#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/48/4024871.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_4024871
loop_
_publ_author_name
'Szilvia Hajdok'
'Jürgen Conrad'
'Heiko Leutbecher'
'Sabine Strobel'
'Thomas Schleid'
'Uwe Beifuss'
_publ_section_title
;
The Laccase-Catalyzed Domino Reaction between Catechols and Heterocyclic
1,3-Dicarbonyls and the Unambiguous Structure Elucidation of the Products
by NMR Spectroscopy and X-ray Crystal Structure Analysis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7230
_journal_page_last               7237
_journal_paper_doi               10.1021/jo9011915
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C18 H17 N O7'
_chemical_formula_sum            'C18 H17 N O7'
_chemical_formula_weight         359.33
_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                90.973(3)
_cell_angle_beta                 99.975(3)
_cell_angle_gamma                100.225(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6700(4)
_cell_length_b                   10.6575(5)
_cell_length_c                   10.9645(6)
_cell_measurement_reflns_used    4855
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.82
_cell_measurement_theta_min      0.41
_cell_volume                     867.65(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.1692
_diffrn_reflns_av_sigmaI/netI    0.0936
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14236
_diffrn_reflns_theta_full        23.80
_diffrn_reflns_theta_max         23.80
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SCALEPACK (W. Minor & Z. Otwinowski)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0652
_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)+(0.0353P)²+0.3851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                1640
_reflns_number_total             2654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9011915_si_001.cif
_cod_data_source_block           c:\crystal\x-red\ihapr08
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024871
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1548(5) 0.6536(4) 0.4090(4) 0.0426(10) Uani 1 1 d . . .
O1 O 0.1076(4) 0.6931(3) 0.3063(3) 0.0624(8) Uani 1 1 d . . .
N2 N 0.1525(4) 0.7250(3) 0.5181(3) 0.0441(8) Uani 1 1 d . . .
C21 C 0.0947(7) 0.8490(4) 0.4963(6) 0.0605(13) Uani 1 1 d . . .
H22 H -0.035(10) 0.828(8) 0.434(7) 0.17(3) Uiso 1 1 d . . .
H23 H 0.031(7) 0.876(6) 0.559(5) 0.103(19) Uiso 1 1 d . . .
H24 H 0.202(9) 0.915(6) 0.511(6) 0.14(2) Uiso 1 1 d . . .
C3 C 0.2076(5) 0.6878(4) 0.6370(4) 0.0426(10) Uani 1 1 d . . .
C31 C 0.2088(7) 0.7762(5) 0.7442(5) 0.0572(13) Uani 1 1 d . . .
H32 H 0.261(5) 0.740(4) 0.828(4) 0.057(12) Uiso 1 1 d . . .
H33 H 0.280(6) 0.848(5) 0.734(4) 0.064(15) Uiso 1 1 d . . .
H34 H 0.089(7) 0.801(5) 0.749(4) 0.082(15) Uiso 1 1 d . . .
C4 C 0.2619(5) 0.5731(4) 0.6551(4) 0.0405(10) Uani 1 1 d . . .
H4 H 0.293(4) 0.543(3) 0.731(3) 0.028(9) Uiso 1 1 d . . .
C4A C 0.2627(4) 0.4990(3) 0.5501(3) 0.0351(9) Uani 1 1 d . . .
O5 O 0.3140(3) 0.3815(2) 0.5511(2) 0.0398(6) Uani 1 1 d . . .
C5A C 0.2986(4) 0.3437(3) 0.4262(3) 0.0344(9) Uani 1 1 d . . .
C6 C 0.3317(5) 0.2295(3) 0.3809(3) 0.0372(9) Uani 1 1 d . . .
O6 O 0.3899(4) 0.1329(3) 0.4459(2) 0.0529(8) Uani 1 1 d . . .
C61 C 0.4317(7) 0.1452(5) 0.5783(4) 0.0484(11) Uani 1 1 d . . .
H62 H 0.317(6) 0.153(4) 0.609(4) 0.061(13) Uiso 1 1 d . . .
H63 H 0.505(5) 0.224(4) 0.608(4) 0.057(13) Uiso 1 1 d . . .
H64 H 0.476(5) 0.069(4) 0.603(3) 0.042(10) Uiso 1 1 d . . .
C7 C 0.3030(5) 0.2139(4) 0.2523(3) 0.0410(10) Uani 1 1 d . . .
O7 O 0.3363(3) 0.1022(3) 0.1986(2) 0.0498(7) Uani 1 1 d . . .
C71 C 0.1893(6) 0.0064(4) 0.1654(4) 0.0498(11) Uani 1 1 d . . .
O71 O 0.0466(4) 0.0129(3) 0.1889(4) 0.0802(11) Uani 1 1 d . . .
C72 C 0.2371(10) -0.1015(6) 0.0981(6) 0.0691(15) Uani 1 1 d . . .
H72C H 0.175(10) -0.179(8) 0.117(7) 0.16(3) Uiso 1 1 d . . .
H72B H 0.182(10) -0.098(7) 0.020(8) 0.16(3) Uiso 1 1 d . . .
H72A H 0.357(11) -0.084(8) 0.096(7) 0.18(4) Uiso 1 1 d . . .
C8 C 0.2473(5) 0.3064(4) 0.1760(3) 0.0420(10) Uani 1 1 d . . .
O8 O 0.2157(4) 0.2797(3) 0.0478(2) 0.0549(8) Uani 1 1 d . . .
C81 C 0.3575(7) 0.3064(4) -0.0109(4) 0.0556(12) Uani 1 1 d . . .
O81 O 0.5068(5) 0.3508(4) 0.0427(3) 0.0837(11) Uani 1 1 d . . .
C82 C 0.3034(11) 0.2705(8) -0.1457(4) 0.0788(18) Uani 1 1 d . . .
H83 H 0.397(7) 0.308(5) -0.177(5) 0.085(19) Uiso 1 1 d . . .
H84 H 0.253(9) 0.180(8) -0.150(6) 0.14(3) Uiso 1 1 d . . .
H85 H 0.193(10) 0.309(7) -0.178(6) 0.16(3) Uiso 1 1 d . . .
C9 C 0.2155(5) 0.4187(4) 0.2212(4) 0.0451(10) Uani 1 1 d . . .
H9 H 0.171(5) 0.484(4) 0.165(4) 0.068(13) Uiso 1 1 d . . .
C9A C 0.2393(4) 0.4365(3) 0.3489(3) 0.0361(9) Uani 1 1 d . . .
C9B C 0.2143(4) 0.5354(3) 0.4327(3) 0.0352(9) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 121.1(4) . . ?
O1 C1 C9B 125.7(4) . . ?
N2 C1 C9B 113.2(3) . . ?
C3 N2 C1 124.2(3) . . ?
C3 N2 C21 121.4(4) . . ?
C1 N2 C21 114.3(4) . . ?
N2 C21 H22 106(4) . . ?
N2 C21 H23 114(3) . . ?
H22 C21 H23 87(4) . . ?
N2 C21 H24 107(4) . . ?
H22 C21 H24 139(5) . . ?
H23 C21 H24 100(5) . . ?
C4 C3 N2 120.4(3) . . ?
C4 C3 C31 120.9(4) . . ?
N2 C3 C31 118.7(4) . . ?
C3 C31 H32 111(2) . . ?
C3 C31 H33 106(3) . . ?
H32 C31 H33 109(4) . . ?
C3 C31 H34 115(3) . . ?
H32 C31 H34 110(3) . . ?
H33 C31 H34 105(4) . . ?
C3 C4 C4A 117.0(4) . . ?
C3 C4 H4 124(2) . . ?
C4A C4 H4 119(2) . . ?
C9B C4A O5 111.8(3) . . ?
C9B C4A C4 123.4(4) . . ?
O5 C4A C4 124.8(3) . . ?
C4A O5 C5A 105.3(3) . . ?
C6 C5A C9A 122.8(3) . . ?
C6 C5A O5 126.4(3) . . ?
C9A C5A O5 110.8(3) . . ?
O6 C6 C5A 128.3(3) . . ?
O6 C6 C7 116.6(3) . . ?
C5A C6 C7 115.1(3) . . ?
C6 O6 C61 119.7(3) . . ?
O6 C61 H62 107(2) . . ?
O6 C61 H63 113(2) . . ?
H62 C61 H63 101(3) . . ?
O6 C61 H64 105(2) . . ?
H62 C61 H64 114(3) . . ?
H63 C61 H64 117(3) . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 O7 119.0(3) . . ?
C6 C7 O7 118.9(3) . . ?
C71 O7 C7 115.7(3) . . ?
O71 C71 O7 122.5(4) . . ?
O71 C71 C72 126.7(5) . . ?
O7 C71 C72 110.8(4) . . ?
C71 C72 H72C 111(5) . . ?
C71 C72 H72B 104(5) . . ?
H72C C72 H72B 99(6) . . ?
C71 C72 H72A 108(5) . . ?
H72C C72 H72A 125(7) . . ?
H72B C72 H72A 106(6) . . ?
C9 C8 C7 122.5(3) . . ?
C9 C8 O8 119.7(3) . . ?
C7 C8 O8 117.7(3) . . ?
C81 O8 C8 117.4(3) . . ?
O81 C81 O8 122.6(4) . . ?
O81 C81 C82 126.3(5) . . ?
O8 C81 C82 111.1(5) . . ?
C81 C82 H83 103(3) . . ?
C81 C82 H84 105(4) . . ?
H83 C82 H84 127(6) . . ?
C81 C82 H85 107(4) . . ?
H83 C82 H85 111(5) . . ?
H84 C82 H85 102(5) . . ?
C8 C9 C9A 117.1(4) . . ?
C8 C9 H9 122(2) . . ?
C9A C9 H9 121(2) . . ?
C9 C9A C5A 120.4(3) . . ?
C9 C9A C9B 134.9(3) . . ?
C5A C9A C9B 104.7(3) . . ?
C4A C9B C1 121.7(3) . . ?
C4A C9B C9A 107.4(3) . . ?
C1 C9B C9A 131.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.227(4) . ?
C1 N2 1.411(5) . ?
C1 C9B 1.427(5) . ?
N2 C3 1.387(5) . ?
N2 C21 1.477(5) . ?
C21 H22 1.09(8) . ?
C21 H23 0.98(6) . ?
C21 H24 0.97(7) . ?
C3 C4 1.367(6) . ?
C3 C31 1.491(6) . ?
C31 H32 1.04(4) . ?
C31 H33 0.88(5) . ?
C31 H34 1.01(5) . ?
C4 C4A 1.386(5) . ?
C4 H4 0.90(3) . ?
C4A C9B 1.359(5) . ?
C4A O5 1.378(4) . ?
O5 C5A 1.400(4) . ?
C5A C6 1.387(5) . ?
C5A C9A 1.400(5) . ?
C6 O6 1.357(4) . ?
C6 C7 1.392(5) . ?
O6 C61 1.430(5) . ?
C61 H62 1.01(4) . ?
C61 H63 0.94(4) . ?
C61 H64 0.96(4) . ?
C7 C8 1.382(5) . ?
C7 O7 1.401(4) . ?
O7 C71 1.372(5) . ?
C71 O71 1.181(5) . ?
C71 C72 1.489(6) . ?
C72 H72C 0.92(8) . ?
C72 H72B 0.89(8) . ?
C72 H72A 0.91(8) . ?
C8 C9 1.365(5) . ?
C8 O8 1.400(4) . ?
O8 C81 1.347(5) . ?
C81 O81 1.203(5) . ?
C81 C82 1.488(6) . ?
C82 H83 0.89(5) . ?
C82 H84 0.98(8) . ?
C82 H85 1.02(7) . ?
C9 C9A 1.385(5) . ?
C9 H9 1.00(4) . ?
C9A C9B 1.447(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659045
