####################################################################### 
# 
# 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_r5
_database_code_depnum_ccdc_archive 'CCDC 1873561'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2018-10-16 deposited with the CCDC.	2019-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 N3'
_chemical_formula_sum            'C13 H9 N3'
_chemical_formula_weight         207.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.5247(3)
_cell_length_b                   8.38410(10)
_cell_length_c                   21.2450(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.969(2)
_cell_angle_gamma                90
_cell_volume                     1983.12(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15225
_cell_measurement_theta_min      4.2160
_cell_measurement_theta_max      79.7270

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.017
_exptl_absorpt_coefficient_mu    0.683
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
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   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21586
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.308
_diffrn_reflns_theta_max         74.501
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2020
_reflns_number_gt                1821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.9245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2020
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.57956(7) 0.75553(9) 0.53013(4) 0.0184(2) Uani 1 1 d . . . . .
N2 N 0.73683(7) 0.56697(10) 0.57324(4) 0.0204(2) Uani 1 1 d . . . . .
N3 N 0.75659(7) 0.62593(10) 0.63208(4) 0.0212(2) Uani 1 1 d . . . . .
C1 C 0.64795(8) 0.63273(11) 0.52411(4) 0.0175(2) Uani 1 1 d . . . . .
C9 C 0.59841(8) 0.81660(11) 0.59098(4) 0.0177(2) Uani 1 1 d . . . . .
C11 C 0.62986(8) 0.55502(11) 0.45970(4) 0.0180(2) Uani 1 1 d . . . . .
C12 C 0.70464(9) 0.43084(11) 0.45036(5) 0.0207(2) Uani 1 1 d . . . . .
H12 H 0.767212 0.396975 0.484861 0.025 Uiso 1 1 calc R U . . .
C8 C 0.52922(9) 0.94616(11) 0.60389(5) 0.0205(2) Uani 1 1 d . . . . .
H8 H 0.471543 0.993624 0.570275 0.025 Uiso 1 1 calc R U . . .
C16 C 0.53610(9) 0.60448(11) 0.40733(5) 0.0205(2) Uani 1 1 d . . . . .
H16 H 0.485292 0.686326 0.413010 0.025 Uiso 1 1 calc R U . . .
C4 C 0.68792(8) 0.74929(11) 0.64289(5) 0.0184(2) Uani 1 1 d . . . . .
C7 C 0.54823(9) 1.00063(11) 0.66637(5) 0.0218(2) Uani 1 1 d . . . . .
H7 H 0.502040 1.084808 0.674953 0.026 Uiso 1 1 calc R U . . .
C15 C 0.51865(9) 0.53176(12) 0.34686(5) 0.0236(2) Uani 1 1 d . . . . .
H15 H 0.456484 0.565503 0.312119 0.028 Uiso 1 1 calc R U . . .
C5 C 0.70625(9) 0.80932(12) 0.70700(5) 0.0211(2) Uani 1 1 d . . . . .
H5 H 0.765215 0.765491 0.740996 0.025 Uiso 1 1 calc R U . . .
C14 C 0.59375(9) 0.40879(12) 0.33810(5) 0.0232(2) Uani 1 1 d . . . . .
H14 H 0.582115 0.360664 0.297504 0.028 Uiso 1 1 calc R U . . .
C13 C 0.68617(9) 0.35783(12) 0.39002(5) 0.0229(2) Uani 1 1 d . . . . .
H13 H 0.735797 0.274557 0.384326 0.027 Uiso 1 1 calc R U . . .
C6 C 0.63677(9) 0.93187(12) 0.71848(5) 0.0219(2) Uani 1 1 d . . . . .
H6 H 0.647384 0.970598 0.760611 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
N10 C1 1.3228(12) . ?
N10 C9 1.3549(12) . ?
N2 N3 1.3082(11) . ?
N2 C1 1.3749(12) . ?
N3 C4 1.3574(12) . ?
C1 C11 1.4809(12) . ?
C9 C8 1.4156(13) . ?
C9 C4 1.4181(13) . ?
C11 C12 1.3980(13) . ?
C11 C16 1.3988(13) . ?
C12 C13 1.3865(13) . ?
C12 H12 0.9300 . ?
C8 C7 1.3669(13) . ?
C8 H8 0.9300 . ?
C16 C15 1.3889(13) . ?
C16 H16 0.9300 . ?
C4 C5 1.4158(13) . ?
C7 C6 1.4197(14) . ?
C7 H7 0.9300 . ?
C15 C14 1.3892(14) . ?
C15 H15 0.9300 . ?
C5 C6 1.3628(14) . ?
C5 H5 0.9300 . ?
C14 C13 1.3881(14) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C6 H6 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
C1 N10 C9 115.70(8) . . ?
N3 N2 C1 119.05(8) . . ?
N2 N3 C4 118.97(8) . . ?
N10 C1 N2 125.76(8) . . ?
N10 C1 C11 119.11(8) . . ?
N2 C1 C11 115.13(8) . . ?
N10 C9 C8 121.02(9) . . ?
N10 C9 C4 119.79(8) . . ?
C8 C9 C4 119.20(9) . . ?
C12 C11 C16 119.06(9) . . ?
C12 C11 C1 120.93(9) . . ?
C16 C11 C1 120.01(9) . . ?
C13 C12 C11 120.47(9) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C7 C8 C9 119.17(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C15 C16 C11 120.21(9) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
N3 C4 C5 119.01(8) . . ?
N3 C4 C9 120.69(8) . . ?
C5 C4 C9 120.29(9) . . ?
C8 C7 C6 121.62(9) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C16 C15 C14 120.22(9) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C6 C5 C4 119.45(9) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C13 C14 C15 119.92(9) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C12 C13 C14 120.12(9) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C5 C6 C7 120.25(9) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035



