# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_exp_7111
_database_code_depnum_ccdc_archive 'CCDC 1944448'
loop_
_audit_author_name
_audit_author_address
'Li-Ming Zhao'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2019-08-08 downloaded from the CCDC.
;
_audit_creation_date             2019-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N4 O4'
_chemical_formula_sum            'C17 H14 N4 O4'
_chemical_formula_weight         338.32
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_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'
'-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                   12.2898(13)
_cell_length_b                   11.4074(13)
_cell_length_c                   22.636(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3173.5(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8620
_cell_measurement_theta_min      4.3310
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.04267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.1300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9906
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  88.00   1.00   10.00    --   15.49 178.00  60.00   52
  2  ω    -66.00  -1.00   1.00   10.00    --  -16.28 -57.00 120.00   65
  3  ω    -76.00 -33.00   1.00   10.00    --  -16.28 -38.00-180.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0206257000
_diffrn_orient_matrix_UB_12      -0.0492605000
_diffrn_orient_matrix_UB_13      0.0154327000
_diffrn_orient_matrix_UB_21      0.0064299000
_diffrn_orient_matrix_UB_22      -0.0348917000
_diffrn_orient_matrix_UB_23      -0.0257246000
_diffrn_orient_matrix_UB_31      0.0535409000
_diffrn_orient_matrix_UB_32      -0.0148183000
_diffrn_orient_matrix_UB_33      0.0090413000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1570
_reflns_number_total             3429
_reflns_odcompleteness_completeness 99.59
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      0.923
_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)+(0.0106P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.007 and sigma for
terminal atoms of 0.014
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C6(H6), C14(H14), C12(H12), C13(H13), C10(H10),
 C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O4 O 0.47662(13) 0.33729(15) 0.51876(9) 0.0494(5) Uani 1 1 d . . . . .
O3 O 0.25880(16) 0.27250(16) 0.68275(9) 0.0546(6) Uani 1 1 d . . . . .
N3 N 0.31268(16) 0.36962(18) 0.59838(11) 0.0410(6) Uani 1 1 d . . . . .
N2 N 0.50004(17) 0.38438(18) 0.57478(11) 0.0454(6) Uani 1 1 d . . . . .
N4 N 0.29189(16) 0.36381(18) 0.53538(10) 0.0431(6) Uani 1 1 d . . . . .
N1 N 0.5299(2) 0.5675(2) 0.83976(13) 0.0540(7) Uani 1 1 d . . . . .
O2 O 0.46779(19) 0.63616(18) 0.86335(10) 0.0769(8) Uani 1 1 d . . . . .
O1 O 0.61396(18) 0.53180(19) 0.86330(10) 0.0776(7) Uani 1 1 d . . . . .
C7 C 0.4211(2) 0.3930(2) 0.61218(13) 0.0347(7) Uani 1 1 d . . . . .
C3 C 0.3811(2) 0.5195(2) 0.69895(13) 0.0394(7) Uani 1 1 d . . . . .
H3 H 0.317533 0.544367 0.680469 0.047 Uiso 1 1 calc R . . . .
C1 C 0.5023(2) 0.5240(2) 0.78014(13) 0.0409(7) Uani 1 1 d . . . . .
C4 C 0.44752(19) 0.4376(2) 0.67150(13) 0.0358(7) Uani 1 1 d . . . . .
C5 C 0.5415(2) 0.4000(2) 0.69954(13) 0.0432(8) Uani 1 1 d . . . . .
H5 H 0.586376 0.345415 0.681187 0.052 Uiso 1 1 calc R . . . .
C9 C 0.3572(2) 0.2534(2) 0.44910(13) 0.0389(7) Uani 1 1 d . U . . .
C2 C 0.4088(2) 0.5642(2) 0.75342(13) 0.0432(7) Uani 1 1 d . . . . .
H2 H 0.365340 0.620201 0.771749 0.052 Uiso 1 1 calc R . . . .
C6 C 0.5687(2) 0.4428(2) 0.75423(14) 0.0443(8) Uani 1 1 d . . . . .
H6 H 0.631292 0.417072 0.773328 0.053 Uiso 1 1 calc R . . . .
C17 C 0.2467(2) 0.2936(2) 0.63091(14) 0.0450(8) Uani 1 1 d . . . . .
C14 C 0.3673(2) 0.3388(2) 0.40633(15) 0.0460(8) Uani 1 1 d . . . . .
H14 H 0.384295 0.415368 0.417065 0.055 Uiso 1 1 calc R . . . .
C12 C 0.3259(2) 0.1990(3) 0.33078(14) 0.0542(8) Uani 1 1 d . . . . .
H12 H 0.316210 0.180978 0.291067 0.065 Uiso 1 1 calc R . . . .
C8 C 0.3723(2) 0.2803(2) 0.51351(13) 0.0461(8) Uani 1 1 d . U . . .
H8 H 0.370769 0.208073 0.536943 0.055 Uiso 1 1 calc R . . . .
C13 C 0.3524(2) 0.3108(3) 0.34788(14) 0.0523(8) Uani 1 1 d . . . . .
H13 H 0.360321 0.368814 0.319331 0.063 Uiso 1 1 calc R . . . .
C10 C 0.3300(2) 0.1406(2) 0.43227(15) 0.0560(9) Uani 1 1 d . . . . .
H10 H 0.322513 0.082373 0.460721 0.067 Uiso 1 1 calc R . . . .
C15 C 0.1769(2) 0.3207(3) 0.53334(14) 0.0560(9) Uani 1 1 d . . . . .
H15A H 0.165129 0.272966 0.498475 0.067 Uiso 1 1 calc R . . . .
H15B H 0.126538 0.386162 0.532481 0.067 Uiso 1 1 calc R . . . .
C11 C 0.3141(2) 0.1141(3) 0.37345(15) 0.0588(9) Uani 1 1 d . . . . .
H11 H 0.295127 0.038227 0.362541 0.071 Uiso 1 1 calc R . . . .
C16 C 0.1607(2) 0.2484(3) 0.58904(14) 0.0602(9) Uani 1 1 d . . . . .
H16A H 0.088424 0.260192 0.605171 0.072 Uiso 1 1 calc R . . . .
H16B H 0.171088 0.165631 0.581086 0.072 Uiso 1 1 calc R . . . .


_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
O4 N2 1.407(3) . ?
O4 C8 1.442(3) . ?
O3 C17 1.207(3) . ?
N3 N4 1.450(3) . ?
N3 C7 1.394(3) . ?
N3 C17 1.397(3) . ?
N2 C7 1.292(3) . ?
N4 C8 1.460(3) . ?
N4 C15 1.497(3) . ?
N1 O2 1.217(3) . ?
N1 O1 1.232(3) . ?
N1 C1 1.477(4) . ?
C7 C4 1.472(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C3 C2 1.377(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.366(3) . ?
C4 C5 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C9 C14 1.379(3) . ?
C9 C8 1.501(4) . ?
C9 C10 1.383(3) . ?
C2 H2 0.9300 . ?
C6 H6 0.9300 . ?
C17 C16 1.510(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C12 C11 1.375(4) . ?
C8 H8 0.9800 . ?
C13 H13 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.520(4) . ?
C11 H11 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
N2 O4 C8 115.4(2) . . ?
C7 N3 N4 113.4(2) . . ?
C7 N3 C17 123.7(2) . . ?
C17 N3 N4 112.8(2) . . ?
C7 N2 O4 117.8(2) . . ?
N3 N4 C8 104.1(2) . . ?
N3 N4 C15 102.2(2) . . ?
C8 N4 C15 114.5(2) . . ?
O2 N1 O1 123.3(3) . . ?
O2 N1 C1 118.3(3) . . ?
O1 N1 C1 118.4(3) . . ?
N3 C7 C4 118.8(2) . . ?
N2 C7 N3 123.8(3) . . ?
N2 C7 C4 117.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C1 N1 118.7(3) . . ?
C6 C1 N1 118.9(3) . . ?
C6 C1 C2 122.4(3) . . ?
C3 C4 C7 120.8(2) . . ?
C5 C4 C7 119.6(2) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C14 C9 C8 121.8(3) . . ?
C14 C9 C10 119.1(3) . . ?
C10 C9 C8 119.2(3) . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O3 C17 N3 124.4(3) . . ?
O3 C17 C16 128.9(3) . . ?
N3 C17 C16 106.7(3) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C13 C12 H12 120.6 . . ?
C13 C12 C11 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
O4 C8 N4 106.2(2) . . ?
O4 C8 C9 106.4(2) . . ?
O4 C8 H8 110.6 . . ?
N4 C8 C9 112.3(2) . . ?
N4 C8 H8 110.6 . . ?
C9 C8 H8 110.6 . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 H13 119.3 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
N4 C15 H15A 110.5 . . ?
N4 C15 H15B 110.5 . . ?
N4 C15 C16 106.0(2) . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C17 C16 C15 104.1(2) . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
H16A C16 H16B 109.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 10.235
_oxdiff_exptl_absorpt_empirical_full_min 0.431
