# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_temps3new
_database_code_depnum_ccdc_archive 'CCDC 1556507'
_audit_update_record             
;
2017-06-16 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N3 O'
_chemical_formula_weight         199.21

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.7147(4)
_cell_length_b                   8.3019(6)
_cell_length_c                   20.1261(14)
_cell_angle_alpha                90
_cell_angle_beta                 94.120(5)
_cell_angle_gamma                90
_cell_volume                     952.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11185
_cell_measurement_theta_min      2.029
_cell_measurement_theta_max      25.242

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10738
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.029
_diffrn_reflns_theta_max         26.002
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1875
_reflns_number_gt                1508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'X-Area (STOE, 2010)'
_computing_cell_refinement       'X-Area (STOE, 2010)'
_computing_data_reduction        'X-Area (STOE, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond (Brandenburg)'
_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)+(0.0446P)²+0.1674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1875
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C1 C 0.6248(3) 0.3127(2) 0.55857(8) 0.0437(4) Uani 1 1 d . . . . .
O1 O 0.8240(2) 0.31707(17) 0.58563(6) 0.0633(4) Uani 1 1 d . . . . .
N1 N 0.4334(2) 0.37724(16) 0.58456(7) 0.0456(4) Uani 1 1 d . . . . .
H1 H 0.3018 0.3628 0.5619 0.055 Uiso 1 1 calc R U . . .
C2 C 0.4240(3) 0.46483(18) 0.64413(8) 0.0404(4) Uani 1 1 d . . . . .
C3 C 0.6061(3) 0.4709(2) 0.69329(8) 0.0561(5) Uani 1 1 d . . . . .
H3 H 0.7413 0.4121 0.6871 0.067 Uiso 1 1 calc R U . . .
N2 N 0.5977(3) 0.5569(2) 0.74902(7) 0.0617(5) Uani 1 1 d . . . . .
C4 C 0.4025(3) 0.6386(2) 0.75775(8) 0.0524(4) Uani 1 1 d . . . . .
H4 H 0.3956 0.7002 0.7961 0.063 Uiso 1 1 calc R U . . .
C5 C 0.2106(3) 0.6362(2) 0.71270(9) 0.0544(5) Uani 1 1 d . . . . .
H5 H 0.0753 0.6928 0.7211 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2214(3) 0.5487(2) 0.65483(9) 0.0486(4) Uani 1 1 d . . . . .
H6 H 0.0940 0.5462 0.6234 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5749(3) 0.22914(19) 0.49315(8) 0.0409(4) Uani 1 1 d . . . . .
N3 N 0.3601(2) 0.24564(18) 0.46270(7) 0.0474(4) Uani 1 1 d . . . . .
C8 C 0.3194(3) 0.1682(2) 0.40535(8) 0.0526(5) Uani 1 1 d . . . . .
H8 H 0.1729 0.1807 0.3827 0.063 Uiso 1 1 calc R U . . .
C9 C 0.4804(3) 0.0705(2) 0.37728(8) 0.0532(5) Uani 1 1 d . . . . .
H9 H 0.4420 0.0165 0.3375 0.064 Uiso 1 1 calc R U . . .
C10 C 0.6989(3) 0.0549(2) 0.40958(9) 0.0543(5) Uani 1 1 d . . . . .
H10 H 0.8117 -0.0104 0.3922 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7482(3) 0.1375(2) 0.46813(8) 0.0474(4) Uani 1 1 d . . . . .
H11 H 0.8963 0.1314 0.4904 0.057 Uiso 1 1 calc R U . . .


_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 O1 1.227(2) . ?
C1 N1 1.356(2) . ?
C1 C7 1.497(2) . ?
N1 C2 1.407(2) . ?
C2 C6 1.381(2) . ?
C2 C3 1.385(2) . ?
C3 N2 1.333(2) . ?
N2 C4 1.328(2) . ?
C4 C5 1.372(3) . ?
C5 C6 1.378(2) . ?
C7 N3 1.339(2) . ?
C7 C11 1.373(2) . ?
N3 C8 1.327(2) . ?
C8 C9 1.378(3) . ?
C9 C10 1.372(3) . ?
C10 C11 1.375(2) . ?

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
O1 C1 N1 124.44(15) . . ?
O1 C1 C7 121.08(15) . . ?
N1 C1 C7 114.47(14) . . ?
C1 N1 C2 127.91(14) . . ?
C6 C2 C3 117.76(15) . . ?
C6 C2 N1 118.52(14) . . ?
C3 C2 N1 123.72(15) . . ?
N2 C3 C2 123.36(17) . . ?
C4 N2 C3 117.80(16) . . ?
N2 C4 C5 122.99(16) . . ?
C4 C5 C6 118.93(16) . . ?
C5 C6 C2 119.12(16) . . ?
N3 C7 C11 123.40(15) . . ?
N3 C7 C1 117.75(14) . . ?
C11 C7 C1 118.83(14) . . ?
C8 N3 C7 116.50(15) . . ?
N3 C8 C9 124.16(16) . . ?
C10 C9 C8 118.21(16) . . ?
C9 C10 C11 118.87(17) . . ?
C7 C11 C10 118.80(16) . . ?

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
N1 H1 N3 0.86 2.27 2.6902(19) 110.4 .
C3 H3 O1 0.93 2.27 2.875(2) 122.1 .
C6 H6 O1 0.93 2.53 3.216(2) 130.7 1_455
C9 H9 N2 0.93 2.63 3.428(2) 144.5 4_565

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.028

_shelxl_version_number           2014-3

