# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_cu_d8v18832_0m
_database_code_depnum_ccdc_archive 'CCDC 1875753'
_audit_update_record             
;
2018-10-28 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(R)-3-benzyl-3-((R)-4-hydroxybutan-2-yl)indolin-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H42 N2 O4'
_chemical_formula_weight         590.73

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_H-M_alt        'P 62'
_space_group_name_Hall           'P 62'

_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-y, x, z+1/3'
'-y, x-y, z+2/3'
'-x, -y, z'
'-x+y, -x, z+1/3'
'y, -x+y, z+2/3'

_cell_length_a                   16.0980(5)
_cell_length_b                   16.0980(5)
_cell_length_c                   10.9326(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2453.57(18)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      6.340
_cell_measurement_theta_max      139.969

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30554
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.170
_diffrn_reflns_theta_max         66.970
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2885
_reflns_number_gt                2725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.971

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+0.1994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2885
_refine_ls_number_parameters     220
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.061
_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
O1 O 0.59505(11) 0.63214(11) 0.36288(17) 0.0578(5) Uani 1 1 d . . . . .
O2 O 0.9278(3) 0.9090(3) 0.1693(4) 0.0719(10) Uani 0.5 1 d D U P A 1
H2C H 0.9575 0.9456 0.1131 0.108 Uiso 0.5 1 calc R U P A 1
C19 C 0.9558(10) 0.8390(7) 0.1802(9) 0.0693(19) Uani 0.6 1 d D U P A 1
H19A H 1.0247 0.8725 0.1927 0.083 Uiso 0.6 1 calc R U P A 1
H19B H 0.9435 0.8062 0.1022 0.083 Uiso 0.6 1 calc R U P A 1
O2' O 0.9458(3) 0.9189(3) 0.2693(4) 0.0732(10) Uani 0.5 1 d D U P A 2
H2' H 0.9672 0.9278 0.3391 0.110 Uiso 0.5 1 calc R U P A 2
C19' C 0.9592(16) 0.8508(11) 0.2139(13) 0.069(3) Uani 0.4 1 d D U P A 2
H19C H 1.0272 0.8723 0.2102 0.082 Uiso 0.4 1 calc R U P A 2
H19D H 0.9349 0.8409 0.1308 0.082 Uiso 0.4 1 calc R U P A 2
N1 N 0.60899(12) 0.49808(12) 0.38127(17) 0.0498(5) Uani 1 1 d . . . . .
H1 H 0.5519 0.4560 0.3753 0.060 Uiso 1 1 d R U . . .
C1 C 0.68246(16) 0.47671(15) 0.3984(2) 0.0480(5) Uani 1 1 d . . . . .
C2 C 0.6740(2) 0.38711(18) 0.4036(2) 0.0627(6) Uani 1 1 d . . . . .
H2 H 0.6150 0.3312 0.3954 0.075 Uiso 1 1 calc R U . . .
C3 C 0.7581(2) 0.3847(2) 0.4219(3) 0.0687(7) Uani 1 1 d . . . . .
H3 H 0.7554 0.3257 0.4257 0.082 Uiso 1 1 calc R U . . .
C4 C 0.8448(2) 0.4670(2) 0.4346(2) 0.0679(7) Uani 1 1 d . . . . .
H4 H 0.8997 0.4629 0.4480 0.081 Uiso 1 1 calc R U . . .
C5 C 0.85185(18) 0.55623(19) 0.4276(2) 0.0589(6) Uani 1 1 d . . . . .
H5 H 0.9110 0.6119 0.4359 0.071 Uiso 1 1 calc R U . . .
C6 C 0.76963(16) 0.56128(16) 0.40807(19) 0.0476(5) Uani 1 1 d . . . . .
C7 C 0.75323(14) 0.64572(15) 0.3937(2) 0.0468(5) Uani 1 1 d . . . . .
C8 C 0.64344(15) 0.59366(15) 0.3777(2) 0.0464(5) Uani 1 1 d . . . . .
C9 C 0.78021(18) 0.71147(18) 0.5074(2) 0.0599(6) Uani 1 1 d . . . . .
H9A H 0.8487 0.7406 0.5209 0.072 Uiso 1 1 calc R U . . .
H9B H 0.7670 0.7628 0.4896 0.072 Uiso 1 1 calc R U . . .
C10 C 0.72915(17) 0.66307(17) 0.6242(2) 0.0554(6) Uani 1 1 d . . . . .
C11 C 0.6451(2) 0.6613(2) 0.6578(3) 0.0662(7) Uani 1 1 d . . . . .
H11 H 0.6198 0.6896 0.6071 0.079 Uiso 1 1 calc R U . . .
C12 C 0.5987(2) 0.6184(2) 0.7652(3) 0.0783(8) Uani 1 1 d . . . . .
H12 H 0.5424 0.6177 0.7860 0.094 Uiso 1 1 calc R U . . .
C13 C 0.6346(3) 0.5766(2) 0.8418(3) 0.0823(9) Uani 1 1 d . . . . .
H13 H 0.6029 0.5473 0.9140 0.099 Uiso 1 1 calc R U . . .
C14 C 0.7182(3) 0.5787(3) 0.8103(3) 0.0847(9) Uani 1 1 d . . . . .
H14 H 0.7435 0.5511 0.8619 0.102 Uiso 1 1 calc R U . . .
C15 C 0.7651(2) 0.6215(2) 0.7023(3) 0.0726(8) Uani 1 1 d . . . . .
H15 H 0.8216 0.6223 0.6823 0.087 Uiso 1 1 calc R U . . .
C16 C 0.79986(16) 0.70651(16) 0.2764(2) 0.0501(5) Uani 1 1 d . . . . .
H16 H 0.7793 0.7543 0.2710 0.060 Uiso 1 1 calc R U . . .
C17 C 0.76552(18) 0.64566(18) 0.1602(2) 0.0585(6) Uani 1 1 d . . . . .
H17A H 0.7922 0.6863 0.0899 0.088 Uiso 1 1 calc R U . . .
H17B H 0.6968 0.6135 0.1562 0.088 Uiso 1 1 calc R U . . .
H17C H 0.7860 0.5990 0.1615 0.088 Uiso 1 1 calc R U . . .
C18 C 0.90998(17) 0.76126(19) 0.2808(3) 0.0656(7) Uani 1 1 d D . . . .
H18A H 0.9327 0.7160 0.2715 0.079 Uiso 1 1 calc R U . A 1
H18B H 0.9308 0.7915 0.3603 0.079 Uiso 1 1 calc R U . A 1


_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 C8 1.224(3) . ?
O2 C19 1.413(13) . ?
O2 H2C 0.8200 . ?
C19 C18 1.548(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
O2' C19' 1.362(16) . ?
O2' H2' 0.8200 . ?
C19' C18 1.448(16) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
N1 C8 1.350(3) . ?
N1 C1 1.400(3) . ?
N1 H1 0.8279 . ?
C1 C2 1.381(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.517(3) . ?
C7 C8 1.541(3) . ?
C7 C9 1.547(3) . ?
C7 C16 1.559(3) . ?
C9 C10 1.508(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.378(4) . ?
C10 C11 1.389(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.529(3) . ?
C16 C18 1.536(3) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C19 O2 H2C 109.5 . . ?
O2 C19 C18 119.4(9) . . ?
O2 C19 H19A 107.5 . . ?
C18 C19 H19A 107.5 . . ?
O2 C19 H19B 107.5 . . ?
C18 C19 H19B 107.5 . . ?
H19A C19 H19B 107.0 . . ?
C19' O2' H2' 109.5 . . ?
O2' C19' C18 110.4(11) . . ?
O2' C19' H19C 109.6 . . ?
C18 C19' H19C 109.6 . . ?
O2' C19' H19D 109.6 . . ?
C18 C19' H19D 109.6 . . ?
H19C C19' H19D 108.1 . . ?
C8 N1 C1 111.58(17) . . ?
C8 N1 H1 125.9 . . ?
C1 N1 H1 122.5 . . ?
C2 C1 C6 123.0(2) . . ?
C2 C1 N1 127.5(2) . . ?
C6 C1 N1 109.48(17) . . ?
C1 C2 C3 116.6(3) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 132.0(2) . . ?
C1 C6 C7 109.14(17) . . ?
C6 C7 C8 100.98(17) . . ?
C6 C7 C9 114.51(19) . . ?
C8 C7 C9 108.46(18) . . ?
C6 C7 C16 113.74(18) . . ?
C8 C7 C16 108.00(17) . . ?
C9 C7 C16 110.43(18) . . ?
O1 C8 N1 125.3(2) . . ?
O1 C8 C7 125.91(19) . . ?
N1 C8 C7 108.80(17) . . ?
C10 C9 C7 115.65(19) . . ?
C10 C9 H9A 108.4 . . ?
C7 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C7 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C15 C10 C11 117.9(3) . . ?
C15 C10 C9 121.5(2) . . ?
C11 C10 C9 120.6(2) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.9(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C18 109.8(2) . . ?
C17 C16 C7 112.02(18) . . ?
C18 C16 C7 112.91(19) . . ?
C17 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C7 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19' C18 C16 117.1(9) . . ?
C16 C18 C19 112.8(6) . . ?
C16 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C16 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?

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 N1 C1 C2 -178.4(2) . . . . ?
C8 N1 C1 C6 0.7(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
N1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 C7 177.9(2) . . . . ?
N1 C1 C6 C7 -1.3(2) . . . . ?
C5 C6 C7 C8 -178.9(2) . . . . ?
C1 C6 C7 C8 1.2(2) . . . . ?
C5 C6 C7 C9 -62.6(3) . . . . ?
C1 C6 C7 C9 117.5(2) . . . . ?
C5 C6 C7 C16 65.7(3) . . . . ?
C1 C6 C7 C16 -114.2(2) . . . . ?
C1 N1 C8 O1 179.5(2) . . . . ?
C1 N1 C8 C7 0.1(3) . . . . ?
C6 C7 C8 O1 179.9(2) . . . . ?
C9 C7 C8 O1 59.2(3) . . . . ?
C16 C7 C8 O1 -60.5(3) . . . . ?
C6 C7 C8 N1 -0.8(2) . . . . ?
C9 C7 C8 N1 -121.5(2) . . . . ?
C16 C7 C8 N1 118.8(2) . . . . ?
C6 C7 C9 C10 -57.9(3) . . . . ?
C8 C7 C9 C10 54.0(3) . . . . ?
C16 C7 C9 C10 172.2(2) . . . . ?
C7 C9 C10 C15 88.6(3) . . . . ?
C7 C9 C10 C11 -93.0(3) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?
C9 C10 C11 C12 -179.1(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C11 C10 C15 C14 0.6(4) . . . . ?
C9 C10 C15 C14 178.9(3) . . . . ?
C13 C14 C15 C10 0.1(5) . . . . ?
C6 C7 C16 C17 56.4(2) . . . . ?
C8 C7 C16 C17 -54.8(2) . . . . ?
C9 C7 C16 C17 -173.28(19) . . . . ?
C6 C7 C16 C18 -68.2(2) . . . . ?
C8 C7 C16 C18 -179.4(2) . . . . ?
C9 C7 C16 C18 62.2(2) . . . . ?
O2' C19' C18 C16 70.1(13) . . . . ?
O2' C19' C18 C19 147(7) . . . . ?
C17 C16 C18 C19' 83.6(7) . . . . ?
C7 C16 C18 C19' -150.7(6) . . . . ?
C17 C16 C18 C19 67.6(5) . . . . ?
C7 C16 C18 C19 -166.6(4) . . . . ?
O2 C19 C18 C19' -56(5) . . . . ?
O2 C19 C18 C16 53.9(8) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.021

_shelxl_version_number           2013-4



