#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/13/2211315.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_2211315
loop_
_publ_author_name
'Sadaf Saeed'
'Alam, Samina'
'Andreas Fischer'
'Khan, Naeema'
_publ_section_title
;
 3-Chloro-N'-hydroxy-N-(1-naphthyl)benzenecarboximidamide
;
_journal_coeditor_code           CF2054
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5363
_journal_page_last               o5364
_journal_paper_doi               10.1107/S1600536806042747
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H13 Cl N2 O'
_chemical_formula_moiety         'C17 H13 Cl N2 O'
_chemical_formula_sum            'C17 H13 Cl N2 O'
_chemical_formula_weight         296.74
_chemical_name_systematic
;
3-Chloro-N'-hydroxy-N-(1-naphthyl)benzenecarboximidamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.099(3)
_cell_angle_beta                 93.815(4)
_cell_angle_gamma                103.869(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7217(5)
_cell_length_b                   8.7039(4)
_cell_length_c                   11.9158(4)
_cell_measurement_reflns_used    85
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.5
_cell_measurement_theta_min      4.9
_cell_volume                     747.41(7)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg, 1992)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al.,  2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10909
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         4.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.082
_refine_ls_R_factor_gt           0.043
_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)+(0.0431P)²+0.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.110
_reflns_number_gt                1796
_reflns_number_total             2764
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cf2054.cif
_cod_data_source_block           I
_cod_database_code               2211315
_cod_database_fobs_code          2211315
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,-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
Cl Cl1 1.09774(11) -0.22768(10) 0.53081(6) 0.0899(3) Uani d . 1
C C17 0.4906(3) 0.3541(2) 0.83830(16) 0.0428(5) Uani d . 1
C C8 0.6410(3) 0.2882(2) 0.81859(16) 0.0395(5) Uani d . 1
N N2 0.6596(2) 0.1654(2) 0.87420(14) 0.0484(4) Uani d . 1
O O1 0.8583(2) 0.1113(2) 1.03249(12) 0.0691(5) Uani d . 1
C C7 0.7685(3) 0.0629(2) 0.84256(16) 0.0408(5) Uani d . 1
C C6 0.9170(3) -0.0693(2) 0.68356(17) 0.0452(5) Uani d . 1
N N1 0.8650(3) 0.0228(2) 0.91684(14) 0.0520(5) Uani d . 1
C C5 0.7659(3) -0.0230(2) 0.71904(16) 0.0397(5) Uani d . 1
C C16 0.3566(3) 0.2966(3) 0.9034(2) 0.0567(6) Uani d . 1
C C9 0.7651(3) 0.3469(2) 0.75335(17) 0.0475(5) Uani d . 1
C C4 0.6109(3) -0.0666(2) 0.63978(18) 0.0493(5) Uani d . 1
C C12 0.4788(3) 0.4863(3) 0.79062(19) 0.0553(6) Uani d . 1
C C11 0.6098(4) 0.5424(3) 0.7234(2) 0.0688(7) Uani d . 1
C C3 0.6095(3) -0.1587(3) 0.5274(2) 0.0631(7) Uani d . 1
C C1 0.9108(3) -0.1633(3) 0.57183(18) 0.0533(6) Uani d . 1
C C2 0.7574(4) -0.2085(3) 0.49319(19) 0.0658(7) Uani d . 1
C C15 0.2198(3) 0.3699(3) 0.9236(2) 0.0769(8) Uani d . 1
C C13 0.3334(4) 0.5569(3) 0.8139(3) 0.0776(8) Uani d . 1
C C10 0.7475(4) 0.4738(3) 0.7043(2) 0.0639(6) Uani d . 1
C C14 0.2090(4) 0.5012(4) 0.8784(3) 0.0855(10) Uani d . 1
H H2N 0.6615 0.2043 0.9560 0.058 Uiso d R 1
H H1O 0.9478 0.0969 1.0751 0.083 Uiso d R 1
H H6 1.0228 -0.0369 0.7353 0.054 Uiso calc R 1
H H16 0.3611 0.2079 0.9330 0.068 Uiso calc R 1
H H9 0.8626 0.3024 0.7411 0.057 Uiso calc R 1
H H4 0.4960 -0.0293 0.6669 0.059 Uiso d R 1
H H11 0.6014 0.6283 0.6916 0.083 Uiso calc R 1
H H3 0.5061 -0.1874 0.4740 0.076 Uiso calc R 1
H H2 0.7541 -0.2721 0.4177 0.079 Uiso calc R 1
H H15 0.1330 0.3319 0.9680 0.092 Uiso calc R 1
H H13 0.3238 0.6440 0.7838 0.093 Uiso calc R 1
H H10 0.8317 0.5111 0.6581 0.077 Uiso calc R 1
H H14 0.1153 0.5503 0.8929 0.103 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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_
_diffrn_radiation_wavelength
0.71073
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C16 C17 C12 119.12(19) n
C16 C17 C8 123.28(19) n
C12 C17 C8 117.6(2) n
C9 C8 N2 121.88(17) n
C9 C8 C17 120.77(18) n
N2 C8 C17 117.28(17) n
C7 N2 C8 123.85(17) n
N1 C7 N2 123.14(17) n
N1 C7 C5 115.47(16) n
N2 C7 C5 121.07(16) n
C1 C6 C5 119.9(2) n
C7 N1 O1 111.18(15) n
C6 C5 C4 119.55(18) n
C6 C5 C7 119.36(17) n
C4 C5 C7 120.97(19) n
C15 C16 C17 120.4(2) n
C8 C9 C10 120.5(2) n
C3 C4 C5 119.2(2) n
C11 C12 C13 122.5(2) n
C11 C12 C17 119.6(2) n
C13 C12 C17 117.9(3) n
C10 C11 C12 120.9(2) n
C2 C3 C4 121.2(2) n
C2 C1 C6 120.9(2) n
C2 C1 Cl1 119.76(18) n
C6 C1 Cl1 119.35(18) n
C3 C2 C1 119.1(2) n
C16 C15 C14 120.7(3) n
C14 C13 C12 121.6(3) n
C11 C10 C9 120.6(2) n
C13 C14 C15 120.2(2) n
C7 N2 H2N 114.2 n
C8 N2 H2N 110.4 n
N1 O1 H1O 105.0 n
C1 C6 H6 120.0 n
C5 C6 H6 120.0 n
C15 C16 H16 119.8 n
C17 C16 H16 119.8 n
C8 C9 H9 119.7 n
C10 C9 H9 119.7 n
C3 C4 H4 121.5 n
C5 C4 H4 119.3 n
C10 C11 H11 119.5 n
C12 C11 H11 119.5 n
C2 C3 H3 119.4 n
C4 C3 H3 119.4 n
C3 C2 H2 120.4 n
C1 C2 H2 120.4 n
C16 C15 H15 119.7 n
C14 C15 H15 119.7 n
C14 C13 H13 119.2 n
C12 C13 H13 119.2 n
C11 C10 H10 119.7 n
C9 C10 H10 119.7 n
C13 C14 H14 119.9 n
C15 C14 H14 119.9 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.728(2) n
C17 C16 1.404(3) n
C17 C12 1.420(3) n
C17 C8 1.423(3) n
C8 C9 1.357(3) n
C8 N2 1.417(2) n
N2 C7 1.372(2) n
O1 N1 1.416(2) n
C7 N1 1.283(2) n
C7 C5 1.476(3) n
C6 C1 1.373(3) n
C6 C5 1.382(3) n
C5 C4 1.388(3) n
C16 C15 1.365(3) n
C9 C10 1.399(3) n
C4 C3 1.381(3) n
C12 C11 1.402(3) n
C12 C13 1.416(3) n
C11 C10 1.345(3) n
C3 C2 1.368(3) n
C1 C2 1.373(3) n
C15 C14 1.394(4) n
C13 C14 1.344(4) n
N2 H2N 0.9483 n
O1 H1O 0.8813 n
C6 H6 0.930 n
C16 H16 0.930 n
C9 H9 0.930 n
C4 H4 1.0590 n
C11 H11 0.930 n
C3 H3 0.930 n
C2 H2 0.930 n
C15 H15 0.930 n
C13 H13 0.930 n
C10 H10 0.930 n
C14 H14 0.930 n
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
O1 H1O N1 2_757 0.88 1.98 2.768(2) 147 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126010
