# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ebu1
_database_code_depnum_ccdc_archive 'CCDC 2353527'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '5 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H20 Cl2'
_chemical_formula_weight         499.40

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3543(14)
_cell_length_b                   7.0091(9)
_cell_length_c                   14.5933(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.237(3)
_cell_angle_gamma                90
_cell_volume                     1161.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2539
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.03

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9230
_exptl_absorpt_correction_T_max  0.9594
_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            12148
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2667
_reflns_number_gt                1862
_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)+(0.0340P)²+0.5746P] 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         2667
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.31228(4) 0.81990(8) 0.52021(4) 0.03752(18) Uani 1 1 d . . . . .
C1 C 0.41517(17) 0.6376(3) 0.50881(14) 0.0262(5) Uani 1 1 d . . . . .
C2 C 0.53377(16) 0.6845(3) 0.51867(14) 0.0277(5) Uani 1 1 d . . . . .
H2 H 0.555453 0.812852 0.531510 0.033 Uiso 1 1 calc R U . . .
C3 C 0.62107(16) 0.5474(3) 0.51010(14) 0.0253(5) Uani 1 1 d . . . . .
C11 C 0.74779(16) 0.6064(3) 0.51973(14) 0.0257(5) Uani 1 1 d . . . . .
C12 C 0.80577(16) 0.6786(3) 0.44319(14) 0.0262(5) Uani 1 1 d . . . . .
C13 C 0.75205(18) 0.6879(3) 0.35388(15) 0.0349(5) Uani 1 1 d . . . . .
H13 H 0.672962 0.646324 0.345169 0.042 Uiso 1 1 calc R U . . .
C14 C 0.8121(2) 0.7550(4) 0.28135(17) 0.0437(6) Uani 1 1 d . . . . .
H14 H 0.774455 0.759394 0.222617 0.052 Uiso 1 1 calc R U . . .
C15 C 0.9295(2) 0.8185(4) 0.29164(17) 0.0429(6) Uani 1 1 d . . . . .
H15 H 0.970246 0.865008 0.240032 0.051 Uiso 1 1 calc R U . . .
C16 C 0.98417(19) 0.8132(3) 0.37469(17) 0.0374(6) Uani 1 1 d . . . . .
H16 H 1.063292 0.856218 0.380810 0.045 Uiso 1 1 calc R U . . .
C17 C 0.92520(17) 0.7442(3) 0.45342(16) 0.0283(5) Uani 1 1 d . . . . .
C18 C 0.97960(17) 0.7388(3) 0.53929(16) 0.0318(5) Uani 1 1 d . . . . .
H18 H 1.057985 0.784837 0.546132 0.038 Uiso 1 1 calc R U . . .
C19 C 0.92305(17) 0.6680(3) 0.61583(15) 0.0292(5) Uani 1 1 d . . . . .
C20 C 0.97939(19) 0.6629(3) 0.70413(17) 0.0375(6) Uani 1 1 d . . . . .
H20 H 1.057555 0.709742 0.711313 0.045 Uiso 1 1 calc R U . . .
C21 C 0.9238(2) 0.5927(3) 0.77757(17) 0.0417(6) Uani 1 1 d . . . . .
H21 H 0.962800 0.591269 0.835806 0.050 Uiso 1 1 calc R U . . .
C22 C 0.8074(2) 0.5212(3) 0.76828(16) 0.0394(6) Uani 1 1 d . . . . .
H22 H 0.769155 0.471054 0.820311 0.047 Uiso 1 1 calc R U . . .
C23 C 0.75015(19) 0.5237(3) 0.68592(15) 0.0331(5) Uani 1 1 d . . . . .
H23 H 0.672183 0.475016 0.681116 0.040 Uiso 1 1 calc R U . . .
C24 C 0.80452(17) 0.5980(3) 0.60613(14) 0.0260(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.742(2) . ?
C1 C3 1.386(3) 3_666 ?
C1 C2 1.391(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C11 1.501(3) . ?
C11 C12 1.403(3) . ?
C11 C24 1.405(3) . ?
C12 C13 1.429(3) . ?
C12 C17 1.437(3) . ?
C13 C14 1.356(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.411(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.350(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.427(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.427(3) . ?
C19 C24 1.436(3) . ?
C20 C21 1.348(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.417(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.354(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.428(3) . ?
C23 H23 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
C3 C1 C2 121.64(19) 3_666 . ?
C3 C1 Cl1 120.56(15) 3_666 . ?
C2 C1 Cl1 117.80(16) . . ?
C3 C2 C1 121.23(19) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C1 C3 C2 117.14(17) 3_666 . ?
C1 C3 C11 123.79(18) 3_666 . ?
C2 C3 C11 119.06(18) . . ?
C12 C11 C24 121.04(18) . . ?
C12 C11 C3 119.35(18) . . ?
C24 C11 C3 119.52(18) . . ?
C11 C12 C13 122.98(18) . . ?
C11 C12 C17 119.39(19) . . ?
C13 C12 C17 117.62(19) . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.1(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 122.0(2) . . ?
C18 C17 C12 119.11(19) . . ?
C16 C17 C12 118.9(2) . . ?
C17 C18 C19 122.09(19) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C20 121.88(19) . . ?
C18 C19 C24 119.34(19) . . ?
C20 C19 C24 118.8(2) . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 120.6(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 121.4(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C11 C24 C23 123.31(18) . . ?
C11 C24 C19 119.00(19) . . ?
C23 C24 C19 117.69(19) . . ?

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 C2 C3 -0.1(4) 3_666 . . . ?
Cl1 C1 C2 C3 -179.68(16) . . . . ?
C1 C2 C3 C1 0.1(3) . . . 3_666 ?
C1 C2 C3 C11 178.93(19) . . . . ?
C1 C3 C11 C12 93.9(3) 3_666 . . . ?
C2 C3 C11 C12 -84.9(2) . . . . ?
C1 C3 C11 C24 -89.5(3) 3_666 . . . ?
C2 C3 C11 C24 91.7(2) . . . . ?
C24 C11 C12 C13 179.3(2) . . . . ?
C3 C11 C12 C13 -4.1(3) . . . . ?
C24 C11 C12 C17 0.3(3) . . . . ?
C3 C11 C12 C17 176.83(18) . . . . ?
C11 C12 C13 C14 -178.6(2) . . . . ?
C17 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 -179.6(2) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C11 C12 C17 C18 -1.5(3) . . . . ?
C13 C12 C17 C18 179.42(19) . . . . ?
C11 C12 C17 C16 178.56(19) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C16 C17 C18 C19 -178.7(2) . . . . ?
C12 C17 C18 C19 1.4(3) . . . . ?
C17 C18 C19 C20 -179.9(2) . . . . ?
C17 C18 C19 C24 0.0(3) . . . . ?
C18 C19 C20 C21 -179.6(2) . . . . ?
C24 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C12 C11 C24 C23 -179.2(2) . . . . ?
C3 C11 C24 C23 4.3(3) . . . . ?
C12 C11 C24 C19 1.1(3) . . . . ?
C3 C11 C24 C19 -175.47(18) . . . . ?
C22 C23 C24 C11 -178.9(2) . . . . ?
C22 C23 C24 C19 0.8(3) . . . . ?
C18 C19 C24 C11 -1.2(3) . . . . ?
C20 C19 C24 C11 178.71(19) . . . . ?
C18 C19 C24 C23 179.0(2) . . . . ?
C20 C19 C24 C23 -1.0(3) . . . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052


####################################################################### 
# 
# 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_sve108
_database_code_depnum_ccdc_archive 'CCDC 2353530'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '8 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H40 Cl8 N2'
_chemical_formula_weight         976.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      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                   8.3208(10)
_cell_length_b                   8.8810(11)
_cell_length_c                   16.692(2)
_cell_angle_alpha                102.240(3)
_cell_angle_beta                 99.833(3)
_cell_angle_gamma                103.716(3)
_cell_volume                     1138.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3202
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.15

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             502
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.534
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9236
_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            20391
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.284
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4907
_reflns_number_gt                3003
_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)+(0.0434P)²+0.7065P] 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         4907
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Cl1 Cl -0.36578(9) 0.38982(10) 0.01499(5) 0.0327(2) Uani 1 1 d . . . . .
C2 C -0.1580(3) 0.4515(3) 0.00538(17) 0.0226(6) Uani 1 1 d . . . . .
N3 N -0.0413(3) 0.4322(3) 0.06389(14) 0.0253(6) Uani 1 1 d . . . . .
C4 C 0.1217(3) 0.4813(3) 0.05997(17) 0.0226(6) Uani 1 1 d . . . . .
C11 C 0.2531(3) 0.4594(3) 0.12673(17) 0.0225(6) Uani 1 1 d . . . . .
C12 C 0.2949(3) 0.3133(3) 0.11337(16) 0.0220(6) Uani 1 1 d . . . . .
C13 C 0.2221(4) 0.1864(4) 0.03792(18) 0.0285(7) Uani 1 1 d . . . . .
H13 H 0.140481 0.199807 -0.005273 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2662(4) 0.0471(4) 0.02623(19) 0.0343(8) Uani 1 1 d . . . . .
H14 H 0.217378 -0.034521 -0.025089 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3847(4) 0.0235(4) 0.09032(19) 0.0359(8) Uani 1 1 d . . . . .
H15 H 0.415157 -0.074281 0.081783 0.043 Uiso 1 1 calc R U . . .
C16 C 0.4554(4) 0.1386(4) 0.16376(19) 0.0299(7) Uani 1 1 d . . . . .
H16 H 0.533359 0.119194 0.206306 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4156(3) 0.2885(3) 0.17892(17) 0.0222(6) Uani 1 1 d . . . . .
C18 C 0.4898(3) 0.4087(3) 0.25480(17) 0.0218(6) Uani 1 1 d . . . . .
C19 C 0.4501(3) 0.5561(3) 0.26609(17) 0.0236(6) Uani 1 1 d . . . . .
C20 C 0.5284(4) 0.6847(4) 0.34023(18) 0.0304(7) Uani 1 1 d . . . . .
H20 H 0.609347 0.670371 0.383411 0.036 Uiso 1 1 calc R U . . .
C21 C 0.4905(4) 0.8271(4) 0.35077(19) 0.0360(8) Uani 1 1 d . . . . .
H21 H 0.546700 0.911604 0.400219 0.043 Uiso 1 1 calc R U . . .
C22 C 0.3674(4) 0.8498(4) 0.2883(2) 0.0380(8) Uani 1 1 d . . . . .
H22 H 0.339395 0.948751 0.297023 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2886(4) 0.7323(4) 0.21611(19) 0.0314(7) Uani 1 1 d . . . . .
H23 H 0.206325 0.750066 0.174934 0.038 Uiso 1 1 calc R U . . .
C24 C 0.3283(3) 0.5814(3) 0.20133(17) 0.0235(6) Uani 1 1 d . . . . .
C31 C 0.6073(4) 0.3755(3) 0.32365(17) 0.0239(6) Uani 1 1 d . . . . .
C32 C 0.7772(4) 0.3869(4) 0.32120(18) 0.0285(7) Uani 1 1 d . . . . .
C33 C 0.8776(4) 0.3435(4) 0.38328(19) 0.0352(8) Uani 1 1 d . . . . .
H33 H 0.992375 0.349778 0.381308 0.042 Uiso 1 1 calc R U . . .
C34 C 0.8162(4) 0.2917(4) 0.44738(19) 0.0379(8) Uani 1 1 d . . . . .
C35 C 0.6491(4) 0.2852(4) 0.44948(18) 0.0347(8) Uani 1 1 d . . . . .
H35 H 0.605462 0.251340 0.493755 0.042 Uiso 1 1 calc R U . . .
C36 C 0.5428(4) 0.3263(3) 0.38910(18) 0.0278(7) Uani 1 1 d . . . . .
C37 C 0.8510(4) 0.4434(5) 0.2527(2) 0.0450(9) Uani 1 1 d . . . . .
H37A H 0.974371 0.460456 0.266302 0.067 Uiso 1 1 calc R U . . .
H37B H 0.826608 0.544483 0.248519 0.067 Uiso 1 1 calc R U . . .
H37C H 0.799974 0.361966 0.198846 0.067 Uiso 1 1 calc R U . . .
C38 C 0.9256(5) 0.2417(5) 0.5132(2) 0.0595(12) Uani 1 1 d . . . . .
H38A H 0.895868 0.272101 0.567549 0.089 Uiso 1 1 calc R U . . .
H38B H 1.045751 0.295500 0.518662 0.089 Uiso 1 1 calc R U . . .
H38C H 0.905997 0.124984 0.496144 0.089 Uiso 1 1 calc R U . . .
C39 C 0.3614(4) 0.3171(4) 0.3952(2) 0.0402(8) Uani 1 1 d . . . . .
H39A H 0.333332 0.261198 0.437886 0.060 Uiso 1 1 calc R U . . .
H39B H 0.283909 0.258078 0.340470 0.060 Uiso 1 1 calc R U . . .
H39C H 0.349622 0.425937 0.411167 0.060 Uiso 1 1 calc R U . . .
C41 C 1.1400(4) 0.0287(4) 0.7597(2) 0.0407(8) Uani 1 1 d . . . . .
H41 H 1.203385 -0.049781 0.741096 0.049 Uiso 1 1 calc R U . . .
Cl2 Cl 0.98804(14) -0.06141(15) 0.80846(7) 0.0774(4) Uani 1 1 d . . . . .
Cl3 Cl 1.04063(12) 0.07469(13) 0.67033(6) 0.0573(3) Uani 1 1 d . . . . .
Cl4 Cl 1.28507(13) 0.19925(13) 0.83027(6) 0.0600(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.731(3) . ?
C2 N3 1.324(3) . ?
C2 C4 1.393(4) 2_565 ?
N3 C4 1.340(3) . ?
C4 C11 1.501(4) . ?
C11 C24 1.399(4) . ?
C11 C12 1.405(4) . ?
C12 C13 1.427(4) . ?
C12 C17 1.444(4) . ?
C13 C14 1.356(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.412(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.353(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.429(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.404(4) . ?
C18 C19 1.407(4) . ?
C18 C31 1.503(4) . ?
C19 C20 1.426(4) . ?
C19 C24 1.443(4) . ?
C20 C21 1.358(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.413(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.358(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.436(4) . ?
C23 H23 0.9500 . ?
C31 C36 1.402(4) . ?
C31 C32 1.402(4) . ?
C32 C33 1.395(4) . ?
C32 C37 1.507(4) . ?
C33 C34 1.379(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(5) . ?
C34 C38 1.514(4) . ?
C35 C36 1.392(4) . ?
C35 H35 0.9500 . ?
C36 C39 1.514(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C41 Cl4 1.740(4) . ?
C41 Cl2 1.745(3) . ?
C41 Cl3 1.754(3) . ?
C41 H41 1.0000 . ?

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
N3 C2 C4 124.0(2) . 2_565 ?
N3 C2 Cl1 115.6(2) . . ?
C4 C2 Cl1 120.3(2) 2_565 . ?
C2 N3 C4 117.7(2) . . ?
N3 C4 C2 118.3(2) . 2_565 ?
N3 C4 C11 117.3(2) . . ?
C2 C4 C11 124.4(2) 2_565 . ?
C24 C11 C12 121.3(2) . . ?
C24 C11 C4 120.1(2) . . ?
C12 C11 C4 118.6(2) . . ?
C11 C12 C13 123.0(2) . . ?
C11 C12 C17 118.9(2) . . ?
C13 C12 C17 118.1(3) . . ?
C14 C13 C12 121.8(3) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 C12 120.5(2) . . ?
C16 C17 C12 117.8(3) . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 C31 119.1(2) . . ?
C19 C18 C31 121.1(2) . . ?
C18 C19 C20 121.9(3) . . ?
C18 C19 C24 120.1(3) . . ?
C20 C19 C24 118.0(3) . . ?
C21 C20 C19 121.7(3) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 120.7(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C11 C24 C23 122.3(2) . . ?
C11 C24 C19 119.3(2) . . ?
C23 C24 C19 118.4(3) . . ?
C36 C31 C32 120.0(3) . . ?
C36 C31 C18 119.0(3) . . ?
C32 C31 C18 120.9(2) . . ?
C33 C32 C31 118.7(3) . . ?
C33 C32 C37 120.2(3) . . ?
C31 C32 C37 121.1(3) . . ?
C34 C33 C32 122.4(3) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C33 C34 C35 117.8(3) . . ?
C33 C34 C38 121.7(3) . . ?
C35 C34 C38 120.5(3) . . ?
C34 C35 C36 122.4(3) . . ?
C34 C35 H35 118.8 . . ?
C36 C35 H35 118.8 . . ?
C35 C36 C31 118.7(3) . . ?
C35 C36 C39 119.8(3) . . ?
C31 C36 C39 121.5(3) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
Cl4 C41 Cl2 110.69(19) . . ?
Cl4 C41 Cl3 111.24(19) . . ?
Cl2 C41 Cl3 110.29(18) . . ?
Cl4 C41 H41 108.2 . . ?
Cl2 C41 H41 108.2 . . ?
Cl3 C41 H41 108.2 . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.065


####################################################################### 
# 
# 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_sve109
_database_code_depnum_ccdc_archive 'CCDC 2353531'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'DBAF in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H18'
_chemical_formula_weight         426.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.8885(4)
_cell_length_b                   12.3614(6)
_cell_length_c                   10.6250(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.462(4)
_cell_angle_gamma                90
_cell_volume                     1024.80(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5143
_cell_measurement_theta_min      5.53
_cell_measurement_theta_max      68.67

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.599
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9059
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 2.7.5.0 (STOE, 2022)'
_diffrn_ambient_temperature      200(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            8017
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.525
_diffrn_reflns_theta_max         68.492
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1856
_reflns_number_gt                1216
_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 1.31.186.0 (STOE, 2022)'
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_reduction        'X-Area Integrate 2.5.3.0 (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)+(0.0640P)²+0.2989P] 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         1856
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.8561(3) 0.56389(19) 0.5137(2) 0.0320(5) Uani 1 1 d . . . . .
C2 C 0.8954(3) 0.46744(19) 0.5857(2) 0.0317(5) Uani 1 1 d . . . . .
C3 C 1.0369(3) 0.4041(2) 0.5733(2) 0.0338(6) Uani 1 1 d . . . . .
H3 H 1.060663 0.340400 0.622762 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7612(3) 0.4509(2) 0.6661(2) 0.0325(6) Uani 1 1 d . . . . .
C12 C 0.7298(3) 0.3739(2) 0.7515(2) 0.0365(6) Uani 1 1 d . . . . .
H12 H 0.805747 0.314563 0.770766 0.044 Uiso 1 1 calc R U . . .
C13 C 0.5801(3) 0.3845(2) 0.8112(2) 0.0410(6) Uani 1 1 d . . . . .
H13 H 0.558403 0.331486 0.871616 0.049 Uiso 1 1 calc R U . . .
C14 C 0.4668(3) 0.4677(2) 0.7850(2) 0.0405(6) Uani 1 1 d . . . . .
H14 H 0.368303 0.471220 0.826688 0.049 Uiso 1 1 calc R U . . .
C15 C 0.4948(3) 0.5497(2) 0.6954(2) 0.0346(6) Uani 1 1 d . . . . .
C16 C 0.3905(3) 0.63748(19) 0.6556(2) 0.0350(6) Uani 1 1 d . . . . .
H16 H 0.287260 0.647899 0.690125 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4352(3) 0.7110(2) 0.5655(2) 0.0353(6) Uani 1 1 d . . . . .
C18 C 0.3275(3) 0.8016(2) 0.5266(2) 0.0416(6) Uani 1 1 d . . . . .
H18 H 0.223514 0.810015 0.560670 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3690(3) 0.8753(2) 0.4431(3) 0.0457(7) Uani 1 1 d . . . . .
H19 H 0.294784 0.934934 0.420229 0.055 Uiso 1 1 calc R U . . .
C20 C 0.5221(3) 0.8652(2) 0.3890(3) 0.0433(7) Uani 1 1 d . . . . .
H20 H 0.550735 0.917629 0.330256 0.052 Uiso 1 1 calc R U . . .
C21 C 0.6282(3) 0.7790(2) 0.4221(2) 0.0386(6) Uani 1 1 d . . . . .
H21 H 0.730159 0.772624 0.384945 0.046 Uiso 1 1 calc R U . . .
C22 C 0.5920(3) 0.69885(19) 0.5098(2) 0.0322(6) Uani 1 1 d . . . . .
C23 C 0.6964(3) 0.60911(19) 0.5480(2) 0.0307(5) Uani 1 1 d . . . . .
C24 C 0.6452(3) 0.53830(19) 0.6388(2) 0.0311(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.397(3) 3_766 ?
C1 C2 1.426(3) . ?
C1 C23 1.472(3) . ?
C2 C3 1.386(3) . ?
C2 C11 1.470(3) . ?
C3 H3 0.9500 . ?
C11 C12 1.362(3) . ?
C11 C24 1.419(3) . ?
C12 C13 1.427(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.430(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 C24 1.414(3) . ?
C16 C17 1.402(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.430(3) . ?
C17 C22 1.455(3) . ?
C18 C19 1.345(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.418(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.418(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.406(3) . ?
C23 C24 1.405(3) . ?

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
C3 C1 C2 119.1(2) 3_766 . ?
C3 C1 C23 132.7(2) 3_766 . ?
C2 C1 C23 108.16(18) . . ?
C3 C2 C1 122.4(2) . . ?
C3 C2 C11 129.5(2) . . ?
C1 C2 C11 108.06(19) . . ?
C2 C3 C1 118.4(2) . 3_766 ?
C2 C3 H3 120.8 . . ?
C1 C3 H3 120.8 3_766 . ?
C12 C11 C24 119.6(2) . . ?
C12 C11 C2 134.6(2) . . ?
C24 C11 C2 105.82(19) . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 122.6(2) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C24 116.4(2) . . ?
C16 C15 C14 127.8(2) . . ?
C24 C15 C14 115.7(2) . . ?
C15 C16 C17 121.1(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 C22 121.7(2) . . ?
C18 C17 C22 117.8(2) . . ?
C19 C18 C17 122.0(2) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 122.6(2) . . ?
C20 C21 H21 118.7 . . ?
C22 C21 H21 118.7 . . ?
C23 C22 C21 125.1(2) . . ?
C23 C22 C17 117.5(2) . . ?
C21 C22 C17 117.5(2) . . ?
C24 C23 C22 118.3(2) . . ?
C24 C23 C1 106.04(19) . . ?
C22 C23 C1 135.7(2) . . ?
C23 C24 C15 125.0(2) . . ?
C23 C24 C11 111.92(19) . . ?
C15 C24 C11 123.0(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 C2 C3 0.4(4) 3_766 . . . ?
C23 C1 C2 C3 178.6(2) . . . . ?
C3 C1 C2 C11 -178.3(2) 3_766 . . . ?
C23 C1 C2 C11 -0.1(3) . . . . ?
C1 C2 C3 C1 -0.4(4) . . . 3_766 ?
C11 C2 C3 C1 178.0(2) . . . 3_766 ?
C3 C2 C11 C12 0.4(4) . . . . ?
C1 C2 C11 C12 179.0(3) . . . . ?
C3 C2 C11 C24 -178.3(2) . . . . ?
C1 C2 C11 C24 0.3(2) . . . . ?
C24 C11 C12 C13 -0.3(3) . . . . ?
C2 C11 C12 C13 -178.9(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 178.1(2) . . . . ?
C13 C14 C15 C24 -0.4(4) . . . . ?
C24 C15 C16 C17 -0.9(3) . . . . ?
C14 C15 C16 C17 -179.4(2) . . . . ?
C15 C16 C17 C18 -179.3(2) . . . . ?
C15 C16 C17 C22 -0.1(4) . . . . ?
C16 C17 C18 C19 178.0(2) . . . . ?
C22 C17 C18 C19 -1.2(4) . . . . ?
C17 C18 C19 C20 0.7(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C22 -0.4(4) . . . . ?
C20 C21 C22 C23 -179.6(2) . . . . ?
C20 C21 C22 C17 -0.2(4) . . . . ?
C16 C17 C22 C23 1.2(3) . . . . ?
C18 C17 C22 C23 -179.5(2) . . . . ?
C16 C17 C22 C21 -178.3(2) . . . . ?
C18 C17 C22 C21 1.0(3) . . . . ?
C21 C22 C23 C24 178.2(2) . . . . ?
C17 C22 C23 C24 -1.3(3) . . . . ?
C21 C22 C23 C1 -3.7(4) . . . . ?
C17 C22 C23 C1 176.8(2) . . . . ?
C3 C1 C23 C24 177.8(2) 3_766 . . . ?
C2 C1 C23 C24 -0.2(3) . . . . ?
C3 C1 C23 C22 -0.5(5) 3_766 . . . ?
C2 C1 C23 C22 -178.4(3) . . . . ?
C22 C23 C24 C15 0.3(3) . . . . ?
C1 C23 C24 C15 -178.3(2) . . . . ?
C22 C23 C24 C11 179.0(2) . . . . ?
C1 C23 C24 C11 0.4(3) . . . . ?
C16 C15 C24 C23 0.8(3) . . . . ?
C14 C15 C24 C23 179.5(2) . . . . ?
C16 C15 C24 C11 -177.7(2) . . . . ?
C14 C15 C24 C11 1.0(3) . . . . ?
C12 C11 C24 C23 -179.4(2) . . . . ?
C2 C11 C24 C23 -0.4(3) . . . . ?
C12 C11 C24 C15 -0.6(3) . . . . ?
C2 C11 C24 C15 178.3(2) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.044


####################################################################### 
# 
# 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_sve111
_database_code_depnum_ccdc_archive 'CCDC 2353528'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '6 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H18 Cl2 N2'
_chemical_formula_weight         501.38

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.4735(5)
_cell_length_b                   8.1885(3)
_cell_length_c                   16.7772(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.305(5)
_cell_angle_gamma                90
_cell_volume                     1160.81(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5440
_cell_measurement_theta_min      6.01
_cell_measurement_theta_max      68.38

_exptl_crystal_description       plank
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.708
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 2.7.5.0 (STOE, 2022)'
_diffrn_ambient_temperature      200(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            11856
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.1363
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.016
_diffrn_reflns_theta_max         68.914
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2051
_reflns_number_gt                1259
_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 1.31.186.0 (STOE, 2022)'
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_reduction        'X-Area Integrate 2.5.3.0 (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)+(0.0422P)²+0.3147P] 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         2051
_refine_ls_number_parameters     173
_refine_ls_number_restraints     157
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      0.974
_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 0.56169(10) 0.17051(10) 0.58017(5) 0.0447(3) Uani 0.894(3) 1 d . . P A 1
C1 C 0.5296(3) 0.3565(3) 0.53349(17) 0.0376(7) Uani 0.894(3) 1 d . . P A 1
N2 N 0.4523(3) 0.4640(3) 0.57522(15) 0.0380(6) Uani 0.894(3) 1 d . . P A 1
Cl1B Cl 0.4202(9) 0.3651(11) 0.6593(5) 0.059(3) Uani 0.106(3) 1 d . . P A 2
C1B C 0.4523(3) 0.4640(3) 0.57522(15) 0.0380(6) Uani 0.106(3) 1 d . . P A 2
N2B N 0.5296(3) 0.3565(3) 0.53349(17) 0.0376(7) Uani 0.106(3) 1 d . . P A 2
C3 C 0.4203(3) 0.6119(3) 0.54208(17) 0.0352(7) Uani 1 1 d . . . . .
C11 C 0.3346(3) 0.7320(3) 0.58963(18) 0.0362(7) Uani 1 1 d . . . . .
C12 C 0.4140(3) 0.8060(4) 0.65719(18) 0.0389(7) Uani 1 1 d . . . . .
C13 C 0.5760(4) 0.7740(4) 0.68232(19) 0.0473(8) Uani 1 1 d . . . . .
H13 H 0.633805 0.697539 0.653450 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6485(4) 0.8508(5) 0.7465(2) 0.0566(9) Uani 1 1 d . . . . .
H14 H 0.756771 0.828789 0.761515 0.068 Uiso 1 1 calc R U . . .
C15 C 0.5652(4) 0.9631(5) 0.7915(2) 0.0606(9) Uani 1 1 d . . . . .
H15 H 0.617148 1.015956 0.836575 0.073 Uiso 1 1 calc R U . . .
C16 C 0.4110(4) 0.9951(4) 0.7702(2) 0.0550(9) Uani 1 1 d . . . . .
H16 H 0.356218 1.071041 0.800911 0.066 Uiso 1 1 calc R U . . .
C17 C 0.3289(4) 0.9189(4) 0.70361(19) 0.0454(8) Uani 1 1 d . . . . .
C18 C 0.1720(4) 0.9523(4) 0.6813(2) 0.0476(8) Uani 1 1 d . . . . .
H18 H 0.117012 1.027423 0.712298 0.057 Uiso 1 1 calc R U . . .
C19 C 0.0921(4) 0.8804(3) 0.61548(19) 0.0414(7) Uani 1 1 d . . . . .
C20 C -0.0703(4) 0.9146(4) 0.5928(2) 0.0504(8) Uani 1 1 d . . . . .
H20 H -0.126095 0.988774 0.623915 0.060 Uiso 1 1 calc R U . . .
C21 C -0.1463(4) 0.8439(4) 0.5282(2) 0.0524(8) Uani 1 1 d . . . . .
H21 H -0.254172 0.869457 0.514085 0.063 Uiso 1 1 calc R U . . .
C22 C -0.0663(4) 0.7325(4) 0.4816(2) 0.0490(8) Uani 1 1 d . . . . .
H22 H -0.120686 0.682916 0.436261 0.059 Uiso 1 1 calc R U . . .
C23 C 0.0886(3) 0.6953(4) 0.5010(2) 0.0435(7) Uani 1 1 d . . . . .
H23 H 0.140102 0.618904 0.469170 0.052 Uiso 1 1 calc R U . . .
C24 C 0.1748(3) 0.7679(3) 0.56762(18) 0.0369(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.725(3) . ?
C1 N2 1.327(3) . ?
C1 C3 1.391(4) 3_666 ?
N2 C3 1.352(4) . ?
Cl1B C1B 1.667(8) . ?
C1B N2B 1.327(3) . ?
C1B C3 1.352(4) . ?
N2B C3 1.391(4) 3_666 ?
C3 C11 1.489(4) . ?
C11 C24 1.408(4) . ?
C11 C12 1.411(4) . ?
C12 C13 1.430(4) . ?
C12 C17 1.437(4) . ?
C13 C14 1.354(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.412(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.354(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.417(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(4) . ?
C18 C19 1.383(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.428(4) . ?
C19 C24 1.438(4) . ?
C20 C21 1.349(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.408(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.363(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.419(4) . ?
C23 H23 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 123.6(3) . 3_666 ?
N2 C1 Cl1 114.4(2) . . ?
C3 C1 Cl1 121.9(2) 3_666 . ?
C1 N2 C3 118.0(2) . . ?
N2B C1B C3 118.0(2) . . ?
N2B C1B Cl1B 104.1(3) . . ?
C3 C1B Cl1B 138.0(3) . . ?
C1B N2B C3 123.6(3) . 3_666 ?
N2 C3 C1 118.4(2) . 3_666 ?
C1B C3 C11 117.5(2) . . ?
N2 C3 C11 117.5(2) . . ?
C1 C3 C11 124.1(3) 3_666 . ?
C24 C11 C12 120.8(3) . . ?
C24 C11 C3 119.7(3) . . ?
C12 C11 C3 119.5(2) . . ?
C11 C12 C13 123.2(3) . . ?
C11 C12 C17 118.9(3) . . ?
C13 C12 C17 117.9(3) . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 122.0(3) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 122.1(3) . . ?
C18 C17 C12 119.5(3) . . ?
C16 C17 C12 118.3(3) . . ?
C17 C18 C19 122.4(3) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 122.2(3) . . ?
C18 C19 C24 119.3(3) . . ?
C20 C19 C24 118.5(3) . . ?
C21 C20 C19 121.5(3) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.6(3) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C11 C24 C23 123.2(3) . . ?
C11 C24 C19 119.1(3) . . ?
C23 C24 C19 117.7(3) . . ?

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 0.2(5) 3_666 . . . ?
Cl1 C1 N2 C3 -179.0(2) . . . . ?
C3 C1B N2B C3 0.2(5) . . . 3_666 ?
Cl1B C1B N2B C3 179.6(4) . . . 3_666 ?
N2B C1B C3 C11 -179.6(2) . . . . ?
Cl1B C1B C3 C11 1.4(6) . . . . ?
C1 N2 C3 C1 -0.2(4) . . . 3_666 ?
C1 N2 C3 C11 -179.6(2) . . . . ?
C1B C3 C11 C24 -107.0(3) . . . . ?
N2 C3 C11 C24 -107.0(3) . . . . ?
C1 C3 C11 C24 73.7(4) 3_666 . . . ?
C1B C3 C11 C12 71.8(3) . . . . ?
N2 C3 C11 C12 71.8(3) . . . . ?
C1 C3 C11 C12 -107.5(3) 3_666 . . . ?
C24 C11 C12 C13 180.0(3) . . . . ?
C3 C11 C12 C13 1.1(4) . . . . ?
C24 C11 C12 C17 0.2(4) . . . . ?
C3 C11 C12 C17 -178.6(3) . . . . ?
C11 C12 C13 C14 178.5(3) . . . . ?
C17 C12 C13 C14 -1.8(4) . . . . ?
C12 C13 C14 C15 1.1(5) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 C18 -179.4(3) . . . . ?
C15 C16 C17 C12 -0.8(5) . . . . ?
C11 C12 C17 C18 0.0(4) . . . . ?
C13 C12 C17 C18 -179.8(3) . . . . ?
C11 C12 C17 C16 -178.6(3) . . . . ?
C13 C12 C17 C16 1.6(4) . . . . ?
C16 C17 C18 C19 178.8(3) . . . . ?
C12 C17 C18 C19 0.3(5) . . . . ?
C17 C18 C19 C20 179.7(3) . . . . ?
C17 C18 C19 C24 -0.7(5) . . . . ?
C18 C19 C20 C21 179.7(3) . . . . ?
C24 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 0.5(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 -0.7(5) . . . . ?
C12 C11 C24 C23 -179.1(3) . . . . ?
C3 C11 C24 C23 -0.3(4) . . . . ?
C12 C11 C24 C19 -0.7(4) . . . . ?
C3 C11 C24 C19 178.2(2) . . . . ?
C22 C23 C24 C11 179.7(3) . . . . ?
C22 C23 C24 C19 1.3(4) . . . . ?
C18 C19 C24 C11 0.9(4) . . . . ?
C20 C19 C24 C11 -179.5(3) . . . . ?
C18 C19 C24 C23 179.4(3) . . . . ?
C20 C19 C24 C23 -1.0(4) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_ebo3
_database_code_depnum_ccdc_archive 'CCDC 2353529'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '7 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H42 Cl8'
_chemical_formula_weight         974.47

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

_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                   8.4307(5)
_cell_length_b                   8.8836(5)
_cell_length_c                   16.8457(10)
_cell_angle_alpha                101.3934(17)
_cell_angle_beta                 100.9581(16)
_cell_angle_gamma                103.7267(16)
_cell_volume                     1163.68(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5435
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             502
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.522
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9207
_exptl_absorpt_correction_T_max  0.9607
_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            25481
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         31.094
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7120
_reflns_number_gt                4428
_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)+(0.0554P)²+0.7696P] 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         7120
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cl1 Cl 0.88158(7) 0.12683(7) 0.01055(4) 0.03240(15) Uani 1 1 d . . . . .
C2 C 0.6681(3) 0.0543(2) 0.00235(13) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.6011(3) 0.1301(2) 0.06258(13) 0.0250(4) Uani 1 1 d . . . . .
H3 H 0.672763 0.220324 0.105320 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4322(3) 0.0773(2) 0.06185(12) 0.0225(4) Uani 1 1 d . . . . .
C11 C 0.3673(3) 0.1649(2) 0.12833(12) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.3681(3) 0.1181(2) 0.20324(13) 0.0238(4) Uani 1 1 d . . . . .
C13 C 0.4206(3) -0.0185(3) 0.21761(15) 0.0322(5) Uani 1 1 d . . . . .
H13 H 0.459409 -0.077924 0.175883 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4162(3) -0.0647(3) 0.28942(16) 0.0387(6) Uani 1 1 d . . . . .
H14 H 0.451749 -0.155560 0.297407 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3587(3) 0.0219(3) 0.35262(15) 0.0367(6) Uani 1 1 d . . . . .
H15 H 0.353352 -0.012873 0.402129 0.044 Uiso 1 1 calc R U . . .
C16 C 0.3114(3) 0.1541(3) 0.34278(13) 0.0305(5) Uani 1 1 d . . . . .
H16 H 0.275027 0.211796 0.386175 0.037 Uiso 1 1 calc R U . . .
C17 C 0.3149(3) 0.2087(2) 0.26857(12) 0.0228(4) Uani 1 1 d . . . . .
C18 C 0.2670(3) 0.3462(2) 0.25847(12) 0.0222(4) Uani 1 1 d . . . . .
C19 C 0.2634(3) 0.3903(2) 0.18245(12) 0.0223(4) Uani 1 1 d . . . . .
C20 C 0.2109(3) 0.5267(3) 0.16840(14) 0.0297(5) Uani 1 1 d . . . . .
H20 H 0.179124 0.590005 0.211660 0.036 Uiso 1 1 calc R U . . .
C21 C 0.2053(3) 0.5675(3) 0.09495(15) 0.0369(6) Uani 1 1 d . . . . .
H21 H 0.168135 0.657551 0.086950 0.044 Uiso 1 1 calc R U . . .
C22 C 0.2546(3) 0.4770(3) 0.02988(15) 0.0368(6) Uani 1 1 d . . . . .
H22 H 0.250142 0.506652 -0.021498 0.044 Uiso 1 1 calc R U . . .
C23 C 0.3079(3) 0.3483(3) 0.04043(13) 0.0285(5) Uani 1 1 d . . . . .
H23 H 0.342086 0.289719 -0.003551 0.034 Uiso 1 1 calc R U . . .
C24 C 0.3139(3) 0.2991(2) 0.11634(12) 0.0220(4) Uani 1 1 d . . . . .
C31 C 0.2241(3) 0.4498(2) 0.32790(12) 0.0238(4) Uani 1 1 d . . . . .
C32 C 0.0563(3) 0.4394(3) 0.32826(14) 0.0303(5) Uani 1 1 d . . . . .
C33 C 0.0210(3) 0.5468(3) 0.39039(15) 0.0375(6) Uani 1 1 d . . . . .
H33 H -0.093206 0.539968 0.390354 0.045 Uiso 1 1 calc R U . . .
C34 C 0.1473(4) 0.6623(3) 0.45169(14) 0.0388(6) Uani 1 1 d . . . . .
C35 C 0.3127(3) 0.6681(3) 0.45205(14) 0.0355(6) Uani 1 1 d . . . . .
H35 H 0.400634 0.745064 0.495116 0.043 Uiso 1 1 calc R U . . .
C36 C 0.3546(3) 0.5642(3) 0.39108(13) 0.0281(5) Uani 1 1 d . . . . .
C37 C -0.0864(3) 0.3154(4) 0.26237(17) 0.0464(7) Uani 1 1 d . . . . .
H37A H -0.194199 0.323691 0.273782 0.070 Uiso 1 1 calc R U . . .
H37B H -0.075799 0.208235 0.263269 0.070 Uiso 1 1 calc R U . . .
H37C H -0.082070 0.333697 0.207225 0.070 Uiso 1 1 calc R U . . .
C38 C 0.1076(5) 0.7814(4) 0.51716(18) 0.0610(9) Uani 1 1 d . . . . .
H38A H 0.197648 0.814141 0.568726 0.092 Uiso 1 1 calc R U . . .
H38B H 0.000309 0.731492 0.528529 0.092 Uiso 1 1 calc R U . . .
H38C H 0.099101 0.875672 0.496559 0.092 Uiso 1 1 calc R U . . .
C39 C 0.5369(3) 0.5763(3) 0.39448(16) 0.0412(6) Uani 1 1 d . . . . .
H39A H 0.608468 0.673292 0.436723 0.062 Uiso 1 1 calc R U . . .
H39B H 0.558080 0.581503 0.339715 0.062 Uiso 1 1 calc R U . . .
H39C H 0.563045 0.482027 0.409214 0.062 Uiso 1 1 calc R U . . .
C41 C 0.1222(4) 1.2340(3) 0.76115(17) 0.0443(6) Uani 1 1 d . . . . .
H41 H 0.040480 1.293877 0.743952 0.053 Uiso 1 1 calc R U . . .
Cl3 Cl 0.04888(11) 1.12939(10) 0.82981(5) 0.0670(3) Uani 1 1 d . . . . .
Cl4 Cl 0.13460(11) 1.10548(10) 0.67109(4) 0.0601(2) Uani 1 1 d . . . . .
Cl2 Cl 0.31906(12) 1.37450(11) 0.81053(5) 0.0790(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.730(2) . ?
C2 C3 1.389(3) . ?
C2 C4 1.391(3) 2_655 ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C11 1.500(3) . ?
C11 C12 1.404(3) . ?
C11 C24 1.408(3) . ?
C12 C13 1.434(3) . ?
C12 C17 1.438(3) . ?
C13 C14 1.356(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.357(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.430(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.405(3) . ?
C18 C19 1.408(3) . ?
C18 C31 1.497(3) . ?
C19 C20 1.432(3) . ?
C19 C24 1.437(3) . ?
C20 C21 1.352(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.354(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.427(3) . ?
C23 H23 0.9500 . ?
C31 C32 1.397(3) . ?
C31 C36 1.404(3) . ?
C32 C33 1.397(3) . ?
C32 C37 1.508(3) . ?
C33 C34 1.378(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(4) . ?
C34 C38 1.515(3) . ?
C35 C36 1.396(3) . ?
C35 H35 0.9500 . ?
C36 C39 1.505(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C41 Cl3 1.734(3) . ?
C41 Cl4 1.746(3) . ?
C41 Cl2 1.757(3) . ?
C41 H41 1.0000 . ?

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
C3 C2 C4 121.26(19) . 2_655 ?
C3 C2 Cl1 117.88(16) . . ?
C4 C2 Cl1 120.86(15) 2_655 . ?
C4 C3 C2 121.61(18) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C2 117.13(17) . 2_655 ?
C3 C4 C11 119.05(18) . . ?
C2 C4 C11 123.82(18) 2_655 . ?
C12 C11 C24 120.57(17) . . ?
C12 C11 C4 120.20(18) . . ?
C24 C11 C4 119.16(18) . . ?
C11 C12 C13 122.23(18) . . ?
C11 C12 C17 119.76(18) . . ?
C13 C12 C17 118.01(19) . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.61(18) . . ?
C18 C17 C12 120.16(18) . . ?
C16 C17 C12 118.23(19) . . ?
C17 C18 C19 119.61(17) . . ?
C17 C18 C31 121.27(18) . . ?
C19 C18 C31 119.09(18) . . ?
C18 C19 C20 121.61(17) . . ?
C18 C19 C24 120.58(18) . . ?
C20 C19 C24 117.81(18) . . ?
C21 C20 C19 121.48(19) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.24(19) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C11 C24 C23 122.18(17) . . ?
C11 C24 C19 119.26(18) . . ?
C23 C24 C19 118.56(18) . . ?
C32 C31 C36 119.79(18) . . ?
C32 C31 C18 120.78(19) . . ?
C36 C31 C18 119.35(19) . . ?
C31 C32 C33 119.2(2) . . ?
C31 C32 C37 121.01(19) . . ?
C33 C32 C37 119.8(2) . . ?
C34 C33 C32 121.8(2) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 118.4(2) . . ?
C33 C34 C38 121.3(3) . . ?
C35 C34 C38 120.3(3) . . ?
C34 C35 C36 122.0(2) . . ?
C34 C35 H35 119.0 . . ?
C36 C35 H35 119.0 . . ?
C35 C36 C31 118.8(2) . . ?
C35 C36 C39 119.7(2) . . ?
C31 C36 C39 121.54(19) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
Cl3 C41 Cl4 111.73(16) . . ?
Cl3 C41 Cl2 110.64(16) . . ?
Cl4 C41 Cl2 110.43(15) . . ?
Cl3 C41 H41 108.0 . . ?
Cl4 C41 H41 108.0 . . ?
Cl2 C41 H41 108.0 . . ?

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
C4 C2 C3 C4 0.6(4) 2_655 . . . ?
Cl1 C2 C3 C4 -178.39(17) . . . . ?
C2 C3 C4 C2 -0.5(4) . . . 2_655 ?
C2 C3 C4 C11 -179.6(2) . . . . ?
C3 C4 C11 C12 -90.5(3) . . . . ?
C2 C4 C11 C12 90.5(3) 2_655 . . . ?
C3 C4 C11 C24 86.3(3) . . . . ?
C2 C4 C11 C24 -92.7(3) 2_655 . . . ?
C24 C11 C12 C13 179.6(2) . . . . ?
C4 C11 C12 C13 -3.6(3) . . . . ?
C24 C11 C12 C17 -0.4(3) . . . . ?
C4 C11 C12 C17 176.34(19) . . . . ?
C11 C12 C13 C14 -178.1(2) . . . . ?
C17 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 -1.6(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C18 -179.6(2) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C11 C12 C17 C18 -1.8(3) . . . . ?
C13 C12 C17 C18 178.2(2) . . . . ?
C11 C12 C17 C16 177.7(2) . . . . ?
C13 C12 C17 C16 -2.3(3) . . . . ?
C16 C17 C18 C19 -176.4(2) . . . . ?
C12 C17 C18 C19 3.1(3) . . . . ?
C16 C17 C18 C31 5.3(3) . . . . ?
C12 C17 C18 C31 -175.16(19) . . . . ?
C17 C18 C19 C20 178.2(2) . . . . ?
C31 C18 C19 C20 -3.5(3) . . . . ?
C17 C18 C19 C24 -2.1(3) . . . . ?
C31 C18 C19 C24 176.14(19) . . . . ?
C18 C19 C20 C21 -179.1(2) . . . . ?
C24 C19 C20 C21 1.3(3) . . . . ?
C19 C20 C21 C22 -1.1(4) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C12 C11 C24 C23 -178.6(2) . . . . ?
C4 C11 C24 C23 4.6(3) . . . . ?
C12 C11 C24 C19 1.4(3) . . . . ?
C4 C11 C24 C19 -175.43(18) . . . . ?
C22 C23 C24 C11 179.4(2) . . . . ?
C22 C23 C24 C19 -0.7(3) . . . . ?
C18 C19 C24 C11 -0.1(3) . . . . ?
C20 C19 C24 C11 179.6(2) . . . . ?
C18 C19 C24 C23 179.9(2) . . . . ?
C20 C19 C24 C23 -0.4(3) . . . . ?
C17 C18 C31 C32 -101.5(3) . . . . ?
C19 C18 C31 C32 80.2(3) . . . . ?
C17 C18 C31 C36 81.7(3) . . . . ?
C19 C18 C31 C36 -96.6(2) . . . . ?
C36 C31 C32 C33 1.9(3) . . . . ?
C18 C31 C32 C33 -174.9(2) . . . . ?
C36 C31 C32 C37 -178.6(2) . . . . ?
C18 C31 C32 C37 4.6(3) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C37 C32 C33 C34 -179.8(2) . . . . ?
C32 C33 C34 C35 -1.6(4) . . . . ?
C32 C33 C34 C38 178.1(2) . . . . ?
C33 C34 C35 C36 2.0(4) . . . . ?
C38 C34 C35 C36 -177.7(2) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C34 C35 C36 C39 179.8(2) . . . . ?
C32 C31 C36 C35 -1.5(3) . . . . ?
C18 C31 C36 C35 175.3(2) . . . . ?
C32 C31 C36 C39 178.2(2) . . . . ?
C18 C31 C36 C39 -4.9(3) . . . . ?

_refine_diff_density_max         0.767
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.066


####################################################################### 
# 
# 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_ebo2
_database_code_depnum_ccdc_archive 'CCDC 2353533'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Mes-DBAF in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H40 Cl6'
_chemical_formula_weight         901.56

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1598(15)
_cell_length_b                   20.446(3)
_cell_length_c                   12.1314(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.773(4)
_cell_angle_gamma                90
_cell_volume                     2196.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2336
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      19.37

_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.429
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8780
_exptl_absorpt_correction_T_max  0.9579
_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            17113
_diffrn_reflns_av_unetI/netI     0.0807
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         22.719
_diffrn_reflns_theta_full        22.719
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2952
_reflns_number_gt                1780
_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)+(0.0643P)²+2.5502P] 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         2952
_refine_ls_number_parameters     291
_refine_ls_number_restraints     342
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      0.971
_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
C11 C 0.3626(5) 0.4657(2) 0.4538(4) 0.0242(11) Uani 1 1 d . . . . .
H11 H 0.270380 0.443208 0.423383 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3624(5) 0.5308(2) 0.4876(3) 0.0230(10) Uani 1 1 d . . . . .
C13 C 0.2354(5) 0.5745(2) 0.4858(4) 0.0255(11) Uani 1 1 d . . . . .
C14 C 0.0815(5) 0.5697(2) 0.4501(4) 0.0292(11) Uani 1 1 d . . . . .
H14 H 0.035527 0.530759 0.414682 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0082(5) 0.6233(2) 0.4664(4) 0.0329(12) Uani 1 1 d . . . . .
H15 H -0.114937 0.619699 0.441571 0.039 Uiso 1 1 calc R U . . .
C16 C 0.0541(5) 0.6803(2) 0.5170(4) 0.0329(12) Uani 1 1 d . . . . .
H16 H -0.009878 0.714886 0.528331 0.040 Uiso 1 1 calc R U . . .
C17 C 0.2145(5) 0.6882(2) 0.5527(4) 0.0260(11) Uani 1 1 d . . . . .
C18 C 0.2915(5) 0.7438(2) 0.6050(4) 0.0266(11) Uani 1 1 d . . . . .
C19 C 0.4528(5) 0.7442(2) 0.6350(4) 0.0267(11) Uani 1 1 d . . . . .
C20 C 0.5353(5) 0.7998(2) 0.6885(4) 0.0324(12) Uani 1 1 d . . . . .
H20 H 0.481024 0.836828 0.703891 0.039 Uiso 1 1 calc R U . . .
C21 C 0.6871(5) 0.8017(2) 0.7180(4) 0.0350(12) Uani 1 1 d . . . . .
H21 H 0.738280 0.839376 0.754319 0.042 Uiso 1 1 calc R U . . .
C22 C 0.7709(5) 0.7472(2) 0.6947(4) 0.0368(12) Uani 1 1 d . . . . .
H22 H 0.878015 0.749149 0.714197 0.044 Uiso 1 1 calc R U . . .
C23 C 0.6993(5) 0.6922(2) 0.6446(4) 0.0301(11) Uani 1 1 d . . . . .
H23 H 0.757444 0.656305 0.629980 0.036 Uiso 1 1 calc R U . . .
C24 C 0.5384(5) 0.6878(2) 0.6138(3) 0.0232(10) Uani 1 1 d . . . . .
C25 C 0.4586(5) 0.6319(2) 0.5643(3) 0.0228(10) Uani 1 1 d . . . . .
C26 C 0.5005(5) 0.5654(2) 0.5347(4) 0.0248(10) Uani 1 1 d . . . . .
C27 C 0.3004(5) 0.6347(2) 0.5350(4) 0.0240(10) Uani 1 1 d . . . . .
C31 C 0.2053(5) 0.8017(2) 0.6299(4) 0.0248(10) Uani 1 1 d . . . . .
C32 C 0.1541(5) 0.8499(2) 0.5469(4) 0.0330(12) Uani 1 1 d . . . . .
C33 C 0.0721(6) 0.9024(2) 0.5731(4) 0.0373(12) Uani 1 1 d . . . . .
H33 H 0.037052 0.935167 0.517036 0.045 Uiso 1 1 calc R U . . .
C34 C 0.0401(5) 0.9085(2) 0.6784(4) 0.0356(12) Uani 1 1 d . . . . .
C35 C 0.0903(5) 0.8599(2) 0.7585(4) 0.0322(12) Uani 1 1 d . . . . .
H35 H 0.068768 0.863342 0.830878 0.039 Uiso 1 1 calc R U . . .
C36 C 0.1715(5) 0.8063(2) 0.7360(4) 0.0295(11) Uani 1 1 d . . . . .
C37 C 0.1831(7) 0.8445(3) 0.4303(4) 0.0515(15) Uani 1 1 d . . . . .
H37A H 0.136092 0.881654 0.383313 0.077 Uiso 1 1 calc R U . . .
H37B H 0.139864 0.803629 0.394142 0.077 Uiso 1 1 calc R U . . .
H37C H 0.292134 0.844917 0.437636 0.077 Uiso 1 1 calc R U . . .
C38 C -0.0507(6) 0.9654(2) 0.7043(5) 0.0492(15) Uani 1 1 d . . . . .
H38A H -0.137709 0.948954 0.729010 0.074 Uiso 1 1 calc R U . . .
H38B H -0.086070 0.992154 0.635610 0.074 Uiso 1 1 calc R U . . .
H38C H 0.012754 0.992086 0.765073 0.074 Uiso 1 1 calc R U . . .
C39 C 0.2187(6) 0.7528(2) 0.8240(4) 0.0389(13) Uani 1 1 d . . . . .
H39A H 0.192296 0.765524 0.894343 0.058 Uiso 1 1 calc R U . . .
H39B H 0.328010 0.746091 0.839777 0.058 Uiso 1 1 calc R U . . .
H39C H 0.166341 0.712120 0.794784 0.058 Uiso 1 1 calc R U . . .
C41 C 0.1246(7) 0.5412(3) 0.8747(5) 0.0550(19) Uani 0.889(5) 1 d D U P A 1
H41 H 0.184073 0.504036 0.917504 0.066 Uiso 0.889(5) 1 calc R U P A 1
Cl1 Cl 0.1356(3) 0.60682(12) 0.96995(16) 0.0743(8) Uani 0.889(5) 1 d D U P A 1
Cl2 Cl 0.2025(3) 0.56118(11) 0.76187(19) 0.0821(9) Uani 0.889(5) 1 d D U P A 1
Cl3 Cl -0.0615(3) 0.51578(16) 0.8258(2) 0.1129(13) Uani 0.889(5) 1 d D U P A 1
C41B C 0.181(4) 0.5314(13) 0.849(2) 0.089(16) Uiso 0.111(5) 1 d D U P A 2
H41B H 0.278528 0.510300 0.845814 0.106 Uiso 0.111(5) 1 calc R U P A 2
Cl1B Cl 0.197(3) 0.5826(13) 0.967(2) 0.128(11) Uiso 0.111(5) 1 d D U P A 2
Cl2B Cl 0.102(3) 0.5806(11) 0.7315(18) 0.125(9) Uiso 0.111(5) 1 d D U P A 2
Cl3B Cl 0.040(2) 0.4757(8) 0.8604(14) 0.084(7) Uiso 0.111(5) 1 d D U 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
C11 C26 1.382(6) 3_666 ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 C26 1.435(6) . ?
C12 C13 1.462(6) . ?
C13 C14 1.368(6) . ?
C13 C27 1.431(6) . ?
C14 C15 1.414(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.431(6) . ?
C16 H16 0.9500 . ?
C17 C27 1.395(6) . ?
C17 C18 1.402(6) . ?
C18 C19 1.429(6) . ?
C18 C31 1.496(6) . ?
C19 C20 1.425(6) . ?
C19 C24 1.454(6) . ?
C20 C21 1.346(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.421(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.364(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.428(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.406(6) . ?
C25 C27 1.403(6) . ?
C25 C26 1.482(6) . ?
C31 C32 1.401(6) . ?
C31 C36 1.401(6) . ?
C32 C33 1.393(6) . ?
C32 C37 1.508(6) . ?
C33 C34 1.387(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(6) . ?
C34 C38 1.510(6) . ?
C35 C36 1.391(6) . ?
C35 H35 0.9500 . ?
C36 C39 1.513(6) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C41 Cl3 1.735(6) . ?
C41 Cl2 1.746(6) . ?
C41 Cl1 1.756(6) . ?
C41 H41 1.0000 . ?
C41B Cl2B 1.748(17) . ?
C41B Cl1B 1.750(17) . ?
C41B Cl3B 1.751(17) . ?
C41B H41B 1.0000 . ?

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
C26 C11 C12 118.7(4) 3_666 . ?
C26 C11 H11 120.7 3_666 . ?
C12 C11 H11 120.7 . . ?
C11 C12 C26 121.4(4) . . ?
C11 C12 C13 129.8(4) . . ?
C26 C12 C13 108.8(4) . . ?
C14 C13 C27 118.6(4) . . ?
C14 C13 C12 135.4(4) . . ?
C27 C13 C12 106.0(4) . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 122.1(4) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C27 C17 C18 117.8(4) . . ?
C27 C17 C16 116.2(4) . . ?
C18 C17 C16 126.0(4) . . ?
C17 C18 C19 119.2(4) . . ?
C17 C18 C31 120.2(4) . . ?
C19 C18 C31 120.6(4) . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 C24 117.8(4) . . ?
C18 C19 C24 121.3(4) . . ?
C21 C20 C19 122.4(4) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C20 C21 C22 119.9(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 121.0(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 123.5(4) . . ?
C25 C24 C19 118.4(4) . . ?
C23 C24 C19 118.1(4) . . ?
C27 C25 C24 117.8(4) . . ?
C27 C25 C26 106.9(4) . . ?
C24 C25 C26 135.3(4) . . ?
C11 C26 C12 119.9(4) 3_666 . ?
C11 C26 C25 133.1(4) 3_666 . ?
C12 C26 C25 107.0(4) . . ?
C17 C27 C25 125.4(4) . . ?
C17 C27 C13 123.2(4) . . ?
C25 C27 C13 111.3(4) . . ?
C32 C31 C36 120.1(4) . . ?
C32 C31 C18 120.5(4) . . ?
C36 C31 C18 119.3(4) . . ?
C33 C32 C31 118.6(4) . . ?
C33 C32 C37 120.2(4) . . ?
C31 C32 C37 121.2(4) . . ?
C34 C33 C32 122.1(4) . . ?
C34 C33 H33 118.9 . . ?
C32 C33 H33 118.9 . . ?
C35 C34 C33 118.2(4) . . ?
C35 C34 C38 120.6(4) . . ?
C33 C34 C38 121.2(4) . . ?
C34 C35 C36 121.7(4) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C35 C36 C31 119.2(4) . . ?
C35 C36 C39 120.1(4) . . ?
C31 C36 C39 120.6(4) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C34 C38 H38A 109.5 . . ?
C34 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C34 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
Cl3 C41 Cl2 111.3(3) . . ?
Cl3 C41 Cl1 109.9(4) . . ?
Cl2 C41 Cl1 111.8(3) . . ?
Cl3 C41 H41 107.9 . . ?
Cl2 C41 H41 107.9 . . ?
Cl1 C41 H41 107.9 . . ?
Cl2B C41B Cl1B 104.7(17) . . ?
Cl2B C41B Cl3B 105.9(16) . . ?
Cl1B C41B Cl3B 103.5(17) . . ?
Cl2B C41B H41B 113.9 . . ?
Cl1B C41B H41B 113.9 . . ?
Cl3B C41B H41B 113.9 . . ?

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
C26 C11 C12 C26 -0.7(7) 3_666 . . . ?
C26 C11 C12 C13 -179.3(4) 3_666 . . . ?
C11 C12 C13 C14 -2.4(8) . . . . ?
C26 C12 C13 C14 178.8(5) . . . . ?
C11 C12 C13 C27 177.4(4) . . . . ?
C26 C12 C13 C27 -1.3(5) . . . . ?
C27 C13 C14 C15 -2.2(6) . . . . ?
C12 C13 C14 C15 177.7(5) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C17 1.7(7) . . . . ?
C15 C16 C17 C27 -1.2(6) . . . . ?
C15 C16 C17 C18 179.9(4) . . . . ?
C27 C17 C18 C19 1.6(6) . . . . ?
C16 C17 C18 C19 -179.6(4) . . . . ?
C27 C17 C18 C31 -177.8(4) . . . . ?
C16 C17 C18 C31 1.1(7) . . . . ?
C17 C18 C19 C20 -179.8(4) . . . . ?
C31 C18 C19 C20 -0.5(6) . . . . ?
C17 C18 C19 C24 -0.8(6) . . . . ?
C31 C18 C19 C24 178.6(4) . . . . ?
C18 C19 C20 C21 179.9(4) . . . . ?
C24 C19 C20 C21 0.8(7) . . . . ?
C19 C20 C21 C22 0.7(7) . . . . ?
C20 C21 C22 C23 -1.3(7) . . . . ?
C21 C22 C23 C24 0.2(7) . . . . ?
C22 C23 C24 C25 -178.6(4) . . . . ?
C22 C23 C24 C19 1.3(6) . . . . ?
C20 C19 C24 C25 178.1(4) . . . . ?
C18 C19 C24 C25 -1.0(6) . . . . ?
C20 C19 C24 C23 -1.9(6) . . . . ?
C18 C19 C24 C23 179.1(4) . . . . ?
C23 C24 C25 C27 -178.1(4) . . . . ?
C19 C24 C25 C27 1.9(6) . . . . ?
C23 C24 C25 C26 3.5(8) . . . . ?
C19 C24 C25 C26 -176.4(4) . . . . ?
C11 C12 C26 C11 0.7(7) . . . 3_666 ?
C13 C12 C26 C11 179.6(4) . . . 3_666 ?
C11 C12 C26 C25 -178.2(4) . . . . ?
C13 C12 C26 C25 0.6(5) . . . . ?
C27 C25 C26 C11 -178.4(5) . . . 3_666 ?
C24 C25 C26 C11 0.0(8) . . . 3_666 ?
C27 C25 C26 C12 0.3(5) . . . . ?
C24 C25 C26 C12 178.8(4) . . . . ?
C18 C17 C27 C25 -0.6(7) . . . . ?
C16 C17 C27 C25 -179.6(4) . . . . ?
C18 C17 C27 C13 178.0(4) . . . . ?
C16 C17 C27 C13 -1.0(6) . . . . ?
C24 C25 C27 C17 -1.2(7) . . . . ?
C26 C25 C27 C17 177.5(4) . . . . ?
C24 C25 C27 C13 -180.0(4) . . . . ?
C26 C25 C27 C13 -1.2(5) . . . . ?
C14 C13 C27 C17 2.7(6) . . . . ?
C12 C13 C27 C17 -177.2(4) . . . . ?
C14 C13 C27 C25 -178.5(4) . . . . ?
C12 C13 C27 C25 1.6(5) . . . . ?
C17 C18 C31 C32 -86.3(5) . . . . ?
C19 C18 C31 C32 94.3(5) . . . . ?
C17 C18 C31 C36 91.5(5) . . . . ?
C19 C18 C31 C36 -87.9(5) . . . . ?
C36 C31 C32 C33 1.2(7) . . . . ?
C18 C31 C32 C33 179.0(4) . . . . ?
C36 C31 C32 C37 -177.3(4) . . . . ?
C18 C31 C32 C37 0.5(7) . . . . ?
C31 C32 C33 C34 0.1(7) . . . . ?
C37 C32 C33 C34 178.6(5) . . . . ?
C32 C33 C34 C35 -0.8(7) . . . . ?
C32 C33 C34 C38 -179.2(5) . . . . ?
C33 C34 C35 C36 0.3(7) . . . . ?
C38 C34 C35 C36 178.7(4) . . . . ?
C34 C35 C36 C31 1.0(7) . . . . ?
C34 C35 C36 C39 -177.4(4) . . . . ?
C32 C31 C36 C35 -1.7(6) . . . . ?
C18 C31 C36 C35 -179.5(4) . . . . ?
C32 C31 C36 C39 176.6(4) . . . . ?
C18 C31 C36 C39 -1.2(6) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.058



# start Validation Reply Form
_vrf_THETM01_ebo2                
;
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 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_sve110
_database_code_depnum_ccdc_archive 'CCDC 2353534'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Mes-DBAF-N2 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H37 Cl3 N2'
_chemical_formula_weight         784.17

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                   7.5160(3)
_cell_length_b                   15.7823(6)
_cell_length_c                   17.4357(6)
_cell_angle_alpha                94.217(3)
_cell_angle_beta                 96.767(3)
_cell_angle_gamma                101.960(3)
_cell_volume                     1998.99(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    18116
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      68.71

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.369
_shelx_estimated_absorpt_T_min   0.675
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8679
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_process_details   'STOE X-AREA LANA'
_exptl_absorpt_special_details   'X-Area LANA 2.7.5.0 (STOE, 2022)'
_diffrn_ambient_temperature      200(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            29825
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.565
_diffrn_reflns_theta_max         68.623
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             7124
_reflns_number_gt                4564
_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 1.31.186.0 (STOE, 2022)'
_computing_cell_refinement       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_reduction        'X-Area Integrate 2.5.3.0 (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)+(0.0888P)²+1.8607P] 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         7124
_refine_ls_number_parameters     548
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.1191
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.1873
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.094
_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
C1_1 C 0.9879(4) 0.4154(2) 0.48609(19) 0.0529(8) Uani 1 1 d . . . . .
C2_1 C 1.0581(4) 0.4766(2) 0.43481(18) 0.0540(8) Uani 1 1 d . . . . .
N3_1 N 1.0722(4) 0.56248(17) 0.44754(16) 0.0543(7) Uani 1 1 d . . . . .
C11_1 C 1.1104(4) 0.4295(2) 0.36828(19) 0.0542(8) Uani 1 1 d . . . . .
C12_1 C 1.1838(5) 0.4517(2) 0.3021(2) 0.0576(8) Uani 1 1 d . . . . .
H12_1 H 1.214531 0.510825 0.291528 0.069 Uiso 1 1 calc R U . . .
C13_1 C 1.2122(5) 0.3843(3) 0.2501(2) 0.0643(9) Uani 1 1 d . . . . .
H13_1 H 1.260933 0.399080 0.203777 0.077 Uiso 1 1 calc R U . . .
C14_1 C 1.1722(5) 0.2979(2) 0.2639(2) 0.0611(9) Uani 1 1 d . . . . .
H14_1 H 1.196108 0.255042 0.227757 0.073 Uiso 1 1 calc R U . . .
C15_1 C 1.0956(5) 0.2722(2) 0.33152(19) 0.0564(8) Uani 1 1 d . . . . .
C16_1 C 1.0484(5) 0.1878(2) 0.3530(2) 0.0575(8) Uani 1 1 d . . . . .
C17_1 C 0.9668(5) 0.1726(2) 0.4220(2) 0.0570(8) Uani 1 1 d . . . . .
C18_1 C 0.9109(5) 0.0873(2) 0.4436(2) 0.0641(9) Uani 1 1 d . . . . .
H18_1 H 0.927851 0.039212 0.411418 0.077 Uiso 1 1 calc R U . . .
C19_1 C 0.8334(6) 0.0730(3) 0.5095(2) 0.0714(10) Uani 1 1 d . . . . .
H19_1 H 0.797444 0.015090 0.522617 0.086 Uiso 1 1 calc R U . . .
C20_1 C 0.8057(5) 0.1430(2) 0.5587(2) 0.0680(10) Uani 1 1 d . . . . .
H20_1 H 0.751640 0.131822 0.604538 0.082 Uiso 1 1 calc R U . . .
C21_1 C 0.8561(5) 0.2266(2) 0.5407(2) 0.0605(9) Uani 1 1 d . . . . .
H21_1 H 0.836558 0.273246 0.573981 0.073 Uiso 1 1 calc R U . . .
C22_1 C 0.9377(5) 0.2440(2) 0.4724(2) 0.0564(8) Uani 1 1 d . . . . .
C23_1 C 0.9925(4) 0.3281(2) 0.4511(2) 0.0547(8) Uani 1 1 d . . . . .
C24_1 C 1.0666(4) 0.3407(2) 0.38203(19) 0.0540(8) Uani 1 1 d . . . . .
C31_1 C 1.0947(5) 0.1140(2) 0.3050(2) 0.0611(9) Uani 1 1 d . . . . .
C32_1 C 1.2619(6) 0.0900(2) 0.3258(2) 0.0673(10) Uani 1 1 d . . . . .
C33_1 C 1.3042(7) 0.0227(3) 0.2811(3) 0.0811(12) Uani 1 1 d . . . . .
H33_1 H 1.416394 0.005547 0.295645 0.097 Uiso 1 1 calc R U . . .
C34_1 C 1.1906(8) -0.0201(3) 0.2166(3) 0.0835(13) Uani 1 1 d . . . . .
C35_1 C 1.0255(7) 0.0044(3) 0.1963(3) 0.0859(13) Uani 1 1 d . . . . .
H35_1 H 0.945019 -0.025226 0.151942 0.103 Uiso 1 1 calc R U . . .
C36_1 C 0.9746(6) 0.0719(2) 0.2397(2) 0.0693(10) Uani 1 1 d . . . . .
C37_1 C 1.3935(6) 0.1362(3) 0.3955(3) 0.0832(12) Uani 1 1 d . . . . .
H37A_1 H 1.516250 0.125778 0.391339 0.125 Uiso 1 1 calc R U . . .
H37B_1 H 1.351792 0.114107 0.442879 0.125 Uiso 1 1 calc R U . . .
H37C_1 H 1.398083 0.198885 0.397620 0.125 Uiso 1 1 calc R U . . .
C38_1 C 1.2430(10) -0.0919(4) 0.1664(4) 0.128(2) Uani 1 1 d . . . . .
H38A_1 H 1.132011 -0.135262 0.144363 0.193 Uiso 1 1 calc R U . . .
H38B_1 H 1.325887 -0.119916 0.198200 0.193 Uiso 1 1 calc R U . . .
H38C_1 H 1.304742 -0.066687 0.124222 0.193 Uiso 1 1 calc R U . . .
C39_1 C 0.7980(6) 0.0995(3) 0.2158(3) 0.0945(14) Uani 1 1 d . . . . .
H39A_1 H 0.721152 0.056469 0.175506 0.142 Uiso 1 1 calc R U . . .
H39B_1 H 0.824881 0.156379 0.195460 0.142 Uiso 1 1 calc R U . . .
H39C_1 H 0.732705 0.103711 0.260927 0.142 Uiso 1 1 calc R U . . .
C1_2 C 0.4435(4) 0.4459(2) 0.55111(19) 0.0552(8) Uani 1 1 d . . . . .
C2_2 C 0.4493(4) 0.5370(2) 0.5614(2) 0.0567(8) Uani 1 1 d . . . . .
N3_2 N 0.5058(4) 0.59311(18) 0.51150(16) 0.0555(7) Uani 1 1 d . . . . .
C11_2 C 0.3829(4) 0.5557(2) 0.63547(19) 0.0571(8) Uani 1 1 d . . . . .
C12_2 C 0.3578(5) 0.6289(2) 0.6760(2) 0.0620(9) Uani 1 1 d . . . . .
H12_2 H 0.386234 0.684120 0.656553 0.074 Uiso 1 1 calc R U . . .
C13_2 C 0.2881(5) 0.6200(3) 0.7479(2) 0.0649(10) Uani 1 1 d . . . . .
H13_2 H 0.270691 0.670572 0.776480 0.078 Uiso 1 1 calc R U . . .
C14_2 C 0.2454(5) 0.5426(3) 0.7775(2) 0.0659(10) Uani 1 1 d . . . . .
H14_2 H 0.198616 0.540176 0.825749 0.079 Uiso 1 1 calc R U . . .
C15_2 C 0.2696(5) 0.4636(2) 0.7370(2) 0.0599(9) Uani 1 1 d . . . . .
C16_2 C 0.2286(5) 0.3793(3) 0.7598(2) 0.0618(9) Uani 1 1 d . . . . .
C17_2 C 0.2643(5) 0.3085(2) 0.7131(2) 0.0609(9) Uani 1 1 d . . . . .
C18_2 C 0.2301(5) 0.2224(3) 0.7359(2) 0.0696(10) Uani 1 1 d . . . . .
H18_2 H 0.181918 0.212157 0.783204 0.084 Uiso 1 1 calc R U . . .
C19_2 C 0.2648(6) 0.1546(3) 0.6917(2) 0.0750(11) Uani 1 1 d . . . . .
H19_2 H 0.238864 0.097716 0.708013 0.090 Uiso 1 1 calc R U . . .
C20_2 C 0.3397(6) 0.1683(3) 0.6214(2) 0.0720(10) Uani 1 1 d . . . . .
H20_2 H 0.364527 0.120566 0.591184 0.086 Uiso 1 1 calc R U . . .
C21_2 C 0.3759(5) 0.2490(2) 0.5969(2) 0.0633(9) Uani 1 1 d . . . . .
H21_2 H 0.426074 0.257106 0.549746 0.076 Uiso 1 1 calc R U . . .
C22_2 C 0.3398(5) 0.3222(2) 0.6411(2) 0.0592(9) Uani 1 1 d . . . . .
C23_2 C 0.3740(4) 0.4060(2) 0.6183(2) 0.0567(8) Uani 1 1 d . . . . .
C24_2 C 0.3402(4) 0.4740(2) 0.66613(19) 0.0579(9) Uani 1 1 d . . . . .
C31_2 C 0.1447(5) 0.3654(3) 0.8325(2) 0.0651(9) Uani 1 1 d . . . . .
C32_2 C -0.0456(5) 0.3340(3) 0.8290(2) 0.0679(10) Uani 1 1 d . . . . .
C33_2 C -0.1209(6) 0.3271(3) 0.8980(2) 0.0797(12) Uani 1 1 d . . . . .
H33_2 H -0.249242 0.305398 0.895965 0.096 Uiso 1 1 calc R U . . .
C34_2 C -0.0132(7) 0.3513(3) 0.9700(2) 0.0877(13) Uani 1 1 d . . . . .
C35_2 C 0.1735(7) 0.3815(3) 0.9718(2) 0.0897(14) Uani 1 1 d . . . . .
H35_2 H 0.248321 0.397939 1.020586 0.108 Uiso 1 1 calc R U . . .
C36_2 C 0.2547(6) 0.3885(3) 0.9050(2) 0.0757(11) Uani 1 1 d . . . . .
C37_2 C -0.1674(6) 0.3088(3) 0.7523(2) 0.0805(12) Uani 1 1 d . . . . .
H37A_2 H -0.295212 0.307035 0.759910 0.121 Uiso 1 1 calc R U . . .
H37B_2 H -0.156341 0.251261 0.730836 0.121 Uiso 1 1 calc R U . . .
H37C_2 H -0.129983 0.351745 0.716166 0.121 Uiso 1 1 calc R U . . .
C38_2 C -0.1025(9) 0.3441(5) 1.0441(3) 0.131(2) Uani 1 1 d . . . . .
H38A_2 H -0.110297 0.285399 1.060239 0.197 Uiso 1 1 calc R U . . .
H38B_2 H -0.226148 0.355417 1.034451 0.197 Uiso 1 1 calc R U . . .
H38C_2 H -0.028392 0.386899 1.085316 0.197 Uiso 1 1 calc R U . . .
C39_2 C 0.4595(6) 0.4213(4) 0.9091(3) 0.1011(16) Uani 1 1 d . . . . .
H39A_2 H 0.518534 0.420690 0.962219 0.152 Uiso 1 1 calc R U . . .
H39B_2 H 0.485018 0.480884 0.894338 0.152 Uiso 1 1 calc R U . . .
H39C_2 H 0.507744 0.383578 0.873479 0.152 Uiso 1 1 calc R U . . .
C41 C 0.2981(12) 0.1890(6) 1.0147(5) 0.100(3) Uani 0.560(6) 1 d D U P A 1
H41 H 0.256754 0.237531 0.989048 0.119 Uiso 0.560(6) 1 calc R U P A 1
Cl1 Cl 0.4139(5) 0.1598(3) 0.9463(2) 0.164(2) Uani 0.560(6) 1 d D U P A 1
Cl2 Cl 0.4193(6) 0.2499(4) 1.0958(2) 0.1338(17) Uani 0.560(6) 1 d D U P A 1
Cl3 Cl 0.1012(11) 0.1318(7) 1.0186(6) 0.249(4) Uani 0.560(6) 1 d D U P A 1
C41B C 0.3148(19) 0.1188(10) 1.0608(9) 0.155(6) Uani 0.440(6) 1 d D U P A 2
H41B H 0.303620 0.075300 1.099822 0.186 Uiso 0.440(6) 1 calc R U P A 2
Cl1B Cl 0.4202(13) 0.0729(9) 1.0015(6) 0.284(6) Uani 0.440(6) 1 d D U P A 2
Cl2B Cl 0.4414(13) 0.1977(9) 1.1119(5) 0.231(5) Uani 0.440(6) 1 d D U P A 2
Cl3B Cl 0.1167(14) 0.1159(7) 1.0366(6) 0.236(6) Uani 0.440(6) 1 d D U 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
C1_1 N3_1 1.339(4) 2_766 ?
C1_1 C2_1 1.428(5) . ?
C1_1 C23_1 1.474(5) . ?
C2_1 N3_1 1.337(4) . ?
C2_1 C11_1 1.468(5) . ?
C11_1 C12_1 1.375(5) . ?
C11_1 C24_1 1.417(5) . ?
C12_1 C13_1 1.413(5) . ?
C12_1 H12_1 0.9500 . ?
C13_1 C14_1 1.380(5) . ?
C13_1 H13_1 0.9500 . ?
C14_1 C15_1 1.421(5) . ?
C14_1 H14_1 0.9500 . ?
C15_1 C16_1 1.396(5) . ?
C15_1 C24_1 1.413(5) . ?
C16_1 C17_1 1.428(5) . ?
C16_1 C31_1 1.507(5) . ?
C17_1 C18_1 1.416(5) . ?
C17_1 C22_1 1.446(5) . ?
C18_1 C19_1 1.361(5) . ?
C18_1 H18_1 0.9500 . ?
C19_1 C20_1 1.414(5) . ?
C19_1 H19_1 0.9500 . ?
C20_1 C21_1 1.365(5) . ?
C20_1 H20_1 0.9500 . ?
C21_1 C22_1 1.422(5) . ?
C21_1 H21_1 0.9500 . ?
C22_1 C23_1 1.397(5) . ?
C23_1 C24_1 1.395(5) . ?
C31_1 C36_1 1.397(5) . ?
C31_1 C32_1 1.402(5) . ?
C32_1 C33_1 1.384(5) . ?
C32_1 C37_1 1.508(6) . ?
C33_1 C34_1 1.368(7) . ?
C33_1 H33_1 0.9500 . ?
C34_1 C35_1 1.390(7) . ?
C34_1 C38_1 1.525(6) . ?
C35_1 C36_1 1.404(6) . ?
C35_1 H35_1 0.9500 . ?
C36_1 C39_1 1.504(6) . ?
C37_1 H37A_1 0.9800 . ?
C37_1 H37B_1 0.9800 . ?
C37_1 H37C_1 0.9800 . ?
C38_1 H38A_1 0.9800 . ?
C38_1 H38B_1 0.9800 . ?
C38_1 H38C_1 0.9800 . ?
C39_1 H39A_1 0.9800 . ?
C39_1 H39B_1 0.9800 . ?
C39_1 H39C_1 0.9800 . ?
C1_2 N3_2 1.346(4) 2_666 ?
C1_2 C2_2 1.428(5) . ?
C1_2 C23_2 1.468(5) . ?
C2_2 N3_2 1.328(5) . ?
C2_2 C11_2 1.471(5) . ?
C11_2 C12_2 1.368(5) . ?
C11_2 C24_2 1.422(5) . ?
C12_2 C13_2 1.421(5) . ?
C12_2 H12_2 0.9500 . ?
C13_2 C14_2 1.353(6) . ?
C13_2 H13_2 0.9500 . ?
C14_2 C15_2 1.441(5) . ?
C14_2 H14_2 0.9500 . ?
C15_2 C16_2 1.401(5) . ?
C15_2 C24_2 1.408(5) . ?
C16_2 C17_2 1.423(5) . ?
C16_2 C31_2 1.490(5) . ?
C17_2 C18_2 1.424(5) . ?
C17_2 C22_2 1.451(5) . ?
C18_2 C19_2 1.360(5) . ?
C18_2 H18_2 0.9500 . ?
C19_2 C20_2 1.422(5) . ?
C19_2 H19_2 0.9500 . ?
C20_2 C21_2 1.358(5) . ?
C20_2 H20_2 0.9500 . ?
C21_2 C22_2 1.431(5) . ?
C21_2 H21_2 0.9500 . ?
C22_2 C23_2 1.391(5) . ?
C23_2 C24_2 1.395(5) . ?
C31_2 C32_2 1.406(5) . ?
C31_2 C36_2 1.406(5) . ?
C32_2 C33_2 1.390(5) . ?
C32_2 C37_2 1.507(5) . ?
C33_2 C34_2 1.393(6) . ?
C33_2 H33_2 0.9500 . ?
C34_2 C35_2 1.381(7) . ?
C34_2 C38_2 1.525(6) . ?
C35_2 C36_2 1.378(6) . ?
C35_2 H35_2 0.9500 . ?
C36_2 C39_2 1.510(6) . ?
C37_2 H37A_2 0.9800 . ?
C37_2 H37B_2 0.9800 . ?
C37_2 H37C_2 0.9800 . ?
C38_2 H38A_2 0.9800 . ?
C38_2 H38B_2 0.9800 . ?
C38_2 H38C_2 0.9800 . ?
C39_2 H39A_2 0.9800 . ?
C39_2 H39B_2 0.9800 . ?
C39_2 H39C_2 0.9800 . ?
C41 Cl3 1.577(9) . ?
C41 Cl1 1.651(8) . ?
C41 Cl2 1.699(8) . ?
C41 H41 1.0000 . ?
C41B Cl3B 1.489(12) . ?
C41B Cl2B 1.549(12) . ?
C41B Cl1B 1.593(12) . ?
C41B H41B 1.0000 . ?

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
N3_1 C1_1 C2_1 123.7(3) 2_766 . ?
N3_1 C1_1 C23_1 128.9(3) 2_766 . ?
C2_1 C1_1 C23_1 107.4(3) . . ?
N3_1 C2_1 C1_1 124.0(3) . . ?
N3_1 C2_1 C11_1 127.2(3) . . ?
C1_1 C2_1 C11_1 108.8(3) . . ?
C2_1 N3_1 C1_1 112.2(3) . 2_766 ?
C12_1 C11_1 C24_1 119.3(3) . . ?
C12_1 C11_1 C2_1 135.8(3) . . ?
C24_1 C11_1 C2_1 104.9(3) . . ?
C11_1 C12_1 C13_1 118.2(3) . . ?
C11_1 C12_1 H12_1 120.9 . . ?
C13_1 C12_1 H12_1 120.9 . . ?
C14_1 C13_1 C12_1 122.6(3) . . ?
C14_1 C13_1 H13_1 118.7 . . ?
C12_1 C13_1 H13_1 118.7 . . ?
C13_1 C14_1 C15_1 120.9(3) . . ?
C13_1 C14_1 H14_1 119.5 . . ?
C15_1 C14_1 H14_1 119.5 . . ?
C16_1 C15_1 C24_1 117.5(3) . . ?
C16_1 C15_1 C14_1 127.2(3) . . ?
C24_1 C15_1 C14_1 115.3(3) . . ?
C15_1 C16_1 C17_1 120.2(3) . . ?
C15_1 C16_1 C31_1 119.2(3) . . ?
C17_1 C16_1 C31_1 120.5(3) . . ?
C18_1 C17_1 C16_1 121.4(3) . . ?
C18_1 C17_1 C22_1 117.6(3) . . ?
C16_1 C17_1 C22_1 121.0(3) . . ?
C19_1 C18_1 C17_1 121.3(3) . . ?
C19_1 C18_1 H18_1 119.3 . . ?
C17_1 C18_1 H18_1 119.3 . . ?
C18_1 C19_1 C20_1 120.9(4) . . ?
C18_1 C19_1 H19_1 119.6 . . ?
C20_1 C19_1 H19_1 119.6 . . ?
C21_1 C20_1 C19_1 120.4(4) . . ?
C21_1 C20_1 H20_1 119.8 . . ?
C19_1 C20_1 H20_1 119.8 . . ?
C20_1 C21_1 C22_1 120.2(3) . . ?
C20_1 C21_1 H21_1 119.9 . . ?
C22_1 C21_1 H21_1 119.9 . . ?
C23_1 C22_1 C21_1 122.8(3) . . ?
C23_1 C22_1 C17_1 117.7(3) . . ?
C21_1 C22_1 C17_1 119.5(3) . . ?
C24_1 C23_1 C22_1 120.1(3) . . ?
C24_1 C23_1 C1_1 106.1(3) . . ?
C22_1 C23_1 C1_1 133.9(3) . . ?
C23_1 C24_1 C15_1 123.5(3) . . ?
C23_1 C24_1 C11_1 112.8(3) . . ?
C15_1 C24_1 C11_1 123.7(3) . . ?
C36_1 C31_1 C32_1 120.7(3) . . ?
C36_1 C31_1 C16_1 120.3(3) . . ?
C32_1 C31_1 C16_1 118.9(3) . . ?
C33_1 C32_1 C31_1 118.6(4) . . ?
C33_1 C32_1 C37_1 120.4(4) . . ?
C31_1 C32_1 C37_1 120.9(3) . . ?
C34_1 C33_1 C32_1 122.5(4) . . ?
C34_1 C33_1 H33_1 118.8 . . ?
C32_1 C33_1 H33_1 118.8 . . ?
C33_1 C34_1 C35_1 118.4(4) . . ?
C33_1 C34_1 C38_1 121.7(5) . . ?
C35_1 C34_1 C38_1 119.9(5) . . ?
C34_1 C35_1 C36_1 121.7(4) . . ?
C34_1 C35_1 H35_1 119.1 . . ?
C36_1 C35_1 H35_1 119.1 . . ?
C31_1 C36_1 C35_1 118.0(4) . . ?
C31_1 C36_1 C39_1 120.8(3) . . ?
C35_1 C36_1 C39_1 121.2(4) . . ?
C32_1 C37_1 H37A_1 109.5 . . ?
C32_1 C37_1 H37B_1 109.5 . . ?
H37A_1 C37_1 H37B_1 109.5 . . ?
C32_1 C37_1 H37C_1 109.5 . . ?
H37A_1 C37_1 H37C_1 109.5 . . ?
H37B_1 C37_1 H37C_1 109.5 . . ?
C34_1 C38_1 H38A_1 109.5 . . ?
C34_1 C38_1 H38B_1 109.5 . . ?
H38A_1 C38_1 H38B_1 109.5 . . ?
C34_1 C38_1 H38C_1 109.5 . . ?
H38A_1 C38_1 H38C_1 109.5 . . ?
H38B_1 C38_1 H38C_1 109.5 . . ?
C36_1 C39_1 H39A_1 109.5 . . ?
C36_1 C39_1 H39B_1 109.5 . . ?
H39A_1 C39_1 H39B_1 109.5 . . ?
C36_1 C39_1 H39C_1 109.5 . . ?
H39A_1 C39_1 H39C_1 109.5 . . ?
H39B_1 C39_1 H39C_1 109.5 . . ?
N3_2 C1_2 C2_2 123.1(3) 2_666 . ?
N3_2 C1_2 C23_2 128.3(3) 2_666 . ?
C2_2 C1_2 C23_2 108.6(3) . . ?
N3_2 C2_2 C1_2 124.7(3) . . ?
N3_2 C2_2 C11_2 127.5(3) . . ?
C1_2 C2_2 C11_2 107.8(3) . . ?
C2_2 N3_2 C1_2 112.2(3) . 2_666 ?
C12_2 C11_2 C24_2 119.8(3) . . ?
C12_2 C11_2 C2_2 135.0(4) . . ?
C24_2 C11_2 C2_2 105.2(3) . . ?
C11_2 C12_2 C13_2 118.1(4) . . ?
C11_2 C12_2 H12_2 121.0 . . ?
C13_2 C12_2 H12_2 121.0 . . ?
C14_2 C13_2 C12_2 122.8(3) . . ?
C14_2 C13_2 H13_2 118.6 . . ?
C12_2 C13_2 H13_2 118.6 . . ?
C13_2 C14_2 C15_2 121.2(4) . . ?
C13_2 C14_2 H14_2 119.4 . . ?
C15_2 C14_2 H14_2 119.4 . . ?
C16_2 C15_2 C24_2 117.5(3) . . ?
C16_2 C15_2 C14_2 127.4(3) . . ?
C24_2 C15_2 C14_2 115.1(4) . . ?
C15_2 C16_2 C17_2 119.9(3) . . ?
C15_2 C16_2 C31_2 118.9(3) . . ?
C17_2 C16_2 C31_2 121.2(4) . . ?
C16_2 C17_2 C18_2 121.4(3) . . ?
C16_2 C17_2 C22_2 120.8(3) . . ?
C18_2 C17_2 C22_2 117.8(3) . . ?
C19_2 C18_2 C17_2 121.6(4) . . ?
C19_2 C18_2 H18_2 119.2 . . ?
C17_2 C18_2 H18_2 119.2 . . ?
C18_2 C19_2 C20_2 120.4(4) . . ?
C18_2 C19_2 H19_2 119.8 . . ?
C20_2 C19_2 H19_2 119.8 . . ?
C21_2 C20_2 C19_2 120.6(4) . . ?
C21_2 C20_2 H20_2 119.7 . . ?
C19_2 C20_2 H20_2 119.7 . . ?
C20_2 C21_2 C22_2 121.0(4) . . ?
C20_2 C21_2 H21_2 119.5 . . ?
C22_2 C21_2 H21_2 119.5 . . ?
C23_2 C22_2 C21_2 123.1(3) . . ?
C23_2 C22_2 C17_2 118.3(3) . . ?
C21_2 C22_2 C17_2 118.6(3) . . ?
C22_2 C23_2 C24_2 119.3(3) . . ?
C22_2 C23_2 C1_2 135.2(3) . . ?
C24_2 C23_2 C1_2 105.6(3) . . ?
C23_2 C24_2 C15_2 124.1(4) . . ?
C23_2 C24_2 C11_2 112.8(3) . . ?
C15_2 C24_2 C11_2 123.1(3) . . ?
C32_2 C31_2 C36_2 119.7(4) . . ?
C32_2 C31_2 C16_2 120.4(3) . . ?
C36_2 C31_2 C16_2 119.8(4) . . ?
C33_2 C32_2 C31_2 118.9(4) . . ?
C33_2 C32_2 C37_2 120.1(4) . . ?
C31_2 C32_2 C37_2 121.0(3) . . ?
C32_2 C33_2 C34_2 121.8(4) . . ?
C32_2 C33_2 H33_2 119.1 . . ?
C34_2 C33_2 H33_2 119.1 . . ?
C35_2 C34_2 C33_2 118.2(4) . . ?
C35_2 C34_2 C38_2 121.9(4) . . ?
C33_2 C34_2 C38_2 119.9(5) . . ?
C36_2 C35_2 C34_2 122.2(4) . . ?
C36_2 C35_2 H35_2 118.9 . . ?
C34_2 C35_2 H35_2 118.9 . . ?
C35_2 C36_2 C31_2 119.3(4) . . ?
C35_2 C36_2 C39_2 120.7(4) . . ?
C31_2 C36_2 C39_2 120.0(4) . . ?
C32_2 C37_2 H37A_2 109.5 . . ?
C32_2 C37_2 H37B_2 109.5 . . ?
H37A_2 C37_2 H37B_2 109.5 . . ?
C32_2 C37_2 H37C_2 109.5 . . ?
H37A_2 C37_2 H37C_2 109.5 . . ?
H37B_2 C37_2 H37C_2 109.5 . . ?
C34_2 C38_2 H38A_2 109.5 . . ?
C34_2 C38_2 H38B_2 109.5 . . ?
H38A_2 C38_2 H38B_2 109.5 . . ?
C34_2 C38_2 H38C_2 109.5 . . ?
H38A_2 C38_2 H38C_2 109.5 . . ?
H38B_2 C38_2 H38C_2 109.5 . . ?
C36_2 C39_2 H39A_2 109.5 . . ?
C36_2 C39_2 H39B_2 109.5 . . ?
H39A_2 C39_2 H39B_2 109.5 . . ?
C36_2 C39_2 H39C_2 109.5 . . ?
H39A_2 C39_2 H39C_2 109.5 . . ?
H39B_2 C39_2 H39C_2 109.5 . . ?
Cl3 C41 Cl1 118.0(6) . . ?
Cl3 C41 Cl2 119.7(6) . . ?
Cl1 C41 Cl2 117.8(5) . . ?
Cl3 C41 H41 97.1 . . ?
Cl1 C41 H41 97.1 . . ?
Cl2 C41 H41 97.1 . . ?
Cl3B C41B Cl2B 121.6(10) . . ?
Cl3B C41B Cl1B 117.5(10) . . ?
Cl2B C41B Cl1B 112.8(10) . . ?
Cl3B C41B H41B 99.5 . . ?
Cl2B C41B H41B 99.5 . . ?
Cl1B C41B H41B 99.5 . . ?

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
N3_1 C1_1 C2_1 N3_1 0.3(5) 2_766 . . . ?
C23_1 C1_1 C2_1 N3_1 179.2(3) . . . . ?
N3_1 C1_1 C2_1 C11_1 -179.9(3) 2_766 . . . ?
C23_1 C1_1 C2_1 C11_1 -1.0(3) . . . . ?
C1_1 C2_1 N3_1 C1_1 -0.3(5) . . . 2_766 ?
C11_1 C2_1 N3_1 C1_1 179.9(3) . . . 2_766 ?
N3_1 C2_1 C11_1 C12_1 -0.1(6) . . . . ?
C1_1 C2_1 C11_1 C12_1 -179.9(4) . . . . ?
N3_1 C2_1 C11_1 C24_1 -179.4(3) . . . . ?
C1_1 C2_1 C11_1 C24_1 0.8(3) . . . . ?
C24_1 C11_1 C12_1 C13_1 0.1(5) . . . . ?
C2_1 C11_1 C12_1 C13_1 -179.1(3) . . . . ?
C11_1 C12_1 C13_1 C14_1 -1.1(5) . . . . ?
C12_1 C13_1 C14_1 C15_1 1.3(5) . . . . ?
C13_1 C14_1 C15_1 C16_1 -180.0(3) . . . . ?
C13_1 C14_1 C15_1 C24_1 -0.5(5) . . . . ?
C24_1 C15_1 C16_1 C17_1 2.6(5) . . . . ?
C14_1 C15_1 C16_1 C17_1 -178.0(3) . . . . ?
C24_1 C15_1 C16_1 C31_1 -173.9(3) . . . . ?
C14_1 C15_1 C16_1 C31_1 5.5(5) . . . . ?
C15_1 C16_1 C17_1 C18_1 177.5(3) . . . . ?
C31_1 C16_1 C17_1 C18_1 -6.1(5) . . . . ?
C15_1 C16_1 C17_1 C22_1 -2.3(5) . . . . ?
C31_1 C16_1 C17_1 C22_1 174.1(3) . . . . ?
C16_1 C17_1 C18_1 C19_1 179.9(3) . . . . ?
C22_1 C17_1 C18_1 C19_1 -0.3(5) . . . . ?
C17_1 C18_1 C19_1 C20_1 0.1(6) . . . . ?
C18_1 C19_1 C20_1 C21_1 0.1(6) . . . . ?
C19_1 C20_1 C21_1 C22_1 -0.2(6) . . . . ?
C20_1 C21_1 C22_1 C23_1 -179.8(3) . . . . ?
C20_1 C21_1 C22_1 C17_1 0.1(5) . . . . ?
C18_1 C17_1 C22_1 C23_1 -179.9(3) . . . . ?
C16_1 C17_1 C22_1 C23_1 -0.1(5) . . . . ?
C18_1 C17_1 C22_1 C21_1 0.2(5) . . . . ?
C16_1 C17_1 C22_1 C21_1 -180.0(3) . . . . ?
C21_1 C22_1 C23_1 C24_1 -178.0(3) . . . . ?
C17_1 C22_1 C23_1 C24_1 2.1(5) . . . . ?
C21_1 C22_1 C23_1 C1_1 0.5(6) . . . . ?
C17_1 C22_1 C23_1 C1_1 -179.4(3) . . . . ?
N3_1 C1_1 C23_1 C24_1 179.6(3) 2_766 . . . ?
C2_1 C1_1 C23_1 C24_1 0.8(3) . . . . ?
N3_1 C1_1 C23_1 C22_1 1.0(6) 2_766 . . . ?
C2_1 C1_1 C23_1 C22_1 -177.8(3) . . . . ?
C22_1 C23_1 C24_1 C15_1 -1.9(5) . . . . ?
C1_1 C23_1 C24_1 C15_1 179.3(3) . . . . ?
C22_1 C23_1 C24_1 C11_1 178.5(3) . . . . ?
C1_1 C23_1 C24_1 C11_1 -0.4(4) . . . . ?
C16_1 C15_1 C24_1 C23_1 -0.6(5) . . . . ?
C14_1 C15_1 C24_1 C23_1 179.9(3) . . . . ?
C16_1 C15_1 C24_1 C11_1 179.1(3) . . . . ?
C14_1 C15_1 C24_1 C11_1 -0.4(5) . . . . ?
C12_1 C11_1 C24_1 C23_1 -179.7(3) . . . . ?
C2_1 C11_1 C24_1 C23_1 -0.2(4) . . . . ?
C12_1 C11_1 C24_1 C15_1 0.6(5) . . . . ?
C2_1 C11_1 C24_1 C15_1 -179.9(3) . . . . ?
C15_1 C16_1 C31_1 C36_1 -86.1(4) . . . . ?
C17_1 C16_1 C31_1 C36_1 97.4(4) . . . . ?
C15_1 C16_1 C31_1 C32_1 92.3(4) . . . . ?
C17_1 C16_1 C31_1 C32_1 -84.2(4) . . . . ?
C36_1 C31_1 C32_1 C33_1 -1.1(6) . . . . ?
C16_1 C31_1 C32_1 C33_1 -179.4(3) . . . . ?
C36_1 C31_1 C32_1 C37_1 178.9(4) . . . . ?
C16_1 C31_1 C32_1 C37_1 0.6(5) . . . . ?
C31_1 C32_1 C33_1 C34_1 1.2(6) . . . . ?
C37_1 C32_1 C33_1 C34_1 -178.8(4) . . . . ?
C32_1 C33_1 C34_1 C35_1 -0.9(6) . . . . ?
C32_1 C33_1 C34_1 C38_1 177.7(4) . . . . ?
C33_1 C34_1 C35_1 C36_1 0.6(6) . . . . ?
C38_1 C34_1 C35_1 C36_1 -178.1(4) . . . . ?
C32_1 C31_1 C36_1 C35_1 0.8(6) . . . . ?
C16_1 C31_1 C36_1 C35_1 179.1(4) . . . . ?
C32_1 C31_1 C36_1 C39_1 -178.1(4) . . . . ?
C16_1 C31_1 C36_1 C39_1 0.2(6) . . . . ?
C34_1 C35_1 C36_1 C31_1 -0.5(6) . . . . ?
C34_1 C35_1 C36_1 C39_1 178.3(4) . . . . ?
N3_2 C1_2 C2_2 N3_2 -0.5(5) 2_666 . . . ?
C23_2 C1_2 C2_2 N3_2 179.9(3) . . . . ?
N3_2 C1_2 C2_2 C11_2 179.5(3) 2_666 . . . ?
C23_2 C1_2 C2_2 C11_2 -0.1(4) . . . . ?
C1_2 C2_2 N3_2 C1_2 0.5(5) . . . 2_666 ?
C11_2 C2_2 N3_2 C1_2 -179.6(3) . . . 2_666 ?
N3_2 C2_2 C11_2 C12_2 -0.2(6) . . . . ?
C1_2 C2_2 C11_2 C12_2 179.8(4) . . . . ?
N3_2 C2_2 C11_2 C24_2 -180.0(3) . . . . ?
C1_2 C2_2 C11_2 C24_2 0.0(3) . . . . ?
C24_2 C11_2 C12_2 C13_2 -0.4(5) . . . . ?
C2_2 C11_2 C12_2 C13_2 179.9(3) . . . . ?
C11_2 C12_2 C13_2 C14_2 -0.2(5) . . . . ?
C12_2 C13_2 C14_2 C15_2 0.3(5) . . . . ?
C13_2 C14_2 C15_2 C16_2 -178.8(4) . . . . ?
C13_2 C14_2 C15_2 C24_2 0.2(5) . . . . ?
C24_2 C15_2 C16_2 C17_2 2.1(5) . . . . ?
C14_2 C15_2 C16_2 C17_2 -179.0(3) . . . . ?
C24_2 C15_2 C16_2 C31_2 -176.9(3) . . . . ?
C14_2 C15_2 C16_2 C31_2 2.1(5) . . . . ?
C15_2 C16_2 C17_2 C18_2 177.8(3) . . . . ?
C31_2 C16_2 C17_2 C18_2 -3.3(5) . . . . ?
C15_2 C16_2 C17_2 C22_2 -1.2(5) . . . . ?
C31_2 C16_2 C17_2 C22_2 177.7(3) . . . . ?
C16_2 C17_2 C18_2 C19_2 -179.7(4) . . . . ?
C22_2 C17_2 C18_2 C19_2 -0.7(6) . . . . ?
C17_2 C18_2 C19_2 C20_2 1.0(6) . . . . ?
C18_2 C19_2 C20_2 C21_2 -0.6(6) . . . . ?
C19_2 C20_2 C21_2 C22_2 -0.1(6) . . . . ?
C20_2 C21_2 C22_2 C23_2 -179.8(4) . . . . ?
C20_2 C21_2 C22_2 C17_2 0.4(5) . . . . ?
C16_2 C17_2 C22_2 C23_2 -0.9(5) . . . . ?
C18_2 C17_2 C22_2 C23_2 -179.9(3) . . . . ?
C16_2 C17_2 C22_2 C21_2 179.0(3) . . . . ?
C18_2 C17_2 C22_2 C21_2 0.0(5) . . . . ?
C21_2 C22_2 C23_2 C24_2 -178.0(3) . . . . ?
C17_2 C22_2 C23_2 C24_2 1.9(5) . . . . ?
C21_2 C22_2 C23_2 C1_2 1.7(6) . . . . ?
C17_2 C22_2 C23_2 C1_2 -178.4(3) . . . . ?
N3_2 C1_2 C23_2 C22_2 0.9(6) 2_666 . . . ?
C2_2 C1_2 C23_2 C22_2 -179.5(4) . . . . ?
N3_2 C1_2 C23_2 C24_2 -179.4(3) 2_666 . . . ?
C2_2 C1_2 C23_2 C24_2 0.2(4) . . . . ?
C22_2 C23_2 C24_2 C15_2 -1.0(5) . . . . ?
C1_2 C23_2 C24_2 C15_2 179.2(3) . . . . ?
C22_2 C23_2 C24_2 C11_2 179.6(3) . . . . ?
C1_2 C23_2 C24_2 C11_2 -0.2(4) . . . . ?
C16_2 C15_2 C24_2 C23_2 -1.0(5) . . . . ?
C14_2 C15_2 C24_2 C23_2 179.9(3) . . . . ?
C16_2 C15_2 C24_2 C11_2 178.3(3) . . . . ?
C14_2 C15_2 C24_2 C11_2 -0.8(5) . . . . ?
C12_2 C11_2 C24_2 C23_2 -179.7(3) . . . . ?
C2_2 C11_2 C24_2 C23_2 0.1(4) . . . . ?
C12_2 C11_2 C24_2 C15_2 0.9(5) . . . . ?
C2_2 C11_2 C24_2 C15_2 -179.3(3) . . . . ?
C15_2 C16_2 C31_2 C32_2 99.4(4) . . . . ?
C17_2 C16_2 C31_2 C32_2 -79.5(5) . . . . ?
C15_2 C16_2 C31_2 C36_2 -76.9(5) . . . . ?
C17_2 C16_2 C31_2 C36_2 104.2(4) . . . . ?
C36_2 C31_2 C32_2 C33_2 0.5(6) . . . . ?
C16_2 C31_2 C32_2 C33_2 -175.9(4) . . . . ?
C36_2 C31_2 C32_2 C37_2 179.9(4) . . . . ?
C16_2 C31_2 C32_2 C37_2 3.6(6) . . . . ?
C31_2 C32_2 C33_2 C34_2 0.6(6) . . . . ?
C37_2 C32_2 C33_2 C34_2 -178.8(4) . . . . ?
C32_2 C33_2 C34_2 C35_2 -1.0(7) . . . . ?
C32_2 C33_2 C34_2 C38_2 178.9(5) . . . . ?
C33_2 C34_2 C35_2 C36_2 0.2(8) . . . . ?
C38_2 C34_2 C35_2 C36_2 -179.7(5) . . . . ?
C34_2 C35_2 C36_2 C31_2 0.8(7) . . . . ?
C34_2 C35_2 C36_2 C39_2 -179.6(5) . . . . ?
C32_2 C31_2 C36_2 C35_2 -1.2(6) . . . . ?
C16_2 C31_2 C36_2 C35_2 175.2(4) . . . . ?
C32_2 C31_2 C36_2 C39_2 179.3(4) . . . . ?
C16_2 C31_2 C36_2 C39_2 -4.3(6) . . . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.046



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





####################################################################### 
# 
# 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_sve112
_database_code_depnum_ccdc_archive 'CCDC 2353532'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'DBAF-N2 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H16 N2'
_chemical_formula_weight         428.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8037(16)
_cell_length_b                   5.7081(9)
_cell_length_c                   16.724(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.465(2)
_cell_angle_gamma                90
_cell_volume                     1014.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2718
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.89

_exptl_crystal_description       irregular
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8593
_exptl_absorpt_correction_T_max  0.9594
_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            10502
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2476
_reflns_number_gt                1697
_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)+(0.0552P)²+0.5288P] 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         2476
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1350
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
N1 N 0.41546(14) 1.0029(3) 0.55882(9) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.40826(16) 0.8466(3) 0.49834(10) 0.0307(4) Uani 1 1 d . . . . .
C3 C 0.49051(16) 0.8434(3) 0.44077(11) 0.0311(4) Uani 1 1 d . . . . .
C11 C 0.31785(17) 0.6524(3) 0.47908(11) 0.0335(4) Uani 1 1 d . . . . .
C12 C 0.21784(18) 0.5682(4) 0.51043(12) 0.0395(5) Uani 1 1 d . . . . .
H12 H 0.192251 0.642113 0.555645 0.047 Uiso 1 1 calc R U . . .
C13 C 0.15318(19) 0.3669(4) 0.47354(12) 0.0425(5) Uani 1 1 d . . . . .
H13 H 0.083316 0.309327 0.494850 0.051 Uiso 1 1 calc R U . . .
C14 C 0.18696(19) 0.2531(4) 0.40902(12) 0.0413(5) Uani 1 1 d . . . . .
H14 H 0.141624 0.118171 0.387115 0.050 Uiso 1 1 calc R U . . .
C15 C 0.29057(18) 0.3363(3) 0.37415(11) 0.0355(4) Uani 1 1 d . . . . .
C16 C 0.33708(19) 0.2423(3) 0.30806(12) 0.0401(5) Uani 1 1 d . . . . .
H16 H 0.299308 0.105453 0.281981 0.048 Uiso 1 1 calc R U . . .
C17 C 0.43826(18) 0.3467(3) 0.27978(12) 0.0374(5) Uani 1 1 d . . . . .
C18 C 0.4850(2) 0.2505(4) 0.21238(13) 0.0462(5) Uani 1 1 d . . . . .
H18 H 0.447858 0.112254 0.186949 0.055 Uiso 1 1 calc R U . . .
C19 C 0.5818(2) 0.3532(4) 0.18396(13) 0.0510(6) Uani 1 1 d . . . . .
H19 H 0.611463 0.285255 0.139107 0.061 Uiso 1 1 calc R U . . .
C20 C 0.6393(2) 0.5595(4) 0.22001(13) 0.0478(5) Uani 1 1 d . . . . .
H20 H 0.706079 0.630250 0.198750 0.057 Uiso 1 1 calc R U . . .
C21 C 0.59924(18) 0.6571(4) 0.28514(12) 0.0396(5) Uani 1 1 d . . . . .
H21 H 0.639003 0.794749 0.309324 0.048 Uiso 1 1 calc R U . . .
C22 C 0.49862(17) 0.5555(3) 0.31740(11) 0.0338(4) Uani 1 1 d . . . . .
C23 C 0.45357(17) 0.6463(3) 0.38486(11) 0.0318(4) Uani 1 1 d . . . . .
C24 C 0.35209(17) 0.5377(3) 0.41068(11) 0.0330(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.340(2) . ?
N1 C3 1.341(2) 3_676 ?
C2 C3 1.424(3) . ?
C2 C11 1.474(3) . ?
C3 C23 1.471(2) . ?
C11 C12 1.371(3) . ?
C11 C24 1.424(3) . ?
C12 C13 1.425(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.434(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(3) . ?
C15 C24 1.410(3) . ?
C16 C17 1.400(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.426(3) . ?
C17 C22 1.447(3) . ?
C18 C19 1.358(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.414(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.362(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.422(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.406(3) . ?
C23 C24 1.395(3) . ?

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 N1 C3 112.28(15) . 3_676 ?
N1 C2 C3 124.13(16) . . ?
N1 C2 C11 127.65(17) . . ?
C3 C2 C11 108.22(15) . . ?
N1 C3 C2 123.59(16) 3_676 . ?
N1 C3 C23 128.40(16) 3_676 . ?
C2 C3 C23 108.00(16) . . ?
C12 C11 C24 118.93(18) . . ?
C12 C11 C2 135.84(18) . . ?
C24 C11 C2 105.23(16) . . ?
C11 C12 C13 118.40(19) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 123.05(19) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
C13 C14 C15 120.31(19) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C24 116.46(18) . . ?
C16 C15 C14 127.75(18) . . ?
C24 C15 C14 115.79(18) . . ?
C17 C16 C15 121.14(18) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.89(19) . . ?
C16 C17 C22 121.43(18) . . ?
C18 C17 C22 117.68(19) . . ?
C19 C18 C17 121.1(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 123.63(18) . . ?
C23 C22 C17 117.27(18) . . ?
C21 C22 C17 119.10(17) . . ?
C24 C23 C22 119.38(17) . . ?
C24 C23 C3 106.32(15) . . ?
C22 C23 C3 134.30(18) . . ?
C23 C24 C15 124.29(17) . . ?
C23 C24 C11 112.21(16) . . ?
C15 C24 C11 123.50(17) . . ?

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 N1 C2 C3 -0.1(3) 3_676 . . . ?
C3 N1 C2 C11 179.76(16) 3_676 . . . ?
N1 C2 C3 N1 0.2(3) . . . 3_676 ?
C11 C2 C3 N1 -179.75(16) . . . 3_676 ?
N1 C2 C3 C23 179.56(16) . . . . ?
C11 C2 C3 C23 -0.36(19) . . . . ?
N1 C2 C11 C12 1.0(3) . . . . ?
C3 C2 C11 C12 -179.1(2) . . . . ?
N1 C2 C11 C24 -178.93(17) . . . . ?
C3 C2 C11 C24 0.98(19) . . . . ?
C24 C11 C12 C13 0.7(3) . . . . ?
C2 C11 C12 C13 -179.23(19) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 -179.59(19) . . . . ?
C13 C14 C15 C24 0.0(3) . . . . ?
C24 C15 C16 C17 -0.8(3) . . . . ?
C14 C15 C16 C17 178.72(18) . . . . ?
C15 C16 C17 C18 -179.88(18) . . . . ?
C15 C16 C17 C22 -0.1(3) . . . . ?
C16 C17 C18 C19 178.96(19) . . . . ?
C22 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C19 C20 C21 C22 -0.7(3) . . . . ?
C20 C21 C22 C23 179.42(19) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
C16 C17 C22 C23 1.5(3) . . . . ?
C18 C17 C22 C23 -178.72(17) . . . . ?
C16 C17 C22 C21 -178.66(17) . . . . ?
C18 C17 C22 C21 1.1(3) . . . . ?
C21 C22 C23 C24 178.30(17) . . . . ?
C17 C22 C23 C24 -1.9(2) . . . . ?
C21 C22 C23 C3 -2.6(3) . . . . ?
C17 C22 C23 C3 177.24(18) . . . . ?
N1 C3 C23 C24 178.94(17) 3_676 . . . ?
C2 C3 C23 C24 -0.42(19) . . . . ?
N1 C3 C23 C22 -0.3(3) 3_676 . . . ?
C2 C3 C23 C22 -179.64(19) . . . . ?
C22 C23 C24 C15 1.0(3) . . . . ?
C3 C23 C24 C15 -178.38(16) . . . . ?
C22 C23 C24 C11 -179.55(16) . . . . ?
C3 C23 C24 C11 1.1(2) . . . . ?
C16 C15 C24 C23 0.4(3) . . . . ?
C14 C15 C24 C23 -179.18(17) . . . . ?
C16 C15 C24 C11 -178.97(17) . . . . ?
C14 C15 C24 C11 1.4(3) . . . . ?
C12 C11 C24 C23 178.75(16) . . . . ?
C2 C11 C24 C23 -1.3(2) . . . . ?
C12 C11 C24 C15 -1.8(3) . . . . ?
C2 C11 C24 C15 178.17(16) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.041


