#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/87/2228773.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_2228773
loop_
_publ_author_name
'Farag, Abeer Mohamed'
'Teoh, Siang Guan'
'Osman, Hasnah'
'Hemamalini, Madhukar'
'Fun, Hoong-Kun'
_publ_section_title
;
 3-{(E)-[(4-Formylphenyl)iminiumyl]methyl}naphthalen-2-olate
;
_journal_coeditor_code           IS2641
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o143
_journal_paper_doi               10.1107/S1600536810051822
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H13 N O2'
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29
_chemical_name_systematic
;
3-{(E)-[(4-Formylphenyl)iminiumyl]methyl}naphthalen-2-olate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.979(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3685(8)
_cell_length_b                   12.7437(13)
_cell_length_c                   14.4586(15)
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      3.19
_cell_volume                     1356.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11574
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0799P)²+0.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                1416
_reflns_number_total             2394
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is2641.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228773
_cod_database_fobs_code          2228773
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.6211(3) -0.00216(15) 0.67024(13) 0.0694(7) Uani d . 1 . .
O O2 0.9842(4) -0.31405(18) 0.16917(18) 0.0913(8) Uani d . 1 . .
N N1 0.7418(3) -0.02531(16) 0.50829(17) 0.0496(6) Uani d . 1 . .
C C1 0.6323(4) 0.0967(2) 0.65940(19) 0.0527(7) Uani d . 1 . .
C C2 0.5864(4) 0.1658(2) 0.73351(19) 0.0578(8) Uani d . 1 . .
H H2 0.5496 0.1373 0.7890 0.069 Uiso calc R 1 . .
C C3 0.5952(4) 0.2702(2) 0.72465(19) 0.0563(8) Uani d . 1 . .
H H3 0.5634 0.3119 0.7743 0.068 Uiso calc R 1 . .
C C4 0.6515(4) 0.3201(2) 0.64209(19) 0.0503(7) Uani d . 1 . .
C C5 0.6622(4) 0.4289(2) 0.6367(2) 0.0673(9) Uani d . 1 . .
H H4 0.6302 0.4692 0.6872 0.081 Uiso calc R 1 . .
C C6 0.7185(5) 0.4774(2) 0.5590(2) 0.0804(11) Uani d . 1 . .
H H5 0.7255 0.5502 0.5564 0.096 Uiso calc R 1 . .
C C7 0.7654(5) 0.4169(2) 0.4837(2) 0.0752(10) Uani d . 1 . .
H H6 0.8034 0.4496 0.4302 0.090 Uiso calc R 1 . .
C C8 0.7564(4) 0.3100(2) 0.4871(2) 0.0587(8) Uani d . 1 . .
H H7 0.7884 0.2712 0.4356 0.070 Uiso calc R 1 . .
C C9 0.7000(3) 0.25724(19) 0.56633(17) 0.0450(7) Uani d . 1 . .
C C10 0.6907(3) 0.14332(19) 0.57427(17) 0.0448(7) Uani d . 1 . .
C C11 0.7430(3) 0.07881(19) 0.50285(18) 0.0463(7) Uani d . 1 . .
H H11A 0.7807 0.1098 0.4485 0.056 Uiso calc R 1 . .
C C12 0.7929(3) -0.09668(18) 0.44023(18) 0.0440(7) Uani d . 1 . .
C C13 0.7754(4) -0.20274(19) 0.46048(19) 0.0524(7) Uani d . 1 . .
H H13A 0.7329 -0.2236 0.5175 0.063 Uiso calc R 1 . .
C C14 0.8209(4) -0.2768(2) 0.39614(19) 0.0537(7) Uani d . 1 . .
H H14A 0.8092 -0.3476 0.4104 0.064 Uiso calc R 1 . .
C C15 0.8834(3) -0.24824(19) 0.31103(18) 0.0455(7) Uani d . 1 . .
C C16 0.9013(4) -0.1417(2) 0.29133(19) 0.0534(7) Uani d . 1 . .
H H16A 0.9443 -0.1212 0.2344 0.064 Uiso calc R 1 . .
C C17 0.8566(4) -0.0671(2) 0.35455(18) 0.0513(7) Uani d . 1 . .
H H17A 0.8688 0.0037 0.3403 0.062 Uiso calc R 1 . .
C C18 0.9279(4) -0.3289(2) 0.2450(2) 0.0625(8) Uani d . 1 . .
H H18A 0.9115 -0.3982 0.2629 0.075 Uiso calc R 1 . .
H H1N1 0.698(4) -0.048(2) 0.570(2) 0.086(10) Uiso d . 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
C11 N1 C12 . . 127.2(2) ?
C11 N1 H1N1 . . 110.3(17) ?
C12 N1 H1N1 . . 122.6(17) ?
O1 C1 C2 . . 119.8(2) ?
O1 C1 C10 . . 122.3(2) ?
C2 C1 C10 . . 117.9(2) ?
C3 C2 C1 . . 121.7(3) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C2 C3 C4 . . 122.7(3) ?
C2 C3 H3 . . 118.7 ?
C4 C3 H3 . . 118.7 ?
C5 C4 C9 . . 120.3(3) ?
C5 C4 C3 . . 120.7(3) ?
C9 C4 C3 . . 119.0(2) ?
C6 C5 C4 . . 121.3(3) ?
C6 C5 H4 . . 119.3 ?
C4 C5 H4 . . 119.3 ?
C5 C6 C7 . . 119.1(3) ?
C5 C6 H5 . . 120.5 ?
C7 C6 H5 . . 120.5 ?
C8 C7 C6 . . 120.9(3) ?
C8 C7 H6 . . 119.6 ?
C6 C7 H6 . . 119.6 ?
C7 C8 C9 . . 121.6(3) ?
C7 C8 H7 . . 119.2 ?
C9 C8 H7 . . 119.2 ?
C8 C9 C4 . . 116.8(2) ?
C8 C9 C10 . . 123.9(2) ?
C4 C9 C10 . . 119.3(2) ?
C11 C10 C1 . . 119.3(2) ?
C11 C10 C9 . . 121.2(2) ?
C1 C10 C9 . . 119.5(2) ?
N1 C11 C10 . . 123.1(2) ?
N1 C11 H11A . . 118.5 ?
C10 C11 H11A . . 118.5 ?
C13 C12 C17 . . 119.2(2) ?
C13 C12 N1 . . 117.0(2) ?
C17 C12 N1 . . 123.8(2) ?
C14 C13 C12 . . 119.9(2) ?
C14 C13 H13A . . 120.1 ?
C12 C13 H13A . . 120.1 ?
C13 C14 C15 . . 121.4(2) ?
C13 C14 H14A . . 119.3 ?
C15 C14 H14A . . 119.3 ?
C14 C15 C16 . . 118.4(2) ?
C14 C15 C18 . . 119.5(2) ?
C16 C15 C18 . . 122.1(3) ?
C17 C16 C15 . . 120.9(2) ?
C17 C16 H16A . . 119.5 ?
C15 C16 H16A . . 119.5 ?
C16 C17 C12 . . 120.2(2) ?
C16 C17 H17A . . 119.9 ?
C12 C17 H17A . . 119.9 ?
O2 C18 C15 . . 125.7(3) ?
O2 C18 H18A . . 117.2 ?
C15 C18 H18A . . 117.2 ?
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 . 1.272(3) ?
O2 C18 . 1.201(3) ?
N1 C11 . 1.329(3) ?
N1 C12 . 1.401(3) ?
N1 H1N1 . 1.00(3) ?
C1 C2 . 1.437(4) ?
C1 C10 . 1.446(3) ?
C2 C3 . 1.338(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.427(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.390(4) ?
C4 C9 . 1.413(3) ?
C5 C6 . 1.359(4) ?
C5 H4 . 0.9300 ?
C6 C7 . 1.389(4) ?
C6 H5 . 0.9300 ?
C7 C8 . 1.364(4) ?
C7 H6 . 0.9300 ?
C8 C9 . 1.404(4) ?
C8 H7 . 0.9300 ?
C9 C10 . 1.458(3) ?
C10 C11 . 1.385(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.390(3) ?
C12 C17 . 1.392(3) ?
C13 C14 . 1.374(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.378(4) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.394(3) ?
C15 C18 . 1.448(4) ?
C16 C17 . 1.367(3) ?
C16 H16A . 0.9300 ?
C17 H17A . 0.9300 ?
C18 H18A . 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
_geom_hbond_publ_flag
N1 H1N1 O1 . 1.00(3) 1.68(3) 2.551(3) 143(2) yes
C8 H7 O2 2_755 0.93 2.54 3.399(4) 153 yes
C17 H17A O2 2_755 0.93 2.57 3.453(4) 159 yes
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
O1 C1 C2 C3 . . . . -179.6(3) ?
C10 C1 C2 C3 . . . . 0.6(4) ?
C1 C2 C3 C4 . . . . -0.4(4) ?
C2 C3 C4 C5 . . . . -178.7(3) ?
C2 C3 C4 C9 . . . . 0.0(4) ?
C9 C4 C5 C6 . . . . 0.2(5) ?
C3 C4 C5 C6 . . . . 178.9(3) ?
C4 C5 C6 C7 . . . . 0.3(5) ?
C5 C6 C7 C8 . . . . -0.3(5) ?
C6 C7 C8 C9 . . . . -0.1(5) ?
C7 C8 C9 C4 . . . . 0.6(4) ?
C7 C8 C9 C10 . . . . -179.0(3) ?
C5 C4 C9 C8 . . . . -0.6(4) ?
C3 C4 C9 C8 . . . . -179.3(2) ?
C5 C4 C9 C10 . . . . 178.9(2) ?
C3 C4 C9 C10 . . . . 0.2(4) ?
O1 C1 C10 C11 . . . . -2.4(4) ?
C2 C1 C10 C11 . . . . 177.4(2) ?
O1 C1 C10 C9 . . . . 179.8(2) ?
C2 C1 C10 C9 . . . . -0.3(4) ?
C8 C9 C10 C11 . . . . 1.7(4) ?
C4 C9 C10 C11 . . . . -177.8(2) ?
C8 C9 C10 C1 . . . . 179.4(3) ?
C4 C9 C10 C1 . . . . -0.1(3) ?
C12 N1 C11 C10 . . . . -179.6(2) ?
C1 C10 C11 N1 . . . . 0.2(4) ?
C9 C10 C11 N1 . . . . 177.9(2) ?
C11 N1 C12 C13 . . . . -178.2(2) ?
C11 N1 C12 C17 . . . . 0.8(4) ?
C17 C12 C13 C14 . . . . 0.0(4) ?
N1 C12 C13 C14 . . . . 179.1(2) ?
C12 C13 C14 C15 . . . . -0.3(4) ?
C13 C14 C15 C16 . . . . 0.5(4) ?
C13 C14 C15 C18 . . . . -179.4(3) ?
C14 C15 C16 C17 . . . . -0.5(4) ?
C18 C15 C16 C17 . . . . 179.3(3) ?
C15 C16 C17 C12 . . . . 0.3(4) ?
C13 C12 C17 C16 . . . . 0.0(4) ?
N1 C12 C17 C16 . . . . -179.1(2) ?
C14 C15 C18 O2 . . . . -179.6(3) ?
C16 C15 C18 O2 . . . . 0.5(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656424
