# Electronic Supplementary Material (ESI) for Green 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_famid
_database_code_depnum_ccdc_archive 'CCDC 2097064'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;
_audit_creation_date             2021-07-15
_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 H19 N2 O, Cl'
_chemical_formula_sum            'C16 H19 Cl N2 O'
_chemical_formula_weight         290.78
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C64  H76  N8  O4  Cl4'
_chemical_oxdiff_usercomment     FAMID
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.78804(5)
_cell_length_b                   10.18953(7)
_cell_length_c                   19.93923(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1582.306(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3130
_cell_measurement_theta_min      4.4240
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    2.109
_exptl_absorpt_correction_T_max  0.36450
_exptl_absorpt_correction_T_min  0.28637
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 20 0.1000
6 -5 6 0.1000
4 -3 -16 0.1000
-4 3 -16 0.1000
-6 5 6 0.1000
0 0 -20 0.1000
-6 5 -6 0.1000
-4 3 16 0.1000
4 -3 16 0.1000
6 -5 -6 0.1000
8 0 0 0.1000
4 3 -16 0.1000
-2 8 -10 0.1000
-2 8 10 0.1000
4 3 16 0.1000
-8 0 0 0.1000
-4 -3 16 0.1000
2 -8 10 0.1000
2 -8 -10 0.1000
-4 -3 -16 0.1000
0 10 0 0.1000
2 8 10 0.1000
6 5 6 0.1000
6 5 -6 0.1000
2 8 -10 0.1000
0 -10 0 0.1000
-2 -8 -10 0.1000
-6 -5 -6 0.1000
-6 -5 6 0.1000
-2 -8 10 0.1000

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          0.104
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 -0.0001 19.9994 -1.5109 0.2004 -0.2532
5.9998 -4.9999 5.9997 -0.5685 -1.2893 -0.4583
4.0000 -2.9999 -15.9996 1.1260 -1.0446 -0.0047
-3.9998 3.0000 -15.9995 1.2915 0.7240 0.4098
-5.9999 4.9999 5.9999 -0.3380 1.4095 0.3064
0.0001 0.0001 -19.9994 1.5109 -0.2004 0.2532
-5.9998 4.9999 -5.9997 0.5685 1.2893 0.4583
-4.0000 2.9999 15.9996 -1.1260 1.0446 0.0047
3.9998 -3.0000 15.9995 -1.2915 -0.7240 -0.4098
5.9999 -4.9999 -5.9999 0.3380 -1.4095 -0.3064
7.9998 0.0000 -0.0001 -0.2728 -1.4941 0.4437
4.0000 3.0000 -15.9996 1.0187 -0.7701 0.8534
-1.9999 7.9999 -9.9997 0.6807 0.6394 1.1598
-2.0001 7.9998 9.9997 -0.8302 0.8398 0.9066
3.9998 2.9999 15.9994 -1.3987 -0.4495 0.4483
-7.9998 -0.0000 0.0001 0.2728 1.4941 -0.4437
-4.0000 -3.0000 15.9996 -1.0187 0.7701 -0.8534
1.9999 -7.9999 9.9997 -0.6807 -0.6394 -1.1598
2.0001 -7.9998 -9.9997 0.8302 -0.8398 -0.9066
-3.9998 -2.9999 -15.9994 1.3987 0.4495 -0.4483
-0.0000 9.9998 -0.0000 -0.1787 0.4575 1.4302
1.9998 7.9998 9.9997 -0.9666 0.0927 1.1285
5.9998 4.9999 5.9997 -0.7472 -0.8317 0.9719
5.9999 5.0000 -5.9999 0.1593 -0.9520 1.1238
2.0000 7.9999 -9.9997 0.5443 -0.1077 1.3816
0.0000 -9.9998 0.0000 0.1787 -0.4575 -1.4302
-1.9998 -7.9998 -9.9997 0.9666 -0.0927 -1.1285
-5.9998 -4.9999 -5.9997 0.7472 0.8317 -0.9719
-5.9999 -5.0000 5.9999 -0.1593 0.9520 -1.1238
-2.0000 -7.9999 9.9997 -0.5443 0.1077 -1.3816

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.647
_diffrn_reflns_theta_min         4.435
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     90.00 177.15   0.35    0.50    --  111.50  77.00  90.00  249
  2  ω    101.00 178.00   0.35    0.50    --  111.50  25.00  13.00  220
  3  ω    101.00 178.00   0.35    0.50    --  111.50  15.00 -30.00  220
  4  ω    101.00 178.00   0.35    0.50    --  111.50  30.00-120.00  220
  5  ω    101.00 178.00   0.35    0.50    --  111.50  15.00-180.00  220
  6  ω    -26.00  25.10   0.35    0.50    --  -48.76  19.00-120.00  146
  7  ω   -118.00 -35.75   0.35    0.50    --  -90.00 170.00   0.00  235
  8  ω    -26.00  25.10   0.35    0.50    --  -48.76  19.00 150.00  146
  9  ω    -31.00  25.00   0.35    0.50    --  -48.76  25.00  13.00  160
 10  ω   -121.00 -36.30   0.35    0.50    --  -48.76 -57.00-150.00  242
 11  ω   -121.00 -27.90   0.35    0.50    --  -48.76 -77.00 -60.00  266
 12  ω   -161.00-105.70   0.35    0.50    --  -90.00 -77.00  60.00  158
 13  ω   -121.00 -27.90   0.35    0.50    --  -48.76 -77.00  90.00  266
 14  ω    -25.00  31.00   0.35    0.50    --   48.76 -25.00-150.00  160
 15  ω     95.00 176.90   0.35    0.50    --  111.50 125.00   0.00  234
 16  ω     40.00 103.70   0.35    0.50    --  111.50 -77.00 150.00  182
 17  ω     40.00  69.75   0.35    0.50    --  111.50 -61.00  90.00   85
 18  ω     40.00  69.75   0.35    0.50    --  111.50 -61.00   0.00   85
 19  ω     40.00 103.70   0.35    0.50    --  111.50 -95.00 -60.00  182
 20  ω     57.00 143.10   0.35    0.50    --  111.50-170.00 -15.00  246
 21  ω     40.00 106.85   0.35    0.50    --  111.50-115.00 127.00  191
 22  ω     40.00 106.15   0.35    0.50    --  111.50-103.00  28.00  189
 23  ω     40.00 110.00   0.35    0.50    --  111.50-125.00-180.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0341010000
_diffrn_orient_matrix_UB_12      -0.0178685000
_diffrn_orient_matrix_UB_13      -0.0755493000
_diffrn_orient_matrix_UB_21      -0.1867732000
_diffrn_orient_matrix_UB_22      0.0457541000
_diffrn_orient_matrix_UB_23      0.0100187000
_diffrn_orient_matrix_UB_31      0.0554604000
_diffrn_orient_matrix_UB_32      0.1430188000
_diffrn_orient_matrix_UB_33      -0.0126587000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3329
_reflns_number_total             3379
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.3551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0642
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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_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 0.65239(5) 0.46616(4) 0.24757(2) 0.02541(11) Uani 1 1 d . . . . .
O1 O 0.04047(15) 0.64964(11) 0.23247(6) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.33282(19) 0.65335(14) 0.23283(8) 0.0247(3) Uani 1 1 d . . . . .
H1A H 0.432(3) 0.607(2) 0.2352(11) 0.027(5) Uiso 1 1 d . . . . .
H1B H 0.332(3) 0.741(2) 0.2320(11) 0.032(6) Uiso 1 1 d . . . . .
N2 N 0.03874(17) 0.40772(13) 0.28625(7) 0.0167(3) Uani 1 1 d . . . . .
H2A H -0.064(3) 0.452(2) 0.2713(11) 0.032(6) Uiso 1 1 d . . . . .
H2B H 0.016(3) 0.318(2) 0.2810(10) 0.021(5) Uiso 1 1 d . . . . .
C1 C 0.1829(2) 0.59459(15) 0.23541(8) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.18546(19) 0.44472(14) 0.24175(8) 0.0172(3) Uani 1 1 d . . . . .
H2 H 0.295693 0.416648 0.263092 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1664(2) 0.37722(15) 0.17431(8) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.0131(2) 0.38633(18) 0.13838(9) 0.0249(4) Uani 1 1 d . . . . .
H4 H -0.078243 0.439343 0.154598 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0050(2) 0.3171(2) 0.07857(9) 0.0287(4) Uani 1 1 d . . . . .
H5 H -0.109499 0.322698 0.054179 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1278(3) 0.2403(2) 0.05430(9) 0.0302(4) Uani 1 1 d . . . . .
H6 H 0.114449 0.193202 0.013500 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2801(3) 0.2324(2) 0.08985(10) 0.0324(4) Uani 1 1 d . . . . .
H7 H 0.371837 0.180238 0.073271 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2993(2) 0.30075(18) 0.14977(9) 0.0259(4) Uani 1 1 d . . . . .
H8 H 0.404132 0.294935 0.173977 0.031 Uiso 1 1 calc R U . . .
C9 C -0.1009(2) 0.39630(19) 0.39607(9) 0.0260(4) Uani 1 1 d . . . . .
H9A H -0.093643 0.421817 0.443376 0.039 Uiso 1 1 calc R U . . .
H9B H -0.112143 0.300717 0.392783 0.039 Uiso 1 1 calc R U . . .
H9C H -0.201263 0.438140 0.375514 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0615(2) 0.44025(16) 0.35954(8) 0.0195(3) Uani 1 1 d . . . . .
H10 H 0.072025 0.537652 0.364097 0.023 Uiso 1 1 calc R U . . .
C11 C 0.2212(2) 0.37770(17) 0.38865(8) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.2672(2) 0.24861(19) 0.37467(9) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.200709 0.198509 0.344011 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4103(2) 0.1923(2) 0.40536(9) 0.0275(4) Uani 1 1 d . . . . .
H13 H 0.441763 0.104453 0.395080 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5065(2) 0.2639(2) 0.45072(9) 0.0297(4) Uani 1 1 d . . . . .
H14 H 0.603584 0.225248 0.471751 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4612(2) 0.3920(2) 0.46541(10) 0.0316(4) Uani 1 1 d . . . . .
H15 H 0.526673 0.440994 0.496845 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3196(2) 0.44923(19) 0.43419(8) 0.0260(4) Uani 1 1 d . . . . .
H16 H 0.289972 0.537598 0.444024 0.031 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
O1 C1 1.2442(19) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.89(2) . ?
N1 C1 1.313(2) . ?
N2 H2A 0.96(2) . ?
N2 H2B 0.94(2) . ?
N2 C2 1.495(2) . ?
N2 C10 1.509(2) . ?
C1 C2 1.532(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.518(2) . ?
C3 C4 1.395(2) . ?
C3 C8 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C10 1.527(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.514(2) . ?
C11 C12 1.391(3) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(3) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 122(2) . . ?
C1 N1 H1A 120.9(14) . . ?
C1 N1 H1B 116.8(15) . . ?
H2A N2 H2B 105.4(19) . . ?
C2 N2 H2A 109.4(13) . . ?
C2 N2 H2B 108.8(13) . . ?
C2 N2 C10 115.44(13) . . ?
C10 N2 H2A 107.1(13) . . ?
C10 N2 H2B 110.2(13) . . ?
O1 C1 N1 125.81(14) . . ?
O1 C1 C2 117.70(14) . . ?
N1 C1 C2 116.48(14) . . ?
N2 C2 C1 106.87(12) . . ?
N2 C2 H2 109.4 . . ?
N2 C2 C3 109.68(12) . . ?
C1 C2 H2 109.4 . . ?
C3 C2 C1 112.16(13) . . ?
C3 C2 H2 109.4 . . ?
C4 C3 C2 120.56(15) . . ?
C8 C3 C2 119.66(15) . . ?
C8 C3 C4 119.71(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.50(17) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.69(17) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.57(17) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.22(17) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.30(17) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
N2 C10 C9 107.48(13) . . ?
N2 C10 H10 108.4 . . ?
N2 C10 C11 112.06(13) . . ?
C9 C10 H10 108.4 . . ?
C11 C10 C9 111.99(13) . . ?
C11 C10 H10 108.4 . . ?
C12 C11 C10 122.19(15) . . ?
C12 C11 C16 118.92(16) . . ?
C16 C11 C10 118.78(16) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.44(17) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.16(19) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.89(17) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.14(17) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.44(18) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.91(2) 2.25(2) 3.1494(15) 171(2) . yes
N1 H1B Cl1 0.89(2) 2.33(2) 3.2133(14) 168(2) 3_655 yes
N2 H2A Cl1 0.96(2) 2.27(2) 3.1627(14) 154.6(19) 1_455 yes
N2 H2B O1 0.94(2) 1.79(2) 2.7267(18) 175.7(19) 3_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 -37.23(19) . . . . ?
O1 C1 C2 C3 83.01(18) . . . . ?
N1 C1 C2 N2 143.48(14) . . . . ?
N1 C1 C2 C3 -96.28(17) . . . . ?
N2 C2 C3 C4 51.59(19) . . . . ?
N2 C2 C3 C8 -125.27(16) . . . . ?
N2 C10 C11 C12 -43.2(2) . . . . ?
N2 C10 C11 C16 140.81(15) . . . . ?
C1 C2 C3 C4 -66.99(19) . . . . ?
C1 C2 C3 C8 116.14(16) . . . . ?
C2 N2 C10 C9 179.55(13) . . . . ?
C2 N2 C10 C11 -57.01(18) . . . . ?
C2 C3 C4 C5 -176.15(16) . . . . ?
C2 C3 C8 C7 176.42(17) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C8 C3 C4 C5 0.7(3) . . . . ?
C9 C10 C11 C12 77.6(2) . . . . ?
C9 C10 C11 C16 -98.32(18) . . . . ?
C10 N2 C2 C1 -72.34(16) . . . . ?
C10 N2 C2 C3 165.84(13) . . . . ?
C10 C11 C12 C13 -176.49(16) . . . . ?
C10 C11 C16 C15 175.79(16) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C11 C16 C15 -0.3(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?

_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.504
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,4-dioxane, methanol'
