#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227341.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227341
loop_
_publ_author_name
'Jin, Da-Cheng'
'Piao, Feng-Yu'
'Han, Rong-Bi'
_publ_section_title
;
 (1E)-6-Methoxy-3,4-dihydronaphthalen-1(2H)-one oxime
;
_journal_coeditor_code           CV2749
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2504
_journal_paper_doi               10.1107/S1600536810034574
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 N O2'
_chemical_formula_moiety         'C11 H13 N O2'
_chemical_formula_sum            'C11 H13 N O2'
_chemical_formula_weight         191.22
_chemical_name_systematic
;
(1E)-6-Methoxy-3,4-dihydronaphthalen-1(2H)-one oxime
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 109.02(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.185(6)
_cell_length_b                   15.878(10)
_cell_length_c                   8.053(5)
_cell_measurement_reflns_used    6826
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.08
_cell_volume                     989.4(12)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9568
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.0477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1403
_reflns_number_gt                1724
_reflns_number_total             2260
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv2749.cif
_cod_data_source_block           I
_cod_original_cell_volume        989.4(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227341
_cod_database_fobs_code          2227341
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
C C1 0.22438(15) 0.07109(8) 0.84267(17) 0.0453(3) Uani d . 1 . .
C C2 0.19968(18) 0.05982(10) 0.65136(18) 0.0588(4) Uani d . 1 . .
H H2A 0.0874 0.0819 0.5831 0.071 Uiso calc R 1 . .
H H2B 0.2007 0.0001 0.6260 0.071 Uiso calc R 1 . .
C C3 0.33762(19) 0.10345(11) 0.59483(18) 0.0660(4) Uani d . 1 . .
H H3A 0.3314 0.0837 0.4790 0.079 Uiso calc R 1 . .
H H3B 0.3160 0.1636 0.5874 0.079 Uiso calc R 1 . .
C C4 0.51630(18) 0.08688(11) 0.72171(18) 0.0601(4) Uani d . 1 . .
H H4A 0.5418 0.0272 0.7225 0.072 Uiso calc R 1 . .
H H4B 0.6009 0.1170 0.6836 0.072 Uiso calc R 1 . .
C C5 0.52944(15) 0.11461(7) 0.90409(15) 0.0421(3) Uani d . 1 . .
C C6 0.38514(15) 0.10886(7) 0.95932(15) 0.0408(3) Uani d . 1 . .
C C7 0.39938(17) 0.13786(8) 1.12760(17) 0.0518(3) Uani d . 1 . .
H H7 0.3033 0.1355 1.1650 0.062 Uiso calc R 1 . .
C C8 0.55144(17) 0.16968(9) 1.23853(18) 0.0545(4) Uani d . 1 . .
H H8 0.5583 0.1883 1.3501 0.065 Uiso calc R 1 . .
C C9 0.69544(15) 0.17400(8) 1.18325(16) 0.0466(3) Uani d . 1 . .
C C10 0.68406(15) 0.14690(8) 1.01691(16) 0.0454(3) Uani d . 1 . .
H H10 0.7803 0.1502 0.9799 0.055 Uiso calc R 1 . .
C C11 0.98486(18) 0.22289(12) 1.2455(2) 0.0728(5) Uani d . 1 . .
H H11A 1.0245 0.1709 1.2110 0.109 Uiso calc R 1 . .
H H11B 1.0762 0.2478 1.3397 0.109 Uiso calc R 1 . .
H H11C 0.9512 0.2608 1.1472 0.109 Uiso calc R 1 . .
N N1 0.11395(13) 0.04621(7) 0.91439(15) 0.0541(3) Uani d . 1 . .
O O1 -0.03579(13) 0.01124(8) 0.79076(14) 0.0707(4) Uani d . 1 . .
H H1 -0.0958 -0.0108 0.8427 0.106 Uiso calc R 1 . .
O O2 0.84142(12) 0.20688(7) 1.30220(13) 0.0634(3) Uani d . 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C6 . . 116.90(12) ?
N1 C1 C2 . . 123.19(12) ?
C6 C1 C2 . . 119.86(11) ?
C1 C2 C3 . . 112.97(11) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C4 C3 C2 . . 111.67(13) ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3B . . 109.3 ?
C2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 107.9 ?
C5 C4 C3 . . 110.81(12) ?
C5 C4 H4A . . 109.5 ?
C3 C4 H4A . . 109.5 ?
C5 C4 H4B . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 108.1 ?
C10 C5 C6 . . 120.00(12) ?
C10 C5 C4 . . 120.37(11) ?
C6 C5 C4 . . 119.62(11) ?
C5 C6 C7 . . 118.39(11) ?
C5 C6 C1 . . 119.81(12) ?
C7 C6 C1 . . 121.79(11) ?
C8 C7 C6 . . 121.59(12) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C7 C8 C9 . . 119.60(13) ?
C7 C8 H8 . . 120.2 ?
C9 C8 H8 . . 120.2 ?
O2 C9 C10 . . 124.44(11) ?
O2 C9 C8 . . 115.63(12) ?
C10 C9 C8 . . 119.93(12) ?
C9 C10 C5 . . 120.47(11) ?
C9 C10 H10 . . 119.8 ?
C5 C10 H10 . . 119.8 ?
O2 C11 H11A . . 109.5 ?
O2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
O2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C1 N1 O1 . . 112.30(12) ?
N1 O1 H1 . . 109.5 ?
C9 O2 C11 . . 118.02(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.2833(17) ?
C1 C6 . 1.4724(18) ?
C1 C2 . 1.498(2) ?
C2 C3 . 1.516(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.509(2) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.5032(19) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C10 . 1.3930(19) ?
C5 C6 . 1.3940(18) ?
C6 C7 . 1.3997(19) ?
C7 C8 . 1.3703(19) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.3907(19) ?
C8 H8 . 0.9300 ?
C9 O2 . 1.3681(16) ?
C9 C10 . 1.3808(19) ?
C10 H10 . 0.9300 ?
C11 O2 . 1.415(2) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
N1 O1 . 1.4164(16) ?
O1 H1 . 0.8200 ?
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 H1 N1 3_557 0.82 2.09 2.805(2) 146.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4878084
