# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1041242'
_audit_update_record             
;
2014-12-24 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 Cl N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         428.90
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.5286(2)
_cell_length_b                   10.2653(3)
_cell_length_c                   21.7873(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2131.10(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4582
_cell_measurement_theta_min      2.7264
_cell_measurement_theta_max      24.3014
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896

_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            5299
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             5299
_reflns_number_gt                4551
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0847
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_number_reflns         5299
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.4085P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1806 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)

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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.0052(3) 0.6025(2) 1.01864(11) 0.0185(5) Uani d . . . 1 . .
H H1A -0.103 0.6252 1.0077 0.022 Uiso calc U . R 1 . .
H H1B -0.0041 0.569 1.0613 0.022 Uiso calc U . R 1 . .
C C2 0.0510(3) 0.5003(2) 0.97494(11) 0.0199(5) Uani d . . . 1 . .
H H2A 0.1466 0.4741 0.9878 0.024 Uiso calc U . R 1 . .
H H2B -0.0099 0.4223 0.9762 0.024 Uiso calc U . R 1 . .
C C3 0.0556(2) 0.5531(2) 0.91059(11) 0.0162(5) Uani d . . . 1 . .
C C4 0.0538(2) 0.4694(2) 0.86017(12) 0.0205(5) Uani d . . . 1 . .
H H4 0.0528 0.3779 0.8667 0.025 Uiso calc U . R 1 . .
C C5 0.0536(3) 0.5174(3) 0.80091(11) 0.0221(5) Uani d . . . 1 . .
H H5 0.0527 0.459 0.7671 0.026 Uiso calc U . R 1 . .
C C6 0.0547(3) 0.6512(3) 0.79081(11) 0.0234(6) Uani d . . . 1 . .
H H6 0.0521 0.6847 0.7502 0.028 Uiso calc U . R 1 . .
C C7 0.0596(3) 0.7350(2) 0.84048(11) 0.0207(5) Uani d . . . 1 . .
H H7 0.0622 0.8264 0.8335 0.025 Uiso calc U . R 1 . .
C C8 0.0608(2) 0.6881(2) 0.90050(11) 0.0163(5) Uani d . . . 1 . .
C C9 0.0718(2) 0.7844(2) 0.95278(10) 0.0145(5) Uani d . . . 1 . .
H H9 0.1585 0.8374 0.946 0.017 Uiso calc U . R 1 . .
C C10 -0.0516(2) 0.8796(2) 0.96054(10) 0.0144(5) Uani d . . . 1 . .
H H10 -0.1411 0.8317 0.9525 0.017 Uiso calc U . R 1 . .
C C11 -0.0436(2) 0.9117(2) 1.02864(11) 0.0159(5) Uani d . . . 1 . .
C C12 0.1052(2) 0.8157(3) 1.11403(10) 0.0176(5) Uani d . . . 1 . .
C C13 0.0675(2) 0.9183(2) 1.15940(10) 0.0151(5) Uani d . . . 1 . .
C C14 0.1788(3) 0.9889(3) 1.18387(11) 0.0217(5) Uani d . . . 1 . .
H H14 0.2714 0.975 1.1691 0.026 Uiso calc U . R 1 . .
C C15 0.1547(3) 1.0794(3) 1.22975(12) 0.0283(6) Uani d . . . 1 . .
H H15 0.2301 1.13 1.2454 0.034 Uiso calc U . R 1 . .
C C16 0.0212(3) 1.0960(3) 1.25278(12) 0.0282(6) Uani d . . . 1 . .
H H16 0.005 1.1572 1.2847 0.034 Uiso calc U . R 1 . .
C C17 -0.0891(3) 1.0240(3) 1.22967(12) 0.0275(6) Uani d . . . 1 . .
H H17 -0.1806 1.035 1.2462 0.033 Uiso calc U . R 1 . .
C C18 -0.0672(3) 0.9355(2) 1.18232(11) 0.0208(5) Uani d . . . 1 . .
H H18 -0.1435 0.8873 1.1658 0.025 Uiso calc U . R 1 . .
C C19 -0.0513(3) 1.0039(2) 0.92303(10) 0.0158(5) Uani d . . . 1 . .
C C20 -0.1740(3) 1.0416(2) 0.90063(11) 0.0176(5) Uani d . . . 1 . .
H H20 -0.2509 0.9833 0.9044 0.021 Uiso calc U . R 1 . .
C C21 0.0815(2) 1.0796(2) 0.91561(11) 0.0159(5) Uani d . . . 1 . .
C C22 0.1432(3) 1.0905(2) 0.85779(11) 0.0208(5) Uani d . . . 1 . .
H H22 0.0989 1.0511 0.8234 0.025 Uiso calc U . R 1 . .
C C23 0.2679(3) 1.1578(2) 0.84961(12) 0.0255(6) Uani d . . . 1 . .
H H23 0.3091 1.1632 0.81 0.031 Uiso calc U . R 1 . .
C C24 0.3324(3) 1.2171(2) 0.89933(13) 0.0251(6) Uani d . . . 1 . .
H H24 0.4176 1.2638 0.8939 0.03 Uiso calc U . R 1 . .
C C25 0.2723(3) 1.2079(2) 0.95672(12) 0.0229(5) Uani d . . . 1 . .
H H25 0.316 1.2492 0.9907 0.027 Uiso calc U . R 1 . .
C C26 0.1487(3) 1.1389(2) 0.96534(11) 0.0188(5) Uani d . . . 1 . .
H H26 0.1094 1.132 1.0053 0.023 Uiso calc U . R 1 . .
Cl Cl1 -0.20423(7) 1.18999(6) 0.86502(3) 0.02481(15) Uani d . . . 1 . .
N N1 0.0403(2) 0.81580(19) 1.05609(9) 0.0161(4) Uani d . . . 1 . .
N N2 0.0862(2) 0.71848(18) 1.01337(8) 0.0155(4) Uani d . . . 1 . .
O O1 -0.09652(19) 1.00295(17) 1.05443(7) 0.0213(4) Uani d . . . 1 . .
O O2 0.1911(2) 0.73275(18) 1.12588(8) 0.0302(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.480(3) ?
C1 C2 . 1.514(3) ?
C2 C3 . 1.504(3) ?
C3 C4 . 1.395(3) ?
C3 C8 . 1.403(3) ?
C4 C5 . 1.382(4) ?
C5 C6 . 1.391(4) ?
C6 C7 . 1.383(3) ?
C7 C8 . 1.394(3) ?
C8 C9 . 1.512(3) ?
C9 N2 . 1.490(3) ?
C9 C10 . 1.538(3) ?
C10 C19 . 1.515(3) ?
C10 C11 . 1.522(3) ?
C11 O1 . 1.203(3) ?
C11 N1 . 1.402(3) ?
C12 O2 . 1.208(3) ?
C12 N1 . 1.406(3) ?
C12 C13 . 1.489(3) ?
C13 C18 . 1.389(3) ?
C13 C14 . 1.391(3) ?
C14 C15 . 1.383(4) ?
C15 C16 . 1.378(4) ?
C16 C17 . 1.380(4) ?
C17 C18 . 1.391(3) ?
C19 C20 . 1.325(3) ?
C19 C21 . 1.494(3) ?
C20 Cl1 . 1.733(2) ?
C21 C22 . 1.394(3) ?
C21 C26 . 1.398(3) ?
C22 C23 . 1.386(3) ?
C23 C24 . 1.387(4) ?
C24 C25 . 1.378(4) ?
C25 C26 . 1.387(4) ?
N1 N2 . 1.434(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C2 . . 107.47(19) ?
C3 C2 C1 . . 110.3(2) ?
C4 C3 C8 . . 119.0(2) ?
C4 C3 C2 . . 120.8(2) ?
C8 C3 C2 . . 120.2(2) ?
C5 C4 C3 . . 121.1(2) ?
C4 C5 C6 . . 120.0(2) ?
C7 C6 C5 . . 119.4(2) ?
C6 C7 C8 . . 121.3(2) ?
C7 C8 C3 . . 119.2(2) ?
C7 C8 C9 . . 118.8(2) ?
C3 C8 C9 . . 122.0(2) ?
N2 C9 C8 . . 112.16(18) ?
N2 C9 C10 . . 105.15(17) ?
C8 C9 C10 . . 116.44(19) ?
C19 C10 C11 . . 110.06(18) ?
C19 C10 C9 . . 118.33(19) ?
C11 C10 C9 . . 101.95(18) ?
O1 C11 N1 . . 125.9(2) ?
O1 C11 C10 . . 127.1(2) ?
N1 C11 C10 . . 106.96(19) ?
O2 C12 N1 . . 119.4(2) ?
O2 C12 C13 . . 121.3(2) ?
N1 C12 C13 . . 119.3(2) ?
C18 C13 C14 . . 120.1(2) ?
C18 C13 C12 . . 123.5(2) ?
C14 C13 C12 . . 116.1(2) ?
C15 C14 C13 . . 120.0(2) ?
C16 C15 C14 . . 120.0(3) ?
C15 C16 C17 . . 120.3(2) ?
C16 C17 C18 . . 120.4(2) ?
C13 C18 C17 . . 119.2(2) ?
C20 C19 C21 . . 123.7(2) ?
C20 C19 C10 . . 116.3(2) ?
C21 C19 C10 . . 119.9(2) ?
C19 C20 Cl1 . . 124.7(2) ?
C22 C21 C26 . . 118.2(2) ?
C22 C21 C19 . . 119.8(2) ?
C26 C21 C19 . . 122.0(2) ?
C23 C22 C21 . . 121.2(2) ?
C22 C23 C24 . . 119.9(2) ?
C25 C24 C23 . . 119.6(2) ?
C24 C25 C26 . . 120.7(2) ?
C25 C26 C21 . . 120.4(2) ?
C11 N1 C12 . . 129.4(2) ?
C11 N1 N2 . . 112.73(18) ?
C12 N1 N2 . . 116.60(19) ?
N1 N2 C1 . . 109.31(17) ?
N1 N2 C9 . . 103.35(16) ?
C1 N2 C9 . . 112.33(18) ?



