# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cu_d8v17115_0m
_database_code_depnum_ccdc_archive 'CCDC 1845225'
_audit_update_record             
;
2018-05-24 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;
_audit_creation_date             2017-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'Methyl 1-((4,4-dimethyl-3-phenyl-4,5-dihydroisoxazol-5-yl)methyl)-4-phenylisoquinoline-3-carboxylate'
_chemical_formula_moiety         'C29 H26 N2 O3'
_chemical_formula_sum            'C29 H26 N2 O3'
_chemical_formula_weight         450.52
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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'
'-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                   10.1449(2)
_cell_length_b                   11.6133(3)
_cell_length_c                   40.0056(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4713.29(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8471
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      69.81
_cell_measurement_theta_min      3.314
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1376 before and 0.0701 after correction. The Ratio of minimum to maximum transmission is 0.6955. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'white solid'
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            29650
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.084
_diffrn_reflns_theta_min         4.888
_diffrn_ambient_temperature      301.85
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3452
_reflns_number_total             4456
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0685P)²+1.5826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1408
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17),
 C18(H18), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.53645(16) 0.44550(12) 0.69760(3) 0.0558(4) Uani 1 1 d . . . . .
O2 O 0.33103(17) 0.60843(15) 0.58402(5) 0.0764(5) Uani 1 1 d . . . . .
O3 O 0.36627(16) 0.42261(14) 0.57466(4) 0.0663(5) Uani 1 1 d . . . . .
N1 N 0.55927(19) 0.44288(14) 0.73253(4) 0.0515(4) Uani 1 1 d . . . . .
N2 N 0.56648(16) 0.45194(14) 0.62202(4) 0.0448(4) Uani 1 1 d . . . . .
C1 C 0.6953(2) 0.39970(17) 0.79498(5) 0.0472(5) Uani 1 1 d . . . . .
H1 H 0.723028 0.467110 0.784586 0.057 Uiso 1 1 calc R . . . .
C2 C 0.7260(2) 0.3810(2) 0.82824(5) 0.0551(5) Uani 1 1 d . . . . .
H2 H 0.775180 0.435217 0.839935 0.066 Uiso 1 1 calc R . . . .
C3 C 0.6840(2) 0.2825(2) 0.84409(5) 0.0592(6) Uani 1 1 d . . . . .
H3 H 0.703111 0.270894 0.866576 0.071 Uiso 1 1 calc R . . . .
C4 C 0.6132(2) 0.2006(2) 0.82646(5) 0.0563(5) Uani 1 1 d . . . . .
H4 H 0.585161 0.133745 0.837109 0.068 Uiso 1 1 calc R . . . .
C5 C 0.5840(2) 0.21790(17) 0.79311(5) 0.0462(5) Uani 1 1 d . . . . .
H5 H 0.537668 0.161935 0.781344 0.055 Uiso 1 1 calc R . . . .
C6 C 0.62344(18) 0.31877(15) 0.77691(4) 0.0390(4) Uani 1 1 d . . . . .
C7 C 0.59140(19) 0.34069(15) 0.74124(4) 0.0391(4) Uani 1 1 d . . . . .
C8 C 0.59175(19) 0.25410(14) 0.71287(4) 0.0382(4) Uani 1 1 d . . . . .
C9 C 0.4670(2) 0.17968(18) 0.71345(5) 0.0507(5) Uani 1 1 d . . . . .
H9A H 0.469653 0.129193 0.732436 0.076 Uiso 1 1 calc GR . . . .
H9B H 0.462462 0.134811 0.693326 0.076 Uiso 1 1 calc GR . . . .
H9C H 0.390816 0.228419 0.714938 0.076 Uiso 1 1 calc GR . . . .
C10 C 0.7143(2) 0.17759(18) 0.71308(5) 0.0531(5) Uani 1 1 d . . . . .
H10A H 0.791643 0.224825 0.714711 0.080 Uiso 1 1 calc GR . . . .
H10B H 0.717532 0.133560 0.692792 0.080 Uiso 1 1 calc GR . . . .
H10C H 0.710551 0.126308 0.731882 0.080 Uiso 1 1 calc GR . . . .
C11 C 0.58145(19) 0.33886(15) 0.68302(5) 0.0398(4) Uani 1 1 d . . . . .
H11 H 0.514281 0.310623 0.667441 0.048 Uiso 1 1 calc R . . . .
C12 C 0.7063(2) 0.36382(18) 0.66384(5) 0.0489(5) Uani 1 1 d . . . . .
H12A H 0.740823 0.292285 0.654893 0.059 Uiso 1 1 calc R . . . .
H12B H 0.771579 0.395139 0.679039 0.059 Uiso 1 1 calc R . . . .
C13 C 0.68510(19) 0.44801(16) 0.63535(4) 0.0410(4) Uani 1 1 d . . . . .
C14 C 0.79101(19) 0.51710(16) 0.62330(4) 0.0396(4) Uani 1 1 d . . . . .
C15 C 0.9215(2) 0.50894(18) 0.63588(5) 0.0471(5) Uani 1 1 d . . . . .
H15 H 0.940316 0.456648 0.652828 0.057 Uiso 1 1 calc R . . . .
C16 C 1.0194(2) 0.5766(2) 0.62346(5) 0.0541(5) Uani 1 1 d . . . . .
H16 H 1.104324 0.570617 0.632056 0.065 Uiso 1 1 calc R . . . .
C17 C 0.9931(2) 0.6551(2) 0.59788(6) 0.0573(6) Uani 1 1 d . . . . .
H17 H 1.060509 0.701492 0.589712 0.069 Uiso 1 1 calc R . . . .
C18 C 0.8702(2) 0.66443(18) 0.58482(5) 0.0504(5) Uani 1 1 d . . . . .
H18 H 0.854885 0.716279 0.567534 0.060 Uiso 1 1 calc R . . . .
C19 C 0.76474(19) 0.59633(15) 0.59710(4) 0.0402(4) Uani 1 1 d . . . . .
C20 C 0.63403(19) 0.60204(15) 0.58357(4) 0.0395(4) Uani 1 1 d . . . . .
C21 C 0.54216(19) 0.52749(16) 0.59662(4) 0.0410(4) Uani 1 1 d . . . . .
C22 C 0.4025(2) 0.52655(17) 0.58464(5) 0.0458(5) Uani 1 1 d . . . . .
C23 C 0.2323(3) 0.4097(2) 0.56277(7) 0.0788(8) Uani 1 1 d . . . . .
H23A H 0.219115 0.457822 0.543544 0.118 Uiso 1 1 calc GR . . . .
H23B H 0.171944 0.431954 0.580096 0.118 Uiso 1 1 calc GR . . . .
H23C H 0.216873 0.330790 0.556787 0.118 Uiso 1 1 calc GR . . . .
C24 C 0.60272(19) 0.68189(16) 0.55567(4) 0.0419(4) Uani 1 1 d . . . . .
C25 C 0.6120(2) 0.80009(18) 0.55971(6) 0.0599(6) Uani 1 1 d . . . . .
H25 H 0.634892 0.830162 0.580458 0.072 Uiso 1 1 calc R . . . .
C26 C 0.5878(3) 0.8738(2) 0.53337(7) 0.0759(8) Uani 1 1 d . . . . .
H26 H 0.595795 0.952890 0.536362 0.091 Uiso 1 1 calc R . . . .
C27 C 0.5521(3) 0.8309(2) 0.50295(7) 0.0815(9) Uani 1 1 d . . . . .
H27 H 0.535526 0.880675 0.485233 0.098 Uiso 1 1 calc R . . . .
C28 C 0.5407(3) 0.7144(3) 0.49852(6) 0.0862(10) Uani 1 1 d . . . . .
H28 H 0.515398 0.685163 0.477845 0.103 Uiso 1 1 calc R . . . .
C29 C 0.5668(3) 0.6399(2) 0.52478(5) 0.0648(7) Uani 1 1 d . . . . .
H29 H 0.559958 0.560865 0.521518 0.078 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
O1 N1 1.417(2) . ?
O1 C11 1.443(2) . ?
O2 C22 1.196(2) . ?
O3 C22 1.323(2) . ?
O3 C23 1.448(3) . ?
N1 C7 1.279(2) . ?
N2 C13 1.317(3) . ?
N2 C21 1.365(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.384(3) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(3) . ?
C6 C7 1.485(2) . ?
C7 C8 1.516(2) . ?
C8 C9 1.533(3) . ?
C8 C10 1.528(3) . ?
C8 C11 1.551(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9800 . ?
C11 C12 1.509(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.517(2) . ?
C13 C14 1.425(3) . ?
C14 C15 1.419(3) . ?
C14 C19 1.420(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.356(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.419(3) . ?
C19 C20 1.434(3) . ?
C20 C21 1.375(3) . ?
C20 C24 1.485(2) . ?
C21 C22 1.496(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.385(3) . ?
C24 C29 1.377(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.380(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.364(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.369(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.386(3) . ?
C29 H29 0.9300 . ?

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
N1 O1 C11 109.17(13) . . ?
C22 O3 C23 117.01(19) . . ?
C7 N1 O1 109.30(15) . . ?
C13 N2 C21 119.27(16) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.7(2) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.58(19) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.36(18) . . ?
C1 C6 C7 119.86(17) . . ?
C5 C6 C7 121.78(17) . . ?
N1 C7 C6 118.47(16) . . ?
N1 C7 C8 114.32(16) . . ?
C6 C7 C8 127.21(15) . . ?
C7 C8 C9 111.15(16) . . ?
C7 C8 C10 112.55(16) . . ?
C7 C8 C11 98.93(13) . . ?
C9 C8 C11 108.29(15) . . ?
C10 C8 C9 110.09(16) . . ?
C10 C8 C11 115.35(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 C8 104.76(14) . . ?
O1 C11 H11 108.9 . . ?
O1 C11 C12 107.83(16) . . ?
C8 C11 H11 108.9 . . ?
C12 C11 C8 117.19(16) . . ?
C12 C11 H11 108.9 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C11 C12 C13 112.77(16) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
N2 C13 C12 117.13(17) . . ?
N2 C13 C14 122.17(16) . . ?
C14 C13 C12 120.68(17) . . ?
C15 C14 C13 123.07(17) . . ?
C15 C14 C19 118.69(17) . . ?
C19 C14 C13 118.23(17) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.85(19) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.03(19) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C20 118.83(17) . . ?
C18 C19 C14 118.39(18) . . ?
C18 C19 C20 122.76(17) . . ?
C19 C20 C24 120.68(17) . . ?
C21 C20 C19 117.03(16) . . ?
C21 C20 C24 122.23(17) . . ?
N2 C21 C20 124.38(18) . . ?
N2 C21 C22 113.89(16) . . ?
C20 C21 C22 121.68(17) . . ?
O2 C22 O3 123.4(2) . . ?
O2 C22 C21 125.1(2) . . ?
O3 C22 C21 111.48(17) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C20 121.09(17) . . ?
C29 C24 C20 120.65(18) . . ?
C29 C24 C25 118.24(19) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 120.9(2) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.1(2) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 119.9(2) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C24 C29 C28 120.7(2) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
