# 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_20170906LMF_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1573954'
_audit_update_record             
;
2017-09-12 deposited with the CCDC.
2018-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N4'
_chemical_formula_weight         184.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.3504(4)
_cell_length_b                   24.437(2)
_cell_length_c                   8.5476(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.442(2)
_cell_angle_gamma                90
_cell_volume                     887.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4455
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      27.62
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.985
_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      153(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            5901
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.495
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1551
_reflns_number_gt                1419
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0492P)²+0.4365P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.165(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.5822(4) 0.34049(7) 0.42060(19) 0.0292(4) Uani 1 1 d . . . . .
H1 H 0.677560 0.306911 0.401148 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5860(4) 0.38355(8) 0.31713(19) 0.0322(5) Uani 1 1 d . . . . .
H2 H 0.679820 0.380389 0.226951 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4464(4) 0.43151(8) 0.3511(2) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.445999 0.461972 0.282015 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3242(4) 0.39255(6) 0.56845(18) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.0293(4) 0.44496(7) 0.7334(2) 0.0272(4) Uani 1 1 d . . . . .
H5 H -0.005227 0.476810 0.668204 0.033 Uiso 1 1 calc R U . . .
C6 C -0.0651(4) 0.43769(7) 0.8727(2) 0.0292(4) Uani 1 1 d . . . . .
H6 H -0.178537 0.463241 0.922211 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0367(4) 0.38477(7) 0.93162(18) 0.0275(4) Uani 1 1 d . . . . .
H7 H 0.003388 0.368899 1.028074 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1892(4) 0.36080(6) 0.82682(17) 0.0233(4) Uani 1 1 d . . . . .
C9 C 0.3310(4) 0.30452(7) 0.84089(18) 0.0256(4) Uani 1 1 d . . . . .
H9A H 0.539591 0.306109 0.812363 0.031 Uiso 1 1 calc R U . . .
H9B H 0.363233 0.292165 0.953564 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1327(4) 0.26448(7) 0.73695(19) 0.0259(4) Uani 1 1 d . . . . .
N1 N 0.4492(3) 0.34419(6) 0.54759(15) 0.0264(4) Uani 1 1 d . . . . .
N2 N 0.3122(3) 0.43709(6) 0.47638(17) 0.0297(4) Uani 1 1 d . . . . .
N3 N 0.1853(3) 0.39801(5) 0.70165(15) 0.0226(4) Uani 1 1 d . . . . .
N4 N -0.0276(4) 0.23304(6) 0.66051(18) 0.0362(4) 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 N1 1.339(2) . ?
C1 C2 1.377(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.332(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.329(2) . ?
C4 N2 1.338(2) . ?
C4 N3 1.405(2) . ?
C5 C6 1.352(2) . ?
C5 N3 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.423(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(2) . ?
C7 H7 0.9500 . ?
C8 N3 1.401(2) . ?
C8 C9 1.502(2) . ?
C9 C10 1.470(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N4 1.144(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
N1 C1 C2 122.41(16) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 116.58(16) . . ?
C1 C2 H2 121.7 . . ?
C3 C2 H2 121.7 . . ?
N2 C3 C2 123.03(16) . . ?
N2 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N1 C4 N2 127.57(15) . . ?
N1 C4 N3 116.93(14) . . ?
N2 C4 N3 115.49(14) . . ?
C6 C5 N3 108.49(14) . . ?
C6 C5 H5 125.8 . . ?
N3 C5 H5 125.8 . . ?
C5 C6 C7 107.50(15) . . ?
C5 C6 H6 126.3 . . ?
C7 C6 H6 126.3 . . ?
C8 C7 C6 108.52(14) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
C7 C8 N3 107.26(14) . . ?
C7 C8 C9 126.39(14) . . ?
N3 C8 C9 126.34(14) . . ?
C10 C9 C8 112.57(14) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
N4 C10 C9 177.42(18) . . ?
C4 N1 C1 115.47(14) . . ?
C3 N2 C4 114.92(15) . . ?
C5 N3 C8 108.23(13) . . ?
C5 N3 C4 123.35(13) . . ?
C8 N3 C4 128.34(14) . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.055



