#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/64/1506478.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_1506478
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Chen, Fon-Len'
'Chen, Shang-Hung'
'Liao, Ju-Hsiou'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Intramolecular Diels-Alder cycloadditions of fulvenes. Application to the
 kigelinol, neoamphilectane, and kempane skeletons.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              557
_journal_page_last               560
_journal_paper_doi               10.1021/ol047730m
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C19 H19 N4 O4'
_chemical_formula_weight         367.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.890(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7950(10)
_cell_length_b                   12.533(2)
_cell_length_c                   15.010(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1763.2(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3912
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.100
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.001(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0719
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1300P)²+1.1359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2275
_reflns_number_gt                1851
_reflns_number_total             3077
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol047730msi20041105_120757.cif
_cod_data_source_block           cb14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1506478
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
N1 N 0.3677(4) 1.0526(2) 0.2368(2) 0.0510(8) Uani 1 1 d .
N2 N 0.1255(4) 0.8089(3) -0.0088(2) 0.0632(10) Uani 1 1 d .
N3 N 0.2869(3) 0.6334(2) 0.1015(2) 0.0467(8) Uani 1 1 d .
N4 N 0.3710(3) 0.5544(2) 0.1543(2) 0.0492(8) Uani 1 1 d .
O1 O 0.2888(3) 1.1227(2) 0.1942(2) 0.0708(9) Uani 1 1 d .
O2 O 0.4614(3) 1.0681(2) 0.3094(2) 0.0725(9) Uani 1 1 d .
O3 O 0.0986(3) 0.7183(2) -0.0398(2) 0.0788(10) Uani 1 1 d .
O4 O 0.0687(5) 0.8864(3) -0.0509(3) 0.1175(17) Uani 1 1 d .
C1 C 0.3491(4) 0.9448(3) 0.1992(2) 0.0411(8) Uani 1 1 d .
C2 C 0.2489(4) 0.9261(3) 0.1158(2) 0.0447(9) Uani 1 1 d .
H2 H 0.1947 0.9818 0.0826 0.054 Uiso 1 1 calc R
C3 C 0.2294(4) 0.8230(3) 0.0815(2) 0.0422(8) Uani 1 1 d .
C4 C 0.3079(4) 0.7363(3) 0.1312(2) 0.0395(8) Uani 1 1 d .
C5 C 0.4102(4) 0.7605(3) 0.2161(2) 0.0459(9) Uani 1 1 d .
H5 H 0.4651 0.7059 0.2506 0.055 Uiso 1 1 calc R
C6 C 0.4304(4) 0.8622(3) 0.2489(3) 0.0474(9) Uani 1 1 d .
H6 H 0.4993 0.8764 0.3049 0.057 Uiso 1 1 calc R
C7 C 0.3426(4) 0.4568(3) 0.1287(3) 0.0457(9) Uani 1 1 d .
C8 C 0.2220(4) 0.4242(3) 0.0464(3) 0.0540(10) Uani 1 1 d .
H8 H 0.1480 0.4708 0.0187 0.065 Uiso 1 1 calc R
C9 C 0.2262(5) 0.3109(3) 0.0101(3) 0.0715(13) Uani 1 1 d .
H9A H 0.1434 0.3005 -0.0434 0.086 Uiso 1 1 calc R
H9B H 0.2186 0.2612 0.0579 0.086 Uiso 1 1 calc R
C10 C 0.3595(6) 0.2838(4) -0.0181(3) 0.0832(16) Uani 1 1 d .
H10A H 0.3356 0.2297 -0.0664 0.100 Uiso 1 1 calc R
H10B H 0.3905 0.3469 -0.0442 0.100 Uiso 1 1 calc R
C11 C 0.4806(5) 0.2439(3) 0.0611(3) 0.0641(12) Uani 1 1 d .
C12 C 0.5315(6) 0.1460(4) 0.0609(4) 0.0843(16) Uani 1 1 d .
H12A H 0.4921 0.1006 0.0110 0.101 Uiso 1 1 calc R
H12B H 0.6066 0.1226 0.1106 0.101 Uiso 1 1 calc R
C13 C 0.5458(4) 0.3214(3) 0.1380(3) 0.0516(10) Uani 1 1 d .
C14 C 0.6215(5) 0.4166(3) 0.1120(3) 0.0637(12) Uani 1 1 d .
H14A H 0.6103 0.4415 0.0520 0.076 Uiso 1 1 calc R
C15 C 0.7055(5) 0.4578(4) 0.1887(3) 0.0697(13) Uani 1 1 d .
H15A H 0.7629 0.5178 0.1928 0.084 Uiso 1 1 calc R
C16 C 0.5431(5) 0.4143(3) 0.2799(3) 0.0594(11) Uani 1 1 d .
H16A H 0.5305 0.4902 0.2876 0.071 Uiso 1 1 calc R
H16B H 0.5290 0.3766 0.3330 0.071 Uiso 1 1 calc R
C17 C 0.4396(4) 0.3731(3) 0.1876(3) 0.0489(9) Uani 1 1 d .
H17 H 0.3804 0.3164 0.2021 0.059 Uiso 1 1 calc R
C18 C 0.6920(5) 0.3903(3) 0.2687(3) 0.0622(12) Uani 1 1 d .
H18 H 0.7721 0.3941 0.3257 0.075 Uiso 1 1 calc R
C19 C 0.6642(5) 0.2818(3) 0.2222(3) 0.0609(11) Uani 1 1 d .
H19A H 0.6309 0.2297 0.2589 0.073 Uiso 1 1 calc R
H19B H 0.7460 0.2542 0.2055 0.073 Uiso 1 1 calc R
H3 H 0.225(5) 0.622(3) 0.053(3) 0.062(13) 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
O1 N1 O2 123.4(3)
O1 N1 C1 118.4(3)
O2 N1 C1 118.2(3)
O4 N2 O3 122.1(3)
O4 N2 C3 119.0(3)
O3 N2 C3 118.9(3)
C4 N3 N4 118.9(3)
C7 N4 N3 118.0(3)
C2 C1 C6 120.8(3)
C2 C1 N1 119.4(3)
C6 C1 N1 119.8(3)
C1 C2 C3 119.1(3)
C2 C3 C4 121.8(3)
C2 C3 N2 116.4(3)
C4 C3 N2 121.8(3)
N3 C4 C5 120.1(3)
N3 C4 C3 123.3(3)
C5 C4 C3 116.6(3)
C6 C5 C4 121.4(3)
C5 C6 C1 120.4(3)
N4 C7 C8 123.7(3)
N4 C7 C17 116.1(3)
C8 C7 C17 120.2(3)
C7 C8 C9 116.9(3)
C8 C9 C10 114.9(4)
C11 C10 C9 113.5(4)
C12 C11 C10 121.2(4)
C12 C11 C13 121.6(4)
C10 C11 C13 117.1(3)
C11 C13 C14 116.2(4)
C11 C13 C19 118.5(3)
C14 C13 C19 99.1(3)
C11 C13 C17 115.8(3)
C14 C13 C17 103.7(3)
C19 C13 C17 100.9(3)
C15 C14 C13 108.3(4)
C14 C15 C18 107.5(4)
C18 C16 C17 103.3(3)
C7 C17 C16 115.3(3)
C7 C17 C13 113.2(3)
C16 C17 C13 102.0(3)
C15 C18 C19 100.5(3)
C15 C18 C16 106.4(3)
C19 C18 C16 100.1(3)
C18 C19 C13 94.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.221(4)
N1 O2 1.220(4)
N1 C1 1.455(4)
N2 O4 1.204(4)
N2 O3 1.227(4)
N2 C3 1.450(5)
N3 C4 1.361(4)
N3 N4 1.380(4)
N4 C7 1.289(4)
C1 C2 1.368(5)
C1 C6 1.384(5)
C2 C3 1.383(5)
C3 C4 1.412(5)
C4 C5 1.407(5)
C5 C6 1.360(5)
C7 C8 1.497(5)
C7 C17 1.515(5)
C8 C9 1.526(5)
C9 C10 1.524(7)
C10 C11 1.500(7)
C11 C12 1.325(6)
C11 C13 1.502(6)
C13 C14 1.515(6)
C13 C19 1.529(5)
C13 C17 1.583(5)
C14 C15 1.311(6)
C15 C18 1.506(6)
C16 C18 1.546(6)
C16 C17 1.549(5)
C18 C19 1.517(6)
