# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-hydroxy-1-methylindolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N O2'
_chemical_formula_weight         163.17

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   P21/C

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                   7.8040(16)
_cell_length_b                   13.070(3)
_cell_length_c                   8.4480(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.64(3)
_cell_angle_gamma                90.00
_cell_volume                     816.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   '(North, Phillips & Mathews,1968)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            1608
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.41
_reflns_number_total             1498
_reflns_number_gt                1030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1498
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1547
_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
N N 0.2337(3) 0.39568(14) 0.0859(2) 0.0493(5) Uani 1 1 d . . .
C1 C 0.2163(3) 0.47655(16) -0.0304(3) 0.0481(6) Uani 1 1 d . . .
O1 O 0.3559(3) 0.59941(15) 0.3384(2) 0.0731(7) Uani 1 1 d . . .
H1A H 0.4397 0.6069 0.4257 0.110 Uiso 1 1 calc R . .
O2 O 0.3752(3) 0.36961(15) 0.3649(2) 0.0679(6) Uani 1 1 d . . .
C2 C 0.1139(4) 0.4800(2) -0.1966(3) 0.0600(7) Uani 1 1 d . . .
H2A H 0.0423 0.4250 -0.2487 0.072 Uiso 1 1 calc R . .
C3 C 0.1222(4) 0.5694(2) -0.2830(4) 0.0708(8) Uani 1 1 d . . .
H3A H 0.0537 0.5745 -0.3952 0.085 Uiso 1 1 calc R . .
C4 C 0.2293(4) 0.6508(2) -0.2067(4) 0.0682(8) Uani 1 1 d . . .
H4A H 0.2346 0.7089 -0.2686 0.082 Uiso 1 1 calc R . .
C5 C 0.3295(3) 0.6469(2) -0.0381(4) 0.0601(7) Uani 1 1 d . . .
H5A H 0.4003 0.7021 0.0138 0.072 Uiso 1 1 calc R . .
C6 C 0.3219(3) 0.55926(18) 0.0510(3) 0.0494(6) Uani 1 1 d . . .
C7 C 0.4097(3) 0.53251(18) 0.2315(3) 0.0522(6) Uani 1 1 d . . .
H7A H 0.5417 0.5327 0.2594 0.063 Uiso 1 1 calc R . .
C8 C 0.3410(3) 0.42343(19) 0.2399(3) 0.0512(6) Uani 1 1 d . . .
C9 C 0.1486(4) 0.2956(2) 0.0454(4) 0.0665(8) Uani 1 1 d . . .
H9A H 0.1806 0.2539 0.1440 0.100 Uiso 1 1 calc R . .
H9B H 0.1895 0.2633 -0.0381 0.100 Uiso 1 1 calc R . .
H9C H 0.0196 0.3037 0.0035 0.100 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N 0.0544(12) 0.0394(11) 0.0588(12) -0.0063(9) 0.0248(10) -0.0059(9)
C1 0.0480(13) 0.0434(14) 0.0586(14) -0.0035(11) 0.0252(11) 0.0020(10)
O1 0.0849(14) 0.0599(13) 0.0692(12) -0.0191(9) 0.0169(10) 0.0092(10)
O2 0.0854(14) 0.0570(11) 0.0602(11) 0.0038(9) 0.0217(10) -0.0057(9)
C2 0.0590(15) 0.0624(17) 0.0599(15) -0.0097(13) 0.0209(13) 0.0000(12)
C3 0.083(2) 0.069(2) 0.0610(17) 0.0078(15) 0.0238(15) 0.0143(16)
C4 0.0776(19) 0.0577(18) 0.0756(19) 0.0136(14) 0.0333(16) 0.0122(15)
C5 0.0618(16) 0.0429(14) 0.0801(19) 0.0010(12) 0.0290(15) 0.0010(11)
C6 0.0476(13) 0.0416(13) 0.0620(15) -0.0022(11) 0.0216(11) 0.0011(10)
C7 0.0520(14) 0.0416(14) 0.0637(15) -0.0061(11) 0.0193(12) -0.0011(10)
C8 0.0563(14) 0.0462(14) 0.0547(14) -0.0020(11) 0.0228(12) 0.0050(11)
C9 0.0805(19) 0.0475(15) 0.0771(18) -0.0130(13) 0.0333(15) -0.0146(13)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N C8 1.352(3) . ?
N C1 1.420(3) . ?
N C9 1.458(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.399(3) . ?
O1 C7 1.414(3) . ?
O1 H1A 0.8200 . ?
O2 C8 1.226(3) . ?
C2 C3 1.391(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.500(3) . ?
C7 C8 1.533(3) . ?
C7 H7A 0.9800 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N C1 111.04(19) . . ?
C8 N C9 124.2(2) . . ?
C1 N C9 124.7(2) . . ?
C2 C1 C6 122.3(2) . . ?
C2 C1 N 128.8(2) . . ?
C6 C1 N 108.9(2) . . ?
C7 O1 H1A 109.5 . . ?
C1 C2 C3 117.0(3) . . ?
C1 C2 H2A 121.5 . . ?
C3 C2 H2A 121.5 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 131.4(2) . . ?
C1 C6 C7 109.0(2) . . ?
O1 C7 C6 111.90(19) . . ?
O1 C7 C8 111.5(2) . . ?
C6 C7 C8 102.17(19) . . ?
O1 C7 H7A 110.4 . . ?
C6 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O2 C8 N 124.9(2) . . ?
O2 C8 C7 126.2(2) . . ?
N C8 C7 108.9(2) . . ?
N C9 H9A 109.5 . . ?
N C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N C1 C2 -177.2(2) . . . . ?
C9 N C1 C2 3.2(4) . . . . ?
C8 N C1 C6 2.0(3) . . . . ?
C9 N C1 C6 -177.6(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
N C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -1.8(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -178.8(2) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
N C1 C6 C5 178.8(2) . . . . ?
C2 C1 C6 C7 177.7(2) . . . . ?
N C1 C6 C7 -1.6(3) . . . . ?
C5 C6 C7 O1 60.9(3) . . . . ?
C1 C6 C7 O1 -118.7(2) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C1 C6 C7 C8 0.6(2) . . . . ?
C1 N C8 O2 177.8(2) . . . . ?
C9 N C8 O2 -2.5(4) . . . . ?
C1 N C8 C7 -1.5(3) . . . . ?
C9 N C8 C7 178.1(2) . . . . ?
O1 C7 C8 O2 -59.2(3) . . . . ?
C6 C7 C8 O2 -178.8(2) . . . . ?
O1 C7 C8 N 120.2(2) . . . . ?
C6 C7 C8 N 0.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, hexane'
_database_code_depnum_ccdc_archive 'CCDC 1016276'
