##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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_global
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2009-04-22
_journal_date_accepted     2009-04-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      6
_journal_page_first     o1210
_journal_page_last     o1210
_journal_paper_category     QO
_journal_coeditor_code     HK2674
_publ_contact_author_name     'Sun jie'
_publ_contact_author_address
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No.5 Nanjing,
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     sunjie5516@126.com
_publ_contact_author_fax     '86 25 ?'
_publ_contact_author_phone     '86 25 83587440'
_publ_section_title
;
N-(2-Hydroxyethyl)-1,8-naphthalimide
;
loop_
    _publ_author_name
    _publ_author_address
    'Sun, Jie'
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Yuan, Ai-lin'
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Wang, Hai-Bo'
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Sun, Jie'
;
College of Food Science and Light Industry,
Nanjing University of Technology,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(2-Hydroxyethyl)naphthalene-1,8-dicarboximide
;
_chemical_name_common     'N-(2-Hydroxyethyl)-1,8-naphthalimide'
_chemical_formula_moiety     'C14 H11 N O3'
_chemical_formula_sum     'C14 H11 N O3'
_chemical_formula_iupac     'C14 H11 N O3'
_chemical_formula_weight     241.24
_chemical_melting_point     413
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5480(15)
_cell_length_b     8.8300(18)
_cell_length_c     10.101(2)
_cell_angle_alpha     96.760(19)
_cell_angle_beta     109.94(3)
_cell_angle_gamma     114.60(3)
_cell_volume     548.2(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     13
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     green
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.461
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     252
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9695
_exptl_absorpt_correction_T_max     0.9897
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2159
_diffrn_reflns_av_R_equivalents     0.0227
_diffrn_reflns_av_sigmaI/netI     0.0336
_diffrn_reflns_theta_min     2.25
_diffrn_reflns_theta_max     25.27
_diffrn_reflns_theta_full     25.27
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
_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 > 2sigma(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     1995
_reflns_number_gt     1330
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0876
_refine_ls_R_factor_gt     0.0538
_refine_ls_wR_factor_gt     0.1384
_refine_ls_wR_factor_ref     0.2079
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     1.000
_refine_ls_number_reflns     1995
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w=1/[σ²(Fo²)+(0.1P)²+0.4P] 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     0.290
_refine_diff_density_min     -0.307
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.035(10)
_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
    '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     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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 0.4860(4) 0.2063(3) -0.0242(2) 0.0624(7) Uani d . 1 . .
    H H1A 0.4763 0.2711 -0.0749 0.094 Uiso calc R 1 . .
    O O2 0.6221(4) 0.5936(3) 0.1937(3) 0.0677(8) Uani d . 1 . .
    O O3 0.2875(4) 0.1029(3) 0.3070(3) 0.0729(8) Uani d . 1 . .
    N N 0.4553(4) 0.3481(3) 0.2496(3) 0.0480(7) Uani d . 1 . .
    C C1 0.3020(6) 0.1341(5) 0.0027(4) 0.0599(9) Uani d . 1 . .
    H H1B 0.3052 0.0455 0.0504 0.072 Uiso calc R 1 . .
    H H1C 0.1746 0.0767 -0.0913 0.072 Uiso calc R 1 . .
    C C2 0.2818(5) 0.2660(5) 0.0982(4) 0.0610(10) Uani d . 1 . .
    H H2A 0.2828 0.3566 0.0522 0.073 Uiso calc R 1 . .
    H H2B 0.1439 0.2081 0.1026 0.073 Uiso calc R 1 . .
    C C3 0.6193(5) 0.5166(4) 0.2858(3) 0.0472(8) Uani d . 1 . .
    C C4 0.4392(5) 0.2495(4) 0.3487(4) 0.0509(8) Uani d . 1 . .
    C C5 0.6124(5) 0.3314(4) 0.5006(3) 0.0464(8) Uani d . 1 . .
    C C6 0.6103(6) 0.2394(5) 0.6016(4) 0.0601(10) Uani d . 1 . .
    H H6A 0.4975 0.1263 0.5743 0.072 Uiso calc R 1 . .
    C C7 0.7759(7) 0.3145(5) 0.7442(4) 0.0677(11) Uani d . 1 . .
    H H7A 0.7726 0.2510 0.8114 0.081 Uiso calc R 1 . .
    C C8 0.9433(6) 0.4804(5) 0.7870(4) 0.0601(9) Uani d . 1 . .
    H H8A 1.0531 0.5286 0.8826 0.072 Uiso calc R 1 . .
    C C9 0.9504(5) 0.5784(4) 0.6872(3) 0.0450(7) Uani d . 1 . .
    C C10 0.7830(5) 0.5027(4) 0.5413(3) 0.0407(7) Uani d . 1 . .
    C C11 0.7899(5) 0.5973(4) 0.4390(3) 0.0423(7) Uani d . 1 . .
    C C12 0.9566(5) 0.7653(4) 0.4817(4) 0.0494(8) Uani d . 1 . .
    H H12A 0.9611 0.8282 0.4142 0.059 Uiso calc R 1 . .
    C C13 1.1206(5) 0.8421(4) 0.6277(4) 0.0560(9) Uani d . 1 . .
    H H13A 1.2317 0.9562 0.6562 0.067 Uiso calc R 1 . .
    C C14 1.1181(5) 0.7516(5) 0.7266(4) 0.0536(9) Uani d . 1 . .
    H H14A 1.2283 0.8041 0.8222 0.064 Uiso calc R 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 0.0681(16) 0.0792(17) 0.0581(15) 0.0486(14) 0.0293(12) 0.0251(12)
    O2 0.0783(17) 0.0742(17) 0.0564(15) 0.0431(14) 0.0243(13) 0.0308(13)
    O3 0.0595(16) 0.0526(15) 0.0854(19) 0.0114(13) 0.0330(14) 0.0078(13)
    N 0.0442(15) 0.0521(15) 0.0468(15) 0.0266(13) 0.0177(12) 0.0061(12)
    C1 0.057(2) 0.059(2) 0.053(2) 0.0252(17) 0.0200(16) 0.0039(16)
    C2 0.0468(19) 0.068(2) 0.055(2) 0.0298(17) 0.0112(16) 0.0000(17)
    C3 0.0512(19) 0.0525(18) 0.0517(19) 0.0341(16) 0.0260(15) 0.0161(15)
    C4 0.0480(19) 0.0451(18) 0.063(2) 0.0226(16) 0.0310(16) 0.0069(15)
    C5 0.0514(18) 0.0469(17) 0.0566(19) 0.0302(15) 0.0327(16) 0.0148(15)
    C6 0.078(2) 0.056(2) 0.075(3) 0.0383(19) 0.054(2) 0.0285(18)
    C7 0.095(3) 0.081(3) 0.063(2) 0.057(2) 0.049(2) 0.039(2)
    C8 0.073(2) 0.081(3) 0.051(2) 0.052(2) 0.0338(18) 0.0238(18)
    C9 0.0469(17) 0.0588(19) 0.0434(17) 0.0359(16) 0.0232(14) 0.0123(14)
    C10 0.0421(16) 0.0460(16) 0.0483(17) 0.0291(14) 0.0260(14) 0.0120(13)
    C11 0.0455(17) 0.0447(16) 0.0463(17) 0.0296(14) 0.0214(14) 0.0119(13)
    C12 0.0551(19) 0.0443(17) 0.062(2) 0.0293(15) 0.0328(16) 0.0171(15)
    C13 0.0434(18) 0.0478(18) 0.068(2) 0.0186(15) 0.0238(17) 0.0021(17)
    C14 0.0481(18) 0.065(2) 0.0490(19) 0.0339(17) 0.0190(15) 0.0025(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 C1 . 1.403(4) ?
    O1 H1A . 0.8200 ?
    O2 C3 . 1.216(4) ?
    O3 C4 . 1.214(4) ?
    N C2 . 1.470(4) ?
    N C3 . 1.383(4) ?
    N C4 . 1.404(4) ?
    C1 C2 . 1.515(5) ?
    C1 H1B . 0.9700 ?
    C1 H1C . 0.9700 ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C11 . 1.476(4) ?
    C4 C5 . 1.474(5) ?
    C5 C6 . 1.378(5) ?
    C5 C10 . 1.409(4) ?
    C6 C7 . 1.391(5) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.366(5) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.404(5) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.418(4) ?
    C9 C14 . 1.414(5) ?
    C10 C11 . 1.405(4) ?
    C11 C12 . 1.376(4) ?
    C12 C13 . 1.410(5) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.351(5) ?
    C13 H13A . 0.9300 ?
    C14 H14A . 0.9300 ?
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 H1A . . 109.5 ?
    C3 N C4 . . 124.6(3) ?
    C3 N C2 . . 118.3(3) ?
    C4 N C2 . . 117.1(3) ?
    O1 C1 C2 . . 114.2(3) ?
    O1 C1 H1B . . 108.7 ?
    C2 C1 H1B . . 108.7 ?
    O1 C1 H1C . . 108.7 ?
    C2 C1 H1C . . 108.7 ?
    H1B C1 H1C . . 107.6 ?
    N C2 C1 . . 113.5(3) ?
    N C2 H2A . . 108.9 ?
    C1 C2 H2A . . 108.9 ?
    N C2 H2B . . 108.9 ?
    C1 C2 H2B . . 108.9 ?
    H2A C2 H2B . . 107.7 ?
    O2 C3 N . . 120.7(3) ?
    O2 C3 C11 . . 121.9(3) ?
    N C3 C11 . . 117.4(3) ?
    O3 C4 N . . 119.8(3) ?
    O3 C4 C5 . . 123.0(3) ?
    N C4 C5 . . 117.2(3) ?
    C6 C5 C10 . . 120.1(3) ?
    C6 C5 C4 . . 120.1(3) ?
    C10 C5 C4 . . 119.8(3) ?
    C5 C6 C7 . . 120.4(3) ?
    C5 C6 H6A . . 119.8 ?
    C7 C6 H6A . . 119.8 ?
    C8 C7 C6 . . 120.9(3) ?
    C8 C7 H7A . . 119.6 ?
    C6 C7 H7A . . 119.6 ?
    C7 C8 C9 . . 120.4(3) ?
    C7 C8 H8A . . 119.8 ?
    C9 C8 H8A . . 119.8 ?
    C8 C9 C14 . . 122.6(3) ?
    C8 C9 C10 . . 119.2(3) ?
    C14 C9 C10 . . 118.2(3) ?
    C11 C10 C5 . . 120.9(3) ?
    C11 C10 C9 . . 120.0(3) ?
    C5 C10 C9 . . 119.1(3) ?
    C12 C11 C10 . . 119.9(3) ?
    C12 C11 C3 . . 120.0(3) ?
    C10 C11 C3 . . 120.1(3) ?
    C11 C12 C13 . . 120.1(3) ?
    C11 C12 H12A . . 119.9 ?
    C13 C12 H12A . . 119.9 ?
    C14 C13 C12 . . 120.7(3) ?
    C14 C13 H13A . . 119.7 ?
    C12 C13 H13A . . 119.7 ?
    C13 C14 C9 . . 121.1(3) ?
    C13 C14 H14A . . 119.4 ?
    C9 C14 H14A . . 119.4 ?
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
    C3 N C2 C1 . . . . 103.2(4) ?
    C4 N C2 C1 . . . . -78.1(4) ?
    O1 C1 C2 N . . . . -64.6(4) ?
    C4 N C3 O2 . . . . 180.0(3) ?
    C2 N C3 O2 . . . . -1.4(4) ?
    C4 N C3 C11 . . . . 0.5(4) ?
    C2 N C3 C11 . . . . 179.1(2) ?
    C3 N C4 O3 . . . . 179.1(3) ?
    C2 N C4 O3 . . . . 0.5(4) ?
    C3 N C4 C5 . . . . -1.2(4) ?
    C2 N C4 C5 . . . . -179.9(2) ?
    O3 C4 C5 C6 . . . . 2.0(5) ?
    N C4 C5 C6 . . . . -177.7(3) ?
    O3 C4 C5 C10 . . . . -179.6(3) ?
    N C4 C5 C10 . . . . 0.8(4) ?
    C10 C5 C6 C7 . . . . 0.1(5) ?
    C4 C5 C6 C7 . . . . 178.5(3) ?
    C5 C6 C7 C8 . . . . 0.0(5) ?
    C6 C7 C8 C9 . . . . 0.2(5) ?
    C7 C8 C9 C14 . . . . 178.9(3) ?
    C7 C8 C9 C10 . . . . -0.6(5) ?
    C6 C5 C10 C11 . . . . 178.8(3) ?
    C4 C5 C10 C11 . . . . 0.4(4) ?
    C6 C5 C10 C9 . . . . -0.4(4) ?
    C4 C5 C10 C9 . . . . -178.9(2) ?
    C8 C9 C10 C11 . . . . -178.6(3) ?
    C14 C9 C10 C11 . . . . 1.9(4) ?
    C8 C9 C10 C5 . . . . 0.7(4) ?
    C14 C9 C10 C5 . . . . -178.9(2) ?
    C5 C10 C11 C12 . . . . 179.1(2) ?
    C9 C10 C11 C12 . . . . -1.6(4) ?
    C5 C10 C11 C3 . . . . -1.1(4) ?
    C9 C10 C11 C3 . . . . 178.1(2) ?
    O2 C3 C11 C12 . . . . 1.0(4) ?
    N C3 C11 C12 . . . . -179.6(3) ?
    O2 C3 C11 C10 . . . . -178.8(3) ?
    N C3 C11 C10 . . . . 0.7(4) ?
    C10 C11 C12 C13 . . . . 0.2(4) ?
    C3 C11 C12 C13 . . . . -179.5(3) ?
    C11 C12 C13 C14 . . . . 0.9(4) ?
    C12 C13 C14 C9 . . . . -0.6(5) ?
    C8 C9 C14 C13 . . . . 179.7(3) ?
    C10 C9 C14 C13 . . . . -0.8(4) ?
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 H1A O2 2_665 0.82 1.97 2.771(4) 165
    C2 H2A O2 . 0.97 2.31 2.714(5) 104
