#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222047.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222047
loop_
_publ_author_name
'Sun, Jie'
'Yuan, Ai-lin'
'Wang, Hai-Bo'
'Sun, Jie'
_publ_section_title
;
 N-(2-Hydroxyethyl)-1,8-naphthalimide
;
_journal_coeditor_code           HK2674
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1210
_journal_paper_doi               10.1107/S1600536809015621
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H11 N O3'
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_melting_point          413
_chemical_name_common            N-(2-Hydroxyethyl)-1,8-naphthalimide
_chemical_name_systematic
;
N-(2-Hydroxyethyl)naphthalene-1,8-dicarboximide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.760(19)
_cell_angle_beta                 109.94(3)
_cell_angle_gamma                114.60(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5480(15)
_cell_length_b                   8.8300(18)
_cell_length_c                   10.101(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     548.2(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2159
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.307
_refine_ls_extinction_coef       0.035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1P)²+0.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.2079
_reflns_number_gt                1330
_reflns_number_total             1995
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2674.cif
_cod_data_source_block           I
_cod_database_code               2222047
_cod_database_fobs_code          2222047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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 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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 194302
