#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/60/1506028.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_1506028
loop_
_publ_author_name
'Focken, Thilo'
'Charette, André B'
_publ_section_title
;
 Stereoselective synthesis of pyridinones: application to the synthesis of
 (-)-barrenazines.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2985
_journal_page_last               2988
_journal_paper_doi               10.1021/ol0609006
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C26 H28 N2 O2'
_chemical_formula_sum            'C26 H28 N2 O2'
_chemical_formula_weight         400.50
_chemical_name_systematic        ?
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                   9.9053(2)
_cell_length_b                   13.1534(3)
_cell_length_c                   17.1989(4)
_cell_measurement_reflns_used    6444
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.89
_cell_measurement_theta_min      3.36
_cell_volume                     2240.82(9)
_computing_cell_refinement       'SMART (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker AXS Smart 2K/Platform'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26983
_diffrn_reflns_theta_full        72.88
_diffrn_reflns_theta_max         72.88
_diffrn_reflns_theta_min         4.23
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         215
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  0.9000
_exptl_absorpt_correction_T_min  0.8500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), 1873 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0280
_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)+(0.0472P)²+0.3259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0730
_reflns_number_gt                4341
_reflns_number_total             4421
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol0609006si20060523_050824.cif
_cod_data_source_block           cha117
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (32
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (42 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1506028
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
O33 O 0.07943(8) 0.19299(6) 0.49818(5) 0.02897(19) Uani 1 1 d .
N1 N 0.42074(9) 0.18866(7) 0.63395(5) 0.01791(18) Uani 1 1 d .
C1 C 0.40062(11) 0.12117(8) 0.57443(7) 0.0221(2) Uani 1 1 d .
H1 H 0.4703 0.0734 0.5641 0.027 Uiso 1 1 calc R
C2 C 0.28924(12) 0.11735(9) 0.52934(7) 0.0238(2) Uani 1 1 d .
H2 H 0.2784 0.0627 0.4938 0.029 Uiso 1 1 calc R
C3 C 0.18624(11) 0.19478(9) 0.53417(6) 0.0219(2) Uani 1 1 d .
C4 C 0.22657(12) 0.28566(8) 0.58298(7) 0.0219(2) Uani 1 1 d .
H4A H 0.1440 0.3222 0.5994 0.026 Uiso 1 1 calc R
H4B H 0.2807 0.3327 0.5506 0.026 Uiso 1 1 calc R
C5 C 0.30835(10) 0.25690(8) 0.65533(6) 0.0181(2) Uani 1 1 d .
H5 H 0.3479 0.3206 0.6774 0.022 Uiso 1 1 calc R
C6 C 0.53282(11) 0.18414(8) 0.68457(6) 0.0176(2) Uani 1 1 d .
N6 N 0.53402(9) 0.24531(7) 0.74183(5) 0.01934(19) Uani 1 1 d .
C7 C 0.64048(11) 0.23781(8) 0.80040(6) 0.0200(2) Uani 1 1 d .
H7 H 0.7152 0.1940 0.7802 0.024 Uiso 1 1 calc R
C8 C 0.57752(12) 0.18802(9) 0.87163(6) 0.0237(2) Uani 1 1 d .
H8A H 0.6425 0.1886 0.9153 0.028 Uiso 1 1 calc R
H8B H 0.4960 0.2261 0.8877 0.028 Uiso 1 1 calc R
O9 O 0.54259(9) 0.08673(6) 0.85258(5) 0.02681(18) Uani 1 1 d .
C10 C 0.48366(15) 0.03497(11) 0.91602(8) 0.0375(3) Uani 1 1 d .
H10A H 0.3970 0.0667 0.9290 0.056 Uiso 1 1 calc R
H10B H 0.5441 0.0387 0.9610 0.056 Uiso 1 1 calc R
H10C H 0.4689 -0.0364 0.9020 0.056 Uiso 1 1 calc R
C11 C 0.69574(12) 0.34499(9) 0.81859(7) 0.0248(2) Uani 1 1 d .
H11 H 0.6196 0.3870 0.8392 0.030 Uiso 1 1 calc R
C12 C 0.74695(16) 0.39521(11) 0.74474(9) 0.0398(3) Uani 1 1 d .
H12A H 0.8244 0.3570 0.7246 0.060 Uiso 1 1 calc R
H12B H 0.7747 0.4651 0.7562 0.060 Uiso 1 1 calc R
H12C H 0.6749 0.3959 0.7057 0.060 Uiso 1 1 calc R
C13 C 0.80759(12) 0.34338(10) 0.87995(8) 0.0299(3) Uani 1 1 d .
H13A H 0.8397 0.4128 0.8891 0.045 Uiso 1 1 calc R
H13B H 0.8826 0.3012 0.8615 0.045 Uiso 1 1 calc R
H13C H 0.7721 0.3151 0.9285 0.045 Uiso 1 1 calc R
C14 C 0.63777(11) 0.10611(8) 0.66465(6) 0.0177(2) Uani 1 1 d .
C15 C 0.62076(11) 0.00519(8) 0.68797(6) 0.0210(2) Uani 1 1 d .
H15 H 0.5439 -0.0135 0.7177 0.025 Uiso 1 1 calc R
C16 C 0.71540(13) -0.06772(8) 0.66790(7) 0.0243(2) Uani 1 1 d .
H16 H 0.7027 -0.1364 0.6834 0.029 Uiso 1 1 calc R
C17 C 0.82916(12) -0.04055(9) 0.62509(7) 0.0249(2) Uani 1 1 d .
H17 H 0.8938 -0.0907 0.6110 0.030 Uiso 1 1 calc R
C18 C 0.84789(11) 0.06036(9) 0.60294(6) 0.0235(2) Uani 1 1 d .
H18 H 0.9261 0.0793 0.5744 0.028 Uiso 1 1 calc R
C19 C 0.75236(11) 0.13333(8) 0.62248(6) 0.0198(2) Uani 1 1 d .
H19 H 0.7652 0.2020 0.6071 0.024 Uiso 1 1 calc R
C20 C 0.22405(11) 0.20914(8) 0.71604(6) 0.0188(2) Uani 1 1 d .
C21 C 0.15579(11) 0.17447(8) 0.76681(6) 0.0202(2) Uani 1 1 d .
C22 C 0.07290(11) 0.13423(8) 0.82848(6) 0.0185(2) Uani 1 1 d .
C23 C -0.04266(11) 0.07773(8) 0.81108(6) 0.0206(2) Uani 1 1 d .
H23 H -0.0652 0.0639 0.7584 0.025 Uiso 1 1 calc R
C24 C -0.12461(11) 0.04173(9) 0.87038(7) 0.0241(2) Uani 1 1 d .
H24 H -0.2036 0.0040 0.8581 0.029 Uiso 1 1 calc R
C25 C -0.09187(12) 0.06056(9) 0.94748(7) 0.0255(2) Uani 1 1 d .
H25 H -0.1481 0.0357 0.9880 0.031 Uiso 1 1 calc R
C26 C 0.02338(13) 0.11580(9) 0.96507(7) 0.0269(2) Uani 1 1 d .
H26 H 0.0462 0.1284 1.0178 0.032 Uiso 1 1 calc R
C27 C 0.10563(12) 0.15278(8) 0.90636(7) 0.0231(2) Uani 1 1 d .
H27 H 0.1842 0.1907 0.9190 0.028 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C6 123.23(9) y
C1 N1 C5 118.06(9) y
C6 N1 C5 117.70(8) y
C2 C1 N1 124.94(11) y
C2 C1 H1 117.5 ?
N1 C1 H1 117.5 ?
C1 C2 C3 121.22(10) y
C1 C2 H2 119.4 ?
C3 C2 H2 119.4 ?
O33 C3 C2 124.56(11) y
O33 C3 C4 121.51(10) y
C2 C3 C4 113.72(9) y
C3 C4 C5 113.25(9) y
C3 C4 H4A 108.9 ?
C5 C4 H4A 108.9 ?
C3 C4 H4B 108.9 ?
C5 C4 H4B 108.9 ?
H4A C4 H4B 107.7 ?
N1 C5 C20 110.10(8) y
N1 C5 C4 110.27(9) y
C20 C5 C4 112.35(9) y
N1 C5 H5 108 ?
C20 C5 H5 108 ?
C4 C5 H5 108 ?
N6 C6 N1 117.27(9) y
N6 C6 C14 127.09(9) y
N1 C6 C14 115.64(9) y
C6 N6 C7 119.85(9) y
N6 C7 C8 106.74(9) y
N6 C7 C11 109.50(9) y
C8 C7 C11 112.01(9) y
N6 C7 H7 109.5 ?
C8 C7 H7 109.5 ?
C11 C7 H7 109.5 ?
O9 C8 C7 108.59(9) y
O9 C8 H8A 110 ?
C7 C8 H8A 110 ?
O9 C8 H8B 110 ?
C7 C8 H8B 110 ?
H8A C8 H8B 108.4 ?
C10 O9 C8 112.09(9) y
O9 C10 H10A 109.5 ?
O9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C12 C11 C13 109.93(11) y
C12 C11 C7 110.24(10) y
C13 C11 C7 112.56(9) y
C12 C11 H11 108 ?
C13 C11 H11 108 ?
C7 C11 H11 108 ?
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C11 C13 H13A 109.5 ?
C11 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C11 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C19 C14 C15 119.46(10) y
C19 C14 C6 120.48(9) y
C15 C14 C6 120.06(10) y
C16 C15 C14 120.32(10) y
C16 C15 H15 119.8 ?
C14 C15 H15 119.8 ?
C15 C16 C17 120.12(10) y
C15 C16 H16 119.9 ?
C17 C16 H16 119.9 ?
C16 C17 C18 119.79(10) y
C16 C17 H17 120.1 ?
C18 C17 H17 120.1 ?
C19 C18 C17 120.09(10) y
C19 C18 H18 120 ?
C17 C18 H18 120 ?
C18 C19 C14 120.21(10) y
C18 C19 H19 119.9 ?
C14 C19 H19 119.9 ?
C21 C20 C5 177.15(11) y
C20 C21 C22 179.10(12) y
C23 C22 C27 119.17(10) y
C23 C22 C21 120.28(10) y
C27 C22 C21 120.54(10) y
C24 C23 C22 120.24(10) y
C24 C23 H23 119.9 ?
C22 C23 H23 119.9 ?
C23 C24 C25 120.34(11) y
C23 C24 H24 119.8 ?
C25 C24 H24 119.8 ?
C26 C25 C24 119.63(11) y
C26 C25 H25 120.2 ?
C24 C25 H25 120.2 ?
C27 C26 C25 120.61(11) y
C27 C26 H26 119.7 ?
C25 C26 H26 119.7 ?
C26 C27 C22 120.0(1) y
C26 C27 H27 120 ?
C22 C27 H27 120 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O33 C3 1.2260(14) y
N1 C1 1.3697(14) y
N1 C6 1.4120(13) y
N1 C5 1.4766(13) y
C1 C2 1.3494(16) y
C1 H1 0.95 ?
C2 C3 1.4439(17) y
C2 H2 0.95 ?
C3 C4 1.5145(15) y
C4 C5 1.5322(15) y
C4 H4a 0.99 ?
C4 H4b 0.99 ?
C5 C20 1.4772(15) y
C5 H5 1 ?
C6 N6 1.2717(14) y
C6 C14 1.5005(15) y
N6 C7 1.4617(13) y
C7 C8 1.5228(15) y
C7 C11 1.5443(15) y
C7 H7 1 ?
C8 O9 1.4150(14) y
C8 H8a 0.99 ?
C8 H8b 0.99 ?
O9 C10 1.4123(15) y
C10 H10a 0.98 ?
C10 H10b 0.98 ?
C10 H10c 0.98 ?
C11 C12 1.5188(19) y
C11 C13 1.5303(16) y
C11 H11 1 ?
C12 H12a 0.98 ?
C12 H12b 0.98 ?
C12 H12c 0.98 ?
C13 H13a 0.98 ?
C13 H13b 0.98 ?
C13 H13c 0.98 ?
C14 C19 1.3938(15) y
C14 C15 1.3968(15) y
C15 C16 1.3848(16) y
C15 H15 0.95 ?
C16 C17 1.3928(17) y
C16 H16 0.95 ?
C17 C18 1.3932(18) y
C17 H17 0.95 ?
C18 C19 1.3891(16) y
C18 H18 0.95 ?
C19 H19 0.95 ?
C20 C21 1.1948(16) y
C21 C22 1.4420(15) y
C22 C23 1.3972(15) y
C22 C27 1.3996(16) y
C23 C24 1.3867(16) y
C23 H23 0.95 ?
C24 C25 1.3875(18) y
C24 H24 0.95 ?
C25 C26 1.3866(18) y
C25 H25 0.95 ?
C26 C27 1.3856(16) y
C26 H26 0.95 ?
C27 H27 0.95 ?
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
C6 N1 C1 C2 173.75(11)
C5 N1 C1 C2 5.54(16)
N1 C1 C2 C3 8.07(19)
C1 C2 C3 O33 -175.75(11)
C1 C2 C3 C4 9.54(16)
O33 C3 C4 C5 146.77(10)
C2 C3 C4 C5 -38.34(14)
C1 N1 C5 C20 90.61(11)
C6 N1 C5 C20 -78.27(11)
C1 N1 C5 C4 -33.92(12)
C6 N1 C5 C4 157.20(9)
C3 C4 C5 N1 49.85(12)
C3 C4 C5 C20 -73.38(12)
C1 N1 C6 N6 -173.8(1)
C5 N1 C6 N6 -5.55(13)
C1 N1 C6 C14 5.77(14)
C5 N1 C6 C14 174.02(9)
N1 C6 N6 C7 174.13(9)
C14 C6 N6 C7 -5.38(16)
C6 N6 C7 C8 -104.20(11)
C6 N6 C7 C11 134.36(10)
N6 C7 C8 O9 66.34(11)
C11 C7 C8 O9 -173.83(9)
C7 C8 O9 C10 179.81(10)
N6 C7 C11 C12 -57.12(12)
C8 C7 C11 C12 -175.33(10)
N6 C7 C11 C13 179.74(10)
C8 C7 C11 C13 61.53(13)
N6 C6 C14 C19 -83.89(14)
N1 C6 C14 C19 96.59(12)
N6 C6 C14 C15 96.48(14)
N1 C6 C14 C15 -83.04(12)
C19 C14 C15 C16 -1.43(16)
C6 C14 C15 C16 178.19(10)
C14 C15 C16 C17 0.79(17)
C15 C16 C17 C18 0.42(17)
C16 C17 C18 C19 -0.99(17)
C17 C18 C19 C14 0.34(16)
C15 C14 C19 C18 0.86(16)
C6 C14 C19 C18 -178.76(10)
C27 C22 C23 C24 0.83(16)
C21 C22 C23 C24 -177.99(10)
C22 C23 C24 C25 -0.68(16)
C23 C24 C25 C26 0.09(17)
C24 C25 C26 C27 0.35(18)
C25 C26 C27 C22 -0.19(17)
C23 C22 C27 C26 -0.40(16)
C21 C22 C27 C26 178.43(10)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199793 ChemSpider
