# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1402759'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 N4 O5'
_chemical_formula_weight         337.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.8007(6)
_cell_length_b                   10.7877(5)
_cell_length_c                   20.2847(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.562(7)
_cell_angle_gamma                90
_cell_volume                     1706.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12571
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      27.16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9476
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17932
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.138
_diffrn_reflns_theta_max         27.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3775
_reflns_number_gt                2142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-Area
_computing_cell_refinement       X-Area
_computing_data_reduction        X-Area
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3775
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2504(2) -0.03217(18) 0.23259(9) 0.0533(5) Uani 1 1 d . . . . .
C2 C 0.1384(3) -0.1404(2) 0.25333(12) 0.0784(7) Uani 1 1 d . . . . .
H2A H 0.1318 -0.2005 0.2185 0.118 Uiso 1 1 calc R U . . .
H2B H 0.0254 -0.1107 0.2623 0.118 Uiso 1 1 calc R U . . .
H2C H 0.1875 -0.1781 0.2923 0.118 Uiso 1 1 calc R U . . .
C3 C 0.2757(3) 0.0583(2) 0.29006(10) 0.0770(7) Uani 1 1 d . . . . .
H3A H 0.3322 0.0166 0.3264 0.115 Uiso 1 1 calc R U . . .
H3B H 0.1661 0.0882 0.3035 0.115 Uiso 1 1 calc R U . . .
H3C H 0.3447 0.1268 0.2764 0.115 Uiso 1 1 calc R U . . .
C4 C 0.1662(3) 0.03195(19) 0.17264(9) 0.0590(5) Uani 1 1 d . . . . .
H4A H 0.1235 -0.0308 0.1421 0.071 Uiso 1 1 calc R U . . .
H4B H 0.0688 0.0798 0.1870 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2861(3) 0.11637(17) 0.13709(9) 0.0534(5) Uani 1 1 d . . . . .
H5 H 0.3302 0.1808 0.1671 0.064 Uiso 1 1 calc R U . . .
C6 C 0.4330(3) 0.0392(2) 0.11197(10) 0.0670(6) Uani 1 1 d . . . . .
H6A H 0.5087 0.0926 0.0875 0.080 Uiso 1 1 calc R U . . .
H6B H 0.3872 -0.0227 0.0817 0.080 Uiso 1 1 calc R U . . .
C7 C 0.5369(3) -0.02550(18) 0.16632(10) 0.0587(5) Uani 1 1 d . . . . .
C8 C 0.6430(4) -0.1287(2) 0.13621(14) 0.0954(9) Uani 1 1 d . . . . .
H8A H 0.7181 -0.1637 0.1695 0.143 Uiso 1 1 calc R U . . .
H8B H 0.7097 -0.0954 0.1013 0.143 Uiso 1 1 calc R U . . .
H8C H 0.5679 -0.1919 0.1188 0.143 Uiso 1 1 calc R U . . .
C9 C 0.6576(3) 0.0649(2) 0.20249(15) 0.0897(8) Uani 1 1 d . . . . .
H9A H 0.5928 0.1335 0.2188 0.135 Uiso 1 1 calc R U . . .
H9B H 0.7416 0.0948 0.1726 0.135 Uiso 1 1 calc R U . . .
H9C H 0.7143 0.0231 0.2388 0.135 Uiso 1 1 calc R U . . .
C10 C 0.2173(2) 0.28719(17) 0.05710(8) 0.0503(5) Uani 1 1 d . . . . .
C11 C 0.3153(3) 0.37806(18) 0.09228(10) 0.0619(6) Uani 1 1 d . . . . .
H11 H 0.3645 0.3570 0.1330 0.074 Uiso 1 1 calc R U . . .
C12 C 0.3399(3) 0.49401(19) 0.06876(10) 0.0636(6) Uani 1 1 d . . . . .
H12 H 0.4029 0.5514 0.0936 0.076 Uiso 1 1 calc R U . . .
C13 C 0.2704(3) 0.52699(19) 0.00724(10) 0.0569(5) Uani 1 1 d . . . . .
C14 C 0.1731(2) 0.44578(18) -0.02855(9) 0.0534(5) Uani 1 1 d . . . . .
H14 H 0.1253 0.4695 -0.0691 0.064 Uiso 1 1 calc R U . . .
C15 C 0.1451(2) 0.32727(17) -0.00458(8) 0.0494(4) Uani 1 1 d . . . . .
N1 N 0.4205(2) -0.08243(13) 0.21481(7) 0.0512(4) Uani 1 1 d . . . . .
N2 N 0.1944(2) 0.17326(15) 0.08081(8) 0.0605(5) Uani 1 1 d . . . . .
H2 H 0.1178 0.1284 0.0610 0.073 Uiso 1 1 calc R U . . .
N3 N 0.0378(2) 0.24720(17) -0.04543(7) 0.0589(4) Uani 1 1 d . . . . .
N4 N 0.3002(3) 0.65118(18) -0.01819(10) 0.0691(5) Uani 1 1 d . . . . .
O1 O 0.4937(2) -0.15380(13) 0.25781(7) 0.0732(4) Uani 1 1 d . . . . .
O2 O 0.0110(2) 0.13966(15) -0.02806(7) 0.0759(5) Uani 1 1 d . . . . .
O3 O -0.0241(2) 0.28922(15) -0.09672(7) 0.0823(5) Uani 1 1 d . . . . .
O4 O 0.2292(3) 0.68068(15) -0.07017(9) 0.0914(5) Uani 1 1 d . . . . .
O5 O 0.3963(3) 0.72043(16) 0.01326(9) 0.0948(6) Uani 1 1 d . . . . .


_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
C1 N1 1.487(3) . ?
C1 C2 1.524(3) . ?
C1 C3 1.529(3) . ?
C1 C4 1.531(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.504(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.465(2) . ?
C5 C6 1.515(3) . ?
C5 H5 0.9800 . ?
C6 C7 1.520(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N1 1.489(3) . ?
C7 C8 1.525(3) . ?
C7 C9 1.529(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.334(2) . ?
C10 C11 1.423(3) . ?
C10 C15 1.425(2) . ?
C11 C12 1.354(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.356(3) . ?
C13 N4 1.456(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 N3 1.448(2) . ?
N1 O1 1.2857(18) . ?
N2 H2 0.8600 . ?
N3 O3 1.2224(19) . ?
N3 O2 1.232(2) . ?
N4 O4 1.220(2) . ?
N4 O5 1.226(2) . ?

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
N1 C1 C2 108.05(16) . . ?
N1 C1 C3 108.67(16) . . ?
C2 C1 C3 109.97(18) . . ?
N1 C1 C4 109.76(15) . . ?
C2 C1 C4 109.18(16) . . ?
C3 C1 C4 111.15(16) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C1 113.30(16) . . ?
C5 C4 H4A 108.9 . . ?
C1 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C1 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N2 C5 C4 109.29(15) . . ?
N2 C5 C6 108.99(16) . . ?
C4 C5 C6 108.34(16) . . ?
N2 C5 H5 110.1 . . ?
C4 C5 H5 110.1 . . ?
C6 C5 H5 110.1 . . ?
C5 C6 C7 113.65(17) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N1 C7 C6 110.25(16) . . ?
N1 C7 C8 108.11(18) . . ?
C6 C7 C8 109.22(18) . . ?
N1 C7 C9 108.95(18) . . ?
C6 C7 C9 111.36(18) . . ?
C8 C7 C9 108.9(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 121.95(16) . . ?
N2 C10 C15 122.88(17) . . ?
C11 C10 C15 115.17(17) . . ?
C12 C11 C10 122.59(18) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 119.76(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.84(18) . . ?
C14 C13 N4 119.78(18) . . ?
C12 C13 N4 119.36(19) . . ?
C13 C14 C15 119.91(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.68(17) . . ?
C14 C15 N3 116.32(16) . . ?
C10 C15 N3 122.00(17) . . ?
O1 N1 C1 115.89(15) . . ?
O1 N1 C7 115.31(16) . . ?
C1 N1 C7 125.03(14) . . ?
C10 N2 C5 126.85(16) . . ?
C10 N2 H2 116.6 . . ?
C5 N2 H2 116.6 . . ?
O3 N3 O2 121.75(17) . . ?
O3 N3 C15 118.36(18) . . ?
O2 N3 C15 119.89(15) . . ?
O4 N4 O5 123.23(19) . . ?
O4 N4 C13 118.2(2) . . ?
O5 N4 C13 118.52(18) . . ?

_refine_diff_density_max         0.120
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.026

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1402760'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H25 N4 O5'
_chemical_formula_weight         353.40

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.0768(7)
_cell_length_b                   25.637(4)
_cell_length_c                   10.7812(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.712(8)
_cell_angle_gamma                90
_cell_volume                     1915.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3489
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.90

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_T_max  1.0110
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13314
_diffrn_reflns_av_unetI/netI     0.1664
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         26.905
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4085
_reflns_number_gt                1227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-Area
_computing_cell_refinement       X-Area
_computing_data_reduction        X-Area
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4085
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2069
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0432
_refine_ls_goodness_of_fit_ref   0.724
_refine_ls_restrained_S_all      0.724
_refine_ls_shift/su_max          0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7516(7) -0.00984(13) 0.3103(3) 0.0672(11) Uani 1 1 d . . . . .
C2 C 0.8740(6) -0.00210(13) 0.2284(3) 0.0749(11) Uani 1 1 d . . . . .
H2 H 0.9970 -0.0166 0.2452 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8126(5) 0.02746(12) 0.1205(3) 0.0682(10) Uani 1 1 d . . . . .
H3 H 0.8955 0.0334 0.0652 0.082 Uiso 1 1 calc R U . . .
C4 C 0.6276(5) 0.04833(12) 0.0944(3) 0.0515(8) Uani 1 1 d . . . . .
C5 C 0.5068(5) 0.03881(13) 0.1788(3) 0.0632(10) Uani 1 1 d . . . . .
H5 H 0.3821 0.0523 0.1620 0.076 Uiso 1 1 calc R U . . .
C6 C 0.5684(6) 0.00987(13) 0.2866(3) 0.0709(11) Uani 1 1 d . . . . .
H6 H 0.4867 0.0038 0.3426 0.085 Uiso 1 1 calc R U . . .
C7 C 0.6500(5) 0.09886(12) -0.0999(3) 0.0526(8) Uani 1 1 d . . . . .
C8 C 0.6146(5) 0.16597(11) -0.2661(3) 0.0553(9) Uani 1 1 d . . . . .
H8 H 0.7404 0.1790 -0.2215 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6350(5) 0.14141(11) -0.3908(3) 0.0593(9) Uani 1 1 d . . . . .
H9A H 0.5095 0.1291 -0.4345 0.071 Uiso 1 1 calc R U . . .
H9B H 0.7197 0.1114 -0.3734 0.071 Uiso 1 1 calc R U . . .
C10 C 0.7152(5) 0.17884(12) -0.4774(3) 0.0563(9) Uani 1 1 d . . . . .
C11 C 0.9308(5) 0.18943(14) -0.4328(3) 0.0801(11) Uani 1 1 d . . . . .
H11A H 1.0005 0.1571 -0.4274 0.120 Uiso 1 1 calc R U . . .
H11B H 0.9744 0.2121 -0.4921 0.120 Uiso 1 1 calc R U . . .
H11C H 0.9531 0.2057 -0.3510 0.120 Uiso 1 1 calc R U . . .
C12 C 0.6789(6) 0.15574(13) -0.6107(3) 0.0862(12) Uani 1 1 d . . . . .
H12A H 0.7450 0.1230 -0.6090 0.129 Uiso 1 1 calc R U . . .
H12B H 0.5429 0.1504 -0.6402 0.129 Uiso 1 1 calc R U . . .
H12C H 0.7259 0.1793 -0.6666 0.129 Uiso 1 1 calc R U . . .
C13 C 0.4745(5) 0.21102(12) -0.2964(3) 0.0617(9) Uani 1 1 d . . . . .
H13A H 0.4557 0.2263 -0.2175 0.074 Uiso 1 1 calc R U . . .
H13B H 0.3509 0.1976 -0.3405 0.074 Uiso 1 1 calc R U . . .
C14 C 0.5395(5) 0.25395(12) -0.3775(3) 0.0535(8) Uani 1 1 d . . . . .
C15 C 0.6978(6) 0.28786(13) -0.2996(3) 0.0797(12) Uani 1 1 d . . . . .
H15A H 0.6515 0.3032 -0.2303 0.120 Uiso 1 1 calc R U . . .
H15B H 0.8089 0.2667 -0.2673 0.120 Uiso 1 1 calc R U . . .
H15C H 0.7326 0.3149 -0.3523 0.120 Uiso 1 1 calc R U . . .
C16 C 0.3654(5) 0.28811(13) -0.4324(3) 0.0759(11) Uani 1 1 d . . . . .
H16A H 0.3174 0.3042 -0.3645 0.114 Uiso 1 1 calc R U . . .
H16B H 0.4036 0.3146 -0.4852 0.114 Uiso 1 1 calc R U . . .
H16C H 0.2659 0.2669 -0.4818 0.114 Uiso 1 1 calc R U . . .
N1 N 0.6090(4) 0.22985(9) -0.4852(2) 0.0542(7) Uani 1 1 d . . . . .
N2 N 0.5362(4) 0.13009(10) -0.1844(2) 0.0628(8) Uani 1 1 d . . . . .
H2A H 0.4133 0.1288 -0.1903 0.075 Uiso 1 1 calc R U . . .
N3 N 0.5542(4) 0.07886(9) -0.0112(2) 0.0551(7) Uani 1 1 d . . . . .
H3A H 0.4334 0.0862 -0.0225 0.066 Uiso 1 1 calc R U . . .
N4 N 0.8204(7) -0.04061(13) 0.4258(3) 0.0896(11) Uani 1 1 d . . . . .
O1 O 0.6336(3) 0.26106(8) -0.57457(19) 0.0722(7) Uani 1 1 d . . . . .
O2 O 0.8191(3) 0.08977(8) -0.10051(19) 0.0645(7) Uani 1 1 d . . . . .
O3 O 0.7104(5) -0.04625(12) 0.4994(3) 0.1262(13) Uani 1 1 d . . . . .
O4 O 0.9840(6) -0.05783(12) 0.4449(3) 0.1206(13) Uani 1 1 d . . . . .
O5W O 0.1785(4) 0.13168(11) -0.0964(3) 0.0813(7) Uani 1 1 d D . . . .
H1W H 0.158(6) 0.1650(5) -0.077(3) 0.120(16) Uiso 1 1 d D . . . .
H2W H 0.065(3) 0.1153(16) -0.104(4) 0.16(2) Uiso 1 1 d D . . . .


_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
C1 C6 1.366(5) . ?
C1 C2 1.372(5) . ?
C1 N4 1.471(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 N3 1.392(3) . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.221(4) . ?
C7 N2 1.350(4) . ?
C7 N3 1.378(3) . ?
C8 N2 1.459(3) . ?
C8 C13 1.514(4) . ?
C8 C9 1.517(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.527(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N1 1.502(3) . ?
C10 C12 1.527(4) . ?
C10 C11 1.529(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.533(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.485(3) . ?
C14 C15 1.528(4) . ?
C14 C16 1.530(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 O1 1.291(3) . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
N4 O4 1.217(4) . ?
N4 O3 1.227(4) . ?
O5W H1W 0.899(5) . ?
O5W H2W 0.898(5) . ?

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
C6 C1 C2 121.7(3) . . ?
C6 C1 N4 119.7(4) . . ?
C2 C1 N4 118.6(4) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 N3 124.2(3) . . ?
C5 C4 N3 117.2(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O2 C7 N2 124.1(3) . . ?
O2 C7 N3 123.6(3) . . ?
N2 C7 N3 112.3(3) . . ?
N2 C8 C13 107.3(2) . . ?
N2 C8 C9 112.9(3) . . ?
C13 C8 C9 107.6(2) . . ?
N2 C8 H8 109.6 . . ?
C13 C8 H8 109.6 . . ?
C9 C8 H8 109.6 . . ?
C8 C9 C10 113.3(3) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
N1 C10 C9 109.7(3) . . ?
N1 C10 C12 107.4(3) . . ?
C9 C10 C12 108.6(3) . . ?
N1 C10 C11 108.6(3) . . ?
C9 C10 C11 113.0(3) . . ?
C12 C10 C11 109.3(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 C14 114.3(3) . . ?
C8 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C8 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N1 C14 C15 110.1(3) . . ?
N1 C14 C16 107.7(3) . . ?
C15 C14 C16 109.3(3) . . ?
N1 C14 C13 109.4(3) . . ?
C15 C14 C13 111.5(3) . . ?
C16 C14 C13 108.7(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 N1 C14 116.2(2) . . ?
O1 N1 C10 116.1(2) . . ?
C14 N1 C10 124.0(2) . . ?
C7 N2 C8 122.3(3) . . ?
C7 N2 H2A 118.9 . . ?
C8 N2 H2A 118.9 . . ?
C7 N3 C4 128.5(3) . . ?
C7 N3 H3A 115.8 . . ?
C4 N3 H3A 115.8 . . ?
O4 N4 O3 123.7(4) . . ?
O4 N4 C1 118.5(4) . . ?
O3 N4 C1 117.7(4) . . ?
H1W O5W H2W 106(4) . . ?

_refine_diff_density_max         0.105
_refine_diff_density_min         -0.083
_refine_diff_density_rms         0.023

_shelxl_version_number           2014-3

