# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_123
_database_code_depnum_ccdc_archive 'CCDC 1827731'
_audit_update_record             
;
2018-07-07 deposited with the CCDC.
2018-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Cl N O'
_chemical_formula_weight         401.91

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.441(3)
_cell_length_b                   8.545(2)
_cell_length_c                   13.063(3)
_cell_angle_alpha                89.906(4)
_cell_angle_beta                 112.470(5)
_cell_angle_gamma                90.128(4)
_cell_volume                     1077.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12942
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4538
_reflns_number_gt                4145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0582P)²+0.2806P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_number_reflns         4538
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
Cl1 Cl 0.05331(8) 0.32739(15) -0.04320(5) 0.0945(3) Uani 1 1 d . . .
O1 O 0.2408(2) -0.1397(2) 0.61845(17) 0.0691(5) Uani 1 1 d . . .
N1 N 0.2924(2) 0.0128(2) 0.65255(16) 0.0497(4) Uani 1 1 d . . .
C1 C 0.38545(18) 0.3114(2) 0.72577(14) 0.0374(4) Uani 1 1 d . . .
C2 C 0.43425(19) 0.3573(2) 0.64553(16) 0.0404(4) Uani 1 1 d . . .
C3 C 0.5729(2) 0.4158(3) 0.67982(19) 0.0537(6) Uani 1 1 d . . .
H3 H 0.6063 0.4473 0.6265 0.068(8) Uiso 1 1 d R . .
C4 C 0.6563(2) 0.4266(3) 0.7885(2) 0.0588(6) Uani 1 1 d . . .
H4 H 0.7454 0.4666 0.8083 0.068(8) Uiso 1 1 d R . .
C5 C 0.6112(2) 0.3785(3) 0.87212(17) 0.0474(5) Uani 1 1 d . . .
C6 C 0.6976(2) 0.3886(3) 0.9871(2) 0.0603(6) Uani 1 1 d . . .
H6 H 0.7866 0.4296 1.0087 0.071(8) Uiso 1 1 d R . .
C7 C 0.6512(3) 0.3395(4) 1.06523(18) 0.0668(7) Uani 1 1 d . . .
H7 H 0.7090 0.3467 1.1397 0.085(9) Uiso 1 1 d R . .
C8 C 0.5173(3) 0.2781(4) 1.03495(19) 0.0675(7) Uani 1 1 d . . .
H8 H 0.4876 0.2437 1.0897 0.063(8) Uiso 1 1 d R . .
C9 C 0.4303(3) 0.2679(3) 0.92546(18) 0.0543(5) Uani 1 1 d . . .
H9 H 0.3415 0.2275 0.9066 0.059(7) Uiso 1 1 d R . .
C10 C 0.4739(2) 0.3186(2) 0.84113(15) 0.0415(4) Uani 1 1 d . . .
C11 C 0.3460(2) 0.3439(2) 0.52697(15) 0.0418(4) Uani 1 1 d . . .
H11 H 0.2680 0.2805 0.5084 0.061(7) Uiso 1 1 d R . .
C12 C 0.3672(2) 0.4140(3) 0.44422(17) 0.0450(4) Uani 1 1 d . . .
H12 H 0.4414 0.4833 0.4633 0.047(6) Uiso 1 1 d R . .
C13 C 0.2854(2) 0.3926(2) 0.32558(16) 0.0423(4) Uani 1 1 d . . .
C14 C 0.1745(2) 0.2897(3) 0.28394(17) 0.0499(5) Uani 1 1 d . . .
H14 H 0.1481 0.2318 0.3329 0.061(7) Uiso 1 1 d R . .
C15 C 0.1020(2) 0.2720(3) 0.17071(19) 0.0561(6) Uani 1 1 d . . .
H15 H 0.0278 0.2029 0.1439 0.095(11) Uiso 1 1 d R . .
C16 C 0.1419(2) 0.3572(4) 0.09904(17) 0.0584(6) Uani 1 1 d . . .
C17 C 0.2494(3) 0.4606(4) 0.1357(2) 0.0670(7) Uani 1 1 d . . .
H17 H 0.2743 0.5182 0.0857 0.076(9) Uiso 1 1 d R . .
C18 C 0.3213(3) 0.4781(3) 0.2490(2) 0.0605(6) Uani 1 1 d . . .
H18 H 0.3952 0.5478 0.2747 0.101(12) Uiso 1 1 d R . .
C19 C 0.2357(2) 0.2643(2) 0.69380(15) 0.0386(4) Uani 1 1 d . . .
C20 C 0.1965(2) 0.1015(3) 0.65769(17) 0.0454(5) Uani 1 1 d . . .
C21 C 0.0471(3) 0.0542(5) 0.6279(4) 0.0881(11) Uani 1 1 d . . .
H21A H 0.0072 0.0303 0.5494 0.21(3) Uiso 1 1 d R . .
H21B H 0.0463 -0.0417 0.6674 0.20(3) Uiso 1 1 d R . .
C22 C -0.0357(4) 0.1588(5) 0.6546(9) 0.207(4) Uani 1 1 d . . .
H22A H -0.0484 0.1202 0.7199 0.51(11) Uiso 1 1 d R . .
H22B H -0.1251 0.1501 0.5939 0.19(2) Uiso 1 1 d R . .
C23 C -0.0092(2) 0.3233(4) 0.66759(19) 0.0571(6) Uani 1 1 d . . .
H23A H -0.0396 0.3579 0.7254 0.121(13) Uiso 1 1 d R . .
H23B H -0.0637 0.3789 0.6003 0.069(8) Uiso 1 1 d R . .
C24 C 0.1410(2) 0.3666(3) 0.70012(15) 0.0438(4) Uani 1 1 d . . .
C25 C 0.1766(3) 0.5304(3) 0.7422(2) 0.0591(6) Uani 1 1 d . . .
H25A H 0.1597 0.5431 0.8090 0.137(17) Uiso 1 1 d R . .
H25B H 0.1201 0.6027 0.6872 0.097(11) Uiso 1 1 d R . .
H25C H 0.2726 0.5505 0.7573 0.101(12) Uiso 1 1 d R . .
C26 C 0.3495(4) -0.2320(4) 0.6106(3) 0.0813(9) Uani 1 1 d . . .
H26A H 0.3761 -0.1915 0.5531 0.095(11) Uiso 1 1 d R . .
H26B H 0.3184 -0.3381 0.5937 0.086(10) Uiso 1 1 d R . .
H26C H 0.4276 -0.2290 0.6800 0.100(13) Uiso 1 1 d R . .


_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 C16 1.749(2) . ?
O1 N1 1.415(2) . ?
O1 C26 1.418(4) . ?
N1 C20 1.279(3) . ?
C1 C2 1.385(3) . ?
C1 C10 1.437(2) . ?
C1 C19 1.510(3) . ?
C2 C3 1.431(3) . ?
C2 C11 1.473(2) . ?
C3 C4 1.356(3) . ?
C3 H3 0.9294 . ?
C4 C5 1.405(3) . ?
C4 H4 0.9294 . ?
C5 C10 1.427(3) . ?
C5 C6 1.429(3) . ?
C6 C7 1.352(4) . ?
C6 H6 0.9294 . ?
C7 C8 1.400(4) . ?
C7 H7 0.9299 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9295 . ?
C9 C10 1.410(3) . ?
C9 H9 0.9294 . ?
C11 C12 1.326(3) . ?
C11 H11 0.9292 . ?
C12 C13 1.467(3) . ?
C12 H12 0.9292 . ?
C13 C14 1.387(3) . ?
C13 C18 1.399(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9291 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9293 . ?
C16 C17 1.362(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9292 . ?
C18 H18 0.9293 . ?
C19 C24 1.347(3) . ?
C19 C20 1.476(3) . ?
C20 C21 1.510(3) . ?
C21 C22 1.379(7) . ?
C21 H21A 0.9701 . ?
C21 H21B 0.9692 . ?
C22 C23 1.430(5) . ?
C22 H22A 0.9693 . ?
C22 H22B 0.9697 . ?
C23 C24 1.506(3) . ?
C23 H23A 0.9705 . ?
C23 H23B 0.9699 . ?
C24 C25 1.498(3) . ?
C25 H25A 0.9602 . ?
C25 H25B 0.9602 . ?
C25 H25C 0.9596 . ?
C26 H26A 0.9593 . ?
C26 H26B 0.9597 . ?
C26 H26C 0.9599 . ?

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
N1 O1 C26 108.5(2) . . ?
C20 N1 O1 110.60(18) . . ?
C2 C1 C10 120.46(16) . . ?
C2 C1 C19 120.44(15) . . ?
C10 C1 C19 118.95(15) . . ?
C1 C2 C3 118.79(17) . . ?
C1 C2 C11 120.71(16) . . ?
C3 C2 C11 120.50(17) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C10 118.82(18) . . ?
C4 C5 C6 122.3(2) . . ?
C10 C5 C6 118.8(2) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 118.46(18) . . ?
C9 C10 C1 122.44(18) . . ?
C5 C10 C1 119.10(17) . . ?
C12 C11 C2 126.16(19) . . ?
C12 C11 H11 116.9 . . ?
C2 C11 H11 116.9 . . ?
C11 C12 C13 126.4(2) . . ?
C11 C12 H12 116.7 . . ?
C13 C12 H12 116.9 . . ?
C14 C13 C18 117.39(19) . . ?
C14 C13 C12 123.70(18) . . ?
C18 C13 C12 118.9(2) . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 Cl1 119.89(19) . . ?
C15 C16 Cl1 118.2(2) . . ?
C16 C17 C18 118.8(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C13 121.5(2) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.1 . . ?
C24 C19 C20 120.84(18) . . ?
C24 C19 C1 121.17(19) . . ?
C20 C19 C1 117.98(17) . . ?
N1 C20 C19 116.70(18) . . ?
N1 C20 C21 125.5(2) . . ?
C19 C20 C21 117.8(2) . . ?
C22 C21 C20 116.6(3) . . ?
C22 C21 H21A 110.4 . . ?
C20 C21 H21A 108.2 . . ?
C22 C21 H21B 106.3 . . ?
C20 C21 H21B 107.8 . . ?
H21A C21 H21B 107.3 . . ?
C21 C22 C23 123.9(4) . . ?
C21 C22 H22A 108.2 . . ?
C23 C22 H22A 108.3 . . ?
C21 C22 H22B 104.2 . . ?
C23 C22 H22B 104.7 . . ?
H22A C22 H22B 106.3 . . ?
C22 C23 C24 114.0(3) . . ?
C22 C23 H23A 106.7 . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23B 110.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.6 . . ?
C19 C24 C25 123.1(2) . . ?
C19 C24 C23 122.2(2) . . ?
C25 C24 C23 114.7(2) . . ?
C24 C25 H25A 109.6 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 109.4 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.6 . . ?
O1 C26 H26A 109.6 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.4 . . ?
O1 C26 H26C 109.4 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.038
