# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1523273'
_audit_update_record             
;
2016-12-18 deposited with the CCDC.
2017-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
4-((3-Methyl-2,3-dihydrobenzofuran-3-yl)methyl)-3-phenylisoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   7.1675(4)
_cell_length_b                   13.1365(8)
_cell_length_c                   10.0074(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.0748(19)
_cell_angle_gamma                90
_cell_volume                     924.71(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4014
_cell_measurement_theta_min      3.101
_cell_measurement_theta_max      27.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            14464
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.101
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4285
_reflns_number_gt                2516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.997

_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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.9(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4285
_refine_ls_number_parameters     245
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
N1 N 0.8018(4) 0.0186(2) 0.9705(3) 0.0530(9) Uani 1 1 d . . . . .
C9 C 0.4273(4) 0.0461(3) 0.6471(3) 0.0408(8) Uani 1 1 d . . . . .
H9A H 0.4541 -0.0193 0.6099 0.049 Uiso 1 1 calc R U . . .
H9B H 0.4258 0.0967 0.5763 0.049 Uiso 1 1 calc R U . . .
C3 C 0.0377(5) -0.0539(4) 0.4720(4) 0.0619(11) Uani 1 1 d . . . . .
H3 H 0.1074 -0.1137 0.4897 0.074 Uiso 1 1 calc R U . . .
C7 C -0.0292(6) 0.1137(3) 0.5299(4) 0.0526(10) Uani 1 1 d . . . . .
C2 C 0.0771(4) 0.0279(3) 0.5570(3) 0.0423(9) Uani 1 1 d . . . . .
C1 C 0.2252(4) 0.0416(3) 0.6841(3) 0.0447(9) Uani 1 1 d . . . . .
C6 C -0.1751(6) 0.1228(4) 0.4188(5) 0.0752(14) Uani 1 1 d . . . . .
H6 H -0.2460 0.1823 0.4025 0.090 Uiso 1 1 calc R U . . .
O1 O 0.0271(4) 0.1894(2) 0.6216(3) 0.0830(10) Uani 1 1 d . . . . .
C4 C -0.1085(6) -0.0464(4) 0.3581(4) 0.0733(13) Uani 1 1 d . . . . .
H4 H -0.1356 -0.1013 0.2989 0.088 Uiso 1 1 calc R U . . .
C5 C -0.2115(6) 0.0408(4) 0.3335(4) 0.0720(13) Uani 1 1 d . . . . .
H5 H -0.3085 0.0448 0.2572 0.086 Uiso 1 1 calc R U . . .
C8 C 0.1583(6) 0.1451(3) 0.7330(4) 0.0652(12) Uani 1 1 d . . . . .
H8A H 0.0967 0.1348 0.8102 0.078 Uiso 1 1 calc R U . . .
H8B H 0.2663 0.1900 0.7609 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6414(4) 0.1756(3) 0.7945(3) 0.0410(9) Uani 1 1 d . . . . .
C16 C 0.7756(5) 0.1967(3) 0.9135(4) 0.0457(9) Uani 1 1 d . . . . .
C10 C 0.5864(4) 0.0715(3) 0.7645(3) 0.0393(9) Uani 1 1 d . . . . .
C18 C 0.6807(5) -0.0022(3) 0.8504(3) 0.0410(9) Uani 1 1 d . . . . .
C17 C 0.8414(5) 0.1137(3) 0.9991(4) 0.0541(11) Uani 1 1 d . . . . .
H17 H 0.9193 0.1281 1.0825 0.065 Uiso 1 1 calc R U . . .
C15 C 0.8431(6) 0.2964(3) 0.9432(4) 0.0596(11) Uani 1 1 d . . . . .
H15 H 0.9323 0.3091 1.0221 0.072 Uiso 1 1 calc R U . . .
C12 C 0.5756(6) 0.2596(3) 0.7093(4) 0.0585(11) Uani 1 1 d . . . . .
H12 H 0.4849 0.2493 0.6306 0.070 Uiso 1 1 calc R U . . .
C13 C 0.6433(6) 0.3552(3) 0.7409(5) 0.0691(12) Uani 1 1 d . . . . .
H13 H 0.5980 0.4090 0.6835 0.083 Uiso 1 1 calc R U . . .
C14 C 0.7787(7) 0.3736(3) 0.8574(5) 0.0705(12) Uani 1 1 d . . . . .
H14 H 0.8253 0.4392 0.8764 0.085 Uiso 1 1 calc R U . . .
C19 C 0.6694(5) -0.1135(3) 0.8189(4) 0.0462(9) Uani 1 1 d . . . . .
C24 C 0.7201(5) -0.1488(3) 0.7004(4) 0.0534(10) Uani 1 1 d . . . . .
H24 H 0.7495 -0.1027 0.6370 0.064 Uiso 1 1 calc R U . . .
C20 C 0.6267(6) -0.1842(3) 0.9108(4) 0.0609(11) Uani 1 1 d . . . . .
H20 H 0.5955 -0.1620 0.9920 0.073 Uiso 1 1 calc R U . . .
C21 C 0.6293(7) -0.2864(4) 0.8844(6) 0.0770(15) Uani 1 1 d . . . . .
H21 H 0.5963 -0.3328 0.9461 0.092 Uiso 1 1 calc R U . . .
C23 C 0.7271(6) -0.2516(4) 0.6756(5) 0.0700(12) Uani 1 1 d . . . . .
H23 H 0.7637 -0.2744 0.5965 0.084 Uiso 1 1 calc R U . . .
C22 C 0.6808(7) -0.3208(4) 0.7665(7) 0.0827(15) Uani 1 1 d . . . . .
H22 H 0.6842 -0.3902 0.7487 0.099 Uiso 1 1 calc R U . . .
C25 C 0.2146(5) -0.0393(4) 0.7898(4) 0.0746(14) Uani 1 1 d . . . . .
H25A H 0.0885 -0.0411 0.8091 0.112 Uiso 1 1 calc R U . . .
H25B H 0.3040 -0.0239 0.8717 0.112 Uiso 1 1 calc R U . . .
H25C H 0.2446 -0.1044 0.7558 0.112 Uiso 1 1 calc R U . . .


_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
N1 C17 1.301(5) . ?
N1 C18 1.368(4) . ?
C9 C10 1.509(4) . ?
C9 C1 1.563(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 C2 1.366(5) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9300 . ?
C7 C2 1.358(5) . ?
C7 O1 1.361(5) . ?
C7 C6 1.377(5) . ?
C2 C1 1.503(4) . ?
C1 C25 1.512(5) . ?
C1 C8 1.552(5) . ?
C6 C5 1.368(6) . ?
C6 H6 0.9300 . ?
O1 C8 1.437(5) . ?
C4 C5 1.360(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 C16 1.408(4) . ?
C11 C12 1.419(5) . ?
C11 C10 1.439(5) . ?
C16 C15 1.407(5) . ?
C16 C17 1.410(5) . ?
C10 C18 1.382(4) . ?
C18 C19 1.494(5) . ?
C17 H17 0.9300 . ?
C15 C14 1.352(6) . ?
C15 H15 0.9300 . ?
C12 C13 1.360(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C19 C20 1.383(5) . ?
C19 C24 1.385(5) . ?
C24 C23 1.375(5) . ?
C24 H24 0.9300 . ?
C20 C21 1.370(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(8) . ?
C21 H21 0.9300 . ?
C23 C22 1.371(7) . ?
C23 H23 0.9300 . ?
C22 H22 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C17 N1 C18 117.4(3) . . ?
C10 C9 C1 114.8(3) . . ?
C10 C9 H9A 108.6 . . ?
C1 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C1 C9 H9B 108.6 . . ?
H9A C9 H9B 107.5 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C2 C7 O1 112.9(3) . . ?
C2 C7 C6 122.9(4) . . ?
O1 C7 C6 124.2(4) . . ?
C7 C2 C3 119.1(3) . . ?
C7 C2 C1 110.4(3) . . ?
C3 C2 C1 130.5(4) . . ?
C2 C1 C25 112.7(3) . . ?
C2 C1 C8 99.3(3) . . ?
C25 C1 C8 109.6(3) . . ?
C2 C1 C9 109.9(3) . . ?
C25 C1 C9 111.5(3) . . ?
C8 C1 C9 113.5(3) . . ?
C5 C6 C7 117.4(4) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C7 O1 C8 107.0(3) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
O1 C8 C1 107.8(3) . . ?
O1 C8 H8A 110.1 . . ?
C1 C8 H8A 110.1 . . ?
O1 C8 H8B 110.1 . . ?
C1 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
C16 C11 C12 116.7(3) . . ?
C16 C11 C10 118.6(3) . . ?
C12 C11 C10 124.7(3) . . ?
C15 C16 C11 120.9(4) . . ?
C15 C16 C17 122.0(3) . . ?
C11 C16 C17 117.1(3) . . ?
C18 C10 C11 117.0(3) . . ?
C18 C10 C9 122.4(3) . . ?
C11 C10 C9 120.5(3) . . ?
N1 C18 C10 123.9(3) . . ?
N1 C18 C19 112.4(3) . . ?
C10 C18 C19 123.6(3) . . ?
N1 C17 C16 125.1(3) . . ?
N1 C17 H17 117.4 . . ?
C16 C17 H17 117.4 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.1(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C20 C19 C24 118.2(4) . . ?
C20 C19 C18 121.8(3) . . ?
C24 C19 C18 119.8(3) . . ?
C23 C24 C19 120.5(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C21 C20 C19 121.1(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C22 C23 C24 120.6(4) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C22 C21 119.3(5) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C1 C25 H25A 109.5 . . ?
C1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
O1 C7 C2 C3 -179.1(3) . . . . ?
C6 C7 C2 C3 -0.7(6) . . . . ?
O1 C7 C2 C1 1.2(4) . . . . ?
C6 C7 C2 C1 179.6(4) . . . . ?
C4 C3 C2 C7 1.1(6) . . . . ?
C4 C3 C2 C1 -179.3(3) . . . . ?
C7 C2 C1 C25 124.3(4) . . . . ?
C3 C2 C1 C25 -55.3(5) . . . . ?
C7 C2 C1 C8 8.5(4) . . . . ?
C3 C2 C1 C8 -171.2(4) . . . . ?
C7 C2 C1 C9 -110.8(3) . . . . ?
C3 C2 C1 C9 69.6(5) . . . . ?
C10 C9 C1 C2 173.5(3) . . . . ?
C10 C9 C1 C25 -60.9(4) . . . . ?
C10 C9 C1 C8 63.4(4) . . . . ?
C2 C7 C6 C5 -0.1(6) . . . . ?
O1 C7 C6 C5 178.1(4) . . . . ?
C2 C7 O1 C8 -11.4(5) . . . . ?
C6 C7 O1 C8 170.2(4) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C7 C6 C5 C4 0.5(7) . . . . ?
C7 O1 C8 C1 16.5(4) . . . . ?
C2 C1 C8 O1 -14.8(4) . . . . ?
C25 C1 C8 O1 -133.0(3) . . . . ?
C9 C1 C8 O1 101.7(3) . . . . ?
C12 C11 C16 C15 -1.5(5) . . . . ?
C10 C11 C16 C15 176.0(3) . . . . ?
C12 C11 C16 C17 179.8(3) . . . . ?
C10 C11 C16 C17 -2.7(4) . . . . ?
C16 C11 C10 C18 -4.7(4) . . . . ?
C12 C11 C10 C18 172.6(3) . . . . ?
C16 C11 C10 C9 173.0(3) . . . . ?
C12 C11 C10 C9 -9.7(5) . . . . ?
C1 C9 C10 C18 87.5(4) . . . . ?
C1 C9 C10 C11 -90.2(4) . . . . ?
C17 N1 C18 C10 -5.8(5) . . . . ?
C17 N1 C18 C19 171.3(3) . . . . ?
C11 C10 C18 N1 9.4(4) . . . . ?
C9 C10 C18 N1 -168.3(3) . . . . ?
C11 C10 C18 C19 -167.3(3) . . . . ?
C9 C10 C18 C19 14.9(5) . . . . ?
C18 N1 C17 C16 -2.7(5) . . . . ?
C15 C16 C17 N1 -171.8(4) . . . . ?
C11 C16 C17 N1 6.8(5) . . . . ?
C11 C16 C15 C14 0.3(5) . . . . ?
C17 C16 C15 C14 178.9(4) . . . . ?
C16 C11 C12 C13 1.4(5) . . . . ?
C10 C11 C12 C13 -176.0(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C16 C15 C14 C13 1.1(6) . . . . ?
C12 C13 C14 C15 -1.3(6) . . . . ?
N1 C18 C19 C20 53.6(5) . . . . ?
C10 C18 C19 C20 -129.3(4) . . . . ?
N1 C18 C19 C24 -120.2(3) . . . . ?
C10 C18 C19 C24 56.9(5) . . . . ?
C20 C19 C24 C23 0.0(6) . . . . ?
C18 C19 C24 C23 174.1(3) . . . . ?
C24 C19 C20 C21 -1.6(6) . . . . ?
C18 C19 C20 C21 -175.5(3) . . . . ?
C19 C20 C21 C22 2.0(7) . . . . ?
C19 C24 C23 C22 1.2(6) . . . . ?
C24 C23 C22 C21 -0.9(7) . . . . ?
C20 C21 C22 C23 -0.7(7) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

