##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 985334'
_chemical_name_systematic
;
4-Formyl-2-nitrophenyl benzoate
;
_chemical_name_common     '4-formyl-2-nitrophenyl benzoate'
_chemical_formula_moiety     'C14 H9 N O5'
_chemical_formula_sum     'C14 H9 N O5'
_chemical_formula_iupac     'C14 H9 N O5'
_chemical_formula_weight     271.22
_chemical_melting_point     457.0(10)
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     11.3478(11)
_cell_length_b     3.7101(5)
_cell_length_c     27.723(2)
_cell_angle_alpha     90.00
_cell_angle_beta     94.979(9)
_cell_angle_gamma     90.00
_cell_volume     1162.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     977
_cell_measurement_theta_min     3.907
_cell_measurement_theta_max     73.2798
_cell_measurement_temperature     123
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.549
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     1.017
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2010)
;
_exptl_absorpt_correction_T_min     0.8125
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     123
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method     'omega scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4231
_diffrn_reflns_av_R_equivalents     0.0485
_diffrn_reflns_av_sigmaI/netI     0.0791
_diffrn_reflns_theta_min     3.91
_diffrn_reflns_theta_max     69.98
_diffrn_reflns_theta_full     69.98
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -4
_diffrn_reflns_limit_k_max     4
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2213
_reflns_number_gt     1403
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0979
_refine_ls_R_factor_gt     0.0647
_refine_ls_wR_factor_gt     0.1551
_refine_ls_wR_factor_ref     0.1902
_refine_ls_goodness_of_fit_ref     0.993
_refine_ls_restrained_S_all     0.993
_refine_ls_number_reflns     2213
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0857P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.366
_refine_diff_density_min     -0.282
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0028(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'C' 'C' 0.0181 0.0091
                         '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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
 'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006)'
_computing_publication_material     'WinGX (Farrugia, 2012)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.89645(19) 0.3296(7) 0.43051(7) 0.0419(7) Uani d . 1 1 . .
    O O2 0.73248(18) 0.0150(7) 0.40350(7) 0.0398(6) Uani d . 1 1 . .
    O O5 0.8819(2) -0.0584(8) 0.18661(8) 0.0510(8) Uani d . 1 1 . .
    O O3 0.5482(2) 0.4580(8) 0.37507(8) 0.0457(7) Uani d . 1 1 . .
    O O4 0.46029(19) 0.1854(8) 0.31290(7) 0.0462(7) Uani d . 1 1 . .
    N N1 0.5497(2) 0.2761(9) 0.33830(9) 0.0374(7) Uani d . 1 1 . .
    C C7 0.8124(3) 0.1534(10) 0.43947(10) 0.0356(8) Uani d . 1 1 . .
    C C1 0.7763(3) 0.0601(10) 0.48775(11) 0.0363(8) Uani d . 1 1 . .
    C C2 0.6678(3) -0.1079(9) 0.49328(11) 0.0370(8) Uani d . 1 1 . .
    H H2 0.6164 -0.1707 0.4657 0.044 Uiso calc R 1 1 . .
    C C3 0.6360(3) -0.1820(11) 0.53964(11) 0.0404(8) Uani d . 1 1 . .
    H H3 0.5626 -0.2956 0.5439 0.048 Uiso calc R 1 1 . .
    C C4 0.7118(3) -0.0895(10) 0.57954(12) 0.0441(9) Uani d . 1 1 . .
    H H4 0.6897 -0.1382 0.6112 0.053 Uiso calc R 1 1 . .
    C C5 0.8190(3) 0.0722(11) 0.57390(11) 0.0436(9) Uani d . 1 1 . .
    H H5 0.8708 0.1306 0.6016 0.052 Uiso calc R 1 1 . .
    C C6 0.8514(3) 0.1497(10) 0.52809(11) 0.0393(8) Uani d . 1 1 . .
    H H6 0.9249 0.2641 0.5243 0.047 Uiso calc R 1 1 . .
    C C8 0.7551(3) 0.0466(10) 0.35567(11) 0.0353(8) Uani d . 1 1 . .
    C C9 0.6635(3) 0.1614(10) 0.32282(11) 0.0345(8) Uani d . 1 1 . .
    C C10 0.6769(3) 0.1666(10) 0.27316(11) 0.0364(8) Uani d . 1 1 . .
    H H10 0.6138 0.2447 0.2508 0.044 Uiso calc R 1 1 . .
    C C11 0.7821(3) 0.0577(10) 0.25704(11) 0.0369(8) Uani d . 1 1 . .
    C C12 0.8741(3) -0.0597(10) 0.29011(11) 0.0375(8) Uani d . 1 1 . .
    H H12 0.9469 -0.1342 0.2788 0.045 Uiso calc R 1 1 . .
    C C13 0.8601(3) -0.0684(10) 0.33923(11) 0.0380(8) Uani d . 1 1 . .
    H H13 0.9224 -0.1530 0.3615 0.046 Uiso calc R 1 1 . .
    C C14 0.7966(3) 0.0616(11) 0.20439(11) 0.0399(9) Uani d . 1 1 . .
    H H14 0.731(3) 0.180(10) 0.1847(11) 0.039(9) Uiso d . 1 1 . .
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
    O1 0.0400(13) 0.0533(16) 0.0313(12) -0.0048(12) -0.0026(10) 0.0012(11)
    O2 0.0384(12) 0.0560(16) 0.0233(11) -0.0044(11) -0.0075(9) 0.0031(11)
    O5 0.0475(15) 0.072(2) 0.0329(12) 0.0034(14) -0.0016(11) -0.0037(13)
    O3 0.0450(14) 0.0584(18) 0.0329(12) -0.0017(12) -0.0009(10) -0.0091(12)
    O4 0.0376(13) 0.0667(19) 0.0322(12) 0.0026(12) -0.0085(10) -0.0034(12)
    N1 0.0377(15) 0.0472(18) 0.0259(12) 0.0007(13) -0.0056(11) 0.0023(13)
    C7 0.0355(17) 0.043(2) 0.0264(15) 0.0041(15) -0.0074(13) -0.0006(15)
    C1 0.0355(17) 0.045(2) 0.0271(16) 0.0055(15) -0.0036(13) 0.0026(15)
    C2 0.0397(18) 0.041(2) 0.0283(16) 0.0030(15) -0.0070(13) 0.0004(15)
    C3 0.0380(17) 0.047(2) 0.0353(17) 0.0033(16) 0.0003(14) 0.0018(16)
    C4 0.047(2) 0.054(2) 0.0310(16) 0.0024(18) -0.0013(14) 0.0038(17)
    C5 0.0449(19) 0.055(2) 0.0281(16) 0.0046(17) -0.0122(14) -0.0049(16)
    C6 0.0365(17) 0.048(2) 0.0320(16) 0.0003(16) -0.0038(13) 0.0022(16)
    C8 0.0381(17) 0.0407(19) 0.0258(15) -0.0061(15) -0.0051(13) 0.0036(14)
    C9 0.0332(16) 0.0404(19) 0.0285(15) -0.0025(15) -0.0051(12) -0.0003(15)
    C10 0.0362(17) 0.044(2) 0.0266(15) -0.0005(16) -0.0091(13) 0.0055(15)
    C11 0.0383(18) 0.044(2) 0.0271(15) -0.0036(15) -0.0043(13) -0.0019(15)
    C12 0.0363(17) 0.042(2) 0.0333(16) -0.0043(15) -0.0043(13) -0.0043(15)
    C13 0.0384(17) 0.044(2) 0.0292(16) -0.0008(15) -0.0087(13) 0.0034(15)
    C14 0.0382(18) 0.050(2) 0.0301(17) -0.0024(16) -0.0064(14) 0.0008(16)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C7 . 1.200(4) ?
    O2 C8 . 1.377(4) ?
    O2 C7 . 1.387(3) ?
    O5 C14 . 1.208(4) ?
    O3 N1 . 1.224(3) ?
    O4 N1 . 1.231(3) ?
    N1 C9 . 1.459(4) ?
    C7 C1 . 1.475(4) ?
    C1 C6 . 1.387(4) ?
    C1 C2 . 1.399(5) ?
    C2 C3 . 1.392(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.384(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.377(5) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.383(5) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C8 C13 . 1.380(5) ?
    C8 C9 . 1.388(4) ?
    C9 C10 . 1.398(4) ?
    C10 C11 . 1.372(4) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.398(4) ?
    C11 C14 . 1.483(4) ?
    C12 C13 . 1.385(4) ?
    C12 H12 . 0.9500 ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.99(3) ?
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
    C8 O2 C7 . . 119.7(3) ?
    O3 N1 O4 . . 123.9(3) ?
    O3 N1 C9 . . 118.8(2) ?
    O4 N1 C9 . . 117.3(3) ?
    O1 C7 O2 . . 122.3(3) ?
    O1 C7 C1 . . 127.2(3) ?
    O2 C7 C1 . . 110.5(3) ?
    C6 C1 C2 . . 120.2(3) ?
    C6 C1 C7 . . 118.4(3) ?
    C2 C1 C7 . . 121.4(3) ?
    C3 C2 C1 . . 119.3(3) ?
    C3 C2 H2 . . 120.3 ?
    C1 C2 H2 . . 120.3 ?
    C4 C3 C2 . . 119.7(3) ?
    C4 C3 H3 . . 120.1 ?
    C2 C3 H3 . . 120.1 ?
    C5 C4 C3 . . 120.7(3) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 120.2(3) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C5 C6 C1 . . 119.8(3) ?
    C5 C6 H6 . . 120.1 ?
    C1 C6 H6 . . 120.1 ?
    O2 C8 C13 . . 122.0(3) ?
    O2 C8 C9 . . 117.8(3) ?
    C13 C8 C9 . . 119.8(3) ?
    C8 C9 C10 . . 120.8(3) ?
    C8 C9 N1 . . 121.9(3) ?
    C10 C9 N1 . . 117.4(3) ?
    C11 C10 C9 . . 119.3(3) ?
    C11 C10 H10 . . 120.4 ?
    C9 C10 H10 . . 120.4 ?
    C10 C11 C12 . . 120.0(3) ?
    C10 C11 C14 . . 119.5(3) ?
    C12 C11 C14 . . 120.5(3) ?
    C13 C12 C11 . . 120.6(3) ?
    C13 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
    C8 C13 C12 . . 119.6(3) ?
    C8 C13 H13 . . 120.2 ?
    C12 C13 H13 . . 120.2 ?
    O5 C14 C11 . . 124.0(3) ?
    O5 C14 H14 . . 122.0(19) ?
    C11 C14 H14 . . 114.0(19) ?
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
    C8 O2 C7 O1 . . . . 6.7(5) ?
    C8 O2 C7 C1 . . . . -174.7(3) ?
    O1 C7 C1 C6 . . . . -7.0(6) ?
    O2 C7 C1 C6 . . . . 174.5(3) ?
    O1 C7 C1 C2 . . . . 171.6(4) ?
    O2 C7 C1 C2 . . . . -6.9(5) ?
    C6 C1 C2 C3 . . . . 0.3(5) ?
    C7 C1 C2 C3 . . . . -178.2(3) ?
    C1 C2 C3 C4 . . . . -0.1(5) ?
    C2 C3 C4 C5 . . . . -0.6(6) ?
    C3 C4 C5 C6 . . . . 1.1(6) ?
    C4 C5 C6 C1 . . . . -0.8(6) ?
    C2 C1 C6 C5 . . . . 0.1(6) ?
    C7 C1 C6 C5 . . . . 178.7(3) ?
    C7 O2 C8 C13 . . . . 53.3(5) ?
    C7 O2 C8 C9 . . . . -133.8(3) ?
    O2 C8 C9 C10 . . . . -173.9(3) ?
    C13 C8 C9 C10 . . . . -0.8(5) ?
    O2 C8 C9 N1 . . . . 5.3(5) ?
    C13 C8 C9 N1 . . . . 178.3(3) ?
    O3 N1 C9 C8 . . . . 40.2(5) ?
    O4 N1 C9 C8 . . . . -140.5(3) ?
    O3 N1 C9 C10 . . . . -140.6(3) ?
    O4 N1 C9 C10 . . . . 38.6(5) ?
    C8 C9 C10 C11 . . . . -0.2(5) ?
    N1 C9 C10 C11 . . . . -179.4(3) ?
    C9 C10 C11 C12 . . . . 0.5(5) ?
    C9 C10 C11 C14 . . . . 179.8(3) ?
    C10 C11 C12 C13 . . . . 0.2(5) ?
    C14 C11 C12 C13 . . . . -179.1(3) ?
    O2 C8 C13 C12 . . . . 174.3(3) ?
    C9 C8 C13 C12 . . . . 1.6(5) ?
    C11 C12 C13 C8 . . . . -1.3(5) ?
    C10 C11 C14 O5 . . . . -173.3(4) ?
    C12 C11 C14 O5 . . . . 5.9(6) ?
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
    C10 H10 O4 2_655 0.95 2.50 3.343(4) 148.0
    C12 H12 O5 2_745 0.95 2.62 3.346(4) 133.9
data_global
_journal_date_recd_electronic     2014-02-04
_journal_date_accepted     2014-02-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      3
_journal_page_first     o268
_journal_page_last     o268
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814002694
_journal_coeditor_code     HG5380
_publ_contact_author_name     'Dr. Rodolfo Moreno-Fuquen'
_publ_contact_author_address
;
     Departamento de Química. Facultad de Ciencias,
     Universidad del Valle, Apartado 25360, Santiago de Cali,
     Colombia
;
_publ_contact_author_email     'rodimo26@yahoo.es'
_publ_contact_author_fax     '57 23 392440'
_publ_contact_author_phone     '57 23 393248'
_publ_section_title
;
4-Formyl-2-nitrophenyl benzoate
;
loop_
    _publ_author_name
    _publ_author_address
    'Moreno-Fuquen, Rodolfo'
;    Departamento de Química, Facultad de Ciencias,
     Universidad del Valle
     Apartado 25360, Santiago de Cali,
     Colombia
;
    'Hernandez, Geraldine'
;    Departamento de Química, Facultad de Ciencias,
     Universidad del Valle
     Apartado 25360, Santiago de Cali,
     Colombia
;
    'Kennedy, Alan R.'
;    WestCHEM, Department of Pure and Applied Chemistry,
     University of Strathclyde,
     295 Cathedral Street, Glasgow G1 1XL,
     Scotland
;
_exptl_special_details
;
IR spectra was recorded on a FT---IR SHIMADZU IR-Affinity-1 spectrophotometer.
IR (KBr) 3434.14cm⁻¹ (aromatic, C-H); 1755.69 cm⁻¹ (ester, C=O);
1702.79 cm⁻¹ (benzaldehyde, C=O), 1224.92 cm⁻¹ (ester, C-O); 1532.44
cm⁻¹, 1359.50 cm⁻¹ (-NO2); 1078.89 cm⁻¹ (C=C).
Absorption correction: CrysAlisPro, Agilent Technologies,
Version 1.171.34.46 (release 25-11-2010 CrysAlis171 .NET).
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
