# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1414910'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H18 Cl2 N2 O2'
_chemical_formula_sum            'C32 H18 Cl2 N2 O2'
_chemical_formula_weight         533.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   7.5637(5)
_cell_length_b                   27.8153(18)
_cell_length_c                   11.7714(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.895(6)
_cell_angle_gamma                90.00
_cell_volume                     2458.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5964
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.25

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
CrysAlis (Oxford Diffraction, 2006)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18631
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0830
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.25
_reflns_number_total             5964
_reflns_number_gt                2985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.4499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5964
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7803(4) -0.04613(11) 0.4054(2) 0.0412(7) Uani 1 1 d . . .
C2 C 0.6880(4) -0.03046(11) 0.2959(2) 0.0416(7) Uani 1 1 d . . .
C3 C 0.7016(3) -0.06070(11) 0.1923(2) 0.0416(7) Uani 1 1 d . . .
C4 C 0.6551(4) -0.04011(12) 0.0862(2) 0.0522(8) Uani 1 1 d . . .
H4 H 0.6156 -0.0084 0.0817 0.063 Uiso 1 1 calc R . .
C5 C 0.6660(4) -0.06557(14) -0.0130(3) 0.0618(9) Uani 1 1 d . . .
H5 H 0.6342 -0.0512 -0.0838 0.074 Uiso 1 1 calc R . .
C6 C 0.7239(5) -0.11222(14) -0.0064(3) 0.0633(9) Uani 1 1 d . . .
H6 H 0.7325 -0.1294 -0.0733 0.076 Uiso 1 1 calc R . .
C7 C 0.7694(5) -0.13375(13) 0.0974(3) 0.0620(9) Uani 1 1 d . . .
H7 H 0.8060 -0.1657 0.1010 0.074 Uiso 1 1 calc R . .
C8 C 0.7607(4) -0.10803(11) 0.1968(3) 0.0509(8) Uani 1 1 d . . .
H8 H 0.7948 -0.1225 0.2672 0.061 Uiso 1 1 calc R . .
C9 C 0.7539(3) 0.09201(11) 0.8127(2) 0.0414(7) Uani 1 1 d . . .
C10 C 0.7606(4) 0.14479(10) 0.8326(2) 0.0426(7) Uani 1 1 d . . .
C11 C 0.6977(4) 0.16188(12) 0.9309(3) 0.0564(8) Uani 1 1 d . . .
H11 H 0.6507 0.1408 0.9808 0.068 Uiso 1 1 calc R . .
C12 C 0.7058(5) 0.21074(14) 0.9541(3) 0.0751(11) Uani 1 1 d . . .
H12 H 0.6611 0.2225 1.0189 0.090 Uiso 1 1 calc R . .
C13 C 0.7783(6) 0.24156(14) 0.8830(4) 0.0789(12) Uani 1 1 d . . .
H13 H 0.7836 0.2742 0.9000 0.095 Uiso 1 1 calc R . .
C14 C 0.8438(5) 0.22500(13) 0.7863(3) 0.0663(10) Uani 1 1 d . . .
H14 H 0.8945 0.2463 0.7386 0.080 Uiso 1 1 calc R . .
C15 C 0.8341(4) 0.17655(12) 0.7603(3) 0.0526(8) Uani 1 1 d . . .
H15 H 0.8767 0.1652 0.6944 0.063 Uiso 1 1 calc R . .
C16 C 0.4536(4) 0.17795(10) 0.6068(3) 0.0461(7) Uani 1 1 d . . .
H16 H 0.4833 0.1845 0.6843 0.055 Uiso 1 1 calc R . .
C17 C 0.3413(4) 0.20769(11) 0.5389(3) 0.0519(8) Uani 1 1 d . . .
C18 C 0.2994(4) 0.19998(12) 0.4229(3) 0.0582(9) Uani 1 1 d . . .
H18 H 0.2274 0.2219 0.3792 0.070 Uiso 1 1 calc R . .
C19 C 0.3631(4) 0.16027(11) 0.3716(3) 0.0556(8) Uani 1 1 d . . .
H19 H 0.3343 0.1548 0.2936 0.067 Uiso 1 1 calc R . .
C20 C 0.4713(4) 0.12867(11) 0.4390(2) 0.0443(7) Uani 1 1 d . . .
C21 C 0.5222(4) 0.13749(10) 0.5567(2) 0.0408(7) Uani 1 1 d . . .
C22 C 0.6328(3) 0.09714(10) 0.5981(2) 0.0384(6) Uani 1 1 d . . .
C23 C 0.7255(3) 0.07513(10) 0.6939(2) 0.0381(6) Uani 1 1 d . . .
C24 C 0.6349(3) 0.06548(10) 0.5039(2) 0.0391(6) Uani 1 1 d . . .
C25 C 0.7249(3) 0.02370(10) 0.5399(2) 0.0373(6) Uani 1 1 d . . .
C26 C 0.7917(3) -0.02204(10) 0.5065(2) 0.0386(6) Uani 1 1 d . . .
C27 C 0.8889(3) -0.04160(10) 0.6128(2) 0.0385(7) Uani 1 1 d . . .
C28 C 0.8778(3) -0.00947(10) 0.7032(2) 0.0370(6) Uani 1 1 d . . .
C29 C 0.9589(4) -0.01907(10) 0.8124(2) 0.0426(7) Uani 1 1 d . . .
H29 H 0.9509 0.0025 0.8720 0.051 Uiso 1 1 calc R . .
C30 C 1.0525(4) -0.06172(11) 0.8303(3) 0.0504(8) Uani 1 1 d . . .
H30 H 1.1088 -0.0691 0.9028 0.061 Uiso 1 1 calc R . .
C31 C 1.0626(4) -0.09323(11) 0.7414(3) 0.0489(7) Uani 1 1 d . . .
C32 C 0.9821(4) -0.08405(10) 0.6316(2) 0.0454(7) Uani 1 1 d . . .
H32 H 0.9906 -0.1058 0.5724 0.055 Uiso 1 1 calc R . .
N1 N 0.5416(3) 0.08524(9) 0.40857(19) 0.0469(6) Uani 1 1 d . . .
H1 H 0.5287 0.0728 0.3412 0.056 Uiso 1 1 calc R . .
N2 N 0.7769(3) 0.03063(8) 0.65738(18) 0.0365(5) Uani 1 1 d . . .
O1 O 0.6024(3) 0.00697(8) 0.28675(17) 0.0568(6) Uani 1 1 d . . .
O2 O 0.7686(3) 0.06377(8) 0.89300(16) 0.0562(6) Uani 1 1 d . . .
Cl1 Cl 1.18151(15) -0.14650(3) 0.76695(8) 0.0817(3) Uani 1 1 d . . .
Cl2 Cl 0.24958(15) 0.25733(3) 0.60087(9) 0.0804(3) Uani 1 1 d . . .
H1A H 0.843(3) -0.0759(10) 0.407(2) 0.038(7) Uiso 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 C26 1.359(4) . ?
C1 C2 1.457(4) . ?
C1 H1A 0.95(3) . ?
C2 O1 1.224(3) . ?
C2 C3 1.495(4) . ?
C3 C4 1.380(4) . ?
C3 C8 1.390(4) . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O2 1.223(3) . ?
C9 C23 1.466(4) . ?
C9 C10 1.486(4) . ?
C10 C11 1.387(4) . ?
C10 C15 1.388(4) . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 C21 1.399(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 Cl2 1.744(3) . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9300 . ?
C20 N1 1.384(4) . ?
C20 C21 1.414(4) . ?
C21 C22 1.449(4) . ?
C22 C23 1.396(4) . ?
C22 C24 1.417(4) . ?
C23 N2 1.382(3) . ?
C24 N1 1.367(3) . ?
C24 C25 1.387(4) . ?
C25 N2 1.405(3) . ?
C25 C26 1.441(4) . ?
C26 C27 1.477(4) . ?
C27 C32 1.379(4) . ?
C27 C28 1.400(4) . ?
C28 C29 1.382(4) . ?
C28 N2 1.421(3) . ?
C29 C30 1.385(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.374(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.385(4) . ?
C31 Cl1 1.741(3) . ?
C32 H32 0.9300 . ?
N1 H1 0.8600 . ?

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 C1 C2 126.9(3) . . ?
C26 C1 H1A 115.3(16) . . ?
C2 C1 H1A 117.8(16) . . ?
O1 C2 C1 121.7(3) . . ?
O1 C2 C3 119.6(3) . . ?
C1 C2 C3 118.8(3) . . ?
C4 C3 C8 118.2(3) . . ?
C4 C3 C2 118.0(3) . . ?
C8 C3 C2 123.8(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C3 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
O2 C9 C23 121.4(3) . . ?
O2 C9 C10 121.0(3) . . ?
C23 C9 C10 117.7(2) . . ?
C11 C10 C15 119.7(3) . . ?
C11 C10 C9 117.4(3) . . ?
C15 C10 C9 122.7(3) . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 119.7(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C10 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C17 C16 C21 118.3(3) . . ?
C17 C16 H16 120.9 . . ?
C21 C16 H16 120.9 . . ?
C16 C17 C18 122.4(3) . . ?
C16 C17 Cl2 118.9(2) . . ?
C18 C17 Cl2 118.7(2) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 118.2(3) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
N1 C20 C19 128.7(3) . . ?
N1 C20 C21 109.7(2) . . ?
C19 C20 C21 121.6(3) . . ?
C16 C21 C20 118.8(3) . . ?
C16 C21 C22 135.2(3) . . ?
C20 C21 C22 105.9(2) . . ?
C23 C22 C24 108.0(2) . . ?
C23 C22 C21 145.6(3) . . ?
C24 C22 C21 106.2(2) . . ?
N2 C23 C22 105.9(2) . . ?
N2 C23 C9 124.7(2) . . ?
C22 C23 C9 129.2(3) . . ?
N1 C24 C25 140.7(3) . . ?
N1 C24 C22 109.8(2) . . ?
C25 C24 C22 109.4(2) . . ?
C24 C25 N2 104.8(2) . . ?
C24 C25 C26 146.3(3) . . ?
N2 C25 C26 108.9(2) . . ?
C1 C26 C25 133.4(3) . . ?
C1 C26 C27 122.2(3) . . ?
C25 C26 C27 104.5(2) . . ?
C32 C27 C28 120.1(3) . . ?
C32 C27 C26 130.1(3) . . ?
C28 C27 C26 109.9(2) . . ?
C29 C28 C27 121.5(3) . . ?
C29 C28 N2 131.5(3) . . ?
C27 C28 N2 106.9(2) . . ?
C28 C29 C30 117.9(3) . . ?
C28 C29 H29 121.0 . . ?
C30 C29 H29 121.0 . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 122.3(3) . . ?
C30 C31 Cl1 119.1(2) . . ?
C32 C31 Cl1 118.6(2) . . ?
C27 C32 C31 117.8(3) . . ?
C27 C32 H32 121.1 . . ?
C31 C32 H32 121.1 . . ?
C24 N1 C20 108.4(2) . . ?
C24 N1 H1 125.8 . . ?
C20 N1 H1 125.8 . . ?
C23 N2 C25 111.9(2) . . ?
C23 N2 C28 138.0(2) . . ?
C25 N2 C28 109.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.046
