##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.1.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2007-10-25
_journal_date_accepted     2007-12-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o263
_journal_page_last     o263
_journal_paper_category     QO
_journal_coeditor_code     EZ2108
_publ_contact_author_name     'Fang-Fang Jian'
_publ_contact_author_address
;
New Materials and Function Coordination Chemistry Laboratory
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
_publ_contact_author_email     ffj2003@163169.net
_publ_contact_author_fax     '86-532-84023606'
_publ_contact_author_phone     '86-532-84023606'
_publ_section_title
;
N-(4-Aminophenyl)-1,8-naphthalimide hemihydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Fang-Fang Jian' .
;
New Materials and Functional Coordination Chemistry Laboratory
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
    'Li-Ming Wang' .
;
New Materials and Functional Coordination Chemistry Laboratory
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
    'Li Du' .
;
New Materials and Functional Coordination Chemistry Laboratory
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
    'Jing Wang' .
;
New Materials and Functional Coordination Chemistry Laboratory
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(4-Aminophenyl)-1,8-naphthalimide hemihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H12 N2 O2, 0.5H2 O'
_chemical_formula_sum     'C18 H13 N2 O2.5'
_chemical_formula_iupac     'C18 H12 N2 O2, 0.5H2 O'
_chemical_formula_weight     297.31
_chemical_melting_point     286
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'A b a 2'
_symmetry_space_group_name_Hall     'A2 -2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z'
    'x, y+1/2, z+1/2'
    '-x, -y+1/2, z+1/2'
    'x+1/2, -y+1, z+1/2'
    '-x+1/2, y+1, z+1/2'
_cell_length_a     22.926(5)
_cell_length_b     17.930(4)
_cell_length_c     6.8360(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2810.0(10)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     512
_cell_measurement_theta_min     2
_cell_measurement_theta_max     22
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.406
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1240
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(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
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5656
_diffrn_reflns_av_R_equivalents     0.0266
_diffrn_reflns_av_sigmaI/netI     0.0298
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     24.99
_diffrn_reflns_theta_full     24.99
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -27
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -20
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     7
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     ?
_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 > 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     1359
_reflns_number_gt     1308
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0716
_refine_ls_R_factor_gt     0.0691
_refine_ls_wR_factor_gt     0.1623
_refine_ls_wR_factor_ref     0.1637
_refine_ls_goodness_of_fit_ref     1.331
_refine_ls_restrained_S_all     1.331
_refine_ls_number_reflns     1359
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.062P)²+2.2916P] 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     0.237
_refine_diff_density_min     -0.211
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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     'NRCVAX (Gabe et al.,  1989)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.42928(16) 0.07821(19) 0.8275(7) 0.0704(12) Uani d . 1 . .
    O O2 0.27279(15) 0.22571(18) 0.9326(8) 0.0675(12) Uani d . 1 . .
    N N1 0.35109(17) 0.15181(19) 0.8761(6) 0.0447(10) Uani d . 1 . .
    N N2 0.4972(2) 0.3999(3) 0.9511(11) 0.095(2) Uani d . 1 . .
    H H2A 0.5002 0.4314 0.8566 0.115 Uiso calc R 1 . .
    H H2B 0.5170 0.4064 1.0567 0.115 Uiso calc R 1 . .
    C C1 0.2903(2) 0.1646(3) 0.8953(8) 0.0502(13) Uani d . 1 . .
    C C2 0.2527(2) 0.0997(2) 0.8651(7) 0.0481(12) Uani d . 1 . .
    C C3 0.1932(2) 0.1090(3) 0.8646(8) 0.0609(15) Uani d . 1 . .
    H H3A 0.1772 0.1563 0.8800 0.073 Uiso calc R 1 . .
    C C4 0.1569(3) 0.0475(4) 0.8411(10) 0.080(2) Uani d . 1 . .
    H H4A 0.1167 0.0543 0.8394 0.096 Uiso calc R 1 . .
    C C5 0.1787(3) -0.0214(4) 0.8208(10) 0.080(2) Uani d . 1 . .
    H H5A 0.1533 -0.0616 0.8090 0.096 Uiso calc R 1 . .
    C C6 0.2396(3) -0.0341(3) 0.8168(9) 0.0641(16) Uani d . 1 . .
    C C7 0.2649(4) -0.1041(3) 0.7944(10) 0.082(2) Uani d . 1 . .
    H H7A 0.2409 -0.1457 0.7839 0.099 Uiso calc R 1 . .
    C C8 0.3234(4) -0.1134(3) 0.7875(11) 0.083(2) Uani d . 1 . .
    H H8A 0.3391 -0.1610 0.7732 0.100 Uiso calc R 1 . .
    C C9 0.3604(3) -0.0517(3) 0.8017(9) 0.0669(16) Uani d . 1 . .
    H H9A 0.4005 -0.0581 0.7927 0.080 Uiso calc R 1 . .
    C C10 0.3376(3) 0.0183(3) 0.8289(8) 0.0538(13) Uani d . 1 . .
    C C11 0.2765(2) 0.0281(3) 0.8369(8) 0.0509(12) Uani d . 1 . .
    C C12 0.3765(2) 0.0826(2) 0.8410(8) 0.0512(13) Uani d . 1 . .
    C C13 0.3889(2) 0.2158(3) 0.8965(9) 0.0522(14) Uani d . 1 . .
    C C14 0.4212(2) 0.2260(3) 1.0623(10) 0.0602(15) Uani d . 1 . .
    H H14A 0.4190 0.1914 1.1632 0.072 Uiso calc R 1 . .
    C C15 0.4569(3) 0.2869(3) 1.0813(11) 0.0629(15) Uani d . 1 . .
    H H15A 0.4787 0.2932 1.1949 0.075 Uiso calc R 1 . .
    C C16 0.4609(2) 0.3390(3) 0.9330(10) 0.0577(14) Uani d . 1 . .
    C C17 0.4289(2) 0.3279(3) 0.7643(9) 0.0565(14) Uani d . 1 . .
    H H17A 0.4319 0.3619 0.6619 0.068 Uiso calc R 1 . .
    C C18 0.3928(2) 0.2670(3) 0.7466(9) 0.0544(14) Uani d . 1 . .
    H H18A 0.3710 0.2603 0.6332 0.065 Uiso calc R 1 . .
    O O1W 0.5000 0.0000 0.0917(13) 0.089(2) Uani d S 1 . .
    H H1W1 0.4830 0.0421 0.0966 0.107 Uiso d PR 0.50 . .
    H H2W1 0.5239 0.0012 -0.0033 0.107 Uiso d PR 0.50 . .
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 0.055(2) 0.063(2) 0.094(3) 0.0129(17) 0.011(3) 0.010(2)
    O2 0.067(2) 0.0447(18) 0.091(3) 0.0124(16) -0.001(3) 0.000(2)
    N1 0.053(2) 0.0357(18) 0.046(2) -0.0006(16) -0.004(2) 0.0032(18)
    N2 0.102(4) 0.079(3) 0.106(5) -0.039(3) -0.022(4) 0.011(4)
    C1 0.055(3) 0.045(2) 0.050(3) 0.009(2) -0.003(3) 0.005(2)
    C2 0.055(3) 0.055(2) 0.034(3) -0.004(2) -0.004(2) 0.010(2)
    C3 0.063(3) 0.078(4) 0.042(3) -0.004(3) -0.004(3) 0.009(3)
    C4 0.065(4) 0.116(5) 0.060(4) -0.028(4) -0.001(3) 0.021(4)
    C5 0.097(5) 0.087(4) 0.056(4) -0.044(4) -0.012(4) 0.018(4)
    C6 0.090(5) 0.059(3) 0.043(3) -0.027(3) -0.005(3) 0.013(3)
    C7 0.136(7) 0.052(3) 0.058(4) -0.030(4) -0.018(4) 0.013(3)
    C8 0.142(7) 0.042(3) 0.065(4) 0.002(4) -0.006(5) -0.001(3)
    C9 0.102(4) 0.047(3) 0.052(4) 0.008(3) 0.001(3) 0.001(3)
    C10 0.079(4) 0.037(2) 0.045(3) 0.003(2) 0.006(3) 0.011(2)
    C11 0.072(3) 0.048(3) 0.032(2) -0.007(2) -0.002(3) 0.008(2)
    C12 0.060(3) 0.043(3) 0.050(3) 0.010(2) 0.001(3) 0.007(2)
    C13 0.053(3) 0.038(2) 0.066(4) 0.004(2) 0.001(3) 0.004(3)
    C14 0.063(3) 0.055(3) 0.063(4) -0.002(3) -0.015(3) 0.012(3)
    C15 0.061(3) 0.058(3) 0.071(4) -0.006(3) -0.016(3) -0.003(3)
    C16 0.053(3) 0.045(3) 0.075(4) -0.007(2) 0.000(3) -0.007(3)
    C17 0.067(3) 0.039(2) 0.063(4) -0.003(2) -0.006(3) 0.012(3)
    C18 0.059(3) 0.044(3) 0.060(4) 0.000(2) -0.007(3) 0.001(3)
    O1W 0.098(5) 0.093(4) 0.078(4) 0.028(4) 0.000 0.000
_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 C12 . 1.217(6) y
    O2 C1 . 1.194(6) y
    N1 C12 . 1.391(6) ?
    N1 C1 . 1.419(6) ?
    N1 C13 . 1.445(6) ?
    N2 C16 . 1.379(6) ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    C1 C2 . 1.462(7) ?
    C2 C3 . 1.375(8) ?
    C2 C11 . 1.408(7) ?
    C3 C4 . 1.391(8) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.340(9) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.416(9) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.391(8) ?
    C6 C11 . 1.406(6) ?
    C7 C8 . 1.353(10) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.397(9) ?
    C8 H8A . 0.9300 ?
    C9 C10 . 1.372(7) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.413(7) ?
    C10 C12 . 1.461(7) ?
    C13 C14 . 1.366(8) ?
    C13 C18 . 1.379(7) ?
    C14 C15 . 1.371(7) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.381(8) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.381(8) ?
    C17 C18 . 1.375(7) ?
    C17 H17A . 0.9300 ?
    C18 H18A . 0.9300 ?
    O1W H1W1 . 0.8501 ?
    O1W H2W1 . 0.8501 ?
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
    C12 N1 C1 . . 124.8(4) ?
    C12 N1 C13 . . 118.3(4) ?
    C1 N1 C13 . . 116.9(4) ?
    C16 N2 H2A . . 120.0 ?
    C16 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    O2 C1 N1 . . 119.8(4) ?
    O2 C1 C2 . . 124.2(5) ?
    N1 C1 C2 . . 115.9(4) ?
    C3 C2 C11 . . 119.6(5) ?
    C3 C2 C1 . . 119.2(5) ?
    C11 C2 C1 . . 121.1(5) ?
    C2 C3 C4 . . 119.9(6) ?
    C2 C3 H3A . . 120.1 ?
    C4 C3 H3A . . 120.1 ?
    C5 C4 C3 . . 121.3(6) ?
    C5 C4 H4A . . 119.4 ?
    C3 C4 H4A . . 119.4 ?
    C4 C5 C6 . . 121.2(6) ?
    C4 C5 H5A . . 119.4 ?
    C6 C5 H5A . . 119.4 ?
    C7 C6 C11 . . 118.5(6) ?
    C7 C6 C5 . . 123.9(6) ?
    C11 C6 C5 . . 117.6(5) ?
    C8 C7 C6 . . 121.9(6) ?
    C8 C7 H7A . . 119.1 ?
    C6 C7 H7A . . 119.1 ?
    C7 C8 C9 . . 120.1(6) ?
    C7 C8 H8A . . 120.0 ?
    C9 C8 H8A . . 120.0 ?
    C10 C9 C8 . . 120.2(7) ?
    C10 C9 H9A . . 119.9 ?
    C8 C9 H9A . . 119.9 ?
    C9 C10 C11 . . 119.8(5) ?
    C9 C10 C12 . . 119.8(5) ?
    C11 C10 C12 . . 120.3(4) ?
    C6 C11 C2 . . 120.3(5) ?
    C6 C11 C10 . . 119.5(5) ?
    C2 C11 C10 . . 120.2(5) ?
    O1 C12 N1 . . 119.2(4) ?
    O1 C12 C10 . . 123.5(4) ?
    N1 C12 C10 . . 117.3(4) ?
    C14 C13 C18 . . 119.5(5) ?
    C14 C13 N1 . . 120.8(5) ?
    C18 C13 N1 . . 119.7(5) ?
    C13 C14 C15 . . 120.6(6) ?
    C13 C14 H14A . . 119.7 ?
    C15 C14 H14A . . 119.7 ?
    C14 C15 C16 . . 120.5(6) ?
    C14 C15 H15A . . 119.7 ?
    C16 C15 H15A . . 119.7 ?
    N2 C16 C17 . . 120.6(6) ?
    N2 C16 C15 . . 120.6(6) ?
    C17 C16 C15 . . 118.8(5) ?
    C18 C17 C16 . . 120.4(5) ?
    C18 C17 H17A . . 119.8 ?
    C16 C17 H17A . . 119.8 ?
    C17 C18 C13 . . 120.2(5) ?
    C17 C18 H18A . . 119.9 ?
    C13 C18 H18A . . 119.9 ?
    H1W1 O1W H2W1 . . 107.7 ?
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
    N2 H2A O1W 5 0.86 2.19 3.046(6) 171.5 y
    N2 H2B O1 6_655 0.86 2.24 3.099(5) 178.4 y
    O1W H1W1 O1 1_554 0.85 2.30 2.800(5) 117.6 y
    O1W H2W1 O1 2_654 0.85 2.12 2.800(5) 136.4 y
    C15 H15A Cg1 6 0.93 2.96 . 139.88 y
