# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 2258909'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        6-chloro-3-iodoimidazo[1,2-a]pyrazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H3 Cl I N3'
_chemical_formula_sum            'C6 H3 Cl I N3'
_chemical_formula_weight         279.46

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.0804(3)
_cell_length_b                   9.9981(5)
_cell_length_c                   13.2176(7)
_cell_angle_alpha                78.932(4)
_cell_angle_beta                 86.169(4)
_cell_angle_gamma                79.771(4)
_cell_volume                     775.61(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3526
_cell_measurement_theta_min      2.1240
_cell_measurement_theta_max      30.6980

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.403
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            13809
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.106
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3820
_reflns_number_gt                2961
_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 1.171.40.82a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+2.0157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3820
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.52239(5) 0.52237(3) 0.64719(3) 0.02218(10) Uani 1 1 d . . . . .
I2 I 0.68652(5) 1.18227(3) 0.14406(2) 0.02189(10) Uani 1 1 d . . . . .
Cl1 Cl -0.2650(2) 0.48531(14) 0.92880(10) 0.0256(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9368(2) 0.67299(14) 0.44905(11) 0.0293(3) Uani 1 1 d . . . . .
N2 N 0.3243(7) 0.3332(4) 0.8222(3) 0.0188(9) Uani 1 1 d . . . . .
N6 N 0.5147(7) 1.0021(4) 0.3324(3) 0.0186(9) Uani 1 1 d . . . . .
N3 N 0.0242(7) 0.2545(5) 0.9787(3) 0.0227(9) Uani 1 1 d . . . . .
N1 N 0.5816(8) 0.1384(4) 0.8649(3) 0.0228(9) Uani 1 1 d . . . . .
N5 N 0.5206(7) 0.7783(5) 0.4918(3) 0.0229(9) Uani 1 1 d . . . . .
N4 N 0.1534(7) 1.0882(5) 0.3634(4) 0.0273(11) Uani 1 1 d . . . . .
C3 C 0.1259(8) 0.4204(6) 0.8323(4) 0.0214(11) Uani 1 1 d . . . . .
H3 H 0.089468 0.506570 0.786919 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3768(9) 0.2065(5) 0.8883(4) 0.0213(11) Uani 1 1 d . . . . .
C2 C 0.5053(9) 0.3447(5) 0.7564(4) 0.0204(10) Uani 1 1 d . . . . .
C4 C -0.0157(9) 0.3767(6) 0.9107(4) 0.0227(11) Uani 1 1 d . . . . .
C9 C 0.7069(8) 0.9067(6) 0.3496(4) 0.0222(11) Uani 1 1 d . . . . .
H9 H 0.838441 0.916081 0.307728 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7015(9) 0.7989(5) 0.4282(4) 0.0222(11) Uani 1 1 d . . . . .
C1 C 0.6556(9) 0.2259(5) 0.7851(4) 0.0232(11) Uani 1 1 d . . . . .
H1 H 0.798193 0.207358 0.751907 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3380(9) 0.8714(5) 0.4757(4) 0.0217(11) Uani 1 1 d . . . . .
H11 H 0.211459 0.860588 0.520840 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4614(8) 1.1176(6) 0.2602(4) 0.0215(11) Uani 1 1 d . . . . .
C5 C 0.2138(9) 0.1720(6) 0.9673(4) 0.0246(11) Uani 1 1 d . . . . .
H5 H 0.243816 0.086030 1.013420 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3222(9) 0.9863(6) 0.3943(4) 0.0243(11) Uani 1 1 d . . . . .
C7 C 0.2395(9) 1.1669(6) 0.2790(4) 0.0273(12) Uani 1 1 d . . . . .
H7 H 0.156198 1.246010 0.238324 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
I1 C2 2.076(5) . ?
I2 C8 2.074(5) . ?
Cl1 C4 1.732(5) . ?
Cl2 C10 1.728(5) . ?
N2 C2 1.364(6) . ?
N2 C3 1.372(7) . ?
N2 C6 1.392(6) . ?
N6 C8 1.354(7) . ?
N6 C9 1.373(7) . ?
N6 C12 1.397(6) . ?
N3 C5 1.311(7) . ?
N3 C4 1.364(7) . ?
N1 C1 1.342(7) . ?
N1 C6 1.356(7) . ?
N5 C11 1.316(7) . ?
N5 C10 1.360(7) . ?
N4 C12 1.335(7) . ?
N4 C7 1.367(7) . ?
C3 C4 1.360(7) . ?
C3 H3 0.9500 . ?
C6 C5 1.427(7) . ?
C2 C1 1.370(7) . ?
C9 C10 1.349(7) . ?
C9 H9 0.9500 . ?
C1 H1 0.9500 . ?
C11 C12 1.410(8) . ?
C11 H11 0.9500 . ?
C8 C7 1.375(7) . ?
C5 H5 0.9500 . ?
C7 H7 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
C2 N2 C3 132.3(5) . . ?
C2 N2 C6 105.8(4) . . ?
C3 N2 C6 121.8(4) . . ?
C8 N6 C9 132.5(4) . . ?
C8 N6 C12 106.8(4) . . ?
C9 N6 C12 120.6(5) . . ?
C5 N3 C4 117.5(5) . . ?
C1 N1 C6 103.3(4) . . ?
C11 N5 C10 117.3(5) . . ?
C12 N4 C7 104.4(4) . . ?
C4 C3 N2 116.3(5) . . ?
C4 C3 H3 121.8 . . ?
N2 C3 H3 121.8 . . ?
N1 C6 N2 111.7(5) . . ?
N1 C6 C5 131.7(5) . . ?
N2 C6 C5 116.5(5) . . ?
N2 C2 C1 105.7(4) . . ?
N2 C2 I1 121.6(4) . . ?
C1 C2 I1 132.5(4) . . ?
C3 C4 N3 125.3(5) . . ?
C3 C4 Cl1 118.0(4) . . ?
N3 C4 Cl1 116.7(4) . . ?
C10 C9 N6 117.4(5) . . ?
C10 C9 H9 121.3 . . ?
N6 C9 H9 121.3 . . ?
C9 C10 N5 124.9(5) . . ?
C9 C10 Cl2 118.7(4) . . ?
N5 C10 Cl2 116.3(4) . . ?
N1 C1 C2 113.4(5) . . ?
N1 C1 H1 123.3 . . ?
C2 C1 H1 123.3 . . ?
N5 C11 C12 122.8(5) . . ?
N5 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
N6 C8 C7 105.9(4) . . ?
N6 C8 I2 122.3(4) . . ?
C7 C8 I2 131.7(4) . . ?
N3 C5 C6 122.5(5) . . ?
N3 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
N4 C12 N6 111.1(5) . . ?
N4 C12 C11 131.9(5) . . ?
N6 C12 C11 117.0(5) . . ?
N4 C7 C8 111.8(5) . . ?
N4 C7 H7 124.1 . . ?
C8 C7 H7 124.1 . . ?

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
C2 N2 C3 C4 -177.5(5) . . . . ?
C6 N2 C3 C4 0.5(7) . . . . ?
C1 N1 C6 N2 1.1(6) . . . . ?
C1 N1 C6 C5 -177.8(6) . . . . ?
C2 N2 C6 N1 -0.9(6) . . . . ?
C3 N2 C6 N1 -179.3(4) . . . . ?
C2 N2 C6 C5 178.2(5) . . . . ?
C3 N2 C6 C5 -0.2(7) . . . . ?
C3 N2 C2 C1 178.4(5) . . . . ?
C6 N2 C2 C1 0.2(6) . . . . ?
C3 N2 C2 I1 2.3(8) . . . . ?
C6 N2 C2 I1 -175.9(3) . . . . ?
N2 C3 C4 N3 -0.2(8) . . . . ?
N2 C3 C4 Cl1 178.3(4) . . . . ?
C5 N3 C4 C3 -0.4(8) . . . . ?
C5 N3 C4 Cl1 -178.9(4) . . . . ?
C8 N6 C9 C10 -177.9(5) . . . . ?
C12 N6 C9 C10 -0.4(7) . . . . ?
N6 C9 C10 N5 -0.3(8) . . . . ?
N6 C9 C10 Cl2 177.5(4) . . . . ?
C11 N5 C10 C9 -0.6(8) . . . . ?
C11 N5 C10 Cl2 -178.4(4) . . . . ?
C6 N1 C1 C2 -1.0(6) . . . . ?
N2 C2 C1 N1 0.5(6) . . . . ?
I1 C2 C1 N1 176.0(4) . . . . ?
C10 N5 C11 C12 2.2(8) . . . . ?
C9 N6 C8 C7 176.8(5) . . . . ?
C12 N6 C8 C7 -0.9(6) . . . . ?
C9 N6 C8 I2 0.7(8) . . . . ?
C12 N6 C8 I2 -177.0(4) . . . . ?
C4 N3 C5 C6 0.7(8) . . . . ?
N1 C6 C5 N3 178.4(5) . . . . ?
N2 C6 C5 N3 -0.4(8) . . . . ?
C7 N4 C12 N6 1.7(6) . . . . ?
C7 N4 C12 C11 -178.8(6) . . . . ?
C8 N6 C12 N4 -0.5(6) . . . . ?
C9 N6 C12 N4 -178.6(5) . . . . ?
C8 N6 C12 C11 179.9(5) . . . . ?
C9 N6 C12 C11 1.8(7) . . . . ?
N5 C11 C12 N4 177.7(6) . . . . ?
N5 C11 C12 N6 -2.8(8) . . . . ?
C12 N4 C7 C8 -2.3(6) . . . . ?
N6 C8 C7 N4 2.1(6) . . . . ?
I2 C8 C7 N4 177.6(4) . . . . ?

_refine_diff_density_max         2.044
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.180

####################################################################### 
# 
# 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_test2
_database_code_depnum_ccdc_archive 'CCDC 2258911'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
6-chloro-8-iodo-2-(4-methoxyphenyl)imidazo[1,2-a]pyrazine-3-carbonitrile
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Cl I N4 O'
_chemical_formula_sum            'C14 H8 Cl I N4 O'
_chemical_formula_weight         410.59

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.9084(3)
_cell_length_b                   8.9556(3)
_cell_length_c                   9.5787(3)
_cell_angle_alpha                75.6990(10)
_cell_angle_beta                 74.5870(10)
_cell_angle_gamma                80.1380(10)
_cell_volume                     709.30(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8936
_cell_measurement_theta_min      2.8760
_cell_measurement_theta_max      35.8900

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.449
_shelx_estimated_absorpt_T_min   0.441
_shelx_estimated_absorpt_T_max   0.710
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6067
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode generator'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            10790
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.163
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2820
_reflns_number_gt                2610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²+0.5053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2820
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0551
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.89149(2) 0.67599(2) 0.16971(2) 0.03041(7) Uani 1 1 d . . . . .
Cl1 Cl 1.44635(7) 0.39127(7) 0.32621(7) 0.02704(13) Uani 1 1 d . . . . .
O1 O 0.4519(2) 1.2445(2) 0.8842(2) 0.0279(4) Uani 1 1 d . . . . .
N1 N 1.1791(2) 0.5393(2) 0.2751(2) 0.0205(4) Uani 1 1 d . . . . .
C1 C 1.0509(3) 0.6330(3) 0.3029(3) 0.0199(4) Uani 1 1 d . . . . .
N2 N 0.8870(2) 0.8036(2) 0.4714(2) 0.0200(4) Uani 1 1 d . . . . .
C2 C 1.0113(3) 0.7097(3) 0.4230(3) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.9122(3) 0.8421(3) 0.5910(3) 0.0191(4) Uani 1 1 d . . . . .
N3 N 1.1202(2) 0.6851(2) 0.5082(2) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.6581(3) 1.0057(3) 0.6245(3) 0.0229(5) Uani 1 1 d . . . . .
H9 H 0.6426(6) 0.9797(10) 0.543(3) 0.028 Uiso 1 1 calc R U . . .
C5 C 1.1458(3) 0.7798(3) 0.7177(3) 0.0262(5) Uani 1 1 d . . . . .
C4 C 1.0585(3) 0.7711(3) 0.6157(3) 0.0202(5) Uani 1 1 d . . . . .
N4 N 1.2177(3) 0.7881(3) 0.7972(3) 0.0412(6) Uani 1 1 d . . . . .
C6 C 1.2566(3) 0.5879(3) 0.4811(3) 0.0217(5) Uani 1 1 d . . . . .
H6 H 1.327(3) 0.5716(7) 0.537(2) 0.026 Uiso 1 1 calc R U . . .
C7 C 1.2789(3) 0.5179(3) 0.3653(3) 0.0210(5) Uani 1 1 d . . . . .
C8 C 0.7958(3) 0.9455(3) 0.6728(3) 0.0196(4) Uani 1 1 d . . . . .
C10 C 0.5458(3) 1.1036(3) 0.6978(3) 0.0244(5) Uani 1 1 d . . . . .
H10 H 0.457(3) 1.1421(15) 0.6650(13) 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5675(3) 1.1444(3) 0.8222(3) 0.0211(5) Uani 1 1 d . . . . .
C14 C 0.4680(3) 1.2906(3) 1.0117(3) 0.0265(5) Uani 1 1 d . . . . .
H14A H 0.474(2) 1.2057(18) 1.0857(17) 0.040 Uiso 1 1 calc R U . . .
H14B H 0.384(2) 1.357(2) 1.0420(15) 0.040 Uiso 1 1 calc R U . . .
H14C H 0.556(2) 1.338(2) 0.9883(8) 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8153(3) 0.9855(3) 0.7983(3) 0.0219(5) Uani 1 1 d . . . . .
H13 H 0.901(3) 0.9472(15) 0.8308(13) 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7027(3) 1.0845(3) 0.8729(3) 0.0212(5) Uani 1 1 d . . . . .
H12 H 0.7179 1.1110 0.9579 0.025 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
I1 C1 2.079(2) . ?
Cl1 C7 1.727(2) . ?
O1 C11 1.356(3) . ?
O1 C14 1.430(3) . ?
N1 C1 1.304(3) . ?
N1 C7 1.357(3) . ?
C1 C2 1.418(3) . ?
N2 C2 1.323(3) . ?
N2 C3 1.356(3) . ?
C2 N3 1.384(3) . ?
C3 C4 1.402(3) . ?
C3 C8 1.464(3) . ?
N3 C6 1.371(3) . ?
N3 C4 1.379(3) . ?
C9 C10 1.376(3) . ?
C9 C8 1.401(3) . ?
C9 H9 0.91(3) . ?
C5 N4 1.140(3) . ?
C5 C4 1.424(3) . ?
C6 C7 1.360(3) . ?
C6 H6 0.90(3) . ?
C8 C13 1.396(3) . ?
C10 C11 1.398(3) . ?
C10 H10 0.91(3) . ?
C11 C12 1.391(3) . ?
C14 H14A 0.908(19) . ?
C14 H14B 0.908(19) . ?
C14 H14C 0.908(19) . ?
C13 C12 1.390(3) . ?
C13 H13 0.88(3) . ?
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
C11 O1 C14 118.16(19) . . ?
C1 N1 C7 117.4(2) . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 I1 120.43(17) . . ?
C2 C1 I1 116.49(17) . . ?
C2 N2 C3 106.42(19) . . ?
N2 C2 N3 111.7(2) . . ?
N2 C2 C1 132.0(2) . . ?
N3 C2 C1 116.3(2) . . ?
N2 C3 C4 109.9(2) . . ?
N2 C3 C8 120.9(2) . . ?
C4 C3 C8 129.2(2) . . ?
C6 N3 C4 131.9(2) . . ?
C6 N3 C2 121.92(19) . . ?
C4 N3 C2 106.15(19) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
N4 C5 C4 178.7(3) . . ?
N3 C4 C3 105.8(2) . . ?
N3 C4 C5 120.9(2) . . ?
C3 C4 C5 133.2(2) . . ?
C7 C6 N3 116.2(2) . . ?
C7 C6 H6 121.9 . . ?
N3 C6 H6 121.9 . . ?
N1 C7 C6 125.1(2) . . ?
N1 C7 Cl1 116.00(17) . . ?
C6 C7 Cl1 118.88(19) . . ?
C13 C8 C9 118.4(2) . . ?
C13 C8 C3 122.8(2) . . ?
C9 C8 C3 118.8(2) . . ?
C9 C10 C11 120.3(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
O1 C11 C12 124.5(2) . . ?
O1 C11 C10 115.7(2) . . ?
C12 C11 C10 119.8(2) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 C8 121.3(2) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?

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
C7 N1 C1 C2 -1.2(3) . . . . ?
C7 N1 C1 I1 179.21(16) . . . . ?
C3 N2 C2 N3 -0.3(3) . . . . ?
C3 N2 C2 C1 179.9(2) . . . . ?
N1 C1 C2 N2 -177.6(2) . . . . ?
I1 C1 C2 N2 2.0(3) . . . . ?
N1 C1 C2 N3 2.5(3) . . . . ?
I1 C1 C2 N3 -177.82(15) . . . . ?
C2 N2 C3 C4 0.9(3) . . . . ?
C2 N2 C3 C8 -179.8(2) . . . . ?
N2 C2 N3 C6 178.1(2) . . . . ?
C1 C2 N3 C6 -2.1(3) . . . . ?
N2 C2 N3 C4 -0.5(3) . . . . ?
C1 C2 N3 C4 179.4(2) . . . . ?
C6 N3 C4 C3 -177.4(2) . . . . ?
C2 N3 C4 C3 1.0(2) . . . . ?
C6 N3 C4 C5 5.6(4) . . . . ?
C2 N3 C4 C5 -176.0(2) . . . . ?
N2 C3 C4 N3 -1.2(3) . . . . ?
C8 C3 C4 N3 179.6(2) . . . . ?
N2 C3 C4 C5 175.3(3) . . . . ?
C8 C3 C4 C5 -3.9(4) . . . . ?
C4 N3 C6 C7 178.5(2) . . . . ?
C2 N3 C6 C7 0.3(3) . . . . ?
C1 N1 C7 C6 -0.8(4) . . . . ?
C1 N1 C7 Cl1 179.30(17) . . . . ?
N3 C6 C7 N1 1.2(4) . . . . ?
N3 C6 C7 Cl1 -178.89(17) . . . . ?
C10 C9 C8 C13 0.8(4) . . . . ?
C10 C9 C8 C3 -179.8(2) . . . . ?
N2 C3 C8 C13 178.6(2) . . . . ?
C4 C3 C8 C13 -2.2(4) . . . . ?
N2 C3 C8 C9 -0.7(3) . . . . ?
C4 C3 C8 C9 178.4(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C14 O1 C11 C12 -0.9(3) . . . . ?
C14 O1 C11 C10 -179.9(2) . . . . ?
C9 C10 C11 O1 178.4(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C9 C8 C13 C12 -0.9(4) . . . . ?
C3 C8 C13 C12 179.7(2) . . . . ?
C8 C13 C12 C11 0.3(4) . . . . ?
O1 C11 C12 C13 -178.4(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?

_refine_diff_density_max         1.195
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.080

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_test1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2258910'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
5-allyl-6-chloroimidazo[1,2-a]pyrazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 Cl N3'
_chemical_formula_sum            'C9 H8 Cl N3'
_chemical_formula_weight         193.63

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.2253(10)
_cell_length_b                   7.3421(4)
_cell_length_c                   9.4392(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.538(7)
_cell_angle_gamma                90
_cell_volume                     878.64(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3079
_cell_measurement_theta_min      2.2090
_cell_measurement_theta_max      30.5660

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.385
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            14527
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.206
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2173
_reflns_number_gt                1735
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.3383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cl1 Cl 0.17023(4) -0.37270(6) 1.04448(5) 0.03333(17) Uani 1 1 d . . . . .
N1 N 0.32234(11) 0.0381(2) 0.92986(15) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.34221(14) 0.2206(2) 0.92120(19) 0.0268(4) Uani 1 1 d . . . . .
H1 H 0.3134(8) 0.311(2) 0.9555(9) 0.032 Uiso 1 1 calc R U . . .
C2 C 0.41732(15) 0.2305(3) 0.8466(2) 0.0289(4) Uani 1 1 d . . . . .
H2 H 0.4448(7) 0.337(3) 0.8248(6) 0.035 Uiso 1 1 calc R U . . .
N2 N 0.44597(12) 0.0631(2) 0.80902(17) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.38770(13) -0.0534(2) 0.85993(18) 0.0236(4) Uani 1 1 d . . . . .
N3 N 0.31644(12) -0.3376(2) 0.91039(17) 0.0265(3) Uani 1 1 d . . . . .
C6 C 0.25363(13) -0.0547(2) 0.99092(18) 0.0235(4) Uani 1 1 d . . . . .
C4 C 0.38113(14) -0.2451(2) 0.85456(19) 0.0265(4) Uani 1 1 d . . . . .
H4 H 0.4243(10) -0.3086(15) 0.8097(11) 0.032 Uiso 1 1 calc R U . . .
C5 C 0.25482(14) -0.2389(2) 0.97584(18) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.18715(14) 0.0558(3) 1.06427(19) 0.0269(4) Uani 1 1 d . . . . .
H7A H 0.1631(4) -0.0236(12) 1.1316(10) 0.032 Uiso 1 1 calc R U . . .
H7B H 0.2313(7) 0.1509(14) 1.1240(9) 0.032 Uiso 1 1 calc R U . . .
C8 C 0.09260(15) 0.1440(2) 0.9602(2) 0.0288(4) Uani 1 1 d . . . . .
H8 H 0.0521(10) 0.2195(18) 1.0024(10) 0.035 Uiso 1 1 calc R U . . .
C9 C 0.06093(16) 0.1262(3) 0.8163(2) 0.0368(5) Uani 1 1 d . . . . .
H9A H 0.0987(7) 0.0522(14) 0.7687(9) 0.044 Uiso 1 1 calc R U . . .
H9B H 0.0006(11) 0.1875(11) 0.7612(10) 0.044 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
Cl1 C5 1.7463(18) . ?
N1 C1 1.372(2) . ?
N1 C6 1.386(2) . ?
N1 C3 1.400(2) . ?
C1 C2 1.373(3) . ?
C1 H1 0.87(2) . ?
C2 N2 1.362(2) . ?
C2 H2 0.91(2) . ?
N2 C3 1.329(2) . ?
C3 C4 1.410(3) . ?
N3 C4 1.314(2) . ?
N3 C5 1.363(2) . ?
C6 C5 1.360(3) . ?
C6 C7 1.502(2) . ?
C4 H4 0.93(2) . ?
C7 C8 1.500(3) . ?
C7 H7A 0.980(14) . ?
C7 H7B 0.980(14) . ?
C8 C9 1.309(3) . ?
C8 H8 0.93(2) . ?
C9 H9A 0.935(17) . ?
C9 H9B 0.935(17) . ?

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 C6 131.63(15) . . ?
C1 N1 C3 106.62(14) . . ?
C6 N1 C3 121.75(15) . . ?
N1 C1 C2 105.13(16) . . ?
N1 C1 H1 127.4 . . ?
C2 C1 H1 127.4 . . ?
N2 C2 C1 112.41(17) . . ?
N2 C2 H2 123.8 . . ?
C1 C2 H2 123.8 . . ?
C3 N2 C2 104.68(15) . . ?
N2 C3 N1 111.16(15) . . ?
N2 C3 C4 131.71(16) . . ?
N1 C3 C4 117.13(15) . . ?
C4 N3 C5 116.64(15) . . ?
C5 C6 N1 114.63(15) . . ?
C5 C6 C7 127.63(16) . . ?
N1 C6 C7 117.74(16) . . ?
N3 C4 C3 122.80(16) . . ?
N3 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
C6 C5 N3 127.03(16) . . ?
C6 C5 Cl1 119.53(13) . . ?
N3 C5 Cl1 113.44(13) . . ?
C8 C7 C6 114.80(15) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 126.69(18) . . ?
C9 C8 H8 116.7 . . ?
C7 C8 H8 116.7 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 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
C6 N1 C1 C2 -179.28(17) . . . . ?
C3 N1 C1 C2 0.32(19) . . . . ?
N1 C1 C2 N2 -0.4(2) . . . . ?
C1 C2 N2 C3 0.3(2) . . . . ?
C2 N2 C3 N1 -0.11(19) . . . . ?
C2 N2 C3 C4 179.60(18) . . . . ?
C1 N1 C3 N2 -0.14(19) . . . . ?
C6 N1 C3 N2 179.51(14) . . . . ?
C1 N1 C3 C4 -179.89(14) . . . . ?
C6 N1 C3 C4 -0.2(2) . . . . ?
C1 N1 C6 C5 179.00(16) . . . . ?
C3 N1 C6 C5 -0.6(2) . . . . ?
C1 N1 C6 C7 -0.8(3) . . . . ?
C3 N1 C6 C7 179.69(14) . . . . ?
C5 N3 C4 C3 -0.3(3) . . . . ?
N2 C3 C4 N3 -178.99(17) . . . . ?
N1 C3 C4 N3 0.7(3) . . . . ?
N1 C6 C5 N3 1.1(3) . . . . ?
C7 C6 C5 N3 -179.22(16) . . . . ?
N1 C6 C5 Cl1 -178.75(11) . . . . ?
C7 C6 C5 Cl1 1.0(3) . . . . ?
C4 N3 C5 C6 -0.6(3) . . . . ?
C4 N3 C5 Cl1 179.17(13) . . . . ?
C5 C6 C7 C8 -101.0(2) . . . . ?
N1 C6 C7 C8 78.7(2) . . . . ?
C6 C7 C8 C9 3.7(3) . . . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_test1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2258912'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2023-04-25 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
6-chloro-2-iodoimidazo[1,2-a]pyrazine-3-carbonitrile
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H2 Cl I N4'
_chemical_formula_sum            'C7 H2 Cl I N4'
_chemical_formula_weight         304.48

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.2171(2)
_cell_length_b                   5.69960(10)
_cell_length_c                   18.6448(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.8020(10)
_cell_angle_gamma                90
_cell_volume                     860.47(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9896
_cell_measurement_theta_min      2.5704
_cell_measurement_theta_max      36.3227

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    2.350
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.983
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_T_max  0.7410
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode generator'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            18326
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.743
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2609
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0022P)²+0.9066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2609
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0386
_refine_ls_wR_factor_gt          0.0369
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
I1 I 0.85486(2) 0.74141(2) 0.18507(2) 0.01984(4) Uani 1 1 d . . . . .
N1 N 0.65437(19) 0.7874(3) 0.03423(8) 0.0188(3) Uani 1 1 d . . . . .
C1 C 0.7662(2) 0.6551(3) 0.07770(9) 0.0166(3) Uani 1 1 d . . . . .
Cl1 Cl 0.62360(6) 0.25313(8) -0.22923(2) 0.02658(10) Uani 1 1 d . . . . .
C2 C 0.8147(2) 0.4615(3) 0.04092(9) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.72775(17) 0.4772(2) -0.02889(8) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.6301(2) 0.4174(3) -0.15145(9) 0.0172(3) Uani 1 1 d . . . . .
N4 N 1.0366(2) 0.1472(3) 0.07819(9) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.6324(2) 0.6784(3) -0.03084(9) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.7279(2) 0.3421(3) -0.08940(9) 0.0158(3) Uani 1 1 d . . . . .
H3 H 0.7893(15) 0.211(3) -0.08829(10) 0.019 Uiso 1 1 calc R U . . .
N3 N 0.53529(19) 0.6133(3) -0.15729(8) 0.0185(3) Uani 1 1 d . . . . .
C5 C 0.5360(2) 0.7398(3) -0.09823(9) 0.0181(3) Uani 1 1 d . . . . .
H5 H 0.4661(16) 0.884(3) -0.10118(12) 0.022 Uiso 1 1 calc R U . . .
C7 C 0.9351(2) 0.2853(3) 0.06229(9) 0.0175(3) 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
I1 C1 2.0698(17) . ?
N1 C6 1.347(2) . ?
N1 C1 1.348(2) . ?
C1 C2 1.392(2) . ?
Cl1 C4 1.7194(18) . ?
C2 N2 1.377(2) . ?
C2 C7 1.418(2) . ?
N2 C3 1.366(2) . ?
N2 C6 1.385(2) . ?
C4 N3 1.355(2) . ?
C4 C3 1.361(2) . ?
N4 C7 1.149(2) . ?
C6 C5 1.411(2) . ?
C3 H3 0.90(2) . ?
N3 C5 1.316(2) . ?
C5 H5 1.00(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 104.85(14) . . ?
N1 C1 C2 111.72(15) . . ?
N1 C1 I1 122.70(13) . . ?
C2 C1 I1 125.57(13) . . ?
N2 C2 C1 105.56(14) . . ?
N2 C2 C7 122.43(15) . . ?
C1 C2 C7 131.83(16) . . ?
C3 N2 C2 132.13(15) . . ?
C3 N2 C6 121.65(15) . . ?
C2 N2 C6 106.18(14) . . ?
N3 C4 C3 125.19(16) . . ?
N3 C4 Cl1 116.48(13) . . ?
C3 C4 Cl1 118.33(14) . . ?
N1 C6 N2 111.69(15) . . ?
N1 C6 C5 131.00(16) . . ?
N2 C6 C5 117.27(15) . . ?
C4 C3 N2 116.17(15) . . ?
C4 C3 H3 121.9 . . ?
N2 C3 H3 121.9 . . ?
C5 N3 C4 117.63(15) . . ?
N3 C5 C6 122.09(16) . . ?
N3 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
N4 C7 C2 177.4(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
C6 N1 C1 C2 -0.5(2) . . . . ?
C6 N1 C1 I1 178.27(12) . . . . ?
N1 C1 C2 N2 0.2(2) . . . . ?
I1 C1 C2 N2 -178.55(12) . . . . ?
N1 C1 C2 C7 175.26(18) . . . . ?
I1 C1 C2 C7 -3.5(3) . . . . ?
C1 C2 N2 C3 177.74(17) . . . . ?
C7 C2 N2 C3 2.1(3) . . . . ?
C1 C2 N2 C6 0.23(18) . . . . ?
C7 C2 N2 C6 -175.45(16) . . . . ?
C1 N1 C6 N2 0.6(2) . . . . ?
C1 N1 C6 C5 -176.86(19) . . . . ?
C3 N2 C6 N1 -178.38(15) . . . . ?
C2 N2 C6 N1 -0.6(2) . . . . ?
C3 N2 C6 C5 -0.5(2) . . . . ?
C2 N2 C6 C5 177.32(16) . . . . ?
N3 C4 C3 N2 0.3(3) . . . . ?
Cl1 C4 C3 N2 -179.38(12) . . . . ?
C2 N2 C3 C4 -176.81(17) . . . . ?
C6 N2 C3 C4 0.4(2) . . . . ?
C3 C4 N3 C5 -0.8(3) . . . . ?
Cl1 C4 N3 C5 178.86(13) . . . . ?
C4 N3 C5 C6 0.7(3) . . . . ?
N1 C6 C5 N3 177.34(18) . . . . ?
N2 C6 C5 N3 0.0(3) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3

