# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_sj_1
_database_code_depnum_ccdc_archive 'CCDC 997089'
_audit_update_record             
;
2014-04-13 deposited with the CCDC.
2014-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H22 N4 O4'
_chemical_formula_sum            'C21 H22 N4 O4'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method acetonitrile
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         394.43

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_chemical_absolute_configuration ?

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

_cell_length_a                   5.9906(6)
_cell_length_b                   15.7335(18)
_cell_length_c                   21.9353(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2067.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10672
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3576
_reflns_number_gt                2281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1086
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5260(5) 0.41802(19) 0.94067(12) 0.0572(8) Uani 1 1 d . . .
C5 C 0.8257(5) 0.41384(19) 0.86876(13) 0.0532(7) Uani 1 1 d . . .
C6 C 0.7127(5) 0.37737(18) 0.91672(12) 0.0554(8) Uani 1 1 d . . .
H6 H 0.7608 0.3260 0.9330 0.066 Uiso 1 1 calc R . .
C2 C 0.4572(6) 0.4953(2) 0.91696(14) 0.0710(9) Uani 1 1 d . . .
H2 H 0.3312 0.5222 0.9325 0.085 Uiso 1 1 calc R . .
C4 C 0.7621(6) 0.49150(19) 0.84550(14) 0.0682(8) Uani 1 1 d . . .
H4 H 0.8419 0.5163 0.8138 0.082 Uiso 1 1 calc R . .
C3 C 0.5775(7) 0.5322(2) 0.87003(16) 0.0809(10) Uani 1 1 d . . .
H3 H 0.5340 0.5848 0.8548 0.097 Uiso 1 1 calc R . .
C8 C 1.4051(5) 0.20852(19) 0.79779(12) 0.0530(7) Uani 1 1 d . . .
C7 C 1.3295(5) 0.12650(18) 0.81168(13) 0.0534(7) Uani 1 1 d . . .
H7 H 1.1877 0.1190 0.8280 0.064 Uiso 1 1 calc R . .
C12 C 1.4638(5) 0.05695(19) 0.80128(12) 0.0531(7) Uani 1 1 d . . .
C9 C 1.6153(5) 0.2195(2) 0.77227(13) 0.0603(8) Uani 1 1 d . . .
H9 H 1.6654 0.2735 0.7619 0.072 Uiso 1 1 calc R . .
C10 C 1.7491(5) 0.1495(2) 0.76244(13) 0.0646(8) Uani 1 1 d . . .
H10 H 1.8903 0.1568 0.7456 0.078 Uiso 1 1 calc R . .
C11 C 1.6772(5) 0.0686(2) 0.77714(13) 0.0620(8) Uani 1 1 d . . .
H11 H 1.7705 0.0221 0.7710 0.074 Uiso 1 1 calc R . .
C13 C 0.4067(6) 0.3766(2) 0.99245(14) 0.0654(9) Uani 1 1 d . . .
C14 C 0.0857(6) 0.3824(2) 1.05465(15) 0.0987(13) Uani 1 1 d . . .
H14A H 0.1708 0.3894 1.0914 0.148 Uiso 1 1 calc R . .
H14B H 0.0544 0.3231 1.0485 0.148 Uiso 1 1 calc R . .
H14C H -0.0521 0.4132 1.0580 0.148 Uiso 1 1 calc R . .
C15 C 1.2372(6) -0.0518(2) 0.85399(14) 0.0656(8) Uani 1 1 d . . .
C16 C 1.0873(7) -0.1786(2) 0.90413(16) 0.0816(11) Uani 1 1 d . . .
C19 C 1.1425(11) -0.2713(3) 0.8951(2) 0.152(3) Uani 1 1 d . . .
H19A H 1.1031 -0.2880 0.8544 0.227 Uiso 1 1 calc R . .
H19B H 1.0600 -0.3049 0.9238 0.227 Uiso 1 1 calc R . .
H19C H 1.2995 -0.2800 0.9012 0.227 Uiso 1 1 calc R . .
C18 C 0.8468(8) -0.1590(4) 0.8938(3) 0.154(2) Uani 1 1 d . . .
H18A H 0.8049 -0.1764 0.8535 0.231 Uiso 1 1 calc R . .
H18B H 0.8227 -0.0990 0.8982 0.231 Uiso 1 1 calc R . .
H18C H 0.7577 -0.1890 0.9232 0.231 Uiso 1 1 calc R . .
C17 C 1.1660(9) -0.1509(3) 0.96628(18) 0.1215(18) Uani 1 1 d . . .
H17A H 1.0985 -0.1862 0.9969 0.182 Uiso 1 1 calc R . .
H17B H 1.1240 -0.0928 0.9730 0.182 Uiso 1 1 calc R . .
H17C H 1.3254 -0.1561 0.9685 0.182 Uiso 1 1 calc R . .
O4 O 1.2298(4) -0.13624(14) 0.85789(9) 0.0797(7) Uani 1 1 d . . .
O2 O 0.2124(4) 0.41468(16) 1.00331(10) 0.0823(7) Uani 1 1 d . . .
O1 O 0.4746(4) 0.31630(16) 1.02006(11) 0.0820(7) Uani 1 1 d . . .
O3 O 1.1215(4) -0.00357(15) 0.88324(12) 0.0945(8) Uani 1 1 d . . .
C20 C 1.2609(5) 0.28205(18) 0.81010(13) 0.0533(7) Uani 1 1 d . . .
C21 C 1.0915(5) 0.29194(18) 0.85123(13) 0.0543(7) Uani 1 1 d . . .
H21 H 1.0424 0.2526 0.8799 0.065 Uiso 1 1 calc R . .
N1 N 1.0111(4) 0.37025(15) 0.84165(10) 0.0544(6) Uani 1 1 d . . .
N4 N 1.3969(4) -0.02719(15) 0.81389(11) 0.0640(7) Uani 1 1 d . . .
H4A H 1.4641 -0.0669 0.7942 0.077 Uiso 1 1 calc R . .
N2 N 1.1225(5) 0.40871(17) 0.79568(12) 0.0757(8) Uani 1 1 d . . .
N3 N 1.2741(5) 0.35488(17) 0.77698(12) 0.0761(8) 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 C2 1.385(4) . ?
C1 C6 1.391(4) . ?
C1 C13 1.492(4) . ?
C5 C6 1.376(4) . ?
C5 C4 1.378(4) . ?
C5 N1 1.435(4) . ?
C2 C3 1.384(4) . ?
C4 C3 1.386(4) . ?
C8 C9 1.389(4) . ?
C8 C7 1.401(4) . ?
C8 C20 1.469(4) . ?
C7 C12 1.377(4) . ?
C12 C11 1.396(4) . ?
C12 N4 1.411(3) . ?
C9 C10 1.379(4) . ?
C10 C11 1.381(4) . ?
C13 O1 1.197(4) . ?
C13 O2 1.330(4) . ?
C14 O2 1.450(4) . ?
C15 O3 1.212(3) . ?
C15 O4 1.332(4) . ?
C15 N4 1.356(4) . ?
C16 O4 1.484(4) . ?
C16 C18 1.491(6) . ?
C16 C17 1.507(5) . ?
C16 C19 1.509(5) . ?
C20 N3 1.359(3) . ?
C20 C21 1.367(4) . ?
C21 N1 1.339(3) . ?
N1 N2 1.352(3) . ?
N2 N3 1.308(3) . ?

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
C2 C1 C6 120.0(3) . . ?
C2 C1 C13 121.8(3) . . ?
C6 C1 C13 118.2(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 N1 119.9(3) . . ?
C4 C5 N1 119.0(3) . . ?
C5 C6 C1 119.5(3) . . ?
C3 C2 C1 119.5(3) . . ?
C5 C4 C3 119.1(3) . . ?
C2 C3 C4 120.7(3) . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 C20 120.6(3) . . ?
C7 C8 C20 119.7(3) . . ?
C12 C7 C8 120.5(3) . . ?
C7 C12 C11 119.6(3) . . ?
C7 C12 N4 123.2(3) . . ?
C11 C12 N4 117.3(3) . . ?
C10 C9 C8 119.4(3) . . ?
C9 C10 C11 121.2(3) . . ?
C10 C11 C12 119.7(3) . . ?
O1 C13 O2 124.3(3) . . ?
O1 C13 C1 124.7(3) . . ?
O2 C13 C1 111.0(3) . . ?
O3 C15 O4 124.9(3) . . ?
O3 C15 N4 124.6(3) . . ?
O4 C15 N4 110.5(3) . . ?
O4 C16 C18 111.1(3) . . ?
O4 C16 C17 108.0(3) . . ?
C18 C16 C17 112.3(4) . . ?
O4 C16 C19 102.6(3) . . ?
C18 C16 C19 113.1(5) . . ?
C17 C16 C19 109.3(4) . . ?
C15 O4 C16 120.7(3) . . ?
C13 O2 C14 116.1(3) . . ?
N3 C20 C21 107.5(3) . . ?
N3 C20 C8 122.1(3) . . ?
C21 C20 C8 130.4(3) . . ?
N1 C21 C20 105.5(2) . . ?
C21 N1 N2 110.6(2) . . ?
C21 N1 C5 130.8(2) . . ?
N2 N1 C5 118.5(2) . . ?
C15 N4 C12 126.6(3) . . ?
N3 N2 N1 106.7(2) . . ?
N2 N3 C20 109.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039

