#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:14:32 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180174 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/70/7107086.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_7107086
loop_
_publ_author_name
'Yan-Ping Zhu'
'Qing-He Gao'
'Mi Lian'
'Jing-Jing Yuan'
'Mei-Cai Liu'
'Qin Zhao'
'Yan Yang'
'An-Xin Wu'
_publ_section_title
;
 Sustainable Byproduct Catalyzed Domino Strategy: Facile Synthesis of
 a-formyloxy and Acetoxy Ketones via Iodination/Nucleophilic
 Substitution/Hydrolyzation/Oxidation Sequences
;
_journal_name_full               Chem.Commun.
_journal_page_first              12700
_journal_paper_doi               10.1039/c1cc15819h
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C9 H7 N O5'
_chemical_formula_weight         209.16
_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                 97.759(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6790(10)
_cell_length_b                   15.1737(15)
_cell_length_c                   6.3703(6)
_cell_measurement_reflns_used    5192
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.51
_cell_volume                     927.02(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1244
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11219
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.072(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0539
_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)+(0.0869P)²+0.0954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.1656
_reflns_number_gt                1844
_reflns_number_total             2289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15819h.txt
_cod_data_source_block           t
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7107086
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 0.59429(14) 0.86120(9) -0.0868(2) 0.0506(3) Uani 1 1 d .
C2 C 0.46180(15) 0.83962(9) -0.1802(2) 0.0546(4) Uani 1 1 d .
H2 H 0.4473 0.8132 -0.3132 0.065 Uiso 1 1 calc R
C3 C 0.35112(14) 0.85815(9) -0.0717(2) 0.0532(4) Uani 1 1 d .
H3 H 0.2609 0.8436 -0.1312 0.064 Uiso 1 1 calc R
C4 C 0.37382(14) 0.89862(8) 0.1275(2) 0.0483(3) Uani 1 1 d .
C5 C 0.50976(14) 0.91837(9) 0.2177(2) 0.0519(3) Uani 1 1 d .
H5 H 0.5254 0.9446 0.3508 0.062 Uiso 1 1 calc R
C6 C 0.62092(14) 0.89941(9) 0.1115(2) 0.0541(4) Uani 1 1 d .
H6 H 0.7117 0.9120 0.1717 0.065 Uiso 1 1 calc R
C7 C 0.25772(15) 0.92483(8) 0.2455(2) 0.0520(3) Uani 1 1 d .
C8 C 0.11207(15) 0.89698(11) 0.1550(2) 0.0596(4) Uani 1 1 d .
H8A H 0.0880 0.9233 0.0161 0.072 Uiso 1 1 calc R
H8B H 0.1093 0.8334 0.1382 0.072 Uiso 1 1 calc R
C10 C 0.01385(19) 0.87702(13) 0.4655(3) 0.0731(5) Uani 1 1 d .
H10 H -0.0516 0.8912 0.5544 0.088 Uiso 1 1 calc R
N1 N 0.71245(14) 0.84328(9) -0.2036(2) 0.0614(4) Uani 1 1 d .
O1 O 0.68900(14) 0.81188(9) -0.3802(2) 0.0804(4) Uani 1 1 d .
O2 O 0.82801(13) 0.86375(13) -0.1197(2) 0.0998(5) Uani 1 1 d .
O3 O 0.27868(12) 0.96835(9) 0.40546(19) 0.0747(4) Uani 1 1 d .
O4 O 0.01206(11) 0.92306(8) 0.28849(18) 0.0656(3) Uani 1 1 d .
O5 O 0.09352(17) 0.81860(10) 0.5191(2) 0.0945(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0528(7) 0.0422(7) 0.0546(7) 0.0036(5) -0.0003(5) -0.0025(5)
C2 0.0589(8) 0.0497(7) 0.0520(7) -0.0069(5) -0.0039(6) -0.0060(6)
C3 0.0484(7) 0.0507(7) 0.0563(7) -0.0075(5) -0.0087(5) -0.0058(5)
C4 0.0507(7) 0.0387(6) 0.0519(7) -0.0012(5) -0.0055(5) -0.0019(5)
C5 0.0540(7) 0.0487(7) 0.0488(7) -0.0047(5) -0.0086(5) -0.0042(5)
C6 0.0477(7) 0.0531(7) 0.0569(7) 0.0007(6) -0.0095(5) -0.0053(5)
C7 0.0543(8) 0.0427(7) 0.0562(7) -0.0040(5) -0.0030(6) -0.0022(5)
C8 0.0504(7) 0.0651(9) 0.0606(8) -0.0089(6) -0.0021(6) 0.0018(6)
C10 0.0655(10) 0.0776(11) 0.0748(10) 0.0012(8) 0.0049(8) -0.0115(8)
N1 0.0589(7) 0.0599(7) 0.0648(7) 0.0037(5) 0.0062(6) -0.0044(5)
O1 0.0810(8) 0.0805(8) 0.0819(8) -0.0235(6) 0.0186(6) -0.0099(6)
O2 0.0524(7) 0.1637(15) 0.0822(9) -0.0099(9) 0.0045(6) -0.0140(8)
O3 0.0680(7) 0.0776(7) 0.0781(7) -0.0315(6) 0.0083(5) -0.0135(5)
O4 0.0526(6) 0.0732(7) 0.0695(7) -0.0037(5) 0.0025(5) 0.0077(5)
O5 0.1027(11) 0.0758(9) 0.1010(10) 0.0212(7) -0.0004(8) -0.0079(7)
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
C2 C1 C6 122.82(14)
C2 C1 N1 118.64(13)
C6 C1 N1 118.54(12)
C1 C2 C3 118.36(12)
C1 C2 H2 120.8
C3 C2 H2 120.8
C2 C3 C4 120.40(12)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 119.44(13)
C5 C4 C7 117.95(11)
C3 C4 C7 122.57(12)
C6 C5 C4 120.57(12)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 118.38(12)
C5 C6 H6 120.8
C1 C6 H6 120.8
O3 C7 C4 121.34(13)
O3 C7 C8 121.12(13)
C4 C7 C8 117.53(11)
O4 C8 C7 111.61(12)
O4 C8 H8A 109.3
C7 C8 H8A 109.3
O4 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 108.0
O5 C10 O4 124.65(18)
O5 C10 H10 117.7
O4 C10 H10 117.7
O2 N1 O1 123.64(14)
O2 N1 C1 117.63(13)
O1 N1 C1 118.68(13)
C10 O4 C8 115.39(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3783(19)
C1 C6 1.3823(19)
C1 N1 1.471(2)
C2 C3 1.380(2)
C2 H2 0.9300
C3 C4 1.3998(17)
C3 H3 0.9300
C4 C5 1.3955(18)
C4 C7 1.488(2)
C5 C6 1.377(2)
C5 H5 0.9300
C6 H6 0.9300
C7 O3 1.2081(16)
C7 C8 1.510(2)
C8 O4 1.4279(19)
C8 H8A 0.9700
C8 H8B 0.9700
C10 O5 1.194(2)
C10 O4 1.325(2)
C10 H10 0.9300
N1 O2 1.2130(17)
N1 O1 1.2150(18)
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
C10 H10 O2 0.93 2.55 3.397(2) 151.9 1_456
C8 H8B O5 0.97 2.43 3.382(2) 168.2 4_575
C3 H3 O5 0.93 2.60 3.408(2) 145.7 1_554
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
C6 C1 C2 C3 0.9(2)
N1 C1 C2 C3 -178.78(11)
C1 C2 C3 C4 0.6(2)
C2 C3 C4 C5 -1.4(2)
C2 C3 C4 C7 176.29(12)
C3 C4 C5 C6 0.8(2)
C7 C4 C5 C6 -176.99(11)
C4 C5 C6 C1 0.6(2)
C2 C1 C6 C5 -1.5(2)
N1 C1 C6 C5 178.19(12)
C5 C4 C7 O3 6.1(2)
C3 C4 C7 O3 -171.60(14)
C5 C4 C7 C8 -175.37(12)
C3 C4 C7 C8 6.9(2)
O3 C7 C8 O4 -4.1(2)
C4 C7 C8 O4 177.45(11)
C2 C1 N1 O2 179.10(15)
C6 C1 N1 O2 -0.6(2)
C2 C1 N1 O1 1.6(2)
C6 C1 N1 O1 -178.05(13)
O5 C10 O4 C8 1.7(2)
C7 C8 O4 C10 -73.43(17)
