# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_sem-720(2)
_database_code_depnum_ccdc_archive 'CCDC 1406083'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;
_audit_creation_date             2015-03-31
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(3S*,4aR*,8aS*)-8-hydroxy-2-(4-methoxyphenyl)-8a-methyl-3-phenyl-3,4,4a,5-tetrahydroisoquinoline-1,6(2H,8aH)-dione '
_chemical_formula_moiety         '4(C23 H23 N O4)'
_chemical_formula_sum            'C92 H92 N4 O16'
_chemical_formula_weight         1509.70
_chemical_absolute_configuration unk
_chemical_melting_point          191
_chemical_oxdiff_formula         'O4 N H23 C40'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z+1/2'
3 '-x+1/2, y, z+1/2'
4 'x+1/2, -y, z'

_cell_length_a                   13.1515(8)
_cell_length_b                   9.4791(4)
_cell_length_c                   14.8569(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1852.13(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1860
_cell_measurement_theta_min      3.3940
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6087
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.7482
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   77.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  2 omega  -42.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -19.0000 -180.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0404982000
_diffrn_orient_matrix_UB_12      0.0470737000
_diffrn_orient_matrix_UB_13      -0.0094331000
_diffrn_orient_matrix_UB_21      0.0024630000
_diffrn_orient_matrix_UB_22      0.0186463000
_diffrn_orient_matrix_UB_23      0.0462189000
_diffrn_orient_matrix_UB_31      0.0356041000
_diffrn_orient_matrix_UB_32      -0.0549451000
_diffrn_orient_matrix_UB_33      0.0075488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3269
_reflns_number_total             3623
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.5(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.2856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1129
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
O3 O -0.26144(13) -0.49282(17) 0.24287(11) 0.0204(4) Uani 1 1 d . . .
H3 H -0.2962 -0.4228 0.2530 0.031 Uiso 1 1 d R . .
O4 O -0.57041(12) 0.29027(17) 0.24846(12) 0.0220(4) Uani 1 1 d . . .
O2 O -0.08330(13) -0.69486(17) 0.00397(12) 0.0249(4) Uani 1 1 d . . .
O1 O -0.36384(13) -0.27351(18) 0.21576(12) 0.0263(4) Uani 1 1 d . . .
N1 N -0.33399(14) -0.1371(2) 0.09447(13) 0.0157(4) Uani 1 1 d . . .
C16 C -0.39132(16) -0.0243(2) 0.13636(15) 0.0159(5) Uani 1 1 d . . .
C1 C -0.27668(17) -0.1008(2) 0.01042(16) 0.0195(5) Uani 1 1 d . . .
H1 H -0.2136 -0.0533 0.0283 0.023 Uiso 1 1 calc R . .
C12 C -0.4882(2) 0.0672(3) -0.12726(18) 0.0264(6) Uani 1 1 d . . .
H12 H -0.5549 0.0481 -0.1440 0.032 Uiso 1 1 calc R . .
C18 C -0.55394(18) 0.0741(3) 0.17439(17) 0.0194(5) Uani 1 1 d . . .
H18 H -0.6245 0.0684 0.1744 0.023 Uiso 1 1 calc R . .
C19 C -0.50617(17) 0.1909(2) 0.21286(17) 0.0175(5) Uani 1 1 d . . .
C9 C -0.22985(16) -0.4904(2) 0.15732(16) 0.0166(5) Uani 1 1 d . . .
C5 C -0.32616(17) -0.2595(2) 0.13902(16) 0.0178(5) Uani 1 1 d . . .
C10 C -0.33724(17) 0.0012(2) -0.04783(16) 0.0181(5) Uani 1 1 d . . .
C22 C -0.52447(19) 0.4030(2) 0.29753(16) 0.0217(5) Uani 1 1 d . . .
H22A H -0.4813 0.4563 0.2581 0.033 Uiso 1 1 calc R . .
H22B H -0.4848 0.3650 0.3460 0.033 Uiso 1 1 calc R . .
H22C H -0.5765 0.4633 0.3214 0.033 Uiso 1 1 calc R . .
C7 C -0.13127(17) -0.5935(2) 0.03455(17) 0.0193(5) Uani 1 1 d . . .
C21 C -0.34377(18) 0.0899(2) 0.17489(17) 0.0189(5) Uani 1 1 d . . .
H21 H -0.2731 0.0946 0.1751 0.023 Uiso 1 1 calc R . .
C20 C -0.40033(17) 0.1992(3) 0.21381(17) 0.0203(5) Uani 1 1 d . . .
H20 H -0.3678 0.2762 0.2399 0.024 Uiso 1 1 calc R . .
C3 C -0.20210(17) -0.3430(2) 0.02211(16) 0.0183(5) Uani 1 1 d . . .
H3A H -0.1458 -0.2977 0.0541 0.022 Uiso 1 1 calc R . .
C15 C -0.28976(19) 0.1247(3) -0.07678(16) 0.0241(5) Uani 1 1 d . . .
H15 H -0.2231 0.1438 -0.0598 0.029 Uiso 1 1 calc R . .
C11 C -0.43611(18) -0.0267(3) -0.07478(17) 0.0231(5) Uani 1 1 d . . .
H11 H -0.4674 -0.1102 -0.0570 0.028 Uiso 1 1 calc R . .
C14 C -0.3429(2) 0.2201(3) -0.13166(18) 0.0262(6) Uani 1 1 d . . .
H14 H -0.3116 0.3023 -0.1517 0.031 Uiso 1 1 calc R . .
C8 C -0.16247(17) -0.5867(2) 0.12736(16) 0.0185(5) Uani 1 1 d . . .
H8 H -0.1352 -0.6510 0.1680 0.022 Uiso 1 1 calc R . .
C17 C -0.49736(17) -0.0327(2) 0.13633(16) 0.0180(5) Uani 1 1 d . . .
H17 H -0.5297 -0.1102 0.1107 0.022 Uiso 1 1 calc R . .
C13 C -0.4420(2) 0.1906(3) -0.15556(17) 0.0265(6) Uani 1 1 d . . .
H13 H -0.4780 0.2542 -0.1910 0.032 Uiso 1 1 calc R . .
C4 C -0.28072(17) -0.3879(2) 0.09218(16) 0.0180(5) Uani 1 1 d . . .
C2 C -0.2478(2) -0.2344(2) -0.04144(17) 0.0205(5) Uani 1 1 d . . .
H2A H -0.3077 -0.2735 -0.0701 0.025 Uiso 1 1 calc R . .
H2B H -0.1989 -0.2112 -0.0881 0.025 Uiso 1 1 calc R . .
C23 C -0.37276(18) -0.4692(3) 0.05099(17) 0.0225(5) Uani 1 1 d . . .
H23A H -0.4076 -0.4093 0.0090 0.034 Uiso 1 1 calc R . .
H23B H -0.4186 -0.4963 0.0982 0.034 Uiso 1 1 calc R . .
H23C H -0.3487 -0.5520 0.0205 0.034 Uiso 1 1 calc R . .
C6 C -0.15893(19) -0.4723(3) -0.02745(16) 0.0220(5) Uani 1 1 d . . .
H6A H -0.2088 -0.5050 -0.0708 0.026 Uiso 1 1 calc R . .
H6B H -0.0988 -0.4438 -0.0606 0.026 Uiso 1 1 calc R . .


_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
O3 H3 0.8200 . ?
O3 C9 1.337(3) . ?
O4 C19 1.372(3) . ?
O4 C22 1.427(3) . ?
O2 C7 1.236(3) . ?
O1 C5 1.250(3) . ?
N1 C16 1.448(3) . ?
N1 C1 1.499(3) . ?
N1 C5 1.340(3) . ?
C16 C21 1.375(3) . ?
C16 C17 1.397(3) . ?
C1 H1 0.9800 . ?
C1 C10 1.522(3) . ?
C1 C2 1.531(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.367(4) . ?
C12 C13 1.384(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(3) . ?
C18 C17 1.378(3) . ?
C19 C20 1.394(3) . ?
C9 C8 1.348(3) . ?
C9 C4 1.525(3) . ?
C5 C4 1.525(3) . ?
C10 C15 1.395(3) . ?
C10 C11 1.386(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C7 C8 1.440(3) . ?
C7 C6 1.517(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.400(3) . ?
C20 H20 0.9300 . ?
C3 H3A 0.9800 . ?
C3 C4 1.528(3) . ?
C3 C2 1.521(3) . ?
C3 C6 1.538(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.404(4) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.379(4) . ?
C8 H8 0.9300 . ?
C17 H17 0.9300 . ?
C13 H13 0.9300 . ?
C4 C23 1.560(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 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
C9 O3 H3 109.5 . . ?
C19 O4 C22 116.76(17) . . ?
C16 N1 C1 116.77(17) . . ?
C5 N1 C16 117.82(19) . . ?
C5 N1 C1 124.88(18) . . ?
C21 C16 N1 121.54(19) . . ?
C21 C16 C17 119.9(2) . . ?
C17 C16 N1 118.5(2) . . ?
N1 C1 H1 107.8 . . ?
N1 C1 C10 110.87(18) . . ?
N1 C1 C2 110.74(19) . . ?
C10 C1 H1 107.8 . . ?
C10 C1 C2 111.66(19) . . ?
C2 C1 H1 107.8 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(2) . . ?
O4 C19 C18 115.2(2) . . ?
O4 C19 C20 124.9(2) . . ?
C20 C19 C18 119.9(2) . . ?
O3 C9 C8 120.4(2) . . ?
O3 C9 C4 118.54(19) . . ?
C8 C9 C4 120.7(2) . . ?
O1 C5 N1 120.8(2) . . ?
O1 C5 C4 119.1(2) . . ?
N1 C5 C4 119.8(2) . . ?
C15 C10 C1 118.3(2) . . ?
C11 C10 C1 122.3(2) . . ?
C11 C10 C15 119.4(2) . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C7 C8 122.2(2) . . ?
O2 C7 C6 119.2(2) . . ?
C8 C7 C6 118.6(2) . . ?
C16 C21 H21 119.6 . . ?
C16 C21 C20 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C19 C20 C21 119.0(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C4 C3 H3A 107.6 . . ?
C4 C3 C6 110.74(19) . . ?
C2 C3 H3A 107.6 . . ?
C2 C3 C4 110.14(19) . . ?
C2 C3 C6 112.82(19) . . ?
C6 C3 H3A 107.6 . . ?
C10 C15 H15 120.1 . . ?
C10 C15 C14 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.3 . . ?
C9 C8 C7 122.3(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C9 C4 C3 108.23(18) . . ?
C9 C4 C23 105.96(18) . . ?
C5 C4 C9 113.00(19) . . ?
C5 C4 C3 110.72(19) . . ?
C5 C4 C23 105.62(18) . . ?
C3 C4 C23 113.3(2) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 C1 110.2(2) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C23 H23A 109.5 . . ?
C4 C23 H23B 109.5 . . ?
C4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7 C6 C3 113.7(2) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C3 C6 H6A 108.8 . . ?
C3 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?

_exptl_crystal_recrystallization_method 
'slow evaporation from methanol solution'
