#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227435.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_2227435
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Quah, Ching Kheng'
Nithinchandra
'Kalluraya, Balakrishna'
_publ_section_title
;
 3-(5-Nitro-2-furyl)-1-phenylprop-2-yn-1-one
;
_journal_coeditor_code           FJ2357
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3031
_journal_page_last               o3032
_journal_paper_doi               10.1107/S1600536810043850
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H7 N O4'
_chemical_formula_moiety         'C13 H7 N O4'
_chemical_formula_sum            'C13 H7 N O4'
_chemical_formula_weight         241.20
_chemical_name_systematic
;
3-(5-Nitro-2-furyl)-1-phenylprop-2-yn-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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4685(2)
_cell_length_b                   7.30060(10)
_cell_length_c                   15.2642(2)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      37.55
_cell_measurement_theta_min      2.79
_cell_volume                     1090.07(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII 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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40673
_diffrn_reflns_theta_full        37.66
_diffrn_reflns_theta_max         37.66
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.278
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         5796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0678P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                4934
_reflns_number_total             5796
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2357.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227435
_cod_database_fobs_code          2227435
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.11630(5) 0.27415(7) 1.04906(3) 0.01471(9) Uani d . 1 . .
O O2 -0.39290(6) 0.35131(8) 1.11730(4) 0.02350(11) Uani d . 1 . .
O O3 -0.19217(6) 0.23310(8) 1.19322(4) 0.02173(10) Uani d . 1 . .
O O4 0.31281(5) 0.03921(7) 0.98678(3) 0.01702(9) Uani d . 1 . .
N N1 -0.27662(6) 0.30540(8) 1.12394(4) 0.01630(10) Uani d . 1 . .
C C1 -0.23941(6) 0.33853(8) 1.04384(4) 0.01429(10) Uani d . 1 . .
C C2 -0.31207(6) 0.41459(9) 0.95952(5) 0.01643(11) Uani d . 1 . .
H H2 -0.3984 0.4675 0.9412 0.020 Uiso calc R 1 . .
C C3 -0.22679(6) 0.39527(9) 0.90560(5) 0.01704(11) Uani d . 1 . .
H H3 -0.2463 0.4335 0.8441 0.020 Uiso calc R 1 . .
C C4 -0.11011(6) 0.30936(9) 0.96198(4) 0.01464(10) Uani d . 1 . .
C C5 0.00843(6) 0.25151(9) 0.94661(5) 0.01623(11) Uani d . 1 . .
C C6 0.10953(6) 0.20010(9) 0.93282(4) 0.01633(11) Uani d . 1 . .
C C7 0.23677(6) 0.13782(8) 0.92494(4) 0.01320(10) Uani d . 1 . .
C C8 0.27014(6) 0.19941(8) 0.84344(4) 0.01292(10) Uani d . 1 . .
C C9 0.17614(7) 0.29769(9) 0.76987(4) 0.01676(11) Uani d . 1 . .
H H9 0.0897 0.3240 0.7707 0.020 Uiso calc R 1 . .
C C10 0.21317(8) 0.35576(10) 0.69539(5) 0.02011(12) Uani d . 1 . .
H H10 0.1514 0.4214 0.6463 0.024 Uiso calc R 1 . .
C C11 0.34271(8) 0.31575(10) 0.69438(5) 0.02020(12) Uani d . 1 . .
H H11 0.3673 0.3559 0.6448 0.024 Uiso calc R 1 . .
C C12 0.43585(7) 0.21588(10) 0.76724(5) 0.01871(11) Uani d . 1 . .
H H12 0.5219 0.1886 0.7658 0.022 Uiso calc R 1 . .
C C13 0.39983(6) 0.15728(9) 0.84181(4) 0.01523(10) Uani d . 1 . .
H H13 0.4615 0.0904 0.8904 0.018 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C4 . . 104.51(5) ?
O3 N1 O2 . . 125.05(6) ?
O3 N1 C1 . . 118.47(5) ?
O2 N1 C1 . . 116.48(6) ?
O1 C1 C2 . . 113.56(5) ?
O1 C1 N1 . . 115.88(5) ?
C2 C1 N1 . . 130.40(5) ?
C1 C2 C3 . . 104.66(5) ?
C1 C2 H2 . . 127.7 ?
C3 C2 H2 . . 127.7 ?
C4 C3 C2 . . 106.57(6) ?
C4 C3 H3 . . 126.7 ?
C2 C3 H3 . . 126.7 ?
C3 C4 O1 . . 110.71(5) ?
C3 C4 C5 . . 132.41(6) ?
O1 C4 C5 . . 116.88(5) ?
C6 C5 C4 . . 179.25(7) ?
C5 C6 C7 . . 175.08(7) ?
O4 C7 C6 . . 118.85(5) ?
O4 C7 C8 . . 122.88(5) ?
C6 C7 C8 . . 118.26(5) ?
C9 C8 C13 . . 120.49(5) ?
C9 C8 C7 . . 121.50(5) ?
C13 C8 C7 . . 118.01(5) ?
C10 C9 C8 . . 119.41(6) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C9 C10 C11 . . 120.06(6) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.49(6) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 119.86(6) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C8 . . 119.67(6) ?
C12 C13 H13 . . 120.2 ?
C8 C13 H13 . . 120.2 ?
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
O1 C1 . 1.3472(7) ?
O1 C4 . 1.3779(8) ?
O2 N1 . 1.2315(7) ?
O3 N1 . 1.2298(8) ?
O4 C7 . 1.2278(8) ?
N1 C1 . 1.4298(8) ?
C1 C2 . 1.3586(9) ?
C2 C3 . 1.4205(9) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.3701(9) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.4073(8) ?
C5 C6 . 1.2100(8) ?
C6 C7 . 1.4525(8) ?
C7 C8 . 1.4770(8) ?
C8 C9 . 1.3990(8) ?
C8 C13 . 1.4010(8) ?
C9 C10 . 1.3915(9) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.3927(11) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.3953(10) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.3880(9) ?
C12 H12 . 0.9300 ?
C13 H13 . 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
C2 H2 O2 3_467 0.9300 2.4400 3.3548(9) 170.00 yes
C11 H11 O4 4_565 0.9300 2.4000 3.2487(9) 152.00 yes
C3 H3 Cg1 2_556 0.9300 2.8600 3.6284(7) 141.00 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 O1 C1 C2 . . . . -0.69(7) ?
C4 O1 C1 N1 . . . . 175.17(5) ?
O3 N1 C1 O1 . . . . 4.75(9) ?
O2 N1 C1 O1 . . . . -174.73(6) ?
O3 N1 C1 C2 . . . . 179.76(7) ?
O2 N1 C1 C2 . . . . 0.28(11) ?
O1 C1 C2 C3 . . . . 0.46(8) ?
N1 C1 C2 C3 . . . . -174.65(7) ?
C1 C2 C3 C4 . . . . -0.02(7) ?
C2 C3 C4 O1 . . . . -0.40(7) ?
C2 C3 C4 C5 . . . . 178.65(7) ?
C1 O1 C4 C3 . . . . 0.65(7) ?
C1 O1 C4 C5 . . . . -178.56(6) ?
O4 C7 C8 C9 . . . . 174.06(6) ?
C6 C7 C8 C9 . . . . -7.19(9) ?
O4 C7 C8 C13 . . . . -6.23(9) ?
C6 C7 C8 C13 . . . . 172.52(6) ?
C13 C8 C9 C10 . . . . -0.90(10) ?
C7 C8 C9 C10 . . . . 178.80(6) ?
C8 C9 C10 C11 . . . . 0.11(10) ?
C9 C10 C11 C12 . . . . 0.64(11) ?
C10 C11 C12 C13 . . . . -0.61(11) ?
C11 C12 C13 C8 . . . . -0.18(10) ?
C9 C8 C13 C12 . . . . 0.93(10) ?
C7 C8 C13 C12 . . . . -178.78(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9250741
