#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/59/1505984.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_1505984
loop_
_publ_author_name
'Smith, 3rd, Amos B'
'Kürti, Laszló'
'Davulcu, Akin H.'
_publ_section_title
;
 A new modular indole synthesis. Construction of the highly strained CDEF
 parent tetracycle of nodulisporic acids A and B.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2167
_journal_page_last               2170
_journal_paper_doi               10.1021/ol0606536
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C27 H29 N O'
_chemical_formula_weight         383.51
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.249(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.451(3)
_cell_length_b                   8.1850(10)
_cell_length_c                   13.7757(17)
_cell_measurement_temperature    143(1)
_cell_volume                     2040.5(5)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5590
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8486
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.8(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0313
_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)+(0.0402P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                2709
_reflns_number_total             3028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0606536si20060316_102242.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        2040.4(4)
_cod_original_sg_symbol_H-M      'C 2      '
_cod_database_code               1505984
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
C1 C 0.75406(10) 0.0099(2) 0.63631(12) 0.0347(4) Uani 1 1 d .
H1A H 0.7141 -0.0414 0.5903 0.046 Uiso 1 1 calc R
H1B H 0.7589 -0.0426 0.7004 0.046 Uiso 1 1 calc R
C2 C 0.82878(10) 0.0011(2) 0.59702(13) 0.0362(4) Uani 1 1 d .
H2A H 0.8653 -0.0629 0.6414 0.048 Uiso 1 1 calc R
H2B H 0.8209 -0.0477 0.5316 0.048 Uiso 1 1 calc R
C3 C 0.85379(10) 0.1778(2) 0.59374(11) 0.0317(5) Uani 1 1 d .
C4 C 0.91290(10) 0.2644(2) 0.57290(12) 0.0359(5) Uani 1 1 d .
H4 H 0.9514 0.2115 0.5511 0.048 Uiso 1 1 calc R
C5 C 0.91356(10) 0.4361(2) 0.58558(12) 0.0359(4) Uani 1 1 d .
H5 H 0.9533 0.4941 0.5707 0.048 Uiso 1 1 calc R
C6 C 0.85860(9) 0.5238(3) 0.61886(11) 0.0334(4) Uani 1 1 d .
H6 H 0.8622 0.6366 0.6265 0.044 Uiso 1 1 calc R
C7 C 0.79717(9) 0.4382(2) 0.64081(12) 0.0304(4) Uani 1 1 d .
C8 C 0.80055(10) 0.2707(2) 0.62324(11) 0.0307(4) Uani 1 1 d .
C9 C 0.72964(9) 0.4549(2) 0.67825(11) 0.0288(4) Uani 1 1 d .
C10 C 0.69863(9) 0.3012(2) 0.68009(11) 0.0292(4) Uani 1 1 d .
C11 C 0.62202(9) 0.3055(2) 0.70094(11) 0.0273(4) Uani 1 1 d .
C12 C 0.59863(10) 0.1735(2) 0.76658(13) 0.0365(5) Uani 1 1 d .
H12A H 0.6369 0.1593 0.8252 0.049 Uiso 1 1 calc R
H12B H 0.5925 0.0706 0.7310 0.049 Uiso 1 1 calc R
C13 C 0.52526(10) 0.2209(2) 0.79745(13) 0.0356(4) Uani 1 1 d .
H13A H 0.4854 0.2117 0.7402 0.047 Uiso 1 1 calc R
H13B H 0.5155 0.1439 0.8468 0.047 Uiso 1 1 calc R
C14 C 0.52510(10) 0.3937(2) 0.83939(11) 0.0295(4) Uani 1 1 d .
H14 H 0.5599 0.3921 0.9029 0.039 Uiso 1 1 calc R
C15 C 0.45050(9) 0.4416(2) 0.86281(11) 0.0290(4) Uani 1 1 d .
C16 C 0.40093(10) 0.3255(3) 0.88434(11) 0.0351(4) Uani 1 1 d .
H16 H 0.4128 0.2155 0.8808 0.047 Uiso 1 1 calc R
C17 C 0.33440(10) 0.3671(2) 0.91086(11) 0.0350(5) Uani 1 1 d .
H17 H 0.3026 0.2865 0.9252 0.047 Uiso 1 1 calc R
C18 C 0.31636(10) 0.5305(2) 0.91563(11) 0.0321(4) Uani 1 1 d .
C19 C 0.36367(10) 0.6483(2) 0.89062(12) 0.0340(4) Uani 1 1 d .
H19 H 0.3501 0.7578 0.8903 0.045 Uiso 1 1 calc R
C20 C 0.43073(10) 0.6067(2) 0.86611(11) 0.0294(4) Uani 1 1 d .
C21 C 0.47948(11) 0.7431(2) 0.84209(13) 0.0347(5) Uani 1 1 d .
H21A H 0.4848 0.8241 0.8944 0.046 Uiso 1 1 calc R
H21B H 0.4551 0.7955 0.7813 0.046 Uiso 1 1 calc R
C22 C 0.55631(10) 0.6886(2) 0.83004(12) 0.0321(4) Uani 1 1 d .
H22A H 0.5774 0.7708 0.7931 0.043 Uiso 1 1 calc R
H22B H 0.5880 0.6787 0.8948 0.043 Uiso 1 1 calc R
C23 C 0.55358(9) 0.5260(2) 0.77633(11) 0.0252(4) Uani 1 1 d .
H23 H 0.5191 0.5350 0.7128 0.034 Uiso 1 1 calc R
C24 C 0.62789(9) 0.4699(2) 0.75762(11) 0.0266(4) Uani 1 1 d .
H24 H 0.6571 0.4452 0.8233 0.035 Uiso 1 1 calc R
C25 C 0.67842(9) 0.5815(2) 0.70792(12) 0.0288(4) Uani 1 1 d .
H25A H 0.6506 0.6384 0.6509 0.038 Uiso 1 1 calc R
H25B H 0.7050 0.6602 0.7542 0.038 Uiso 1 1 calc R
C26 C 0.56818(9) 0.3136(2) 0.60031(11) 0.0350(4) Uani 1 1 d .
H26A H 0.5776 0.4109 0.5658 0.053 Uiso 1 1 calc R
H26B H 0.5183 0.3155 0.6109 0.053 Uiso 1 1 calc R
H26C H 0.5751 0.2195 0.5615 0.053 Uiso 1 1 calc R
C27 C 0.20766(10) 0.4693(3) 0.97846(13) 0.0427(5) Uani 1 1 d .
H27A H 0.1913 0.3904 0.9273 0.064 Uiso 1 1 calc R
H27B H 0.1655 0.5223 0.9958 0.064 Uiso 1 1 calc R
H27C H 0.2355 0.4152 1.0356 0.064 Uiso 1 1 calc R
N1 N 0.74132(8) 0.18733(18) 0.64375(10) 0.0326(4) Uani 1 1 d .
O1 O 0.25327(7) 0.58822(16) 0.94372(9) 0.0418(3) 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
N1 C1 C2 103.33(14)
C3 C2 C1 104.88(14)
C8 C3 C4 114.83(17)
C8 C3 C2 106.31(15)
C4 C3 C2 138.83(17)
C3 C4 C5 118.27(17)
C6 C5 C4 124.29(17)
C5 C6 C7 118.76(19)
C8 C7 C6 112.62(16)
C8 C7 C9 103.02(15)
C6 C7 C9 144.33(19)
N1 C8 C3 115.79(16)
N1 C8 C7 113.01(15)
C3 C8 C7 131.14(17)
C10 C9 C7 108.01(16)
C10 C9 C25 109.61(14)
C7 C9 C25 142.12(17)
N1 C10 C9 109.92(14)
N1 C10 C11 135.66(16)
C9 C10 C11 113.01(15)
C10 C11 C12 118.94(14)
C10 C11 C26 107.19(12)
C12 C11 C26 110.89(14)
C10 C11 C24 98.15(13)
C12 C11 C24 108.47(12)
C26 C11 C24 112.69(14)
C11 C12 C13 110.45(15)
C14 C13 C12 113.77(15)
C15 C14 C13 112.72(14)
C15 C14 C23 111.07(14)
C13 C14 C23 114.23(12)
C16 C15 C20 117.74(16)
C16 C15 C14 121.87(17)
C20 C15 C14 120.37(15)
C17 C16 C15 122.68(19)
C18 C17 C16 118.87(18)
O1 C18 C17 124.64(16)
O1 C18 C19 115.96(17)
C17 C18 C19 119.40(17)
C20 C19 C18 121.59(18)
C19 C20 C15 119.63(16)
C19 C20 C21 117.99(17)
C15 C20 C21 122.37(15)
C20 C21 C22 114.40(16)
C23 C22 C21 111.48(14)
C24 C23 C22 113.79(14)
C24 C23 C14 107.58(14)
C22 C23 C14 108.85(12)
C23 C24 C11 111.86(13)
C23 C24 C25 122.45(14)
C11 C24 C25 106.09(12)
C9 C25 C24 100.15(13)
C8 N1 C10 105.99(14)
C8 N1 C1 109.42(14)
C10 N1 C1 143.20(15)
C18 O1 C27 116.43(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.478(2)
C1 C2 1.578(2)
C2 C3 1.521(3)
C3 C8 1.365(2)
C3 C4 1.377(2)
C4 C5 1.416(3)
C5 C6 1.391(2)
C6 C7 1.414(2)
C7 C8 1.396(3)
C7 C9 1.445(2)
C8 N1 1.364(2)
C9 C10 1.385(2)
C9 C25 1.512(2)
C10 N1 1.376(2)
C10 C11 1.497(2)
C11 C12 1.525(2)
C11 C26 1.541(2)
C11 C24 1.548(2)
C12 C13 1.546(2)
C13 C14 1.528(2)
C14 C15 1.525(2)
C14 C23 1.543(2)
C15 C16 1.390(2)
C15 C20 1.403(2)
C16 C17 1.390(2)
C17 C18 1.383(3)
C18 O1 1.380(2)
C18 C19 1.388(2)
C19 C20 1.387(2)
C20 C21 1.511(2)
C21 C22 1.526(2)
C22 C23 1.519(2)
C23 C24 1.515(2)
C24 C25 1.556(2)
C27 O1 1.429(2)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21194055 ChemSpider
