# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_mo_D8V491_0m
_database_code_depnum_ccdc_archive 'CCDC 1035254'
_audit_update_record             
;
2014-11-20 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_formula_moiety         'C14 H17 N3 O5, C H4 O'
_chemical_formula_sum            'C15 H21 N3 O6'
_chemical_formula_weight         339.35
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.1672(17)
_cell_length_b                   6.8153(14)
_cell_length_c                   22.813(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.975(7)
_cell_angle_gamma                90
_cell_volume                     1577.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1470
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.60
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9084.
The λ/2 correction factor is 0.0000.
;
_exptl_crystal_density_diffrn    1.4292
_exptl_crystal_F_000             720.4332
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10403
_diffrn_reflns_theta_full        25.0257
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.60
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                1834
_reflns_number_total             2771
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_refine_diff_density_max         0.4934
_refine_diff_density_min         -0.5288
_refine_diff_density_rms         0.1258
_refine_ls_d_res_high            0.8401
_refine_ls_d_res_low             7.8466
_refine_ls_goodness_of_fit_ref   1.0504
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.0504
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.1019


_exptl_crystal_description       prism
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.055

_diffrn_ambient_temperature      122(2)
_cell_measurement_temperature    122(2)


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_refinement_flags_posn
O1 O 0.81594(17) 0.8483(3) 0.55372(8) 0.0283(5) Uani 1.000000 .
H1 H 0.879(3) 0.843(5) 0.5777(13) 0.0424(8) Uiso 1.000000 R
O2 O 0.53327(16) 0.6373(3) 0.42693(8) 0.0202(4) Uani 1.000000 .
H2 H 0.487(3) 0.743(4) 0.4243(12) 0.0304(7) Uiso 1.000000 R
O3 O 0.52446(15) 0.4189(3) 0.32030(7) 0.0151(4) Uani 1.000000 .
H3 H 0.578(3) 0.512(4) 0.3224(11) 0.0227(6) Uiso 1.000000 R
O4 O 0.42313(16) 0.0274(2) 0.41477(7) 0.0172(4) Uani 1.000000 .
H4 H 0.347(2) 0.061(4) 0.4284(11) 0.0258(6) Uiso 1.000000 R
O5 O 0.94680(15) 0.2171(2) 0.38386(7) 0.0170(4) Uani 1.000000 .
O6 O 0.71353(15) -0.3068(3) 0.30304(7) 0.0185(4) Uani 1.000000 .
N1 N 0.72610(17) 0.1568(3) 0.36101(8) 0.0125(5) Uani 1.000000 .
N2 N 0.86549(18) -0.0730(3) 0.34008(8) 0.0127(5) Uani 1.000000 .
N3 N 0.65457(18) -0.0155(3) 0.34622(8) 0.0134(5) Uani 1.000000 .
C1 C 0.8438(3) 0.7429(5) 0.50226(13) 0.0367(8) Uani 1.000000 .
H1a H 0.9095(13) 0.8119(14) 0.4821(4) 0.0551(12) Uiso 1.000000 GR
H1b H 0.8758(17) 0.6145(10) 0.51301(14) 0.0551(12) Uiso 1.000000 GR
H1c H 0.7648(5) 0.731(2) 0.4769(4) 0.0551(12) Uiso 1.000000 GR
C2 C 0.4540(2) 0.4641(4) 0.41823(10) 0.0143(6) Uani 1.000000 .
H2a H 0.4443(2) 0.3990(4) 0.45550(10) 0.0172(7) Uiso 1.000000 R
H2b H 0.3670(2) 0.4984(4) 0.40117(10) 0.0172(7) Uiso 1.000000 R
C3 C 0.5229(2) 0.3298(3) 0.37713(10) 0.0120(5) Uani 1.000000 .
C4 C 0.6662(2) 0.2920(4) 0.40180(10) 0.0127(5) Uani 1.000000 .
H4a H 0.7136(2) 0.4169(4) 0.40021(10) 0.0152(7) Uiso 1.000000 R
C5 C 0.8566(2) 0.1135(4) 0.36361(10) 0.0120(6) Uani 1.000000 .
C6 C 0.9863(2) -0.1668(3) 0.32707(10) 0.0128(6) Uani 1.000000 .
C7 C 1.0118(2) -0.3537(4) 0.34734(10) 0.0156(6) Uani 1.000000 .
H7 H 0.9531(2) -0.4168(4) 0.37055(10) 0.0187(7) Uiso 1.000000 R
C8 C 1.1264(2) -0.4472(4) 0.33268(10) 0.0179(6) Uani 1.000000 .
H8 H 1.1443(2) -0.5743(4) 0.34578(10) 0.0215(7) Uiso 1.000000 R
C9 C 1.2137(2) -0.3518(4) 0.29867(10) 0.0163(6) Uani 1.000000 .
H9 H 1.2904(2) -0.4147(4) 0.28898(10) 0.0196(7) Uiso 1.000000 R
C10 C 0.4457(2) 0.1385(4) 0.36336(10) 0.0131(6) Uani 1.000000 .
H10 H 0.3599(2) 0.1731(4) 0.34383(10) 0.0157(7) Uiso 1.000000 R
C11 C 0.5189(2) 0.0123(4) 0.32181(10) 0.0148(6) Uani 1.000000 .
H11a H 0.5189(2) 0.0753(4) 0.28370(10) 0.0177(7) Uiso 1.000000 R
H11b H 0.4755(2) -0.1140(4) 0.31671(10) 0.0177(7) Uiso 1.000000 R
C12 C 0.7404(2) -0.1504(4) 0.32692(10) 0.0145(6) Uani 1.000000 .
C13 C 1.1874(2) -0.1631(4) 0.27901(10) 0.0161(6) Uani 1.000000 .
H13 H 1.2468(2) -0.0989(4) 0.25646(10) 0.0193(7) Uiso 1.000000 R
C14 C 1.0727(2) -0.0694(4) 0.29277(10) 0.0159(6) Uani 1.000000 .
H14 H 1.0540(2) 0.0569(4) 0.27921(10) 0.0190(7) Uiso 1.000000 R
C15 C 0.6837(2) 0.2187(4) 0.46487(10) 0.0192(6) Uani 1.000000 .
H15a H 0.6344(12) 0.0997(12) 0.46859(18) 0.0287(9) Uiso 1.000000 GR
H15b H 0.7754(3) 0.194(2) 0.4750(2) 0.0287(9) Uiso 1.000000 GR
H15c H 0.6523(14) 0.3164(9) 0.49081(12) 0.0287(9) Uiso 1.000000 GR


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 H1 0.82(3) . ?
O1 C1 1.421(3) . ?
O2 H2 0.86(3) . ?
O2 C2 1.436(3) . ?
O3 H3 0.84(3) . ?
O3 C3 1.433(3) . ?
O4 H4 0.88(2) . ?
O4 C10 1.428(3) . ?
O5 C5 1.223(3) . ?
O6 C12 1.219(3) . ?
N1 N3 1.410(3) . ?
N1 C4 1.471(3) . ?
N1 C5 1.356(3) . ?
N2 C5 1.385(3) . ?
N2 C6 1.434(3) . ?
N2 C12 1.391(3) . ?
N3 C11 1.464(3) . ?
N3 C12 1.361(3) . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C3 1.516(3) . ?
C3 C4 1.547(3) . ?
C3 C10 1.543(3) . ?
C4 H4a 0.9800 . ?
C4 C15 1.522(3) . ?
C6 C7 1.374(3) . ?
C6 C14 1.386(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C13 1.382(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.513(3) . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9300 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 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
C1 O1 H1 110(2) . . ?
C2 O2 H2 112.4(19) . . ?
C3 O3 H3 108.5(18) . . ?
C10 O4 H4 110.1(17) . . ?
C4 N1 N3 116.35(16) . . ?
C5 N1 N3 108.43(18) . . ?
C5 N1 C4 123.70(19) . . ?
C6 N2 C5 124.71(19) . . ?
C12 N2 C5 110.37(19) . . ?
C12 N2 C6 124.77(19) . . ?
C11 N3 N1 116.14(19) . . ?
C12 N3 N1 107.96(17) . . ?
C12 N3 C11 124.9(2) . . ?
H1a C1 O1 109.5 . . ?
H1b C1 O1 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 O1 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
H2a C2 O2 110.19(12) . . ?
H2b C2 O2 110.19(12) . . ?
H2b C2 H2a 108.5 . . ?
C3 C2 O2 107.62(17) . . ?
C3 C2 H2a 110.19(13) . . ?
C3 C2 H2b 110.19(13) . . ?
C2 C3 O3 109.76(19) . . ?
C4 C3 O3 109.29(17) . . ?
C4 C3 C2 109.85(19) . . ?
C10 C3 O3 102.21(18) . . ?
C10 C3 C2 112.68(17) . . ?
C10 C3 C4 112.75(19) . . ?
C3 C4 N1 107.14(18) . . ?
H4a C4 N1 107.14(11) . . ?
H4a C4 C3 107.14(13) . . ?
C15 C4 N1 111.5(2) . . ?
C15 C4 C3 116.34(18) . . ?
C15 C4 H4a 107.14(14) . . ?
N1 C5 O5 126.7(2) . . ?
N2 C5 O5 127.5(2) . . ?
N2 C5 N1 105.8(2) . . ?
C7 C6 N2 119.2(2) . . ?
C14 C6 N2 119.3(2) . . ?
C14 C6 C7 121.5(2) . . ?
H7 C7 C6 120.45(13) . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H7 120.45(15) . . ?
H8 C8 C7 119.95(15) . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.95(15) . . ?
H9 C9 C8 119.91(15) . . ?
C13 C9 C8 120.2(2) . . ?
C13 C9 H9 119.91(13) . . ?
C3 C10 O4 112.90(18) . . ?
H10 C10 O4 108.24(11) . . ?
H10 C10 C3 108.24(12) . . ?
C11 C10 O4 109.1(2) . . ?
C11 C10 C3 110.02(17) . . ?
C11 C10 H10 108.24(13) . . ?
C10 C11 N3 109.06(19) . . ?
H11a C11 N3 109.87(12) . . ?
H11a C11 C10 109.87(13) . . ?
H11b C11 N3 109.87(13) . . ?
H11b C11 C10 109.87(12) . . ?
H11b C11 H11a 108.3 . . ?
N2 C12 O6 127.0(2) . . ?
N3 C12 O6 127.3(2) . . ?
N3 C12 N2 105.7(2) . . ?
H13 C13 C9 119.91(13) . . ?
C14 C13 C9 120.2(2) . . ?
C14 C13 H13 119.91(15) . . ?
C13 C14 C6 119.0(2) . . ?
H14 C14 C6 120.52(14) . . ?
H14 C14 C13 120.52(15) . . ?
H15a C15 C4 109.5 . . ?
H15b C15 C4 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C4 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?


