#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/59/1505986.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_1505986
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            'C17 H17 N O'
_chemical_formula_weight         251.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.239(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.006(3)
_cell_length_b                   9.2753(16)
_cell_length_c                   17.100(4)
_cell_measurement_temperature    143(1)
_cell_volume                     2602.4(9)
_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 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21039
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.348
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.1162
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3065
_refine_ls_wR_factor_ref         0.3240
_reflns_number_gt                3631
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0606536si20060316_113657.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               1505986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.7423(2) 0.4334(4) 0.6963(2) 0.0591(10) Uani 1 1 d .
N1 N 0.47157(19) 0.3493(3) 0.57019(19) 0.0304(7) Uani 1 1 d .
C1 C 0.5461(2) 0.2837(4) 0.5937(2) 0.0293(9) Uani 1 1 d .
C2 C 0.5625(2) 0.1312(4) 0.5808(2) 0.0314(9) Uani 1 1 d .
H2a H 0.5682 0.1176 0.5263 0.042 Uiso 1 1 calc R
H2b H 0.5175 0.0721 0.5871 0.042 Uiso 1 1 calc R
C3 C 0.6410(3) 0.0861(5) 0.6427(3) 0.0416(10) Uani 1 1 d .
H3a H 0.6312 0.0803 0.6960 0.055 Uiso 1 1 calc R
H3b H 0.6571 -0.0089 0.6288 0.055 Uiso 1 1 calc R
C4 C 0.7092(3) 0.1917(5) 0.6450(3) 0.0435(10) Uani 1 1 d .
H4a H 0.7233 0.1869 0.5937 0.058 Uiso 1 1 calc R
H4b H 0.7567 0.1617 0.6871 0.058 Uiso 1 1 calc R
C5 C 0.6900(2) 0.3476(5) 0.6606(2) 0.0399(10) Uani 1 1 d .
C6 C 0.6045(2) 0.3883(4) 0.6305(2) 0.0323(9) Uani 1 1 d .
C7 C 0.5625(3) 0.5234(4) 0.6320(2) 0.0362(10) Uani 1 1 d .
C8 C 0.5735(3) 0.6668(4) 0.6605(2) 0.0458(11) Uani 1 1 d .
H8 H 0.6251 0.7020 0.6859 0.061 Uiso 1 1 calc R
C9 C 0.5051(4) 0.7534(4) 0.6493(3) 0.0496(12) Uani 1 1 d .
H9 H 0.5130 0.8480 0.6676 0.066 Uiso 1 1 calc R
C10 C 0.4234(3) 0.7095(4) 0.6119(3) 0.0491(12) Uani 1 1 d .
H10 H 0.3797 0.7725 0.6068 0.065 Uiso 1 1 calc R
C11 C 0.4120(3) 0.5687(4) 0.5836(3) 0.0402(10) Uani 1 1 d .
C12 C 0.4816(2) 0.4914(4) 0.5941(2) 0.0318(9) Uani 1 1 d .
C13 C 0.3423(3) 0.4672(4) 0.5433(3) 0.0430(10) Uani 1 1 d .
H13a H 0.3161 0.4989 0.4886 0.057 Uiso 1 1 calc R
H13b H 0.3019 0.4636 0.5741 0.057 Uiso 1 1 calc R
C14 C 0.3835(2) 0.3144(4) 0.5424(2) 0.0313(9) Uani 1 1 d .
H14 H 0.3705 0.2767 0.4869 0.042 Uiso 1 1 calc R
C15 C 0.3608(2) 0.2051(4) 0.5982(2) 0.0346(9) Uani 1 1 d .
C16 C 0.3795(3) 0.2462(5) 0.6864(2) 0.0461(11) Uani 1 1 d .
H16a H 0.4023 0.3415 0.6936 0.069 Uiso 1 1 calc R
H16b H 0.4180 0.1791 0.7180 0.069 Uiso 1 1 calc R
H16c H 0.3303 0.2442 0.7038 0.069 Uiso 1 1 calc R
C17 C 0.3288(3) 0.0797(4) 0.5695(3) 0.0426(10) Uani 1 1 d .
H17a H 0.3166 0.0115 0.6045 0.057 Uiso 1 1 calc R
H17b H 0.3184 0.0597 0.5145 0.057 Uiso 1 1 calc R
O1' O 0.8099(2) 0.5816(4) 0.2514(2) 0.0594(10) Uani 1 1 d .
N1' N 0.9240(2) 0.6489(3) 0.52356(19) 0.0363(8) Uani 1 1 d .
C1' C 0.9032(2) 0.7187(4) 0.4513(2) 0.0323(9) Uani 1 1 d .
C2' C 0.9183(3) 0.8739(4) 0.4381(2) 0.0361(9) Uani 1 1 d .
H2a' H 0.9751 0.8876 0.4389 0.048 Uiso 1 1 calc R
H2b' H 0.9073 0.9310 0.4815 0.048 Uiso 1 1 calc R
C3' C 0.8647(3) 0.9243(5) 0.3580(3) 0.0535(12) Uani 1 1 d .
H3a' H 0.8103 0.9408 0.3640 0.071 Uiso 1 1 calc R
H3b' H 0.8853 1.0159 0.3444 0.071 Uiso 1 1 calc R
C4' C 0.8593(4) 0.8223(5) 0.2896(3) 0.0562(13) Uani 1 1 d .
H4a' H 0.9100 0.8270 0.2738 0.075 Uiso 1 1 calc R
H4b' H 0.8162 0.8549 0.2438 0.075 Uiso 1 1 calc R
C5' C 0.8430(3) 0.6654(5) 0.3064(2) 0.0400(10) Uani 1 1 d .
C6' C 0.8677(2) 0.6178(4) 0.3900(2) 0.0352(9) Uani 1 1 d .
C7' C 0.8642(2) 0.4801(4) 0.4295(3) 0.0369(9) Uani 1 1 d .
C8' C 0.8357(3) 0.3374(5) 0.4147(3) 0.0500(12) Uani 1 1 d .
H8' H 0.8111 0.3051 0.3625 0.067 Uiso 1 1 calc R
C9' C 0.8460(3) 0.2468(5) 0.4817(4) 0.0532(13) Uani 1 1 d .
H9' H 0.8279 0.1523 0.4719 0.071 Uiso 1 1 calc R
C10' C 0.8806(3) 0.2848(5) 0.5610(4) 0.0562(14) Uani 1 1 d .
H10' H 0.8846 0.2183 0.6026 0.075 Uiso 1 1 calc R
C11' C 0.9093(3) 0.4244(5) 0.5777(3) 0.0431(11) Uani 1 1 d .
C12' C 0.8996(2) 0.5084(4) 0.5099(3) 0.0361(9) Uani 1 1 d .
C13' C 0.9485(3) 0.5236(5) 0.6491(3) 0.0498(12) Uani 1 1 d .
H13a' H 1.0030 0.4907 0.6760 0.066 Uiso 1 1 calc R
H13b' H 0.9162 0.5248 0.6882 0.066 Uiso 1 1 calc R
C14' C 0.9514(2) 0.6783(4) 0.6120(2) 0.0351(9) Uani 1 1 d .
H14' H 1.0075 0.7145 0.6264 0.047 Uiso 1 1 calc R
C15' C 0.8960(3) 0.7858(5) 0.6368(2) 0.0370(10) Uani 1 1 d .
C16' C 0.8085(3) 0.7476(5) 0.6184(3) 0.0451(11) Uani 1 1 d .
H16a' H 0.7998 0.6558 0.5916 0.068 Uiso 1 1 calc R
H16b' H 0.7769 0.8198 0.5837 0.068 Uiso 1 1 calc R
H16c' H 0.7921 0.7426 0.6679 0.068 Uiso 1 1 calc R
C17' C 0.9261(3) 0.9074(5) 0.6738(3) 0.0498(12) Uani 1 1 d .
H17a' H 0.8917 0.9730 0.6894 0.066 Uiso 1 1 calc R
H17b' H 0.9815 0.9270 0.6842 0.066 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
C1 N1 C12 107.8(3)
C1 N1 C14 140.9(3)
C12 N1 C14 109.9(3)
N1 C1 C6 108.3(3)
N1 C1 C2 125.7(3)
C6 C1 C2 126.0(3)
C1 C2 C3 109.1(3)
C4 C3 C2 111.5(3)
C3 C4 C5 115.0(4)
O1 C5 C6 122.1(4)
O1 C5 C4 122.8(4)
C6 C5 C4 115.1(3)
C1 C6 C7 108.0(3)
C1 C6 C5 120.0(4)
C7 C6 C5 132.0(4)
C12 C7 C8 112.8(4)
C12 C7 C6 103.9(3)
C8 C7 C6 143.2(4)
C9 C8 C7 117.9(4)
C8 C9 C10 125.5(4)
C11 C10 C9 117.0(4)
C12 C11 C10 114.5(4)
C12 C11 C13 106.3(3)
C10 C11 C13 139.2(4)
C11 C12 N1 115.5(4)
C11 C12 C7 132.3(4)
N1 C12 C7 111.9(3)
C11 C13 C14 105.2(3)
N1 C14 C15 110.4(3)
N1 C14 C13 102.3(3)
C15 C14 C13 114.0(3)
C17 C15 C16 123.4(4)
C17 C15 C14 120.4(4)
C16 C15 C14 116.2(3)
C1' N1' C12' 107.7(3)
C1' N1' C14' 140.9(3)
C12' N1' C14' 110.4(3)
N1' C1' C6' 108.5(4)
N1' C1' C2' 125.8(3)
C6' C1' C2' 125.6(3)
C1' C2' C3' 110.5(3)
C4' C3' C2' 114.5(4)
C3' C4' C5' 115.9(4)
O1' C5' C6' 121.0(4)
O1' C5' C4' 121.8(4)
C6' C5' C4' 117.2(3)
C1' C6' C5' 119.1(4)
C1' C6' C7' 107.4(3)
C5' C6' C7' 133.6(4)
C12' C7' C8' 113.5(4)
C12' C7' C6' 103.7(3)
C8' C7' C6' 142.7(4)
C9' C8' C7' 117.1(5)
C10' C9' C8' 125.8(5)
C9' C10' C11' 118.6(5)
C12' C11' C10' 113.5(5)
C12' C11' C13' 105.2(4)
C10' C11' C13' 141.2(4)
N1' C12' C11' 115.6(4)
N1' C12' C7' 112.7(4)
C11' C12' C7' 131.5(4)
C11' C13' C14' 106.2(3)
N1' C14' C15' 110.8(3)
N1' C14' C13' 102.0(3)
C15' C14' C13' 113.7(3)
C17' C15' C16' 122.9(4)
C17' C15' C14' 120.3(4)
C16' C15' C14' 116.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.228(5)
N1 C1 1.367(5)
N1 C12 1.377(5)
N1 C14 1.482(5)
C1 C6 1.413(5)
C1 C2 1.470(5)
C2 C3 1.527(5)
C3 C4 1.510(6)
C4 C5 1.522(6)
C5 C6 1.458(6)
C6 C7 1.446(6)
C7 C12 1.389(6)
C7 C8 1.412(6)
C8 C9 1.385(7)
C9 C10 1.427(8)
C10 C11 1.389(6)
C11 C12 1.355(6)
C11 C13 1.528(6)
C13 C14 1.583(5)
C14 C15 1.510(5)
C15 C17 1.323(6)
C15 C16 1.507(6)
O1' C5' 1.235(5)
N1' C1' 1.356(5)
N1' C12' 1.370(5)
N1' C14' 1.486(5)
C1' C6' 1.417(6)
C1' C2' 1.490(6)
C2' C3' 1.506(6)
C3' C4' 1.488(7)
C4' C5' 1.523(7)
C5' C6' 1.449(6)
C6' C7' 1.453(6)
C7' C12' 1.373(6)
C7' C8' 1.410(6)
C8' C9' 1.395(8)
C9' C10' 1.374(8)
C10' C11' 1.387(7)
C11' C12' 1.370(6)
C11' C13' 1.534(7)
C13' C14' 1.574(6)
C14' C15' 1.506(5)
C15' C17' 1.329(7)
C15' C16' 1.481(6)
