#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/21/4102121.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_4102121
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 unk
_chemical_formula_moiety         'C23 H28 O4'
_chemical_formula_sum            'C23 H28 O4'
_chemical_formula_weight         368.45
_chemical_name_common            'estrone derivative 11c'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8778(15)
_cell_length_b                   11.951(2)
_cell_length_c                   18.680(3)
_cell_measurement_reflns_used    2476
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.29
_cell_measurement_theta_min      2.77
_cell_volume                     1981.9(6)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0901
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20956
_diffrn_reflns_theta_full        28.53
_diffrn_reflns_theta_max         28.53
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0232P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                3433
_reflns_number_total             5002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910039e_si_002.cif
_cod_data_source_block           y
_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_cell_volume        1981.8(6)
_cod_database_code               4102121
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.54465(13) 0.48198(9) 0.21491(6) 0.0249(3) Uani 1 1 d . . .
O2 O 0.68860(14) 0.36368(10) 0.28111(6) 0.0310(3) Uani 1 1 d . . .
O3 O 0.82063(15) 0.63728(10) 0.22619(7) 0.0346(3) Uani 1 1 d . . .
O4 O 1.01442(15) -0.19444(10) 0.00274(6) 0.0365(3) Uani 1 1 d . . .
C1 C 0.6713(2) 0.42475(14) 0.23029(9) 0.0231(4) Uani 1 1 d . . .
C2 C 0.79067(18) 0.45165(14) 0.17450(9) 0.0214(4) Uani 1 1 d . . .
C3 C 0.8177(2) 0.57828(15) 0.17387(10) 0.0259(4) Uani 1 1 d . . .
C4 C 0.8453(3) 0.61515(15) 0.09770(10) 0.0372(5) Uani 1 1 d . . .
H4A H 0.9423 0.6556 0.0937 0.045 Uiso 1 1 calc R . .
H4B H 0.7633 0.6647 0.0809 0.045 Uiso 1 1 calc R . .
C5 C 0.8492(2) 0.50678(14) 0.05411(9) 0.0319(5) Uani 1 1 d . . .
H5A H 0.9532 0.4774 0.0506 0.038 Uiso 1 1 calc R . .
H5B H 0.8093 0.5190 0.0053 0.038 Uiso 1 1 calc R . .
C6 C 0.7479(2) 0.42614(14) 0.09645(8) 0.0232(4) Uani 1 1 d . . .
H6 H 0.6414 0.4512 0.0894 0.028 Uiso 1 1 calc R . .
C7 C 0.7558(2) 0.30274(15) 0.07551(9) 0.0247(4) Uani 1 1 d . . .
H7 H 0.6598 0.2682 0.0927 0.030 Uiso 1 1 calc R . .
C8 C 0.7589(2) 0.28520(15) -0.00476(10) 0.0349(5) Uani 1 1 d . . .
H8A H 0.6761 0.3283 -0.0270 0.042 Uiso 1 1 calc R . .
H8B H 0.8553 0.3139 -0.0241 0.042 Uiso 1 1 calc R . .
C9 C 0.7427(2) 0.16444(16) -0.02405(10) 0.0369(5) Uani 1 1 d . . .
H9A H 0.7642 0.1553 -0.0757 0.044 Uiso 1 1 calc R . .
H9B H 0.6370 0.1413 -0.0158 0.044 Uiso 1 1 calc R . .
C10 C 0.8451(2) 0.08836(14) 0.01780(9) 0.0260(4) Uani 1 1 d . . .
C11 C 0.8765(2) -0.01870(14) -0.00908(9) 0.0286(4) Uani 1 1 d . . .
H11 H 0.8314 -0.0421 -0.0527 0.034 Uiso 1 1 calc R . .
C12 C 0.9718(2) -0.09042(15) 0.02672(9) 0.0271(4) Uani 1 1 d . . .
C13 C 1.0339(2) -0.05755(15) 0.09179(9) 0.0268(4) Uani 1 1 d . . .
H13 H 1.0982 -0.1070 0.1174 0.032 Uiso 1 1 calc R . .
C14 C 1.0018(2) 0.04683(14) 0.11899(9) 0.0238(4) Uani 1 1 d . . .
H14 H 1.0439 0.0681 0.1637 0.029 Uiso 1 1 calc R . .
C15 C 0.9084(2) 0.12303(14) 0.08245(9) 0.0207(4) Uani 1 1 d . . .
C16 C 0.88081(19) 0.23793(14) 0.11039(9) 0.0210(4) Uani 1 1 d . . .
C17 C 0.96295(19) 0.28201(14) 0.16378(9) 0.0236(4) Uani 1 1 d . . .
H17 H 1.0397 0.2368 0.1842 0.028 Uiso 1 1 calc R . .
C18 C 0.94215(19) 0.39724(14) 0.19336(9) 0.0255(4) Uani 1 1 d . . .
H18A H 1.0243 0.4456 0.1752 0.031 Uiso 1 1 calc R . .
H18B H 0.9516 0.3939 0.2461 0.031 Uiso 1 1 calc R . .
C19 C 0.41867(19) 0.48891(15) 0.26787(9) 0.0254(4) Uani 1 1 d . . .
C20 C 0.4781(2) 0.53676(16) 0.33772(9) 0.0345(5) Uani 1 1 d . . .
H20A H 0.5473 0.4831 0.3598 0.052 Uiso 1 1 calc R . .
H20B H 0.3937 0.5511 0.3703 0.052 Uiso 1 1 calc R . .
H20C H 0.5315 0.6069 0.3281 0.052 Uiso 1 1 calc R . .
C21 C 0.3117(2) 0.57040(15) 0.23233(10) 0.0329(5) Uani 1 1 d . . .
H21A H 0.3616 0.6430 0.2266 0.049 Uiso 1 1 calc R . .
H21B H 0.2216 0.5794 0.2621 0.049 Uiso 1 1 calc R . .
H21C H 0.2825 0.5416 0.1852 0.049 Uiso 1 1 calc R . .
C22 C 0.3478(2) 0.37435(15) 0.27607(10) 0.0353(5) Uani 1 1 d . . .
H22A H 0.3167 0.3465 0.2290 0.053 Uiso 1 1 calc R . .
H22B H 0.2595 0.3797 0.3074 0.053 Uiso 1 1 calc R . .
H22C H 0.4212 0.3227 0.2971 0.053 Uiso 1 1 calc R . .
C23 C 0.9398(3) -0.23602(16) -0.06014(9) 0.0471(6) Uani 1 1 d . . .
H23A H 0.8306 -0.2351 -0.0525 0.071 Uiso 1 1 calc R . .
H23B H 0.9729 -0.3128 -0.0696 0.071 Uiso 1 1 calc R . .
H23C H 0.9650 -0.1885 -0.1012 0.071 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 0.0016 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C19 120.75(13) . . ?
C12 O4 C23 116.89(15) . . ?
O2 C1 O1 125.53(16) . . ?
O2 C1 C2 125.28(16) . . ?
O1 C1 C2 109.17(14) . . ?
C1 C2 C3 108.86(14) . . ?
C1 C2 C18 111.34(14) . . ?
C3 C2 C18 106.44(14) . . ?
C1 C2 C6 115.84(13) . . ?
C3 C2 C6 103.14(14) . . ?
C18 C2 C6 110.49(14) . . ?
O3 C3 C4 126.16(17) . . ?
O3 C3 C2 125.09(17) . . ?
C4 C3 C2 108.72(15) . . ?
C3 C4 C5 104.96(15) . . ?
C4 C5 C6 104.10(14) . . ?
C7 C6 C2 115.03(14) . . ?
C7 C6 C5 116.54(14) . . ?
C2 C6 C5 102.66(14) . . ?
C16 C7 C8 110.14(15) . . ?
C16 C7 C6 114.87(15) . . ?
C8 C7 C6 112.84(14) . . ?
C9 C8 C7 111.75(16) . . ?
C8 C9 C10 113.58(15) . . ?
C15 C10 C11 120.05(16) . . ?
C15 C10 C9 120.91(16) . . ?
C11 C10 C9 119.04(16) . . ?
C12 C11 C10 121.07(17) . . ?
O4 C12 C11 125.00(17) . . ?
O4 C12 C13 115.54(17) . . ?
C11 C12 C13 119.46(17) . . ?
C14 C13 C12 119.75(17) . . ?
C13 C14 C15 121.93(17) . . ?
C10 C15 C14 117.70(16) . . ?
C10 C15 C16 120.73(16) . . ?
C14 C15 C16 121.55(16) . . ?
C17 C16 C15 122.17(16) . . ?
C17 C16 C7 121.40(16) . . ?
C15 C16 C7 116.42(15) . . ?
C16 C17 C18 124.65(16) . . ?
C17 C18 C2 114.43(14) . . ?
O1 C19 C21 102.42(13) . . ?
O1 C19 C22 109.13(14) . . ?
C21 C19 C22 111.41(15) . . ?
O1 C19 C20 109.24(14) . . ?
C21 C19 C20 110.63(15) . . ?
C22 C19 C20 113.43(14) . . ?
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 C1 1.3467(19) . ?
O1 C19 1.4953(18) . ?
O2 C1 1.2073(19) . ?
O3 C3 1.205(2) . ?
O4 C12 1.3744(19) . ?
O4 C23 1.437(2) . ?
C1 C2 1.521(2) . ?
C2 C3 1.532(2) . ?
C2 C18 1.535(2) . ?
C2 C6 1.537(2) . ?
C3 C4 1.510(2) . ?
C4 C5 1.530(2) . ?
C5 C6 1.537(2) . ?
C6 C7 1.527(2) . ?
C7 C16 1.502(2) . ?
C7 C8 1.514(2) . ?
C8 C9 1.494(2) . ?
C9 C10 1.505(2) . ?
C10 C15 1.395(2) . ?
C10 C11 1.402(2) . ?
C11 C12 1.378(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.377(2) . ?
C14 C15 1.408(2) . ?
C15 C16 1.489(2) . ?
C16 C17 1.343(2) . ?
C17 C18 1.495(2) . ?
C19 C21 1.514(2) . ?
C19 C22 1.515(2) . ?
C19 C20 1.519(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660096
