# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1049376'
_audit_update_record             
;
2015-02-13 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Cl N O3'
_chemical_formula_weight         363.78

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   18.6725(14)
_cell_length_b                   9.6689(7)
_cell_length_c                   19.3848(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3499.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1504
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9318
_exptl_absorpt_correction_T_max  0.9538
_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  ?
_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            38173
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         25.01
_reflns_number_total             6120
_reflns_number_gt                5527
_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)+(0.0561P)²+0.9334P] 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_number_reflns         6120
_refine_ls_number_parameters     471
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.007
_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 0.80270(5) 0.66689(11) 0.54093(4) 0.0847(3) Uani 1 1 d . . .
Cl2 Cl 0.44815(6) 0.18991(13) 1.00140(5) 0.0987(4) Uani 1 1 d . . .
O1 O 0.53873(12) 0.7697(2) 0.76853(12) 0.0561(5) Uani 1 1 d . . .
O4 O 0.71543(12) 0.2623(2) 0.77445(13) 0.0605(6) Uani 1 1 d . . .
N1 N 0.48039(10) 0.5014(2) 0.81325(10) 0.0405(4) Uani 1 1 d . . .
O5 O 0.79773(11) -0.2923(2) 0.84858(15) 0.0722(7) Uani 1 1 d . . .
N2 N 0.77076(11) -0.0101(2) 0.73520(11) 0.0476(5) Uani 1 1 d . . .
O2 O 0.45099(10) 0.2116(2) 0.70489(12) 0.0578(5) Uani 1 1 d . . .
C14 C 0.62908(13) 0.6635(2) 0.70213(13) 0.0421(5) Uani 1 1 d . . .
C35 C 0.62315(13) 0.1655(2) 0.84284(14) 0.0441(5) Uani 1 1 d . . .
C9 C 0.44531(12) 0.3799(2) 0.79462(13) 0.0418(5) Uani 1 1 d . . .
C11 C 0.53313(13) 0.4177(2) 0.71741(14) 0.0448(5) Uani 1 1 d . . .
H11 H 0.5635 0.4069 0.6798 0.054 Uiso 1 1 calc R . .
C36 C 0.57142(14) 0.0623(3) 0.84631(16) 0.0529(6) Uani 1 1 d . . .
H36 H 0.5737 -0.0130 0.8165 0.063 Uiso 1 1 calc R . .
C32 C 0.71636(14) -0.0871(3) 0.83112(16) 0.0543(7) Uani 1 1 d . . .
H32 H 0.6853 -0.0959 0.8683 0.065 Uiso 1 1 calc R . .
C1 C 0.46371(14) 0.5652(3) 0.87671(13) 0.0446(6) Uani 1 1 d . . .
C31 C 0.77117(14) -0.1782(3) 0.81375(18) 0.0537(7) Uani 1 1 d . . .
C17 C 0.73767(15) 0.6690(3) 0.60543(15) 0.0537(7) Uani 1 1 d . . .
C33 C 0.71638(13) 0.0196(3) 0.78273(14) 0.0489(6) Uani 1 1 d . . .
C34 C 0.68671(14) 0.1571(3) 0.79545(14) 0.0475(6) Uani 1 1 d . . .
C10 C 0.47874(13) 0.3284(2) 0.73671(14) 0.0453(6) Uani 1 1 d . . .
C40 C 0.61681(16) 0.2804(3) 0.88426(16) 0.0531(7) Uani 1 1 d . . .
H40 H 0.6492 0.3528 0.8796 0.064 Uiso 1 1 calc R . .
C30 C 0.80482(13) -0.1312(3) 0.75556(17) 0.0529(7) Uani 1 1 d . . .
C12 C 0.53422(12) 0.5267(2) 0.76453(13) 0.0424(5) Uani 1 1 d . . .
C15 C 0.67886(13) 0.5572(2) 0.69939(14) 0.0472(6) Uani 1 1 d . . .
H15 H 0.6753 0.4840 0.7303 0.057 Uiso 1 1 calc R . .
C13 C 0.56583(13) 0.6618(2) 0.74980(13) 0.0426(5) Uani 1 1 d . . .
C38 C 0.51399(17) 0.1827(3) 0.93766(16) 0.0623(8) Uani 1 1 d . . .
C8 C 0.38451(14) 0.3321(3) 0.83130(14) 0.0501(6) Uani 1 1 d . . .
H8 H 0.3601 0.2534 0.8168 0.060 Uiso 1 1 calc R . .
O3 O 0.55645(12) 0.1443(2) 0.66151(15) 0.0803(7) Uani 1 1 d . . .
C20 C 0.49391(16) 0.1264(3) 0.66918(15) 0.0534(6) Uani 1 1 d . . .
C23 C 0.74400(18) 0.1510(3) 0.64059(17) 0.0632(8) Uani 1 1 d . . .
H23 H 0.7009 0.1762 0.6611 0.076 Uiso 1 1 calc R . .
C6 C 0.40283(15) 0.5170(3) 0.91268(14) 0.0545(6) Uani 1 1 d . . .
O6 O 0.68968(13) -0.3723(3) 0.87622(14) 0.0815(7) Uani 1 1 d U . .
C19 C 0.63777(15) 0.7753(3) 0.65801(15) 0.0503(7) Uani 1 1 d . . .
H19 H 0.6065 0.8498 0.6611 0.060 Uiso 1 1 calc R . .
C16 C 0.73393(15) 0.5585(3) 0.65121(16) 0.0562(7) Uani 1 1 d . . .
H16 H 0.7674 0.4873 0.6496 0.067 Uiso 1 1 calc R . .
C41 C 0.75332(16) -0.3830(3) 0.87795(16) 0.0572(7) Uani 1 1 d U . .
C37 C 0.51652(16) 0.0714(3) 0.89407(17) 0.0614(7) Uani 1 1 d . . .
H37 H 0.4817 0.0028 0.8965 0.074 Uiso 1 1 calc R . .
C18 C 0.69167(16) 0.7778(3) 0.60999(15) 0.0557(7) Uani 1 1 d . . .
H18 H 0.6968 0.8534 0.5807 0.067 Uiso 1 1 calc R . .
C39 C 0.56229(17) 0.2891(3) 0.93299(16) 0.0620(8) Uani 1 1 d . . .
H39 H 0.5587 0.3656 0.9618 0.074 Uiso 1 1 calc R . .
C27 C 0.85067(16) 0.0065(3) 0.63798(16) 0.0594(7) Uani 1 1 d . . .
C2 C 0.50705(16) 0.6684(3) 0.90557(14) 0.0561(7) Uani 1 1 d . . .
H2 H 0.5485 0.6971 0.8832 0.067 Uiso 1 1 calc R . .
C28 C 0.88970(16) -0.1098(3) 0.66421(18) 0.0662(8) Uani 1 1 d . . .
H28 H 0.9319 -0.1372 0.6428 0.079 Uiso 1 1 calc R . .
C29 C 0.86593(15) -0.1787(3) 0.71888(18) 0.0598(8) Uani 1 1 d . . .
H29 H 0.8894 -0.2585 0.7332 0.072 Uiso 1 1 calc R . .
C7 C 0.36260(15) 0.4024(3) 0.88734(16) 0.0565(7) Uani 1 1 d . . .
H7 H 0.3208 0.3759 0.9098 0.068 Uiso 1 1 calc R . .
C22 C 0.78798(14) 0.0527(3) 0.67163(15) 0.0528(6) Uani 1 1 d . . .
C21 C 0.4527(2) 0.0060(4) 0.6420(2) 0.0864(11) Uani 1 1 d . . .
H21A H 0.4852 -0.0665 0.6294 0.130 Uiso 1 1 calc R . .
H21B H 0.4257 0.0340 0.6023 0.130 Uiso 1 1 calc R . .
H21C H 0.4205 -0.0270 0.6770 0.130 Uiso 1 1 calc R . .
C24 C 0.7650(2) 0.2107(5) 0.57912(19) 0.0812(10) Uani 1 1 d . . .
H24 H 0.7358 0.2766 0.5583 0.097 Uiso 1 1 calc R . .
C26 C 0.8704(2) 0.0729(4) 0.57648(18) 0.0770(10) Uani 1 1 d . . .
H26 H 0.9128 0.0474 0.5548 0.092 Uiso 1 1 calc R . .
C42 C 0.7940(2) -0.4949(3) 0.9123(2) 0.0900(11) Uani 1 1 d . . .
H42A H 0.7996 -0.5711 0.8811 0.135 Uiso 1 1 calc R . .
H42B H 0.7685 -0.5251 0.9526 0.135 Uiso 1 1 calc R . .
H42C H 0.8403 -0.4610 0.9256 0.135 Uiso 1 1 calc R . .
C5 C 0.38522(19) 0.5805(4) 0.97544(16) 0.0704(8) Uani 1 1 d . . .
H5 H 0.3448 0.5513 0.9994 0.084 Uiso 1 1 calc R . .
C4 C 0.4265(2) 0.6850(4) 1.00222(18) 0.0773(10) Uani 1 1 d . . .
H4 H 0.4135 0.7274 1.0434 0.093 Uiso 1 1 calc R . .
C3 C 0.4875(2) 0.7267(3) 0.96761(17) 0.0686(9) Uani 1 1 d . . .
H3 H 0.5159 0.7958 0.9866 0.082 Uiso 1 1 calc R . .
C25 C 0.8295(2) 0.1732(4) 0.54794(19) 0.0858(11) Uani 1 1 d . . .
H25 H 0.8443 0.2169 0.5077 0.103 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
Cl1 C17 1.743(3) . ?
Cl2 C38 1.744(3) . ?
O1 C13 1.215(3) . ?
O4 C34 1.220(3) . ?
N1 C9 1.392(3) . ?
N1 C12 1.401(3) . ?
N1 C1 1.411(3) . ?
O5 C41 1.335(4) . ?
O5 C31 1.385(4) . ?
N2 C30 1.390(3) . ?
N2 C33 1.401(3) . ?
N2 C22 1.411(4) . ?
O2 C20 1.342(3) . ?
O2 C10 1.387(3) . ?
C14 C15 1.386(4) . ?
C14 C19 1.388(4) . ?
C14 C13 1.500(3) . ?
C35 C40 1.376(4) . ?
C35 C36 1.391(4) . ?
C35 C34 1.503(4) . ?
C9 C10 1.378(4) . ?
C9 C8 1.417(3) . ?
C11 C10 1.384(3) . ?
C11 C12 1.395(4) . ?
C36 C37 1.384(4) . ?
C32 C31 1.391(4) . ?
C32 C33 1.394(4) . ?
C1 C2 1.401(4) . ?
C1 C6 1.413(4) . ?
C31 C30 1.369(5) . ?
C17 C18 1.361(4) . ?
C17 C16 1.391(4) . ?
C33 C34 1.462(4) . ?
C40 C39 1.391(4) . ?
C30 C29 1.421(4) . ?
C12 C13 1.462(3) . ?
C15 C16 1.389(4) . ?
C38 C37 1.369(5) . ?
C38 C39 1.371(5) . ?
C8 C7 1.345(4) . ?
O3 C20 1.190(3) . ?
C20 C21 1.492(4) . ?
C23 C24 1.381(5) . ?
C23 C22 1.393(4) . ?
C6 C5 1.402(4) . ?
C6 C7 1.426(4) . ?
O6 C41 1.193(4) . ?
C19 C18 1.371(4) . ?
C41 C42 1.480(4) . ?
C27 C26 1.404(5) . ?
C27 C22 1.412(4) . ?
C27 C28 1.433(5) . ?
C2 C3 1.378(4) . ?
C28 C29 1.328(5) . ?
C24 C25 1.396(6) . ?
C26 C25 1.353(5) . ?
C5 C4 1.372(5) . ?
C4 C3 1.382(5) . ?

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
C9 N1 C12 108.05(19) . . ?
C9 N1 C1 119.4(2) . . ?
C12 N1 C1 132.0(2) . . ?
C41 O5 C31 120.6(2) . . ?
C30 N2 C33 108.5(2) . . ?
C30 N2 C22 120.4(2) . . ?
C33 N2 C22 130.7(2) . . ?
C20 O2 C10 120.4(2) . . ?
C15 C14 C19 118.4(2) . . ?
C15 C14 C13 122.9(2) . . ?
C19 C14 C13 118.7(2) . . ?
C40 C35 C36 119.4(3) . . ?
C40 C35 C34 117.9(2) . . ?
C36 C35 C34 122.6(2) . . ?
C10 C9 N1 107.6(2) . . ?
C10 C9 C8 130.8(2) . . ?
N1 C9 C8 121.4(2) . . ?
C10 C11 C12 107.7(2) . . ?
C37 C36 C35 120.1(3) . . ?
C31 C32 C33 107.8(3) . . ?
C2 C1 N1 122.2(2) . . ?
C2 C1 C6 120.2(2) . . ?
N1 C1 C6 117.6(2) . . ?
C30 C31 O5 120.1(3) . . ?
C30 C31 C32 109.1(2) . . ?
O5 C31 C32 130.5(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 Cl1 119.7(2) . . ?
C16 C17 Cl1 118.9(2) . . ?
C32 C33 N2 106.9(2) . . ?
C32 C33 C34 124.0(3) . . ?
N2 C33 C34 124.9(2) . . ?
O4 C34 C33 122.4(3) . . ?
O4 C34 C35 120.4(2) . . ?
C33 C34 C35 116.8(2) . . ?
C9 C10 C11 109.1(2) . . ?
C9 C10 O2 119.2(2) . . ?
C11 C10 O2 131.4(2) . . ?
C35 C40 C39 120.5(3) . . ?
C31 C30 N2 107.7(2) . . ?
C31 C30 C29 132.4(3) . . ?
N2 C30 C29 119.9(3) . . ?
C11 C12 N1 107.4(2) . . ?
C11 C12 C13 123.6(2) . . ?
N1 C12 C13 125.3(2) . . ?
C14 C15 C16 121.0(2) . . ?
O1 C13 C12 122.7(2) . . ?
O1 C13 C14 120.2(2) . . ?
C12 C13 C14 116.6(2) . . ?
C37 C38 C39 121.8(3) . . ?
C37 C38 Cl2 119.5(3) . . ?
C39 C38 Cl2 118.7(3) . . ?
C7 C8 C9 119.0(3) . . ?
O3 C20 O2 124.2(3) . . ?
O3 C20 C21 125.2(3) . . ?
O2 C20 C21 110.7(3) . . ?
C24 C23 C22 119.4(3) . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 121.0(3) . . ?
C1 C6 C7 120.7(2) . . ?
C18 C19 C14 121.2(3) . . ?
C15 C16 C17 118.2(3) . . ?
O6 C41 O5 123.3(3) . . ?
O6 C41 C42 126.0(3) . . ?
O5 C41 C42 110.7(3) . . ?
C38 C37 C36 119.3(3) . . ?
C17 C18 C19 119.6(3) . . ?
C38 C39 C40 118.7(3) . . ?
C26 C27 C22 117.7(3) . . ?
C26 C27 C28 121.8(3) . . ?
C22 C27 C28 120.4(3) . . ?
C3 C2 C1 119.1(3) . . ?
C29 C28 C27 120.4(3) . . ?
C28 C29 C30 120.4(3) . . ?
C8 C7 C6 120.7(3) . . ?
C23 C22 N2 122.4(3) . . ?
C23 C22 C27 120.3(3) . . ?
N2 C22 C27 117.2(3) . . ?
C23 C24 C25 120.7(4) . . ?
C25 C26 C27 121.8(3) . . ?
C4 C5 C6 121.3(3) . . ?
C5 C4 C3 119.6(3) . . ?
C2 C3 C4 121.5(3) . . ?
C26 C25 C24 119.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.044
