# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ale268_chloro
_database_code_depnum_ccdc_archive 'CCDC 1441247'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C69 H78 Cl2 N4 O14'
_chemical_formula_weight         1258.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 b 2'

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

_cell_length_a                   16.4941(7)
_cell_length_b                   16.4941(7)
_cell_length_c                   24.5221(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6671.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    2842
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      71.88


_exptl_crystal_description       plate
_exptl_crystal_colour            'dark blue'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2664
_exptl_absorpt_coefficient_mu    1.420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.297
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12925
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0871
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         72.03
_reflns_number_total             5854
_reflns_number_gt                3215
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.1178P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.22(8)
_refine_ls_number_reflns         5854
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0749
_refine_ls_wR_factor_ref         0.2164
_refine_ls_wR_factor_gt          0.1875
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
C33 C 0.6662(4) 0.2066(5) 0.7703(2) 0.0672(19) Uani 1 1 d . . .
H33A H 0.7184 0.2293 0.7817 0.101 Uiso 1 1 calc R . .
H33B H 0.6223 0.2345 0.7896 0.101 Uiso 1 1 calc R . .
H33C H 0.6594 0.2138 0.7309 0.101 Uiso 1 1 calc R . .
C31 C 0.6638(4) 0.1161(5) 0.78412(19) 0.0585(18) Uani 1 1 d . . .
C32 C 0.6636(4) 0.1114(5) 0.8471(2) 0.069(2) Uani 1 1 d . . .
H32A H 0.6634 0.0545 0.8586 0.103 Uiso 1 1 calc R . .
H32B H 0.6151 0.1386 0.8613 0.103 Uiso 1 1 calc R . .
H32C H 0.7122 0.1383 0.8615 0.103 Uiso 1 1 calc R . .
C34 C 0.5826(4) 0.0766(5) 0.7661(2) 0.073(2) Uani 1 1 d . . .
H34A H 0.5801 0.0747 0.7262 0.110 Uiso 1 1 calc R . .
H34B H 0.5371 0.1088 0.7801 0.110 Uiso 1 1 calc R . .
H34C H 0.5793 0.0215 0.7808 0.110 Uiso 1 1 calc R . .
C29 C 1.1064(8) -0.4192(6) 0.6110(5) 0.143(5) Uani 1 1 d . . .
H29A H 1.1451 -0.4461 0.5867 0.214 Uiso 1 1 calc R . .
H29B H 1.0526 -0.4187 0.5940 0.214 Uiso 1 1 calc R . .
H29C H 1.1037 -0.4487 0.6457 0.214 Uiso 1 1 calc R . .
C30 C 1.2207(6) -0.3325(6) 0.6469(5) 0.130(4) Uani 1 1 d . . .
H30A H 1.2372 -0.2764 0.6540 0.195 Uiso 1 1 calc R . .
H30B H 1.2590 -0.3576 0.6214 0.195 Uiso 1 1 calc R . .
H30C H 1.2204 -0.3630 0.6812 0.195 Uiso 1 1 calc R . .
C28 C 1.1320(7) -0.2870(7) 0.5672(3) 0.121(4) Uani 1 1 d . . .
H28A H 1.1490 -0.2308 0.5733 0.181 Uiso 1 1 calc R . .
H28B H 1.0769 -0.2877 0.5524 0.181 Uiso 1 1 calc R . .
H28C H 1.1691 -0.3129 0.5413 0.181 Uiso 1 1 calc R . .
Cl1X Cl 1.3076(5) -0.0735(4) 1.0174(3) 0.302(4) Uani 1 1 d . . .
C1X C 1.3247(6) -0.1753(6) 1.0000 0.157(9) Uani 1 2 d S . .
H1X1 H 1.2896 -0.1902 0.9688 0.189 Uiso 0.50 1 calc PR . .
H1X2 H 1.3098 -0.2104 1.0312 0.189 Uiso 0.50 1 calc PR . .
O1 O 0.9021(2) -0.0619(2) 0.85722(11) 0.0450(9) Uani 1 1 d . . .
O2 O 0.9848(2) -0.1195(2) 0.62478(11) 0.0469(10) Uani 1 1 d . . .
O7 O 0.8010(3) 0.0472(3) 0.53239(12) 0.0556(12) Uani 1 1 d . . .
N1 N 1.0358(3) -0.1647(3) 0.70785(15) 0.0428(11) Uani 1 1 d . . .
C6 C 0.9067(3) -0.0626(3) 0.80759(17) 0.0381(12) Uani 1 1 d . . .
O6 O 0.6857(3) 0.1386(3) 0.56405(15) 0.0706(14) Uani 1 1 d . . .
N2 N 0.8492(3) -0.0159(3) 0.77399(14) 0.0419(11) Uani 1 1 d . . .
C2 C 0.9806(4) -0.1177(3) 0.67471(17) 0.0442(13) Uani 1 1 d . . .
C12 C 0.8156(3) 0.0173(3) 0.68174(17) 0.0411(13) Uani 1 1 d . . .
C16 C 0.8345(4) 0.0105(4) 0.62510(16) 0.0451(14) Uani 1 1 d . . .
H16 H 0.8784 -0.0227 0.6137 0.054 Uiso 1 1 calc R . .
C8 C 0.8649(3) -0.0256(3) 0.71850(17) 0.0386(12) Uani 1 1 d . . .
O3 O 1.1316(3) -0.1579(3) 0.94812(13) 0.0585(12) Uani 1 1 d . . .
O4 O 1.1902(3) -0.2993(3) 0.93536(14) 0.0611(12) Uani 1 1 d . . .
C21 C 1.1171(4) -0.1913(4) 0.89840(19) 0.0462(14) Uani 1 1 d . . .
C14 C 0.7242(4) 0.1015(4) 0.6055(2) 0.0565(17) Uani 1 1 d . . .
C1 C 0.9325(3) -0.0765(3) 0.71380(16) 0.0388(13) Uani 1 1 d . . .
C5 C 0.9584(3) -0.0995(3) 0.76751(18) 0.0397(13) Uani 1 1 d . . .
C4 C 1.0213(3) -0.1545(3) 0.76336(17) 0.0396(12) Uani 1 1 d . . .
C15 C 0.7898(4) 0.0516(4) 0.58723(19) 0.0502(15) Uani 1 1 d . . .
O5 O 1.0118(4) -0.3182(3) 0.67296(15) 0.0676(13) Uani 1 1 d . . .
C25 C 1.1019(4) -0.2076(3) 0.6817(2) 0.0474(14) Uani 1 1 d . . .
H25A H 1.1460 -0.2161 0.7085 0.057 Uiso 1 1 calc R . .
H25B H 1.1237 -0.1740 0.6517 0.057 Uiso 1 1 calc R . .
C13 C 0.7050(4) 0.1061(4) 0.65987(19) 0.0561(17) Uani 1 1 d . . .
H13 H 0.6598 0.1379 0.6706 0.067 Uiso 1 1 calc R . .
C19 C 1.1362(4) -0.3116(4) 0.8441(2) 0.0489(14) Uani 1 1 d . . .
H19 H 1.1553 -0.3657 0.8401 0.059 Uiso 1 1 calc R . .
C9 C 0.7852(3) 0.0297(3) 0.79296(18) 0.0412(13) Uani 1 1 d . . .
H9 H 0.7766 0.0329 0.8312 0.049 Uiso 1 1 calc R . .
C10 C 0.7346(3) 0.0699(4) 0.75967(19) 0.0470(15) Uani 1 1 d . . .
C20 C 1.1491(3) -0.2705(4) 0.8922(2) 0.0470(14) Uani 1 1 d . . .
C26 C 1.0756(5) -0.2889(4) 0.6592(2) 0.0588(17) Uani 1 1 d . . .
C36 C 0.8611(4) -0.0097(4) 0.51501(18) 0.0576(17) Uani 1 1 d . . .
H36A H 0.9132 0.0038 0.5320 0.086 Uiso 1 1 calc R . .
H36B H 0.8665 -0.0072 0.4752 0.086 Uiso 1 1 calc R . .
H36C H 0.8448 -0.0645 0.5259 0.086 Uiso 1 1 calc R . .
C18 C 1.0956(3) -0.2745(3) 0.80128(18) 0.0434(13) Uani 1 1 d . . .
H18 H 1.0878 -0.3030 0.7680 0.052 Uiso 1 1 calc R . .
C17 C 1.0661(4) -0.1955(4) 0.80665(19) 0.0458(14) Uani 1 1 d . . .
C24 C 1.1034(5) -0.0765(4) 0.9555(2) 0.075(2) Uani 1 1 d . . .
H24A H 1.1298 -0.0408 0.9289 0.113 Uiso 1 1 calc R . .
H24B H 1.1166 -0.0582 0.9925 0.113 Uiso 1 1 calc R . .
H24C H 1.0445 -0.0746 0.9502 0.113 Uiso 1 1 calc R . .
C35 C 0.6179(5) 0.1919(7) 0.5778(3) 0.103(3) Uani 1 1 d . . .
H35A H 0.5738 0.1598 0.5936 0.155 Uiso 1 1 calc R . .
H35B H 0.5986 0.2191 0.5447 0.155 Uiso 1 1 calc R . .
H35C H 0.6359 0.2326 0.6042 0.155 Uiso 1 1 calc R . .
C23 C 1.2275(6) -0.3769(5) 0.9305(3) 0.085(3) Uani 1 1 d . . .
H23A H 1.1862 -0.4176 0.9218 0.128 Uiso 1 1 calc R . .
H23B H 1.2539 -0.3911 0.9650 0.128 Uiso 1 1 calc R . .
H23C H 1.2681 -0.3755 0.9013 0.128 Uiso 1 1 calc R . .
C22 C 1.0771(4) -0.1560(4) 0.85669(18) 0.0467(14) Uani 1 1 d . . .
H22 H 1.0559 -0.1029 0.8614 0.056 Uiso 1 1 calc R . .
C27 C 1.1338(6) -0.3332(5) 0.6214(4) 0.088(3) Uani 1 1 d . . .
C11 C 0.7498(4) 0.0655(4) 0.70018(17) 0.0462(14) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C33 C31 1.530(10) . ?
C31 C10 1.519(8) . ?
C31 C32 1.547(6) . ?
C31 C34 1.553(9) . ?
C29 C27 1.511(13) . ?
C30 C27 1.564(13) . ?
C28 C27 1.533(13) . ?
Cl1X C1X 1.756(10) . ?
C1X Cl1X 1.756(10) 7_637 ?
O1 C6 1.219(5) . ?
O2 C2 1.227(5) . ?
O7 C15 1.359(5) . ?
O7 C36 1.429(7) . ?
N1 C4 1.392(5) . ?
N1 C2 1.445(7) . ?
N1 C25 1.450(7) . ?
C6 C5 1.436(7) . ?
C6 N2 1.474(6) . ?
O6 C14 1.346(6) . ?
O6 C35 1.461(8) . ?
N2 C9 1.376(7) . ?
N2 C8 1.395(5) . ?
C2 C1 1.418(7) . ?
C12 C8 1.406(7) . ?
C12 C11 1.418(8) . ?
C12 C16 1.428(5) . ?
C16 C15 1.367(7) . ?
C8 C1 1.400(8) . ?
O3 C21 1.359(6) . ?
O3 C24 1.434(8) . ?
O4 C20 1.344(6) . ?
O4 C23 1.426(8) . ?
C21 C22 1.349(7) . ?
C21 C20 1.418(8) . ?
C14 C13 1.372(6) . ?
C14 C15 1.431(8) . ?
C1 C5 1.435(6) . ?
C5 C4 1.382(8) . ?
C4 C17 1.460(7) . ?
O5 C26 1.207(8) . ?
C25 C26 1.513(8) . ?
C13 C11 1.404(7) . ?
C19 C20 1.377(7) . ?
C19 C18 1.387(7) . ?
C9 C10 1.343(7) . ?
C10 C11 1.482(6) . ?
C26 C27 1.520(10) . ?
C18 C17 1.397(8) . ?
C17 C22 1.401(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
C10 C31 C33 112.5(5) . . ?
C10 C31 C32 111.8(5) . . ?
C33 C31 C32 105.6(6) . . ?
C10 C31 C34 109.9(6) . . ?
C33 C31 C34 111.6(5) . . ?
C32 C31 C34 105.1(5) . . ?
Cl1X C1X Cl1X 111.5(10) . 7_637 ?
C15 O7 C36 115.1(4) . . ?
C4 N1 C2 112.1(4) . . ?
C4 N1 C25 128.3(5) . . ?
C2 N1 C25 119.2(4) . . ?
O1 C6 C5 136.4(5) . . ?
O1 C6 N2 120.8(5) . . ?
C5 C6 N2 102.7(4) . . ?
C14 O6 C35 117.4(5) . . ?
C9 N2 C8 122.4(4) . . ?
C9 N2 C6 126.1(4) . . ?
C8 N2 C6 111.4(4) . . ?
O2 C2 C1 135.9(6) . . ?
O2 C2 N1 120.8(5) . . ?
C1 C2 N1 103.2(4) . . ?
C8 C12 C11 121.4(4) . . ?
C8 C12 C16 117.2(5) . . ?
C11 C12 C16 121.5(5) . . ?
C15 C16 C12 120.2(5) . . ?
N2 C8 C1 107.3(4) . . ?
N2 C8 C12 117.4(5) . . ?
C1 C8 C12 135.3(4) . . ?
C21 O3 C24 115.8(4) . . ?
C20 O4 C23 118.0(5) . . ?
C22 C21 O3 126.3(5) . . ?
C22 C21 C20 119.8(5) . . ?
O3 C21 C20 113.8(5) . . ?
O6 C14 C13 126.8(6) . . ?
O6 C14 C15 112.5(4) . . ?
C13 C14 C15 120.7(5) . . ?
C8 C1 C2 142.0(4) . . ?
C8 C1 C5 108.6(4) . . ?
C2 C1 C5 109.1(5) . . ?
C4 C5 C1 109.2(4) . . ?
C4 C5 C6 140.7(5) . . ?
C1 C5 C6 109.9(4) . . ?
C5 C4 N1 106.3(4) . . ?
C5 C4 C17 129.1(4) . . ?
N1 C4 C17 124.6(5) . . ?
O7 C15 C16 124.9(5) . . ?
O7 C15 C14 116.3(5) . . ?
C16 C15 C14 118.7(5) . . ?
N1 C25 C26 112.2(5) . . ?
C14 C13 C11 122.4(6) . . ?
C20 C19 C18 120.3(6) . . ?
C10 C9 N2 122.7(4) . . ?
C9 C10 C11 118.0(5) . . ?
C9 C10 C31 119.1(4) . . ?
C11 C10 C31 122.9(5) . . ?
O4 C20 C19 125.4(5) . . ?
O4 C20 C21 115.4(5) . . ?
C19 C20 C21 119.3(5) . . ?
O5 C26 C25 120.2(6) . . ?
O5 C26 C27 121.9(7) . . ?
C25 C26 C27 117.9(7) . . ?
C19 C18 C17 120.6(5) . . ?
C18 C17 C22 118.1(5) . . ?
C18 C17 C4 122.7(5) . . ?
C22 C17 C4 119.2(5) . . ?
C21 C22 C17 121.8(5) . . ?
C29 C27 C26 111.5(8) . . ?
C29 C27 C28 108.4(8) . . ?
C26 C27 C28 106.1(7) . . ?
C29 C27 C30 110.4(8) . . ?
C26 C27 C30 109.4(7) . . ?
C28 C27 C30 111.1(9) . . ?
C13 C11 C12 116.4(4) . . ?
C13 C11 C10 125.5(5) . . ?
C12 C11 C10 118.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        72.03
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.065
