# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_krl_d_247b
_database_code_depnum_ccdc_archive 'CCDC 2257695'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 N16'
_chemical_formula_sum            'C6 N16'
_chemical_formula_weight         296.22

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   12.0754(3)
_cell_length_b                   10.5591(3)
_cell_length_c                   8.8651(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1130.35(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3259
_cell_measurement_theta_min      4.1810
_cell_measurement_theta_max      75.6620

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5814
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.187
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.904
_reflns_number_total             1983
_reflns_number_gt                1820
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.646
_reflns_Friedel_fraction_max     0.707
_reflns_Friedel_fraction_full    0.793

_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0704P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1983
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_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
N18 N 0.38900(19) 0.2111(2) 0.8590(4) 0.0310(6) Uani 1 1 d . . . . .
N17 N 0.38808(19) 0.3042(3) 0.7681(3) 0.0300(6) Uani 1 1 d . . . . .
N21 N 0.3620(2) -0.0459(3) 0.2735(4) 0.0350(7) Uani 1 1 d . . . . .
N20 N 0.3698(2) -0.0164(3) 0.4125(4) 0.0365(7) Uani 1 1 d . . . . .
N10 N 0.36760(17) 0.6111(2) 0.1647(4) 0.0307(6) Uani 1 1 d . . . . .
N9 N 0.36754(18) 0.5331(3) 0.0519(3) 0.0313(6) Uani 1 1 d . . . . .
N8 N 0.37107(18) 0.4094(3) 0.0945(3) 0.0290(6) Uani 1 1 d . . . . .
N3 N 0.3814(2) 0.1432(3) 0.5841(3) 0.0293(6) Uani 1 1 d . . . . .
N1 N 0.3729(2) 0.1930(3) 0.3199(3) 0.0285(6) Uani 1 1 d . . . . .
N13 N 0.38076(17) 0.4872(3) 0.5461(3) 0.0268(6) Uani 1 1 d . . . . .
N11 N 0.37182(18) 0.5349(2) 0.2895(4) 0.0267(6) Uani 1 1 d . . . . .
C6 C 0.3762(2) 0.3162(3) 0.3585(4) 0.0250(6) Uani 1 1 d . . . . .
C2 C 0.3752(2) 0.1140(3) 0.4357(4) 0.0288(7) Uani 1 1 d . . . . .
C7 C 0.3736(2) 0.4131(3) 0.2442(4) 0.0271(7) Uani 1 1 d . . . . .
C12 C 0.3757(2) 0.5705(3) 0.4403(4) 0.0277(7) Uani 1 1 d . . . . .
C4 C 0.3835(2) 0.2644(3) 0.6178(4) 0.0269(7) Uani 1 1 d . . . . .
N16 N 0.3744(2) 0.7756(3) 0.7125(4) 0.0445(8) Uani 1 1 d . . . . .
N19 N 0.3894(2) 0.1384(3) 0.9494(4) 0.0392(7) Uani 1 1 d . . . . .
C5 C 0.3809(2) 0.3611(3) 0.5066(4) 0.0265(7) Uani 1 1 d . . . . .
N15 N 0.3737(2) 0.7325(3) 0.5971(4) 0.0325(7) Uani 1 1 d . . . . .
N14 N 0.37299(18) 0.7006(3) 0.4588(3) 0.0315(6) Uani 1 1 d . . . . .
N22 N 0.3549(2) -0.0879(3) 0.1586(4) 0.0447(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N18 N19 1.109(5) . ?
N18 N17 1.271(4) . ?
N17 C4 1.398(5) . ?
N21 N22 1.114(5) . ?
N21 N20 1.274(5) . ?
N20 C2 1.394(4) . ?
N10 N9 1.295(4) . ?
N10 N11 1.369(4) . ?
N9 N8 1.360(4) . ?
N8 C7 1.328(4) . ?
N3 C4 1.315(4) . ?
N3 C2 1.353(5) . ?
N1 C2 1.323(4) . ?
N1 C6 1.346(4) . ?
N13 C12 1.287(4) . ?
N13 C5 1.377(4) . ?
N11 C7 1.348(4) . ?
N11 C12 1.389(5) . ?
C6 C5 1.397(5) . ?
C6 C7 1.440(5) . ?
C12 N14 1.383(4) . ?
C4 C5 1.420(4) . ?
N16 N15 1.119(4) . ?
N15 N14 1.272(4) . ?

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
N19 N18 N17 173.1(4) . . ?
N18 N17 C4 111.9(3) . . ?
N22 N21 N20 170.7(3) . . ?
N21 N20 C2 112.8(3) . . ?
N9 N10 N11 104.5(2) . . ?
N10 N9 N8 113.4(3) . . ?
C7 N8 N9 104.4(3) . . ?
C4 N3 C2 116.4(3) . . ?
C2 N1 C6 114.3(3) . . ?
C12 N13 C5 118.4(3) . . ?
C7 N11 N10 108.7(3) . . ?
C7 N11 C12 123.0(3) . . ?
N10 N11 C12 128.3(3) . . ?
N1 C6 C5 124.6(3) . . ?
N1 C6 C7 120.5(3) . . ?
C5 C6 C7 114.9(3) . . ?
N1 C2 N3 127.7(3) . . ?
N1 C2 N20 120.5(3) . . ?
N3 C2 N20 111.8(3) . . ?
N8 C7 N11 109.0(3) . . ?
N8 C7 C6 133.0(3) . . ?
N11 C7 C6 117.9(3) . . ?
N13 C12 N14 126.4(3) . . ?
N13 C12 N11 121.2(3) . . ?
N14 C12 N11 112.4(3) . . ?
N3 C4 N17 120.7(3) . . ?
N3 C4 C5 122.8(3) . . ?
N17 C4 C5 116.5(3) . . ?
N13 C5 C6 124.6(3) . . ?
N13 C5 C4 121.2(3) . . ?
C6 C5 C4 114.2(3) . . ?
N16 N15 N14 171.4(3) . . ?
N15 N14 C12 112.1(3) . . ?

_refine_diff_density_max         0.559
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.185



