#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/70/2007070.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_2007070
loop_
_publ_author_name
'Chiaroni, Angèle'
'Riche, Claude'
'Dumas Franc̨oise'
'Mauduit, Marc'
'Miet, Christine'
_publ_section_title
;6-Allyl-8,8-dimethyl-3-oxo-2-(1-phenylethyl)-2-azabicyclo[4.3.0]non-1(9)-ene-5-carboxylic
 Acid, a Key Compound in the Asymmetric Synthesis of Quadrone
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              401
_journal_page_last               403
_journal_paper_doi               10.1107/S0108270197015448
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C22 H27 N O3'
_chemical_formula_structural     'C22 H27 N O3'
_chemical_formula_sum            'C22 H27 N O3'
_chemical_formula_weight         353.45
_chemical_melting_point          423
_chemical_name_systematic
;
[N-(1'-Phenylethyl)-2-azabicyclo[4,3,0]-6-allyl-8,8-dimethyl-3-oxonon
-5-yl]-carboxylic acid
;
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.154(7)
_cell_length_b                   13.154(7)
_cell_length_c                   11.869(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.2
_cell_measurement_theta_min      8.7
_cell_volume                     2054(2)
_computing_cell_refinement       'Philips PW1100/20 software'
_computing_data_collection       'Philips PW1100/20 software'
_computing_data_reduction        'PHIL (Riche, 1981)'
_computing_molecular_graphics
'R3M (Riche, 1983) and  ORTEP (Johnson, 1963)'
_computing_publication_material  'ACTACIF (Riche, 1992)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Philips PW1100'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3951
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 600
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.54
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.092
_refine_ls_abs_structure_details 'given by chemistry'
_refine_ls_extinction_coef       0.045(3)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.083
_refine_ls_goodness_of_fit_obs   1.095
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.329
_refine_ls_restrained_S_obs      1.095
_refine_ls_R_factor_all          0.040
_refine_ls_R_factor_obs          .031
_refine_ls_shift/esd_max         -0.006
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0349P)²+0.0942P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.095
_refine_ls_wR_factor_obs         .073
_reflns_number_observed          1682
_reflns_number_total             1899
_reflns_observed_criterion       I>2sigma(I)
_cod_data_source_file            cf1188.cif
_cod_data_source_block           cf1188
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 'Tetragonal' changed to 'tetragonal'
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.0942P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.0942P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2007070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 .16473(15) .36462(15) .2837(2) .0433(5) Uani d . 1 . C
N2 .19588(12) .44797(13) .2162(2) .0463(4) Uani d . 1 . N
C3 .1353(2) .4836(2) .1320 .0489(5) Uani d . 1 . C
C4 .0277(2) .4454(2) .1202(3) .0537(5) Uani d . 1 . C
H4A .0216(2) .4128(2) .0472(3) .064 Uiso calc R 1 . H
H4B -.0172(2) .5038(2) .1199(3) .064 Uiso calc R 1 . H
C5 -.01056(15) .3712(2) .2091(2) .0477(5) Uani d . 1 . C
H5 -.06626(15) .3309(2) .1774(2) .057 Uiso calc R 1 . H
C6 .0785(2) .2992(2) .2412(2) .0472(5) Uani d . 1 . C
C7 .0595(2) .2280(2) .3420(3) .0599(6) Uani d . 1 . C
H7A .0564(2) .1580(2) .3166(3) .072 Uiso calc R 1 . H
H7B -.0047(2) .2447(2) .3777(3) .072 Uiso calc R 1 . H
C8 .1479(2) .2414(2) .4272(2) .0490(5) Uani d . 1 . C
C9 .2024(2) .3332(2) .3809(2) .0479(5) Uani d . 1 . C
H9 .2568(2) .3645(2) .4170(2) .058 Uiso calc R 1 . H
C10 .29963(15) .4910(2) .2261(3) .0487(5) Uani d . 1 . C
H10 .30624(15) .5390(2) .1634(3) .058 Uiso calc R 1 . H
C11 .3796(2) .4087(2) .2045(3) .0621(6) Uani d . 1 . C
H11A .4462(2) .4385(3) .2064(15) .081 Uiso calc R 1 . H
H11B .3681(8) .3787(9) .1318(7) .081 Uiso calc R 1 . H
H11C .3746(9) .3572(7) .2616(9) .081 Uiso calc R 1 . H
C12 .31484(15) .55389(15) .3321(3) .0470(5) Uani d . 1 . C
C13 .4109(2) .5962(2) .3532(3) .0564(6) Uani d . 1 . C
H13 .4645(2) .5814(2) .3049(3) .068 Uiso calc R 1 . H
C14 .4273(2) .6593(2) .4444(3) .0659(7) Uani d . 1 . C
H14 .4916(2) .6863(2) .4570(3) .079 Uiso calc R 1 . H
C15 .3488(2) .6824(2) .5166(3) .0723(7) Uani d . 1 . C
H15 .3597(2) .7244(2) .5785(3) .087 Uiso calc R 1 . H
C16 .2541(2) .6425(2) .4958(3) .0709(7) Uani d . 1 . C
H16 .2007(2) .6581(2) .5441(3) .085 Uiso calc R 1 . H
C17 .2367(2) .5800(2) .4046(3) .0566(5) Uani d . 1 . C
H17 .1716(2) .5549(2) .3917(3) .068 Uiso calc R 1 . H
O18 .16750(13) .54749(13) .0653(2) .0679(5) Uani d . 1 . O
C19 -.0491(2) .4292(2) .3105(2) .0510(5) Uani d . 1 . C
O20 -.01597(14) .51002(14) .3403(2) .0707(5) Uani d . 1 . O
O21 -.12374(13) .38168(14) .3640(2) .0737(5) Uani d . 1 . O
H21 -.1356(16) .4109(14) .4235(13) .096 Uiso calc R 1 . H
C22 .1129(2) .2386(2) .1355(3) .0620(6) Uani d . 1 . C
H22A .1402(2) .2860(2) .0807(3) .074 Uiso calc R 1 . H
H22B .1674(2) .1929(2) .1571(3) .074 Uiso calc R 1 . H
C23 .0306(2) .1778(2) .0808(4) .0855(9) Uani d . 1 . C
H23 -.0021(2) .1297(2) .1253(4) .103 Uiso calc R 1 . H
C24 .0005(4) .1858(4) -.0224(4) .134(2) Uani d . 1 . C
H24A .0308(4) .2329(4) -.0701(4) .187 Uiso calc R 1 . H
H24B -.0516(4) .1444(4) -.0489(4) .187 Uiso calc R 1 . H
C25 .2173(2) .1488(2) .4317(3) .0695(7) Uani d . 1 . C
H25A .1792(4) .0908(4) .4570(14) .090 Uiso calc R 1 . H
H25B .2722(8) .1615(6) .4830(12) .090 Uiso calc R 1 . H
H25C .2441(10) .1355(8) .3579(4) .090 Uiso calc R 1 . H
C26 .1088(2) .2623(2) .5458(3) .0713(7) Uani d . 1 . C
H26A .0724(11) .2039(5) .5729(6) .093 Uiso calc R 1 . H
H26B .0641(11) .3200(8) .5444(4) .093 Uiso calc R 1 . H
H26C .1652(2) .2761(13) .5948(4) .093 Uiso calc R 1 . H
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'
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'
H H 0.0000 0.0000 '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
_geom_angle_publ_flag
C9 C1 N2 128.8(2) yes
C9 C1 C6 113.3(2) yes
N2 C1 C6 117.9(2) yes
C3 N2 C1 120.8(2) yes
C3 N2 C10 117.8(2) ?
C1 N2 C10 121.1(2) ?
O18 C3 N2 120.4(2) ?
O18 C3 C4 119.4(2) ?
N2 C3 C4 120.2(2) yes
C3 C4 C5 117.3(2) yes
C19 C5 C4 109.9(2) ?
C19 C5 C6 111.4(2) ?
C4 C5 C6 108.1(2) yes
C1 C6 C7 102.1(2) yes
C1 C6 C5 107.5(2) yes
C7 C6 C5 116.1(2) yes
C1 C6 C22 110.1(2) ?
C7 C6 C22 111.2(2) ?
C5 C6 C22 109.5(2) ?
C6 C7 C8 108.4(2) yes
C9 C8 C25 111.6(2) ?
C9 C8 C26 110.6(2) ?
C25 C8 C26 108.3(2) ?
C9 C8 C7 102.1(2) yes
C25 C8 C7 112.4(2) ?
C26 C8 C7 111.7(2) ?
C1 C9 C8 113.0(2) yes
N2 C10 C12 113.3(2) ?
N2 C10 C11 110.4(2) ?
C12 C10 C11 115.7(2) ?
C17 C12 C13 117.3(2) ?
C17 C12 C10 123.5(2) ?
C13 C12 C10 118.9(2) ?
C14 C13 C12 121.3(2) ?
C15 C14 C13 120.2(2) ?
C16 C15 C14 119.0(3) ?
C15 C16 C17 121.3(2) ?
C16 C17 C12 120.9(2) ?
O20 C19 O21 123.0(2) ?
O20 C19 C5 123.9(2) ?
O21 C19 C5 113.1(2) ?
C23 C22 C6 114.5(2) ?
C24 C23 C22 126.3(4) ?
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 C9 . 1.322(3) yes
C1 N2 . 1.419(3) yes
C1 C6 . 1.510(3) yes
N2 C3 . 1.361(3) yes
N2 C10 . 1.482(3) ?
C3 O18 . 1.230(3) ?
C3 C4 . 1.508(3) yes
C4 C5 . 1.523(3) yes
C5 C19 . 1.512(3) ?
C5 C6 . 1.554(3) yes
C6 C7 . 1.540(3) yes
C6 C22 . 1.554(3) ?
C7 C8 . 1.551(3) yes
C8 C9 . 1.508(3) yes
C8 C25 . 1.524(3) ?
C8 C26 . 1.523(3) ?
C10 C12 . 1.519(3) ?
C10 C11 . 1.531(3) ?
C12 C17 . 1.383(3) ?
C12 C13 . 1.403(3) ?
C13 C14 . 1.381(4) ?
C14 C15 . 1.375(4) ?
C15 C16 . 1.374(4) ?
C16 C17 . 1.379(4) ?
C19 O20 . 1.203(3) ?
C19 O21 . 1.325(3) ?
C22 C23 . 1.494(4) ?
C23 C24 . 1.291(6) ?
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
_geom_torsion_publ_flag
C1 N2 C3 C4 9.1(3) yes
N2 C3 C4 C5 3.3(3) yes
C3 C4 C5 C6 -37.5(2) yes
C4 C5 C6 C1 58.3(2) yes
C5 C6 C1 N2 -50.8(2) yes
C6 C1 N2 C3 16.3(3) yes
C1 C6 C7 C8 -10.8(2) yes
C6 C7 C8 C9 10.0(2) yes
C7 C8 C9 C1 -5.3(2) yes
C8 C9 C1 C6 -1.6(2) yes
C9 C1 C6 C7 7.9(2) yes
C9 C1 N2 C3 -165.1(2) ?
C9 C1 N2 C10 22.1(3) ?
C1 N2 C10 C11 57.3(3) ?
C1 N2 C10 C12 -74.3(2) yes
C3 N2 C10 C12 112.1(2) yes
N2 C10 C12 C13 178.0(2) yes
N2 C10 C12 C17 -8.2(3) ?
C1 C6 C5 C19 -62.5(2) ?
C7 C6 C5 C19 51.0(3) ?
C6 C5 C19 O20 89.2(3) ?
C6 C5 C19 O21 -90.7(2) ?
C1 C6 C22 C23 -175.1(2) ?
C6 C22 C23 C24 122.0(4) ?
C5 C6 C22 C23 -57.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21186066
