# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_BE25
_database_code_depnum_ccdc_archive 'CCDC 1525857'
_audit_update_record             
;
2017-01-06 deposited with the CCDC.
2017-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl N O'
_chemical_formula_sum            'C22 H14 Cl N O'
_chemical_formula_weight         343.79

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'

_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                   11.8090(9)
_cell_length_b                   13.9475(11)
_cell_length_c                   10.4695(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.4770(10)
_cell_angle_gamma                90
_cell_volume                     1721.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3833
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      23.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   
'Sheldrick,G.M.,(2003),University of gottingen,Germany'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16319
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.262
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3033
_reflns_number_gt                2754
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+1.3730P] 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         3033
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.357
_refine_ls_restrained_S_all      1.357
_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 0.2310(3) 0.0586(2) 0.4507(3) 0.0485(8) Uani 1 1 d . . . . .
H1 H 0.1658 0.0404 0.4025 0.058 Uiso 1 1 calc R U . . .
C2 C 0.2288(3) 0.0530(2) 0.5849(3) 0.0407(7) Uani 1 1 d . . . . .
C3 C 0.3243(3) 0.0764(2) 0.6599(3) 0.0371(7) Uani 1 1 d . . . . .
C4 C 0.4216(3) 0.1074(2) 0.5966(3) 0.0376(7) Uani 1 1 d . . . . .
C5 C 0.4129(3) 0.1122(2) 0.4612(3) 0.0411(7) Uani 1 1 d . . . . .
C6 C 0.5081(3) 0.1430(2) 0.3970(3) 0.0510(9) Uani 1 1 d . . . . .
H6 H 0.5034 0.1463 0.3081 0.061 Uiso 1 1 calc R U . . .
C7 C 0.6060(3) 0.1679(2) 0.4622(3) 0.0528(9) Uani 1 1 d . . . . .
H7 H 0.6679 0.1884 0.4187 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6133(3) 0.1625(2) 0.5957(3) 0.0476(8) Uani 1 1 d . . . . .
C9 C 0.5251(3) 0.1324(2) 0.6627(3) 0.0431(8) Uani 1 1 d . . . . .
H9 H 0.5329 0.1282 0.7514 0.052 Uiso 1 1 calc R U . . .
C10 C 0.3284(2) 0.0644(2) 0.8018(3) 0.0390(7) Uani 1 1 d . . . . .
C11 C 0.3225(3) -0.0265(2) 0.8534(3) 0.0474(8) Uani 1 1 d . . . . .
H11 H 0.3159 -0.0795 0.7995 0.057 Uiso 1 1 calc R U . . .
C12 C 0.3262(3) -0.0394(3) 0.9840(3) 0.0616(10) Uani 1 1 d . . . . .
H12 H 0.3233 -0.1011 1.0175 0.074 Uiso 1 1 calc R U . . .
C13 C 0.3341(3) 0.0376(3) 1.0646(3) 0.0682(11) Uani 1 1 d . . . . .
H13 H 0.3359 0.0287 1.1527 0.082 Uiso 1 1 calc R U . . .
C14 C 0.3394(4) 0.1279(3) 1.0145(3) 0.0701(11) Uani 1 1 d . . . . .
H14 H 0.3445 0.1806 1.0690 0.084 Uiso 1 1 calc R U . . .
C15 C 0.3373(3) 0.1417(3) 0.8837(3) 0.0555(9) Uani 1 1 d . . . . .
H15 H 0.3418 0.2034 0.8508 0.067 Uiso 1 1 calc R U . . .
C16 C 0.1208(3) 0.0216(2) 0.6407(3) 0.0485(8) Uani 1 1 d . . . . .
C17 C 0.0666(3) 0.0881(2) 0.7295(3) 0.0453(8) Uani 1 1 d . . . . .
C18 C -0.0009(3) 0.0525(3) 0.8212(4) 0.0640(10) Uani 1 1 d . . . . .
H18 H -0.0139 -0.0131 0.8263 0.077 Uiso 1 1 calc R U . . .
C19 C -0.0494(3) 0.1146(4) 0.9059(4) 0.0792(13) Uani 1 1 d . . . . .
H19 H -0.0931 0.0903 0.9694 0.095 Uiso 1 1 calc R U . . .
C20 C -0.0330(4) 0.2112(4) 0.8964(4) 0.0821(14) Uani 1 1 d . . . . .
H20 H -0.0658 0.2525 0.9532 0.099 Uiso 1 1 calc R U . . .
C21 C 0.0314(3) 0.2471(3) 0.8036(4) 0.0752(12) Uani 1 1 d . . . . .
H21 H 0.0411 0.3130 0.7961 0.090 Uiso 1 1 calc R U . . .
C22 C 0.0819(3) 0.1860(3) 0.7212(4) 0.0598(10) Uani 1 1 d . . . . .
H22 H 0.1269 0.2108 0.6592 0.072 Uiso 1 1 calc R U . . .
Cl1 Cl 0.74099(8) 0.19319(8) 0.67735(10) 0.0701(3) Uani 1 1 d . . . . .
N1 N 0.3172(2) 0.0875(2) 0.3891(2) 0.0509(7) Uani 1 1 d . . . . .
O1 O 0.0788(2) -0.05513(19) 0.6105(3) 0.0747(8) 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 N1 1.302(4) . ?
C1 C2 1.409(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(4) . ?
C2 C16 1.500(5) . ?
C3 C4 1.428(4) . ?
C3 C10 1.492(4) . ?
C4 C9 1.412(4) . ?
C4 C5 1.417(4) . ?
C5 N1 1.365(4) . ?
C5 C6 1.411(4) . ?
C6 C7 1.351(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.357(4) . ?
C8 Cl1 1.741(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.378(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.377(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.366(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O1 1.213(4) . ?
C16 C17 1.486(5) . ?
C17 C18 1.377(5) . ?
C17 C22 1.380(5) . ?
C18 C19 1.388(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.365(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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 C1 C2 125.0(3) . . ?
N1 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 C16 122.3(3) . . ?
C1 C2 C16 118.1(3) . . ?
C2 C3 C4 117.5(3) . . ?
C2 C3 C10 121.2(3) . . ?
C4 C3 C10 121.2(3) . . ?
C9 C4 C5 119.1(3) . . ?
C9 C4 C3 123.0(3) . . ?
C5 C4 C3 117.9(3) . . ?
N1 C5 C6 118.1(3) . . ?
N1 C5 C4 123.2(3) . . ?
C6 C5 C4 118.7(3) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 Cl1 119.4(3) . . ?
C7 C8 Cl1 118.5(3) . . ?
C8 C9 C4 119.5(3) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
C15 C10 C11 118.6(3) . . ?
C15 C10 C3 121.9(3) . . ?
C11 C10 C3 119.5(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.5(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.3(3) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
O1 C16 C17 122.0(3) . . ?
O1 C16 C2 120.0(3) . . ?
C17 C16 C2 118.0(3) . . ?
C18 C17 C22 119.0(4) . . ?
C18 C17 C16 120.0(3) . . ?
C22 C17 C16 121.0(3) . . ?
C17 C18 C19 119.9(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.1(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C1 N1 C5 116.8(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
N1 C1 C2 C3 -2.0(5) . . . . ?
N1 C1 C2 C16 177.8(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C16 C2 C3 C4 -178.6(3) . . . . ?
C1 C2 C3 C10 -175.4(3) . . . . ?
C16 C2 C3 C10 4.9(5) . . . . ?
C2 C3 C4 C9 -179.2(3) . . . . ?
C10 C3 C4 C9 -2.7(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C10 C3 C4 C5 176.7(3) . . . . ?
C9 C4 C5 N1 178.5(3) . . . . ?
C3 C4 C5 N1 -1.0(4) . . . . ?
C9 C4 C5 C6 -0.8(4) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
N1 C5 C6 C7 -179.5(3) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C6 C7 C8 Cl1 179.1(3) . . . . ?
C7 C8 C9 C4 -1.3(5) . . . . ?
Cl1 C8 C9 C4 -180.0(2) . . . . ?
C5 C4 C9 C8 1.5(4) . . . . ?
C3 C4 C9 C8 -179.1(3) . . . . ?
C2 C3 C10 C15 -114.1(4) . . . . ?
C4 C3 C10 C15 69.5(4) . . . . ?
C2 C3 C10 C11 65.4(4) . . . . ?
C4 C3 C10 C11 -110.9(3) . . . . ?
C15 C10 C11 C12 -0.5(5) . . . . ?
C3 C10 C11 C12 180.0(3) . . . . ?
C10 C11 C12 C13 1.0(6) . . . . ?
C11 C12 C13 C14 -0.6(6) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
C3 C10 C15 C14 179.2(3) . . . . ?
C13 C14 C15 C10 0.8(6) . . . . ?
C3 C2 C16 O1 -123.1(4) . . . . ?
C1 C2 C16 O1 57.2(4) . . . . ?
C3 C2 C16 C17 58.6(4) . . . . ?
C1 C2 C16 C17 -121.1(3) . . . . ?
O1 C16 C17 C18 28.4(5) . . . . ?
C2 C16 C17 C18 -153.4(3) . . . . ?
O1 C16 C17 C22 -151.1(4) . . . . ?
C2 C16 C17 C22 27.2(5) . . . . ?
C22 C17 C18 C19 -2.0(5) . . . . ?
C16 C17 C18 C19 178.6(3) . . . . ?
C17 C18 C19 C20 1.9(6) . . . . ?
C18 C19 C20 C21 -0.1(7) . . . . ?
C19 C20 C21 C22 -1.4(7) . . . . ?
C20 C21 C22 C17 1.2(6) . . . . ?
C18 C17 C22 C21 0.5(5) . . . . ?
C16 C17 C22 C21 179.9(3) . . . . ?
C2 C1 N1 C5 1.2(5) . . . . ?
C6 C5 N1 C1 179.5(3) . . . . ?
C4 C5 N1 C1 0.2(5) . . . . ?

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043

