# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1046944'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-hydroxy-3-((3-methyl-4-nitroisoxazol-5-yl)methyl)indolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N3 O5'
_chemical_formula_weight         289.25
_chemical_absolute_configuration ad

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.60650(10)
_cell_length_b                   7.18580(10)
_cell_length_c                   11.1840(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.9850(10)
_cell_angle_gamma                90.00
_cell_volume                     645.794(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3160
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4451
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2841
_reflns_number_gt                2751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.059(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(8)
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C13 C 0.14808(15) -0.11621(19) -0.22609(12) 0.0370(3) Uani 1 1 d . . .
C12 C 0.34164(13) 0.03719(15) -0.06034(11) 0.0313(2) Uani 1 1 d . . .
C11 C 0.08843(14) 0.06546(18) -0.23726(11) 0.0350(2) Uani 1 1 d . . .
C10 C 0.22028(15) 0.37368(19) 0.06386(13) 0.0382(3) Uani 1 1 d . . .
C9 C 0.11590(15) 0.2502(2) -0.04047(13) 0.0410(3) Uani 1 1 d . . .
H9A H 0.0160 0.3169 -0.0910 0.049 Uiso 1 1 calc R . .
H9B H 0.0822 0.1431 -0.0028 0.049 Uiso 1 1 calc R . .
C8 C 0.20548(13) 0.18159(16) -0.12989(12) 0.0324(2) Uani 1 1 d . . .
C7 C 0.32507(17) 0.3521(2) 0.18630(14) 0.0443(3) Uani 1 1 d . . .
C6 C 0.39287(19) 0.5325(3) 0.22892(15) 0.0533(4) Uani 1 1 d . . .
C5 C 0.06916(19) -0.2547(2) -0.31095(16) 0.0513(4) Uani 1 1 d . . .
H5A H 0.1100 -0.3757 -0.3017 0.062 Uiso 1 1 calc R . .
C4 C -0.05568(17) 0.1128(2) -0.33698(14) 0.0466(3) Uani 1 1 d . . .
H4A H -0.0974 0.2334 -0.3454 0.056 Uiso 1 1 calc R . .
C3 C 0.5171(3) 0.5923(4) 0.35441(19) 0.0835(7) Uani 1 1 d . . .
H3A H 0.5366 0.7236 0.3524 0.125 Uiso 1 1 calc R . .
H3B H 0.6195 0.5262 0.3703 0.125 Uiso 1 1 calc R . .
H3C H 0.4752 0.5655 0.4214 0.125 Uiso 1 1 calc R . .
C2 C -0.13686(18) -0.0255(3) -0.42473(14) 0.0533(4) Uani 1 1 d . . .
H2A H -0.2337 0.0034 -0.4930 0.064 Uiso 1 1 calc R . .
C1 C -0.0753(2) -0.2040(3) -0.41152(15) 0.0562(4) Uani 1 1 d . . .
H1A H -0.1317 -0.2935 -0.4714 0.067 Uiso 1 1 calc R . .
N3 N 0.29819(13) -0.12763(15) -0.12000(11) 0.0395(2) Uani 1 1 d . . .
H3D H 0.3553 -0.2281 -0.0962 0.047 Uiso 1 1 calc R . .
N2 N 0.33030(19) 0.6540(2) 0.13898(15) 0.0574(4) Uani 1 1 d . . .
N1 N 0.3592(2) 0.1813(2) 0.25632(14) 0.0641(4) Uani 1 1 d . . .
O5 O 0.46793(9) 0.06773(12) 0.03273(8) 0.0364(2) Uani 1 1 d . . .
O4 O 0.27116(11) 0.32801(12) -0.18096(9) 0.0395(2) Uani 1 1 d . . .
H4B H 0.3454 0.3802 -0.1230 0.059 Uiso 1 1 calc R . .
O3 O 0.22120(12) 0.55384(14) 0.03337(10) 0.0463(2) Uani 1 1 d . . .
O2 O 0.2569(2) 0.0560(2) 0.22222(17) 0.0845(4) Uani 1 1 d . . .
O1 O 0.4895(3) 0.1733(3) 0.34797(16) 0.1150(8) 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
C13 0.0334(5) 0.0346(6) 0.0384(6) 0.0013(5) 0.0074(5) -0.0020(5)
C12 0.0277(5) 0.0298(5) 0.0361(5) 0.0031(4) 0.0111(4) 0.0001(4)
C11 0.0305(5) 0.0360(6) 0.0358(6) -0.0001(5) 0.0085(5) -0.0028(5)
C10 0.0315(5) 0.0373(6) 0.0490(7) -0.0051(6) 0.0182(5) 0.0016(5)
C9 0.0281(5) 0.0445(7) 0.0487(7) -0.0078(6) 0.0118(5) -0.0016(5)
C8 0.0249(5) 0.0297(5) 0.0384(6) 0.0026(4) 0.0063(4) 0.0008(4)
C7 0.0414(6) 0.0517(8) 0.0424(6) -0.0059(6) 0.0184(5) 0.0014(6)
C6 0.0452(7) 0.0728(11) 0.0485(8) -0.0223(8) 0.0248(6) -0.0137(7)
C5 0.0489(8) 0.0417(7) 0.0551(8) -0.0107(6) 0.0087(6) -0.0055(6)
C4 0.0357(6) 0.0509(8) 0.0453(7) 0.0046(6) 0.0048(6) 0.0031(5)
C3 0.0739(12) 0.124(2) 0.0533(10) -0.0356(11) 0.0234(9) -0.0344(13)
C2 0.0373(6) 0.0696(10) 0.0417(7) -0.0013(7) 0.0004(5) -0.0056(7)
C1 0.0489(8) 0.0631(10) 0.0470(8) -0.0153(7) 0.0054(6) -0.0134(7)
N3 0.0362(5) 0.0283(5) 0.0450(6) 0.0005(5) 0.0035(4) 0.0026(4)
N2 0.0667(8) 0.0490(8) 0.0636(8) -0.0192(7) 0.0322(7) -0.0162(6)
N1 0.0828(10) 0.0670(10) 0.0475(7) 0.0084(7) 0.0294(7) 0.0171(8)
O5 0.0277(4) 0.0344(4) 0.0404(4) 0.0013(4) 0.0042(3) 0.0001(3)
O4 0.0366(4) 0.0330(5) 0.0436(5) 0.0066(4) 0.0081(3) -0.0024(3)
O3 0.0475(5) 0.0377(5) 0.0541(5) -0.0046(4) 0.0186(4) 0.0012(4)
O2 0.1253(13) 0.0506(7) 0.0909(10) 0.0097(8) 0.0549(10) 0.0038(9)
O1 0.1268(16) 0.1269(19) 0.0598(9) 0.0252(10) -0.0051(10) 0.0327(13)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
C13 C5 1.3749(19) . ?
C13 C11 1.3919(19) . ?
C13 N3 1.4091(15) . ?
C12 O5 1.2258(14) . ?
C12 N3 1.3451(16) . ?
C12 C8 1.5499(15) . ?
C11 C4 1.3810(17) . ?
C11 C8 1.5122(16) . ?
C10 O3 1.3395(17) . ?
C10 C7 1.3521(19) . ?
C10 C9 1.4848(18) . ?
C9 C8 1.5460(17) . ?
C8 O4 1.4085(14) . ?
C7 N1 1.429(2) . ?
C7 C6 1.432(2) . ?
C6 N2 1.295(2) . ?
C6 C3 1.491(2) . ?
C5 C1 1.393(2) . ?
C4 C2 1.396(2) . ?
C2 C1 1.376(3) . ?
N2 O3 1.4142(17) . ?
N1 O1 1.220(2) . ?
N1 O2 1.221(2) . ?

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
C5 C13 C11 122.79(12) . . ?
C5 C13 N3 128.05(13) . . ?
C11 C13 N3 109.13(11) . . ?
O5 C12 N3 125.68(10) . . ?
O5 C12 C8 125.98(10) . . ?
N3 C12 C8 108.34(10) . . ?
C4 C11 C13 119.95(12) . . ?
C4 C11 C8 130.96(12) . . ?
C13 C11 C8 109.08(10) . . ?
O3 C10 C7 107.83(12) . . ?
O3 C10 C9 115.76(12) . . ?
C7 C10 C9 136.35(14) . . ?
C10 C9 C8 113.41(10) . . ?
O4 C8 C11 109.89(10) . . ?
O4 C8 C9 112.93(10) . . ?
C11 C8 C9 110.17(9) . . ?
O4 C8 C12 111.26(9) . . ?
C11 C8 C12 101.42(9) . . ?
C9 C8 C12 110.57(10) . . ?
C10 C7 N1 125.84(15) . . ?
C10 C7 C6 106.12(14) . . ?
N1 C7 C6 128.04(14) . . ?
N2 C6 C7 110.21(14) . . ?
N2 C6 C3 119.72(19) . . ?
C7 C6 C3 130.1(2) . . ?
C13 C5 C1 116.46(15) . . ?
C11 C4 C2 118.11(14) . . ?
C1 C2 C4 120.80(13) . . ?
C2 C1 C5 121.89(14) . . ?
C12 N3 C13 112.00(10) . . ?
C6 N2 O3 105.83(12) . . ?
O1 N1 O2 124.8(2) . . ?
O1 N1 C7 116.6(2) . . ?
O2 N1 C7 118.59(15) . . ?
C10 O3 N2 109.99(11) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.038
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1046945'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3-(1-(3-ethyl-4-nitroisoxazol-5-yl)ethyl)-3-hydroxy-5-methoxyindolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N3 O6'
_chemical_formula_weight         347.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.5271(6)
_cell_length_b                   7.4112(3)
_cell_length_c                   16.5010(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7630(10)
_cell_angle_gamma                90.00
_cell_volume                     1648.55(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1464
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      20.73

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10871
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.44
_reflns_number_total             3768
_reflns_number_gt                2006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0828P)²+0.2502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0049(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3768
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1830
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C4 C 0.58363(17) 0.0470(3) 0.66488(15) 0.0457(6) Uani 1 1 d . . .
H4A H 0.5964 0.1649 0.6496 0.055 Uiso 1 1 calc R . .
C5 C 0.39618(16) 0.1053(3) 0.68942(16) 0.0404(6) Uani 1 1 d . . .
C6 C 0.21409(18) -0.0956(4) 0.54952(17) 0.0525(7) Uani 1 1 d . . .
C7 C 0.34336(17) 0.1542(3) 0.60387(16) 0.0445(6) Uani 1 1 d . . .
H7A H 0.2860 0.2295 0.6136 0.053 Uiso 1 1 calc R . .
C10 C 0.30411(17) -0.0124(3) 0.56171(16) 0.0465(6) Uani 1 1 d . . .
C11 C 0.65745(18) -0.0834(4) 0.66738(17) 0.0502(7) Uani 1 1 d . . .
C12 C 0.47359(18) -0.1781(3) 0.70911(16) 0.0464(6) Uani 1 1 d . . .
C14 C 0.49066(16) -0.0030(3) 0.68575(15) 0.0405(6) Uani 1 1 d . . .
C15 C 0.32970(18) -0.0324(3) 0.72844(16) 0.0452(6) Uani 1 1 d . . .
C16 C 0.6384(2) -0.2605(4) 0.68832(19) 0.0596(8) Uani 1 1 d . . .
H16A H 0.6885 -0.3465 0.6881 0.072 Uiso 1 1 calc R . .
C20 C 0.2305(2) -0.2649(4) 0.5120(2) 0.0667(8) Uani 1 1 d . . .
C21 C 0.4087(2) 0.2646(4) 0.55151(18) 0.0619(8) Uani 1 1 d . . .
H21A H 0.3726 0.2912 0.5003 0.093 Uiso 1 1 calc R . .
H21B H 0.4672 0.1969 0.5423 0.093 Uiso 1 1 calc R . .
H21C H 0.4273 0.3753 0.5789 0.093 Uiso 1 1 calc R . .
C22 C 0.5447(2) -0.3102(4) 0.70969(19) 0.0593(8) Uani 1 1 d . . .
H22A H 0.5308 -0.4284 0.7238 0.071 Uiso 1 1 calc R . .
C23 C 0.8282(2) -0.1441(4) 0.6492(2) 0.0774(10) Uani 1 1 d . . .
H23A H 0.8863 -0.0827 0.6338 0.116 Uiso 1 1 calc R . .
H23B H 0.8121 -0.2414 0.6120 0.116 Uiso 1 1 calc R . .
H23C H 0.8409 -0.1914 0.7033 0.116 Uiso 1 1 calc R . .
C24 C 0.1597(3) -0.4224(5) 0.4890(3) 0.0965(13) Uani 1 1 d . . .
H24A H 0.1973 -0.5331 0.4855 0.116 Uiso 1 1 calc R . .
H24B H 0.1137 -0.4377 0.5305 0.116 Uiso 1 1 calc R . .
C25 C 0.1049(3) -0.3857(6) 0.4110(3) 0.1139(15) Uani 1 1 d . . .
H25A H 0.0611 -0.4847 0.3967 0.171 Uiso 1 1 calc R . .
H25B H 0.1506 -0.3711 0.3700 0.171 Uiso 1 1 calc R . .
H25C H 0.0668 -0.2772 0.4149 0.171 Uiso 1 1 calc R . .
N3 N 0.37539(15) -0.1915(3) 0.73271(14) 0.0537(6) Uani 1 1 d . . .
H3A H 0.3488 -0.2899 0.7479 0.064 Uiso 1 1 calc R . .
N2 N 0.32336(18) -0.2811(3) 0.50024(17) 0.0701(8) Uani 1 1 d . . .
N1 N 0.12097(18) -0.0268(4) 0.57169(16) 0.0702(8) Uani 1 1 d . . .
O6 O 0.41328(13) 0.2625(2) 0.73601(11) 0.0543(5) Uani 1 1 d . . .
H6A H 0.3617 0.3207 0.7359 0.081 Uiso 1 1 calc R . .
O5 O 0.37076(11) -0.1213(2) 0.53135(11) 0.0539(5) Uani 1 1 d . . .
O4 O 0.24528(13) -0.0018(2) 0.74985(12) 0.0582(5) Uani 1 1 d . . .
O3 O 0.74796(13) -0.0218(3) 0.64725(13) 0.0687(6) Uani 1 1 d . . .
O2 O 0.11638(15) 0.1300(4) 0.59345(18) 0.1009(9) Uani 1 1 d . . .
O1 O 0.05026(16) -0.1273(4) 0.56767(17) 0.1013(9) 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
C4 0.0399(13) 0.0497(14) 0.0473(16) 0.0014(12) 0.0030(12) 0.0032(11)
C5 0.0364(12) 0.0377(11) 0.0483(15) -0.0023(11) 0.0099(11) 0.0001(10)
C6 0.0371(13) 0.0710(17) 0.0499(17) -0.0091(13) 0.0069(12) 0.0064(13)
C7 0.0403(13) 0.0432(13) 0.0503(16) 0.0030(11) 0.0059(12) 0.0083(10)
C10 0.0391(13) 0.0546(14) 0.0463(15) 0.0003(12) 0.0076(12) 0.0081(12)
C11 0.0394(13) 0.0632(16) 0.0482(16) 0.0005(13) 0.0044(12) 0.0021(12)
C12 0.0419(13) 0.0480(13) 0.0496(16) 0.0074(12) 0.0066(12) 0.0043(11)
C14 0.0386(13) 0.0418(12) 0.0410(14) -0.0007(11) 0.0032(11) 0.0011(10)
C15 0.0453(14) 0.0432(13) 0.0484(16) 0.0019(11) 0.0114(12) -0.0011(11)
C16 0.0489(16) 0.0613(17) 0.069(2) 0.0051(15) 0.0073(15) 0.0146(13)
C20 0.0562(17) 0.075(2) 0.069(2) -0.0183(16) 0.0083(16) -0.0040(15)
C21 0.0651(18) 0.0581(16) 0.063(2) 0.0177(14) 0.0069(15) 0.0038(14)
C22 0.0588(17) 0.0478(14) 0.072(2) 0.0135(14) 0.0070(15) 0.0089(13)
C23 0.0417(15) 0.088(2) 0.103(3) -0.011(2) 0.0063(17) 0.0141(15)
C24 0.081(2) 0.095(3) 0.109(3) -0.047(2) -0.019(2) 0.006(2)
C25 0.102(3) 0.100(3) 0.137(4) -0.013(3) -0.007(3) 0.013(2)
N3 0.0524(13) 0.0429(11) 0.0679(16) 0.0121(11) 0.0178(12) 0.0009(10)
N2 0.0630(16) 0.0655(15) 0.082(2) -0.0264(14) 0.0100(14) -0.0002(13)
N1 0.0419(14) 0.107(2) 0.0614(17) -0.0225(16) 0.0033(12) 0.0081(15)
O6 0.0512(10) 0.0465(10) 0.0657(13) -0.0139(9) 0.0085(9) -0.0027(8)
O5 0.0432(10) 0.0555(10) 0.0643(13) -0.0108(9) 0.0121(9) 0.0076(8)
O4 0.0486(10) 0.0520(10) 0.0782(14) 0.0033(10) 0.0292(10) 0.0005(9)
O3 0.0368(10) 0.0760(13) 0.0943(17) 0.0029(12) 0.0113(10) 0.0073(9)
O2 0.0497(13) 0.125(2) 0.127(2) -0.0578(18) -0.0029(13) 0.0266(13)
O1 0.0445(12) 0.146(2) 0.116(2) -0.0192(18) 0.0215(13) -0.0151(15)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
C4 C14 1.382(3) . ?
C4 C11 1.388(3) . ?
C5 O6 1.404(3) . ?
C5 C14 1.515(3) . ?
C5 C15 1.536(3) . ?
C5 C7 1.571(3) . ?
C6 C10 1.365(3) . ?
C6 C20 1.425(4) . ?
C6 N1 1.434(3) . ?
C7 C10 1.493(3) . ?
C7 C21 1.524(4) . ?
C10 O5 1.338(3) . ?
C11 O3 1.373(3) . ?
C11 C16 1.386(4) . ?
C12 C22 1.371(3) . ?
C12 C14 1.379(3) . ?
C12 N3 1.418(3) . ?
C15 O4 1.244(3) . ?
C15 N3 1.330(3) . ?
C16 C22 1.394(4) . ?
C20 N2 1.293(4) . ?
C20 C24 1.537(4) . ?
C23 O3 1.413(3) . ?
C24 C25 1.457(5) . ?
N2 O5 1.422(3) . ?
N1 O1 1.210(3) . ?
N1 O2 1.220(3) . ?

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
C14 C4 C11 118.3(2) . . ?
O6 C5 C14 111.12(19) . . ?
O6 C5 C15 113.4(2) . . ?
C14 C5 C15 100.94(18) . . ?
O6 C5 C7 110.03(18) . . ?
C14 C5 C7 114.1(2) . . ?
C15 C5 C7 106.95(18) . . ?
C10 C6 C20 107.0(2) . . ?
C10 C6 N1 126.4(3) . . ?
C20 C6 N1 126.5(3) . . ?
C10 C7 C21 112.3(2) . . ?
C10 C7 C5 110.22(19) . . ?
C21 C7 C5 113.1(2) . . ?
O5 C10 C6 107.0(2) . . ?
O5 C10 C7 116.7(2) . . ?
C6 C10 C7 136.1(2) . . ?
O3 C11 C16 124.3(2) . . ?
O3 C11 C4 114.5(2) . . ?
C16 C11 C4 121.2(2) . . ?
C22 C12 C14 122.7(2) . . ?
C22 C12 N3 128.3(2) . . ?
C14 C12 N3 109.0(2) . . ?
C12 C14 C4 119.9(2) . . ?
C12 C14 C5 109.0(2) . . ?
C4 C14 C5 131.0(2) . . ?
O4 C15 N3 125.4(2) . . ?
O4 C15 C5 125.5(2) . . ?
N3 C15 C5 109.0(2) . . ?
C11 C16 C22 120.3(2) . . ?
N2 C20 C6 109.6(3) . . ?
N2 C20 C24 119.1(3) . . ?
C6 C20 C24 131.3(3) . . ?
C12 C22 C16 117.5(3) . . ?
C25 C24 C20 109.8(4) . . ?
C15 N3 C12 111.4(2) . . ?
C20 N2 O5 106.5(2) . . ?
O1 N1 O2 122.9(3) . . ?
O1 N1 C6 118.3(3) . . ?
O2 N1 C6 118.8(3) . . ?
C10 O5 N2 109.87(18) . . ?
C11 O3 C23 118.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_matq1120
_database_code_depnum_ccdc_archive 'CCDC 1046946'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-04-14 downloaded from the CCDC.
;
_audit_creation_date             2015-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_chemical_name_common            ?
_chemical_name_systematic        
3-((4-amino-3-methylisoxazol-5-yl)methyl)-3-hydroxyindolin-2-one
_chemical_formula_moiety         'C13 H13 N3 O3'
_chemical_formula_sum            'C13 H13 N3 O3'
_chemical_formula_weight         259.26
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3186(4)
_cell_length_b                   11.7574(8)
_cell_length_c                   16.3886(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.537(7)
_cell_angle_gamma                90
_cell_volume                     1211.84(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    569
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      23.8730
_cell_measurement_theta_min      3.9770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.1087
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4709
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         3.466
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   65.00   95.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  -90.0000 20

#__ type_ start__ end____ width___ exp.time_
  2 omega   29.00   89.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946    0.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   90.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946    0.0000  120.0000 82
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1005160000
_diffrn_orient_matrix_UB_12      -0.0239132000
_diffrn_orient_matrix_UB_13      -0.0058745000
_diffrn_orient_matrix_UB_21      -0.0125508000
_diffrn_orient_matrix_UB_22      0.0169727000
_diffrn_orient_matrix_UB_23      -0.0417086000
_diffrn_orient_matrix_UB_31      0.0497096000
_diffrn_orient_matrix_UB_32      0.0526830000
_diffrn_orient_matrix_UB_33      0.0108001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1277
_reflns_number_total             2393
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1623
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2C), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1820(4) 0.6282(2) 0.41327(14) 0.0586(8) Uani 1 1 d . . . . .
O2 O 0.1680(3) 0.53975(18) 0.31793(14) 0.0408(7) Uani 1 1 d . . . . .
H2 H 0.1402 0.4796 0.3398 0.061 Uiso 1 1 calc GR . . . .
O3 O 0.3653(4) 0.71859(18) 0.20837(14) 0.0453(7) Uani 1 1 d . . . . .
N1 N -0.3724(5) 0.5403(2) 0.30438(17) 0.0422(8) Uani 1 1 d . . . . .
H1 H -0.4917 0.5330 0.3251 0.051 Uiso 1 1 calc R . . . .
N2 N -0.0949(5) 0.8391(3) 0.0956(2) 0.0387(8) Uani 1 1 d . . . . .
N3 N 0.4544(5) 0.7567(2) 0.13756(18) 0.0456(8) Uani 1 1 d . . . . .
C1 C -0.3363(6) 0.5033(3) 0.2254(2) 0.0382(9) Uani 1 1 d . . . . .
C2 C -0.4766(6) 0.4477(3) 0.1697(3) 0.0544(11) Uani 1 1 d . . . . .
H2C H -0.6131 0.4291 0.1818 0.065 Uiso 1 1 calc R . . . .
C3 C -0.4056(7) 0.4205(3) 0.0943(2) 0.0613(12) Uani 1 1 d . . . . .
H3 H -0.4965 0.3829 0.0552 0.074 Uiso 1 1 calc R . . . .
C4 C -0.2017(7) 0.4483(3) 0.0765(2) 0.0563(11) Uani 1 1 d . . . . .
H4 H -0.1575 0.4301 0.0256 0.068 Uiso 1 1 calc R . . . .
C5 C -0.0642(6) 0.5033(3) 0.1344(2) 0.0437(9) Uani 1 1 d . . . . .
H5 H 0.0731 0.5214 0.1229 0.052 Uiso 1 1 calc R . . . .
C6 C -0.1323(5) 0.5310(2) 0.20928(19) 0.0346(8) Uani 1 1 d . . . . .
C7 C -0.0229(5) 0.5915(3) 0.28361(19) 0.0340(8) Uani 1 1 d . . . . .
C8 C -0.1976(6) 0.5889(3) 0.3441(2) 0.0400(9) Uani 1 1 d . . . . .
C9 C 0.0242(6) 0.7171(3) 0.26859(19) 0.0397(9) Uani 1 1 d . . . . .
H9A H -0.1102 0.7570 0.2588 0.048 Uiso 1 1 calc R . . . .
H9B H 0.0977 0.7481 0.3184 0.048 Uiso 1 1 calc R . . . .
C10 C 0.1524(5) 0.7426(2) 0.1999(2) 0.0345(8) Uani 1 1 d . . . . .
C11 C 0.1033(5) 0.7934(2) 0.12643(19) 0.0314(8) Uani 1 1 d . . . . .
C12 C 0.2965(6) 0.8005(3) 0.0896(2) 0.0362(8) Uani 1 1 d . . . . .
C13 C 0.3325(6) 0.8541(3) 0.0100(2) 0.0476(10) Uani 1 1 d . . . . .
H13A H 0.2984 0.9336 0.0117 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.2435 0.8182 -0.0333 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.4789 0.8453 0.0001 0.071 Uiso 1 1 calc GR . . . .
H2A H -0.205(6) 0.799(3) 0.1095(19) 0.043(11) Uiso 1 1 d . . . . .
H2B H -0.113(7) 0.843(3) 0.043(3) 0.086(16) Uiso 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
O1 0.0482(18) 0.099(2) 0.0306(14) -0.0025(13) 0.0118(13) -0.0025(15)
O2 0.0285(14) 0.0495(16) 0.0448(15) 0.0131(11) 0.0057(11) -0.0023(11)
O3 0.0393(15) 0.0519(15) 0.0453(15) 0.0122(11) 0.0071(12) 0.0018(12)
N1 0.0271(17) 0.0550(18) 0.0460(19) 0.0104(14) 0.0117(14) 0.0023(14)
N2 0.0285(18) 0.053(2) 0.0348(19) 0.0009(14) 0.0051(15) 0.0008(15)
N3 0.0338(18) 0.0536(19) 0.051(2) 0.0134(14) 0.0118(15) 0.0018(14)
C1 0.032(2) 0.041(2) 0.040(2) 0.0034(15) -0.0036(17) -0.0012(17)
C2 0.035(2) 0.055(2) 0.071(3) 0.000(2) -0.009(2) -0.0004(19)
C3 0.068(3) 0.056(2) 0.055(3) -0.011(2) -0.016(2) -0.004(2)
C4 0.074(3) 0.056(3) 0.038(2) -0.0046(17) -0.002(2) 0.003(2)
C5 0.043(2) 0.048(2) 0.041(2) 0.0008(16) 0.0081(18) 0.0023(18)
C6 0.033(2) 0.0353(19) 0.0358(19) 0.0040(14) 0.0039(16) -0.0031(16)
C7 0.0283(19) 0.043(2) 0.0311(18) 0.0048(14) 0.0074(15) -0.0014(16)
C8 0.034(2) 0.051(2) 0.036(2) 0.0144(16) 0.0070(17) 0.0007(17)
C9 0.043(2) 0.043(2) 0.0338(19) 0.0028(14) 0.0113(17) -0.0036(17)
C10 0.032(2) 0.0327(18) 0.039(2) 0.0003(14) 0.0043(16) -0.0040(16)
C11 0.0270(19) 0.0331(18) 0.0349(19) -0.0009(14) 0.0071(15) -0.0008(15)
C12 0.034(2) 0.0344(19) 0.041(2) 0.0016(14) 0.0094(17) -0.0004(16)
C13 0.041(2) 0.058(2) 0.046(2) 0.0053(17) 0.0186(18) 0.0005(19)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C8 1.220(4) . ?
O2 H2 0.8200 . ?
O2 C7 1.418(4) . ?
O3 N3 1.411(3) . ?
O3 C10 1.368(4) . ?
N1 H1 0.8600 . ?
N1 C1 1.406(4) . ?
N1 C8 1.353(4) . ?
N2 C11 1.410(4) . ?
N2 H2A 0.89(4) . ?
N2 H2B 0.87(4) . ?
N3 C12 1.315(4) . ?
C1 C2 1.375(4) . ?
C1 C6 1.380(4) . ?
C2 H2C 0.9300 . ?
C2 C3 1.391(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(4) . ?
C6 C7 1.518(4) . ?
C7 C8 1.553(4) . ?
C7 C9 1.532(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.479(4) . ?
C10 C11 1.353(4) . ?
C11 C12 1.416(4) . ?
C12 C13 1.486(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C7 O2 H2 109.5 . . ?
C10 O3 N3 108.5(2) . . ?
C1 N1 H1 124.0 . . ?
C8 N1 H1 124.0 . . ?
C8 N1 C1 112.1(3) . . ?
C11 N2 H2A 113(2) . . ?
C11 N2 H2B 114(3) . . ?
H2A N2 H2B 105(3) . . ?
C12 N3 O3 106.0(3) . . ?
C2 C1 N1 127.4(4) . . ?
C2 C1 C6 122.7(3) . . ?
C6 C1 N1 109.9(3) . . ?
C1 C2 H2C 121.4 . . ?
C1 C2 C3 117.1(4) . . ?
C3 C2 H2C 121.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 108.6(3) . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 C7 132.0(3) . . ?
O2 C7 C6 114.9(3) . . ?
O2 C7 C8 111.6(2) . . ?
O2 C7 C9 107.8(3) . . ?
C6 C7 C8 101.9(3) . . ?
C6 C7 C9 113.8(2) . . ?
C9 C7 C8 106.4(2) . . ?
O1 C8 N1 126.5(3) . . ?
O1 C8 C7 126.0(3) . . ?
N1 C8 C7 107.4(3) . . ?
C7 C9 H9A 108.2 . . ?
C7 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C7 116.5(3) . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
O3 C10 C9 119.1(3) . . ?
C11 C10 O3 108.7(3) . . ?
C11 C10 C9 132.2(3) . . ?
N2 C11 C12 126.6(3) . . ?
C10 C11 N2 127.3(3) . . ?
C10 C11 C12 105.8(3) . . ?
N3 C12 C11 111.0(3) . . ?
N3 C12 C13 121.3(3) . . ?
C11 C12 C13 127.6(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C7 C8 O1 56.8(4) . . . . ?
O2 C7 C8 N1 -126.2(3) . . . . ?
O2 C7 C9 C10 72.6(4) . . . . ?
O3 N3 C12 C11 0.3(4) . . . . ?
O3 N3 C12 C13 177.4(3) . . . . ?
O3 C10 C11 N2 -175.3(3) . . . . ?
O3 C10 C11 C12 -0.3(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N1 C1 C6 C5 -179.4(3) . . . . ?
N1 C1 C6 C7 0.0(4) . . . . ?
N2 C11 C12 N3 175.0(3) . . . . ?
N2 C11 C12 C13 -1.8(5) . . . . ?
N3 O3 C10 C9 -176.3(3) . . . . ?
N3 O3 C10 C11 0.4(3) . . . . ?
C1 N1 C8 O1 -179.8(3) . . . . ?
C1 N1 C8 C7 3.3(4) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C6 C7 O2 122.6(3) . . . . ?
C1 C6 C7 C8 1.8(3) . . . . ?
C1 C6 C7 C9 -112.4(3) . . . . ?
C2 C1 C6 C5 0.5(5) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 0.1(5) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 O2 -58.1(4) . . . . ?
C5 C6 C7 C8 -178.9(3) . . . . ?
C5 C6 C7 C9 66.9(4) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C6 C7 C8 O1 -180.0(3) . . . . ?
C6 C7 C8 N1 -3.0(3) . . . . ?
C6 C7 C9 C10 -56.2(4) . . . . ?
C7 C9 C10 O3 -73.1(4) . . . . ?
C7 C9 C10 C11 111.0(4) . . . . ?
C8 N1 C1 C2 177.9(3) . . . . ?
C8 N1 C1 C6 -2.2(4) . . . . ?
C8 C7 C9 C10 -167.6(3) . . . . ?
C9 C7 C8 O1 -60.6(4) . . . . ?
C9 C7 C8 N1 116.4(3) . . . . ?
C9 C10 C11 N2 0.9(6) . . . . ?
C9 C10 C11 C12 175.9(3) . . . . ?
C10 O3 N3 C12 -0.5(3) . . . . ?
C10 C11 C12 N3 0.0(4) . . . . ?
C10 C11 C12 C13 -176.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 1416533413.32
_olex2_submission_special_instructions 'No special instructions were received'
