#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/21/4102124.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_4102124
loop_
_publ_author_name
'Christoph Schotes'
'Antonio Mezzetti'
_publ_section_title
;
 Asymmetric Diels-Alder Reactions of Unsaturated β-Ketoesters Catalyzed
 by Chiral Ruthenium PNNP Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3652
_journal_page_last               3653
_journal_paper_doi               10.1021/ja910039e
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H32 O6'
_chemical_formula_sum            'C23 H32 O6'
_chemical_formula_weight         404.49
_chemical_name_common            'Camphanic Acid Ester ent-16'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 108.615(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.2734(15)
_cell_length_b                   7.0211(9)
_cell_length_c                   13.0651(17)
_cell_measurement_reflns_used    2131
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.24
_cell_measurement_theta_min      2.76
_cell_volume                     1067.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11210
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0461
_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)+(0.0646P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                2111
_reflns_number_total             2880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910039e_si_006.cif
_cod_data_source_block           CS059_min
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4102124
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2852(2) 1.0813(4) 0.8111(2) 0.0483(7) Uani 1 1 d . . .
O2 O 0.34622(17) 0.8186(3) 0.74936(17) 0.0333(5) Uani 1 1 d . . .
O3 O 0.03747(16) 0.6884(3) 0.74384(16) 0.0287(5) Uani 1 1 d . . .
O4 O 0.09370(17) 0.8732(4) 0.62977(17) 0.0430(6) Uani 1 1 d . . .
O5 O -0.3673(2) 0.7079(4) 0.6119(2) 0.0532(7) Uani 1 1 d . . .
O6 O -0.18055(17) 0.7106(3) 0.62663(17) 0.0324(5) Uani 1 1 d . . .
C1 C 0.1564(2) 0.6232(4) 0.7943(2) 0.0276(7) Uani 1 1 d . . .
H1A H 0.1889 0.5797 0.7372 0.033 Uiso 1 1 calc R . .
C2 C 0.2368(2) 0.7716(4) 0.8666(2) 0.0242(6) Uani 1 1 d . . .
C3 C 0.1784(3) 0.8763(5) 0.9374(2) 0.0305(7) Uani 1 1 d . . .
H3A H 0.1420 0.9931 0.8990 0.037 Uiso 1 1 calc R . .
H3B H 0.1161 0.7943 0.9457 0.037 Uiso 1 1 calc R . .
C4 C 0.2548(3) 0.9321(5) 1.0480(2) 0.0317(7) Uani 1 1 d . . .
C5 C 0.3629(3) 0.8745(5) 1.0899(2) 0.0332(7) Uani 1 1 d . . .
C6 C 0.4165(3) 0.7396(5) 1.0301(3) 0.0368(8) Uani 1 1 d . . .
H6A H 0.4624 0.6441 1.0817 0.044 Uiso 1 1 calc R . .
H6B H 0.4698 0.8122 1.0017 0.044 Uiso 1 1 calc R . .
C7 C 0.3310(2) 0.6363(5) 0.9374(2) 0.0290(7) Uani 1 1 d . . .
H7A H 0.3735 0.5800 0.8909 0.035 Uiso 1 1 calc R . .
C8 C 0.2610(3) 0.4780(5) 0.9676(3) 0.0342(7) Uani 1 1 d . . .
H8A H 0.2400 0.5140 1.0321 0.041 Uiso 1 1 calc R . .
H8B H 0.3053 0.3576 0.9828 0.041 Uiso 1 1 calc R . .
C9 C 0.1532(3) 0.4565(5) 0.8684(3) 0.0371(8) Uani 1 1 d . . .
H9A H 0.1546 0.3337 0.8316 0.045 Uiso 1 1 calc R . .
H9B H 0.0829 0.4617 0.8899 0.045 Uiso 1 1 calc R . .
C10 C 0.2888(2) 0.9102(5) 0.8068(2) 0.0300(7) Uani 1 1 d . . .
C11 C 0.3944(3) 0.9345(6) 0.6843(3) 0.0487(9) Uani 1 1 d . . .
H11A H 0.4337 0.8532 0.6462 0.073 Uiso 1 1 calc R . .
H11B H 0.4495 1.0243 0.7306 0.073 Uiso 1 1 calc R . .
H11C H 0.3328 1.0053 0.6316 0.073 Uiso 1 1 calc R . .
C12 C 0.4424(3) 0.9417(6) 1.1974(3) 0.0470(9) Uani 1 1 d . . .
H12A H 0.4010 1.0288 1.2305 0.070 Uiso 1 1 calc R . .
H12B H 0.5082 1.0081 1.1867 0.070 Uiso 1 1 calc R . .
H12C H 0.4698 0.8319 1.2450 0.070 Uiso 1 1 calc R . .
C13 C 0.1940(3) 1.0590(6) 1.1063(3) 0.0495(10) Uani 1 1 d . . .
H13A H 0.2467 1.0905 1.1781 0.074 Uiso 1 1 calc R . .
H13B H 0.1268 0.9923 1.1136 0.074 Uiso 1 1 calc R . .
H13C H 0.1692 1.1764 1.0648 0.074 Uiso 1 1 calc R . .
C14 C 0.0195(3) 0.8071(5) 0.6607(2) 0.0286(7) Uani 1 1 d . . .
C15 C -0.1053(2) 0.8572(4) 0.6079(2) 0.0261(6) Uani 1 1 d . . .
C16 C -0.2858(3) 0.7947(5) 0.6059(3) 0.0348(7) Uani 1 1 d . . .
C17 C -0.2747(3) 0.9996(5) 0.5750(2) 0.0331(7) Uani 1 1 d . . .
C18 C -0.2594(3) 0.9805(5) 0.4612(2) 0.0379(8) Uani 1 1 d . . .
H18A H -0.3213 0.9014 0.4126 0.046 Uiso 1 1 calc R . .
H18B H -0.2598 1.1071 0.4277 0.046 Uiso 1 1 calc R . .
C19 C -0.1418(3) 0.8833(5) 0.4845(2) 0.0344(7) Uani 1 1 d . . .
H19A H -0.0870 0.9654 0.4633 0.041 Uiso 1 1 calc R . .
H19B H -0.1488 0.7594 0.4469 0.041 Uiso 1 1 calc R . .
C20 C -0.1496(2) 1.0399(4) 0.6488(2) 0.0278(6) Uani 1 1 d . . .
C21 C -0.1368(3) 1.0344(5) 0.7695(2) 0.0366(8) Uani 1 1 d . . .
H21A H -0.1662 1.1533 0.7900 0.055 Uiso 1 1 calc R . .
H21B H -0.0554 1.0197 0.8118 0.055 Uiso 1 1 calc R . .
H21C H -0.1806 0.9267 0.7839 0.055 Uiso 1 1 calc R . .
C22 C -0.0973(3) 1.2246(5) 0.6250(3) 0.0398(8) Uani 1 1 d . . .
H22A H -0.1297 1.3325 0.6531 0.060 Uiso 1 1 calc R . .
H22B H -0.1147 1.2387 0.5468 0.060 Uiso 1 1 calc R . .
H22C H -0.0138 1.2215 0.6598 0.060 Uiso 1 1 calc R . .
C23 C -0.3704(3) 1.1302(6) 0.5821(3) 0.0498(10) Uani 1 1 d . . .
H23A H -0.4437 1.0869 0.5314 0.075 Uiso 1 1 calc R . .
H23B H -0.3547 1.2605 0.5637 0.075 Uiso 1 1 calc R . .
H23C H -0.3746 1.1277 0.6557 0.075 Uiso 1 1 calc R . .
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 0.0000 '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 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C11 116.6(3) . . ?
C14 O3 C1 116.4(2) . . ?
C16 O6 C15 105.8(2) . . ?
O3 C1 C9 107.5(2) . . ?
O3 C1 C2 114.6(2) . . ?
C9 C1 C2 105.8(2) . . ?
C10 C2 C3 111.1(2) . . ?
C10 C2 C1 114.5(2) . . ?
C3 C2 C1 111.4(2) . . ?
C10 C2 C7 110.1(2) . . ?
C3 C2 C7 109.7(2) . . ?
C1 C2 C7 99.3(2) . . ?
C4 C3 C2 116.0(3) . . ?
C5 C4 C3 123.6(3) . . ?
C5 C4 C13 124.1(3) . . ?
C3 C4 C13 112.4(3) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 C12 123.6(3) . . ?
C6 C5 C12 114.9(3) . . ?
C5 C6 C7 114.3(3) . . ?
C6 C7 C8 116.4(3) . . ?
C6 C7 C2 112.2(3) . . ?
C8 C7 C2 103.0(2) . . ?
C7 C8 C9 104.9(3) . . ?
C1 C9 C8 105.7(3) . . ?
O1 C10 O2 122.4(3) . . ?
O1 C10 C2 126.2(3) . . ?
O2 C10 C2 111.3(3) . . ?
O4 C14 O3 124.8(3) . . ?
O4 C14 C15 121.6(3) . . ?
O3 C14 C15 113.6(2) . . ?
O6 C15 C14 111.4(2) . . ?
O6 C15 C19 105.8(2) . . ?
C14 C15 C19 114.9(2) . . ?
O6 C15 C20 102.4(2) . . ?
C14 C15 C20 116.8(2) . . ?
C19 C15 C20 104.2(2) . . ?
O5 C16 O6 121.6(3) . . ?
O5 C16 C17 130.7(3) . . ?
O6 C16 C17 107.7(3) . . ?
C16 C17 C23 114.9(3) . . ?
C16 C17 C20 99.4(2) . . ?
C23 C17 C20 118.8(3) . . ?
C16 C17 C18 102.7(3) . . ?
C23 C17 C18 116.1(3) . . ?
C20 C17 C18 102.2(2) . . ?
C19 C18 C17 103.9(2) . . ?
C18 C19 C15 101.7(2) . . ?
C22 C20 C21 108.6(3) . . ?
C22 C20 C15 114.6(2) . . ?
C21 C20 C15 113.6(2) . . ?
C22 C20 C17 115.2(3) . . ?
C21 C20 C17 112.9(2) . . ?
C15 C20 C17 91.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.204(4) . ?
O2 C10 1.346(4) . ?
O2 C11 1.434(4) . ?
O3 C14 1.330(4) . ?
O3 C1 1.470(3) . ?
O4 C14 1.202(3) . ?
O5 C16 1.195(4) . ?
O6 C16 1.367(4) . ?
O6 C15 1.455(3) . ?
C1 C9 1.527(4) . ?
C1 C2 1.535(4) . ?
C2 C10 1.511(4) . ?
C2 C3 1.528(4) . ?
C2 C7 1.553(4) . ?
C3 C4 1.502(4) . ?
C4 C5 1.327(4) . ?
C4 C13 1.514(4) . ?
C5 C6 1.506(5) . ?
C5 C12 1.508(4) . ?
C6 C7 1.510(4) . ?
C7 C8 1.531(5) . ?
C8 C9 1.536(4) . ?
C14 C15 1.506(4) . ?
C15 C19 1.539(4) . ?
C15 C20 1.554(4) . ?
C16 C17 1.512(5) . ?
C17 C23 1.516(5) . ?
C17 C20 1.555(4) . ?
C17 C18 1.563(4) . ?
C18 C19 1.536(4) . ?
C20 C22 1.523(4) . ?
C20 C21 1.534(4) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O3 C1 C9 -167.0(2) . . . . ?
C14 O3 C1 C2 75.7(3) . . . . ?
O3 C1 C2 C10 -84.3(3) . . . . ?
C9 C1 C2 C10 157.4(2) . . . . ?
O3 C1 C2 C3 42.8(3) . . . . ?
C9 C1 C2 C3 -75.4(3) . . . . ?
O3 C1 C2 C7 158.4(2) . . . . ?
C9 C1 C2 C7 40.2(3) . . . . ?
C10 C2 C3 C4 -85.5(3) . . . . ?
C1 C2 C3 C4 145.6(3) . . . . ?
C7 C2 C3 C4 36.6(3) . . . . ?
C2 C3 C4 C5 -8.9(5) . . . . ?
C2 C3 C4 C13 171.8(3) . . . . ?
C3 C4 C5 C6 -2.6(5) . . . . ?
C13 C4 C5 C6 176.6(3) . . . . ?
C3 C4 C5 C12 175.3(3) . . . . ?
C13 C4 C5 C12 -5.5(5) . . . . ?
C4 C5 C6 C7 -16.2(5) . . . . ?
C12 C5 C6 C7 165.8(3) . . . . ?
C5 C6 C7 C8 -73.3(4) . . . . ?
C5 C6 C7 C2 45.0(4) . . . . ?
C10 C2 C7 C6 68.0(3) . . . . ?
C3 C2 C7 C6 -54.6(3) . . . . ?
C1 C2 C7 C6 -171.5(2) . . . . ?
C10 C2 C7 C8 -166.0(2) . . . . ?
C3 C2 C7 C8 71.4(3) . . . . ?
C1 C2 C7 C8 -45.5(3) . . . . ?
C6 C7 C8 C9 157.6(3) . . . . ?
C2 C7 C8 C9 34.4(3) . . . . ?
O3 C1 C9 C8 -142.8(2) . . . . ?
C2 C1 C9 C8 -20.0(3) . . . . ?
C7 C8 C9 C1 -9.1(3) . . . . ?
C11 O2 C10 O1 -5.8(4) . . . . ?
C11 O2 C10 C2 176.7(3) . . . . ?
C3 C2 C10 O1 -1.0(4) . . . . ?
C1 C2 C10 O1 126.3(3) . . . . ?
C7 C2 C10 O1 -122.9(3) . . . . ?
C3 C2 C10 O2 176.3(2) . . . . ?
C1 C2 C10 O2 -56.3(3) . . . . ?
C7 C2 C10 O2 54.5(3) . . . . ?
C1 O3 C14 O4 -5.3(4) . . . . ?
C1 O3 C14 C15 175.9(2) . . . . ?
C16 O6 C15 C14 161.7(2) . . . . ?
C16 O6 C15 C19 -72.8(3) . . . . ?
C16 O6 C15 C20 36.0(3) . . . . ?
O4 C14 C15 O6 156.8(3) . . . . ?
O3 C14 C15 O6 -24.3(3) . . . . ?
O4 C14 C15 C19 36.5(4) . . . . ?
O3 C14 C15 C19 -144.6(3) . . . . ?
O4 C14 C15 C20 -86.0(3) . . . . ?
O3 C14 C15 C20 92.9(3) . . . . ?
C15 O6 C16 O5 178.2(3) . . . . ?
C15 O6 C16 C17 -0.8(3) . . . . ?
O5 C16 C17 C23 18.8(5) . . . . ?
O6 C16 C17 C23 -162.3(3) . . . . ?
O5 C16 C17 C20 146.8(4) . . . . ?
O6 C16 C17 C20 -34.3(3) . . . . ?
O5 C16 C17 C18 -108.3(4) . . . . ?
O6 C16 C17 C18 70.6(3) . . . . ?
C16 C17 C18 C19 -67.1(3) . . . . ?
C23 C17 C18 C19 166.6(3) . . . . ?
C20 C17 C18 C19 35.6(3) . . . . ?
C17 C18 C19 C15 0.6(3) . . . . ?
O6 C15 C19 C18 70.5(3) . . . . ?
C14 C15 C19 C18 -166.2(3) . . . . ?
C20 C15 C19 C18 -37.0(3) . . . . ?
O6 C15 C20 C22 -171.9(3) . . . . ?
C14 C15 C20 C22 66.1(3) . . . . ?
C19 C15 C20 C22 -61.9(3) . . . . ?
O6 C15 C20 C21 62.4(3) . . . . ?
C14 C15 C20 C21 -59.6(3) . . . . ?
C19 C15 C20 C21 172.5(3) . . . . ?
O6 C15 C20 C17 -53.4(2) . . . . ?
C14 C15 C20 C17 -175.4(3) . . . . ?
C19 C15 C20 C17 56.7(2) . . . . ?
C16 C17 C20 C22 168.6(3) . . . . ?
C23 C17 C20 C22 -66.0(4) . . . . ?
C18 C17 C20 C22 63.3(3) . . . . ?
C16 C17 C20 C21 -65.7(3) . . . . ?
C23 C17 C20 C21 59.6(4) . . . . ?
C18 C17 C20 C21 -171.1(3) . . . . ?
C16 C17 C20 C15 50.6(2) . . . . ?
C23 C17 C20 C15 176.0(3) . . . . ?
C18 C17 C20 C15 -54.7(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660098
