# Electronic Supplementary Material (ESI) for Green 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. 
# 
#######################################################################

data_1062
_database_code_depnum_ccdc_archive 'CCDC 1852051'
_audit_update_record             
;
2018-06-27 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.2(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_creation_date             2017-05-31
_chemical_formula_sum            'C33 H27 N3 O2'
_chemical_formula_weight         497.570
_refine_ls_R_factor_all          0.061
_cell_length_a                   20.2486(10)
_cell_length_b                   6.7682(2)
_cell_length_c                   20.858(1)
_cell_angle_alpha                90.000
_cell_angle_beta                 118.296(6)
_cell_angle_gamma                90.000
_cell_volume                     2517.0(2)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_space_group_crystal_system      monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  -P_2yn

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C1 C 0.6607(1) 0.6508(2) 0.3479(1) 1.000 4 e ? d Uani 0.0161(4)
C2 C 0.7142(1) 0.7893(3) 0.3504(1) 1.000 4 e ? d Uani 0.0172(4)
H2 H 0.7621 0.7943 0.3899 1.000 4 e ? calc Uiso 0.02100
C3 C 0.6933(1) 0.9150(2) 0.2932(1) 1.000 4 e ? d Uani 0.0167(4)
C4 C 0.5653(1) 0.7712(2) 0.2284(1) 1.000 4 e ? d Uani 0.0158(4)
C5 C 0.5890(1) 0.6432(2) 0.2898(1) 1.000 4 e ? d Uani 0.0157(3)
C6 C 0.5492(1) 0.4888(3) 0.3033(1) 1.000 4 e ? d Uani 0.0161(4)
C7 C 0.5983(1) 0.4011(2) 0.3687(1) 1.000 4 e ? d Uani 0.0159(4)
C8 C 0.7355(1) 0.4631(3) 0.4609(1) 1.000 4 e ? d Uani 0.0167(4)
C9 C 0.7692(1) 0.2798(3) 0.4689(1) 1.000 4 e ? d Uani 0.0203(4)
H9 H 0.7472 0.1835 0.4332 1.000 4 e ? calc Uiso 0.02400
C10 C 0.8367(1) 0.2425(3) 0.5314(1) 1.000 4 e ? d Uani 0.0249(4)
H10 H 0.8596 0.1197 0.5380 1.000 4 e ? calc Uiso 0.03000
C11 C 0.8699(1) 0.3885(3) 0.5842(1) 1.000 4 e ? d Uani 0.0273(4)
H11 H 0.9153 0.3637 0.6256 1.000 4 e ? calc Uiso 0.03300
C12 C 0.8355(1) 0.5705(3) 0.5753(1) 1.000 4 e ? d Uani 0.0247(4)
H12 H 0.8579 0.6680 0.6105 1.000 4 e ? calc Uiso 0.03000
C13 C 0.7677(1) 0.6077(3) 0.5139(1) 1.000 4 e ? d Uani 0.0206(4)
H13 H 0.7440 0.7290 0.5084 1.000 4 e ? calc Uiso 0.02500
C14 C 0.7458(1) 1.0664(3) 0.2906(1) 1.000 4 e ? d Uani 0.0217(4)
H14A H 0.7487 1.0515 0.2462 1.000 4 e ? calc Uiso 0.03300
H14B H 0.7946 1.0485 0.3315 1.000 4 e ? calc Uiso 0.03300
H14C H 0.7276 1.1962 0.2924 1.000 4 e ? calc Uiso 0.03300
C15 C 0.6005(1) 1.0351(3) 0.1718(1) 1.000 4 e ? d Uani 0.0172(4)
C16 C 0.5768(1) 1.2254(3) 0.1743(1) 1.000 4 e ? d Uani 0.0199(4)
H16 H 0.5739 1.2688 0.2153 1.000 4 e ? calc Uiso 0.02400
C17 C 0.5573(1) 1.3515(3) 0.1154(1) 1.000 4 e ? d Uani 0.0233(4)
H17 H 0.5411 1.4794 0.1166 1.000 4 e ? calc Uiso 0.02800
C18 C 0.5621(1) 1.2854(3) 0.0548(1) 1.000 4 e ? d Uani 0.0230(4)
H18 H 0.5495 1.3697 0.0155 1.000 4 e ? calc Uiso 0.02800
C19 C 0.5855(1) 1.0943(3) 0.0526(1) 1.000 4 e ? d Uani 0.0233(4)
H19 H 0.5884 1.0506 0.0117 1.000 4 e ? calc Uiso 0.02800
C20 C 0.6047(1) 0.9677(3) 0.1112(1) 1.000 4 e ? d Uani 0.0208(4)
H20 H 0.6202 0.8392 0.1098 1.000 4 e ? calc Uiso 0.02500
C21 C 0.4142(1) 0.4361(2) 0.2704(1) 1.000 4 e ? d Uani 0.0162(4)
C22 C 0.3420(1) 0.4320(2) 0.2121(1) 1.000 4 e ? d Uani 0.0177(4)
H22 H 0.3356 0.4306 0.1649 1.000 4 e ? calc Uiso 0.02100
C23 C 0.2791(1) 0.4299(2) 0.2224(1) 1.000 4 e ? d Uani 0.0182(4)
H23 H 0.2314 0.4283 0.1825 1.000 4 e ? calc Uiso 0.02200
C24 C 0.2878(1) 0.4302(2) 0.2927(1) 1.000 4 e ? d Uani 0.0174(4)
C25 C 0.3598(1) 0.4316(2) 0.3514(1) 1.000 4 e ? d Uani 0.0181(4)
H25 H 0.3660 0.4306 0.3986 1.000 4 e ? calc Uiso 0.02200
C26 C 0.4227(1) 0.4345(2) 0.3409(1) 1.000 4 e ? d Uani 0.0172(4)
H26 H 0.4705 0.4354 0.3808 1.000 4 e ? calc Uiso 0.02100
C27 C 0.1559(1) 0.4322(3) 0.2486(1) 1.000 4 e ? d Uani 0.0206(4)
H27A H 0.1487 0.3171 0.2191 1.000 4 e ? calc Uiso 0.03100
H27B H 0.1497 0.5487 0.2200 1.000 4 e ? calc Uiso 0.03100
H27C H 0.1198 0.4327 0.2661 1.000 4 e ? calc Uiso 0.03100
C28 C 0.5877(1) 0.2287(3) 0.4053(1) 1.000 4 e ? d Uani 0.0169(4)
C29 C 0.5447(1) 0.0708(3) 0.3625(1) 1.000 4 e ? d Uani 0.0204(4)
H29 H 0.5250 0.0765 0.3122 1.000 4 e ? calc Uiso 0.02400
C30 C 0.5310(1) -0.0934(3) 0.3939(1) 1.000 4 e ? d Uani 0.0245(4)
H30 H 0.5019 -0.1964 0.3646 1.000 4 e ? calc Uiso 0.02900
C31 C 0.5607(1) -0.1047(3) 0.4689(1) 1.000 4 e ? d Uani 0.0314(5)
H31 H 0.5520 -0.2156 0.4901 1.000 4 e ? calc Uiso 0.03800
C32 C 0.6033(1) 0.0504(3) 0.5119(1) 1.000 4 e ? d Uani 0.0343(5)
H32 H 0.6231 0.0433 0.5622 1.000 4 e ? calc Uiso 0.04100
C33 C 0.6169(1) 0.2159(3) 0.4809(1) 1.000 4 e ? d Uani 0.0245(4)
H33 H 0.6455 0.3190 0.5104 1.000 4 e ? calc Uiso 0.02900
N1 N 0.6668(1) 0.5068(2) 0.3964(1) 1.000 4 e ? d Uani 0.0165(3)
N2 N 0.6209(1) 0.9049(2) 0.2335(1) 1.000 4 e ? d Uani 0.0163(3)
N3 N 0.4744(1) 0.4433(2) 0.2537(1) 1.000 4 e ? d Uani 0.0174(3)
H3 H 0.4643 0.4177 0.2096 1.000 4 e ? calc Uiso 0.02100
O1 O 0.5030(1) 0.7691(2) 0.1738(1) 1.000 4 e ? d Uani 0.0215(3)
O2 O 0.2299(1) 0.4294(2) 0.3091(1) 1.000 4 e ? d Uani 0.0206(3)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.415(2) no
C1 C5 . . 1.383(2) no
C1 N1 . . 1.367(2) no
C2 H2 . . 0.9300 no
C2 C3 . . 1.360(2) no
C3 C14 . . 1.496(2) no
C3 N2 . . 1.404(2) no
C4 C5 . . 1.428(2) no
C4 N2 . . 1.408(2) no
C4 O1 . . 1.236(2) no
C5 C6 . . 1.426(2) no
C6 C7 . . 1.384(2) no
C6 N3 . . 1.405(2) no
C7 C28 . . 1.465(2) no
C7 N1 . . 1.417(2) no
C8 C9 . . 1.388(2) no
C8 C13 . . 1.387(2) no
C8 N1 . . 1.434(2) no
C9 H9 . . 0.9300 no
C9 C10 . . 1.393(2) no
C10 H10 . . 0.9300 no
C10 C11 . . 1.392(3) no
C11 H11 . . 0.9300 no
C11 C12 . . 1.384(3) no
C12 H12 . . 0.9300 no
C12 C13 . . 1.385(3) no
C13 H13 . . 0.9300 no
C14 H14A . . 0.9600 no
C14 H14B . . 0.9600 no
C14 H14C . . 0.9600 no
C15 C16 . . 1.384(2) no
C15 C20 . . 1.383(2) no
C15 N2 . . 1.449(2) no
C16 H16 . . 0.9300 no
C16 C17 . . 1.391(2) no
C17 H17 . . 0.9300 no
C17 C18 . . 1.387(3) no
C18 H18 . . 0.9300 no
C18 C19 . . 1.386(3) no
C19 H19 . . 0.9300 no
C19 C20 . . 1.389(2) no
C20 H20 . . 0.9300 no
C21 C22 . . 1.389(2) no
C21 C26 . . 1.397(2) no
C21 N3 . . 1.418(2) no
C22 H22 . . 0.9300 no
C22 C23 . . 1.389(2) no
C23 H23 . . 0.9300 no
C23 C24 . . 1.391(2) no
C24 C25 . . 1.391(2) no
C24 O2 . . 1.369(2) no
C25 H25 . . 0.9300 no
C25 C26 . . 1.392(2) no
C26 H26 . . 0.9300 no
C27 H27A . . 0.9600 no
C27 H27B . . 0.9600 no
C27 H27C . . 0.9600 no
C27 O2 . . 1.429(2) no
C28 C29 . . 1.400(2) no
C28 C33 . . 1.399(2) no
C29 H29 . . 0.9300 no
C29 C30 . . 1.383(2) no
C30 H30 . . 0.9300 no
C30 C31 . . 1.387(3) no
C31 H31 . . 0.9300 no
C31 C32 . . 1.385(3) no
C32 H32 . . 0.9300 no
C32 C33 . . 1.384(3) no
C33 H33 . . 0.9300 no
N3 H3 . . 0.8600 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 C1 C2 . . . 121.63(16) no
N1 C1 C2 . . . 130.26(16) no
N1 C1 C5 . . . 108.11(15) no
C1 C2 H2 . . . 121.10 no
C3 C2 C1 . . . 117.88(16) no
C3 C2 H2 . . . 121.10 no
C2 C3 C14 . . . 121.94(16) no
C2 C3 N2 . . . 120.52(15) no
N2 C3 C14 . . . 117.53(15) no
N2 C4 C5 . . . 113.97(14) no
O1 C4 C5 . . . 125.52(16) no
O1 C4 N2 . . . 120.49(15) no
C1 C5 C4 . . . 122.00(15) no
C1 C5 C6 . . . 108.08(15) no
C6 C5 C4 . . . 129.90(16) no
C7 C6 C5 . . . 107.46(15) no
C7 C6 N3 . . . 130.67(16) no
N3 C6 C5 . . . 121.83(15) no
C6 C7 C28 . . . 129.84(16) no
C6 C7 N1 . . . 107.00(15) no
N1 C7 C28 . . . 123.13(15) no
C9 C8 N1 . . . 120.04(16) no
C13 C8 C9 . . . 121.05(16) no
C13 C8 N1 . . . 118.90(16) no
C8 C9 H9 . . . 120.60 no
C8 C9 C10 . . . 118.90(17) no
C10 C9 H9 . . . 120.60 no
C9 C10 H10 . . . 119.90 no
C11 C10 C9 . . . 120.24(18) no
C11 C10 H10 . . . 119.90 no
C10 C11 H11 . . . 120.00 no
C12 C11 C10 . . . 120.05(17) no
C12 C11 H11 . . . 120.00 no
C11 C12 H12 . . . 119.90 no
C11 C12 C13 . . . 120.13(18) no
C13 C12 H12 . . . 119.90 no
C8 C13 H13 . . . 120.20 no
C12 C13 C8 . . . 119.60(18) no
C12 C13 H13 . . . 120.20 no
C3 C14 H14A . . . 109.50 no
C3 C14 H14B . . . 109.50 no
C3 C14 H14C . . . 109.50 no
H14A C14 H14B . . . 109.50 no
H14A C14 H14C . . . 109.50 no
H14B C14 H14C . . . 109.50 no
C16 C15 N2 . . . 119.37(15) no
C20 C15 C16 . . . 120.93(16) no
C20 C15 N2 . . . 119.70(16) no
C15 C16 H16 . . . 120.20 no
C15 C16 C17 . . . 119.70(17) no
C17 C16 H16 . . . 120.20 no
C16 C17 H17 . . . 120.20 no
C18 C17 C16 . . . 119.63(17) no
C18 C17 H17 . . . 120.20 no
C17 C18 H18 . . . 119.90 no
C19 C18 C17 . . . 120.28(17) no
C19 C18 H18 . . . 119.90 no
C18 C19 H19 . . . 119.90 no
C18 C19 C20 . . . 120.22(17) no
C20 C19 H19 . . . 119.90 no
C15 C20 C19 . . . 119.24(17) no
C15 C20 H20 . . . 120.40 no
C19 C20 H20 . . . 120.40 no
C22 C21 C26 . . . 118.32(15) no
C22 C21 N3 . . . 117.18(15) no
C26 C21 N3 . . . 124.50(15) no
C21 C22 H22 . . . 119.10 no
C23 C22 C21 . . . 121.78(16) no
C23 C22 H22 . . . 119.10 no
C22 C23 H23 . . . 120.10 no
C22 C23 C24 . . . 119.72(16) no
C24 C23 H23 . . . 120.10 no
C25 C24 C23 . . . 119.04(16) no
O2 C24 C23 . . . 124.60(16) no
O2 C24 C25 . . . 116.36(15) no
C24 C25 H25 . . . 119.50 no
C24 C25 C26 . . . 121.05(16) no
C26 C25 H25 . . . 119.50 no
C21 C26 H26 . . . 120.00 no
C25 C26 C21 . . . 120.09(16) no
C25 C26 H26 . . . 120.00 no
H27A C27 H27B . . . 109.50 no
H27A C27 H27C . . . 109.50 no
H27B C27 H27C . . . 109.50 no
O2 C27 H27A . . . 109.50 no
O2 C27 H27B . . . 109.50 no
O2 C27 H27C . . . 109.50 no
C29 C28 C7 . . . 118.47(16) no
C33 C28 C7 . . . 123.25(16) no
C33 C28 C29 . . . 118.26(17) no
C28 C29 H29 . . . 119.50 no
C30 C29 C28 . . . 121.06(18) no
C30 C29 H29 . . . 119.50 no
C29 C30 H30 . . . 120.00 no
C29 C30 C31 . . . 120.05(18) no
C31 C30 H30 . . . 120.00 no
C30 C31 H31 . . . 120.20 no
C32 C31 C30 . . . 119.53(18) no
C32 C31 H31 . . . 120.20 no
C31 C32 H32 . . . 119.60 no
C33 C32 C31 . . . 120.74(19) no
C33 C32 H32 . . . 119.60 no
C28 C33 H33 . . . 119.80 no
C32 C33 C28 . . . 120.35(18) no
C32 C33 H33 . . . 119.80 no
C1 N1 C7 . . . 109.29(14) no
C1 N1 C8 . . . 123.22(14) no
C7 N1 C8 . . . 127.21(14) no
C3 N2 C4 . . . 123.98(14) no
C3 N2 C15 . . . 119.74(14) no
C4 N2 C15 . . . 116.27(14) no
C6 N3 C21 . . . 125.40(14) no
C6 N3 H3 . . . 117.30 no
C21 N3 H3 . . . 117.30 no
C24 O2 C27 . . . 116.28(13) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C14 . . . . -179.86(15) no
C1 C2 C3 N2 . . . . -0.6(2) no
C1 C5 C6 C7 . . . . -1.72(19) no
C1 C5 C6 N3 . . . . -179.71(15) no
C2 C1 C5 C4 . . . . 1.4(3) no
C2 C1 C5 C6 . . . . 179.72(15) no
C2 C1 N1 C7 . . . . -178.17(17) no
C2 C1 N1 C8 . . . . -3.8(3) no
C2 C3 N2 C4 . . . . 1.1(3) no
C2 C3 N2 C15 . . . . -177.74(15) no
C4 C5 C6 C7 . . . . 176.43(17) no
C4 C5 C6 N3 . . . . -1.6(3) no
C5 C1 C2 C3 . . . . -0.6(3) no
C5 C1 N1 C7 . . . . 1.12(19) no
C5 C1 N1 C8 . . . . 175.47(15) no
C5 C4 N2 C3 . . . . -0.4(2) no
C5 C4 N2 C15 . . . . 178.53(14) no
C5 C6 C7 C28 . . . . -175.71(17) no
C5 C6 C7 N1 . . . . 2.35(18) no
C5 C6 N3 C21 . . . . -125.22(18) no
C6 C7 C28 C29 . . . . 36.2(3) no
C6 C7 C28 C33 . . . . -142.29(19) no
C6 C7 N1 C1 . . . . -2.19(19) no
C6 C7 N1 C8 . . . . -176.25(15) no
C7 C6 N3 C21 . . . . 57.3(3) no
C7 C28 C29 C30 . . . . -178.21(16) no
C7 C28 C33 C32 . . . . 178.55(17) no
C8 C9 C10 C11 . . . . -1.0(3) no
C9 C8 C13 C12 . . . . 1.3(3) no
C9 C8 N1 C1 . . . . -116.12(19) no
C9 C8 N1 C7 . . . . 57.2(2) no
C9 C10 C11 C12 . . . . 0.9(3) no
C10 C11 C12 C13 . . . . 0.3(3) no
C11 C12 C13 C8 . . . . -1.4(3) no
C13 C8 C9 C10 . . . . -0.1(3) no
C13 C8 N1 C1 . . . . 62.8(2) no
C13 C8 N1 C7 . . . . -123.91(18) no
C14 C3 N2 C4 . . . . -179.59(15) no
C14 C3 N2 C15 . . . . 1.6(2) no
C15 C16 C17 C18 . . . . -0.3(3) no
C16 C15 C20 C19 . . . . 0.6(3) no
C16 C15 N2 C3 . . . . -83.3(2) no
C16 C15 N2 C4 . . . . 97.72(19) no
C16 C17 C18 C19 . . . . 0.6(3) no
C17 C18 C19 C20 . . . . -0.3(3) no
C18 C19 C20 C15 . . . . -0.3(3) no
C20 C15 C16 C17 . . . . -0.3(3) no
C20 C15 N2 C3 . . . . 96.8(2) no
C20 C15 N2 C4 . . . . -82.1(2) no
C21 C22 C23 C24 . . . . -0.6(3) no
C22 C21 C26 C25 . . . . -0.9(2) no
C22 C21 N3 C6 . . . . 166.12(16) no
C22 C23 C24 C25 . . . . -0.3(3) no
C22 C23 C24 O2 . . . . 179.62(16) no
C23 C24 C25 C26 . . . . 0.6(3) no
C23 C24 O2 C27 . . . . -1.2(2) no
C24 C25 C26 C21 . . . . 0.0(3) no
C25 C24 O2 C27 . . . . 178.72(15) no
C26 C21 C22 C23 . . . . 1.1(3) no
C26 C21 N3 C6 . . . . -13.4(3) no
C28 C7 N1 C1 . . . . 176.03(15) no
C28 C7 N1 C8 . . . . 2.0(3) no
C28 C29 C30 C31 . . . . -0.7(3) no
C29 C28 C33 C32 . . . . 0.1(3) no
C29 C30 C31 C32 . . . . 0.7(3) no
C30 C31 C32 C33 . . . . -0.3(3) no
C31 C32 C33 C28 . . . . -0.1(3) no
C33 C28 C29 C30 . . . . 0.3(3) no
N1 C1 C2 C3 . . . . 178.59(17) no
N1 C1 C5 C4 . . . . -177.97(15) no
N1 C1 C5 C6 . . . . 0.36(19) no
N1 C7 C28 C29 . . . . -141.63(17) no
N1 C7 C28 C33 . . . . 39.9(3) no
N1 C8 C9 C10 . . . . 178.77(15) no
N1 C8 C13 C12 . . . . -177.58(15) no
N2 C4 C5 C1 . . . . -0.9(2) no
N2 C4 C5 C6 . . . . -178.80(16) no
N2 C15 C16 C17 . . . . 179.84(16) no
N2 C15 C20 C19 . . . . -179.52(16) no
N3 C6 C7 C28 . . . . 2.0(3) no
N3 C6 C7 N1 . . . . -179.90(16) no
N3 C21 C22 C23 . . . . -178.36(15) no
N3 C21 C26 C25 . . . . 178.61(15) no
O1 C4 C5 C1 . . . . 177.93(16) no
O1 C4 C5 C6 . . . . 0.0(3) no
O1 C4 N2 C3 . . . . -179.23(15) no
O1 C4 N2 C15 . . . . -0.3(2) no
O2 C24 C25 C26 . . . . -179.35(15) no
