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

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_x2068fin
_database_code_depnum_ccdc_archive 'CCDC 1028558'
_audit_update_record             
;
2014-10-10 deposited with the CCDC.
2014-12-02 downloaded from the CCDC.
;

_audit_creation_date             2014-08-18T10:46:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C28 H23 N O2'
_chemical_formula_weight         405.47
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.43230(10)
_cell_length_b                   10.40300(10)
_cell_length_c                   21.1950(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2079.74(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    19230
_cell_measurement_theta_min      4.163
_cell_measurement_theta_max      67.794

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             856

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.34a (release 02-06-2014 CrysAlis171 .NET)
        (compiled Jun  2 2014,16:24:16)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.60413
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.356
_diffrn_orient_matrix_ub_11      -0.0342181
_diffrn_orient_matrix_ub_12      -0.0033325
_diffrn_orient_matrix_ub_13      -0.0710508
_diffrn_orient_matrix_ub_21      0.0938015
_diffrn_orient_matrix_ub_22      -0.1201789
_diffrn_orient_matrix_ub_23      -0.0076107
_diffrn_orient_matrix_ub_31      -0.1293066
_diffrn_orient_matrix_ub_32      -0.0863921
_diffrn_orient_matrix_ub_33      0.0133177
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_number            31480
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.172
_diffrn_reflns_theta_max         67.716
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3765
_reflns_number_gt                3725
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.34a (release 02-06-2014 CrysAlis171 .NET)
        (compiled Jun  2 2014,16:24:16)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.34a (release 02-06-2014 CrysAlis171 .NET)
        (compiled Jun  2 2014,16:24:16)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.34a (release 02-06-2014 CrysAlis171 .NET)
        (compiled Jun  2 2014,16:24:16)
;
_computing_structure_solution    
;
 SHELXS-2014
 Program for Crystal Structure Analysis (Release 2014-3)
 G. M. Sheldrick, Institüt für Anorganische Chemie der Universität,
 Tammanstrasse 4, D-3400 Göttingen, Germany.
 G. M. Sheldrick, Acta. Cryst., 2008, A64, 112 - 122
;
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEP3 for Windows
 L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
;
_computing_publication_material  
;
 WINGX
 L.J. Farrugia,
 J. Appl. Cryst., 2012, 45, 849-854.
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.3197P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3765
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.068
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51259(14) -0.03203(13) 0.41614(6) 0.0276(3) Uani 1 d . .
O2 O 0.71334(12) 0.13995(12) 0.18652(5) 0.0265(3) Uani 1 d . .
N1 N 0.02733(15) 0.18265(14) 0.22033(7) 0.0246(3) Uani 1 d . .
C1 C 0.10714(18) 0.20226(16) 0.27392(8) 0.0223(3) Uani 1 d . .
C2 C 0.20496(17) 0.10694(15) 0.28028(7) 0.0207(3) Uani 1 d . .
C3 C 0.18420(16) 0.02086(15) 0.22792(7) 0.0201(3) Uani 1 d . .
C4 C 0.24965(19) -0.09372(16) 0.20833(8) 0.0241(4) Uani 1 d . .
C5 C 0.1994(2) -0.15503(17) 0.15523(8) 0.0271(4) Uani 1 d . .
C6 C 0.08413(19) -0.10579(17) 0.12095(8) 0.0263(4) Uani 1 d . .
C7 C 0.01812(18) 0.00715(17) 0.13864(8) 0.0255(4) Uani 1 d . .
C8 C 0.07064(17) 0.07026(16) 0.19203(8) 0.0217(3) Uani 1 d . .
C9 C 0.30450(17) 0.08361(15) 0.33485(7) 0.0201(3) Uani 1 d . .
C10 C 0.46059(17) 0.07317(15) 0.31621(7) 0.0203(3) Uani 1 d . .
C11 C 0.55377(18) 0.01167(15) 0.35739(8) 0.0226(3) Uani 1 d . .
C12 C 0.69173(19) -0.01399(16) 0.33924(8) 0.0254(4) Uani 1 d . .
C13 C 0.74122(18) 0.02642(16) 0.28115(9) 0.0253(4) Uani 1 d . .
C14 C 0.65234(18) 0.09590(15) 0.24146(8) 0.0220(3) Uani 1 d . .
C15 C 0.51225(18) 0.11739(15) 0.25853(8) 0.0207(3) Uani 1 d . .
C16 C 0.6240(2) 0.20863(18) 0.14421(9) 0.0286(4) Uani 1 d . .
C17 C 0.28228(17) 0.17938(16) 0.38880(7) 0.0216(3) Uani 1 d . .
C18 C 0.20689(17) 0.14544(16) 0.44393(7) 0.0221(3) Uani 1 d . .
C19 C 0.1926(2) 0.23636(18) 0.49219(8) 0.0273(4) Uani 1 d . .
C20 C 0.2516(2) 0.35776(18) 0.48699(9) 0.0313(4) Uani 1 d . .
C21 C 0.3266(2) 0.39032(17) 0.43318(9) 0.0312(4) Uani 1 d . .
C22 C 0.34101(19) 0.30194(17) 0.38465(9) 0.0269(4) Uani 1 d . .
C23 C 0.14767(17) 0.01396(16) 0.45441(8) 0.0222(3) Uani 1 d . .
C24 C 0.05039(18) -0.04262(17) 0.41325(8) 0.0237(3) Uani 1 d . .
C25 C -0.00147(18) -0.16496(17) 0.42510(8) 0.0260(4) Uani 1 d . .
C26 C 0.0420(2) -0.23313(17) 0.47790(8) 0.0282(4) Uani 1 d . .
C27 C 0.1380(2) -0.17772(18) 0.51911(8) 0.0289(4) Uani 1 d . .
C28 C 0.18997(19) -0.05545(18) 0.50777(8) 0.0266(4) Uani 1 d . .
H1N1 H -0.053(3) 0.223(2) 0.2107(10) 0.029(5) Uiso 1 d . .
H1O1 H 0.440(3) 0.009(3) 0.4291(13) 0.054(8) Uiso 1 d . .
H1 H 0.090(2) 0.2749(19) 0.3018(10) 0.024(5) Uiso 1 d . .
H4 H 0.329(2) -0.1320(19) 0.2325(9) 0.025(5) Uiso 1 d . .
H5 H 0.242(2) -0.234(2) 0.1410(10) 0.031(5) Uiso 1 d . .
H6 H 0.049(2) -0.153(2) 0.0835(10) 0.026(5) Uiso 1 d . .
H7 H -0.065(2) 0.042(2) 0.1151(10) 0.029(5) Uiso 1 d . .
H9 H 0.2777(19) -0.0006(19) 0.3513(8) 0.016(4) Uiso 1 d . .
H12 H 0.755(3) -0.060(2) 0.3679(11) 0.037(6) Uiso 1 d . .
H13 H 0.833(2) 0.011(2) 0.2675(9) 0.028(5) Uiso 1 d . .
H15 H 0.447(2) 0.1609(18) 0.2307(9) 0.020(5) Uiso 1 d . .
H16A H 0.541(2) 0.153(2) 0.1308(9) 0.028(5) Uiso 1 d . .
H16B H 0.586(2) 0.285(2) 0.1647(10) 0.029(5) Uiso 1 d . .
H16C H 0.682(3) 0.233(2) 0.1080(11) 0.035(6) Uiso 1 d . .
H19 H 0.139(2) 0.2131(19) 0.5295(10) 0.022(5) Uiso 1 d . .
H20 H 0.242(3) 0.418(2) 0.5222(12) 0.045(7) Uiso 1 d . .
H21 H 0.367(2) 0.473(2) 0.4296(10) 0.039(6) Uiso 1 d . .
H22 H 0.393(2) 0.3235(19) 0.3470(10) 0.026(5) Uiso 1 d . .
H24 H 0.020(2) 0.0051(19) 0.3758(9) 0.023(5) Uiso 1 d . .
H25 H -0.071(2) -0.203(2) 0.3974(10) 0.025(5) Uiso 1 d . .
H26 H 0.003(2) -0.320(2) 0.4862(9) 0.026(5) Uiso 1 d . .
H27 H 0.166(3) -0.224(2) 0.5558(11) 0.041(6) Uiso 1 d . .
H28 H 0.258(3) -0.020(2) 0.5362(11) 0.041(6) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C11 1.381(2) . ?
O1 H1O1 0.85(3) . ?
O2 C14 1.377(2) . ?
O2 C16 1.423(2) . ?
N1 C8 1.376(2) . ?
N1 C1 1.378(2) . ?
N1 H1N1 0.89(2) . ?
C1 C2 1.361(2) . ?
C1 H1 0.97(2) . ?
C2 C3 1.439(2) . ?
C2 C9 1.509(2) . ?
C3 C4 1.405(2) . ?
C3 C8 1.411(2) . ?
C4 C5 1.378(2) . ?
C4 H4 0.99(2) . ?
C5 C6 1.404(3) . ?
C5 H5 0.96(2) . ?
C6 C7 1.381(3) . ?
C6 H6 0.99(2) . ?
C7 C8 1.399(2) . ?
C7 H7 1.00(2) . ?
C9 C10 1.528(2) . ?
C9 C17 1.531(2) . ?
C9 H9 0.98(2) . ?
C10 C11 1.394(2) . ?
C10 C15 1.394(2) . ?
C11 C12 1.383(3) . ?
C12 C13 1.382(3) . ?
C12 H12 0.98(2) . ?
C13 C14 1.390(2) . ?
C13 H13 0.93(2) . ?
C14 C15 1.388(2) . ?
C15 H15 0.962(19) . ?
C16 H16A 1.02(2) . ?
C16 H16B 0.97(2) . ?
C16 H16C 0.98(2) . ?
C17 C22 1.393(2) . ?
C17 C18 1.413(2) . ?
C18 C19 1.400(2) . ?
C18 C23 1.494(2) . ?
C19 C20 1.384(3) . ?
C19 H19 0.97(2) . ?
C20 C21 1.384(3) . ?
C20 H20 0.98(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.95(2) . ?
C22 H22 0.96(2) . ?
C23 C24 1.396(2) . ?
C23 C28 1.400(2) . ?
C24 C25 1.386(3) . ?
C24 H24 0.98(2) . ?
C25 C26 1.387(3) . ?
C25 H25 0.97(2) . ?
C26 C27 1.384(3) . ?
C26 H26 0.99(2) . ?
C27 C28 1.384(3) . ?
C27 H27 0.96(2) . ?
C28 H28 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 H1O1 110.5(18) . . ?
C14 O2 C16 116.91(13) . . ?
C8 N1 C1 108.84(14) . . ?
C8 N1 H1N1 123.7(14) . . ?
C1 N1 H1N1 125.6(14) . . ?
C2 C1 N1 110.13(15) . . ?
C2 C1 H1 128.2(12) . . ?
N1 C1 H1 121.7(12) . . ?
C1 C2 C3 106.53(14) . . ?
C1 C2 C9 127.93(15) . . ?
C3 C2 C9 125.13(14) . . ?
C4 C3 C8 118.91(15) . . ?
C4 C3 C2 134.09(15) . . ?
C8 C3 C2 107.00(14) . . ?
C5 C4 C3 118.88(16) . . ?
C5 C4 H4 119.7(11) . . ?
C3 C4 H4 121.4(11) . . ?
C4 C5 C6 121.34(17) . . ?
C4 C5 H5 120.5(13) . . ?
C6 C5 H5 118.2(13) . . ?
C7 C6 C5 121.24(16) . . ?
C7 C6 H6 119.4(12) . . ?
C5 C6 H6 119.3(12) . . ?
C6 C7 C8 117.33(16) . . ?
C6 C7 H7 122.0(13) . . ?
C8 C7 H7 120.7(13) . . ?
N1 C8 C7 130.25(16) . . ?
N1 C8 C3 107.46(14) . . ?
C7 C8 C3 122.28(15) . . ?
C2 C9 C10 114.37(13) . . ?
C2 C9 C17 112.49(13) . . ?
C10 C9 C17 111.79(13) . . ?
C2 C9 H9 104.9(11) . . ?
C10 C9 H9 106.1(11) . . ?
C17 C9 H9 106.4(10) . . ?
C11 C10 C15 118.69(15) . . ?
C11 C10 C9 118.56(14) . . ?
C15 C10 C9 122.68(14) . . ?
O1 C11 C12 116.85(15) . . ?
O1 C11 C10 122.56(15) . . ?
C12 C11 C10 120.51(15) . . ?
C13 C12 C11 120.45(16) . . ?
C13 C12 H12 119.8(14) . . ?
C11 C12 H12 119.8(14) . . ?
C12 C13 C14 119.57(16) . . ?
C12 C13 H13 122.7(13) . . ?
C14 C13 H13 117.7(13) . . ?
O2 C14 C15 124.36(15) . . ?
O2 C14 C13 115.64(15) . . ?
C15 C14 C13 120.00(15) . . ?
C14 C15 C10 120.54(15) . . ?
C14 C15 H15 121.4(11) . . ?
C10 C15 H15 118.1(11) . . ?
O2 C16 H16A 110.3(12) . . ?
O2 C16 H16B 110.3(13) . . ?
H16A C16 H16B 107.6(18) . . ?
O2 C16 H16C 107.1(14) . . ?
H16A C16 H16C 111.2(17) . . ?
H16B C16 H16C 110.4(18) . . ?
C22 C17 C18 118.76(15) . . ?
C22 C17 C9 119.60(15) . . ?
C18 C17 C9 121.61(15) . . ?
C19 C18 C17 118.96(16) . . ?
C19 C18 C23 118.29(15) . . ?
C17 C18 C23 122.68(14) . . ?
C20 C19 C18 121.30(17) . . ?
C20 C19 H19 120.2(12) . . ?
C18 C19 H19 118.5(12) . . ?
C21 C20 C19 119.62(16) . . ?
C21 C20 H20 121.2(14) . . ?
C19 C20 H20 119.2(14) . . ?
C20 C21 C22 119.95(17) . . ?
C20 C21 H21 119.7(14) . . ?
C22 C21 H21 120.3(14) . . ?
C21 C22 C17 121.40(17) . . ?
C21 C22 H22 120.7(12) . . ?
C17 C22 H22 117.9(12) . . ?
C24 C23 C28 118.34(16) . . ?
C24 C23 C18 122.59(15) . . ?
C28 C23 C18 119.07(15) . . ?
C25 C24 C23 120.37(16) . . ?
C25 C24 H24 120.6(12) . . ?
C23 C24 H24 119.0(12) . . ?
C24 C25 C26 120.76(17) . . ?
C24 C25 H25 120.2(12) . . ?
C26 C25 H25 119.0(12) . . ?
C27 C26 C25 119.31(16) . . ?
C27 C26 H26 120.8(12) . . ?
C25 C26 H26 119.9(12) . . ?
C28 C27 C26 120.32(16) . . ?
C28 C27 H27 120.7(15) . . ?
C26 C27 H27 118.9(15) . . ?
C27 C28 C23 120.89(16) . . ?
C27 C28 H28 118.7(15) . . ?
C23 C28 H28 120.4(15) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
" (S)-2-([1,1'-biphenyl]-2-yl(1H-indol-3-yl)methyl)-4-methoxyphenol "
_chemical_melting_point          363.15
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
