# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1544842'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41

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   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3863(16)
_cell_length_b                   17.598(3)
_cell_length_c                   11.455(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.320(4)
_cell_angle_gamma                90.00
_cell_volume                     1815.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5306
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18272
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4121
_reflns_number_gt                3514
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0621P)²+0.2905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4121
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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
O1 O 0.33621(8) 0.99771(4) 0.19023(7) 0.02660(19) Uani 1 1 d . . .
N1 N 0.54754(9) 1.03439(5) 0.33681(7) 0.02097(19) Uani 1 1 d . . .
C1 C 0.73750(12) 1.14878(6) 0.46158(10) 0.0261(2) Uani 1 1 d . . .
H1 H 0.6450 1.1622 0.4062 0.031 Uiso 1 1 calc R . .
C2 C 0.83874(14) 1.20526(6) 0.51319(11) 0.0345(3) Uani 1 1 d . . .
H2 H 0.8147 1.2570 0.4934 0.041 Uiso 1 1 calc R . .
C3 C 0.97460(13) 1.18669(6) 0.59338(12) 0.0343(3) Uani 1 1 d . . .
H3 H 1.0442 1.2255 0.6277 0.041 Uiso 1 1 calc R . .
C4 C 1.00837(12) 1.11118(6) 0.62322(10) 0.0285(2) Uani 1 1 d . . .
H4 H 1.1010 1.0982 0.6787 0.034 Uiso 1 1 calc R . .
C5 C 0.90713(11) 1.05462(6) 0.57221(9) 0.0235(2) Uani 1 1 d . . .
H5 H 0.9312 1.0031 0.5933 0.028 Uiso 1 1 calc R . .
C6 C 0.77030(11) 1.07235(5) 0.49024(9) 0.0200(2) Uani 1 1 d . . .
C7 C 0.66155(11) 1.01207(6) 0.43326(9) 0.0192(2) Uani 1 1 d . . .
C8 C 0.67610(11) 0.93765(5) 0.47507(9) 0.0204(2) Uani 1 1 d . . .
H8 H 0.7556 0.9249 0.5442 0.025 Uiso 1 1 calc R . .
C9 C 0.57565(11) 0.88044(5) 0.41731(9) 0.0196(2) Uani 1 1 d . . .
C10 C 0.46070(11) 0.90321(6) 0.31852(9) 0.0201(2) Uani 1 1 d . . .
C11 C 0.45469(11) 0.98013(6) 0.28658(9) 0.0207(2) Uani 1 1 d . . .
C12 C 0.23704(12) 0.93162(6) 0.16613(9) 0.0228(2) Uani 1 1 d . . .
H12 H 0.1541 0.9404 0.2035 0.027 Uiso 1 1 calc R . .
C13 C 0.33226(12) 0.86376(6) 0.23110(9) 0.0249(2) Uani 1 1 d . . .
H13A H 0.2767 0.8319 0.2745 0.030 Uiso 1 1 calc R . .
H13B H 0.3659 0.8318 0.1728 0.030 Uiso 1 1 calc R . .
C14 C 0.17331(11) 0.92121(5) 0.03116(9) 0.0210(2) Uani 1 1 d . . .
C15 C 0.26368(13) 0.92416(6) -0.04589(10) 0.0285(2) Uani 1 1 d . . .
H15 H 0.3655 0.9372 -0.0144 0.034 Uiso 1 1 calc R . .
C16 C 0.20619(15) 0.90816(7) -0.16892(11) 0.0352(3) Uani 1 1 d . . .
H16 H 0.2689 0.9100 -0.2211 0.042 Uiso 1 1 calc R . .
C17 C 0.05779(14) 0.88954(6) -0.21561(10) 0.0333(3) Uani 1 1 d . . .
H17 H 0.0189 0.8777 -0.2995 0.040 Uiso 1 1 calc R . .
C18 C -0.03349(13) 0.88827(6) -0.13985(11) 0.0321(3) Uani 1 1 d . . .
H18 H -0.1359 0.8766 -0.1720 0.038 Uiso 1 1 calc R . .
C19 C 0.02405(12) 0.90396(6) -0.01663(10) 0.0261(2) Uani 1 1 d . . .
H19 H -0.0392 0.9029 0.0351 0.031 Uiso 1 1 calc R . .
C20 C 0.59818(11) 0.80079(5) 0.46200(9) 0.0206(2) Uani 1 1 d . . .
C21 C 0.65874(12) 0.78548(6) 0.58572(9) 0.0253(2) Uani 1 1 d . . .
H21 H 0.6810 0.8263 0.6423 0.030 Uiso 1 1 calc R . .
C22 C 0.68681(13) 0.71115(6) 0.62703(10) 0.0295(2) Uani 1 1 d . . .
H22 H 0.7273 0.7015 0.7115 0.035 Uiso 1 1 calc R . .
C23 C 0.65587(12) 0.65107(6) 0.54547(11) 0.0299(3) Uani 1 1 d . . .
H23 H 0.6775 0.6004 0.5736 0.036 Uiso 1 1 calc R . .
C24 C 0.59330(13) 0.66527(6) 0.42288(11) 0.0305(3) Uani 1 1 d . . .
H24 H 0.5706 0.6242 0.3668 0.037 Uiso 1 1 calc R . .
C25 C 0.56358(12) 0.73944(6) 0.38159(10) 0.0256(2) Uani 1 1 d . . .
H25 H 0.5191 0.7486 0.2975 0.031 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 C11 1.3641(12) . ?
O1 C12 1.4666(12) . ?
N1 C11 1.3117(13) . ?
N1 C7 1.3622(13) . ?
C1 C2 1.3873(15) . ?
C1 C6 1.3981(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.3851(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3865(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3867(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3966(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4896(13) . ?
C7 C8 1.3880(14) . ?
C8 C9 1.4105(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.3853(13) . ?
C9 C20 1.4868(14) . ?
C10 C11 1.3992(14) . ?
C10 C13 1.5033(13) . ?
C12 C14 1.5040(14) . ?
C12 C13 1.5508(14) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3863(16) . ?
C14 C19 1.3870(14) . ?
C15 C16 1.3890(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3839(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3804(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3898(16) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.3969(14) . ?
C20 C21 1.3969(14) . ?
C21 C22 1.3907(15) . ?
C21 H21 0.9500 . ?
C22 C23 1.3866(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.3841(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3896(15) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C11 O1 C12 107.61(7) . . ?
C11 N1 C7 114.80(9) . . ?
C2 C1 C6 120.66(10) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.42(10) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.59(10) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.12(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.98(10) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.23(9) . . ?
C5 C6 C7 121.53(9) . . ?
C1 C6 C7 120.24(9) . . ?
N1 C7 C8 122.05(9) . . ?
N1 C7 C6 115.81(9) . . ?
C8 C7 C6 122.14(9) . . ?
C7 C8 C9 121.58(9) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 116.18(9) . . ?
C10 C9 C20 123.83(9) . . ?
C8 C9 C20 119.98(9) . . ?
C9 C10 C11 117.28(9) . . ?
C9 C10 C13 134.85(9) . . ?
C11 C10 C13 107.86(8) . . ?
N1 C11 O1 118.68(9) . . ?
N1 C11 C10 128.07(9) . . ?
O1 C11 C10 113.25(8) . . ?
O1 C12 C14 109.76(8) . . ?
O1 C12 C13 105.70(8) . . ?
C14 C12 C13 114.12(8) . . ?
O1 C12 H12 109.0 . . ?
C14 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C10 C13 C12 102.13(8) . . ?
C10 C13 H13A 111.3 . . ?
C12 C13 H13A 111.3 . . ?
C10 C13 H13B 111.3 . . ?
C12 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C15 C14 C19 119.20(10) . . ?
C15 C14 C12 120.81(9) . . ?
C19 C14 C12 119.88(10) . . ?
C14 C15 C16 120.37(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.13(12) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.74(11) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.17(11) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.36(11) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C25 C20 C21 118.21(9) . . ?
C25 C20 C9 121.16(9) . . ?
C21 C20 C9 120.61(9) . . ?
C22 C21 C20 120.71(10) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.28(10) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.65(10) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.15(10) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.95(10) . . ?
C24 C25 H25 119.5 . . ?
C20 C25 H25 119.5 . . ?

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
C6 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 0.55(19) . . . . ?
C3 C4 C5 C6 0.11(18) . . . . ?
C4 C5 C6 C1 -0.47(16) . . . . ?
C4 C5 C6 C7 179.00(10) . . . . ?
C2 C1 C6 C5 0.18(17) . . . . ?
C2 C1 C6 C7 -179.30(11) . . . . ?
C11 N1 C7 C8 -0.69(14) . . . . ?
C11 N1 C7 C6 178.77(9) . . . . ?
C5 C6 C7 N1 -166.58(9) . . . . ?
C1 C6 C7 N1 12.88(14) . . . . ?
C5 C6 C7 C8 12.88(15) . . . . ?
C1 C6 C7 C8 -167.66(10) . . . . ?
N1 C7 C8 C9 1.98(16) . . . . ?
C6 C7 C8 C9 -177.44(9) . . . . ?
C7 C8 C9 C10 -1.25(15) . . . . ?
C7 C8 C9 C20 177.73(9) . . . . ?
C8 C9 C10 C11 -0.54(14) . . . . ?
C20 C9 C10 C11 -179.47(9) . . . . ?
C8 C9 C10 C13 179.46(11) . . . . ?
C20 C9 C10 C13 0.53(19) . . . . ?
C7 N1 C11 O1 179.26(9) . . . . ?
C7 N1 C11 C10 -1.32(16) . . . . ?
C12 O1 C11 N1 -169.81(9) . . . . ?
C12 O1 C11 C10 10.69(12) . . . . ?
C9 C10 C11 N1 1.97(17) . . . . ?
C13 C10 C11 N1 -178.03(10) . . . . ?
C9 C10 C11 O1 -178.58(9) . . . . ?
C13 C10 C11 O1 1.42(12) . . . . ?
C11 O1 C12 C14 -141.31(9) . . . . ?
C11 O1 C12 C13 -17.80(10) . . . . ?
C9 C10 C13 C12 168.06(11) . . . . ?
C11 C10 C13 C12 -11.94(11) . . . . ?
O1 C12 C13 C10 17.76(10) . . . . ?
C14 C12 C13 C10 138.47(9) . . . . ?
O1 C12 C14 C15 46.88(13) . . . . ?
C13 C12 C14 C15 -71.54(12) . . . . ?
O1 C12 C14 C19 -136.99(10) . . . . ?
C13 C12 C14 C19 104.59(11) . . . . ?
C19 C14 C15 C16 -1.60(16) . . . . ?
C12 C14 C15 C16 174.55(10) . . . . ?
C14 C15 C16 C17 0.36(18) . . . . ?
C15 C16 C17 C18 1.17(18) . . . . ?
C16 C17 C18 C19 -1.44(17) . . . . ?
C15 C14 C19 C18 1.33(16) . . . . ?
C12 C14 C19 C18 -174.86(9) . . . . ?
C17 C18 C19 C14 0.19(17) . . . . ?
C10 C9 C20 C25 34.42(16) . . . . ?
C8 C9 C20 C25 -144.48(10) . . . . ?
C10 C9 C20 C21 -147.43(11) . . . . ?
C8 C9 C20 C21 33.67(15) . . . . ?
C25 C20 C21 C22 1.44(16) . . . . ?
C9 C20 C21 C22 -176.76(10) . . . . ?
C20 C21 C22 C23 0.46(18) . . . . ?
C21 C22 C23 C24 -1.64(18) . . . . ?
C22 C23 C24 C25 0.89(18) . . . . ?
C23 C24 C25 C20 1.05(18) . . . . ?
C21 C20 C25 C24 -2.19(16) . . . . ?
C9 C20 C25 C24 176.00(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038
