##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1448516'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
1-Ethyl-3-nitroquinolin-4(1H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H10 N2 O3'
_chemical_formula_sum     'C11 H10 N2 O3'
_chemical_formula_iupac     'C11 H10 N2 O3'
_chemical_formula_weight     218.21
_chemical_melting_point     495
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     5.1565(6)
_cell_length_b     12.4881(9)
_cell_length_c     15.1083(12)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     972.90(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6181
_cell_measurement_theta_min     2.70
_cell_measurement_theta_max     28.32
_cell_measurement_temperature     193(2)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.490
_exptl_crystal_size_mid     0.300
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.490
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.111
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     0.948
_shelx_estimated_absorpt_T_max     0.978
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     193(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Stoe IPDS 2T'
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_method     'rotation method'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     3974
_diffrn_reflns_av_R_equivalents     0.0187
_diffrn_reflns_theta_min     2.696
_diffrn_reflns_theta_max     28.166
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     2353
_reflns_number_gt     2133
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0384
_refine_ls_R_factor_gt     0.0331
_refine_ls_wR_factor_gt     0.0836
_refine_ls_wR_factor_ref     0.0879
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     2353
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0465P)²+0.2026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.234
_refine_diff_density_min     -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x determined using 819 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     2.3(7)
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2011)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2011)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2011)
;
_computing_structure_solution
;
SIR2004 (Burla et al.,  2005)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.2084(3) 0.47445(12) 0.65359(10) 0.0228(3) Uani d 1 . .
    C C2 0.3882(4) 0.47659(14) 0.71683(11) 0.0233(4) Uani d 1 . .
    H H2 0.4890 0.4140 0.7265 0.028 Uiso calc 1 . .
    C C3 0.4353(4) 0.56468(15) 0.76878(12) 0.0232(4) Uani d 1 . .
    C C4 0.2937(4) 0.66408(14) 0.75900(11) 0.0222(3) Uani d 1 . .
    C C4A 0.0942(3) 0.65770(14) 0.68842(11) 0.0223(4) Uani d 1 . .
    C C5 -0.0628(4) 0.74724(16) 0.67303(13) 0.0274(4) Uani d 1 . .
    H H5 -0.0392 0.8100 0.7077 0.033 Uiso calc 1 . .
    C C6 -0.2510(4) 0.74565(17) 0.60848(14) 0.0318(4) Uani d 1 . .
    H H6 -0.3600 0.8061 0.5998 0.038 Uiso calc 1 . .
    C C7 -0.2803(4) 0.65477(18) 0.55584(13) 0.0331(5) Uani d 1 . .
    H H7 -0.4070 0.6544 0.5102 0.040 Uiso calc 1 . .
    C C8 -0.1285(4) 0.56560(17) 0.56906(12) 0.0282(4) Uani d 1 . .
    H H8 -0.1498 0.5043 0.5325 0.034 Uiso calc 1 . .
    C C8A 0.0581(4) 0.56545(15) 0.63672(11) 0.0228(4) Uani d 1 . .
    C C9 0.1748(4) 0.37471(15) 0.60113(12) 0.0272(4) Uani d 1 . .
    H H9A -0.0119 0.3638 0.5888 0.033 Uiso calc 1 . .
    H H9B 0.2368 0.3129 0.6363 0.033 Uiso calc 1 . .
    C C10 0.3217(5) 0.37880(19) 0.51459(14) 0.0376(5) Uani d 1 . .
    H H10A 0.2707 0.3179 0.4776 0.056 Uiso calc 1 . .
    H H10B 0.5084 0.3754 0.5264 0.056 Uiso calc 1 . .
    H H10C 0.2811 0.4458 0.4837 0.056 Uiso calc 1 . .
    N N11 0.6373(3) 0.55207(13) 0.83436(10) 0.0280(4) Uani d 1 . .
    O O12 0.6949(4) 0.62668(14) 0.88100(12) 0.0538(5) Uani d 1 . .
    O O13 0.7418(5) 0.46513(15) 0.84251(15) 0.0701(8) Uani d 1 . .
    O O14 0.3262(3) 0.74669(11) 0.80200(9) 0.0301(3) Uani d 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    N1 C2 . 1.332(2) ?
    N1 C8A . 1.399(2) ?
    N1 C9 . 1.486(2) ?
    C2 C3 . 1.373(2) ?
    C2 H2 . 0.9500 ?
    C3 N11 . 1.446(2) ?
    C3 C4 . 1.448(2) ?
    C4 O14 . 1.231(2) ?
    C4 C4A . 1.484(2) ?
    C4A C5 . 1.400(2) ?
    C4A C8A . 1.404(2) ?
    C5 C6 . 1.376(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.394(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.376(3) ?
    C7 H7 . 0.9500 ?
    C8 C8A . 1.404(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.512(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    N11 O12 . 1.205(2) ?
    N11 O13 . 1.218(2) ?
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
    C2 N1 C8A . . 120.01(15) ?
    C2 N1 C9 . . 118.71(15) ?
    C8A N1 C9 . . 121.28(15) ?
    N1 C2 C3 . . 123.33(16) ?
    N1 C2 H2 . . 118.3 ?
    C3 C2 H2 . . 118.3 ?
    C2 C3 N11 . . 115.59(16) ?
    C2 C3 C4 . . 122.64(16) ?
    N11 C3 C4 . . 121.77(16) ?
    O14 C4 C3 . . 126.59(17) ?
    O14 C4 C4A . . 121.26(17) ?
    C3 C4 C4A . . 112.15(15) ?
    C5 C4A C8A . . 119.09(16) ?
    C5 C4A C4 . . 118.52(16) ?
    C8A C4A C4 . . 122.39(16) ?
    C6 C5 C4A . . 120.93(19) ?
    C6 C5 H5 . . 119.5 ?
    C4A C5 H5 . . 119.5 ?
    C5 C6 C7 . . 119.53(19) ?
    C5 C6 H6 . . 120.2 ?
    C7 C6 H6 . . 120.2 ?
    C8 C7 C6 . . 120.94(19) ?
    C8 C7 H7 . . 119.5 ?
    C6 C7 H7 . . 119.5 ?
    C7 C8 C8A . . 119.79(18) ?
    C7 C8 H8 . . 120.1 ?
    C8A C8 H8 . . 120.1 ?
    N1 C8A C8 . . 120.89(17) ?
    N1 C8A C4A . . 119.45(15) ?
    C8 C8A C4A . . 119.65(17) ?
    N1 C9 C10 . . 112.00(16) ?
    N1 C9 H9A . . 109.2 ?
    C10 C9 H9A . . 109.2 ?
    N1 C9 H9B . . 109.2 ?
    C10 C9 H9B . . 109.2 ?
    H9A C9 H9B . . 107.9 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    O12 N11 O13 . . 121.38(17) ?
    O12 N11 C3 . . 119.60(16) ?
    O13 N11 C3 . . 119.00(16) ?
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
    C8A N1 C2 C3 . . . . 0.7(3) ?
    C9 N1 C2 C3 . . . . 179.78(16) ?
    N1 C2 C3 N11 . . . . 179.74(16) ?
    N1 C2 C3 C4 . . . . -0.4(3) ?
    C2 C3 C4 O14 . . . . -179.06(18) ?
    N11 C3 C4 O14 . . . . 0.8(3) ?
    C2 C3 C4 C4A . . . . 0.9(2) ?
    N11 C3 C4 C4A . . . . -179.29(15) ?
    O14 C4 C4A C5 . . . . -1.7(3) ?
    C3 C4 C4A C5 . . . . 178.35(16) ?
    O14 C4 C4A C8A . . . . 178.16(17) ?
    C3 C4 C4A C8A . . . . -1.8(2) ?
    C8A C4A C5 C6 . . . . 0.2(3) ?
    C4 C4A C5 C6 . . . . -179.94(17) ?
    C4A C5 C6 C7 . . . . -2.0(3) ?
    C5 C6 C7 C8 . . . . 1.7(3) ?
    C6 C7 C8 C8A . . . . 0.3(3) ?
    C2 N1 C8A C8 . . . . 178.58(17) ?
    C9 N1 C8A C8 . . . . -0.4(2) ?
    C2 N1 C8A C4A . . . . -1.6(2) ?
    C9 N1 C8A C4A . . . . 179.37(16) ?
    C7 C8 C8A N1 . . . . 177.65(18) ?
    C7 C8 C8A C4A . . . . -2.2(3) ?
    C5 C4A C8A N1 . . . . -177.91(16) ?
    C4 C4A C8A N1 . . . . 2.2(2) ?
    C5 C4A C8A C8 . . . . 1.9(2) ?
    C4 C4A C8A C8 . . . . -177.99(16) ?
    C2 N1 C9 C10 . . . . -96.4(2) ?
    C8A N1 C9 C10 . . . . 82.6(2) ?
    C2 C3 N11 O12 . . . . 178.05(19) ?
    C4 C3 N11 O12 . . . . -1.8(3) ?
    C2 C3 N11 O13 . . . . -3.6(3) ?
    C4 C3 N11 O13 . . . . 176.6(2) ?
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
    C2 H2 O13 . 0.95 2.28 2.636(3) 102
    C2 H2 O14 4_646 0.95 2.34 3.239(2) 159
    C9 H9B O14 4_646 0.99 2.57 3.364(3) 137
    C9 H9B O12 4_646 0.99 2.37 3.181(3) 139
data_New_Global_Publ_Block
_journal_date_recd_electronic     2016-01-18
_journal_date_accepted     2016-01-20
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      2
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616001255
_journal_coeditor_code     TK5417
_publ_contact_author_name     'Heiner Detert'
_publ_contact_author_address
;
University Mainz
Duesbergweg 10-14
55099 Mainz
Germany
;
_publ_contact_author_email     detert@uni-mainz.de
_publ_contact_author_fax            .496131E-302
_publ_contact_author_phone            .496131E-302
_publ_section_title
;
1-Ethyl-3-nitroquinolin-4(1H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Limbach, Daniel'
;
University Mainz
Duesbergweg 10-14
55099 Mainz
Germany
;
    'Stengelin, Elena'
;
University Mainz
Duesbergweg 10-14
55099 Mainz
Germany
;
    'Schollmeyer, Dieter'
;
University Mainz
Duesbergweg 10-14
55099 Mainz
Germany
;
    'Detert, Heiner'
;
University Mainz
Duesbergweg 10-14
55099 Mainz
Germany
;
_publ_section_synopsis
;
The 15 non-H atoms in the title compound are coplanar with the methyl group
sitting prime to the plane. Supramolecular undulating ribbons sustained by
C---H...O interactions are found in the crystal structure.
;
