#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/52/1505281.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_1505281
loop_
_publ_author_name
'Sünnemann, Hans Wolf'
'Hofmeister, Anja'
'Magull, Jörg'
'Banwell, Martin G.'
'de Meijere, Armin'
_publ_section_title
;
 Stille/Diels-Alder reaction sequences: diversity-oriented access to novel
 steroids.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              517
_journal_page_last               520
_journal_paper_doi               10.1021/ol062878m
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C26 H36 N2 O3'
_chemical_formula_weight         424.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_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                   8.6266(17)
_cell_length_b                   14.638(3)
_cell_length_c                   19.114(4)
_cell_measurement_temperature    133(2)
_cell_volume                     2413.6(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34977
_diffrn_reflns_theta_full        24.85
_diffrn_reflns_theta_max         24.85
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0341
_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)+(0.0331P)²+0.2740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                3645
_reflns_number_total             4138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol062878msi20061127_063916.cif
_cod_data_source_block           ha506
_cod_original_cell_volume        2413.7(8)
_cod_database_code               1505281
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
O2 O 0.04147(14) 0.50679(8) 0.08140(6) 0.0373(3) Uani 1 1 d .
O3 O -0.30106(13) 0.24972(8) -0.39268(6) 0.0343(3) Uani 1 1 d .
O1 O -0.11462(14) 0.39964(9) 0.12845(6) 0.0425(3) Uani 1 1 d .
C1 C -0.1345(2) 0.49548(11) -0.05408(9) 0.0343(4) Uani 1 1 d .
H1A H -0.2261 0.5115 -0.0828 0.041 Uiso 1 1 calc R
H1B H -0.0689 0.5507 -0.0499 0.041 Uiso 1 1 calc R
C2 C -0.1885(2) 0.46604(12) 0.01899(9) 0.0359(4) Uani 1 1 d .
H2A H -0.2383 0.5186 0.0426 0.043 Uiso 1 1 calc R
H2B H -0.2669 0.4170 0.0143 0.043 Uiso 1 1 calc R
C3 C -0.05581(19) 0.43197(11) 0.06339(9) 0.0335(4) Uani 1 1 d .
C4 C 0.03682(19) 0.35721(12) 0.02632(9) 0.0330(4) Uani 1 1 d .
H4A H -0.0289 0.3023 0.0203 0.040 Uiso 1 1 calc R
H4B H 0.1274 0.3401 0.0553 0.040 Uiso 1 1 calc R
C5 C 0.09224(18) 0.39083(11) -0.04550(9) 0.0313(4) Uani 1 1 d .
H5A H 0.1555 0.4469 -0.0366 0.038 Uiso 1 1 calc R
C6 C 0.20066(18) 0.32227(12) -0.08212(9) 0.0369(4) Uani 1 1 d .
H6A H 0.2564 0.2858 -0.0457 0.044 Uiso 1 1 calc R
C7 C 0.11148(18) 0.25611(12) -0.13091(9) 0.0332(4) Uani 1 1 d .
H7A H 0.1891 0.2168 -0.1555 0.040 Uiso 1 1 calc R
C8 C 0.02203(18) 0.31061(11) -0.18659(8) 0.0305(4) Uani 1 1 d .
H8A H 0.1003 0.3394 -0.2183 0.037 Uiso 1 1 calc R
C9 C -0.07515(18) 0.38790(11) -0.15457(9) 0.0307(4) Uani 1 1 d .
C10 C -0.04356(18) 0.42075(11) -0.09043(9) 0.0293(4) Uani 1 1 d .
C11 C -0.1986(2) 0.42953(12) -0.20183(10) 0.0372(4) Uani 1 1 d .
C12 C -0.28040(19) 0.36411(11) -0.25232(9) 0.0349(4) Uani 1 1 d .
H12A H -0.3574 0.3274 -0.2261 0.042 Uiso 1 1 calc R
H12B H -0.3367 0.4000 -0.2881 0.042 Uiso 1 1 calc R
C13 C -0.16680(18) 0.30043(11) -0.28830(8) 0.0299(4) Uani 1 1 d .
C14 C -0.07903(17) 0.24840(11) -0.23131(8) 0.0301(4) Uani 1 1 d .
H14A H -0.1586 0.2210 -0.1996 0.036 Uiso 1 1 calc R
C15 C 0.0000(2) 0.16887(12) -0.27004(9) 0.0415(4) Uani 1 1 d .
H15A H 0.0118 0.1152 -0.2390 0.050 Uiso 1 1 calc R
H15B H 0.1034 0.1872 -0.2876 0.050 Uiso 1 1 calc R
C16 C -0.1118(2) 0.14756(13) -0.33148(10) 0.0437(4) Uani 1 1 d .
H16A H -0.0567 0.1518 -0.3768 0.052 Uiso 1 1 calc R
H16B H -0.1555 0.0854 -0.3267 0.052 Uiso 1 1 calc R
C17 C -0.24170(19) 0.22035(11) -0.32709(9) 0.0317(4) Uani 1 1 d .
H17A H -0.3288 0.1957 -0.2982 0.038 Uiso 1 1 calc R
C19 C 0.00820(19) 0.19617(12) -0.09021(9) 0.0320(4) Uani 1 1 d .
C18 C -0.0586(2) 0.35328(13) -0.33800(9) 0.0417(4) Uani 1 1 d .
H18A H -0.0112 0.4044 -0.3128 0.063 Uiso 1 1 calc R
H18B H -0.1185 0.3767 -0.3777 0.063 Uiso 1 1 calc R
H18C H 0.0228 0.3123 -0.3552 0.063 Uiso 1 1 calc R
C20 C 0.3157(2) 0.37047(14) -0.12564(11) 0.0499(5) Uani 1 1 d .
C21 C -0.4389(2) 0.20658(12) -0.42086(9) 0.0369(4) Uani 1 1 d .
C22 C -0.4050(3) 0.10824(14) -0.44099(16) 0.0787(8) Uani 1 1 d .
H22A H -0.3122 0.1061 -0.4705 0.118 Uiso 1 1 calc R
H22B H -0.4934 0.0832 -0.4668 0.118 Uiso 1 1 calc R
H22C H -0.3876 0.0720 -0.3986 0.118 Uiso 1 1 calc R
C23 C -0.5752(2) 0.2132(2) -0.37101(12) 0.0685(7) Uani 1 1 d .
H23A H -0.5855 0.2763 -0.3544 0.103 Uiso 1 1 calc R
H23B H -0.5580 0.1726 -0.3310 0.103 Uiso 1 1 calc R
H23C H -0.6703 0.1951 -0.3954 0.103 Uiso 1 1 calc R
C24 C -0.4738(2) 0.26289(15) -0.48540(9) 0.0478(5) Uani 1 1 d .
H24A H -0.4916 0.3266 -0.4718 0.072 Uiso 1 1 calc R
H24B H -0.5667 0.2388 -0.5084 0.072 Uiso 1 1 calc R
H24C H -0.3858 0.2597 -0.5177 0.072 Uiso 1 1 calc R
C25 C 0.0036(2) 0.41474(14) 0.17941(10) 0.0495(5) Uani 1 1 d .
H25A H 0.0589 0.3572 0.1901 0.059 Uiso 1 1 calc R
H25B H -0.0414 0.4391 0.2232 0.059 Uiso 1 1 calc R
C26 C 0.1128(2) 0.48389(14) 0.14649(10) 0.0463(5) Uani 1 1 d .
H26A H 0.1235 0.5386 0.1766 0.056 Uiso 1 1 calc R
H26B H 0.2167 0.4569 0.1389 0.056 Uiso 1 1 calc R
N1 N -0.07037(17) 0.14699(10) -0.05923(8) 0.0403(3) Uani 1 1 d .
N2 N 0.4008(2) 0.40949(15) -0.16091(11) 0.0713(6) Uani 1 1 d .
H11A H -0.281(2) 0.4598(13) -0.1714(11) 0.049(5) Uiso 1 1 d .
H11B H -0.143(2) 0.4767(13) -0.2290(10) 0.042(5) Uiso 1 1 d .
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
C3 O2 C26 106.53(13)
C17 O3 C21 119.44(13)
C3 O1 C25 106.86(13)
C10 C1 C2 111.83(13)
C3 C2 C1 112.01(14)
O2 C3 O1 104.77(13)
O2 C3 C2 109.21(14)
O1 C3 C2 109.31(13)
O2 C3 C4 110.79(13)
O1 C3 C4 110.67(13)
C2 C3 C4 111.84(14)
C3 C4 C5 110.36(13)
C10 C5 C4 111.00(13)
C10 C5 C6 113.57(14)
C4 C5 C6 112.75(14)
C20 C6 C5 110.69(14)
C20 C6 C7 107.08(15)
C5 C6 C7 112.29(13)
C19 C7 C8 111.78(13)
C19 C7 C6 110.79(14)
C8 C7 C6 109.97(14)
C14 C8 C9 110.60(13)
C14 C8 C7 111.43(13)
C9 C8 C7 112.36(13)
C10 C9 C11 122.62(15)
C10 C9 C8 121.08(15)
C11 C9 C8 116.10(14)
C9 C10 C1 124.85(15)
C9 C10 C5 124.70(14)
C1 C10 C5 110.41(13)
C9 C11 C12 116.46(14)
C13 C12 C11 111.85(14)
C12 C13 C14 107.62(13)
C12 C13 C17 114.68(14)
C14 C13 C17 99.94(13)
C12 C13 C18 111.25(14)
C14 C13 C18 112.91(14)
C17 C13 C18 110.00(14)
C8 C14 C13 112.66(14)
C8 C14 C15 117.95(14)
C13 C14 C15 104.67(13)
C14 C15 C16 103.94(14)
C17 C16 C15 105.70(14)
O3 C17 C13 110.36(13)
O3 C17 C16 114.91(14)
C13 C17 C16 104.34(13)
N1 C19 C7 177.91(18)
N2 C20 C6 177.4(2)
O3 C21 C24 103.23(14)
O3 C21 C23 112.00(15)
C24 C21 C23 108.81(16)
O3 C21 C22 110.46(15)
C24 C21 C22 110.36(18)
C23 C21 C22 111.6(2)
O1 C25 C26 105.28(15)
O2 C26 C25 104.47(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C3 1.422(2)
O2 C26 1.428(2)
O3 C17 1.4209(19)
O3 C21 1.450(2)
O1 C3 1.424(2)
O1 C25 1.427(2)
C1 C10 1.515(2)
C1 C2 1.534(2)
C2 C3 1.510(2)
C3 C4 1.529(2)
C4 C5 1.535(2)
C5 C10 1.517(2)
C5 C6 1.540(2)
C6 C20 1.475(3)
C6 C7 1.549(2)
C7 C19 1.473(3)
C7 C8 1.538(2)
C8 C14 1.523(2)
C8 C9 1.535(2)
C9 C10 1.345(2)
C9 C11 1.524(2)
C11 C12 1.532(2)
C12 C13 1.517(2)
C13 C14 1.530(2)
C13 C17 1.530(2)
C13 C18 1.540(2)
C14 C15 1.539(2)
C15 C16 1.551(3)
C16 C17 1.549(2)
C19 N1 1.152(2)
C20 N2 1.149(3)
C21 C24 1.514(3)
C21 C23 1.517(3)
C21 C22 1.518(3)
C25 C26 1.519(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21199625
