#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/48/2014825.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_2014825
loop_
_publ_author_name
'Araya-Maturana, Ramiro'
'Heredia-Moya, Jorge'
'Pessoa-Mahana, Hernán'
'Weiss-López, Boris'
'Muñoz, Juan Carlos'
_publ_section_title
;
 (2Z)-3-(5-Hydroxy-4-oxo-4H-chromen-3-yl)acrylonitrile
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o237
_journal_page_last               o239
_journal_paper_doi               10.1107/S0108270105004841
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H7 N O3'
_chemical_formula_moiety         'C12 H7 N O3'
_chemical_formula_sum            'C12 H7 N O3'
_chemical_formula_weight         213.19
_chemical_name_systematic
;
(2Z)-3-(5-hydroxy-4-oxo-4H-chromen-3-yl)acrylonitrile
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.099(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2251(11)
_cell_length_b                   11.1930(17)
_cell_length_c                   12.2219(18)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.49
_cell_volume                     969.9(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT-Plus NT (Bruker, 2002)'
_computing_molecular_graphics    'XP in SHELXTL-PC (Sheldrick, 1994)'
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  'XL in SHELXTL-NT'
_computing_structure_solution    'XS in SHELXTL-NT (Bruker, 2002)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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    0.0358
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6913
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0414
_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)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                1494
_reflns_number_total             2172
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1370.cif
_cod_data_source_block           I
_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 

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_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_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014825
_cod_database_fobs_code          2014825
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
C1 0.21236(17) 0.11441(11) 0.08159(11) 0.0452(3) Uani d . 1 . . C
C2 0.15267(18) 0.21046(12) 0.01397(11) 0.0526(4) Uani d . 1 . . C
H2 0.1258 0.2826 0.0453 0.063 Uiso calc R 1 . . H
C3 0.13249(19) 0.20019(13) -0.09990(11) 0.0557(4) Uani d . 1 . . C
H3 0.0918 0.2659 -0.1446 0.067 Uiso calc R 1 . . H
C4 0.17134(19) 0.09451(13) -0.14926(11) 0.0540(4) Uani d . 1 . . C
H4 0.1561 0.0879 -0.2263 0.065 Uiso calc R 1 . . H
C5 0.23328(16) -0.00066(11) -0.08071(10) 0.0430(3) Uani d . 1 . . C
C6 0.25632(14) 0.00497(10) 0.03493(9) 0.0403(3) Uani d . 1 . . C
C7 0.32552(19) -0.20164(12) -0.06960(11) 0.0498(3) Uani d . 1 . . C
H7 0.3483 -0.2712 -0.1064 0.060 Uiso calc R 1 . . H
C8 0.34848(17) -0.20640(11) 0.04215(10) 0.0430(3) Uani d . 1 . . C
C9 0.32047(16) -0.09831(11) 0.10284(10) 0.0414(3) Uani d . 1 . . C
C10 0.40502(19) -0.31420(12) 0.10657(11) 0.0529(4) Uani d . 1 . . C
H10 0.4858 -0.3034 0.1749 0.063 Uiso calc R 1 . . H
C11 0.3552(2) -0.42569(13) 0.07951(11) 0.0561(4) Uani d . 1 . . C
H11 0.4054 -0.4860 0.1287 0.067 Uiso calc R 1 . . H
C12 0.2296(2) -0.45883(12) -0.02024(13) 0.0548(4) Uani d . 1 . . C
N1 0.1298(2) -0.48676(12) -0.09987(12) 0.0747(4) Uani d . 1 . . N
O1 0.22579(16) 0.12602(9) 0.19233(7) 0.0636(3) Uani d . 1 . . O
H1 0.2614 0.0627 0.2231 0.095 Uiso calc R 1 . . H
O2 0.27246(13) -0.10473(8) -0.13224(7) 0.0530(3) Uani d . 1 . . O
O3 0.34752(13) -0.09620(8) 0.20650(7) 0.0567(3) Uani d . 1 . . O
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
C1 0.0420(7) 0.0461(8) 0.0469(7) -0.0055(5) 0.0069(6) -0.0054(6)
C2 0.0519(8) 0.0417(7) 0.0654(9) -0.0012(6) 0.0140(7) -0.0013(6)
C3 0.0538(8) 0.0471(8) 0.0659(9) 0.0010(6) 0.0112(7) 0.0145(7)
C4 0.0570(8) 0.0597(9) 0.0449(8) -0.0007(7) 0.0086(6) 0.0088(6)
C5 0.0434(7) 0.0437(7) 0.0425(7) -0.0030(6) 0.0097(5) -0.0015(5)
C6 0.0352(6) 0.0435(7) 0.0417(7) -0.0049(5) 0.0064(5) -0.0006(5)
C7 0.0571(8) 0.0435(7) 0.0502(8) 0.0021(6) 0.0142(6) -0.0026(6)
C8 0.0402(7) 0.0465(8) 0.0419(7) 0.0010(5) 0.0068(5) -0.0002(5)
C9 0.0361(6) 0.0490(8) 0.0388(7) -0.0029(5) 0.0063(5) -0.0017(5)
C10 0.0532(8) 0.0561(9) 0.0479(8) 0.0087(7) 0.0058(6) 0.0021(6)
C11 0.0641(9) 0.0489(9) 0.0562(9) 0.0114(7) 0.0136(7) 0.0083(6)
C12 0.0668(9) 0.0426(8) 0.0600(9) 0.0019(7) 0.0244(8) 0.0030(7)
N1 0.0940(10) 0.0646(9) 0.0662(9) -0.0126(8) 0.0175(8) -0.0039(7)
O1 0.0860(7) 0.0547(6) 0.0491(6) 0.0028(5) 0.0108(5) -0.0114(4)
O2 0.0697(6) 0.0505(6) 0.0396(5) 0.0032(5) 0.0129(4) 0.0009(4)
O3 0.0674(6) 0.0624(6) 0.0383(5) 0.0065(5) 0.0052(4) -0.0005(4)
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 118.91(12)
O1 C1 C6 120.79(11)
C2 C1 C6 120.30(12)
C1 C2 C3 120.20(13)
C1 C2 H2 119.9
C3 C2 H2 119.9
C2 C3 C4 121.50(13)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 117.83(13)
C5 C4 H4 121.1
C3 C4 H4 121.1
C4 C5 O2 116.56(12)
C4 C5 C6 122.98(12)
O2 C5 C6 120.46(11)
C5 C6 C1 117.18(11)
C5 C6 C9 120.58(11)
C1 C6 C9 122.23(11)
O2 C7 C8 125.31(12)
O2 C7 H7 117.3
C8 C7 H7 117.3
C7 C8 C9 118.89(12)
C7 C8 C10 123.31(12)
C9 C8 C10 117.78(11)
O3 C9 C6 122.63(11)
O3 C9 C8 121.69(11)
C6 C9 C8 115.67(11)
C11 C10 C8 127.75(13)
C11 C10 H10 116.1
C8 C10 H10 116.1
C10 C11 C12 123.95(13)
C10 C11 H11 118.0
C12 C11 H11 118.0
N1 C12 C11 179.17(16)
C1 O1 H1 109.5
C7 O2 C5 118.94(10)
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
C1 O1 . 1.3445(15) ?
C1 C2 . 1.3739(18) ?
C1 C6 . 1.4129(17) ?
C2 C3 . 1.3760(17) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.381(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3758(18) ?
C4 H4 . 0.9300 ?
C5 O2 . 1.3792(15) ?
C5 C6 . 1.3923(17) ?
C6 C9 . 1.4464(17) ?
C7 O2 . 1.3404(16) ?
C7 C8 . 1.3448(17) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.4535(18) ?
C8 C10 . 1.4556(18) ?
C9 O3 . 1.2444(14) ?
C10 C11 . 1.323(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.422(2) ?
C11 H11 . 0.9300 ?
C12 N1 . 1.1379(18) ?
O1 H1 . 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O3 . 0.82 1.91 2.6327(14) 147
C10 H10 O1 2_645 0.93 2.51 3.3286(17) 147
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
O1 C1 C2 C3 -178.17(11)
C6 C1 C2 C3 1.00(19)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 -0.7(2)
C3 C4 C5 O2 -179.48(11)
C3 C4 C5 C6 0.6(2)
C4 C5 C6 C1 0.23(18)
O2 C5 C6 C1 -179.66(10)
C4 C5 C6 C9 179.49(11)
O2 C5 C6 C9 -0.41(17)
O1 C1 C6 C5 178.11(11)
C2 C1 C6 C5 -1.04(17)
O1 C1 C6 C9 -1.14(18)
C2 C1 C6 C9 179.71(10)
O2 C7 C8 C9 -2.10(19)
O2 C7 C8 C10 179.51(12)
C5 C6 C9 O3 178.11(11)
C1 C6 C9 O3 -2.67(18)
C5 C6 C9 C8 -2.97(16)
C1 C6 C9 C8 176.25(10)
C7 C8 C9 O3 -176.91(11)
C10 C8 C9 O3 1.57(18)
C7 C8 C9 C6 4.16(17)
C10 C8 C9 C6 -177.36(10)
C7 C8 C10 C11 -37.1(2)
C9 C8 C10 C11 144.50(14)
C8 C10 C11 C12 -1.5(2)
C10 C11 C12 N1 166(11)
C8 C7 O2 C5 -1.47(19)
C4 C5 O2 C7 -177.18(11)
C6 C5 O2 C7 2.72(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654019
