# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_BPI_190_00
_database_code_depnum_ccdc_archive 'CCDC 2072411'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT088_BPI_190_00          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.34 Note  
RESPONSE: This is due to the number of modeled disorder atom sites in the 
          structure.
;
_vrf_PLAT250_BPI_190_00          
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.8 Note  
RESPONSE: Due to the disorder atom sites.
;
_vrf_PLAT906_BPI_190_00          
;
PROBLEM: Large K Value in the Analysis of Variance ......     14.528 Check 
RESPONSE: Due to diffuse scattering from the metal pin on the holder and weak
          high angle data.
;
_vrf_PLAT911_BPI_190_00          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT088_BPI_210_00_autored  
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.42 Note  
RESPONSE: This is due to the number of modeled disorder atom sites in the 
          structure.
;
_vrf_PLAT250_BPI_210_00_autored  
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: Due to the disordered atom sites.
;
_vrf_PLAT906_BPI_210_00_autored  
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.130 Check 
RESPONSE: Due to diffuse scattering from the metal pin on the holder and weak
          high angle data.
;
_vrf_PLAT088_BPI_230_00_autored  
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.46 Note  
RESPONSE: This is due to the number of modeled disorder atom sites in the 
          structure.
;
_vrf_PLAT250_BPI_230_00_autored  
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: Due to the disordered atom sites.
;
_vrf_PLAT906_BPI_230_00_autored  
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.439 Check 
RESPONSE: Due to diffuse scattering from the metal pin on the holder and weak
          high angle data.
;
_vrf_PLAT088_BPI_250_00          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.49 Note  
RESPONSE: This is due to the number of modeled disorder atom sites in the 
          structure.
;
_vrf_PLAT906_BPI_250_00          
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.652 Check 
RESPONSE: Due to diffuse scattering from the metal pin on the holder and weak
          high angle data.
;
_vrf_PLAT088_BPI_270_00          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.52 Note  
RESPONSE: This is due to the number of modeled disorder atom sites in the 
          structure.
;
_vrf_PLAT906_BPI_270_00          
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.193 Check 
RESPONSE: Due to diffuse scattering from the metal pin on the holder and weak
          high angle data.
;
_vrf_PLAT088_BPI_290_00          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.54 Note  
RESPONSE: This is due to the number of modeled disorder atom sites in the 
          structure.
;
_vrf_PLAT906_BPI_290_00          
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.145 Check 
RESPONSE: Due to diffuse scattering from the metal pin on the holder and weak
          high angle data.
;
# end Validation Reply Form

_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48  H28  N12  '
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.498(2)
_cell_length_b                   7.0467(10)
_cell_length_c                   9.0692(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.821(16)
_cell_angle_gamma                90
_cell_volume                     957.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4272
_cell_measurement_temperature    190.00(10)
_cell_measurement_theta_max      30.7220
_cell_measurement_theta_min      2.7190
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.565
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 1 -12 0.0715
-20 -4 0 0.1270
-6 0 13 0.0659
20 3 -5 0.0934
16 3 5 0.1311
-8 9 1 0.0169
7 -9 1 0.0094
11 -4 -11 0.0728

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.4517 0.5131 -12.4016 -0.1135 0.0016 -0.9935
-19.8909 -3.5463 0.3394 0.9879 -0.0251 0.1533
-6.3502 0.2663 12.7675 -0.1047 0.0040 0.9945
20.3925 3.0794 -5.3839 -0.8457 0.0209 -0.5333
16.1258 3.4302 4.7502 -0.9676 0.0251 0.2511
-8.0473 9.2104 0.6446 -0.0253 -0.9945 0.1015
7.1564 -9.2690 0.7579 0.0256 0.9996 0.0090
10.7404 -4.0346 -11.0552 0.0104 0.4449 -0.8955

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5921
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.332
_diffrn_reflns_theta_min         2.719
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      190.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -30.00  192
  2  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -90.00  192
  3  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 120.00  190
  4  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00-150.00  190
  5  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 -90.00  190
  6  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00  60.00  190
  7  ω    -23.00   6.00   0.50   27.23    --    5.37 -99.00 -90.00   58
  8  ω    -23.00  39.00   0.50   27.23    --    5.37 -99.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0432858000
_diffrn_orient_matrix_UB_12      -0.0385452000
_diffrn_orient_matrix_UB_13      -0.0289228000
_diffrn_orient_matrix_UB_21      0.0180339000
_diffrn_orient_matrix_UB_22      -0.0930058000
_diffrn_orient_matrix_UB_23      0.0112207000
_diffrn_orient_matrix_UB_31      -0.0064567000
_diffrn_orient_matrix_UB_32      0.0001481000
_diffrn_orient_matrix_UB_33      0.0746785000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                766
_reflns_number_total             1064
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1064
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0784
_refine_ls_restrained_S_all      1.070
_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)+(0.0609P)²+1.6690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2021
_refine_special_details          
;
Atom sites C2 < C9, N2 and N3 were positionally disordered and modeled edit
as split sites A and B. The site occupancies of the two sites were constrained to a total value of 1 and refined to 0.49 and 0.51 for the A and B sites, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, the rigid bond restraint RIGU and free variable DFIX restraints were applied.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A = C6A-C7A = C9A-C8A = C9A-C5A = C1-C2A = C2A-C3A = C1-C2B = C2B-C3B
 1.38199 with sigma of 0.02
 C5B-C6B = C6B-C7B = C8B-C9B = C9B-C5B
 1.38199 with sigma of 0.02
 N1-C1 = C7A-N3A = C7B-N3B = C8A-N3A = C8B-N3B
 1.31751 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C1, N2B, C2B, N3B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N2A, C2A, C3A, N3A,
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H1B)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(N2B)=Sof(N3B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=0.5*(1-FVAR(2))
 Sof(N2A)=Sof(C3A)=Sof(N3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=0.5*FVAR(2)
 Sof(H1A)=Sof(C2A)=Sof(H2A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1B), C1(H1A), C2B(H2B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B),
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.3157(2) 0.500000 0.0389(4) 0.0544(9) Uani 1 2 d DS T P A .
C1 C 0.35992(17) 0.6593(5) 0.0832(4) 0.0609(9) Uani 1 1 d D . . . .
H1B H 0.335418 0.774125 0.035534 0.073 Uiso 0.505(11) 1 calc R U P A 2
H1A H 0.327604 0.775240 0.069260 0.073 Uiso 0.495(11) 1 calc R U P A 1
N2B N 0.5626(5) 0.500000 0.3690(8) 0.064(3) Uani 0.505(11) 2 d S T P A 2
C2B C 0.4411(7) 0.6692(18) 0.1967(14) 0.063(3) Uani 0.505(11) 1 d D . P A 2
H2B H 0.466786 0.787563 0.234715 0.075 Uiso 0.505(11) 1 calc R U P A 2
N3B N 0.8905(8) 0.500000 0.6470(14) 0.051(3) Uani 0.505(11) 2 d DS T P A 2
C3B C 0.4817(6) 0.500000 0.2503(13) 0.055(3) Uani 0.505(11) 2 d DS T P A 2
C4B C 0.6339(7) 0.500000 0.3328(13) 0.041(2) Uani 0.505(11) 2 d S T P A 2
H4B H 0.631797 0.500000 0.227220 0.050 Uiso 0.505(11) 2 calc R U P A 2
C5B C 0.7218(14) 0.500000 0.4418(19) 0.034(4) Uani 0.505(11) 2 d DS T P A 2
C6B C 0.7983(9) 0.500000 0.393(2) 0.059(5) Uani 0.505(11) 2 d DS T P A 2
H6B H 0.794661 0.500000 0.286866 0.070 Uiso 0.505(11) 2 calc R U P A 2
C7B C 0.8808(9) 0.500000 0.4968(18) 0.063(4) Uani 0.505(11) 2 d DS T P A 2
H7B H 0.932750 0.500000 0.459575 0.076 Uiso 0.505(11) 2 calc R U P A 2
C8B C 0.8171(8) 0.500000 0.6925(15) 0.046(3) Uani 0.505(11) 2 d DS T P A 2
H8B H 0.822947 0.500000 0.799387 0.055 Uiso 0.505(11) 2 calc R U P A 2
C9B C 0.7310(10) 0.500000 0.5976(16) 0.043(3) Uani 0.505(11) 2 d DS T P A 2
H9B H 0.680297 0.500000 0.638245 0.051 Uiso 0.505(11) 2 calc R U P A 2
N2A N 0.5900(5) 0.500000 0.2539(9) 0.064(3) Uani 0.495(11) 2 d S T P A 1
C2A C 0.4512(7) 0.6655(18) 0.1491(15) 0.062(3) Uani 0.495(11) 1 d D . P A 1
H2A H 0.481217 0.783929 0.168493 0.075 Uiso 0.495(11) 1 calc R U P A 1
C3A C 0.4973(6) 0.500000 0.1857(12) 0.051(2) Uani 0.495(11) 2 d DS T P A 1
N3A N 0.9018(7) 0.500000 0.5922(15) 0.045(2) Uani 0.495(11) 2 d DS T P A 1
C4A C 0.6222(8) 0.500000 0.3898(15) 0.045(3) Uani 0.495(11) 2 d S T P A 1
H4A H 0.582952 0.500000 0.454938 0.054 Uiso 0.495(11) 2 calc R U P A 1
C5A C 0.7190(16) 0.500000 0.460(2) 0.042(5) Uani 0.495(11) 2 d DS T P A 1
C6A C 0.7783(8) 0.500000 0.369(2) 0.041(3) Uani 0.495(11) 2 d DS T P A 1
H6A H 0.757918 0.500000 0.260724 0.050 Uiso 0.495(11) 2 calc R U P A 1
C7A C 0.8685(9) 0.500000 0.4419(14) 0.049(3) Uani 0.495(11) 2 d DS T P A 1
H7A H 0.909539 0.500000 0.380050 0.059 Uiso 0.495(11) 2 calc R U P A 1
C8A C 0.8444(10) 0.500000 0.6746(15) 0.048(3) Uani 0.495(11) 2 d DS T P A 1
H8A H 0.866814 0.500000 0.782400 0.058 Uiso 0.495(11) 2 calc R U P A 1
C9A C 0.7524(11) 0.500000 0.6149(19) 0.047(4) Uani 0.495(11) 2 d DS T P A 1
H9A H 0.713442 0.500000 0.680548 0.056 Uiso 0.495(11) 2 calc R U P A 1


_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 C1 1.323(4) 6_565 ?
N1 C1 1.323(4) . ?
C1 H1B 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2B 1.409(10) . ?
C1 C2A 1.388(10) . ?
N2B C3B 1.429(11) . ?
N2B C4B 1.231(15) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.377(10) . ?
N3B C7B 1.332(13) . ?
N3B C8B 1.306(12) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.46(2) . ?
C5B C6B 1.367(14) . ?
C5B C9B 1.383(13) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.380(12) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.390(10) . ?
C9B H9B 0.9500 . ?
N2A C3A 1.412(11) . ?
N2A C4A 1.206(15) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.363(10) . ?
N3A C7A 1.328(11) . ?
N3A C8A 1.299(13) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.47(2) . ?
C5A C6A 1.387(14) . ?
C5A C9A 1.364(15) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.386(10) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.390(12) . ?
C9A H9A 0.9500 . ?

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 C1 116.0(3) 6_565 . ?
N1 C1 H1B 117.9 . . ?
N1 C1 H1A 118.3 . . ?
N1 C1 C2B 124.1(6) . . ?
N1 C1 C2A 123.3(6) . . ?
C2B C1 H1B 117.9 . . ?
C2A C1 H1A 118.3 . . ?
C4B N2B C3B 118.3(9) . . ?
C1 C2B H2B 121.4 . . ?
C3B C2B C1 117.2(10) . . ?
C3B C2B H2B 121.4 . . ?
C8B N3B C7B 116.3(9) . . ?
C2B C3B N2B 120.0(6) 6_565 . ?
C2B C3B N2B 120.0(6) . . ?
C2B C3B C2B 119.9(12) 6_565 . ?
N2B C4B H4B 117.8 . . ?
N2B C4B C5B 124.3(11) . . ?
C5B C4B H4B 117.8 . . ?
C6B C5B C4B 121.1(14) . . ?
C6B C5B C9B 117(2) . . ?
C9B C5B C4B 121.6(14) . . ?
C5B C6B H6B 119.7 . . ?
C5B C6B C7B 120.5(18) . . ?
C7B C6B H6B 119.7 . . ?
N3B C7B C6B 122.7(12) . . ?
N3B C7B H7B 118.6 . . ?
C6B C7B H7B 118.6 . . ?
N3B C8B H8B 117.3 . . ?
N3B C8B C9B 125.4(12) . . ?
C9B C8B H8B 117.3 . . ?
C5B C9B C8B 117.7(18) . . ?
C5B C9B H9B 121.2 . . ?
C8B C9B H9B 121.2 . . ?
C4A N2A C3A 123.8(8) . . ?
C1 C2A H2A 120.3 . . ?
C3A C2A C1 119.4(10) . . ?
C3A C2A H2A 120.3 . . ?
C2A C3A N2A 121.2(6) . . ?
C2A C3A N2A 121.2(6) 6_565 . ?
C2A C3A C2A 117.6(12) 6_565 . ?
C8A N3A C7A 116.6(10) . . ?
N2A C4A H4A 118.2 . . ?
N2A C4A C5A 123.6(11) . . ?
C5A C4A H4A 118.2 . . ?
C6A C5A C4A 119.8(16) . . ?
C9A C5A C4A 121.5(16) . . ?
C9A C5A C6A 119(2) . . ?
C5A C6A H6A 121.5 . . ?
C7A C6A C5A 117.1(19) . . ?
C7A C6A H6A 121.5 . . ?
N3A C7A C6A 124.8(12) . . ?
N3A C7A H7A 117.6 . . ?
C6A C7A H7A 117.6 . . ?
N3A C8A H8A 117.9 . . ?
N3A C8A C9A 124.1(13) . . ?
C9A C8A H8A 117.9 . . ?
C5A C9A C8A 119(2) . . ?
C5A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?

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 C1 C2B C3B 8.4(14) . . . . ?
N1 C1 C2A C3A -7.2(15) . . . . ?
C1 N1 C1 C2B -13.7(9) 6_565 . . . ?
C1 N1 C1 C2A 10.9(10) 6_565 . . . ?
C1 C2B C3B N2B -177.9(10) . . . . ?
C1 C2B C3B C2B -2(2) . . . 6_565 ?
C1 C2A C3A N2A -179.5(10) . . . . ?
C1 C2A C3A C2A 3(2) . . . 6_565 ?
N2B C4B C5B C6B 180.000(2) . . . . ?
N2B C4B C5B C9B 0.000(2) . . . . ?
N3B C8B C9B C5B 0.000(3) . . . . ?
C3B N2B C4B C5B 180.000(2) . . . . ?
C4B N2B C3B C2B 92.3(10) . . . 6_565 ?
C4B N2B C3B C2B -92.3(10) . . . . ?
C4B C5B C6B C7B 180.000(3) . . . . ?
C4B C5B C9B C8B 180.000(3) . . . . ?
C5B C6B C7B N3B 0.000(3) . . . . ?
C6B C5B C9B C8B 0.000(3) . . . . ?
C7B N3B C8B C9B 0.000(3) . . . . ?
C8B N3B C7B C6B 0.000(3) . . . . ?
C9B C5B C6B C7B 0.000(4) . . . . ?
N2A C4A C5A C6A 0.000(4) . . . . ?
N2A C4A C5A C9A 180.000(2) . . . . ?
C3A N2A C4A C5A 180.000(3) . . . . ?
N3A C8A C9A C5A 0.000(3) . . . . ?
C4A N2A C3A C2A -91.2(10) . . . 6_565 ?
C4A N2A C3A C2A 91.2(10) . . . . ?
C4A C5A C6A C7A 180.000(2) . . . . ?
C4A C5A C9A C8A 180.000(3) . . . . ?
C5A C6A C7A N3A 0.000(3) . . . . ?
C6A C5A C9A C8A 0.000(2) . . . . ?
C7A N3A C8A C9A 0.000(3) . . . . ?
C8A N3A C7A C6A 0.000(3) . . . . ?
C9A C5A C6A C7A 0.000(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_original_sample_id hut21_46
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1354
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.832
####################################################################### 
# 
# 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_BPI_210_00_autored
_database_code_depnum_ccdc_archive 'CCDC 2072412'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.5861(9)
_cell_length_b                   7.0608(4)
_cell_length_c                   9.0691(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.198(7)
_cell_angle_gamma                90
_cell_volume                     963.15(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4813
_cell_measurement_temperature    210.05(10)
_cell_measurement_theta_max      31.0810
_cell_measurement_theta_min      3.0760
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 1 -12 0.0715
-20 -4 0 0.1270
-7 0 13 0.0659
20 3 -5 0.0934
16 4 5 0.1311
-9 9 1 0.0169
8 -9 1 0.0094
11 -4 -11 0.0728

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.6970 0.5508 -12.3876 -0.1135 0.0016 -0.9935
-19.5109 -4.0218 0.2765 0.9879 -0.0251 0.1533
-6.6898 0.3342 12.7672 -0.1047 0.0040 0.9945
20.1862 3.4795 -5.3273 -0.8457 0.0209 -0.5333
15.6349 3.9029 4.8091 -0.9676 0.0251 0.2511
-9.1313 9.0370 0.6540 -0.0253 -0.9945 0.1015
8.2130 -9.0928 0.7477 0.0256 0.9996 0.0090
11.4778 -3.9709 -11.0535 0.0104 0.4449 -0.8955

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.353
_diffrn_reflns_theta_min         2.708
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210.05(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -30.00  192
  2  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -90.00  192
  3  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 120.00  190
  4  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00-150.00  190
  5  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 -90.00  190
  6  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00  60.00  190
  7  ω    -23.00   6.00   0.50   27.23    --    5.37 -99.00 -90.00   58
  8  ω    -23.00  39.00   0.50   27.23    --    5.37 -99.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0421272000
_diffrn_orient_matrix_UB_12      -0.0432609000
_diffrn_orient_matrix_UB_13      -0.0291393000
_diffrn_orient_matrix_UB_21      0.0201566000
_diffrn_orient_matrix_UB_22      -0.0906414000
_diffrn_orient_matrix_UB_23      0.0132449000
_diffrn_orient_matrix_UB_31      -0.0066238000
_diffrn_orient_matrix_UB_32      -0.0008537000
_diffrn_orient_matrix_UB_33      0.0744463000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                859
_reflns_number_total             1076
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1076
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.030
_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)+(0.0629P)²+0.1263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1145
_refine_special_details          
'Atom sites C2 < C9, N2 and N3 were positionally disordered and modeled as split sites A and B. The site occupancies of the two sites were constrained to a total value of 1 and refined to 0.51 and 0.49 for the A and B sites, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, the rigid bond restraint RIGU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A = C6A-C7A = C9A-C8A = C9A-C5A = C1-C2A = C2A-C3A = C1-C2B = C2B-C3B
 1.38005 with sigma of 0.02
 C5B-C6B = C6B-C7B = C8B-C9B = C9B-C5B
 1.38005 with sigma of 0.02
 N1-C1 = C7A-N3A = C7B-N3B = C8A-N3A = C8B-N3B
 1.32696 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C1, N2B, C2B, N3B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N2A, C2A, C3A, N3A,
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H1B)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(N2B)=Sof(N3B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=0.5*(1-FVAR(2))
 Sof(N2A)=Sof(C3A)=Sof(N3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=0.5*FVAR(2)
 Sof(H1A)=Sof(C2A)=Sof(H2A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1B), C1(H1A), C2B(H2B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B),
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.31579(8) 0.500000 0.03899(15) 0.0551(4) Uani 1 2 d DS T P A .
C1 C 0.35984(7) 0.65950(18) 0.08421(14) 0.0621(4) Uani 1 1 d D . . . .
H1B H 0.335921 0.774137 0.035579 0.075 Uiso 0.494(5) 1 calc R U P A 2
H1A H 0.327352 0.774788 0.073083 0.075 Uiso 0.506(5) 1 calc R U P A 1
N2B N 0.5628(2) 0.500000 0.3691(3) 0.0588(10) Uani 0.494(5) 2 d S T P A 2
C2B C 0.4399(3) 0.6685(8) 0.2000(5) 0.0576(10) Uani 0.494(5) 1 d D . P A 2
H2B H 0.464533 0.786852 0.239820 0.069 Uiso 0.494(5) 1 calc R U P A 2
N3B N 0.8896(4) 0.500000 0.6466(6) 0.0526(14) Uani 0.494(5) 2 d DS T P A 2
C3B C 0.4819(2) 0.500000 0.2544(5) 0.0479(9) Uani 0.494(5) 2 d DS T P A 2
C4B C 0.6329(4) 0.500000 0.3332(6) 0.0496(12) Uani 0.494(5) 2 d S T P A 2
H4B H 0.629983 0.500000 0.227271 0.060 Uiso 0.494(5) 2 calc R U P A 2
C5B C 0.7222(10) 0.500000 0.4422(14) 0.046(2) Uani 0.494(5) 2 d DS T P A 2
C6B C 0.7978(5) 0.500000 0.3933(13) 0.063(2) Uani 0.494(5) 2 d DS T P A 2
H6B H 0.793964 0.500000 0.287040 0.075 Uiso 0.494(5) 2 calc R U P A 2
C7B C 0.8790(5) 0.500000 0.4971(9) 0.0607(18) Uani 0.494(5) 2 d DS T P A 2
H7B H 0.930601 0.500000 0.459950 0.073 Uiso 0.494(5) 2 calc R U P A 2
C8B C 0.8163(5) 0.500000 0.6952(9) 0.0564(15) Uani 0.494(5) 2 d DS T P A 2
H8B H 0.822574 0.500000 0.802284 0.068 Uiso 0.494(5) 2 calc R U P A 2
C9B C 0.7318(6) 0.500000 0.5988(11) 0.0489(16) Uani 0.494(5) 2 d DS T P A 2
H9B H 0.681127 0.500000 0.638599 0.059 Uiso 0.494(5) 2 calc R U P A 2
N2A N 0.5898(2) 0.500000 0.2489(4) 0.0725(12) Uani 0.506(5) 2 d S T P A 1
C2A C 0.4513(3) 0.6659(8) 0.1471(5) 0.0621(11) Uani 0.506(5) 1 d D . P A 1
H2A H 0.481534 0.784002 0.164112 0.075 Uiso 0.506(5) 1 calc R U P A 1
C3A C 0.4973(2) 0.500000 0.1842(5) 0.0541(9) Uani 0.506(5) 2 d DS T P A 1
N3A N 0.9015(4) 0.500000 0.5924(7) 0.0505(12) Uani 0.506(5) 2 d DS T P A 1
C4A C 0.6222(4) 0.500000 0.3860(7) 0.0514(12) Uani 0.506(5) 2 d S T P A 1
H4A H 0.583422 0.500000 0.451185 0.062 Uiso 0.506(5) 2 calc R U P A 1
C5A C 0.7184(10) 0.500000 0.4560(14) 0.043(2) Uani 0.506(5) 2 d DS T P A 1
C6A C 0.7796(5) 0.500000 0.3684(12) 0.0491(14) Uani 0.506(5) 2 d DS T P A 1
H6A H 0.759893 0.500000 0.260006 0.059 Uiso 0.506(5) 2 calc R U P A 1
C7A C 0.8694(5) 0.500000 0.4412(7) 0.0548(14) Uani 0.506(5) 2 d DS T P A 1
H7A H 0.910383 0.500000 0.380030 0.066 Uiso 0.506(5) 2 calc R U P A 1
C8A C 0.8423(5) 0.500000 0.6743(8) 0.0536(15) Uani 0.506(5) 2 d DS T P A 1
H8A H 0.863710 0.500000 0.782520 0.064 Uiso 0.506(5) 2 calc R U P A 1
C9A C 0.7525(6) 0.500000 0.6122(11) 0.0556(19) Uani 0.506(5) 2 d DS T P A 1
H9A H 0.713485 0.500000 0.676940 0.067 Uiso 0.506(5) 2 calc R U P A 1


_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 C1 1.3267(13) . ?
N1 C1 1.3268(13) 6_565 ?
C1 H1B 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2B 1.407(5) . ?
C1 C2A 1.391(5) . ?
N2B C3B 1.409(4) . ?
N2B C4B 1.219(7) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.385(5) . ?
N3B C7B 1.323(6) . ?
N3B C8B 1.327(6) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.482(15) . ?
C5B C6B 1.363(11) . ?
C5B C9B 1.389(11) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.365(7) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.377(6) . ?
C9B H9B 0.9500 . ?
N2A C3A 1.407(4) . ?
N2A C4A 1.213(7) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.368(5) . ?
N3A C7A 1.330(6) . ?
N3A C8A 1.328(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.466(15) . ?
C5A C6A 1.393(10) . ?
C5A C9A 1.376(11) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.382(6) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.365(7) . ?
C9A H9A 0.9500 . ?

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 C1 116.17(13) . 6_565 ?
N1 C1 H1B 118.1 . . ?
N1 C1 H1A 118.4 . . ?
N1 C1 C2B 123.7(2) . . ?
N1 C1 C2A 123.1(2) . . ?
C2B C1 H1B 118.1 . . ?
C2A C1 H1A 118.4 . . ?
C4B N2B C3B 119.6(4) . . ?
C1 C2B H2B 121.0 . . ?
C3B C2B C1 118.1(4) . . ?
C3B C2B H2B 121.0 . . ?
C7B N3B C8B 116.9(5) . . ?
C2B C3B N2B 120.7(2) . . ?
C2B C3B N2B 120.7(2) 6_565 . ?
N2B C4B H4B 117.5 . . ?
N2B C4B C5B 125.0(6) . . ?
C5B C4B H4B 117.5 . . ?
C6B C5B C4B 121.6(9) . . ?
C6B C5B C9B 117.6(14) . . ?
C9B C5B C4B 120.8(10) . . ?
C5B C6B H6B 120.0 . . ?
C5B C6B C7B 120.0(12) . . ?
C7B C6B H6B 120.0 . . ?
N3B C7B C6B 123.5(8) . . ?
N3B C7B H7B 118.3 . . ?
C6B C7B H7B 118.3 . . ?
N3B C8B H8B 118.2 . . ?
N3B C8B C9B 123.5(8) . . ?
C9B C8B H8B 118.2 . . ?
C5B C9B H9B 120.8 . . ?
C8B C9B C5B 118.5(11) . . ?
C8B C9B H9B 120.8 . . ?
C4A N2A C3A 122.2(4) . . ?
C1 C2A H2A 120.4 . . ?
C3A C2A C1 119.2(4) . . ?
C3A C2A H2A 120.4 . . ?
C2A C3A N2A 121.1(2) . . ?
C2A C3A N2A 121.1(2) 6_565 . ?
C2A C3A C2A 117.8(5) 6_565 . ?
C8A N3A C7A 116.6(5) . . ?
N2A C4A H4A 118.4 . . ?
N2A C4A C5A 123.2(6) . . ?
C5A C4A H4A 118.4 . . ?
C6A C5A C4A 121.9(10) . . ?
C9A C5A C4A 121.4(9) . . ?
C9A C5A C6A 116.7(13) . . ?
C5A C6A H6A 120.4 . . ?
C7A C6A C5A 119.1(11) . . ?
C7A C6A H6A 120.4 . . ?
N3A C7A C6A 123.6(7) . . ?
N3A C7A H7A 118.2 . . ?
C6A C7A H7A 118.2 . . ?
N3A C8A H8A 118.1 . . ?
N3A C8A C9A 123.8(7) . . ?
C9A C8A H8A 118.1 . . ?
C5A C9A H9A 119.9 . . ?
C8A C9A C5A 120.2(11) . . ?
C8A C9A H9A 119.9 . . ?

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 C1 C2B C3B 9.8(4) . . . . ?
N1 C1 C2A C3A -9.3(5) . . . . ?
C1 N1 C1 C2B -14.3(3) 6_565 . . . ?
C1 N1 C1 C2A 13.2(3) 6_565 . . . ?
C1 C2B C3B N2B 179.3(4) . . . . ?
C1 C2B C3B C2B -4.5(6) . . . 6_565 ?
C1 C2A C3A N2A -179.6(4) . . . . ?
C1 C2A C3A C2A 4.6(7) . . . 6_565 ?
N2B C4B C5B C6B 180.000(1) . . . . ?
N2B C4B C5B C9B 0.000(2) . . . . ?
N3B C8B C9B C5B 0.000(2) . . . . ?
C3B N2B C4B C5B 180.000(2) . . . . ?
C4B N2B C3B C2B 92.0(3) . . . 6_565 ?
C4B N2B C3B C2B -92.0(3) . . . . ?
C4B C5B C6B C7B 180.000(2) . . . . ?
C4B C5B C9B C8B 180.000(2) . . . . ?
C5B C6B C7B N3B 0.000(1) . . . . ?
C6B C5B C9B C8B 0.000(2) . . . . ?
C7B N3B C8B C9B 0.000(2) . . . . ?
C8B N3B C7B C6B 0.000(2) . . . . ?
C9B C5B C6B C7B 0.000(2) . . . . ?
N2A C4A C5A C6A 0.000(2) . . . . ?
N2A C4A C5A C9A 180.000(2) . . . . ?
C3A N2A C4A C5A 180.000(2) . . . . ?
N3A C8A C9A C5A 0.000(2) . . . . ?
C4A N2A C3A C2A 92.2(3) . . . . ?
C4A N2A C3A C2A -92.2(3) . . . 6_565 ?
C4A C5A C6A C7A 180.000(2) . . . . ?
C4A C5A C9A C8A 180.000(2) . . . . ?
C5A C6A C7A N3A 0.000(2) . . . . ?
C6A C5A C9A C8A 0.000(2) . . . . ?
C7A N3A C8A C9A 0.000(2) . . . . ?
C8A N3A C7A C6A 0.000(1) . . . . ?
C9A C5A C6A C7A 0.000(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1450
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.974
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_BPI_250_00
_database_code_depnum_ccdc_archive 'CCDC 2072414'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.6639(12)
_cell_length_b                   7.0936(6)
_cell_length_c                   9.0904(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.663(9)
_cell_angle_gamma                90
_cell_volume                     972.56(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4481
_cell_measurement_temperature    250.05(10)
_cell_measurement_theta_max      29.8540
_cell_measurement_theta_min      2.6870
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 1 -12 0.0715
-19 -5 0 0.1270
-7 0 13 0.0659
20 4 -6 0.0934
15 5 5 0.1311
-11 9 0 0.0169
10 -9 1 0.0094
12 -4 -11 0.0728

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.6527 0.5776 -12.4515 -0.1135 0.0016 -0.9935
-18.7917 -4.8561 0.4774 0.9879 -0.0251 0.1533
-6.8057 0.4941 12.7882 -0.1047 0.0040 0.9945
19.5864 4.1653 -5.5161 -0.8457 0.0209 -0.5333
14.9146 4.7485 4.6291 -0.9676 0.0251 0.2511
-10.7966 8.6699 0.4753 -0.0253 -0.9945 0.1015
9.8824 -8.7162 0.9320 0.0256 0.9996 0.0090
12.2572 -3.8656 -11.0091 0.0104 0.4449 -0.8955

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8449
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.353
_diffrn_reflns_theta_min         2.701
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.05(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -30.00  192
  2  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -90.00  192
  3  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 120.00  190
  4  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00-150.00  190
  5  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 -90.00  190
  6  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00  60.00  190
  7  ω    -23.00   6.00   0.50   27.23    --    5.37 -99.00 -90.00   58
  8  ω    -23.00  39.00   0.50   27.23    --    5.37 -99.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0400230000
_diffrn_orient_matrix_UB_12      -0.0512541000
_diffrn_orient_matrix_UB_13      -0.0275038000
_diffrn_orient_matrix_UB_21      0.0239253000
_diffrn_orient_matrix_UB_22      -0.0858116000
_diffrn_orient_matrix_UB_23      0.0163585000
_diffrn_orient_matrix_UB_31      -0.0062287000
_diffrn_orient_matrix_UB_32      -0.0001360000
_diffrn_orient_matrix_UB_33      0.0744573000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                808
_reflns_number_total             1086
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.079
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1086
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      0.988
_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)+(0.0636P)²+0.0934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          
'Atom sites C2 < C9, N2 and N3 were positionally disordered and modeled as split sites A and B. The site occupancies of the two sites were constrained to a total value of 1 and refined to 0.51 and 0.49 for the A and B sites, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, the rigid bond restraint RIGU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A = C6A-C7A = C9A-C8A = C9A-C5A = C1-C2A = C2A-C3A = C1-C2B = C2B-C3B
 1.37729 with sigma of 0.02
 C5B-C6B = C6B-C7B = C8B-C9B = C9B-C5B
 1.37729 with sigma of 0.02
 N1-C1 = C7A-N3A = C7B-N3B = C8A-N3A = C8B-N3B
 1.32462 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C1, N2B, C2B, N3B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N2A, C2A, C3A, N3A,
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H1b)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(N2B)=Sof(N3B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=0.5*(1-FVAR(2))
 Sof(N2A)=Sof(C3A)=Sof(N3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=0.5*FVAR(2)
 Sof(H1a)=Sof(C2A)=Sof(H2A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1b), C1(H1a), C2B(H2B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B),
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.31597(8) 0.500000 0.03994(15) 0.0644(4) Uani 1 2 d DS T P A .
C1 C 0.36009(7) 0.65831(18) 0.08480(14) 0.0681(4) Uani 1 1 d D . . . .
H1B H 0.334650 0.772730 0.038801 0.082 Uiso 0.490(6) 1 calc R U P A 2
H1A H 0.328271 0.773867 0.068321 0.082 Uiso 0.510(6) 1 calc R U P A 1
N2B N 0.5647(2) 0.500000 0.3637(3) 0.0656(12) Uani 0.490(6) 2 d S T P A 2
C2B C 0.4415(5) 0.6682(13) 0.1952(8) 0.0662(15) Uani 0.490(6) 1 d D . P A 2
H2B H 0.467186 0.786114 0.232368 0.079 Uiso 0.490(6) 1 calc R U P A 2
N3B N 0.8907(6) 0.500000 0.6408(9) 0.0587(17) Uani 0.490(6) 2 d DS T P A 2
C3B C 0.4837(3) 0.500000 0.2489(5) 0.0539(10) Uani 0.490(6) 2 d DS T P A 2
C4B C 0.6353(4) 0.500000 0.3270(6) 0.0549(11) Uani 0.490(6) 2 d S T P A 2
H4B H 0.632392 0.500000 0.221232 0.066 Uiso 0.490(6) 2 calc R U P A 2
C5B C 0.7233(9) 0.500000 0.4374(12) 0.0507(19) Uani 0.490(6) 2 d DS T P A 2
C6B C 0.7980(6) 0.500000 0.3857(16) 0.074(3) Uani 0.490(6) 2 d DS T P A 2
H6B H 0.793580 0.500000 0.279429 0.089 Uiso 0.490(6) 2 calc R U P A 2
C7B C 0.8790(6) 0.500000 0.4912(12) 0.072(2) Uani 0.490(6) 2 d DS T P A 2
H7B H 0.930349 0.500000 0.454475 0.086 Uiso 0.490(6) 2 calc R U P A 2
C8B C 0.8178(6) 0.500000 0.6895(13) 0.0605(17) Uani 0.490(6) 2 d DS T P A 2
H8B H 0.824544 0.500000 0.796563 0.073 Uiso 0.490(6) 2 calc R U P A 2
C9B C 0.7334(7) 0.500000 0.5933(12) 0.0571(16) Uani 0.490(6) 2 d DS T P A 2
H9B H 0.683193 0.500000 0.633005 0.069 Uiso 0.490(6) 2 calc R U P A 2
N2A N 0.5884(2) 0.500000 0.2561(4) 0.0793(13) Uani 0.510(6) 2 d S T P A 1
C2A C 0.4498(5) 0.6637(13) 0.1542(9) 0.0709(16) Uani 0.510(6) 1 d D . P A 1
H2A H 0.479444 0.781407 0.176237 0.085 Uiso 0.510(6) 1 calc R U P A 1
C3A C 0.4959(3) 0.500000 0.1910(5) 0.0604(11) Uani 0.510(6) 2 d DS T P A 1
N3A N 0.9010(5) 0.500000 0.5972(9) 0.0583(16) Uani 0.510(6) 2 d DS T P A 1
C4A C 0.6207(3) 0.500000 0.3915(7) 0.0581(10) Uani 0.510(6) 2 d S T P A 1
H4A H 0.582432 0.500000 0.456702 0.070 Uiso 0.510(6) 2 calc R U P A 1
C5A C 0.7175(8) 0.500000 0.4615(13) 0.0516(18) Uani 0.510(6) 2 d DS T P A 1
C6A C 0.7781(5) 0.500000 0.3763(13) 0.0568(15) Uani 0.510(6) 2 d DS T P A 1
H6A H 0.757808 0.500000 0.267934 0.068 Uiso 0.510(6) 2 calc R U P A 1
C7A C 0.8680(7) 0.500000 0.4469(9) 0.0640(16) Uani 0.510(6) 2 d DS T P A 1
H7A H 0.907991 0.500000 0.384718 0.077 Uiso 0.510(6) 2 calc R U P A 1
C8A C 0.8426(6) 0.500000 0.6785(11) 0.0614(18) Uani 0.510(6) 2 d DS T P A 1
H8A H 0.864665 0.500000 0.786633 0.074 Uiso 0.510(6) 2 calc R U P A 1
C9A C 0.7519(7) 0.500000 0.6170(11) 0.062(2) Uani 0.510(6) 2 d DS T P A 1
H9A H 0.713534 0.500000 0.681997 0.075 Uiso 0.510(6) 2 calc R U P A 1


_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 C1 1.3239(13) . ?
N1 C1 1.3239(13) 6_565 ?
C1 H1B 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2B 1.396(8) . ?
C1 C2A 1.377(8) . ?
N2B C3B 1.409(5) . ?
N2B C4B 1.237(8) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.387(7) . ?
N3B C7B 1.322(7) . ?
N3B C8B 1.331(6) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.470(13) . ?
C5B C6B 1.374(9) . ?
C5B C9B 1.383(9) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.368(8) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.374(7) . ?
C9B H9B 0.9500 . ?
N2A C3A 1.410(6) . ?
N2A C4A 1.198(8) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.361(8) . ?
N3A C7A 1.325(6) . ?
N3A C8A 1.321(7) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.477(13) . ?
C5A C6A 1.377(8) . ?
C5A C9A 1.370(9) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.381(7) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.380(7) . ?
C9A H9A 0.9500 . ?

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 C1 116.03(13) . 6_565 ?
N1 C1 H1B 117.8 . . ?
N1 C1 H1A 118.4 . . ?
N1 C1 C2B 124.3(4) . . ?
N1 C1 C2A 123.2(4) . . ?
C2B C1 H1B 117.8 . . ?
C2A C1 H1A 118.4 . . ?
C4B N2B C3B 119.5(4) . . ?
C1 C2B H2B 121.1 . . ?
C3B C2B C1 117.8(7) . . ?
C3B C2B H2B 121.1 . . ?
C7B N3B C8B 116.7(7) . . ?
C2B C3B N2B 120.6(4) . . ?
C2B C3B N2B 120.6(4) 6_565 . ?
C2B C3B C2B 118.7(8) 6_565 . ?
N2B C4B H4B 118.1 . . ?
N2B C4B C5B 123.8(6) . . ?
C5B C4B H4B 118.1 . . ?
C6B C5B C4B 119.7(8) . . ?
C6B C5B C9B 118.5(13) . . ?
C9B C5B C4B 121.8(9) . . ?
C5B C6B H6B 120.8 . . ?
C7B C6B C5B 118.4(13) . . ?
C7B C6B H6B 120.8 . . ?
N3B C7B C6B 124.4(10) . . ?
N3B C7B H7B 117.8 . . ?
C6B C7B H7B 117.8 . . ?
N3B C8B H8B 118.2 . . ?
N3B C8B C9B 123.5(10) . . ?
C9B C8B H8B 118.2 . . ?
C5B C9B H9B 120.8 . . ?
C8B C9B C5B 118.5(13) . . ?
C8B C9B H9B 120.8 . . ?
C4A N2A C3A 122.2(4) . . ?
C1 C2A H2A 120.1 . . ?
C3A C2A C1 119.8(7) . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A N2A 121.3(4) 6_565 . ?
C2A C3A N2A 121.3(4) . . ?
C2A C3A C2A 117.2(8) . 6_565 ?
C8A N3A C7A 116.1(7) . . ?
N2A C4A H4A 118.6 . . ?
N2A C4A C5A 122.8(6) . . ?
C5A C4A H4A 118.6 . . ?
C6A C5A C4A 122.7(9) . . ?
C9A C5A C4A 121.1(8) . . ?
C9A C5A C6A 116.2(13) . . ?
C5A C6A H6A 119.7 . . ?
C5A C6A C7A 120.7(11) . . ?
C7A C6A H6A 119.7 . . ?
N3A C7A C6A 123.0(10) . . ?
N3A C7A H7A 118.5 . . ?
C6A C7A H7A 118.5 . . ?
N3A C8A H8A 117.8 . . ?
N3A C8A C9A 124.5(9) . . ?
C9A C8A H8A 117.8 . . ?
C5A C9A C8A 119.6(12) . . ?
C5A C9A H9A 120.2 . . ?
C8A C9A H9A 120.2 . . ?

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 C1 C2B C3B 7.6(7) . . . . ?
N1 C1 C2A C3A -5.5(8) . . . . ?
C1 N1 C1 C2B -11.9(4) 6_565 . . . ?
C1 N1 C1 C2A 9.4(5) 6_565 . . . ?
C1 C2B C3B N2B -178.1(4) . . . . ?
C1 C2B C3B C2B -2.6(10) . . . 6_565 ?
C1 C2A C3A N2A 177.2(5) . . . . ?
C1 C2A C3A C2A 1.0(11) . . . 6_565 ?
N2B C4B C5B C6B 180.000(1) . . . . ?
N2B C4B C5B C9B 0.000(2) . . . . ?
N3B C8B C9B C5B 0.000(2) . . . . ?
C3B N2B C4B C5B 180.000(1) . . . . ?
C4B N2B C3B C2B -92.3(4) . . . . ?
C4B N2B C3B C2B 92.3(4) . . . 6_565 ?
C4B C5B C6B C7B 180.000(2) . . . . ?
C4B C5B C9B C8B 180.000(2) . . . . ?
C5B C6B C7B N3B 0.000(2) . . . . ?
C6B C5B C9B C8B 0.000(2) . . . . ?
C7B N3B C8B C9B 0.000(2) . . . . ?
C8B N3B C7B C6B 0.000(2) . . . . ?
C9B C5B C6B C7B 0.000(2) . . . . ?
N2A C4A C5A C6A 0.000(2) . . . . ?
N2A C4A C5A C9A 180.000(2) . . . . ?
C3A N2A C4A C5A 180.000(1) . . . . ?
N3A C8A C9A C5A 0.000(2) . . . . ?
C4A N2A C3A C2A 92.0(5) . . . . ?
C4A N2A C3A C2A -92.0(5) . . . 6_565 ?
C4A C5A C6A C7A 180.000(2) . . . . ?
C4A C5A C9A C8A 180.000(2) . . . . ?
C5A C6A C7A N3A 0.000(2) . . . . ?
C6A C5A C9A C8A 0.000(2) . . . . ?
C7A N3A C8A C9A 0.000(2) . . . . ?
C8A N3A C7A C6A 0.000(1) . . . . ?
C9A C5A C6A C7A 0.000(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1417
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.764
####################################################################### 
# 
# 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_BPI_270_00
_database_code_depnum_ccdc_archive 'CCDC 2072415'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.6931(11)
_cell_length_b                   7.1110(5)
_cell_length_c                   9.0908(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.856(8)
_cell_angle_gamma                90
_cell_volume                     975.88(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4178
_cell_measurement_temperature    270.06(10)
_cell_measurement_theta_max      29.8770
_cell_measurement_theta_min      2.7140
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 1 -13 0.0715
-19 -5 1 0.1270
-6 0 13 0.0659
20 4 -6 0.0934
16 4 4 0.1311
-10 9 1 0.0169
9 -9 1 0.0094
12 -4 -11 0.0728

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.2644 0.7050 -12.5083 -0.1135 0.0016 -0.9935
-19.2459 -4.5465 0.6576 0.9879 -0.0251 0.1533
-6.3014 0.2925 12.8065 -0.1047 0.0040 0.9945
19.7937 3.9674 -5.6853 -0.8457 0.0209 -0.5333
15.5406 4.3783 4.4674 -0.9676 0.0251 0.2511
-10.2878 8.8577 0.8735 -0.0253 -0.9945 0.1015
9.4210 -8.9234 0.5359 0.0256 0.9996 0.0090
11.6459 -3.8083 -11.2193 0.0104 0.4449 -0.8955

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.699
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      270.06(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -30.00  192
  2  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -90.00  192
  3  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 120.00  190
  4  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00-150.00  190
  5  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 -90.00  190
  6  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00  60.00  190
  7  ω    -23.00   6.00   0.50   27.23    --    5.37 -99.00 -90.00   58
  8  ω    -23.00  39.00   0.50   27.23    --    5.37 -99.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0409762000
_diffrn_orient_matrix_UB_12      -0.0477644000
_diffrn_orient_matrix_UB_13      -0.0272439000
_diffrn_orient_matrix_UB_21      0.0224373000
_diffrn_orient_matrix_UB_22      -0.0875335000
_diffrn_orient_matrix_UB_23      0.0133494000
_diffrn_orient_matrix_UB_31      -0.0049786000
_diffrn_orient_matrix_UB_32      -0.0017488000
_diffrn_orient_matrix_UB_33      0.0752459000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                786
_reflns_number_total             1091
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.072
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.023
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1091
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      0.989
_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)+(0.0651P)²+0.0717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          
'Atom sites C2 < C9, N2 and N3 were positionally disordered and modeled as split sites A and B. The site occupancies of the two sites were constrained to a total value of 1 and refined to 0.51 and 0.49 for the A and B sites, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, the rigid bond restraint RIGU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A = C6A-C7A = C9A-C8A = C9A-C5A = C1-C2A = C2A-C3A = C1-C2B = C2B-C3B
 1.37583 with sigma of 0.02
 C5B-C6B = C6B-C7B = C8B-C9B = C9B-C5B
 1.37583 with sigma of 0.02
 N1-C1 = C7A-N3A = C7B-N3B = C8A-N3A = C8B-N3B
 1.32266 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C1, N2B, C2B, N3B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N2A, C2A, C3A, N3A,
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H1b)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(N2B)=Sof(N3B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=0.5*(1-FVAR(2))
 Sof(N2A)=Sof(C3A)=Sof(N3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=0.5*FVAR(2)
 Sof(H1a)=Sof(C2A)=Sof(H2A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1b), C1(H1a), C2B(H2B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B),
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.31614(8) 0.500000 0.04042(16) 0.0697(4) Uani 1 2 d DS T P A .
C1 C 0.36026(7) 0.65790(19) 0.08529(15) 0.0738(4) Uani 1 1 d D . . . .
H1B H 0.334670 0.772125 0.039566 0.089 Uiso 0.493(7) 1 calc R U P A 2
H1A H 0.328499 0.773224 0.068789 0.089 Uiso 0.507(7) 1 calc R U P A 1
N2B N 0.5652(2) 0.500000 0.3627(4) 0.0698(13) Uani 0.493(7) 2 d S T P A 2
C2B C 0.4420(5) 0.6675(13) 0.1955(9) 0.0713(17) Uani 0.493(7) 1 d D . P A 2
H2B H 0.468010 0.785039 0.232477 0.086 Uiso 0.493(7) 1 calc R U P A 2
N3B N 0.8906(6) 0.500000 0.6411(9) 0.0654(19) Uani 0.493(7) 2 d DS T P A 2
C3B C 0.4838(3) 0.500000 0.2489(6) 0.0567(10) Uani 0.493(7) 2 d DS T P A 2
C4B C 0.6350(4) 0.500000 0.3263(6) 0.0596(11) Uani 0.493(7) 2 d S T P A 2
H4B H 0.631986 0.500000 0.220539 0.071 Uiso 0.493(7) 2 calc R U P A 2
C5B C 0.7237(8) 0.500000 0.4380(12) 0.0538(19) Uani 0.493(7) 2 d DS T P A 2
C6B C 0.7978(6) 0.500000 0.3836(16) 0.079(3) Uani 0.493(7) 2 d DS T P A 2
H6B H 0.793232 0.500000 0.277229 0.095 Uiso 0.493(7) 2 calc R U P A 2
C7B C 0.8785(7) 0.500000 0.4915(12) 0.078(2) Uani 0.493(7) 2 d DS T P A 2
H7B H 0.929976 0.500000 0.455592 0.094 Uiso 0.493(7) 2 calc R U P A 2
C8B C 0.8182(6) 0.500000 0.6896(13) 0.0656(18) Uani 0.493(7) 2 d DS T P A 2
H8B H 0.825007 0.500000 0.796737 0.079 Uiso 0.493(7) 2 calc R U P A 2
C9B C 0.7337(7) 0.500000 0.5929(12) 0.0624(17) Uani 0.493(7) 2 d DS T P A 2
H9B H 0.683565 0.500000 0.632312 0.075 Uiso 0.493(7) 2 calc R U P A 2
N2A N 0.5885(2) 0.500000 0.2566(5) 0.0850(14) Uani 0.507(7) 2 d S T P A 1
C2A C 0.4492(5) 0.6630(14) 0.1542(9) 0.0755(18) Uani 0.507(7) 1 d D . P A 1
H2A H 0.478817 0.780463 0.176461 0.091 Uiso 0.507(7) 1 calc R U P A 1
C3A C 0.4955(3) 0.500000 0.1908(6) 0.0643(11) Uani 0.507(7) 2 d DS T P A 1
N3A N 0.9013(6) 0.500000 0.5983(10) 0.0609(16) Uani 0.507(7) 2 d DS T P A 1
C4A C 0.6208(4) 0.500000 0.3924(7) 0.0636(11) Uani 0.507(7) 2 d S T P A 1
H4A H 0.582754 0.500000 0.457756 0.076 Uiso 0.507(7) 2 calc R U P A 1
C5A C 0.7171(9) 0.500000 0.4612(14) 0.058(2) Uani 0.507(7) 2 d DS T P A 1
C6A C 0.7775(6) 0.500000 0.3784(13) 0.0621(15) Uani 0.507(7) 2 d DS T P A 1
H6A H 0.756984 0.500000 0.269887 0.074 Uiso 0.507(7) 2 calc R U P A 1
C7A C 0.8679(7) 0.500000 0.4475(10) 0.0681(17) Uani 0.507(7) 2 d DS T P A 1
H7A H 0.907394 0.500000 0.384696 0.082 Uiso 0.507(7) 2 calc R U P A 1
C8A C 0.8430(6) 0.500000 0.6784(11) 0.0661(19) Uani 0.507(7) 2 d DS T P A 1
H8A H 0.864948 0.500000 0.786679 0.079 Uiso 0.507(7) 2 calc R U P A 1
C9A C 0.7524(7) 0.500000 0.6167(12) 0.067(2) Uani 0.507(7) 2 d DS T P A 1
H9A H 0.714366 0.500000 0.682081 0.081 Uiso 0.507(7) 2 calc R U P A 1


_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 C1 1.3237(14) 6_565 ?
N1 C1 1.3237(14) . ?
C1 H1B 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2B 1.398(8) . ?
C1 C2A 1.366(8) . ?
N2B C3B 1.407(5) . ?
N2B C4B 1.227(8) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.382(8) . ?
N3B C7B 1.321(8) . ?
N3B C8B 1.326(7) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.481(12) . ?
C5B C6B 1.384(8) . ?
C5B C9B 1.374(10) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.374(9) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.376(7) . ?
C9B H9B 0.9500 . ?
N2A C3A 1.418(6) . ?
N2A C4A 1.199(9) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.360(8) . ?
N3A C7A 1.327(7) . ?
N3A C8A 1.316(7) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.469(14) . ?
C5A C6A 1.362(8) . ?
C5A C9A 1.370(10) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.386(8) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.379(7) . ?
C9A H9A 0.9500 . ?

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 C1 116.05(14) 6_565 . ?
N1 C1 H1B 117.9 . . ?
N1 C1 H1A 118.4 . . ?
N1 C1 C2B 124.3(4) . . ?
N1 C1 C2A 123.2(4) . . ?
C2B C1 H1B 117.9 . . ?
C2A C1 H1A 118.4 . . ?
C4B N2B C3B 120.0(4) . . ?
C1 C2B H2B 121.2 . . ?
C3B C2B C1 117.6(7) . . ?
C3B C2B H2B 121.2 . . ?
C7B N3B C8B 116.6(8) . . ?
C2B C3B N2B 120.4(4) . . ?
C2B C3B N2B 120.4(4) 6_565 . ?
C2B C3B C2B 119.1(9) 6_565 . ?
N2B C4B H4B 118.1 . . ?
N2B C4B C5B 123.8(6) . . ?
C5B C4B H4B 118.1 . . ?
C6B C5B C4B 118.7(8) . . ?
C9B C5B C4B 121.7(9) . . ?
C9B C5B C6B 119.6(13) . . ?
C5B C6B H6B 121.7 . . ?
C7B C6B C5B 116.5(12) . . ?
C7B C6B H6B 121.7 . . ?
N3B C7B C6B 125.4(10) . . ?
N3B C7B H7B 117.3 . . ?
C6B C7B H7B 117.3 . . ?
N3B C8B H8B 118.3 . . ?
N3B C8B C9B 123.4(10) . . ?
C9B C8B H8B 118.3 . . ?
C5B C9B C8B 118.4(13) . . ?
C5B C9B H9B 120.8 . . ?
C8B C9B H9B 120.8 . . ?
C4A N2A C3A 122.1(4) . . ?
C1 C2A H2A 120.0 . . ?
C3A C2A C1 120.0(8) . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A N2A 121.5(5) . . ?
C2A C3A N2A 121.5(5) 6_565 . ?
C2A C3A C2A 116.9(9) 6_565 . ?
C8A N3A C7A 115.7(8) . . ?
N2A C4A H4A 118.9 . . ?
N2A C4A C5A 122.3(6) . . ?
C5A C4A H4A 118.9 . . ?
C6A C5A C4A 123.7(9) . . ?
C6A C5A C9A 115.1(13) . . ?
C9A C5A C4A 121.2(9) . . ?
C5A C6A H6A 119.0 . . ?
C5A C6A C7A 122.0(11) . . ?
C7A C6A H6A 119.0 . . ?
N3A C7A C6A 122.3(10) . . ?
N3A C7A H7A 118.9 . . ?
C6A C7A H7A 118.9 . . ?
N3A C8A H8A 117.6 . . ?
N3A C8A C9A 124.8(9) . . ?
C9A C8A H8A 117.6 . . ?
C5A C9A C8A 120.1(12) . . ?
C5A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?

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 C1 C2B C3B 7.2(8) . . . . ?
N1 C1 C2A C3A -5.3(9) . . . . ?
C1 N1 C1 C2B -11.7(5) 6_565 . . . ?
C1 N1 C1 C2A 9.4(5) 6_565 . . . ?
C1 C2B C3B N2B -178.5(5) . . . . ?
C1 C2B C3B C2B -2.1(11) . . . 6_565 ?
C1 C2A C3A N2A 177.4(5) . . . . ?
C1 C2A C3A C2A 0.7(12) . . . 6_565 ?
N2B C4B C5B C6B 180.000(1) . . . . ?
N2B C4B C5B C9B 0.000(2) . . . . ?
N3B C8B C9B C5B 0.000(2) . . . . ?
C3B N2B C4B C5B 180.000(1) . . . . ?
C4B N2B C3B C2B 91.9(5) . . . 6_565 ?
C4B N2B C3B C2B -91.9(5) . . . . ?
C4B C5B C6B C7B 180.000(2) . . . . ?
C4B C5B C9B C8B 180.000(2) . . . . ?
C5B C6B C7B N3B 0.000(2) . . . . ?
C6B C5B C9B C8B 0.000(2) . . . . ?
C7B N3B C8B C9B 0.000(2) . . . . ?
C8B N3B C7B C6B 0.000(2) . . . . ?
C9B C5B C6B C7B 0.000(3) . . . . ?
N2A C4A C5A C6A 0.000(2) . . . . ?
N2A C4A C5A C9A 180.000(2) . . . . ?
C3A N2A C4A C5A 180.000(1) . . . . ?
N3A C8A C9A C5A 0.000(2) . . . . ?
C4A N2A C3A C2A -91.7(5) . . . 6_565 ?
C4A N2A C3A C2A 91.7(5) . . . . ?
C4A C5A C6A C7A 180.000(2) . . . . ?
C4A C5A C9A C8A 180.000(2) . . . . ?
C5A C6A C7A N3A 0.000(2) . . . . ?
C6A C5A C9A C8A 0.000(2) . . . . ?
C7A N3A C8A C9A 0.000(2) . . . . ?
C8A N3A C7A C6A 0.000(2) . . . . ?
C9A C5A C6A C7A 0.000(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1424
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_BPI_230_00_autored
_database_code_depnum_ccdc_archive 'CCDC 2072413'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.6264(11)
_cell_length_b                   7.0823(5)
_cell_length_c                   9.0843(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.399(8)
_cell_angle_gamma                90
_cell_volume                     969.27(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4735
_cell_measurement_temperature    230.06(10)
_cell_measurement_theta_max      29.8730
_cell_measurement_theta_min      2.7050
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 1 -12 0.0607
-19 -4 0 0.1241
-7 0 13 0.0777
20 4 -5 0.0912
15 4 5 0.1385
-10 9 0 0.0147
9 -9 1 0.0129
12 -4 -11 0.0641

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.7698 0.5188 -12.4179 -0.1135 0.0016 -0.9935
-19.1404 -4.4799 0.3462 0.9879 -0.0251 0.1533
-6.8486 0.4704 12.7830 -0.1047 0.0040 0.9945
19.9166 3.8368 -5.3962 -0.8457 0.0209 -0.5333
15.2244 4.3864 4.7500 -0.9676 0.0251 0.2511
-9.9875 8.8514 0.4652 -0.0253 -0.9945 0.1015
9.0604 -8.8967 0.9400 0.0256 0.9996 0.0090
11.9619 -3.9610 -10.9883 0.0104 0.4449 -0.8955

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8389
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_min         2.704
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230.06(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -30.00  192
  2  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -90.00  192
  3  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 120.00  190
  4  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00-150.00  190
  5  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 -90.00  190
  6  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00  60.00  190
  7  ω    -23.00   6.00   0.50   27.23    --    5.37 -99.00 -90.00   58
  8  ω    -23.00  39.00   0.50   27.23    --    5.37 -99.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0409817000
_diffrn_orient_matrix_UB_12      -0.0476111000
_diffrn_orient_matrix_UB_13      -0.0283919000
_diffrn_orient_matrix_UB_21      0.0222114000
_diffrn_orient_matrix_UB_22      -0.0881069000
_diffrn_orient_matrix_UB_23      0.0154530000
_diffrn_orient_matrix_UB_31      -0.0066720000
_diffrn_orient_matrix_UB_32      0.0000333000
_diffrn_orient_matrix_UB_33      0.0742231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                838
_reflns_number_total             1082
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.025
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1082
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      0.990
_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)+(0.0677P)²+0.0811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          
'Atom sites C2 < C9, N2 and N3 were positionally disordered and modeled as split sites A and B. The site occupancies of the two sites were constrained to a total value of 1 and refined to 0.51 and 0.49 for the A and B sites, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, the rigid bond restraint RIGU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A = C6A-C7A = C9A-C8A = C9A-C5A = C1-C2A = C2A-C3A = C1-C2B = C2B-C3B
 1.37762 with sigma of 0.02
 C5B-C6B = C6B-C7B = C8B-C9B = C9B-C5B
 1.37762 with sigma of 0.02
 N1-C1 = C7A-N3A = C7B-N3B = C8A-N3A = C8B-N3B
 1.32877 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C1, N2B, C2B, N3B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N2A, C2A, C3A, N3A,
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H1b)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(N2B)=Sof(N3B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=0.5*(1-FVAR(2))
 Sof(N2A)=Sof(C3A)=Sof(N3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=0.5*FVAR(2)
 Sof(H1a)=Sof(C2A)=Sof(H2A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1b), C1(H1a), C2B(H2B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B),
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.31587(8) 0.500000 0.03965(14) 0.0599(4) Uani 1 2 d DS T P A .
C1 C 0.36004(7) 0.65919(17) 0.08446(14) 0.0640(4) Uani 1 1 d D . . . .
H1B H 0.334810 0.773604 0.037869 0.077 Uiso 0.488(6) 1 calc R U P A 2
H1A H 0.328233 0.775014 0.069025 0.077 Uiso 0.512(6) 1 calc R U P A 1
N2B N 0.5641(2) 0.500000 0.3646(3) 0.0618(11) Uani 0.488(6) 2 d S T P A 2
C2B C 0.4413(4) 0.6695(11) 0.1959(7) 0.0610(13) Uani 0.488(6) 1 d D . P A 2
H2B H 0.466868 0.787525 0.233447 0.073 Uiso 0.488(6) 1 calc R U P A 2
N3B N 0.8905(6) 0.500000 0.6416(8) 0.0560(16) Uani 0.488(6) 2 d DS T P A 2
C3B C 0.4833(2) 0.500000 0.2494(5) 0.0500(9) Uani 0.488(6) 2 d DS T P A 2
C4B C 0.6347(3) 0.500000 0.3280(6) 0.0520(10) Uani 0.488(6) 2 d S T P A 2
H4B H 0.632087 0.500000 0.222353 0.062 Uiso 0.488(6) 2 calc R U P A 2
C5B C 0.7236(8) 0.500000 0.4396(12) 0.0475(19) Uani 0.488(6) 2 d DS T P A 2
C6B C 0.7981(5) 0.500000 0.3851(15) 0.069(2) Uani 0.488(6) 2 d DS T P A 2
H6B H 0.793475 0.500000 0.278708 0.083 Uiso 0.488(6) 2 calc R U P A 2
C7B C 0.8793(6) 0.500000 0.4912(11) 0.067(2) Uani 0.488(6) 2 d DS T P A 2
H7B H 0.930894 0.500000 0.454663 0.080 Uiso 0.488(6) 2 calc R U P A 2
C8B C 0.8167(5) 0.500000 0.6891(12) 0.0572(16) Uani 0.488(6) 2 d DS T P A 2
H8B H 0.823215 0.500000 0.796049 0.069 Uiso 0.488(6) 2 calc R U P A 2
C9B C 0.7321(7) 0.500000 0.5946(11) 0.0528(16) Uani 0.488(6) 2 d DS T P A 2
H9B H 0.681657 0.500000 0.634276 0.063 Uiso 0.488(6) 2 calc R U P A 2
N2A N 0.5887(2) 0.500000 0.2545(4) 0.0759(12) Uani 0.512(6) 2 d S T P A 1
C2A C 0.4497(4) 0.6634(11) 0.1522(7) 0.0671(15) Uani 0.512(6) 1 d D . P A 1
H2A H 0.479563 0.781245 0.173135 0.081 Uiso 0.512(6) 1 calc R U P A 1
C3A C 0.4961(3) 0.500000 0.1893(5) 0.0582(10) Uani 0.512(6) 2 d DS T P A 1
N3A N 0.9009(5) 0.500000 0.5969(9) 0.0551(15) Uani 0.512(6) 2 d DS T P A 1
C4A C 0.6207(3) 0.500000 0.3906(6) 0.0546(10) Uani 0.512(6) 2 d S T P A 1
H4A H 0.582196 0.500000 0.455802 0.066 Uiso 0.512(6) 2 calc R U P A 1
C5A C 0.7168(8) 0.500000 0.4594(12) 0.0474(17) Uani 0.512(6) 2 d DS T P A 1
C6A C 0.7779(5) 0.500000 0.3764(12) 0.0536(14) Uani 0.512(6) 2 d DS T P A 1
H6A H 0.758055 0.500000 0.268087 0.064 Uiso 0.512(6) 2 calc R U P A 1
C7A C 0.8676(7) 0.500000 0.4462(9) 0.0615(15) Uani 0.512(6) 2 d DS T P A 1
H7A H 0.907557 0.500000 0.383614 0.074 Uiso 0.512(6) 2 calc R U P A 1
C8A C 0.8427(5) 0.500000 0.6790(10) 0.0559(16) Uani 0.512(6) 2 d DS T P A 1
H8A H 0.864251 0.500000 0.787102 0.067 Uiso 0.512(6) 2 calc R U P A 1
C9A C 0.7521(6) 0.500000 0.6157(10) 0.0564(18) Uani 0.512(6) 2 d DS T P A 1
H9A H 0.713469 0.500000 0.680726 0.068 Uiso 0.512(6) 2 calc R U P A 1


_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 C1 1.3281(13) 6_565 ?
N1 C1 1.3281(13) . ?
C1 H1B 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2B 1.400(7) . ?
C1 C2A 1.373(7) . ?
N2B C3B 1.409(5) . ?
N2B C4B 1.233(7) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.392(6) . ?
N3B C7B 1.330(7) . ?
N3B C8B 1.335(6) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.486(13) . ?
C5B C6B 1.382(8) . ?
C5B C9B 1.379(10) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.374(8) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.371(6) . ?
C9B H9B 0.9500 . ?
N2A C3A 1.409(5) . ?
N2A C4A 1.204(7) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.360(7) . ?
N3A C7A 1.330(6) . ?
N3A C8A 1.321(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.465(13) . ?
C5A C6A 1.365(8) . ?
C5A C9A 1.380(9) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.376(7) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.378(6) . ?
C9A H9A 0.9500 . ?

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 C1 116.19(13) 6_565 . ?
N1 C1 H1B 117.9 . . ?
N1 C1 H1A 118.6 . . ?
N1 C1 C2B 124.3(3) . . ?
N1 C1 C2A 122.8(3) . . ?
C2B C1 H1B 117.9 . . ?
C2A C1 H1A 118.6 . . ?
C4B N2B C3B 119.3(4) . . ?
C1 C2B H2B 121.3 . . ?
C3B C2B C1 117.4(6) . . ?
C3B C2B H2B 121.3 . . ?
C7B N3B C8B 116.2(7) . . ?
C2B C3B N2B 120.4(3) . . ?
C2B C3B N2B 120.4(3) 6_565 . ?
N2B C4B H4B 118.1 . . ?
N2B C4B C5B 123.8(5) . . ?
C5B C4B H4B 118.1 . . ?
C6B C5B C4B 118.7(8) . . ?
C9B C5B C4B 121.1(9) . . ?
C9B C5B C6B 120.2(13) . . ?
C5B C6B H6B 121.4 . . ?
C7B C6B C5B 117.3(12) . . ?
C7B C6B H6B 121.4 . . ?
N3B C7B C6B 124.4(9) . . ?
N3B C7B H7B 117.8 . . ?
C6B C7B H7B 117.8 . . ?
N3B C8B H8B 117.6 . . ?
N3B C8B C9B 124.8(9) . . ?
C9B C8B H8B 117.6 . . ?
C5B C9B H9B 121.5 . . ?
C8B C9B C5B 117.1(12) . . ?
C8B C9B H9B 121.5 . . ?
C4A N2A C3A 122.1(4) . . ?
C1 C2A H2A 119.8 . . ?
C3A C2A C1 120.4(6) . . ?
C3A C2A H2A 119.8 . . ?
C2A C3A N2A 121.6(4) 6_565 . ?
C2A C3A N2A 121.6(4) . . ?
C2A C3A C2A 116.7(7) . 6_565 ?
C8A N3A C7A 116.1(7) . . ?
N2A C4A H4A 118.7 . . ?
N2A C4A C5A 122.5(6) . . ?
C5A C4A H4A 118.7 . . ?
C6A C5A C4A 123.5(9) . . ?
C6A C5A C9A 114.9(12) . . ?
C9A C5A C4A 121.6(8) . . ?
C5A C6A H6A 119.3 . . ?
C5A C6A C7A 121.5(11) . . ?
C7A C6A H6A 119.3 . . ?
N3A C7A C6A 123.2(9) . . ?
N3A C7A H7A 118.4 . . ?
C6A C7A H7A 118.4 . . ?
N3A C8A H8A 118.3 . . ?
N3A C8A C9A 123.4(8) . . ?
C9A C8A H8A 118.3 . . ?
C5A C9A H9A 119.5 . . ?
C8A C9A C5A 121.0(11) . . ?
C8A C9A H9A 119.5 . . ?

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 C1 C2B C3B 8.0(6) . . . . ?
N1 C1 C2A C3A -6.2(6) . . . . ?
C1 N1 C1 C2B -12.4(4) 6_565 . . . ?
C1 N1 C1 C2A 10.0(4) 6_565 . . . ?
C1 C2B C3B N2B -178.2(4) . . . . ?
C1 C2B C3B C2B -2.9(8) . . . 6_565 ?
C1 C2A C3A N2A 178.0(4) . . . . ?
C1 C2A C3A C2A 1.8(9) . . . 6_565 ?
N2B C4B C5B C6B 180.000(1) . . . . ?
N2B C4B C5B C9B 0.000(2) . . . . ?
N3B C8B C9B C5B 0.000(2) . . . . ?
C3B N2B C4B C5B 180.000(1) . . . . ?
C4B N2B C3B C2B -92.4(4) . . . . ?
C4B N2B C3B C2B 92.4(4) . . . 6_565 ?
C4B C5B C6B C7B 180.000(2) . . . . ?
C4B C5B C9B C8B 180.000(2) . . . . ?
C5B C6B C7B N3B 0.000(2) . . . . ?
C6B C5B C9B C8B 0.000(2) . . . . ?
C7B N3B C8B C9B 0.000(2) . . . . ?
C8B N3B C7B C6B 0.000(2) . . . . ?
C9B C5B C6B C7B 0.000(2) . . . . ?
N2A C4A C5A C6A 0.000(2) . . . . ?
N2A C4A C5A C9A 180.000(1) . . . . ?
C3A N2A C4A C5A 180.000(1) . . . . ?
N3A C8A C9A C5A 0.000(2) . . . . ?
C4A N2A C3A C2A -92.0(4) . . . 6_565 ?
C4A N2A C3A C2A 92.0(4) . . . . ?
C4A C5A C6A C7A 180.000(2) . . . . ?
C4A C5A C9A C8A 180.000(2) . . . . ?
C5A C6A C7A N3A 0.000(2) . . . . ?
C6A C5A C9A C8A 0.000(2) . . . . ?
C7A N3A C8A C9A 0.000(2) . . . . ?
C8A N3A C7A C6A 0.000(1) . . . . ?
C9A C5A C6A C7A 0.000(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1465
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.351
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# 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_BPI_290_00
_database_code_depnum_ccdc_archive 'CCDC 2072416'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
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, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   15.7226(13)
_cell_length_b                   7.1311(6)
_cell_length_c                   9.0875(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.081(10)
_cell_angle_gamma                90
_cell_volume                     979.02(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3950
_cell_measurement_temperature    290.06(11)
_cell_measurement_theta_max      29.9090
_cell_measurement_theta_min      3.0400
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.549
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 1 -13 0.0715
-20 -4 1 0.1270
-6 0 13 0.0659
20 4 -6 0.0934
16 4 4 0.1311
-10 9 1 0.0169
9 -9 0 0.0094
11 -4 -11 0.0728

_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
10.2606 0.7181 -12.5149 -0.1135 0.0016 -0.9935
-19.5131 -4.3461 0.6957 0.9879 -0.0251 0.1533
-6.2373 0.2339 12.8047 -0.1047 0.0040 0.9945
20.0082 3.8107 -5.7187 -0.8457 0.0209 -0.5333
15.8165 4.1672 4.4311 -0.9676 0.0251 0.2511
-9.8736 8.9875 0.9875 -0.0253 -0.9945 0.1015
9.0086 -9.0579 0.4215 0.0256 0.9996 0.0090
11.4304 -3.8352 -11.2724 0.0104 0.4449 -0.8955

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8659
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.696
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.06(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -30.00  192
  2  ω    -28.00  68.00   0.50   27.23    --   -5.21  77.00 -90.00  192
  3  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 120.00  190
  4  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00-150.00  190
  5  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00 -90.00  190
  6  ω    -17.00  78.00   0.50   27.23    --    5.37  77.00  60.00  190
  7  ω    -23.00   6.00   0.50   27.23    --    5.37 -99.00 -90.00   58
  8  ω    -23.00  39.00   0.50   27.23    --    5.37 -99.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0415006000
_diffrn_orient_matrix_UB_12      -0.0453820000
_diffrn_orient_matrix_UB_13      -0.0275603000
_diffrn_orient_matrix_UB_21      0.0214309000
_diffrn_orient_matrix_UB_22      -0.0884708000
_diffrn_orient_matrix_UB_23      0.0123654000
_diffrn_orient_matrix_UB_31      -0.0046867000
_diffrn_orient_matrix_UB_32      -0.0021473000
_diffrn_orient_matrix_UB_33      0.0754229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                767
_reflns_number_total             1093
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.079
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.024
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1093
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      0.977
_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)+(0.0642P)²+0.0869P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1174
_refine_special_details          
'Atom sites C2 < C9, N2 and N3 were positionally disordered and modeled as split sites A and B. The site occupancies of the two sites were constrained to a total value of 1 and refined to 0.50 and 0.50 for the A and B sites, respectively. To help maintain reasonable ADP and bond length values for the disordered sites, the rigid bond restraint RIGU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C6A-C5A = C6A-C7A = C9A-C8A = C9A-C5A = C1-C2A = C2A-C3A = C1-C2B = C2B-C3B
 1.37367 with sigma of 0.02
 C5B-C6B = C6B-C7B = C8B-C9B = C9B-C5B
 1.37367 with sigma of 0.02
 N1-C1 = C7A-N3A = C7B-N3B = C8A-N3A = C8B-N3B
 1.32102 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N1, C1, N2B, C2B, N3B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N2A, C2A, C3A, N3A,
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H1B)=Sof(C2B)=Sof(H2B)=1-FVAR(1)
 Sof(N2B)=Sof(N3B)=Sof(C3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(C6B)=Sof(H6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=0.5*(1-FVAR(2))
 Sof(N2A)=Sof(C3A)=Sof(N3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(H6A)=
 Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=0.5*FVAR(2)
 Sof(H1A)=Sof(C2A)=Sof(H2A)=FVAR(1)
 1(DFIX)=1(DFIX)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1B), C1(H1A), C2B(H2B), C4B(H4B), C6B(H6B), C7B(H7B), C8B(H8B), C9B(H9B),
 C2A(H2A), C4A(H4A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.31627(9) 0.500000 0.04076(17) 0.0755(4) Uani 1 2 d DS T P A .
C1 C 0.36034(8) 0.6572(2) 0.08562(16) 0.0798(4) Uani 1 1 d D . . . .
H1B H 0.334682 0.771259 0.040147 0.096 Uiso 0.495(7) 1 calc R U P A 2
H1A H 0.328588 0.772193 0.069027 0.096 Uiso 0.505(7) 1 calc R U P A 1
N2B N 0.5658(3) 0.500000 0.3628(4) 0.0748(14) Uani 0.495(7) 2 d S T P A 2
C2B C 0.4418(6) 0.6661(14) 0.1950(10) 0.0761(18) Uani 0.495(7) 1 d D . P A 2
H2B H 0.467763 0.783353 0.231899 0.091 Uiso 0.495(7) 1 calc R U P A 2
N3B N 0.8910(7) 0.500000 0.6398(11) 0.072(2) Uani 0.495(7) 2 d DS T P A 2
C3B C 0.4839(3) 0.500000 0.2487(6) 0.0606(11) Uani 0.495(7) 2 d DS T P A 2
C4B C 0.6357(4) 0.500000 0.3263(6) 0.0650(12) Uani 0.495(7) 2 d S T P A 2
H4B H 0.632511 0.500000 0.220299 0.078 Uiso 0.495(7) 2 calc R U P A 2
C5B C 0.7236(9) 0.500000 0.4369(13) 0.058(2) Uani 0.495(7) 2 d DS T P A 2
C6B C 0.7976(6) 0.500000 0.3845(17) 0.085(3) Uani 0.495(7) 2 d DS T P A 2
H6B H 0.792391 0.500000 0.277795 0.102 Uiso 0.495(7) 2 calc R U P A 2
C7B C 0.8789(7) 0.500000 0.4897(14) 0.085(3) Uani 0.495(7) 2 d DS T P A 2
H7B H 0.929830 0.500000 0.452729 0.102 Uiso 0.495(7) 2 calc R U P A 2
C8B C 0.8185(6) 0.500000 0.6881(13) 0.0702(19) Uani 0.495(7) 2 d DS T P A 2
H8B H 0.825529 0.500000 0.795370 0.084 Uiso 0.495(7) 2 calc R U P A 2
C9B C 0.7341(8) 0.500000 0.5919(13) 0.0685(19) Uani 0.495(7) 2 d DS T P A 2
H9B H 0.684210 0.500000 0.631584 0.082 Uiso 0.495(7) 2 calc R U P A 2
N2A N 0.5886(2) 0.500000 0.2578(5) 0.0896(15) Uani 0.505(7) 2 d S T P A 1
C2A C 0.4501(6) 0.6625(15) 0.1552(11) 0.082(2) Uani 0.505(7) 1 d D . P A 1
H2A H 0.479640 0.779606 0.177464 0.098 Uiso 0.505(7) 1 calc R U P A 1
C3A C 0.4962(3) 0.500000 0.1921(6) 0.0693(13) Uani 0.505(7) 2 d DS T P A 1
N3A N 0.9012(7) 0.500000 0.5985(12) 0.0702(19) Uani 0.505(7) 2 d DS T P A 1
C4A C 0.6210(4) 0.500000 0.3919(8) 0.0679(12) Uani 0.505(7) 2 d S T P A 1
H4A H 0.583215 0.500000 0.457329 0.081 Uiso 0.505(7) 2 calc R U P A 1
C5A C 0.7173(9) 0.500000 0.4617(14) 0.062(2) Uani 0.505(7) 2 d DS T P A 1
C6A C 0.7772(6) 0.500000 0.3775(14) 0.0671(17) Uani 0.505(7) 2 d DS T P A 1
H6A H 0.756762 0.500000 0.268807 0.081 Uiso 0.505(7) 2 calc R U P A 1
C7A C 0.8668(8) 0.500000 0.4484(11) 0.077(2) Uani 0.505(7) 2 d DS T P A 1
H7A H 0.906193 0.500000 0.385742 0.092 Uiso 0.505(7) 2 calc R U P A 1
C8A C 0.8438(6) 0.500000 0.6787(13) 0.074(2) Uani 0.505(7) 2 d DS T P A 1
H8A H 0.866135 0.500000 0.787090 0.089 Uiso 0.505(7) 2 calc R U P A 1
C9A C 0.7530(8) 0.500000 0.6171(12) 0.072(2) Uani 0.505(7) 2 d DS T P A 1
H9A H 0.715281 0.500000 0.682779 0.087 Uiso 0.505(7) 2 calc R U P A 1


_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 C1 1.3216(15) 6_565 ?
N1 C1 1.3216(15) . ?
C1 H1B 0.9500 . ?
C1 H1A 0.9500 . ?
C1 C2B 1.388(9) . ?
C1 C2A 1.377(9) . ?
N2B C3B 1.412(6) . ?
N2B C4B 1.234(9) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.378(8) . ?
N3B C7B 1.325(9) . ?
N3B C8B 1.331(7) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.466(13) . ?
C5B C6B 1.374(9) . ?
C5B C9B 1.372(10) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.368(9) . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
C8B C9B 1.372(7) . ?
C9B H9B 0.9500 . ?
N2A C3A 1.409(6) . ?
N2A C4A 1.183(10) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.359(9) . ?
N3A C7A 1.321(8) . ?
N3A C8A 1.308(8) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.471(15) . ?
C5A C6A 1.368(9) . ?
C5A C9A 1.368(10) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.378(8) . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.382(7) . ?
C9A H9A 0.9500 . ?

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 C1 116.06(15) 6_565 . ?
N1 C1 H1B 118.0 . . ?
N1 C1 H1A 118.4 . . ?
N1 C1 C2B 124.1(4) . . ?
N1 C1 C2A 123.2(5) . . ?
C2B C1 H1B 118.0 . . ?
C2A C1 H1A 118.4 . . ?
C4B N2B C3B 120.1(4) . . ?
C1 C2B H2B 120.9 . . ?
C3B C2B C1 118.1(8) . . ?
C3B C2B H2B 120.9 . . ?
C7B N3B C8B 116.6(9) . . ?
C2B C3B N2B 120.7(5) . . ?
C2B C3B N2B 120.7(5) 6_565 . ?
C2B C3B C2B 118.5(9) 6_565 . ?
N2B C4B H4B 118.1 . . ?
N2B C4B C5B 123.8(6) . . ?
C5B C4B H4B 118.1 . . ?
C6B C5B C4B 119.3(9) . . ?
C9B C5B C4B 121.8(10) . . ?
C9B C5B C6B 118.9(13) . . ?
C5B C6B H6B 120.8 . . ?
C7B C6B C5B 118.4(13) . . ?
C7B C6B H6B 120.8 . . ?
N3B C7B C6B 124.0(12) . . ?
N3B C7B H7B 118.0 . . ?
C6B C7B H7B 118.0 . . ?
N3B C8B H8B 118.1 . . ?
N3B C8B C9B 123.8(10) . . ?
C9B C8B H8B 118.1 . . ?
C5B C9B H9B 120.8 . . ?
C8B C9B C5B 118.4(13) . . ?
C8B C9B H9B 120.8 . . ?
C4A N2A C3A 122.4(5) . . ?
C1 C2A H2A 120.0 . . ?
C3A C2A C1 119.9(9) . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A N2A 121.4(5) . . ?
C2A C3A N2A 121.4(5) 6_565 . ?
C2A C3A C2A 117.0(10) 6_565 . ?
C8A N3A C7A 115.3(9) . . ?
N2A C4A H4A 118.6 . . ?
N2A C4A C5A 122.9(7) . . ?
C5A C4A H4A 118.6 . . ?
C6A C5A C4A 123.0(10) . . ?
C9A C5A C4A 121.6(9) . . ?
C9A C5A C6A 115.4(13) . . ?
C5A C6A H6A 119.6 . . ?
C5A C6A C7A 120.8(12) . . ?
C7A C6A H6A 119.6 . . ?
N3A C7A C6A 123.8(12) . . ?
N3A C7A H7A 118.1 . . ?
C6A C7A H7A 118.1 . . ?
N3A C8A H8A 117.6 . . ?
N3A C8A C9A 124.8(10) . . ?
C9A C8A H8A 117.6 . . ?
C5A C9A C8A 120.0(13) . . ?
C5A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?

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 C1 C2B C3B 7.2(9) . . . . ?
N1 C1 C2A C3A -5.4(10) . . . . ?
C1 N1 C1 C2B -11.5(5) 6_565 . . . ?
C1 N1 C1 C2A 9.4(6) 6_565 . . . ?
C1 C2B C3B N2B -178.4(5) . . . . ?
C1 C2B C3B C2B -2.2(12) . . . 6_565 ?
C1 C2A C3A N2A 177.4(6) . . . . ?
C1 C2A C3A C2A 0.9(14) . . . 6_565 ?
N2B C4B C5B C6B 180.000(2) . . . . ?
N2B C4B C5B C9B 0.000(2) . . . . ?
N3B C8B C9B C5B 0.000(2) . . . . ?
C3B N2B C4B C5B 180.000(1) . . . . ?
C4B N2B C3B C2B 91.9(5) . . . 6_565 ?
C4B N2B C3B C2B -91.9(5) . . . . ?
C4B C5B C6B C7B 180.000(2) . . . . ?
C4B C5B C9B C8B 180.000(2) . . . . ?
C5B C6B C7B N3B 0.000(2) . . . . ?
C6B C5B C9B C8B 0.000(2) . . . . ?
C7B N3B C8B C9B 0.000(2) . . . . ?
C8B N3B C7B C6B 0.000(2) . . . . ?
C9B C5B C6B C7B 0.000(2) . . . . ?
N2A C4A C5A C6A 0.000(2) . . . . ?
N2A C4A C5A C9A 180.000(2) . . . . ?
C3A N2A C4A C5A 180.000(2) . . . . ?
N3A C8A C9A C5A 0.000(2) . . . . ?
C4A N2A C3A C2A -91.8(6) . . . 6_565 ?
C4A N2A C3A C2A 91.8(6) . . . . ?
C4A C5A C6A C7A 180.000(2) . . . . ?
C4A C5A C9A C8A 180.000(2) . . . . ?
C5A C6A C7A N3A 0.000(3) . . . . ?
C6A C5A C9A C8A 0.000(2) . . . . ?
C7A N3A C8A C9A 0.000(2) . . . . ?
C8A N3A C7A C6A 0.000(1) . . . . ?
C9A C5A C6A C7A 0.000(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   1411
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.417
_oxdiff_exptl_absorpt_empirical_full_min 0.770

# END of CIF
####################################################################### 
# 
# 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_PI_190_a
_database_code_depnum_ccdc_archive 'CCDC 2072417'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_190_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1B      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.66850(5)
_cell_length_b                   7.45207(6)
_cell_length_c                   23.56855(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     995.585(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    13215
_cell_measurement_theta_min      3.729
_cell_measurement_theta_max      77.187
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.71 4.70 2.20 0.0636
3.57 0.06 -3.70 0.0545
-3.57 -0.03 3.71 0.0485
-2.85 2.80 3.84 0.0538
0.66 -0.37 14.99 0.0244
-0.39 0.28 -15.17 0.0246
2.79 -0.95 -9.51 0.0528
0.81 -3.65 9.45 0.0666
0.19 -4.43 -6.10 0.0646
0.13 -3.03 -11.90 0.0486
2.54 2.10 8.87 0.0670
1.19 -0.31 -14.44 0.0337
-0.15 1.72 -14.27 0.0357
-3.44 1.70 -0.14 0.0408
0.00 -4.00 5.98 0.0646

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.236
_diffrn_reflns_theta_min         3.751
_diffrn_ambient_temperature      189.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2021
_reflns_number_total             2085
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(18)
_refine_ls_extinction_coef       0.0048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.080
_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)+(0.0459P)²+0.0838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1475(3) 0.5461(2) 0.53184(6) 0.0415(3) Uani 1 1 d . . . . .
H1A H 0.033(4) 0.626(3) 0.5379(9) 0.050 Uiso 1 1 d . U . . .
H1B H 0.219(4) 0.510(3) 0.5648(8) 0.050 Uiso 1 1 d . U . . .
C7 C 0.5878(3) 0.58288(19) 0.28074(6) 0.0325(3) Uani 1 1 d . . . . .
H7 H 0.437257 0.637962 0.277649 0.039 Uiso 1 1 calc R U . . .
N2 N 0.6572(2) 0.52387(17) 0.32844(5) 0.0339(3) Uani 1 1 d . . . . .
C1 C 0.2701(3) 0.54672(19) 0.48177(6) 0.0321(3) Uani 1 1 d . . . . .
C2 C 0.1853(3) 0.6394(2) 0.43382(6) 0.0347(3) Uani 1 1 d . . . . .
H2 H 0.042609 0.705748 0.436387 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3075(3) 0.6350(2) 0.38312(6) 0.0348(3) Uani 1 1 d . . . . .
H3 H 0.246822 0.697625 0.351190 0.042 Uiso 1 1 calc R U . . .
C4 C 0.5194(3) 0.5396(2) 0.37804(6) 0.0310(3) Uani 1 1 d . . . . .
C5 C 0.6037(3) 0.4490(2) 0.42582(6) 0.0339(3) Uani 1 1 d . . . . .
H5 H 0.747912 0.384552 0.423333 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4825(3) 0.4512(2) 0.47643(6) 0.0360(3) Uani 1 1 d . . . . .
H6 H 0.543252 0.387305 0.508113 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7387(3) 0.56665(18) 0.23024(6) 0.0306(3) Uani 1 1 d . . . . .
C9 C 0.6698(3) 0.6413(2) 0.17881(6) 0.0352(3) Uani 1 1 d . . . . .
H9 H 0.520945 0.698947 0.175427 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8197(3) 0.6311(2) 0.13253(6) 0.0381(4) Uani 1 1 d . . . . .
H10 H 0.770558 0.685289 0.098013 0.046 Uiso 1 1 calc R U . . .
N3 N 1.0294(2) 0.54949(18) 0.13363(5) 0.0369(3) Uani 1 1 d . . . . .
C11 C 1.0914(3) 0.4735(2) 0.18304(7) 0.0371(3) Uani 1 1 d . . . . .
H11 H 1.237614 0.411402 0.184594 0.044 Uiso 1 1 calc R U . . .
C12 C 0.9563(3) 0.4795(2) 0.23180(6) 0.0355(3) Uani 1 1 d . . . . .
H12 H 1.010736 0.425236 0.265837 0.043 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
N1 H1A 0.89(2) . ?
N1 H1B 0.92(2) . ?
N1 C1 1.3694(18) . ?
C7 H7 0.9500 . ?
C7 N2 1.2695(19) . ?
C7 C8 1.4705(19) . ?
N2 C4 1.4110(18) . ?
C1 C2 1.409(2) . ?
C1 C6 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(2) . ?
C4 C5 1.397(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.390(2) . ?
C8 C12 1.394(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C10 N3 1.335(2) . ?
N3 C11 1.342(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 112.4(19) . . ?
C1 N1 H1A 120.4(14) . . ?
C1 N1 H1B 120.5(14) . . ?
N2 C7 H7 119.7 . . ?
N2 C7 C8 120.54(13) . . ?
C8 C7 H7 119.7 . . ?
C7 N2 C4 122.24(13) . . ?
N1 C1 C2 121.33(13) . . ?
N1 C1 C6 120.69(13) . . ?
C6 C1 C2 117.97(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.75(14) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.05(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 N2 125.99(13) . . ?
C5 C4 N2 116.00(13) . . ?
C5 C4 C3 118.01(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.47(13) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.75(13) . . ?
C5 C6 H6 119.6 . . ?
C9 C8 C7 120.64(13) . . ?
C9 C8 C12 117.27(13) . . ?
C12 C8 C7 122.09(12) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.50(13) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 118.1 . . ?
N3 C10 C9 123.78(13) . . ?
N3 C10 H10 118.1 . . ?
C10 N3 C11 116.24(12) . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.26(13) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 118.91(13) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.92(2) 2.21(2) 3.1012(19) 165.7(19) 2_665 yes

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 C1 C2 C3 -178.23(14) . . . . ?
N1 C1 C6 C5 178.81(15) . . . . ?
C7 N2 C4 C3 -7.1(2) . . . . ?
C7 N2 C4 C5 172.17(14) . . . . ?
C7 C8 C9 C10 177.14(14) . . . . ?
C7 C8 C12 C11 -178.35(14) . . . . ?
N2 C7 C8 C9 -175.83(14) . . . . ?
N2 C7 C8 C12 3.1(2) . . . . ?
N2 C4 C5 C6 -178.69(14) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C3 C4 N2 179.19(14) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C8 C7 N2 C4 178.92(12) . . . . ?
C8 C9 C10 N3 1.3(2) . . . . ?
C9 C8 C12 C11 0.6(2) . . . . ?
C9 C10 N3 C11 0.5(2) . . . . ?
C10 N3 C11 C12 -1.9(2) . . . . ?
N3 C11 C12 C8 1.3(2) . . . . ?
C12 C8 C9 C10 -1.8(2) . . . . ?

_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_PI_230_sc_a
_database_code_depnum_ccdc_archive 'CCDC 2072419'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_PI_230_sc_a         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.942 Why?  
RESPONSE: Due to the conversion of the unit cell during the data collection.
;
_vrf_PLAT353_PI_230_sc_a         
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1B      .       1.07 Ang.  
RESPONSE: The proton was allowed to free refine it's position.
;
_vrf_STRVA01_PI_230_sc_a         
;
PROBLEM: Flack parameter is too small
RESPONSE: Due to the conversion of the unit cell during the data collection.
;
_vrf_PLAT340_PI_230_sc_a         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00536 Ang.  
RESPONSE: Due to the crystal converting at this temperature.
;
_vrf_PLAT420_PI_230_sc_a         
;
PROBLEM: D-H Without Acceptor       N1       --H1B      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT915_PI_230_sc_a         
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         66 %     
RESPONSE: Due to loss of data from changes in the unit cell.
;
_vrf_PLAT978_PI_230_sc_a         
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The remaining residual electron density is located outside of the 
          molecule or between carbon and nitrogen atoms.
;
_vrf_PLAT911_PI_230_sc_a         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         63 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7302(10)
_cell_length_b                   7.4150(11)
_cell_length_c                   23.579(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1001.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    6619
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      75.309
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.81 -4.62 2.17 0.0636
0.34 -0.29 -15.14 0.0246
-0.61 0.38 14.99 0.0244
0.11 -1.72 -14.20 0.0357
-1.30 0.25 -14.27 0.0337
-2.54 -2.12 9.09 0.0670
-0.23 2.97 -11.88 0.0486
-0.84 3.60 9.44 0.0666
-3.69 -0.16 -3.35 0.0545
-2.93 0.84 -9.22 0.0528
3.69 0.13 3.36 0.0485
3.00 -2.69 3.59 0.0538
-0.03 3.96 5.91 0.0646
-0.29 4.36 -6.11 0.0646
3.57 -1.59 -0.44 0.0408

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6340
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.787
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.878
_diffrn_reflns_theta_min         3.749
_diffrn_ambient_temperature      229.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.508
_reflns_Friedel_fraction_full    0.752
_reflns_Friedel_fraction_max     0.662
_reflns_number_gt                1416
_reflns_number_total             1659
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(6)
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.078
_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)+(0.0958P)²+0.1838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1504(6) 0.5457(6) 0.53153(14) 0.0624(10) Uani 1 1 d . . . . .
H1A H 0.036(9) 0.608(7) 0.537(2) 0.075 Uiso 1 1 d . U . . .
H1B H 0.229(8) 0.508(7) 0.571(2) 0.075 Uiso 1 1 d . U . . .
C7 C 0.5893(7) 0.5822(6) 0.28063(16) 0.0551(11) Uani 1 1 d . . . . .
H7 H 0.440554 0.634646 0.277399 0.066 Uiso 1 1 calc R U . . .
N2 N 0.6577(5) 0.5244(5) 0.32813(12) 0.0546(9) Uani 1 1 d . . . . .
C1 C 0.2716(7) 0.5468(6) 0.48137(14) 0.0500(10) Uani 1 1 d . . . . .
C2 C 0.1878(7) 0.6399(6) 0.43351(15) 0.0550(11) Uani 1 1 d . . . . .
H2 H 0.048431 0.706231 0.436080 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3082(7) 0.6349(6) 0.38282(15) 0.0530(10) Uani 1 1 d . . . . .
H3 H 0.248268 0.696868 0.351235 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5192(6) 0.5389(6) 0.37751(14) 0.0489(9) Uani 1 1 d . . . . .
C5 C 0.6041(6) 0.4512(7) 0.42513(15) 0.0527(10) Uani 1 1 d . . . . .
H5 H 0.747532 0.390091 0.422971 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4830(7) 0.4516(6) 0.47551(15) 0.0548(10) Uani 1 1 d . . . . .
H6 H 0.542491 0.387166 0.506637 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7403(7) 0.5684(6) 0.23005(15) 0.0501(9) Uani 1 1 d . . . . .
C9 C 0.6714(7) 0.6410(6) 0.17901(16) 0.0556(10) Uani 1 1 d . . . . .
H9 H 0.524518 0.696218 0.175440 0.067 Uiso 1 1 calc R U . . .
C10 C 0.8216(7) 0.6318(7) 0.13281(15) 0.0584(11) Uani 1 1 d . . . . .
H10 H 0.773649 0.686349 0.098773 0.070 Uiso 1 1 calc R U . . .
N3 N 1.0287(6) 0.5508(5) 0.13359(13) 0.0569(9) Uani 1 1 d . . . . .
C11 C 1.0913(7) 0.4753(7) 0.18286(16) 0.0591(11) Uani 1 1 d . . . . .
H11 H 1.235520 0.415129 0.184562 0.071 Uiso 1 1 calc R U . . .
C12 C 0.9562(7) 0.4809(6) 0.23141(16) 0.0558(10) Uani 1 1 d . . . . .
H12 H 1.009119 0.426320 0.265026 0.067 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
N1 H1A 0.81(5) . ?
N1 H1B 1.08(5) . ?
N1 C1 1.371(5) . ?
C7 H7 0.9400 . ?
C7 N2 1.262(5) . ?
C7 C8 1.477(5) . ?
N2 C4 1.413(4) . ?
C1 C2 1.407(5) . ?
C1 C6 1.409(6) . ?
C2 H2 0.9400 . ?
C2 C3 1.380(5) . ?
C3 H3 0.9400 . ?
C3 C4 1.409(6) . ?
C4 C5 1.386(5) . ?
C5 H5 0.9400 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9400 . ?
C8 C9 1.376(5) . ?
C8 C12 1.397(6) . ?
C9 H9 0.9400 . ?
C9 C10 1.390(5) . ?
C10 H10 0.9400 . ?
C10 N3 1.330(6) . ?
N3 C11 1.338(5) . ?
C11 H11 0.9400 . ?
C11 C12 1.383(5) . ?
C12 H12 0.9400 . ?

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
H1A N1 H1B 110(5) . . ?
C1 N1 H1A 123(4) . . ?
C1 N1 H1B 123(3) . . ?
N2 C7 H7 119.6 . . ?
N2 C7 C8 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C7 N2 C4 122.1(4) . . ?
N1 C1 C2 121.5(4) . . ?
N1 C1 C6 121.1(3) . . ?
C2 C1 C6 117.4(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 N2 126.4(3) . . ?
C5 C4 N2 115.8(3) . . ?
C5 C4 C3 117.8(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.3 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 C12 117.1(3) . . ?
C12 C8 C7 122.2(3) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 117.8 . . ?
N3 C10 C9 124.3(4) . . ?
N3 C10 H10 117.8 . . ?
C10 N3 C11 116.1(3) . . ?
N3 C11 H11 118.1 . . ?
N3 C11 C12 123.8(4) . . ?
C12 C11 H11 118.1 . . ?
C8 C12 H12 120.3 . . ?
C11 C12 C8 119.4(3) . . ?
C11 C12 H12 120.3 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 1.08(5) 2.07(5) 3.112(5) 162(4) 2_665 yes

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 C1 C2 C3 -177.9(4) . . . . ?
N1 C1 C6 C5 179.5(4) . . . . ?
C7 N2 C4 C3 -8.3(7) . . . . ?
C7 N2 C4 C5 172.7(4) . . . . ?
C7 C8 C9 C10 177.5(4) . . . . ?
C7 C8 C12 C11 -178.8(4) . . . . ?
N2 C7 C8 C9 -176.1(4) . . . . ?
N2 C7 C8 C12 4.4(6) . . . . ?
N2 C4 C5 C6 -178.5(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C3 C4 N2 -179.8(4) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 2.4(7) . . . . ?
C4 C5 C6 C1 -2.3(7) . . . . ?
C6 C1 C2 C3 0.9(6) . . . . ?
C8 C7 N2 C4 178.7(4) . . . . ?
C8 C9 C10 N3 2.4(7) . . . . ?
C9 C8 C12 C11 1.7(6) . . . . ?
C9 C10 N3 C11 -0.3(7) . . . . ?
C10 N3 C11 C12 -1.2(7) . . . . ?
N3 C11 C12 C8 0.5(7) . . . . ?
C12 C8 C9 C10 -3.0(6) . . . . ?

_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_PI_210_a
_database_code_depnum_ccdc_archive 'CCDC 2072418'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_210_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1B      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.67404(5)
_cell_length_b                   7.47072(6)
_cell_length_c                   23.5754(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     999.343(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    12585
_cell_measurement_theta_min      3.731
_cell_measurement_theta_max      77.158
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.72 4.70 2.20 0.0636
0.21 -4.44 -6.11 0.0646
-2.86 2.80 3.81 0.0538
-3.58 -0.04 3.66 0.0485
2.80 -0.94 -9.48 0.0528
3.58 0.07 -3.65 0.0545
0.81 -3.66 9.45 0.0666
0.00 -4.01 5.97 0.0646
0.14 -3.04 -11.91 0.0486
2.53 2.11 8.91 0.0670
1.20 -0.30 -14.42 0.0337
-3.45 1.70 -0.18 0.0408
-0.14 1.73 -14.27 0.0357
0.65 -0.38 15.00 0.0244
-0.38 0.28 -15.18 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18712
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.306
_diffrn_reflns_theta_min         3.750
_diffrn_ambient_temperature      209.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2018
_reflns_number_total             2092
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(19)
_refine_ls_extinction_coef       0.0047(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.072
_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)+(0.0457P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0838
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.1488(3) 0.5462(2) 0.53163(6) 0.0466(4) Uani 1 1 d . . . . .
H1A H 0.038(4) 0.627(3) 0.5379(10) 0.056 Uiso 1 1 d . U . . .
H1B H 0.220(4) 0.509(3) 0.5639(9) 0.056 Uiso 1 1 d . U . . .
C7 C 0.5888(3) 0.5830(2) 0.28075(7) 0.0371(4) Uani 1 1 d . . . . .
H7 H 0.440188 0.637713 0.277719 0.044 Uiso 1 1 calc R U . . .
N2 N 0.6574(2) 0.52394(18) 0.32828(5) 0.0385(3) Uani 1 1 d . . . . .
C1 C 0.2710(3) 0.5467(2) 0.48157(6) 0.0362(3) Uani 1 1 d . . . . .
C2 C 0.1865(3) 0.6393(2) 0.43373(7) 0.0390(4) Uani 1 1 d . . . . .
H2 H 0.045553 0.704920 0.436329 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3081(3) 0.6350(2) 0.38305(7) 0.0389(4) Uani 1 1 d . . . . .
H3 H 0.247968 0.696847 0.351488 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5197(3) 0.5398(2) 0.37790(6) 0.0350(3) Uani 1 1 d . . . . .
C5 C 0.6039(3) 0.4494(2) 0.42562(7) 0.0383(4) Uani 1 1 d . . . . .
H5 H 0.746394 0.385739 0.423142 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4830(3) 0.4514(2) 0.47615(7) 0.0404(4) Uani 1 1 d . . . . .
H6 H 0.543011 0.388235 0.507448 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7393(3) 0.56691(19) 0.23020(6) 0.0349(3) Uani 1 1 d . . . . .
C9 C 0.6706(3) 0.6416(2) 0.17886(7) 0.0399(4) Uani 1 1 d . . . . .
H9 H 0.523562 0.698551 0.175537 0.048 Uiso 1 1 calc R U . . .
C10 C 0.8201(3) 0.6315(2) 0.13268(7) 0.0430(4) Uani 1 1 d . . . . .
H10 H 0.771593 0.685490 0.098607 0.052 Uiso 1 1 calc R U . . .
N3 N 1.0290(3) 0.5499(2) 0.13356(6) 0.0415(3) Uani 1 1 d . . . . .
C11 C 1.0911(3) 0.4740(2) 0.18290(7) 0.0422(4) Uani 1 1 d . . . . .
H11 H 1.235772 0.412818 0.184426 0.051 Uiso 1 1 calc R U . . .
C12 C 0.9561(3) 0.4800(2) 0.23162(7) 0.0403(4) Uani 1 1 d . . . . .
H12 H 1.009894 0.426209 0.265253 0.048 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
N1 H1A 0.89(2) . ?
N1 H1B 0.91(2) . ?
N1 C1 1.369(2) . ?
C7 H7 0.9400 . ?
C7 N2 1.266(2) . ?
C7 C8 1.471(2) . ?
N2 C4 1.4118(19) . ?
C1 C2 1.407(2) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.400(2) . ?
C4 C5 1.396(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.375(2) . ?
C6 H6 0.9400 . ?
C8 C9 1.389(2) . ?
C8 C12 1.391(2) . ?
C9 H9 0.9400 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9400 . ?
C10 N3 1.333(2) . ?
N3 C11 1.341(2) . ?
C11 H11 0.9400 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9400 . ?

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
H1A N1 H1B 113(2) . . ?
C1 N1 H1A 120.2(15) . . ?
C1 N1 H1B 119.9(15) . . ?
N2 C7 H7 119.7 . . ?
N2 C7 C8 120.69(15) . . ?
C8 C7 H7 119.7 . . ?
C7 N2 C4 122.28(14) . . ?
N1 C1 C2 121.31(15) . . ?
N1 C1 C6 120.74(14) . . ?
C6 C1 C2 117.94(14) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.79(15) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.02(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 N2 126.08(14) . . ?
C5 C4 N2 115.95(14) . . ?
C5 C4 C3 117.97(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.47(14) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.81(14) . . ?
C5 C6 H6 119.6 . . ?
C9 C8 C7 120.69(14) . . ?
C9 C8 C12 117.17(14) . . ?
C12 C8 C7 122.13(14) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.50(15) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 118.0 . . ?
N3 C10 C9 123.93(15) . . ?
N3 C10 H10 118.0 . . ?
C10 N3 C11 116.15(14) . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.15(15) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 119.06(15) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.91(2) 2.22(2) 3.104(2) 166(2) 2_665 yes

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 C1 C2 C3 -178.24(16) . . . . ?
N1 C1 C6 C5 178.89(16) . . . . ?
C7 N2 C4 C3 -6.8(3) . . . . ?
C7 N2 C4 C5 172.34(15) . . . . ?
C7 C8 C9 C10 177.09(15) . . . . ?
C7 C8 C12 C11 -178.31(15) . . . . ?
N2 C7 C8 C9 -175.93(15) . . . . ?
N2 C7 C8 C12 3.0(2) . . . . ?
N2 C4 C5 C6 -178.62(15) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 N2 179.18(15) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C8 C7 N2 C4 178.86(14) . . . . ?
C8 C9 C10 N3 1.5(3) . . . . ?
C9 C8 C12 C11 0.7(2) . . . . ?
C9 C10 N3 C11 0.3(3) . . . . ?
C10 N3 C11 C12 -1.6(3) . . . . ?
N3 C11 C12 C8 1.2(3) . . . . ?
C12 C8 C9 C10 -1.9(2) . . . . ?

_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_PI_230_lc_a
_database_code_depnum_ccdc_archive 'CCDC 2072420'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_RINTA01_PI_230_lc_a         
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE: The unit cell conversion was not fully completed at this 
          temperature.
;
_vrf_STRVA01_PI_230_lc_a         
;
PROBLEM: Flack test results are meaningless.
RESPONSE: Due to structure conversion.
;
_vrf_PLAT911_PI_230_lc_a         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
_vrf_PLAT020_PI_230_lc_a         
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.176 Report
RESPONSE: The unit cell conversion was not fully completed at this 
          temperature.
;
_vrf_PLAT340_PI_230_lc_a         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00627 Ang.  
RESPONSE: Due to poor fitting reflections.
;
_vrf_PLAT420_PI_230_lc_a         
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8323(8)
_cell_length_b                   7.3764(7)
_cell_length_c                   23.496(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1010.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    5650
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      75.309
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.81 -4.62 2.17 0.0636
0.34 -0.29 -15.14 0.0246
-0.61 0.38 14.99 0.0244
0.11 -1.72 -14.20 0.0357
-1.30 0.25 -14.27 0.0337
-2.54 -2.12 9.09 0.0670
-0.23 2.97 -11.88 0.0486
-0.84 3.60 9.44 0.0666
-3.69 -0.16 -3.35 0.0545
-2.93 0.84 -9.22 0.0528
3.69 0.13 3.36 0.0485
3.00 -2.69 3.59 0.0538
-0.03 3.96 5.91 0.0646
-0.29 4.36 -6.11 0.0646
3.57 -1.59 -0.44 0.0408

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1761
_diffrn_reflns_av_unetI/netI     0.1192
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8670
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.855
_diffrn_reflns_theta_min         3.762
_diffrn_ambient_temperature      229.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.630
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                1626
_reflns_number_total             1998
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Flack x determined using 501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.046
_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)+(0.1556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2012
_refine_ls_wR_factor_ref         0.2313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1803(8) 0.5342(6) 0.5222(2) 0.0575(11) Uani 1 1 d D . . . .
H1A H 0.069(8) 0.611(6) 0.534(3) 0.069 Uiso 1 1 d D U . . .
H1B H 0.262(10) 0.476(8) 0.549(2) 0.069 Uiso 1 1 d D U . . .
N2 N 0.5931(6) 0.6085(4) 0.30819(17) 0.0461(10) Uani 1 1 d . . . . .
C7 C 0.7859(7) 0.5477(5) 0.2933(2) 0.0444(10) Uani 1 1 d . . . . .
H7 H 0.876890 0.486727 0.320187 0.053 Uiso 1 1 calc R U . . .
C1 C 0.2879(7) 0.5573(5) 0.4710(2) 0.0447(10) Uani 1 1 d . . . . .
C2 C 0.1936(7) 0.6627(5) 0.4276(2) 0.0446(10) Uani 1 1 d . . . . .
H2 H 0.055573 0.725110 0.434144 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2990(7) 0.6769(5) 0.3752(2) 0.0439(10) Uani 1 1 d . . . . .
H3 H 0.230612 0.747974 0.346669 0.053 Uiso 1 1 calc R U . . .
C4 C 0.5057(7) 0.5878(5) 0.36370(19) 0.0405(9) Uani 1 1 d . . . . .
C5 C 0.6041(7) 0.4850(5) 0.4077(2) 0.0454(10) Uani 1 1 d . . . . .
H5 H 0.744208 0.425194 0.401387 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4982(7) 0.4706(5) 0.4599(2) 0.0456(10) Uani 1 1 d . . . . .
H6 H 0.567740 0.401396 0.488766 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8720(7) 0.5694(5) 0.2351(2) 0.0426(9) Uani 1 1 d . . . . .
C9 C 0.7396(7) 0.6467(5) 0.1916(2) 0.0454(10) Uani 1 1 d . . . . .
H9 H 0.591608 0.690695 0.199297 0.054 Uiso 1 1 calc R U . . .
C10 C 0.8295(8) 0.6575(5) 0.1370(2) 0.0485(11) Uani 1 1 d . . . . .
H10 H 0.739482 0.711195 0.108421 0.058 Uiso 1 1 calc R U . . .
N3 N 1.0371(6) 0.5956(4) 0.12293(17) 0.0470(9) Uani 1 1 d . . . . .
C11 C 1.1615(7) 0.5247(5) 0.1645(2) 0.0471(10) Uani 1 1 d . . . . .
H11 H 1.308324 0.480888 0.155356 0.057 Uiso 1 1 calc R U . . .
C12 C 1.0896(8) 0.5110(6) 0.2203(2) 0.0476(11) Uani 1 1 d . . . . .
H12 H 1.187829 0.462206 0.248096 0.057 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
N1 H1A 0.90(3) . ?
N1 H1B 0.90(3) . ?
N1 C1 1.368(6) . ?
N2 C7 1.261(6) . ?
N2 C4 1.409(6) . ?
C7 H7 0.9400 . ?
C7 C8 1.464(6) . ?
C1 C2 1.395(6) . ?
C1 C6 1.408(6) . ?
C2 H2 0.9400 . ?
C2 C3 1.380(6) . ?
C3 H3 0.9400 . ?
C3 C4 1.399(6) . ?
C4 C5 1.404(6) . ?
C5 H5 0.9400 . ?
C5 C6 1.379(6) . ?
C6 H6 0.9400 . ?
C8 C9 1.403(6) . ?
C8 C12 1.385(6) . ?
C9 H9 0.9400 . ?
C9 C10 1.388(7) . ?
C10 H10 0.9400 . ?
C10 N3 1.336(6) . ?
N3 C11 1.323(6) . ?
C11 H11 0.9400 . ?
C11 C12 1.381(7) . ?
C12 H12 0.9400 . ?

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
H1A N1 H1B 118(6) . . ?
C1 N1 H1A 121(4) . . ?
C1 N1 H1B 116(4) . . ?
C7 N2 C4 122.8(4) . . ?
N2 C7 H7 119.1 . . ?
N2 C7 C8 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
N1 C1 C2 122.1(4) . . ?
N1 C1 C6 120.4(4) . . ?
C2 C1 C6 117.5(4) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 N2 116.1(4) . . ?
C3 C4 C5 117.6(4) . . ?
C5 C4 N2 126.3(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.3(4) . . ?
C5 C6 H6 119.3 . . ?
C9 C8 C7 122.4(4) . . ?
C12 C8 C7 121.0(4) . . ?
C12 C8 C9 116.6(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.3 . . ?
N3 C10 C9 123.5(4) . . ?
N3 C10 H10 118.3 . . ?
C11 N3 C10 116.7(4) . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.3(4) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.2 . . ?
C11 C12 C8 119.6(4) . . ?
C11 C12 H12 120.2 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(3) 2.16(3) 3.038(6) 166(6) 2_665 yes

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 C1 C2 C3 -176.7(4) . . . . ?
N1 C1 C6 C5 176.9(4) . . . . ?
N2 C7 C8 C9 -4.8(6) . . . . ?
N2 C7 C8 C12 176.2(4) . . . . ?
N2 C4 C5 C6 -178.0(3) . . . . ?
C7 N2 C4 C3 174.3(4) . . . . ?
C7 N2 C4 C5 -6.6(6) . . . . ?
C7 C8 C9 C10 -177.9(3) . . . . ?
C7 C8 C12 C11 176.6(4) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C1 C6 C5 -1.7(6) . . . . ?
C2 C3 C4 N2 178.3(3) . . . . ?
C2 C3 C4 C5 -0.9(6) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 N2 C7 C8 179.4(3) . . . . ?
C4 C5 C6 C1 0.3(6) . . . . ?
C6 C1 C2 C3 1.9(6) . . . . ?
C8 C9 C10 N3 0.9(6) . . . . ?
C9 C8 C12 C11 -2.4(5) . . . . ?
C9 C10 N3 C11 -1.6(6) . . . . ?
C10 N3 C11 C12 0.2(6) . . . . ?
N3 C11 C12 C8 1.8(6) . . . . ?
C12 C8 C9 C10 1.1(5) . . . . ?

_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_PI_290_a
_database_code_depnum_ccdc_archive 'CCDC 2072423'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_290_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.19 Note  
RESPONSE: The molecule is pedaling at this temperature, resulting in a
          number of disordered atom positions.
;
_vrf_PLAT420_PI_290_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT978_PI_290_a            
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The remaining residual electron density is located outside of the 
          molecule or between carbon and nitrogen atoms.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.86556(7)
_cell_length_b                   7.46244(9)
_cell_length_c                   23.3965(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1024.09(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9002
_cell_measurement_theta_min      3.75
_cell_measurement_theta_max      77.109
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.81 4.69 2.06 0.0636
0.30 -4.43 -5.99 0.0646
-3.01 2.74 3.50 0.0538
-3.71 -0.11 3.33 0.0485
2.95 -0.89 -9.16 0.0528
3.71 0.14 -3.32 0.0545
0.83 -3.63 9.51 0.0666
0.02 -4.00 5.98 0.0646
0.24 -3.04 -11.77 0.0486
2.54 2.17 9.03 0.0670
1.32 -0.29 -14.21 0.0337
-3.58 1.62 -0.50 0.0408
-0.10 1.71 -14.20 0.0357
0.60 -0.35 14.96 0.0244
-0.32 0.26 -15.11 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16960
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.281
_diffrn_reflns_theta_min         3.778
_diffrn_ambient_temperature      290.35
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                1895
_reflns_number_total             2117
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       0.0070(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.011
_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)+(0.0580P)²+0.0213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0962
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.90 and 0.10, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.27051 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.49412 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1731(4) 0.5371(3) 0.52279(8) 0.0759(5) Uani 1 1 d . . . . .
H1A H 0.053(5) 0.616(4) 0.5321(11) 0.091 Uiso 1 1 d . U . . .
H1B H 0.244(5) 0.482(4) 0.5510(12) 0.091 Uiso 1 1 d . U . . .
N2A N 0.5892(4) 0.6063(3) 0.30814(10) 0.0566(5) Uani 0.900(4) 1 d D U P A 1
C7A C 0.7810(4) 0.5440(3) 0.29372(9) 0.0566(6) Uani 0.900(4) 1 d D U P A 1
H7A H 0.868566 0.483699 0.320700 0.068 Uiso 0.900(4) 1 calc R U P A 1
N2B N 0.667(4) 0.549(3) 0.3239(8) 0.061(4) Uani 0.100(4) 1 d D U P A 2
C7B C 0.602(4) 0.609(3) 0.2754(9) 0.064(4) Uani 0.100(4) 1 d D U P A 2
H7B H 0.460162 0.661494 0.270705 0.076 Uiso 0.100(4) 1 calc R U P A 2
C1 C 0.2832(3) 0.5564(3) 0.47144(7) 0.0560(4) Uani 1 1 d . . . . .
C2 C 0.1917(3) 0.6607(3) 0.42763(8) 0.0590(5) Uani 1 1 d . . . . .
H2 H 0.056739 0.723186 0.433745 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2990(3) 0.6721(3) 0.37537(8) 0.0581(5) Uani 1 1 d . . . . .
H3 H 0.233461 0.740960 0.346605 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5025(3) 0.5835(2) 0.36459(7) 0.0549(4) Uani 1 1 d . . . . .
C5 C 0.5979(3) 0.4831(3) 0.40885(8) 0.0603(5) Uani 1 1 d . . . . .
H5 H 0.735877 0.424523 0.403034 0.072 Uiso 1 1 calc R U . . .
C6 C 0.4903(3) 0.4694(3) 0.46120(8) 0.0604(5) Uani 1 1 d . . . . .
H6 H 0.556543 0.401259 0.490048 0.072 Uiso 1 1 calc R U . . .
C8A C 0.8689(5) 0.5647(3) 0.23528(9) 0.0516(6) Uani 0.900(4) 1 d D U P A 1
C9A C 0.7421(5) 0.6434(4) 0.19179(12) 0.0570(6) Uani 0.900(4) 1 d . U P A 1
H9A H 0.597115 0.688327 0.199160 0.068 Uiso 0.900(4) 1 calc R U P A 1
C10A C 0.8333(7) 0.6541(6) 0.13781(12) 0.0631(7) Uani 0.900(4) 1 d . U P A 1
H10A H 0.745960 0.707768 0.109408 0.076 Uiso 0.900(4) 1 calc R U P A 1
N3A N 1.0392(6) 0.5924(5) 0.12346(12) 0.0603(6) Uani 0.900(4) 1 d . U P A 1
C11A C 1.1601(5) 0.5205(4) 0.16542(12) 0.0601(7) Uani 0.900(4) 1 d . U P A 1
H11A H 1.304893 0.477523 0.156803 0.072 Uiso 0.900(4) 1 calc R U P A 1
C12A C 1.0847(5) 0.5053(3) 0.22135(11) 0.0585(6) Uani 0.900(4) 1 d . U P A 1
H12A H 1.178527 0.455501 0.249190 0.070 Uiso 0.900(4) 1 calc R U P A 1
C8B C 0.767(4) 0.590(2) 0.2255(8) 0.052(3) Uani 0.100(4) 1 d DG U P A 2
C9B C 0.696(3) 0.663(3) 0.1738(10) 0.058(3) Uani 0.100(4) 1 d G U P A 2
H9B H 0.552993 0.716736 0.170924 0.070 Uiso 0.100(4) 1 calc R U P A 2
C10B C 0.838(5) 0.657(5) 0.1264(8) 0.059(3) Uani 0.100(4) 1 d G U P A 2
H10B H 0.791141 0.705623 0.091832 0.070 Uiso 0.100(4) 1 calc R U P A 2
N3B N 1.052(5) 0.577(5) 0.1307(9) 0.059(4) Uani 0.100(4) 1 d G U P A 2
C11B C 1.123(3) 0.504(3) 0.1824(11) 0.058(3) Uani 0.100(4) 1 d G U P A 2
H11B H 1.265502 0.450374 0.185251 0.069 Uiso 0.100(4) 1 calc R U P A 2
C12B C 0.980(4) 0.510(3) 0.2298(8) 0.054(3) Uani 0.100(4) 1 d G U P A 2
H12B H 1.027357 0.461483 0.264344 0.064 Uiso 0.100(4) 1 calc R U 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
N1 H1A 0.94(3) . ?
N1 H1B 0.88(3) . ?
N1 C1 1.372(2) . ?
N2A C7A 1.263(3) . ?
N2A C4 1.426(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.469(3) . ?
N2B C7B 1.28(2) . ?
N2B C4 1.38(2) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.52(2) . ?
C1 C2 1.394(3) . ?
C1 C6 1.398(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 C5 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9300 . ?
C8A C9A 1.391(3) . ?
C8A C12A 1.380(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.374(4) . ?
C10A H10A 0.9300 . ?
C10A N3A 1.335(3) . ?
N3A C11A 1.324(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.386(3) . ?
C12A H12A 0.9300 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9300 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9300 . ?

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
H1A N1 H1B 118(2) . . ?
C1 N1 H1A 119.3(17) . . ?
C1 N1 H1B 118.8(18) . . ?
C7A N2A C4 121.4(2) . . ?
N2A C7A H7A 119.3 . . ?
N2A C7A C8A 121.5(2) . . ?
C8A C7A H7A 119.3 . . ?
C7B N2B C4 110.0(18) . . ?
N2B C7B H7B 121.1 . . ?
N2B C7B C8B 117.7(19) . . ?
C8B C7B H7B 121.1 . . ?
N1 C1 C2 121.43(18) . . ?
N1 C1 C6 120.68(17) . . ?
C2 C1 C6 117.89(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.74(19) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.65(17) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 144.7(9) . . ?
N2B C4 C5 97.5(9) . . ?
C3 C4 N2A 114.73(17) . . ?
C3 C4 C5 117.77(17) . . ?
C5 C4 N2A 127.50(19) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.97(17) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.95(17) . . ?
C5 C6 H6 119.5 . . ?
C9A C8A C7A 122.5(3) . . ?
C12A C8A C7A 120.5(3) . . ?
C12A C8A C9A 117.0(2) . . ?
C8A C9A H9A 120.4 . . ?
C10A C9A C8A 119.2(2) . . ?
C10A C9A H9A 120.4 . . ?
C9A C10A H10A 117.9 . . ?
N3A C10A C9A 124.3(2) . . ?
N3A C10A H10A 117.9 . . ?
C11A N3A C10A 115.9(2) . . ?
N3A C11A H11A 117.9 . . ?
N3A C11A C12A 124.2(2) . . ?
C12A C11A H11A 117.9 . . ?
C8A C12A C11A 119.3(2) . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 116.3(18) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 123.6(18) . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
N3B C10B C9B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C10B N3B C11B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
C12B C11B N3B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.88(3) 2.19(3) 3.054(3) 166(2) 2_665 yes
N1 H1B N3B 0.88(3) 2.26(8) 3.11(7) 164(5) 2_665 yes

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 C1 C2 C3 -176.99(18) . . . . ?
N1 C1 C6 C5 177.65(19) . . . . ?
N2A C7A C8A C9A -4.1(3) . . . . ?
N2A C7A C8A C12A 176.0(2) . . . . ?
N2A C4 C5 C6 -178.19(18) . . . . ?
C7A N2A C4 C3 174.78(19) . . . . ?
C7A N2A C4 C5 -5.6(3) . . . . ?
C7A C8A C9A C10A -178.3(3) . . . . ?
C7A C8A C12A C11A 177.6(2) . . . . ?
N2B C7B C8B C9B -177.4(19) . . . . ?
N2B C7B C8B C12B 1(3) . . . . ?
N2B C4 C5 C6 -178.2(8) . . . . ?
C7B N2B C4 C3 -8(3) . . . . ?
C7B N2B C4 C5 171.4(16) . . . . ?
C7B C8B C9B C10B 178.2(19) . . . . ?
C7B C8B C12B C11B -178(2) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C3 C4 N2A 178.90(18) . . . . ?
C2 C3 C4 N2B 178.6(14) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 N2A C7A C8A 178.93(18) . . . . ?
C4 N2B C7B C8B 177.2(15) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C8A C9A C10A N3A 0.3(4) . . . . ?
C9A C8A C12A C11A -2.3(3) . . . . ?
C9A C10A N3A C11A -1.5(4) . . . . ?
C10A N3A C11A C12A 0.7(3) . . . . ?
N3A C11A C12A C8A 1.2(4) . . . . ?
C12A C8A C9A C10A 1.6(3) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_250_a
_database_code_depnum_ccdc_archive 'CCDC 2072421'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_250_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.21 Note  
RESPONSE: The molecule begins to pedal at this temperature, resulting in a
          number of disordered atom positions. 
;
_vrf_PLAT420_PI_250_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT721_PI_250_a            
;
PROBLEM: Bond    Calc     1.41(8), Rep     1.39000 Dev...       0.02 Ang.  
RESPONSE: This bond was constrained with an AFIX 66 command.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.85572(6)
_cell_length_b                   7.39661(7)
_cell_length_c                   23.4514(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1015.738(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    11471
_cell_measurement_theta_min      3.745
_cell_measurement_theta_max      77.188
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.82 4.64 2.11 0.0636
0.30 -4.39 -6.04 0.0646
-3.01 2.71 3.57 0.0538
-3.70 -0.13 3.38 0.0485
2.94 -0.87 -9.22 0.0528
3.70 0.15 -3.38 0.0545
0.85 -3.60 9.48 0.0666
0.03 -3.97 5.96 0.0646
0.24 -3.01 -11.82 0.0486
2.54 2.15 9.03 0.0670
1.31 -0.28 -14.26 0.0337
-3.58 1.60 -0.44 0.0408
-0.11 1.70 -14.21 0.0357
0.61 -0.35 14.97 0.0244
-0.33 0.26 -15.13 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19288
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.368
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      249.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2011
_reflns_number_total             2122
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0055(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2122
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      0.995
_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)+(0.0450P)²+0.0641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0799
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.28211 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.49565 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1788(3) 0.5353(2) 0.52229(7) 0.0600(4) Uani 1 1 d . . . . .
H1A H 0.057(4) 0.609(3) 0.5313(10) 0.072 Uiso 1 1 d . U . . .
H1B H 0.256(4) 0.482(3) 0.5508(10) 0.072 Uiso 1 1 d . U . . .
N2A N 0.5914(3) 0.6087(2) 0.30793(7) 0.0455(4) Uani 0.969(3) 1 d D U P A 1
C7A C 0.7850(3) 0.5470(2) 0.29346(7) 0.0449(4) Uani 0.969(3) 1 d D U P A 1
H7A H 0.875086 0.486617 0.320620 0.054 Uiso 0.969(3) 1 calc R U P A 1
N2B N 0.658(10) 0.561(8) 0.321(2) 0.048(5) Uani 0.031(3) 1 d D U P A 2
C7B C 0.586(8) 0.605(8) 0.270(2) 0.050(5) Uani 0.031(3) 1 d D U P A 2
H7B H 0.435502 0.641277 0.262563 0.059 Uiso 0.031(3) 1 calc R U P A 2
C1 C 0.2877(3) 0.5573(2) 0.47100(7) 0.0443(4) Uani 1 1 d . . . . .
C2 C 0.1930(3) 0.6628(2) 0.42757(7) 0.0467(4) Uani 1 1 d . . . . .
H2 H 0.055883 0.725562 0.434089 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2995(3) 0.6756(2) 0.37506(7) 0.0450(4) Uani 1 1 d . . . . .
H3 H 0.231627 0.745619 0.346226 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5045(3) 0.5874(2) 0.36385(6) 0.0421(4) Uani 1 1 d . . . . .
C5 C 0.6023(3) 0.4853(2) 0.40790(7) 0.0462(4) Uani 1 1 d . . . . .
H5 H 0.742229 0.426130 0.401736 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4961(3) 0.4705(2) 0.46010(7) 0.0474(4) Uani 1 1 d . . . . .
H6 H 0.564521 0.400975 0.488965 0.057 Uiso 1 1 calc R U . . .
C8A C 0.8709(4) 0.5683(2) 0.23497(7) 0.0411(4) Uani 0.969(3) 1 d D U P A 1
C9A C 0.7406(3) 0.6459(3) 0.19170(9) 0.0448(5) Uani 0.969(3) 1 d . U P A 1
H9A H 0.593626 0.690552 0.199489 0.054 Uiso 0.969(3) 1 calc R U P A 1
C10A C 0.8294(3) 0.6566(3) 0.13734(9) 0.0491(5) Uani 0.969(3) 1 d . U P A 1
H10A H 0.739189 0.709851 0.108761 0.059 Uiso 0.969(3) 1 calc R U P A 1
N3A N 1.0369(3) 0.5953(2) 0.12291(7) 0.0466(4) Uani 0.969(3) 1 d . U P A 1
C11A C 1.1613(3) 0.5240(3) 0.16483(11) 0.0463(5) Uani 0.969(3) 1 d . U P A 1
H11A H 1.307884 0.480683 0.155846 0.056 Uiso 0.969(3) 1 calc R U P A 1
C12A C 1.0882(4) 0.5096(3) 0.22080(9) 0.0458(4) Uani 0.969(3) 1 d . U P A 1
H12A H 1.184868 0.460561 0.248829 0.055 Uiso 0.969(3) 1 calc R U P A 1
C8B C 0.770(9) 0.591(7) 0.225(2) 0.043(4) Uani 0.031(3) 1 d DG U P A 2
C9B C 0.719(7) 0.670(7) 0.172(3) 0.046(4) Uani 0.031(3) 1 d G U P A 2
H9B H 0.577230 0.726736 0.166745 0.055 Uiso 0.031(3) 1 calc R U P A 2
C10B C 0.878(11) 0.665(9) 0.1283(19) 0.047(4) Uani 0.031(3) 1 d G U P A 2
H10B H 0.843600 0.718803 0.092981 0.056 Uiso 0.031(3) 1 calc R U P A 2
N3B N 1.088(9) 0.581(9) 0.137(2) 0.045(4) Uani 0.031(3) 1 d G U P A 2
C11B C 1.139(7) 0.502(6) 0.189(3) 0.043(3) Uani 0.031(3) 1 d G U P A 2
H11B H 1.280760 0.445554 0.194326 0.052 Uiso 0.031(3) 1 calc R U P A 2
C12B C 0.980(11) 0.507(6) 0.2328(18) 0.043(3) Uani 0.031(3) 1 d G U P A 2
H12B H 1.014393 0.453485 0.268092 0.051 Uiso 0.031(3) 1 calc R U 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
N1 H1A 0.92(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.371(2) . ?
N2A C7A 1.268(2) . ?
N2A C4 1.416(2) . ?
C7A H7A 0.9400 . ?
C7A C8A 1.469(2) . ?
N2B C7B 1.30(4) . ?
N2B C4 1.37(6) . ?
C7B H7B 0.9400 . ?
C7B C8B 1.52(3) . ?
C1 C2 1.398(2) . ?
C1 C6 1.402(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.391(2) . ?
C4 C5 1.402(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.378(2) . ?
C6 H6 0.9400 . ?
C8A C9A 1.393(2) . ?
C8A C12A 1.385(3) . ?
C9A H9A 0.9400 . ?
C9A C10A 1.379(3) . ?
C10A H10A 0.9400 . ?
C10A N3A 1.340(3) . ?
N3A C11A 1.333(2) . ?
C11A H11A 0.9400 . ?
C11A C12A 1.385(3) . ?
C12A H12A 0.9400 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9400 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9400 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9400 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9400 . ?

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
H1A N1 H1B 119(2) . . ?
C1 N1 H1A 119.3(15) . . ?
C1 N1 H1B 118.1(15) . . ?
C7A N2A C4 121.96(17) . . ?
N2A C7A H7A 119.4 . . ?
N2A C7A C8A 121.16(17) . . ?
C8A C7A H7A 119.4 . . ?
C7B N2B C4 115(5) . . ?
N2B C7B H7B 123.3 . . ?
N2B C7B C8B 113(5) . . ?
C8B C7B H7B 123.3 . . ?
N1 C1 C2 121.41(16) . . ?
N1 C1 C6 120.66(15) . . ?
C2 C1 C6 117.91(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.52(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.67(15) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 141(2) . . ?
N2B C4 C5 102(2) . . ?
C3 C4 N2A 115.66(14) . . ?
C3 C4 C5 117.77(15) . . ?
C5 C4 N2A 126.56(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.86(15) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.24(15) . . ?
C5 C6 H6 119.4 . . ?
C9A C8A C7A 122.4(2) . . ?
C12A C8A C7A 120.3(2) . . ?
C12A C8A C9A 117.22(15) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A C8A 119.38(16) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 118.1 . . ?
N3A C10A C9A 123.77(18) . . ?
N3A C10A H10A 118.1 . . ?
C11A N3A C10A 116.30(16) . . ?
N3A C11A H11A 117.9 . . ?
N3A C11A C12A 124.12(17) . . ?
C12A C11A H11A 117.9 . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A C8A 119.16(16) . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 116(5) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 124(5) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B N3B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
C12B C11B N3B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.90(2) 2.16(3) 3.045(2) 169(2) 2_665 yes
N1 H1B N3B 0.90(2) 2.26(16) 3.13(19) 163(11) 2_665 yes

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 C1 C2 C3 -176.53(16) . . . . ?
N1 C1 C6 C5 177.17(16) . . . . ?
N2A C7A C8A C9A -4.2(3) . . . . ?
N2A C7A C8A C12A 176.16(17) . . . . ?
N2A C4 C5 C6 -177.77(15) . . . . ?
C7A N2A C4 C3 174.51(16) . . . . ?
C7A N2A C4 C5 -6.5(3) . . . . ?
C7A C8A C9A C10A -178.01(16) . . . . ?
C7A C8A C12A C11A 177.19(16) . . . . ?
N2B C7B C8B C9B -167(5) . . . . ?
N2B C7B C8B C12B 12(7) . . . . ?
N2B C4 C5 C6 -178(2) . . . . ?
C7B N2B C4 C3 -14(8) . . . . ?
C7B N2B C4 C5 165(5) . . . . ?
C7B C8B C9B C10B 179(4) . . . . ?
C7B C8B C12B C11B -179(5) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C3 C4 N2A 178.52(15) . . . . ?
C2 C3 C4 N2B 178(4) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 N2A C7A C8A 179.15(14) . . . . ?
C4 N2B C7B C8B 174(4) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 C3 2.0(2) . . . . ?
C8A C9A C10A N3A 0.3(3) . . . . ?
C9A C8A C12A C11A -2.5(2) . . . . ?
C9A C10A N3A C11A -1.3(3) . . . . ?
C10A N3A C11A C12A 0.4(3) . . . . ?
N3A C11A C12A C8A 1.5(3) . . . . ?
C12A C8A C9A C10A 1.6(2) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_270_a
_database_code_depnum_ccdc_archive 'CCDC 2072422'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_270_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.23 Note  
RESPONSE: The molecule is pedaling at this temperature, resulting in a
          number of disordered atom positions.
;
_vrf_PLAT420_PI_270_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT978_PI_270_a            
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The remaining residual electron density is located outside of the 
          molecule or between carbon and nitrogen atoms.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.86140(6)
_cell_length_b                   7.42624(8)
_cell_length_c                   23.4280(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1019.778(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    10372
_cell_measurement_theta_min      3.748
_cell_measurement_theta_max      77.169
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.81 4.66 -2.07 0.0636
-0.30 -4.41 6.01 0.0646
3.01 2.72 -3.52 0.0538
3.71 -0.12 -3.35 0.0485
-2.95 -0.88 9.18 0.0528
-3.71 0.14 3.34 0.0545
-0.84 -3.61 -9.51 0.0666
-0.02 -3.98 -5.98 0.0646
-0.24 -3.03 11.79 0.0486
-2.54 2.16 -9.04 0.0670
-1.32 -0.29 14.23 0.0337
3.58 1.61 0.49 0.0408
0.10 1.70 14.22 0.0357
-0.60 -0.35 -14.97 0.0244
0.33 0.26 15.13 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.309
_diffrn_reflns_theta_min         3.773
_diffrn_ambient_temperature      269.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                1976
_reflns_number_total             2131
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 743 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       0.0059(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.004
_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)+(0.0469P)²+0.0520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.95 and 0.05, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.28219 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.50679 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1769(3) 0.5357(3) 0.52242(7) 0.0669(5) Uani 1 1 d . . . . .
H1A H 0.057(4) 0.611(3) 0.5319(10) 0.080 Uiso 1 1 d . U . . .
H1B H 0.254(4) 0.482(3) 0.5512(11) 0.080 Uiso 1 1 d . U . . .
N2A N 0.5907(3) 0.6078(2) 0.30799(8) 0.0504(4) Uani 0.947(4) 1 d D U P A 1
C7A C 0.7836(3) 0.5457(3) 0.29348(8) 0.0499(5) Uani 0.947(4) 1 d D U P A 1
H7A H 0.871904 0.485620 0.320389 0.060 Uiso 0.947(4) 1 calc R U P A 1
N2B N 0.663(6) 0.556(5) 0.3236(13) 0.055(4) Uani 0.053(4) 1 d D U P A 2
C7B C 0.598(6) 0.616(5) 0.2742(14) 0.057(4) Uani 0.053(4) 1 d D U P A 2
H7B H 0.456614 0.670305 0.268750 0.069 Uiso 0.053(4) 1 calc R U P A 2
C1 C 0.2864(3) 0.5570(2) 0.47110(7) 0.0492(4) Uani 1 1 d . . . . .
C2 C 0.1926(3) 0.6618(2) 0.42751(7) 0.0522(4) Uani 1 1 d . . . . .
H2 H 0.056987 0.723701 0.433818 0.063 Uiso 1 1 calc R U . . .
C3 C 0.2996(3) 0.6745(2) 0.37513(7) 0.0507(4) Uani 1 1 d . . . . .
H3 H 0.233319 0.743823 0.346535 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5038(3) 0.5860(2) 0.36413(7) 0.0476(4) Uani 1 1 d . . . . .
C5 C 0.6005(3) 0.4845(2) 0.40809(7) 0.0522(4) Uani 1 1 d . . . . .
H5 H 0.738554 0.425887 0.402048 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4937(3) 0.4701(2) 0.46043(7) 0.0528(4) Uani 1 1 d . . . . .
H6 H 0.560758 0.401420 0.489062 0.063 Uiso 1 1 calc R U . . .
C8A C 0.8705(5) 0.5668(3) 0.23511(8) 0.0460(4) Uani 0.947(4) 1 d D U P A 1
C9A C 0.7415(4) 0.6451(3) 0.19180(10) 0.0505(5) Uani 0.947(4) 1 d . U P A 1
H9A H 0.596593 0.690015 0.199465 0.061 Uiso 0.947(4) 1 calc R U P A 1
C10A C 0.8307(4) 0.6555(4) 0.13747(10) 0.0555(6) Uani 0.947(4) 1 d . U P A 1
H10A H 0.741900 0.708355 0.109145 0.067 Uiso 0.947(4) 1 calc R U P A 1
N3A N 1.0376(4) 0.5941(4) 0.12305(8) 0.0525(5) Uani 0.947(4) 1 d . U P A 1
C11A C 1.1604(4) 0.5226(3) 0.16498(10) 0.0522(5) Uani 0.947(4) 1 d . U P A 1
H11A H 1.305197 0.479582 0.156128 0.063 Uiso 0.947(4) 1 calc R U P A 1
C12A C 1.0873(4) 0.5077(3) 0.22094(9) 0.0515(5) Uani 0.947(4) 1 d . U P A 1
H12A H 1.182471 0.458815 0.248660 0.062 Uiso 0.947(4) 1 calc R U P A 1
C8B C 0.771(6) 0.590(4) 0.2252(13) 0.046(3) Uani 0.053(4) 1 d DG U P A 2
C9B C 0.706(5) 0.663(5) 0.1730(17) 0.052(4) Uani 0.053(4) 1 d G U P A 2
H9B H 0.562318 0.713719 0.168722 0.063 Uiso 0.053(4) 1 calc R U P A 2
C10B C 0.857(8) 0.661(7) 0.1272(12) 0.053(4) Uani 0.053(4) 1 d G U P A 2
H10B H 0.813914 0.709297 0.092288 0.064 Uiso 0.053(4) 1 calc R U P A 2
N3B N 1.073(7) 0.585(7) 0.1336(14) 0.052(4) Uani 0.053(4) 1 d G U P A 2
C11B C 1.137(5) 0.512(5) 0.1858(18) 0.050(3) Uani 0.053(4) 1 d G U P A 2
H11B H 1.281638 0.461716 0.190097 0.060 Uiso 0.053(4) 1 calc R U P A 2
C12B C 0.987(7) 0.515(4) 0.2316(12) 0.047(3) Uani 0.053(4) 1 d G U P A 2
H12B H 1.030045 0.466136 0.266531 0.056 Uiso 0.053(4) 1 calc R U 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
N1 H1A 0.93(3) . ?
N1 H1B 0.90(3) . ?
N1 C1 1.372(2) . ?
N2A C7A 1.267(3) . ?
N2A C4 1.420(2) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.468(3) . ?
N2B C7B 1.30(3) . ?
N2B C4 1.35(3) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.55(3) . ?
C1 C2 1.397(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C4 C5 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9300 . ?
C8A C9A 1.393(3) . ?
C8A C12A 1.385(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.378(3) . ?
C10A H10A 0.9300 . ?
C10A N3A 1.339(3) . ?
N3A C11A 1.329(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.384(3) . ?
C12A H12A 0.9300 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9300 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9300 . ?

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
H1A N1 H1B 118(2) . . ?
C1 N1 H1A 119.7(15) . . ?
C1 N1 H1B 118.1(16) . . ?
C7A N2A C4 121.81(18) . . ?
N2A C7A H7A 119.3 . . ?
N2A C7A C8A 121.39(19) . . ?
C8A C7A H7A 119.3 . . ?
C7B N2B C4 111(3) . . ?
N2B C7B H7B 122.4 . . ?
N2B C7B C8B 115(3) . . ?
C8B C7B H7B 122.4 . . ?
N1 C1 C2 121.37(17) . . ?
N1 C1 C6 120.68(16) . . ?
C2 C1 C6 117.93(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.58(17) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.58(16) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 143.6(15) . . ?
N2B C4 C5 98.5(15) . . ?
C3 C4 N2A 115.27(15) . . ?
C3 C4 C5 117.90(16) . . ?
C5 C4 N2A 126.83(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.86(15) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.13(15) . . ?
C5 C6 H6 119.4 . . ?
C9A C8A C7A 122.3(2) . . ?
C12A C8A C7A 120.5(2) . . ?
C12A C8A C9A 117.11(17) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A C8A 119.38(18) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 118.1 . . ?
N3A C10A C9A 123.9(2) . . ?
N3A C10A H10A 118.1 . . ?
C11A N3A C10A 116.14(18) . . ?
N3A C11A H11A 117.8 . . ?
N3A C11A C12A 124.36(19) . . ?
C12A C11A H11A 117.8 . . ?
C8A C12A H12A 120.5 . . ?
C11A C12A C8A 119.09(18) . . ?
C11A C12A H12A 120.5 . . ?
C9B C8B C7B 115(3) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 125(3) . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
N3B C10B C9B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
N3B C11B C12B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.90(3) 2.16(3) 3.048(3) 169(2) 2_665 yes
N1 H1B N3B 0.90(3) 2.24(12) 3.12(13) 166(7) 2_665 yes

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 C1 C2 C3 -176.73(17) . . . . ?
N1 C1 C6 C5 177.25(17) . . . . ?
N2A C7A C8A C9A -4.1(3) . . . . ?
N2A C7A C8A C12A 176.08(18) . . . . ?
N2A C4 C5 C6 -177.88(16) . . . . ?
C7A N2A C4 C3 174.63(17) . . . . ?
C7A N2A C4 C5 -6.3(3) . . . . ?
C7A C8A C9A C10A -177.9(2) . . . . ?
C7A C8A C12A C11A 177.25(18) . . . . ?
N2B C7B C8B C9B -177(3) . . . . ?
N2B C7B C8B C12B -2(4) . . . . ?
N2B C4 C5 C6 -178.8(15) . . . . ?
C7B N2B C4 C3 -9(5) . . . . ?
C7B N2B C4 C5 171(3) . . . . ?
C7B C8B C9B C10B 175(3) . . . . ?
C7B C8B C12B C11B -174(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
C2 C3 C4 N2A 178.49(16) . . . . ?
C2 C3 C4 N2B 179(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 N2A C7A C8A 179.15(15) . . . . ?
C4 N2B C7B C8B 179(2) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 1.7(3) . . . . ?
C8A C9A C10A N3A 0.0(3) . . . . ?
C9A C8A C12A C11A -2.5(3) . . . . ?
C9A C10A N3A C11A -1.2(3) . . . . ?
C10A N3A C11A C12A 0.4(3) . . . . ?
N3A C11A C12A C8A 1.5(3) . . . . ?
C12A C8A C9A C10A 1.9(3) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_230_2
_database_code_depnum_ccdc_archive 'CCDC 2072426'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_230_2            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.17 Note  
RESPONSE: The molecule is pedaling at this temperature, resulting in a
          number of disordered atom positions.
;
_vrf_PLAT420_PI_230_2            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.85010(6)
_cell_length_b                   7.36978(7)
_cell_length_c                   23.4676(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1011.783(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    12345
_cell_measurement_theta_min      3.743
_cell_measurement_theta_max      77.216
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.82 -4.62 -2.13 0.0636
0.30 4.37 6.07 0.0646
-3.01 -2.69 -3.57 0.0538
-3.70 0.13 -3.37 0.0485
2.94 0.86 9.22 0.0528
3.70 -0.15 3.36 0.0545
0.84 3.59 -9.47 0.0666
0.03 3.96 -5.94 0.0646
0.24 2.99 11.85 0.0486
2.54 -2.14 -9.07 0.0670
1.31 0.27 14.27 0.0337
-3.58 -1.59 0.45 0.0408
-0.11 -1.71 14.22 0.0357
0.60 0.36 -14.99 0.0244
-0.33 -0.27 15.14 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19324
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.377
_diffrn_reflns_theta_min         3.767
_diffrn_ambient_temperature      229.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2009
_reflns_number_total             2107
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       0.0054(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2107
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      0.999
_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)+(0.0420P)²+0.0768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.98 and 0.02, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.27754 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.49168 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1804(3) 0.5347(2) 0.52229(6) 0.0542(4) Uani 1 1 d . . . . .
H1A H 0.061(4) 0.607(3) 0.5313(9) 0.065 Uiso 1 1 d . U . . .
H1B H 0.263(4) 0.482(3) 0.5509(10) 0.065 Uiso 1 1 d . U . . .
N2A N 0.5919(3) 0.6093(2) 0.30798(7) 0.0411(4) Uani 0.976(3) 1 d D U P A 1
C7A C 0.7865(3) 0.5477(2) 0.29347(7) 0.0404(4) Uani 0.976(3) 1 d D U P A 1
H7A H 0.877162 0.487540 0.320599 0.048 Uiso 0.976(3) 1 calc R U P A 1
N2B N 0.656(16) 0.568(11) 0.315(3) 0.043(5) Uani 0.024(3) 1 d D U P A 2
C7B C 0.579(9) 0.583(10) 0.264(2) 0.045(5) Uani 0.024(3) 1 d D U P A 2
H7B H 0.423550 0.586925 0.253894 0.054 Uiso 0.024(3) 1 calc R U P A 2
C1 C 0.2888(3) 0.5576(2) 0.47095(6) 0.0400(4) Uani 1 1 d . . . . .
C2 C 0.1935(3) 0.6634(2) 0.42763(7) 0.0420(4) Uani 1 1 d . . . . .
H2 H 0.056208 0.726251 0.434230 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2996(3) 0.6763(2) 0.37507(7) 0.0406(3) Uani 1 1 d . . . . .
H3 H 0.231136 0.746307 0.346263 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5054(3) 0.5880(2) 0.36379(6) 0.0379(3) Uani 1 1 d . . . . .
C5 C 0.6038(3) 0.4858(2) 0.40770(6) 0.0415(4) Uani 1 1 d . . . . .
H5 H 0.743884 0.426622 0.401446 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4978(3) 0.4707(2) 0.46007(6) 0.0423(4) Uani 1 1 d . . . . .
H6 H 0.566712 0.401116 0.488904 0.051 Uiso 1 1 calc R U . . .
C8A C 0.8716(4) 0.5692(2) 0.23500(7) 0.0369(4) Uani 0.976(3) 1 d D U P A 1
C9A C 0.7401(3) 0.6466(2) 0.19173(10) 0.0401(4) Uani 0.976(3) 1 d . U P A 1
H9A H 0.592760 0.690935 0.199585 0.048 Uiso 0.976(3) 1 calc R U P A 1
C10A C 0.8284(4) 0.6574(3) 0.13735(8) 0.0438(5) Uani 0.976(3) 1 d . U P A 1
H10A H 0.737703 0.710730 0.108833 0.053 Uiso 0.976(3) 1 calc R U P A 1
N3A N 1.0365(3) 0.5961(2) 0.12281(6) 0.0419(4) Uani 0.976(3) 1 d . U P A 1
C11A C 1.1618(3) 0.5250(2) 0.16468(10) 0.0414(4) Uani 0.976(3) 1 d . U P A 1
H11A H 1.308663 0.482017 0.155615 0.050 Uiso 0.976(3) 1 calc R U P A 1
C12A C 1.0895(4) 0.5105(2) 0.22063(8) 0.0408(4) Uani 0.976(3) 1 d . U P A 1
H12A H 1.186759 0.461583 0.248558 0.049 Uiso 0.976(3) 1 calc R U P A 1
C8B C 0.774(10) 0.594(8) 0.221(3) 0.037(4) Uani 0.024(3) 1 d DG U P A 2
C9B C 0.733(7) 0.668(7) 0.168(3) 0.040(4) Uani 0.024(3) 1 d G U P A 2
H9B H 0.592298 0.723759 0.159943 0.049 Uiso 0.024(3) 1 calc R U P A 2
C10B C 0.901(12) 0.659(9) 0.126(2) 0.042(4) Uani 0.024(3) 1 d G U P A 2
H10B H 0.873114 0.709465 0.089679 0.050 Uiso 0.024(3) 1 calc R U P A 2
N3B N 1.109(10) 0.577(9) 0.137(3) 0.041(4) Uani 0.024(3) 1 d G U P A 2
C11B C 1.150(8) 0.503(7) 0.191(3) 0.039(3) Uani 0.024(3) 1 d G U P A 2
H11B H 1.291142 0.446640 0.198771 0.047 Uiso 0.024(3) 1 calc R U P A 2
C12B C 0.983(13) 0.511(8) 0.233(2) 0.038(3) Uani 0.024(3) 1 d G U P A 2
H12B H 1.010328 0.460933 0.269036 0.045 Uiso 0.024(3) 1 calc R U 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
N1 H1A 0.90(2) . ?
N1 H1B 0.91(2) . ?
N1 C1 1.372(2) . ?
N2A C7A 1.272(2) . ?
N2A C4 1.413(2) . ?
C7A H7A 0.9400 . ?
C7A C8A 1.468(2) . ?
N2B C7B 1.28(4) . ?
N2B C4 1.46(9) . ?
C7B H7B 0.9400 . ?
C7B C8B 1.52(4) . ?
C1 C2 1.397(2) . ?
C1 C6 1.403(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.394(2) . ?
C4 C5 1.400(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9400 . ?
C8A C9A 1.396(2) . ?
C8A C12A 1.388(2) . ?
C9A H9A 0.9400 . ?
C9A C10A 1.379(3) . ?
C10A H10A 0.9400 . ?
C10A N3A 1.343(2) . ?
N3A C11A 1.333(2) . ?
C11A H11A 0.9400 . ?
C11A C12A 1.384(2) . ?
C12A H12A 0.9400 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9400 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9400 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9400 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9400 . ?

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
H1A N1 H1B 119(2) . . ?
C1 N1 H1A 119.5(14) . . ?
C1 N1 H1B 117.0(14) . . ?
C7A N2A C4 121.93(16) . . ?
N2A C7A H7A 119.5 . . ?
N2A C7A C8A 121.02(16) . . ?
C8A C7A H7A 119.5 . . ?
C7B N2B C4 121(7) . . ?
N2B C7B H7B 124.6 . . ?
N2B C7B C8B 111(7) . . ?
C8B C7B H7B 124.6 . . ?
N1 C1 C2 121.54(15) . . ?
N1 C1 C6 120.42(15) . . ?
C2 C1 C6 118.02(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.52(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.63(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2A 115.68(14) . . ?
C3 C4 N2B 136(3) . . ?
C3 C4 C5 117.80(14) . . ?
C5 C4 N2A 126.51(14) . . ?
C5 C4 N2B 106(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.91(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.09(14) . . ?
C5 C6 H6 119.5 . . ?
C9A C8A C7A 122.5(2) . . ?
C12A C8A C7A 120.3(2) . . ?
C12A C8A C9A 117.18(15) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A C8A 119.37(15) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 118.1 . . ?
N3A C10A C9A 123.73(17) . . ?
N3A C10A H10A 118.1 . . ?
C11A N3A C10A 116.34(15) . . ?
N3A C11A H11A 117.9 . . ?
N3A C11A C12A 124.16(16) . . ?
C12A C11A H11A 117.9 . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A C8A 119.18(16) . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 119(6) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 121(6) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B N3B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C10B N3B C11B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
N3B C11B C12B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.91(2) 2.13(2) 3.039(2) 171(2) 2_665 yes
N1 H1B N3B 0.91(2) 2.21(16) 3.1(2) 160(14) 2_665 yes

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 C1 C2 C3 -176.36(15) . . . . ?
N1 C1 C6 C5 177.04(15) . . . . ?
N2A C7A C8A C9A -4.2(3) . . . . ?
N2A C7A C8A C12A 176.30(16) . . . . ?
N2A C4 C5 C6 -177.75(15) . . . . ?
C7A N2A C4 C3 174.44(16) . . . . ?
C7A N2A C4 C5 -6.7(3) . . . . ?
C7A C8A C9A C10A -178.00(15) . . . . ?
C7A C8A C12A C11A 177.16(15) . . . . ?
N2B C7B C8B C9B -159(6) . . . . ?
N2B C7B C8B C12B 29(8) . . . . ?
N2B C4 C5 C6 -178(4) . . . . ?
C7B N2B C4 C3 -25(10) . . . . ?
C7B N2B C4 C5 153(7) . . . . ?
C7B C8B C9B C10B -172(5) . . . . ?
C7B C8B C12B C11B 172(5) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C3 C4 N2A 178.54(15) . . . . ?
C2 C3 C4 N2B 178(5) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 N2A C7A C8A 179.14(14) . . . . ?
C4 N2B C7B C8B 169(6) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 C3 2.1(2) . . . . ?
C8A C9A C10A N3A 0.4(3) . . . . ?
C9A C8A C12A C11A -2.3(2) . . . . ?
C9A C10A N3A C11A -1.4(2) . . . . ?
C10A N3A C11A C12A 0.5(2) . . . . ?
N3A C11A C12A C8A 1.4(3) . . . . ?
C12A C8A C9A C10A 1.5(2) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_230_a
_database_code_depnum_ccdc_archive 'CCDC 2072257'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_230_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.05 Note  
RESPONSE: Due to the increased number of parameters needed to model the pedal
          motion of the molecule.
;
_vrf_PLAT420_PI_230_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT721_PI_230_a            
;
PROBLEM: Bond    Calc    1.37(11), Rep     1.39000 Dev...       0.02 Ang.  
RESPONSE: Due to issues with constraining the minor disordered components.
;
_vrf_PLAT911_PI_230_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.85038(8)
_cell_length_b                   7.37100(11)
_cell_length_c                   23.4704(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1012.12(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    7407
_cell_measurement_theta_min      3.737
_cell_measurement_theta_max      76.891
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.72 -3.32 1.02 0.0741
1.48 1.49 13.20 0.0499
0.97 -1.29 -14.15 0.0373
-3.75 0.72 -1.08 0.0703
0.03 -0.11 15.23 0.0188
-0.86 -4.66 0.16 0.0580
0.35 2.47 12.98 0.0415
-0.16 0.22 -15.21 0.0132
2.11 2.09 -10.78 0.0514
2.61 3.47 0.42 0.0664
0.72 4.70 -0.20 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9643
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.117
_diffrn_reflns_theta_min         3.766
_diffrn_ambient_temperature      229.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                1952
_reflns_number_total             2043
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(19)
_refine_ls_extinction_coef       0.0073(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     403
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      0.987
_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)+(0.0399P)²+0.0652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0737
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.27329 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.49799 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
6.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8200(3) 0.4651(2) 0.47773(6) 0.0538(4) Uani 1 1 d . . . . .
H1A H 0.940(4) 0.387(3) 0.4685(9) 0.065 Uiso 1 1 d . U . . .
H1B H 0.741(4) 0.518(3) 0.4496(9) 0.065 Uiso 1 1 d . U . . .
N2A N 0.4082(3) 0.3906(2) 0.69208(7) 0.0408(4) Uani 0.977(3) 1 d D U P A 1
C7A C 0.2134(3) 0.4522(2) 0.70658(7) 0.0399(4) Uani 0.977(3) 1 d D U P A 1
H7A H 0.122600 0.512261 0.679444 0.048 Uiso 0.977(3) 1 calc R U P A 1
N2B N 0.356(18) 0.426(13) 0.684(3) 0.041(4) Uani 0.023(3) 1 d D U P A 2
C7B C 0.427(10) 0.392(10) 0.734(2) 0.042(4) Uani 0.023(3) 1 d D U P A 2
H7B H 0.578472 0.364322 0.743875 0.050 Uiso 0.023(3) 1 calc R U P A 2
C1 C 0.7114(3) 0.4424(2) 0.52911(6) 0.0395(4) Uani 1 1 d . . . . .
C2 C 0.8066(3) 0.3368(2) 0.57244(7) 0.0415(4) Uani 1 1 d . . . . .
H2 H 0.943880 0.273857 0.565859 0.050 Uiso 1 1 calc R U . . .
C3 C 0.7006(3) 0.3240(2) 0.62493(7) 0.0401(3) Uani 1 1 d . . . . .
H3 H 0.769218 0.254179 0.653765 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4943(3) 0.4120(2) 0.63620(6) 0.0375(3) Uani 1 1 d . . . . .
C5 C 0.3962(3) 0.5142(2) 0.59227(6) 0.0412(4) Uani 1 1 d . . . . .
H5 H 0.255950 0.573222 0.598493 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5023(3) 0.5294(2) 0.53990(6) 0.0420(4) Uani 1 1 d . . . . .
H6 H 0.433605 0.599139 0.511066 0.050 Uiso 1 1 calc R U . . .
C8A C 0.1286(4) 0.4309(2) 0.76503(7) 0.0368(4) Uani 0.977(3) 1 d D U P A 1
C9A C 0.2595(3) 0.3535(2) 0.80819(9) 0.0397(4) Uani 0.977(3) 1 d . U P A 1
H9A H 0.406639 0.308934 0.800290 0.048 Uiso 0.977(3) 1 calc R U P A 1
C10A C 0.1718(3) 0.3427(3) 0.86258(8) 0.0434(5) Uani 0.977(3) 1 d . U P A 1
H10A H 0.262855 0.289595 0.891055 0.052 Uiso 0.977(3) 1 calc R U P A 1
N3A N -0.0366(3) 0.4038(2) 0.87720(6) 0.0413(4) Uani 0.977(3) 1 d . U P A 1
C11A C -0.1621(3) 0.4751(2) 0.83532(11) 0.0412(4) Uani 0.977(3) 1 d . U P A 1
H11A H -0.308779 0.518434 0.844377 0.049 Uiso 0.977(3) 1 calc R U P A 1
C12A C -0.0894(4) 0.4892(2) 0.77937(8) 0.0407(4) Uani 0.977(3) 1 d . U P A 1
H12A H -0.186696 0.537814 0.751384 0.049 Uiso 0.977(3) 1 calc R U P A 1
C8B C 0.229(11) 0.404(9) 0.777(3) 0.038(3) Uani 0.023(3) 1 d DG U P A 2
C9B C 0.276(8) 0.335(8) 0.831(3) 0.040(3) Uani 0.023(3) 1 d G U P A 2
H9B H 0.417125 0.278943 0.837838 0.048 Uiso 0.023(3) 1 calc R U P A 2
C10B C 0.113(14) 0.348(10) 0.874(2) 0.041(3) Uani 0.023(3) 1 d G U P A 2
H10B H 0.145217 0.301990 0.910012 0.049 Uiso 0.023(3) 1 calc R U P A 2
N3B N -0.096(11) 0.431(9) 0.863(3) 0.040(3) Uani 0.023(3) 1 d G U P A 2
C11B C -0.143(8) 0.500(7) 0.809(4) 0.039(3) Uani 0.023(3) 1 d G U P A 2
H11B H -0.284135 0.555566 0.801524 0.047 Uiso 0.023(3) 1 calc R U P A 2
C12B C 0.020(13) 0.486(8) 0.766(2) 0.039(3) Uani 0.023(3) 1 d G U P A 2
H12B H -0.012230 0.532520 0.729349 0.046 Uiso 0.023(3) 1 calc R U 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
N1 H1A 0.93(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.373(2) . ?
N2A C7A 1.273(3) . ?
N2A C4 1.414(2) . ?
C7A H7A 0.9400 . ?
C7A C8A 1.467(2) . ?
N2B C7B 1.27(4) . ?
N2B C4 1.39(10) . ?
C7B H7B 0.9400 . ?
C7B C8B 1.53(4) . ?
C1 C2 1.397(2) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.396(2) . ?
C4 C5 1.400(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9400 . ?
C8A C9A 1.392(2) . ?
C8A C12A 1.388(2) . ?
C9A H9A 0.9400 . ?
C9A C10A 1.378(3) . ?
C10A H10A 0.9400 . ?
C10A N3A 1.345(2) . ?
N3A C11A 1.335(2) . ?
C11A H11A 0.9400 . ?
C11A C12A 1.384(2) . ?
C12A H12A 0.9400 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9400 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9400 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9400 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9400 . ?

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
H1A N1 H1B 119.1(19) . . ?
C1 N1 H1A 118.4(13) . . ?
C1 N1 H1B 117.5(14) . . ?
C7A N2A C4 121.82(15) . . ?
N2A C7A H7A 119.5 . . ?
N2A C7A C8A 120.94(16) . . ?
C8A C7A H7A 119.5 . . ?
C7B N2B C4 123(8) . . ?
N2B C7B H7B 124.8 . . ?
N2B C7B C8B 110(7) . . ?
C8B C7B H7B 124.8 . . ?
N1 C1 C2 121.54(15) . . ?
N1 C1 C6 120.36(15) . . ?
C2 C1 C6 118.08(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.53(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.67(14) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 134(3) . . ?
N2B C4 C5 108(3) . . ?
C3 C4 N2A 115.60(14) . . ?
C3 C4 C5 117.74(14) . . ?
C5 C4 N2A 126.64(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.96(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.98(14) . . ?
C5 C6 H6 119.5 . . ?
C9A C8A C7A 122.6(2) . . ?
C12A C8A C7A 120.3(2) . . ?
C12A C8A C9A 117.14(15) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A C8A 119.55(15) . . ?
C10A C9A H9A 120.2 . . ?
C9A C10A H10A 118.2 . . ?
N3A C10A C9A 123.69(17) . . ?
N3A C10A H10A 118.2 . . ?
C11A N3A C10A 116.27(15) . . ?
N3A C11A H11A 118.0 . . ?
N3A C11A C12A 124.01(15) . . ?
C12A C11A H11A 118.0 . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A C8A 119.28(15) . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 115(6) . . ?
C9B C8B C12B 120.00(5) . . ?
C12B C8B C7B 125(6) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B N3B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.00(6) . . ?
N3B C11B H11B 120.0 . . ?
N3B C11B C12B 120.00(5) . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.90(2) 2.16(2) 3.041(2) 170(2) 2_564 yes
N1 H1B N3B 0.90(2) 2.24(16) 3.1(2) 160(14) 2_564 yes

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 C1 C2 C3 176.37(15) . . . . ?
N1 C1 C6 C5 -177.16(16) . . . . ?
N2A C7A C8A C9A 4.0(3) . . . . ?
N2A C7A C8A C12A -176.20(17) . . . . ?
N2A C4 C5 C6 177.64(16) . . . . ?
C7A N2A C4 C3 -174.54(17) . . . . ?
C7A N2A C4 C5 6.7(3) . . . . ?
C7A C8A C9A C10A 178.02(16) . . . . ?
C7A C8A C12A C11A -177.15(15) . . . . ?
N2B C7B C8B C9B 168(6) . . . . ?
N2B C7B C8B C12B -16(9) . . . . ?
N2B C4 C5 C6 178(5) . . . . ?
C7B N2B C4 C3 18(13) . . . . ?
C7B N2B C4 C5 -160(8) . . . . ?
C7B C8B C9B C10B 176(5) . . . . ?
C7B C8B C12B C11B -175(6) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C2 C3 C4 N2A -178.56(16) . . . . ?
C2 C3 C4 N2B -178(6) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 N2A C7A C8A -179.08(15) . . . . ?
C4 N2B C7B C8B -175(7) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
C8A C9A C10A N3A -0.2(3) . . . . ?
C9A C8A C12A C11A 2.6(2) . . . . ?
C9A C10A N3A C11A 1.2(3) . . . . ?
C10A N3A C11A C12A -0.2(2) . . . . ?
N3A C11A C12A C8A -1.7(3) . . . . ?
C12A C8A C9A C10A -1.8(2) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_olex2_exptl_crystal_mounting_method 
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.98 and 0.02, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_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_PI_190_2
_database_code_depnum_ccdc_archive 'CCDC 2072428'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_190_2            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.83741(5)
_cell_length_b                   7.32430(6)
_cell_length_c                   23.48978(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1004.304(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    13700
_cell_measurement_theta_min      3.744
_cell_measurement_theta_max      77.235
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.81 4.59 -2.16 0.0636
-0.30 -4.34 6.09 0.0646
3.00 2.68 -3.61 0.0538
3.69 -0.13 -3.39 0.0485
-2.93 -0.85 9.25 0.0528
-3.69 0.15 3.39 0.0545
-0.84 -3.57 -9.46 0.0666
-0.03 -3.93 -5.93 0.0646
-0.24 -2.97 11.87 0.0486
-2.53 2.12 -9.07 0.0670
-1.30 -0.26 14.29 0.0337
3.57 1.58 0.42 0.0408
0.11 1.70 14.22 0.0357
-0.61 -0.36 -14.99 0.0244
0.33 0.27 15.15 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19699
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.369
_diffrn_reflns_theta_min         3.763
_diffrn_ambient_temperature      189.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2031
_reflns_number_total             2105
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 809 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(16)
_refine_ls_extinction_coef       0.0051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.061
_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)+(0.0375P)²+0.1107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0727
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1817(3) 0.5339(2) 0.52235(6) 0.0430(4) Uani 1 1 d . . . . .
H1A H 0.065(4) 0.611(3) 0.5324(9) 0.052 Uiso 1 1 d . U . . .
H1B H 0.261(4) 0.481(3) 0.5507(9) 0.052 Uiso 1 1 d . U . . .
N2 N 0.5931(2) 0.60994(17) 0.30813(5) 0.0334(3) Uani 1 1 d . . . . .
C7 C 0.7885(3) 0.5487(2) 0.29349(6) 0.0331(3) Uani 1 1 d . . . . .
H7 H 0.881338 0.488190 0.320810 0.040 Uiso 1 1 calc R U . . .
C1 C 0.2901(3) 0.5577(2) 0.47104(6) 0.0322(3) Uani 1 1 d . . . . .
C2 C 0.1935(3) 0.6640(2) 0.42770(6) 0.0340(3) Uani 1 1 d . . . . .
H2 H 0.054064 0.727376 0.434404 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2995(3) 0.6774(2) 0.37521(6) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.229774 0.748513 0.346170 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5065(3) 0.58891(19) 0.36382(6) 0.0305(3) Uani 1 1 d . . . . .
C5 C 0.6062(3) 0.4862(2) 0.40772(6) 0.0332(3) Uani 1 1 d . . . . .
H5 H 0.748464 0.426548 0.401372 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5001(3) 0.4709(2) 0.46007(6) 0.0339(3) Uani 1 1 d . . . . .
H6 H 0.570433 0.400407 0.489173 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8723(3) 0.5704(2) 0.23489(6) 0.0308(3) Uani 1 1 d . . . . .
C9 C 0.7393(3) 0.6478(2) 0.19179(6) 0.0329(3) Uani 1 1 d . . . . .
H9 H 0.590142 0.692734 0.199896 0.039 Uiso 1 1 calc R U . . .
C10 C 0.8267(3) 0.6585(2) 0.13730(6) 0.0360(3) Uani 1 1 d . . . . .
H10 H 0.734189 0.712242 0.108553 0.043 Uiso 1 1 calc R U . . .
N3 N 1.0354(2) 0.59702(18) 0.12267(5) 0.0343(3) Uani 1 1 d . . . . .
C11 C 1.1625(3) 0.5264(2) 0.16432(6) 0.0343(3) Uani 1 1 d . . . . .
H11 H 1.311208 0.483076 0.154977 0.041 Uiso 1 1 calc R U . . .
C12 C 1.0912(3) 0.5123(2) 0.22043(6) 0.0336(3) Uani 1 1 d . . . . .
H12 H 1.190581 0.463487 0.248610 0.040 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
N1 H1A 0.92(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.3725(19) . ?
N2 C7 1.273(2) . ?
N2 C4 1.4111(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.4694(19) . ?
C1 C2 1.400(2) . ?
C1 C6 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(2) . ?
C4 C5 1.403(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9500 . ?
C8 C9 1.396(2) . ?
C8 C12 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9500 . ?
C10 N3 1.343(2) . ?
N3 C11 1.3324(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 117.1(18) . . ?
C1 N1 H1A 119.5(13) . . ?
C1 N1 H1B 117.9(13) . . ?
C7 N2 C4 122.24(13) . . ?
N2 C7 H7 119.6 . . ?
N2 C7 C8 120.89(14) . . ?
C8 C7 H7 119.6 . . ?
N1 C1 C2 121.56(14) . . ?
N1 C1 C6 120.40(14) . . ?
C2 C1 C6 118.02(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.48(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.66(13) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2 115.92(12) . . ?
C3 C4 C5 117.84(13) . . ?
C5 C4 N2 126.23(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.77(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.19(13) . . ?
C5 C6 H6 119.4 . . ?
C9 C8 C7 122.55(13) . . ?
C12 C8 C7 120.14(13) . . ?
C12 C8 C9 117.31(13) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.34(13) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.2 . . ?
N3 C10 C9 123.60(14) . . ?
N3 C10 H10 118.2 . . ?
C11 N3 C10 116.58(13) . . ?
N3 C11 H11 118.0 . . ?
N3 C11 C12 124.04(14) . . ?
C12 C11 H11 118.0 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 119.07(14) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(2) 2.14(2) 3.033(2) 170.2(19) 2_665 yes

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 C1 C2 C3 -176.26(14) . . . . ?
N1 C1 C6 C5 176.89(14) . . . . ?
N2 C7 C8 C9 -4.0(2) . . . . ?
N2 C7 C8 C12 176.26(14) . . . . ?
N2 C4 C5 C6 -177.67(13) . . . . ?
C7 N2 C4 C3 174.33(14) . . . . ?
C7 N2 C4 C5 -6.8(2) . . . . ?
C7 C8 C9 C10 -177.95(13) . . . . ?
C7 C8 C12 C11 177.04(13) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C3 C4 N2 178.40(14) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 N2 C7 C8 179.04(12) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 C3 2.1(2) . . . . ?
C8 C9 C10 N3 0.4(2) . . . . ?
C9 C8 C12 C11 -2.7(2) . . . . ?
C9 C10 N3 C11 -1.5(2) . . . . ?
C10 N3 C11 C12 0.5(2) . . . . ?
N3 C11 C12 C8 1.6(2) . . . . ?
C12 C8 C9 C10 1.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# END of CIF

####################################################################### 
# 
# 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_PI_270_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2072255'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_STRVA01_PI_270_a            
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The molecule is not chiral and the same atom positions were 
          maintained throughout the variable temperature experiment. 
;
_vrf_PLAT089_PI_270_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.09 Note  
RESPONSE: Due to the increased number of parameters needed to model the pedal
          motion of the molecule.
;
_vrf_PLAT420_PI_270_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT906_PI_270_a            
;
PROBLEM: Large K Value in the Analysis of Variance ......      3.279 Check 
RESPONSE: Due to issues with absorption correction caused by the structure 
          going through an "extreme" unit cell change between 290K and 270K.
;
_vrf_PLAT911_PI_270_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8556(5)
_cell_length_b                   7.4394(6)
_cell_length_c                   23.4466(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1021.39(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    6738
_cell_measurement_theta_min      3.701
_cell_measurement_theta_max      77.423
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.72 3.34 1.08 0.0741
-0.73 -4.72 -0.21 0.0528
-2.62 -3.49 0.44 0.0664
-2.13 -2.09 -10.71 0.0514
-0.34 -2.48 12.92 0.0415
0.86 4.69 0.17 0.0580
-0.01 0.11 15.17 0.0188
0.14 -0.22 -15.15 0.0132
3.75 -0.72 -1.14 0.0703
-0.98 1.30 -14.07 0.0373
-1.47 -1.50 13.16 0.0499

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7420
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.108
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      269.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                1875
_reflns_number_total             2045
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 689 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.0066(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     403
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      0.962
_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)+(0.0499P)²+0.0485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.95 and 0.05, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.2682 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.49122 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
6.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8236(4) 0.4638(3) 0.47755(7) 0.0673(5) Uani 1 1 d . . . . .
H1A H 0.942(5) 0.386(4) 0.4681(11) 0.081 Uiso 1 1 d . U . . .
H1B H 0.745(5) 0.516(4) 0.4496(11) 0.081 Uiso 1 1 d . U . . .
N2A N 0.4092(3) 0.3921(2) 0.69200(8) 0.0514(5) Uani 0.949(4) 1 d D U P A 1
C7A C 0.2164(4) 0.4542(3) 0.70649(8) 0.0516(5) Uani 0.949(4) 1 d D U P A 1
H7A H 0.127797 0.514109 0.679619 0.062 Uiso 0.949(4) 1 calc R U P A 1
N2B N 0.333(7) 0.444(5) 0.6764(14) 0.054(4) Uani 0.051(4) 1 d D U P A 2
C7B C 0.401(6) 0.391(5) 0.7250(14) 0.055(4) Uani 0.051(4) 1 d D U P A 2
H7B H 0.548079 0.345962 0.730294 0.066 Uiso 0.051(4) 1 calc R U P A 2
C1 C 0.7143(3) 0.4428(3) 0.52886(7) 0.0496(4) Uani 1 1 d . . . . .
C2 C 0.8075(3) 0.3380(3) 0.57248(8) 0.0525(5) Uani 1 1 d . . . . .
H2 H 0.942953 0.275853 0.566191 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7006(3) 0.3258(3) 0.62490(8) 0.0514(4) Uani 1 1 d . . . . .
H3 H 0.767144 0.256833 0.653496 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4960(3) 0.4141(2) 0.63597(7) 0.0479(4) Uani 1 1 d . . . . .
C5 C 0.3992(3) 0.5155(3) 0.59182(8) 0.0532(5) Uani 1 1 d . . . . .
H5 H 0.260875 0.573930 0.597794 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5065(3) 0.5298(3) 0.53948(8) 0.0539(5) Uani 1 1 d . . . . .
H6 H 0.439546 0.598388 0.510845 0.065 Uiso 1 1 calc R U . . .
C8A C 0.1300(5) 0.4333(3) 0.76489(8) 0.0468(5) Uani 0.949(4) 1 d D U P A 1
C9A C 0.2584(4) 0.3549(3) 0.80830(10) 0.0514(5) Uani 0.949(4) 1 d . U P A 1
H9A H 0.403542 0.310066 0.800745 0.062 Uiso 0.949(4) 1 calc R U P A 1
C10A C 0.1687(5) 0.3445(5) 0.86241(10) 0.0560(6) Uani 0.949(4) 1 d . U P A 1
H10A H 0.257432 0.291487 0.890685 0.067 Uiso 0.949(4) 1 calc R U P A 1
N3A N -0.0380(4) 0.4057(4) 0.87693(9) 0.0535(6) Uani 0.949(4) 1 d . U P A 1
C11A C -0.1607(4) 0.4775(3) 0.83495(11) 0.0531(6) Uani 0.949(4) 1 d . U P A 1
H11A H -0.305582 0.520705 0.843708 0.064 Uiso 0.949(4) 1 calc R U P A 1
C12A C -0.0866(5) 0.4922(3) 0.77904(10) 0.0524(5) Uani 0.949(4) 1 d . U P A 1
H12A H -0.181621 0.541108 0.751302 0.063 Uiso 0.949(4) 1 calc R U P A 1
C8B C 0.233(7) 0.404(5) 0.7740(14) 0.049(3) Uani 0.051(4) 1 d DG U P A 2
C9B C 0.304(6) 0.337(6) 0.8264(18) 0.052(3) Uani 0.051(4) 1 d G U P A 2
H9B H 0.449357 0.287767 0.830308 0.062 Uiso 0.051(4) 1 calc R U P A 2
C10B C 0.158(9) 0.344(8) 0.8731(13) 0.053(3) Uani 0.051(4) 1 d G U P A 2
H10B H 0.205414 0.299019 0.908195 0.064 Uiso 0.051(4) 1 calc R U P A 2
N3B N -0.059(8) 0.417(9) 0.8673(16) 0.052(3) Uani 0.051(4) 1 d G U P A 2
C11B C -0.130(6) 0.484(6) 0.815(2) 0.051(3) Uani 0.051(4) 1 d G U P A 2
H11B H -0.274742 0.533671 0.810987 0.061 Uiso 0.051(4) 1 calc R U P A 2
C12B C 0.017(7) 0.478(5) 0.7682(14) 0.049(3) Uani 0.051(4) 1 d G U P A 2
H12B H -0.030802 0.522421 0.733100 0.059 Uiso 0.051(4) 1 calc R U 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
N1 H1A 0.93(3) . ?
N1 H1B 0.89(3) . ?
N1 C1 1.372(2) . ?
N2A C7A 1.266(3) . ?
N2A C4 1.418(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.468(3) . ?
N2B C7B 1.27(3) . ?
N2B C4 1.36(4) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.51(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.401(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.401(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C8A C9A 1.393(3) . ?
C8A C12A 1.382(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.375(3) . ?
C10A H10A 0.9300 . ?
C10A N3A 1.338(3) . ?
N3A C11A 1.331(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.385(3) . ?
C12A H12A 0.9300 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9300 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9300 . ?

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
H1A N1 H1B 119(2) . . ?
C1 N1 H1A 119.0(16) . . ?
C1 N1 H1B 117.2(18) . . ?
C7A N2A C4 121.8(2) . . ?
N2A C7A H7A 119.4 . . ?
N2A C7A C8A 121.3(2) . . ?
C8A C7A H7A 119.4 . . ?
C7B N2B C4 111(3) . . ?
N2B C7B H7B 121.5 . . ?
N2B C7B C8B 117(3) . . ?
C8B C7B H7B 121.5 . . ?
N1 C1 C2 121.57(18) . . ?
N1 C1 C6 120.57(18) . . ?
C2 C1 C6 117.85(17) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.71(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.68(17) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 144.0(16) . . ?
N2B C4 C5 98.2(16) . . ?
C3 C4 N2A 115.30(17) . . ?
C3 C4 C5 117.72(17) . . ?
C5 C4 N2A 126.97(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.90(17) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.12(17) . . ?
C5 C6 H6 119.4 . . ?
C9A C8A C7A 122.7(2) . . ?
C12A C8A C7A 120.4(2) . . ?
C12A C8A C9A 116.91(19) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A C8A 119.4(2) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 117.9 . . ?
N3A C10A C9A 124.1(2) . . ?
N3A C10A H10A 117.9 . . ?
C11A N3A C10A 115.9(2) . . ?
N3A C11A H11A 117.9 . . ?
N3A C11A C12A 124.2(2) . . ?
C12A C11A H11A 117.9 . . ?
C8A C12A C11A 119.32(19) . . ?
C8A C12A H12A 120.3 . . ?
C11A C12A H12A 120.3 . . ?
C9B C8B C7B 117(3) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 123(3) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B N3B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C10B N3B C11B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
C12B C11B N3B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.89(3) 2.17(3) 3.050(3) 170(2) 2_564 yes
N1 H1B N3B 0.89(3) 2.27(13) 3.14(15) 166(8) 2_564 yes

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 C1 C2 C3 176.71(19) . . . . ?
N1 C1 C6 C5 -177.41(19) . . . . ?
N2A C7A C8A C9A 4.0(3) . . . . ?
N2A C7A C8A C12A -176.0(2) . . . . ?
N2A C4 C5 C6 177.95(18) . . . . ?
C7A N2A C4 C3 -174.73(19) . . . . ?
C7A N2A C4 C5 6.0(3) . . . . ?
C7A C8A C9A C10A 178.2(2) . . . . ?
C7A C8A C12A C11A -177.4(2) . . . . ?
N2B C7B C8B C9B 177(4) . . . . ?
N2B C7B C8B C12B -3(5) . . . . ?
N2B C4 C5 C6 179.4(16) . . . . ?
C7B N2B C4 C3 13(5) . . . . ?
C7B N2B C4 C5 -168(3) . . . . ?
C7B C8B C9B C10B -180(3) . . . . ?
C7B C8B C12B C11B 180(4) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C3 C4 N2A -178.73(18) . . . . ?
C2 C3 C4 N2B 179(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 N2A C7A C8A -178.93(17) . . . . ?
C4 N2B C7B C8B -176(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
C8A C9A C10A N3A -0.1(3) . . . . ?
C9A C8A C12A C11A 2.6(3) . . . . ?
C9A C10A N3A C11A 1.2(3) . . . . ?
C10A N3A C11A C12A -0.3(3) . . . . ?
N3A C11A C12A C8A -1.6(3) . . . . ?
C12A C8A C9A C10A -1.8(3) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_130_a
_database_code_depnum_ccdc_archive 'CCDC 2072262'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_130_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT911_PI_130_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.82153(8)
_cell_length_b                   7.27320(13)
_cell_length_c                   23.5087(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     995.39(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6716
_cell_measurement_theta_min      3.734
_cell_measurement_theta_max      76.058
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9477
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.724
_diffrn_reflns_theta_min         3.760
_diffrn_ambient_temperature      129.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                1933
_reflns_number_total             2005
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 752 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(17)
_refine_ls_extinction_coef       0.0044(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.072
_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)+(0.0399P)²+0.1601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0760
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8181(3) 0.4671(2) 0.47755(6) 0.0305(3) Uani 1 1 d . . . . .
H1A H 0.935(4) 0.389(3) 0.4679(9) 0.037 Uiso 1 1 d . U . . .
H1B H 0.738(4) 0.521(3) 0.4495(9) 0.037 Uiso 1 1 d . U . . .
N2 N 0.4063(2) 0.38901(19) 0.69173(6) 0.0246(3) Uani 1 1 d . . . . .
N3 N -0.0342(2) 0.40187(19) 0.87766(6) 0.0251(3) Uani 1 1 d . . . . .
C1 C 0.7095(3) 0.4422(2) 0.52879(6) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.8073(3) 0.3353(2) 0.57209(7) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.947284 0.271847 0.565359 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7010(3) 0.3217(2) 0.62466(7) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.771315 0.250435 0.653702 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4925(3) 0.4104(2) 0.63602(6) 0.0225(3) Uani 1 1 d . . . . .
C5 C 0.3917(3) 0.5131(2) 0.59204(6) 0.0241(3) Uani 1 1 d . . . . .
H5 H 0.248470 0.572329 0.598359 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4979(3) 0.5293(2) 0.53969(6) 0.0247(3) Uani 1 1 d . . . . .
H6 H 0.427080 0.600245 0.510625 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2096(3) 0.4503(2) 0.70642(7) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.115748 0.510496 0.679121 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1267(3) 0.4286(2) 0.76507(7) 0.0229(3) Uani 1 1 d . . . . .
C9 C 0.2615(3) 0.3513(2) 0.80808(7) 0.0239(3) Uani 1 1 d . . . . .
H9 H 0.411081 0.306518 0.799764 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1757(3) 0.3404(2) 0.86269(7) 0.0259(4) Uani 1 1 d . . . . .
H10 H 0.269564 0.286672 0.891261 0.031 Uiso 1 1 calc R U . . .
C11 C -0.1632(3) 0.4722(2) 0.83602(7) 0.0248(3) Uani 1 1 d . . . . .
H11 H -0.312362 0.515266 0.845526 0.030 Uiso 1 1 calc R U . . .
C12 C -0.0933(3) 0.4863(2) 0.77982(7) 0.0248(4) Uani 1 1 d . . . . .
H12 H -0.194126 0.534613 0.751781 0.030 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
N1 H1A 0.91(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.372(2) . ?
N2 C4 1.4110(19) . ?
N2 C7 1.276(2) . ?
N3 C10 1.348(2) . ?
N3 C11 1.335(2) . ?
C1 C2 1.402(2) . ?
C1 C6 1.409(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.400(2) . ?
C4 C5 1.404(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.469(2) . ?
C8 C9 1.398(2) . ?
C8 C12 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 118.5(18) . . ?
C1 N1 H1A 118.7(13) . . ?
C1 N1 H1B 117.5(13) . . ?
C7 N2 C4 122.12(14) . . ?
C11 N3 C10 116.44(14) . . ?
N1 C1 C2 121.57(15) . . ?
N1 C1 C6 120.21(15) . . ?
C2 C1 C6 118.19(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.41(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.62(15) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2 115.76(13) . . ?
C3 C4 C5 117.84(14) . . ?
C5 C4 N2 126.40(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.93(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 120.97(14) . . ?
C5 C6 H6 119.5 . . ?
N2 C7 H7 119.6 . . ?
N2 C7 C8 120.74(14) . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 122.52(14) . . ?
C12 C8 C7 120.25(14) . . ?
C12 C8 C9 117.24(14) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.53(14) . . ?
C10 C9 H9 120.2 . . ?
N3 C10 C9 123.51(15) . . ?
N3 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.19(15) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 119.02(15) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(2) 2.14(2) 3.026(2) 169.2(19) 2_564 yes

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 C1 C2 C3 175.98(15) . . . . ?
N1 C1 C6 C5 -176.79(15) . . . . ?
N2 C4 C5 C6 177.47(14) . . . . ?
N2 C7 C8 C9 3.9(2) . . . . ?
N2 C7 C8 C12 -176.24(15) . . . . ?
N3 C11 C12 C8 -1.7(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C2 C3 C4 N2 -178.38(14) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C4 N2 C7 C8 -178.88(13) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
C7 N2 C4 C3 -174.34(15) . . . . ?
C7 N2 C4 C5 6.7(2) . . . . ?
C7 C8 C9 C10 177.94(14) . . . . ?
C7 C8 C12 C11 -177.00(14) . . . . ?
C8 C9 C10 N3 -0.4(2) . . . . ?
C9 C8 C12 C11 2.9(2) . . . . ?
C10 N3 C11 C12 -0.6(2) . . . . ?
C11 N3 C10 C9 1.6(2) . . . . ?
C12 C8 C9 C10 -1.9(2) . . . . ?

_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_PI_210_2
_database_code_depnum_ccdc_archive 'CCDC 2072427'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_210_2            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.84375(5)
_cell_length_b                   7.34622(6)
_cell_length_c                   23.48048(20)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1008.005(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    13057
_cell_measurement_theta_min      3.743
_cell_measurement_theta_max      77.15
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.82 4.61 -2.16 0.0636
-0.30 -4.35 6.09 0.0646
3.00 2.68 -3.60 0.0538
3.70 -0.13 -3.39 0.0485
-2.94 -0.85 9.25 0.0528
-3.70 0.15 3.39 0.0545
-0.85 -3.58 -9.46 0.0666
-0.03 -3.94 -5.93 0.0646
-0.24 -2.98 11.86 0.0486
-2.54 2.13 -9.06 0.0670
-1.30 -0.26 14.28 0.0337
3.57 1.59 0.42 0.0408
0.11 1.71 14.21 0.0357
-0.61 -0.36 -14.99 0.0244
0.33 0.27 15.14 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19537
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.359
_diffrn_reflns_theta_min         3.765
_diffrn_ambient_temperature      209.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2032
_reflns_number_total             2112
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.102
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(18)
_refine_ls_extinction_coef       0.0052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.073
_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)+(0.0372P)²+0.0981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0742
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1812(3) 0.5342(2) 0.52233(6) 0.0480(4) Uani 1 1 d . . . . .
H1A H 0.063(4) 0.612(3) 0.5316(9) 0.058 Uiso 1 1 d . U . . .
H1B H 0.261(4) 0.482(3) 0.5509(9) 0.058 Uiso 1 1 d . U . . .
N2 N 0.5928(2) 0.60955(18) 0.30806(5) 0.0373(3) Uani 1 1 d . . . . .
C7 C 0.7876(3) 0.5485(2) 0.29346(6) 0.0370(3) Uani 1 1 d . . . . .
H7 H 0.879066 0.488730 0.320560 0.044 Uiso 1 1 calc R U . . .
C1 C 0.2897(3) 0.5576(2) 0.47094(6) 0.0356(3) Uani 1 1 d . . . . .
C2 C 0.1935(3) 0.6636(2) 0.42768(6) 0.0375(3) Uani 1 1 d . . . . .
H2 H 0.055777 0.726275 0.434301 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2997(3) 0.6768(2) 0.37517(6) 0.0360(3) Uani 1 1 d . . . . .
H3 H 0.231044 0.747142 0.346418 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5062(3) 0.5884(2) 0.36381(6) 0.0338(3) Uani 1 1 d . . . . .
C5 C 0.6052(3) 0.4861(2) 0.40771(6) 0.0366(3) Uani 1 1 d . . . . .
H5 H 0.745674 0.427078 0.401465 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4992(3) 0.4708(2) 0.46003(6) 0.0374(3) Uani 1 1 d . . . . .
H6 H 0.568509 0.401148 0.488838 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8721(3) 0.5698(2) 0.23489(6) 0.0340(3) Uani 1 1 d . . . . .
C9 C 0.7398(3) 0.6473(2) 0.19175(6) 0.0367(3) Uani 1 1 d . . . . .
H9 H 0.592477 0.691847 0.199722 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8275(3) 0.6580(2) 0.13728(7) 0.0399(4) Uani 1 1 d . . . . .
H10 H 0.736381 0.711124 0.108785 0.048 Uiso 1 1 calc R U . . .
N3 N 1.0360(2) 0.59650(18) 0.12276(5) 0.0384(3) Uani 1 1 d . . . . .
C11 C 1.1621(3) 0.5258(2) 0.16451(7) 0.0383(4) Uani 1 1 d . . . . .
H11 H 1.309083 0.482792 0.155395 0.046 Uiso 1 1 calc R U . . .
C12 C 1.0900(3) 0.5116(2) 0.22052(6) 0.0375(3) Uani 1 1 d . . . . .
H12 H 1.187806 0.463042 0.248445 0.045 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
N1 H1A 0.92(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.3739(19) . ?
N2 C7 1.271(2) . ?
N2 C4 1.4122(19) . ?
C7 H7 0.9400 . ?
C7 C8 1.470(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.384(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.396(2) . ?
C4 C5 1.401(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9400 . ?
C8 C9 1.396(2) . ?
C8 C12 1.385(2) . ?
C9 H9 0.9400 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9400 . ?
C10 N3 1.343(2) . ?
N3 C11 1.332(2) . ?
C11 H11 0.9400 . ?
C11 C12 1.385(2) . ?
C12 H12 0.9400 . ?

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
H1A N1 H1B 118.1(19) . . ?
C1 N1 H1A 118.3(13) . . ?
C1 N1 H1B 118.0(13) . . ?
C7 N2 C4 122.16(13) . . ?
N2 C7 H7 119.5 . . ?
N2 C7 C8 121.07(14) . . ?
C8 C7 H7 119.5 . . ?
N1 C1 C2 121.46(15) . . ?
N1 C1 C6 120.41(14) . . ?
C2 C1 C6 118.11(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.40(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.68(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2 115.83(13) . . ?
C3 C4 C5 117.78(14) . . ?
C5 C4 N2 126.39(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.88(14) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.12(14) . . ?
C5 C6 H6 119.4 . . ?
C9 C8 C7 122.43(14) . . ?
C12 C8 C7 120.28(14) . . ?
C12 C8 C9 117.28(14) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.35(14) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.2 . . ?
N3 C10 C9 123.56(14) . . ?
N3 C10 H10 118.2 . . ?
C11 N3 C10 116.49(14) . . ?
N3 C11 H11 118.0 . . ?
N3 C11 C12 124.07(14) . . ?
C12 C11 H11 118.0 . . ?
C8 C12 H12 120.4 . . ?
C11 C12 C8 119.19(14) . . ?
C11 C12 H12 120.4 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(2) 2.14(2) 3.036(2) 170.6(19) 2_665 yes

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 C1 C2 C3 -176.34(15) . . . . ?
N1 C1 C6 C5 176.97(15) . . . . ?
N2 C7 C8 C9 -3.9(2) . . . . ?
N2 C7 C8 C12 176.33(14) . . . . ?
N2 C4 C5 C6 -177.71(14) . . . . ?
C7 N2 C4 C3 174.28(14) . . . . ?
C7 N2 C4 C5 -6.8(2) . . . . ?
C7 C8 C9 C10 -178.02(14) . . . . ?
C7 C8 C12 C11 177.18(14) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C3 C4 N2 178.44(14) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C4 N2 C7 C8 178.99(13) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C6 C1 C2 C3 2.0(2) . . . . ?
C8 C9 C10 N3 0.3(2) . . . . ?
C9 C8 C12 C11 -2.6(2) . . . . ?
C9 C10 N3 C11 -1.4(2) . . . . ?
C10 N3 C11 C12 0.5(2) . . . . ?
N3 C11 C12 C8 1.5(2) . . . . ?
C12 C8 C9 C10 1.8(2) . . . . ?

_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_PI_290_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2072254'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_290_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.05 Note  
RESPONSE: Due to the increased number of parameters needed to model the pedal
          motion of the molecule.
;
_vrf_PLAT420_PI_290_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1B      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT978_PI_290_a            
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The remaining residual electron density is located outside of the 
          molecule or between carbon and nitrogen atoms.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H11 N3)'
_chemical_formula_sum            'C24 H22 N6'
_chemical_formula_weight         394.47
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.72610(10)
_cell_length_b                   7.54720(10)
_cell_length_c                   23.5464(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1017.58(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    6741
_cell_measurement_theta_min      3.722
_cell_measurement_theta_max      76.74
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.64 3.43 -1.05 0.0741
-0.87 4.76 -0.18 0.0580
-3.66 -0.77 1.11 0.0703
0.73 -4.80 0.22 0.0528
2.58 -3.52 -0.42 0.0664
-0.15 -0.22 15.24 0.0132
0.02 0.10 -15.26 0.0188
0.36 -2.53 -12.99 0.0415
1.45 -1.52 -13.23 0.0499
2.08 -2.11 10.80 0.0514
0.94 1.34 14.17 0.0373

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9716
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.963
_diffrn_reflns_theta_min         3.754
_diffrn_ambient_temperature      289.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                1859
_reflns_number_total             2062
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.096
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 Flack x determined using 679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       0.0107(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2062
_refine_ls_number_restraints     226
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.020
_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)+(0.0511P)²+0.0289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.84 and 0.16, respectively. To help maintain reasonable ADP values for the minor components, SIMU, free variable DFIX restraints, and AFIX 66 constraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.9 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.47547 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim C7A \\sim N2B \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3A \\sim C8B \\sim C9B
\\sim C10B \\sim C11B \\sim C12B \\sim N3B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N1 N 0.8466(3) 0.4545(3) 0.46968(7) 0.0713(5) Uani 1 1 d D . . . .
H1A H 0.775(4) 0.494(3) 0.4383(7) 0.069(6) Uiso 1 1 d D . . . .
H1B H 0.957(4) 0.373(3) 0.4639(10) 0.085(7) Uiso 1 1 d D . . . .
N2A N 0.3411(4) 0.4751(3) 0.67226(10) 0.0547(6) Uani 0.844(5) 1 d . U P A 1
C7A C 0.4074(4) 0.4145(3) 0.71976(12) 0.0540(6) Uani 0.844(5) 1 d D U P A 1
H7A H 0.552448 0.359824 0.722655 0.065 Uiso 0.844(5) 1 calc R U P A 1
N2B N 0.414(2) 0.4123(18) 0.6858(6) 0.058(3) Uani 0.156(5) 1 d . U P A 2
C7B C 0.233(2) 0.4822(17) 0.7020(5) 0.061(3) Uani 0.156(5) 1 d D U P A 2
H7B H 0.146681 0.550467 0.676696 0.073 Uiso 0.156(5) 1 calc R U P A 2
C1 C 0.7270(3) 0.4520(2) 0.52000(6) 0.0544(4) Uani 1 1 d . . . . .
C2 C 0.5182(3) 0.5457(3) 0.52600(7) 0.0613(4) Uani 1 1 d . . . . .
H2 H 0.459125 0.608717 0.495249 0.074 Uiso 1 1 calc R U . . .
C3 C 0.3990(3) 0.5464(3) 0.57647(7) 0.0606(4) Uani 1 1 d . . . . .
H3 H 0.259376 0.608768 0.579205 0.073 Uiso 1 1 calc R U . . .
C4 C 0.4827(3) 0.4559(2) 0.62361(7) 0.0555(4) Uani 1 1 d . . . . .
C5 C 0.6910(3) 0.3614(3) 0.61800(7) 0.0604(5) Uani 1 1 d . . . . .
H5 H 0.749857 0.299316 0.648960 0.073 Uiso 1 1 calc R U . . .
C6 C 0.8108(3) 0.3590(2) 0.56714(7) 0.0588(4) Uani 1 1 d . . . . .
H6 H 0.948899 0.294743 0.564189 0.071 Uiso 1 1 calc R U . . .
C8A C 0.2586(5) 0.4295(3) 0.77038(10) 0.0496(5) Uani 0.844(5) 1 d D U P A 1
C9A C 0.3258(5) 0.3561(4) 0.82191(12) 0.0594(6) Uani 0.844(5) 1 d . U P A 1
H9A H 0.469573 0.299822 0.825574 0.071 Uiso 0.844(5) 1 calc R U P A 1
C10A C 0.1742(7) 0.3681(5) 0.86804(13) 0.0648(8) Uani 0.844(5) 1 d . U P A 1
H10A H 0.220285 0.315983 0.902031 0.078 Uiso 0.844(5) 1 calc R U P A 1
N3A N -0.0311(7) 0.4487(6) 0.86671(13) 0.0623(8) Uani 0.844(5) 1 d . U P A 1
C11A C -0.0891(5) 0.5215(5) 0.81735(13) 0.0629(7) Uani 0.844(5) 1 d . U P A 1
H11A H -0.230782 0.581490 0.815419 0.075 Uiso 0.844(5) 1 calc R U P A 1
C12A C 0.0444(6) 0.5150(4) 0.76895(11) 0.0577(7) Uani 0.844(5) 1 d . U P A 1
H12A H -0.008310 0.567285 0.735569 0.069 Uiso 0.844(5) 1 calc R U P A 1
C8B C 0.148(3) 0.4606(17) 0.7610(4) 0.052(2) Uani 0.156(5) 1 d DG U P A 2
C9B C 0.276(2) 0.3677(19) 0.8013(6) 0.058(3) Uani 0.156(5) 1 d G U P A 2
H9B H 0.419508 0.318187 0.791466 0.069 Uiso 0.156(5) 1 calc R U P A 2
C10B C 0.191(3) 0.349(3) 0.8562(5) 0.063(3) Uani 0.156(5) 1 d G U P A 2
H10B H 0.277227 0.286859 0.883171 0.075 Uiso 0.156(5) 1 calc R U P A 2
N3B N -0.023(4) 0.423(3) 0.8709(5) 0.060(3) Uani 0.156(5) 1 d G U P A 2
C11B C -0.151(2) 0.516(2) 0.8307(7) 0.067(3) Uani 0.156(5) 1 d G U P A 2
H11B H -0.294484 0.565432 0.840494 0.080 Uiso 0.156(5) 1 calc R U P A 2
C12B C -0.066(3) 0.5346(16) 0.7757(5) 0.066(3) Uani 0.156(5) 1 d G U P A 2
H12B H -0.152208 0.596763 0.748788 0.079 Uiso 0.156(5) 1 calc R U 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
N1 H1A 0.898(17) . ?
N1 H1B 0.891(19) . ?
N1 C1 1.369(2) . ?
N2A C7A 1.266(4) . ?
N2A C4 1.411(3) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.470(3) . ?
N2B C7B 1.22(2) . ?
N2B C4 1.552(15) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.481(14) . ?
C1 C2 1.396(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 C5 1.396(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C8A C9A 1.389(3) . ?
C8A C12A 1.386(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.394(4) . ?
C10A H10A 0.9300 . ?
C10A N3A 1.324(4) . ?
N3A C11A 1.328(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.373(4) . ?
C12A H12A 0.9300 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9300 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9300 . ?

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
H1A N1 H1B 115(2) . . ?
C1 N1 H1A 119.2(14) . . ?
C1 N1 H1B 118.6(16) . . ?
C7A N2A C4 120.5(2) . . ?
N2A C7A H7A 119.5 . . ?
N2A C7A C8A 121.0(2) . . ?
C8A C7A H7A 119.5 . . ?
C7B N2B C4 114.7(13) . . ?
N2B C7B H7B 119.2 . . ?
N2B C7B C8B 121.6(14) . . ?
C8B C7B H7B 119.2 . . ?
N1 C1 C2 120.59(16) . . ?
N1 C1 C6 121.48(16) . . ?
C2 C1 C6 117.92(15) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.07(16) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.28(16) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 N2A 113.58(17) . . ?
C3 C4 N2B 140.4(5) . . ?
C3 C4 C5 118.08(15) . . ?
C5 C4 N2A 128.34(17) . . ?
C5 C4 N2B 101.4(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.91(16) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.74(16) . . ?
C5 C6 H6 119.6 . . ?
C9A C8A C7A 121.1(2) . . ?
C12A C8A C7A 122.0(2) . . ?
C12A C8A C9A 116.9(2) . . ?
C8A C9A H9A 120.6 . . ?
C8A C9A C10A 118.8(2) . . ?
C10A C9A H9A 120.6 . . ?
C9A C10A H10A 117.8 . . ?
N3A C10A C9A 124.4(3) . . ?
N3A C10A H10A 117.8 . . ?
C10A N3A C11A 115.7(2) . . ?
N3A C11A H11A 117.5 . . ?
N3A C11A C12A 124.9(2) . . ?
C12A C11A H11A 117.5 . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A C8A 119.3(2) . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 121.4(11) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 118.6(11) . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
N3B C10B C9B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
N3B C11B C12B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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 C1 C2 C3 -178.94(18) . . . . ?
N1 C1 C6 C5 178.37(17) . . . . ?
N2A C7A C8A C9A 177.0(2) . . . . ?
N2A C7A C8A C12A -2.2(3) . . . . ?
N2A C4 C5 C6 -178.80(18) . . . . ?
C7A N2A C4 C3 -173.0(2) . . . . ?
C7A N2A C4 C5 6.2(3) . . . . ?
C7A C8A C9A C10A -177.5(3) . . . . ?
C7A C8A C12A C11A 178.7(2) . . . . ?
N2B C7B C8B C9B 3.5(18) . . . . ?
N2B C7B C8B C12B -176.2(11) . . . . ?
N2B C4 C5 C6 177.9(5) . . . . ?
C7B N2B C4 C3 -3.9(15) . . . . ?
C7B N2B C4 C5 179.4(10) . . . . ?
C7B C8B C9B C10B -179.6(14) . . . . ?
C7B C8B C12B C11B 179.7(14) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C3 C4 N2A 178.36(18) . . . . ?
C2 C3 C4 N2B -177.2(7) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 N2A C7A C8A -178.33(18) . . . . ?
C4 N2B C7B C8B -177.3(10) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C8A C9A C10A N3A -1.4(4) . . . . ?
C9A C8A C12A C11A -0.5(3) . . . . ?
C9A C10A N3A C11A -0.2(4) . . . . ?
C10A N3A C11A C12A 1.5(4) . . . . ?
N3A C11A C12A C8A -1.1(4) . . . . ?
C12A C8A C9A C10A 1.7(4) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_100_a
_database_code_depnum_ccdc_archive 'CCDC 2072263'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_100_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT911_PI_100_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.81332(8)
_cell_length_b                   7.24959(14)
_cell_length_c                   23.5153(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     991.03(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6344
_cell_measurement_theta_min      3.733
_cell_measurement_theta_max      76.513
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.71 -3.27 0.82 0.0741
1.50 1.43 13.22 0.0499
0.93 -1.23 -14.26 0.0373
-3.72 0.70 -0.92 0.0703
0.06 -0.15 15.26 0.0188
-0.85 -4.59 0.05 0.0580
0.38 2.39 13.07 0.0415
-0.19 0.26 -15.23 0.0132
2.08 2.08 -10.81 0.0514
2.60 3.41 0.43 0.0664
0.71 4.62 -0.08 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9303
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.172
_diffrn_reflns_theta_min         3.759
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                1927
_reflns_number_total             1998
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(18)
_refine_ls_extinction_coef       0.0039(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.076
_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)+(0.0467P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8180(3) 0.4675(2) 0.47745(6) 0.0254(4) Uani 1 1 d . . . . .
H1A H 0.933(4) 0.390(3) 0.4675(10) 0.030 Uiso 1 1 d . U . . .
H1B H 0.739(4) 0.523(3) 0.4487(10) 0.030 Uiso 1 1 d . U . . .
N2 N 0.4061(3) 0.3885(2) 0.69168(6) 0.0211(4) Uani 1 1 d . . . . .
N3 N -0.0335(3) 0.4012(2) 0.87779(6) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.7095(3) 0.4422(2) 0.52865(7) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.8077(3) 0.3350(2) 0.57201(7) 0.0207(4) Uani 1 1 d . . . . .
H2 H 0.947984 0.271508 0.565291 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7013(3) 0.3212(2) 0.62455(7) 0.0203(4) Uani 1 1 d . . . . .
H3 H 0.772027 0.249844 0.653576 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4921(3) 0.4099(2) 0.63596(7) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.3909(3) 0.5127(3) 0.59196(7) 0.0207(4) Uani 1 1 d . . . . .
H5 H 0.247375 0.571973 0.598279 0.025 Uiso 1 1 calc R U . . .
C6 C 0.4970(3) 0.5291(2) 0.53958(7) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.425765 0.599936 0.510521 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2090(3) 0.4501(2) 0.70637(7) 0.0206(4) Uani 1 1 d . . . . .
H7 H 0.114963 0.510737 0.679120 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1262(3) 0.4281(2) 0.76507(7) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.2623(3) 0.3505(3) 0.80802(7) 0.0207(4) Uani 1 1 d . . . . .
H9 H 0.412072 0.305747 0.799621 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1766(3) 0.3397(3) 0.86270(7) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.270933 0.286053 0.891241 0.027 Uiso 1 1 calc R U . . .
C11 C -0.1634(3) 0.4714(2) 0.83624(7) 0.0212(4) Uani 1 1 d . . . . .
H11 H -0.312777 0.514451 0.845851 0.025 Uiso 1 1 calc R U . . .
C12 C -0.0941(3) 0.4855(3) 0.77993(7) 0.0215(4) Uani 1 1 d . . . . .
H12 H -0.195572 0.533691 0.751957 0.026 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
N1 H1A 0.90(2) . ?
N1 H1B 0.91(2) . ?
N1 C1 1.372(2) . ?
N2 C4 1.411(2) . ?
N2 C7 1.278(2) . ?
N3 C10 1.348(2) . ?
N3 C11 1.335(2) . ?
C1 C2 1.403(2) . ?
C1 C6 1.410(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(2) . ?
C4 C5 1.405(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.470(2) . ?
C8 C9 1.401(2) . ?
C8 C12 1.392(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 117(2) . . ?
C1 N1 H1A 118.9(15) . . ?
C1 N1 H1B 118.7(14) . . ?
C7 N2 C4 122.03(15) . . ?
C11 N3 C10 116.48(15) . . ?
N1 C1 C2 121.67(17) . . ?
N1 C1 C6 120.20(16) . . ?
C2 C1 C6 118.10(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.45(17) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.66(16) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2 115.77(15) . . ?
C3 C4 C5 117.76(16) . . ?
C5 C4 N2 126.45(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.98(15) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.00(16) . . ?
C5 C6 H6 119.5 . . ?
N2 C7 H7 119.7 . . ?
N2 C7 C8 120.61(16) . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.40(16) . . ?
C12 C8 C7 120.29(16) . . ?
C12 C8 C9 117.31(16) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.37(16) . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 123.58(16) . . ?
N3 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.20(16) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 118.99(16) . . ?
C11 C12 H12 120.5 . . ?

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 C1 C2 C3 175.91(16) . . . . ?
N1 C1 C6 C5 -176.68(17) . . . . ?
N2 C4 C5 C6 177.41(16) . . . . ?
N2 C7 C8 C9 4.1(3) . . . . ?
N2 C7 C8 C12 -176.11(17) . . . . ?
N3 C11 C12 C8 -1.7(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C2 C3 C4 N2 -178.29(16) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 N2 C7 C8 -179.00(15) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C6 C1 C2 C3 -2.2(3) . . . . ?
C7 N2 C4 C3 -174.51(16) . . . . ?
C7 N2 C4 C5 6.7(3) . . . . ?
C7 C8 C9 C10 177.79(16) . . . . ?
C7 C8 C12 C11 -176.83(16) . . . . ?
C8 C9 C10 N3 -0.4(3) . . . . ?
C9 C8 C12 C11 2.9(3) . . . . ?
C10 N3 C11 C12 -0.6(3) . . . . ?
C11 N3 C10 C9 1.7(3) . . . . ?
C12 C8 C9 C10 -2.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# END of CIF
####################################################################### 
# 
# 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_PI_190_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2072259'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_190_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT911_PI_190_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.83819(7)
_cell_length_b                   7.32399(9)
_cell_length_c                   23.4915(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1004.47(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    7634
_cell_measurement_theta_min      3.736
_cell_measurement_theta_max      77.069
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.72 3.30 0.95 0.0741
-1.49 -1.47 13.20 0.0499
-0.95 1.26 -14.18 0.0373
3.74 -0.71 -1.03 0.0703
-0.04 0.12 15.23 0.0188
0.86 4.63 0.11 0.0580
-0.36 -2.44 13.00 0.0415
0.17 -0.23 -15.20 0.0132
-2.10 -2.09 -10.78 0.0514
-2.61 -3.45 0.43 0.0664
-0.72 -4.67 -0.15 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9593
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.255
_diffrn_reflns_theta_min         3.763
_diffrn_ambient_temperature      189.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                1949
_reflns_number_total             2025
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 756 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(16)
_refine_ls_extinction_coef       0.0059(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.047
_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)+(0.0331P)²+0.1216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8183(3) 0.4662(2) 0.47768(6) 0.0423(4) Uani 1 1 d . . . . .
H1A H 0.936(4) 0.390(3) 0.4684(8) 0.051 Uiso 1 1 d . U . . .
H1B H 0.739(3) 0.519(3) 0.4491(8) 0.051 Uiso 1 1 d . U . . .
N2 N 0.4068(2) 0.38995(17) 0.69185(5) 0.0327(3) Uani 1 1 d . . . . .
N3 N -0.0356(2) 0.40289(18) 0.87736(5) 0.0338(3) Uani 1 1 d . . . . .
C1 C 0.7100(3) 0.4424(2) 0.52897(6) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.8064(3) 0.3359(2) 0.57227(6) 0.0332(3) Uani 1 1 d . . . . .
H2 H 0.945496 0.272216 0.565540 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7005(3) 0.3228(2) 0.62476(6) 0.0317(3) Uani 1 1 d . . . . .
H3 H 0.770404 0.251947 0.653837 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4936(3) 0.4112(2) 0.63614(6) 0.0297(3) Uani 1 1 d . . . . .
C5 C 0.3939(3) 0.5137(2) 0.59230(6) 0.0324(3) Uani 1 1 d . . . . .
H5 H 0.251605 0.573215 0.598667 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4998(3) 0.5292(2) 0.53991(6) 0.0331(3) Uani 1 1 d . . . . .
H6 H 0.429402 0.599699 0.510818 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2116(3) 0.4511(2) 0.70649(6) 0.0322(3) Uani 1 1 d . . . . .
H7 H 0.118656 0.511366 0.679132 0.039 Uiso 1 1 calc R U . . .
C8 C 0.1276(3) 0.4298(2) 0.76508(6) 0.0300(3) Uani 1 1 d . . . . .
C9 C 0.2607(3) 0.3524(2) 0.80818(6) 0.0323(3) Uani 1 1 d . . . . .
H9 H 0.409907 0.307589 0.800081 0.039 Uiso 1 1 calc R U . . .
C10 C 0.1733(3) 0.3416(2) 0.86263(6) 0.0352(3) Uani 1 1 d . . . . .
H10 H 0.265913 0.287917 0.891353 0.042 Uiso 1 1 calc R U . . .
C11 C -0.1623(3) 0.4734(2) 0.83564(6) 0.0338(3) Uani 1 1 d . . . . .
H11 H -0.311032 0.516696 0.844937 0.041 Uiso 1 1 calc R U . . .
C12 C -0.0911(3) 0.4878(2) 0.77956(6) 0.0330(3) Uani 1 1 d . . . . .
H12 H -0.190552 0.536606 0.751416 0.040 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
N1 H1A 0.91(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.3720(19) . ?
N2 C4 1.4120(18) . ?
N2 C7 1.272(2) . ?
N3 C10 1.345(2) . ?
N3 C11 1.3321(19) . ?
C1 C2 1.400(2) . ?
C1 C6 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(2) . ?
C4 C5 1.401(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.4695(19) . ?
C8 C9 1.396(2) . ?
C8 C12 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.385(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 118.0(17) . . ?
C1 N1 H1A 118.7(13) . . ?
C1 N1 H1B 118.1(12) . . ?
C7 N2 C4 122.23(13) . . ?
C11 N3 C10 116.34(13) . . ?
N1 C1 C2 121.57(14) . . ?
N1 C1 C6 120.37(14) . . ?
C2 C1 C6 118.04(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.46(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.69(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2 115.90(12) . . ?
C3 C4 C5 117.84(13) . . ?
C5 C4 N2 126.25(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.85(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.08(13) . . ?
C5 C6 H6 119.5 . . ?
N2 C7 H7 119.5 . . ?
N2 C7 C8 120.99(14) . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 122.44(13) . . ?
C12 C8 C7 120.27(13) . . ?
C12 C8 C9 117.29(13) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.31(13) . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 123.72(14) . . ?
N3 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.22(14) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 119.07(14) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(2) 2.14(2) 3.033(2) 170.2(18) 2_564 yes

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 C1 C2 C3 176.14(14) . . . . ?
N1 C1 C6 C5 -176.90(15) . . . . ?
N2 C4 C5 C6 177.71(14) . . . . ?
N2 C7 C8 C9 3.9(2) . . . . ?
N2 C7 C8 C12 -176.28(14) . . . . ?
N3 C11 C12 C8 -1.6(2) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C2 C3 C4 N2 -178.57(14) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 N2 C7 C8 -178.90(13) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C7 N2 C4 C3 -174.34(14) . . . . ?
C7 N2 C4 C5 6.7(2) . . . . ?
C7 C8 C9 C10 178.08(14) . . . . ?
C7 C8 C12 C11 -177.18(13) . . . . ?
C8 C9 C10 N3 -0.4(2) . . . . ?
C9 C8 C12 C11 2.6(2) . . . . ?
C10 N3 C11 C12 -0.5(2) . . . . ?
C11 N3 C10 C9 1.5(2) . . . . ?
C12 C8 C9 C10 -1.7(2) . . . . ?

_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_PI_270_2
_database_code_depnum_ccdc_archive 'CCDC 2072424'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_270_2            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.22 Note  
RESPONSE: The molecule is pedaling at this temperature, resulting in a
          number of disordered atom positions.
;
_vrf_PLAT420_PI_270_2            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT978_PI_270_2            
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The remaining residual electron density is located outside of the 
          molecule or between carbon and nitrogen atoms.
;
_vrf_PLAT721_PI_270_2            
;
PROBLEM: Bond    Calc     1.41(8), Rep     1.39000 Dev...       0.02 Ang.  
RESPONSE: This bond length is constrained with an AFIX 66 command.
;
_vrf_STRVA01_PI_270_2            
;
PROBLEM: Flack parameter is too small
RESPONSE: ...
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.86137(6)
_cell_length_b                   7.42616(8)
_cell_length_c                   23.4265(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1019.695(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    10371
_cell_measurement_theta_min      3.746
_cell_measurement_theta_max      77.052
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.81 4.66 2.07 0.0636
0.30 -4.41 -6.01 0.0646
-3.01 2.72 3.52 0.0538
-3.71 -0.12 3.34 0.0485
2.95 -0.88 -9.18 0.0528
3.71 0.14 -3.33 0.0545
0.84 -3.61 9.50 0.0666
0.02 -3.98 5.98 0.0646
0.25 -3.03 -11.79 0.0486
2.54 2.16 9.04 0.0670
1.32 -0.29 -14.23 0.0337
-3.58 1.61 -0.49 0.0408
-0.10 1.70 -14.21 0.0357
0.60 -0.35 14.97 0.0244
-0.32 0.26 -15.12 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18569
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.320
_diffrn_reflns_theta_min         3.774
_diffrn_ambient_temperature      269.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                1970
_reflns_number_total             2128
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(2)
_refine_ls_extinction_coef       0.0063(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      0.998
_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)+(0.0505P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0861
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.94 and 0.06, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.28543 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.49818 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1767(3) 0.5360(3) 0.52244(7) 0.0672(5) Uani 1 1 d . . . . .
H1A H 0.056(4) 0.614(3) 0.5314(10) 0.081 Uiso 1 1 d . U . . .
H1B H 0.252(4) 0.481(3) 0.5513(11) 0.081 Uiso 1 1 d . U . . .
N2A N 0.5904(3) 0.6076(2) 0.30797(8) 0.0503(4) Uani 0.945(4) 1 d D U P A 1
C7A C 0.7834(3) 0.5459(3) 0.29347(8) 0.0504(5) Uani 0.945(4) 1 d D U P A 1
H7A H 0.871955 0.486001 0.320391 0.061 Uiso 0.945(4) 1 calc R U P A 1
N2B N 0.666(6) 0.554(4) 0.3234(13) 0.055(4) Uani 0.055(4) 1 d D U P A 2
C7B C 0.598(6) 0.617(5) 0.2742(13) 0.057(4) Uani 0.055(4) 1 d D U P A 2
H7B H 0.457555 0.673218 0.269303 0.068 Uiso 0.055(4) 1 calc R U P A 2
C1 C 0.2861(3) 0.5569(2) 0.47105(7) 0.0499(4) Uani 1 1 d . . . . .
C2 C 0.1927(3) 0.6620(2) 0.42753(7) 0.0522(4) Uani 1 1 d . . . . .
H2 H 0.057415 0.724314 0.433900 0.063 Uiso 1 1 calc R U . . .
C3 C 0.2994(3) 0.6745(2) 0.37511(7) 0.0510(4) Uani 1 1 d . . . . .
H3 H 0.232923 0.743696 0.346508 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5036(3) 0.5861(2) 0.36408(7) 0.0481(4) Uani 1 1 d . . . . .
C5 C 0.6006(3) 0.4844(2) 0.40814(7) 0.0527(4) Uani 1 1 d . . . . .
H5 H 0.738614 0.425693 0.402101 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4937(3) 0.4703(2) 0.46043(7) 0.0529(4) Uani 1 1 d . . . . .
H6 H 0.560885 0.401901 0.489132 0.063 Uiso 1 1 calc R U . . .
C8A C 0.8700(4) 0.5669(3) 0.23510(8) 0.0460(5) Uani 0.945(4) 1 d D U P A 1
C9A C 0.7416(4) 0.6452(3) 0.19171(10) 0.0506(5) Uani 0.945(4) 1 d . U P A 1
H9A H 0.596639 0.690161 0.199298 0.061 Uiso 0.945(4) 1 calc R U P A 1
C10A C 0.8309(5) 0.6554(4) 0.13753(10) 0.0559(6) Uani 0.945(4) 1 d . U P A 1
H10A H 0.741986 0.708071 0.109202 0.067 Uiso 0.945(4) 1 calc R U P A 1
N3A N 1.0379(4) 0.5942(4) 0.12299(8) 0.0529(5) Uani 0.945(4) 1 d . U P A 1
C11A C 1.1607(4) 0.5225(3) 0.16499(10) 0.0523(5) Uani 0.945(4) 1 d . U P A 1
H11A H 1.305436 0.479386 0.156167 0.063 Uiso 0.945(4) 1 calc R U P A 1
C12A C 1.0873(4) 0.5080(3) 0.22098(9) 0.0518(5) Uani 0.945(4) 1 d . U P A 1
H12A H 1.182459 0.459282 0.248748 0.062 Uiso 0.945(4) 1 calc R U P A 1
C8B C 0.768(6) 0.593(4) 0.2253(12) 0.048(3) Uani 0.055(4) 1 d DG U P A 2
C9B C 0.703(5) 0.667(5) 0.1733(16) 0.052(4) Uani 0.055(4) 1 d G U P A 2
H9B H 0.559792 0.719527 0.169415 0.063 Uiso 0.055(4) 1 calc R U P A 2
C10B C 0.852(8) 0.662(7) 0.1271(12) 0.053(4) Uani 0.055(4) 1 d G U P A 2
H10B H 0.808014 0.711761 0.092316 0.064 Uiso 0.055(4) 1 calc R U P A 2
N3B N 1.065(7) 0.583(7) 0.1329(14) 0.053(4) Uani 0.055(4) 1 d G U P A 2
C11B C 1.130(5) 0.509(5) 0.1849(17) 0.050(3) Uani 0.055(4) 1 d G U P A 2
H11B H 1.273503 0.456170 0.188719 0.060 Uiso 0.055(4) 1 calc R U P A 2
C12B C 0.982(6) 0.514(4) 0.2310(12) 0.047(3) Uani 0.055(4) 1 d G U P A 2
H12B H 1.025283 0.463935 0.265819 0.056 Uiso 0.055(4) 1 calc R U 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
N1 H1A 0.94(3) . ?
N1 H1B 0.90(3) . ?
N1 C1 1.373(2) . ?
N2A C7A 1.267(3) . ?
N2A C4 1.419(2) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.467(3) . ?
N2B C7B 1.30(3) . ?
N2B C4 1.37(3) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.53(3) . ?
C1 C2 1.396(2) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(2) . ?
C4 C5 1.399(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9300 . ?
C8A C9A 1.392(3) . ?
C8A C12A 1.387(3) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.375(3) . ?
C10A H10A 0.9300 . ?
C10A N3A 1.340(3) . ?
N3A C11A 1.330(3) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.385(3) . ?
C12A H12A 0.9300 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9300 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9300 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9300 . ?

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
H1A N1 H1B 119(2) . . ?
C1 N1 H1A 118.6(15) . . ?
C1 N1 H1B 118.5(16) . . ?
C7A N2A C4 121.85(18) . . ?
N2A C7A H7A 119.3 . . ?
N2A C7A C8A 121.35(19) . . ?
C8A C7A H7A 119.3 . . ?
C7B N2B C4 110(3) . . ?
N2B C7B H7B 122.5 . . ?
N2B C7B C8B 115(3) . . ?
C8B C7B H7B 122.5 . . ?
N1 C1 C2 121.37(17) . . ?
N1 C1 C6 120.69(16) . . ?
C2 C1 C6 117.94(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.62(17) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.59(16) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 144.1(14) . . ?
N2B C4 C5 98.0(14) . . ?
C3 C4 N2A 115.34(15) . . ?
C3 C4 C5 117.88(16) . . ?
C5 C4 N2A 126.77(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.76(15) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.18(15) . . ?
C5 C6 H6 119.4 . . ?
C9A C8A C7A 122.5(2) . . ?
C12A C8A C7A 120.4(2) . . ?
C12A C8A C9A 117.01(17) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A C8A 119.42(18) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 117.9 . . ?
N3A C10A C9A 124.1(2) . . ?
N3A C10A H10A 117.9 . . ?
C11A N3A C10A 115.95(18) . . ?
N3A C11A H11A 117.8 . . ?
N3A C11A C12A 124.32(19) . . ?
C12A C11A H11A 117.8 . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A C8A 119.13(18) . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 115(3) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 124(3) . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
N3B C10B C9B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
N3B C11B C12B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.90(3) 2.16(3) 3.047(3) 168(2) 2_665 yes
N1 H1B N3B 0.90(3) 2.24(11) 3.12(12) 165(7) 2_665 yes

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 C1 C2 C3 -176.79(17) . . . . ?
N1 C1 C6 C5 177.36(17) . . . . ?
N2A C7A C8A C9A -4.0(3) . . . . ?
N2A C7A C8A C12A 176.10(18) . . . . ?
N2A C4 C5 C6 -177.88(16) . . . . ?
C7A N2A C4 C3 174.51(17) . . . . ?
C7A N2A C4 C5 -6.4(3) . . . . ?
C7A C8A C9A C10A -178.0(2) . . . . ?
C7A C8A C12A C11A 177.24(18) . . . . ?
N2B C7B C8B C9B -177(3) . . . . ?
N2B C7B C8B C12B -2(4) . . . . ?
N2B C4 C5 C6 -178.8(14) . . . . ?
C7B N2B C4 C3 -8(4) . . . . ?
C7B N2B C4 C5 172(3) . . . . ?
C7B C8B C9B C10B 176(3) . . . . ?
C7B C8B C12B C11B -175(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C3 C4 N2A 178.55(16) . . . . ?
C2 C3 C4 N2B 179(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 N2A C7A C8A 179.16(15) . . . . ?
C4 N2B C7B C8B 179(2) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
C8A C9A C10A N3A -0.1(3) . . . . ?
C9A C8A C12A C11A -2.7(3) . . . . ?
C9A C10A N3A C11A -1.0(3) . . . . ?
C10A N3A C11A C12A 0.2(3) . . . . ?
N3A C11A C12A C8A 1.7(3) . . . . ?
C12A C8A C9A C10A 2.0(3) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_210_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2072258'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_STRVA01_PI_210_a            
;
PROBLEM: Flack parameter is too small
RESPONSE: The molecule is not chiral and the same atom positions were 
          maintained throughout the variable temperature experiment.
;
_vrf_PLAT420_PI_210_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT911_PI_210_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.84449(8)
_cell_length_b                   7.34651(10)
_cell_length_c                   23.4842(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1008.33(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    7642
_cell_measurement_theta_min      3.736
_cell_measurement_theta_max      76.887
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.72 3.31 0.99 0.0741
-1.48 -1.48 13.20 0.0499
-0.96 1.27 -14.16 0.0373
3.74 -0.71 -1.06 0.0703
-0.03 0.12 15.23 0.0188
0.86 4.64 0.13 0.0580
-0.35 -2.45 12.99 0.0415
0.16 -0.23 -15.20 0.0132
-2.11 -2.09 -10.77 0.0514
-2.61 -3.46 0.43 0.0664
-0.72 -4.68 -0.17 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9654
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.433
_diffrn_reflns_theta_min         3.764
_diffrn_ambient_temperature      209.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.637
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                1956
_reflns_number_total             2033
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.30(18)
_refine_ls_extinction_coef       0.0065(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.055
_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)+(0.0350P)²+0.1020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0700
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8191(3) 0.4657(2) 0.47771(6) 0.0476(4) Uani 1 1 d . . . . .
H1A H 0.936(4) 0.388(3) 0.4683(8) 0.057 Uiso 1 1 d . U . . .
H1B H 0.739(4) 0.518(3) 0.4500(9) 0.057 Uiso 1 1 d . U . . .
N2 N 0.4072(2) 0.39052(18) 0.69193(5) 0.0369(3) Uani 1 1 d . . . . .
N3 N -0.0362(2) 0.40335(18) 0.87725(5) 0.0380(3) Uani 1 1 d . . . . .
C1 C 0.7105(3) 0.4423(2) 0.52906(6) 0.0351(3) Uani 1 1 d . . . . .
C2 C 0.8064(3) 0.3363(2) 0.57237(6) 0.0372(3) Uani 1 1 d . . . . .
H2 H 0.943872 0.273368 0.565750 0.045 Uiso 1 1 calc R U . . .
C3 C 0.7005(3) 0.3235(2) 0.62485(6) 0.0356(3) Uani 1 1 d . . . . .
H3 H 0.769370 0.253520 0.653646 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4940(3) 0.4116(2) 0.63617(6) 0.0333(3) Uani 1 1 d . . . . .
C5 C 0.3948(3) 0.5139(2) 0.59227(6) 0.0365(3) Uani 1 1 d . . . . .
H5 H 0.254261 0.572765 0.598505 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5010(3) 0.5293(2) 0.53992(6) 0.0372(3) Uani 1 1 d . . . . .
H6 H 0.431868 0.599081 0.511122 0.045 Uiso 1 1 calc R U . . .
C7 C 0.2125(3) 0.4515(2) 0.70653(6) 0.0367(3) Uani 1 1 d . . . . .
H7 H 0.120929 0.511102 0.679427 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1280(3) 0.4303(2) 0.76511(6) 0.0337(3) Uani 1 1 d . . . . .
C9 C 0.2601(3) 0.3527(2) 0.80826(6) 0.0362(3) Uani 1 1 d . . . . .
H9 H 0.407420 0.308077 0.800316 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1725(3) 0.3422(2) 0.86266(6) 0.0393(4) Uani 1 1 d . . . . .
H10 H 0.263771 0.289341 0.891159 0.047 Uiso 1 1 calc R U . . .
C11 C -0.1622(3) 0.4743(2) 0.83543(7) 0.0378(3) Uani 1 1 d . . . . .
H11 H -0.309125 0.517496 0.844530 0.045 Uiso 1 1 calc R U . . .
C12 C -0.0901(3) 0.4884(2) 0.77952(6) 0.0371(3) Uani 1 1 d . . . . .
H12 H -0.187907 0.536848 0.751590 0.045 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
N1 H1A 0.92(2) . ?
N1 H1B 0.89(2) . ?
N1 C1 1.3736(19) . ?
N2 C4 1.4129(19) . ?
N2 C7 1.270(2) . ?
N3 C10 1.344(2) . ?
N3 C11 1.3337(19) . ?
C1 C2 1.398(2) . ?
C1 C6 1.404(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.382(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.395(2) . ?
C4 C5 1.401(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C7 C8 1.470(2) . ?
C8 C9 1.396(2) . ?
C8 C12 1.386(2) . ?
C9 H9 0.9400 . ?
C9 C10 1.379(2) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9400 . ?

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
H1A N1 H1B 119.0(18) . . ?
C1 N1 H1A 118.5(13) . . ?
C1 N1 H1B 117.0(13) . . ?
C7 N2 C4 122.23(13) . . ?
C11 N3 C10 116.37(13) . . ?
N1 C1 C2 121.52(15) . . ?
N1 C1 C6 120.37(14) . . ?
C2 C1 C6 118.08(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.46(14) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.71(14) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 N2 115.87(13) . . ?
C3 C4 C5 117.80(13) . . ?
C5 C4 N2 126.32(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.86(13) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.06(14) . . ?
C5 C6 H6 119.5 . . ?
N2 C7 H7 119.5 . . ?
N2 C7 C8 121.09(14) . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 122.48(14) . . ?
C12 C8 C7 120.31(14) . . ?
C12 C8 C9 117.20(13) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.36(14) . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 123.69(14) . . ?
N3 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N3 C11 H11 118.0 . . ?
N3 C11 C12 124.06(14) . . ?
C12 C11 H11 118.0 . . ?
C8 C12 H12 120.4 . . ?
C11 C12 C8 119.27(14) . . ?
C11 C12 H12 120.4 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.89(2) 2.16(2) 3.037(2) 170.0(19) 2_564 yes

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 C1 C2 C3 176.18(15) . . . . ?
N1 C1 C6 C5 -177.00(15) . . . . ?
N2 C4 C5 C6 177.67(14) . . . . ?
N2 C7 C8 C9 3.8(2) . . . . ?
N2 C7 C8 C12 -176.34(14) . . . . ?
N3 C11 C12 C8 -1.7(2) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C2 C3 C4 N2 -178.59(14) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 N2 C7 C8 -178.96(13) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
C7 N2 C4 C3 -174.33(14) . . . . ?
C7 N2 C4 C5 6.8(2) . . . . ?
C7 C8 C9 C10 178.01(14) . . . . ?
C7 C8 C12 C11 -177.19(14) . . . . ?
C8 C9 C10 N3 -0.1(2) . . . . ?
C9 C8 C12 C11 2.7(2) . . . . ?
C10 N3 C11 C12 -0.3(2) . . . . ?
C11 N3 C10 C9 1.2(2) . . . . ?
C12 C8 C9 C10 -1.8(2) . . . . ?

_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_PI_250_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2072256'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_PI_250_a            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.08 Note  
RESPONSE: Due to the increased number of parameters needed to model the pedal
          motion of the molecule.
;
_vrf_PLAT420_PI_250_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT911_PI_250_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report
RESPONSE: These reflections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.85593(8)
_cell_length_b                   7.39741(11)
_cell_length_c                   23.4532(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1015.96(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    7252
_cell_measurement_theta_min      3.741
_cell_measurement_theta_max      77.171
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.72 3.34 -1.02 0.0741
1.48 -1.49 -13.19 0.0499
0.97 1.29 14.13 0.0373
-3.75 -0.72 1.09 0.0703
0.02 0.11 -15.21 0.0188
-0.87 4.67 -0.14 0.0580
0.35 -2.47 -12.96 0.0415
-0.15 -0.23 15.18 0.0132
2.12 -2.09 10.74 0.0514
2.62 -3.47 -0.44 0.0664
0.73 -4.71 0.18 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9716
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.278
_diffrn_reflns_theta_min         3.769
_diffrn_ambient_temperature      249.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                1937
_reflns_number_total             2053
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 740 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_coef       0.0069(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     403
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      0.990
_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)+(0.0373P)²+0.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0732
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.97 and 0.03, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.28162 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.50767 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
6.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8213(3) 0.4646(2) 0.47773(6) 0.0593(4) Uani 1 1 d . . . . .
H1A H 0.941(4) 0.387(3) 0.4682(9) 0.071 Uiso 1 1 d . U . . .
H1B H 0.742(4) 0.516(3) 0.4498(9) 0.071 Uiso 1 1 d . U . . .
N2A N 0.4087(3) 0.3913(2) 0.69203(7) 0.0444(4) Uani 0.968(3) 1 d D U P A 1
C7A C 0.2145(3) 0.4530(2) 0.70653(7) 0.0443(4) Uani 0.968(3) 1 d D U P A 1
H7A H 0.124201 0.513105 0.679358 0.053 Uiso 0.968(3) 1 calc R U P A 1
N2B N 0.330(10) 0.437(7) 0.679(2) 0.046(4) Uani 0.032(3) 1 d D U P A 2
C7B C 0.414(8) 0.386(7) 0.7274(19) 0.048(4) Uani 0.032(3) 1 d D U P A 2
H7B H 0.562287 0.341456 0.733059 0.058 Uiso 0.032(3) 1 calc R U P A 2
C1 C 0.7125(3) 0.4427(2) 0.52904(6) 0.0432(4) Uani 1 1 d . . . . .
C2 C 0.8068(3) 0.3371(2) 0.57244(7) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.943657 0.274056 0.565915 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7004(3) 0.3246(2) 0.62496(7) 0.0441(4) Uani 1 1 d . . . . .
H3 H 0.768453 0.254959 0.653846 0.053 Uiso 1 1 calc R U . . .
C4 C 0.4951(3) 0.4127(2) 0.63608(6) 0.0411(3) Uani 1 1 d . . . . .
C5 C 0.3977(3) 0.5146(2) 0.59213(7) 0.0458(4) Uani 1 1 d . . . . .
H5 H 0.257792 0.573724 0.598313 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5040(3) 0.5296(2) 0.53979(7) 0.0462(4) Uani 1 1 d . . . . .
H6 H 0.435558 0.599048 0.510909 0.055 Uiso 1 1 calc R U . . .
C8A C 0.1290(4) 0.4319(2) 0.76495(7) 0.0403(4) Uani 0.968(3) 1 d D U P A 1
C9A C 0.2588(3) 0.3542(3) 0.80818(9) 0.0440(4) Uani 0.968(3) 1 d . U P A 1
H9A H 0.405709 0.309421 0.800356 0.053 Uiso 0.968(3) 1 calc R U P A 1
C10A C 0.1706(4) 0.3434(4) 0.86250(9) 0.0486(5) Uani 0.968(3) 1 d . U P A 1
H10A H 0.261304 0.290293 0.891018 0.058 Uiso 0.968(3) 1 calc R U P A 1
N3A N -0.0373(3) 0.4044(3) 0.87713(7) 0.0458(5) Uani 0.968(3) 1 d . U P A 1
C11A C -0.1614(3) 0.4759(3) 0.83516(9) 0.0457(5) Uani 0.968(3) 1 d . U P A 1
H11A H -0.307930 0.519382 0.844133 0.055 Uiso 0.968(3) 1 calc R U P A 1
C12A C -0.0883(4) 0.4903(3) 0.77925(8) 0.0448(4) Uani 0.968(3) 1 d . U P A 1
H12A H -0.185116 0.539195 0.751245 0.054 Uiso 0.968(3) 1 calc R U P A 1
C8B C 0.231(8) 0.410(7) 0.7746(19) 0.043(3) Uani 0.032(3) 1 d DG U P A 2
C9B C 0.294(8) 0.337(7) 0.827(3) 0.045(3) Uani 0.032(3) 1 d G U P A 2
H9B H 0.437621 0.282317 0.831438 0.054 Uiso 0.032(3) 1 calc R U P A 2
C10B C 0.143(12) 0.344(10) 0.8727(18) 0.046(3) Uani 0.032(3) 1 d G U P A 2
H10B H 0.185212 0.295001 0.908131 0.055 Uiso 0.032(3) 1 calc R U P A 2
N3B N -0.070(10) 0.425(9) 0.866(2) 0.045(3) Uani 0.032(3) 1 d G U P A 2
C11B C -0.132(7) 0.498(7) 0.814(3) 0.044(3) Uani 0.032(3) 1 d G U P A 2
H11B H -0.276108 0.551877 0.809252 0.052 Uiso 0.032(3) 1 calc R U P A 2
C12B C 0.018(10) 0.490(6) 0.7680(18) 0.043(3) Uani 0.032(3) 1 d G U P A 2
H12B H -0.023702 0.539195 0.732558 0.051 Uiso 0.032(3) 1 calc R U 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
N1 H1A 0.93(2) . ?
N1 H1B 0.89(2) . ?
N1 C1 1.371(2) . ?
N2A C7A 1.272(2) . ?
N2A C4 1.415(2) . ?
C7A H7A 0.9400 . ?
C7A C8A 1.467(2) . ?
N2B C7B 1.29(4) . ?
N2B C4 1.41(5) . ?
C7B H7B 0.9400 . ?
C7B C8B 1.55(3) . ?
C1 C2 1.397(2) . ?
C1 C6 1.402(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.392(2) . ?
C4 C5 1.398(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9400 . ?
C8A C9A 1.391(2) . ?
C8A C12A 1.385(3) . ?
C9A H9A 0.9400 . ?
C9A C10A 1.377(3) . ?
C10A H10A 0.9400 . ?
C10A N3A 1.343(3) . ?
N3A C11A 1.333(2) . ?
C11A H11A 0.9400 . ?
C11A C12A 1.384(2) . ?
C12A H12A 0.9400 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9400 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9400 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9400 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9400 . ?

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
H1A N1 H1B 118(2) . . ?
C1 N1 H1A 119.1(14) . . ?
C1 N1 H1B 117.1(14) . . ?
C7A N2A C4 121.85(17) . . ?
N2A C7A H7A 119.4 . . ?
N2A C7A C8A 121.12(17) . . ?
C8A C7A H7A 119.4 . . ?
C7B N2B C4 109(4) . . ?
N2B C7B H7B 125.2 . . ?
N2B C7B C8B 110(4) . . ?
C8B C7B H7B 125.2 . . ?
N1 C1 C2 121.46(15) . . ?
N1 C1 C6 120.54(15) . . ?
C2 C1 C6 117.99(14) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.54(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.64(15) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2A 115.48(14) . . ?
C3 C4 N2B 142(2) . . ?
C3 C4 C5 117.80(14) . . ?
C5 C4 N2A 126.71(15) . . ?
C5 C4 N2B 100(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.97(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.03(14) . . ?
C5 C6 H6 119.5 . . ?
C9A C8A C7A 122.55(19) . . ?
C12A C8A C7A 120.42(19) . . ?
C12A C8A C9A 117.03(15) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A C8A 119.56(16) . . ?
C10A C9A H9A 120.2 . . ?
C9A C10A H10A 118.1 . . ?
N3A C10A C9A 123.83(18) . . ?
N3A C10A H10A 118.1 . . ?
C11A N3A C10A 116.05(16) . . ?
N3A C11A H11A 117.9 . . ?
N3A C11A C12A 124.16(16) . . ?
C12A C11A H11A 117.9 . . ?
C8A C12A H12A 120.3 . . ?
C11A C12A C8A 119.33(16) . . ?
C11A C12A H12A 120.3 . . ?
C9B C8B C7B 114(5) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 126(4) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C9B C10B N3B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.00(6) . . ?
N3B C11B H11B 120.0 . . ?
C12B C11B N3B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.89(2) 2.17(2) 3.045(2) 171(2) 2_564 yes
N1 H1B N3B 0.89(2) 2.25(15) 3.11(18) 164(10) 2_564 yes

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 C1 C2 C3 176.47(16) . . . . ?
N1 C1 C6 C5 -177.24(16) . . . . ?
N2A C7A C8A C9A 4.0(3) . . . . ?
N2A C7A C8A C12A -176.18(17) . . . . ?
N2A C4 C5 C6 177.71(15) . . . . ?
C7A N2A C4 C3 -174.54(16) . . . . ?
C7A N2A C4 C5 6.6(3) . . . . ?
C7A C8A C9A C10A 178.08(18) . . . . ?
C7A C8A C12A C11A -177.27(16) . . . . ?
N2B C7B C8B C9B 172(4) . . . . ?
N2B C7B C8B C12B -6(6) . . . . ?
N2B C4 C5 C6 -180(2) . . . . ?
C7B N2B C4 C3 16(7) . . . . ?
C7B N2B C4 C5 -166(4) . . . . ?
C7B C8B C9B C10B -178(4) . . . . ?
C7B C8B C12B C11B 178(5) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C2 C3 C4 N2A -178.61(15) . . . . ?
C2 C3 C4 N2B 178(3) . . . . ?
C2 C3 C4 C5 0.3(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 N2A C7A C8A -179.09(14) . . . . ?
C4 N2B C7B C8B -179(4) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 C1 C2 C3 -2.2(2) . . . . ?
C8A C9A C10A N3A -0.1(3) . . . . ?
C9A C8A C12A C11A 2.6(2) . . . . ?
C9A C10A N3A C11A 1.1(3) . . . . ?
C10A N3A C11A C12A -0.2(3) . . . . ?
N3A C11A C12A C8A -1.7(3) . . . . ?
C12A C8A C9A C10A -1.8(2) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_170_a
_database_code_depnum_ccdc_archive 'CCDC 2072260'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_170_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.83221(8)
_cell_length_b                   7.30484(11)
_cell_length_c                   23.5004(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1001.20(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7274
_cell_measurement_theta_min      3.738
_cell_measurement_theta_max      77.051
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.72 -3.29 -0.91 0.0741
-1.49 1.46 -13.20 0.0499
-0.95 -1.26 14.20 0.0373
3.73 0.71 0.99 0.0703
-0.05 -0.13 -15.24 0.0188
0.86 -4.62 -0.10 0.0580
-0.37 2.42 -13.02 0.0415
0.18 0.24 15.21 0.0132
-2.09 2.08 10.79 0.0514
-2.61 3.44 -0.42 0.0664
-0.72 4.65 0.14 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.221
_diffrn_reflns_theta_min         3.762
_diffrn_ambient_temperature      169.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                1943
_reflns_number_total             2014
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 756 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(15)
_refine_ls_extinction_coef       0.0049(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.083
_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)+(0.0319P)²+0.1414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8180(3) 0.4666(2) 0.47763(6) 0.0381(4) Uani 1 1 d . . . . .
H1A H 0.937(4) 0.390(3) 0.4681(8) 0.046 Uiso 1 1 d . U . . .
H1B H 0.738(4) 0.518(3) 0.4491(9) 0.046 Uiso 1 1 d . U . . .
N2 N 0.4067(2) 0.38964(18) 0.69187(5) 0.0298(3) Uani 1 1 d . . . . .
N3 N -0.0350(2) 0.40257(18) 0.87748(5) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.7098(3) 0.4424(2) 0.52894(6) 0.0285(3) Uani 1 1 d . . . . .
C2 C 0.8068(3) 0.3357(2) 0.57223(6) 0.0298(3) Uani 1 1 d . . . . .
H2 H 0.946166 0.272005 0.565514 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7006(3) 0.3225(2) 0.62471(6) 0.0286(3) Uani 1 1 d . . . . .
H3 H 0.770568 0.251449 0.653777 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4931(3) 0.4110(2) 0.63611(6) 0.0270(3) Uani 1 1 d . . . . .
C5 C 0.3932(3) 0.5134(2) 0.59220(6) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.250611 0.572891 0.598522 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4992(3) 0.5291(2) 0.53985(6) 0.0300(3) Uani 1 1 d . . . . .
H6 H 0.428598 0.599678 0.510755 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2109(3) 0.4509(2) 0.70649(6) 0.0294(3) Uani 1 1 d . . . . .
H7 H 0.117739 0.511333 0.679159 0.035 Uiso 1 1 calc R U . . .
C8 C 0.1271(3) 0.4293(2) 0.76513(6) 0.0274(3) Uani 1 1 d . . . . .
C9 C 0.2610(3) 0.3519(2) 0.80812(6) 0.0292(3) Uani 1 1 d . . . . .
H9 H 0.410317 0.307126 0.799900 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1743(3) 0.3411(2) 0.86266(7) 0.0316(4) Uani 1 1 d . . . . .
H10 H 0.267405 0.287283 0.891317 0.038 Uiso 1 1 calc R U . . .
C11 C -0.1626(3) 0.4730(2) 0.83578(6) 0.0303(3) Uani 1 1 d . . . . .
H11 H -0.311548 0.516178 0.845143 0.036 Uiso 1 1 calc R U . . .
C12 C -0.0918(3) 0.4873(2) 0.77967(6) 0.0299(3) Uani 1 1 d . . . . .
H12 H -0.191674 0.536035 0.751563 0.036 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
N1 H1A 0.92(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.3724(19) . ?
N2 C4 1.4126(19) . ?
N2 C7 1.274(2) . ?
N3 C10 1.347(2) . ?
N3 C11 1.3337(19) . ?
C1 C2 1.401(2) . ?
C1 C6 1.406(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C4 C5 1.401(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.470(2) . ?
C8 C9 1.396(2) . ?
C8 C12 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 117.9(18) . . ?
C1 N1 H1A 118.8(13) . . ?
C1 N1 H1B 117.9(13) . . ?
C7 N2 C4 122.08(13) . . ?
C11 N3 C10 116.40(13) . . ?
N1 C1 C2 121.61(15) . . ?
N1 C1 C6 120.27(14) . . ?
C2 C1 C6 118.10(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.37(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.74(14) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 N2 115.81(13) . . ?
C3 C4 C5 117.76(14) . . ?
C5 C4 N2 126.42(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.93(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.06(14) . . ?
C5 C6 H6 119.5 . . ?
N2 C7 H7 119.6 . . ?
N2 C7 C8 120.85(14) . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 122.40(14) . . ?
C12 C8 C7 120.23(14) . . ?
C12 C8 C9 117.37(14) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.37(14) . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 123.57(14) . . ?
N3 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.19(14) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 119.05(14) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(2) 2.14(2) 3.030(2) 170.8(19) 2_564 yes

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 C1 C2 C3 176.15(15) . . . . ?
N1 C1 C6 C5 -176.90(15) . . . . ?
N2 C4 C5 C6 177.60(14) . . . . ?
N2 C7 C8 C9 4.0(2) . . . . ?
N2 C7 C8 C12 -176.29(15) . . . . ?
N3 C11 C12 C8 -1.5(2) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
C2 C3 C4 N2 -178.46(14) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C4 N2 C7 C8 -178.98(13) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C7 N2 C4 C3 -174.35(14) . . . . ?
C7 N2 C4 C5 6.7(2) . . . . ?
C7 C8 C9 C10 177.95(14) . . . . ?
C7 C8 C12 C11 -177.06(14) . . . . ?
C8 C9 C10 N3 -0.4(2) . . . . ?
C9 C8 C12 C11 2.7(2) . . . . ?
C10 N3 C11 C12 -0.6(2) . . . . ?
C11 N3 C10 C9 1.6(2) . . . . ?
C12 C8 C9 C10 -1.8(2) . . . . ?

_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_PI_250_2
_database_code_depnum_ccdc_archive 'CCDC 2072425'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT089_2_250_2             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.19 Note  
RESPONSE: The molecule is pedaling at this temperature, resulting in a
          number of disordered atom positions.
;
_vrf_PLAT420_PI_250_2            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT721_PI_250_2            
;
PROBLEM: Bond    Calc     1.41(8), Rep     1.39000 Dev...       0.02 Ang.  
RESPONSE: This bond length is constrained with an AFIX 66 command.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.85561(6)
_cell_length_b                   7.39670(7)
_cell_length_c                   23.4494(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1015.647(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    11476
_cell_measurement_theta_min      3.746
_cell_measurement_theta_max      76.905
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-0.82 4.64 2.09 0.0636
0.31 -4.39 -6.03 0.0646
-3.01 2.71 3.54 0.0538
-3.71 -0.12 3.35 0.0485
2.95 -0.87 -9.19 0.0528
3.71 0.15 -3.34 0.0545
0.84 -3.60 9.50 0.0666
0.03 -3.96 5.97 0.0646
0.25 -3.01 -11.81 0.0486
2.54 2.15 9.05 0.0670
1.31 -0.28 -14.25 0.0337
-3.58 1.60 -0.48 0.0408
-0.10 1.70 -14.22 0.0357
0.60 -0.35 14.98 0.0244
-0.32 0.26 -15.13 0.0246

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19051
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.382
_diffrn_reflns_theta_min         3.770
_diffrn_ambient_temperature      249.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2002
_reflns_number_total             2119
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 780 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.006
_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)+(0.0491P)²+0.0545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0834
_refine_special_details          
'At this temperature the molecule has started pedal motion. The disordered sites (A and B) were allowed to refine to a total value of 1. The refined values for the A and B sites were 0.97 and 0.03, respectively. To help maintain reasonable ADP values for the minor components, SIMU and free variable DFIX restraints were applied.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 N2A-C7A = N2B-C7B
 1.2818 with sigma of 0.02
 C7A-C8A = C7B-C8B
 1.50775 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N2A \\sim N2B \\sim C7A \\sim C7B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N3A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N3B \\sim C8B
\\sim C9B \\sim C10B \\sim C11B \\sim C12B: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(N2B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=
 Sof(N3B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(1)
 Sof(N2A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=
 Sof(N3A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B), C2(H2), C3(H3), C5(H5), C6(H6), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B)
5.b Fitted hexagon refined as free rotating group:
 C8B(C9B,C10B,N3B,C11B,C12B)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.1786(3) 0.5351(3) 0.52228(7) 0.0603(4) Uani 1 1 d . . . . .
H1A H 0.057(4) 0.609(3) 0.5319(10) 0.072 Uiso 1 1 d . U . . .
H1B H 0.258(4) 0.483(3) 0.5510(10) 0.072 Uiso 1 1 d . U . . .
N2A N 0.5911(3) 0.6086(2) 0.30792(7) 0.0456(4) Uani 0.967(3) 1 d D U P A 1
C7A C 0.7851(3) 0.5470(2) 0.29350(7) 0.0451(4) Uani 0.967(3) 1 d D U P A 1
H7A H 0.875169 0.486663 0.320679 0.054 Uiso 0.967(3) 1 calc R U P A 1
N2B N 0.658(10) 0.566(8) 0.320(2) 0.047(5) Uani 0.033(3) 1 d D U P A 2
C7B C 0.579(8) 0.593(7) 0.2690(19) 0.050(5) Uani 0.033(3) 1 d D U P A 2
H7B H 0.423694 0.612992 0.260542 0.060 Uiso 0.033(3) 1 calc R U P A 2
C1 C 0.2876(3) 0.5573(2) 0.47091(7) 0.0446(4) Uani 1 1 d . . . . .
C2 C 0.1932(3) 0.6630(2) 0.42750(7) 0.0468(4) Uani 1 1 d . . . . .
H2 H 0.056178 0.725883 0.434034 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2994(3) 0.6757(2) 0.37504(7) 0.0450(4) Uani 1 1 d . . . . .
H3 H 0.231449 0.745564 0.346184 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5050(3) 0.5874(2) 0.36386(7) 0.0428(4) Uani 1 1 d . . . . .
C5 C 0.6023(3) 0.4854(2) 0.40782(7) 0.0470(4) Uani 1 1 d . . . . .
H5 H 0.742164 0.426169 0.401627 0.056 Uiso 1 1 calc R U . . .
C6 C 0.4960(3) 0.4704(2) 0.46014(7) 0.0473(4) Uani 1 1 d . . . . .
H6 H 0.564454 0.400881 0.489018 0.057 Uiso 1 1 calc R U . . .
C8A C 0.8710(4) 0.5683(2) 0.23498(7) 0.0414(4) Uani 0.967(3) 1 d D U P A 1
C9A C 0.7408(3) 0.6460(3) 0.19169(9) 0.0451(5) Uani 0.967(3) 1 d . U P A 1
H9A H 0.593848 0.690793 0.199491 0.054 Uiso 0.967(3) 1 calc R U P A 1
C10A C 0.8294(4) 0.6565(3) 0.13732(9) 0.0495(5) Uani 0.967(3) 1 d . U P A 1
H10A H 0.739057 0.709665 0.108738 0.059 Uiso 0.967(3) 1 calc R U P A 1
N3A N 1.0370(3) 0.5952(3) 0.12285(7) 0.0470(4) Uani 0.967(3) 1 d . U P A 1
C11A C 1.1615(3) 0.5239(3) 0.16477(10) 0.0467(5) Uani 0.967(3) 1 d . U P A 1
H11A H 1.308148 0.480735 0.155782 0.056 Uiso 0.967(3) 1 calc R U P A 1
C12A C 1.0884(4) 0.5095(3) 0.22074(9) 0.0460(4) Uani 0.967(3) 1 d . U P A 1
H12A H 1.185111 0.460483 0.248756 0.055 Uiso 0.967(3) 1 calc R U P A 1
C8B C 0.772(8) 0.590(6) 0.2241(19) 0.042(4) Uani 0.033(3) 1 d DG U P A 2
C9B C 0.720(6) 0.670(7) 0.172(3) 0.046(4) Uani 0.033(3) 1 d G U P A 2
H9B H 0.576791 0.724797 0.166548 0.055 Uiso 0.033(3) 1 calc R U P A 2
C10B C 0.879(10) 0.668(9) 0.1281(18) 0.047(4) Uani 0.033(3) 1 d G U P A 2
H10B H 0.843717 0.721620 0.092866 0.057 Uiso 0.033(3) 1 calc R U P A 2
N3B N 1.090(8) 0.586(9) 0.136(2) 0.046(4) Uani 0.033(3) 1 d G U P A 2
C11B C 1.142(6) 0.507(6) 0.188(3) 0.044(3) Uani 0.033(3) 1 d G U P A 2
H11B H 1.285445 0.451457 0.193809 0.053 Uiso 0.033(3) 1 calc R U P A 2
C12B C 0.983(10) 0.508(6) 0.2323(17) 0.043(3) Uani 0.033(3) 1 d G U P A 2
H12B H 1.018520 0.454632 0.267492 0.052 Uiso 0.033(3) 1 calc R U 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
N1 H1A 0.93(2) . ?
N1 H1B 0.91(3) . ?
N1 C1 1.373(2) . ?
N2A C7A 1.270(2) . ?
N2A C4 1.414(2) . ?
C7A H7A 0.9400 . ?
C7A C8A 1.470(2) . ?
N2B C7B 1.29(4) . ?
N2B C4 1.38(6) . ?
C7B H7B 0.9400 . ?
C7B C8B 1.55(3) . ?
C1 C2 1.397(2) . ?
C1 C6 1.402(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.382(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.394(2) . ?
C4 C5 1.399(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9400 . ?
C8A C9A 1.394(2) . ?
C8A C12A 1.386(3) . ?
C9A H9A 0.9400 . ?
C9A C10A 1.379(3) . ?
C10A H10A 0.9400 . ?
C10A N3A 1.341(3) . ?
N3A C11A 1.333(2) . ?
C11A H11A 0.9400 . ?
C11A C12A 1.385(3) . ?
C12A H12A 0.9400 . ?
C8B C9B 1.3900 . ?
C8B C12B 1.3900 . ?
C9B H9B 0.9400 . ?
C9B C10B 1.3900 . ?
C10B H10B 0.9400 . ?
C10B N3B 1.3900 . ?
N3B C11B 1.3900 . ?
C11B H11B 0.9400 . ?
C11B C12B 1.3900 . ?
C12B H12B 0.9400 . ?

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
H1A N1 H1B 118(2) . . ?
C1 N1 H1A 120.0(15) . . ?
C1 N1 H1B 117.7(15) . . ?
C7A N2A C4 121.76(17) . . ?
N2A C7A H7A 119.5 . . ?
N2A C7A C8A 121.09(17) . . ?
C8A C7A H7A 119.5 . . ?
C7B N2B C4 116(4) . . ?
N2B C7B H7B 124.4 . . ?
N2B C7B C8B 111(5) . . ?
C8B C7B H7B 124.4 . . ?
N1 C1 C2 121.46(16) . . ?
N1 C1 C6 120.52(15) . . ?
C2 C1 C6 118.00(15) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.56(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.62(15) . . ?
C4 C3 H3 119.2 . . ?
N2B C4 C3 139(2) . . ?
N2B C4 C5 103(2) . . ?
C3 C4 N2A 115.50(14) . . ?
C3 C4 C5 117.76(15) . . ?
C5 C4 N2A 126.73(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.97(15) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.05(15) . . ?
C5 C6 H6 119.5 . . ?
C9A C8A C7A 122.5(2) . . ?
C12A C8A C7A 120.4(2) . . ?
C12A C8A C9A 117.17(16) . . ?
C8A C9A H9A 120.3 . . ?
C10A C9A C8A 119.40(17) . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A H10A 118.1 . . ?
N3A C10A C9A 123.78(18) . . ?
N3A C10A H10A 118.1 . . ?
C11A N3A C10A 116.30(16) . . ?
N3A C11A H11A 118.0 . . ?
N3A C11A C12A 124.09(17) . . ?
C12A C11A H11A 118.0 . . ?
C8A C12A H12A 120.4 . . ?
C11A C12A C8A 119.22(16) . . ?
C11A C12A H12A 120.4 . . ?
C9B C8B C7B 116(5) . . ?
C9B C8B C12B 120.0 . . ?
C12B C8B C7B 124(5) . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
N3B C10B C9B 120.0 . . ?
N3B C10B H10B 120.0 . . ?
C11B N3B C10B 120.0 . . ?
N3B C11B H11B 120.0 . . ?
N3B C11B C12B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C8B C12B H12B 120.0 . . ?
C11B C12B C8B 120.0 . . ?
C11B C12B H12B 120.0 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3A 0.91(3) 2.15(3) 3.044(2) 170(2) 2_665 yes
N1 H1B N3B 0.91(3) 2.25(16) 3.13(18) 164(10) 2_665 yes

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 C1 C2 C3 -176.45(16) . . . . ?
N1 C1 C6 C5 177.15(16) . . . . ?
N2A C7A C8A C9A -4.1(3) . . . . ?
N2A C7A C8A C12A 176.25(17) . . . . ?
N2A C4 C5 C6 -177.60(16) . . . . ?
C7A N2A C4 C3 174.50(16) . . . . ?
C7A N2A C4 C5 -6.8(3) . . . . ?
C7A C8A C9A C10A -177.92(17) . . . . ?
C7A C8A C12A C11A 177.17(16) . . . . ?
N2B C7B C8B C9B -162(4) . . . . ?
N2B C7B C8B C12B 21(6) . . . . ?
N2B C4 C5 C6 -179(2) . . . . ?
C7B N2B C4 C3 -22(7) . . . . ?
C7B N2B C4 C5 158(4) . . . . ?
C7B C8B C9B C10B -178(4) . . . . ?
C7B C8B C12B C11B 177(4) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C1 C6 C5 -1.4(2) . . . . ?
C2 C3 C4 N2A 178.45(16) . . . . ?
C2 C3 C4 N2B 180(4) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C4 N2A C7A C8A 179.27(15) . . . . ?
C4 N2B C7B C8B 173(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 C1 C2 C3 2.1(2) . . . . ?
C8A C9A C10A N3A 0.2(3) . . . . ?
C9A C8A C12A C11A -2.5(2) . . . . ?
C9A C10A N3A C11A -1.2(3) . . . . ?
C10A N3A C11A C12A 0.4(3) . . . . ?
N3A C11A C12A C8A 1.5(3) . . . . ?
C12A C8A C9A C10A 1.7(2) . . . . ?
C8B C9B C10B N3B 0.0 . . . . ?
C9B C8B C12B C11B 0.0 . . . . ?
C9B C10B N3B C11B 0.0 . . . . ?
C10B N3B C11B C12B 0.0 . . . . ?
N3B C11B C12B C8B 0.0 . . . . ?
C12B C8B C9B C10B 0.0 . . . . ?

_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_PI_150_a
_database_code_depnum_ccdc_archive 'CCDC 2072261'
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_PI_150_a            
;
PROBLEM: D-H Without Acceptor       N1       --H1A      .     Please Check 
RESPONSE: The hydrogen atom points at a neighboring phenyl ring.
;
_vrf_PLAT911_PI_150_a            
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These relections were omitted during the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N3'
_chemical_formula_sum            'C12 H11 N3'
_chemical_formula_weight         197.24
_chemical_absolute_configuration ?
_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 0.0181 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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.82676(8)
_cell_length_b                   7.28832(12)
_cell_length_c                   23.5058(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     998.23(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6993
_cell_measurement_theta_min      3.737
_cell_measurement_theta_max      77.185
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.71 -3.28 -0.90 0.0741
-1.49 1.45 -13.21 0.0499
-0.94 -1.25 14.22 0.0373
3.73 0.71 0.98 0.0703
-0.05 -0.13 -15.25 0.0188
0.85 -4.61 -0.09 0.0580
-0.37 2.42 -13.03 0.0415
0.18 0.24 15.22 0.0132
-2.09 2.08 10.80 0.0514
-2.60 3.43 -0.42 0.0664
-0.72 4.65 0.13 0.0528

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9524
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.366
_diffrn_reflns_theta_min         3.761
_diffrn_ambient_temperature      149.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                1944
_reflns_number_total             2008
_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       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 753 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(16)
_refine_ls_extinction_coef       0.0045(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.066
_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)+(0.0345P)²+0.1558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0708
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.8181(3) 0.4668(2) 0.47758(6) 0.0340(3) Uani 1 1 d . . . . .
H1A H 0.935(4) 0.389(3) 0.4682(8) 0.041 Uiso 1 1 d . U . . .
H1B H 0.738(4) 0.519(3) 0.4491(9) 0.041 Uiso 1 1 d . U . . .
N2 N 0.4064(2) 0.38926(18) 0.69179(5) 0.0271(3) Uani 1 1 d . . . . .
N3 N -0.0345(2) 0.40218(18) 0.87757(5) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.7096(3) 0.4424(2) 0.52886(6) 0.0259(3) Uani 1 1 d . . . . .
C2 C 0.8069(3) 0.3355(2) 0.57214(6) 0.0269(3) Uani 1 1 d . . . . .
H2 H 0.946521 0.271896 0.565375 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7010(3) 0.3220(2) 0.62471(6) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.771317 0.251051 0.653775 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4928(3) 0.4105(2) 0.63602(6) 0.0246(3) Uani 1 1 d . . . . .
C5 C 0.3925(3) 0.5133(2) 0.59214(6) 0.0267(3) Uani 1 1 d . . . . .
H5 H 0.249713 0.572833 0.598503 0.032 Uiso 1 1 calc R U . . .
C6 C 0.4983(3) 0.5292(2) 0.53978(6) 0.0270(3) Uani 1 1 d . . . . .
H6 H 0.427416 0.599723 0.510699 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2101(3) 0.4506(2) 0.70647(6) 0.0267(3) Uani 1 1 d . . . . .
H7 H 0.116612 0.510972 0.679174 0.032 Uiso 1 1 calc R U . . .
C8 C 0.1269(3) 0.4289(2) 0.76511(6) 0.0251(3) Uani 1 1 d . . . . .
C9 C 0.2614(3) 0.3514(2) 0.80810(6) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.410794 0.306546 0.799823 0.032 Uiso 1 1 calc R U . . .
C10 C 0.1750(3) 0.3407(2) 0.86271(7) 0.0287(3) Uani 1 1 d . . . . .
H10 H 0.268476 0.287103 0.891344 0.034 Uiso 1 1 calc R U . . .
C11 C -0.1628(3) 0.4726(2) 0.83589(7) 0.0276(3) Uani 1 1 d . . . . .
H11 H -0.311833 0.515859 0.845333 0.033 Uiso 1 1 calc R U . . .
C12 C -0.0925(3) 0.4866(2) 0.77974(6) 0.0273(3) Uani 1 1 d . . . . .
H12 H -0.192983 0.534903 0.751651 0.033 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
N1 H1A 0.91(2) . ?
N1 H1B 0.90(2) . ?
N1 C1 1.3729(19) . ?
N2 C4 1.4126(19) . ?
N2 C7 1.276(2) . ?
N3 C10 1.346(2) . ?
N3 C11 1.3349(19) . ?
C1 C2 1.401(2) . ?
C1 C6 1.408(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.399(2) . ?
C4 C5 1.402(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.470(2) . ?
C8 C9 1.398(2) . ?
C8 C12 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?

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
H1A N1 H1B 117.9(18) . . ?
C1 N1 H1A 118.4(13) . . ?
C1 N1 H1B 118.0(13) . . ?
C7 N2 C4 122.14(13) . . ?
C11 N3 C10 116.45(13) . . ?
N1 C1 C2 121.56(15) . . ?
N1 C1 C6 120.32(14) . . ?
C2 C1 C6 118.11(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.48(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.54(14) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 N2 115.75(13) . . ?
C3 C4 C5 117.89(14) . . ?
C5 C4 N2 126.35(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.92(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.02(14) . . ?
C5 C6 H6 119.5 . . ?
N2 C7 H7 119.6 . . ?
N2 C7 C8 120.80(14) . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 122.42(14) . . ?
C12 C8 C7 120.23(14) . . ?
C12 C8 C9 117.35(14) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.35(14) . . ?
C10 C9 H9 120.3 . . ?
N3 C10 C9 123.56(14) . . ?
N3 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N3 C11 H11 117.9 . . ?
N3 C11 C12 124.17(14) . . ?
C12 C11 H11 117.9 . . ?
C8 C12 H12 120.5 . . ?
C11 C12 C8 119.05(14) . . ?
C11 C12 H12 120.5 . . ?

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
_geom_hbond_publ_flag
N1 H1B N3 0.90(2) 2.14(2) 3.028(2) 170.8(19) 2_564 yes

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 C1 C2 C3 176.04(15) . . . . ?
N1 C1 C6 C5 -176.79(15) . . . . ?
N2 C4 C5 C6 177.56(14) . . . . ?
N2 C7 C8 C9 4.0(2) . . . . ?
N2 C7 C8 C12 -176.20(15) . . . . ?
N3 C11 C12 C8 -1.7(2) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
C2 C3 C4 N2 -178.44(14) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C4 N2 C7 C8 -178.97(13) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C7 N2 C4 C3 -174.44(14) . . . . ?
C7 N2 C4 C5 6.8(2) . . . . ?
C7 C8 C9 C10 177.89(14) . . . . ?
C7 C8 C12 C11 -176.95(14) . . . . ?
C8 C9 C10 N3 -0.3(2) . . . . ?
C9 C8 C12 C11 2.9(2) . . . . ?
C10 N3 C11 C12 -0.5(2) . . . . ?
C11 N3 C10 C9 1.6(2) . . . . ?
C12 C8 C9 C10 -1.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
