# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_898-ad-28
_database_code_depnum_ccdc_archive 'CCDC 2165854'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;Birla Institute of Technology and Science Pilani Hyderabad Campus
India
;
_audit_update_record             
;
2022-04-09 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2021-09-22
_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         'C20 H18 N2 O'
_chemical_formula_sum            'C20 H18 N2 O'
_chemical_formula_weight         302.36
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H18 N2 O'
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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   15.2367(5)
_cell_length_b                   15.2367(5)
_cell_length_c                   18.0166(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3622.3(3)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      78.3210
_cell_measurement_theta_min      4.1470
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.914
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14266
_diffrn_reflns_point_group_measured_fraction_full 0.631
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.158
_diffrn_reflns_theta_min         4.153
_diffrn_ambient_temperature      93(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  39.00   0.50   16.00    --    0.00  37.00-180.00  114
  2  ω    -47.00  19.00   0.50   16.00    --    0.00 -37.00 120.00  132
  3  ω     38.00 127.00   0.50   65.00    --  107.20 -30.00 -30.00  178
  4  ω     23.00  90.00   0.50   65.00    --  107.20 -30.00-120.00  134
  5  ω     51.00 135.00   0.50   65.00    --  107.20 -82.00-180.00  168
  6  ω    122.00 195.00   0.50   65.00    --  107.20  82.00  30.00  146
  7  ω    107.00 139.00   0.50   65.00    --  107.20 -82.00 120.00   64
  8  ω     20.00  81.00   0.50   65.00    --  107.20 -82.00 120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0798981000
_diffrn_orient_matrix_UB_12      -0.0336171000
_diffrn_orient_matrix_UB_13      -0.0028946000
_diffrn_orient_matrix_UB_21      0.0834298000
_diffrn_orient_matrix_UB_22      0.1104856000
_diffrn_orient_matrix_UB_23      -0.0136290000
_diffrn_orient_matrix_UB_31      0.0165776000
_diffrn_orient_matrix_UB_32      0.0169647000
_diffrn_orient_matrix_UB_33      0.0844289000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.230
_reflns_Friedel_fraction_full    0.262
_reflns_Friedel_fraction_max     0.224
_reflns_number_gt                5291
_reflns_number_total             6302
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.496
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         6302
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.043
_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)+(0.1200P)²+0.5054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1859
_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:
 C119(H11A,H11B), C19(H19A,H19B), C219(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 N101(H101), N1(H1), N201(H201), C115(H115), C202(H202), C203(H203), C2(H2),
 C114(H114), C15(H15), C113(H113), C18(H18), C210(H210), C21(H21), C204(H204),
 C112(H112), C214(H214), C217(H217), C17(H17), C118(H118), C211(H211),
 C117(H117), C4(H4), C110(H110), C212(H212), C111(H111), C215(H215), C105(H105),
  C102(H102), C213(H213), C218(H218), C3(H3), C14(H14), C5(H5), C13(H13),
 C12(H12), C10(H10), C104(H104), C103(H103), C11(H11)
2.c Idealised Me refined as rotating group:
 C220(H22A,H22B,H22C), C20(H20A,H20B,H20C), C120(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_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
O201 O 0.2683(3) 0.6927(3) 0.58620(17) 0.0457(8) Uani 1 1 d . . . . .
O101 O 0.7098(3) 1.2881(3) 0.69616(17) 0.0434(7) Uani 1 1 d . . . . .
O1 O 0.0133(3) 1.0704(3) 0.49936(17) 0.0487(8) Uani 1 1 d . . . . .
N102 N 0.5912(3) 1.4995(3) 0.8274(2) 0.0478(9) Uani 1 1 d . . . . .
N101 N 0.6622(3) 1.2739(3) 0.8888(2) 0.0365(7) Uani 1 1 d . . . . .
H101 H 0.667469 1.294366 0.935103 0.044 Uiso 1 1 calc R U . . .
N1 N 0.0086(3) 1.0440(3) 0.6934(2) 0.0426(9) Uani 1 1 d . . . . .
H1 H 0.013351 1.019292 0.736430 0.051 Uiso 1 1 calc R U . . .
N201 N 0.3245(3) 0.6987(3) 0.77720(19) 0.0364(8) Uani 1 1 d . . . . .
H201 H 0.345255 0.683767 0.818393 0.044 Uiso 1 1 calc R U . . .
C201 C 0.2671(3) 0.7446(3) 0.7744(2) 0.0289(7) Uani 1 1 d . . . . .
C1 C -0.0340(3) 1.1030(3) 0.6843(2) 0.0343(8) Uani 1 1 d . . . . .
N2 N 0.3188(3) 1.1521(4) 0.6608(3) 0.0546(11) Uani 1 1 d . . . . .
C101 C 0.6069(3) 1.1756(3) 0.8667(3) 0.0383(9) Uani 1 1 d . . . . .
C208 C 0.3468(3) 0.6776(3) 0.7020(2) 0.0322(8) Uani 1 1 d . . . . .
C115 C 0.6200(4) 1.4381(4) 0.8616(3) 0.0407(10) Uani 1 1 d . . . . .
H115 H 0.607712 1.417464 0.912088 0.049 Uiso 1 1 calc R U . . .
C8 C 0.0456(3) 1.0262(3) 0.6239(2) 0.0361(9) Uani 1 1 d . . . . .
C116 C 0.6699(4) 1.4107(3) 0.8111(3) 0.0379(9) Uani 1 1 d . . . . .
C207 C 0.2787(3) 0.7058(3) 0.6537(2) 0.0338(8) Uani 1 1 d . . . . .
C209 C 0.3117(3) 0.5648(3) 0.6937(2) 0.0351(9) Uani 1 1 d . . . . .
C16 C 0.1603(4) 1.0861(3) 0.6222(2) 0.0383(9) Uani 1 1 d . . . . .
C202 C 0.2375(3) 0.7834(3) 0.8341(2) 0.0347(8) Uani 1 1 d . . . . .
H202 H 0.258979 0.782228 0.883418 0.042 Uiso 1 1 calc R U . . .
C107 C 0.6826(3) 1.2642(3) 0.7602(2) 0.0356(9) Uani 1 1 d . . . . .
N202 N 0.5961(4) 0.8505(4) 0.6152(3) 0.0664(14) Uani 1 1 d . . . . .
C7 C 0.0053(4) 1.0743(3) 0.5666(2) 0.0369(9) Uani 1 1 d . . . . .
C6 C -0.0386(4) 1.1233(3) 0.6088(2) 0.0381(9) Uani 1 1 d . . . . .
C216 C 0.4561(4) 0.7476(4) 0.6814(3) 0.0421(10) Uani 1 1 d . . . . .
C109 C 0.8280(3) 1.3969(3) 0.8343(2) 0.0347(9) Uani 1 1 d . . . . .
C108 C 0.7118(3) 1.3412(3) 0.8259(2) 0.0328(8) Uani 1 1 d . . . . .
C205 C 0.2355(3) 0.7487(3) 0.7024(2) 0.0368(9) Uani 1 1 d . . . . .
C203 C 0.1756(4) 0.8233(4) 0.8180(3) 0.0418(10) Uani 1 1 d . . . . .
H203 H 0.155053 0.850227 0.857503 0.050 Uiso 1 1 calc R U . . .
C2 C -0.0733(4) 1.1407(4) 0.7376(3) 0.0467(11) Uani 1 1 d . . . . .
H2 H -0.068632 1.130085 0.789089 0.056 Uiso 1 1 calc R U . . .
C106 C 0.6210(4) 1.1650(3) 0.7908(3) 0.0430(10) Uani 1 1 d . . . . .
C114 C 0.8905(4) 1.4874(4) 0.7968(3) 0.0479(11) Uani 1 1 d . . . . .
H114 H 0.861457 1.517786 0.767030 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2208(4) 1.0959(4) 0.6810(3) 0.0445(10) Uani 1 1 d . . . . .
H15 H 0.197510 1.067473 0.728855 0.053 Uiso 1 1 calc R U . . .
C113 C 0.9961(4) 1.5334(5) 0.8032(3) 0.0614(16) Uani 1 1 d . . . . .
H113 H 1.038487 1.595726 0.778589 0.074 Uiso 1 1 calc R U . . .
C18 C 0.3233(4) 1.1817(4) 0.5887(4) 0.0564(13) Uani 1 1 d . . . . .
H18 H 0.383291 1.222586 0.561055 0.068 Uiso 1 1 calc R U . . .
C210 C 0.2110(4) 0.4945(4) 0.7054(3) 0.0441(10) Uani 1 1 d . . . . .
H210 H 0.164906 0.516513 0.719203 0.053 Uiso 1 1 calc R U . . .
C21 C 0.1723(4) 0.7877(4) 0.6881(3) 0.0459(11) Uani 1 1 d . . . . .
H21 H 0.150030 0.788459 0.639005 0.055 Uiso 1 1 calc R U . . .
C204 C 0.1422(4) 0.8256(4) 0.7463(3) 0.0483(11) Uani 1 1 d . . . . .
H204 H 0.099143 0.853027 0.737664 0.058 Uiso 1 1 calc R U . . .
C9 C 0.0033(4) 0.9136(4) 0.6092(3) 0.0551(14) Uani 1 1 d . . . . .
C112 C 1.0386(4) 1.4886(6) 0.8450(3) 0.0628(17) Uani 1 1 d . . . . .
H112 H 1.110190 1.519471 0.848935 0.075 Uiso 1 1 calc R U . . .
C214 C 0.3784(4) 0.5315(4) 0.6731(3) 0.0440(10) Uani 1 1 d . . . . .
H214 H 0.447874 0.579464 0.664775 0.053 Uiso 1 1 calc R U . . .
C217 C 0.5406(4) 0.7797(5) 0.7286(3) 0.0607(15) Uani 1 1 d . . . . .
H217 H 0.540247 0.760573 0.778830 0.073 Uiso 1 1 calc R U . . .
C17 C 0.2273(4) 1.1427(4) 0.5635(3) 0.0492(11) Uani 1 1 d . . . . .
H17 H 0.208078 1.151594 0.515119 0.059 Uiso 1 1 calc R U . . .
C118 C 0.6242(5) 1.5155(4) 0.7559(3) 0.0532(13) Uani 1 1 d . . . . .
H118 H 0.614993 1.556373 0.720463 0.064 Uiso 1 1 calc R U . . .
C211 C 0.1760(5) 0.3900(4) 0.6970(3) 0.0603(15) Uani 1 1 d . . . . .
H211 H 0.106571 0.341384 0.704599 0.072 Uiso 1 1 calc R U . . .
C117 C 0.6737(5) 1.4615(4) 0.7443(3) 0.0520(12) Uani 1 1 d . . . . .
H117 H 0.704831 1.458883 0.699271 0.062 Uiso 1 1 calc R U . . .
C4 C -0.1241(5) 1.2133(5) 0.6389(4) 0.0648(16) Uani 1 1 d . . . . .
H4 H -0.157219 1.249236 0.624057 0.078 Uiso 1 1 calc R U . . .
C110 C 0.8726(4) 1.3535(4) 0.8759(3) 0.0432(10) Uani 1 1 d . . . . .
H110 H 0.831218 1.291651 0.901408 0.052 Uiso 1 1 calc R U . . .
C212 C 0.2452(6) 0.3591(4) 0.6772(3) 0.0608(16) Uani 1 1 d . . . . .
H212 H 0.223066 0.288996 0.672384 0.073 Uiso 1 1 calc R U . . .
C111 C 0.9774(4) 1.3995(5) 0.8808(3) 0.0590(14) Uani 1 1 d . . . . .
H111 H 1.006844 1.368565 0.909507 0.071 Uiso 1 1 calc R U . . .
C119 C 0.5377(5) 1.5456(5) 0.8620(4) 0.0618(15) Uani 1 1 d . . . . .
H11A H 0.496572 1.502727 0.903906 0.074 Uiso 1 1 calc R U . . .
H11B H 0.490904 1.548888 0.825403 0.074 Uiso 1 1 calc R U . . .
C215 C 0.4928(4) 0.7903(5) 0.6125(3) 0.0541(13) Uani 1 1 d . . . . .
H215 H 0.452321 0.779428 0.569580 0.065 Uiso 1 1 calc R U . . .
C105 C 0.5758(5) 1.0698(4) 0.7572(4) 0.0582(14) Uani 1 1 d . . . . .
H105 H 0.586677 1.062268 0.706212 0.070 Uiso 1 1 calc R U . . .
C102 C 0.5460(4) 1.0900(4) 0.9106(4) 0.0563(14) Uani 1 1 d . . . . .
H102 H 0.536641 1.096518 0.961974 0.068 Uiso 1 1 calc R U . . .
C213 C 0.3441(6) 0.4290(4) 0.6649(3) 0.0578(14) Uani 1 1 d . . . . .
H213 H 0.390183 0.407230 0.650467 0.069 Uiso 1 1 calc R U . . .
C218 C 0.6250(5) 0.8457(7) 0.6860(5) 0.084(2) Uani 1 1 d . . . . .
H218 H 0.692644 0.881964 0.703952 0.100 Uiso 1 1 calc R U . . .
C3 C -0.1191(5) 1.1941(5) 0.7129(3) 0.0589(14) Uani 1 1 d . . . . .
H3 H -0.148077 1.218392 0.748343 0.071 Uiso 1 1 calc R U . . .
C14 C -0.0773(5) 0.8403(5) 0.6477(5) 0.074(2) Uani 1 1 d . . . . .
H14 H -0.110449 0.857664 0.684762 0.088 Uiso 1 1 calc R U . . .
C5 C -0.0815(5) 1.1806(5) 0.5861(3) 0.0573(14) Uani 1 1 d . . . . .
H5 H -0.081492 1.196938 0.535208 0.069 Uiso 1 1 calc R U . . .
C13 C -0.1110(6) 0.7346(6) 0.6303(6) 0.095(3) Uani 1 1 d . . . . .
H13 H -0.166213 0.681344 0.656218 0.114 Uiso 1 1 calc R U . . .
C12 C -0.0615(7) 0.7138(7) 0.5757(6) 0.088(3) Uani 1 1 d . . . . .
H12 H -0.083796 0.644925 0.564197 0.105 Uiso 1 1 calc R U . . .
C10 C 0.0491(6) 0.8839(5) 0.5545(4) 0.0672(19) Uani 1 1 d . . . . .
H10 H 0.105303 0.934787 0.527811 0.081 Uiso 1 1 calc R U . . .
C104 C 0.5140(5) 0.9862(4) 0.8015(6) 0.080(2) Uani 1 1 d . . . . .
H104 H 0.480256 0.920440 0.779983 0.096 Uiso 1 1 calc R U . . .
C103 C 0.5009(5) 0.9977(5) 0.8773(5) 0.0682(18) Uani 1 1 d . . . . .
H103 H 0.459355 0.939209 0.906225 0.082 Uiso 1 1 calc R U . . .
C11 C 0.0153(7) 0.7846(6) 0.5386(5) 0.082(3) Uani 1 1 d . . . . .
H11 H 0.047264 0.766854 0.500881 0.099 Uiso 1 1 calc R U . . .
C220 C 0.7379(5) 0.8865(6) 0.5354(4) 0.0678(16) Uani 1 1 d . . . . .
H22A H 0.771937 0.920439 0.489221 0.102 Uiso 1 1 calc R U . . .
H22B H 0.704858 0.812950 0.528784 0.102 Uiso 1 1 calc R U . . .
H22C H 0.787915 0.907487 0.575473 0.102 Uiso 1 1 calc R U . . .
C20 C 0.4133(5) 1.2512(6) 0.7684(4) 0.0763(19) Uani 1 1 d . . . . .
H20A H 0.437927 1.317756 0.745460 0.114 Uiso 1 1 calc R U . . .
H20B H 0.461054 1.256098 0.806848 0.114 Uiso 1 1 calc R U . . .
H20C H 0.346710 1.228329 0.790776 0.114 Uiso 1 1 calc R U . . .
C19 C 0.4047(5) 1.1783(6) 0.7117(4) 0.0720(18) Uani 1 1 d . . . . .
H19A H 0.395084 1.115965 0.736178 0.086 Uiso 1 1 calc R U . . .
H19B H 0.468342 1.207559 0.682696 0.086 Uiso 1 1 calc R U . . .
C219 C 0.6620(6) 0.9144(6) 0.5544(5) 0.081(2) Uani 1 1 d . . . . .
H21A H 0.620036 0.906480 0.510172 0.097 Uiso 1 1 calc R U . . .
H21B H 0.696215 0.986468 0.569674 0.097 Uiso 1 1 calc R U . . .
C120 C 0.6083(8) 1.6490(9) 0.8897(7) 0.136(5) Uani 1 1 d . . . . .
H12A H 0.657153 1.688227 0.850628 0.204 Uiso 1 1 calc R U . . .
H12B H 0.644553 1.644831 0.933215 0.204 Uiso 1 1 calc R U . . .
H12C H 0.569973 1.682504 0.903426 0.204 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
O201 C207 1.229(5) . ?
O101 C107 1.218(6) . ?
O1 C7 1.221(5) . ?
N102 C115 1.364(6) . ?
N102 C118 1.360(7) . ?
N102 C119 1.457(7) . ?
N101 H101 0.8800 . ?
N101 C101 1.360(6) . ?
N101 C108 1.461(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.357(6) . ?
N1 C8 1.452(6) . ?
N201 H201 0.8800 . ?
N201 C201 1.366(5) . ?
N201 C208 1.471(5) . ?
C201 C202 1.406(5) . ?
C201 C205 1.397(5) . ?
C1 C6 1.405(6) . ?
C1 C2 1.398(6) . ?
N2 C15 1.347(7) . ?
N2 C18 1.367(8) . ?
N2 C19 1.479(8) . ?
C101 C106 1.405(7) . ?
C101 C102 1.407(7) . ?
C208 C207 1.571(6) . ?
C208 C209 1.530(6) . ?
C208 C216 1.507(6) . ?
C115 H115 0.9500 . ?
C115 C116 1.377(6) . ?
C8 C16 1.515(7) . ?
C8 C7 1.559(6) . ?
C8 C9 1.525(6) . ?
C116 C108 1.508(6) . ?
C116 C117 1.417(7) . ?
C207 C205 1.436(6) . ?
C209 C210 1.380(7) . ?
C209 C214 1.394(7) . ?
C16 C15 1.364(7) . ?
C16 C17 1.423(7) . ?
C202 H202 0.9500 . ?
C202 C203 1.383(6) . ?
C107 C108 1.567(6) . ?
C107 C106 1.432(7) . ?
N202 C215 1.371(7) . ?
N202 C218 1.363(10) . ?
N202 C219 1.476(9) . ?
C7 C6 1.443(6) . ?
C6 C5 1.389(6) . ?
C216 C217 1.411(7) . ?
C216 C215 1.383(7) . ?
C109 C108 1.541(6) . ?
C109 C114 1.397(6) . ?
C109 C110 1.382(7) . ?
C205 C21 1.385(7) . ?
C203 H203 0.9500 . ?
C203 C204 1.395(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(9) . ?
C106 C105 1.395(7) . ?
C114 H114 0.9500 . ?
C114 C113 1.402(8) . ?
C15 H15 0.9500 . ?
C113 H113 0.9500 . ?
C113 C112 1.377(10) . ?
C18 H18 0.9500 . ?
C18 C17 1.352(8) . ?
C210 H210 0.9500 . ?
C210 C211 1.413(8) . ?
C21 H21 0.9500 . ?
C21 C204 1.382(7) . ?
C204 H204 0.9500 . ?
C9 C14 1.365(10) . ?
C9 C10 1.406(9) . ?
C112 H112 0.9500 . ?
C112 C111 1.364(10) . ?
C214 H214 0.9500 . ?
C214 C213 1.386(8) . ?
C217 H217 0.9500 . ?
C217 C218 1.400(9) . ?
C17 H17 0.9500 . ?
C118 H118 0.9500 . ?
C118 C117 1.382(7) . ?
C211 H211 0.9500 . ?
C211 C212 1.399(10) . ?
C117 H117 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.376(9) . ?
C4 C5 1.377(8) . ?
C110 H110 0.9500 . ?
C110 C111 1.389(7) . ?
C212 H212 0.9500 . ?
C212 C213 1.359(10) . ?
C111 H111 0.9500 . ?
C119 H11A 0.9900 . ?
C119 H11B 0.9900 . ?
C119 C120 1.481(12) . ?
C215 H215 0.9500 . ?
C105 H105 0.9500 . ?
C105 C104 1.396(10) . ?
C102 H102 0.9500 . ?
C102 C103 1.356(9) . ?
C213 H213 0.9500 . ?
C218 H218 0.9500 . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.459(11) . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.371(14) . ?
C12 H12 0.9500 . ?
C12 C11 1.310(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(8) . ?
C104 H104 0.9500 . ?
C104 C103 1.405(11) . ?
C103 H103 0.9500 . ?
C11 H11 0.9500 . ?
C220 H22A 0.9800 . ?
C220 H22B 0.9800 . ?
C220 H22C 0.9800 . ?
C220 C219 1.459(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.465(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C219 H21A 0.9900 . ?
C219 H21B 0.9900 . ?
C120 H12A 0.9800 . ?
C120 H12B 0.9800 . ?
C120 H12C 0.9800 . ?

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
C115 N102 C119 126.0(5) . . ?
C118 N102 C115 109.5(4) . . ?
C118 N102 C119 124.4(5) . . ?
C101 N101 H101 124.3 . . ?
C101 N101 C108 111.3(4) . . ?
C108 N101 H101 124.3 . . ?
C1 N1 H1 123.9 . . ?
C1 N1 C8 112.2(3) . . ?
C8 N1 H1 123.9 . . ?
C201 N201 H201 124.6 . . ?
C201 N201 C208 110.8(3) . . ?
C208 N201 H201 124.6 . . ?
N201 C201 C202 127.5(4) . . ?
N201 C201 C205 112.4(4) . . ?
C205 C201 C202 120.1(4) . . ?
N1 C1 C6 110.8(4) . . ?
N1 C1 C2 129.4(4) . . ?
C2 C1 C6 119.8(4) . . ?
C15 N2 C18 108.8(4) . . ?
C15 N2 C19 123.6(5) . . ?
C18 N2 C19 127.5(5) . . ?
N101 C101 C106 111.5(4) . . ?
N101 C101 C102 127.9(5) . . ?
C106 C101 C102 120.5(5) . . ?
N201 C208 C207 101.2(3) . . ?
N201 C208 C209 110.3(3) . . ?
N201 C208 C216 111.5(4) . . ?
C209 C208 C207 110.2(3) . . ?
C216 C208 C207 108.5(3) . . ?
C216 C208 C209 114.4(4) . . ?
N102 C115 H115 125.5 . . ?
N102 C115 C116 109.0(4) . . ?
C116 C115 H115 125.5 . . ?
N1 C8 C16 110.1(3) . . ?
N1 C8 C7 101.8(3) . . ?
N1 C8 C9 112.0(4) . . ?
C16 C8 C7 108.0(4) . . ?
C16 C8 C9 112.6(4) . . ?
C9 C8 C7 111.7(3) . . ?
C115 C116 C108 126.0(4) . . ?
C115 C116 C117 105.9(4) . . ?
C117 C116 C108 128.1(4) . . ?
O201 C207 C208 123.6(4) . . ?
O201 C207 C205 128.8(4) . . ?
C205 C207 C208 107.6(3) . . ?
C210 C209 C208 119.1(4) . . ?
C210 C209 C214 119.2(4) . . ?
C214 C209 C208 121.7(4) . . ?
C15 C16 C8 124.3(4) . . ?
C15 C16 C17 105.7(4) . . ?
C17 C16 C8 130.0(4) . . ?
C201 C202 H202 121.4 . . ?
C203 C202 C201 117.2(4) . . ?
C203 C202 H202 121.4 . . ?
O101 C107 C108 124.4(4) . . ?
O101 C107 C106 128.8(4) . . ?
C106 C107 C108 106.9(4) . . ?
C215 N202 C219 126.1(6) . . ?
C218 N202 C215 106.9(5) . . ?
C218 N202 C219 126.8(6) . . ?
O1 C7 C8 124.2(4) . . ?
O1 C7 C6 129.2(4) . . ?
C6 C7 C8 106.6(3) . . ?
C1 C6 C7 108.1(4) . . ?
C5 C6 C1 121.0(4) . . ?
C5 C6 C7 131.0(4) . . ?
C217 C216 C208 126.2(4) . . ?
C215 C216 C208 126.7(4) . . ?
C215 C216 C217 107.1(5) . . ?
C114 C109 C108 121.6(4) . . ?
C110 C109 C108 119.6(4) . . ?
C110 C109 C114 118.6(4) . . ?
N101 C108 C116 112.2(4) . . ?
N101 C108 C107 102.0(3) . . ?
N101 C108 C109 111.0(3) . . ?
C116 C108 C107 109.4(4) . . ?
C116 C108 C109 113.8(3) . . ?
C109 C108 C107 107.8(3) . . ?
C201 C205 C207 107.5(4) . . ?
C21 C205 C201 121.4(4) . . ?
C21 C205 C207 131.1(4) . . ?
C202 C203 H203 118.5 . . ?
C202 C203 C204 122.9(4) . . ?
C204 C203 H203 118.5 . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.8(5) . . ?
C3 C2 H2 121.1 . . ?
C101 C106 C107 108.1(4) . . ?
C105 C106 C101 121.2(5) . . ?
C105 C106 C107 130.6(5) . . ?
C109 C114 H114 120.0 . . ?
C109 C114 C113 119.9(5) . . ?
C113 C114 H114 120.0 . . ?
N2 C15 C16 109.5(4) . . ?
N2 C15 H15 125.3 . . ?
C16 C15 H15 125.3 . . ?
C114 C113 H113 119.9 . . ?
C112 C113 C114 120.3(6) . . ?
C112 C113 H113 119.9 . . ?
N2 C18 H18 126.0 . . ?
C17 C18 N2 108.1(5) . . ?
C17 C18 H18 126.0 . . ?
C209 C210 H210 119.8 . . ?
C209 C210 C211 120.3(5) . . ?
C211 C210 H210 119.8 . . ?
C205 C21 H21 120.5 . . ?
C204 C21 C205 119.1(4) . . ?
C204 C21 H21 120.5 . . ?
C203 C204 H204 120.3 . . ?
C21 C204 C203 119.3(4) . . ?
C21 C204 H204 120.3 . . ?
C14 C9 C8 122.2(6) . . ?
C14 C9 C10 118.8(6) . . ?
C10 C9 C8 119.0(6) . . ?
C113 C112 H112 120.2 . . ?
C111 C112 C113 119.6(5) . . ?
C111 C112 H112 120.2 . . ?
C209 C214 H214 119.8 . . ?
C213 C214 C209 120.4(5) . . ?
C213 C214 H214 119.8 . . ?
C216 C217 H217 127.2 . . ?
C218 C217 C216 105.7(6) . . ?
C218 C217 H217 127.2 . . ?
C16 C17 H17 126.1 . . ?
C18 C17 C16 107.9(5) . . ?
C18 C17 H17 126.1 . . ?
N102 C118 H118 126.3 . . ?
N102 C118 C117 107.5(4) . . ?
C117 C118 H118 126.3 . . ?
C210 C211 H211 120.5 . . ?
C212 C211 C210 118.9(6) . . ?
C212 C211 H211 120.5 . . ?
C116 C117 H117 125.9 . . ?
C118 C117 C116 108.1(4) . . ?
C118 C117 H117 125.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C109 C110 H110 119.7 . . ?
C109 C110 C111 120.6(5) . . ?
C111 C110 H110 119.7 . . ?
C211 C212 H212 119.8 . . ?
C213 C212 C211 120.4(5) . . ?
C213 C212 H212 119.8 . . ?
C112 C111 C110 120.9(6) . . ?
C112 C111 H111 119.5 . . ?
C110 C111 H111 119.5 . . ?
N102 C119 H11A 109.2 . . ?
N102 C119 H11B 109.2 . . ?
N102 C119 C120 111.9(6) . . ?
H11A C119 H11B 107.9 . . ?
C120 C119 H11A 109.2 . . ?
C120 C119 H11B 109.2 . . ?
N202 C215 C216 110.0(5) . . ?
N202 C215 H215 125.0 . . ?
C216 C215 H215 125.0 . . ?
C106 C105 H105 121.4 . . ?
C106 C105 C104 117.2(6) . . ?
C104 C105 H105 121.4 . . ?
C101 C102 H102 121.0 . . ?
C103 C102 C101 118.1(6) . . ?
C103 C102 H102 121.0 . . ?
C214 C213 H213 119.6 . . ?
C212 C213 C214 120.7(6) . . ?
C212 C213 H213 119.6 . . ?
N202 C218 C217 110.2(5) . . ?
N202 C218 H218 124.9 . . ?
C217 C218 H218 124.9 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(5) . . ?
C4 C3 H3 118.8 . . ?
C9 C14 H14 121.0 . . ?
C9 C14 C13 117.9(8) . . ?
C13 C14 H14 121.0 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.6(5) . . ?
C4 C5 H5 120.7 . . ?
C14 C13 H13 120.7 . . ?
C12 C13 C14 118.7(8) . . ?
C12 C13 H13 120.7 . . ?
C13 C12 H12 118.5 . . ?
C11 C12 C13 122.9(8) . . ?
C11 C12 H12 118.5 . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.1(8) . . ?
C11 C10 H10 118.9 . . ?
C105 C104 H104 119.5 . . ?
C105 C104 C103 121.0(6) . . ?
C103 C104 H104 119.5 . . ?
C102 C103 C104 121.9(6) . . ?
C102 C103 H103 119.0 . . ?
C104 C103 H103 119.0 . . ?
C12 C11 C10 119.5(9) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
H22A C220 H22B 109.5 . . ?
H22A C220 H22C 109.5 . . ?
H22B C220 H22C 109.5 . . ?
C219 C220 H22A 109.5 . . ?
C219 C220 H22B 109.5 . . ?
C219 C220 H22C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
N2 C19 H19A 109.3 . . ?
N2 C19 H19B 109.3 . . ?
C20 C19 N2 111.7(6) . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
N202 C219 H21A 109.4 . . ?
N202 C219 H21B 109.4 . . ?
C220 C219 N202 111.0(6) . . ?
C220 C219 H21A 109.4 . . ?
C220 C219 H21B 109.4 . . ?
H21A C219 H21B 108.0 . . ?
C119 C120 H12A 109.5 . . ?
C119 C120 H12B 109.5 . . ?
C119 C120 H12C 109.5 . . ?
H12A C120 H12B 109.5 . . ?
H12A C120 H12C 109.5 . . ?
H12B C120 H12C 109.5 . . ?

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 H1 O1 0.88 2.01 2.872(5) 167.1 3_465 yes
N201 H201 O201 0.88 2.10 2.895(5) 149.1 3_565 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
O201 C207 C205 C201 178.2(4) . . . . ?
O201 C207 C205 C21 -0.8(9) . . . . ?
O101 C107 C108 N101 -179.0(4) . . . . ?
O101 C107 C108 C116 62.1(5) . . . . ?
O101 C107 C108 C109 -62.0(5) . . . . ?
O101 C107 C106 C101 -177.7(5) . . . . ?
O101 C107 C106 C105 0.2(9) . . . . ?
O1 C7 C6 C1 177.5(5) . . . . ?
O1 C7 C6 C5 -1.6(10) . . . . ?
N102 C115 C116 C108 -178.3(4) . . . . ?
N102 C115 C116 C117 2.0(6) . . . . ?
N102 C118 C117 C116 0.3(7) . . . . ?
N101 C101 C106 C107 -5.4(5) . . . . ?
N101 C101 C106 C105 176.4(5) . . . . ?
N101 C101 C102 C103 -176.8(5) . . . . ?
N1 C1 C6 C7 -0.6(5) . . . . ?
N1 C1 C6 C5 178.6(5) . . . . ?
N1 C1 C2 C3 -175.7(5) . . . . ?
N1 C8 C16 C15 41.5(6) . . . . ?
N1 C8 C16 C17 -137.9(5) . . . . ?
N1 C8 C7 O1 -174.8(5) . . . . ?
N1 C8 C7 C6 6.4(5) . . . . ?
N1 C8 C9 C14 14.7(6) . . . . ?
N1 C8 C9 C10 -165.0(4) . . . . ?
N201 C201 C202 C203 -177.6(4) . . . . ?
N201 C201 C205 C207 -2.4(5) . . . . ?
N201 C201 C205 C21 176.7(4) . . . . ?
N201 C208 C207 O201 -174.7(4) . . . . ?
N201 C208 C207 C205 6.1(4) . . . . ?
N201 C208 C209 C210 58.5(5) . . . . ?
N201 C208 C209 C214 -122.8(4) . . . . ?
N201 C208 C216 C217 39.8(7) . . . . ?
N201 C208 C216 C215 -142.0(5) . . . . ?
C201 N201 C208 C207 -7.7(4) . . . . ?
C201 N201 C208 C209 -124.3(4) . . . . ?
C201 N201 C208 C216 107.5(4) . . . . ?
C201 C202 C203 C204 0.4(7) . . . . ?
C201 C205 C21 C204 1.6(8) . . . . ?
C1 N1 C8 C16 107.3(4) . . . . ?
C1 N1 C8 C7 -7.1(5) . . . . ?
C1 N1 C8 C9 -126.5(4) . . . . ?
C1 C6 C5 C4 -3.1(9) . . . . ?
C1 C2 C3 C4 -2.0(9) . . . . ?
N2 C18 C17 C16 -0.3(6) . . . . ?
C101 N101 C108 C116 113.0(4) . . . . ?
C101 N101 C108 C107 -3.9(4) . . . . ?
C101 N101 C108 C109 -118.5(4) . . . . ?
C101 C106 C105 C104 1.7(8) . . . . ?
C101 C102 C103 C104 0.3(9) . . . . ?
C208 N201 C201 C202 -174.6(4) . . . . ?
C208 N201 C201 C205 6.8(5) . . . . ?
C208 C207 C205 C201 -2.6(5) . . . . ?
C208 C207 C205 C21 178.4(5) . . . . ?
C208 C209 C210 C211 179.0(4) . . . . ?
C208 C209 C214 C213 -179.0(4) . . . . ?
C208 C216 C217 C218 -178.4(5) . . . . ?
C208 C216 C215 N202 179.5(5) . . . . ?
C115 N102 C118 C117 1.0(7) . . . . ?
C115 N102 C119 C120 93.5(9) . . . . ?
C115 C116 C108 N101 22.4(6) . . . . ?
C115 C116 C108 C107 134.8(5) . . . . ?
C115 C116 C108 C109 -104.6(5) . . . . ?
C115 C116 C117 C118 -1.4(6) . . . . ?
C8 N1 C1 C6 5.2(5) . . . . ?
C8 N1 C1 C2 -176.5(4) . . . . ?
C8 C16 C15 N2 178.9(4) . . . . ?
C8 C16 C17 C18 -179.3(5) . . . . ?
C8 C7 C6 C1 -3.8(5) . . . . ?
C8 C7 C6 C5 177.1(6) . . . . ?
C8 C9 C14 C13 -179.1(5) . . . . ?
C8 C9 C10 C11 179.9(5) . . . . ?
C207 C208 C209 C210 -52.4(5) . . . . ?
C207 C208 C209 C214 126.4(4) . . . . ?
C207 C208 C216 C217 150.4(5) . . . . ?
C207 C208 C216 C215 -31.5(6) . . . . ?
C207 C205 C21 C204 -179.5(5) . . . . ?
C209 C208 C207 O201 -58.0(5) . . . . ?
C209 C208 C207 C205 122.8(4) . . . . ?
C209 C208 C216 C217 -86.2(6) . . . . ?
C209 C208 C216 C215 91.9(6) . . . . ?
C209 C210 C211 C212 0.5(8) . . . . ?
C209 C214 C213 C212 -0.6(8) . . . . ?
C16 C8 C7 O1 69.2(6) . . . . ?
C16 C8 C7 C6 -109.6(4) . . . . ?
C16 C8 C9 C14 139.5(5) . . . . ?
C16 C8 C9 C10 -40.2(6) . . . . ?
C202 C201 C205 C207 178.9(4) . . . . ?
C202 C201 C205 C21 -2.0(7) . . . . ?
C202 C203 C204 C21 -0.7(8) . . . . ?
C107 C106 C105 C104 -176.0(5) . . . . ?
C7 C8 C16 C15 151.9(4) . . . . ?
C7 C8 C16 C17 -27.6(6) . . . . ?
C7 C8 C9 C14 -98.7(6) . . . . ?
C7 C8 C9 C10 81.6(5) . . . . ?
C7 C6 C5 C4 175.8(6) . . . . ?
C6 C1 C2 C3 2.4(7) . . . . ?
C216 C208 C207 O201 67.9(5) . . . . ?
C216 C208 C207 C205 -111.3(4) . . . . ?
C216 C208 C209 C210 -174.9(4) . . . . ?
C216 C208 C209 C214 3.9(6) . . . . ?
C216 C217 C218 N202 -3.2(9) . . . . ?
C109 C114 C113 C112 1.4(8) . . . . ?
C109 C110 C111 C112 0.2(8) . . . . ?
C108 N101 C101 C106 6.0(5) . . . . ?
C108 N101 C101 C102 -177.5(5) . . . . ?
C108 C116 C117 C118 179.0(5) . . . . ?
C108 C107 C106 C101 2.7(5) . . . . ?
C108 C107 C106 C105 -179.3(5) . . . . ?
C108 C109 C114 C113 -177.0(4) . . . . ?
C108 C109 C110 C111 176.3(4) . . . . ?
C205 C201 C202 C203 1.0(6) . . . . ?
C205 C21 C204 C203 -0.3(8) . . . . ?
C2 C1 C6 C7 -179.0(4) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
C106 C101 C102 C103 -0.7(8) . . . . ?
C106 C107 C108 N101 0.6(4) . . . . ?
C106 C107 C108 C116 -118.3(4) . . . . ?
C106 C107 C108 C109 117.5(4) . . . . ?
C106 C105 C104 C103 -2.1(10) . . . . ?
C114 C109 C108 N101 -158.3(4) . . . . ?
C114 C109 C108 C116 -30.6(6) . . . . ?
C114 C109 C108 C107 90.9(5) . . . . ?
C114 C109 C110 C111 0.6(7) . . . . ?
C114 C113 C112 C111 -0.6(9) . . . . ?
C15 N2 C18 C17 -0.7(6) . . . . ?
C15 N2 C19 C20 -70.4(8) . . . . ?
C15 C16 C17 C18 1.1(6) . . . . ?
C113 C112 C111 C110 -0.2(9) . . . . ?
C18 N2 C15 C16 1.4(6) . . . . ?
C18 N2 C19 C20 107.1(7) . . . . ?
C210 C209 C214 C213 -0.2(7) . . . . ?
C210 C211 C212 C213 -1.3(8) . . . . ?
C9 C8 C16 C15 -84.2(6) . . . . ?
C9 C8 C16 C17 96.3(6) . . . . ?
C9 C8 C7 O1 -55.2(7) . . . . ?
C9 C8 C7 C6 126.0(5) . . . . ?
C9 C14 C13 C12 -0.9(10) . . . . ?
C9 C10 C11 C12 -0.8(9) . . . . ?
C214 C209 C210 C211 0.2(7) . . . . ?
C217 C216 C215 N202 -2.1(7) . . . . ?
C17 C16 C15 N2 -1.5(6) . . . . ?
C118 N102 C115 C116 -2.0(6) . . . . ?
C118 N102 C119 C120 -83.2(9) . . . . ?
C211 C212 C213 C214 1.3(8) . . . . ?
C117 C116 C108 N101 -158.0(5) . . . . ?
C117 C116 C108 C107 -45.6(6) . . . . ?
C117 C116 C108 C109 74.9(6) . . . . ?
C110 C109 C108 N101 26.2(5) . . . . ?
C110 C109 C108 C116 153.8(4) . . . . ?
C110 C109 C108 C107 -84.7(5) . . . . ?
C110 C109 C114 C113 -1.4(7) . . . . ?
C119 N102 C115 C116 -179.1(5) . . . . ?
C119 N102 C118 C117 178.2(6) . . . . ?
C215 N202 C218 C217 1.9(9) . . . . ?
C215 N202 C219 C220 -121.9(7) . . . . ?
C215 C216 C217 C218 3.2(7) . . . . ?
C105 C104 C103 C102 1.1(11) . . . . ?
C102 C101 C106 C107 177.8(4) . . . . ?
C102 C101 C106 C105 -0.3(7) . . . . ?
C218 N202 C215 C216 0.1(8) . . . . ?
C218 N202 C219 C220 63.4(11) . . . . ?
C3 C4 C5 C6 3.6(10) . . . . ?
C14 C9 C10 C11 0.2(8) . . . . ?
C14 C13 C12 C11 0.4(11) . . . . ?
C5 C4 C3 C2 -1.0(10) . . . . ?
C13 C12 C11 C10 0.5(11) . . . . ?
C10 C9 C14 C13 0.6(8) . . . . ?
C19 N2 C15 C16 179.3(5) . . . . ?
C19 N2 C18 C17 -178.5(6) . . . . ?
C219 N202 C215 C216 -175.4(6) . . . . ?
C219 N202 C218 C217 177.4(7) . . . . ?

_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 1.970
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_1355_ad-686_20230202
_database_code_depnum_ccdc_archive 'CCDC 2361190'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;Birla Institute of Technology and Science Pilani, Hyderabad Campus
India
;
_audit_update_record             
;
2024-06-07 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H14 N2 O3 S'
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'
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                   9.0312(2)
_cell_length_b                   16.1924(3)
_cell_length_c                   9.2203(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.644(2)
_cell_angle_gamma                90
_cell_volume                     1336.37(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4146
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      79.2810
_cell_measurement_theta_min      4.9050
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.793
_exptl_absorpt_coefficient_mu    2.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.568
_diffrn_reflns_theta_min         4.941
_diffrn_ambient_temperature      133(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  13.00   0.50    1.03    --    0.00 -57.00-120.00   84
  2  ω    -88.00 -52.00   0.50    1.03    --    0.00 -57.00-120.00   72
  3  ω    -87.00 -49.00   0.50    1.03    --    0.00 -57.00 -30.00   76
  4  ω    -39.00  20.00   0.50    1.03    --    0.00 -57.00 -30.00  118
  5  ω     36.00 139.00   0.50    4.11    --  107.20 -82.00 -30.00  206
  6  ω     84.00 150.00   0.50    4.11    --  107.20  15.00  90.00  132
  7  ω     91.00 127.00   0.50    4.11    --  107.20 -30.00 -30.00   72
  8  ω     26.00  52.00   0.50    4.11    --  107.20 -82.00 -90.00   52
  9  ω     52.00  85.00   0.50    4.11    --  107.20 -30.00 -30.00   66
 10  ω     68.00 108.00   0.50    4.11    --  107.20 -82.00 -90.00   80
 11  ω     21.00 135.00   0.50    4.11    --  107.20 -15.00-120.00  228
 12  ω     20.00  56.00   0.50    4.11    --  107.20 -30.00 -90.00   72
 13  ω     83.00 110.00   0.50    4.11    --  107.20 -30.00 -90.00   54
 14  ω     20.00 132.00   0.50    4.11    --  107.20 -61.00 -30.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0783438000
_diffrn_orient_matrix_UB_12      -0.0113111000
_diffrn_orient_matrix_UB_13      -0.1576453000
_diffrn_orient_matrix_UB_21      0.1531228000
_diffrn_orient_matrix_UB_22      -0.0020923000
_diffrn_orient_matrix_UB_23      -0.0561990000
_diffrn_orient_matrix_UB_31      0.0058049000
_diffrn_orient_matrix_UB_32      -0.0944594000
_diffrn_orient_matrix_UB_33      0.0201268000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2508
_reflns_number_total             2808
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.086
_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)+(0.0549P)²+0.6433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1129
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.29142(4) 0.42753(2) 0.50636(4) 0.02471(14) Uani 1 1 d . . . . .
O1 O 0.35341(14) 0.36921(7) 0.63990(14) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.14040(14) 0.40528(8) 0.46049(14) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.39860(16) 0.42018(8) 0.40740(16) 0.0361(3) Uani 1 1 d . . . . .
N1 N 0.29611(17) 0.51797(8) 0.57655(16) 0.0261(3) Uani 1 1 d . . . . .
H1 H 0.349136 0.558533 0.546249 0.031 Uiso 1 1 calc R U . . .
N2 N 0.20634(17) 0.74099(8) 0.83215(16) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.29036(19) 0.38087(10) 0.77104(19) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.22646(18) 0.45571(10) 0.80409(18) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.1737(2) 0.46096(11) 0.9391(2) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.131048 0.511358 0.966190 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1817(2) 0.39462(12) 1.0349(2) 0.0375(4) Uani 1 1 d . . . . .
H4 H 0.144515 0.399675 1.126140 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2443(3) 0.32084(12) 0.9967(2) 0.0415(5) Uani 1 1 d . . . . .
H5 H 0.249227 0.275125 1.061772 0.050 Uiso 1 1 calc R U . . .
C6 C 0.2996(2) 0.31351(11) 0.8646(2) 0.0355(4) Uani 1 1 d . . . . .
H6 H 0.343072 0.263190 0.838295 0.043 Uiso 1 1 calc R U . . .
C7 C 0.20305(18) 0.52790(9) 0.69781(17) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.095831 0.527524 0.653370 0.026 Uiso 1 1 calc R U . . .
C8 C 0.23517(19) 0.61055(9) 0.76722(18) 0.0233(3) Uani 1 1 d . . . . .
C9 C 0.13889(19) 0.67656(10) 0.75420(18) 0.0244(3) Uani 1 1 d . . . . .
H9 H 0.041746 0.677238 0.700065 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3457(2) 0.71736(11) 0.8930(2) 0.0335(4) Uani 1 1 d . . . . .
H10 H 0.416068 0.751185 0.951307 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3674(2) 0.63667(11) 0.8561(2) 0.0320(4) Uani 1 1 d . . . . .
H11 H 0.454249 0.604408 0.884497 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1437(2) 0.82418(11) 0.8378(2) 0.0342(4) Uani 1 1 d . . . . .
H12A H 0.168168 0.846356 0.938240 0.041 Uiso 1 1 calc R U . . .
H12B H 0.033567 0.821080 0.815410 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2026(3) 0.88220(12) 0.7317(2) 0.0459(5) Uani 1 1 d . . . . .
H13A H 0.174139 0.862020 0.631622 0.069 Uiso 1 1 calc R U . . .
H13B H 0.311703 0.885057 0.752764 0.069 Uiso 1 1 calc R U . . .
H13C H 0.160216 0.937333 0.741384 0.069 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
S1 O1 1.5931(13) . ?
S1 O2 1.4197(13) . ?
S1 O3 1.4208(13) . ?
S1 N1 1.5994(14) . ?
O1 C1 1.416(2) . ?
N1 H1 0.8800 . ?
N1 C7 1.494(2) . ?
N2 C9 1.364(2) . ?
N2 C10 1.363(2) . ?
N2 C12 1.465(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.386(2) . ?
C2 C3 1.393(2) . ?
C2 C7 1.522(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.495(2) . ?
C8 C9 1.373(2) . ?
C8 C11 1.420(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.371(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.504(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
O1 S1 N1 104.02(7) . . ?
O2 S1 O1 107.74(8) . . ?
O2 S1 O3 119.81(8) . . ?
O2 S1 N1 109.00(8) . . ?
O3 S1 O1 104.32(8) . . ?
O3 S1 N1 110.67(8) . . ?
C1 O1 S1 116.17(10) . . ?
S1 N1 H1 122.8 . . ?
C7 N1 S1 114.47(10) . . ?
C7 N1 H1 122.8 . . ?
C9 N2 C12 125.10(16) . . ?
C10 N2 C9 108.99(14) . . ?
C10 N2 C12 125.69(15) . . ?
C2 C1 O1 121.87(15) . . ?
C6 C1 O1 115.39(15) . . ?
C6 C1 C2 122.73(17) . . ?
C1 C2 C7 123.60(15) . . ?
C3 C2 C1 116.69(15) . . ?
C3 C2 C7 119.58(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.80(17) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.61(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.32(17) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.83(17) . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C2 110.81(13) . . ?
N1 C7 H7 107.6 . . ?
N1 C7 C8 108.68(12) . . ?
C2 C7 H7 107.6 . . ?
C8 C7 C2 114.17(13) . . ?
C8 C7 H7 107.6 . . ?
C9 C8 C7 125.09(15) . . ?
C9 C8 C11 107.02(14) . . ?
C11 C8 C7 127.89(15) . . ?
N2 C9 C8 108.43(15) . . ?
N2 C9 H9 125.8 . . ?
C8 C9 H9 125.8 . . ?
N2 C10 H10 125.7 . . ?
N2 C10 C11 108.68(16) . . ?
C11 C10 H10 125.7 . . ?
C8 C11 H11 126.6 . . ?
C10 C11 C8 106.87(16) . . ?
C10 C11 H11 126.6 . . ?
N2 C12 H12A 109.1 . . ?
N2 C12 H12B 109.1 . . ?
N2 C12 C13 112.30(16) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
S1 O1 C1 C2 -24.7(2) . . . . ?
S1 O1 C1 C6 156.59(13) . . . . ?
S1 N1 C7 C2 45.54(16) . . . . ?
S1 N1 C7 C8 171.76(11) . . . . ?
O1 S1 N1 C7 -60.11(13) . . . . ?
O1 C1 C2 C3 -177.36(15) . . . . ?
O1 C1 C2 C7 6.8(2) . . . . ?
O1 C1 C6 C5 178.18(17) . . . . ?
O2 S1 O1 C1 -67.60(13) . . . . ?
O2 S1 N1 C7 54.61(14) . . . . ?
O3 S1 O1 C1 164.06(11) . . . . ?
O3 S1 N1 C7 -171.62(12) . . . . ?
N1 S1 O1 C1 48.01(13) . . . . ?
N1 C7 C8 C9 108.58(18) . . . . ?
N1 C7 C8 C11 -70.8(2) . . . . ?
N2 C10 C11 C8 0.6(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C7 N1 -17.0(2) . . . . ?
C1 C2 C7 C8 -140.12(16) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C7 C8 C9 -127.16(17) . . . . ?
C2 C7 C8 C11 53.5(2) . . . . ?
C3 C2 C7 N1 167.28(15) . . . . ?
C3 C2 C7 C8 44.2(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C1 C2 C7 -174.53(16) . . . . ?
C7 C2 C3 C4 174.85(17) . . . . ?
C7 C8 C9 N2 179.99(15) . . . . ?
C7 C8 C11 C10 179.38(17) . . . . ?
C9 N2 C10 C11 -1.0(2) . . . . ?
C9 N2 C12 C13 -96.7(2) . . . . ?
C9 C8 C11 C10 -0.1(2) . . . . ?
C10 N2 C9 C8 1.0(2) . . . . ?
C10 N2 C12 C13 77.3(2) . . . . ?
C11 C8 C9 N2 -0.6(2) . . . . ?
C12 N2 C9 C8 175.83(16) . . . . ?
C12 N2 C10 C11 -175.83(17) . . . . ?

_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 2.014
_oxdiff_exptl_absorpt_empirical_full_min 0.763
####################################################################### 
# 
# 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_ad959_20240828
_database_code_depnum_ccdc_archive 'CCDC 2380259'
loop_
_audit_author_name
_audit_author_address
'Krishnan Rangan'
;Birla Institute of Technology and Science Pilani, Hyderabad Campus
India
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-08-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 N2 O'
_chemical_formula_sum            'C25 H22 N2 O'
_chemical_formula_weight         366.44
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H22 N2 O '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   19.9908(8)
_cell_length_b                   15.7652(5)
_cell_length_c                   5.8187(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1833.82(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8496
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.8170
_cell_measurement_theta_min      1.6410
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14236
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.049
_diffrn_reflns_theta_min         1.645
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  14.00   0.50    7.36    --   11.50 -22.00-102.00   50
  2  ω    -13.00  12.00   0.50    7.36    --   11.50  22.00  62.00   50
  3  ω     20.00  46.00   0.50    7.36    --  -11.70  22.00  62.00   52
  4  ω     28.00  54.00   0.50    7.36    --   11.50  77.00 150.00   52
  5  ω    -77.00  35.00   0.50    7.36    --   11.50 -77.00-150.00  224
  6  ω     74.00 100.00   0.50    7.36    --   11.50  77.00 150.00   52
  7  ω    -13.00  19.00   0.50    7.36    --   11.50  77.00  30.00   64
  8  ω     59.00  85.00   0.50    7.36    --   11.50  77.00  30.00   52
  9  ω   -101.00   8.00   0.50    7.36    --  -11.70 -77.00 120.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0225205000
_diffrn_orient_matrix_UB_12      0.0325853000
_diffrn_orient_matrix_UB_13      0.0327938000
_diffrn_orient_matrix_UB_21      0.0271795000
_diffrn_orient_matrix_UB_22      -0.0285796000
_diffrn_orient_matrix_UB_23      -0.0119357000
_diffrn_orient_matrix_UB_31      0.0035849000
_diffrn_orient_matrix_UB_32      0.0120903000
_diffrn_orient_matrix_UB_33      -0.1167884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3673
_reflns_number_total             4140
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1308 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.094
_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)+(0.0412P)²+0.0739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0860
_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 O(H) groups
2.a Riding coordinates:
 N1(H1A)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.25270(6) 0.18858(8) 0.7877(2) 0.0216(3) Uani 1 1 d . . . . .
H1 H 0.276309 0.226094 0.850421 0.032 Uiso 1 1 calc R U . . .
N1 N 0.30366(7) 0.26852(9) 0.2252(3) 0.0173(4) Uani 1 1 d . . . . .
H1A H 0.324975 0.313731 0.175229 0.021 Uiso 1 1 d R U . . .
N2 N 0.31474(7) 0.45712(9) 0.8249(3) 0.0172(4) Uani 1 1 d . . . . .
C1 C 0.34583(9) 0.19784(11) 0.2648(3) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.39975(9) 0.17155(11) 0.1339(4) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.413869 0.202809 0.003060 0.024 Uiso 1 1 calc R U . . .
C3 C 0.43272(10) 0.09746(11) 0.2009(4) 0.0236(5) Uani 1 1 d . . . . .
H3 H 0.469745 0.077827 0.113443 0.028 Uiso 1 1 calc R U . . .
C4 C 0.41239(10) 0.05198(12) 0.3929(4) 0.0236(5) Uani 1 1 d . . . . .
H4 H 0.436087 0.002359 0.437111 0.028 Uiso 1 1 calc R U . . .
C5 C 0.35769(9) 0.07854(11) 0.5206(4) 0.0210(4) Uani 1 1 d . . . . .
H5 H 0.343224 0.047052 0.650611 0.025 Uiso 1 1 calc R U . . .
C6 C 0.32451(9) 0.15183(11) 0.4551(3) 0.0172(4) Uani 1 1 d . . . . .
C7 C 0.26194(10) 0.19157(10) 0.5480(3) 0.0164(4) Uani 1 1 d . . . . .
H7 H 0.223546 0.160181 0.477939 0.020 Uiso 1 1 calc R U . . .
C8 C 0.26230(9) 0.28309(10) 0.4359(3) 0.0156(4) Uani 1 1 d . . . . .
C9 C 0.19142(9) 0.31122(10) 0.3768(3) 0.0161(4) Uani 1 1 d . . . . .
C10 C 0.13973(9) 0.29601(11) 0.5319(4) 0.0195(4) Uani 1 1 d . . . . .
H10 H 0.148884 0.267775 0.672632 0.023 Uiso 1 1 calc R U . . .
C11 C 0.07500(10) 0.32178(11) 0.4824(4) 0.0214(4) Uani 1 1 d . . . . .
H11 H 0.040033 0.310826 0.588868 0.026 Uiso 1 1 calc R U . . .
C12 C 0.06106(10) 0.36354(12) 0.2777(4) 0.0236(5) Uani 1 1 d . . . . .
H12 H 0.016777 0.381681 0.244586 0.028 Uiso 1 1 calc R U . . .
C13 C 0.11206(10) 0.37851(12) 0.1226(4) 0.0239(5) Uani 1 1 d . . . . .
H13 H 0.102837 0.406885 -0.017880 0.029 Uiso 1 1 calc R U . . .
C14 C 0.17682(10) 0.35210(11) 0.1719(4) 0.0205(4) Uani 1 1 d . . . . .
H14 H 0.211530 0.362193 0.063789 0.025 Uiso 1 1 calc R U . . .
C15 C 0.26832(9) 0.41803(11) 0.6893(3) 0.0162(4) Uani 1 1 d . . . . .
H15 H 0.223776 0.437075 0.665272 0.019 Uiso 1 1 calc R U . . .
C16 C 0.29634(9) 0.34656(11) 0.5927(3) 0.0153(4) Uani 1 1 d . . . . .
C17 C 0.36345(9) 0.34313(11) 0.6742(3) 0.0175(4) Uani 1 1 d . . . . .
H17 H 0.395745 0.301130 0.636770 0.021 Uiso 1 1 calc R U . . .
C18 C 0.37305(9) 0.41160(11) 0.8167(4) 0.0181(4) Uani 1 1 d . . . . .
H18 H 0.413236 0.425039 0.895912 0.022 Uiso 1 1 calc R U . . .
C19 C 0.30014(10) 0.53010(11) 0.9769(4) 0.0221(5) Uani 1 1 d . . . . .
H19A H 0.272089 0.510828 1.107069 0.026 Uiso 1 1 calc R U . . .
H19B H 0.274492 0.573190 0.890005 0.026 Uiso 1 1 calc R U . . .
C20 C 0.36334(9) 0.56983(11) 1.0690(4) 0.0179(4) Uani 1 1 d . . . . .
C21 C 0.39878(10) 0.62827(11) 0.9376(4) 0.0210(4) Uani 1 1 d . . . . .
H21 H 0.381862 0.645369 0.792209 0.025 Uiso 1 1 calc R U . . .
C22 C 0.45833(10) 0.66161(12) 1.0168(4) 0.0266(5) Uani 1 1 d . . . . .
H22 H 0.482491 0.700899 0.924917 0.032 Uiso 1 1 calc R U . . .
C23 C 0.48285(10) 0.63799(13) 1.2291(4) 0.0281(5) Uani 1 1 d . . . . .
H23 H 0.524114 0.660398 1.282657 0.034 Uiso 1 1 calc R U . . .
C24 C 0.44733(10) 0.58188(13) 1.3628(4) 0.0274(5) Uani 1 1 d . . . . .
H24 H 0.463721 0.566555 1.510264 0.033 Uiso 1 1 calc R U . . .
C25 C 0.38776(10) 0.54751(12) 1.2838(4) 0.0230(4) Uani 1 1 d . . . . .
H25 H 0.363636 0.508616 1.376949 0.028 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 H1 0.8400 . ?
O1 C7 1.408(2) . ?
N1 H1A 0.8798 . ?
N1 C1 1.416(2) . ?
N1 C8 1.497(2) . ?
N2 C15 1.365(2) . ?
N2 C18 1.370(2) . ?
N2 C19 1.480(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.391(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.500(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.583(2) . ?
C8 C9 1.524(3) . ?
C8 C16 1.515(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.378(2) . ?
C16 C17 1.424(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.508(3) . ?
C20 C21 1.391(3) . ?
C20 C25 1.387(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 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
C7 O1 H1 109.5 . . ?
C1 N1 H1A 113.8 . . ?
C1 N1 C8 108.43(15) . . ?
C8 N1 H1A 114.4 . . ?
C15 N2 C18 108.77(14) . . ?
C15 N2 C19 124.20(15) . . ?
C18 N2 C19 126.58(16) . . ?
C2 C1 N1 127.59(18) . . ?
C2 C1 C6 121.39(17) . . ?
C6 C1 N1 110.95(16) . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.70(19) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.21(19) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.40(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.82(19) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 108.94(16) . . ?
C5 C6 C1 120.46(18) . . ?
C5 C6 C7 130.44(18) . . ?
O1 C7 C6 116.89(16) . . ?
O1 C7 H7 106.7 . . ?
O1 C7 C8 116.05(15) . . ?
C6 C7 H7 106.7 . . ?
C6 C7 C8 103.21(15) . . ?
C8 C7 H7 106.7 . . ?
N1 C8 C7 101.54(13) . . ?
N1 C8 C9 111.92(15) . . ?
N1 C8 C16 110.28(14) . . ?
C9 C8 C7 110.72(15) . . ?
C16 C8 C7 110.84(15) . . ?
C16 C8 C9 111.18(14) . . ?
C10 C9 C8 119.58(17) . . ?
C14 C9 C8 121.67(17) . . ?
C14 C9 C10 118.75(17) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.50(19) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.52(18) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.09(19) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.85(19) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N2 C15 H15 125.4 . . ?
N2 C15 C16 109.17(16) . . ?
C16 C15 H15 125.4 . . ?
C15 C16 C8 127.07(17) . . ?
C15 C16 C17 106.16(16) . . ?
C17 C16 C8 126.76(16) . . ?
C16 C17 H17 126.2 . . ?
C18 C17 C16 107.61(16) . . ?
C18 C17 H17 126.2 . . ?
N2 C18 C17 108.28(16) . . ?
N2 C18 H18 125.9 . . ?
C17 C18 H18 125.9 . . ?
N2 C19 H19A 109.3 . . ?
N2 C19 H19B 109.3 . . ?
N2 C19 C20 111.70(15) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C21 C20 C19 120.42(19) . . ?
C25 C20 C19 120.62(18) . . ?
C25 C20 C21 118.94(19) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.1(2) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.76(19) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.1(2) . . ?
C24 C25 H25 119.9 . . ?

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 C7 C8 N1 154.01(15) . . . . ?
O1 C7 C8 C9 -87.0(2) . . . . ?
O1 C7 C8 C16 36.9(2) . . . . ?
N1 C1 C2 C3 -177.43(17) . . . . ?
N1 C1 C6 C5 178.15(16) . . . . ?
N1 C1 C6 C7 2.2(2) . . . . ?
N1 C8 C9 C10 154.80(16) . . . . ?
N1 C8 C9 C14 -25.4(2) . . . . ?
N1 C8 C16 C15 129.41(19) . . . . ?
N1 C8 C16 C17 -52.2(2) . . . . ?
N2 C15 C16 C8 178.28(17) . . . . ?
N2 C15 C16 C17 -0.4(2) . . . . ?
N2 C19 C20 C21 82.7(2) . . . . ?
N2 C19 C20 C25 -96.0(2) . . . . ?
C1 N1 C8 C7 -24.68(17) . . . . ?
C1 N1 C8 C9 -142.81(14) . . . . ?
C1 N1 C8 C16 92.87(16) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C7 O1 -146.05(16) . . . . ?
C1 C6 C7 C8 -17.39(19) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C6 C7 -175.01(16) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 174.89(19) . . . . ?
C5 C6 C7 O1 38.6(3) . . . . ?
C5 C6 C7 C8 167.22(18) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C7 C8 N1 24.82(18) . . . . ?
C6 C7 C8 C9 143.81(16) . . . . ?
C6 C7 C8 C16 -92.32(17) . . . . ?
C7 C8 C9 C10 42.3(2) . . . . ?
C7 C8 C9 C14 -137.95(16) . . . . ?
C7 C8 C16 C15 -118.9(2) . . . . ?
C7 C8 C16 C17 59.5(2) . . . . ?
C8 N1 C1 C2 -167.73(17) . . . . ?
C8 N1 C1 C6 15.26(19) . . . . ?
C8 C9 C10 C11 179.41(16) . . . . ?
C8 C9 C14 C13 -178.95(17) . . . . ?
C8 C16 C17 C18 -178.22(18) . . . . ?
C9 C8 C16 C15 4.7(3) . . . . ?
C9 C8 C16 C17 -176.91(17) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C9 C14 C13 0.8(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C15 N2 C18 C17 0.1(2) . . . . ?
C15 N2 C19 C20 -168.95(17) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C16 C8 C9 C10 -81.38(19) . . . . ?
C16 C8 C9 C14 98.4(2) . . . . ?
C16 C17 C18 N2 -0.4(2) . . . . ?
C18 N2 C15 C16 0.2(2) . . . . ?
C18 N2 C19 C20 19.5(3) . . . . ?
C19 N2 C15 C16 -172.60(17) . . . . ?
C19 N2 C18 C17 172.69(18) . . . . ?
C19 C20 C21 C22 -176.84(17) . . . . ?
C19 C20 C25 C24 177.40(17) . . . . ?
C20 C21 C22 C23 -0.9(3) . . . . ?
C21 C20 C25 C24 -1.3(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C23 C24 C25 C20 -0.3(3) . . . . ?
C25 C20 C21 C22 1.9(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 2.416
_oxdiff_exptl_absorpt_empirical_full_min 0.423
