# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_per114
_audit_block_doi                 10.5517/ccdc.csd.cc24wx32
_database_code_depnum_ccdc_archive 'CCDC 1993024'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0CC01236J 2020
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-03-26 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
ehsan.hamzehpoor@mail.mcgill.ca
thierry.maris@umontreal.ca
_chemical_name_common            DCDNF
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H4 N4 O5'
_chemical_formula_sum            'C15 H4 N4 O5'
_chemical_formula_weight         320.22
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.8806(3)
_cell_length_b                   8.6623(3)
_cell_length_c                   19.5240(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.543(1)
_cell_angle_gamma                90
_cell_volume                     1326.56(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.033
_cell_measurement_theta_min      5.591
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8588.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method Sublimation
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.100
_diffrn_reflns_theta_min         5.591
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2476
_reflns_number_total             2517
_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       
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2019) V8.40A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2517
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.041
_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)+(0.0506P)²+0.5421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C12(H12)
;
_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
O1 O 0.16337(11) 0.32424(11) 0.34513(4) 0.0261(2) Uani 1 1 d . . . . .
O2 O 0.94400(10) 0.63979(10) 0.26608(5) 0.0249(2) Uani 1 1 d . . . . .
O3 O 0.69866(11) 0.72230(10) 0.21961(4) 0.0234(2) Uani 1 1 d . . . . .
O4 O 0.72931(11) 0.44017(10) 0.15790(4) 0.0240(2) Uani 1 1 d . . . . .
O5 O 0.61784(12) 0.58887(11) 0.07554(5) 0.0287(2) Uani 1 1 d . . . . .
N1 N 0.78775(12) 0.64134(11) 0.26036(5) 0.0202(2) Uani 1 1 d . . . . .
N2 N 0.60875(13) 0.50914(12) 0.12657(5) 0.0213(2) Uani 1 1 d . . . . .
N3 N 0.84303(15) 0.38944(14) 0.54343(6) 0.0316(3) Uani 1 1 d . . . . .
N4 N -0.09116(14) 0.33124(15) 0.02810(6) 0.0313(3) Uani 1 1 d . . . . .
C1 C 0.27332(15) 0.37945(14) 0.31358(6) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.45101(15) 0.42111(14) 0.34059(6) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.52537(15) 0.39882(14) 0.40671(6) 0.0228(3) Uani 1 1 d . . . . .
H3 H 0.463688 0.353227 0.440972 0.027 Uiso 1 1 calc R U . . .
C4 C 0.69460(16) 0.44561(14) 0.42158(6) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.78031(15) 0.52198(14) 0.37240(6) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.893599 0.557762 0.383462 0.026 Uiso 1 1 calc R U . . .
C6 C 0.69828(15) 0.54521(13) 0.30704(6) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.53562(15) 0.48713(13) 0.28775(6) 0.0188(2) Uani 1 1 d . . . . .
C8 C 0.42214(15) 0.47061(13) 0.22202(6) 0.0187(2) Uani 1 1 d . . . . .
C9 C 0.44146(15) 0.48552(13) 0.15200(6) 0.0196(3) Uani 1 1 d . . . . .
C10 C 0.30734(15) 0.45934(14) 0.10186(6) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.322125 0.475786 0.054700 0.026 Uiso 1 1 calc R U . . .
C11 C 0.15093(15) 0.40881(14) 0.12109(6) 0.0217(3) Uani 1 1 d . . . . .
C12 C 0.12818(15) 0.38433(14) 0.19031(6) 0.0210(3) Uani 1 1 d . . . . .
H12 H 0.022938 0.347112 0.203740 0.025 Uiso 1 1 calc R U . . .
C13 C 0.26336(15) 0.41591(13) 0.23860(6) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.77998(16) 0.41611(15) 0.48935(7) 0.0250(3) Uani 1 1 d . . . . .
C15 C 0.01601(16) 0.36817(15) 0.06866(6) 0.0243(3) 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
O1 C1 1.2092(15) . ?
O2 N1 1.2257(13) . ?
O3 N1 1.2287(13) . ?
O4 N2 1.2335(13) . ?
O5 N2 1.2200(14) . ?
N1 C6 1.4647(15) . ?
N2 C9 1.4673(15) . ?
N3 C14 1.1461(18) . ?
N4 C15 1.1461(17) . ?
C1 C2 1.4921(16) . ?
C1 C13 1.4922(16) . ?
C2 C3 1.3789(17) . ?
C2 C7 1.4032(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3973(17) . ?
C4 C5 1.3933(18) . ?
C4 C14 1.4479(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3883(17) . ?
C6 C7 1.3946(17) . ?
C7 C8 1.4984(16) . ?
C8 C9 1.3961(17) . ?
C8 C13 1.4047(16) . ?
C9 C10 1.3881(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3933(17) . ?
C11 C12 1.3967(17) . ?
C11 C15 1.4463(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3801(17) . ?

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
O2 N1 O3 124.85(10) . . ?
O2 N1 C6 118.48(10) . . ?
O3 N1 C6 116.62(9) . . ?
O4 N2 C9 116.03(10) . . ?
O5 N2 O4 125.17(10) . . ?
O5 N2 C9 118.74(10) . . ?
O1 C1 C2 127.58(11) . . ?
O1 C1 C13 127.67(11) . . ?
C2 C1 C13 104.72(10) . . ?
C3 C2 C1 126.62(11) . . ?
C3 C2 C7 123.80(11) . . ?
C7 C2 C1 109.58(10) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.69(11) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 C14 119.25(11) . . ?
C5 C4 C3 120.73(11) . . ?
C5 C4 C14 120.01(11) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.25(11) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 N1 116.42(10) . . ?
C5 C6 C7 122.02(11) . . ?
C7 C6 N1 121.48(11) . . ?
C2 C7 C8 107.70(10) . . ?
C6 C7 C2 115.98(11) . . ?
C6 C7 C8 136.28(11) . . ?
C9 C8 C7 135.83(11) . . ?
C9 C8 C13 116.15(11) . . ?
C13 C8 C7 107.83(10) . . ?
C8 C9 N2 122.06(10) . . ?
C10 C9 N2 115.59(10) . . ?
C10 C9 C8 121.86(11) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.64(11) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.53(11) . . ?
C10 C11 C15 119.66(11) . . ?
C12 C11 C15 119.58(11) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 117.92(11) . . ?
C13 C12 H12 121.0 . . ?
C8 C13 C1 109.50(10) . . ?
C12 C13 C1 126.32(11) . . ?
C12 C13 C8 123.74(11) . . ?
N3 C14 C4 177.64(14) . . ?
N4 C15 C11 177.74(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 N3 0.95 2.45 3.3403(16) 156.9 3_766 yes

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
O1 C1 C2 C3 2.6(2) . . . . ?
O1 C1 C2 C7 -177.89(12) . . . . ?
O1 C1 C13 C8 -176.70(12) . . . . ?
O1 C1 C13 C12 -4.1(2) . . . . ?
O2 N1 C6 C5 31.39(15) . . . . ?
O2 N1 C6 C7 -151.82(11) . . . . ?
O3 N1 C6 C5 -146.12(11) . . . . ?
O3 N1 C6 C7 30.68(16) . . . . ?
O4 N2 C9 C8 36.55(16) . . . . ?
O4 N2 C9 C10 -135.55(11) . . . . ?
O5 N2 C9 C8 -146.18(11) . . . . ?
O5 N2 C9 C10 41.72(15) . . . . ?
N1 C6 C7 C2 -168.76(10) . . . . ?
N1 C6 C7 C8 13.7(2) . . . . ?
N2 C9 C10 C11 168.65(10) . . . . ?
C1 C2 C3 C4 179.73(11) . . . . ?
C1 C2 C7 C6 174.20(10) . . . . ?
C1 C2 C7 C8 -7.58(13) . . . . ?
C2 C1 C13 C8 1.40(13) . . . . ?
C2 C1 C13 C12 173.97(11) . . . . ?
C2 C3 C4 C5 4.46(18) . . . . ?
C2 C3 C4 C14 -176.52(11) . . . . ?
C2 C7 C8 C9 -166.01(13) . . . . ?
C2 C7 C8 C13 8.44(13) . . . . ?
C3 C2 C7 C6 -6.27(18) . . . . ?
C3 C2 C7 C8 171.95(11) . . . . ?
C3 C4 C5 C6 -2.92(18) . . . . ?
C4 C5 C6 N1 173.24(10) . . . . ?
C4 C5 C6 C7 -3.54(18) . . . . ?
C5 C6 C7 C2 7.85(17) . . . . ?
C5 C6 C7 C8 -169.70(12) . . . . ?
C6 C7 C8 C9 11.7(2) . . . . ?
C6 C7 C8 C13 -173.88(13) . . . . ?
C7 C2 C3 C4 0.28(19) . . . . ?
C7 C8 C9 N2 7.3(2) . . . . ?
C7 C8 C9 C10 178.96(12) . . . . ?
C7 C8 C13 C1 -5.91(13) . . . . ?
C7 C8 C13 C12 -178.71(11) . . . . ?
C8 C9 C10 C11 -3.47(18) . . . . ?
C9 C8 C13 C1 169.79(10) . . . . ?
C9 C8 C13 C12 -3.02(17) . . . . ?
C9 C10 C11 C12 -0.01(18) . . . . ?
C9 C10 C11 C15 -174.44(11) . . . . ?
C10 C11 C12 C13 1.79(18) . . . . ?
C11 C12 C13 C1 -171.79(11) . . . . ?
C11 C12 C13 C8 -0.22(18) . . . . ?
C13 C1 C2 C3 -175.51(12) . . . . ?
C13 C1 C2 C7 4.01(13) . . . . ?
C13 C8 C9 N2 -166.77(10) . . . . ?
C13 C8 C9 C10 4.84(17) . . . . ?
C14 C4 C5 C6 178.08(11) . . . . ?
C15 C11 C12 C13 176.22(11) . . . . ?

_olex2_date_sample_data_collection 2020-02-18
_olex2_date_sample_submission    2020-02-18
_olex2_exptl_crystal_mounting_method 'mounted on  cryoloop'
_olex2_submission_original_sample_id DP-EH-DCN-NIT
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       semiconductivity
