 0.0065 1.3106 0.8040 0.095 Uiso 1 1 calc R . .
N1 N 0.2787(2) 0.5488(7) 0.9401(3) 0.0373(9) Uani 1 1 d . . .
H1N1 H 0.302(2) 0.500(8) 1.000(4) 0.041(13) Uiso 1 1 d . . .
N2 N 0.4518(2) 0.2139(8) 1.0452(3) 0.0523(11) Uani 1 1 d . . .
N3 N 0.4096(2) -0.0821(7) 0.7864(3) 0.0367(8) Uani 1 1 d . . .
H1N3 H 0.440(2) -0.104(8) 0.844(4) 0.041(13) Uiso 1 1 d . . .
O1 O 0.25044(15) 0.4546(6) 0.7593(2) 0.0388(8) Uani 1 1 d . . .
H1O1 H 0.273(2) 0.304(9) 0.706(4) 0.048(12) Uiso 1 1 d . . .
O2 O 0.31475(15) 0.1269(5) 0.6822(2) 0.0370(7) Uani 1 1 d . . .
O3 O 0.05614(19) 1.2401(7) 0.9569(3) 0.0617(10) Uani 1 1 d . . .
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
O1 C1 N1 117.6(4) . . ?
O1 C1 C2 119.4(3) . . ?
N1 C1 C2 123.0(3) . . ?
C1 C2 C4 121.1(3) . . ?
C1 C2 C3 119.4(3) . . ?
C4 C2 C3 119.5(4) . . ?
O2 C3 N3 119.6(4) . . ?
O2 C3 C2 119.5(4) . . ?
N3 C3 C2 120.9(3) . . ?
N2 C4 C2 177.5(4) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 118.2(4) . . ?
C11 C6 N1 123.7(4) . . ?
C7 C6 N1 118.1(4) . . ?
C8 C7 C6 120.6(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
O3 C9 C8 116.3(4) . . ?
O3 C9 C10 125.5(4) . . ?
C8 C9 C10 118.2(4) . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C6 C11 C10 121.4(4) . . ?
C6 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C6 127.3(3) . . ?
C1 N1 H1N1 113(3) . . ?
C6 N1 H1N1 119(3) . . ?
C3 N3 C5 123.9(4) . . ?
C3 N3 H1N3 122(3) . . ?
C5 N3 H1N3 114(3) . . ?
C1 O1 H1O1 102(2) . . ?
C3 O2 H1O1 100.9(19) . . ?
C9 O3 C12 117.8(4) . . ?
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
C1 O1 1.301(4) . ?
C1 N1 1.327(5) . ?
C1 C2 1.401(5) . ?
C2 C4 1.415(5) . ?
C2 C3 1.440(5) . ?
C3 O2 1.277(4) . ?
C3 N3 1.308(5) . ?
C4 N2 1.130(5) . ?
C5 N3 1.442(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.363(6) . ?
C6 C7 1.386(5) . ?
C6 N1 1.416(5) . ?
C7 C8 1.363(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C9 O3 1.357(5) . ?
C9 C10 1.380(6) . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 O3 1.415(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1N1 0.82(5) . ?
N3 H1N3 0.82(4) . ?
O1 H1O1 1.17(5) . ?
O2 H1O1 1.30(5) . ?
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
N1 H1N1 O2 0.82(5) 2.32(5) 3.081(4) 155(4) 4_566
O1 H1O1 O2 1.17(5) 1.30(5) 2.424(4) 159(4) .
N3 H1N3 N2 0.82(4) 2.23(4) 3.006(5) 158(4) 3_657
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658824
