# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                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.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_ax0389

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '2-(1-(1H-Indol-3-yl)ethyl)phenol '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N O1.50'
_chemical_formula_weight         246.30
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   18.2584(3)
_cell_length_b                   5.6362(1)
_cell_length_c                   12.3333(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.487(1)
_cell_angle_gamma                90.00
_cell_volume                     1263.38(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7196
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      66.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microfocus
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7959
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         66.55
_reflns_number_total             2229
_reflns_number_gt                2219
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_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)+(0.0386P)²+0.2749P] 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       0.0076(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(18)
_refine_ls_number_reflns         2229
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C1 C 0.68945(7) 0.0321(2) 0.38371(9) 0.0253(3) Uani 1 1 d . . .
H1C H 0.6443 -0.0432 0.3950 0.030 Uiso 1 1 calc R . .
C2 C 0.69579(6) 0.2369(2) 0.32653(8) 0.0203(2) Uani 1 1 d . . .
C3 C 0.77328(6) 0.2854(2) 0.33003(8) 0.0204(2) Uani 1 1 d . . .
C4 C 0.81062(6) 0.1019(2) 0.39006(8) 0.0245(2) Uani 1 1 d . . .
C5 C 0.88723(7) 0.0953(3) 0.40892(9) 0.0323(3) Uani 1 1 d . . .
H5 H 0.9117 -0.0302 0.4491 0.039 Uiso 1 1 calc R . .
C6 C 0.92602(7) 0.2780(3) 0.36693(10) 0.0362(3) Uani 1 1 d . . .
H6 H 0.9782 0.2781 0.3781 0.043 Uiso 1 1 calc R . .
C7 C 0.88986(7) 0.4637(3) 0.30803(10) 0.0327(3) Uani 1 1 d . . .
H7 H 0.9181 0.5878 0.2806 0.039 Uiso 1 1 calc R . .
C8 C 0.81425(6) 0.4701(2) 0.28912(9) 0.0249(2) Uani 1 1 d . . .
H8 H 0.7903 0.5970 0.2492 0.030 Uiso 1 1 calc R . .
C9 C 0.63529(6) 0.3857(2) 0.26929(9) 0.0213(2) Uani 1 1 d . . .
H9 H 0.6405 0.5500 0.2996 0.026 Uiso 1 1 calc R . .
C10 C 0.64126(5) 0.40211(19) 0.14679(8) 0.0201(2) Uani 1 1 d . . .
C11 C 0.60714(6) 0.5907(2) 0.08726(9) 0.0226(2) Uani 1 1 d . . .
C12 C 0.60950(6) 0.6046(2) -0.02517(9) 0.0263(3) Uani 1 1 d . . .
H12 H 0.5863 0.7330 -0.0648 0.032 Uiso 1 1 calc R . .
C13 C 0.64578(6) 0.4309(2) -0.07926(9) 0.0262(3) Uani 1 1 d . . .
H13 H 0.6473 0.4406 -0.1559 0.031 Uiso 1 1 calc R . .
C14 C 0.67979(6) 0.2431(2) -0.02179(9) 0.0256(2) Uani 1 1 d . . .
H14 H 0.7046 0.1240 -0.0586 0.031 Uiso 1 1 calc R . .
C15 C 0.67705(5) 0.2314(2) 0.09039(9) 0.0217(2) Uani 1 1 d . . .
H15 H 0.7004 0.1027 0.1296 0.026 Uiso 1 1 calc R . .
C16 C 0.55867(6) 0.2950(2) 0.29016(9) 0.0280(3) Uani 1 1 d . . .
H16A H 0.5534 0.2996 0.3685 0.042 Uiso 1 1 calc R . .
H16B H 0.5526 0.1315 0.2638 0.042 Uiso 1 1 calc R . .
H16C H 0.5210 0.3960 0.2516 0.042 Uiso 1 1 calc R . .
N1 N 0.75801(6) -0.0498(2) 0.42264(8) 0.0297(2) Uani 1 1 d . . .
O1 O 0.57161(5) 0.75660(15) 0.14376(6) 0.0288(2) Uani 1 1 d . . .
O2 O 0.5000 0.1003(2) 0.0000 0.0304(3) Uani 1 2 d S . .
H1A H 0.7676(9) -0.172(3) 0.4617(14) 0.045(5) Uiso 1 1 d . . .
H1B H 0.5499(10) 0.862(3) 0.0945(13) 0.048(5) Uiso 1 1 d . . .
H2 H 0.4670(11) 0.192(4) 0.0214(16) 0.069(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0279(6) 0.0246(6) 0.0241(5) -0.0013(4) 0.0065(4) -0.0044(4)
C2 0.0231(5) 0.0222(5) 0.0158(4) -0.0036(4) 0.0032(4) -0.0030(4)
C3 0.0234(5) 0.0236(6) 0.0143(4) -0.0026(4) 0.0022(4) 0.0015(4)
C4 0.0300(6) 0.0270(6) 0.0167(5) -0.0004(4) 0.0034(4) 0.0026(5)
C5 0.0311(6) 0.0392(7) 0.0260(6) 0.0005(5) -0.0013(5) 0.0130(6)
C6 0.0207(5) 0.0482(8) 0.0391(6) -0.0038(6) -0.0007(5) 0.0035(6)
C7 0.0244(6) 0.0372(7) 0.0366(6) 0.0002(6) 0.0044(5) -0.0041(5)
C8 0.0243(6) 0.0265(6) 0.0239(5) 0.0018(5) 0.0027(4) -0.0010(5)
C9 0.0194(5) 0.0217(5) 0.0228(5) -0.0043(4) 0.0020(4) -0.0021(4)
C10 0.0154(5) 0.0216(6) 0.0230(5) -0.0020(4) 0.0000(4) -0.0039(4)
C11 0.0186(5) 0.0209(5) 0.0281(5) -0.0037(5) 0.0014(4) -0.0026(4)
C12 0.0242(5) 0.0255(6) 0.0282(6) 0.0035(5) -0.0035(4) -0.0005(5)
C13 0.0262(5) 0.0313(6) 0.0211(5) 0.0008(5) 0.0017(4) -0.0037(5)
C14 0.0244(5) 0.0275(6) 0.0250(5) -0.0044(5) 0.0036(4) 0.0000(5)
C15 0.0179(5) 0.0225(5) 0.0244(5) -0.0005(5) -0.0002(4) -0.0006(5)
C16 0.0215(5) 0.0362(7) 0.0268(5) -0.0057(5) 0.0056(4) -0.0019(5)
N1 0.0376(6) 0.0265(6) 0.0255(5) 0.0091(4) 0.0054(4) 0.0044(4)
O1 0.0309(4) 0.0238(4) 0.0312(4) -0.0030(4) 0.0005(3) 0.0085(4)
O2 0.0239(6) 0.0223(6) 0.0434(7) 0.000 -0.0055(5) 0.000

_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
C1 C2 1.3636(16) . ?
C1 N1 1.3768(16) . ?
C1 H1C 0.9500 . ?
C2 C3 1.4375(15) . ?
C2 C9 1.5076(15) . ?
C3 C8 1.4038(16) . ?
C3 C4 1.4092(16) . ?
C4 N1 1.3742(16) . ?
C4 C5 1.3964(17) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3785(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.5278(14) . ?
C9 C16 1.5341(15) . ?
C9 H9 1.0000 . ?
C10 C15 1.3868(15) . ?
C10 C11 1.4032(15) . ?
C11 O1 1.3666(13) . ?
C11 C12 1.3937(16) . ?
C12 C13 1.3882(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3868(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3908(15) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 H1A 0.848(18) . ?
O1 H1B 0.913(18) . ?
O2 H2 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 110.17(10) . . ?
C2 C1 H1C 124.9 . . ?
N1 C1 H1C 124.9 . . ?
C1 C2 C3 106.09(10) . . ?
C1 C2 C9 128.20(10) . . ?
C3 C2 C9 125.70(10) . . ?
C8 C3 C4 119.05(10) . . ?
C8 C3 C2 133.37(10) . . ?
C4 C3 C2 107.57(10) . . ?
N1 C4 C5 130.68(11) . . ?
N1 C4 C3 107.07(10) . . ?
C5 C4 C3 122.25(11) . . ?
C6 C5 C4 117.39(12) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C7 121.24(11) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 121.42(12) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 118.64(11) . . ?
C7 C8 H8 120.7 . . ?
C3 C8 H8 120.7 . . ?
C2 C9 C10 112.23(8) . . ?
C2 C9 C16 112.03(10) . . ?
C10 C9 C16 109.79(8) . . ?
C2 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
C16 C9 H9 107.5 . . ?
C15 C10 C11 118.02(10) . . ?
C15 C10 C9 122.39(9) . . ?
C11 C10 C9 119.54(9) . . ?
O1 C11 C12 122.02(10) . . ?
O1 C11 C10 117.39(9) . . ?
C12 C11 C10 120.59(10) . . ?
C13 C12 C11 120.00(11) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.23(10) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.19(10) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 121.97(10) . . ?
C10 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 N1 C1 109.10(10) . . ?
C4 N1 H1A 123.9(12) . . ?
C1 N1 H1A 127.0(12) . . ?
C11 O1 H1B 107.6(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
N1 C1 C2 C3 0.08(12) . . . . ?
N1 C1 C2 C9 179.50(10) . . . . ?
C1 C2 C3 C8 -178.37(11) . . . . ?
C9 C2 C3 C8 2.18(18) . . . . ?
C1 C2 C3 C4 0.37(11) . . . . ?
C9 C2 C3 C4 -179.08(10) . . . . ?
C8 C3 C4 N1 178.29(9) . . . . ?
C2 C3 C4 N1 -0.67(11) . . . . ?
C8 C3 C4 C5 -1.02(16) . . . . ?
C2 C3 C4 C5 -179.98(10) . . . . ?
N1 C4 C5 C6 -178.68(12) . . . . ?
C3 C4 C5 C6 0.44(17) . . . . ?
C4 C5 C6 C7 0.31(19) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 C3 -0.11(18) . . . . ?
C4 C3 C8 C7 0.83(16) . . . . ?
C2 C3 C8 C7 179.46(11) . . . . ?
C1 C2 C9 C10 -118.42(12) . . . . ?
C3 C2 C9 C10 60.90(13) . . . . ?
C1 C2 C9 C16 5.63(15) . . . . ?
C3 C2 C9 C16 -175.05(10) . . . . ?
C2 C9 C10 C15 24.22(13) . . . . ?
C16 C9 C10 C15 -101.07(11) . . . . ?
C2 C9 C10 C11 -158.35(9) . . . . ?
C16 C9 C10 C11 76.35(12) . . . . ?
C15 C10 C11 O1 179.53(9) . . . . ?
C9 C10 C11 O1 1.98(14) . . . . ?
C15 C10 C11 C12 -0.06(15) . . . . ?
C9 C10 C11 C12 -177.61(9) . . . . ?
O1 C11 C12 C13 -179.50(10) . . . . ?
C10 C11 C12 C13 0.07(16) . . . . ?
C11 C12 C13 C14 -0.03(17) . . . . ?
C12 C13 C14 C15 -0.01(16) . . . . ?
C11 C10 C15 C14 0.02(15) . . . . ?
C9 C10 C15 C14 177.49(9) . . . . ?
C13 C14 C15 C10 0.01(16) . . . . ?
C5 C4 N1 C1 179.95(12) . . . . ?
C3 C4 N1 C1 0.72(12) . . . . ?
C2 C1 N1 C4 -0.51(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.55
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: heptane/ethanol'
_database_code_depnum_ccdc_archive 'CCDC 1016204'
