# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_zhq2018100201_0m
_database_code_depnum_ccdc_archive 'CCDC 1878486'
loop_
_audit_author_name
_audit_author_address
'Haoqiang Zhao'
;No. 59 Zhongguancun Street, Haidian District Beijing, 100872, P.R. China
China
;
_audit_update_record             
;
2018-11-12 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2018-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 F3 N2 O'
_chemical_formula_sum            'C12 H9 F3 N2 O'
_chemical_formula_weight         254.21
_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'
F F 0.0171 0.0103 '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'

_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.891(5)
_cell_length_b                   11.795(2)
_cell_length_c                   8.809(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.038(8)
_cell_angle_gamma                90
_cell_volume                     2271.3(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2672
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.366
_cell_measurement_theta_min      2.998
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1254 before and 0.0825 after correction. The Ratio of minimum to maximum transmission is 0.7648. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10800
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.997
_diffrn_ambient_temperature      200.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                1506
_reflns_number_total             2598
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    ?
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      0.880
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2599
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 F00E, C00G, F00H, F00I
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F00H, C00G, F00E, F00I
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0002
 C00G, F00H, F00E, F00I
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(F00J)=Sof(F00F)=Sof(F0AA)=1-FVAR(1)
 Sof(F00E)=Sof(F00H)=Sof(F00I)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C004(H004), C006(H006), C00A(H00A), C00C(H00E), C00D(H00F), C00F(H00G)
4.b Idealised Me refined as rotating group:
 C00B(H00B,H00C,H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O001 O 0.32274(8) 0.18202(14) 0.8319(2) 0.0441(6) Uani 1 1 d . . . . .
N002 N 0.25844(10) 0.37495(15) 0.5884(2) 0.0351(5) Uani 1 1 d . . . . .
N003 N 0.33310(10) 0.37148(14) 0.7895(2) 0.0338(5) Uani 1 1 d . . . . .
C004 C 0.22517(12) 0.37390(18) 0.8444(3) 0.0374(6) Uani 1 1 d . . . . .
H004 H 0.2359 0.3723 0.9504 0.045 Uiso 1 1 calc R . . . .
C005 C 0.26948(12) 0.37315(16) 0.7386(3) 0.0326(6) Uani 1 1 d . . . . .
C006 C 0.19980(12) 0.37656(18) 0.5385(3) 0.0374(6) Uani 1 1 d . . . . .
H006 H 0.1905 0.3765 0.4320 0.045 Uiso 1 1 calc R . . . .
C007 C 0.35664(12) 0.26561(19) 0.8388(3) 0.0372(6) Uani 1 1 d . . . . .
C008 C 0.15216(12) 0.37834(17) 0.6346(3) 0.0377(6) Uani 1 1 d . . . . .
C009 C 0.36733(12) 0.46966(19) 0.7900(3) 0.0384(6) Uani 1 1 d . . . . .
C00A C 0.16529(12) 0.37709(18) 0.7913(3) 0.0388(6) Uani 1 1 d . . . . .
H00A H 0.1332 0.3784 0.8599 0.047 Uiso 1 1 calc R . . . .
C00B C 0.33669(13) 0.5753(2) 0.7321(4) 0.0480(7) Uani 1 1 d . . . . .
H00B H 0.3217 0.5640 0.6264 0.072 Uiso 1 1 calc GR . . . .
H00C H 0.3660 0.6381 0.7373 0.072 Uiso 1 1 calc GR . . . .
H00D H 0.3022 0.5932 0.7946 0.072 Uiso 1 1 calc GR . . . .
C00C C 0.42628(13) 0.4662(2) 0.8428(4) 0.0505(8) Uani 1 1 d . . . . .
H00E H 0.4502 0.5334 0.8456 0.061 Uiso 1 1 calc R . . . .
C00D C 0.41924(13) 0.2672(2) 0.8925(3) 0.0478(7) Uani 1 1 d . . . . .
H00F H 0.4380 0.1989 0.9283 0.057 Uiso 1 1 calc R . . . .
F00E F 0.0799(3) 0.3881(10) 0.4275(6) 0.129(3) Uani 0.635(9) 1 d . U P A 1
C00F C 0.45241(14) 0.3635(2) 0.8937(4) 0.0528(8) Uani 1 1 d . . . . .
H00G H 0.4941 0.3618 0.9295 0.063 Uiso 1 1 calc R . . . .
C00G C 0.08730(14) 0.3788(2) 0.5738(4) 0.0500(7) Uani 1 1 d . U . . .
F00H F 0.0557(2) 0.2924(4) 0.6134(11) 0.106(2) Uani 0.635(9) 1 d . U P A 1
F00I F 0.05583(19) 0.4662(4) 0.6262(9) 0.0958(18) Uani 0.635(9) 1 d . U P A 1
F00J F 0.0501(3) 0.3697(17) 0.6684(9) 0.141(7) Uani 0.365(9) 1 d . . P A 2
F00F F 0.0771(6) 0.4530(10) 0.476(2) 0.139(7) Uani 0.365(9) 1 d . . P A 2
F0AA F 0.0793(4) 0.2829(8) 0.4870(16) 0.109(4) Uani 0.365(9) 1 d . . P A 2


_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
O001 C007 1.234(3) . ?
N002 C005 1.333(3) . ?
N002 C006 1.335(3) . ?
N003 C005 1.441(3) . ?
N003 C007 1.411(3) . ?
N003 C009 1.379(3) . ?
C004 C005 1.380(4) . ?
C004 C00A 1.369(4) . ?
C006 C008 1.378(4) . ?
C007 C00D 1.426(4) . ?
C008 C00A 1.395(4) . ?
C008 C00G 1.491(4) . ?
C009 C00B 1.492(4) . ?
C009 C00C 1.349(4) . ?
C00C C00F 1.402(4) . ?
C00D C00F 1.348(4) . ?
F00E C00G 1.295(6) . ?
C00G F00H 1.291(5) . ?
C00G F00I 1.336(5) . ?
C00G F00J 1.201(7) . ?
C00G F00F 1.237(8) . ?
C00G F0AA 1.371(7) . ?

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
C005 N002 C006 116.6(2) . . ?
C007 N003 C005 116.07(19) . . ?
C009 N003 C005 120.37(19) . . ?
C009 N003 C007 123.6(2) . . ?
C00A C004 C005 117.6(2) . . ?
N002 C005 N003 115.5(2) . . ?
N002 C005 C004 125.0(2) . . ?
C004 C005 N003 119.5(2) . . ?
N002 C006 C008 123.0(2) . . ?
O001 C007 N003 118.9(2) . . ?
O001 C007 C00D 126.3(2) . . ?
N003 C007 C00D 114.8(2) . . ?
C006 C008 C00A 119.0(3) . . ?
C006 C008 C00G 121.1(3) . . ?
C00A C008 C00G 119.9(3) . . ?
N003 C009 C00B 117.8(2) . . ?
C00C C009 N003 119.0(2) . . ?
C00C C009 C00B 123.2(2) . . ?
C004 C00A C008 118.8(2) . . ?
C009 C00C C00F 120.2(3) . . ?
C00F C00D C007 121.4(3) . . ?
C00D C00F C00C 121.0(3) . . ?
F00E C00G C008 115.1(4) . . ?
F00E C00G F00I 103.9(5) . . ?
F00H C00G C008 114.4(3) . . ?
F00H C00G F00E 107.2(5) . . ?
F00H C00G F00I 102.9(5) . . ?
F00I C00G C008 112.2(3) . . ?
F00J C00G C008 114.7(5) . . ?
F00J C00G F00F 116.1(9) . . ?
F00J C00G F0AA 104.0(7) . . ?
F00F C00G C008 112.7(6) . . ?
F00F C00G F0AA 100.6(9) . . ?
F0AA C00G C008 106.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_5929
_database_code_depnum_ccdc_archive 'CCDC 2102000'
loop_
_audit_author_name
_audit_author_address
'haoqiang zhao'
;Renmin University of China
China
;
_audit_update_record             
;
2021-08-07 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N4'
_chemical_formula_weight         253.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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                   12.5969(7)
_cell_length_b                   7.4254(3)
_cell_length_c                   15.4359(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.168(7)
_cell_angle_gamma                90
_cell_volume                     1327.40(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.618
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7148
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.817
_diffrn_reflns_theta_max         74.048
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2547
_reflns_number_gt                2113
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0716P)²+0.1858P] 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-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0025(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2547
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1321
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
N5 N 0.35701(11) 0.42459(18) 0.19766(8) 0.0413(3) Uani 1 1 d . . . . .
N9 N 0.29090(11) 0.35223(19) 0.42848(8) 0.0459(3) Uani 1 1 d . . . . .
H9 H 0.276448 0.336870 0.477990 0.055 Uiso 1 1 calc R U . . .
N3 N 0.24590(12) 0.18190(18) 0.19135(9) 0.0441(3) Uani 1 1 d . . . . .
N7 N 0.38852(12) 0.53304(19) 0.35362(9) 0.0466(3) Uani 1 1 d . . . . .
C1 C 0.24599(13) 0.2399(2) 0.35487(10) 0.0393(3) Uani 1 1 d . . . . .
C10 C 0.17019(13) 0.0909(2) 0.35943(10) 0.0414(4) Uani 1 1 d . . . . .
C4 C 0.29606(14) 0.2790(2) 0.14755(10) 0.0444(4) Uani 1 1 d . . . . .
H4 H 0.290884 0.251613 0.087227 0.053 Uiso 1 1 calc R U . . .
C6 C 0.34371(12) 0.4192(2) 0.28131(10) 0.0385(3) Uani 1 1 d . . . . .
C15 C 0.19107(15) -0.0808(2) 0.33318(12) 0.0489(4) Uani 1 1 d . . . . .
H15 H 0.251391 -0.097932 0.313635 0.059 Uiso 1 1 calc R U . . .
C11 C 0.07737(14) 0.1188(2) 0.38701(11) 0.0462(4) Uani 1 1 d . . . . .
C8 C 0.35806(14) 0.4878(2) 0.42427(11) 0.0483(4) Uani 1 1 d . . . . .
H8 H 0.387559 0.560302 0.477591 0.058 Uiso 1 1 calc R U . . .
C17 C 0.41378(16) 0.5717(2) 0.16797(12) 0.0511(4) Uani 1 1 d . . . . .
H17 H 0.480638 0.611581 0.223314 0.061 Uiso 1 1 calc R U . . .
C2 C 0.27444(12) 0.2693(2) 0.27687(10) 0.0379(3) Uani 1 1 d . . . . .
C14 C 0.12386(16) -0.2261(2) 0.33567(13) 0.0548(4) Uani 1 1 d . . . . .
H14 H 0.139967 -0.340429 0.319468 0.066 Uiso 1 1 calc R U . . .
C16 C 0.04501(17) 0.3005(3) 0.41130(15) 0.0587(5) Uani 1 1 d . . . . .
H16A H 0.100009 0.336590 0.472134 0.088 Uiso 1 1 calc R U . . .
H16B H -0.030538 0.294674 0.412485 0.088 Uiso 1 1 calc R U . . .
H16C H 0.044848 0.386580 0.364850 0.088 Uiso 1 1 calc R U . . .
C13 C 0.03262(16) -0.1999(2) 0.36241(13) 0.0564(5) Uani 1 1 d . . . . .
H13 H -0.013621 -0.296590 0.363842 0.068 Uiso 1 1 calc R U . . .
C12 C 0.01023(15) -0.0297(3) 0.38703(13) 0.0541(4) Uani 1 1 d . . . . .
H12 H -0.052076 -0.013829 0.404267 0.065 Uiso 1 1 calc R U . . .
C19 C 0.45698(18) 0.5068(3) 0.09498(14) 0.0637(5) Uani 1 1 d . . . . .
H19A H 0.507766 0.406077 0.119582 0.095 Uiso 1 1 calc R U . . .
H19B H 0.498026 0.602351 0.079762 0.095 Uiso 1 1 calc R U . . .
H19C H 0.392608 0.470650 0.039196 0.095 Uiso 1 1 calc R U . . .
C18 C 0.3319(3) 0.7293(3) 0.1332(2) 0.0882(8) Uani 1 1 d . . . . .
H18A H 0.267988 0.695738 0.076506 0.132 Uiso 1 1 calc R U . . .
H18B H 0.371771 0.829454 0.120500 0.132 Uiso 1 1 calc R U . . .
H18C H 0.303915 0.762683 0.180511 0.132 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
N5 C6 1.3664(18) . ?
N5 C4 1.375(2) . ?
N5 C17 1.474(2) . ?
N9 C8 1.333(2) . ?
N9 C1 1.342(2) . ?
N9 H9 0.8600 . ?
N3 C4 1.308(2) . ?
N3 C2 1.3854(19) . ?
N7 C8 1.334(2) . ?
N7 C6 1.336(2) . ?
C1 C2 1.4019(19) . ?
C1 C10 1.481(2) . ?
C10 C15 1.394(2) . ?
C10 C11 1.408(2) . ?
C4 H4 0.9300 . ?
C6 C2 1.399(2) . ?
C15 C14 1.381(2) . ?
C15 H15 0.9300 . ?
C11 C12 1.390(2) . ?
C11 C16 1.499(3) . ?
C8 H8 0.9300 . ?
C17 C19 1.510(2) . ?
C17 C18 1.512(3) . ?
C17 H17 0.9800 . ?
C14 C13 1.379(3) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 C12 1.381(3) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C6 N5 C4 105.04(12) . . ?
C6 N5 C17 124.78(13) . . ?
C4 N5 C17 129.79(12) . . ?
C8 N9 C1 119.49(12) . . ?
C8 N9 H9 120.3 . . ?
C1 N9 H9 120.3 . . ?
C4 N3 C2 103.72(13) . . ?
C8 N7 C6 111.16(14) . . ?
N9 C1 C2 117.73(14) . . ?
N9 C1 C10 119.27(12) . . ?
C2 C1 C10 123.00(13) . . ?
C15 C10 C11 119.75(15) . . ?
C15 C10 C1 118.08(13) . . ?
C11 C10 C1 122.15(15) . . ?
N3 C4 N5 114.77(13) . . ?
N3 C4 H4 122.6 . . ?
N5 C4 H4 122.6 . . ?
N7 C6 N5 127.04(14) . . ?
N7 C6 C2 126.51(13) . . ?
N5 C6 C2 106.45(12) . . ?
C14 C15 C10 121.23(15) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C12 C11 C10 117.48(16) . . ?
C12 C11 C16 119.25(15) . . ?
C10 C11 C16 123.21(15) . . ?
N9 C8 N7 128.50(14) . . ?
N9 C8 H8 115.7 . . ?
N7 C8 H8 115.7 . . ?
N5 C17 C19 110.88(15) . . ?
N5 C17 C18 109.71(15) . . ?
C19 C17 C18 112.22(17) . . ?
N5 C17 H17 108.0 . . ?
C19 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
N3 C2 C6 110.02(12) . . ?
N3 C2 C1 133.41(14) . . ?
C6 C2 C1 116.55(13) . . ?
C13 C14 C15 119.40(17) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C13 C12 119.71(16) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C12 C11 122.41(16) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 N9 C1 C2 1.3(2) . . . . ?
C8 N9 C1 C10 -179.22(14) . . . . ?
N9 C1 C10 C15 -132.46(15) . . . . ?
C2 C1 C10 C15 47.0(2) . . . . ?
N9 C1 C10 C11 49.1(2) . . . . ?
C2 C1 C10 C11 -131.47(16) . . . . ?
C2 N3 C4 N5 0.46(18) . . . . ?
C6 N5 C4 N3 -0.19(19) . . . . ?
C17 N5 C4 N3 -173.17(15) . . . . ?
C8 N7 C6 N5 -179.96(15) . . . . ?
C8 N7 C6 C2 -0.6(2) . . . . ?
C4 N5 C6 N7 179.31(15) . . . . ?
C17 N5 C6 N7 -7.3(2) . . . . ?
C4 N5 C6 C2 -0.17(16) . . . . ?
C17 N5 C6 C2 173.26(14) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
C1 C10 C15 C14 -179.99(15) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C1 C10 C11 C12 178.73(14) . . . . ?
C15 C10 C11 C16 -176.64(16) . . . . ?
C1 C10 C11 C16 1.8(2) . . . . ?
C1 N9 C8 N7 0.8(3) . . . . ?
C6 N7 C8 N9 -1.2(3) . . . . ?
C6 N5 C17 C19 157.00(16) . . . . ?
C4 N5 C17 C19 -31.3(2) . . . . ?
C6 N5 C17 C18 -78.5(2) . . . . ?
C4 N5 C17 C18 93.2(2) . . . . ?
C4 N3 C2 C6 -0.56(17) . . . . ?
C4 N3 C2 C1 177.60(17) . . . . ?
N7 C6 C2 N3 -179.02(15) . . . . ?
N5 C6 C2 N3 0.46(17) . . . . ?
N7 C6 C2 C1 2.5(2) . . . . ?
N5 C6 C2 C1 -178.04(13) . . . . ?
N9 C1 C2 N3 179.24(16) . . . . ?
C10 C1 C2 N3 -0.2(3) . . . . ?
N9 C1 C2 C6 -2.7(2) . . . . ?
C10 C1 C2 C6 177.83(13) . . . . ?
C10 C15 C14 C13 1.6(3) . . . . ?
C15 C14 C13 C12 -0.5(3) . . . . ?
C14 C13 C12 C11 -0.7(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C16 C11 C12 C13 177.84(18) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.041



