# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

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

data_cckd_54dia2_25aug2020_0m_a_sqd
_database_code_depnum_ccdc_archive 'CCDC 2086430'
loop_
_audit_author_name
_audit_author_address
'Joseph F. DeJesus'
;Queens University
Canada
;
_audit_update_record             
;
2021-05-28 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Cl N O'
_chemical_formula_sum            'C26 H22 Cl N O'
_chemical_formula_weight         399.89

# start Validation Reply Form
_vrf_PLAT601_cckd_54dia2_25aug2020_0m_a_sqd 
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        190 Ang**3
RESPONSE:  SQUEEZE was used to remove disordered toluene on an inversion center.
;
# end Validation Reply Form

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'
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'

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

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

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

_cell_length_a                   7.5536(3)
_cell_length_b                   15.5289(6)
_cell_length_c                   19.9941(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.8470(10)
_cell_angle_gamma                90
_cell_volume                     2317.39(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.4432
_cell_measurement_theta_max      26.37

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7020
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SABABS (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8 Venture Duo'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34942
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4737
_reflns_number_gt                3970
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0617P)²+0.6014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4737
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.61200(7) 0.12314(3) 0.66304(3) 0.06178(18) Uani 1 1 d . . . . .
O1 O 0.31817(16) 0.50868(7) 0.50752(5) 0.0388(3) Uani 1 1 d . . . . .
H1 H 0.301339 0.554963 0.485727 1.000 Uiso 1 1 calc R U . . .
N1 N -0.08361(19) 0.39627(10) 0.60421(8) 0.0403(3) Uani 1 1 d . . . . .
H3 H -0.142(4) 0.3524(17) 0.5915(13) 0.076(8) Uiso 1 1 d . . . . .
C1 C 0.0890(2) 0.41191(10) 0.58178(7) 0.0305(3) Uani 1 1 d . . . . .
H2 H 0.066433 0.410320 0.531181 0.037 Uiso 1 1 calc R U . . .
C2 C 0.15098(19) 0.50434(9) 0.60197(7) 0.0290(3) Uani 1 1 d . . . . .
H4 H 0.058796 0.544872 0.578552 0.035 Uiso 1 1 calc R U . . .
C3 C 0.1604(2) 0.51803(10) 0.67787(8) 0.0310(3) Uani 1 1 d . . . . .
H5A H 0.259879 0.483373 0.702315 0.037 Uiso 1 1 calc R U . . .
H5B H 0.185649 0.579426 0.688770 0.037 Uiso 1 1 calc R U . . .
C4 C -0.01224(19) 0.49253(9) 0.70126(8) 0.0305(3) Uani 1 1 d . . . . .
C5 C -0.1235(2) 0.43090(10) 0.66468(8) 0.0321(3) Uani 1 1 d . . . . .
C6 C -0.2801(2) 0.40535(12) 0.68838(9) 0.0414(4) Uani 1 1 d . . . . .
H6 H -0.355100 0.362966 0.664258 0.050 Uiso 1 1 calc R U . . .
C7 C -0.3268(2) 0.44076(14) 0.74608(9) 0.0495(5) Uani 1 1 d . . . . .
H7 H -0.433241 0.422324 0.761685 0.059 Uiso 1 1 calc R U . . .
C8 C -0.2208(2) 0.50286(13) 0.78162(9) 0.0462(4) Uani 1 1 d . . . . .
H8 H -0.254033 0.527748 0.821275 0.055 Uiso 1 1 calc R U . . .
C9 C -0.0654(2) 0.52836(11) 0.75868(8) 0.0365(4) Uani 1 1 d . . . . .
H9 H 0.007083 0.571581 0.782854 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3291(2) 0.52615(9) 0.57885(7) 0.0297(3) Uani 1 1 d . . . . .
H10 H 0.421721 0.486688 0.603364 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3930(2) 0.61728(9) 0.59378(7) 0.0301(3) Uani 1 1 d . . . . .
C12 C 0.2757(2) 0.68854(10) 0.57902(8) 0.0357(4) Uani 1 1 d . . . . .
H11 H 0.152884 0.678695 0.561976 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3367(2) 0.77089(10) 0.58896(9) 0.0384(4) Uani 1 1 d . . . . .
H12 H 0.255118 0.817534 0.580053 0.046 Uiso 1 1 calc R U . . .
C14 C 0.5199(2) 0.78790(10) 0.61237(8) 0.0338(3) Uani 1 1 d . . . . .
C15 C 0.6386(2) 0.71732(10) 0.62749(7) 0.0317(3) Uani 1 1 d . . . . .
C16 C 0.5697(2) 0.63271(10) 0.61824(7) 0.0310(3) Uani 1 1 d . . . . .
H13 H 0.648176 0.585273 0.629296 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8222(2) 0.73419(11) 0.65080(9) 0.0403(4) Uani 1 1 d . . . . .
H14 H 0.902978 0.687503 0.661252 0.048 Uiso 1 1 calc R U . . .
C18 C 0.8842(3) 0.81681(12) 0.65840(9) 0.0467(4) Uani 1 1 d . . . . .
H15 H 1.007604 0.827195 0.674053 0.056 Uiso 1 1 calc R U . . .
C19 C 0.7662(3) 0.88644(12) 0.64314(9) 0.0488(5) Uani 1 1 d . . . . .
H16 H 0.810585 0.943667 0.648413 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5887(3) 0.87281(11) 0.62086(9) 0.0432(4) Uani 1 1 d . . . . .
H17 H 0.510474 0.920571 0.610941 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2249(2) 0.34184(9) 0.60432(7) 0.0287(3) Uani 1 1 d . . . . .
C22 C 0.2423(2) 0.30465(10) 0.66831(8) 0.0331(3) Uani 1 1 d . . . . .
H18 H 0.170934 0.325467 0.700043 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3615(2) 0.23788(10) 0.68666(8) 0.0361(4) Uani 1 1 d . . . . .
H19 H 0.372183 0.213030 0.730519 0.043 Uiso 1 1 calc R U . . .
C24 C 0.4641(2) 0.20812(10) 0.64034(9) 0.0371(4) Uani 1 1 d . . . . .
C25 C 0.4515(2) 0.24356(10) 0.57668(9) 0.0388(4) Uani 1 1 d . . . . .
H20 H 0.524040 0.222663 0.545377 0.047 Uiso 1 1 calc R U . . .
C26 C 0.3320(2) 0.30991(10) 0.55905(8) 0.0336(3) Uani 1 1 d . . . . .
H21 H 0.322343 0.334376 0.515087 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C24 1.7432(16) . ?
O1 C10 1.4416(18) . ?
N1 C5 1.398(2) . ?
N1 C1 1.463(2) . ?
C1 C21 1.516(2) . ?
C1 C2 1.544(2) . ?
C2 C3 1.523(2) . ?
C2 C10 1.526(2) . ?
C3 C4 1.505(2) . ?
C4 C9 1.389(2) . ?
C4 C5 1.403(2) . ?
C5 C6 1.398(2) . ?
C6 C7 1.372(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.382(2) . ?
C10 C11 1.510(2) . ?
C11 C16 1.370(2) . ?
C11 C12 1.420(2) . ?
C12 C13 1.363(2) . ?
C13 C14 1.416(2) . ?
C14 C20 1.418(2) . ?
C14 C15 1.419(2) . ?
C15 C16 1.415(2) . ?
C15 C17 1.418(2) . ?
C17 C18 1.366(2) . ?
C18 C19 1.405(3) . ?
C19 C20 1.363(3) . ?
C21 C22 1.391(2) . ?
C21 C26 1.394(2) . ?
C22 C23 1.385(2) . ?
C23 C24 1.376(2) . ?
C24 C25 1.376(2) . ?
C25 C26 1.380(2) . ?

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
C5 N1 C1 121.49(13) . . ?
N1 C1 C21 112.61(13) . . ?
N1 C1 C2 108.84(12) . . ?
C21 C1 C2 115.14(12) . . ?
C3 C2 C10 111.25(12) . . ?
C3 C2 C1 110.86(12) . . ?
C10 C2 C1 111.91(12) . . ?
C4 C3 C2 111.29(12) . . ?
C9 C4 C5 118.54(14) . . ?
C9 C4 C3 121.73(14) . . ?
C5 C4 C3 119.73(13) . . ?
C6 C5 N1 119.37(15) . . ?
C6 C5 C4 119.16(15) . . ?
N1 C5 C4 121.45(14) . . ?
C7 C6 C5 120.78(16) . . ?
C6 C7 C8 120.62(16) . . ?
C7 C8 C9 119.02(17) . . ?
C8 C9 C4 121.84(16) . . ?
O1 C10 C11 109.85(12) . . ?
O1 C10 C2 109.82(12) . . ?
C11 C10 C2 114.73(12) . . ?
C16 C11 C12 118.72(14) . . ?
C16 C11 C10 119.94(13) . . ?
C12 C11 C10 121.23(14) . . ?
C13 C12 C11 120.94(15) . . ?
C12 C13 C14 120.97(15) . . ?
C13 C14 C20 122.32(16) . . ?
C13 C14 C15 118.66(14) . . ?
C20 C14 C15 119.02(16) . . ?
C16 C15 C17 122.41(15) . . ?
C16 C15 C14 118.82(14) . . ?
C17 C15 C14 118.77(15) . . ?
C11 C16 C15 121.84(14) . . ?
C18 C17 C15 120.77(17) . . ?
C17 C18 C19 120.20(17) . . ?
C20 C19 C18 120.74(16) . . ?
C19 C20 C14 120.50(17) . . ?
C22 C21 C26 117.87(14) . . ?
C22 C21 C1 122.33(13) . . ?
C26 C21 C1 119.74(13) . . ?
C23 C22 C21 121.31(14) . . ?
C24 C23 C22 118.93(14) . . ?
C23 C24 C25 121.47(15) . . ?
C23 C24 Cl1 118.93(13) . . ?
C25 C24 Cl1 119.60(13) . . ?
C24 C25 C26 118.97(15) . . ?
C25 C26 C21 121.45(14) . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.038

