#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/63/2236383.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_2236383
loop_
_publ_author_name
'Akbal, Tufan'
'Ağar Alaman, Ayşen'
'Gümüş, Sümeyye'
'Erdönmez, Ahmet'
_publ_section_title
;
 (E)-1-[(3-Bromophenyl)iminomethyl]naphthalen-2-ol
;
_journal_coeditor_code           IS5182
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2779
_journal_paper_doi               10.1107/S1600536812034824
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H12 Br N O'
_chemical_formula_moiety         'C17 H12 Br N O'
_chemical_formula_sum            'C17 H12 Br N O'
_chemical_formula_weight         326.19
_chemical_melting_point_gt       398
_chemical_melting_point_lt       400
_chemical_name_systematic
;
(E)-1-[(3-Bromophenyl)iminomethyl]naphthalen-2-ol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 107.772(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.3965(19)
_cell_length_b                   4.8657(2)
_cell_length_c                   19.0124(11)
_cell_measurement_reflns_used    14469
_cell_measurement_temperature    296
_cell_measurement_theta_max      26
_cell_measurement_theta_min      1.4
_cell_volume                     2765.8(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'WinGX (Farrugia, 1999) and SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scans'
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14469
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.36
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.966
_exptl_absorpt_correction_T_max  0.680
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.465
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0468
_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)+(0.0492P)²+3.7545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1174
_reflns_number_gt                1992
_reflns_number_total             2706
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5182.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236383
_cod_database_fobs_code          2236383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Br Br1 0.051469(14) 0.50605(11) 0.33169(2) 0.0901(2) Uani d . 1 1
N N1 0.16786(9) -0.1439(6) 0.51791(14) 0.0553(7) Uani d . 1 1
O O1 0.22611(8) -0.3797(6) 0.62422(15) 0.0750(7) Uani d . 1 1
H H1A 0.2164 -0.2890 0.5863 0.112 Uiso calc R 1 1
C C1 0.11528(11) 0.1582(7) 0.42764(17) 0.0533(8) Uani d . 1 1
H H1 0.0910 0.0929 0.4410 0.064 Uiso calc R 1 1
C C2 0.15784(11) 0.0544(6) 0.46103(16) 0.0504(8) Uani d . 1 1
C C3 0.19318(12) 0.1518(9) 0.4388(2) 0.0642(9) Uani d . 1 1
H H3 0.2217 0.0813 0.4602 0.077 Uiso calc R 1 1
C C4 0.18636(14) 0.3517(9) 0.3854(2) 0.0721(11) Uani d . 1 1
H H4 0.2104 0.4153 0.3712 0.087 Uiso calc R 1 1
C C5 0.14434(14) 0.4590(8) 0.35266(19) 0.0664(10) Uani d . 1 1
H H5 0.1397 0.5952 0.3168 0.080 Uiso calc R 1 1
C C6 0.10943(12) 0.3588(8) 0.37456(17) 0.0573(8) Uani d . 1 1
C C7 0.13773(11) -0.2878(7) 0.53452(16) 0.0509(7) Uani d . 1 1
H H7 0.1079 -0.2624 0.5071 0.061 Uiso calc R 1 1
C C9 0.19303(11) -0.5211(7) 0.63643(18) 0.0583(8) Uani d . 1 1
C C8 0.14817(10) -0.4839(6) 0.59306(16) 0.0493(7) Uani d . 1 1
C C10 0.20366(13) -0.7094(8) 0.69535(19) 0.0672(10) Uani d . 1 1
H H10 0.2332 -0.7301 0.7245 0.081 Uiso calc R 1 1
C C11 0.17155(14) -0.8593(9) 0.70984(19) 0.0671(10) Uani d . 1 1
H H11 0.1796 -0.9824 0.7491 0.080 Uiso calc R 1 1
C C12 0.12580(12) -0.8380(7) 0.66784(17) 0.0569(8) Uani d . 1 1
C C13 0.11370(11) -0.6490(7) 0.60843(16) 0.0495(7) Uani d . 1 1
C C14 0.06822(12) -0.6362(9) 0.5669(2) 0.0658(9) Uani d . 1 1
H H14 0.0592 -0.5161 0.5271 0.079 Uiso calc R 1 1
C C15 0.03683(14) -0.7972(9) 0.5839(2) 0.0783(11) Uani d . 1 1
H H15 0.0070 -0.7845 0.5556 0.094 Uiso calc R 1 1
C C16 0.04908(16) -0.9769(9) 0.6424(3) 0.0837(12) Uani d . 1 1
H H16 0.0275 -1.0840 0.6537 0.100 Uiso calc R 1 1
C C17 0.09253(16) -0.9979(8) 0.6835(2) 0.0753(11) Uani d . 1 1
H H17 0.1005 -1.1207 0.7228 0.090 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 0.0016 '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'
Br Br -0.2901 2.4595 '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
C7 N1 C2 123.3(3)
C9 O1 H1A 109.5
C6 C1 C2 119.2(3)
C6 C1 H1 120.4
C2 C1 H1 120.4
C3 C2 C1 119.0(3)
C3 C2 N1 117.1(3)
C1 C2 N1 123.9(3)
C4 C3 C2 120.6(4)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.9(4)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 118.1(4)
C6 C5 H5 121.0
C4 C5 H5 121.0
C1 C6 C5 122.3(3)
C1 C6 Br1 118.7(3)
C5 C6 Br1 119.1(3)
N1 C7 C8 122.9(3)
N1 C7 H7 118.6
C8 C7 H7 118.6
C9 C8 C7 119.5(3)
C9 C8 C13 119.1(3)
C7 C8 C13 121.4(3)
O1 C9 C10 118.0(3)
O1 C9 C8 121.9(3)
C10 C9 C8 120.1(3)
C11 C10 C9 120.5(3)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 122.8(3)
C10 C11 H11 118.6
C12 C11 H11 118.6
C17 C12 C13 119.5(3)
C17 C12 C11 122.1(3)
C13 C12 C11 118.4(3)
C14 C13 C12 117.1(3)
C14 C13 C8 123.8(3)
C12 C13 C8 119.1(3)
C15 C14 C13 121.5(4)
C15 C14 H14 119.3
C13 C14 H14 119.3
C14 C15 C16 120.7(4)
C14 C15 H15 119.7
C16 C15 H15 119.7
C17 C16 C15 119.9(4)
C17 C16 H16 120.0
C15 C16 H16 120.0
C16 C17 C12 121.3(4)
C16 C17 H17 119.3
C12 C17 H17 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C6 1.893(4)
N1 C7 1.291(4)
N1 C2 1.411(4)
O1 C9 1.324(4)
O1 H1A 0.8200
C1 C6 1.375(5)
C1 C2 1.388(4)
C1 H1 0.9300
C3 C4 1.375(6)
C3 C2 1.386(5)
C3 H3 0.9300
C4 H4 0.9300
C5 C4 1.378(6)
C5 H5 0.9300
C6 C5 1.375(5)
C7 C8 1.426(4)
C7 H7 0.9300
C9 C10 1.406(5)
C9 C8 1.410(4)
C10 H10 0.9300
C11 C10 1.339(6)
C11 C12 1.418(5)
C11 H11 0.9300
C12 C17 1.405(5)
C12 C13 1.416(4)
C13 C14 1.406(5)
C13 C8 1.447(5)
C14 C15 1.372(6)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.353(6)
C16 C15 1.373(6)
C16 H16 0.9300
C17 H17 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 N1 1_555 0.82 1.82 2.548(4) 147
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
C2 N1 C7 C8 -178.8(3)
C10 C11 C12 C17 179.6(4)
C10 C11 C12 C13 -0.4(5)
C17 C12 C13 C14 -1.1(5)
C11 C12 C13 C14 178.8(3)
C17 C12 C13 C8 179.6(3)
C11 C12 C13 C8 -0.4(4)
O1 C9 C8 C7 -0.4(5)
C10 C9 C8 C7 178.6(3)
O1 C9 C8 C13 178.8(3)
C10 C9 C8 C13 -2.2(5)
N1 C7 C8 C9 1.5(5)
N1 C7 C8 C13 -177.7(3)
C14 C13 C8 C9 -177.5(3)
C12 C13 C8 C9 1.7(4)
C14 C13 C8 C7 1.7(5)
C12 C13 C8 C7 -179.1(3)
C2 C1 C6 C5 0.7(5)
C2 C1 C6 Br1 -178.1(2)
C4 C3 C2 C1 1.1(5)
C4 C3 C2 N1 -177.9(3)
C6 C1 C2 C3 -1.3(5)
C6 C1 C2 N1 177.6(3)
C7 N1 C2 C3 -166.9(3)
C7 N1 C2 C1 14.2(5)
C1 C6 C5 C4 0.3(5)
Br1 C6 C5 C4 179.0(3)
C12 C11 C10 C9 -0.1(6)
O1 C9 C10 C11 -179.5(3)
C8 C9 C10 C11 1.5(5)
C12 C13 C14 C15 0.9(5)
C8 C13 C14 C15 -179.9(3)
C2 C3 C4 C5 -0.2(6)
C6 C5 C4 C3 -0.5(6)
C13 C14 C15 C16 -0.1(6)
C17 C16 C15 C14 -0.5(7)
C15 C16 C17 C12 0.3(6)
C13 C12 C17 C16 0.6(6)
C11 C12 C17 C16 -179.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21476548
