# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_chr23
_database_code_depnum_ccdc_archive 'CCDC 2260642'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '2b in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 Cl2 N2'
_chemical_formula_weight         489.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3303(6)
_cell_length_b                   12.1997(9)
_cell_length_c                   14.8086(11)
_cell_angle_alpha                68.470(6)
_cell_angle_beta                 74.945(6)
_cell_angle_gamma                80.004(6)
_cell_volume                     1346.76(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    6462
_cell_measurement_theta_min      5.52
_cell_measurement_theta_max      58.81

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    2.308
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8308
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 2.6.2.0 (STOE, 2021)'
_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Genix3D Cu HF'
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 5.81
_diffrn_reflns_number            9334
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.910
_diffrn_reflns_theta_max         56.906
_diffrn_reflns_theta_full        56.906
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3566
_reflns_number_gt                2004
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)'
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_reduction        'X-Area Integrate 2.5.1.0 (STOE, 2021)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.2096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3566
_refine_ls_number_parameters     327
_refine_ls_number_restraints     307
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1364
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1_1 Cl 0.35383(13) 0.27608(8) 0.02675(8) 0.0802(4) Uani 1 1 d D . . . .
C1_1 C 0.4370(5) 0.4029(3) 0.0127(3) 0.0553(10) Uani 1 1 d D . . . .
N2_1 N 0.3462(4) 0.4690(3) 0.0629(2) 0.0587(8) Uani 1 1 d D . . . .
C3_1 C 0.4085(5) 0.5694(3) 0.0518(3) 0.0556(9) Uani 1 1 d D . . . .
C4_1 C 0.3167(5) 0.6429(3) 0.1063(3) 0.0606(10) Uani 1 1 d D . . . .
C5_1 C 0.2526(5) 0.7104(3) 0.1497(3) 0.0612(10) Uani 1 1 d D . . . .
C11_1 C 0.1872(4) 0.7968(3) 0.1976(3) 0.0565(9) Uani 1 1 d D . . . .
C12_1 C 0.2663(5) 0.8983(3) 0.1675(3) 0.0669(11) Uani 1 1 d D . . . .
H12_1 H 0.360450 0.910032 0.116061 0.080 Uiso 1 1 calc R U . . .
C13_1 C 0.2089(5) 0.9829(3) 0.2122(3) 0.0684(11) Uani 1 1 d D . . . .
H13_1 H 0.264582 1.050947 0.189758 0.082 Uiso 1 1 calc R U . . .
C14_1 C 0.0703(5) 0.9690(3) 0.2896(3) 0.0587(10) Uani 1 1 d D . . . .
C15_1 C -0.0074(5) 0.8667(3) 0.3193(3) 0.0730(12) Uani 1 1 d D . . . .
H15_1 H -0.100894 0.854784 0.371267 0.088 Uiso 1 1 calc R U . . .
C16_1 C 0.0475(5) 0.7816(3) 0.2755(3) 0.0732(12) Uani 1 1 d D . . . .
H16_1 H -0.008631 0.713788 0.297705 0.088 Uiso 1 1 calc R U . . .
C17_1 C 0.0020(5) 1.0603(3) 0.3390(3) 0.0711(11) Uani 1 1 d D . . . .
H17A_1 H -0.099811 1.099578 0.317179 0.085 Uiso 1 1 calc R U . . .
H17B_1 H -0.028375 1.019395 0.410124 0.085 Uiso 1 1 calc R U . . .
C18_1 C 0.1136(5) 1.1532(3) 0.3212(3) 0.0779(12) Uani 1 1 d D . . . .
H18A_1 H 0.142893 1.195604 0.250373 0.094 Uiso 1 1 calc R U . . .
H18B_1 H 0.215850 1.114688 0.342855 0.094 Uiso 1 1 calc R U . . .
C19_1 C 0.0374(5) 1.2421(3) 0.3742(3) 0.0766(12) Uani 1 1 d D . . . .
H19A_1 H -0.064858 1.280770 0.352677 0.092 Uiso 1 1 calc R U . . .
H19B_1 H 0.008383 1.199903 0.445147 0.092 Uiso 1 1 calc R U . . .
C20_1 C 0.1512(6) 1.3349(4) 0.3554(3) 0.0943(14) Uani 1 1 d D . . . .
H20A_1 H 0.179977 1.377298 0.284498 0.113 Uiso 1 1 calc R U . . .
H20B_1 H 0.253490 1.296301 0.376873 0.113 Uiso 1 1 calc R U . . .
C21_1 C 0.0741(7) 1.4232(4) 0.4088(4) 0.1136(17) Uani 1 1 d D . . . .
H21A_1 H 0.151774 1.480300 0.393817 0.170 Uiso 1 1 calc R U . . .
H21B_1 H 0.048133 1.382170 0.479177 0.170 Uiso 1 1 calc R U . . .
H21C_1 H -0.026240 1.462859 0.386996 0.170 Uiso 1 1 calc R U . . .
Cl1_2 Cl 0.66829(14) -0.00218(11) 0.14580(9) 0.1021(5) Uani 1 1 d D . . . .
C1_2 C 0.8578(5) -0.0022(4) 0.0627(3) 0.0650(11) Uani 1 1 d D . . . .
N2_2 N 0.8955(4) -0.0902(3) 0.0288(2) 0.0693(9) Uani 1 1 d D . . . .
C3_2 C 1.0425(5) -0.0900(3) -0.0373(3) 0.0618(10) Uani 1 1 d D . . . .
C4_2 C 1.0895(5) -0.1831(3) -0.0772(3) 0.0670(11) Uani 1 1 d D . . . .
C5_2 C 1.1338(5) -0.2602(3) -0.1121(3) 0.0669(11) Uani 1 1 d D . . . .
C11_2 C 1.1884(5) -0.3545(3) -0.1524(3) 0.0587(10) Uani 1 1 d D . . . .
C12_2 C 1.3480(5) -0.3597(3) -0.2112(3) 0.0640(10) Uani 1 1 d D . . . .
H12_2 H 1.417599 -0.300481 -0.226882 0.077 Uiso 1 1 calc R U . . .
C13_2 C 1.4023(5) -0.4529(3) -0.2460(3) 0.0689(11) Uani 1 1 d D . . . .
H13_2 H 1.509671 -0.456229 -0.284342 0.083 Uiso 1 1 calc R U . . .
C14_2 C 1.3015(5) -0.5416(3) -0.2256(3) 0.0661(11) Uani 1 1 d D . . . .
C15_2 C 1.1426(5) -0.5327(3) -0.1697(3) 0.0742(12) Uani 1 1 d D . . . .
H15_2 H 1.072094 -0.590786 -0.155901 0.089 Uiso 1 1 calc R U . . .
C16_2 C 1.0846(5) -0.4406(3) -0.1336(3) 0.0703(11) Uani 1 1 d D . . . .
H16_2 H 0.976050 -0.436543 -0.096843 0.084 Uiso 1 1 calc R U . . .
C17_2 C 1.3650(6) -0.6460(4) -0.2595(4) 0.0913(14) Uani 1 1 d D . . . .
H17A_2 H 1.451118 -0.691487 -0.224102 0.110 Uiso 1 1 calc R U . . .
H17B_2 H 1.274135 -0.695742 -0.239544 0.110 Uiso 1 1 calc R U . . .
C18_2 C 1.4323(9) -0.6223(5) -0.3642(4) 0.148(2) Uani 1 1 d D . . . .
H18A_2 H 1.532342 -0.580936 -0.385562 0.178 Uiso 0.507(3) 1 calc R U P A 1
H18B_2 H 1.351237 -0.574241 -0.402640 0.178 Uiso 0.507(3) 1 calc R U P A 1
H18C_2 H 1.550180 -0.613785 -0.375380 0.178 Uiso 0.219(3) 1 calc R U P A 2
H18D_2 H 1.381617 -0.545326 -0.398469 0.178 Uiso 0.219(3) 1 calc R U P A 2
H18E_2 H 1.485155 -0.548942 -0.388860 0.178 Uiso 0.274(3) 1 calc R U P A 3
H18F_2 H 1.337913 -0.606578 -0.395454 0.178 Uiso 0.274(3) 1 calc R U P A 3
C19_2 C 1.4748(16) -0.7505(8) -0.3780(6) 0.074(3) Uani 0.507(3) 1 d D . P A 1
H19A_2 H 1.563213 -0.795317 -0.344342 0.088 Uiso 0.507(3) 1 calc R U P A 1
H19B_2 H 1.376929 -0.794680 -0.350082 0.088 Uiso 0.507(3) 1 calc R U P A 1
C20_2 C 1.529(2) -0.7297(8) -0.4871(7) 0.097(3) Uani 0.507(3) 1 d D . P A 1
H20A_2 H 1.628274 -0.687025 -0.515899 0.116 Uiso 0.507(3) 1 calc R U P A 1
H20B_2 H 1.441168 -0.686144 -0.521701 0.116 Uiso 0.507(3) 1 calc R U P A 1
C19B_2 C 1.418(2) -0.707(2) -0.4191(19) 0.094(10) Uiso 0.219(3) 1 d D . P A 2
H19C_2 H 1.336222 -0.763068 -0.378390 0.113 Uiso 0.219(3) 1 calc R U P A 2
H19D_2 H 1.385274 -0.662413 -0.481651 0.113 Uiso 0.219(3) 1 calc R U P A 2
C20B_2 C 1.587(3) -0.770(2) -0.437(2) 0.103(10) Uiso 0.219(3) 1 d D . P A 2
H20C_2 H 1.621405 -0.814187 -0.374372 0.124 Uiso 0.219(3) 1 calc R U P A 2
H20D_2 H 1.668905 -0.715105 -0.479014 0.124 Uiso 0.219(3) 1 calc R U P A 2
C19C_2 C 1.5626(19) -0.7148(15) -0.4059(14) 0.083(7) Uiso 0.274(3) 1 d D . P A
3
H19E_2 H 1.647728 -0.675023 -0.461653 0.099 Uiso 0.274(3) 1 calc R U P A 3
H19F_2 H 1.615618 -0.772293 -0.354548 0.099 Uiso 0.274(3) 1 calc R U P A 3
C20C_2 C 1.452(2) -0.771(2) -0.437(2) 0.120(9) Uiso 0.274(3) 1 d D . P A 3
H20E_2 H 1.390629 -0.710937 -0.482921 0.144 Uiso 0.274(3) 1 calc R U P A 3
H20F_2 H 1.372532 -0.814429 -0.379939 0.144 Uiso 0.274(3) 1 calc R U P A 3
C21_2 C 1.5656(9) -0.8586(5) -0.4904(5) 0.165(3) Uani 1 1 d D . . . .
H21A_2 H 1.602034 -0.855658 -0.558269 0.247 Uiso 0.507(3) 1 calc R U P A 1
H21B_2 H 1.651456 -0.900021 -0.454665 0.247 Uiso 0.507(3) 1 calc R U P A 1
H21C_2 H 1.465942 -0.899148 -0.460417 0.247 Uiso 0.507(3) 1 calc R U P A 1
H21D H 1.670371 -0.903011 -0.504354 0.247 Uiso 0.219(3) 1 calc R U P A 2
H21E H 1.483353 -0.911894 -0.447530 0.247 Uiso 0.219(3) 1 calc R U P A 2
H21F H 1.530528 -0.813492 -0.551455 0.247 Uiso 0.219(3) 1 calc R U P A 2
H21G H 1.496407 -0.895847 -0.511308 0.247 Uiso 0.274(3) 1 calc R U P A 3
H21H H 1.643530 -0.814830 -0.547293 0.247 Uiso 0.274(3) 1 calc R U P A 3
H21I H 1.625501 -0.917939 -0.444693 0.247 Uiso 0.274(3) 1 calc R U P A 3


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1_1 C1_1 1.726(3) . ?
C1_1 N2_1 1.308(4) . ?
C1_1 C3_1 1.399(5) 2_665 ?
N2_1 C3_1 1.351(4) . ?
C3_1 C4_1 1.419(5) . ?
C4_1 C5_1 1.196(4) . ?
C5_1 C11_1 1.436(5) . ?
C11_1 C12_1 1.376(4) . ?
C11_1 C16_1 1.392(4) . ?
C12_1 C13_1 1.377(4) . ?
C12_1 H12_1 0.9300 . ?
C13_1 C14_1 1.384(5) . ?
C13_1 H13_1 0.9300 . ?
C14_1 C15_1 1.379(4) . ?
C14_1 C17_1 1.503(4) . ?
C15_1 C16_1 1.373(5) . ?
C15_1 H15_1 0.9300 . ?
C16_1 H16_1 0.9300 . ?
C17_1 C18_1 1.496(5) . ?
C17_1 H17A_1 0.9700 . ?
C17_1 H17B_1 0.9700 . ?
C18_1 C19_1 1.524(5) . ?
C18_1 H18A_1 0.9700 . ?
C18_1 H18B_1 0.9700 . ?
C19_1 C20_1 1.504(5) . ?
C19_1 H19A_1 0.9700 . ?
C19_1 H19B_1 0.9700 . ?
C20_1 C21_1 1.523(5) . ?
C20_1 H20A_1 0.9700 . ?
C20_1 H20B_1 0.9700 . ?
C21_1 H21A_1 0.9600 . ?
C21_1 H21B_1 0.9600 . ?
C21_1 H21C_1 0.9600 . ?
Cl1_2 C1_2 1.731(4) . ?
C1_2 N2_2 1.304(4) . ?
C1_2 C3_2 1.395(5) 2_755 ?
N2_2 C3_2 1.354(4) . ?
C3_2 C4_2 1.418(5) . ?
C4_2 C5_2 1.194(4) . ?
C5_2 C11_2 1.437(5) . ?
C11_2 C16_2 1.381(5) . ?
C11_2 C12_2 1.393(4) . ?
C12_2 C13_2 1.375(4) . ?
C12_2 H12_2 0.9300 . ?
C13_2 C14_2 1.382(5) . ?
C13_2 H13_2 0.9300 . ?
C14_2 C15_2 1.377(5) . ?
C14_2 C17_2 1.501(5) . ?
C15_2 C16_2 1.378(5) . ?
C15_2 H15_2 0.9300 . ?
C16_2 H16_2 0.9300 . ?
C17_2 C18_2 1.441(6) . ?
C17_2 H17A_2 0.9700 . ?
C17_2 H17B_2 0.9700 . ?
C18_2 C19B_2 1.568(13) . ?
C18_2 C19C_2 1.605(12) . ?
C18_2 C19_2 1.618(8) . ?
C18_2 H18A_2 0.9700 . ?
C18_2 H18B_2 0.9700 . ?
C18_2 H18C_2 0.9700 . ?
C18_2 H18D_2 0.9700 . ?
C18_2 H18E_2 0.9700 . ?
C18_2 H18F_2 0.9700 . ?
C19_2 C20_2 1.495(10) . ?
C19_2 H19A_2 0.9700 . ?
C19_2 H19B_2 0.9700 . ?
C20_2 C21_2 1.565(8) . ?
C20_2 H20A_2 0.9700 . ?
C20_2 H20B_2 0.9700 . ?
C19B_2 C20B_2 1.489(15) . ?
C19B_2 H19C_2 0.9700 . ?
C19B_2 H19D_2 0.9700 . ?
C20B_2 C21_2 1.611(14) . ?
C20B_2 H20C_2 0.9700 . ?
C20B_2 H20D_2 0.9700 . ?
C19C_2 C20C_2 1.487(14) . ?
C19C_2 H19E_2 0.9700 . ?
C19C_2 H19F_2 0.9700 . ?
C20C_2 C21_2 1.592(14) . ?
C20C_2 H20E_2 0.9700 . ?
C20C_2 H20F_2 0.9700 . ?
C21_2 H21A_2 0.9600 . ?
C21_2 H21B_2 0.9600 . ?
C21_2 H21C_2 0.9600 . ?
C21_2 H21D 0.9600 . ?
C21_2 H21E 0.9600 . ?
C21_2 H21F 0.9600 . ?
C21_2 H21G 0.9600 . ?
C21_2 H21H 0.9600 . ?
C21_2 H21I 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
N2_1 C1_1 C3_1 124.2(3) . 2_665 ?
N2_1 C1_1 Cl1_1 116.3(3) . . ?
C3_1 C1_1 Cl1_1 119.5(3) 2_665 . ?
C1_1 N2_1 C3_1 117.0(3) . . ?
N2_1 C3_1 C1_1 118.8(3) . 2_665 ?
N2_1 C3_1 C4_1 119.2(3) . . ?
C1_1 C3_1 C4_1 122.0(3) 2_665 . ?
C5_1 C4_1 C3_1 173.8(4) . . ?
C4_1 C5_1 C11_1 175.3(4) . . ?
C12_1 C11_1 C16_1 117.9(3) . . ?
C12_1 C11_1 C5_1 119.4(3) . . ?
C16_1 C11_1 C5_1 122.7(3) . . ?
C11_1 C12_1 C13_1 121.3(4) . . ?
C11_1 C12_1 H12_1 119.4 . . ?
C13_1 C12_1 H12_1 119.4 . . ?
C12_1 C13_1 C14_1 121.5(4) . . ?
C12_1 C13_1 H13_1 119.3 . . ?
C14_1 C13_1 H13_1 119.3 . . ?
C15_1 C14_1 C13_1 116.6(3) . . ?
C15_1 C14_1 C17_1 120.3(3) . . ?
C13_1 C14_1 C17_1 123.1(3) . . ?
C16_1 C15_1 C14_1 122.7(4) . . ?
C16_1 C15_1 H15_1 118.6 . . ?
C14_1 C15_1 H15_1 118.6 . . ?
C15_1 C16_1 C11_1 120.0(4) . . ?
C15_1 C16_1 H16_1 120.0 . . ?
C11_1 C16_1 H16_1 120.0 . . ?
C18_1 C17_1 C14_1 117.0(3) . . ?
C18_1 C17_1 H17A_1 108.1 . . ?
C14_1 C17_1 H17A_1 108.1 . . ?
C18_1 C17_1 H17B_1 108.1 . . ?
C14_1 C17_1 H17B_1 108.1 . . ?
H17A_1 C17_1 H17B_1 107.3 . . ?
C17_1 C18_1 C19_1 114.3(3) . . ?
C17_1 C18_1 H18A_1 108.7 . . ?
C19_1 C18_1 H18A_1 108.7 . . ?
C17_1 C18_1 H18B_1 108.7 . . ?
C19_1 C18_1 H18B_1 108.7 . . ?
H18A_1 C18_1 H18B_1 107.6 . . ?
C20_1 C19_1 C18_1 113.5(3) . . ?
C20_1 C19_1 H19A_1 108.9 . . ?
C18_1 C19_1 H19A_1 108.9 . . ?
C20_1 C19_1 H19B_1 108.9 . . ?
C18_1 C19_1 H19B_1 108.9 . . ?
H19A_1 C19_1 H19B_1 107.7 . . ?
C19_1 C20_1 C21_1 113.2(4) . . ?
C19_1 C20_1 H20A_1 108.9 . . ?
C21_1 C20_1 H20A_1 108.9 . . ?
C19_1 C20_1 H20B_1 108.9 . . ?
C21_1 C20_1 H20B_1 108.9 . . ?
H20A_1 C20_1 H20B_1 107.8 . . ?
C20_1 C21_1 H21A_1 109.5 . . ?
C20_1 C21_1 H21B_1 109.5 . . ?
H21A_1 C21_1 H21B_1 109.5 . . ?
C20_1 C21_1 H21C_1 109.5 . . ?
H21A_1 C21_1 H21C_1 109.5 . . ?
H21B_1 C21_1 H21C_1 109.5 . . ?
N2_2 C1_2 C3_2 125.2(3) . 2_755 ?
N2_2 C1_2 Cl1_2 116.2(3) . . ?
C3_2 C1_2 Cl1_2 118.6(3) 2_755 . ?
C1_2 N2_2 C3_2 116.6(3) . . ?
N2_2 C3_2 C1_2 118.2(3) . 2_755 ?
N2_2 C3_2 C4_2 119.1(4) . . ?
C1_2 C3_2 C4_2 122.7(4) 2_755 . ?
C5_2 C4_2 C3_2 178.0(4) . . ?
C4_2 C5_2 C11_2 178.8(4) . . ?
C16_2 C11_2 C12_2 119.1(3) . . ?
C16_2 C11_2 C5_2 120.9(3) . . ?
C12_2 C11_2 C5_2 120.0(4) . . ?
C13_2 C12_2 C11_2 119.8(4) . . ?
C13_2 C12_2 H12_2 120.1 . . ?
C11_2 C12_2 H12_2 120.1 . . ?
C12_2 C13_2 C14_2 121.8(4) . . ?
C12_2 C13_2 H13_2 119.1 . . ?
C14_2 C13_2 H13_2 119.1 . . ?
C15_2 C14_2 C13_2 117.4(3) . . ?
C15_2 C14_2 C17_2 121.2(4) . . ?
C13_2 C14_2 C17_2 121.3(4) . . ?
C14_2 C15_2 C16_2 122.2(4) . . ?
C14_2 C15_2 H15_2 118.9 . . ?
C16_2 C15_2 H15_2 118.9 . . ?
C15_2 C16_2 C11_2 119.6(4) . . ?
C15_2 C16_2 H16_2 120.2 . . ?
C11_2 C16_2 H16_2 120.2 . . ?
C18_2 C17_2 C14_2 117.4(4) . . ?
C18_2 C17_2 H17A_2 108.0 . . ?
C14_2 C17_2 H17A_2 108.0 . . ?
C18_2 C17_2 H17B_2 108.0 . . ?
C14_2 C17_2 H17B_2 108.0 . . ?
H17A_2 C17_2 H17B_2 107.2 . . ?
C17_2 C18_2 C19B_2 122.7(11) . . ?
C17_2 C18_2 C19C_2 122.3(8) . . ?
C17_2 C18_2 C19_2 105.5(5) . . ?
C17_2 C18_2 H18A_2 110.6 . . ?
C19_2 C18_2 H18A_2 110.6 . . ?
C17_2 C18_2 H18B_2 110.6 . . ?
C19_2 C18_2 H18B_2 110.6 . . ?
H18A_2 C18_2 H18B_2 108.8 . . ?
C17_2 C18_2 H18C_2 106.7 . . ?
C19B_2 C18_2 H18C_2 106.7 . . ?
C17_2 C18_2 H18D_2 106.7 . . ?
C19B_2 C18_2 H18D_2 106.7 . . ?
H18C_2 C18_2 H18D_2 106.6 . . ?
C17_2 C18_2 H18E_2 106.8 . . ?
C19C_2 C18_2 H18E_2 106.8 . . ?
C17_2 C18_2 H18F_2 106.8 . . ?
C19C_2 C18_2 H18F_2 106.8 . . ?
H18E_2 C18_2 H18F_2 106.6 . . ?
C20_2 C19_2 C18_2 107.4(6) . . ?
C20_2 C19_2 H19A_2 110.2 . . ?
C18_2 C19_2 H19A_2 110.2 . . ?
C20_2 C19_2 H19B_2 110.2 . . ?
C18_2 C19_2 H19B_2 110.2 . . ?
H19A_2 C19_2 H19B_2 108.5 . . ?
C19_2 C20_2 C21_2 102.4(7) . . ?
C19_2 C20_2 H20A_2 111.3 . . ?
C21_2 C20_2 H20A_2 111.3 . . ?
C19_2 C20_2 H20B_2 111.3 . . ?
C21_2 C20_2 H20B_2 111.3 . . ?
H20A_2 C20_2 H20B_2 109.2 . . ?
C20B_2 C19B_2 C18_2 106.1(12) . . ?
C20B_2 C19B_2 H19C_2 110.5 . . ?
C18_2 C19B_2 H19C_2 110.5 . . ?
C20B_2 C19B_2 H19D_2 110.5 . . ?
C18_2 C19B_2 H19D_2 110.5 . . ?
H19C_2 C19B_2 H19D_2 108.7 . . ?
C19B_2 C20B_2 C21_2 104.4(11) . . ?
C19B_2 C20B_2 H20C_2 110.9 . . ?
C21_2 C20B_2 H20C_2 110.9 . . ?
C19B_2 C20B_2 H20D_2 110.9 . . ?
C21_2 C20B_2 H20D_2 110.9 . . ?
H20C_2 C20B_2 H20D_2 108.9 . . ?
C20C_2 C19C_2 C18_2 101.6(10) . . ?
C20C_2 C19C_2 H19E_2 111.5 . . ?
C18_2 C19C_2 H19E_2 111.5 . . ?
C20C_2 C19C_2 H19F_2 111.5 . . ?
C18_2 C19C_2 H19F_2 111.5 . . ?
H19E_2 C19C_2 H19F_2 109.3 . . ?
C19C_2 C20C_2 C21_2 108.2(11) . . ?
C19C_2 C20C_2 H20E_2 110.1 . . ?
C21_2 C20C_2 H20E_2 110.1 . . ?
C19C_2 C20C_2 H20F_2 110.1 . . ?
C21_2 C20C_2 H20F_2 110.1 . . ?
H20E_2 C20C_2 H20F_2 108.4 . . ?
C20_2 C21_2 H21A_2 109.5 . . ?
C20_2 C21_2 H21B_2 109.5 . . ?
H21A_2 C21_2 H21B_2 109.5 . . ?
C20_2 C21_2 H21C_2 109.5 . . ?
H21A_2 C21_2 H21C_2 109.5 . . ?
H21B_2 C21_2 H21C_2 109.5 . . ?
C20B_2 C21_2 H21D 109.5 . . ?
C20B_2 C21_2 H21E 109.5 . . ?
H21D C21_2 H21E 109.5 . . ?
C20B_2 C21_2 H21F 109.5 . . ?
H21D C21_2 H21F 109.5 . . ?
H21E C21_2 H21F 109.5 . . ?
C20C_2 C21_2 H21G 109.5 . . ?
C20C_2 C21_2 H21H 109.5 . . ?
H21G C21_2 H21H 109.5 . . ?
C20C_2 C21_2 H21I 109.5 . . ?
H21G C21_2 H21I 109.5 . . ?
H21H C21_2 H21I 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
C3_1 C1_1 N2_1 C3_1 -0.9(6) 2_665 . . . ?
Cl1_1 C1_1 N2_1 C3_1 -179.2(2) . . . . ?
C1_1 N2_1 C3_1 C1_1 0.8(5) . . . 2_665 ?
C1_1 N2_1 C3_1 C4_1 -178.6(3) . . . . ?
C16_1 C11_1 C12_1 C13_1 -0.5(6) . . . . ?
C5_1 C11_1 C12_1 C13_1 -179.3(4) . . . . ?
C11_1 C12_1 C13_1 C14_1 0.6(6) . . . . ?
C12_1 C13_1 C14_1 C15_1 -0.3(6) . . . . ?
C12_1 C13_1 C14_1 C17_1 -178.9(3) . . . . ?
C13_1 C14_1 C15_1 C16_1 0.0(6) . . . . ?
C17_1 C14_1 C15_1 C16_1 178.6(4) . . . . ?
C14_1 C15_1 C16_1 C11_1 0.1(6) . . . . ?
C12_1 C11_1 C16_1 C15_1 0.2(6) . . . . ?
C5_1 C11_1 C16_1 C15_1 178.9(4) . . . . ?
C15_1 C14_1 C17_1 C18_1 165.4(4) . . . . ?
C13_1 C14_1 C17_1 C18_1 -16.1(5) . . . . ?
C14_1 C17_1 C18_1 C19_1 -179.4(3) . . . . ?
C17_1 C18_1 C19_1 C20_1 -179.9(4) . . . . ?
C18_1 C19_1 C20_1 C21_1 -179.9(4) . . . . ?
C3_2 C1_2 N2_2 C3_2 -0.9(6) 2_755 . . . ?
Cl1_2 C1_2 N2_2 C3_2 179.1(3) . . . . ?
C1_2 N2_2 C3_2 C1_2 0.9(6) . . . 2_755 ?
C1_2 N2_2 C3_2 C4_2 -179.5(3) . . . . ?
C16_2 C11_2 C12_2 C13_2 -2.8(5) . . . . ?
C5_2 C11_2 C12_2 C13_2 177.2(3) . . . . ?
C11_2 C12_2 C13_2 C14_2 1.0(6) . . . . ?
C12_2 C13_2 C14_2 C15_2 0.8(6) . . . . ?
C12_2 C13_2 C14_2 C17_2 -176.8(4) . . . . ?
C13_2 C14_2 C15_2 C16_2 -0.9(6) . . . . ?
C17_2 C14_2 C15_2 C16_2 176.7(4) . . . . ?
C14_2 C15_2 C16_2 C11_2 -0.8(6) . . . . ?
C12_2 C11_2 C16_2 C15_2 2.7(6) . . . . ?
C5_2 C11_2 C16_2 C15_2 -177.3(4) . . . . ?
C15_2 C14_2 C17_2 C18_2 126.5(5) . . . . ?
C13_2 C14_2 C17_2 C18_2 -55.9(6) . . . . ?
C14_2 C17_2 C18_2 C19B_2 -147.8(10) . . . . ?
C14_2 C17_2 C18_2 C19C_2 156.6(8) . . . . ?
C14_2 C17_2 C18_2 C19_2 -175.4(6) . . . . ?
C17_2 C18_2 C19_2 C20_2 174.4(11) . . . . ?
C18_2 C19_2 C20_2 C21_2 -179.9(8) . . . . ?
C17_2 C18_2 C19B_2 C20B_2 -105(2) . . . . ?
C18_2 C19B_2 C20B_2 C21_2 178.6(16) . . . . ?
C17_2 C18_2 C19C_2 C20C_2 100.0(16) . . . . ?
C18_2 C19C_2 C20C_2 C21_2 174.9(15) . . . . ?

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041


# start Validation Reply Form
_vrf_THETM01_chr23               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: We have cut the dataset at a resolution of 0.92 A due to 
I/sigma and R(int) criteria. Despite of using a high intensity source 
and long irradiation times this was the best achievable resolution. 
The data to parameter ratio is still acceptable. In order to compensate 
for the lack of information we used all possible local symmetry 
restraints (SHELX SAME command) and rigid bond restraints (SHELX RIGU 
command) for all atoms. 
;
####################################################################### 
# 
# 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_chr26
_database_code_depnum_ccdc_archive 'CCDC 2260644'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '2f in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H8 Cl4 N2'
_chemical_formula_weight         418.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   3.8745(6)
_cell_length_b                   11.2406(18)
_cell_length_c                   20.211(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.300(4)
_cell_angle_gamma                90
_cell_volume                     880.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2540
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.30

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7922
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9089
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         27.226
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1913
_reflns_number_gt                1597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.1191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1913
_refine_ls_number_parameters     152
_refine_ls_number_restraints     94
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1510
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_restrained_S_all      1.268
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.2232(4) 0.74253(11) 0.44809(6) 0.0407(4) Uani 1 1 d . . . . .
C1 C -0.0966(11) 0.6041(4) 0.4766(2) 0.0269(10) Uani 1 1 d . . . . .
N2 N 0.0588(10) 0.5341(3) 0.43498(18) 0.0279(8) Uani 1 1 d . . . . .
C3 C 0.1588(11) 0.4263(4) 0.4571(2) 0.0238(9) Uani 1 1 d . . . . .
C4 C 0.3245(12) 0.3483(4) 0.4128(2) 0.0274(10) Uani 1 1 d . . . . .
C5 C 0.4565(12) 0.2808(4) 0.3759(2) 0.0294(10) Uani 1 1 d . . . . .
Cl2 Cl 0.7255(5) 0.05268(14) 0.43277(7) 0.0485(5) Uani 0.901(4) 1 d D . P A 1
C11 C 0.6057(14) 0.2014(5) 0.3297(3) 0.0249(11) Uani 0.901(4) 1 d D . P A 1
C12 C 0.7368(13) 0.0912(5) 0.3501(3) 0.0279(11) Uani 0.901(4) 1 d D . P A 1
C13 C 0.8823(14) 0.0130(5) 0.3057(3) 0.0346(12) Uani 0.901(4) 1 d D . P A 1
H13 H 0.976075 -0.060581 0.320590 0.042 Uiso 0.901(4) 1 calc R U P A 1
C14 C 0.8897(16) 0.0432(6) 0.2395(3) 0.0383(14) Uani 0.901(4) 1 d D . P A 1
H14 H 0.989628 -0.009785 0.208729 0.046 Uiso 0.901(4) 1 calc R U P A 1
C15 C 0.7519(15) 0.1504(6) 0.2179(3) 0.0389(13) Uani 0.901(4) 1 d D . P A 1
H15 H 0.750105 0.169617 0.172108 0.047 Uiso 0.901(4) 1 calc R U P A 1
C16 C 0.6184(15) 0.2287(6) 0.2624(3) 0.0326(12) Uani 0.901(4) 1 d D . P A 1
H16 H 0.532439 0.303164 0.247149 0.039 Uiso 0.901(4) 1 calc R U P A 1
Cl2B Cl 0.521(4) 0.3026(13) 0.2400(8) 0.049(5) Uani 0.099(4) 1 d D . P A 2
C11B C 0.655(12) 0.165(3) 0.3463(13) 0.013(11) Uiso 0.099(4) 1 d D . P A 2
C12B C 0.658(14) 0.173(3) 0.2772(14) 0.039(14) Uiso 0.099(4) 1 d D . P A 2
H12B H 0.551890 0.238860 0.255940 0.047 Uiso 0.099(4) 1 calc R U P A 2
C13B C 0.812(12) 0.086(3) 0.2388(17) 0.016(11) Uiso 0.099(4) 1 d D . P A 2
H13B H 0.813262 0.090633 0.191891 0.019 Uiso 0.099(4) 1 calc R U P A 2
C14B C 0.963(16) -0.007(4) 0.273(2) 0.051(17) Uiso 0.099(4) 1 d D . P A 2
H14B H 1.103267 -0.061243 0.249798 0.062 Uiso 0.099(4) 1 calc R U P A 2
C15B C 0.918(18) -0.025(4) 0.340(2) 0.06(2) Uiso 0.099(4) 1 d D . P A 2
H15B H 0.981144 -0.099103 0.359839 0.076 Uiso 0.099(4) 1 calc R U P A 2
C16B C 0.783(14) 0.064(4) 0.3779(17) 0.031(14) Uiso 0.099(4) 1 d D . P A 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.727(5) . ?
C1 N2 1.308(6) . ?
C1 C3 1.408(6) 3_566 ?
N2 C3 1.346(6) . ?
C3 C4 1.418(6) . ?
C4 C5 1.186(6) . ?
C5 C11 1.424(6) . ?
C5 C11B 1.63(3) . ?
Cl2 C12 1.727(6) . ?
C11 C16 1.396(8) . ?
C11 C12 1.399(7) . ?
C12 C13 1.385(7) . ?
C13 C14 1.380(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
Cl2B C12B 1.723(18) . ?
C11B C16B 1.39(2) . ?
C11B C12B 1.398(19) . ?
C12B C13B 1.388(19) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.38(2) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.38(2) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.37(2) . ?
C15B H15B 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
N2 C1 C3 123.9(4) . 3_566 ?
N2 C1 Cl1 117.3(3) . . ?
C3 C1 Cl1 118.9(3) 3_566 . ?
C1 N2 C3 117.4(4) . . ?
N2 C3 C1 118.7(4) . 3_566 ?
N2 C3 C4 118.6(4) . . ?
C1 C3 C4 122.7(4) 3_566 . ?
C5 C4 C3 178.3(5) . . ?
C4 C5 C11 177.7(5) . . ?
C4 C5 C11B 162.5(10) . . ?
C16 C11 C12 117.5(5) . . ?
C16 C11 C5 121.8(5) . . ?
C12 C11 C5 120.7(5) . . ?
C13 C12 C11 121.4(5) . . ?
C13 C12 Cl2 119.2(5) . . ?
C11 C12 Cl2 119.4(4) . . ?
C14 C13 C12 119.4(6) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.2(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.1(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.5(6) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C16B C11B C12B 120(2) . . ?
C16B C11B C5 130(2) . . ?
C12B C11B C5 110(2) . . ?
C13B C12B C11B 122(2) . . ?
C13B C12B Cl2B 119(2) . . ?
C11B C12B Cl2B 118(2) . . ?
C13B C12B H12B 118.9 . . ?
C11B C12B H12B 118.9 . . ?
Cl2B C12B H12B 8.1 . . ?
C14B C13B C12B 116(2) . . ?
C14B C13B H13B 122.2 . . ?
C12B C13B H13B 122.2 . . ?
C13B C14B C15B 123(3) . . ?
C13B C14B H14B 118.5 . . ?
C15B C14B H14B 118.5 . . ?
C16B C15B C14B 120(3) . . ?
C16B C15B H15B 120.2 . . ?
C14B C15B H15B 120.2 . . ?
C15B C16B C11B 119(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 N2 C3 1.1(7) 3_566 . . . ?
Cl1 C1 N2 C3 179.8(3) . . . . ?
C1 N2 C3 C1 -1.1(7) . . . 3_566 ?
C1 N2 C3 C4 179.3(4) . . . . ?
C16 C11 C12 C13 1.7(8) . . . . ?
C5 C11 C12 C13 180.0(5) . . . . ?
C16 C11 C12 Cl2 -179.7(4) . . . . ?
C5 C11 C12 Cl2 -1.4(7) . . . . ?
C11 C12 C13 C14 -1.8(8) . . . . ?
Cl2 C12 C13 C14 179.6(4) . . . . ?
C12 C13 C14 C15 -0.2(9) . . . . ?
C13 C14 C15 C16 2.2(9) . . . . ?
C14 C15 C16 C11 -2.3(9) . . . . ?
C12 C11 C16 C15 0.4(8) . . . . ?
C5 C11 C16 C15 -177.9(5) . . . . ?
C4 C5 C11B C16B 0(11) . . . . ?
C4 C5 C11B C12B 174(4) . . . . ?
C16B C11B C12B C13B -6(9) . . . . ?
C5 C11B C12B C13B 180(5) . . . . ?
C16B C11B C12B Cl2B -176(4) . . . . ?
C5 C11B C12B Cl2B 9(6) . . . . ?
C11B C12B C13B C14B 0(9) . . . . ?
Cl2B C12B C13B C14B 170(5) . . . . ?
C12B C13B C14B C15B 10(10) . . . . ?
C13B C14B C15B C16B -14(11) . . . . ?
C14B C15B C16B C11B 8(10) . . . . ?
C12B C11B C16B C15B 2(9) . . . . ?
C5 C11B C16B C15B 175(5) . . . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_chr25
_database_code_depnum_ccdc_archive 'CCDC 2260643'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '2e in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H8 Br2 Cl2 N2'
_chemical_formula_weight         507.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8978(4)
_cell_length_b                   10.0989(10)
_cell_length_c                   12.0105(12)
_cell_angle_alpha                102.910(2)
_cell_angle_beta                 97.478(2)
_cell_angle_gamma                99.650(2)
_cell_volume                     447.34(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1567
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      21.93

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_F_000             246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    4.835
_shelx_estimated_absorpt_T_min   0.553
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7995
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6293
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.767
_diffrn_reflns_theta_max         27.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1873
_reflns_number_gt                1327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1873
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.46601(11) 0.16990(4) 0.06454(3) 0.04853(17) Uani 0.9780(12) 1 d . . P
A 1
Cl1 Cl 1.0082(2) 0.06595(9) 0.76036(7) 0.0403(3) Uani 1 1 d . . . . .
C1 C 1.0005(8) 0.0292(3) 0.6131(3) 0.0261(8) Uani 1 1 d . . . . .
N2 N 0.9029(6) 0.1197(2) 0.5585(2) 0.0266(6) Uani 1 1 d . . . . .
C3 C 0.9013(8) 0.0934(3) 0.4432(3) 0.0250(7) Uani 1 1 d . . . . .
C4 C 0.7977(8) 0.1916(3) 0.3840(3) 0.0281(8) Uani 1 1 d . . . . .
C5 C 0.7058(8) 0.2728(3) 0.3345(3) 0.0286(8) Uani 1 1 d . . . . .
C11 C 0.5815(8) 0.3729(3) 0.2798(3) 0.0254(8) Uani 1 1 d . . . . .
C12 C 0.4559(8) 0.3432(3) 0.1614(3) 0.0286(8) Uani 1 1 d . . . . .
H12 H 0.458259 0.254755 0.113672 0.034 Uiso 0.0220(12) 1 calc R U P A 2
C13 C 0.3280(8) 0.4401(4) 0.1120(3) 0.0370(9) Uani 1 1 d . . . . .
H13 H 0.243251 0.418330 0.030872 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3239(8) 0.5688(3) 0.1810(3) 0.0394(9) Uani 1 1 d . . . . .
H14 H 0.233349 0.635165 0.147270 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4502(8) 0.6018(3) 0.2987(3) 0.0364(9) Uani 1 1 d . . . . .
H15 H 0.448137 0.690642 0.345817 0.044 Uiso 1 1 calc R U . A .
C16 C 0.5788(9) 0.5050(4) 0.3469(3) 0.0331(9) Uani 1 1 d . . . . .
H16 H 0.668047 0.528243 0.427796 0.040 Uiso 0.9780(12) 1 calc R U P A 1
Br1B Br 0.663(8) 0.544(3) 0.421(2) 0.089(11) Uiso 0.0220(12) 1 d . . P A -2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.883(3) . ?
Cl1 C1 1.720(3) . ?
C1 N2 1.315(4) . ?
C1 C3 1.410(4) 2_756 ?
N2 C3 1.349(4) . ?
C3 C4 1.424(4) . ?
C4 C5 1.190(4) . ?
C5 C11 1.437(4) . ?
C11 C12 1.390(4) . ?
C11 C16 1.398(4) . ?
C11 Br1B 2.08(3) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(4) . ?
C15 Br1B 1.85(3) . ?
C15 H15 0.9500 . ?
C16 Br1B 0.88(3) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C3 123.2(3) . 2_756 ?
N2 C1 Cl1 117.1(2) . . ?
C3 C1 Cl1 119.7(2) 2_756 . ?
C1 N2 C3 117.7(3) . . ?
N2 C3 C1 119.0(3) . 2_756 ?
N2 C3 C4 117.8(3) . . ?
C1 C3 C4 123.1(3) 2_756 . ?
C5 C4 C3 179.0(4) . . ?
C4 C5 C11 176.5(4) . . ?
C12 C11 C16 117.8(3) . . ?
C12 C11 C5 122.5(3) . . ?
C16 C11 C5 119.8(3) . . ?
C12 C11 Br1B 136.4(8) . . ?
C16 C11 Br1B 18.8(8) . . ?
C5 C11 Br1B 101.1(8) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 Br1 118.6(3) . . ?
C11 C12 Br1 120.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 Br1B 27.0(9) . . ?
C14 C15 Br1B 146.3(10) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
Br1B C15 H15 93.4 . . ?
Br1B C16 C15 108(2) . . ?
Br1B C16 C11 130(2) . . ?
C15 C16 C11 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C16 Br1B C15 45.1(15) . . ?
C16 Br1B C11 30.8(14) . . ?
C15 Br1B C11 75.8(10) . . ?

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
C3 C1 N2 C3 -0.7(5) 2_756 . . . ?
Cl1 C1 N2 C3 178.9(2) . . . . ?
C1 N2 C3 C1 0.6(5) . . . 2_756 ?
C1 N2 C3 C4 -179.7(3) . . . . ?
C16 C11 C12 C13 -1.0(5) . . . . ?
C5 C11 C12 C13 177.9(3) . . . . ?
Br1B C11 C12 C13 -3.6(12) . . . . ?
C16 C11 C12 Br1 177.8(2) . . . . ?
C5 C11 C12 Br1 -3.3(4) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
Br1 C12 C13 C14 -178.9(2) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C13 C14 C15 Br1B 3.0(17) . . . . ?
C14 C15 C16 Br1B 176(2) . . . . ?
C14 C15 C16 C11 -0.7(5) . . . . ?
Br1B C15 C16 C11 -177(2) . . . . ?
C12 C11 C16 Br1B -174(3) . . . . ?
C5 C11 C16 Br1B 7(3) . . . . ?
C12 C11 C16 C15 1.3(5) . . . . ?
C5 C11 C16 C15 -177.6(3) . . . . ?
Br1B C11 C16 C15 176(3) . . . . ?
C11 C16 Br1B C15 176(3) . . . . ?
C15 C16 Br1B C11 -176(3) . . . . ?
C14 C15 Br1B C16 -7(3) . . . . ?
C16 C15 Br1B C11 2.0(13) . . . . ?
C14 C15 Br1B C11 -4(2) . . . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_chr34
_database_code_depnum_ccdc_archive 'CCDC 2260645'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '3b in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 N2 S2'
_chemical_formula_weight         484.69

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7524(8)
_cell_length_b                   8.7141(17)
_cell_length_c                   15.891(3)
_cell_angle_alpha                102.232(6)
_cell_angle_beta                 91.437(4)
_cell_angle_gamma                99.209(4)
_cell_volume                     633.68(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1353
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      20.50

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             258
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5536
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.314
_diffrn_reflns_theta_max         20.717
_diffrn_reflns_theta_full        20.717
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1316
_reflns_number_gt                1044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+0.2649P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1316
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.38261(19) 1.10500(10) 0.64369(6) 0.0367(3) Uani 1 1 d . . . . .
C2 C -0.1662(6) 1.0297(4) 0.56365(19) 0.0283(8) Uani 1 1 d . . . . .
N3 N -0.1047(6) 0.8839(3) 0.54992(18) 0.0317(7) Uani 1 1 d . . . . .
C4 C 0.0659(7) 0.8535(4) 0.4836(2) 0.0280(8) Uani 1 1 d . . . . .
C5 C 0.1733(7) 0.7095(4) 0.4547(2) 0.0310(9) Uani 1 1 d . . . . .
H5 H 0.128911 0.619799 0.480045 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3436(7) 0.7113(4) 0.3883(2) 0.0288(9) Uani 1 1 d . . . . .
C11 C 0.4960(7) 0.5871(4) 0.3443(2) 0.0271(8) Uani 1 1 d . . . . .
C12 C 0.4903(7) 0.4480(4) 0.3743(2) 0.0334(9) Uani 1 1 d . . . . .
H12 H 0.381247 0.432985 0.422072 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6396(7) 0.3318(4) 0.3361(2) 0.0344(9) Uani 1 1 d . . . . .
H13 H 0.634332 0.239200 0.358966 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7976(7) 0.3458(4) 0.2652(2) 0.0321(9) Uani 1 1 d . . . . .
C15 C 0.8004(7) 0.4840(4) 0.2347(2) 0.0410(10) Uani 1 1 d . . . . .
H15 H 0.906487 0.497599 0.186194 0.049 Uiso 1 1 calc R U . . .
C16 C 0.6535(7) 0.6024(4) 0.2730(2) 0.0400(10) Uani 1 1 d . . . . .
H16 H 0.660017 0.695357 0.250381 0.048 Uiso 1 1 calc R U . . .
C17 C 0.9490(7) 0.2138(4) 0.2226(2) 0.0389(9) Uani 1 1 d . . . . .
H17A H 1.036091 0.169727 0.267557 0.047 Uiso 1 1 calc R U . . .
H17B H 1.104742 0.257434 0.189687 0.047 Uiso 1 1 calc R U . . .
C18 C 0.7471(7) 0.0802(4) 0.1619(2) 0.0384(9) Uani 1 1 d . . . . .
H18A H 0.589970 0.038746 0.195037 0.046 Uiso 1 1 calc R U . . .
H18B H 0.661601 0.125140 0.117040 0.046 Uiso 1 1 calc R U . . .
C19 C 0.8871(7) -0.0566(4) 0.1181(2) 0.0388(10) Uani 1 1 d . . . . .
H19A H 0.972352 -0.101893 0.162818 0.047 Uiso 1 1 calc R U . . .
H19B H 1.044166 -0.015418 0.084814 0.047 Uiso 1 1 calc R U . . .
C20 C 0.6848(8) -0.1881(4) 0.0580(2) 0.0497(11) Uani 1 1 d . . . . .
H20A H 0.590700 -0.141581 0.015494 0.060 Uiso 1 1 calc R U . . .
H20B H 0.534228 -0.233664 0.091997 0.060 Uiso 1 1 calc R U . . .
C21 C 0.8275(9) -0.3212(4) 0.0100(2) 0.0649(13) Uani 1 1 d . . . . .
H21A H 0.687453 -0.397349 -0.030957 0.097 Uiso 1 1 calc R U . . .
H21B H 0.903662 -0.375667 0.051175 0.097 Uiso 1 1 calc R U . . .
H21C H 0.983860 -0.276658 -0.021467 0.097 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 C2 1.742(3) . ?
S1 C6 1.763(3) 2_576 ?
C2 N3 1.324(4) . ?
C2 C4 1.419(4) 2_576 ?
N3 C4 1.353(4) . ?
C4 C5 1.421(4) . ?
C5 C6 1.348(4) . ?
C5 H5 0.9500 . ?
C6 C11 1.463(4) . ?
C11 C12 1.390(4) . ?
C11 C16 1.391(4) . ?
C12 C13 1.374(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(4) . ?
C14 C17 1.503(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.526(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.508(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.512(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.513(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C2 S1 C6 91.45(16) . 2_576 ?
N3 C2 C4 125.4(3) . 2_576 ?
N3 C2 S1 124.1(3) . . ?
C4 C2 S1 110.5(3) 2_576 . ?
C2 N3 C4 112.9(3) . . ?
N3 C4 C2 121.8(3) . 2_576 ?
N3 C4 C5 126.0(3) . . ?
C2 C4 C5 112.2(3) 2_576 . ?
C6 C5 C4 114.1(3) . . ?
C6 C5 H5 122.9 . . ?
C4 C5 H5 122.9 . . ?
C5 C6 C11 128.9(3) . . ?
C5 C6 S1 111.7(2) . 2_576 ?
C11 C6 S1 119.3(2) . 2_576 ?
C12 C11 C16 117.4(3) . . ?
C12 C11 C6 120.0(3) . . ?
C16 C11 C6 122.6(3) . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C15 116.7(3) . . ?
C13 C14 C17 120.7(3) . . ?
C15 C14 C17 122.5(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C11 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C14 C17 C18 112.0(3) . . ?
C14 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C14 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 114.2(3) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 113.7(3) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.9(3) . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C6 S1 C2 N3 -179.0(3) 2_576 . . . ?
C6 S1 C2 C4 1.3(2) 2_576 . . 2_576 ?
C4 C2 N3 C4 -0.8(5) 2_576 . . . ?
S1 C2 N3 C4 179.5(2) . . . . ?
C2 N3 C4 C2 0.8(5) . . . 2_576 ?
C2 N3 C4 C5 178.5(3) . . . . ?
N3 C4 C5 C6 -178.7(3) . . . . ?
C2 C4 C5 C6 -0.9(4) 2_576 . . . ?
C4 C5 C6 C11 178.1(3) . . . . ?
C4 C5 C6 S1 -0.1(3) . . . 2_576 ?
C5 C6 C11 C12 -4.5(5) . . . . ?
S1 C6 C11 C12 173.6(2) 2_576 . . . ?
C5 C6 C11 C16 176.5(3) . . . . ?
S1 C6 C11 C16 -5.4(4) 2_576 . . . ?
C16 C11 C12 C13 1.4(5) . . . . ?
C6 C11 C12 C13 -177.7(3) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C12 C13 C14 C17 -177.5(3) . . . . ?
C13 C14 C15 C16 0.0(5) . . . . ?
C17 C14 C15 C16 178.1(3) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C12 C11 C16 C15 -0.8(5) . . . . ?
C6 C11 C16 C15 178.3(3) . . . . ?
C13 C14 C17 C18 80.4(4) . . . . ?
C15 C14 C17 C18 -97.6(4) . . . . ?
C14 C17 C18 C19 -179.3(3) . . . . ?
C17 C18 C19 C20 -180.0(3) . . . . ?
C18 C19 C20 C21 176.6(3) . . . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041


# start Validation Reply Form
_vrf_THETM01_chr34               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: We have cut the dataset at a resolution of 1.00 A due to 
I/sigma and R(int) criteria. Despite of using a high intensity source 
and long irradiation times this was the best achievable resolution. 
The data to parameter ratio is still acceptable.
;
# end Validation Reply Form

#==================================================================
