# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelxl6
_audit_block_doi                 10.5517/ccwfkf8
_database_code_depnum_ccdc_archive 'CCDC 817390'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp206073v 2011
_audit_update_record             
;
2011-03-14 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;
#TrackingRef 'flch11hb3_100K.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
indolin-2-one
;
_chemical_name_common            2-oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6075(1)
_cell_length_b                   13.0331(3)
_cell_length_c                   14.8275(3)
_cell_angle_alpha                114.825(2)
_cell_angle_beta                 100.483(2)
_cell_angle_gamma                91.664(2)
_cell_volume                     960.32(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    7748
_cell_measurement_theta_min      3.0926
_cell_measurement_theta_max      34.5420

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9464
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(1)
_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  
;
Oxford Diffraction Diffractometer with Sapphire3 detector
;
_diffrn_measurement_method       'ω - scan'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7481
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3329
_reflns_number_gt                2890
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0660P)²+0.0000P] 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       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
O1 O 0.81220(14) 0.75102(7) 0.23984(6) 0.0196(2) Uani 1 1 d . . .
N1 N 0.55763(18) 0.59414(8) 0.21148(7) 0.0153(2) Uani 1 1 d . . .
H1N H 0.473(2) 0.6256(12) 0.2579(10) 0.018 Uiso 1 1 d . . .
C1 C 0.5134(2) 0.47799(10) 0.14366(8) 0.0136(3) Uani 1 1 d . . .
C2 C 0.3387(2) 0.39690(10) 0.13732(9) 0.0159(3) Uani 1 1 d . . .
H2 H 0.2297 0.4155 0.1825 0.019 Uiso 1 1 calc R . .
C3 C 0.3291(2) 0.28657(10) 0.06176(9) 0.0176(3) Uani 1 1 d . . .
H3 H 0.2101 0.2289 0.0549 0.021 Uiso 1 1 calc R . .
C4 C 0.4899(2) 0.25941(10) -0.00360(9) 0.0178(3) Uani 1 1 d . . .
H4 H 0.4804 0.1835 -0.0542 0.021 Uiso 1 1 calc R . .
C5 C 0.6653(2) 0.34252(10) 0.00431(9) 0.0161(3) Uani 1 1 d . . .
H5 H 0.7757 0.3237 -0.0403 0.019 Uiso 1 1 calc R . .
C6 C 0.67634(19) 0.45297(10) 0.07816(8) 0.0135(3) Uani 1 1 d . . .
C7 C 0.8338(2) 0.56168(10) 0.10562(8) 0.0142(3) Uani 1 1 d . . .
H7A H 0.8139 0.5818 0.0475 0.017 Uiso 1 1 calc R . .
H7B H 1.0082 0.5550 0.1270 0.017 Uiso 1 1 calc R . .
C8 C 0.7402(2) 0.64937(10) 0.19328(8) 0.0143(3) Uani 1 1 d . . .
O1A O 0.18154(15) 0.63777(7) 0.32562(6) 0.0202(2) Uani 1 1 d . . .
N1A N -0.01175(17) 0.70604(9) 0.46043(7) 0.0153(2) Uani 1 1 d . . .
H1NA H -0.116(2) 0.7468(11) 0.4424(10) 0.018 Uiso 1 1 d . . .
C1A C 0.00419(19) 0.69951(9) 0.55376(8) 0.0137(3) Uani 1 1 d . . .
C2A C -0.1327(2) 0.74814(10) 0.62675(9) 0.0159(3) Uani 1 1 d . . .
H2A H -0.2580 0.7928 0.6182 0.019 Uiso 1 1 calc R . .
C3A C -0.0786(2) 0.72859(10) 0.71343(9) 0.0170(3) Uani 1 1 d . . .
H3A H -0.1708 0.7597 0.7645 0.020 Uiso 1 1 calc R . .
C4A C 0.1071(2) 0.66471(10) 0.72668(9) 0.0181(3) Uani 1 1 d . . .
H4A H 0.1428 0.6543 0.7872 0.022 Uiso 1 1 calc R . .
C5A C 0.2414(2) 0.61591(10) 0.65200(9) 0.0168(3) Uani 1 1 d . . .
H5A H 0.3680 0.5720 0.6610 0.020 Uiso 1 1 calc R . .
C6A C 0.1879(2) 0.63234(9) 0.56480(8) 0.0141(3) Uani 1 1 d . . .
C7A C 0.2925(2) 0.59164(10) 0.47098(8) 0.0154(3) Uani 1 1 d . . .
H7AA H 0.2657 0.5076 0.4338 0.018 Uiso 1 1 calc R . .
H7BA H 0.4698 0.6171 0.4883 0.018 Uiso 1 1 calc R . .
C8A C 0.1528(2) 0.64617(10) 0.40877(8) 0.0150(3) Uani 1 1 d . . .
O1B O 0.61287(15) 0.85066(8) 0.44994(6) 0.0228(2) Uani 1 1 d . . .
N1B N 0.33044(18) 0.86636(8) 0.32398(7) 0.0166(2) Uani 1 1 d . . .
H1NB H 0.215(2) 0.8114(12) 0.3167(10) 0.020 Uiso 1 1 d . . .
C1B C 0.3210(2) 0.92260(10) 0.26068(8) 0.0154(3) Uani 1 1 d . . .
C2B C 0.1328(2) 0.91417(10) 0.18215(9) 0.0179(3) Uani 1 1 d . . .
H2B H -0.019(2) 0.8685(11) 0.1663(10) 0.022 Uiso 1 1 d . . .
C3B C 0.1727(2) 0.97636(10) 0.12853(9) 0.0211(3) Uani 1 1 d . . .
H3B H 0.0474 0.9726 0.0743 0.025 Uiso 1 1 calc R . .
C4B C 0.3922(2) 1.04385(10) 0.15276(9) 0.0220(3) Uani 1 1 d . . .
H4B H 0.4165 1.0841 0.1140 0.026 Uiso 1 1 calc R . .
C5B C 0.5769(2) 1.05302(10) 0.23340(9) 0.0201(3) Uani 1 1 d . . .
H5B H 0.7258 1.1003 0.2506 0.024 Uiso 1 1 calc R . .
C6B C 0.5407(2) 0.99243(9) 0.28806(9) 0.0165(3) Uani 1 1 d . . .
C7B C 0.6984(2) 0.98343(10) 0.37714(9) 0.0184(3) Uani 1 1 d . . .
H7AB H 0.719(2) 1.0546(12) 0.4385(10) 0.022 Uiso 1 1 d . . .
H7BB H 0.862(3) 0.9619(11) 0.3647(10) 0.022 Uiso 1 1 d . . .
C8B C 0.5506(2) 0.89258(10) 0.39002(9) 0.0171(3) Uani 1 1 d . . .


_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 1.2224(14) . ?
N1 C8 1.3636(15) . ?
N1 C1 1.4048(15) . ?
N1 H1N 0.873(14) . ?
C1 C2 1.3813(16) . ?
C1 C6 1.3997(16) . ?
C2 C3 1.3952(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3881(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3939(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3862(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5049(16) . ?
C7 C8 1.5189(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O1A C8A 1.2319(14) . ?
N1A C8A 1.3582(15) . ?
N1A C1A 1.4087(15) . ?
N1A H1NA 0.880(14) . ?
C1A C2A 1.3847(16) . ?
C1A C6A 1.4019(16) . ?
C2A C3A 1.3950(17) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3890(18) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3919(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3795(16) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.5021(16) . ?
C7A C8A 1.5131(17) . ?
C7A H7AA 0.9900 . ?
C7A H7BA 0.9900 . ?
O1B C8B 1.2311(15) . ?
N1B C8B 1.3618(15) . ?
N1B C1B 1.4080(15) . ?
N1B H1NB 0.909(14) . ?
C1B C2B 1.3857(16) . ?
C1B C6B 1.3975(16) . ?
C2B C3B 1.3907(18) . ?
C2B H2B 0.957(13) . ?
C3B C4B 1.3887(17) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3926(18) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3819(17) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.5006(17) . ?
C7B C8B 1.5218(18) . ?
C7B H7AB 0.974(14) . ?
C7B H7BB 0.992(14) . ?

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
C8 N1 C1 111.91(10) . . ?
C8 N1 H1N 125.7(9) . . ?
C1 N1 H1N 122.4(9) . . ?
C2 C1 C6 122.60(11) . . ?
C2 C1 N1 128.11(10) . . ?
C6 C1 N1 109.29(10) . . ?
C1 C2 C3 117.20(11) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.29(11) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.56(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.10(11) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.24(11) . . ?
C5 C6 C7 133.01(11) . . ?
C1 C6 C7 107.74(10) . . ?
C6 C7 C8 103.64(9) . . ?
C6 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
O1 C8 N1 125.40(11) . . ?
O1 C8 C7 127.20(10) . . ?
N1 C8 C7 107.40(10) . . ?
C8A N1A C1A 111.49(10) . . ?
C8A N1A H1NA 127.5(8) . . ?
C1A N1A H1NA 121.0(8) . . ?
C2A C1A C6A 122.14(11) . . ?
C2A C1A N1A 128.63(11) . . ?
C6A C1A N1A 109.23(10) . . ?
C1A C2A C3A 117.05(11) . . ?
C1A C2A H2A 121.5 . . ?
C3A C2A H2A 121.5 . . ?
C4A C3A C2A 121.48(11) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C3A C4A C5A 120.52(11) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 118.97(11) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C5A C6A C1A 119.80(11) . . ?
C5A C6A C7A 132.50(11) . . ?
C1A C6A C7A 107.70(10) . . ?
C6A C7A C8A 103.54(9) . . ?
C6A C7A H7AA 111.1 . . ?
C8A C7A H7AA 111.1 . . ?
C6A C7A H7BA 111.1 . . ?
C8A C7A H7BA 111.1 . . ?
H7AA C7A H7BA 109.0 . . ?
O1A C8A N1A 125.66(11) . . ?
O1A C8A C7A 126.33(11) . . ?
N1A C8A C7A 108.01(10) . . ?
C8B N1B C1B 111.61(10) . . ?
C8B N1B H1NB 122.7(8) . . ?
C1B N1B H1NB 125.1(8) . . ?
C2B C1B C6B 122.41(11) . . ?
C2B C1B N1B 128.49(11) . . ?
C6B C1B N1B 109.10(10) . . ?
C1B C2B C3B 117.19(11) . . ?
C1B C2B H2B 121.3(8) . . ?
C3B C2B H2B 121.5(8) . . ?
C4B C3B C2B 121.28(11) . . ?
C4B C3B H3B 119.4 . . ?
C2B C3B H3B 119.4 . . ?
C3B C4B C5B 120.57(12) . . ?
C3B C4B H4B 119.7 . . ?
C5B C4B H4B 119.7 . . ?
C6B C5B C4B 119.10(11) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C5B C6B C1B 119.41(11) . . ?
C5B C6B C7B 132.42(11) . . ?
C1B C6B C7B 108.17(11) . . ?
C6B C7B C8B 103.16(9) . . ?
C6B C7B H7AB 111.1(8) . . ?
C8B C7B H7AB 109.1(8) . . ?
C6B C7B H7BB 112.4(8) . . ?
C8B C7B H7BB 112.0(8) . . ?
H7AB C7B H7BB 109.0(11) . . ?
O1B C8B N1B 125.18(11) . . ?
O1B C8B C7B 127.23(11) . . ?
N1B C8B C7B 107.58(10) . . ?

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
C8 N1 C1 C2 -177.92(11) . . . . ?
C8 N1 C1 C6 1.32(13) . . . . ?
C6 C1 C2 C3 -0.07(16) . . . . ?
N1 C1 C2 C3 179.09(10) . . . . ?
C1 C2 C3 C4 0.59(16) . . . . ?
C2 C3 C4 C5 -0.43(17) . . . . ?
C3 C4 C5 C6 -0.27(17) . . . . ?
C4 C5 C6 C1 0.76(16) . . . . ?
C4 C5 C6 C7 -178.13(11) . . . . ?
C2 C1 C6 C5 -0.61(16) . . . . ?
N1 C1 C6 C5 -179.90(9) . . . . ?
C2 C1 C6 C7 178.55(10) . . . . ?
N1 C1 C6 C7 -0.75(12) . . . . ?
C5 C6 C7 C8 178.99(11) . . . . ?
C1 C6 C7 C8 0.00(11) . . . . ?
C1 N1 C8 O1 178.61(10) . . . . ?
C1 N1 C8 C7 -1.29(12) . . . . ?
C6 C7 C8 O1 -179.12(11) . . . . ?
C6 C7 C8 N1 0.77(11) . . . . ?
C8A N1A C1A C2A -179.56(11) . . . . ?
C8A N1A C1A C6A 0.05(13) . . . . ?
C6A C1A C2A C3A 0.70(16) . . . . ?
N1A C1A C2A C3A -179.73(11) . . . . ?
C1A C2A C3A C4A 1.02(16) . . . . ?
C2A C3A C4A C5A -1.52(17) . . . . ?
C3A C4A C5A C6A 0.26(17) . . . . ?
C4A C5A C6A C1A 1.42(16) . . . . ?
C4A C5A C6A C7A -179.19(11) . . . . ?
C2A C1A C6A C5A -1.94(16) . . . . ?
N1A C1A C6A C5A 178.42(10) . . . . ?
C2A C1A C6A C7A 178.53(10) . . . . ?
N1A C1A C6A C7A -1.11(12) . . . . ?
C5A C6A C7A C8A -177.82(12) . . . . ?
C1A C6A C7A C8A 1.63(11) . . . . ?
C1A N1A C8A O1A -179.26(11) . . . . ?
C1A N1A C8A C7A 1.02(12) . . . . ?
C6A C7A C8A O1A 178.67(11) . . . . ?
C6A C7A C8A N1A -1.61(12) . . . . ?
C8B N1B C1B C2B 177.35(11) . . . . ?
C8B N1B C1B C6B -2.22(13) . . . . ?
C6B C1B C2B C3B 1.69(17) . . . . ?
N1B C1B C2B C3B -177.83(11) . . . . ?
C1B C2B C3B C4B 0.10(18) . . . . ?
C2B C3B C4B C5B -1.49(18) . . . . ?
C3B C4B C5B C6B 1.11(18) . . . . ?
C4B C5B C6B C1B 0.62(17) . . . . ?
C4B C5B C6B C7B -179.99(12) . . . . ?
C2B C1B C6B C5B -2.08(17) . . . . ?
N1B C1B C6B C5B 177.52(10) . . . . ?
C2B C1B C6B C7B 178.40(10) . . . . ?
N1B C1B C6B C7B -2.00(13) . . . . ?
C5B C6B C7B C8B -174.55(12) . . . . ?
C1B C6B C7B C8B 4.89(12) . . . . ?
C1B N1B C8B O1B -175.83(11) . . . . ?
C1B N1B C8B C7B 5.38(13) . . . . ?
C6B C7B C8B O1B 175.06(11) . . . . ?
C6B C7B C8B N1B -6.18(12) . . . . ?

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
N1 H1N O1A 0.873(14) 2.043(14) 2.8628(13) 155.9(12) .
N1A H1NA O1B 0.880(14) 2.054(14) 2.8923(14) 159.1(12) 1_455
N1B H1NB O1A 0.909(14) 2.326(15) 3.0819(13) 140.4(11) .
N1B H1NB O1 0.909(14) 2.286(13) 3.0189(13) 137.5(11) 1_455
C7B H7BB O1 0.992(14) 2.560(13) 3.0222(15) 108.3(9) .
C2B H2B O1 0.957(13) 2.474(14) 3.2174(15) 134.5(10) 1_455

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034




####################################################################### 
# 
# 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_shelxl4
_audit_block_doi                 10.5517/ccwfkc6
_database_code_depnum_ccdc_archive 'CCDC 817388'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp206073v 2011
_audit_update_record             
;
2011-03-14 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;
#TrackingRef 'flch11hb2_100k.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
indolin-2-one
;
_chemical_name_common            2-oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   14.2644(9)
_cell_length_b                   12.9569(8)
_cell_length_c                   6.9931(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.393(6)
_cell_angle_gamma                90.00
_cell_volume                     1271.28(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2448
_cell_measurement_theta_min      2.8923
_cell_measurement_theta_max      34.5254

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9461
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(1)
_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  
;
Oxford Diffraction Diffractometer with Sapphire3 detector
;
_diffrn_measurement_method       'ω - scan'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8282
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0743
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2253
_reflns_number_gt                1406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0201P)²+0.0000P] 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       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2253
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_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
O1 O 0.26247(9) 0.41876(10) 1.02439(18) 0.0185(3) Uani 1 1 d . . .
N1 N 0.12358(11) 0.32415(12) 0.9535(2) 0.0154(4) Uani 1 1 d . . .
H1N H 0.1507(13) 0.2642(14) 0.997(2) 0.018 Uiso 1 1 d . . .
C1 C 0.02956(12) 0.33990(14) 0.8573(2) 0.0124(4) Uani 1 1 d . . .
C2 C -0.04573(12) 0.27082(15) 0.8357(2) 0.0142(4) Uani 1 1 d . . .
H2 H -0.0376 0.2023 0.8841 0.017 Uiso 1 1 calc R . .
C3 C -0.13397(13) 0.30642(15) 0.7399(3) 0.0179(5) Uani 1 1 d . . .
H3 H -0.1872 0.2611 0.7225 0.021 Uiso 1 1 calc R . .
C4 C -0.14583(13) 0.40640(15) 0.6695(3) 0.0174(5) Uani 1 1 d . . .
H4 H -0.2068 0.4287 0.6049 0.021 Uiso 1 1 calc R . .
C5 C -0.06864(13) 0.47479(15) 0.6928(3) 0.0148(5) Uani 1 1 d . . .
H5 H -0.0766 0.5433 0.6442 0.018 Uiso 1 1 calc R . .
C6 C 0.01945(13) 0.44072(14) 0.7879(2) 0.0128(5) Uani 1 1 d . . .
C7 C 0.11420(12) 0.49399(14) 0.8417(3) 0.0142(5) Uani 1 1 d . . .
H7A H 0.1096 0.5547 0.9254 0.017 Uiso 1 1 calc R . .
H7B H 0.1386 0.5164 0.7245 0.017 Uiso 1 1 calc R . .
C8 C 0.17736(14) 0.41094(15) 0.9514(3) 0.0147(4) Uani 1 1 d . . .
O1A O 0.22459(9) 0.36468(9) 0.54922(17) 0.0184(3) Uani 1 1 d . . .
N1A N 0.35670(11) 0.26577(12) 0.6665(2) 0.0146(4) Uani 1 1 d . . .
H1NA H 0.3283(12) 0.2055(14) 0.635(2) 0.018 Uiso 1 1 d . . .
C1A C 0.45352(12) 0.28223(14) 0.7465(3) 0.0132(4) Uani 1 1 d . . .
C2A C 0.52254(13) 0.20941(14) 0.8091(2) 0.0166(5) Uani 1 1 d . . .
H2A H 0.5081 0.1378 0.8029 0.020 Uiso 1 1 calc R . .
C3A C 0.61454(13) 0.24471(14) 0.8821(3) 0.0174(5) Uani 1 1 d . . .
H3A H 0.6639 0.1964 0.9249 0.021 Uiso 1 1 calc R . .
C4A C 0.63462(13) 0.34917(14) 0.8927(3) 0.0174(5) Uani 1 1 d . . .
H4A H 0.6975 0.3718 0.9435 0.021 Uiso 1 1 calc R . .
C5A C 0.56344(13) 0.42170(15) 0.8297(3) 0.0165(5) Uani 1 1 d . . .
H5A H 0.5773 0.4935 0.8377 0.020 Uiso 1 1 calc R . .
C6A C 0.47254(13) 0.38742(14) 0.7556(3) 0.0139(4) Uani 1 1 d . . .
C7A C 0.38118(13) 0.44364(14) 0.6728(3) 0.0164(5) Uani 1 1 d . . .
H7AA H 0.3884 0.4842 0.5564 0.020 Uiso 1 1 calc R . .
H7BA H 0.3616 0.4903 0.7705 0.020 Uiso 1 1 calc R . .
C8A C 0.30991(13) 0.35638(14) 0.6204(3) 0.0146(5) Uani 1 1 d . . .


_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 1.233(2) . ?
N1 C8 1.363(2) . ?
N1 C1 1.403(2) . ?
N1 H1N 0.896(18) . ?
C1 C2 1.385(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.393(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.504(2) . ?
C7 C8 1.519(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O1A C8A 1.234(2) . ?
N1A C8A 1.360(2) . ?
N1A C1A 1.410(2) . ?
N1A H1NA 0.890(18) . ?
C1A C2A 1.377(2) . ?
C1A C6A 1.389(2) . ?
C2A C3A 1.396(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.383(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.395(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.380(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.514(3) . ?
C7A C8A 1.520(2) . ?
C7A H7AA 0.9900 . ?
C7A H7BA 0.9900 . ?

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
C8 N1 C1 111.47(16) . . ?
C8 N1 H1N 120.6(11) . . ?
C1 N1 H1N 127.3(11) . . ?
C2 C1 C6 122.62(16) . . ?
C2 C1 N1 127.84(17) . . ?
C6 C1 N1 109.50(16) . . ?
C1 C2 C3 116.98(18) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 121.48(18) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.50(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.75(18) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.67(17) . . ?
C5 C6 C7 132.15(17) . . ?
C1 C6 C7 108.15(15) . . ?
C6 C7 C8 103.04(15) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
O1 C8 N1 125.26(18) . . ?
O1 C8 C7 126.91(17) . . ?
N1 C8 C7 107.83(16) . . ?
C8A N1A C1A 111.55(15) . . ?
C8A N1A H1NA 121.2(12) . . ?
C1A N1A H1NA 127.0(12) . . ?
C2A C1A C6A 122.38(16) . . ?
C2A C1A N1A 128.01(17) . . ?
C6A C1A N1A 109.62(16) . . ?
C1A C2A C3A 117.56(17) . . ?
C1A C2A H2A 121.2 . . ?
C3A C2A H2A 121.2 . . ?
C4A C3A C2A 120.81(17) . . ?
C4A C3A H3A 119.6 . . ?
C2A C3A H3A 119.6 . . ?
C3A C4A C5A 120.69(18) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 118.86(18) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C5A C6A C1A 119.70(17) . . ?
C5A C6A C7A 132.40(17) . . ?
C1A C6A C7A 107.90(16) . . ?
C6A C7A C8A 103.08(15) . . ?
C6A C7A H7AA 111.1 . . ?
C8A C7A H7AA 111.1 . . ?
C6A C7A H7BA 111.1 . . ?
C8A C7A H7BA 111.1 . . ?
H7AA C7A H7BA 109.1 . . ?
O1A C8A N1A 125.24(17) . . ?
O1A C8A C7A 126.91(17) . . ?
N1A C8A C7A 107.85(16) . . ?

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
C8 N1 C1 C2 -177.71(18) . . . . ?
C8 N1 C1 C6 0.0(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
N1 C1 C2 C3 177.44(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -177.82(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C5 -177.98(16) . . . . ?
C2 C1 C6 C7 178.33(17) . . . . ?
N1 C1 C6 C7 0.51(19) . . . . ?
C5 C6 C7 C8 177.49(18) . . . . ?
C1 C6 C7 C8 -0.74(19) . . . . ?
C1 N1 C8 O1 -179.62(18) . . . . ?
C1 N1 C8 C7 -0.5(2) . . . . ?
C6 C7 C8 O1 179.87(18) . . . . ?
C6 C7 C8 N1 0.71(19) . . . . ?
C8A N1A C1A C2A -179.70(18) . . . . ?
C8A N1A C1A C6A 0.3(2) . . . . ?
C6A C1A C2A C3A -0.6(3) . . . . ?
N1A C1A C2A C3A 179.42(18) . . . . ?
C1A C2A C3A C4A 0.8(3) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C3A C4A C5A C6A -0.3(3) . . . . ?
C4A C5A C6A C1A 0.5(3) . . . . ?
C4A C5A C6A C7A -178.69(19) . . . . ?
C2A C1A C6A C5A -0.1(3) . . . . ?
N1A C1A C6A C5A 179.93(18) . . . . ?
C2A C1A C6A C7A 179.30(17) . . . . ?
N1A C1A C6A C7A -0.7(2) . . . . ?
C5A C6A C7A C8A -179.9(2) . . . . ?
C1A C6A C7A C8A 0.8(2) . . . . ?
C1A N1A C8A O1A -179.57(18) . . . . ?
C1A N1A C8A C7A 0.2(2) . . . . ?
C6A C7A C8A O1A 179.19(18) . . . . ?
C6A C7A C8A N1A -0.6(2) . . . . ?

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
N1 H1N O1A 0.896(18) 1.973(19) 2.857(2) 168.5(16) 4_566
N1A H1NA O1 0.890(18) 1.951(18) 2.833(2) 171.1(16) 4_565

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_shelxl3
_audit_block_doi                 10.5517/ccwfkb5
_database_code_depnum_ccdc_archive 'CCDC 817387'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp206073v 2011
_audit_update_record             
;
2011-03-14 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;
#TrackingRef 'flch11hb2_295K.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
indolin-2-one
;
_chemical_name_common            2-oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   14.4305(9)
_cell_length_b                   13.1657(10)
_cell_length_c                   7.0872(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.958(7)
_cell_angle_gamma                90.00
_cell_volume                     1317.26(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(1)
_cell_measurement_reflns_used    1935
_cell_measurement_theta_min      2.8763
_cell_measurement_theta_max      34.4677

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(1)
_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  
;
Oxford Diffraction Diffractometer with Sapphire3 detector
;
_diffrn_measurement_method       'ω - scan'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8745
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2327
_reflns_number_gt                1245
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0231P)²+0.0000P] 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       0.0045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2327
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.26231(11) 0.41595(12) 1.0282(2) 0.0527(5) Uani 1 1 d . . .
N1 N 0.12455(13) 0.32404(15) 0.9534(3) 0.0437(6) Uani 1 1 d . . .
C1 C -0.06683(16) 0.47234(19) 0.6918(3) 0.0435(7) Uani 1 1 d . . .
H1 H -0.0747 0.5385 0.6454 0.052 Uiso 1 1 calc R . .
C2 C -0.14307(17) 0.4047(2) 0.6645(4) 0.0504(7) Uani 1 1 d . . .
H2 H -0.2026 0.4262 0.6001 0.060 Uiso 1 1 calc R . .
C3 C -0.13092(17) 0.3068(2) 0.7319(4) 0.0501(7) Uani 1 1 d . . .
H3 H -0.1827 0.2631 0.7117 0.060 Uiso 1 1 calc R . .
C4 C -0.04353(15) 0.27126(19) 0.8294(3) 0.0427(7) Uani 1 1 d . . .
H4 H -0.0354 0.2049 0.8746 0.051 Uiso 1 1 calc R . .
C5 C 0.03085(15) 0.33967(18) 0.8557(3) 0.0361(6) Uani 1 1 d . . .
C6 C 0.17786(18) 0.40872(18) 0.9542(3) 0.0397(6) Uani 1 1 d . . .
C7 C 0.11457(15) 0.49129(17) 0.8464(3) 0.0398(7) Uani 1 1 d . . .
H7A H 0.1105 0.5491 0.9291 0.048 Uiso 1 1 calc R . .
H7B H 0.1374 0.5140 0.7339 0.048 Uiso 1 1 calc R . .
C8 C 0.02044(15) 0.43833(18) 0.7892(3) 0.0342(6) Uani 1 1 d . . .
H1N H 0.1515(14) 0.2639(16) 0.994(3) 0.041 Uiso 1 1 d . . .
O1A O 0.22389(11) 0.36367(12) 0.5513(2) 0.0551(5) Uani 1 1 d . . .
N1A N 0.35774(13) 0.26811(15) 0.6574(3) 0.0416(6) Uani 1 1 d . . .
C1A C 0.56252(16) 0.42260(19) 0.8192(4) 0.0478(7) Uani 1 1 d . . .
H1A H 0.5754 0.4918 0.8285 0.057 Uiso 1 1 calc R . .
C2A C 0.63389(17) 0.3524(2) 0.8767(4) 0.0535(8) Uani 1 1 d . . .
H2A H 0.6953 0.3748 0.9258 0.064 Uiso 1 1 calc R . .
C3A C 0.61551(16) 0.2504(2) 0.8625(4) 0.0529(7) Uani 1 1 d . . .
H3A H 0.6647 0.2043 0.9010 0.063 Uiso 1 1 calc R . .
C4A C 0.52424(17) 0.21468(18) 0.7912(4) 0.0482(7) Uani 1 1 d . . .
H4A H 0.5112 0.1455 0.7822 0.058 Uiso 1 1 calc R . .
C5A C 0.45444(15) 0.28524(18) 0.7348(3) 0.0356(6) Uani 1 1 d . . .
C6A C 0.30937(17) 0.35683(18) 0.6183(3) 0.0410(6) Uani 1 1 d . . .
C7A C 0.37975(16) 0.44296(18) 0.6714(4) 0.0467(7) Uani 1 1 d . . .
H7AA H 0.3838 0.4837 0.5593 0.056 Uiso 1 1 calc R . .
H7BA H 0.3626 0.4864 0.7693 0.056 Uiso 1 1 calc R . .
C8A C 0.47166(16) 0.38815(18) 0.7477(3) 0.0389(6) Uani 1 1 d . . .
H1NA H 0.3307(15) 0.2092(17) 0.633(3) 0.047 Uiso 1 1 d . . .


_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 C6 1.227(3) . ?
N1 C6 1.354(3) . ?
N1 C5 1.401(3) . ?
N1 H1N 0.90(2) . ?
C1 C8 1.379(3) . ?
C1 C2 1.397(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C8 1.379(3) . ?
C6 C7 1.520(3) . ?
C7 C8 1.506(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1A C6A 1.230(3) . ?
N1A C6A 1.359(3) . ?
N1A C5A 1.408(3) . ?
N1A H1NA 0.87(2) . ?
C1A C8A 1.381(3) . ?
C1A C2A 1.381(3) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.369(3) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.391(3) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.368(3) . ?
C4A H4A 0.9300 . ?
C5A C8A 1.377(3) . ?
C6A C7A 1.517(3) . ?
C7A C8A 1.508(3) . ?
C7A H7AA 0.9700 . ?
C7A H7BA 0.9700 . ?

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
C6 N1 C5 111.7(2) . . ?
C6 N1 H1N 120.9(13) . . ?
C5 N1 H1N 126.5(13) . . ?
C8 C1 C2 118.3(2) . . ?
C8 C1 H1 120.9 . . ?
C2 C1 H1 120.9 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.6(2) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
C4 C5 C8 122.7(2) . . ?
C4 C5 N1 127.8(2) . . ?
C8 C5 N1 109.4(2) . . ?
O1 C6 N1 125.4(2) . . ?
O1 C6 C7 126.8(2) . . ?
N1 C6 C7 107.8(2) . . ?
C8 C7 C6 102.63(19) . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
C6 C7 H7B 111.2 . . ?
H7A C7 H7B 109.2 . . ?
C1 C8 C5 120.0(2) . . ?
C1 C8 C7 131.6(2) . . ?
C5 C8 C7 108.41(19) . . ?
C6A N1A C5A 111.55(19) . . ?
C6A N1A H1NA 122.3(15) . . ?
C5A N1A H1NA 126.1(15) . . ?
C8A C1A C2A 118.8(2) . . ?
C8A C1A H1A 120.6 . . ?
C2A C1A H1A 120.6 . . ?
C3A C2A C1A 120.9(2) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C2A C3A C4A 120.8(2) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A H3A 119.6 . . ?
C5A C4A C3A 117.5(2) . . ?
C5A C4A H4A 121.3 . . ?
C3A C4A H4A 121.3 . . ?
C4A C5A C8A 122.5(2) . . ?
C4A C5A N1A 128.0(2) . . ?
C8A C5A N1A 109.5(2) . . ?
O1A C6A N1A 125.0(2) . . ?
O1A C6A C7A 127.4(2) . . ?
N1A C6A C7A 107.6(2) . . ?
C8A C7A C6A 103.0(2) . . ?
C8A C7A H7AA 111.2 . . ?
C6A C7A H7AA 111.2 . . ?
C8A C7A H7BA 111.2 . . ?
C6A C7A H7BA 111.2 . . ?
H7AA C7A H7BA 109.1 . . ?
C5A C8A C1A 119.5(2) . . ?
C5A C8A C7A 108.3(2) . . ?
C1A C8A C7A 132.2(2) . . ?

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
C8 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C8 -0.2(3) . . . . ?
C3 C4 C5 N1 177.9(2) . . . . ?
C6 N1 C5 C4 -178.7(2) . . . . ?
C6 N1 C5 C8 -0.3(3) . . . . ?
C5 N1 C6 O1 -179.4(2) . . . . ?
C5 N1 C6 C7 0.1(3) . . . . ?
O1 C6 C7 C8 179.7(2) . . . . ?
N1 C6 C7 C8 0.2(3) . . . . ?
C2 C1 C8 C5 0.4(3) . . . . ?
C2 C1 C8 C7 -178.2(3) . . . . ?
C4 C5 C8 C1 -0.1(4) . . . . ?
N1 C5 C8 C1 -178.5(2) . . . . ?
C4 C5 C8 C7 178.9(2) . . . . ?
N1 C5 C8 C7 0.4(3) . . . . ?
C6 C7 C8 C1 178.4(2) . . . . ?
C6 C7 C8 C5 -0.3(3) . . . . ?
C8A C1A C2A C3A 0.4(4) . . . . ?
C1A C2A C3A C4A -0.5(4) . . . . ?
C2A C3A C4A C5A 0.6(4) . . . . ?
C3A C4A C5A C8A -0.4(4) . . . . ?
C3A C4A C5A N1A 179.5(2) . . . . ?
C6A N1A C5A C4A 179.9(2) . . . . ?
C6A N1A C5A C8A -0.2(3) . . . . ?
C5A N1A C6A O1A -179.4(2) . . . . ?
C5A N1A C6A C7A 0.8(3) . . . . ?
O1A C6A C7A C8A 179.1(3) . . . . ?
N1A C6A C7A C8A -1.1(3) . . . . ?
C4A C5A C8A C1A 0.2(4) . . . . ?
N1A C5A C8A C1A -179.7(2) . . . . ?
C4A C5A C8A C7A 179.3(2) . . . . ?
N1A C5A C8A C7A -0.6(3) . . . . ?
C2A C1A C8A C5A -0.2(4) . . . . ?
C2A C1A C8A C7A -179.0(3) . . . . ?
C6A C7A C8A C5A 1.0(3) . . . . ?
C6A C7A C8A C1A 179.9(3) . . . . ?

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
N1 H1N O1A 0.90(2) 1.97(2) 2.869(2) 170.5(19) 4_566
N1A H1NA O1 0.87(2) 1.98(2) 2.843(2) 170(2) 4_565

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_shelxl2
_audit_block_doi                 10.5517/ccwfk94
_database_code_depnum_ccdc_archive 'CCDC 817386'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp206073v 2011
_audit_update_record             
;
2011-03-14 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;
#TrackingRef 'flch11hb1_100k.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
indolin-2-one
;
_chemical_name_common            2-oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   12.8234(3)
_cell_length_b                   8.0674(2)
_cell_length_c                   13.4505(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.531(2)
_cell_angle_gamma                90.00
_cell_volume                     1294.38(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    5826
_cell_measurement_theta_min      2.5196
_cell_measurement_theta_max      34.4168

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(1)
_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  
;
Oxford Diffraction Diffractometer with Sapphire3 detector
;
_diffrn_measurement_method       'ω - scan'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8307
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2296
_reflns_number_gt                1930
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0558P)²+0.0526P] 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       0.0127(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_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
O1 O 0.33469(6) 1.02828(10) 1.10513(6) 0.0225(2) Uani 1 1 d . . .
N1 N 0.20223(8) 0.95077(12) 0.94410(8) 0.0184(2) Uani 1 1 d . . .
H1N H 0.2407(11) 0.9845(16) 0.9060(10) 0.022 Uiso 1 1 d . . .
C1 C 0.10037(9) 0.86384(14) 0.90704(9) 0.0167(3) Uani 1 1 d . . .
C2 C 0.03277(9) 0.82820(14) 0.80257(9) 0.0193(3) Uani 1 1 d . . .
H2 H 0.0525 0.8625 0.7442 0.023 Uiso 1 1 calc R . .
C3 C -0.06542(10) 0.73994(15) 0.78656(9) 0.0215(3) Uani 1 1 d . . .
H3 H -0.1137 0.7135 0.7158 0.026 Uiso 1 1 calc R . .
C4 C -0.09408(10) 0.68987(16) 0.87169(10) 0.0244(3) Uani 1 1 d . . .
H4 H -0.1614 0.6296 0.8587 0.029 Uiso 1 1 calc R . .
C5 C -0.02463(10) 0.72745(15) 0.97642(9) 0.0236(3) Uani 1 1 d . . .
H5 H -0.0441 0.6930 1.0349 0.028 Uiso 1 1 calc R . .
C6 C 0.07275(9) 0.81546(14) 0.99377(9) 0.0182(3) Uani 1 1 d . . .
C7 C 0.16317(9) 0.87745(15) 1.09389(9) 0.0207(3) Uani 1 1 d . . .
H7A H 0.1994 0.7847 1.1425 0.025 Uiso 1 1 calc R . .
H7B H 0.1327 0.9573 1.1322 0.025 Uiso 1 1 calc R . .
C8 C 0.24513(9) 0.96146(14) 1.05209(9) 0.0179(3) Uani 1 1 d . . .
O1A O 0.67182(7) 0.93105(10) 1.17230(6) 0.0234(2) Uani 1 1 d . . .
N1A N 0.54255(8) 0.81507(12) 1.02039(7) 0.0178(2) Uani 1 1 d . . .
H1NA H 0.5712(11) 0.8566(15) 0.9751(10) 0.021 Uiso 1 1 d . . .
C1A C 0.44978(9) 0.70773(14) 0.99428(9) 0.0163(3) Uani 1 1 d . . .
C2A C 0.37992(9) 0.65256(15) 0.89530(9) 0.0198(3) Uani 1 1 d . . .
H2A H 0.3901 0.6870 0.8319 0.024 Uiso 1 1 calc R . .
C3A C 0.29400(10) 0.54455(15) 0.89152(10) 0.0229(3) Uani 1 1 d . . .
H3A H 0.2448 0.5040 0.8244 0.028 Uiso 1 1 calc R . .
C4A C 0.27894(10) 0.49496(16) 0.98418(10) 0.0237(3) Uani 1 1 d . . .
H4A H 0.2200 0.4205 0.9798 0.028 Uiso 1 1 calc R . .
C5A C 0.34958(10) 0.55355(15) 1.08358(10) 0.0216(3) Uani 1 1 d . . .
H5A H 0.3389 0.5204 1.1470 0.026 Uiso 1 1 calc R . .
C6A C 0.43530(9) 0.66063(14) 1.08837(9) 0.0177(3) Uani 1 1 d . . .
C7A C 0.52380(10) 0.74474(16) 1.18044(9) 0.0200(3) Uani 1 1 d . . .
H7AA H 0.5744(11) 0.6692(16) 1.2344(10) 0.024 Uiso 1 1 d . . .
H7BA H 0.4920(11) 0.8203(17) 1.2181(10) 0.024 Uiso 1 1 d . . .
C8A C 0.58975(9) 0.84175(14) 1.12712(9) 0.0179(3) Uani 1 1 d . . .


_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 1.2317(14) . ?
N1 C8 1.3540(15) . ?
N1 C1 1.4030(14) . ?
N1 H1N 0.875(14) . ?
C1 C2 1.3836(15) . ?
C1 C6 1.3936(16) . ?
C2 C3 1.3927(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3850(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3959(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3798(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5039(15) . ?
C7 C8 1.5210(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O1A C8A 1.2355(14) . ?
N1A C8A 1.3549(14) . ?
N1A C1A 1.4078(15) . ?
N1A H1NA 0.885(14) . ?
C1A C2A 1.3776(16) . ?
C1A C6A 1.3975(15) . ?
C2A C3A 1.3910(17) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3883(18) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3937(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3808(16) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.5001(16) . ?
C7A C8A 1.5123(16) . ?
C7A H7AA 0.986(13) . ?
C7A H7BA 0.973(14) . ?

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
C8 N1 C1 111.82(10) . . ?
C8 N1 H1N 120.9(8) . . ?
C1 N1 H1N 126.8(8) . . ?
C2 C1 C6 122.34(11) . . ?
C2 C1 N1 128.27(11) . . ?
C6 C1 N1 109.39(10) . . ?
C1 C2 C3 117.21(11) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 121.35(11) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.42(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.02(11) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 119.65(10) . . ?
C5 C6 C7 132.46(10) . . ?
C1 C6 C7 107.89(10) . . ?
C6 C7 C8 103.15(9) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
O1 C8 N1 125.07(11) . . ?
O1 C8 C7 127.21(10) . . ?
N1 C8 C7 107.72(9) . . ?
C8A N1A C1A 111.71(10) . . ?
C8A N1A H1NA 122.2(8) . . ?
C1A N1A H1NA 126.0(8) . . ?
C2A C1A C6A 122.14(11) . . ?
C2A C1A N1A 129.05(10) . . ?
C6A C1A N1A 108.80(10) . . ?
C1A C2A C3A 117.58(11) . . ?
C1A C2A H2A 121.2 . . ?
C3A C2A H2A 121.2 . . ?
C4A C3A C2A 121.14(11) . . ?
C4A C3A H3A 119.4 . . ?
C2A C3A H3A 119.4 . . ?
C3A C4A C5A 120.52(11) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 118.88(11) . . ?
C6A C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
C5A C6A C1A 119.73(10) . . ?
C5A C6A C7A 132.04(10) . . ?
C1A C6A C7A 108.23(10) . . ?
C6A C7A C8A 103.17(9) . . ?
C6A C7A H7AA 115.0(7) . . ?
C8A C7A H7AA 109.7(8) . . ?
C6A C7A H7BA 112.3(7) . . ?
C8A C7A H7BA 109.7(8) . . ?
H7AA C7A H7BA 106.9(10) . . ?
O1A C8A N1A 125.62(11) . . ?
O1A C8A C7A 126.31(10) . . ?
N1A C8A C7A 108.07(10) . . ?

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
C8 N1 C1 C2 -179.87(11) . . . . ?
C8 N1 C1 C6 0.71(13) . . . . ?
C6 C1 C2 C3 -0.33(17) . . . . ?
N1 C1 C2 C3 -179.68(10) . . . . ?
C1 C2 C3 C4 -0.05(17) . . . . ?
C2 C3 C4 C5 0.15(18) . . . . ?
C3 C4 C5 C6 0.14(18) . . . . ?
C4 C5 C6 C1 -0.51(18) . . . . ?
C4 C5 C6 C7 178.87(12) . . . . ?
C2 C1 C6 C5 0.62(18) . . . . ?
N1 C1 C6 C5 -179.92(10) . . . . ?
C2 C1 C6 C7 -178.89(10) . . . . ?
N1 C1 C6 C7 0.57(13) . . . . ?
C5 C6 C7 C8 179.12(12) . . . . ?
C1 C6 C7 C8 -1.45(12) . . . . ?
C1 N1 C8 O1 178.48(11) . . . . ?
C1 N1 C8 C7 -1.65(13) . . . . ?
C6 C7 C8 O1 -178.27(11) . . . . ?
C6 C7 C8 N1 1.87(12) . . . . ?
C8A N1A C1A C2A 179.34(11) . . . . ?
C8A N1A C1A C6A -0.28(13) . . . . ?
C6A C1A C2A C3A -1.01(17) . . . . ?
N1A C1A C2A C3A 179.41(11) . . . . ?
C1A C2A C3A C4A 0.33(17) . . . . ?
C2A C3A C4A C5A 0.43(19) . . . . ?
C3A C4A C5A C6A -0.52(18) . . . . ?
C4A C5A C6A C1A -0.14(17) . . . . ?
C4A C5A C6A C7A 179.80(12) . . . . ?
C2A C1A C6A C5A 0.93(17) . . . . ?
N1A C1A C6A C5A -179.42(10) . . . . ?
C2A C1A C6A C7A -179.02(10) . . . . ?
N1A C1A C6A C7A 0.63(12) . . . . ?
C5A C6A C7A C8A 179.35(12) . . . . ?
C1A C6A C7A C8A -0.71(12) . . . . ?
C1A N1A C8A O1A -179.66(11) . . . . ?
C1A N1A C8A C7A -0.19(13) . . . . ?
C6A C7A C8A O1A -179.99(11) . . . . ?
C6A C7A C8A N1A 0.54(12) . . . . ?

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
N1 H1N O1A 0.875(14) 1.924(14) 2.7973(13) 176.8(12) 3_677
N1A H1NA O1 0.885(14) 2.107(14) 2.9794(13) 168.6(11) 3_677
C7A H7AA O1 0.986(13) 2.337(13) 3.2892(14) 161.9(10) 2_647

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_shelxl5
_audit_block_doi                 10.5517/ccwfkd7
_database_code_depnum_ccdc_archive 'CCDC 817389'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp206073v 2011
_audit_update_record             
;
2011-03-14 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;
#TrackingRef 'flch11hb3_295K.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
indolin-2-one
;
_chemical_name_common            2-oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6520(5)
_cell_length_b                   13.1283(18)
_cell_length_c                   14.9297(10)
_cell_angle_alpha                114.314(19)
_cell_angle_beta                 100.619(10)
_cell_angle_gamma                91.595(9)
_cell_volume                     985.6(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    3135
_cell_measurement_theta_min      3.0598
_cell_measurement_theta_max      34.4802

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9478
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(1)
_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  
;
Oxford Diffraction Diffractometer with Sapphire3 detector
;
_diffrn_measurement_method       'ω - scan'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6889
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.06
_reflns_number_total             3423
_reflns_number_gt                2614
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0460P)²+0.0000P] 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       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3423
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
O1 O 0.80984(16) 0.74702(8) 0.23807(7) 0.0538(3) Uani 1 1 d . . .
N1 N 0.55863(18) 0.59280(9) 0.21115(8) 0.0389(3) Uani 1 1 d . . .
H1N H 0.475(2) 0.6239(11) 0.2554(10) 0.047 Uiso 1 1 d . . .
C1 C 0.5154(2) 0.47860(10) 0.14537(8) 0.0325(3) Uani 1 1 d . . .
C2 C 0.3444(2) 0.39860(11) 0.13981(10) 0.0404(3) Uani 1 1 d . . .
H2 H 0.2389 0.4165 0.1837 0.049 Uiso 1 1 calc R . .
C3 C 0.3352(2) 0.29035(11) 0.06648(10) 0.0472(3) Uani 1 1 d . . .
H3 H 0.2203 0.2345 0.0605 0.057 Uiso 1 1 calc R . .
C4 C 0.4932(2) 0.26384(11) 0.00231(10) 0.0481(3) Uani 1 1 d . . .
H4 H 0.4845 0.1904 -0.0461 0.058 Uiso 1 1 calc R . .
C5 C 0.6652(2) 0.34571(11) 0.00923(9) 0.0416(3) Uani 1 1 d . . .
H5 H 0.7720 0.3276 -0.0341 0.050 Uiso 1 1 calc R . .
C6 C 0.6759(2) 0.45393(10) 0.08101(8) 0.0326(3) Uani 1 1 d . . .
C7 C 0.8305(2) 0.56080(10) 0.10689(9) 0.0356(3) Uani 1 1 d . . .
H7A H 0.8103 0.5801 0.0500 0.043 Uiso 1 1 calc R . .
H7B H 1.0003 0.5544 0.1277 0.043 Uiso 1 1 calc R . .
C8 C 0.7389(2) 0.64711(11) 0.19257(9) 0.0372(3) Uani 1 1 d . . .
O1A O 0.18529(17) 0.63712(9) 0.32606(7) 0.0553(3) Uani 1 1 d . . .
N1A N -0.00653(18) 0.70666(9) 0.45821(8) 0.0399(3) Uani 1 1 d . . .
H1NA H -0.103(2) 0.7449(11) 0.4384(10) 0.048 Uiso 1 1 d . . .
C1A C 0.0059(2) 0.70139(10) 0.55082(8) 0.0329(3) Uani 1 1 d . . .
C2A C -0.1293(2) 0.74999(11) 0.62195(9) 0.0417(3) Uani 1 1 d . . .
H2A H -0.2495 0.7939 0.6128 0.050 Uiso 1 1 calc R . .
C3A C -0.0794(2) 0.73098(11) 0.70787(10) 0.0468(3) Uani 1 1 d . . .
H3A H -0.1698 0.7618 0.7568 0.056 Uiso 1 1 calc R . .
C4A C 0.1008(2) 0.66756(12) 0.72226(10) 0.0482(3) Uani 1 1 d . . .
H4A H 0.1334 0.6576 0.7813 0.058 Uiso 1 1 calc R . .
C5A C 0.2337(2) 0.61857(11) 0.64974(9) 0.0441(3) Uani 1 1 d . . .
H5A H 0.3545 0.5752 0.6594 0.053 Uiso 1 1 calc R . .
C6A C 0.1855(2) 0.63461(10) 0.56319(9) 0.0336(3) Uani 1 1 d . . .
C7A C 0.2913(2) 0.59375(11) 0.47161(9) 0.0383(3) Uani 1 1 d . . .
H7AA H 0.2653 0.5123 0.4366 0.046 Uiso 1 1 calc R . .
H7BA H 0.4637 0.6181 0.4890 0.046 Uiso 1 1 calc R . .
C8A C 0.1558(2) 0.64683(11) 0.40829(9) 0.0379(3) Uani 1 1 d . . .
O1B O 0.60916(18) 0.85087(9) 0.44721(7) 0.0663(3) Uani 1 1 d . . .
N1B N 0.3302(2) 0.86557(9) 0.32187(8) 0.0441(3) Uani 1 1 d . . .
H1NB H 0.215(2) 0.8129(12) 0.3161(10) 0.053 Uiso 1 1 d . . .
C1B C 0.3208(2) 0.92087(10) 0.25842(9) 0.0383(3) Uani 1 1 d . . .
C2B C 0.1364(2) 0.91164(12) 0.18060(11) 0.0479(3) Uani 1 1 d . . .
H2B H -0.012(3) 0.8662(11) 0.1649(10) 0.057 Uiso 1 1 d . . .
C3B C 0.1744(3) 0.97251(13) 0.12692(12) 0.0584(4) Uani 1 1 d . . .
H3B H 0.0527 0.9681 0.0738 0.070 Uiso 1 1 calc R . .
C4B C 0.3886(3) 1.03952(12) 0.15047(12) 0.0620(4) Uani 1 1 d . . .
H4B H 0.4111 1.0785 0.1124 0.074 Uiso 1 1 calc R . .
C5B C 0.5706(3) 1.04931(11) 0.23038(12) 0.0551(4) Uani 1 1 d . . .
H5B H 0.7145 1.0955 0.2469 0.066 Uiso 1 1 calc R . .
C6B C 0.5360(2) 0.98996(10) 0.28506(10) 0.0420(3) Uani 1 1 d . . .
C7B C 0.6915(3) 0.98088(12) 0.37310(11) 0.0504(4) Uani 1 1 d . . .
H7AB H 0.715(2) 1.0509(13) 0.4345(11) 0.061 Uiso 1 1 d . . .
H7BB H 0.855(3) 0.9619(12) 0.3630(10) 0.061 Uiso 1 1 d . . .
C8B C 0.5472(2) 0.89216(11) 0.38748(10) 0.0463(3) Uani 1 1 d . . .


_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 1.2162(15) . ?
N1 C8 1.3601(16) . ?
N1 C1 1.3966(16) . ?
N1 H1N 0.856(12) . ?
C1 C2 1.3731(17) . ?
C1 C6 1.3905(16) . ?
C2 C3 1.3837(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.3762(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3875(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3740(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.4973(17) . ?
C7 C8 1.5071(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1A C8A 1.2243(14) . ?
N1A C8A 1.3507(16) . ?
N1A C1A 1.4016(15) . ?
N1A H1NA 0.846(14) . ?
C1A C2A 1.3738(16) . ?
C1A C6A 1.3950(16) . ?
C2A C3A 1.3862(18) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.3752(19) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3794(18) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3733(16) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.4933(16) . ?
C7A C8A 1.5068(17) . ?
C7A H7AA 0.9700 . ?
C7A H7BA 0.9700 . ?
O1B C8B 1.2269(16) . ?
N1B C8B 1.3556(17) . ?
N1B C1B 1.4062(16) . ?
N1B H1NB 0.903(14) . ?
C1B C2B 1.3713(18) . ?
C1B C6B 1.3873(17) . ?
C2B C3B 1.3813(19) . ?
C2B H2B 0.949(14) . ?
C3B C4B 1.375(2) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.383(2) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.3733(19) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.491(2) . ?
C7B C8B 1.512(2) . ?
C7B H7AB 0.978(15) . ?
C7B H7BB 0.986(14) . ?

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
C8 N1 C1 111.93(10) . . ?
C8 N1 H1N 125.3(9) . . ?
C1 N1 H1N 122.7(9) . . ?
C2 C1 C6 122.39(11) . . ?
C2 C1 N1 128.37(11) . . ?
C6 C1 N1 109.24(10) . . ?
C1 C2 C3 117.47(12) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.15(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.58(12) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.14(12) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.27(11) . . ?
C5 C6 C7 132.93(11) . . ?
C1 C6 C7 107.79(10) . . ?
C6 C7 C8 103.75(9) . . ?
C6 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
O1 C8 N1 125.20(11) . . ?
O1 C8 C7 127.52(11) . . ?
N1 C8 C7 107.28(11) . . ?
C8A N1A C1A 111.91(10) . . ?
C8A N1A H1NA 125.7(9) . . ?
C1A N1A H1NA 122.4(9) . . ?
C2A C1A C6A 121.92(11) . . ?
C2A C1A N1A 129.15(11) . . ?
C6A C1A N1A 108.93(10) . . ?
C1A C2A C3A 117.36(12) . . ?
C1A C2A H2A 121.3 . . ?
C3A C2A H2A 121.3 . . ?
C4A C3A C2A 121.42(11) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C3A C4A C5A 120.51(12) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 119.26(12) . . ?
C6A C5A H5A 120.4 . . ?
C4A C5A H5A 120.4 . . ?
C5A C6A C1A 119.51(11) . . ?
C5A C6A C7A 132.68(11) . . ?
C1A C6A C7A 107.80(10) . . ?
C6A C7A C8A 103.69(9) . . ?
C6A C7A H7AA 111.0 . . ?
C8A C7A H7AA 111.0 . . ?
C6A C7A H7BA 111.0 . . ?
C8A C7A H7BA 111.0 . . ?
H7AA C7A H7BA 109.0 . . ?
O1A C8A N1A 125.88(12) . . ?
O1A C8A C7A 126.48(11) . . ?
N1A C8A C7A 107.64(10) . . ?
C8B N1B C1B 111.45(12) . . ?
C8B N1B H1NB 122.9(9) . . ?
C1B N1B H1NB 125.3(9) . . ?
C2B C1B C6B 122.38(13) . . ?
C2B C1B N1B 128.32(12) . . ?
C6B C1B N1B 109.30(11) . . ?
C1B C2B C3B 117.30(14) . . ?
C1B C2B H2B 121.4(8) . . ?
C3B C2B H2B 121.3(8) . . ?
C4B C3B C2B 121.35(14) . . ?
C4B C3B H3B 119.3 . . ?
C2B C3B H3B 119.3 . . ?
C3B C4B C5B 120.48(14) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B H4B 119.8 . . ?
C6B C5B C4B 119.10(14) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C5B C6B C1B 119.37(13) . . ?
C5B C6B C7B 132.73(13) . . ?
C1B C6B C7B 107.89(12) . . ?
C6B C7B C8B 103.69(11) . . ?
C6B C7B H7AB 112.5(8) . . ?
C8B C7B H7AB 108.4(8) . . ?
C6B C7B H7BB 113.3(8) . . ?
C8B C7B H7BB 113.0(9) . . ?
H7AB C7B H7BB 106.1(12) . . ?
O1B C8B N1B 125.04(14) . . ?
O1B C8B C7B 127.59(13) . . ?
N1B C8B C7B 107.36(12) . . ?

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
C8 N1 C1 C2 -178.16(12) . . . . ?
C8 N1 C1 C6 1.30(14) . . . . ?
C6 C1 C2 C3 -0.29(18) . . . . ?
N1 C1 C2 C3 179.11(11) . . . . ?
C1 C2 C3 C4 0.64(19) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.11(19) . . . . ?
C4 C5 C6 C1 0.45(18) . . . . ?
C4 C5 C6 C7 -178.13(12) . . . . ?
C2 C1 C6 C5 -0.26(18) . . . . ?
N1 C1 C6 C5 -179.76(10) . . . . ?
C2 C1 C6 C7 178.65(11) . . . . ?
N1 C1 C6 C7 -0.84(13) . . . . ?
C5 C6 C7 C8 178.86(12) . . . . ?
C1 C6 C7 C8 0.16(12) . . . . ?
C1 N1 C8 O1 178.99(11) . . . . ?
C1 N1 C8 C7 -1.16(13) . . . . ?
C6 C7 C8 O1 -179.56(12) . . . . ?
C6 C7 C8 N1 0.59(12) . . . . ?
C8A N1A C1A C2A -179.52(12) . . . . ?
C8A N1A C1A C6A -0.05(14) . . . . ?
C6A C1A C2A C3A 0.51(18) . . . . ?
N1A C1A C2A C3A 179.92(12) . . . . ?
C1A C2A C3A C4A 1.05(19) . . . . ?
C2A C3A C4A C5A -1.6(2) . . . . ?
C3A C4A C5A C6A 0.6(2) . . . . ?
C4A C5A C6A C1A 0.95(18) . . . . ?
C4A C5A C6A C7A -179.38(12) . . . . ?
C2A C1A C6A C5A -1.52(18) . . . . ?
N1A C1A C6A C5A 178.96(11) . . . . ?
C2A C1A C6A C7A 178.74(11) . . . . ?
N1A C1A C6A C7A -0.78(13) . . . . ?
C5A C6A C7A C8A -178.47(13) . . . . ?
C1A C6A C7A C8A 1.22(12) . . . . ?
C1A N1A C8A O1A -179.68(12) . . . . ?
C1A N1A C8A C7A 0.85(14) . . . . ?
C6A C7A C8A O1A 179.28(12) . . . . ?
C6A C7A C8A N1A -1.25(13) . . . . ?
C8B N1B C1B C2B 177.18(12) . . . . ?
C8B N1B C1B C6B -2.21(14) . . . . ?
C6B C1B C2B C3B 1.45(19) . . . . ?
N1B C1B C2B C3B -177.87(12) . . . . ?
C1B C2B C3B C4B 0.1(2) . . . . ?
C2B C3B C4B C5B -1.3(2) . . . . ?
C3B C4B C5B C6B 0.9(2) . . . . ?
C4B C5B C6B C1B 0.59(19) . . . . ?
C4B C5B C6B C7B 179.55(13) . . . . ?
C2B C1B C6B C5B -1.82(19) . . . . ?
N1B C1B C6B C5B 177.62(11) . . . . ?
C2B C1B C6B C7B 178.99(12) . . . . ?
N1B C1B C6B C7B -1.58(14) . . . . ?
C5B C6B C7B C8B -174.77(13) . . . . ?
C1B C6B C7B C8B 4.28(13) . . . . ?
C1B N1B C8B O1B -175.53(12) . . . . ?
C1B N1B C8B C7B 4.94(14) . . . . ?
C6B C7B C8B O1B 174.93(12) . . . . ?
C6B C7B C8B N1B -5.56(13) . . . . ?

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
N1 H1N O1A 0.856(12) 2.078(13) 2.8835(13) 156.5(12) .
N1A H1NA O1B 0.846(14) 2.156(14) 2.9467(15) 155.3(12) 1_455
N1B H1NB O1A 0.903(14) 2.375(14) 3.1154(16) 139.2(11) .
N1B H1NB O1 0.903(14) 2.330(14) 3.0695(15) 139.1(12) 1_455
C7B H7BB O1 0.986(14) 2.637(14) 3.0744(19) 107.1(10) .
C2B H2B O1 0.949(14) 2.525(14) 3.2716(18) 135.6(11) 1_455

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.026
####################################################################### 
# 
# 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_shelxl1
_audit_block_doi                 10.5517/ccwfk83
_database_code_depnum_ccdc_archive 'CCDC 817385'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jp206073v 2011
_audit_update_record             
;
2011-03-14 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;
#TrackingRef 'flch11hb1_295K.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
indolin-2-one
;
_chemical_name_common            2-oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   12.7471(5)
_cell_length_b                   8.2941(3)
_cell_length_c                   13.5772(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.406(5)
_cell_angle_gamma                90.00
_cell_volume                     1336.44(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    3042
_cell_measurement_theta_min      3.0417
_cell_measurement_theta_max      34.4746

_exptl_crystal_description       polyhedron
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_T_max  0.9687
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(1)
_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  
;
Oxford Diffraction Diffractometer with Sapphire3 detector
;
_diffrn_measurement_method       'ω - scan'
_diffrn_detector_area_resol_mean 16.0328
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8578
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2359
_reflns_number_gt                1565
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0208P)²+0.0526P] 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       0.0132(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2359
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_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
O1 O 0.33627(7) 1.02986(12) 1.10381(7) 0.0590(3) Uani 1 1 d . . .
N1 N 0.20373(9) 0.95517(15) 0.94423(9) 0.0468(3) Uani 1 1 d . . .
H1N H 0.2408(11) 0.9920(15) 0.9047(10) 0.056 Uiso 1 1 d . . .
C1 C 0.10263(10) 0.86847(15) 0.90743(10) 0.0415(3) Uani 1 1 d . . .
C2 C 0.03583(11) 0.83266(17) 0.80444(10) 0.0514(4) Uani 1 1 d . . .
H2 H 0.0553 0.8662 0.7480 0.062 Uiso 1 1 calc R . .
C3 C -0.06164(11) 0.74459(18) 0.78809(12) 0.0579(4) Uani 1 1 d . . .
H3 H -0.1087 0.7194 0.7194 0.070 Uiso 1 1 calc R . .
C4 C -0.08973(12) 0.69411(19) 0.87140(13) 0.0658(5) Uani 1 1 d . . .
H4 H -0.1553 0.6348 0.8587 0.079 Uiso 1 1 calc R . .
C5 C -0.02099(11) 0.73097(19) 0.97453(11) 0.0629(4) Uani 1 1 d . . .
H5 H -0.0399 0.6961 1.0310 0.075 Uiso 1 1 calc R . .
C6 C 0.07514(10) 0.81930(17) 0.99228(10) 0.0449(4) Uani 1 1 d . . .
C7 C 0.16541(10) 0.88053(17) 1.09167(10) 0.0519(4) Uani 1 1 d . . .
H7A H 0.2020 0.7923 1.1385 0.062 Uiso 1 1 calc R . .
H7B H 0.1345 0.9551 1.1291 0.062 Uiso 1 1 calc R . .
C8 C 0.24664(11) 0.96488(17) 1.05075(11) 0.0464(4) Uani 1 1 d . . .
O1A O 0.66837(8) 0.92661(13) 1.17101(7) 0.0621(3) Uani 1 1 d . . .
N1A N 0.53892(9) 0.81359(14) 1.02099(9) 0.0452(3) Uani 1 1 d . . .
H1NA H 0.5667(10) 0.8575(15) 0.9763(10) 0.054 Uiso 1 1 d . . .
C1A C 0.44724(10) 0.70634(16) 0.99525(10) 0.0406(3) Uani 1 1 d . . .
C2A C 0.37767(11) 0.65301(18) 0.89746(10) 0.0516(4) Uani 1 1 d . . .
H2A H 0.3869 0.6877 0.8360 0.062 Uiso 1 1 calc R . .
C3A C 0.29331(12) 0.54577(19) 0.89386(12) 0.0601(4) Uani 1 1 d . . .
H3A H 0.2452 0.5069 0.8288 0.072 Uiso 1 1 calc R . .
C4A C 0.27923(12) 0.49565(19) 0.98459(12) 0.0641(5) Uani 1 1 d . . .
H4A H 0.2219 0.4235 0.9802 0.077 Uiso 1 1 calc R . .
C5A C 0.34969(11) 0.55162(18) 1.08278(12) 0.0578(4) Uani 1 1 d . . .
H5A H 0.3400 0.5175 1.1442 0.069 Uiso 1 1 calc R . .
C6A C 0.43400(10) 0.65829(16) 1.08786(10) 0.0429(3) Uani 1 1 d . . .
C7A C 0.52210(12) 0.7405(2) 1.17864(11) 0.0499(4) Uani 1 1 d . . .
H7AA H 0.5714(10) 0.6688(16) 1.2298(10) 0.060 Uiso 1 1 d . . .
H7BA H 0.4903(10) 0.8168(16) 1.2171(10) 0.060 Uiso 1 1 d . . .
C8A C 0.58674(11) 0.83845(17) 1.12649(11) 0.0462(4) Uani 1 1 d . . .


_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 1.2304(14) . ?
N1 C8 1.3491(16) . ?
N1 C1 1.3991(16) . ?
N1 H1N 0.889(13) . ?
C1 C2 1.3782(16) . ?
C1 C6 1.3824(17) . ?
C2 C3 1.3875(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3879(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3715(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.5064(17) . ?
C7 C8 1.5134(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O1A C8A 1.2344(15) . ?
N1A C8A 1.3523(16) . ?
N1A C1A 1.4075(16) . ?
N1A H1NA 0.884(13) . ?
C1A C2A 1.3731(17) . ?
C1A C6A 1.3868(17) . ?
C2A C3A 1.3825(18) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.3726(19) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3876(18) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3741(18) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.4949(18) . ?
C7A C8A 1.5054(18) . ?
C7A H7AA 0.955(12) . ?
C7A H7BA 0.996(13) . ?

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
C8 N1 C1 111.94(12) . . ?
C8 N1 H1N 122.0(9) . . ?
C1 N1 H1N 125.7(8) . . ?
C2 C1 C6 122.09(13) . . ?
C2 C1 N1 128.36(13) . . ?
C6 C1 N1 109.55(12) . . ?
C1 C2 C3 117.48(13) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.14(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.43(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.31(14) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.54(12) . . ?
C5 C6 C7 132.76(13) . . ?
C1 C6 C7 107.70(12) . . ?
C6 C7 C8 103.20(11) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
O1 C8 N1 125.47(13) . . ?
O1 C8 C7 126.95(12) . . ?
N1 C8 C7 107.58(11) . . ?
C8A N1A C1A 111.83(11) . . ?
C8A N1A H1NA 121.7(9) . . ?
C1A N1A H1NA 126.4(8) . . ?
C2A C1A C6A 122.33(13) . . ?
C2A C1A N1A 128.93(12) . . ?
C6A C1A N1A 108.74(11) . . ?
C1A C2A C3A 117.45(13) . . ?
C1A C2A H2A 121.3 . . ?
C3A C2A H2A 121.3 . . ?
C4A C3A C2A 121.19(14) . . ?
C4A C3A H3A 119.4 . . ?
C2A C3A H3A 119.4 . . ?
C3A C4A C5A 120.67(15) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C6A C5A C4A 118.93(14) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C5A C6A C1A 119.42(13) . . ?
C5A C6A C7A 132.33(12) . . ?
C1A C6A C7A 108.25(12) . . ?
C6A C7A C8A 103.52(11) . . ?
C6A C7A H7AA 114.4(8) . . ?
C8A C7A H7AA 110.5(8) . . ?
C6A C7A H7BA 113.3(7) . . ?
C8A C7A H7BA 107.5(8) . . ?
H7AA C7A H7BA 107.4(11) . . ?
O1A C8A N1A 125.63(13) . . ?
O1A C8A C7A 126.71(12) . . ?
N1A C8A C7A 107.66(12) . . ?

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
C8 N1 C1 C2 -179.27(13) . . . . ?
C8 N1 C1 C6 0.83(16) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C2 C3 -179.76(13) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 179.15(14) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
N1 C1 C6 C5 -179.58(13) . . . . ?
C2 C1 C6 C7 -179.42(12) . . . . ?
N1 C1 C6 C7 0.50(15) . . . . ?
C5 C6 C7 C8 178.65(15) . . . . ?
C1 C6 C7 C8 -1.45(15) . . . . ?
C1 N1 C8 O1 177.68(13) . . . . ?
C1 N1 C8 C7 -1.76(15) . . . . ?
C6 C7 C8 O1 -177.50(13) . . . . ?
C6 C7 C8 N1 1.93(15) . . . . ?
C8A N1A C1A C2A 179.44(13) . . . . ?
C8A N1A C1A C6A -0.01(15) . . . . ?
C6A C1A C2A C3A -1.0(2) . . . . ?
N1A C1A C2A C3A 179.60(13) . . . . ?
C1A C2A C3A C4A 0.5(2) . . . . ?
C2A C3A C4A C5A 0.0(2) . . . . ?
C3A C4A C5A C6A 0.0(2) . . . . ?
C4A C5A C6A C1A -0.5(2) . . . . ?
C4A C5A C6A C7A 179.70(14) . . . . ?
C2A C1A C6A C5A 1.0(2) . . . . ?
N1A C1A C6A C5A -179.46(12) . . . . ?
C2A C1A C6A C7A -179.12(13) . . . . ?
N1A C1A C6A C7A 0.37(15) . . . . ?
C5A C6A C7A C8A 179.25(14) . . . . ?
C1A C6A C7A C8A -0.56(15) . . . . ?
C1A N1A C8A O1A 179.98(13) . . . . ?
C1A N1A C8A C7A -0.36(15) . . . . ?
C6A C7A C8A O1A -179.79(13) . . . . ?
C6A C7A C8A N1A 0.55(15) . . . . ?

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
N1 H1N O1A 0.889(13) 1.929(13) 2.8159(15) 175.4(12) 3_677
N1A H1NA O1 0.884(13) 2.138(13) 3.0093(15) 168.4(11) 3_677
C7A H7AA O1 0.955(12) 2.424(13) 3.3382(17) 160.2(11) 2_647

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.024
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1526388'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-oxindole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.2387(7)
_cell_length_b                   7.2236(4)
_cell_length_c                   8.0822(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.325(6)
_cell_angle_gamma                90
_cell_volume                     695.29(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(1)
_cell_measurement_reflns_used    1200
_cell_measurement_theta_min      3.8190
_cell_measurement_theta_max      24.2770

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41q (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
SuperNova diffractometer (Agilent Technologies) with Atlas detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_reflns_number            5463
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.298
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1417
_reflns_number_gt                888
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+0.0023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1417
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1220
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_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 0.51735(12) 0.2434(2) 0.72794(17) 0.0776(5) Uani 1 1 d . . . . .
N1 N 0.38930(12) 0.4419(2) 0.57493(17) 0.0558(5) Uani 1 1 d . . . . .
H1 H 0.4195 0.5424 0.6209 0.067 Uiso 1 1 calc R U . . .
C1 C 0.29087(15) 0.4358(3) 0.4469(2) 0.0530(5) Uani 1 1 d . . . . .
C2 C 0.22466(19) 0.5795(3) 0.3716(3) 0.0747(7) Uani 1 1 d . . . . .
H2 H 0.2426 0.7015 0.4034 0.090 Uiso 1 1 calc R U . . .
C3 C 0.1305(2) 0.5371(5) 0.2471(3) 0.0885(8) Uani 1 1 d . . . . .
H3 H 0.0841 0.6319 0.1937 0.106 Uiso 1 1 calc R U . . .
C4 C 0.10430(19) 0.3569(5) 0.2011(3) 0.0871(8) Uani 1 1 d . . . . .
H4 H 0.0402 0.3311 0.1172 0.105 Uiso 1 1 calc R U . . .
C5 C 0.17229(18) 0.2124(4) 0.2781(2) 0.0734(7) Uani 1 1 d . . . . .
H5 H 0.1543 0.0906 0.2457 0.088 Uiso 1 1 calc R U . . .
C6 C 0.26575(15) 0.2514(3) 0.4020(2) 0.0558(5) Uani 1 1 d . . . . .
C7 C 0.35519(16) 0.1327(3) 0.5096(2) 0.0596(6) Uani 1 1 d . . . . .
H7A H 0.3951 0.0623 0.4399 0.072 Uiso 1 1 calc R U . . .
H7B H 0.3236 0.0480 0.5792 0.072 Uiso 1 1 calc R U . . .
C8 C 0.43123(16) 0.2723(3) 0.6178(2) 0.0561(5) Uani 1 1 d . . . . .


_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 1.231(2) . ?
N1 C8 1.342(2) . ?
N1 C1 1.396(2) . ?
N1 H1 0.8600 . ?
C1 C2 1.370(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(3) . ?
C7 C8 1.507(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C8 N1 C1 112.08(15) . . ?
C8 N1 H1 124.0 . . ?
C1 N1 H1 124.0 . . ?
C2 C1 C6 122.36(19) . . ?
C2 C1 N1 128.79(19) . . ?
C6 C1 N1 108.85(16) . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 118.99(19) . . ?
C5 C6 C7 133.1(2) . . ?
C1 C6 C7 107.89(15) . . ?
C6 C7 C8 102.96(16) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
O1 C8 N1 123.66(18) . . ?
O1 C8 C7 128.11(18) . . ?
N1 C8 C7 108.22(15) . . ?

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
C8 N1 C1 C2 179.73(18) . . . . ?
C8 N1 C1 C6 0.1(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
N1 C1 C2 C3 -179.79(17) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 179.72(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
N1 C1 C6 C5 -179.96(15) . . . . ?
C2 C1 C6 C7 -179.82(18) . . . . ?
N1 C1 C6 C7 -0.12(19) . . . . ?
C5 C6 C7 C8 179.94(19) . . . . ?
C1 C6 C7 C8 0.13(18) . . . . ?
C1 N1 C8 O1 -179.81(17) . . . . ?
C1 N1 C8 C7 0.0(2) . . . . ?
C6 C7 C8 O1 179.7(2) . . . . ?
C6 C7 C8 N1 -0.10(18) . . . . ?

_refine_diff_density_max         0.112
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1526389'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-indolinone
_chemical_name_common            oxindole
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.0455(3)
_cell_length_b                   7.0949(2)
_cell_length_c                   7.9670(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.314(3)
_cell_angle_gamma                90
_cell_volume                     667.64(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2870
_cell_measurement_theta_min      3.8780
_cell_measurement_theta_max      35.2610

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41q (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
SuperNova diffractometer (Agilent Technologies) with Atlas detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_reflns_number            5323
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.350
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1366
_reflns_number_gt                1164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.1430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1366
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_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 0.51600(7) 0.24339(12) 0.72192(11) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.38771(8) 0.44822(14) 0.57202(12) 0.0190(3) Uani 1 1 d . . . . .
H1 H 0.4181 0.5528 0.6196 0.023 Uiso 1 1 calc R U . . .
C1 C 0.28978(9) 0.44233(17) 0.44402(14) 0.0183(3) Uani 1 1 d . . . . .
C2 C 0.22410(10) 0.59072(18) 0.36983(15) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.2427 0.7173 0.4026 0.029 Uiso 1 1 calc R U . . .
C3 C 0.12938(10) 0.5477(2) 0.24492(16) 0.0276(3) Uani 1 1 d . . . . .
H3 H 0.0825 0.6467 0.1909 0.033 Uiso 1 1 calc R U . . .
C4 C 0.10243(10) 0.3622(2) 0.19815(15) 0.0273(3) Uani 1 1 d . . . . .
H4 H 0.0371 0.3358 0.1133 0.033 Uiso 1 1 calc R U . . .
C5 C 0.17030(10) 0.21409(19) 0.27456(15) 0.0237(3) Uani 1 1 d . . . . .
H5 H 0.1517 0.0874 0.2420 0.028 Uiso 1 1 calc R U . . .
C6 C 0.26485(10) 0.25421(17) 0.39823(14) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.35310(10) 0.13155(17) 0.50508(14) 0.0200(3) Uani 1 1 d . . . . .
H7A H 0.3950 0.0575 0.4325 0.024 Uiso 1 1 calc R U . . .
H7B H 0.3187 0.0443 0.5774 0.024 Uiso 1 1 calc R U . . .
C8 C 0.43002(10) 0.27393(16) 0.61383(15) 0.0192(3) Uani 1 1 d . . . . .


_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 1.2294(14) . ?
N1 C8 1.3540(15) . ?
N1 C1 1.4004(14) . ?
N1 H1 0.8800 . ?
C1 C2 1.3785(17) . ?
C1 C6 1.4006(17) . ?
C2 C3 1.3928(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3955(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3815(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5023(16) . ?
C7 C8 1.5214(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
C8 N1 C1 112.00(9) . . ?
C8 N1 H1 124.0 . . ?
C1 N1 H1 124.0 . . ?
C2 C1 N1 128.32(11) . . ?
C2 C1 C6 122.71(11) . . ?
N1 C1 C6 108.97(10) . . ?
C1 C2 C3 117.36(12) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 121.01(12) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.68(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.11(12) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.13(11) . . ?
C5 C6 C7 132.65(11) . . ?
C1 C6 C7 108.22(10) . . ?
C6 C7 C8 102.84(9) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
O1 C8 N1 123.92(11) . . ?
O1 C8 C7 128.11(10) . . ?
N1 C8 C7 107.97(9) . . ?

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
C8 N1 C1 C2 179.99(11) . . . . ?
C8 N1 C1 C6 0.30(13) . . . . ?
N1 C1 C2 C3 -179.46(10) . . . . ?
C6 C1 C2 C3 0.19(17) . . . . ?
C1 C2 C3 C4 0.27(18) . . . . ?
C2 C3 C4 C5 -0.47(18) . . . . ?
C3 C4 C5 C6 0.21(17) . . . . ?
C4 C5 C6 C1 0.23(16) . . . . ?
C4 C5 C6 C7 179.10(11) . . . . ?
C2 C1 C6 C5 -0.45(17) . . . . ?
N1 C1 C6 C5 179.27(9) . . . . ?
C2 C1 C6 C7 -179.57(10) . . . . ?
N1 C1 C6 C7 0.14(12) . . . . ?
C5 C6 C7 C8 -179.42(12) . . . . ?
C1 C6 C7 C8 -0.47(11) . . . . ?
C1 N1 C8 O1 179.42(10) . . . . ?
C1 N1 C8 C7 -0.60(12) . . . . ?
C6 C7 C8 O1 -179.38(11) . . . . ?
C6 C7 C8 N1 0.64(11) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.040

