# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_19mdw2h
_database_code_depnum_ccdc_archive 'CCDC 1984160'
loop_
_audit_author_name
_audit_author_address
'Chunhua Tony Hu'
;New York University
United States of America
;
_audit_update_record             
;
2020-02-14 deposited with the CCDC.	2020-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H7 N3 O'
_chemical_formula_weight         137.15

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   34.428(5)
_cell_length_b                   3.8120(6)
_cell_length_c                   19.787(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2596.8(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1162
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      18.86

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18380
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_av_R_equivalents  0.1332
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.568
_diffrn_reflns_theta_max         20.834
_diffrn_reflns_theta_full        20.834
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2728
_reflns_number_gt                1998
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0460P)²] 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_abs_structure_details 
;
 Flack x determined using 763 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   3.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     397
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.6304(2) 0.3671(17) 0.6878(4) 0.031(2) Uani 1 1 d . . . . .
N1 N 0.5798(3) 0.799(2) 0.9113(5) 0.033(3) Uani 1 1 d . . . . .
N2 N 0.6851(3) 0.423(2) 0.7504(5) 0.029(2) Uani 1 1 d D . . . .
H2N H 0.697(3) 0.44(3) 0.789(3) 0.034 Uiso 1 1 d D U . . .
N3 N 0.7109(3) 0.281(2) 0.7021(5) 0.032(2) Uani 1 1 d D . . . .
H3A H 0.711(3) 0.43(2) 0.669(4) 0.039 Uiso 1 1 d D U . . .
H3B H 0.702(3) 0.094(16) 0.683(5) 0.039 Uiso 1 1 d D U . . .
C1 C 0.5634(3) 0.644(3) 0.8578(7) 0.035(3) Uani 1 1 d . . . . .
H1 H 0.536157 0.606352 0.858216 0.041 Uiso 1 1 calc R U . . .
C2 C 0.5843(3) 0.537(2) 0.8019(6) 0.029(3) Uani 1 1 d . . . . .
H2A H 0.571232 0.433496 0.764644 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6242(3) 0.581(2) 0.8001(6) 0.022(3) Uani 1 1 d . . . . .
C4 C 0.6411(3) 0.756(3) 0.8544(6) 0.026(3) Uani 1 1 d . . . . .
H4 H 0.668149 0.807334 0.854355 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6180(3) 0.856(3) 0.9086(7) 0.034(3) Uani 1 1 d . . . . .
H5 H 0.629993 0.971303 0.945677 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6467(3) 0.448(2) 0.7405(6) 0.023(3) Uani 1 1 d . . . . .
O2 O 0.71516(19) 0.7864(17) 0.5832(4) 0.0291(19) Uani 1 1 d . . . . .
N4 N 0.7726(3) 1.351(2) 0.3763(5) 0.028(3) Uani 1 1 d . . . . .
N5 N 0.6619(3) 0.991(2) 0.5284(5) 0.025(2) Uani 1 1 d D . . . .
H5N H 0.650(3) 1.08(2) 0.493(3) 0.030 Uiso 1 1 d D U . . .
N6 N 0.6356(3) 0.842(2) 0.5746(5) 0.030(3) Uani 1 1 d D . . . .
H6A H 0.646(3) 0.70(2) 0.604(4) 0.036 Uiso 1 1 d D U . . .
H6B H 0.634(3) 0.97(2) 0.611(3) 0.036 Uiso 1 1 d D U . . .
C7 C 0.7838(3) 1.337(3) 0.4409(7) 0.026(3) Uani 1 1 d . . . . .
H7 H 0.808823 1.424356 0.451964 0.031 Uiso 1 1 calc R U . . .
C8 C 0.7611(3) 1.202(2) 0.4932(6) 0.026(3) Uani 1 1 d . . . . .
H8 H 0.770549 1.193417 0.538290 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7242(3) 1.081(2) 0.4771(6) 0.023(3) Uani 1 1 d . . . . .
C10 C 0.7121(3) 1.099(3) 0.4104(6) 0.026(3) Uani 1 1 d . . . . .
H10 H 0.686809 1.022634 0.398049 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7370(3) 1.229(3) 0.3624(6) 0.032(3) Uani 1 1 d . . . . .
H11 H 0.728513 1.231696 0.316661 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7001(3) 0.938(3) 0.5347(6) 0.023(3) Uani 1 1 d . . . . .
O3 O 0.5323(2) 0.4116(18) 0.4163(4) 0.0289(19) Uani 1 1 d . . . . .
N7 N 0.4759(3) 0.977(2) 0.6237(5) 0.028(3) Uani 1 1 d . . . . .
N8 N 0.5859(3) 0.508(2) 0.4786(5) 0.027(2) Uani 1 1 d D . . . .
H8N H 0.595(3) 0.60(2) 0.515(3) 0.033 Uiso 1 1 d D U . . .
N9 N 0.6116(3) 0.342(2) 0.4329(5) 0.029(2) Uani 1 1 d D . . . .
H9A H 0.604(2) 0.158(15) 0.411(3) 0.034 Uiso 1 1 d D U . . .
H9B H 0.617(3) 0.523(16) 0.409(4) 0.034 Uiso 1 1 d D U . . .
C13 C 0.4656(3) 0.970(3) 0.5587(7) 0.029(3) Uani 1 1 d . . . . .
H13 H 0.441408 1.071276 0.546479 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4881(3) 0.822(3) 0.5079(6) 0.027(3) Uani 1 1 d . . . . .
H14 H 0.479024 0.818779 0.462609 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5241(3) 0.681(2) 0.5241(6) 0.025(3) Uani 1 1 d . . . . .
C16 C 0.5354(3) 0.690(2) 0.5911(6) 0.027(3) Uani 1 1 d . . . . .
H16 H 0.559907 0.597308 0.604250 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5109(3) 0.836(3) 0.6387(6) 0.029(3) Uani 1 1 d . . . . .
H17 H 0.519097 0.836881 0.684591 0.035 Uiso 1 1 calc R U . . .
C18 C 0.5477(4) 0.521(3) 0.4687(7) 0.026(3) Uani 1 1 d . . . . .
O4 O 0.6148(2) -0.1459(18) 0.3199(4) 0.031(2) Uani 1 1 d D . . . .
N10 N 0.6727(3) -0.412(2) 0.0905(5) 0.038(3) Uani 1 1 d . . . . .
N11 N 0.5628(3) -0.145(2) 0.2486(5) 0.029(2) Uani 1 1 d D . . . .
H11N H 0.554(3) -0.15(3) 0.207(2) 0.035 Uiso 1 1 d D U . . .
N12 N 0.5350(3) -0.046(2) 0.2981(5) 0.036(3) Uani 1 1 d D . . . .
H12A H 0.540(3) 0.10(2) 0.330(4) 0.043 Uiso 1 1 d D U . . .
H12B H 0.528(3) -0.216(19) 0.323(4) 0.043 Uiso 1 1 d D U . . .
C19 C 0.6862(3) -0.272(3) 0.1468(6) 0.033(3) Uani 1 1 d . . . . .
H19 H 0.713128 -0.220005 0.148473 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6646(3) -0.197(3) 0.2029(6) 0.031(3) Uani 1 1 d . . . . .
H20 H 0.676287 -0.093709 0.241583 0.037 Uiso 1 1 calc R U . . .
C21 C 0.6252(3) -0.275(3) 0.2021(6) 0.025(3) Uani 1 1 d . . . . .
C22 C 0.6099(3) -0.428(3) 0.1448(6) 0.025(3) Uani 1 1 d . . . . .
H22 H 0.583245 -0.490128 0.142640 0.031 Uiso 1 1 calc R U . . .
C23 C 0.6344(4) -0.489(3) 0.0903(6) 0.034(3) Uani 1 1 d . . . . .
H23 H 0.623616 -0.591293 0.050662 0.041 Uiso 1 1 calc R U . . .
C24 C 0.6007(4) -0.182(3) 0.2625(6) 0.027(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 C6 1.225(13) . ?
N1 C5 1.335(13) . ?
N1 C1 1.337(14) . ?
N2 C6 1.341(14) . ?
N2 N3 1.415(14) . ?
N2 H2N 0.866(16) . ?
N3 H3A 0.861(16) . ?
N3 H3B 0.864(16) . ?
C1 C2 1.380(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(13) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(14) . ?
C3 C6 1.498(15) . ?
C4 C5 1.389(15) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
O2 C12 1.237(13) . ?
N4 C7 1.338(14) . ?
N4 C11 1.339(13) . ?
N5 C12 1.335(14) . ?
N5 N6 1.407(13) . ?
N5 H5N 0.861(16) . ?
N6 H6A 0.862(16) . ?
N6 H6B 0.861(16) . ?
C7 C8 1.394(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.387(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(15) . ?
C9 C12 1.511(16) . ?
C10 C11 1.371(15) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
O3 C18 1.236(14) . ?
N7 C13 1.335(13) . ?
N7 C17 1.353(13) . ?
N8 C18 1.330(14) . ?
N8 N9 1.413(13) . ?
N8 H8N 0.862(16) . ?
N9 H9A 0.867(16) . ?
N9 H9B 0.861(16) . ?
C13 C14 1.387(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(15) . ?
C15 C18 1.494(16) . ?
C16 C17 1.382(14) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O4 C24 1.243(13) . ?
N10 C19 1.318(14) . ?
N10 C23 1.352(14) . ?
N11 C24 1.341(14) . ?
N11 N12 1.420(13) . ?
N11 H11N 0.866(16) . ?
N12 H12A 0.860(16) . ?
N12 H12B 0.858(16) . ?
C19 C20 1.367(15) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(15) . ?
C21 C24 1.504(15) . ?
C22 C23 1.388(16) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C5 N1 C1 117.0(10) . . ?
C6 N2 N3 123.3(10) . . ?
C6 N2 H2N 127(8) . . ?
N3 N2 H2N 108(7) . . ?
N2 N3 H3A 105(7) . . ?
N2 N3 H3B 113(7) . . ?
H3A N3 H3B 101(10) . . ?
N1 C1 C2 123.1(10) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 120.1(11) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 116.9(10) . . ?
C2 C3 C6 119.6(11) . . ?
C4 C3 C6 123.5(10) . . ?
C5 C4 C3 119.1(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 123.6(12) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O1 C6 N2 124.0(11) . . ?
O1 C6 C3 121.2(10) . . ?
N2 C6 C3 114.8(11) . . ?
C7 N4 C11 116.6(10) . . ?
C12 N5 N6 120.9(9) . . ?
C12 N5 H5N 126(7) . . ?
N6 N5 H5N 112(7) . . ?
N5 N6 H6A 114(7) . . ?
N5 N6 H6B 111(7) . . ?
H6A N6 H6B 80(9) . . ?
N4 C7 C8 124.2(10) . . ?
N4 C7 H7 117.9 . . ?
C8 C7 H7 117.9 . . ?
C9 C8 C7 117.7(10) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C8 C9 C10 118.6(10) . . ?
C8 C9 C12 116.8(11) . . ?
C10 C9 C12 124.7(10) . . ?
C11 C10 C9 119.3(10) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N4 C11 C10 123.7(11) . . ?
N4 C11 H11 118.2 . . ?
C10 C11 H11 118.2 . . ?
O2 C12 N5 123.8(10) . . ?
O2 C12 C9 121.5(10) . . ?
N5 C12 C9 114.7(11) . . ?
C13 N7 C17 116.1(10) . . ?
C18 N8 N9 122.8(10) . . ?
C18 N8 H8N 118(7) . . ?
N9 N8 H8N 119(7) . . ?
N8 N9 H9A 119(4) . . ?
N8 N9 H9B 98(7) . . ?
H9A N9 H9B 116(9) . . ?
N7 C13 C14 123.9(11) . . ?
N7 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C13 C14 C15 119.3(11) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 117.6(11) . . ?
C16 C15 C18 124.1(10) . . ?
C14 C15 C18 118.3(11) . . ?
C15 C16 C17 119.5(10) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
N7 C17 C16 123.6(10) . . ?
N7 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
O3 C18 N8 122.3(11) . . ?
O3 C18 C15 121.4(11) . . ?
N8 C18 C15 116.4(12) . . ?
C19 N10 C23 115.7(10) . . ?
C24 N11 N12 122.9(10) . . ?
C24 N11 H11N 121(7) . . ?
N12 N11 H11N 115(7) . . ?
N11 N12 H12A 122(8) . . ?
N11 N12 H12B 114(7) . . ?
H12A N12 H12B 97(10) . . ?
N10 C19 C20 125.5(11) . . ?
N10 C19 H19 117.3 . . ?
C20 C19 H19 117.3 . . ?
C19 C20 C21 118.5(11) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
C22 C21 C20 118.2(10) . . ?
C22 C21 C24 122.6(10) . . ?
C20 C21 C24 119.3(10) . . ?
C21 C22 C23 118.6(10) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
N10 C23 C22 123.5(11) . . ?
N10 C23 H23 118.2 . . ?
C22 C23 H23 118.2 . . ?
O4 C24 N11 123.7(11) . . ?
O4 C24 C21 122.2(11) . . ?
N11 C24 C21 114.1(11) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045

# start Validation Reply Form
_vrf_THETM01_19mdw2h             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal is a thin needle and does not diffract well
even with an exposure time of 50 seconds per frame.
;
_vrf_PLAT089_19mdw2h             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.56 Note  
RESPONSE: The crystal is a thin needle and does not diffract well
even with an exposure time of 50 seconds per frame.
;
_vrf_PLAT340_19mdw2h             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0162 Ang.  
RESPONSE: The crystal is a thin needle and does not diffract well
even with an exposure time of 50 seconds per frame.
;
# end Validation Reply Form


