#------------------------------------------------------------------------------
#$Date: 2018-06-14 04:32:00 +0300 (Thu, 14 Jun 2018) $
#$Revision: 208360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/48/2004825.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_2004825
loop_
_publ_author_name
'Durruthy Carbonell, O.'
'Hernandez, R. A.'
'Roque Infante, E. M.'
'Au-Alvarez, O.'
_publ_section_title
;
 Structure of N-(2-furylmethyl)-α-cyano-2-furanacrylamide.
 Addendum
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1318
_journal_page_last               1318
_journal_paper_doi               10.1107/S010827019501612X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_type_scat_source
'International Tables Vol III Tables 4.2.6.8 and 6.1.1.4'
_cell_angle_alpha                94.1(2)
_cell_angle_beta                 93.8(2)
_cell_angle_gamma                93.6(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3050(10)
_cell_length_b                   9.486(2)
_cell_length_c                   11.437(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      11
_cell_volume                     571.5(3)
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0052
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2585
_diffrn_reflns_theta_max         30.60
_diffrn_standards_decay_%        <5
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.166
_refine_ls_extinction_coef       0.141(11)
_refine_ls_extinction_method
;
SHELXL-93 (Sheldrick, 1993) with Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_goodness_of_fit_obs   1.095
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2324
_refine_ls_R_factor_obs          0.0364
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0559P)²+0.0953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1003
_reflns_number_observed          2283
_reflns_number_total             2325
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab1319.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-14

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.0953P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        571.5(2)
_cod_database_code               2004825
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
O3 -0.6514(2) .77170(10) .37894(8) .0511(3)
O2 .0555(2) .43250(10) .32729(8) .0542(3)
O1 -0.2578(2) .09160(10) .09639(9) .0526(3)
C13 -0.7777(3) .8524(2) .45550(10) .0569(4)
C12 -0.6870(3) .8440(2) .56650(10) .0576(4)
C11 -0.4898(3) .7516(2) .56140(10) .0518(3)
C10 -0.4731(2) .70940(10) .44640(10) .0411(3)
C9 -0.3098(2) .61370(10) .39480(10) .0409(3)
C7 -0.3024(2) .56240(10) .28190(10) .0376(3)
C8 -0.4727(2) .59830(10) .18800(10) .0402(3)
C6 -0.1080(2) .45870(10) .25320(10) .0389(3)
C5 .0475(2) .29440(10) .10500(10) .0463(3)
C4 -.0213(2) .14760(10) .13410(10) .0395(3)
C3 .1086(3) .0485(2) .18440(10) .0496(3)
C2 -.0545(3) -.0774(2) .17780(10) .0523(3)
C1 -0.2705(3) -.0464(2) .12460(10) .0542(3)
N2 -0.5977(2) .61990(10) .10690(10) .0552(3)
N1 -0.1275(2) .39730(10) .14323(9) .0440(3)
H4 .2150 .3234 .1411 .056(4)
H5 .0556 .2950 .0206 .063(5)
H3 .276(4) .065(2) .216(2) .077(5)
H2 -.013(3) -0.170(2) .205(2) .071(5)
H7 -0.189(3) .583(2) .4500(10) .048(4)
H10 -0.909(3) .904(2) .416(2) .070(5)
H9 -0.746(4) .891(2) .634(2) .075(5)
H8 -0.388(3) .721(2) .623(2) .073(5)
H1 -0.431(4) -.099(2) .099(2) .072(5)
H6 -0.2461 .4194 .0943 .060(5)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 O3 C10 105.77(14)
C4 O1 C1 106.6(2)
C12 C13 O3 111.5(2)
C12 C13 H10 135.7(11)
O3 C13 H10 112.8(11)
C13 C12 C11 106.2(2)
C13 C12 H9 126.1(11)
C11 C12 H9 127.7(11)
C10 C11 C12 107.0(2)
C10 C11 H8 124.1(12)
C12 C11 H8 128.9(12)
C11 C10 O3 109.6(2)
C11 C10 C9 129.3(2)
O3 C10 C9 121.11(14)
C7 C9 C10 130.2(2)
C7 C9 H7 117.1(9)
C10 C9 H7 112.7(9)
C9 C7 C8 123.9(2)
C9 C7 C6 118.3(2)
C8 C7 C6 117.9(2)
N2 C8 C7 174.25(13)
O2 C6 N1 122.8(2)
O2 C6 C7 121.0(2)
N1 C6 C7 116.2(2)
N1 C5 C4 114.18(15)
N1 C5 H4 108.7(2)
C4 C5 H4 108.7(2)
N1 C5 H5 108.7(2)
C4 C5 H5 108.7(2)
H4 C5 H5 107.6(2)
C3 C4 O1 109.3(2)
C3 C4 C5 133.41(15)
O1 C4 C5 117.0(2)
C4 C3 C2 107.19(15)
C4 C3 H3 123.1(12)
C2 C3 H3 129.7(12)
C1 C2 C3 106.2(2)
C1 C2 H2 126.8(11)
C3 C2 H2 127.0(10)
C2 C1 O1 110.7(2)
C2 C1 H1 135.2(11)
O1 C1 H1 114.1(11)
C6 N1 C5 121.5(2)
C6 N1 H6 119.3(2)
C5 N1 H6 119.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C13 1.360(3)
O3 C10 1.371(3)
O2 C6 1.221(3)
O1 C4 1.361(3)
O1 C1 1.370(2)
C13 C12 1.337(3)
C13 H10 0.98(2)
C12 C11 1.408(3)
C12 H9 0.95(2)
C11 C10 1.358(2)
C11 H8 0.94(2)
C10 C9 1.419(3)
C9 C7 1.351(2)
C9 H7 0.95(2)
C7 C8 1.430(3)
C7 C6 1.505(3)
C8 N2 1.143(3)
C6 N1 1.343(2)
C5 N1 1.454(3)
C5 C4 1.483(2)
C5 H4 0.970(2)
C5 H5 0.9699(13)
C4 C3 1.340(3)
C3 C2 1.425(3)
C3 H3 0.94(2)
C2 C1 1.321(3)
C2 H2 0.99(2)
C1 H1 0.98(2)
N1 H6 0.860(2)
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
C10 O3 C13 C12 0.3(2) ?
O3 C13 C12 C11 -0.2(2) ?
C13 C12 C11 C10 0.0(2) ?
C12 C11 C10 O3 0.1(2) ?
C12 C11 C10 C9 -178.18(14) ?
C13 O3 C10 C11 -0.2(2) ?
C13 O3 C10 C9 178.23(12) ?
C11 C10 C9 C7 174.54(14) ?
O3 C10 C9 C7 -3.6(2) ?
C10 C9 C7 C8 -0.4(2) yes
C10 C9 C7 C6 -178.87(12) yes
C9 C7 C8 N2 178.1(13) ?
C6 C7 C8 N2 -3.4(14) ?
C9 C7 C6 O2 -7.4(2) ?
C8 C7 C6 O2 174.03(12) ?
C9 C7 C6 N1 172.04(11) ?
C8 C7 C6 N1 -6.5(2) ?
C1 O1 C4 C3 -0.29(14) ?
C1 O1 C4 C5 175.21(11) ?
N1 C5 C4 C3 -131.1(2) ?
N1 C5 C4 O1 54.7(2) ?
O1 C4 C3 C2 0.29(14) ?
C5 C4 C3 C2 -174.18(12) ?
C4 C3 C2 C1 -0.2(2) ?
C3 C2 C1 O1 0.0(2) ?
C4 O1 C1 C2 0.2(2) ?
O2 C6 N1 C5 0.0(2) ?
C7 C6 N1 C5 -179.46(10) ?
C4 C5 N1 C6 84.2(2) ?
H7 C9 C7 C8 179.7(9) yes
