# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20160725jnd_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1858811'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 N3 O'
_chemical_formula_weight         234.23

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                   5.7918(6)
_cell_length_b                   13.7380(14)
_cell_length_c                   13.4519(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.436(4)
_cell_angle_gamma                90
_cell_volume                     1049.09(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1866
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      26.61

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5889
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1839
_reflns_number_gt                1348
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0608P)²+0.7531P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1839
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.7778(4) 0.76461(18) 0.34888(17) 0.0187(6) Uani 1 1 d . . . . .
C2 C 0.8918(4) 0.80972(18) 0.27912(18) 0.0198(6) Uani 1 1 d . . . . .
H2 H 0.8322 0.8024 0.2101 0.024 Uiso 1 1 calc R U . . .
C3 C 1.0903(5) 0.86474(19) 0.31079(19) 0.0240(6) Uani 1 1 d . . . . .
H3 H 1.1645 0.8947 0.2637 0.029 Uiso 1 1 calc R U . . .
C4 C 1.1796(5) 0.8752(2) 0.41454(19) 0.0261(7) Uani 1 1 d . . . . .
H4 H 1.3133 0.9131 0.4362 0.031 Uiso 1 1 calc R U . . .
C5 C 1.0734(5) 0.8306(2) 0.48522(19) 0.0257(7) Uani 1 1 d . . . . .
H5 H 1.1355 0.8381 0.5540 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8737(5) 0.77441(19) 0.45361(17) 0.0198(6) Uani 1 1 d . . . . .
C7 C 0.5697(4) 0.70634(18) 0.32111(17) 0.0172(6) Uani 1 1 d . . . . .
C8 C 0.2603(5) 0.62846(19) 0.24769(18) 0.0184(6) Uani 1 1 d . . . . .
C9 C 0.0729(5) 0.58858(19) 0.17851(19) 0.0234(6) Uani 1 1 d . . . . .
H9 H 0.0564 0.6004 0.1094 0.028 Uiso 1 1 calc R U . . .
C10 C -0.0870(5) 0.5314(2) 0.21479(19) 0.0262(7) Uani 1 1 d . . . . .
H10 H -0.2134 0.5047 0.1695 0.031 Uiso 1 1 calc R U . . .
C11 C -0.0632(5) 0.5126(2) 0.31864(19) 0.0266(7) Uani 1 1 d . . . . .
H11 H -0.1743 0.4738 0.3410 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1223(5) 0.55050(19) 0.38847(19) 0.0231(6) Uani 1 1 d . . . . .
H12 H 0.1394 0.5379 0.4575 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2817(5) 0.60824(18) 0.35102(18) 0.0199(6) Uani 1 1 d . . . . .
C14 C 0.5729(5) 0.66893(19) 0.50209(18) 0.0208(6) Uani 1 1 d . . . . .
N1 N 0.7667(4) 0.72681(16) 0.52492(14) 0.0219(5) Uani 1 1 d . . . . .
N2 N 0.4829(4) 0.65923(15) 0.39780(14) 0.0183(5) Uani 1 1 d . . . . .
N3 N 0.4406(4) 0.68958(15) 0.23061(14) 0.0192(5) Uani 1 1 d . . . . .
O1 O 0.4795(3) 0.62918(14) 0.56457(12) 0.0279(5) 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 C2 1.395(3) . ?
C1 C6 1.415(3) . ?
C1 C7 1.433(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.403(3) . ?
C7 N3 1.317(3) . ?
C7 N2 1.393(3) . ?
C8 C9 1.394(4) . ?
C8 N3 1.394(3) . ?
C8 C13 1.399(3) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.400(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9300 . ?
C13 N2 1.398(3) . ?
C14 O1 1.215(3) . ?
C14 N1 1.360(3) . ?
C14 N2 1.403(3) . ?

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 C6 118.9(2) . . ?
C2 C1 C7 123.9(2) . . ?
C6 C1 C7 117.2(2) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 N1 120.3(2) . . ?
C5 C6 C1 119.9(2) . . ?
N1 C6 C1 119.8(2) . . ?
N3 C7 N2 112.4(2) . . ?
N3 C7 C1 129.3(2) . . ?
N2 C7 C1 118.3(2) . . ?
C9 C8 N3 129.5(2) . . ?
C9 C8 C13 119.3(2) . . ?
N3 C8 C13 111.2(2) . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 116.9(2) . . ?
C11 C12 H12 121.5 . . ?
C13 C12 H12 121.5 . . ?
C12 C13 N2 132.8(2) . . ?
C12 C13 C8 122.7(2) . . ?
N2 C13 C8 104.5(2) . . ?
O1 C14 N1 124.5(2) . . ?
O1 C14 N2 121.4(2) . . ?
N1 C14 N2 114.1(2) . . ?
C14 N1 C6 125.1(2) . . ?
C7 N2 C13 106.89(19) . . ?
C7 N2 C14 125.4(2) . . ?
C13 N2 C14 127.5(2) . . ?
C7 N3 C8 105.1(2) . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.057



