#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239556.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_2239556
loop_
_publ_author_name
'Khelifa Baghdouche, Ammar'
'Mosbah, Salima'
'Belhocine, Youghourta'
'Bencharif, Leïla'
_publ_section_title
;
 Zwitterionic
 1-{(E)-[(2-methylphenyl)iminiumyl]methyl}naphthalen-2-olate
;
_journal_coeditor_code           HB7171
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o676
_journal_paper_doi               10.1107/S1600536814008794
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H15 N O'
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_chemical_name_systematic
;
1-{(E)-[(2-Methylphenyl)iminiumyl]methyl}naphthalen-2-olate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3627(5)
_cell_length_b                   12.4007(10)
_cell_length_c                   14.4365(12)
_cell_measurement_reflns_used    3889
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.82
_cell_volume                     1318.09(18)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14320
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.187
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.2897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.103
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                1439
_reflns_number_total             1721
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7171sup1.cf
_cod_data_source_block           I
_cod_database_code               2239556
_cod_database_fobs_code          2239556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
O O1 0.9691(3) 0.33259(13) 0.36389(11) 0.0330(4) Uani d . 1 1
C C2 0.9303(3) 0.23027(19) 0.36261(17) 0.0263(5) Uani d . 1 1
C C3 0.9485(3) 0.1707(2) 0.27755(17) 0.0285(5) Uani d . 1 1
H H3 0.9881 0.2069 0.2232 0.034 Uiso calc R 1 1
C C4 0.9106(3) 0.06523(19) 0.27381(16) 0.0278(5) Uani d . 1 1
H H4 0.925 0.0282 0.2167 0.033 Uiso calc R 1 1
C C5 0.8489(3) 0.00629(18) 0.35345(16) 0.0241(5) Uani d . 1 1
C C6 0.8096(4) -0.10430(19) 0.34660(18) 0.0312(6) Uani d . 1 1
H H6 0.8193 -0.1391 0.288 0.037 Uiso calc R 1 1
C C7 0.7575(4) -0.16291(19) 0.42255(17) 0.0338(6) Uani d . 1 1
H H7 0.734 -0.238 0.4173 0.041 Uiso calc R 1 1
C C8 0.7395(4) -0.11076(18) 0.50764(17) 0.0301(6) Uani d . 1 1
H H8 0.7034 -0.151 0.5605 0.036 Uiso calc R 1 1
C C9 0.7730(3) -0.00172(18) 0.51646(16) 0.0251(5) Uani d . 1 1
H H9 0.7577 0.0322 0.5749 0.03 Uiso calc R 1 1
C C10 0.8301(3) 0.06008(17) 0.43913(15) 0.0215(5) Uani d . 1 1
C C11 0.8716(3) 0.17464(18) 0.44429(16) 0.0220(5) Uani d . 1 1
C C12 0.8560(3) 0.23193(18) 0.52831(16) 0.0234(5) Uani d . 1 1
H H12 0.8199 0.1937 0.5823 0.028 Uiso calc R 1 1
N N13 0.8891(3) 0.33555(15) 0.53540(13) 0.0240(4) Uani d . 1 1
H H13 0.9142 0.3715 0.4844 0.029 Uiso calc R 1 1
C C14 0.8867(3) 0.39324(17) 0.62052(15) 0.0231(5) Uani d . 1 1
C C15 0.9417(3) 0.34405(19) 0.70234(17) 0.0274(5) Uani d . 1 1
H H15 0.98 0.2709 0.7018 0.033 Uiso calc R 1 1
C C16 0.9410(4) 0.4015(2) 0.78481(18) 0.0317(6) Uani d . 1 1
H H16 0.9789 0.368 0.8407 0.038 Uiso calc R 1 1
C C17 0.8846(4) 0.5081(2) 0.78508(18) 0.0331(6) Uani d . 1 1
H H17 0.8822 0.5475 0.8415 0.04 Uiso calc R 1 1
C C18 0.8319(4) 0.55710(19) 0.70344(18) 0.0313(6) Uani d . 1 1
H H18 0.7946 0.6304 0.7046 0.038 Uiso calc R 1 1
C C19 0.8321(3) 0.50159(18) 0.61949(16) 0.0257(5) Uani d . 1 1
C C20 0.7722(4) 0.55641(19) 0.53136(18) 0.0325(6) Uani d . 1 1
H H20A 0.8649 0.5461 0.4834 0.049 Uiso calc R 1 1
H H20B 0.7558 0.6337 0.5429 0.049 Uiso calc R 1 1
H H20C 0.6571 0.5251 0.5105 0.049 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
C C 0.0033 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
O1 C2 C11 121.6(2)
O1 C2 C3 119.5(2)
C11 C2 C3 118.9(2)
C4 C3 C2 121.1(2)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 122.1(2)
C3 C4 H4 119
C5 C4 H4 119
C6 C5 C10 120.2(2)
C6 C5 C4 120.4(2)
C10 C5 C4 119.5(2)
C7 C6 C5 121.3(2)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C8 119.0(2)
C6 C7 H7 120.5
C8 C7 H7 120.5
C9 C8 C7 121.2(2)
C9 C8 H8 119.4
C7 C8 H8 119.4
C8 C9 C10 120.7(2)
C8 C9 H9 119.7
C10 C9 H9 119.7
C5 C10 C9 117.6(2)
C5 C10 C11 119.1(2)
C9 C10 C11 123.3(2)
C12 C11 C2 119.3(2)
C12 C11 C10 121.2(2)
C2 C11 C10 119.4(2)
N13 C12 C11 123.1(2)
N13 C12 H12 118.5
C11 C12 H12 118.5
C12 N13 C14 123.91(19)
C12 N13 H13 118
C14 N13 H13 118
C15 C14 C19 120.9(2)
C15 C14 N13 120.7(2)
C19 C14 N13 118.4(2)
C16 C15 C14 120.2(2)
C16 C15 H15 119.9
C14 C15 H15 119.9
C17 C16 C15 119.6(2)
C17 C16 H16 120.2
C15 C16 H16 120.2
C18 C17 C16 120.1(2)
C18 C17 H17 120
C16 C17 H17 120
C17 C18 C19 121.6(2)
C17 C18 H18 119.2
C19 C18 H18 119.2
C18 C19 C14 117.7(2)
C18 C19 C20 120.7(2)
C14 C19 C20 121.6(2)
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.301(3)
C2 C11 1.433(3)
C2 C3 1.439(3)
C3 C4 1.339(3)
C3 H3 0.95
C4 C5 1.436(3)
C4 H4 0.95
C5 C6 1.405(3)
C5 C10 1.412(3)
C6 C7 1.370(3)
C6 H6 0.95
C7 C8 1.395(3)
C7 H7 0.95
C8 C9 1.380(3)
C8 H8 0.95
C9 C10 1.418(3)
C9 H9 0.95
C10 C11 1.455(3)
C11 C12 1.410(3)
C12 N13 1.312(3)
C12 H12 0.95
N13 C14 1.422(3)
N13 H13 0.88
C14 C15 1.390(3)
C14 C19 1.403(3)
C15 C16 1.387(3)
C15 H15 0.95
C16 C17 1.385(3)
C16 H16 0.95
C17 C18 1.382(4)
C17 H17 0.95
C18 C19 1.394(3)
C18 H18 0.95
C19 C20 1.508(3)
C20 H20A 0.98
C20 H20B 0.98
C20 H20C 0.98
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N13 H13 O1 0.88 1.85 2.546(3) 134 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
O1 C2 C3 C4 179.7(2)
C11 C2 C3 C4 0.4(4)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 179.7(2)
C3 C4 C5 C10 -1.1(4)
C10 C5 C6 C7 -1.8(4)
C4 C5 C6 C7 177.4(2)
C5 C6 C7 C8 1.5(4)
C6 C7 C8 C9 0.0(4)
C7 C8 C9 C10 -1.1(4)
C6 C5 C10 C9 0.7(3)
C4 C5 C10 C9 -178.5(2)
C6 C5 C10 C11 -180.0(2)
C4 C5 C10 C11 0.8(3)
C8 C9 C10 C5 0.7(3)
C8 C9 C10 C11 -178.6(2)
O1 C2 C11 C12 -0.2(4)
C3 C2 C11 C12 179.0(2)
O1 C2 C11 C10 -179.9(2)
C3 C2 C11 C10 -0.6(3)
C5 C10 C11 C12 -179.6(2)
C9 C10 C11 C12 -0.4(3)
C5 C10 C11 C2 0.0(3)
C9 C10 C11 C2 179.3(2)
C2 C11 C12 N13 1.6(3)
C10 C11 C12 N13 -178.8(2)
C11 C12 N13 C14 -175.4(2)
C12 N13 C14 C15 33.7(3)
C12 N13 C14 C19 -148.0(2)
C19 C14 C15 C16 0.9(4)
N13 C14 C15 C16 179.2(2)
C14 C15 C16 C17 0.1(4)
C15 C16 C17 C18 -0.9(4)
C16 C17 C18 C19 0.6(4)
C17 C18 C19 C14 0.4(4)
C17 C18 C19 C20 179.4(3)
C15 C14 C19 C18 -1.2(3)
N13 C14 C19 C18 -179.5(2)
C15 C14 C19 C20 179.9(2)
N13 C14 C19 C20 1.5(3)
