#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/75/2237534.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_2237534
loop_
_publ_author_name
'Ganesh, G.'
'Murugavel, K.'
'Kannan, P. S.'
'Amirthaganesan, S.'
'SubbiahPandi, A.'
_publ_section_title
;
 N-[(1E)-5-(3-Chlorophenyl)-3-methylcyclohex-2-en-1-ylidene]hydroxylamine
;
_journal_coeditor_code           NK2191
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o449
_journal_paper_doi               10.1107/S1600536813004698
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C13 H14 Cl N O'
_chemical_formula_moiety         'C13 H14 Cl N O'
_chemical_formula_sum            'C13 H14 Cl N O'
_chemical_formula_weight         235.70
_chemical_name_systematic
N-[(1E)-5-(3-Chlorophenyl)-3-methylcyclohex-2-en-1-ylidene]hydroxylamine
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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            16
_cell_length_a                   19.7898(8)
_cell_length_b                   19.7898(8)
_cell_length_c                   12.4416(11)
_cell_measurement_reflns_used    2394
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.5
_cell_volume                     4872.6(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω and φ 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  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19841
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.496
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2394
_refine_ls_number_restraints     93
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1164P)²+10.7128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2168
_refine_ls_wR_factor_ref         0.2417
_reflns_number_gt                1765
_reflns_number_total             2394
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nk2191.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2237534
_cod_database_fobs_code          2237534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5714(9) 0.6964(10) 0.5126(13) 0.064(4) Uani d PDU 0.560(6) 1 A 1
H H1 0.5873 0.7176 0.5632 0.095 Uiso calc PR 0.560(6) 1 A 1
N N1 0.5172(8) 0.6572(8) 0.5484(11) 0.055(4) Uani d PDU 0.560(6) 1 A 1
C C1 0.5202(8) 0.6216(9) 0.3560(9) 0.053(4) Uani d PDU 0.560(6) 1 A 1
H H1A 0.5687 0.6283 0.3589 0.064 Uiso calc PR 0.560(6) 1 A 1
H H1B 0.5010 0.6582 0.3141 0.064 Uiso calc PR 0.560(6) 1 A 1
C C2 0.4922(8) 0.6246(8) 0.4677(7) 0.036(3) Uani d PDU 0.560(6) 1 A 1
C C3 0.4336(8) 0.5833(7) 0.4904(12) 0.044(4) Uani d PDU 0.560(6) 1 A 1
H H3 0.4135 0.5871 0.5577 0.053 Uiso calc PR 0.560(6) 1 A 1
C C4 0.4070(6) 0.5404(6) 0.4205(13) 0.043(3) Uani d PDU 0.560(6) 1 A 1
C C5 0.4409(10) 0.5208(11) 0.3142(15) 0.055(5) Uani d PDU 0.560(6) 1 A 1
H H5A 0.4480 0.4723 0.3128 0.067 Uiso calc PR 0.560(6) 1 A 1
H H5B 0.4111 0.5323 0.2550 0.067 Uiso calc PR 0.560(6) 1 A 1
C C6 0.5054(4) 0.5550(4) 0.2999(5) 0.0570(18) Uani d PDU 0.560(6) 1 A 1
H H6 0.5377 0.5238 0.3331 0.068 Uiso calc PR 0.560(6) 1 A 1
C C7 0.34307(17) 0.49939(17) 0.4407(3) 0.057(2) Uani d PDU 0.560(6) 1 A 1
H H7A 0.3338 0.4715 0.3793 0.085 Uiso calc PR 0.560(6) 1 A 1
H H7B 0.3058 0.5295 0.4527 0.085 Uiso calc PR 0.560(6) 1 A 1
H H7C 0.3494 0.4713 0.5028 0.085 Uiso calc PR 0.560(6) 1 A 1
C C8 0.52861(17) 0.55769(17) 0.1822(3) 0.0421(17) Uani d PRDU 0.560(6) 1 A 1
C C9 0.58200(17) 0.51926(17) 0.1431(3) 0.0541(19) Uani d PRU 0.560(6) 1 A 1
H H9 0.6054 0.4904 0.1888 0.065 Uiso calc PR 0.560(6) 1 A 1
C C10 0.60045(17) 0.52400(17) 0.0355(3) 0.063(3) Uani d PRDU 0.560(6) 1 A 1
C C11 0.56550(17) 0.56717(17) -0.0328(3) 0.066(3) Uani d PRU 0.560(6) 1 A 1
H H11 0.5778 0.5703 -0.1048 0.080 Uiso calc PR 0.560(6) 1 A 1
C C12 0.51211(17) 0.60561(17) 0.0063(3) 0.057(2) Uani d PRU 0.560(6) 1 A 1
H H12 0.4887 0.6345 -0.0395 0.069 Uiso calc PR 0.560(6) 1 A 1
C C13 0.49367(17) 0.60087(17) 0.1138(3) 0.055(2) Uani d PRU 0.560(6) 1 A 1
H H13 0.4580 0.6266 0.1400 0.066 Uiso calc PR 0.560(6) 1 A 1
Cl Cl1 0.6641(5) 0.4726(6) -0.0028(7) 0.105(2) Uani d PDU 0.560(6) 1 A 1
O O1' 0.5722(9) 0.6919(14) 0.5195(19) 0.072(7) Uani d PDU 0.440(6) 1 A 2
H H1' 0.5786 0.7190 0.5682 0.108 Uiso calc PR 0.440(6) 1 A 2
N N1' 0.5138(8) 0.6543(11) 0.5411(14) 0.049(5) Uani d PDU 0.440(6) 1 A 2
C C1' 0.5283(9) 0.6052(12) 0.3642(11) 0.054(5) Uani d PDU 0.440(6) 1 A 2
H H1'1 0.5638 0.5713 0.3650 0.064 Uiso calc PR 0.440(6) 1 A 2
H H1'2 0.5491 0.6484 0.3485 0.064 Uiso calc PR 0.440(6) 1 A 2
C C2' 0.4964(11) 0.6083(10) 0.4731(9) 0.039(4) Uani d PDU 0.440(6) 1 A 2
C C3' 0.4381(9) 0.5666(9) 0.4972(14) 0.036(3) Uani d PDU 0.440(6) 1 A 2
H H3' 0.4183 0.5704 0.5647 0.043 Uiso calc PR 0.440(6) 1 A 2
C C4' 0.4117(7) 0.5234(8) 0.4276(16) 0.040(3) Uani d PDU 0.440(6) 1 A 2
C C5' 0.4337(12) 0.5340(13) 0.3107(17) 0.049(4) Uani d PDU 0.440(6) 1 A 2
H H5'1 0.4548 0.4921 0.2880 0.059 Uiso calc PR 0.440(6) 1 A 2
H H5'2 0.3926 0.5384 0.2689 0.059 Uiso calc PR 0.440(6) 1 A 2
C C6' 0.4783(3) 0.5882(4) 0.2756(5) 0.0406(16) Uani d PDU 0.440(6) 1 A 2
H H6' 0.4491 0.6280 0.2699 0.049 Uiso calc PR 0.440(6) 1 A 2
C C7' 0.3566(2) 0.4738(2) 0.4612(4) 0.052(2) Uani d PDU 0.440(6) 1 A 2
H H7'1 0.3422 0.4482 0.3997 0.078 Uiso calc PR 0.440(6) 1 A 2
H H7'2 0.3188 0.4983 0.4900 0.078 Uiso calc PR 0.440(6) 1 A 2
H H7'3 0.3740 0.4437 0.5149 0.078 Uiso calc PR 0.440(6) 1 A 2
C C8' 0.5110(2) 0.5810(2) 0.1653(4) 0.039(2) Uani d PRDU 0.440(6) 1 A 2
C C9' 0.5606(2) 0.5320(2) 0.1517(4) 0.0379(19) Uani d PRU 0.440(6) 1 A 2
H H9' 0.5722 0.5039 0.2086 0.046 Uiso calc PR 0.440(6) 1 A 2
C C10' 0.5928(2) 0.5251(2) 0.0530(4) 0.045(2) Uani d PRDU 0.440(6) 1 A 2
C C11' 0.5754(2) 0.5671(2) -0.0321(4) 0.052(3) Uani d PRU 0.440(6) 1 A 2
H H11' 0.5969 0.5625 -0.0981 0.063 Uiso calc PR 0.440(6) 1 A 2
C C12' 0.5258(2) 0.6161(2) -0.0185(4) 0.058(3) Uani d PRU 0.440(6) 1 A 2
H H12' 0.5141 0.6443 -0.0755 0.070 Uiso calc PR 0.440(6) 1 A 2
C C13' 0.4936(2) 0.6231(2) 0.0802(4) 0.049(2) Uani d PRU 0.440(6) 1 A 2
H H13' 0.4604 0.6558 0.0892 0.059 Uiso calc PR 0.440(6) 1 A 2
Cl Cl1' 0.6585(5) 0.4711(6) 0.0291(8) 0.0866(18) Uani d PDU 0.440(6) 1 A 2
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 O1 H1 109.5
C2 N1 O1 108.8(13)
C2 C1 C6 112.9(9)
C2 C1 H1A 109.0
C6 C1 H1A 109.0
C2 C1 H1B 109.0
C6 C1 H1B 109.0
H1A C1 H1B 107.8
N1 C2 C3 115.9(11)
N1 C2 C1 126.9(11)
C3 C2 C1 117.1(7)
C4 C3 C2 123.5(9)
C4 C3 H3 118.2
C2 C3 H3 118.2
C3 C4 C7 124.2(11)
C3 C4 C5 123.7(9)
C7 C4 C5 111.8(7)
C6 C5 C4 111.8(9)
C6 C5 H5A 109.3
C4 C5 H5A 109.3
C6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 107.9
C5 C6 C1 121.1(10)
C5 C6 C8 113.3(8)
C1 C6 C8 110.5(7)
C5 C6 H6 103.2
C1 C6 H6 103.2
C8 C6 H6 103.2
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 120.0
C9 C8 C6 122.9(4)
C13 C8 C6 117.1(4)
C8 C9 C10 120.0
C8 C9 H9 120.0
C10 C9 H9 120.0
C9 C10 C11 120.0
C9 C10 Cl1 115.3(3)
C11 C10 Cl1 124.6(3)
C12 C11 C10 120.0
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 120.0
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C8 120.0
C12 C13 H13 120.0
C8 C13 H13 120.0
N1' O1' H1' 109.5
C2' N1' O1' 118.0(16)
C2' C1' C6' 113.0(10)
C2' C1' H1'1 109.0
C6' C1' H1'1 109.0
C2' C1' H1'2 109.0
C6' C1' H1'2 109.0
H1'1 C1' H1'2 107.8
N1' C2' C3' 118.6(13)
N1' C2' C1' 120.7(13)
C3' C2' C1' 120.0(9)
C4' C3' C2' 123.1(10)
C4' C3' H3' 118.5
C2' C3' H3' 118.5
C3' C4' C7' 121.2(13)
C3' C4' C5' 114.8(10)
C7' C4' C5' 123.4(10)
C6' C5' C4' 123.9(11)
C6' C5' H5'1 106.4
C4' C5' H5'1 106.4
C6' C5' H5'2 106.4
C4' C5' H5'2 106.4
H5'1 C5' H5'2 106.4
C5' C6' C1' 109.9(12)
C5' C6' C8' 117.3(9)
C1' C6' C8' 113.4(7)
C5' C6' H6' 105.0
C1' C6' H6' 105.0
C8' C6' H6' 105.0
C4' C7' H7'1 109.5
C4' C7' H7'2 109.5
H7'1 C7' H7'2 109.5
C4' C7' H7'3 109.5
H7'1 C7' H7'3 109.5
H7'2 C7' H7'3 109.5
C13' C8' C9' 120.0
C13' C8' C6' 121.7(3)
C9' C8' C6' 118.3(3)
C10' C9' C8' 120.0
C10' C9' H9' 120.0
C8' C9' H9' 120.0
C11' C10' C9' 120.0
C11' C10' Cl1' 115.5(4)
C9' C10' Cl1' 124.4(4)
C10' C11' C12' 120.0
C10' C11' H11' 120.0
C12' C11' H11' 120.0
C13' C12' C11' 120.0
C13' C12' H12' 120.0
C11' C12' H12' 120.0
C12' C13' C8' 120.0
C12' C13' H13' 120.0
C8' C13' H13' 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.396(7)
O1 H1 0.8200
N1 C2 1.292(8)
C1 C2 1.497(7)
C1 C6 1.520(12)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.448(7)
C3 C4 1.324(7)
C3 H3 0.9300
C4 C7 1.524(6)
C4 C5 1.532(10)
C5 C6 1.456(10)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C8 1.535(6)
C6 H6 0.9800
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.3900
C8 C13 1.3900
C9 C10 1.3900
C9 H9 0.9300
C10 C11 1.3900
C10 Cl1 1.687(5)
C11 C12 1.3900
C11 H11 0.9300
C12 C13 1.3900
C12 H12 0.9300
C13 H13 0.9300
O1' N1' 1.400(7)
O1' H1' 0.8200
N1' C2' 1.290(9)
C1' C2' 1.496(8)
C1' C6' 1.520(13)
C1' H1'1 0.9700
C1' H1'2 0.9700
C2' C3' 1.449(8)
C3' C4' 1.324(8)
C3' H3' 0.9300
C4' C7' 1.525(7)
C4' C5' 1.533(10)
C5' C6' 1.454(10)
C5' H5'1 0.9700
C5' H5'2 0.9700
C6' C8' 1.525(6)
C6' H6' 0.9800
C7' H7'1 0.9600
C7' H7'2 0.9600
C7' H7'3 0.9600
C8' C13' 1.3900
C8' C9' 1.3900
C9' C10' 1.3900
C9' H9' 0.9300
C10' C11' 1.3900
C10' Cl1' 1.710(6)
C11' C12' 1.3900
C11' H11' 0.9300
C12' C13' 1.3900
C12' H12' 0.9300
C13' H13' 0.9300
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 N1 C2 C3 -177.7(17)
O1 N1 C2 C1 7(3)
C6 C1 C2 N1 149(2)
C6 C1 C2 C3 -27(2)
N1 C2 C3 C4 -171.4(18)
C1 C2 C3 C4 5(3)
C2 C3 C4 C7 -176.5(15)
C2 C3 C4 C5 10(3)
C3 C4 C5 C6 0(3)
C7 C4 C5 C6 -174.3(14)
C4 C5 C6 C1 -25(3)
C4 C5 C6 C8 -159.4(14)
C2 C1 C6 C5 38(2)
C2 C1 C6 C8 174.1(12)
C5 C6 C8 C9 -108.1(13)
C1 C6 C8 C9 112.4(10)
C5 C6 C8 C13 71.8(13)
C1 C6 C8 C13 -67.7(10)
C13 C8 C9 C10 0.0
C6 C8 C9 C10 179.9(3)
C8 C9 C10 C11 0.0
C8 C9 C10 Cl1 -177.8(5)
C9 C10 C11 C12 0.0
Cl1 C10 C11 C12 177.6(6)
C10 C11 C12 C13 0.0
C11 C12 C13 C8 0.0
C9 C8 C13 C12 0.0
C6 C8 C13 C12 -179.9(3)
O1' N1' C2' C3' 177(2)
O1' N1' C2' C1' -13(4)
C6' C1' C2' N1' -140(2)
C6' C1' C2' C3' 30(3)
N1' C2' C3' C4' 172(2)
C1' C2' C3' C4' 2(3)
C2' C3' C4' C7' 171.5(18)
C2' C3' C4' C5' -16(3)
C3' C4' C5' C6' -2(4)
C7' C4' C5' C6' 170.0(19)
C4' C5' C6' C1' 32(3)
C4' C5' C6' C8' 163(2)
C2' C1' C6' C5' -43(2)
C2' C1' C6' C8' -176.8(15)
C5' C6' C8' C13' 111.6(16)
C1' C6' C8' C13' -118.5(12)
C5' C6' C8' C9' -70.0(16)
C1' C6' C8' C9' 59.9(12)
C13' C8' C9' C10' 0.0
C6' C8' C9' C10' -178.4(4)
C8' C9' C10' C11' 0.0
C8' C9' C10' Cl1' 175.1(6)
C9' C10' C11' C12' 0.0
Cl1' C10' C11' C12' -175.5(6)
C10' C11' C12' C13' 0.0
C11' C12' C13' C8' 0.0
C9' C8' C13' C12' 0.0
C6' C8' C13' C12' 178.4(4)
