# 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_wanghb211
_database_code_depnum_ccdc_archive 'CCDC 1585181'
_audit_update_record             
;
2017-11-13 deposited with the CCDC.
2018-03-27 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 H14 N4 O'
_chemical_formula_weight         254.28

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/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                   7.753(2)
_cell_length_b                   14.532(4)
_cell_length_c                   11.144(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.574(6)
_cell_angle_gamma                90
_cell_volume                     1241.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3469
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.41

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      1.360
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.088
_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_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            7080
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2437
_reflns_number_gt                1972
_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    '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)+(0.0459P)²+0.2178P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2437
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_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
O1 O 0.08830(13) 0.82432(7) 1.00706(9) 0.0565(3) Uani 1 1 d . . . . .
N1 N 0.28522(16) 0.90477(8) 0.70306(9) 0.0529(3) Uani 1 1 d . . . . .
N2 N 0.36706(14) 1.04657(7) 0.78430(9) 0.0448(3) Uani 1 1 d . . . . .
N3 N 0.44570(15) 1.19144(8) 0.85393(10) 0.0497(3) Uani 1 1 d . . . . .
N4 N 0.13471(15) 0.79867(8) 0.81293(10) 0.0486(3) Uani 1 1 d . . . . .
C1 C 0.45588(18) 1.25308(10) 0.94052(12) 0.0512(3) Uani 1 1 d . . . . .
H1A H 0.5012 1.3104 0.9250 0.061 Uiso 1 1 calc R U . . .
C2 C 0.40404(18) 1.23988(10) 1.05503(13) 0.0522(4) Uani 1 1 d . . . . .
H2A H 0.4164 1.2866 1.1127 0.063 Uiso 1 1 calc R U . . .
C3 C 0.33583(17) 1.15759(10) 1.07901(11) 0.0485(3) Uani 1 1 d . . . . .
H3A H 0.3012 1.1466 1.1541 0.058 Uiso 1 1 calc R U . . .
C4 C 0.31754(15) 1.08826(9) 0.98881(10) 0.0397(3) Uani 1 1 d . . . . .
C5 C 0.37628(16) 1.10779(9) 0.87617(10) 0.0401(3) Uani 1 1 d . . . . .
C6 C 0.24428(16) 1.00214(9) 1.00229(11) 0.0416(3) Uani 1 1 d . . . . .
H6A H 0.2054 0.9865 1.0746 0.050 Uiso 1 1 calc R U . . .
C7 C 0.22986(15) 0.94040(9) 0.90811(10) 0.0390(3) Uani 1 1 d . . . . .
C8 C 0.29563(16) 0.96561(9) 0.79993(10) 0.0412(3) Uani 1 1 d . . . . .
C9 C 0.14643(16) 0.85124(9) 0.91731(11) 0.0431(3) Uani 1 1 d . . . . .
C10 C 0.2081(2) 0.82831(10) 0.71500(12) 0.0545(4) Uani 1 1 d . . . . .
H10A H 0.2008 0.7880 0.6496 0.065 Uiso 1 1 calc R U . . .
C11 C 0.05460(19) 0.70656(10) 0.80921(14) 0.0556(4) Uani 1 1 d . . . . .
H11A H 0.0022 0.6928 0.7266 0.067 Uiso 1 1 calc R U . . .
H11B H -0.0374 0.7064 0.8594 0.067 Uiso 1 1 calc R U . . .
C12 C 0.18577(19) 0.63257(10) 0.85330(13) 0.0545(4) Uani 1 1 d . . . . .
H12A H 0.2795 0.6341 0.8046 0.065 Uiso 1 1 calc R U . . .
H12B H 0.2357 0.6455 0.9366 0.065 Uiso 1 1 calc R U . . .
C13 C 0.1067(2) 0.53778(10) 0.84665(15) 0.0598(4) Uani 1 1 d . . . . .
H13A H 0.0613 0.5238 0.7628 0.072 Uiso 1 1 calc R U . . .
H13B H 0.0096 0.5371 0.8924 0.072 Uiso 1 1 calc R U . . .
C14 C 0.2354(3) 0.46417(12) 0.89565(18) 0.0793(5) Uani 1 1 d . . . . .
H14A H 0.1785 0.4053 0.8893 0.119 Uiso 1 1 calc R U . . .
H14B H 0.3306 0.4635 0.8496 0.119 Uiso 1 1 calc R U . . .
H14C H 0.2789 0.4768 0.9792 0.119 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
O1 C9 1.2211(15) . ?
N1 C10 1.2783(18) . ?
N1 C8 1.3884(16) . ?
N2 C8 1.3229(17) . ?
N2 C5 1.3502(16) . ?
N3 C1 1.3104(17) . ?
N3 C5 1.3671(17) . ?
N4 C10 1.3729(18) . ?
N4 C9 1.3834(17) . ?
N4 C11 1.4736(18) . ?
C1 C2 1.4071(19) . ?
C2 C3 1.350(2) . ?
C3 C4 1.4154(18) . ?
C4 C6 1.3918(18) . ?
C4 C5 1.4263(17) . ?
C6 C7 1.3726(18) . ?
C7 C8 1.4251(17) . ?
C7 C9 1.4586(19) . ?
C11 C12 1.511(2) . ?
C12 C13 1.505(2) . ?
C13 C14 1.508(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
C10 N1 C8 116.52(11) . . ?
C8 N2 C5 117.52(11) . . ?
C1 N3 C5 117.16(11) . . ?
C10 N4 C9 120.81(12) . . ?
C10 N4 C11 119.04(12) . . ?
C9 N4 C11 119.99(11) . . ?
N3 C1 C2 125.50(13) . . ?
C3 C2 C1 118.26(13) . . ?
C2 C3 C4 119.38(12) . . ?
C6 C4 C3 124.25(11) . . ?
C6 C4 C5 117.58(11) . . ?
C3 C4 C5 118.18(12) . . ?
N2 C5 N3 115.23(11) . . ?
N2 C5 C4 123.27(12) . . ?
N3 C5 C4 121.50(11) . . ?
C7 C6 C4 119.56(11) . . ?
C6 C7 C8 118.70(12) . . ?
C6 C7 C9 120.89(11) . . ?
C8 C7 C9 120.41(11) . . ?
N2 C8 N1 116.16(11) . . ?
N2 C8 C7 123.35(11) . . ?
N1 C8 C7 120.49(12) . . ?
O1 C9 N4 121.73(13) . . ?
O1 C9 C7 124.32(12) . . ?
N4 C9 C7 113.93(11) . . ?
N1 C10 N4 127.68(13) . . ?
N4 C11 C12 112.14(12) . . ?
C13 C12 C11 112.69(12) . . ?
C12 C13 C14 112.87(14) . . ?

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
C5 N3 C1 C2 1.1(2) . . . . ?
N3 C1 C2 C3 -0.8(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C6 -177.97(12) . . . . ?
C2 C3 C4 C5 1.42(19) . . . . ?
C8 N2 C5 N3 -177.86(11) . . . . ?
C8 N2 C5 C4 1.75(18) . . . . ?
C1 N3 C5 N2 179.54(11) . . . . ?
C1 N3 C5 C4 -0.07(18) . . . . ?
C6 C4 C5 N2 -1.31(18) . . . . ?
C3 C4 C5 N2 179.26(11) . . . . ?
C6 C4 C5 N3 178.28(11) . . . . ?
C3 C4 C5 N3 -1.16(18) . . . . ?
C3 C4 C6 C7 178.82(11) . . . . ?
C5 C4 C6 C7 -0.58(17) . . . . ?
C4 C6 C7 C8 1.86(17) . . . . ?
C4 C6 C7 C9 -177.14(10) . . . . ?
C5 N2 C8 N1 178.89(11) . . . . ?
C5 N2 C8 C7 -0.35(18) . . . . ?
C10 N1 C8 N2 -176.41(12) . . . . ?
C10 N1 C8 C7 2.86(19) . . . . ?
C6 C7 C8 N2 -1.46(18) . . . . ?
C9 C7 C8 N2 177.55(11) . . . . ?
C6 C7 C8 N1 179.33(11) . . . . ?
C9 C7 C8 N1 -1.66(18) . . . . ?
C10 N4 C9 O1 -176.94(12) . . . . ?
C11 N4 C9 O1 -1.64(19) . . . . ?
C10 N4 C9 C7 4.24(17) . . . . ?
C11 N4 C9 C7 179.53(11) . . . . ?
C6 C7 C9 O1 -1.69(19) . . . . ?
C8 C7 C9 O1 179.33(12) . . . . ?
C6 C7 C9 N4 177.10(11) . . . . ?
C8 C7 C9 N4 -1.88(16) . . . . ?
C8 N1 C10 N4 -0.4(2) . . . . ?
C9 N4 C10 N1 -3.4(2) . . . . ?
C11 N4 C10 N1 -178.75(15) . . . . ?
C10 N4 C11 C12 87.19(16) . . . . ?
C9 N4 C11 C12 -88.18(15) . . . . ?
N4 C11 C12 C13 -178.37(12) . . . . ?
C11 C12 C13 C14 -177.50(13) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.033

