# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1040251'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2014-12-18
_chemical_formula_sum            'C12 H13 N3 O2'
_chemical_formula_structural     C13H14N4O2
_chemical_formula_analytical     C13H14N4O2
_chemical_name_common            
;
2-amino-8a-methoxy-6,7,8,8a-tetrahydro-4H-chromene-3,4,4(4aH,5H)-tricarbonitrile
;
_chemical_name_systematic        
;
2-amino-8a-methoxy-6,7,8,8a-tetrahydro-4H-chromene-3,4,4(4aH,5H)-tricarbonitrile
;
_chemical_formula_weight         231.250
_chemical_formula_weight_meas    258.000
_refine_ls_R_factor_all          0.039
_cell_length_a                   8.1414(6)
_cell_length_b                   8.9768(7)
_cell_length_c                   8.9788(7)
_cell_angle_alpha                75.259(1)
_cell_angle_beta                 87.305(1)
_cell_angle_gamma                65.104(1)
_cell_volume                     574.3(1)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? 1.200
N ? 1.200
C ? 1.200
H ? 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
O1 O 0.0184(1) 0.4835(1) 0.8066(1) 1.000 2 i ? d Uani 0.0238(2)
O2 O 0.2762(1) 0.2870(1) 0.9640(1) 1.000 2 i ? d Uani 0.0229(2)
N1 N -0.1027(2) 0.7655(2) 0.7395(2) 1.000 2 i ? d Uani 0.0279(3)
N2 N 0.1578(2) 0.8771(1) 0.4169(1) 1.000 2 i ? d Uani 0.0279(3)
N3 N 0.4326(2) 0.4259(2) 0.3309(1) 1.000 2 i ? d Uani 0.0295(3)
C1 C 0.0210(2) 0.6242(2) 0.7103(2) 1.000 2 i ? d Uani 0.0212(3)
C2 C 0.1384(2) 0.6123(2) 0.5938(2) 1.000 2 i ? d Uani 0.0207(3)
C3 C 0.2612(2) 0.4425(2) 0.5809(1) 1.000 2 i ? d Uani 0.0200(3)
C4 C 0.2832(2) 0.3011(2) 0.6904(2) 1.000 2 i ? d Uani 0.0206(3)
C5 C 0.4134(2) 0.1231(2) 0.6895(2) 1.000 2 i ? d Uani 0.0255(3)
C6 C 0.3215(2) 0.0019(2) 0.7233(2) 1.000 2 i ? d Uani 0.0299(3)
C7 C 0.2260(2) 0.0099(2) 0.8733(2) 1.000 2 i ? d Uani 0.0310(3)
C8 C 0.0868(2) 0.1913(2) 0.8655(2) 1.000 2 i ? d Uani 0.0257(3)
C9 C 0.1719(2) 0.3168(2) 0.8298(1) 1.000 2 i ? d Uani 0.0208(3)
C10 C 0.3683(2) 0.3945(2) 0.9547(2) 1.000 2 i ? d Uani 0.0303(3)
C12 C 0.1481(2) 0.7588(2) 0.4967(2) 1.000 2 i ? d Uani 0.0212(3)
C13 C 0.3589(2) 0.4313(2) 0.4431(2) 1.000 2 i ? d Uani 0.0215(3)
H82 H 0.027(2) 0.2002(19) 0.9617(18) 1.000 2 i ? d Uiso 0.026(4)
H81 H -0.008(2) 0.2286(19) 0.7840(19) 1.000 2 i ? d Uiso 0.029(4)
H52 H 0.515(2) 0.0820(19) 0.7736(19) 1.000 2 i ? d Uiso 0.032(4)
H62 H 0.411(2) -0.113(2) 0.7303(19) 1.000 2 i ? d Uiso 0.034(4)
H51 H 0.472(2) 0.1242(19) 0.5891(19) 1.000 2 i ? d Uiso 0.027(4)
H2 H -0.166(2) 0.752(2) 0.824(2) 1.000 2 i ? d Uiso 0.043(5)
H1 H -0.114(2) 0.866(2) 0.685(2) 1.000 2 i ? d Uiso 0.034(4)
H61 H 0.231(2) 0.033(2) 0.638(2) 1.000 2 i ? d Uiso 0.035(4)
H103 H 0.451(3) 0.382(2) 0.875(2) 1.000 2 i ? d Uiso 0.049(5)
H102 H 0.434(2) 0.361(2) 1.053(2) 1.000 2 i ? d Uiso 0.035(4)
H72 H 0.163(2) -0.063(2) 0.891(2) 1.000 2 i ? d Uiso 0.039(4)
H71 H 0.319(2) -0.030(2) 0.962(2) 1.000 2 i ? d Uiso 0.040(5)
H101 H 0.281(3) 0.513(3) 0.938(2) 1.000 2 i ? d Uiso 0.053(5)



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
O1 C1 . . 1.3456(15) no
O1 C9 . . 1.4615(15) no
O2 C9 . . 1.4093(16) no
O2 C10 . . 1.4368(17) no
N1 C1 . . 1.3270(17) no
N1 H2 . . 0.91(2) no
N1 H1 . . 0.881(18) no
N2 C12 . . 1.1508(17) no
N3 C13 . . 1.1493(17) no
C1 C2 . . 1.3770(18) no
C2 C12 . . 1.4120(18) no
C2 C3 . . 1.4597(17) no
C3 C4 . . 1.3420(18) no
C3 C13 . . 1.4407(17) no
C4 C5 . . 1.5019(18) no
C4 C9 . . 1.5110(17) no
C5 C6 . . 1.527(2) no
C5 H52 . . 1.022(17) no
C5 H51 . . 0.999(16) no
C6 C7 . . 1.525(2) no
C6 H62 . . 0.970(16) no
C6 H61 . . 0.986(18) no
C7 C8 . . 1.528(2) no
C7 H72 . . 0.972(18) no
C7 H71 . . 1.010(18) no
C8 C9 . . 1.5178(18) no
C8 H82 . . 0.975(16) no
C8 H81 . . 0.977(17) no
C10 H103 . . 0.95(2) no
C10 H102 . . 0.966(18) no
C10 H101 . . 0.97(2) 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
C1 O1 C9 . . . 122.16(9) no
C9 O2 C10 . . . 115.75(10) no
C1 N1 H2 . . . 116.5(11) no
C1 N1 H1 . . . 121.0(11) no
H2 N1 H1 . . . 122.2(16) no
N1 C1 O1 . . . 112.23(11) no
N1 C1 C2 . . . 127.08(12) no
O1 C1 C2 . . . 120.65(11) no
C1 C2 C12 . . . 121.02(11) no
C1 C2 C3 . . . 117.75(11) no
C12 C2 C3 . . . 121.10(11) no
C4 C3 C13 . . . 120.37(11) no
C4 C3 C2 . . . 122.50(12) no
C13 C3 C2 . . . 117.13(11) no
C3 C4 C5 . . . 125.69(12) no
C3 C4 C9 . . . 119.02(11) no
C5 C4 C9 . . . 115.28(11) no
C4 C5 C6 . . . 111.88(11) no
C4 C5 H52 . . . 107.8(9) no
C6 C5 H52 . . . 108.7(9) no
C4 C5 H51 . . . 109.5(9) no
C6 C5 H51 . . . 112.0(9) no
H52 C5 H51 . . . 106.8(12) no
C7 C6 C5 . . . 110.61(12) no
C7 C6 H62 . . . 110.(1) no
C5 C6 H62 . . . 109.9(9) no
C7 C6 H61 . . . 109.0(9) no
C5 C6 H61 . . . 109.7(9) no
H62 C6 H61 . . . 107.5(14) no
C6 C7 C8 . . . 110.68(12) no
C6 C7 H72 . . . 109.8(10) no
C8 C7 H72 . . . 108.4(10) no
C6 C7 H71 . . . 109.4(10) no
C8 C7 H71 . . . 109.4(10) no
H72 C7 H71 . . . 109.1(14) no
C9 C8 C7 . . . 112.06(12) no
C9 C8 H82 . . . 107.8(9) no
C7 C8 H82 . . . 112.1(9) no
C9 C8 H81 . . . 107.3(9) no
C7 C8 H81 . . . 110.2(9) no
H82 C8 H81 . . . 107.2(12) no
O2 C9 O1 . . . 108.19(10) no
O2 C9 C4 . . . 112.37(10) no
O1 C9 C4 . . . 112.43(10) no
O2 C9 C8 . . . 106.82(10) no
O1 C9 C8 . . . 104.64(10) no
C4 C9 C8 . . . 111.93(11) no
O2 C10 H103 . . . 110.9(11) no
O2 C10 H102 . . . 107.(1) no
H103 C10 H102 . . . 109.8(15) no
O2 C10 H101 . . . 110.3(11) no
H103 C10 H101 . . . 111.0(16) no
H102 C10 H101 . . . 107.8(15) no
N2 C12 C2 . . . 179.20(14) no
N3 C13 C3 . . . 178.12(14) 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
N1 H2 O2 . . 2_567 0.91(2) 2.08(2) 2.9787(15) 171.2(16) no
N1 H1 N2 . . 2_576 0.881(18) 2.130(18) 3.0038(17) 171.2(15) no
