# 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_per1132
_database_code_depnum_ccdc_archive 'CCDC 1984327'
loop_
_audit_author_name
_audit_author_address
'Chartrand D.'
;Universite de Montreal
Canada
;
_audit_update_record             
;
2020-02-16 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
daniel.chartrand.1@umontreal.ca
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H2.5 N1.5 O2.5)'
_chemical_formula_sum            'C14 H5 N3 O5'
_chemical_formula_weight         295.21
_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/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                   5.0814(2)
_cell_length_b                   6.9825(3)
_cell_length_c                   17.0804(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.994(2)
_cell_angle_gamma                90
_cell_volume                     604.56(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5405
_cell_measurement_temperature    100
_cell_measurement_theta_max      69.996
_cell_measurement_theta_min      5.192
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_T_max  0.8644
_exptl_absorpt_correction_T_min  0.8139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0731 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.9416. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.055
_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  0.0173
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15821
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.084
_diffrn_reflns_theta_min         5.192
_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 0.996
_diffrn_measured_fraction_theta_max 0.997
_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_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1075
_reflns_number_total             1152
_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 (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.080
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         1152
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.064
_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)+(0.0727P)²+0.0424P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O2-N2 \\sim N2-O3 \\sim O4-N3A \\sim N3A-O5A \\sim N3A-O5B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5A \\sim O5B: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.05
N3A \\sim N3B: within 2A with sigma of 0.008 and sigma for terminal atoms of
0.04
4. Others
 Sof(O5A)=Sof(N1A)=Sof(N3A)=Sof(C1A)=Sof(H12)=0.5*(1-FVAR(2))
 Sof(O5B)=Sof(N1B)=Sof(N3B)=Sof(C1B)=Sof(H2)=0.5*FVAR(2)
 Fixed Sof: O1(0.5) O2(0.5) O3(0.5) O4(0.5) N2(0.5) C2(0.5) C3(0.5) H3(0.5)
 C4(0.5) C5(0.5) H5(0.5) C6(0.5) C7(0.5) C8(0.5) C9(0.5) H9(0.5) C10(0.5)
 C11(0.5) H11(0.5) C12(0.5) C13(0.5) C14(0.5)
5.a Riding coordinates:
 C2(H2)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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 1.4290(3) 1.2827(3) 0.44308(11) 0.0478(4) Uani 0.5 1 d . . P A -1
O2 O 0.7301(15) 1.4745(10) 0.7449(3) 0.134(2) Uani 0.5 1 d D . P A -1
O3 O 1.0140(4) 1.6412(4) 0.68598(11) 0.0822(6) Uani 0.5 1 d D . P A -1
O4 O 1.1783(10) 0.4534(7) 0.2619(4) 0.0988(16) Uani 0.5 1 d D . P . .
O5A O 1.5085(6) 0.6371(5) 0.26854(16) 0.0684(7) Uani 0.372(3) 1 d D U P B -1
O5B O 1.401(4) 0.704(3) 0.2328(11) 0.144(5) Uani 0.128(3) 1 d D U P B -2
N1A N 0.4475(5) 0.7242(4) 0.59809(17) 0.0585(8) Uani 0.372(3) 1 d . . P B -1
N1B N 0.4918(16) 0.6243(13) 0.5509(5) 0.054(3) Uani 0.128(3) 1 d . . P B -2
N3B N 1.258(5) 0.623(3) 0.2799(14) 0.067(4) Uani 0.128(3) 1 d . U P B -2
N2 N 0.8868(6) 1.5043(6) 0.6959(2) 0.0727(8) Uani 0.5 1 d D . P A -1
N3A N 1.2964(17) 0.5826(11) 0.2930(5) 0.0720(18) Uani 0.372(3) 1 d D U P B -1
C1A C 0.5794(5) 0.8550(4) 0.59685(14) 0.0457(7) Uani 0.372(3) 1 d . . P B -1
C1B C 0.6565(14) 0.6741(10) 0.5141(5) 0.040(2) Uani 0.128(3) 1 d . . P B -2
C2 C 0.7474(10) 1.0292(10) 0.5954(4) 0.0507(12) Uani 0.5 1 d . . P . .
H2 H 0.641870 0.918807 0.598064 0.061 Uiso 0.128(3) 1 d R . P B -2
C3 C 0.7369(11) 1.1873(12) 0.6474(4) 0.0569(18) Uani 0.5 1 d . . P A -1
H3 H 0.617183 1.187216 0.687711 0.068 Uiso 0.5 1 calc R . P A -1
C4 C 0.9039(13) 1.3421(11) 0.6385(3) 0.0516(14) Uani 0.5 1 d . . P A -1
C5 C 1.0833(10) 1.3527(8) 0.5805(3) 0.0423(10) Uani 0.5 1 d . . P A -1
H5 H 1.194671 1.460652 0.575567 0.051 Uiso 0.5 1 calc R . P A -1
C6 C 1.0898(9) 1.1946(10) 0.5299(3) 0.0419(14) Uani 0.5 1 d . . P A -1
C7 C 1.2635(3) 1.1736(2) 0.46465(9) 0.0390(4) Uani 0.5 1 d . . P A -1
C8 C 1.1907(9) 0.9811(6) 0.4302(3) 0.0383(10) Uani 0.5 1 d . . P A -1
C9 C 1.2885(11) 0.8815(9) 0.3705(3) 0.0433(11) Uani 0.5 1 d . . P A -1
H9 H 1.425414 0.932413 0.341568 0.052 Uiso 0.5 1 calc R . P A -1
C10 C 1.1807(13) 0.7021(9) 0.3533(4) 0.0504(15) Uani 0.5 1 d . . P . .
C11 C 0.9796(10) 0.6278(6) 0.3924(4) 0.0462(12) Uani 0.5 1 d . . P B -1
H11 H 0.905008 0.507212 0.377634 0.055 Uiso 0.5 1 calc R . P B -1
C12 C 0.8854(7) 0.7300(10) 0.4539(3) 0.0412(10) Uani 0.5 1 d . . P . .
H12 H 0.747863 0.678985 0.482562 0.049 Uiso 0.372(3) 1 calc R . P B -1
C13 C 0.9932(9) 0.9072(8) 0.47331(19) 0.0371(9) Uani 0.5 1 d . . P A -1
C14 C 0.9228(11) 1.0356(7) 0.5372(3) 0.0440(10) Uani 0.5 1 d . . P A -1


_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 C7 1.211(2) . ?
O2 N2 1.213(6) . ?
O3 N2 1.173(5) . ?
O4 N3B 1.28(2) . ?
O4 N3A 1.188(9) . ?
O5A N3A 1.242(10) . ?
O5B N3B 1.26(3) . ?
N1A C1A 1.134(4) . ?
N1B C1B 1.136(12) . ?
N3B C10 1.45(2) . ?
N2 C4 1.504(8) . ?
N3A C10 1.479(12) . ?
C1A C2 1.487(7) . ?
C1B C12 1.652(9) . ?
C2 C3 1.420(7) . ?
C2 C14 1.381(5) . ?
C3 C4 1.389(7) . ?
C4 C5 1.394(5) . ?
C5 C6 1.404(5) . ?
C6 C7 1.476(5) . ?
C6 C14 1.408(5) . ?
C7 C8 1.503(4) . ?
C8 C9 1.357(5) . ?
C8 C13 1.385(4) . ?
C9 C10 1.391(5) . ?
C10 C11 1.362(5) . ?
C11 C12 1.382(5) . ?
C12 C13 1.385(4) . ?
C13 C14 1.476(5) . ?

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
O4 N3B C10 118(2) . . ?
O5B N3B O4 117(2) . . ?
O5B N3B C10 125.7(17) . . ?
O2 N2 C4 113.0(7) . . ?
O3 N2 O2 129.3(7) . . ?
O3 N2 C4 117.6(4) . . ?
O4 N3A O5A 120.4(9) . . ?
O4 N3A C10 121.8(9) . . ?
O5A N3A C10 117.2(7) . . ?
N1A C1A C2 178.8(4) . . ?
N1B C1B C12 174.2(10) . . ?
C3 C2 C1A 125.4(6) . . ?
C14 C2 C1A 116.0(7) . . ?
C14 C2 C3 118.6(6) . . ?
C4 C3 C2 119.1(6) . . ?
C3 C4 N2 116.8(7) . . ?
C3 C4 C5 123.6(6) . . ?
C5 C4 N2 119.5(7) . . ?
C4 C5 C6 116.1(5) . . ?
C5 C6 C7 125.8(6) . . ?
C5 C6 C14 121.6(5) . . ?
C14 C6 C7 112.6(6) . . ?
O1 C7 C6 129.2(3) . . ?
O1 C7 C8 126.9(3) . . ?
C6 C7 C8 103.9(3) . . ?
C9 C8 C7 131.3(6) . . ?
C9 C8 C13 121.7(4) . . ?
C13 C8 C7 107.0(5) . . ?
C8 C9 C10 117.5(6) . . ?
C9 C10 N3A 119.1(7) . . ?
C11 C10 N3A 118.4(7) . . ?
C11 C10 C9 122.5(6) . . ?
C10 C11 C12 119.2(4) . . ?
C11 C12 C13 119.4(4) . . ?
C8 C13 C14 112.9(7) . . ?
C12 C13 C8 119.7(4) . . ?
C12 C13 C14 127.5(8) . . ?
C2 C14 C6 120.8(6) . . ?
C2 C14 C13 135.6(9) . . ?
C6 C14 C13 103.6(8) . . ?

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 C7 C8 C9 1.6(5) . . . . ?
O1 C7 C8 C13 179.93(18) . . . . ?
O2 N2 C4 C3 2.0(6) . . . . ?
O2 N2 C4 C5 -177.6(5) . . . . ?
O3 N2 C4 C3 -175.1(3) . . . . ?
O3 N2 C4 C5 5.2(5) . . . . ?
O4 N3A C10 C9 -160.9(6) . . . . ?
O4 N3A C10 C11 22.1(8) . . . . ?
O5A N3A C10 C9 10.0(8) . . . . ?
O5A N3A C10 C11 -167.0(4) . . . . ?
N2 C4 C5 C6 179.2(3) . . . . ?
N3A C10 C11 C12 174.0(4) . . . . ?
C1A C2 C3 C4 -179.2(4) . . . . ?
C1A C2 C14 C6 179.4(3) . . . . ?
C1A C2 C14 C13 -0.9(5) . . . . ?
C2 C3 C4 N2 -179.2(4) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C2 C14 C6 0.6(5) . . . . ?
C3 C2 C14 C13 -179.7(3) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C4 C5 C6 C14 0.5(4) . . . . ?
C5 C6 C7 O1 0.6(4) . . . . ?
C5 C6 C7 C8 -180.0(3) . . . . ?
C5 C6 C14 C2 -0.6(4) . . . . ?
C5 C6 C14 C13 179.6(3) . . . . ?
C6 C7 C8 C9 -177.8(4) . . . . ?
C6 C7 C8 C13 0.5(3) . . . . ?
C7 C6 C14 C2 179.6(3) . . . . ?
C7 C6 C14 C13 -0.2(3) . . . . ?
C7 C8 C9 C10 178.8(4) . . . . ?
C7 C8 C13 C12 179.4(2) . . . . ?
C7 C8 C13 C14 -0.6(2) . . . . ?
C8 C9 C10 N3A -175.1(5) . . . . ?
C8 C9 C10 C11 1.8(7) . . . . ?
C8 C13 C14 C2 -179.2(4) . . . . ?
C8 C13 C14 C6 0.5(2) . . . . ?
C9 C8 C13 C12 -2.1(4) . . . . ?
C9 C8 C13 C14 177.9(3) . . . . ?
C9 C10 C11 C12 -2.8(6) . . . . ?
C10 C11 C12 C13 1.4(5) . . . . ?
C11 C12 C13 C8 1.0(4) . . . . ?
C11 C12 C13 C14 -179.0(2) . . . . ?
C12 C13 C14 C2 0.8(5) . . . . ?
C12 C13 C14 C6 -179.5(3) . . . . ?
C13 C8 C9 C10 0.7(6) . . . . ?
C14 C2 C3 C4 -0.5(6) . . . . ?
C14 C6 C7 O1 -179.6(2) . . . . ?
C14 C6 C7 C8 -0.2(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT088_per1132             
;
PROBLEM: Poor Data / Parameter Ratio .................... 5.05 Note
RESPONSE: The entire molecule has positionnal disorder because it 
is sitting on an inversion center despite the absence of such symmetry
 in the molecule. This requires defining double the atoms
from the diffraction pattern of a smaller volume cell, limiting the number of
reflections available. 
;
_vrf_PLAT315_per1132             
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C2B Check
RESPONSE: Checkcif seems to have difficulties assigning the bonds to the nitrile
moieties due to the disorder. C1a is bond to N1a and C2, C1b is bond to N2a and
C12. These are correctly displayed in the connectivity list of the cif file. 
;
_vrf_PLAT430_per1132             
;
PROBLEM: Short Inter D...A Contact O4 ..O5B . 2.75 Ang.
RESPONSE: O4 was set to part 0 to have proper bond listing for the disordered
part of this nitro group (N3a O5a and N3b O5b). As part -1 it would not interact 
with the generated O5a and O5b in adjacent molecules. This match with the
expected 50% disorder of the main molecule.
;
_exptl_crystal_recrystallization_method 'Vapour deposition'
