#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152648.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_7152648
loop_
_publ_author_name
'Pillay, Adushan'
'Rousseau, Amanda L.'
'Fernandes, Manuel A.'
'de Koning, Charles B.'
_publ_section_title
;
 The synthesis of the pyranonaphthoquinones dehydroherbarin and
 anhydrofusarubin using Wacker oxidation methodology as a key step and
 other unexpected oxidation reactions with ceric ammonium nitrate and
 salcomine.
;
_journal_issue                   38
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7809
_journal_page_last               7819
_journal_paper_doi               10.1039/c2ob26126j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C16 H15 N O9'
_chemical_formula_sum            'C16 H15 N O9'
_chemical_formula_weight         365.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.246(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.913(4)
_cell_length_b                   13.475(4)
_cell_length_c                   8.404(3)
_cell_measurement_reflns_used    925
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.94
_cell_volume                     1571.2(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.1022
_diffrn_reflns_av_sigmaI/netI    0.1561
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7954
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.1857
_refine_ls_R_factor_gt           0.0497
_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)+(0.0354P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1010
_reflns_number_total             2722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26126j.txt
_cod_data_source_block           11m_cdk_adushan4_0s-cmpd17
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7152648
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.7945(3) 0.1080(3) 0.4411(5) 0.0281(11) Uani 1 1 d .
C2 C 0.7955(3) 0.2193(3) 0.4379(5) 0.0270(11) Uani 1 1 d .
C3 C 0.8691(3) 0.2662(3) 0.5322(5) 0.0308(12) Uani 1 1 d .
H3 H 0.9152 0.2288 0.5961 0.037 Uiso 1 1 calc R
C4 C 0.8726(3) 0.3694(4) 0.5297(5) 0.0346(12) Uani 1 1 d .
C5 C 0.8058(3) 0.4232(3) 0.4356(5) 0.0363(12) Uani 1 1 d .
H5 H 0.8099 0.4935 0.4353 0.044 Uiso 1 1 calc R
C6 C 0.7334(3) 0.3772(3) 0.3420(5) 0.0290(11) Uani 1 1 d .
C7 C 0.7251(3) 0.2724(3) 0.3442(5) 0.0287(11) Uani 1 1 d .
C8 C 0.6490(3) 0.2185(3) 0.2524(5) 0.0317(12) Uani 1 1 d .
C9 C 0.6534(3) 0.1081(3) 0.2477(5) 0.0278(11) Uani 1 1 d .
C10 C 0.7196(3) 0.0571(3) 0.3377(5) 0.0279(11) Uani 1 1 d .
C11 C 1.0123(3) 0.3787(3) 0.7148(5) 0.0470(14) Uani 1 1 d .
H11A H 0.9841 0.3330 0.7891 0.070 Uiso 1 1 calc R
H11B H 1.0507 0.4289 0.7752 0.070 Uiso 1 1 calc R
H11C H 1.0537 0.3417 0.6464 0.070 Uiso 1 1 calc R
C12 C 0.6764(3) 0.5339(3) 0.2411(5) 0.0424(13) Uani 1 1 d .
H12A H 0.6677 0.5617 0.3468 0.064 Uiso 1 1 calc R
H12B H 0.6272 0.5609 0.1635 0.064 Uiso 1 1 calc R
H12C H 0.7405 0.5514 0.2090 0.064 Uiso 1 1 calc R
C13 C 0.5786(3) 0.0576(3) 0.1393(5) 0.0357(12) Uani 1 1 d .
H13A H 0.5157 0.0620 0.1864 0.043 Uiso 1 1 calc R
H13B H 0.5728 0.0929 0.0357 0.043 Uiso 1 1 calc R
C14 C 0.7220(3) -0.0544(3) 0.3320(5) 0.0321(12) Uani 1 1 d .
H14 H 0.7358 -0.0822 0.4416 0.039 Uiso 1 1 calc R
C15 C 0.6283(3) -0.0989(4) 0.2535(5) 0.0358(12) Uani 1 1 d .
C16 C 0.6377(3) -0.2054(3) 0.2016(5) 0.0440(13) Uani 1 1 d .
H16A H 0.6593 -0.2463 0.2939 0.066 Uiso 1 1 calc R
H16B H 0.6848 -0.2097 0.1208 0.066 Uiso 1 1 calc R
H16C H 0.5750 -0.2295 0.1563 0.066 Uiso 1 1 calc R
N1 N 0.8732(3) -0.1393(3) 0.3048(6) 0.0551(12) Uani 1 1 d .
O1 O 0.85381(18) 0.0597(2) 0.5232(3) 0.0362(8) Uani 1 1 d .
O2 O 0.9372(2) 0.4262(2) 0.6185(4) 0.0444(8) Uani 1 1 d .
O3 O 0.66721(19) 0.4274(2) 0.2468(3) 0.0375(8) Uani 1 1 d .
O4 O 0.5792(2) 0.2579(2) 0.1775(3) 0.0467(9) Uani 1 1 d .
O5 O 0.60026(19) -0.0441(2) 0.1120(3) 0.0369(8) Uani 1 1 d .
O6 O 0.56119(19) -0.0862(2) 0.3695(3) 0.0429(9) Uani 1 1 d .
H6 H 0.5116 -0.1199 0.3442 0.064 Uiso 1 1 calc R
O7 O 0.79979(19) -0.0789(2) 0.2317(3) 0.0387(8) Uani 1 1 d .
O8 O 0.8618(3) -0.1766(3) 0.4321(5) 0.0752(13) Uani 1 1 d .
O9 O 0.9389(2) -0.1480(3) 0.2182(4) 0.0763(13) Uani 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 C1 C10 120.2(4)
O1 C1 C2 122.3(4)
C10 C1 C2 117.4(4)
C3 C2 C7 122.5(4)
C3 C2 C1 116.7(4)
C7 C2 C1 120.8(4)
C4 C3 C2 117.9(4)
C4 C3 H3 121.1
C2 C3 H3 121.1
O2 C4 C5 114.1(4)
O2 C4 C3 125.2(4)
C5 C4 C3 120.7(4)
C6 C5 C4 121.6(4)
C6 C5 H5 119.2
C4 C5 H5 119.2
O3 C6 C5 123.3(4)
O3 C6 C7 116.9(4)
C5 C6 C7 119.8(4)
C2 C7 C6 117.4(4)
C2 C7 C8 119.5(4)
C6 C7 C8 123.1(4)
O4 C8 C7 124.6(4)
O4 C8 C9 116.6(4)
C7 C8 C9 118.8(4)
C10 C9 C8 121.7(4)
C10 C9 C13 122.0(4)
C8 C9 C13 116.3(4)
C9 C10 C1 121.4(4)
C9 C10 C14 120.7(4)
C1 C10 C14 117.8(4)
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
O3 C12 H12A 109.5
O3 C12 H12B 109.5
H12A C12 H12B 109.5
O3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
O5 C13 C9 113.0(3)
O5 C13 H13A 109.0
C9 C13 H13A 109.0
O5 C13 H13B 109.0
C9 C13 H13B 109.0
H13A C13 H13B 107.8
O7 C14 C10 105.3(3)
O7 C14 C15 107.8(3)
C10 C14 C15 112.5(4)
O7 C14 H14 110.3
C10 C14 H14 110.3
C15 C14 H14 110.3
O6 C15 O5 111.0(4)
O6 C15 C16 113.0(4)
O5 C15 C16 106.0(3)
O6 C15 C14 103.9(3)
O5 C15 C14 109.0(4)
C16 C15 C14 113.9(4)
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O8 N1 O9 130.3(5)
O8 N1 O7 119.3(4)
O9 N1 O7 110.3(4)
C4 O2 C11 119.0(4)
C6 O3 C12 117.3(3)
C13 O5 C15 114.2(3)
C15 O6 H6 109.5
N1 O7 C14 115.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.223(4)
C1 C10 1.475(5)
C1 C2 1.501(5)
C2 C3 1.398(5)
C2 C7 1.406(5)
C3 C4 1.392(6)
C3 H3 0.9500
C4 O2 1.361(5)
C4 C5 1.380(5)
C5 C6 1.379(5)
C5 H5 0.9500
C6 O3 1.354(4)
C6 C7 1.417(5)
C7 C8 1.457(5)
C8 O4 1.237(5)
C8 C9 1.490(6)
C9 C10 1.338(5)
C9 C13 1.495(5)
C10 C14 1.504(5)
C11 O2 1.425(4)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 O3 1.442(4)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 O5 1.425(4)
C13 H13A 0.9900
C13 H13B 0.9900
C14 O7 1.458(4)
C14 C15 1.539(5)
C14 H14 1.0000
C15 O6 1.409(4)
C15 O5 1.430(5)
C15 C16 1.510(5)
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
N1 O8 1.203(5)
N1 O9 1.216(4)
N1 O7 1.411(4)
O6 H6 0.8400
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
_geom_hbond_site_symmetry_A
O6 H6 O4 0.84 2.08 2.876(4) 159.2 2_645
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
O1 C1 C2 C3 1.0(6)
C10 C1 C2 C3 -177.8(4)
O1 C1 C2 C7 -178.8(4)
C10 C1 C2 C7 2.4(6)
C7 C2 C3 C4 -1.2(6)
C1 C2 C3 C4 179.0(4)
C2 C3 C4 O2 177.6(4)
C2 C3 C4 C5 -0.5(6)
O2 C4 C5 C6 -177.9(4)
C3 C4 C5 C6 0.4(7)
C4 C5 C6 O3 -179.2(4)
C4 C5 C6 C7 1.5(7)
C3 C2 C7 C6 3.0(6)
C1 C2 C7 C6 -177.3(4)
C3 C2 C7 C8 -178.2(4)
C1 C2 C7 C8 1.5(6)
O3 C6 C7 C2 177.6(4)
C5 C6 C7 C2 -3.1(6)
O3 C6 C7 C8 -1.1(6)
C5 C6 C7 C8 178.2(4)
C2 C7 C8 O4 173.5(4)
C6 C7 C8 O4 -7.8(7)
C2 C7 C8 C9 -6.0(6)
C6 C7 C8 C9 172.7(4)
O4 C8 C9 C10 -172.7(4)
C7 C8 C9 C10 6.8(6)
O4 C8 C9 C13 6.1(6)
C7 C8 C9 C13 -174.4(4)
C8 C9 C10 C1 -2.8(6)
C13 C9 C10 C1 178.4(4)
C8 C9 C10 C14 179.4(4)
C13 C9 C10 C14 0.6(6)
O1 C1 C10 C9 179.5(4)
C2 C1 C10 C9 -1.8(6)
O1 C1 C10 C14 -2.7(6)
C2 C1 C10 C14 176.1(3)
C10 C9 C13 O5 -15.0(6)
C8 C9 C13 O5 166.1(3)
C9 C10 C14 O7 101.4(4)
C1 C10 C14 O7 -76.5(4)
C9 C10 C14 C15 -15.8(5)
C1 C10 C14 C15 166.4(3)
O7 C14 C15 O6 170.7(3)
C10 C14 C15 O6 -73.6(4)
O7 C14 C15 O5 -70.9(4)
C10 C14 C15 O5 44.8(5)
O7 C14 C15 C16 47.2(5)
C10 C14 C15 C16 162.9(4)
C5 C4 O2 C11 -177.2(4)
C3 C4 O2 C11 4.6(6)
C5 C6 O3 C12 2.1(6)
C7 C6 O3 C12 -178.7(3)
C9 C13 O5 C15 47.5(5)
O6 C15 O5 C13 51.1(4)
C16 C15 O5 C13 174.3(3)
C14 C15 O5 C13 -62.7(4)
O8 N1 O7 C14 9.6(6)
O9 N1 O7 C14 -173.5(4)
C10 C14 O7 N1 122.3(3)
C15 C14 O7 N1 -117.3(4)
