# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ewq
_database_code_depnum_ccdc_archive 'CCDC 1431312'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2016-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'2-(2-hydroxy-2-phenylcyclohexyloxy)isoindoline-1,3-dione '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36

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   'C c'
_space_group_name_Hall           'C -2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   14.19(3)
_cell_length_b                   16.50(3)
_cell_length_c                   7.736(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.18(3)
_cell_angle_gamma                90.00
_cell_volume                     1776(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5583
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2990
_reflns_number_gt                2404
_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)+(0.0800P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(12)
_refine_ls_number_reflns         2990
_refine_ls_number_parameters     230
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C8 C 0.33664(18) 0.51788(18) 0.0627(3) 0.0471(6) Uani 1 1 d . . .
C7 C 0.24675(17) 0.54129(17) -0.0624(3) 0.0466(6) Uani 1 1 d . . .
C1 C 0.25719(15) 0.39887(18) -0.0530(3) 0.0476(6) Uani 1 1 d . . .
C2 C 0.19985(17) 0.47032(17) -0.1307(3) 0.0482(7) Uani 1 1 d . . .
C3 C 0.11121(19) 0.4734(2) -0.2454(4) 0.0612(8) Uani 1 1 d . . .
H3 H 0.0796 0.4265 -0.2917 0.073 Uiso 1 1 calc R . .
C6 C 0.2079(2) 0.6175(2) -0.1048(4) 0.0604(7) Uani 1 1 d . . .
H6 H 0.2398 0.6645 -0.0597 0.073 Uiso 1 1 calc R . .
C4 C 0.0717(2) 0.5504(2) -0.2880(4) 0.0703(9) Uani 1 1 d . . .
H4 H 0.0127 0.5547 -0.3645 0.084 Uiso 1 1 calc R . .
C5 C 0.1186(2) 0.6203(2) -0.2186(4) 0.0696(9) Uani 1 1 d . . .
H5 H 0.0898 0.6703 -0.2486 0.083 Uiso 1 1 calc R . .
C9 C 0.52260(16) 0.28817(18) 0.2604(3) 0.0502(6) Uani 1 1 d . . .
C14 C 0.58474(18) 0.33977(19) 0.4041(3) 0.0537(7) Uani 1 1 d . . .
H14A H 0.5435 0.3750 0.4571 0.064 Uiso 1 1 calc R . .
H14B H 0.6187 0.3044 0.4956 0.064 Uiso 1 1 calc R . .
C10 C 0.47225(17) 0.34300(17) 0.1063(3) 0.0472(6) Uani 1 1 d . . .
H10 H 0.4396 0.3089 0.0091 0.057 Uiso 1 1 calc R . .
C11 C 0.54135(18) 0.3999(2) 0.0391(4) 0.0587(7) Uani 1 1 d . . .
H11A H 0.5047 0.4378 -0.0434 0.070 Uiso 1 1 calc R . .
H11B H 0.5815 0.3685 -0.0242 0.070 Uiso 1 1 calc R . .
C12 C 0.6056(2) 0.4474(2) 0.1851(4) 0.0649(8) Uani 1 1 d . . .
H12A H 0.5669 0.4860 0.2354 0.078 Uiso 1 1 calc R . .
H12B H 0.6527 0.4776 0.1356 0.078 Uiso 1 1 calc R . .
C13 C 0.65760(17) 0.39147(19) 0.3308(4) 0.0616(8) Uani 1 1 d . . .
H13A H 0.6948 0.4237 0.4247 0.074 Uiso 1 1 calc R . .
H13B H 0.7015 0.3565 0.2838 0.074 Uiso 1 1 calc R . .
C15 C 0.44972(18) 0.23437(19) 0.3314(4) 0.0592(7) Uani 1 1 d . . .
C20 C 0.4063(2) 0.1702(3) 0.2286(5) 0.0863(11) Uani 1 1 d . . .
H20 H 0.4205 0.1610 0.1179 0.104 Uiso 1 1 calc R . .
C16 C 0.4258(2) 0.2474(2) 0.4970(5) 0.0724(9) Uani 1 1 d . . .
H16 H 0.4537 0.2902 0.5668 0.087 Uiso 1 1 calc R . .
C19 C 0.3405(3) 0.1192(3) 0.2925(7) 0.1076(15) Uani 1 1 d . . .
H19 H 0.3119 0.0760 0.2247 0.129 Uiso 1 1 calc R . .
C17 C 0.3605(3) 0.1968(3) 0.5583(6) 0.0973(13) Uani 1 1 d . . .
H17 H 0.3456 0.2060 0.6685 0.117 Uiso 1 1 calc R . .
C18 C 0.3189(3) 0.1343(4) 0.4582(8) 0.1081(17) Uani 1 1 d . . .
H18 H 0.2754 0.1010 0.5002 0.130 Uiso 1 1 calc R . .
O3 O 0.39998(11) 0.38803(11) 0.1822(2) 0.0486(4) Uani 1 1 d . . .
O2 O 0.39499(14) 0.56004(13) 0.1564(3) 0.0631(5) Uani 1 1 d . . .
O4 O 0.58269(14) 0.23733(14) 0.1747(3) 0.0623(6) Uani 1 1 d . . .
O1 O 0.24199(13) 0.32667(14) -0.0721(3) 0.0652(5) Uani 1 1 d . . .
N1 N 0.33876(13) 0.43250(13) 0.0550(3) 0.0449(5) Uani 1 1 d . . .
H4A H 0.618(2) 0.219(2) 0.249(4) 0.056(9) 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
C8 O2 1.209(4) . ?
C8 N1 1.410(4) . ?
C8 C7 1.495(4) . ?
C7 C6 1.386(5) . ?
C7 C2 1.399(4) . ?
C1 O1 1.214(4) . ?
C1 N1 1.404(4) . ?
C1 C2 1.491(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.401(5) . ?
C6 C5 1.397(5) . ?
C4 C5 1.386(5) . ?
C9 O4 1.445(4) . ?
C9 C14 1.535(4) . ?
C9 C15 1.542(4) . ?
C9 C10 1.556(4) . ?
C14 C13 1.532(4) . ?
C10 O3 1.477(3) . ?
C10 C11 1.520(4) . ?
C11 C12 1.524(5) . ?
C12 C13 1.531(4) . ?
C15 C20 1.393(5) . ?
C15 C16 1.405(5) . ?
C20 C19 1.415(6) . ?
C16 C17 1.396(5) . ?
C19 C18 1.397(8) . ?
C17 C18 1.355(7) . ?
O3 N1 1.389(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
O2 C8 N1 125.6(2) . . ?
O2 C8 C7 129.7(3) . . ?
N1 C8 C7 104.7(2) . . ?
C6 C7 C2 122.1(3) . . ?
C6 C7 C8 129.6(3) . . ?
C2 C7 C8 108.2(2) . . ?
O1 C1 N1 124.5(2) . . ?
O1 C1 C2 131.0(2) . . ?
N1 C1 C2 104.5(3) . . ?
C3 C2 C7 121.0(3) . . ?
C3 C2 C1 129.9(3) . . ?
C7 C2 C1 109.1(2) . . ?
C2 C3 C4 117.0(3) . . ?
C7 C6 C5 116.7(3) . . ?
C5 C4 C3 121.6(3) . . ?
C4 C5 C6 121.6(3) . . ?
O4 C9 C14 110.3(2) . . ?
O4 C9 C15 109.0(3) . . ?
C14 C9 C15 113.1(2) . . ?
O4 C9 C10 102.1(2) . . ?
C14 C9 C10 110.3(3) . . ?
C15 C9 C10 111.6(2) . . ?
C13 C14 C9 112.0(2) . . ?
O3 C10 C11 111.7(3) . . ?
O3 C10 C9 103.8(2) . . ?
C11 C10 C9 113.0(2) . . ?
C10 C11 C12 113.4(3) . . ?
C11 C12 C13 111.7(3) . . ?
C12 C13 C14 110.2(2) . . ?
C20 C15 C16 118.6(3) . . ?
C20 C15 C9 119.1(3) . . ?
C16 C15 C9 122.3(3) . . ?
C15 C20 C19 120.1(4) . . ?
C17 C16 C15 120.8(4) . . ?
C18 C19 C20 119.5(4) . . ?
C18 C17 C16 120.4(4) . . ?
C17 C18 C19 120.7(4) . . ?
N1 O3 C10 111.8(2) . . ?
O3 N1 C1 122.9(2) . . ?
O3 N1 C8 120.9(2) . . ?
C1 N1 C8 113.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.088
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloro methane'
