# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_jmc_071603_0m
_database_code_depnum_ccdc_archive 'CCDC 1864586'
_audit_update_record             
;
2018-08-29 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_audit_creation_date             2016-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 N3 O'
_chemical_formula_sum            'C9 H9 N3 O'
_chemical_formula_weight         175.19
_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   6.1464(11)
_cell_length_b                   6.8359(12)
_cell_length_c                   19.339(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     812.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.514
_cell_measurement_theta_min      3.478
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8556.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12301
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         2.106
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1070
_reflns_number_total             1339
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.123
_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)+(0.0508P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H6B(0.5) H6A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6B,H6A)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.75337(19) 0.7500 0.48931(7) 0.0143(3) Uani 1 2 d S T P . .
N1 N 0.4134(2) 0.7500 0.31146(8) 0.0113(3) Uani 1 2 d S T P . .
N2 N 0.4388(2) 0.7500 0.42623(7) 0.0086(3) Uani 1 2 d S T P . .
N3 N 0.4379(2) 0.7500 0.54814(7) 0.0110(3) Uani 1 2 d S T P . .
C1 C 0.2068(3) 0.7500 0.34057(9) 0.0112(4) Uani 1 2 d S T P . .
H1 H 0.0752 0.7500 0.3148 0.013 Uiso 1 2 calc RS T P . .
C2 C 0.2174(3) 0.7500 0.41056(9) 0.0106(4) Uani 1 2 d S T P . .
H2 H 0.0992 0.7500 0.4422 0.013 Uiso 1 2 calc RS T P . .
C3 C 0.5463(3) 0.7500 0.36410(9) 0.0105(4) Uani 1 2 d S T P . .
H3 H 0.7003 0.7500 0.3599 0.013 Uiso 1 2 calc RS T P . .
C4 C 0.5541(3) 0.7500 0.49069(9) 0.0082(3) Uani 1 2 d S T P . .
C5 C 0.5279(3) 0.7500 0.61901(8) 0.0089(3) Uani 1 2 d S T P . .
H5A H 0.6105 0.8696 0.6310 0.011 Uiso 0.5 1 calc R . . . .
H5B H 0.6105 0.6304 0.6310 0.011 Uiso 0.5 1 calc R . . . .
C6 C 0.2062(3) 0.7500 0.56958(9) 0.0105(3) Uani 1 2 d S T P . .
H6B H 0.1254 0.6304 0.5564 0.013 Uiso 0.5 1 calc R . . . .
H6A H 0.1254 0.8696 0.5564 0.013 Uiso 0.5 1 calc R . . . .
C7 C 0.2901(3) 0.7500 0.64481(9) 0.0093(3) Uani 1 2 d S T P . .
C8 C 0.1918(2) 0.8445(2) 0.70646(6) 0.0127(3) Uani 1 1 d . . . . .
H8 H 0.1547 0.9623 0.7297 0.015 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
O1 C4 1.225(2) . ?
N1 C1 1.389(2) . ?
N1 C3 1.305(2) . ?
N2 C2 1.394(2) . ?
N2 C3 1.371(2) . ?
N2 C4 1.434(2) . ?
N3 C4 1.321(2) . ?
N3 C5 1.478(2) . ?
N3 C6 1.483(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.355(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C7 1.544(2) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 C7 1.544(2) . ?
C7 C8 1.4847(19) 8_575 ?
C7 C8 1.4847(19) . ?
C8 C8 1.293(3) 8_575 ?
C8 H8 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
C3 N1 C1 104.83(15) . . ?
C2 N2 C4 132.18(15) . . ?
C3 N2 C2 106.25(14) . . ?
C3 N2 C4 121.56(14) . . ?
C4 N3 C5 125.29(14) . . ?
C4 N3 C6 138.97(15) . . ?
C5 N3 C6 95.74(12) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 N1 111.13(16) . . ?
C2 C1 H1 124.4 . . ?
N2 C2 H2 127.3 . . ?
C1 C2 N2 105.32(15) . . ?
C1 C2 H2 127.3 . . ?
N1 C3 N2 112.46(16) . . ?
N1 C3 H3 123.8 . . ?
N2 C3 H3 123.8 . . ?
O1 C4 N2 118.38(15) . . ?
O1 C4 N3 123.98(16) . . ?
N3 C4 N2 117.64(14) . . ?
N3 C5 H5A 114.2 . . ?
N3 C5 H5B 114.2 . . ?
N3 C5 C7 86.88(12) . . ?
H5A C5 H5B 111.3 . . ?
C7 C5 H5A 114.2 . . ?
C7 C5 H5B 114.2 . . ?
N3 C6 H6B 114.2 . . ?
N3 C6 H6A 114.2 . . ?
N3 C6 C7 86.71(12) . . ?
H6B C6 H6A 111.4 . . ?
C7 C6 H6B 114.2 . . ?
C7 C6 H6A 114.2 . . ?
C6 C7 C5 90.67(13) . . ?
C8 C7 C5 130.13(12) 8_575 . ?
C8 C7 C5 130.13(12) . . ?
C8 C7 C6 128.38(12) 8_575 . ?
C8 C7 C6 128.38(12) . . ?
C8 C7 C8 51.61(12) . 8_575 ?
C7 C8 H8 147.9 . . ?
C8 C8 C7 64.20(6) 8_575 . ?
C8 C8 H8 147.9 8_575 . ?

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
N1 C1 C2 N2 0.000(0) . . . . ?
N3 C5 C7 C6 0.000(1) . . . . ?
N3 C5 C7 C8 -145.30(11) . . . . ?
N3 C5 C7 C8 145.30(11) . . . 8_575 ?
N3 C6 C7 C5 0.000(1) . . . . ?
N3 C6 C7 C8 -146.27(10) . . . 8_575 ?
N3 C6 C7 C8 146.27(10) . . . . ?
C1 N1 C3 N2 0.000(0) . . . . ?
C2 N2 C3 N1 0.000(0) . . . . ?
C2 N2 C4 O1 180.000(1) . . . . ?
C2 N2 C4 N3 0.000(1) . . . . ?
C3 N1 C1 C2 0.000(1) . . . . ?
C3 N2 C2 C1 0.000(0) . . . . ?
C3 N2 C4 O1 0.000(1) . . . . ?
C3 N2 C4 N3 180.000(1) . . . . ?
C4 N2 C2 C1 180.000(1) . . . . ?
C4 N2 C3 N1 180.000(0) . . . . ?
C4 N3 C5 C7 180.000(1) . . . . ?
C4 N3 C6 C7 180.000(1) . . . . ?
C5 N3 C4 O1 0.000(1) . . . . ?
C5 N3 C4 N2 180.000(1) . . . . ?
C5 N3 C6 C7 0.000(1) . . . . ?
C5 C7 C8 C8 -114.05(13) . . . 8_575 ?
C6 N3 C4 O1 180.000(1) . . . . ?
C6 N3 C4 N2 0.000(1) . . . . ?
C6 N3 C5 C7 0.000(1) . . . . ?
C6 C7 C8 C8 112.52(12) . . . 8_575 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
