#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/74/1517437.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_1517437
loop_
_publ_author_name
'Peng, Xie-Xue'
'Deng, Yun-Jing'
'Yang, Xiu-Long'
'Zhang, Lin'
'Yu, Wei'
'Han, Bing'
_publ_section_title
;
 Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient
 Oxyoximation and Aminooximation of Alkenes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4650
_journal_paper_doi               10.1021/ol502258n
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C24 H28 N4 O4'
_chemical_formula_weight         436.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.789(2)
_cell_angle_beta                 73.020(3)
_cell_angle_gamma                86.307(2)
_cell_formula_units_Z            1
_cell_length_a                   6.2135(13)
_cell_length_b                   9.640(2)
_cell_length_c                   9.692(2)
_cell_measurement_temperature    296(2)
_cell_volume                     553.2(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3265
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0947
_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)+(0.0000P)²+1.5570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1795
_reflns_number_gt                1400
_reflns_number_total             1660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502258n_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517435--1517439.cif.
;
_cod_original_cell_volume        553.1(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1517437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.3575(5) 0.7483(3) 0.2582(3) 0.0556(8) Uani 1 1 d .
O2 O 0.2318(9) 1.0295(6) 0.0921(7) 0.131(2) Uani 1 1 d .
N1 N 0.2979(5) 0.7128(3) 0.4079(4) 0.0451(8) Uani 1 1 d .
N2 N 0.4276(9) 0.9997(5) 0.0698(6) 0.0932(19) Uani 1 1 d .
C1 C 0.3817(10) 0.6623(5) 0.9074(5) 0.0689(14) Uani 1 1 d .
H1 H 0.3621 0.6490 1.0063 0.083 Uiso 1 1 calc R
C2 C 0.5878(9) 0.6323(5) 0.8110(5) 0.0613(13) Uani 1 1 d .
H2 H 0.7072 0.5975 0.8449 0.074 Uiso 1 1 calc R
C3 C 0.6184(7) 0.6536(5) 0.6641(5) 0.0509(11) Uani 1 1 d .
H3 H 0.7590 0.6340 0.5998 0.061 Uiso 1 1 calc R
C4 C 0.4404(6) 0.7042(4) 0.6112(4) 0.0397(9) Uani 1 1 d .
C5 C 0.2326(7) 0.7337(4) 0.7107(5) 0.0513(11) Uani 1 1 d .
H5 H 0.1119 0.7684 0.6781 0.062 Uiso 1 1 calc R
C6 C 0.2043(9) 0.7121(5) 0.8570(5) 0.0642(13) Uani 1 1 d .
H6 H 0.0644 0.7314 0.9221 0.077 Uiso 1 1 calc R
C7 C 0.4660(6) 0.7284(4) 0.4549(4) 0.0376(9) Uani 1 1 d .
C8 C 0.6775(7) 0.7730(4) 0.3381(4) 0.0445(10) Uani 1 1 d .
C9 C 0.5681(8) 0.8188(5) 0.2170(6) 0.0654(14) Uani 1 1 d .
H9 H 0.6637 0.7829 0.1262 0.079 Uiso 1 1 calc R
C10 C 0.5254(10) 0.9701(6) 0.1933(6) 0.0770(16) Uani 1 1 d .
H10A H 0.6655 1.0172 0.1733 0.092 Uiso 1 1 calc R
H10B H 0.4220 1.0060 0.2803 0.092 Uiso 1 1 calc R
C11 C 0.8314(7) 0.6448(5) 0.2879(5) 0.0546(11) Uani 1 1 d .
H11A H 0.8826 0.6033 0.3665 0.082 Uiso 1 1 calc R
H11B H 0.9588 0.6721 0.2093 0.082 Uiso 1 1 calc R
H11C H 0.7494 0.5785 0.2565 0.082 Uiso 1 1 calc R
C12 C 0.8039(7) 0.8843(5) 0.3825(5) 0.0553(12) Uani 1 1 d .
H12A H 0.7018 0.9615 0.4175 0.083 Uiso 1 1 calc R
H12B H 0.9232 0.9156 0.3005 0.083 Uiso 1 1 calc R
H12C H 0.8662 0.8458 0.4575 0.083 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 O1 C9 108.9(3) . .
C7 N1 O1 109.2(3) . .
O2 N2 N2 121.3(6) . 2_675
O2 N2 C10 120.2(6) . .
N2 N2 C10 118.4(6) 2_675 .
C2 C1 C6 119.7(4) . .
C2 C1 H1 120.1 . .
C6 C1 H1 120.1 . .
C1 C2 C3 120.4(5) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C2 C3 C4 120.6(4) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C5 C4 C3 118.1(4) . .
C5 C4 C7 119.5(4) . .
C3 C4 C7 122.4(4) . .
C6 C5 C4 120.7(4) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C5 C6 C1 120.5(5) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
N1 C7 C4 119.2(3) . .
N1 C7 C8 114.1(3) . .
C4 C7 C8 126.7(3) . .
C12 C8 C7 114.1(4) . .
C12 C8 C11 111.3(3) . .
C7 C8 C11 109.6(3) . .
C12 C8 C9 115.7(3) . .
C7 C8 C9 98.4(3) . .
C11 C8 C9 106.8(4) . .
C10 C9 O1 110.1(4) . .
C10 C9 C8 116.7(4) . .
O1 C9 C8 104.3(3) . .
C10 C9 H9 108.5 . .
O1 C9 H9 108.5 . .
C8 C9 H9 108.5 . .
C9 C10 N2 110.9(5) . .
C9 C10 H10A 109.5 . .
N2 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
N2 C10 H10B 109.5 . .
H10A C10 H10B 108.0 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.410(4) .
O1 C9 1.450(5) .
O2 N2 1.192(7) .
N1 C7 1.276(5) .
N2 N2 1.389(12) 2_675
N2 C10 1.495(7) .
C1 C2 1.374(7) .
C1 C6 1.377(7) .
C1 H1 0.9300 .
C2 C3 1.382(6) .
C2 H2 0.9300 .
C3 C4 1.397(5) .
C3 H3 0.9300 .
C4 C5 1.394(6) .
C4 C7 1.479(5) .
C5 C6 1.378(7) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.525(5) .
C8 C12 1.525(6) .
C8 C11 1.531(6) .
C8 C9 1.545(6) .
C9 C10 1.478(8) .
C9 H9 0.9800 .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
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
C9 O1 N1 C7 -12.6(4) .
C6 C1 C2 C3 0.8(7) .
C1 C2 C3 C4 -0.7(7) .
C2 C3 C4 C5 0.6(6) .
C2 C3 C4 C7 180.0(4) .
C3 C4 C5 C6 -0.6(6) .
C7 C4 C5 C6 -180.0(4) .
C4 C5 C6 C1 0.7(7) .
C2 C1 C6 C5 -0.8(7) .
O1 N1 C7 C4 176.9(3) .
O1 N1 C7 C8 -2.5(4) .
C5 C4 C7 N1 -32.1(5) .
C3 C4 C7 N1 148.5(4) .
C5 C4 C7 C8 147.3(4) .
C3 C4 C7 C8 -32.1(6) .
N1 C7 C8 C12 138.2(4) .
C4 C7 C8 C12 -41.2(5) .
N1 C7 C8 C11 -96.2(4) .
C4 C7 C8 C11 84.4(5) .
N1 C7 C8 C9 15.1(4) .
C4 C7 C8 C9 -164.3(4) .
N1 O1 C9 C10 -104.3(4) .
N1 O1 C9 C8 21.7(5) .
C12 C8 C9 C10 -21.0(6) .
C7 C8 C9 C10 100.9(5) .
C11 C8 C9 C10 -145.6(4) .
C12 C8 C9 O1 -142.7(4) .
C7 C8 C9 O1 -20.7(4) .
C11 C8 C9 O1 92.7(4) .
O1 C9 C10 N2 -63.6(6) .
C8 C9 C10 N2 177.8(4) .
O2 N2 C10 C9 103.8(7) .
N2 N2 C10 C9 -80.3(7) 2_675
