#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/65/2236542.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_2236542
loop_
_publ_author_name
'Sharif, Hafiz Muhammad Adeel'
'Alvi, Dildar Ahmed'
'Yousuf, S.'
_publ_section_title
;
 2-[(E)-(Naphthalen-2-yl)iminomethyl]phenol
;
_journal_coeditor_code           PV2571
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2629
_journal_paper_doi               10.1107/S1600536812033843
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H13 N O'
_chemical_formula_moiety         'C17 H13 N O'
_chemical_formula_sum            'C17 H13 N O'
_chemical_formula_weight         247.28
_chemical_name_systematic
;
2-[(E)-(Naphthalen-2-yl)iminomethyl]phenol
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6348(17)
_cell_length_b                   5.8768(7)
_cell_length_c                   15.869(2)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.57
_cell_volume                     1271.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6852
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.091
_refine_ls_abs_structure_details
'Not determined; Friedel pairs (1082) were not merged.'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0376
_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)+(0.0383P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                1655
_reflns_number_total             2300
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2571.cif
_cod_data_source_block           I
_cod_original_cell_volume        1271.5(3)
_cod_database_code               2236542
_cod_database_fobs_code          2236542
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.51540(13) 1.1177(3) 0.40612(13) 0.0846(6) Uani d D 1 1
N N1 0.58509(13) 0.7914(3) 0.50171(12) 0.0592(5) Uani d . 1 1
C C1 0.73882(15) 0.8452(4) 0.56875(14) 0.0542(5) Uani d . 1 1
H H1B 0.7413 0.9851 0.5415 0.065 Uiso calc R 1 1
C C2 0.81650(15) 0.7835(4) 0.62265(13) 0.0519(5) Uani d . 1 1
C C3 0.89755(15) 0.9265(4) 0.63756(14) 0.0626(6) Uani d . 1 1
H H3A 0.9012 1.0662 0.6103 0.075 Uiso calc R 1 1
C C4 0.97028(19) 0.8641(4) 0.69100(17) 0.0718(7) Uani d . 1 1
H H4A 1.0229 0.9616 0.7001 0.086 Uiso calc R 1 1
C C5 0.96686(19) 0.6547(5) 0.73249(15) 0.0707(7) Uani d . 1 1
H H5A 1.0167 0.6140 0.7695 0.085 Uiso calc R 1 1
C C6 0.89085(18) 0.5111(4) 0.71880(14) 0.0664(7) Uani d . 1 1
H H6A 0.8901 0.3702 0.7455 0.080 Uiso calc R 1 1
C C7 0.81231(16) 0.5715(4) 0.66451(13) 0.0552(6) Uani d . 1 1
C C8 0.73097(17) 0.4295(4) 0.64880(16) 0.0662(7) Uani d . 1 1
H H8A 0.7274 0.2883 0.6750 0.079 Uiso calc R 1 1
C C9 0.65784(16) 0.4950(4) 0.59615(17) 0.0694(7) Uani d . 1 1
H H9A 0.6051 0.3977 0.5869 0.083 Uiso calc R 1 1
C C10 0.66026(15) 0.7071(3) 0.55524(14) 0.0527(5) Uani d . 1 1
C C11 0.50538(16) 0.6824(4) 0.49001(14) 0.0591(6) Uani d . 1 1
H H11A 0.4976 0.5400 0.5147 0.071 Uiso calc R 1 1
C C12 0.42625(15) 0.7755(4) 0.43905(13) 0.0538(6) Uani d . 1 1
C C13 0.33980(16) 0.6545(4) 0.43146(16) 0.0676(6) Uani d . 1 1
H H13A 0.3340 0.5137 0.4577 0.081 Uiso calc R 1 1
C C14 0.26177(19) 0.7392(5) 0.38553(15) 0.0753(7) Uani d . 1 1
H H14A 0.2040 0.6559 0.3808 0.090 Uiso calc R 1 1
C C15 0.27038(18) 0.9489(5) 0.34667(16) 0.0738(7) Uani d . 1 1
H H15A 0.2179 1.0067 0.3159 0.089 Uiso calc R 1 1
C C16 0.35529(17) 1.0725(5) 0.35294(16) 0.0709(7) Uani d . 1 1
H H16A 0.3606 1.2121 0.3257 0.085 Uiso calc R 1 1
C C17 0.43405(15) 0.9890(4) 0.40022(15) 0.0596(6) Uani d . 1 1
H H1C 0.5580(15) 1.045(4) 0.4354(15) 0.085(9) Uiso d D 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 0.0016 '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
C17 O1 H1C 108.4(18)
C11 N1 C10 121.78(19)
C10 C1 C2 122.3(2)
C10 C1 H1B 118.9
C2 C1 H1B 118.9
C3 C2 C1 122.6(2)
C3 C2 C7 118.60(19)
C1 C2 C7 118.80(19)
C4 C3 C2 121.2(2)
C4 C3 H3A 119.4
C2 C3 H3A 119.4
C3 C4 C5 120.6(2)
C3 C4 H4A 119.7
C5 C4 H4A 119.7
C6 C5 C4 119.9(2)
C6 C5 H5A 120.0
C4 C5 H5A 120.0
C5 C6 C7 121.3(2)
C5 C6 H6A 119.4
C7 C6 H6A 119.4
C8 C7 C2 118.1(2)
C8 C7 C6 123.5(2)
C2 C7 C6 118.4(2)
C9 C8 C7 121.3(2)
C9 C8 H8A 119.4
C7 C8 H8A 119.4
C8 C9 C10 121.2(2)
C8 C9 H9A 119.4
C10 C9 H9A 119.4
C1 C10 C9 118.3(2)
C1 C10 N1 116.99(18)
C9 C10 N1 124.66(19)
N1 C11 C12 121.6(2)
N1 C11 H11A 119.2
C12 C11 H11A 119.2
C13 C12 C17 119.1(2)
C13 C12 C11 119.2(2)
C17 C12 C11 121.6(2)
C12 C13 C14 121.2(2)
C12 C13 H13A 119.4
C14 C13 H13A 119.4
C13 C14 C15 119.4(2)
C13 C14 H14A 120.3
C15 C14 H14A 120.3
C16 C15 C14 120.8(2)
C16 C15 H15A 119.6
C14 C15 H15A 119.6
C15 C16 C17 120.1(3)
C15 C16 H16A 120.0
C17 C16 H16A 120.0
O1 C17 C16 118.2(2)
O1 C17 C12 122.3(2)
C16 C17 C12 119.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.346(3)
O1 H1C 0.86(2)
N1 C11 1.275(2)
N1 C10 1.421(2)
C1 C10 1.361(3)
C1 C2 1.409(3)
C1 H1B 0.9300
C2 C3 1.408(3)
C2 C7 1.413(3)
C3 C4 1.355(3)
C3 H3A 0.9300
C4 C5 1.396(3)
C4 H4A 0.9300
C5 C6 1.354(3)
C5 H5A 0.9300
C6 C7 1.419(3)
C6 H6A 0.9300
C7 C8 1.410(3)
C8 C9 1.356(3)
C8 H8A 0.9300
C9 C10 1.406(3)
C9 H9A 0.9300
C11 C12 1.455(3)
C11 H11A 0.9300
C12 C13 1.382(3)
C12 C17 1.402(3)
C13 C14 1.382(3)
C13 H13A 0.9300
C14 C15 1.383(3)
C14 H14A 0.9300
C15 C16 1.370(3)
C15 H15A 0.9300
C16 C17 1.399(3)
C16 H16A 0.9300
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
O1 H1C N1 0.86(2) 1.86(2) 2.623(3) 147(2) 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
C10 C1 C2 C3 -179.4(2)
C10 C1 C2 C7 -0.4(3)
C1 C2 C3 C4 178.8(2)
C7 C2 C3 C4 -0.2(3)
C2 C3 C4 C5 0.3(4)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 C7 -1.8(4)
C3 C2 C7 C8 -179.76(19)
C1 C2 C7 C8 1.2(3)
C3 C2 C7 C6 -0.9(3)
C1 C2 C7 C6 -179.89(19)
C5 C6 C7 C8 -179.3(2)
C5 C6 C7 C2 1.9(3)
C2 C7 C8 C9 -1.0(3)
C6 C7 C8 C9 -179.8(2)
C7 C8 C9 C10 -0.1(4)
C2 C1 C10 C9 -0.7(3)
C2 C1 C10 N1 177.97(18)
C8 C9 C10 C1 0.9(3)
C8 C9 C10 N1 -177.6(2)
C11 N1 C10 C1 -174.8(2)
C11 N1 C10 C9 3.8(3)
C10 N1 C11 C12 176.38(18)
N1 C11 C12 C13 -177.2(2)
N1 C11 C12 C17 0.2(3)
C17 C12 C13 C14 0.8(3)
C11 C12 C13 C14 178.27(19)
C12 C13 C14 C15 -0.1(3)
C13 C14 C15 C16 0.3(4)
C14 C15 C16 C17 -1.1(4)
C15 C16 C17 O1 -178.7(2)
C15 C16 C17 C12 1.7(3)
C13 C12 C17 O1 178.9(2)
C11 C12 C17 O1 1.5(3)
C13 C12 C17 C16 -1.6(3)
C11 C12 C17 C16 -179.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 15123032
