#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/30/2223067.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_2223067
loop_
_publ_author_name
'Yuan, Xian-You'
'Zhang, Min'
'Ng, Seik Weng'
_publ_section_title
;
 Perillartine
;
_journal_coeditor_code           HB5034
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2149
_journal_paper_doi               10.1107/S1600536809031225
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H15 N O'
_chemical_formula_moiety         'C10 H15 N O'
_chemical_formula_sum            'C10 H15 N O'
_chemical_formula_weight         165.23
_chemical_name_common            Perillartine
_chemical_name_systematic
;
4-(1-Methylvinyl)cyclohexene-1-carbaldehyde oxime
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.1500(10)
_cell_angle_beta                 95.6580(10)
_cell_angle_gamma                104.6020(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2679(6)
_cell_length_b                   8.1702(7)
_cell_length_c                   8.9426(8)
_cell_measurement_reflns_used    1889
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.9
_cell_measurement_theta_min      2.4
_cell_volume                     488.25(7)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART'
_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  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4074
_diffrn_reflns_theta_full        27.05
_diffrn_reflns_theta_max         27.05
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             180
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.121
_refine_ls_abs_structure_details none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0433
_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)+(0.0793P)²+0.0172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                1457
_reflns_number_total             2078
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5034.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2223067
_cod_database_fobs_code          2223067
loop_
_symmetry_equiv_pos_as_xyz
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5000(4) 0.5002(4) 0.5001(3) 0.0885(8) Uani d D 1 . .
O O2 0.7482(4) 0.9157(4) 0.6717(4) 0.0922(8) Uani d D 1 . .
N N1 0.4289(4) 0.6405(4) 0.4831(3) 0.0724(8) Uani d . 1 . .
N N2 0.8170(4) 0.7770(4) 0.6971(3) 0.0727(7) Uani d . 1 . .
C C1 0.2564(5) 0.5857(4) 0.4097(4) 0.0699(8) Uani d . 1 . .
H H1A 0.1932 0.4649 0.3775 0.084 Uiso calc R 1 . .
C C2 0.1551(5) 0.7069(4) 0.3745(4) 0.0657(8) Uani d . 1 B .
C C3 -0.0246(5) 0.6464(4) 0.2976(4) 0.0758(9) Uani d . 1 . .
H H3 -0.0836 0.5251 0.2706 0.091 Uiso calc R 1 . .
C C4 -0.1401(5) 0.7574(4) 0.2510(4) 0.0776(9) Uani d . 1 B .
H H4A -0.2386 0.7643 0.3161 0.093 Uiso calc R 1 . .
H H4B -0.2048 0.7010 0.1425 0.093 Uiso calc R 1 . .
C C5 -0.0167(5) 0.9448(4) 0.2672(4) 0.0760(9) Uani d . 1 . .
H H5 0.0572 0.9363 0.1809 0.091 Uiso calc R 1 A 1
C C6 0.1263(6) 1.0142(4) 0.4182(6) 0.0973(13) Uani d . 1 B .
H H6A 0.0572 1.0176 0.5058 0.117 Uiso calc R 1 . .
H H6B 0.2013 1.1345 0.4291 0.117 Uiso calc R 1 . .
C C7 0.2618(6) 0.9016(5) 0.4248(5) 0.0905(12) Uani d . 1 . .
H H7A 0.3552 0.9237 0.3567 0.109 Uiso calc R 1 B .
H H7B 0.3320 0.9354 0.5314 0.109 Uiso calc R 1 . .
C C8 -0.1413(5) 1.0638(4) 0.2484(4) 0.0784(10) Uani d PD 0.50 B 1
C C9 -0.2394(18) 1.127(2) 0.3557(11) 0.088(3) Uani d PDU 0.50 B 1
H H9A -0.3134 1.1999 0.3366 0.105 Uiso calc PR 0.50 B 1
H H9B -0.2342 1.0994 0.4501 0.105 Uiso calc PR 0.50 B 1
C C10 -0.1478(19) 1.1072(18) 0.0954(12) 0.093(3) Uani d PDU 0.50 B 1
H H10A -0.2124 1.0017 0.0107 0.139 Uiso calc PR 0.50 B 1
H H10B -0.0186 1.1541 0.0797 0.139 Uiso calc PR 0.50 B 1
H H10C -0.2167 1.1936 0.0979 0.139 Uiso calc PR 0.50 B 1
C C8' -0.1413(5) 1.0638(4) 0.2484(4) 0.0784(10) Uani d P 0.50 B 2
C C9' -0.1960(17) 1.0794(19) 0.1074(12) 0.088(3) Uani d PD 0.50 B 2
H H9'A -0.2772 1.1487 0.0964 0.105 Uiso calc PR 0.50 B 2
H H9'B -0.1529 1.0210 0.0200 0.105 Uiso calc PR 0.50 B 2
C C10' -0.208(2) 1.157(2) 0.3937(11) 0.093(3) Uani d PD 0.50 B 2
H H10D -0.2765 1.2350 0.3683 0.139 Uiso calc PR 0.50 B 2
H H10E -0.0981 1.2236 0.4747 0.139 Uiso calc PR 0.50 B 2
H H10F -0.2922 1.0702 0.4303 0.139 Uiso calc PR 0.50 B 2
C C11 0.9893(5) 0.8319(4) 0.7688(4) 0.0733(9) Uani d . 1 . .
H H11 1.0553 0.9518 0.7953 0.088 Uiso calc R 1 . .
C C12 1.0866(5) 0.7107(4) 0.8108(4) 0.0644(8) Uani d . 1 . .
C C13 1.2696(5) 0.7692(4) 0.8782(5) 0.0781(10) Uani d . 1 . .
H H13 1.3307 0.8898 0.9017 0.094 Uiso calc R 1 . .
C C14 1.3864(5) 0.6556(4) 0.9198(5) 0.0798(10) Uani d . 1 . .
H H14A 1.4061 0.6763 1.0328 0.096 Uiso calc R 1 . .
H H14B 1.5121 0.6889 0.8899 0.096 Uiso calc R 1 . .
C C15 1.2887(4) 0.4597(4) 0.8383(4) 0.0632(7) Uani d . 1 . .
H H15 1.2949 0.4391 0.7262 0.076 Uiso calc R 1 . .
C C16 1.0754(4) 0.4179(4) 0.8527(5) 0.0746(9) Uani d . 1 . .
H H16A 1.0134 0.2921 0.8053 0.090 Uiso calc R 1 . .
H H16B 1.0640 0.4475 0.9631 0.090 Uiso calc R 1 . .
C C17 0.9742(5) 0.5210(4) 0.7724(5) 0.0763(10) Uani d . 1 . .
H H17A 0.9523 0.4671 0.6594 0.092 Uiso calc R 1 . .
H H17B 0.8492 0.5137 0.8041 0.092 Uiso calc R 1 . .
C C18 1.3935(4) 0.3442(4) 0.8964(4) 0.0666(8) Uani d . 1 . .
C C19 1.4889(6) 0.2566(5) 0.8038(5) 0.0813(9) Uani d . 1 . .
H H19A 1.5548 0.1866 0.8401 0.098 Uiso calc R 1 . .
H H19B 1.4904 0.2646 0.7021 0.098 Uiso calc R 1 . .
C C20 1.3869(7) 0.3355(6) 1.0597(5) 0.0934(11) Uani d . 1 . .
H H20A 1.4500 0.2509 1.0786 0.140 Uiso calc R 1 . .
H H20B 1.2548 0.2998 1.0733 0.140 Uiso calc R 1 . .
H H20C 1.4516 0.4500 1.1328 0.140 Uiso calc R 1 . .
H H1 0.599(5) 0.568(5) 0.568(5) 0.115(18) Uiso d D 1 . .
H H2 0.641(4) 0.866(5) 0.609(5) 0.110(17) Uiso d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 O1 H1 . . 94(3) ?
N2 O2 H2 . . 106(3) ?
C1 N1 O1 . . 111.9(3) ?
C11 N2 O2 . . 112.1(3) ?
N1 C1 C2 . . 121.6(3) ?
N1 C1 H1A . . 119.2 ?
C2 C1 H1A . . 119.2 ?
C3 C2 C1 . . 120.4(3) ?
C3 C2 C7 . . 121.3(3) ?
C1 C2 C7 . . 118.3(3) ?
C2 C3 C4 . . 125.1(3) ?
C2 C3 H3 . . 117.5 ?
C4 C3 H3 . . 117.5 ?
C3 C4 C5 . . 112.7(3) ?
C3 C4 H4A . . 109.1 ?
C5 C4 H4A . . 109.1 ?
C3 C4 H4B . . 109.1 ?
C5 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.8 ?
C6 C5 C8 . . 114.0(3) ?
C6 C5 C4 . . 109.6(3) ?
C8 C5 C4 . . 111.3(3) ?
C6 C5 H5 . . 107.2 ?
C8 C5 H5 . . 107.2 ?
C4 C5 H5 . . 107.2 ?
C5 C6 C7 . . 112.3(3) ?
C5 C6 H6A . . 109.2 ?
C7 C6 H6A . . 109.2 ?
C5 C6 H6B . . 109.2 ?
C7 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C2 C7 C6 . . 111.9(3) ?
C2 C7 H7A . . 109.2 ?
C6 C7 H7A . . 109.2 ?
C2 C7 H7B . . 109.2 ?
C6 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
C9 C8 C10 . . 120.8(8) ?
C9 C8 C5 . . 124.4(6) ?
C10 C8 C5 . . 114.7(6) ?
C8 C9 H9A . . 120.0 ?
C8 C9 H9B . . 120.0 ?
H9A C9 H9B . . 120.0 ?
H9'A C9' H9'B . . 120.0 ?
H10D C10' H10E . . 109.5 ?
H10D C10' H10F . . 109.5 ?
H10E C10' H10F . . 109.5 ?
N2 C11 C12 . . 121.0(3) ?
N2 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C13 C12 C11 . . 120.0(3) ?
C13 C12 C17 . . 121.9(3) ?
C11 C12 C17 . . 118.0(3) ?
C12 C13 C14 . . 124.6(3) ?
C12 C13 H13 . . 117.7 ?
C14 C13 H13 . . 117.7 ?
C13 C14 C15 . . 112.1(3) ?
C13 C14 H14A . . 109.2 ?
C15 C14 H14A . . 109.2 ?
C13 C14 H14B . . 109.2 ?
C15 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C18 C15 C14 . . 112.0(2) ?
C18 C15 C16 . . 114.2(2) ?
C14 C15 C16 . . 108.9(3) ?
C18 C15 H15 . . 107.1 ?
C14 C15 H15 . . 107.1 ?
C16 C15 H15 . . 107.1 ?
C17 C16 C15 . . 111.1(2) ?
C17 C16 H16A . . 109.4 ?
C15 C16 H16A . . 109.4 ?
C17 C16 H16B . . 109.4 ?
C15 C16 H16B . . 109.4 ?
H16A C16 H16B . . 108.0 ?
C12 C17 C16 . . 112.7(3) ?
C12 C17 H17A . . 109.0 ?
C16 C17 H17A . . 109.0 ?
C12 C17 H17B . . 109.0 ?
C16 C17 H17B . . 109.0 ?
H17A C17 H17B . . 107.8 ?
C19 C18 C20 . . 122.0(3) ?
C19 C18 C15 . . 120.0(3) ?
C20 C18 C15 . . 118.0(3) ?
C18 C19 H19A . . 120.0 ?
C18 C19 H19B . . 120.0 ?
H19A C19 H19B . . 120.0 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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
O1 N1 . 1.407(3) ?
O1 H1 . 0.85(4) ?
O2 N2 . 1.408(3) ?
O2 H2 . 0.85(4) ?
N1 C1 . 1.266(4) ?
N2 C11 . 1.261(5) ?
C1 C2 . 1.451(4) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.320(5) ?
C2 C7 . 1.506(5) ?
C3 C4 . 1.487(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.529(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.500(5) ?
C5 C8 . 1.514(4) ?
C5 H5 . 0.9800 ?
C6 C7 . 1.515(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.327(8) ?
C8 C10 . 1.500(8) ?
C9 H9A . 0.9300 ?
C9 H9B . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C9' H9'A . 0.9300 ?
C9' H9'B . 0.9300 ?
C10' H10D . 0.9600 ?
C10' H10E . 0.9600 ?
C10' H10F . 0.9600 ?
C11 C12 . 1.455(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.316(5) ?
C12 C17 . 1.489(5) ?
C13 C14 . 1.495(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.520(4) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C18 . 1.511(4) ?
C15 C16 . 1.527(4) ?
C15 H15 . 0.9800 ?
C16 C17 . 1.514(4) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.316(5) ?
C18 C20 . 1.485(5) ?
C19 H19A . 0.9300 ?
C19 H19B . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
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 H1 N2 . 0.85(4) 2.00(2) 2.831(4) 164(5) yes
O2 H2 N1 . 0.85(4) 2.04(2) 2.811(4) 150(4) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C1 C2 . . . . -178.2(3) ?
N1 C1 C2 C3 . . . . 179.9(3) ?
N1 C1 C2 C7 . . . . 1.2(5) ?
C1 C2 C3 C4 . . . . -178.0(3) ?
C7 C2 C3 C4 . . . . 0.7(6) ?
C2 C3 C4 C5 . . . . 13.1(5) ?
C3 C4 C5 C6 . . . . -42.4(4) ?
C3 C4 C5 C8 . . . . -169.4(3) ?
C8 C5 C6 C7 . . . . -174.0(4) ?
C4 C5 C6 C7 . . . . 60.5(5) ?
C3 C2 C7 C6 . . . . 15.8(5) ?
C1 C2 C7 C6 . . . . -165.5(3) ?
C5 C6 C7 C2 . . . . -46.7(5) ?
C6 C5 C8 C9 . . . . -51.0(9) ?
C4 C5 C8 C9 . . . . 73.5(8) ?
C6 C5 C8 C10 . . . . 129.0(7) ?
C4 C5 C8 C10 . . . . -106.4(7) ?
O2 N2 C11 C12 . . . . 178.3(3) ?
N2 C11 C12 C13 . . . . 176.4(3) ?
N2 C11 C12 C17 . . . . -2.5(5) ?
C11 C12 C13 C14 . . . . -177.1(3) ?
C17 C12 C13 C14 . . . . 1.7(6) ?
C12 C13 C14 C15 . . . . 15.1(6) ?
C13 C14 C15 C18 . . . . -172.6(3) ?
C13 C14 C15 C16 . . . . -45.3(4) ?
C18 C15 C16 C17 . . . . -172.3(3) ?
C14 C15 C16 C17 . . . . 61.8(4) ?
C13 C12 C17 C16 . . . . 13.8(5) ?
C11 C12 C17 C16 . . . . -167.3(3) ?
C15 C16 C17 C12 . . . . -45.5(4) ?
C14 C15 C18 C19 . . . . -109.8(4) ?
C16 C15 C18 C19 . . . . 125.9(3) ?
C14 C15 C18 C20 . . . . 69.4(4) ?
C16 C15 C18 C20 . . . . -54.9(4) ?
