#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:31:12 +0100 (lun 21 de mar de 2016) $
#$Revision: 178482 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/03/4030335.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_4030335
loop_
_publ_author_name
'Li, Dan-Dan'
'Li, Zhong-Yuan'
'Wang, Guan-Wu'
_publ_section_title
;
 Catalyst-Free Approach to Construct C-C Bond Initiated by N-O Bond
 Cleavage under Thermal Conditions.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              190
_journal_paper_doi               10.1021/jo502287y
_journal_volume                  80
_journal_year                    2014
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           86
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-P 4bc'
_symmetry_space_group_name_H-M   'P 42/n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.5426(4)
_cell_length_b                   25.5426(4)
_cell_length_c                   4.67850(10)
_cell_measurement_reflns_used    4578
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      62.6286
_cell_measurement_theta_min      3.4578
_cell_volume                     3052.37(9)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction Ltd.)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            12408
_diffrn_reflns_theta_full        62.72
_diffrn_reflns_theta_max         62.72
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.789
_exptl_absorpt_correction_T_max  0.8455
_exptl_absorpt_correction_T_min  0.7642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0515
_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)+(0.0794P)²+1.1038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                1898
_reflns_number_total             2447
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502287y_si_002.cif
_cod_data_source_block           120309
_cod_depositor_comments          'Adding full bibliography for 4030335.cif.'
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               4030335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -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 0.24159(7) -0.02437(8) 0.2351(4) 0.0562(5) Uani 1 1 d . . .
O1 O 0.32998(7) -0.03563(8) 0.3026(4) 0.0796(6) Uani 1 1 d . . .
O3 O 0.06362(7) 0.02230(8) 0.2172(5) 0.0972(8) Uani 1 1 d . A .
O4 O 0.21745(8) -0.11124(8) -0.1160(6) 0.0921(7) Uani 1 1 d . . .
N2 N 0.14399(7) -0.09488(7) 0.1324(4) 0.0591(5) Uani 1 1 d . . .
C9 C 0.15156(8) 0.00117(9) 0.2357(5) 0.0543(6) Uani 1 1 d . A .
C8 C 0.20122(8) 0.00785(8) 0.3327(5) 0.0520(6) Uani 1 1 d . . .
C1 C 0.22663(8) 0.04427(8) 0.5403(5) 0.0526(6) Uani 1 1 d . . .
C10 C 0.14057(9) -0.04161(9) 0.0200(5) 0.0585(6) Uani 1 1 d . . .
H10A H 0.1057 -0.0363 -0.0572 0.070 Uiso 1 1 calc R . .
H10B H 0.1652 -0.0382 -0.1368 0.070 Uiso 1 1 calc R . .
C2 C 0.20852(9) 0.08528(9) 0.7065(5) 0.0589(6) Uani 1 1 d . . .
H2 H 0.1732 0.0941 0.7048 0.071 Uiso 1 1 calc R . .
C6 C 0.27959(9) 0.03123(9) 0.5504(5) 0.0583(6) Uani 1 1 d . . .
C7 C 0.28932(9) -0.01292(10) 0.3547(5) 0.0600(6) Uani 1 1 d . . .
C15 C 0.10826(10) 0.03522(10) 0.3163(7) 0.0717(8) Uani 1 1 d DU . .
C3 C 0.24339(10) 0.11331(10) 0.8762(5) 0.0630(6) Uani 1 1 d . . .
C4 C 0.29586(11) 0.09925(11) 0.8820(6) 0.0728(7) Uani 1 1 d . . .
H4 H 0.3189 0.1180 0.9968 0.087 Uiso 1 1 calc R . .
C5 C 0.31446(10) 0.05806(11) 0.7212(6) 0.0702(7) Uani 1 1 d . . .
H5 H 0.3496 0.0486 0.7277 0.084 Uiso 1 1 calc R . .
C11 C 0.10244(11) -0.11049(12) 0.3275(7) 0.0807(8) Uani 1 1 d . . .
H11A H 0.0708 -0.1162 0.2217 0.121 Uiso 1 1 calc R . .
H11B H 0.0969 -0.0833 0.4659 0.121 Uiso 1 1 calc R . .
H11C H 0.1123 -0.1422 0.4236 0.121 Uiso 1 1 calc R . .
C14 C 0.22359(12) 0.15908(11) 1.0498(7) 0.0825(8) Uani 1 1 d . . .
H14B H 0.2315 0.1911 0.9520 0.124 Uiso 1 1 calc R . .
H14C H 0.2403 0.1591 1.2337 0.124 Uiso 1 1 calc R . .
H14A H 0.1864 0.1561 1.0741 0.124 Uiso 1 1 calc R . .
C12 C 0.18195(11) -0.12713(10) 0.0403(7) 0.0718(7) Uani 1 1 d . . .
C16 C 0.01938(11) 0.05580(13) 0.2705(9) 0.1016(12) Uani 1 1 d . . .
H16C H 0.0137 0.0586 0.4728 0.152 Uiso 1 1 calc R A .
H16A H -0.0112 0.0413 0.1815 0.152 Uiso 1 1 calc R . .
H16B H 0.0261 0.0899 0.1928 0.152 Uiso 1 1 calc R . .
C13 C 0.18076(15) -0.18304(12) 0.1375(11) 0.1146(13) Uani 1 1 d . . .
H13C H 0.2081 -0.2022 0.0438 0.172 Uiso 1 1 calc R . .
H13A H 0.1475 -0.1982 0.0902 0.172 Uiso 1 1 calc R . .
H13B H 0.1859 -0.1845 0.3406 0.172 Uiso 1 1 calc R . .
O2 O 0.11455(14) 0.08399(15) 0.3550(11) 0.0943(11) Uani 0.540(3) 1 d PDU A 2
O2' O 0.10371(17) 0.05596(18) 0.5740(13) 0.0943(11) Uani 0.460(3) 1 d PD A 1
H1 H 0.2375(10) -0.0515(10) 0.097(6) 0.071(8) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 N1 C8 113.4(2)
C7 N1 H1 121.9(16)
C8 N1 H1 124.7(16)
C15 O3 C16 119.0(2)
C12 N2 C11 124.0(2)
C12 N2 C10 119.9(2)
C11 N2 C10 115.9(2)
C8 C9 C15 123.2(2)
C8 C9 C10 119.2(2)
C15 C9 C10 117.6(2)
C9 C8 N1 120.4(2)
C9 C8 C1 134.6(2)
N1 C8 C1 105.01(18)
C2 C1 C6 119.1(2)
C2 C1 C8 133.8(2)
C6 C1 C8 107.17(19)
N2 C10 C9 114.90(19)
N2 C10 H10A 108.5
C9 C10 H10A 108.5
N2 C10 H10B 108.5
C9 C10 H10B 108.5
H10A C10 H10B 107.5
C1 C2 C3 119.7(2)
C1 C2 H2 120.1
C3 C2 H2 120.1
C5 C6 C1 121.9(2)
C5 C6 C7 129.2(2)
C1 C6 C7 109.0(2)
O1 C7 N1 125.2(2)
O1 C7 C6 129.4(2)
N1 C7 C6 105.45(19)
O2 C15 O3 114.8(3)
O2 C15 O2' 59.2(3)
O3 C15 O2' 110.9(3)
O2 C15 C9 121.8(3)
O3 C15 C9 115.5(2)
O2' C15 C9 122.8(3)
C4 C3 C2 119.8(2)
C4 C3 C14 120.9(2)
C2 C3 C14 119.4(2)
C5 C4 C3 121.3(2)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 118.2(2)
C4 C5 H5 120.9
C6 C5 H5 120.9
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C3 C14 H14B 109.5
C3 C14 H14C 109.5
H14B C14 H14C 109.5
C3 C14 H14A 109.5
H14B C14 H14A 109.5
H14C C14 H14A 109.5
O4 C12 N2 121.3(2)
O4 C12 C13 120.5(3)
N2 C12 C13 118.2(3)
O3 C16 H16C 109.5
O3 C16 H16A 109.5
H16C C16 H16A 109.5
O3 C16 H16B 109.5
H16C C16 H16B 109.5
H16A C16 H16B 109.5
C12 C13 H13C 109.5
C12 C13 H13A 109.5
H13C C13 H13A 109.5
C12 C13 H13B 109.5
H13C C13 H13B 109.5
H13A C13 H13B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.373(3)
N1 C8 1.396(3)
N1 H1 0.95(3)
O1 C7 1.214(3)
O3 C15 1.274(3)
O3 C16 1.439(3)
O4 C12 1.234(3)
N2 C12 1.343(3)
N2 C11 1.455(3)
N2 C10 1.461(3)
C9 C8 1.358(3)
C9 C15 1.457(3)
C9 C10 1.514(3)
C8 C1 1.493(3)
C1 C2 1.384(3)
C1 C6 1.394(3)
C10 H10A 0.9700
C10 H10B 0.9700
C2 C3 1.391(3)
C2 H2 0.9300
C6 C5 1.379(3)
C6 C7 1.474(3)
C15 O2 1.269(4)
C15 O2' 1.322(6)
C3 C4 1.388(4)
C3 C14 1.511(4)
C4 C5 1.378(4)
C4 H4 0.9300
C5 H5 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C14 H14A 0.9600
C12 C13 1.499(4)
C16 H16C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C13 H13C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O4 0.95(3) 1.89(3) 2.829(3) 167(2)
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
C15 C9 C8 N1 -176.4(2)
C10 C9 C8 N1 -0.1(3)
C15 C9 C8 C1 4.2(4)
C10 C9 C8 C1 -179.5(2)
C7 N1 C8 C9 -179.6(2)
C7 N1 C8 C1 0.0(2)
C9 C8 C1 C2 -1.2(4)
N1 C8 C1 C2 179.3(2)
C9 C8 C1 C6 179.5(3)
N1 C8 C1 C6 0.1(2)
C12 N2 C10 C9 -113.4(2)
C11 N2 C10 C9 70.7(3)
C8 C9 C10 N2 70.5(3)
C15 C9 C10 N2 -112.9(3)
C6 C1 C2 C3 1.2(3)
C8 C1 C2 C3 -178.0(2)
C2 C1 C6 C5 -0.1(4)
C8 C1 C6 C5 179.3(2)
C2 C1 C6 C7 -179.5(2)
C8 C1 C6 C7 -0.1(3)
C8 N1 C7 O1 180.0(2)
C8 N1 C7 C6 0.0(3)
C5 C6 C7 O1 0.7(4)
C1 C6 C7 O1 -180.0(3)
C5 C6 C7 N1 -179.2(2)
C1 C6 C7 N1 0.1(3)
C16 O3 C15 O2 -26.1(5)
C16 O3 C15 O2' 38.5(5)
C16 O3 C15 C9 -175.8(3)
C8 C9 C15 O2 35.7(5)
C10 C9 C15 O2 -140.7(4)
C8 C9 C15 O3 -176.9(3)
C10 C9 C15 O3 6.6(4)
C8 C9 C15 O2' -35.8(5)
C10 C9 C15 O2' 147.8(4)
C1 C2 C3 C4 -1.3(4)
C1 C2 C3 C14 178.1(2)
C2 C3 C4 C5 0.4(4)
C14 C3 C4 C5 -179.0(3)
C3 C4 C5 C6 0.7(4)
C1 C6 C5 C4 -0.9(4)
C7 C6 C5 C4 178.4(3)
C11 N2 C12 O4 -177.0(3)
C10 N2 C12 O4 7.5(4)
C11 N2 C12 C13 1.8(4)
C10 N2 C12 C13 -173.7(3)
