# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1819537'
_audit_update_record             
;
2018-01-26 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(1S,7aS)-1-(4-bromobenzoyl)-7a-phenyl-1H-azirino[1,2-a]indol-7(7aH)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Br N O2, C H Cl3'
_chemical_formula_sum            'C23 H15 Br Cl3 N O2'
_chemical_formula_weight         523.61

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9551(9)
_cell_length_b                   10.2283(9)
_cell_length_c                   11.7216(9)
_cell_angle_alpha                102.790(2)
_cell_angle_beta                 98.700(2)
_cell_angle_gamma                103.152(2)
_cell_volume                     1107.55(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8285
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.41

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    2.238
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  2.85
_exptl_absorpt_correction_T_max  29.44
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19987
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3879
_reflns_number_gt                3224
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3879
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18268(3) 0.60093(3) 0.35819(3) 0.04541(16) Uani 1 1 d . . .
Cl2 Cl 0.21111(11) 0.16458(13) 1.08613(10) 0.0725(3) Uani 1 1 d . . .
Cl1 Cl 0.51101(12) 0.24496(14) 1.15408(11) 0.0835(4) Uani 1 1 d . . .
Cl3 Cl 0.36529(17) 0.44512(11) 1.10625(11) 0.0898(4) Uani 1 1 d . . .
O2 O 0.2755(2) 0.2843(2) 0.80754(18) 0.0370(5) Uani 1 1 d . . .
C3 C 0.2339(3) 0.5062(3) 0.4721(2) 0.0292(6) Uani 1 1 d . . .
C4 C 0.3190(3) 0.4179(3) 0.4483(3) 0.0325(6) Uani 1 1 d . . .
H4A H 0.3515 0.4062 0.3774 0.039 Uiso 1 1 calc R . .
N1 N 0.5108(2) 0.1782(2) 0.8262(2) 0.0291(5) Uani 1 1 d . . .
C7 C 0.3401(3) 0.2909(3) 0.7280(2) 0.0282(6) Uani 1 1 d . . .
C1 C 0.2195(3) 0.4537(3) 0.6578(3) 0.0334(7) Uani 1 1 d . . .
H1A H 0.1851 0.4648 0.7278 0.040 Uiso 1 1 calc R . .
C5 C 0.3548(3) 0.3478(3) 0.5304(2) 0.0307(6) Uani 1 1 d . . .
H5A H 0.4125 0.2889 0.5152 0.037 Uiso 1 1 calc R . .
O1 O 0.5064(3) -0.1001(3) 0.5772(2) 0.0551(7) Uani 1 1 d . . .
C18 C 0.2898(3) -0.0172(3) 0.7119(3) 0.0300(6) Uani 1 1 d . . .
C17 C 0.4327(3) 0.0705(3) 0.7160(2) 0.0272(6) Uani 1 1 d . . .
C24 C 0.3657(3) 0.2704(3) 1.0671(3) 0.0402(7) Uani 1 1 d . . .
H24A H 0.3714 0.2437 0.9828 0.048 Uiso 1 1 calc R . .
C19 C 0.2544(3) -0.0534(3) 0.8115(3) 0.0359(7) Uani 1 1 d . . .
H19A H 0.3210 -0.0225 0.8833 0.043 Uiso 1 1 calc R . .
C15 C 0.6758(3) 0.0785(3) 0.7387(3) 0.0400(8) Uani 1 1 d . . .
C8 C 0.4589(3) 0.2231(3) 0.7193(2) 0.0285(6) Uani 1 1 d . . .
H8A H 0.5298 0.2602 0.6767 0.034 Uiso 1 1 calc R . .
C6 C 0.3055(3) 0.3641(3) 0.6365(2) 0.0255(6) Uani 1 1 d . . .
C9 C 0.6573(3) 0.1793(3) 0.8310(3) 0.0356(7) Uani 1 1 d . . .
C2 C 0.1851(3) 0.5253(3) 0.5768(3) 0.0364(7) Uani 1 1 d . . .
H2A H 0.1294 0.5861 0.5924 0.044 Uiso 1 1 calc R . .
C16 C 0.5369(3) 0.0004(3) 0.6618(3) 0.0371(7) Uani 1 1 d . . .
C10 C 0.7704(3) 0.2710(4) 0.9155(3) 0.0496(9) Uani 1 1 d . . .
H10A H 0.7582 0.3384 0.9778 0.060 Uiso 1 1 calc R . .
C23 C 0.1899(4) -0.0650(3) 0.6055(3) 0.0469(8) Uani 1 1 d . . .
H23A H 0.2119 -0.0420 0.5368 0.056 Uiso 1 1 calc R . .
C13 C 0.8096(4) 0.0655(5) 0.7288(4) 0.0577(10) Uani 1 1 d . . .
H13A H 0.8216 -0.0034 0.6677 0.069 Uiso 1 1 calc R . .
C21 C 0.0224(4) -0.1813(4) 0.7017(4) 0.0553(10) Uani 1 1 d . . .
H21A H -0.0675 -0.2353 0.6987 0.066 Uiso 1 1 calc R . .
C20 C 0.1215(4) -0.1351(3) 0.8070(4) 0.0504(9) Uani 1 1 d . . .
H20A H 0.0992 -0.1588 0.8754 0.060 Uiso 1 1 calc R . .
C12 C 0.9226(4) 0.1559(5) 0.8106(5) 0.0725(14) Uani 1 1 d . . .
H12A H 1.0133 0.1499 0.8048 0.087 Uiso 1 1 calc R . .
C11 C 0.9039(4) 0.2576(5) 0.9030(4) 0.0680(13) Uani 1 1 d . . .
H11A H 0.9828 0.3182 0.9580 0.082 Uiso 1 1 calc R . .
C22 C 0.0559(4) -0.1479(4) 0.6018(4) 0.0587(11) Uani 1 1 d . . .
H22A H -0.0111 -0.1805 0.5302 0.070 Uiso 1 1 calc 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
Br1 C3 1.891(3) . ?
Cl2 C24 1.744(3) . ?
Cl1 C24 1.744(3) . ?
Cl3 C24 1.746(3) . ?
O2 C7 1.215(3) . ?
C3 C2 1.378(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.374(4) . ?
N1 C9 1.448(4) . ?
N1 C17 1.471(4) . ?
N1 C8 1.488(3) . ?
C7 C6 1.481(4) . ?
C7 C8 1.506(4) . ?
C1 C6 1.398(4) . ?
C1 C2 1.371(4) . ?
C5 C6 1.394(4) . ?
O1 C16 1.204(4) . ?
C18 C19 1.372(4) . ?
C18 C23 1.384(4) . ?
C18 C17 1.487(4) . ?
C17 C8 1.513(4) . ?
C17 C16 1.526(4) . ?
C19 C20 1.381(5) . ?
C15 C13 1.388(4) . ?
C15 C9 1.386(4) . ?
C15 C16 1.471(5) . ?
C9 C10 1.378(5) . ?
C10 C11 1.393(6) . ?
C23 C22 1.398(5) . ?
C13 C12 1.360(6) . ?
C21 C20 1.372(5) . ?
C21 C22 1.357(6) . ?
C12 C11 1.393(7) . ?

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 C3 C4 121.2(3) . . ?
C2 C3 Br1 119.4(2) . . ?
C4 C3 Br1 119.3(2) . . ?
C5 C4 C3 119.3(3) . . ?
C9 N1 C17 104.7(2) . . ?
C9 N1 C8 108.7(2) . . ?
C17 N1 C8 61.53(17) . . ?
O2 C7 C6 121.9(2) . . ?
O2 C7 C8 120.5(3) . . ?
C6 C7 C8 117.6(2) . . ?
C6 C1 C2 120.9(3) . . ?
C4 C5 C6 120.6(2) . . ?
C19 C18 C23 118.8(3) . . ?
C19 C18 C17 121.4(3) . . ?
C23 C18 C17 119.8(3) . . ?
N1 C17 C8 59.79(17) . . ?
N1 C17 C18 119.9(2) . . ?
C8 C17 C18 121.6(2) . . ?
N1 C17 C16 108.3(2) . . ?
C8 C17 C16 114.4(2) . . ?
C18 C17 C16 118.6(2) . . ?
Cl2 C24 Cl1 109.35(18) . . ?
Cl2 C24 Cl3 110.60(18) . . ?
Cl1 C24 Cl3 110.55(18) . . ?
C20 C19 C18 121.1(3) . . ?
C13 C15 C9 121.0(3) . . ?
C13 C15 C16 130.3(3) . . ?
C9 C15 C16 108.7(3) . . ?
N1 C8 C17 58.67(17) . . ?
N1 C8 C7 115.7(2) . . ?
C17 C8 C7 119.4(2) . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 118.3(2) . . ?
C5 C6 C7 123.0(2) . . ?
C15 C9 C10 121.5(3) . . ?
C15 C9 N1 113.2(3) . . ?
C10 C9 N1 125.2(3) . . ?
C3 C2 C1 119.2(3) . . ?
O1 C16 C15 129.6(3) . . ?
O1 C16 C17 125.6(3) . . ?
C15 C16 C17 104.8(2) . . ?
C9 C10 C11 116.6(4) . . ?
C18 C23 C22 119.7(4) . . ?
C15 C13 C12 118.3(4) . . ?
C20 C21 C22 119.9(3) . . ?
C19 C20 C21 119.9(4) . . ?
C11 C12 C13 120.6(3) . . ?
C12 C11 C10 121.9(4) . . ?
C21 C22 C23 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.064
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
