#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/08/2230819.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_2230819
loop_
_publ_author_name
'Harrad, Mohamed Anoir'
'Boualy, Brahim'
'Oudahmane, Abdelghani'
'Avignant, Daniel'
'Rizzoli, Corrado'
_publ_section_title
;
 (Z)-4-(2-Naphthylamino)pent-3-en-2-one
;
_journal_coeditor_code           NG5187
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1818
_journal_paper_doi               10.1107/S1600536811024494
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H15 N O'
_chemical_formula_moiety         'C15 H15 N O'
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_chemical_name_systematic
;
(Z)-4-(2-Naphthylamino)pent-3-en-2-one
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2417(18)
_cell_length_b                   8.2532(10)
_cell_length_c                   26.570(4)
_cell_measurement_reflns_used    1094
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.41
_cell_measurement_theta_min      3.07
_cell_volume                     2465.2(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and SCHAKAL97
(Keller, 1997)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PARST95 (Nardelli,
1995)'
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9535
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS, Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.151
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0498
_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)+(0.0749P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                1179
_reflns_number_total             2221
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng5187.cif
_cod_data_source_block           I
_cod_database_code               2230819
_cod_database_fobs_code          2230819
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
-x,y+1/2,-z+1/2
x+1/2,-y+1/2,-z
-x,-y,-z
x-1/2,y,-z-1/2
x,-y-1/2,z-1/2
-x-1/2,y-1/2,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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.37331(17) 0.7158(2) 0.48799(6) 0.0702(6) Uani d . 1 1 . .
N N1 0.3060(2) 0.5679(2) 0.57214(7) 0.0544(6) Uani d . 1 1 . .
H H1N 0.359(2) 0.602(3) 0.5479(9) 0.081(9) Uiso d . 1 1 . .
C C1 0.3453(2) 0.5091(3) 0.61903(8) 0.0468(6) Uani d . 1 1 . .
C C2 0.2893(2) 0.5426(3) 0.66352(8) 0.0526(6) Uani d . 1 1 . .
H H2 0.2212 0.6066 0.6633 0.063 Uiso calc R 1 1 . .
C C3 0.3326(2) 0.4819(2) 0.70984(8) 0.0465(6) Uani d . 1 1 . .
C C4 0.2751(2) 0.5120(3) 0.75613(9) 0.0616(7) Uani d . 1 1 . .
H H4 0.2051 0.5722 0.7566 0.074 Uiso calc R 1 1 . .
C C5 0.3207(3) 0.4541(3) 0.80021(9) 0.0713(8) Uani d . 1 1 . .
H H5 0.2816 0.4749 0.8304 0.086 Uiso calc R 1 1 . .
C C6 0.4261(3) 0.3634(3) 0.80025(10) 0.0714(8) Uani d . 1 1 . .
H H6 0.4565 0.3241 0.8304 0.086 Uiso calc R 1 1 . .
C C7 0.4840(2) 0.3327(3) 0.75657(10) 0.0646(7) Uani d . 1 1 . .
H H7 0.5540 0.2727 0.7571 0.077 Uiso calc R 1 1 . .
C C8 0.4395(2) 0.3907(2) 0.71006(8) 0.0489(6) Uani d . 1 1 . .
C C9 0.4972(2) 0.3633(3) 0.66390(9) 0.0573(7) Uani d . 1 1 . .
H H9 0.5681 0.3050 0.6635 0.069 Uiso calc R 1 1 . .
C C10 0.4518(2) 0.4200(2) 0.61962(8) 0.0546(6) Uani d . 1 1 . .
H H10 0.4917 0.3996 0.5896 0.065 Uiso calc R 1 1 . .
C C11 0.0924(2) 0.5082(3) 0.58249(9) 0.0661(7) Uani d . 1 1 . .
H H11A 0.0820 0.5612 0.6143 0.099 Uiso calc R 1 1 . .
H H11B 0.1095 0.3956 0.5879 0.099 Uiso calc R 1 1 . .
H H11C 0.0209 0.5183 0.5630 0.099 Uiso calc R 1 1 . .
C C12 0.1937(2) 0.5854(3) 0.55465(8) 0.0517(6) Uani d . 1 1 . .
C C13 0.1742(2) 0.6647(3) 0.50990(8) 0.0563(7) Uani d . 1 1 . .
H H13 0.0958 0.6769 0.4993 0.068 Uiso calc R 1 1 . .
C C14 0.2644(3) 0.7286(3) 0.47888(9) 0.0574(7) Uani d . 1 1 . .
C C15 0.2277(3) 0.8137(3) 0.43102(9) 0.0835(9) Uani d . 1 1 . .
H H15A 0.2948 0.8702 0.4172 0.125 Uiso calc R 1 1 . .
H H15B 0.1654 0.8897 0.4383 0.125 Uiso calc R 1 1 . .
H H15C 0.1995 0.7353 0.4071 0.125 Uiso calc R 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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
C12 N1 C1 . . 129.3(2) ?
C12 N1 H1N . . 109.5(16) ?
C1 N1 H1N . . 121.1(16) ?
C2 C1 C10 . . 119.2(2) ?
C2 C1 N1 . . 123.4(2) ?
C10 C1 N1 . . 117.24(19) ?
C1 C2 C3 . . 121.4(2) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C4 C3 C2 . . 122.5(2) ?
C4 C3 C8 . . 118.6(2) ?
C2 C3 C8 . . 118.90(19) ?
C5 C4 C3 . . 120.9(2) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 120.4(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C7 C6 C5 . . 120.3(2) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 121.0(2) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 122.9(2) ?
C9 C8 C3 . . 118.25(19) ?
C7 C8 C3 . . 118.8(2) ?
C10 C9 C8 . . 121.6(2) ?
C10 C9 H9 . . 119.2 ?
C8 C9 H9 . . 119.2 ?
C9 C10 C1 . . 120.5(2) ?
C9 C10 H10 . . 119.7 ?
C1 C10 H10 . . 119.7 ?
C12 C11 H11A . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C12 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N1 C12 C13 . . 119.8(2) ?
N1 C12 C11 . . 119.6(2) ?
C13 C12 C11 . . 120.5(2) ?
C12 C13 C14 . . 124.7(2) ?
C12 C13 H13 . . 117.7 ?
C14 C13 H13 . . 117.7 ?
O1 C14 C13 . . 124.0(2) ?
O1 C14 C15 . . 118.0(2) ?
C13 C14 C15 . . 118.0(2) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 C14 . 1.252(3) ?
N1 C12 . 1.353(3) ?
N1 C1 . 1.408(3) ?
N1 H1N . 0.92(3) ?
C1 C2 . 1.368(3) ?
C1 C10 . 1.405(3) ?
C2 C3 . 1.415(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.412(3) ?
C3 C8 . 1.418(3) ?
C4 C5 . 1.365(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.401(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.354(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.416(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.406(3) ?
C9 C10 . 1.365(3) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.500(3) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.375(3) ?
C13 C14 . 1.410(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.510(3) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
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
N1 H1N O1 . 0.92(2) 1.85(2) 2.657(2) 144(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4552970
