# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_933
_database_code_depnum_ccdc_archive 'CCDC 2094903'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Cl3 N6 O2'
_chemical_formula_sum            'C16 H17 Cl3 N6 O2'
_chemical_formula_weight         431.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.1174(6)
_cell_length_b                   18.2984(12)
_cell_length_c                   12.9072(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.790(7)
_cell_angle_gamma                90
_cell_volume                     1876.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2734
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.8970
_cell_measurement_theta_min      3.7160
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12805
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.124
_diffrn_reflns_theta_min         3.479
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  56.00   1.00   60.00    --   22.36-152.00 162.00   25
  2  ω     12.00  37.00   1.00   60.00    --   22.36-122.00 -37.00   25
  3  ω    -79.00 -33.00   1.00   60.00    --  -23.92 122.00  44.00   46
  4  ω    -76.00 -39.00   1.00   60.00    --  -23.92 152.00-155.00   37
  5  ω    -96.00   2.00   1.00   60.00    --  -23.92 -38.00  90.00   98
  6  ω    -93.00  -3.00   1.00   60.00    --  -23.92 -57.00-150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0056139000
_diffrn_orient_matrix_UB_12      0.0384750000
_diffrn_orient_matrix_UB_13      -0.0048292000
_diffrn_orient_matrix_UB_21      0.0382407000
_diffrn_orient_matrix_UB_22      0.0025012000
_diffrn_orient_matrix_UB_23      0.0544271000
_diffrn_orient_matrix_UB_31      0.0805008000
_diffrn_orient_matrix_UB_32      -0.0038700000
_diffrn_orient_matrix_UB_33      -0.0128336000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3163
_reflns_number_total             4875
_reflns_odcompleteness_completeness 98.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.048
_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)+(0.1100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.2073
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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
Cl3 Cl 0.18094(10) 0.79117(4) 0.94559(7) 0.0573(3) Uani 1 1 d . . . . .
Cl1 Cl 0.28286(14) 0.67474(5) 1.09150(7) 0.0680(3) Uani 1 1 d . . . . .
Cl2 Cl 0.53395(10) 0.76455(6) 1.02815(8) 0.0697(3) Uani 1 1 d . . . . .
O1 O 0.0660(3) 0.37125(12) 0.84047(17) 0.0520(5) Uani 1 1 d . . . . .
O2 O 0.2331(3) 0.40480(13) 0.18074(16) 0.0582(6) Uani 1 1 d . . . . .
N3 N 0.3098(3) 0.60441(12) 0.89893(17) 0.0395(5) Uani 1 1 d . . . . .
N4 N 0.2914(3) 0.55232(12) 0.62304(17) 0.0384(5) Uani 1 1 d . . . . .
N5 N 0.3262(3) 0.58011(13) 0.53954(17) 0.0392(5) Uani 1 1 d . . . . .
N1 N 0.3795(3) 0.70953(13) 0.80857(19) 0.0424(5) Uani 1 1 d . . . . .
N2 N 0.4148(4) 0.70404(17) 0.6387(2) 0.0462(6) Uani 1 1 d . . . . .
N6 N 0.2871(3) 0.48941(13) 0.83166(18) 0.0460(6) Uani 1 1 d . . . . .
C2 C 0.3419(3) 0.67369(14) 0.8886(2) 0.0373(6) Uani 1 1 d . . . . .
C7 C 0.2867(3) 0.53335(15) 0.4500(2) 0.0374(6) Uani 1 1 d . . . . .
C4 C 0.3058(3) 0.56101(15) 0.8127(2) 0.0369(6) Uani 1 1 d . . . . .
C5 C 0.3247(3) 0.59402(14) 0.7148(2) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.3743(3) 0.66859(15) 0.7201(2) 0.0361(6) Uani 1 1 d . . . . .
C10 C 0.2423(4) 0.44561(16) 0.2701(2) 0.0434(6) Uani 1 1 d . . . . .
C11 C 0.3239(4) 0.51244(17) 0.2722(2) 0.0424(6) Uani 1 1 d . . . . .
C12 C 0.3463(3) 0.55575(17) 0.3603(2) 0.0415(6) Uani 1 1 d . . . . .
C1 C 0.3352(4) 0.72229(16) 0.9845(2) 0.0421(6) Uani 1 1 d . . . . .
C8 C 0.1987(4) 0.46821(17) 0.4449(2) 0.0464(7) Uani 1 1 d . . . . .
C15 C 0.0800(4) 0.43007(17) 0.9139(2) 0.0494(7) Uani 1 1 d . . . . .
H15A H 0.057387 0.412218 0.980373 0.059 Uiso 1 1 calc R U . . .
H15B H -0.003543 0.466926 0.886778 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2753(4) 0.42816(15) 0.7576(2) 0.0443(7) Uani 1 1 d . . . . .
H13A H 0.359172 0.391576 0.785440 0.053 Uiso 1 1 calc R U . . .
H13B H 0.296333 0.445137 0.690321 0.053 Uiso 1 1 calc R U . . .
C9 C 0.1764(4) 0.42451(18) 0.3566(2) 0.0501(7) Uani 1 1 d . . . . .
C14 C 0.1029(4) 0.39546(17) 0.7422(2) 0.0477(7) Uani 1 1 d . . . . .
H14A H 0.020253 0.431547 0.710584 0.057 Uiso 1 1 calc R U . . .
H14B H 0.095175 0.354391 0.693928 0.057 Uiso 1 1 calc R U . . .
C16 C 0.2516(4) 0.46390(17) 0.9331(2) 0.0507(7) Uani 1 1 d . . . . .
H16A H 0.256555 0.504726 0.981618 0.061 Uiso 1 1 calc R U . . .
H16B H 0.335368 0.428246 0.964745 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1668(5) 0.3334(2) 0.1794(3) 0.0667(10) Uani 1 1 d . . . . .
H3A H 0.171561 0.310341 0.113245 0.100 Uiso 1 1 calc R U . . .
H3B H 0.051934 0.335765 0.187477 0.100 Uiso 1 1 calc R U . . .
H3C H 0.231705 0.305558 0.236450 0.100 Uiso 1 1 calc R U . . .
H12 H 0.401(4) 0.6069(17) 0.363(2) 0.045(8) Uiso 1 1 d . . . . .
H8 H 0.151(4) 0.4545(19) 0.504(3) 0.054(9) Uiso 1 1 d . . . . .
H2A H 0.427(4) 0.746(2) 0.646(3) 0.047(10) Uiso 1 1 d . . . . .
H11 H 0.367(4) 0.5236(17) 0.214(3) 0.048(8) Uiso 1 1 d . . . . .
H9 H 0.119(4) 0.378(2) 0.353(3) 0.068(11) Uiso 1 1 d . . . . .
H2B H 0.405(5) 0.683(2) 0.586(3) 0.067(12) Uiso 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
Cl3 C1 1.775(3) . ?
Cl1 C1 1.757(3) . ?
Cl2 C1 1.774(3) . ?
O1 C15 1.423(4) . ?
O1 C14 1.432(3) . ?
O2 C10 1.364(3) . ?
O2 C3 1.412(4) . ?
N3 C2 1.306(3) . ?
N3 C4 1.363(3) . ?
N4 N5 1.275(3) . ?
N4 C5 1.388(3) . ?
N5 C7 1.421(3) . ?
N1 C2 1.312(3) . ?
N1 C6 1.359(3) . ?
N2 C6 1.332(3) . ?
N2 H2A 0.78(3) . ?
N2 H2B 0.78(4) . ?
N6 C4 1.347(4) . ?
N6 C13 1.463(3) . ?
N6 C16 1.473(3) . ?
C2 C1 1.533(4) . ?
C7 C12 1.404(4) . ?
C7 C8 1.385(4) . ?
C4 C5 1.436(4) . ?
C5 C6 1.420(4) . ?
C10 C11 1.388(4) . ?
C10 C9 1.388(4) . ?
C11 C12 1.367(4) . ?
C11 H11 0.92(3) . ?
C12 H12 1.03(3) . ?
C8 C9 1.374(4) . ?
C8 H8 0.95(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.497(4) . ?
C9 H9 0.97(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C14 110.7(2) . . ?
C10 O2 C3 118.2(3) . . ?
C2 N3 C4 117.0(2) . . ?
N5 N4 C5 117.6(2) . . ?
N4 N5 C7 113.3(2) . . ?
C2 N1 C6 114.5(2) . . ?
C6 N2 H2A 116(3) . . ?
C6 N2 H2B 117(3) . . ?
H2A N2 H2B 126(4) . . ?
C4 N6 C13 128.4(2) . . ?
C4 N6 C16 121.3(2) . . ?
C13 N6 C16 109.8(2) . . ?
N3 C2 N1 130.4(2) . . ?
N3 C2 C1 116.1(2) . . ?
N1 C2 C1 113.4(2) . . ?
C12 C7 N5 115.9(2) . . ?
C8 C7 N5 125.8(2) . . ?
C8 C7 C12 118.3(3) . . ?
N3 C4 C5 119.0(2) . . ?
N6 C4 N3 113.7(2) . . ?
N6 C4 C5 127.3(2) . . ?
N4 C5 C4 118.8(2) . . ?
N4 C5 C6 124.9(2) . . ?
C6 C5 C4 116.2(2) . . ?
N1 C6 C5 122.0(2) . . ?
N2 C6 N1 115.1(3) . . ?
N2 C6 C5 122.9(2) . . ?
O2 C10 C11 116.2(3) . . ?
O2 C10 C9 124.4(3) . . ?
C9 C10 C11 119.4(3) . . ?
C10 C11 H11 116.3(19) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 123(2) . . ?
C7 C12 H12 116.9(17) . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 122.5(17) . . ?
Cl1 C1 Cl3 107.71(15) . . ?
Cl1 C1 Cl2 108.43(16) . . ?
Cl2 C1 Cl3 108.87(16) . . ?
C2 C1 Cl3 108.86(19) . . ?
C2 C1 Cl1 113.65(19) . . ?
C2 C1 Cl2 109.22(18) . . ?
C7 C8 H8 119(2) . . ?
C9 C8 C7 121.3(3) . . ?
C9 C8 H8 120(2) . . ?
O1 C15 H15A 109.3 . . ?
O1 C15 H15B 109.3 . . ?
O1 C15 C16 111.6(2) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N6 C13 H13A 109.9 . . ?
N6 C13 H13B 109.9 . . ?
N6 C13 C14 109.1(2) . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C10 C9 H9 118(2) . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 122(2) . . ?
O1 C14 C13 111.4(2) . . ?
O1 C14 H14A 109.3 . . ?
O1 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N6 C16 C15 109.1(2) . . ?
N6 C16 H16A 109.9 . . ?
N6 C16 H16B 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
O2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C15 C16 N6 57.7(3) . . . . ?
O2 C10 C11 C12 -177.0(3) . . . . ?
O2 C10 C9 C8 177.2(3) . . . . ?
N3 C2 C1 Cl3 -120.5(2) . . . . ?
N3 C2 C1 Cl1 -0.5(3) . . . . ?
N3 C2 C1 Cl2 120.7(2) . . . . ?
N3 C4 C5 N4 -168.8(2) . . . . ?
N3 C4 C5 C6 10.1(4) . . . . ?
N4 N5 C7 C12 -170.3(2) . . . . ?
N4 N5 C7 C8 8.5(4) . . . . ?
N4 C5 C6 N1 169.5(2) . . . . ?
N4 C5 C6 N2 -8.8(4) . . . . ?
N5 N4 C5 C4 -172.6(2) . . . . ?
N5 N4 C5 C6 8.5(4) . . . . ?
N5 C7 C12 C11 176.0(3) . . . . ?
N5 C7 C8 C9 -175.7(3) . . . . ?
N1 C2 C1 Cl3 59.4(3) . . . . ?
N1 C2 C1 Cl1 179.4(2) . . . . ?
N1 C2 C1 Cl2 -59.4(3) . . . . ?
N6 C4 C5 N4 12.7(4) . . . . ?
N6 C4 C5 C6 -168.4(3) . . . . ?
N6 C13 C14 O1 -58.2(3) . . . . ?
C2 N3 C4 N6 174.4(2) . . . . ?
C2 N3 C4 C5 -4.4(4) . . . . ?
C2 N1 C6 N2 -179.0(3) . . . . ?
C2 N1 C6 C5 2.6(4) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C4 N3 C2 N1 -3.5(4) . . . . ?
C4 N3 C2 C1 176.4(2) . . . . ?
C4 N6 C13 C14 -113.7(3) . . . . ?
C4 N6 C16 C15 114.7(3) . . . . ?
C4 C5 C6 N1 -9.4(4) . . . . ?
C4 C5 C6 N2 172.3(3) . . . . ?
C5 N4 N5 C7 -179.7(2) . . . . ?
C6 N1 C2 N3 4.4(4) . . . . ?
C6 N1 C2 C1 -175.5(2) . . . . ?
C10 C11 C12 C7 -0.1(5) . . . . ?
C11 C10 C9 C8 -2.8(5) . . . . ?
C12 C7 C8 C9 3.1(5) . . . . ?
C8 C7 C12 C11 -2.9(4) . . . . ?
C15 O1 C14 C13 57.7(3) . . . . ?
C13 N6 C4 N3 179.0(3) . . . . ?
C13 N6 C4 C5 -2.4(5) . . . . ?
C13 N6 C16 C15 -58.0(3) . . . . ?
C9 C10 C11 C12 3.0(5) . . . . ?
C14 O1 C15 C16 -57.5(3) . . . . ?
C16 N6 C4 N3 7.7(4) . . . . ?
C16 N6 C4 C5 -173.7(3) . . . . ?
C16 N6 C13 C14 58.3(3) . . . . ?
C3 O2 C10 C11 173.6(3) . . . . ?
C3 O2 C10 C9 -6.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.099
_oxdiff_exptl_absorpt_empirical_full_min 0.937
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1148
_database_code_depnum_ccdc_archive 'CCDC 2094904'
loop_
_audit_author_name
_audit_author_address
'P. Slepukhin'
;Institute of Organic Synthesis UB RAS (Russia)
Russia
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2021-10-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H15 Cl3 N6 O2'
_chemical_formula_sum            'C16 H15 Cl3 N6 O2'
_chemical_formula_weight         429.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.9266(5)
_cell_length_b                   8.4539(6)
_cell_length_c                   15.2045(9)
_cell_angle_alpha                86.573(5)
_cell_angle_beta                 89.013(5)
_cell_angle_gamma                65.020(7)
_cell_volume                     921.88(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.0030
_cell_measurement_theta_min      2.6600
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.98a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7218
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.66
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9555
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9891
_diffrn_measured_fraction_theta_max 0.9891
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00   7.00   1.00   40.00    --  -18.75 -77.00 -60.00   40
  2  ω    -37.00   3.00   1.00   40.00    --  -18.75 -77.00-180.00   40
  3  ω    -37.00   5.00   1.00   40.00    --  -18.75 -77.00  60.00   42
  4  ω    -39.00  32.00   1.00   40.00    --   21.40 -57.00 150.00   71
  5  ω    -41.00  33.00   1.00   40.00    --   21.40 -57.00 -90.00   74
  6  ω    -41.00  30.00   1.00   40.00    --   21.40 -57.00  30.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0812221000
_diffrn_orient_matrix_UB_12      0.0797151000
_diffrn_orient_matrix_UB_13      0.0008359000
_diffrn_orient_matrix_UB_21      0.0089808000
_diffrn_orient_matrix_UB_22      0.0160719000
_diffrn_orient_matrix_UB_23      -0.0457761000
_diffrn_orient_matrix_UB_31      -0.0553920000
_diffrn_orient_matrix_UB_32      -0.0445358000
_diffrn_orient_matrix_UB_33      -0.0093861000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2746
_reflns_number_total             4521
_reflns_odcompleteness_completeness 98.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.98a (Rigaku OD, 2021)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1300P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2439
_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 > 2sigma(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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl3 Cl 0.77373(19) 0.48564(14) 0.89223(8) 0.0731(4) Uani 0.96 1 d P A 1
Cl2 Cl 0.8087(2) 0.78700(19) 0.94351(9) 0.0857(5) Uani 0.96 1 d P A 1
Cl1 Cl 0.4609(2) 0.7568(2) 0.96481(8) 0.0860(5) Uani 0.96 1 d P A 1
N7 N 0.3424(4) 0.8823(3) 0.55045(17) 0.0390(6) Uani 1 1 d . . .
O1 O 0.0262(4) 0.8372(4) 0.23616(18) 0.0626(8) Uani 1 1 d . . .
O2 O 0.1559(5) 1.5883(3) 0.76365(19) 0.0665(8) Uani 1 1 d . . .
N6 N 0.3256(4) 1.0326(3) 0.58023(18) 0.0396(6) Uani 1 1 d . . .
N2 N 0.4001(4) 1.2456(3) 0.72501(19) 0.0457(7) Uani 1 1 d . . .
N3 N 0.5329(4) 0.9777(4) 0.80087(18) 0.0434(7) Uani 1 1 d . . .
N8 N 0.4333(5) 0.7380(4) 0.60132(19) 0.0478(7) Uani 1 1 d . . .
N1 N 0.5679(5) 0.7041(4) 0.7459(2) 0.0510(8) Uani 1 1 d . . .
C5 C 0.4116(5) 0.9822(4) 0.6592(2) 0.0390(7) Uani 1 1 d . . .
C10 C 0.6594(6) 0.7133(5) 0.8944(3) 0.0552(10) Uani 1 1 d D . .
C9 C 0.4778(5) 0.8011(4) 0.6726(2) 0.0441(8) Uani 1 1 d . . .
C15 C 0.2610(5) 0.8750(4) 0.4689(2) 0.0395(7) Uani 1 1 d . . .
C4 C 0.4474(5) 1.0738(4) 0.7288(2) 0.0389(7) Uani 1 1 d . . .
C2 C 0.5851(5) 0.8035(4) 0.8041(2) 0.0440(8) Uani 1 1 d . A .
C16 C 0.1677(5) 1.0253(4) 0.4164(2) 0.0454(8) Uani 1 1 d . . .
H16 H 0.1590 1.1319 0.4341 0.055 Uiso 1 1 calc R . .
C20 C 0.2768(5) 0.7143(4) 0.4432(2) 0.0477(9) Uani 1 1 d . . .
H20 H 0.3398 0.6131 0.4786 0.057 Uiso 1 1 calc R . .
C18 C 0.1003(5) 0.8594(5) 0.3122(2) 0.0458(8) Uani 1 1 d . . .
C17 C 0.0875(5) 1.0182(5) 0.3378(2) 0.0487(9) Uani 1 1 d . . .
H17 H 0.0254 1.1195 0.3023 0.058 Uiso 1 1 calc R . .
C19 C 0.1974(6) 0.7076(5) 0.3642(3) 0.0519(9) Uani 1 1 d . . .
H19 H 0.2091 0.6007 0.3456 0.062 Uiso 1 1 calc R . .
C11 C 0.4412(6) 1.3321(5) 0.7973(2) 0.0506(9) Uani 1 1 d . . .
H11A H 0.5192 1.3888 0.7761 0.061 Uiso 1 1 calc R . .
H11B H 0.5078 1.2461 0.8441 0.061 Uiso 1 1 calc R . .
C14 C 0.2864(6) 1.3705(4) 0.6556(2) 0.0517(9) Uani 1 1 d . . .
H14A H 0.2538 1.3098 0.6114 0.062 Uiso 1 1 calc R . .
H14B H 0.3553 1.4305 0.6273 0.062 Uiso 1 1 calc R . .
C13 C 0.1119(7) 1.5008(5) 0.6972(3) 0.0653(12) Uani 1 1 d . . .
H13A H 0.0354 1.5859 0.6522 0.078 Uiso 1 1 calc R . .
H13B H 0.0408 1.4403 0.7226 0.078 Uiso 1 1 calc R . .
C12 C 0.2620(6) 1.4652(5) 0.8319(3) 0.0587(10) Uani 1 1 d . . .
H12A H 0.1897 1.4063 0.8577 0.070 Uiso 1 1 calc R . .
H12B H 0.2891 1.5262 0.8777 0.070 Uiso 1 1 calc R . .
C1 C -0.0512(7) 0.9818(6) 0.1742(3) 0.0687(12) Uani 1 1 d . . .
H1A H -0.0878 0.9455 0.1219 0.103 Uiso 1 1 calc R . .
H1B H 0.0399 1.0259 0.1595 0.103 Uiso 1 1 calc R . .
H1C H -0.1581 1.0720 0.1992 0.103 Uiso 1 1 calc R . .
Cl4 Cl 0.661(6) 0.849(4) 0.9738(18) 0.0857(5) Uani 0.04 1 d PD A 2
Cl5 Cl 0.541(4) 0.620(5) 0.952(2) 0.0860(5) Uani 0.04 1 d PD A 2
Cl6 Cl 0.879(3) 0.546(3) 0.8871(19) 0.0731(4) Uani 0.04 1 d PD 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
Cl3 C10 1.749(4) . ?
Cl2 C10 1.748(4) . ?
Cl1 C10 1.804(5) . ?
N7 N6 1.327(3) . ?
N7 N8 1.330(4) . ?
N7 C15 1.424(4) . ?
O1 C18 1.364(4) . ?
O1 C1 1.417(5) . ?
O2 C13 1.417(5) . ?
O2 C12 1.424(5) . ?
N6 C5 1.345(4) . ?
N2 C4 1.336(4) . ?
N2 C11 1.468(4) . ?
N2 C14 1.461(4) . ?
N3 C4 1.331(4) . ?
N3 C2 1.349(4) . ?
N8 C9 1.351(4) . ?
N1 C9 1.359(4) . ?
N1 C2 1.302(4) . ?
C5 C9 1.396(4) . ?
C5 C4 1.448(4) . ?
C10 C2 1.530(5) . ?
C10 Cl4 1.720(18) . ?
C10 Cl5 1.673(17) . ?
C10 Cl6 1.722(16) . ?
C15 C16 1.380(5) . ?
C15 C20 1.390(4) . ?
C16 C17 1.380(5) . ?
C20 C19 1.382(5) . ?
C18 C17 1.383(5) . ?
C18 C19 1.388(5) . ?
C11 C12 1.502(6) . ?
C14 C13 1.514(6) . ?

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
N6 N7 N8 117.3(3) . . ?
N6 N7 C15 121.7(3) . . ?
N8 N7 C15 120.9(2) . . ?
C18 O1 C1 118.2(3) . . ?
C13 O2 C12 109.8(3) . . ?
N7 N6 C5 102.4(2) . . ?
C4 N2 C11 122.2(3) . . ?
C4 N2 C14 125.2(3) . . ?
C14 N2 C11 112.3(3) . . ?
C4 N3 C2 119.2(3) . . ?
N7 N8 C9 102.4(2) . . ?
C2 N1 C9 110.7(3) . . ?
N6 C5 C9 109.2(3) . . ?
N6 C5 C4 134.0(3) . . ?
C9 C5 C4 116.7(3) . . ?
Cl3 C10 Cl1 105.8(2) . . ?
Cl2 C10 Cl3 108.1(2) . . ?
Cl2 C10 Cl1 108.6(2) . . ?
C2 C10 Cl3 113.1(3) . . ?
C2 C10 Cl2 113.7(3) . . ?
C2 C10 Cl1 107.2(3) . . ?
C2 C10 Cl4 115.2(11) . . ?
C2 C10 Cl5 119.3(11) . . ?
C2 C10 Cl6 111.5(10) . . ?
Cl4 C10 Cl3 130.1(12) . . ?
Cl4 C10 Cl2 39.2(14) . . ?
Cl4 C10 Cl1 71.1(14) . . ?
Cl4 C10 Cl6 109.3(17) . . ?
Cl5 C10 Cl3 69.6(12) . . ?
Cl5 C10 Cl2 122.8(12) . . ?
Cl5 C10 Cl1 36.2(12) . . ?
Cl5 C10 Cl4 96.6(18) . . ?
Cl5 C10 Cl6 103.5(11) . . ?
Cl6 C10 Cl3 38.6(10) . . ?
Cl6 C10 Cl2 74.6(10) . . ?
Cl6 C10 Cl1 135.7(9) . . ?
N8 C9 N1 125.4(3) . . ?
N8 C9 C5 108.6(3) . . ?
N1 C9 C5 126.0(3) . . ?
C16 C15 N7 120.4(3) . . ?
C16 C15 C20 120.6(3) . . ?
C20 C15 N7 118.9(3) . . ?
N2 C4 C5 124.3(3) . . ?
N3 C4 N2 119.1(3) . . ?
N3 C4 C5 116.6(3) . . ?
N3 C2 C10 113.5(3) . . ?
N1 C2 N3 130.7(3) . . ?
N1 C2 C10 115.6(3) . . ?
C17 C16 C15 120.3(3) . . ?
C19 C20 C15 118.8(3) . . ?
O1 C18 C17 124.4(3) . . ?
O1 C18 C19 115.4(3) . . ?
C17 C18 C19 120.2(3) . . ?
C16 C17 C18 119.5(3) . . ?
C20 C19 C18 120.5(3) . . ?
N2 C11 C12 109.3(3) . . ?
N2 C14 C13 108.2(3) . . ?
O2 C13 C14 111.2(3) . . ?
O2 C12 C11 111.3(3) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.817
