#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/36/4023637.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_4023637
loop_
_publ_author_name
'Gregory R. Dake'
'Erik E. Fenster'
'Brian O. Patrick'
_publ_section_title
;
 A Synthetic Approach to the Fusicoccane A-B Ring Fragment Based
 on a Pauson-Khand Cycloaddition/Norrish Type 1 Fragmentation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6711
_journal_page_last               6715
_journal_paper_doi               10.1021/jo800933f
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H31 N O2'
_chemical_formula_weight         293.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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                 96.002(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.1125(12)
_cell_length_b                   5.8190(5)
_cell_length_c                   13.5233(14)
_cell_measurement_reflns_used    5414
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.50
_cell_volume                     869.67(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_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  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14299
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3932
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0452
_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)+(0.0625P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                3420
_reflns_number_total             3932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800933f-file003.cif
_cod_data_source_block           gd012
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023637
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
C1 C 0.37005(13) 0.3039(3) 0.31924(11) 0.0231(3) Uani 1 1 d . . .
C2 C 0.32398(14) 0.4734(3) 0.23558(12) 0.0261(3) Uani 1 1 d . . .
H2A H 0.2883 0.6114 0.2638 0.031 Uiso 1 1 calc R . .
H2B H 0.3912 0.5223 0.1978 0.031 Uiso 1 1 calc R . .
C3 C 0.22766(16) 0.3424(3) 0.16772(11) 0.0291(4) Uani 1 1 d . . .
H3A H 0.2608 0.2940 0.1058 0.035 Uiso 1 1 calc R . .
H3B H 0.1562 0.4412 0.1499 0.035 Uiso 1 1 calc R . .
C4 C 0.19176(13) 0.1288(3) 0.22710(11) 0.0227(3) Uani 1 1 d . . .
H4 H 0.2356 -0.0051 0.2015 0.027 Uiso 1 1 calc R . .
C5 C 0.24997(13) 0.1721(3) 0.33596(11) 0.0213(3) Uani 1 1 d . . .
H5 H 0.2714 0.0207 0.3681 0.026 Uiso 1 1 calc R . .
C6 C 0.46116(14) 0.1270(3) 0.28386(12) 0.0252(3) Uani 1 1 d . . .
H6A H 0.4815 0.0166 0.3388 0.030 Uiso 1 1 calc R . .
H6B H 0.4188 0.0396 0.2278 0.030 Uiso 1 1 calc R . .
C7 C 0.57966(14) 0.2154(3) 0.25064(12) 0.0288(4) Uani 1 1 d . . .
H7 H 0.6185 0.3268 0.3005 0.035 Uiso 1 1 calc R . .
C8 C 0.66827(18) 0.0209(4) 0.23271(15) 0.0427(5) Uani 1 1 d . . .
H8A H 0.7370 0.0197 0.2856 0.051 Uiso 1 1 calc R . .
H8B H 0.6270 -0.1300 0.2323 0.051 Uiso 1 1 calc R . .
C9 C 0.66728(15) 0.2866(3) 0.10699(13) 0.0302(4) Uani 1 1 d . . .
C10 C 0.76329(19) 0.4662(4) 0.13801(16) 0.0438(5) Uani 1 1 d . . .
H10A H 0.7815 0.4642 0.2105 0.066 Uiso 1 1 calc R . .
H10B H 0.7333 0.6186 0.1167 0.066 Uiso 1 1 calc R . .
H10C H 0.8369 0.4315 0.1068 0.066 Uiso 1 1 calc R . .
C11 C 0.6340(2) 0.2804(5) -0.00369(14) 0.0509(6) Uani 1 1 d . . .
H11A H 0.7065 0.2489 -0.0370 0.076 Uiso 1 1 calc R . .
H11B H 0.5998 0.4290 -0.0261 0.076 Uiso 1 1 calc R . .
H11C H 0.5740 0.1591 -0.0201 0.076 Uiso 1 1 calc R . .
C12 C 0.43090(16) 0.4335(3) 0.40962(13) 0.0321(4) Uani 1 1 d . . .
H12A H 0.4990 0.5235 0.3898 0.048 Uiso 1 1 calc R . .
H12B H 0.4606 0.3232 0.4613 0.048 Uiso 1 1 calc R . .
H12C H 0.3721 0.5369 0.4356 0.048 Uiso 1 1 calc R . .
C13 C 0.05565(14) 0.0693(3) 0.21120(12) 0.0276(4) Uani 1 1 d . . .
H13 H 0.0084 0.2056 0.2303 0.033 Uiso 1 1 calc R . .
C14 C 0.01958(16) 0.0164(4) 0.10082(14) 0.0370(4) Uani 1 1 d . . .
H14A H 0.0645 -0.1182 0.0813 0.055 Uiso 1 1 calc R . .
H14B H 0.0386 0.1489 0.0605 0.055 Uiso 1 1 calc R . .
H14C H -0.0674 -0.0152 0.0902 0.055 Uiso 1 1 calc R . .
C15 C 0.02328(15) -0.1365(3) 0.27334(13) 0.0319(4) Uani 1 1 d . . .
H15A H 0.0664 -0.2730 0.2533 0.048 Uiso 1 1 calc R . .
H15B H -0.0641 -0.1639 0.2627 0.048 Uiso 1 1 calc R . .
H15C H 0.0469 -0.1048 0.3439 0.048 Uiso 1 1 calc R . .
C16 C 0.16754(14) 0.3054(3) 0.40090(11) 0.0260(3) Uani 1 1 d . . .
H16A H 0.1780 0.4720 0.3897 0.031 Uiso 1 1 calc R . .
H16B H 0.0823 0.2665 0.3787 0.031 Uiso 1 1 calc R . .
C17 C 0.19136(17) 0.2573(3) 0.51322(12) 0.0322(4) Uani 1 1 d . . .
H17A H 0.2762 0.2976 0.5362 0.039 Uiso 1 1 calc R . .
H17B H 0.1381 0.3567 0.5491 0.039 Uiso 1 1 calc R . .
C18 C 0.16984(16) 0.0160(3) 0.53803(12) 0.0335(4) Uani 1 1 d . . .
N1 N 0.15281(18) -0.1717(4) 0.55672(13) 0.0525(5) Uani 1 1 d . . .
O1 O 0.55997(10) 0.3214(2) 0.15498(8) 0.0341(3) Uani 1 1 d . . .
O2 O 0.70911(13) 0.0652(2) 0.13979(11) 0.0462(4) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C1 C2 110.73(14) . . ?
C12 C1 C6 108.93(12) . . ?
C2 C1 C6 111.93(12) . . ?
C12 C1 C5 115.78(12) . . ?
C2 C1 C5 101.23(12) . . ?
C6 C1 C5 108.11(13) . . ?
C3 C2 C1 106.07(13) . . ?
C3 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C2 C3 C4 106.76(12) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C13 C4 C3 114.07(13) . . ?
C13 C4 C5 118.00(12) . . ?
C3 C4 C5 104.72(12) . . ?
C13 C4 H4 106.4 . . ?
C3 C4 H4 106.4 . . ?
C5 C4 H4 106.4 . . ?
C16 C5 C4 113.87(12) . . ?
C16 C5 C1 113.52(13) . . ?
C4 C5 C1 102.49(11) . . ?
C16 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C1 C5 H5 108.9 . . ?
C7 C6 C1 118.56(14) . . ?
C7 C6 H6A 107.7 . . ?
C1 C6 H6A 107.7 . . ?
C7 C6 H6B 107.7 . . ?
C1 C6 H6B 107.7 . . ?
H6A C6 H6B 107.1 . . ?
O1 C7 C6 110.92(13) . . ?
O1 C7 C8 102.42(13) . . ?
C6 C7 C8 112.68(15) . . ?
O1 C7 H7 110.2 . . ?
C6 C7 H7 110.2 . . ?
C8 C7 H7 110.2 . . ?
O2 C8 C7 106.17(15) . . ?
O2 C8 H8A 110.5 . . ?
C7 C8 H8A 110.5 . . ?
O2 C8 H8B 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
O2 C9 O1 104.29(13) . . ?
O2 C9 C11 109.03(16) . . ?
O1 C9 C11 108.96(14) . . ?
O2 C9 C10 109.81(16) . . ?
O1 C9 C10 111.83(14) . . ?
C11 C9 C10 112.56(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 108.97(15) . . ?
C15 C13 C4 112.50(13) . . ?
C14 C13 C4 109.42(13) . . ?
C15 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C4 C13 H13 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C5 114.77(13) . . ?
C17 C16 H16A 108.6 . . ?
C5 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C5 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 112.56(15) . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
N1 C18 C17 179.6(2) . . ?
C7 O1 C9 107.08(12) . . ?
C8 O2 C9 108.63(13) . . ?
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
C1 C12 1.532(2) . ?
C1 C2 1.547(2) . ?
C1 C6 1.554(2) . ?
C1 C5 1.576(2) . ?
C2 C3 1.537(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.554(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C13 1.545(2) . ?
C4 C5 1.565(2) . ?
C4 H4 1.0000 . ?
C5 C16 1.543(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.524(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O1 1.429(2) . ?
C7 C8 1.536(3) . ?
C7 H7 1.0000 . ?
C8 O2 1.404(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O2 1.425(2) . ?
C9 O1 1.4304(19) . ?
C9 C11 1.504(3) . ?
C9 C10 1.521(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.527(2) . ?
C13 C14 1.536(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.540(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.469(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N1 1.141(3) . ?
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
C12 C1 C2 C3 -159.91(13) . . . . ?
C6 C1 C2 C3 78.34(16) . . . . ?
C5 C1 C2 C3 -36.60(15) . . . . ?
C1 C2 C3 C4 16.05(17) . . . . ?
C2 C3 C4 C13 141.81(14) . . . . ?
C2 C3 C4 C5 11.35(16) . . . . ?
C13 C4 C5 C16 -38.82(19) . . . . ?
C3 C4 C5 C16 89.29(15) . . . . ?
C13 C4 C5 C1 -161.85(13) . . . . ?
C3 C4 C5 C1 -33.74(14) . . . . ?
C12 C1 C5 C16 39.56(18) . . . . ?
C2 C1 C5 C16 -80.21(14) . . . . ?
C6 C1 C5 C16 162.04(12) . . . . ?
C12 C1 C5 C4 162.82(13) . . . . ?
C2 C1 C5 C4 43.05(14) . . . . ?
C6 C1 C5 C4 -74.70(14) . . . . ?
C12 C1 C6 C7 -60.51(18) . . . . ?
C2 C1 C6 C7 62.27(18) . . . . ?
C5 C1 C6 C7 172.91(13) . . . . ?
C1 C6 C7 O1 -74.39(18) . . . . ?
C1 C6 C7 C8 171.44(14) . . . . ?
O1 C7 C8 O2 12.4(2) . . . . ?
C6 C7 C8 O2 131.60(16) . . . . ?
C3 C4 C13 C15 -178.12(14) . . . . ?
C5 C4 C13 C15 -54.57(19) . . . . ?
C3 C4 C13 C14 60.60(18) . . . . ?
C5 C4 C13 C14 -175.85(14) . . . . ?
C4 C5 C16 C17 153.09(14) . . . . ?
C1 C5 C16 C17 -90.13(16) . . . . ?
C5 C16 C17 C18 -62.2(2) . . . . ?
C16 C17 C18 N1 -10(34) . . . . ?
C6 C7 O1 C9 -149.32(14) . . . . ?
C8 C7 O1 C9 -28.86(18) . . . . ?
O2 C9 O1 C7 35.01(17) . . . . ?
C11 C9 O1 C7 151.33(17) . . . . ?
C10 C9 O1 C7 -83.59(18) . . . . ?
C7 C8 O2 C9 8.6(2) . . . . ?
O1 C9 O2 C8 -26.49(19) . . . . ?
C11 C9 O2 C8 -142.76(17) . . . . ?
C10 C9 O2 C8 93.49(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658731
