# 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_cg-sp-96
_database_code_depnum_ccdc_archive 'CCDC 2077411'
loop_
_audit_author_name
_audit_author_address
'Chidambaram Gunanathan'
;National Institute of Science Education and Research 
India
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C38 H46 N2 O4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2951(2)
_cell_length_b                   7.8493(3)
_cell_length_c                   16.3441(5)
_cell_angle_alpha                80.613(3)
_cell_angle_beta                 85.440(3)
_cell_angle_gamma                89.520(3)
_cell_volume                     794.25(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7407
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1210
_cell_measurement_theta_min      5.4840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73382
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12051
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.831
_diffrn_reflns_theta_min         5.504
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_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    -99.00 -14.00   0.50    0.88    --  -38.50 141.00-114.00  170
  2  ω    -90.00  -8.00   0.50    0.88    --  -38.50 129.00  73.00  164
  3  ω     36.00 110.00   0.50    0.88    --   49.31-141.00-172.00  148
  4  ω     30.00 103.00   0.50    0.88    --   49.31-129.00  -0.00  146
  5  ω     39.00 115.00   0.50    3.49    --  102.63-129.00  -0.00  152
  6  ω     95.00 167.00   0.50    3.49    --  102.63 129.00  73.00  144
  7  ω     39.00 124.00   0.50    3.49    --  102.63-141.00-172.00  170
  8  ω     88.00 166.00   0.50    3.49    --  102.63 141.00-114.00  156
  9  ω   -105.00 -35.00   0.50    0.88    --  -38.50 -38.00   0.00  140
 10  ω   -105.00 -35.00   0.50    0.88    --  -38.50 -38.00-180.00  140
 11  ω    -42.00  28.00   0.50    0.88    --  -38.50  38.00-180.00  140
 12  ω    -42.00  28.00   0.50    0.88    --  -38.50  38.00 -60.00  140
 13  ω     40.00 116.00   0.50    3.49    --  102.63 -61.00 150.00  152
 14  ω     99.00 171.00   0.50    3.49    --  102.63  30.00 -90.00  144
 15  ω     38.00 107.00   0.50    3.49    --  102.63 -45.00 -30.00  138
 16  ω    103.00 167.00   0.50    3.49    --  102.63  77.00 -30.00  128
 17  ω     38.00 107.00   0.50    3.49    --  102.63 -45.00-180.00  138
 18  ω     35.00 106.00   0.50    3.49    --  102.63 -30.00 120.00  142
 19  ω     98.00 167.00   0.50    3.49    --  102.63  45.00  90.00  138
 20  ω     34.00 107.00   0.50    3.49    --  102.63 -94.00 150.00  146
 21  ω     38.00 126.00   0.50    3.49    --  102.63 -77.00 -30.00  176
 22  ω     95.00 171.00   0.50    3.49    --  102.63  15.00-180.00  152
 23  ω     38.00 107.00   0.50    3.49    --  102.63 -45.00-120.00  138
 24  ω     40.00 116.00   0.50    3.49    --  102.63 -61.00   0.00  152
 25  ω     38.00 112.00   0.50    3.49    --  102.63-125.00 -90.00  148
 26  ω     34.00 107.00   0.50    3.49    --  102.63 -94.00 -30.00  146
 27  ω     90.00 165.00   0.50    3.49    --  102.63  61.00 150.00  150
 28  ω    103.00 167.00   0.50    3.49    --  102.63  77.00-120.00  128
 29  ω     38.00 112.00   0.50    3.49    --  102.63-125.00 120.00  148
 30  ω     99.00 171.00   0.50    3.49    --  102.63  30.00  30.00  144
 31  ω   -101.00 -27.00   0.50    0.88    --  -38.50 -57.00 -90.00  148
 32  ω     38.00 112.00   0.50    0.88    --   49.31  57.00 120.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1437773000
_diffrn_orient_matrix_UB_12      -0.0233417000
_diffrn_orient_matrix_UB_13      -0.0781336000
_diffrn_orient_matrix_UB_21      -0.1601905000
_diffrn_orient_matrix_UB_22      0.1022336000
_diffrn_orient_matrix_UB_23      -0.0553316000
_diffrn_orient_matrix_UB_31      0.1180669000
_diffrn_orient_matrix_UB_32      0.1690570000
_diffrn_orient_matrix_UB_33      0.0042933000
_diffrn_oxdiff_digest_frames     
;
0199e80f5b6b5c2dcd3f935e022fa7c17b00033e592
;
_diffrn_oxdiff_digest_hkl        
;
018773a3b8a7fda95d06f2129fb964651562f5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2845
_reflns_number_total             3191
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0020(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.074
_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)+(0.0752P)²+0.1820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1353
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C15(H15), C10(H10), C12(H12), C16(H16), C5(H5), C13(H13), C3(H3),
 C6(H6), C2(H2)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O17 O 0.21608(14) 0.62020(12) 0.05787(5) 0.0303(2) Uani 1 1 d . . . . .
O20 O 1.20560(14) 0.03516(12) 0.78753(5) 0.0313(2) Uani 1 1 d . . . . .
N9 N 0.52463(17) 0.38079(14) 0.42410(6) 0.0292(3) Uani 1 1 d . . . . .
N8 N 0.62132(18) 0.30697(15) 0.49281(7) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.570736 0.323838 0.541272 0.039 Uiso 1 1 calc R . . . .
C14 C 0.2870(2) 0.54891(16) 0.13299(8) 0.0273(3) Uani 1 1 d . . . . .
C4 C 1.11576(19) 0.08272(16) 0.71371(7) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.4756(2) 0.45480(16) 0.12899(8) 0.0290(3) Uani 1 1 d . . . . .
H15 H 0.542343 0.440937 0.077669 0.035 Uiso 1 1 calc R . . . .
C1 C 0.9111(2) 0.16151(17) 0.56604(8) 0.0300(3) Uani 1 1 d . . . . .
C10 C 0.57295(19) 0.32972(16) 0.35411(8) 0.0281(3) Uani 1 1 d . . . . .
H10 H 0.676309 0.245249 0.350775 0.034 Uiso 1 1 calc R . . . .
C12 C 0.2761(2) 0.49416(17) 0.28235(8) 0.0303(3) Uani 1 1 d . . . . .
H12 H 0.208363 0.506900 0.333654 0.036 Uiso 1 1 calc R . . . .
C16 C 0.5627(2) 0.38230(16) 0.20154(8) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.687429 0.318543 0.198391 0.035 Uiso 1 1 calc R . . . .
C5 C 0.9368(2) -0.01138(17) 0.70196(8) 0.0305(3) Uani 1 1 d . . . . .
H5 H 0.885101 -0.100670 0.743120 0.037 Uiso 1 1 calc R . . . .
C13 C 0.1854(2) 0.56621(17) 0.21018(8) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.057458 0.625781 0.213213 0.037 Uiso 1 1 calc R . . . .
C11 C 0.4676(2) 0.40263(16) 0.27956(8) 0.0273(3) Uani 1 1 d . . . . .
C3 C 1.1920(2) 0.21605(17) 0.65174(8) 0.0310(3) Uani 1 1 d . . . . .
H3 H 1.311187 0.279507 0.659011 0.037 Uiso 1 1 calc R . . . .
C6 C 0.8363(2) 0.02824(17) 0.62901(8) 0.0315(3) Uani 1 1 d . . . . .
H6 H 0.716801 -0.034890 0.621730 0.038 Uiso 1 1 calc R . . . .
C2 C 1.0887(2) 0.25375(17) 0.57884(8) 0.0323(3) Uani 1 1 d . . . . .
H2 H 1.140120 0.343117 0.537669 0.039 Uiso 1 1 calc R . . . .
C7 C 0.8085(2) 0.20038(18) 0.48501(8) 0.0331(3) Uani 1 1 d . . . . .
H7A H 0.910073 0.259625 0.442299 0.040 Uiso 1 1 calc R . . . .
H7B H 0.768250 0.093051 0.468093 0.040 Uiso 1 1 calc R . . . .
C21 C 1.4026(2) 0.11869(17) 0.79738(9) 0.0336(3) Uani 1 1 d . . . . .
H21A H 1.379493 0.241238 0.796700 0.040 Uiso 1 1 calc R . . . .
H21B H 1.507045 0.104486 0.752105 0.040 Uiso 1 1 calc R . . . .
C18 C 0.0148(2) 0.70809(17) 0.05830(8) 0.0317(3) Uani 1 1 d . . . . .
H18A H 0.020165 0.804706 0.088297 0.038 Uiso 1 1 calc R . . . .
H18B H -0.097601 0.629919 0.085220 0.038 Uiso 1 1 calc R . . . .
C19 C -0.0270(2) 0.77094(18) -0.03076(9) 0.0372(3) Uani 1 1 d . . . . .
H19A H -0.024305 0.674953 -0.060472 0.056 Uiso 1 1 calc GR . . . .
H19B H 0.080942 0.853065 -0.055811 0.056 Uiso 1 1 calc GR . . . .
H19C H -0.164227 0.824959 -0.032915 0.056 Uiso 1 1 calc GR . . . .
C22 C 1.4817(2) 0.03769(19) 0.87897(10) 0.0408(4) Uani 1 1 d . . . . .
H22A H 1.494494 -0.084757 0.880616 0.061 Uiso 1 1 calc GR . . . .
H22B H 1.382714 0.060397 0.923662 0.061 Uiso 1 1 calc GR . . . .
H22C H 1.618387 0.085633 0.884810 0.061 Uiso 1 1 calc GR . . . .


_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
O17 C14 1.3707(14) . ?
O17 C18 1.4375(15) . ?
O20 C4 1.3685(14) . ?
O20 C21 1.4398(16) . ?
N9 N8 1.3630(14) . ?
N9 C10 1.2861(17) . ?
N8 H8 0.8600 . ?
N8 C7 1.4486(16) . ?
C14 C15 1.3957(17) . ?
C14 C13 1.3946(18) . ?
C4 C5 1.3951(18) . ?
C4 C3 1.3917(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.3816(17) . ?
C1 C6 1.3983(19) . ?
C1 C2 1.385(2) . ?
C1 C7 1.5051(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.4651(16) . ?
C12 H12 0.9300 . ?
C12 C13 1.3860(17) . ?
C12 C11 1.3997(17) . ?
C16 H16 0.9300 . ?
C16 C11 1.3975(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.3836(17) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.3912(18) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.5014(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.5019(18) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C14 O17 C18 117.85(10) . . ?
C4 O20 C21 117.03(10) . . ?
C10 N9 N8 119.54(10) . . ?
N9 N8 H8 119.7 . . ?
N9 N8 C7 120.64(10) . . ?
C7 N8 H8 119.7 . . ?
O17 C14 C15 115.59(11) . . ?
O17 C14 C13 124.59(11) . . ?
C13 C14 C15 119.82(11) . . ?
O20 C4 C5 116.22(11) . . ?
O20 C4 C3 124.17(11) . . ?
C3 C4 C5 119.61(12) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.76(11) . . ?
C16 C15 H15 120.1 . . ?
C6 C1 C7 121.50(12) . . ?
C2 C1 C6 118.09(12) . . ?
C2 C1 C7 120.37(12) . . ?
N9 C10 H10 119.5 . . ?
N9 C10 C11 120.99(11) . . ?
C11 C10 H10 119.5 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.33(11) . . ?
C11 C12 H12 119.3 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C11 121.48(11) . . ?
C11 C16 H16 119.3 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.95(12) . . ?
C6 C5 H5 120.0 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.67(11) . . ?
C12 C13 H13 120.2 . . ?
C12 C11 C10 123.14(11) . . ?
C16 C11 C10 118.95(11) . . ?
C16 C11 C12 117.90(11) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.53(12) . . ?
C2 C3 H3 120.2 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.18(12) . . ?
C5 C6 H6 119.4 . . ?
C1 C2 C3 121.64(12) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
N8 C7 C1 111.04(10) . . ?
N8 C7 H7A 109.4 . . ?
N8 C7 H7B 109.4 . . ?
C1 C7 H7A 109.4 . . ?
C1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O20 C21 H21A 110.1 . . ?
O20 C21 H21B 110.1 . . ?
O20 C21 C22 108.20(11) . . ?
H21A C21 H21B 108.4 . . ?
C22 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
O17 C18 H18A 110.3 . . ?
O17 C18 H18B 110.3 . . ?
O17 C18 C19 107.24(11) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O17 C14 C15 C16 178.15(10) . . . . ?
O17 C14 C13 C12 -177.43(11) . . . . ?
O20 C4 C5 C6 -179.97(10) . . . . ?
O20 C4 C3 C2 179.93(11) . . . . ?
N9 N8 C7 C1 169.15(11) . . . . ?
N9 C10 C11 C12 -17.25(19) . . . . ?
N9 C10 C11 C16 161.99(12) . . . . ?
N8 N9 C10 C11 178.19(11) . . . . ?
C14 O17 C18 C19 -179.13(10) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
C4 O20 C21 C22 -175.37(10) . . . . ?
C4 C5 C6 C1 0.19(19) . . . . ?
C4 C3 C2 C1 -0.11(19) . . . . ?
C15 C14 C13 C12 1.97(19) . . . . ?
C15 C16 C11 C10 -177.10(11) . . . . ?
C15 C16 C11 C12 2.18(19) . . . . ?
C10 N9 N8 C7 13.51(18) . . . . ?
C5 C4 C3 C2 0.00(18) . . . . ?
C13 C14 C15 C16 -1.31(19) . . . . ?
C13 C12 C11 C10 177.75(11) . . . . ?
C13 C12 C11 C16 -1.50(19) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.03(18) . . . . ?
C6 C1 C2 C3 0.26(19) . . . . ?
C6 C1 C7 N8 82.32(15) . . . . ?
C2 C1 C6 C5 -0.30(19) . . . . ?
C2 C1 C7 N8 -100.14(14) . . . . ?
C7 C1 C6 C5 177.30(11) . . . . ?
C7 C1 C2 C3 -177.36(11) . . . . ?
C21 O20 C4 C5 173.86(11) . . . . ?
C21 O20 C4 C3 -6.07(17) . . . . ?
C18 O17 C14 C15 175.69(11) . . . . ?
C18 O17 C14 C13 -4.88(18) . . . . ?

_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 3.276
_oxdiff_exptl_absorpt_empirical_full_min 0.645
####################################################################### 
# 
# 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_cg-sp-105
_database_code_depnum_ccdc_archive 'CCDC 2077413'
loop_
_audit_author_name
_audit_author_address
'Chidambaram Gunanathan'
;National Institute of Science Education and Research 
India
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 S2'
_chemical_formula_sum            'C16 H17 N2 S2'
_chemical_formula_weight         301.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C72 H76 O8 S1 N1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.33740(10)
_cell_length_b                   17.4593(2)
_cell_length_c                   16.6786(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.0970(10)
_cell_angle_gamma                90
_cell_volume                     1551.96(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9109
_cell_measurement_temperature    246(16)
_cell_measurement_theta_max      75.3640
_cell_measurement_theta_min      3.6810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73703
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10487
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        61.499
_diffrn_reflns_theta_max         61.499
_diffrn_reflns_theta_min         3.668
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      246(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   3.00   0.50    0.62    --  -38.50 114.00-100.00  172
  2  ω   -108.00 -33.00   0.50    0.62    --  -38.50 175.00  37.00  150
  3  ω     19.00  94.00   0.50    0.62    --   49.56-114.00 168.00  150
  4  ω     35.00 109.00   0.50    2.45    --  102.63-114.00 168.00  148
  5  ω     55.00 148.00   0.50    2.45    --  102.63-175.00  30.00  186
  6  ω    103.00 171.00   0.50    2.45    --  102.63 114.00-100.00  136
  7  ω     63.00 147.00   0.50    2.45    --  102.63 175.00  37.00  168
  8  ω    -42.00  28.00   0.50    0.62    --  -38.50  38.00-180.00  140
  9  ω    -44.00  23.00   0.50    0.62    --  -38.50  19.00-120.00  134
 10  ω      0.00  42.00   0.50    0.62    --   49.56 -38.00 150.00   84
 11  ω    103.00 167.00   0.50    2.45    --  102.63  77.00 -60.00  128
 12  ω     63.00 107.00   0.50    2.45    --  102.63 -15.00 -90.00   88
 13  ω     50.00 116.00   0.50    2.45    --  102.63 -61.00 150.00  132
 14  ω     38.00 125.00   0.50    2.45    --  102.63 -77.00 150.00  174
 15  ω     35.00 110.00   0.50    2.45    --  102.63 -15.00 150.00  150
 16  ω    103.00 170.00   0.50    2.45    --  102.63  30.00  90.00  134
 17  ω     43.00 114.00   0.50    2.45    --  102.63 -61.00 -30.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0347166000
_diffrn_orient_matrix_UB_12      -0.0725433000
_diffrn_orient_matrix_UB_13      -0.0507489000
_diffrn_orient_matrix_UB_21      0.0378399000
_diffrn_orient_matrix_UB_22      -0.0478131000
_diffrn_orient_matrix_UB_23      0.0773696000
_diffrn_orient_matrix_UB_31      -0.2844661000
_diffrn_orient_matrix_UB_32      -0.0152300000
_diffrn_orient_matrix_UB_33      -0.0010176000
_diffrn_oxdiff_digest_frames     
;
01a1933f0cb1c68f1b7d2fd92e73df38c7000411de1
;
_diffrn_oxdiff_digest_hkl        
;
015c00e04446160a17e14d67f6f523b0a71e82
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2268
_reflns_number_total             2388
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.047
_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)+(0.0569P)²+0.4876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1037
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C10(H10), C12(H12), C5(H5), C6(H6), C3(H3), C2(H2), C13(H13),
 C16(H16), C15(H15)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S17 S 1.16501(10) 0.08096(3) 0.34303(3) 0.0597(2) Uani 1 1 d . . . . .
S19 S 0.46708(11) 0.89702(3) 0.40769(4) 0.0652(2) Uani 1 1 d . . . . .
N9 N 0.9014(3) 0.45376(9) 0.41570(9) 0.0477(4) Uani 1 1 d . . . . .
N8 N 0.8230(3) 0.52795(9) 0.41771(10) 0.0549(4) Uani 1 1 d . . . . .
H8 H 0.916235 0.561126 0.443104 0.066 Uiso 1 1 calc R . . . .
C11 C 0.8908(3) 0.32812(11) 0.35932(10) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.5557(3) 0.63746(11) 0.38934(10) 0.0441(4) Uani 1 1 d . . . . .
C4 C 0.4941(3) 0.79644(11) 0.40457(10) 0.0438(4) Uani 1 1 d . . . . .
C14 C 1.0447(3) 0.17485(11) 0.34656(10) 0.0448(4) Uani 1 1 d . . . . .
C10 C 0.7995(3) 0.40627(11) 0.36562(11) 0.0466(4) Uani 1 1 d . . . . .
H10 H 0.663633 0.422041 0.332406 0.056 Uiso 1 1 calc R . . . .
C12 C 0.7558(3) 0.27561(11) 0.31156(11) 0.0496(5) Uani 1 1 d . . . . .
H12 H 0.610853 0.291837 0.283073 0.059 Uiso 1 1 calc R . . . .
C5 C 0.3341(3) 0.74605(11) 0.44073(12) 0.0489(5) Uani 1 1 d . . . . .
H5 H 0.204518 0.764918 0.470186 0.059 Uiso 1 1 calc R . . . .
C6 C 0.3664(3) 0.66806(11) 0.43319(12) 0.0494(5) Uani 1 1 d . . . . .
H6 H 0.258148 0.635099 0.458215 0.059 Uiso 1 1 calc R . . . .
C3 C 0.6880(3) 0.76633(11) 0.36159(11) 0.0487(5) Uani 1 1 d . . . . .
H3 H 0.798713 0.799231 0.337580 0.058 Uiso 1 1 calc R . . . .
C2 C 0.7172(3) 0.68882(11) 0.35437(11) 0.0482(4) Uani 1 1 d . . . . .
H2 H 0.847989 0.669963 0.325439 0.058 Uiso 1 1 calc R . . . .
C13 C 0.8295(3) 0.20031(12) 0.30499(11) 0.0509(5) Uani 1 1 d . . . . .
H13 H 0.734470 0.166640 0.272600 0.061 Uiso 1 1 calc R . . . .
C16 C 1.1091(3) 0.30167(12) 0.40025(11) 0.0514(5) Uani 1 1 d . . . . .
H16 H 1.205405 0.335345 0.432237 0.062 Uiso 1 1 calc R . . . .
C15 C 1.1836(3) 0.22697(12) 0.39403(12) 0.0514(5) Uani 1 1 d . . . . .
H15 H 1.329510 0.210735 0.421989 0.062 Uiso 1 1 calc R . . . .
C7 C 0.5881(3) 0.55296(11) 0.37858(12) 0.0510(5) Uani 1 1 d . . . . .
H7A H 0.449832 0.526013 0.401356 0.061 Uiso 1 1 calc R . . . .
H7B H 0.586684 0.540926 0.321780 0.061 Uiso 1 1 calc R . . . .
C20 C 0.2438(5) 0.91413(14) 0.48189(16) 0.0713(6) Uani 1 1 d . . . . .
H20A H 0.083159 0.894344 0.463316 0.107 Uiso 1 1 calc GR . . . .
H20B H 0.230481 0.968208 0.491159 0.107 Uiso 1 1 calc GR . . . .
H20C H 0.297882 0.889011 0.531026 0.107 Uiso 1 1 calc GR . . . .
C18 C 0.9243(4) 0.02806(13) 0.28881(16) 0.0705(6) Uani 1 1 d . . . . .
H18A H 0.907483 0.046358 0.234511 0.106 Uiso 1 1 calc GR . . . .
H18B H 0.768224 0.034690 0.313989 0.106 Uiso 1 1 calc GR . . . .
H18C H 0.967978 -0.025281 0.288822 0.106 Uiso 1 1 calc GR . . . .


_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
S17 C14 1.7626(19) . ?
S17 C18 1.788(2) . ?
S19 C4 1.763(2) . ?
S19 C20 1.789(2) . ?
N9 N8 1.362(2) . ?
N9 C10 1.277(2) . ?
N8 H8 0.8600 . ?
N8 C7 1.449(2) . ?
C11 C10 1.455(3) . ?
C11 C12 1.390(3) . ?
C11 C16 1.397(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.497(3) . ?
C4 C5 1.387(3) . ?
C4 C3 1.394(3) . ?
C14 C13 1.383(3) . ?
C14 C15 1.393(3) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.368(3) . ?
C2 H2 0.9300 . ?
C13 H13 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.369(3) . ?
C15 H15 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C14 S17 C18 104.13(10) . . ?
C4 S19 C20 104.20(10) . . ?
C10 N9 N8 120.85(15) . . ?
N9 N8 H8 118.8 . . ?
N9 N8 C7 122.33(15) . . ?
C7 N8 H8 118.8 . . ?
C12 C11 C10 119.67(16) . . ?
C12 C11 C16 117.05(17) . . ?
C16 C11 C10 123.28(17) . . ?
C6 C1 C2 117.25(18) . . ?
C6 C1 C7 122.36(17) . . ?
C2 C1 C7 120.38(17) . . ?
C5 C4 S19 124.47(14) . . ?
C5 C4 C3 118.45(18) . . ?
C3 C4 S19 117.08(14) . . ?
C13 C14 S17 125.21(15) . . ?
C13 C14 C15 118.50(18) . . ?
C15 C14 S17 116.27(14) . . ?
N9 C10 C11 121.57(16) . . ?
N9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.25(17) . . ?
C13 C12 H12 118.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.26(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.79(18) . . ?
C5 C6 H6 119.1 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.64(17) . . ?
C2 C3 H3 119.7 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.59(17) . . ?
C3 C2 H2 119.2 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 119.97(17) . . ?
C12 C13 H13 120.0 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.07(17) . . ?
C15 C16 H16 119.5 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.15(17) . . ?
C16 C15 H15 119.4 . . ?
N8 C7 C1 110.23(15) . . ?
N8 C7 H7A 109.6 . . ?
N8 C7 H7B 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
S19 C20 H20A 109.5 . . ?
S19 C20 H20B 109.5 . . ?
S19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S17 C18 H18A 109.5 . . ?
S17 C18 H18B 109.5 . . ?
S17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
S17 C14 C13 C12 -179.00(15) . . . . ?
S17 C14 C15 C16 179.15(16) . . . . ?
S19 C4 C5 C6 178.29(14) . . . . ?
S19 C4 C3 C2 -178.12(14) . . . . ?
N9 N8 C7 C1 -178.60(16) . . . . ?
N8 N9 C10 C11 176.21(17) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C11 C16 C15 C14 0.2(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C3 C2 C1 0.0(3) . . . . ?
C10 N9 N8 C7 15.0(3) . . . . ?
C10 C11 C12 C13 -178.22(18) . . . . ?
C10 C11 C16 C15 178.21(18) . . . . ?
C12 C11 C10 N9 171.88(18) . . . . ?
C12 C11 C16 C15 -0.8(3) . . . . ?
C5 C4 C3 C2 0.9(3) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C6 C1 C7 N8 -114.7(2) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C2 C1 C7 N8 65.8(2) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C16 C11 C10 N9 -7.1(3) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C15 C14 C13 C12 -0.5(3) . . . . ?
C7 C1 C6 C5 -178.10(17) . . . . ?
C7 C1 C2 C3 178.36(16) . . . . ?
C20 S19 C4 C5 11.68(19) . . . . ?
C20 S19 C4 C3 -169.33(15) . . . . ?
C18 S17 C14 C13 -8.7(2) . . . . ?
C18 S17 C14 C15 172.77(16) . . . . ?

_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.698
####################################################################### 
# 
# 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_cg-sp-61
_database_code_depnum_ccdc_archive 'CCDC 2077412'
loop_
_audit_author_name
_audit_author_address
'Chidambaram Gunanathan'
;National Institute of Science Education and Research 
India
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 N2'
_chemical_formula_sum            'C20 H26 N2'
_chemical_formula_weight         294.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H52 N4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2530(2)
_cell_length_b                   8.2551(2)
_cell_length_c                   14.7902(2)
_cell_angle_alpha                94.559(2)
_cell_angle_beta                 102.195(2)
_cell_angle_gamma                117.627(3)
_cell_volume                     854.10(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11061
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.2840
_cell_measurement_theta_min      6.1670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83579
_exptl_absorpt_correction_type   multi-scan
_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        61.473
_diffrn_reflns_theta_max         61.473
_diffrn_reflns_theta_min         6.182
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -15.00   0.50    0.25    --  -38.50 143.00  37.00  170
  2  ω    -88.00  -8.00   0.50    0.25    --  -38.50 127.00-132.00  160
  3  ω     29.00 102.00   0.50    0.25    --   49.31-127.00 152.00  146
  4  ω     38.00 114.00   0.50    0.98    --  102.63-127.00 152.00  152
  5  ω     39.00 126.00   0.50    0.98    --  102.63-143.00 -17.00  174
  6  ω     87.00 166.00   0.50    0.98    --  102.63 143.00  37.00  158
  7  ω     96.00 167.00   0.50    0.98    --  102.63 127.00-132.00  142
  8  ω    -42.00  28.00   0.50    0.25    --  -38.50  38.00 -30.00  140
  9  ω   -105.00 -35.00   0.50    0.25    --  -38.50 -38.00 150.00  140
 10  ω     38.00 112.00   0.50    0.25    --   49.31  57.00 150.00  148
 11  ω    -20.00  55.00   0.50    0.25    --   49.31 -19.00 -30.00  150
 12  ω     46.00 116.00   0.50    0.25    --   49.31  38.00-150.00  140
 13  ω     37.00 111.00   0.50    0.25    --   49.31-143.00 -17.00  148
 14  ω     98.00 167.00   0.50    0.98    --  102.63  45.00-120.00  138
 15  ω     38.00 107.00   0.50    0.98    --  102.63 -45.00 120.00  138
 16  ω     34.00 107.00   0.50    0.98    --  102.63 -94.00-120.00  146
 17  ω     97.00 168.00   0.50    0.98    --  102.63 125.00   0.00  142
 18  ω     34.00 107.00   0.50    0.98    --  102.63 -94.00  30.00  146
 19  ω     34.00 107.00   0.50    0.98    --  102.63 -94.00  60.00  146
 20  ω     34.00 111.00   0.50    0.98    --  102.63 -15.00   0.00  154
 21  ω     90.00 165.00   0.50    0.98    --  102.63  61.00 120.00  150
 22  ω     97.00 168.00   0.50    0.98    --  102.63 125.00  90.00  142
 23  ω     35.00 106.00   0.50    0.98    --  102.63 -30.00 120.00  142
 24  ω     38.00 126.00   0.50    0.98    --  102.63 -77.00  60.00  176
 25  ω     97.00 168.00   0.50    0.98    --  102.63 125.00  60.00  142
 26  ω     34.00 107.00   0.50    0.98    --  102.63 -94.00 150.00  146
 27  ω     40.00 116.00   0.50    0.98    --  102.63 -61.00 -90.00  152
 28  ω    103.00 167.00   0.50    0.98    --  102.63  77.00  90.00  128
 29  ω    103.00 167.00   0.50    0.98    --  102.63  77.00-180.00  128
 30  ω     35.00 106.00   0.50    0.98    --  102.63 -30.00 -60.00  142
 31  ω     95.00 171.00   0.50    0.98    --  102.63  15.00-180.00  152
 32  ω     38.00  84.00   0.50    0.25    --   49.31  57.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0970961000
_diffrn_orient_matrix_UB_12      0.0535737000
_diffrn_orient_matrix_UB_13      0.1071653000
_diffrn_orient_matrix_UB_21      -0.1687264000
_diffrn_orient_matrix_UB_22      0.0176423000
_diffrn_orient_matrix_UB_23      0.0182242000
_diffrn_orient_matrix_UB_31      -0.1014688000
_diffrn_orient_matrix_UB_32      -0.2076810000
_diffrn_orient_matrix_UB_33      0.0060804000
_diffrn_oxdiff_digest_frames     
;
016c4ba5fcc49094a53c880df09b4a5ea00006526e7
;
_diffrn_oxdiff_digest_hkl        
;
01cb71a589637cb813e2eb3653d6bae788a79b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2553
_reflns_number_total             2655
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.038
_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)+(0.0838P)²+0.7656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1630
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C5(H5), C15(H15), C13(H13), C3(H3), C10(H10)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N9 N 0.3677(2) 0.7783(2) 0.49885(12) 0.0280(4) Uani 1 1 d . . . . .
N8 N 0.3558(2) 0.8117(2) 0.40931(11) 0.0285(4) Uani 1 1 d . . . . .
H8 H 0.452000 0.903356 0.398882 0.034 Uiso 1 1 calc R . . . .
C5 C 0.2180(3) 1.0102(3) 0.15371(14) 0.0221(4) Uani 1 1 d . . . . .
H5 H 0.221575 1.123815 0.150545 0.027 Uiso 1 1 calc R . . . .
C4 C 0.2286(3) 0.9145(3) 0.07584(14) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.2022(3) 0.9427(3) 0.23629(13) 0.0216(4) Uani 1 1 d . . . . .
C16 C 0.2805(3) 0.6942(3) 0.69066(14) 0.0216(4) Uani 1 1 d . . . . .
C15 C 0.2991(3) 0.6390(3) 0.77702(13) 0.0217(4) Uani 1 1 d . . . . .
H15 H 0.307367 0.713829 0.830141 0.026 Uiso 1 1 calc R . . . .
C11 C 0.2681(3) 0.5813(3) 0.61014(13) 0.0227(5) Uani 1 1 d . . . . .
C1 C 0.1997(3) 0.7726(3) 0.24255(13) 0.0210(4) Uani 1 1 d . . . . .
C14 C 0.3058(3) 0.4762(3) 0.78663(13) 0.0230(5) Uani 1 1 d . . . . .
C2 C 0.2066(3) 0.6718(3) 0.16378(14) 0.0216(4) Uani 1 1 d . . . . .
C13 C 0.2936(3) 0.3673(3) 0.70641(14) 0.0246(5) Uani 1 1 d . . . . .
H13 H 0.299238 0.258345 0.711602 0.030 Uiso 1 1 calc R . . . .
C3 C 0.2204(3) 0.7437(3) 0.08219(14) 0.0235(5) Uani 1 1 d . . . . .
H3 H 0.224276 0.675648 0.030264 0.028 Uiso 1 1 calc R . . . .
C7 C 0.1888(3) 0.6995(3) 0.33265(14) 0.0274(5) Uani 1 1 d . . . . .
H7A H 0.079594 0.693614 0.350108 0.033 Uiso 1 1 calc R . . . .
H7B H 0.169073 0.573416 0.321332 0.033 Uiso 1 1 calc R . . . .
C12 C 0.2734(3) 0.4155(3) 0.61889(14) 0.0241(5) Uani 1 1 d . . . . .
C21 C 0.1884(3) 1.0550(3) 0.31708(14) 0.0297(5) Uani 1 1 d . . . . .
H21A H 0.311517 1.127153 0.362210 0.045 Uiso 1 1 calc GR . . . .
H21B H 0.099784 0.971961 0.347041 0.045 Uiso 1 1 calc GR . . . .
H21C H 0.145217 1.137301 0.293350 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.2696(3) 0.8710(3) 0.68656(15) 0.0297(5) Uani 1 1 d . . . . .
H18A H 0.212286 0.889960 0.733558 0.045 Uiso 1 1 calc GR . . . .
H18B H 0.193912 0.860428 0.625074 0.045 Uiso 1 1 calc GR . . . .
H18C H 0.395656 0.975175 0.698444 0.045 Uiso 1 1 calc GR . . . .
C20 C 0.1971(3) 0.4844(3) 0.16541(15) 0.0298(5) Uani 1 1 d . . . . .
H20A H 0.304222 0.499863 0.213631 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.199757 0.435057 0.105091 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.081195 0.399631 0.178548 0.045 Uiso 1 1 calc GR . . . .
C22 C 0.2491(3) 0.9943(3) -0.01183(15) 0.0321(5) Uani 1 1 d . . . . .
H22A H 0.172233 1.053129 -0.023445 0.048 Uiso 1 1 calc GR . . . .
H22B H 0.208010 0.895622 -0.064785 0.048 Uiso 1 1 calc GR . . . .
H22C H 0.380189 1.084816 -0.003151 0.048 Uiso 1 1 calc GR . . . .
C17 C 0.2558(3) 0.2866(3) 0.53409(15) 0.0358(5) Uani 1 1 d . . . . .
H17A H 0.127025 0.224027 0.494202 0.054 Uiso 1 1 calc GR . . . .
H17B H 0.288648 0.195856 0.555082 0.054 Uiso 1 1 calc GR . . . .
H17C H 0.340448 0.358340 0.499237 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.2464(3) 0.6242(3) 0.51432(16) 0.0344(5) Uani 1 1 d . . . . .
H10 H 0.142934 0.537586 0.464666 0.041 Uiso 1 1 calc R . . . .
C19 C 0.3209(3) 0.4173(3) 0.88033(14) 0.0334(5) Uani 1 1 d . . . . .
H19A H 0.390345 0.526031 0.930440 0.050 Uiso 1 1 calc GR . . . .
H19B H 0.386557 0.346652 0.883652 0.050 Uiso 1 1 calc GR . . . .
H19C H 0.195496 0.341452 0.886682 0.050 Uiso 1 1 calc GR . . . .


_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
N9 N8 1.367(2) . ?
N9 C10 1.279(3) . ?
N8 H8 0.8600 . ?
N8 C7 1.426(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(3) . ?
C5 C6 1.388(3) . ?
C4 C3 1.392(3) . ?
C4 C22 1.506(3) . ?
C6 C1 1.405(3) . ?
C6 C21 1.509(3) . ?
C16 C15 1.392(3) . ?
C16 C11 1.407(3) . ?
C16 C18 1.508(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.387(3) . ?
C11 C12 1.405(3) . ?
C11 C10 1.482(3) . ?
C1 C2 1.404(3) . ?
C1 C7 1.509(3) . ?
C14 C13 1.387(3) . ?
C14 C19 1.505(3) . ?
C2 C3 1.390(3) . ?
C2 C20 1.514(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.383(3) . ?
C3 H3 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C12 C17 1.514(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C10 H10 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C10 N9 N8 120.98(18) . . ?
N9 N8 H8 119.0 . . ?
N9 N8 C7 122.04(16) . . ?
C7 N8 H8 119.0 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.46(17) . . ?
C6 C5 H5 118.8 . . ?
C5 C4 C3 117.50(17) . . ?
C5 C4 C22 120.79(17) . . ?
C3 C4 C22 121.71(18) . . ?
C5 C6 C1 119.34(17) . . ?
C5 C6 C21 118.80(17) . . ?
C1 C6 C21 121.87(17) . . ?
C15 C16 C11 119.00(17) . . ?
C15 C16 C18 118.56(17) . . ?
C11 C16 C18 122.43(17) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 C16 122.31(18) . . ?
C14 C15 H15 118.8 . . ?
C16 C11 C10 124.08(18) . . ?
C12 C11 C16 119.20(17) . . ?
C12 C11 C10 116.70(18) . . ?
C6 C1 C7 120.30(17) . . ?
C2 C1 C6 119.07(17) . . ?
C2 C1 C7 120.63(17) . . ?
C15 C14 C19 121.21(18) . . ?
C13 C14 C15 117.72(17) . . ?
C13 C14 C19 121.05(18) . . ?
C1 C2 C20 121.29(17) . . ?
C3 C2 C1 119.63(17) . . ?
C3 C2 C20 119.08(17) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 C14 122.11(18) . . ?
C12 C13 H13 118.9 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.97(18) . . ?
C2 C3 H3 119.0 . . ?
N8 C7 C1 113.02(16) . . ?
N8 C7 H7A 109.0 . . ?
N8 C7 H7B 109.0 . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C11 C12 C17 121.35(18) . . ?
C13 C12 C11 119.66(18) . . ?
C13 C12 C17 118.99(18) . . ?
C6 C21 H21A 109.5 . . ?
C6 C21 H21B 109.5 . . ?
C6 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C20 H20A 109.5 . . ?
C2 C20 H20B 109.5 . . ?
C2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N9 C10 C11 121.0(2) . . ?
N9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N9 N8 C7 C1 174.31(16) . . . . ?
N8 N9 C10 C11 174.93(18) . . . . ?
C5 C4 C3 C2 -1.5(3) . . . . ?
C5 C6 C1 C2 -2.2(3) . . . . ?
C5 C6 C1 C7 178.09(16) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C21 -179.08(17) . . . . ?
C6 C5 C4 C3 0.8(3) . . . . ?
C6 C5 C4 C22 -178.92(18) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
C6 C1 C2 C20 -177.75(17) . . . . ?
C6 C1 C7 N8 -67.2(2) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C16 C15 C14 C19 -178.41(17) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C16 C11 C12 C17 178.50(17) . . . . ?
C16 C11 C10 N9 57.2(3) . . . . ?
C15 C16 C11 C12 0.4(3) . . . . ?
C15 C16 C11 C10 179.47(17) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
C11 C16 C15 C14 0.0(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C14 C13 C12 C11 1.1(3) . . . . ?
C14 C13 C12 C17 -178.37(18) . . . . ?
C2 C1 C7 N8 113.1(2) . . . . ?
C7 C1 C2 C3 -178.73(16) . . . . ?
C7 C1 C2 C20 1.9(3) . . . . ?
C12 C11 C10 N9 -123.8(2) . . . . ?
C21 C6 C1 C2 177.90(17) . . . . ?
C21 C6 C1 C7 -1.8(3) . . . . ?
C18 C16 C15 C14 178.50(17) . . . . ?
C18 C16 C11 C12 -178.02(17) . . . . ?
C18 C16 C11 C10 1.0(3) . . . . ?
C20 C2 C3 C4 179.63(18) . . . . ?
C22 C4 C3 C2 178.25(18) . . . . ?
C10 N9 N8 C7 14.4(3) . . . . ?
C10 C11 C12 C13 179.93(17) . . . . ?
C10 C11 C12 C17 -0.6(3) . . . . ?
C19 C14 C13 C12 177.86(18) . . . . ?

_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.448
