#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:30:10 +0100 (lun 21 de mar de 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029293.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_4029293
loop_
_publ_author_name
'Zhu, Jia-Liang'
'Wu, Sih-Ting'
'Shie, Jr-Yun'
_publ_section_title
;
 Access to Functionalized Bicyclo[4,3,0]nonenes via Palladium-Catalyzed
 Oxidative Cyclization of 2-Allylcyclohexyl Oximes.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3623
_journal_page_last               3633
_journal_paper_doi               10.1021/jo5005422
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C11 H19 O2'
_chemical_formula_weight         183.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 102.529(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.655(3)
_cell_length_b                   10.193(3)
_cell_length_c                   8.544(2)
_cell_measurement_reflns_used    2266
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.59
_cell_volume                     1075.9(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3099
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_correction_T_min  0.9718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0507
_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)+(0.0965P)²+0.3236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                1561
_reflns_number_total             1753
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5005422_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029293.cif.
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4029293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.1815(3) 0.3390(3) 0.9576(5) 0.0688(9) Uani 1 1 d .
H1A H 0.2236 0.3465 1.0665 0.083 Uiso 1 1 calc R
H1B H 0.1274 0.4080 0.9406 0.083 Uiso 1 1 calc R
C2 C 0.2565(5) 0.3571(5) 0.8396(9) 0.117(2) Uani 1 1 d .
H2A H 0.2873 0.4446 0.8514 0.140 Uiso 1 1 calc R
H2B H 0.3155 0.2944 0.8642 0.140 Uiso 1 1 calc R
C3 C 0.1946(5) 0.3374(6) 0.6676(7) 0.124(2) Uani 1 1 d .
H3 H 0.1903 0.3998 0.5871 0.149 Uiso 1 1 calc R
C4 C 0.1420(4) 0.2066(5) 0.6437(5) 0.0934(16) Uani 1 1 d .
H4A H 0.1973 0.1394 0.6543 0.112 Uiso 1 1 calc R
H4B H 0.0978 0.2015 0.5359 0.112 Uiso 1 1 calc R
C5 C 0.0724(3) 0.1800(3) 0.7614(3) 0.0612(8) Uani 1 1 d .
H5 H 0.0522 0.0870 0.7523 0.073 Uiso 1 1 calc R
C6 C 0.1256(2) 0.2068(2) 0.9363(3) 0.0405(6) Uani 1 1 d .
C7 C 0.0289(3) 0.1989(3) 1.0179(4) 0.0548(7) Uani 1 1 d .
H7 H 0.0135 0.1052 1.0256 0.066 Uiso 1 1 calc R
C8 C -0.0687(3) 0.2560(3) 0.8965(4) 0.0597(8) Uani 1 1 d .
H8 H -0.1281 0.1926 0.8849 0.072 Uiso 1 1 calc R
C9 C -0.0324(3) 0.2605(5) 0.7382(4) 0.0825(12) Uani 1 1 d .
H9A H -0.0194 0.3504 0.7102 0.099 Uiso 1 1 calc R
H9B H -0.0876 0.2232 0.6530 0.099 Uiso 1 1 calc R
C10 C 0.0484(4) 0.2516(6) 1.1889(5) 0.0944(15) Uani 1 1 d .
H10A H 0.1087 0.2066 1.2544 0.142 Uiso 1 1 calc R
H10B H -0.0151 0.2375 1.2312 0.142 Uiso 1 1 calc R
H10C H 0.0637 0.3438 1.1887 0.142 Uiso 1 1 calc R
C11 C -0.1107(2) 0.3860(3) 0.9389(4) 0.0571(7) Uani 1 1 d .
H11A H -0.1303 0.3798 1.0423 0.068 Uiso 1 1 calc R
H11B H -0.0544 0.4519 0.9468 0.068 Uiso 1 1 calc R
O1 O -0.20203(18) 0.4241(3) 0.8212(3) 0.0721(7) Uani 1 1 d .
H1 H -0.2407 0.4720 0.8618 0.108 Uiso 1 1 calc R
O2 O 0.20339(16) 0.10533(18) 0.9884(2) 0.0546(5) Uani 1 1 d .
H2 H 0.2231 0.1076 1.0863 0.082 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0617(19) 0.0538(15) 0.097(3) -0.0150(15) 0.0312(18) 0.0022(14)
C2 0.101(3) 0.087(3) 0.189(7) 0.012(3) 0.092(4) -0.001(3)
C3 0.161(5) 0.123(4) 0.123(4) 0.069(4) 0.104(4) 0.070(4)
C4 0.128(4) 0.115(3) 0.0441(19) 0.0214(19) 0.035(2) 0.073(3)
C5 0.079(2) 0.0643(17) 0.0374(15) -0.0016(12) 0.0062(14) 0.0326(16)
C6 0.0467(14) 0.0388(12) 0.0360(13) 0.0001(9) 0.0086(11) 0.0165(10)
C7 0.0532(15) 0.0641(17) 0.0485(17) 0.0139(13) 0.0143(12) 0.0161(13)
C8 0.0486(16) 0.0635(17) 0.0638(19) -0.0074(13) 0.0051(13) 0.0070(14)
C9 0.082(3) 0.114(3) 0.0447(19) -0.0078(16) -0.0022(18) 0.048(2)
C10 0.078(2) 0.169(4) 0.0403(19) 0.018(2) 0.0220(15) 0.054(3)
C11 0.0439(15) 0.0750(19) 0.0502(17) -0.0022(13) 0.0056(12) 0.0190(14)
O1 0.0640(13) 0.0897(16) 0.0533(13) -0.0189(10) -0.0075(10) 0.0420(12)
O2 0.0607(12) 0.0634(12) 0.0377(10) 0.0054(8) 0.0065(8) 0.0328(10)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 111.5(3)
C6 C1 H1A 109.3
C2 C1 H1A 109.3
C6 C1 H1B 109.3
C2 C1 H1B 109.3
H1A C1 H1B 108.0
C3 C2 C1 110.8(4)
C3 C2 H2A 109.5
C1 C2 H2A 109.5
C3 C2 H2B 109.5
C1 C2 H2B 109.5
H2A C2 H2B 108.1
C4 C3 C2 111.9(3)
C4 C3 H3 124.0
C2 C3 H3 124.0
C3 C4 C5 112.5(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
C4 C5 C6 115.3(3)
C4 C5 C9 115.7(3)
C6 C5 C9 102.5(2)
C4 C5 H5 107.7
C6 C5 H5 107.7
C9 C5 H5 107.7
O2 C6 C1 109.5(2)
O2 C6 C5 107.59(18)
C1 C6 C5 111.9(3)
O2 C6 C7 112.5(2)
C1 C6 C7 112.9(2)
C5 C6 C7 102.1(2)
C10 C7 C6 115.9(3)
C10 C7 C8 116.8(3)
C6 C7 C8 106.0(2)
C10 C7 H7 105.7
C6 C7 H7 105.7
C8 C7 H7 105.7
C11 C8 C9 112.2(3)
C11 C8 C7 116.3(3)
C9 C8 C7 104.9(3)
C11 C8 H8 107.7
C9 C8 H8 107.7
C7 C8 H8 107.7
C8 C9 C5 106.7(3)
C8 C9 H9A 110.4
C5 C9 H9A 110.4
C8 C9 H9B 110.4
C5 C9 H9B 110.4
H9A C9 H9B 108.6
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O1 C11 C8 110.4(3)
O1 C11 H11A 109.6
C8 C11 H11A 109.6
O1 C11 H11B 109.6
C8 C11 H11B 109.6
H11A C11 H11B 108.1
C11 O1 H1 109.5
C6 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.514(4)
C1 C2 1.539(6)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.521(10)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.485(8)
C3 H3 0.9300
C4 C5 1.498(5)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.524(4)
C5 C9 1.537(4)
C5 H5 0.9800
C6 O2 1.431(3)
C6 C7 1.536(4)
C7 C10 1.526(5)
C7 C8 1.544(5)
C7 H7 0.9800
C8 C11 1.501(4)
C8 C9 1.520(5)
C8 H8 0.9800
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 O1 1.412(4)
C11 H11A 0.9700
C11 H11B 0.9700
O1 H1 0.8200
O2 H2 0.8200
