#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/28/2232844.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_2232844
loop_
_publ_author_name
'Zhu, Ruitao'
'Ren, Yuehong'
'Li, Wenjuan'
_publ_section_title
;
 N-(Naphthalen-1-yl)benzamide
;
_journal_coeditor_code           LH5366
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3204
_journal_paper_doi               10.1107/S1600536811045946
_journal_volume                  67
_journal_year                    2011
_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
;
N-(Naphthalen-1-yl)benzamide
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.2630(8)
_cell_length_b                   9.3792(9)
_cell_length_c                   33.806(3)
_cell_measurement_reflns_used    1469
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.446
_cell_measurement_theta_min      2.742
_cell_volume                     2620.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0860
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            12210
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2307
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0559
_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)+(0.0469P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                1253
_reflns_number_total             2307
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5366.cif
_cod_data_source_block           I
_cod_database_code               2232844
_cod_database_fobs_code          2232844
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
N N1 0.2455(2) 0.6961(2) 0.36346(6) 0.0567(6) Uani d . 1 1
H H1 0.2671 0.7855 0.3655 0.068 Uiso calc R 1 1
O O1 0.3279(2) 0.48418(17) 0.33881(5) 0.0644(5) Uani d . 1 1
C C1 0.3422(3) 0.6140(3) 0.34048(7) 0.0511(7) Uani d . 1 1
C C2 0.4657(3) 0.6894(3) 0.31610(7) 0.0439(6) Uani d . 1 1
C C3 0.5181(3) 0.6226(3) 0.28213(8) 0.0538(7) Uani d . 1 1
H H3 0.4779 0.5330 0.2756 0.065 Uiso calc R 1 1
C C4 0.6293(3) 0.6871(3) 0.25781(8) 0.0650(8) Uani d . 1 1
H H4 0.6620 0.6423 0.2346 0.078 Uiso calc R 1 1
C C5 0.6924(3) 0.8183(3) 0.26772(9) 0.0701(8) Uani d . 1 1
H H5 0.7681 0.8617 0.2513 0.084 Uiso calc R 1 1
C C6 0.6433(3) 0.8845(3) 0.30176(9) 0.0717(8) Uani d . 1 1
H H6 0.6874 0.9722 0.3087 0.086 Uiso calc R 1 1
C C7 0.5284(3) 0.8213(3) 0.32578(8) 0.0602(7) Uani d . 1 1
H H7 0.4933 0.8677 0.3485 0.072 Uiso calc R 1 1
C C8 0.1091(3) 0.6407(2) 0.38450(7) 0.0520(7) Uani d . 1 1
C C9 -0.0404(4) 0.6895(3) 0.37506(8) 0.0648(8) Uani d . 1 1
H H9 -0.0521 0.7592 0.3557 0.078 Uiso calc R 1 1
C C10 -0.1779(3) 0.6353(3) 0.39436(9) 0.0813(9) Uani d . 1 1
H H10 -0.2800 0.6700 0.3880 0.098 Uiso calc R 1 1
C C11 -0.1619(4) 0.5323(3) 0.42238(9) 0.0821(9) Uani d . 1 1
H H11 -0.2536 0.4944 0.4344 0.099 Uiso calc R 1 1
C C12 -0.0082(3) 0.4827(3) 0.43327(8) 0.0628(8) Uani d . 1 1
C C13 0.1314(3) 0.5404(2) 0.41501(7) 0.0516(7) Uani d . 1 1
C C14 0.2849(3) 0.4941(3) 0.42846(8) 0.0630(8) Uani d . 1 1
H H14 0.3783 0.5321 0.4173 0.076 Uiso calc R 1 1
C C15 0.2966(4) 0.3944(3) 0.45750(9) 0.0806(9) Uani d . 1 1
H H15 0.3983 0.3662 0.4663 0.097 Uiso calc R 1 1
C C16 0.1598(5) 0.3343(4) 0.47420(9) 0.0965(11) Uani d . 1 1
H H16 0.1698 0.2635 0.4933 0.116 Uiso calc R 1 1
C C17 0.0127(5) 0.3784(3) 0.46272(9) 0.0897(10) Uani d . 1 1
H H17 -0.0783 0.3388 0.4746 0.108 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'
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
C1 N1 C8 122.9(2)
C1 N1 H1 118.5
C8 N1 H1 118.5
O1 C1 N1 122.3(2)
O1 C1 C2 120.8(2)
N1 C1 C2 116.9(2)
C3 C2 C7 119.1(2)
C3 C2 C1 117.4(2)
C7 C2 C1 123.4(2)
C4 C3 C2 120.6(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.1(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 119.8(3)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C7 120.1(3)
C5 C6 H6 119.9
C7 C6 H6 119.9
C2 C7 C6 120.2(2)
C2 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 C13 121.1(2)
C9 C8 N1 118.6(2)
C13 C8 N1 120.2(2)
C8 C9 C10 120.3(3)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 120.2(3)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 120.4(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C11 C12 C17 121.8(3)
C11 C12 C13 119.8(3)
C17 C12 C13 118.3(3)
C8 C13 C12 117.9(2)
C8 C13 C14 123.9(2)
C12 C13 C14 118.2(2)
C15 C14 C13 120.5(3)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 121.1(3)
C14 C15 H15 119.4
C16 C15 H15 119.4
C17 C16 C15 119.7(3)
C17 C16 H16 120.1
C15 C16 H16 120.1
C16 C17 C12 122.1(3)
C16 C17 H17 119.0
C12 C17 H17 119.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.354(3)
N1 C8 1.431(3)
N1 H1 0.8600
O1 C1 1.225(2)
C1 C2 1.490(3)
C2 C3 1.378(3)
C2 C7 1.381(3)
C3 C4 1.373(3)
C3 H3 0.9300
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.369(3)
C5 H5 0.9300
C6 C7 1.383(3)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.356(3)
C8 C13 1.408(3)
C9 C10 1.405(4)
C9 H9 0.9300
C10 C11 1.360(4)
C10 H10 0.9300
C11 C12 1.402(4)
C11 H11 0.9300
C12 C17 1.406(4)
C12 C13 1.415(3)
C13 C14 1.416(3)
C14 C15 1.359(3)
C14 H14 0.9300
C15 C16 1.384(4)
C15 H15 0.9300
C16 C17 1.341(4)
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
_geom_hbond_publ_flag
N1 H1 O1 8_665 0.860 2.214 2.892(3) 135.61 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
C8 N1 C1 O1 -6.5(4)
C8 N1 C1 C2 171.9(2)
O1 C1 C2 C3 24.1(3)
N1 C1 C2 C3 -154.3(2)
O1 C1 C2 C7 -156.2(2)
N1 C1 C2 C7 25.4(3)
C7 C2 C3 C4 -1.1(3)
C1 C2 C3 C4 178.6(2)
C2 C3 C4 C5 1.6(4)
C3 C4 C5 C6 -0.4(4)
C4 C5 C6 C7 -1.2(4)
C3 C2 C7 C6 -0.5(4)
C1 C2 C7 C6 179.8(2)
C5 C6 C7 C2 1.7(4)
C1 N1 C8 C9 -117.0(3)
C1 N1 C8 C13 64.6(3)
C13 C8 C9 C10 -3.2(4)
N1 C8 C9 C10 178.4(2)
C8 C9 C10 C11 -0.7(4)
C9 C10 C11 C12 2.2(4)
C10 C11 C12 C17 178.7(3)
C10 C11 C12 C13 0.1(4)
C9 C8 C13 C12 5.4(3)
N1 C8 C13 C12 -176.3(2)
C9 C8 C13 C14 -174.6(2)
N1 C8 C13 C14 3.7(3)
C11 C12 C13 C8 -3.8(4)
C17 C12 C13 C8 177.6(2)
C11 C12 C13 C14 176.2(2)
C17 C12 C13 C14 -2.4(4)
C8 C13 C14 C15 -178.5(2)
C12 C13 C14 C15 1.5(4)
C13 C14 C15 C16 1.0(4)
C14 C15 C16 C17 -2.6(5)
C15 C16 C17 C12 1.5(5)
C11 C12 C17 C16 -177.6(3)
C13 C12 C17 C16 1.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 62655
