#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113112.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_4113112
loop_
_publ_author_name
'Douglass F. Taber'
'Yigang He'
'Ming Xu'
_publ_section_title
;
 Enantioselective Construction of Carbobicyclic Scaffolds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13900
_journal_page_last               13901
_journal_paper_doi               10.1021/ja045849k
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C25 H24 N2 O6'
_chemical_formula_weight         448.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 106.239(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3195(13)
_cell_length_b                   7.0515(6)
_cell_length_c                   21.4677(19)
_cell_measurement_reflns_used    4859
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.77
_cell_volume                     2226.5(3)
_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      150(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         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10245
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.294
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0862
_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)+(0.0532P)²+0.8401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                2751
_reflns_number_total             3478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045849ksi20040710_083603.cif
_cod_data_source_block           tab36
_cod_database_code               4113112
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.4425(2) 0.2326(5) 0.6461(2) 0.0341(9) Uani 1 1 d .
N2 N 0.2809(2) 0.7890(5) 0.69251(17) 0.0269(8) Uani 1 1 d .
O1 O 0.31156(17) 0.8963(4) 0.46866(12) 0.0249(7) Uani 1 1 d .
O2 O 0.40852(18) 0.6762(4) 0.45262(14) 0.0288(7) Uani 1 1 d .
O3 O 0.4447(2) 0.1241(4) 0.60254(17) 0.0402(8) Uani 1 1 d .
O4 O 0.4695(3) 0.1960(5) 0.70406(18) 0.0636(11) Uani 1 1 d .
O5 O 0.2792(2) 0.7119(4) 0.74288(14) 0.0402(8) Uani 1 1 d .
O6 O 0.2479(2) 0.9445(4) 0.67502(14) 0.0367(8) Uani 1 1 d .
C1 C 0.1454(3) 1.3160(6) 0.5831(2) 0.0317(11) Uani 1 1 d .
H1A H 0.1664 1.1902 0.5938 0.038 Uiso 1 1 calc R
C2 C 0.1170(3) 1.4237(7) 0.6276(2) 0.0392(12) Uani 1 1 d .
H2A H 0.1184 1.3715 0.6686 0.047 Uiso 1 1 calc R
C3 C 0.0868(3) 1.6057(7) 0.6127(2) 0.0410(12) Uani 1 1 d .
H3A H 0.0672 1.6792 0.6434 0.049 Uiso 1 1 calc R
C4 C 0.0847(3) 1.6812(6) 0.5538(2) 0.0362(12) Uani 1 1 d .
H4A H 0.0636 1.8071 0.5435 0.043 Uiso 1 1 calc R
C5 C 0.1131(3) 1.5759(6) 0.5092(2) 0.0294(10) Uani 1 1 d .
H5A H 0.1120 1.6304 0.4686 0.035 Uiso 1 1 calc R
C6 C 0.1434(2) 1.3900(6) 0.5229(2) 0.0233(9) Uani 1 1 d .
C7 C 0.1704(3) 1.2785(6) 0.4753(2) 0.0247(9) Uani 1 1 d .
C8 C 0.1911(2) 1.1857(6) 0.4349(2) 0.0235(9) Uani 1 1 d .
C9 C 0.2133(3) 1.0745(5) 0.38312(19) 0.0225(9) Uani 1 1 d .
C10 C 0.1455(3) 0.9047(6) 0.3623(2) 0.0300(10) Uani 1 1 d .
H10A H 0.1551 0.8459 0.3228 0.036 Uiso 1 1 calc R
H10B H 0.1600 0.8081 0.3971 0.036 Uiso 1 1 calc R
C11 C 0.0474(3) 0.9580(6) 0.3488(2) 0.0371(11) Uani 1 1 d .
H11A H 0.0265 0.9915 0.3850 0.045 Uiso 1 1 calc R
C12 C -0.0117(3) 0.9626(7) 0.2922(3) 0.0512(15) Uani 1 1 d .
H12C H 0.0061 0.9303 0.2545 0.061 Uiso 1 1 calc R
H12A H -0.0727 0.9984 0.2884 0.061 Uiso 1 1 calc R
C13 C 0.2021(2) 1.2022(5) 0.32294(19) 0.0235(9) Uani 1 1 d .
H13A H 0.2202 1.1281 0.2894 0.028 Uiso 1 1 calc R
H13B H 0.1368 1.2334 0.3054 0.028 Uiso 1 1 calc R
C14 C 0.2561(3) 1.3882(5) 0.3337(2) 0.0269(10) Uani 1 1 d .
H14A H 0.2216 1.4838 0.3027 0.032 Uiso 1 1 calc R
H14B H 0.2605 1.4346 0.3780 0.032 Uiso 1 1 calc R
C15 C 0.3518(3) 1.3747(6) 0.3259(2) 0.0298(10) Uani 1 1 d .
H15A H 0.3476 1.3790 0.2791 0.036 Uiso 1 1 calc R
H15B H 0.3868 1.4873 0.3465 0.036 Uiso 1 1 calc R
C16 C 0.4039(2) 1.1981(5) 0.3549(2) 0.0242(9) Uani 1 1 d .
H16A H 0.4696 1.2229 0.3625 0.029 Uiso 1 1 calc R
H16B H 0.3870 1.0942 0.3227 0.029 Uiso 1 1 calc R
C17 C 0.3877(3) 1.1307(5) 0.41868(19) 0.0241(9) Uani 1 1 d .
H17A H 0.4437 1.0693 0.4457 0.029 Uiso 1 1 calc R
H17B H 0.3748 1.2419 0.4428 0.029 Uiso 1 1 calc R
C18 C 0.3090(2) 0.9912(5) 0.40748(18) 0.0211(9) Uani 1 1 d .
H18A H 0.3166 0.8932 0.3758 0.025 Uiso 1 1 calc R
C19 C 0.3643(2) 0.7444(5) 0.48430(19) 0.0200(9) Uani 1 1 d .
C20 C 0.3618(2) 0.6667(5) 0.54866(18) 0.0175(9) Uani 1 1 d .
C21 C 0.4019(2) 0.4922(5) 0.56801(19) 0.0190(9) Uani 1 1 d .
H21A H 0.4289 0.4226 0.5403 0.023 Uiso 1 1 calc R
C22 C 0.4024(2) 0.4211(5) 0.6274(2) 0.0213(9) Uani 1 1 d .
C23 C 0.3660(3) 0.5159(6) 0.6698(2) 0.0258(10) Uani 1 1 d .
H23A H 0.3690 0.4658 0.7114 0.031 Uiso 1 1 calc R
C24 C 0.3248(2) 0.6878(5) 0.64932(18) 0.0196(9) Uani 1 1 d .
C25 C 0.3217(2) 0.7636(5) 0.58975(19) 0.0205(9) Uani 1 1 d .
H25A H 0.2923 0.8816 0.5768 0.025 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'
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
O3 N1 O4 125.1(4)
O3 N1 C22 117.2(4)
O4 N1 C22 117.7(4)
O5 N2 O6 124.3(4)
O5 N2 C24 118.0(3)
O6 N2 C24 117.7(3)
C19 O1 C18 117.2(3)
C2 C1 C6 120.6(4)
C3 C2 C1 120.2(5)
C4 C3 C2 120.0(5)
C3 C4 C5 120.3(4)
C4 C5 C6 120.8(4)
C1 C6 C5 118.0(4)
C1 C6 C7 121.4(4)
C5 C6 C7 120.5(4)
C8 C7 C6 178.7(4)
C7 C8 C9 177.6(4)
C8 C9 C18 110.3(3)
C8 C9 C13 109.0(3)
C18 C9 C13 112.4(3)
C8 C9 C10 110.3(3)
C18 C9 C10 107.5(3)
C13 C9 C10 107.3(3)
C11 C10 C9 114.4(3)
C12 C11 C10 126.0(5)
C14 C13 C9 116.3(3)
C15 C14 C13 115.2(3)
C16 C15 C14 114.7(3)
C15 C16 C17 115.0(3)
C18 C17 C16 112.2(3)
O1 C18 C17 109.4(3)
O1 C18 C9 105.3(3)
C17 C18 C9 116.6(3)
O2 C19 O1 125.9(4)
O2 C19 C20 123.1(3)
O1 C19 C20 111.0(3)
C21 C20 C25 119.0(4)
C21 C20 C19 118.5(3)
C25 C20 C19 122.5(3)
C22 C21 C20 119.4(4)
C21 C22 C23 123.0(4)
C21 C22 N1 118.6(4)
C23 C22 N1 118.4(4)
C22 C23 C24 116.9(4)
C25 C24 C23 122.1(4)
C25 C24 N2 119.6(3)
C23 C24 N2 118.3(4)
C24 C25 C20 119.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O3 1.216(5)
N1 O4 1.224(5)
N1 C22 1.472(5)
N2 O5 1.217(4)
N2 O6 1.221(4)
N2 C24 1.474(5)
O1 C19 1.327(4)
O1 C18 1.465(4)
O2 C19 1.188(5)
C1 C2 1.383(6)
C1 C6 1.384(6)
C2 C3 1.371(6)
C3 C4 1.364(7)
C4 C5 1.374(6)
C5 C6 1.394(5)
C6 C7 1.440(6)
C7 C8 1.197(6)
C8 C9 1.476(6)
C9 C18 1.529(5)
C9 C13 1.545(5)
C9 C10 1.566(5)
C10 C11 1.496(6)
C11 C12 1.297(6)
C13 C14 1.533(5)
C14 C15 1.524(5)
C15 C16 1.516(5)
C16 C17 1.534(5)
C17 C18 1.522(5)
C19 C20 1.497(5)
C20 C21 1.387(5)
C20 C25 1.387(5)
C21 C22 1.368(5)
C22 C23 1.368(6)
C23 C24 1.380(5)
C24 C25 1.375(5)
