# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1508522'
_audit_update_record             
;
2016-10-06 deposited with the CCDC.
2016-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            N-acetyoxyindole
_chemical_melting_point          399
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18

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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4444(8)
_cell_length_b                   8.2789(9)
_cell_length_c                   13.8475(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.494(4)
_cell_angle_gamma                90
_cell_volume                     851.86(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6073
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.99

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8307
_exptl_absorpt_correction_T_max  0.9200
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21338
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.868
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1505
_reflns_number_gt                1300
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.1000P)²] 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         1505
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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
C6 C 0.27105(14) 0.53212(16) 0.53336(9) 0.0383(4) Uani 1 1 d . . . . .
C5 C 0.30224(17) 0.68194(17) 0.49296(10) 0.0440(4) Uani 1 1 d . . . . .
C3 C 0.3581(2) 0.6360(2) 0.68894(12) 0.0596(5) Uani 1 1 d . . . . .
H3 H 0.3775 0.6215 0.7554 0.071 Uiso 1 1 calc R U . . .
C1 C 0.3616(2) 0.80936(19) 0.55123(13) 0.0582(5) Uani 1 1 d . . . . .
H1 H 0.3822 0.9102 0.5244 0.070 Uiso 1 1 calc R U . . .
C2 C 0.3900(2) 0.7848(2) 0.64997(13) 0.0621(5) Uani 1 1 d . . . . .
H2 H 0.4307 0.8692 0.6898 0.075 Uiso 1 1 calc R U . . .
C4 C 0.29763(17) 0.5060(2) 0.63223(10) 0.0495(4) Uani 1 1 d . . . . .
H4 H 0.2759 0.4057 0.6594 0.059 Uiso 1 1 calc R U . . .
N1 N 0.21085(13) 0.42169(13) 0.45823(7) 0.0385(3) Uani 1 1 d . . . . .
C7 C 0.20619(17) 0.50197(19) 0.36771(9) 0.0447(4) Uani 1 1 d . . . . .
O1 O 0.16302(15) 0.44189(14) 0.29027(7) 0.0632(4) Uani 1 1 d . . . . .
C8 C 0.16155(18) 0.26027(17) 0.47398(10) 0.0459(4) Uani 1 1 d . . . . .
O2 O 0.16490(19) 0.20958(16) 0.55594(8) 0.0761(4) Uani 1 1 d . . . . .
C9 C 0.1062(2) 0.15717(19) 0.38969(11) 0.0573(4) Uani 1 1 d . . . . .
H9A H 0.0686 0.0535 0.4120 0.086 Uiso 1 1 calc R U . . .
H9B H 0.2060 0.1437 0.3496 0.086 Uiso 1 1 calc R U . . .
H9C H 0.0082 0.2076 0.3529 0.086 Uiso 1 1 calc R U . . .
C10 C 0.2614(2) 0.67439(19) 0.38573(11) 0.0535(4) Uani 1 1 d . . . . .
H10A H 0.3668 0.7013 0.3512 0.064 Uiso 1 1 calc R U . . .
H10B H 0.1646 0.7479 0.3658 0.064 Uiso 1 1 calc R U . . .

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
C6 0.0363(7) 0.0425(8) 0.0362(8) -0.0019(5) 0.0026(5) 0.0045(5)
C5 0.0422(7) 0.0418(8) 0.0486(8) 0.0012(6) 0.0075(6) 0.0030(5)
C3 0.0579(9) 0.0765(12) 0.0432(8) -0.0151(8) -0.0054(7) 0.0037(8)
C1 0.0535(8) 0.0459(9) 0.0761(12) -0.0074(8) 0.0098(7) -0.0039(7)
C2 0.0521(9) 0.0677(11) 0.0658(11) -0.0250(9) -0.0027(7) -0.0043(8)
C4 0.0549(8) 0.0557(10) 0.0376(8) -0.0004(6) 0.0003(6) 0.0025(6)
N1 0.0461(6) 0.0380(7) 0.0315(6) 0.0010(4) 0.0026(4) 0.0030(4)
C7 0.0509(8) 0.0490(9) 0.0346(8) 0.0048(6) 0.0055(6) 0.0091(6)
O1 0.0891(8) 0.0672(8) 0.0327(6) 0.0001(5) -0.0011(5) 0.0047(6)
C8 0.0521(8) 0.0432(9) 0.0426(8) 0.0026(6) 0.0064(6) 0.0006(6)
O2 0.1270(10) 0.0544(8) 0.0469(7) 0.0107(5) 0.0049(6) -0.0193(7)
C9 0.0654(9) 0.0495(9) 0.0573(10) -0.0082(7) 0.0066(7) -0.0067(7)
C10 0.0671(9) 0.0465(9) 0.0478(9) 0.0105(6) 0.0116(7) 0.0044(7)

_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
C6 C5 1.3861(19) . ?
C6 C4 1.3882(18) . ?
C6 N1 1.4360(16) . ?
C5 C1 1.384(2) . ?
C5 C10 1.499(2) . ?
C3 C2 1.372(3) . ?
C3 C4 1.391(2) . ?
C1 C2 1.386(2) . ?
N1 C8 1.4064(18) . ?
N1 C7 1.4173(17) . ?
C7 O1 1.2076(16) . ?
C7 C10 1.502(2) . ?
C8 O2 1.2089(16) . ?
C8 C9 1.4840(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 C4 121.33(13) . . ?
C5 C6 N1 109.26(11) . . ?
C4 C6 N1 129.41(13) . . ?
C1 C5 C6 120.14(14) . . ?
C1 C5 C10 130.37(14) . . ?
C6 C5 C10 109.49(12) . . ?
C2 C3 C4 122.05(15) . . ?
C5 C1 C2 119.17(16) . . ?
C3 C2 C1 120.03(15) . . ?
C6 C4 C3 117.28(15) . . ?
C8 N1 C7 126.17(11) . . ?
C8 N1 C6 124.43(10) . . ?
C7 N1 C6 109.39(11) . . ?
O1 C7 N1 125.66(14) . . ?
O1 C7 C10 126.45(13) . . ?
N1 C7 C10 107.88(11) . . ?
O2 C8 N1 119.00(12) . . ?
O2 C8 C9 121.84(14) . . ?
N1 C8 C9 119.16(12) . . ?
C5 C10 C7 103.96(11) . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.094

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL aa in P2(1)/n
CELL 0.71073   7.44440   8.27890  13.84750  90.0000  93.4939  90.0000
ZERR    4.00   0.00080   0.00090   0.00150   0.0000   0.0042   0.0000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 40  36  4  8
OMIT -3 50
L.S. 10
ACTA
BOND
FMAP 2
PLAN 5
TEMP 23.000
WGHT    0.100000
FVAR       0.28432
MOLE 1
C6    1    0.271054    0.532118    0.533361    11.00000    0.03628    0.04251 =
         0.03615   -0.00191    0.00256    0.00447
C5    1    0.302243    0.681940    0.492959    11.00000    0.04218    0.04185 =
         0.04857    0.00117    0.00746    0.00297
C3    1    0.358107    0.635980    0.688937    11.00000    0.05794    0.07652 =
         0.04317   -0.01513   -0.00537    0.00368
AFIX  43
H3    2    0.377523    0.621535    0.755356    11.00000   -1.20000
AFIX   0
C1    1    0.361611    0.809361    0.551226    11.00000    0.05345    0.04585 =
         0.07613   -0.00744    0.00984   -0.00387
AFIX  43
H1    2    0.382185    0.910204    0.524446    11.00000   -1.20000
AFIX   0
C2    1    0.390013    0.784793    0.649966    11.00000    0.05206    0.06769 =
         0.06584   -0.02503   -0.00269   -0.00427
AFIX  43
H2    2    0.430724    0.869245    0.689821    11.00000   -1.20000
AFIX   0
C4    1    0.297633    0.506030    0.632231    11.00000    0.05495    0.05567 =
         0.03757   -0.00035    0.00034    0.00247
AFIX  43
H4    2    0.275881    0.405738    0.659429    11.00000   -1.20000
AFIX   0
N1    3    0.210852    0.421692    0.458229    11.00000    0.04610    0.03805 =
         0.03145    0.00098    0.00264    0.00296
C7    1    0.206191    0.501965    0.367709    11.00000    0.05089    0.04898 =
         0.03457    0.00477    0.00554    0.00906
O1    4    0.163016    0.441893    0.290274    11.00000    0.08911    0.06722 =
         0.03271    0.00005   -0.00106    0.00474
C8    1    0.161550    0.260270    0.473978    11.00000    0.05212    0.04325 =
         0.04262    0.00257    0.00638    0.00062
O2    4    0.164896    0.209576    0.555940    11.00000    0.12704    0.05440 =
         0.04691    0.01074    0.00487   -0.01925
C9    1    0.106189    0.157168    0.389688    11.00000    0.06542    0.04948 =
         0.05728   -0.00818    0.00663   -0.00669
AFIX 137
H9A   2    0.068634    0.053460    0.412030    11.00000   -1.50000
H9B   2    0.205956    0.143743    0.349647    11.00000   -1.50000
H9C   2    0.008163    0.207604    0.352860    11.00000   -1.50000
AFIX   0
C10   1    0.261369    0.674393    0.385731    11.00000    0.06712    0.04650 =
         0.04782    0.01053    0.01158    0.00445
AFIX  23
H10A  2    0.366816    0.701328    0.351161    11.00000   -1.20000
H10B  2    0.164577    0.747860    0.365828    11.00000   -1.20000
AFIX   0
HKLF 4

REM  aa in P2(1)/n
REM R1 =  0.0453 for    1300 Fo > 4sig(Fo)  and  0.0515 for all    1505 data
REM    119 parameters refined using      0 restraints

END

WGHT      0.0668      0.1320

REM Highest difference peak  0.198,  deepest hole -0.350,  1-sigma level  0.094
Q1    1  -0.0278  0.0763  0.4130  11.00000  0.05    0.20
Q2    1  -0.0681  0.2139  0.3922  11.00000  0.05    0.17
Q3    1   0.4796  0.9666  0.4714  11.00000  0.05    0.17
Q4    1   0.0274  0.1038  0.5629  11.00000  0.05    0.17
Q5    1   0.5569  0.9253  0.5240  11.00000  0.05    0.17
;
_shelx_res_checksum              23927
