#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/91/2209142.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_2209142
loop_
_publ_author_name
'P. S. Patil'
'Jeannie Bee-Jan Teh'
'Hoong-Kun Fun'
'Ibrahim Abdul Razak'
'S. M. Dharmaprakash'
_publ_section_title
;
 3-(2-Furyl)-1-(4-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           CV2051
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2397
_journal_page_last               o2398
_journal_paper_doi               10.1107/S1600536806017946
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H9 N O4'
_chemical_formula_moiety         'C13 H9 N O4'
_chemical_formula_sum            'C13 H9 N O4'
_chemical_formula_weight         243.21
_chemical_name_systematic
;
3-(2-Furyl)-1-(4-nitrophenyl)prop-2-en-1-one
;
_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                 94.867(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8809(2)
_cell_length_b                   10.6603(4)
_cell_length_c                   26.5500(11)
_cell_measurement_reflns_used    4832
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      37.49
_cell_measurement_theta_min      1.54
_cell_volume                     1094.45(8)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
'SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area-detector'
_diffrn_measurement_method       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  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            28259
_diffrn_reflns_theta_full        37.49
_diffrn_reflns_theta_max         37.49
_diffrn_reflns_theta_min         1.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.8057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         5741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0700
_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)+(0.0956P)²+0.1328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1980
_reflns_number_gt                3956
_reflns_number_total             5741
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2051.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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209142
_cod_database_fobs_code          2209142
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_type_symbol
_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
O O1 -0.1250(3) 0.26693(9) 0.10568(4) 0.0231(2) Uani d . 1
O O2 0.0305(3) 0.59893(8) 0.24281(4) 0.0237(2) Uani d . 1
O O3 1.0335(3) 0.21435(10) 0.42360(4) 0.0336(3) Uani d . 1
O O4 1.0389(3) 0.40418(10) 0.45266(4) 0.0331(3) Uani d . 1
N N1 0.9515(3) 0.32556(11) 0.42030(4) 0.0222(2) Uani d . 1
C C1 0.4735(3) 0.31959(11) 0.29253(5) 0.0180(2) Uani d . 1
H H1A 0.4232 0.2633 0.2662 0.022 Uiso calc R 1
C C2 0.6653(3) 0.28027(11) 0.33638(5) 0.0187(2) Uani d . 1
H H2A 0.7414 0.1978 0.3399 0.022 Uiso calc R 1
C C3 0.7400(3) 0.36659(11) 0.37458(4) 0.0181(2) Uani d . 1
C C4 0.6322(3) 0.49069(12) 0.37111(5) 0.0208(2) Uani d . 1
H H4A 0.6885 0.5470 0.3973 0.025 Uiso calc R 1
C C5 0.4379(3) 0.52820(11) 0.32744(5) 0.0203(2) Uani d . 1
H H5A 0.3609 0.6107 0.3243 0.024 Uiso calc R 1
C C6 0.3562(3) 0.44321(10) 0.28801(4) 0.0160(2) Uani d . 1
C C7 0.1394(3) 0.49038(11) 0.24248(4) 0.0173(2) Uani d . 1
C C8 0.0602(3) 0.40802(11) 0.19861(4) 0.0190(2) Uani d . 1
H H8A 0.1464 0.3266 0.1986 0.023 Uiso calc R 1
C C9 -0.1393(3) 0.45199(11) 0.15827(5) 0.0194(2) Uani d . 1
H H9A -0.2211 0.5335 0.1608 0.023 Uiso calc R 1
C C10 -0.2384(3) 0.38741(11) 0.11227(5) 0.0198(2) Uani d . 1
C C11 -0.4378(4) 0.42569(13) 0.07003(5) 0.0238(3) Uani d . 1
H H11A -0.5449 0.5033 0.0650 0.029 Uiso calc R 1
C C12 -0.4494(4) 0.32378(14) 0.03538(5) 0.0262(3) Uani d . 1
H H12A -0.5655 0.3214 0.0033 0.031 Uiso calc R 1
C C13 -0.2574(4) 0.23088(13) 0.05846(5) 0.0260(3) Uani d . 1
H H13B -0.2204 0.1529 0.0441 0.031 Uiso calc R 1
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
C13 O1 C10 106.24(10)
O4 N1 O3 123.66(11)
O4 N1 C3 118.41(11)
O3 N1 C3 117.92(11)
C2 C1 C6 120.22(11)
C2 C1 H1A 119.9
C6 C1 H1A 119.9
C3 C2 C1 118.51(11)
C3 C2 H2A 120.7
C1 C2 H2A 120.7
C2 C3 C4 122.86(11)
C2 C3 N1 118.34(11)
C4 C3 N1 118.77(10)
C5 C4 C3 118.00(11)
C5 C4 H4A 121.0
C3 C4 H4A 121.0
C4 C5 C6 120.72(11)
C4 C5 H5A 119.6
C6 C5 H5A 119.6
C1 C6 C5 119.67(10)
C1 C6 C7 122.84(10)
C5 C6 C7 117.48(10)
O2 C7 C8 121.18(10)
O2 C7 C6 118.58(10)
C8 C7 C6 120.24(10)
C9 C8 C7 119.21(11)
C9 C8 H8A 120.4
C7 C8 H8A 120.4
C8 C9 C10 127.31(11)
C8 C9 H9A 116.3
C10 C9 H9A 116.3
C11 C10 O1 109.83(11)
C11 C10 C9 130.54(12)
O1 C10 C9 119.63(10)
C10 C11 C12 106.66(12)
C10 C11 H11A 126.7
C12 C11 H11A 126.7
C13 C12 C11 106.27(12)
C13 C12 H12A 126.9
C11 C12 H12A 126.9
C12 C13 O1 111.00(12)
C12 C13 H13B 124.5
O1 C13 H13B 124.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.3690(15)
O1 C10 1.3736(15)
O2 C7 1.2321(14)
O3 N1 1.2287(15)
O4 N1 1.2274(14)
N1 C3 1.4728(15)
C1 C2 1.3921(16)
C1 C6 1.3960(16)
C1 H1A 0.9300
C2 C3 1.3818(16)
C2 H2A 0.9300
C3 C4 1.3882(17)
C4 C5 1.3873(17)
C4 H4A 0.9300
C5 C6 1.4005(16)
C5 H5A 0.9300
C6 C7 1.4998(16)
C7 C8 1.4702(16)
C8 C9 1.3510(16)
C8 H8A 0.9300
C9 C10 1.4262(17)
C9 H9A 0.9300
C10 C11 1.3696(16)
C11 C12 1.422(2)
C11 H11A 0.9300
C12 C13 1.354(2)
C12 H12A 0.9300
C13 H13B 0.9300
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
_geom_hbond_publ_flag
C1 H1A O2 2_545 0.93 2.4812 3.151(2) 129 y
C9 H9A O2 1_555 0.93 2.4125 2.770(2) 103 n
C12 H12A O3 4_365 0.93 2.5468 3.463(2) 169 y
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
C6 C1 C2 C3 -0.96(19)
C1 C2 C3 C4 0.0(2)
C1 C2 C3 N1 -178.27(11)
O4 N1 C3 C2 174.86(12)
O3 N1 C3 C2 -4.38(18)
O4 N1 C3 C4 -3.49(19)
O3 N1 C3 C4 177.26(13)
C2 C3 C4 C5 0.7(2)
N1 C3 C4 C5 178.99(12)
C3 C4 C5 C6 -0.5(2)
C2 C1 C6 C5 1.15(19)
C2 C1 C6 C7 -178.05(12)
C4 C5 C6 C1 -0.40(19)
C4 C5 C6 C7 178.84(12)
C1 C6 C7 O2 175.92(12)
C5 C6 C7 O2 -3.30(17)
C1 C6 C7 C8 -4.10(18)
C5 C6 C7 C8 176.68(11)
O2 C7 C8 C9 -0.86(19)
C6 C7 C8 C9 179.16(11)
C7 C8 C9 C10 178.83(12)
C13 O1 C10 C11 0.08(15)
C13 O1 C10 C9 -179.42(12)
C8 C9 C10 C11 -179.87(14)
C8 C9 C10 O1 -0.5(2)
O1 C10 C11 C12 0.03(16)
C9 C10 C11 C12 179.45(13)
C10 C11 C12 C13 -0.12(16)
C11 C12 C13 O1 0.17(17)
C10 O1 C13 C12 -0.16(16)
