#------------------------------------------------------------------------------
#$Date: 2025-08-18 14:30:32 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/78/1507808.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_1507808
loop_
_publ_author_name
'Chen, Minghua'
'Gan, Lishe'
'Lin, Sheng'
'Wang, Xiaoliang'
'Li, Li'
'Li, Yuhuan'
'Zhu, Chenggen'
'Wang, Yanan'
'Jiang, Bingya'
'Jiang, Jiandong'
'Yang, Yongchun'
'Shi, Jiangong'
_publ_section_title
;
 Alkaloids from the Root of Isatis indigotica.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1167
_journal_page_last               1176
_journal_paper_doi               10.1021/np3002833
_journal_volume                  75
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H8 N2 O3'
_chemical_formula_sum            'C10 H8 N2 O3'
_chemical_formula_weight         204.18
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.031(5)
_cell_length_b                   7.138(8)
_cell_length_c                   17.970(12)
_cell_measurement_reflns_used    1094
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      68.09
_cell_measurement_theta_min      4.92
_cell_volume                     901.9(13)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    ORTEPII(Johnson,1976)andPLUTON(Spek,1990)
_computing_publication_material  'SHELXL97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       \w\k
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4374
_diffrn_reflns_theta_full        68.09
_diffrn_reflns_theta_max         68.09
_diffrn_reflns_theta_min         4.92
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.959
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.074(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0346
_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/[\s^2^(Fo^2^)+(0.0682P)^2^+0.1860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                1467
_reflns_number_total             1532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np3002833_si_003.cif
_cod_data_source_block           5255b-83
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               1507808
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
N1 N -0.0982(2) -0.7989(2) -0.15604(8) 0.0333(4) Uani 1 1 d .
H1A H -0.0792 -0.6940 -0.1784 0.040 Uiso 1 1 calc R
N2 N -0.3655(4) -1.4118(4) -0.26486(13) 0.0712(8) Uani 1 1 d .
O1 O -0.0822(2) -0.9946(2) -0.25744(7) 0.0358(4) Uani 1 1 d .
O2 O 0.00021(17) -1.2505(2) -0.13122(6) 0.0292(4) Uani 1 1 d .
H2A H 0.0002 -1.3094 -0.1704 0.044 Uiso 1 1 calc R
O3 O -0.2152(2) -1.2433(2) 0.02643(7) 0.0342(4) Uani 1 1 d .
H3A H -0.2997 -1.2533 0.0576 0.051 Uiso 1 1 calc R
C2 C -0.1070(3) -0.9644(3) -0.19052(10) 0.0276(4) Uani 1 1 d .
C3 C -0.1492(2) -1.1184(3) -0.13201(9) 0.0248(4) Uani 1 1 d .
C3A C -0.1509(2) -1.0039(3) -0.06114(9) 0.0247(4) Uani 1 1 d .
C4 C -0.1834(3) -1.0575(3) 0.01190(10) 0.0262(4) Uani 1 1 d .
C5 C -0.1785(3) -0.9203(3) 0.06693(10) 0.0321(5) Uani 1 1 d .
H5B H -0.1932 -0.9538 0.1166 0.039 Uiso 1 1 calc R
C6 C -0.1522(3) -0.7356(3) 0.04810(11) 0.0351(5) Uani 1 1 d .
H6B H -0.1514 -0.6461 0.0857 0.042 Uiso 1 1 calc R
C7 C -0.1265(3) -0.6771(3) -0.02519(11) 0.0341(5) Uani 1 1 d .
H7A H -0.1119 -0.5515 -0.0377 0.041 Uiso 1 1 calc R
C7A C -0.1241(3) -0.8174(3) -0.07823(10) 0.0279(4) Uani 1 1 d .
C8 C -0.3438(3) -1.2105(3) -0.14508(10) 0.0316(5) Uani 1 1 d .
H8A H -0.3728 -1.2906 -0.1030 0.038 Uiso 1 1 calc R
H8B H -0.4400 -1.1132 -0.1470 0.038 Uiso 1 1 calc R
C9 C -0.3552(3) -1.3215(3) -0.21302(12) 0.0406(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
N1 0.0481(10) 0.0259(9) 0.0258(8) 0.0031(6) 0.0058(7) -0.0027(7)
N2 0.0790(17) 0.0836(18) 0.0510(13) -0.0252(12) -0.0057(11) -0.0273(15)
O1 0.0502(8) 0.0370(8) 0.0203(6) 0.0022(5) 0.0035(5) -0.0029(7)
O2 0.0349(7) 0.0326(8) 0.0202(6) -0.0042(5) -0.0019(5) 0.0075(6)
O3 0.0466(7) 0.0315(8) 0.0244(6) 0.0025(6) 0.0092(5) -0.0003(7)
C2 0.0303(9) 0.0303(10) 0.0223(8) 0.0011(7) 0.0017(7) -0.0006(8)
C3 0.0282(8) 0.0274(10) 0.0188(8) -0.0005(7) 0.0009(7) 0.0007(7)
C3A 0.0286(8) 0.0258(10) 0.0196(8) -0.0019(7) 0.0008(7) 0.0019(8)
C4 0.0260(9) 0.0288(10) 0.0237(8) 0.0003(7) 0.0022(6) 0.0013(7)
C5 0.0341(10) 0.0414(12) 0.0209(8) -0.0044(8) 0.0029(7) 0.0012(9)
C6 0.0340(9) 0.0378(12) 0.0333(10) -0.0125(9) 0.0040(8) -0.0044(9)
C7 0.0374(10) 0.0297(11) 0.0352(10) -0.0064(8) 0.0034(8) -0.0011(8)
C7A 0.0299(9) 0.0271(11) 0.0267(9) -0.0005(7) 0.0034(7) -0.0002(8)
C8 0.0308(9) 0.0367(11) 0.0271(9) 0.0006(8) 0.0006(7) -0.0024(8)
C9 0.0393(10) 0.0478(13) 0.0346(11) -0.0010(9) -0.0052(8) -0.0115(10)
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
C2 N1 C7A 111.70(16)
C2 N1 H1A 124.2
C7A N1 H1A 124.2
C3 O2 H2A 109.5
C4 O3 H3A 109.5
O1 C2 N1 126.85(17)
O1 C2 C3 124.37(18)
N1 C2 C3 108.76(16)
O2 C3 C3A 111.00(14)
O2 C3 C8 112.25(17)
C3A C3 C8 110.66(14)
O2 C3 C2 109.77(14)
C3A C3 C2 100.90(16)
C8 C3 C2 111.72(15)
C7A C3A C4 120.00(17)
C7A C3A C3 109.46(16)
C4 C3A C3 130.44(18)
O3 C4 C3A 118.35(16)
O3 C4 C5 123.34(18)
C3A C4 C5 118.30(19)
C6 C5 C4 120.23(19)
C6 C5 H5B 119.9
C4 C5 H5B 119.9
C5 C6 C7 122.53(19)
C5 C6 H6B 118.7
C7 C6 H6B 118.7
C7A C7 C6 115.9(2)
C7A C7 H7A 122.1
C6 C7 H7A 122.1
C3A C7A C7 122.95(19)
C3A C7A N1 109.11(16)
C7 C7A N1 127.93(18)
C9 C8 C3 114.20(16)
C9 C8 H8A 108.7
C3 C8 H8A 108.7
C9 C8 H8B 108.7
C3 C8 H8B 108.7
H8A C8 H8B 107.6
N2 C9 C8 178.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.335(3)
N1 C7A 1.416(2)
N1 H1A 0.8600
N2 C9 1.135(3)
O1 C2 1.234(2)
O2 C3 1.411(2)
O2 H2A 0.8200
O3 C4 1.370(3)
O3 H3A 0.8200
C2 C3 1.550(3)
C3 C3A 1.513(2)
C3 C8 1.536(3)
C3A C7A 1.379(3)
C3A C4 1.386(3)
C4 C5 1.392(3)
C5 C6 1.374(3)
C5 H5B 0.9300
C6 C7 1.393(3)
C6 H6B 0.9300
C7 C7A 1.383(3)
C7 H7A 0.9300
C8 C9 1.458(3)
C8 H8A 0.9700
C8 H8B 0.9700
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28516064
2 PubChem 60156057