# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_at1
_database_code_depnum_ccdc_archive 'CCDC 1528029'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N4 O4'
_chemical_formula_sum            'C22 H24 N4 O4'
_chemical_formula_weight         408.45

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.31640(10)
_cell_length_b                   11.5830(3)
_cell_length_c                   17.1059(4)
_cell_angle_alpha                84.2779(12)
_cell_angle_beta                 82.5641(12)
_cell_angle_gamma                85.7426(12)
_cell_volume                     1037.31(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3878
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      23.63

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13176
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.205
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3647
_reflns_number_gt                2687
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0547P)²+0.1644P] 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         3647
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 -0.1888(4) 0.80368(18) 0.84249(11) 0.0532(5) Uani 1 1 d . . . . .
H1 H -0.2054 0.8805 0.8212 0.064 Uiso 1 1 calc R U . . .
C2 C -0.3681(4) 0.7624(2) 0.90250(12) 0.0625(6) Uani 1 1 d . . . . .
H2 H -0.5039 0.8117 0.9212 0.075 Uiso 1 1 calc R U . . .
C3 C -0.3475(4) 0.6504(2) 0.93446(12) 0.0635(6) Uani 1 1 d . . . . .
H3 H -0.4696 0.6225 0.9744 0.076 Uiso 1 1 calc R U . . .
C4 C -0.1458(5) 0.5792(2) 0.90724(14) 0.0743(7) Uani 1 1 d . . . . .
H4 H -0.1294 0.5027 0.9292 0.089 Uiso 1 1 calc R U . . .
C5 C 0.0349(4) 0.62016(19) 0.84703(13) 0.0649(6) Uani 1 1 d . . . . .
H5 H 0.1717 0.5709 0.8290 0.078 Uiso 1 1 calc R U . . .
C6 C 0.0140(3) 0.73261(15) 0.81374(10) 0.0401(4) Uani 1 1 d . . . . .
C7 C 0.2013(3) 0.78131(15) 0.74784(11) 0.0455(5) Uani 1 1 d . . . . .
H7A H 0.1122 0.8209 0.7059 0.055 Uiso 1 1 calc R U . . .
H7B H 0.3000 0.8371 0.7672 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5843(3) 0.71700(16) 0.67361(9) 0.0366(4) Uani 1 1 d . . . . .
C9 C 0.7461(3) 0.61104(15) 0.65167(10) 0.0366(4) Uani 1 1 d . . . . .
C10 C 0.6957(4) 0.50444(16) 0.69399(12) 0.0524(5) Uani 1 1 d . . . . .
H10 H 0.5496 0.4991 0.7301 0.063 Uiso 1 1 calc R U . . .
C11 C 0.8558(4) 0.40705(18) 0.68386(13) 0.0605(6) Uani 1 1 d . . . . .
H11 H 0.8165 0.3367 0.7124 0.073 Uiso 1 1 calc R U . . .
C12 C 1.0734(4) 0.41369(18) 0.63153(12) 0.0569(6) Uani 1 1 d . . . . .
H12 H 1.1872 0.3491 0.6267 0.068 Uiso 1 1 calc R U . . .
C13 C 1.1231(4) 0.51651(17) 0.58594(11) 0.0488(5) Uani 1 1 d . . . . .
H13 H 1.2671 0.5200 0.5488 0.059 Uiso 1 1 calc R U . . .
C14 C 0.9599(3) 0.61484(15) 0.59508(10) 0.0369(4) Uani 1 1 d . . . . .
C15 C 0.8755(3) 0.78905(15) 0.49924(9) 0.0367(4) Uani 1 1 d . . . . .
H15 H 0.7000 0.7905 0.5002 0.044 Uiso 1 1 calc R U . . .
C16 C 1.0370(3) 0.86002(15) 0.45308(9) 0.0379(4) Uani 1 1 d . . . . .
C17 C 0.9875(4) 0.95590(16) 0.39086(10) 0.0451(5) Uani 1 1 d . . . . .
H17A H 0.8072 0.9785 0.3962 0.054 Uiso 1 1 calc R U . . .
H17B H 1.0772 1.0228 0.3990 0.054 Uiso 1 1 calc R U . . .
C18 C 0.9019(3) 0.89414(14) 0.26477(10) 0.0373(4) Uani 1 1 d . . . . .
C19 C 0.8878(3) 0.83003(16) 0.13301(10) 0.0421(4) Uani 1 1 d . . . . .
C20 C 1.0989(4) 0.7983(2) 0.06946(12) 0.0704(7) Uani 1 1 d . . . . .
H20A H 1.2014 0.8635 0.0539 0.106 Uiso 1 1 calc R U . . .
H20B H 1.0272 0.7777 0.0244 0.106 Uiso 1 1 calc R U . . .
H20C H 1.2024 0.7334 0.0896 0.106 Uiso 1 1 calc R U . . .
C21 C 0.7308(4) 0.72721(19) 0.16089(13) 0.0613(6) Uani 1 1 d . . . . .
H21A H 0.8352 0.6656 0.1845 0.092 Uiso 1 1 calc R U . . .
H21B H 0.6647 0.7008 0.1166 0.092 Uiso 1 1 calc R U . . .
H21C H 0.5925 0.7498 0.1993 0.092 Uiso 1 1 calc R U . . .
C22 C 0.7287(4) 0.93567(19) 0.10391(13) 0.0651(6) Uani 1 1 d . . . . .
H22A H 0.5892 0.9518 0.1437 0.098 Uiso 1 1 calc R U . . .
H22B H 0.6643 0.9208 0.0562 0.098 Uiso 1 1 calc R U . . .
H22C H 0.8318 1.0014 0.0934 0.098 Uiso 1 1 calc R U . . .
N1 N 1.0210(2) 0.71601(13) 0.54340(8) 0.0376(4) Uani 1 1 d . . . . .
N2 N 1.2673(3) 0.74075(17) 0.52507(10) 0.0592(5) Uani 1 1 d . . . . .
N3 N 1.2757(3) 0.82856(17) 0.47094(10) 0.0596(5) Uani 1 1 d . . . . .
N4 N 1.0675(3) 0.92270(14) 0.31100(8) 0.0420(4) Uani 1 1 d . . . . .
O1 O 0.3674(2) 0.68748(10) 0.71782(7) 0.0448(3) Uani 1 1 d . . . . .
O2 O 0.6423(2) 0.81517(11) 0.65807(7) 0.0498(4) Uani 1 1 d . . . . .
O3 O 0.6736(2) 0.89988(13) 0.28055(8) 0.0599(4) Uani 1 1 d . . . . .
O4 O 1.0282(2) 0.85970(11) 0.19618(6) 0.0422(3) Uani 1 1 d . . . . .
H1N H 1.216(4) 0.9143(16) 0.2968(11) 0.041(6) Uiso 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 C6 1.376(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.360(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(2) . ?
C7 O1 1.441(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.1955(19) . ?
C8 O1 1.342(2) . ?
C8 C9 1.496(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.395(2) . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9300 . ?
C14 N1 1.427(2) . ?
C15 N1 1.346(2) . ?
C15 C16 1.355(2) . ?
C15 H15 0.9300 . ?
C16 N3 1.358(2) . ?
C16 C17 1.493(2) . ?
C17 N4 1.458(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O3 1.207(2) . ?
C18 N4 1.336(2) . ?
C18 O4 1.3552(19) . ?
C19 O4 1.4712(19) . ?
C19 C21 1.508(3) . ?
C19 C20 1.510(3) . ?
C19 C22 1.515(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 N2 1.351(2) . ?
N2 N3 1.305(2) . ?
N4 H1N 0.797(18) . ?

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 120.91(19) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.16(17) . . ?
C5 C6 C7 123.08(16) . . ?
C1 C6 C7 118.76(16) . . ?
O1 C7 C6 108.91(14) . . ?
O1 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O2 C8 O1 123.52(16) . . ?
O2 C8 C9 125.58(15) . . ?
O1 C8 C9 110.79(15) . . ?
C10 C9 C14 117.66(16) . . ?
C10 C9 C8 118.99(15) . . ?
C14 C9 C8 123.12(15) . . ?
C11 C10 C9 121.86(19) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.80(18) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 120.55(18) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.12(17) . . ?
C13 C14 N1 116.71(16) . . ?
C9 C14 N1 123.16(15) . . ?
N1 C15 C16 105.95(15) . . ?
N1 C15 H15 127.0 . . ?
C16 C15 H15 127.0 . . ?
C15 C16 N3 107.74(16) . . ?
C15 C16 C17 130.57(16) . . ?
N3 C16 C17 121.67(16) . . ?
N4 C17 C16 112.56(15) . . ?
N4 C17 H17A 109.1 . . ?
C16 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
O3 C18 N4 125.55(16) . . ?
O3 C18 O4 124.65(16) . . ?
N4 C18 O4 109.79(15) . . ?
O4 C19 C21 110.79(15) . . ?
O4 C19 C20 102.47(14) . . ?
C21 C19 C20 110.44(17) . . ?
O4 C19 C22 109.78(15) . . ?
C21 C19 C22 112.42(17) . . ?
C20 C19 C22 110.50(17) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 N1 N2 109.67(14) . . ?
C15 N1 C14 130.81(14) . . ?
N2 N1 C14 118.98(14) . . ?
N3 N2 N1 107.25(14) . . ?
N2 N3 C16 109.38(15) . . ?
C18 N4 C17 122.10(17) . . ?
C18 N4 H1N 119.3(14) . . ?
C17 N4 H1N 118.2(14) . . ?
C8 O1 C7 116.60(13) . . ?
C18 O4 C19 120.47(13) . . ?

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
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C1 C6 C7 179.23(19) . . . . ?
C5 C6 C7 O1 10.6(3) . . . . ?
C1 C6 C7 O1 -169.46(16) . . . . ?
O2 C8 C9 C10 159.15(18) . . . . ?
O1 C8 C9 C10 -17.2(2) . . . . ?
O2 C8 C9 C14 -15.2(3) . . . . ?
O1 C8 C9 C14 168.49(15) . . . . ?
C14 C9 C10 C11 3.2(3) . . . . ?
C8 C9 C10 C11 -171.47(18) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -3.8(3) . . . . ?
C11 C12 C13 C14 2.8(3) . . . . ?
C12 C13 C14 C9 1.2(3) . . . . ?
C12 C13 C14 N1 -177.68(16) . . . . ?
C10 C9 C14 C13 -4.1(3) . . . . ?
C8 C9 C14 C13 170.31(16) . . . . ?
C10 C9 C14 N1 174.72(16) . . . . ?
C8 C9 C14 N1 -10.9(3) . . . . ?
N1 C15 C16 N3 -0.42(19) . . . . ?
N1 C15 C16 C17 178.19(17) . . . . ?
C15 C16 C17 N4 -105.0(2) . . . . ?
N3 C16 C17 N4 73.4(2) . . . . ?
C16 C15 N1 N2 -0.12(19) . . . . ?
C16 C15 N1 C14 -171.42(16) . . . . ?
C13 C14 N1 C15 131.93(19) . . . . ?
C9 C14 N1 C15 -46.9(3) . . . . ?
C13 C14 N1 N2 -38.7(2) . . . . ?
C9 C14 N1 N2 142.44(17) . . . . ?
C15 N1 N2 N3 0.6(2) . . . . ?
C14 N1 N2 N3 173.12(15) . . . . ?
N1 N2 N3 C16 -0.9(2) . . . . ?
C15 C16 N3 N2 0.8(2) . . . . ?
C17 C16 N3 N2 -177.93(16) . . . . ?
O3 C18 N4 C17 5.3(3) . . . . ?
O4 C18 N4 C17 -175.95(14) . . . . ?
C16 C17 N4 C18 102.2(2) . . . . ?
O2 C8 O1 C7 -0.7(2) . . . . ?
C9 C8 O1 C7 175.76(14) . . . . ?
C6 C7 O1 C8 -163.25(14) . . . . ?
O3 C18 O4 C19 2.3(3) . . . . ?
N4 C18 O4 C19 -176.44(14) . . . . ?
C21 C19 O4 C18 -62.6(2) . . . . ?
C20 C19 O4 C18 179.64(16) . . . . ?
C22 C19 O4 C18 62.2(2) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.037

