# 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 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_zhuyr0717
_audit_block_doi                 10.5517/cc13bmgj
_database_code_depnum_ccdc_archive 'CCDC 1023107'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4RA09961C 2014
_audit_update_record             
;
2014-09-05 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_date             2014-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H11 N3, 3(H2 O)'
_chemical_formula_sum            'C10 H17 N3 O3'
_chemical_formula_weight         227.26
_chemical_melting_point          ?
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'

_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.
;
_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_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                   7.0612(5)
_cell_length_b                   17.0603(15)
_cell_length_c                   10.3203(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.420(7)
_cell_angle_gamma                90
_cell_volume                     1232.83(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1107
_cell_measurement_temperature    292.3(7)
_cell_measurement_theta_max      26.2320
_cell_measurement_theta_min      3.7540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4855
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_min         3.512
_diffrn_ambient_temperature      292.3(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   27.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  -99.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -76.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5262  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00  104.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   77.00   1.0000   36.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -19.0000 -180.0000 126
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0016901000
_diffrn_orient_matrix_UB_12      -0.0211102000
_diffrn_orient_matrix_UB_13      -0.0593680000
_diffrn_orient_matrix_UB_21      -0.0031247000
_diffrn_orient_matrix_UB_22      0.0358105000
_diffrn_orient_matrix_UB_23      -0.0351063000
_diffrn_orient_matrix_UB_31      0.1012326000
_diffrn_orient_matrix_UB_32      0.0007034000
_diffrn_orient_matrix_UB_33      0.0069095000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1521
_reflns_number_total             2421
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0826P)²+0.1898P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2025
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1C,H1D), O2(H2A,H2B), O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
N1 N 0.8499(4) 0.69365(19) 0.2977(4) 0.0723(8) Uani 1 1 d . . . . .
H1A H 0.884(5) 0.740(2) 0.336(4) 0.086(12) Uiso 1 1 d . . . . .
H1B H 0.831(6) 0.685(3) 0.215(5) 0.117(16) Uiso 1 1 d . . . . .
N2 N 0.7641(3) 0.56459(13) 0.3202(2) 0.0459(6) Uani 1 1 d . . . . .
N3 N 0.6854(3) 0.43413(13) 0.3352(2) 0.0467(6) Uani 1 1 d . . . . .
C1 C 0.8186(3) 0.63234(17) 0.3754(3) 0.0506(7) Uani 1 1 d . . . . .
C2 C 0.8477(4) 0.64284(19) 0.5139(3) 0.0575(8) Uani 1 1 d . . . . .
H2 H 0.8867 0.6911 0.5499 0.069 Uiso 1 1 calc R . . . .
C3 C 0.8178(3) 0.58189(18) 0.5917(3) 0.0531(7) Uani 1 1 d . . . . .
H3 H 0.8346 0.5883 0.6819 0.064 Uiso 1 1 calc R . . . .
C4 C 0.7611(3) 0.50814(16) 0.5373(2) 0.0457(7) Uani 1 1 d . . . . .
C5 C 0.7355(3) 0.50276(15) 0.3984(2) 0.0415(6) Uani 1 1 d . . . . .
C6 C 0.6576(4) 0.37122(17) 0.4058(3) 0.0528(7) Uani 1 1 d . . . . .
C7 C 0.6776(4) 0.37362(19) 0.5441(3) 0.0578(8) Uani 1 1 d . . . . .
H7 H 0.6560 0.3285 0.5905 0.069 Uiso 1 1 calc R . . . .
C8 C 0.7278(3) 0.44070(18) 0.6097(3) 0.0519(7) Uani 1 1 d . . . . .
C9 C 0.6092(5) 0.29644(19) 0.3341(4) 0.0798(10) Uani 1 1 d . . . . .
H9A H 0.5072 0.3055 0.2647 0.120 Uiso 1 1 calc GR . . . .
H9B H 0.5699 0.2581 0.3933 0.120 Uiso 1 1 calc GR . . . .
H9C H 0.7194 0.2776 0.2981 0.120 Uiso 1 1 calc GR . . . .
C10 C 0.7493(5) 0.4438(2) 0.7572(3) 0.0758(10) Uani 1 1 d . . . . .
H10A H 0.7111 0.3945 0.7904 0.114 Uiso 1 1 calc GR . . . .
H10B H 0.6702 0.4848 0.7844 0.114 Uiso 1 1 calc GR . . . .
H10C H 0.8803 0.4540 0.7904 0.114 Uiso 1 1 calc GR . . . .
O1 O 0.6880(4) 0.41393(15) 0.0675(2) 0.0827(8) Uani 1 1 d . . . . .
H1C H 0.6813 0.4163 0.1491 0.124 Uiso 1 1 d G . . . .
H1D H 0.7027 0.4598 0.0383 0.124 Uiso 1 1 d G . . . .
O2 O 0.9705(4) 0.66719(16) 0.9446(4) 0.1219(13) Uani 1 1 d . . . . .
H2A H 1.0693 0.6389 0.9430 0.183 Uiso 1 1 d G . . . .
H2B H 0.8835 0.6404 0.9734 0.183 Uiso 1 1 d G . . . .
O3 O 0.6968(3) 0.5800(2) 0.0480(2) 0.0962(9) Uani 1 1 d . . . . .
H3A H 0.7079 0.5753 0.1306 0.144 Uiso 1 1 d G . . . .
H3B H 0.5808 0.5892 0.0187 0.144 Uiso 1 1 d G . . . .


_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
N1 H1A 0.90(4) . ?
N1 H1B 0.86(5) . ?
N1 C1 1.353(4) . ?
N2 C1 1.324(3) . ?
N2 C5 1.359(3) . ?
N3 C5 1.364(3) . ?
N3 C6 1.326(3) . ?
C1 C2 1.429(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.347(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.414(4) . ?
C4 C5 1.424(3) . ?
C4 C8 1.408(4) . ?
C6 C7 1.417(4) . ?
C6 C9 1.492(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.353(4) . ?
C8 C10 1.511(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1 H1C 0.8499 . ?
O1 H1D 0.8503 . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8499 . ?
O3 H3A 0.8498 . ?
O3 H3B 0.8500 . ?

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
H1A N1 H1B 126(4) . . ?
C1 N1 H1A 118(2) . . ?
C1 N1 H1B 116(3) . . ?
C1 N2 C5 118.7(2) . . ?
C6 N3 C5 118.7(2) . . ?
N1 C1 C2 118.8(3) . . ?
N2 C1 N1 118.7(3) . . ?
N2 C1 C2 122.4(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 116.7(2) . . ?
C8 C4 C3 125.0(3) . . ?
C8 C4 C5 118.2(3) . . ?
N2 C5 N3 115.6(2) . . ?
N2 C5 C4 122.6(2) . . ?
N3 C5 C4 121.8(2) . . ?
N3 C6 C7 121.8(3) . . ?
N3 C6 C9 117.4(3) . . ?
C7 C6 C9 120.7(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.5 . . ?
C4 C8 C10 120.3(3) . . ?
C7 C8 C4 118.5(3) . . ?
C7 C8 C10 121.3(3) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H1C O1 H1D 109.5 . . ?
H2A O2 H2B 109.5 . . ?
H3A O3 H3B 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.6(3) . . . . ?
N2 C1 C2 C3 -0.3(4) . . . . ?
N3 C6 C7 C8 -0.5(4) . . . . ?
C1 N2 C5 N3 -178.0(2) . . . . ?
C1 N2 C5 C4 0.3(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C8 179.5(2) . . . . ?
C3 C4 C5 N2 0.2(3) . . . . ?
C3 C4 C5 N3 178.4(2) . . . . ?
C3 C4 C8 C7 -178.7(2) . . . . ?
C3 C4 C8 C10 0.8(4) . . . . ?
C5 N2 C1 N1 179.0(2) . . . . ?
C5 N2 C1 C2 -0.3(3) . . . . ?
C5 N3 C6 C7 0.3(3) . . . . ?
C5 N3 C6 C9 -178.1(2) . . . . ?
C5 C4 C8 C7 1.6(3) . . . . ?
C5 C4 C8 C10 -178.8(2) . . . . ?
C6 N3 C5 N2 179.2(2) . . . . ?
C6 N3 C5 C4 0.9(3) . . . . ?
C6 C7 C8 C4 -0.5(4) . . . . ?
C6 C7 C8 C10 180.0(2) . . . . ?
C8 C4 C5 N2 179.9(2) . . . . ?
C8 C4 C5 N3 -1.9(3) . . . . ?
C9 C6 C7 C8 177.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
