# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_20160226zy001_0
_database_code_depnum_ccdc_archive 'CCDC 1484200'
_audit_update_record             
;
2016-06-09 deposited with the CCDC.
2016-08-26 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_audit_creation_date             2016-04-05
_chemical_formula_sum            'C19 H24 N2 O5'
_chemical_formula_weight         360.400
_refine_ls_R_factor_all          0.177
_cell_length_a                   12.590(2)
_cell_length_b                   8.3056(13)
_cell_length_c                   17.163(3)
_cell_angle_alpha                90.000
_cell_angle_beta                 97.211(4)
_cell_angle_gamma                90.000
_cell_volume                     1780.5(5)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  -P_2ybc

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 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 0.7256(4) 0.2991(8) 0.6862(3) 1.000 4 e ? d Uani 0.0456(14)
H1A H 0.7535 0.2891 0.6369 1.000 4 e ? calc Uiso 0.06800
H1B H 0.7520 0.2124 0.7203 1.000 4 e ? calc Uiso 0.06800
H1C H 0.7479 0.4000 0.7102 1.000 4 e ? calc Uiso 0.06800
C2 C 0.6048(4) 0.2926(6) 0.6726(3) 1.000 4 e ? d Uani 0.0277(10)
C3 C 0.5451(4) 0.2065(5) 0.7229(3) 1.000 4 e ? d Uani 0.0275(10)
H3 H 0.5810 0.1451 0.7632 1.000 4 e ? calc Uiso 0.03300
C4 C 0.4351(3) 0.2106(5) 0.7140(2) 1.000 4 e ? d Uani 0.0221(9)
H4 H 0.3983 0.1514 0.7480 1.000 4 e ? calc Uiso 0.02700
C5 C 0.3769(3) 0.3035(5) 0.6541(2) 1.000 4 e ? d Uani 0.0170(9)
C6 C 0.4365(3) 0.3839(5) 0.6024(2) 1.000 4 e ? d Uani 0.0194(9)
H6 H 0.4010 0.4421 0.5607 1.000 4 e ? calc Uiso 0.02300
C7 C 0.5465(3) 0.3781(5) 0.6122(2) 1.000 4 e ? d Uani 0.0242(10)
H7 H 0.5834 0.4338 0.5769 1.000 4 e ? calc Uiso 0.02900
C8 C 0.2598(3) 0.3107(5) 0.6492(2) 1.000 4 e ? d Uani 0.0176(9)
C9 C 0.0280(4) 0.1737(6) 0.7224(3) 1.000 4 e ? d Uani 0.0311(11)
H9A H -0.0338 0.2333 0.7352 1.000 4 e ? calc Uiso 0.03700
H9B H 0.0636 0.1276 0.7707 1.000 4 e ? calc Uiso 0.03700
C10 C -0.0090(4) 0.0397(6) 0.6661(3) 1.000 4 e ? d Uani 0.0374(12)
H10A H 0.0504 -0.0321 0.6606 1.000 4 e ? calc Uiso 0.04500
H10B H -0.0647 -0.0220 0.6867 1.000 4 e ? calc Uiso 0.04500
C11 C 0.0367(4) 0.1823(6) 0.5573(3) 1.000 4 e ? d Uani 0.0295(11)
H11A H 0.0126 0.2145 0.5037 1.000 4 e ? calc Uiso 0.03500
H11B H 0.0962 0.1084 0.5568 1.000 4 e ? calc Uiso 0.03500
C12 C 0.0722(3) 0.3301(5) 0.6068(2) 1.000 4 e ? d Uani 0.0230(9)
H12 H 0.0158 0.4121 0.6019 1.000 4 e ? calc Uiso 0.02800
C13 C 0.1803(3) 0.4038(5) 0.5884(2) 1.000 4 e ? d Uani 0.023(1)
C14 C 0.1931(3) 0.3873(6) 0.5018(3) 1.000 4 e ? d Uani 0.0251(10)
C15 C 0.2480(5) 0.2275(8) 0.4010(3) 1.000 4 e ? d Uani 0.0504(16)
H15A H 0.1769 0.2174 0.3722 1.000 4 e ? calc Uiso 0.06000
H15B H 0.2828 0.3197 0.3805 1.000 4 e ? calc Uiso 0.06000
C16 C 0.3078(6) 0.0865(9) 0.3914(3) 1.000 4 e ? d Uani 0.068(2)
H16A H 0.3802 0.1016 0.4152 1.000 4 e ? calc Uiso 0.10300
H16B H 0.3072 0.0647 0.3364 1.000 4 e ? calc Uiso 0.10300
H16C H 0.2765 -0.0026 0.4159 1.000 4 e ? calc Uiso 0.10300
C17 C 0.1800(4) 0.5857(6) 0.6049(3) 1.000 4 e ? d Uani 0.0273(10)
C18 C 0.2767(4) 0.8290(6) 0.5915(4) 1.000 4 e ? d Uani 0.0417(13)
H18A H 0.2635 0.8730 0.6418 1.000 4 e ? calc Uiso 0.05000
H18B H 0.2231 0.8710 0.5511 1.000 4 e ? calc Uiso 0.05000
C19 C 0.3871(5) 0.8734(6) 0.5743(3) 1.000 4 e ? d Uani 0.0442(14)
H19A H 0.4391 0.8338 0.6155 1.000 4 e ? calc Uiso 0.06600
H19B H 0.3928 0.9884 0.5712 1.000 4 e ? calc Uiso 0.06600
H19C H 0.3998 0.8264 0.5252 1.000 4 e ? calc Uiso 0.06600
N1 N 0.1015(3) 0.2845(5) 0.6899(2) 1.000 4 e ? d Uani 0.0257(9)
N2 N 0.2102(3) 0.2449(4) 0.7027(2) 1.000 4 e ? d Uani 0.0230(8)
O1 O 0.1614(3) 0.4862(5) 0.4537(2) 1.000 4 e ? d Uani 0.0425(9)
O2 O 0.2400(3) 0.2513(4) 0.4855(2) 1.000 4 e ? d Uani 0.0340(8)
O002 O -0.0493(3) 0.1050(4) 0.5910(2) 1.000 4 e ? d Uani 0.0333(8)
O3 O 0.1047(3) 0.6604(4) 0.6227(2) 1.000 4 e ? d Uani 0.0407(9)
O4 O 0.2724(3) 0.6516(4) 0.5932(2) 1.000 4 e ? d Uani 0.0368(9)



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 . . 1.510(7) no
C1 H1A . . 0.9600 no
C1 H1B . . 0.9600 no
C1 H1C . . 0.9600 no
C2 C7 . . 1.388(6) no
C2 C3 . . 1.410(6) no
C3 C4 . . 1.374(6) no
C3 H3 . . 0.9300 no
C4 C5 . . 1.414(6) no
C4 H4 . . 0.9300 no
C5 C6 . . 1.400(6) no
C5 C8 . . 1.468(6) no
C6 C7 . . 1.376(6) no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 N2 . . 1.295(5) no
C8 C13 . . 1.557(6) no
C9 N1 . . 1.464(6) no
C9 C10 . . 1.509(7) no
C9 H9A . . 0.9700 no
C9 H9B . . 0.9700 no
C10 O002 . . 1.432(6) no
C10 H10A . . 0.9700 no
C10 H10B . . 0.9700 no
C11 O002 . . 1.441(6) no
C11 C12 . . 1.528(6) no
C11 H11A . . 0.9700 no
C11 H11B . . 0.9700 no
C12 N1 . . 1.476(5) no
C12 C13 . . 1.560(6) no
C12 H12 . . 0.9800 no
C13 C14 . . 1.522(6) no
C13 C17 . . 1.537(6) no
C14 O1 . . 1.197(5) no
C14 O2 . . 1.321(5) no
C15 C16 . . 1.413(9) no
C15 O2 . . 1.480(6) no
C15 H15A . . 0.9700 no
C15 H15B . . 0.9700 no
C16 H16A . . 0.9600 no
C16 H16B . . 0.9600 no
C16 H16C . . 0.9600 no
C17 O3 . . 1.204(5) no
C17 O4 . . 1.324(6) no
C18 O4 . . 1.475(6) no
C18 C19 . . 1.503(7) no
C18 H18A . . 0.9700 no
C18 H18B . . 0.9700 no
C19 H19A . . 0.9600 no
C19 H19B . . 0.9600 no
C19 H19C . . 0.9600 no
N1 N2 . . 1.398(5) 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
C2 C1 H1A . . . 109.50 no
C2 C1 H1B . . . 109.50 no
H1A C1 H1B . . . 109.50 no
C2 C1 H1C . . . 109.50 no
H1A C1 H1C . . . 109.50 no
H1B C1 H1C . . . 109.50 no
C7 C2 C3 . . . 116.4(4) no
C7 C2 C1 . . . 121.7(4) no
C3 C2 C1 . . . 121.8(4) no
C4 C3 C2 . . . 121.8(4) no
C4 C3 H3 . . . 119.10 no
C2 C3 H3 . . . 119.10 no
C3 C4 C5 . . . 121.1(4) no
C3 C4 H4 . . . 119.40 no
C5 C4 H4 . . . 119.40 no
C6 C5 C4 . . . 116.8(4) no
C6 C5 C8 . . . 123.9(4) no
C4 C5 C8 . . . 119.2(4) no
C7 C6 C5 . . . 121.2(4) no
C7 C6 H6 . . . 119.40 no
C5 C6 H6 . . . 119.40 no
C6 C7 C2 . . . 122.6(4) no
C6 C7 H7 . . . 118.70 no
C2 C7 H7 . . . 118.70 no
N2 C8 C5 . . . 120.9(4) no
N2 C8 C13 . . . 110.9(4) no
C5 C8 C13 . . . 128.0(4) no
N1 C9 C10 . . . 112.2(4) no
N1 C9 H9A . . . 109.20 no
C10 C9 H9A . . . 109.20 no
N1 C9 H9B . . . 109.20 no
C10 C9 H9B . . . 109.20 no
H9A C9 H9B . . . 107.90 no
O002 C10 C9 . . . 110.1(4) no
O002 C10 H10A . . . 109.60 no
C9 C10 H10A . . . 109.60 no
O002 C10 H10B . . . 109.60 no
C9 C10 H10B . . . 109.60 no
H10A C10 H10B . . . 108.20 no
O002 C11 C12 . . . 108.5(4) no
O002 C11 H11A . . . 110.00 no
C12 C11 H11A . . . 110.00 no
O002 C11 H11B . . . 110.00 no
C12 C11 H11B . . . 110.00 no
H11A C11 H11B . . . 108.40 no
N1 C12 C11 . . . 110.6(4) no
N1 C12 C13 . . . 100.2(3) no
C11 C12 C13 . . . 113.9(4) no
N1 C12 H12 . . . 110.60 no
C11 C12 H12 . . . 110.60 no
C13 C12 H12 . . . 110.60 no
C14 C13 C17 . . . 105.7(4) no
C14 C13 C8 . . . 118.1(4) no
C17 C13 C8 . . . 112.4(3) no
C14 C13 C12 . . . 111.4(3) no
C17 C13 C12 . . . 109.0(4) no
C8 C13 C12 . . . 100.0(3) no
O1 C14 O2 . . . 124.0(4) no
O1 C14 C13 . . . 123.1(4) no
O2 C14 C13 . . . 112.9(4) no
C16 C15 O2 . . . 109.2(5) no
C16 C15 H15A . . . 109.80 no
O2 C15 H15A . . . 109.80 no
C16 C15 H15B . . . 109.80 no
O2 C15 H15B . . . 109.80 no
H15A C15 H15B . . . 108.30 no
C15 C16 H16A . . . 109.50 no
C15 C16 H16B . . . 109.50 no
H16A C16 H16B . . . 109.50 no
C15 C16 H16C . . . 109.50 no
H16A C16 H16C . . . 109.50 no
H16B C16 H16C . . . 109.50 no
O3 C17 O4 . . . 124.1(4) no
O3 C17 C13 . . . 125.0(4) no
O4 C17 C13 . . . 110.9(4) no
O4 C18 C19 . . . 106.6(4) no
O4 C18 H18A . . . 110.40 no
C19 C18 H18A . . . 110.40 no
O4 C18 H18B . . . 110.40 no
C19 C18 H18B . . . 110.40 no
H18A C18 H18B . . . 108.60 no
C18 C19 H19A . . . 109.50 no
C18 C19 H19B . . . 109.50 no
H19A C19 H19B . . . 109.50 no
C18 C19 H19C . . . 109.50 no
H19A C19 H19C . . . 109.50 no
H19B C19 H19C . . . 109.50 no
N2 N1 C9 . . . 116.4(4) no
N2 N1 C12 . . . 109.4(3) no
C9 N1 C12 . . . 115.9(3) no
C8 N2 N1 . . . 109.9(3) no
C14 O2 C15 . . . 114.1(4) no
C10 O002 C11 . . . 109.3(3) no
C17 O4 C18 . . . 116.8(4) 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
C7 C2 C3 C4 . . . . -1.8(7) no
C1 C2 C3 C4 . . . . 174.9(5) no
C2 C3 C4 C5 . . . . -0.7(7) no
C3 C4 C5 C6 . . . . 3.0(6) no
C3 C4 C5 C8 . . . . -177.0(4) no
C4 C5 C6 C7 . . . . -3.0(6) no
C8 C5 C6 C7 . . . . 177.1(4) no
C5 C6 C7 C2 . . . . 0.6(7) no
C3 C2 C7 C6 . . . . 1.9(7) no
C1 C2 C7 C6 . . . . -174.8(5) no
C6 C5 C8 N2 . . . . -174.1(4) no
C4 C5 C8 N2 . . . . 5.9(6) no
C6 C5 C8 C13 . . . . 0.3(6) no
C4 C5 C8 C13 . . . . -179.7(4) no
N1 C9 C10 O002 . . . . -51.4(5) no
O002 C11 C12 N1 . . . . 55.4(5) no
O002 C11 C12 C13 . . . . 167.3(3) no
N2 C8 C13 C14 . . . . -137.4(4) no
C5 C8 C13 C14 . . . . 47.8(6) no
N2 C8 C13 C17 . . . . 99.1(4) no
C5 C8 C13 C17 . . . . -75.8(5) no
N2 C8 C13 C12 . . . . -16.4(4) no
C5 C8 C13 C12 . . . . 168.7(4) no
N1 C12 C13 C14 . . . . 152.3(4) no
C11 C12 C13 C14 . . . . 34.3(5) no
N1 C12 C13 C17 . . . . -91.4(4) no
C11 C12 C13 C17 . . . . 150.6(4) no
N1 C12 C13 C8 . . . . 26.6(4) no
C11 C12 C13 C8 . . . . -91.4(4) no
C17 C13 C14 O1 . . . . -29.3(6) no
C8 C13 C14 O1 . . . . -156.1(4) no
C12 C13 C14 O1 . . . . 89.0(5) no
C17 C13 C14 O2 . . . . 152.3(4) no
C8 C13 C14 O2 . . . . 25.5(5) no
C12 C13 C14 O2 . . . . -89.4(4) no
C14 C13 C17 O3 . . . . 114.1(5) no
C8 C13 C17 O3 . . . . -115.7(5) no
C12 C13 C17 O3 . . . . -5.8(6) no
C14 C13 C17 O4 . . . . -62.8(4) no
C8 C13 C17 O4 . . . . 67.4(5) no
C12 C13 C17 O4 . . . . 177.4(3) no
C10 C9 N1 N2 . . . . -88.4(5) no
C10 C9 N1 C12 . . . . 42.5(6) no
C11 C12 N1 N2 . . . . 89.6(4) no
C13 C12 N1 N2 . . . . -30.8(4) no
C11 C12 N1 C9 . . . . -44.5(5) no
C13 C12 N1 C9 . . . . -164.9(4) no
C5 C8 N2 N1 . . . . 173.0(3) no
C13 C8 N2 N1 . . . . -2.3(4) no
C9 N1 N2 C8 . . . . 156.0(4) no
C12 N1 N2 C8 . . . . 22.1(4) no
O1 C14 O2 C15 . . . . -1.7(7) no
C13 C14 O2 C15 . . . . 176.7(4) no
C16 C15 O2 C14 . . . . 174.7(5) no
C9 C10 O002 C11 . . . . 65.2(5) no
C12 C11 O002 C10 . . . . -67.2(5) no
O3 C17 O4 C18 . . . . -8.5(7) no
C13 C17 O4 C18 . . . . 168.4(4) no
C19 C18 O4 C17 . . . . -177.8(4) no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H12 O1 . . 3_566 0.9800 2.4600 3.360(6) 152.00 no
_chemical_name_systematic        1
