#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/39/4023939.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_4023939
loop_
_publ_author_name
'Amos B. Smith, III'
'László Kürti'
'Akin H. Davulcu'
'Young Shin Cho'
'Kazuyuki Ohmoto'
_publ_contact_author_address
;Department of Chemistry
University of Pennsylvania
Philadelphia, PA 19104-6323
(215) 898-4860 (TEL)
(215) 898-5129 (FAX) 
;
_publ_contact_author_email       smithab@sas.upenn.edu
_publ_contact_author_fax         '(215) 898-5129'
_publ_contact_author_name        'Amos B. Smith, III'
_publ_contact_author_phone       '(215) 898-4860'
_publ_section_title
;
 Indole Diterpene Synthetic Studies: Development of a Second-Generation
 Synthetic Strategy for (+)-Nodulisporic Acids A and B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4611
_journal_page_last               4620
_journal_paper_doi               10.1021/jo062423a
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H15 N'
_chemical_formula_weight         197.27
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_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
_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                   6.9258(8)
_cell_length_b                   8.8531(11)
_cell_length_c                   17.129(2)
_cell_measurement_temperature    143(1)
_cell_volume                     1050.3(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5408
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7497
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1009P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1699
_reflns_number_gt                1329
_reflns_number_total             1863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062423asi20061218_094306.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4023939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5144(3) 0.6851(2) 0.45530(11) 0.0324(6) Uani 1 1 d . . .
C1 C 0.5135(4) 0.5517(3) 0.41379(15) 0.0318(6) Uani 1 1 d . . .
C2 C 0.5068(5) 0.5401(3) 0.32726(15) 0.0402(7) Uani 1 1 d . . .
H2A H 0.6293 0.5721 0.3053 0.053 Uiso 1 1 calc R . .
H2B H 0.4063 0.6055 0.3069 0.053 Uiso 1 1 calc R . .
C3 C 0.4664(9) 0.3790(4) 0.30460(19) 0.0912(17) Uani 1 1 d . . .
H3A H 0.3278 0.3636 0.3065 0.121 Uiso 1 1 calc R . .
H3B H 0.5064 0.3654 0.2508 0.121 Uiso 1 1 calc R . .
C4 C 0.5555(7) 0.2634(4) 0.35033(18) 0.0777(15) Uani 1 1 d . . .
H4A H 0.6938 0.2680 0.3418 0.103 Uiso 1 1 calc R . .
H4B H 0.5112 0.1662 0.3312 0.103 Uiso 1 1 calc R . .
C5 C 0.5186(5) 0.2700(3) 0.43773(14) 0.0374(7) Uani 1 1 d . . .
H5A H 0.3949 0.2238 0.4494 0.050 Uiso 1 1 calc R . .
H5B H 0.6180 0.2136 0.4650 0.050 Uiso 1 1 calc R . .
C6 C 0.5188(4) 0.4310(3) 0.46559(14) 0.0297(6) Uani 1 1 d . . .
C7 C 0.5201(4) 0.4919(3) 0.54373(14) 0.0309(6) Uani 1 1 d . . .
C8 C 0.5257(4) 0.4525(3) 0.62295(15) 0.0386(7) Uani 1 1 d . . .
H8 H 0.5284 0.3516 0.6380 0.051 Uiso 1 1 calc R . .
C9 C 0.5270(5) 0.5659(3) 0.67836(16) 0.0452(8) Uani 1 1 d . . .
H9 H 0.5302 0.5377 0.7306 0.060 Uiso 1 1 calc R . .
C10 C 0.5240(5) 0.7230(3) 0.66081(15) 0.0412(7) Uani 1 1 d . . .
H10 H 0.5245 0.7949 0.7004 0.055 Uiso 1 1 calc R . .
C11 C 0.5201(4) 0.7652(3) 0.58345(16) 0.0338(6) Uani 1 1 d . . .
C12 C 0.5183(4) 0.6471(3) 0.53176(14) 0.0307(6) Uani 1 1 d . . .
C13 C 0.5172(5) 0.9086(3) 0.53443(16) 0.0363(6) Uani 1 1 d . . .
H13A H 0.6298 0.9703 0.5451 0.048 Uiso 1 1 calc R . .
H13B H 0.4020 0.9675 0.5451 0.048 Uiso 1 1 calc R . .
C14 C 0.5183(4) 0.8512(3) 0.44707(15) 0.0325(6) Uani 1 1 d . . .
H14A H 0.4058 0.8872 0.4189 0.043 Uiso 1 1 calc R . .
H14B H 0.6339 0.8841 0.4200 0.043 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'
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 N1 C1 106.61(19) . . ?
C12 N1 C14 109.90(19) . . ?
C1 N1 C14 143.5(2) . . ?
N1 C1 C6 109.3(2) . . ?
N1 C1 C2 125.0(2) . . ?
C6 C1 C2 125.7(2) . . ?
C1 C2 C3 109.2(2) . . ?
C4 C3 C2 117.2(3) . . ?
C3 C4 C5 116.1(3) . . ?
C6 C5 C4 110.4(2) . . ?
C1 C6 C7 107.7(2) . . ?
C1 C6 C5 121.8(2) . . ?
C7 C6 C5 130.5(2) . . ?
C12 C7 C8 112.9(2) . . ?
C12 C7 C6 103.5(2) . . ?
C8 C7 C6 143.6(2) . . ?
C9 C8 C7 119.0(3) . . ?
C8 C9 C10 124.4(3) . . ?
C11 C10 C9 118.0(2) . . ?
C12 C11 C10 114.5(2) . . ?
C12 C11 C13 106.3(2) . . ?
C10 C11 C13 139.3(2) . . ?
N1 C12 C11 115.8(2) . . ?
N1 C12 C7 112.9(2) . . ?
C11 C12 C7 131.3(2) . . ?
C11 C13 C14 104.7(2) . . ?
N1 C14 C13 103.28(18) . . ?
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
N1 C12 1.353(3) . ?
N1 C1 1.379(3) . ?
N1 C14 1.477(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.486(3) . ?
C2 C3 1.505(4) . ?
C3 C4 1.429(5) . ?
C4 C5 1.520(4) . ?
C5 C6 1.503(3) . ?
C6 C7 1.443(3) . ?
C7 C12 1.389(3) . ?
C7 C8 1.402(3) . ?
C8 C9 1.382(4) . ?
C9 C10 1.423(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.371(4) . ?
C11 C13 1.522(3) . ?
C13 C14 1.581(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21156795
