# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cd15008
_audit_block_doi                 10.5517/ccdc.csd.cc215l2x
_database_code_depnum_ccdc_archive 'CCDC 1882198'
loop_
_audit_author_name
_audit_author_address
'Naiguo Xing'
;Sichuan University
China
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N3'
_chemical_formula_weight         287.35

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                   8.8979(10)
_cell_length_b                   16.1189(18)
_cell_length_c                   10.7902(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.182(3)
_cell_angle_gamma                90
_cell_volume                     1531.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1539
_cell_measurement_theta_min      4.625
_cell_measurement_theta_max      44.963

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9181
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3004
_reflns_number_gt                2142
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0573P)²+0.2190P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0055(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
N1 N 0.84206(18) 0.78307(10) 0.29068(16) 0.0464(4) Uani 1 1 d . . . . .
N2 N 0.78285(18) 1.06535(9) 0.34004(15) 0.0443(4) Uani 1 1 d . . . . .
N3 N 0.98841(18) 1.12862(9) 0.26113(15) 0.0444(4) Uani 1 1 d . . . . .
C1 C 0.7438(2) 0.79841(10) 0.37577(18) 0.0409(5) Uani 1 1 d . . . . .
C2 C 0.6613(2) 0.74361(12) 0.4386(2) 0.0549(6) Uani 1 1 d . . . . .
H2 H 0.6647 0.6867 0.4251 0.066 Uiso 1 1 calc R U . . .
C3 C 0.5742(3) 0.77680(14) 0.5217(2) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.5184 0.7415 0.5660 0.076 Uiso 1 1 calc R U . . .
C4 C 0.5676(3) 0.86204(13) 0.5411(2) 0.0592(6) Uani 1 1 d . . . . .
H4 H 0.5078 0.8826 0.5981 0.071 Uiso 1 1 calc R U . . .
C5 C 0.6476(2) 0.91611(11) 0.47773(19) 0.0464(5) Uani 1 1 d . . . . .
H5 H 0.6412 0.9730 0.4904 0.056 Uiso 1 1 calc R U . . .
C6 C 0.73902(19) 0.88457(10) 0.39383(17) 0.0375(4) Uani 1 1 d . . . . .
C7 C 0.8409(2) 0.92095(10) 0.31679(17) 0.0377(4) Uani 1 1 d . . . . .
C8 C 0.8997(2) 0.85603(11) 0.25717(19) 0.0440(5) Uani 1 1 d . . . . .
H8 H 0.9697 0.8614 0.2013 0.053 Uiso 1 1 calc R U . . .
C9 C 0.8714(2) 1.00908(10) 0.30645(17) 0.0380(4) Uani 1 1 d . . . . .
C10 C 0.8473(2) 1.14521(10) 0.31300(18) 0.0420(5) Uani 1 1 d . . . . .
C11 C 1.0021(2) 1.04987(10) 0.25658(18) 0.0388(4) Uani 1 1 d . . . . .
C12 C 1.1302(2) 1.00979(11) 0.20585(18) 0.0410(5) Uani 1 1 d . . . . .
C13 C 1.1628(2) 1.03391(13) 0.0892(2) 0.0511(5) Uani 1 1 d . . . . .
H13 H 1.1036 1.0742 0.0439 0.061 Uiso 1 1 calc R U . . .
C14 C 1.2822(3) 0.99851(15) 0.0401(2) 0.0657(7) Uani 1 1 d . . . . .
H14 H 1.3022 1.0141 -0.0390 0.079 Uiso 1 1 calc R U . . .
C15 C 1.3712(3) 0.94057(15) 0.1074(3) 0.0695(7) Uani 1 1 d . . . . .
H15 H 1.4522 0.9171 0.0741 0.083 Uiso 1 1 calc R U . . .
C16 C 1.3422(2) 0.91660(13) 0.2239(3) 0.0617(6) Uani 1 1 d . . . . .
H16 H 1.4041 0.8776 0.2697 0.074 Uiso 1 1 calc R U . . .
C17 C 1.2204(2) 0.95064(12) 0.2729(2) 0.0498(5) Uani 1 1 d . . . . .
H17 H 1.1993 0.9337 0.3509 0.060 Uiso 1 1 calc R U . . .
C18 C 0.8817(3) 1.19512(12) 0.4331(2) 0.0536(5) Uani 1 1 d . . . . .
H18A H 0.7895 1.2041 0.4678 0.080 Uiso 1 1 calc R U . . .
H18B H 0.9247 1.2476 0.4152 0.080 Uiso 1 1 calc R U . . .
H18C H 0.9526 1.1652 0.4921 0.080 Uiso 1 1 calc R U . . .
C19 C 0.7375(3) 1.19047(12) 0.2155(2) 0.0578(6) Uani 1 1 d . . . . .
H19A H 0.7192 1.1576 0.1407 0.087 Uiso 1 1 calc R U . . .
H19B H 0.7803 1.2429 0.1967 0.087 Uiso 1 1 calc R U . . .
H19C H 0.6434 1.1996 0.2473 0.087 Uiso 1 1 calc R U . . .
H1 H 0.876(2) 0.7298(14) 0.271(2) 0.065(6) Uiso 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
N1 C8 1.353(2) . ?
N1 C1 1.377(2) . ?
N1 H1 0.94(2) . ?
N2 C9 1.287(2) . ?
N2 C10 1.456(2) . ?
N3 C11 1.277(2) . ?
N3 C10 1.470(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.404(2) . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(2) . ?
C7 C8 1.371(2) . ?
C7 C9 1.453(2) . ?
C8 H8 0.9300 . ?
C9 C11 1.501(2) . ?
C10 C19 1.517(3) . ?
C10 C18 1.519(3) . ?
C11 C12 1.481(2) . ?
C12 C17 1.382(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C8 N1 C1 108.84(16) . . ?
C8 N1 H1 125.9(13) . . ?
C1 N1 H1 124.4(13) . . ?
C9 N2 C10 107.02(15) . . ?
C11 N3 C10 106.67(15) . . ?
N1 C1 C2 129.99(17) . . ?
N1 C1 C6 107.76(16) . . ?
C2 C1 C6 122.25(18) . . ?
C3 C2 C1 117.30(18) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.43(19) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.98(17) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 118.84(17) . . ?
C5 C6 C7 134.36(16) . . ?
C1 C6 C7 106.78(16) . . ?
C8 C7 C6 105.91(15) . . ?
C8 C7 C9 128.48(17) . . ?
C6 C7 C9 125.61(16) . . ?
N1 C8 C7 110.70(17) . . ?
N1 C8 H8 124.6 . . ?
C7 C8 H8 124.6 . . ?
N2 C9 C7 122.62(16) . . ?
N2 C9 C11 109.20(15) . . ?
C7 C9 C11 128.18(16) . . ?
N2 C10 N3 107.31(14) . . ?
N2 C10 C19 109.35(16) . . ?
N3 C10 C19 108.91(16) . . ?
N2 C10 C18 109.56(15) . . ?
N3 C10 C18 109.97(16) . . ?
C19 C10 C18 111.63(16) . . ?
N3 C11 C12 122.04(16) . . ?
N3 C11 C9 109.79(16) . . ?
C12 C11 C9 128.16(15) . . ?
C17 C12 C13 119.17(19) . . ?
C17 C12 C11 121.84(18) . . ?
C13 C12 C11 118.96(17) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.1(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C8 N1 C1 C2 -178.1(2) . . . . ?
C8 N1 C1 C6 1.0(2) . . . . ?
N1 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -177.1(2) . . . . ?
N1 C1 C6 C5 -179.39(17) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C7 -0.8(2) . . . . ?
C2 C1 C6 C7 178.41(18) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
C1 C6 C7 C8 0.3(2) . . . . ?
C5 C6 C7 C9 -1.7(3) . . . . ?
C1 C6 C7 C9 -179.99(17) . . . . ?
C1 N1 C8 C7 -0.8(2) . . . . ?
C6 C7 C8 N1 0.3(2) . . . . ?
C9 C7 C8 N1 -179.39(18) . . . . ?
C10 N2 C9 C7 -178.49(17) . . . . ?
C10 N2 C9 C11 0.9(2) . . . . ?
C8 C7 C9 N2 161.40(19) . . . . ?
C6 C7 C9 N2 -18.2(3) . . . . ?
C8 C7 C9 C11 -17.9(3) . . . . ?
C6 C7 C9 C11 162.53(18) . . . . ?
C9 N2 C10 N3 -1.2(2) . . . . ?
C9 N2 C10 C19 116.77(18) . . . . ?
C9 N2 C10 C18 -120.59(18) . . . . ?
C11 N3 C10 N2 1.1(2) . . . . ?
C11 N3 C10 C19 -117.19(17) . . . . ?
C11 N3 C10 C18 120.19(17) . . . . ?
C10 N3 C11 C12 178.39(17) . . . . ?
C10 N3 C11 C9 -0.5(2) . . . . ?
N2 C9 C11 N3 -0.2(2) . . . . ?
C7 C9 C11 N3 179.11(18) . . . . ?
N2 C9 C11 C12 -179.08(18) . . . . ?
C7 C9 C11 C12 0.3(3) . . . . ?
N3 C11 C12 C17 127.4(2) . . . . ?
C9 C11 C12 C17 -53.9(3) . . . . ?
N3 C11 C12 C13 -50.9(3) . . . . ?
C9 C11 C12 C13 127.8(2) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C11 C12 C13 C14 179.26(18) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C11 C12 C17 C16 -177.88(17) . . . . ?
C15 C16 C17 C12 -1.3(3) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd214108
_audit_block_doi                 10.5517/ccdc.csd.cc206w8d
_database_code_depnum_ccdc_archive 'CCDC 1853653'
loop_
_audit_author_name
_audit_author_address
'Naiguo Xing'
;Sichuan University
China
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 F0.50 N2'
_chemical_formula_weight         180.72

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   9.8331(14)
_cell_length_b                   20.335(3)
_cell_length_c                   9.8331(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1966.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1587
_cell_measurement_theta_min      4.601
_cell_measurement_theta_max      50.458

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5677
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1892
_reflns_number_gt                1724
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.969

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0597P)²+0.3140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 672 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   1.5(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1892
_refine_ls_number_parameters     133
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.002
_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
F1 F 0.6308(7) 0.5209(3) 0.2174(9) 0.115(2) Uani 0.5 1 d . . P . .
N1 N 1.1057(3) 0.26382(13) 0.5385(3) 0.0436(7) Uani 1 1 d . . . . .
N2 N 0.8865(2) 0.28270(12) 0.5472(3) 0.0421(7) Uani 1 1 d . . . . .
C1 C 0.9853(3) 0.24543(15) 0.5927(4) 0.0425(8) Uani 1 1 d . . . . .
C2 C 0.9691(4) 0.1901(2) 0.6905(5) 0.0620(11) Uani 1 1 d . . . . .
H2A H 0.8752 0.1864 0.7164 0.093 Uiso 1 1 calc R U . . .
H2B H 1.0235 0.1982 0.7698 0.093 Uiso 1 1 calc R U . . .
H2C H 0.9980 0.1498 0.6483 0.093 Uiso 1 1 calc R U . . .
C3 C 1.0836(3) 0.31587(16) 0.4540(4) 0.0435(8) Uani 1 1 d . . . . .
C4 C 0.9463(3) 0.32747(15) 0.4588(4) 0.0389(7) Uani 1 1 d . . . . .
C5 C 0.8654(3) 0.37847(16) 0.3926(4) 0.0426(8) Uani 1 1 d . . . . .
C6 C 0.8994(4) 0.4041(2) 0.2662(4) 0.0602(10) Uani 1 1 d . . . . .
H6 H 0.9759 0.3884 0.2212 0.072 Uiso 1 1 calc R U . . .
C7 C 0.8211(5) 0.4526(2) 0.2063(5) 0.0705(12) Uani 1 1 d . . . . .
H7 H 0.8460 0.4698 0.1224 0.085 Uiso 1 1 calc R U . . .
C8 C 0.7067(5) 0.47511(19) 0.2710(6) 0.0694(12) Uani 1 1 d . . . . .
C9 C 0.6703(4) 0.4496(2) 0.3946(6) 0.0722(12) Uani 1 1 d . . . . .
H9 H 0.5921 0.4644 0.4381 0.087 Uiso 1 1 calc R U . . .
C10 C 0.7493(4) 0.40204(19) 0.4542(5) 0.0564(9) Uani 1 1 d . . . . .
H10 H 0.7239 0.3853 0.5385 0.068 Uiso 1 1 calc R U . . .
C11 C 1.1980(4) 0.3494(2) 0.3824(5) 0.0624(11) Uani 1 1 d . . . . .
H11A H 1.1740 0.3945 0.3655 0.094 Uiso 1 1 calc R U . . .
H11B H 1.2154 0.3277 0.2976 0.094 Uiso 1 1 calc R U . . .
H11C H 1.2781 0.3478 0.4381 0.094 Uiso 1 1 calc R U . . .
H1 H 1.193(4) 0.2466(18) 0.554(4) 0.047(9) Uiso 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
F1 C8 1.304(7) . ?
N1 C1 1.351(4) . ?
N1 C3 1.363(5) . ?
N1 H1 0.94(4) . ?
N2 C1 1.311(4) . ?
N2 C4 1.389(4) . ?
C1 C2 1.489(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C4 1.371(4) . ?
C3 C11 1.492(5) . ?
C4 C5 1.461(5) . ?
C5 C10 1.378(5) . ?
C5 C6 1.388(6) . ?
C6 C7 1.383(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(7) . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C1 N1 C3 108.4(3) . . ?
C1 N1 H1 129(2) . . ?
C3 N1 H1 122(2) . . ?
C1 N2 C4 106.2(3) . . ?
N2 C1 N1 110.8(3) . . ?
N2 C1 C2 125.3(3) . . ?
N1 C1 C2 123.9(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 105.6(3) . . ?
N1 C3 C11 121.5(3) . . ?
C4 C3 C11 132.8(3) . . ?
C3 C4 N2 109.0(3) . . ?
C3 C4 C5 130.0(3) . . ?
N2 C4 C5 120.9(3) . . ?
C10 C5 C6 117.6(3) . . ?
C10 C5 C4 120.1(3) . . ?
C6 C5 C4 122.3(3) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
F1 C8 C9 118.7(5) . . ?
F1 C8 C7 121.4(6) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C5 121.7(4) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C4 N2 C1 N1 0.1(4) . . . . ?
C4 N2 C1 C2 -179.8(3) . . . . ?
C3 N1 C1 N2 0.3(4) . . . . ?
C3 N1 C1 C2 -179.9(4) . . . . ?
C1 N1 C3 C4 -0.5(4) . . . . ?
C1 N1 C3 C11 177.5(3) . . . . ?
N1 C3 C4 N2 0.5(4) . . . . ?
C11 C3 C4 N2 -177.1(4) . . . . ?
N1 C3 C4 C5 177.7(3) . . . . ?
C11 C3 C4 C5 0.0(6) . . . . ?
C1 N2 C4 C3 -0.4(4) . . . . ?
C1 N2 C4 C5 -177.9(3) . . . . ?
C3 C4 C5 C10 -148.9(4) . . . . ?
N2 C4 C5 C10 27.9(5) . . . . ?
C3 C4 C5 C6 32.3(5) . . . . ?
N2 C4 C5 C6 -150.8(3) . . . . ?
C10 C5 C6 C7 1.5(6) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C5 C6 C7 C8 -1.2(7) . . . . ?
C6 C7 C8 F1 179.9(5) . . . . ?
C6 C7 C8 C9 0.0(7) . . . . ?
F1 C8 C9 C10 -179.1(5) . . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
C8 C9 C10 C5 -0.4(7) . . . . ?
C6 C5 C10 C9 -0.7(6) . . . . ?
C4 C5 C10 C9 -179.5(4) . . . . ?

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 N2 0.94(4) 2.00(4) 2.920(3) 168(4) 3
N1 H1 N2 0.94(4) 2.00(4) 2.920(3) 168(4) 3

_refine_diff_density_max         0.193
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dm16574
_audit_block_doi                 10.5517/ccdc.csd.cc215l3y
_database_code_depnum_ccdc_archive 'CCDC 1882199'
loop_
_audit_author_name
_audit_author_address
'Naiguo Xing'
;Sichuan University
China
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2020-03-17 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H10 N2'
_chemical_formula_sum            'C10 H10 N2'
_chemical_formula_weight         158.20
_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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   9.612(3)
_cell_length_b                   7.441(2)
_cell_length_c                   24.001(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1716.6(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    296
_cell_measurement_theta_max      22.45
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0620 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9189.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.697
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1168
_reflns_number_total             1974
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1974
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.4079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.032
;
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
N1 N 0.03845(17) 0.2392(2) 0.47293(6) 0.0559(5) Uani 1 1 d . . . . .
N2 N 0.26725(17) 0.2520(2) 0.47817(6) 0.0532(5) Uani 1 1 d . . . . .
H2 H 0.3487 0.2678 0.4921 0.064 Uiso 1 1 calc R . . . .
C1 C -0.1193(2) 0.0528(3) 0.38440(9) 0.0559(6) Uani 1 1 d . . . . .
H1 H -0.1450 0.0252 0.4208 0.067 Uiso 1 1 calc R . . . .
C2 C -0.2055(2) 0.0036(3) 0.34087(10) 0.0667(7) Uani 1 1 d . . . . .
H2A H -0.2885 -0.0562 0.3482 0.080 Uiso 1 1 calc R . . . .
C3 C -0.1690(3) 0.0427(3) 0.28691(10) 0.0720(7) Uani 1 1 d . . . . .
H3 H -0.2266 0.0085 0.2577 0.086 Uiso 1 1 calc R . . . .
C4 C -0.0470(3) 0.1325(4) 0.27629(9) 0.0701(7) Uani 1 1 d . . . . .
H4 H -0.0221 0.1596 0.2398 0.084 Uiso 1 1 calc R . . . .
C5 C 0.0388(2) 0.1827(3) 0.31982(8) 0.0567(6) Uani 1 1 d . . . . .
H5 H 0.1208 0.2443 0.3122 0.068 Uiso 1 1 calc R . . . .
C6 C 0.0048(2) 0.1429(2) 0.37471(8) 0.0447(5) Uani 1 1 d . . . . .
C7 C 0.0951(2) 0.1931(3) 0.42149(7) 0.0441(5) Uani 1 1 d . . . . .
C8 C 0.2380(2) 0.2004(3) 0.42481(7) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.1459(2) 0.2736(3) 0.50482(9) 0.0598(6) Uani 1 1 d . . . . .
H9 H 0.1387 0.3092 0.5419 0.072 Uiso 1 1 calc R . . . .
C10 C 0.3505(2) 0.1593(3) 0.38416(9) 0.0612(6) Uani 1 1 d . . . . .
H10A H 0.3870 0.2695 0.3693 0.092 Uiso 1 1 calc GR . . . .
H10B H 0.3136 0.0877 0.3544 0.092 Uiso 1 1 calc GR . . . .
H10C H 0.4236 0.0944 0.4026 0.092 Uiso 1 1 calc GR . . . .


_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
N1 C7 1.392(2) . ?
N1 C9 1.311(2) . ?
N2 H2 0.8600 . ?
N2 C8 1.366(2) . ?
N2 C9 1.340(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.388(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.373(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 C7 1.468(3) . ?
C7 C8 1.377(3) . ?
C8 C10 1.488(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C9 N1 C7 104.93(17) . . ?
C8 N2 H2 126.2 . . ?
C9 N2 H2 126.2 . . ?
C9 N2 C8 107.58(17) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.1(2) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.64(19) . . ?
C1 C6 C7 120.22(18) . . ?
C5 C6 C7 122.14(18) . . ?
N1 C7 C6 120.64(17) . . ?
C8 C7 N1 109.23(16) . . ?
C8 C7 C6 130.11(17) . . ?
N2 C8 C7 105.69(17) . . ?
N2 C8 C10 121.50(17) . . ?
C7 C8 C10 132.78(18) . . ?
N1 C9 N2 112.57(18) . . ?
N1 C9 H9 123.7 . . ?
N2 C9 H9 123.7 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
N1 C7 C8 N2 -0.4(2) . . . . ?
N1 C7 C8 C10 177.5(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C6 C7 N1 -33.1(3) . . . . ?
C1 C6 C7 C8 145.2(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C7 -179.7(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.3(2) . . . . ?
C5 C6 C7 N1 146.7(2) . . . . ?
C5 C6 C7 C8 -34.9(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C7 C8 N2 -178.87(19) . . . . ?
C6 C7 C8 C10 -0.9(4) . . . . ?
C7 N1 C9 N2 -0.5(3) . . . . ?
C8 N2 C9 N1 0.3(3) . . . . ?
C9 N1 C7 C6 179.20(19) . . . . ?
C9 N1 C7 C8 0.6(2) . . . . ?
C9 N2 C8 C7 0.1(2) . . . . ?
C9 N2 C8 C10 -178.13(19) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
