# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_bb
_audit_block_doi                 10.5517/ccdc.csd.cc1zx7gl
_database_code_depnum_ccdc_archive 'CCDC 1844390'
_audit_update_record             
;
2018-05-19 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_audit_creation_date             2018-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H9 N3 O'
_chemical_formula_sum            'C13 H9 N3 O'
_chemical_formula_weight         223.23
_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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   13.042
_cell_length_b                   5.681
_cell_length_c                   14.602
_cell_angle_alpha                90
_cell_angle_beta                 98.86
_cell_angle_gamma                90
_cell_volume                     1069.0
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1876
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.4910
_cell_measurement_theta_min      3.3910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11018
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        24.812
_diffrn_reflns_theta_max         24.812
_diffrn_reflns_theta_min         1.580
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1187
_reflns_number_total             1780
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         1.186
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.1114
_refine_ls_restrained_S_all      1.102
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2549
_refine_ls_wR_factor_ref         0.2965
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), N2(H2A)
;
_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
C1 C 1.3544(3) 0.1707(9) 0.2702(3) 0.0375(11) Uani 1 1 d . . . . .
H1 H 1.4204 0.1259 0.2982 0.045 Uiso 1 1 calc R . . . .
C2 C 1.2717(4) 0.0177(8) 0.2706(3) 0.0368(11) Uani 1 1 d . . . . .
H2 H 1.2821 -0.1265 0.3008 0.044 Uiso 1 1 calc R . . . .
C3 C 1.1740(3) 0.0785(7) 0.2265(3) 0.0341(11) Uani 1 1 d . . . . .
H3 H 1.1191 -0.0265 0.2253 0.041 Uiso 1 1 calc R . . . .
C4 C 1.1581(3) 0.2945(8) 0.1844(3) 0.0310(11) Uani 1 1 d . . . . .
C5 C 1.2410(4) 0.4513(8) 0.1863(3) 0.0355(11) Uani 1 1 d . . . . .
H5 H 1.2296 0.5987 0.1589 0.043 Uiso 1 1 calc R . . . .
C6 C 1.3398(3) 0.3901(8) 0.2282(3) 0.0384(12) Uani 1 1 d . . . . .
H6 H 1.3951 0.4934 0.2284 0.046 Uiso 1 1 calc R . . . .
C7 C 1.0541(3) 0.3847(8) 0.1386(3) 0.0316(10) Uani 1 1 d . . . . .
C8 C 0.8821(3) 0.2417(7) 0.0636(3) 0.0259(10) Uani 1 1 d . . . . .
C9 C 0.8240(3) 0.4392(7) 0.0771(3) 0.0328(10) Uani 1 1 d . . . . .
H9 H 0.8545 0.5692 0.1091 0.039 Uiso 1 1 calc R . . . .
C10 C 0.7204(3) 0.4376(7) 0.0420(3) 0.0330(11) Uani 1 1 d . . . . .
H10 H 0.6788 0.5655 0.0515 0.040 Uiso 1 1 calc R . . . .
C11 C 0.6778(3) 0.2422(6) -0.0081(3) 0.0250(10) Uani 1 1 d . . . . .
C12 C 0.7426(3) 0.0541(7) -0.0185(3) 0.0332(11) Uani 1 1 d . . . . .
H12 H 0.7141 -0.0762 -0.0516 0.040 Uiso 1 1 calc R . . . .
C13 C 0.5709(3) 0.2362(7) -0.0486(3) 0.0308(11) Uani 1 1 d . . . . .
N1 N 0.8423(3) 0.0489(6) 0.0160(2) 0.0356(10) Uani 1 1 d . . . . .
N2 N 0.9865(3) 0.2194(7) 0.1011(2) 0.0341(10) Uani 1 1 d . . . . .
H2A H 1.0113 0.0794 0.1002 0.041 Uiso 1 1 calc R . . . .
N3 N 0.4851(3) 0.2374(6) -0.0829(3) 0.0424(11) Uani 1 1 d . . . . .
O1 O 1.0327(2) 0.5923(6) 0.1360(2) 0.0477(10) 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
C1 H1 0.9300 . ?
C1 C2 1.386(7) . ?
C1 C6 1.389(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(6) . ?
C4 C5 1.398(6) . ?
C4 C7 1.506(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(6) . ?
C6 H6 0.9300 . ?
C7 N2 1.346(6) . ?
C7 O1 1.211(5) . ?
C8 C9 1.384(6) . ?
C8 N1 1.357(5) . ?
C8 N2 1.393(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(5) . ?
C11 C12 1.384(6) . ?
C11 C13 1.429(6) . ?
C12 H12 0.9300 . ?
C12 N1 1.321(6) . ?
C13 N3 1.154(6) . ?
N2 H2A 0.8600 . ?

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
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.7(4) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 C7 124.5(4) . . ?
C5 C4 C7 115.6(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.8 . . ?
C5 C6 C1 118.5(4) . . ?
C5 C6 H6 120.8 . . ?
N2 C7 C4 115.6(4) . . ?
O1 C7 C4 122.2(4) . . ?
O1 C7 N2 122.2(4) . . ?
C9 C8 N2 122.7(4) . . ?
N1 C8 C9 123.6(4) . . ?
N1 C8 N2 113.7(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.1(4) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(4) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C13 121.3(4) . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 C13 120.6(3) . . ?
C11 C12 H12 118.1 . . ?
N1 C12 C11 123.9(4) . . ?
N1 C12 H12 118.1 . . ?
N3 C13 C11 177.9(5) . . ?
C12 N1 C8 117.0(4) . . ?
C7 N2 C8 129.5(4) . . ?
C7 N2 H2A 115.2 . . ?
C8 N2 H2A 115.2 . . ?

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
C1 C2 C3 C4 -2.0(6) . . . . ?
C2 C1 C6 C5 -0.6(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C2 C3 C4 C7 -176.7(4) . . . . ?
C3 C4 C5 C6 1.5(6) . . . . ?
C3 C4 C7 N2 -30.4(6) . . . . ?
C3 C4 C7 O1 149.4(5) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C4 C7 N2 C8 172.1(4) . . . . ?
C5 C4 C7 N2 152.6(4) . . . . ?
C5 C4 C7 O1 -27.6(6) . . . . ?
C6 C1 C2 C3 2.2(7) . . . . ?
C7 C4 C5 C6 178.6(4) . . . . ?
C8 C9 C10 C11 -1.9(6) . . . . ?
C9 C8 N1 C12 -0.1(6) . . . . ?
C9 C8 N2 C7 -14.3(7) . . . . ?
C9 C10 C11 C12 1.4(6) . . . . ?
C9 C10 C11 C13 -177.9(4) . . . . ?
C10 C11 C12 N1 -0.2(6) . . . . ?
C11 C12 N1 C8 -0.4(6) . . . . ?
C13 C11 C12 N1 179.1(4) . . . . ?
N1 C8 C9 C10 1.3(6) . . . . ?
N1 C8 N2 C7 168.1(4) . . . . ?
N2 C8 C9 C10 -176.0(4) . . . . ?
N2 C8 N1 C12 177.4(4) . . . . ?
O1 C7 N2 C8 -7.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
