# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exp_4214
_database_code_depnum_ccdc_archive 'CCDC 1001245'
_audit_update_record             
;
2014-05-05 deposited with the CCDC.
2015-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H29 Cl3 N2 O7'
_chemical_formula_weight         599.87

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'
N N 0.0311 0.0180 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   11.0927(7)
_cell_length_b                   15.2908(9)
_cell_length_c                   17.2201(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2920.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3544
_cell_measurement_theta_min      3.8430
_cell_measurement_theta_max      68.6080

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    3.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5230
_exptl_absorpt_correction_T_max  0.6091
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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            19017
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         67.24
_reflns_number_total             5243
_reflns_number_gt                3909
_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  ?
_chemical_absolute_configuration ad
_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)+(0.0836P)²+0.5387P] 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     SHELXL
_refine_ls_extinction_coef       0.0056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_number_reflns         5243
_refine_ls_number_parameters     367
_refine_ls_number_restraints     1297
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1389
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5616(2) 0.46916(12) 0.88895(11) 0.1304(7) Uani 1 1 d U . .
Cl2 Cl 0.7448(2) 0.59287(16) 0.91966(13) 0.1583(9) Uani 1 1 d U . .
Cl3 Cl 0.5276(3) 0.5963(3) 1.00763(14) 0.2461(19) Uani 1 1 d U . .
N1 N 0.8569(3) 0.57189(19) 0.70774(19) 0.0582(7) Uani 1 1 d U . .
N2 N 0.3611(3) 0.5603(2) 0.69589(18) 0.0614(8) Uani 1 1 d U . .
O1 O 0.7234(2) 0.49736(16) 0.63155(15) 0.0621(7) Uani 1 1 d U . .
O2 O 0.4611(3) 0.7176(2) 0.80515(16) 0.0782(8) Uani 1 1 d U A .
O3 O 0.4782(3) 0.77755(17) 0.68838(16) 0.0666(7) Uani 1 1 d U . .
O4 O 0.7840(2) 0.68617(18) 0.55369(15) 0.0560(6) Uani 1 1 d U . .
H4 H 0.8268 0.7259 0.5697 0.084 Uiso 1 1 calc R . .
O5 O 0.3540(3) 0.4935(2) 0.73458(19) 0.0898(10) Uani 1 1 d U . .
O6 O 0.2808(3) 0.6136(2) 0.6895(2) 0.0879(10) Uani 1 1 d U . .
O7 O 0.4375(2) 0.67113(15) 0.43046(14) 0.0532(6) Uani 1 1 d U . .
C1 C 0.9582(4) 0.6863(3) 0.7884(3) 0.0740(11) Uani 1 1 d U . .
H1 H 1.0268 0.6533 0.7985 0.089 Uiso 1 1 calc R . .
C2 C 0.9433(4) 0.7691(3) 0.8189(3) 0.0773(12) Uani 1 1 d U . .
H2 H 1.0024 0.7914 0.8517 0.093 Uiso 1 1 calc R . .
C3 C 0.8446(4) 0.8193(3) 0.8025(2) 0.0685(10) Uani 1 1 d U . .
H3 H 0.8379 0.8751 0.8236 0.082 Uiso 1 1 calc R . .
C4 C 0.7540(4) 0.7870(2) 0.7543(2) 0.0562(8) Uani 1 1 d U . .
H4A H 0.6873 0.8213 0.7423 0.067 Uiso 1 1 calc R . .
C5 C 0.7642(3) 0.7037(2) 0.72453(19) 0.0482(7) Uani 1 1 d U . .
C6 C 0.8661(4) 0.6550(2) 0.7421(2) 0.0578(9) Uani 1 1 d U . .
C7 C 0.9479(5) 0.5037(3) 0.7128(3) 0.0866(14) Uani 1 1 d U . .
H7A H 0.9270 0.4566 0.6785 0.130 Uiso 1 1 calc R . .
H7B H 0.9520 0.4824 0.7651 0.130 Uiso 1 1 calc R . .
H7C H 1.0248 0.5272 0.6980 0.130 Uiso 1 1 calc R . .
C8 C 0.7526(3) 0.5632(2) 0.6671(2) 0.0494(8) Uani 1 1 d U . .
C9 C 0.6818(3) 0.6493(2) 0.67303(19) 0.0438(7) Uani 1 1 d U . .
C10 C 0.5577(3) 0.6325(2) 0.71076(19) 0.0454(7) Uani 1 1 d U . .
H10 H 0.5704 0.5992 0.7587 0.054 Uiso 1 1 calc R . .
C11 C 0.4805(3) 0.5770(2) 0.65585(18) 0.0462(7) Uani 1 1 d U . .
H11 H 0.5210 0.5206 0.6486 0.055 Uiso 1 1 calc R . .
C12 C 0.4608(3) 0.6176(2) 0.57615(18) 0.0440(7) Uani 1 1 d U . .
H12 H 0.4134 0.6713 0.5821 0.053 Uiso 1 1 calc R . .
C13 C 0.5834(3) 0.6406(2) 0.53783(18) 0.0423(7) Uani 1 1 d U . .
H13 H 0.6223 0.5848 0.5252 0.051 Uiso 1 1 calc R . .
C14 C 0.6705(3) 0.6898(2) 0.59117(18) 0.0427(7) Uani 1 1 d U . .
H14 H 0.6447 0.7509 0.5957 0.051 Uiso 1 1 calc R . .
C15 C 0.5614(3) 0.6884(2) 0.4591(2) 0.0500(8) Uani 1 1 d U . .
C16 C 0.6454(4) 0.6560(3) 0.3965(2) 0.0732(12) Uani 1 1 d U . .
H16A H 0.6330 0.5944 0.3887 0.110 Uiso 1 1 calc R . .
H16B H 0.7273 0.6662 0.4119 0.110 Uiso 1 1 calc R . .
H16C H 0.6292 0.6866 0.3489 0.110 Uiso 1 1 calc R . .
C17 C 0.5647(4) 0.7872(2) 0.4646(2) 0.0649(10) Uani 1 1 d U . .
H17A H 0.5329 0.8120 0.4177 0.097 Uiso 1 1 calc R . .
H17B H 0.6464 0.8062 0.4716 0.097 Uiso 1 1 calc R . .
H17C H 0.5168 0.8060 0.5079 0.097 Uiso 1 1 calc R . .
C18 C 0.3910(3) 0.5887(2) 0.4450(2) 0.0520(8) Uani 1 1 d U . .
C19 C 0.3371(4) 0.5422(3) 0.3860(2) 0.0620(9) Uani 1 1 d U . .
H19 H 0.3322 0.5651 0.3361 0.074 Uiso 1 1 calc R . .
C20 C 0.2905(4) 0.4609(3) 0.4028(3) 0.0731(11) Uani 1 1 d U . .
H20 H 0.2525 0.4289 0.3639 0.088 Uiso 1 1 calc R . .
C21 C 0.2996(5) 0.4264(3) 0.4763(3) 0.0785(12) Uani 1 1 d U . .
H21 H 0.2695 0.3708 0.4865 0.094 Uiso 1 1 calc R . .
C22 C 0.3535(4) 0.4744(2) 0.5351(2) 0.0625(10) Uani 1 1 d U . .
H22 H 0.3605 0.4505 0.5845 0.075 Uiso 1 1 calc R . .
C23 C 0.3971(3) 0.5577(2) 0.5204(2) 0.0500(8) Uani 1 1 d U . .
C24 C 0.4942(3) 0.7180(2) 0.7316(2) 0.0529(8) Uani 1 1 d U . .
C25 C 0.4022(6) 0.7974(4) 0.8333(4) 0.1068(18) Uani 1 1 d U . .
H25A H 0.4435 0.8183 0.8793 0.128 Uiso 0.480(11) 1 calc PR A 1
H25B H 0.4071 0.8425 0.7938 0.128 Uiso 0.480(11) 1 calc PR A 1
H25C H 0.4470 0.8481 0.8156 0.128 Uiso 0.520(11) 1 d PR A 2
H25D H 0.3217 0.8008 0.8116 0.128 Uiso 0.520(11) 1 d PR A 2
C26 C 0.2851(13) 0.7815(8) 0.8505(11) 0.128(5) Uani 0.480(11) 1 d PU A .
H26A H 0.2805 0.7327 0.8855 0.192 Uiso 0.480(11) 1 d PR . .
H26B H 0.2415 0.7681 0.8038 0.192 Uiso 0.480(11) 1 d PR . .
H26C H 0.2505 0.8321 0.8746 0.192 Uiso 0.480(11) 1 d PR . .
C27 C 0.6302(6) 0.5327(5) 0.9608(3) 0.117(2) Uani 1 1 d U . .
H27 H 0.6661 0.4929 0.9991 0.140 Uiso 1 1 calc R . .
C26' C 0.3974(18) 0.7988(8) 0.9129(7) 0.142(5) Uani 0.520(11) 1 d PU A 2
H26D H 0.3466 0.7527 0.9319 0.213 Uiso 0.520(11) 1 d PR A 2
H26E H 0.3667 0.8542 0.9303 0.213 Uiso 0.520(11) 1 d PR A 2
H26F H 0.4778 0.7908 0.9324 0.213 Uiso 0.520(11) 1 d PR A 2


_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 C27 1.748(7) . ?
Cl2 C27 1.722(7) . ?
Cl3 C27 1.700(6) . ?
N1 C8 1.358(5) . ?
N1 C6 1.405(5) . ?
N1 C7 1.454(5) . ?
N2 O6 1.213(5) . ?
N2 O5 1.222(4) . ?
N2 C11 1.515(4) . ?
O1 C8 1.221(4) . ?
O2 C24 1.319(4) . ?
O2 C25 1.466(6) . ?
O3 C24 1.189(4) . ?
O4 C14 1.416(4) . ?
O7 C18 1.384(4) . ?
O7 C15 1.484(4) . ?
C1 C2 1.380(6) . ?
C1 C6 1.382(5) . ?
C2 C3 1.367(6) . ?
C3 C4 1.395(5) . ?
C4 C5 1.377(5) . ?
C5 C6 1.388(5) . ?
C5 C9 1.521(5) . ?
C8 C9 1.537(4) . ?
C9 C10 1.544(5) . ?
C9 C14 1.545(4) . ?
C10 C24 1.529(5) . ?
C10 C11 1.532(5) . ?
C11 C12 1.522(4) . ?
C12 C23 1.503(4) . ?
C12 C13 1.552(4) . ?
C13 C14 1.530(4) . ?
C13 C15 1.560(4) . ?
C15 C16 1.509(5) . ?
C15 C17 1.513(5) . ?
C18 C19 1.377(5) . ?
C18 C23 1.385(5) . ?
C19 C20 1.376(6) . ?
C20 C21 1.374(6) . ?
C21 C22 1.386(6) . ?
C22 C23 1.385(5) . ?
C25 C26 1.354(15) . ?
C25 C26' 1.372(13) . ?

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
C8 N1 C6 111.6(3) . . ?
C8 N1 C7 123.5(3) . . ?
C6 N1 C7 124.9(3) . . ?
O6 N2 O5 124.3(4) . . ?
O6 N2 C11 119.1(3) . . ?
O5 N2 C11 116.5(4) . . ?
C24 O2 C25 116.0(4) . . ?
C18 O7 C15 116.6(2) . . ?
C2 C1 C6 116.7(4) . . ?
C3 C2 C1 122.2(4) . . ?
C2 C3 C4 120.0(4) . . ?
C5 C4 C3 119.4(4) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 C9 132.4(3) . . ?
C6 C5 C9 108.8(3) . . ?
C1 C6 C5 122.8(4) . . ?
C1 C6 N1 127.6(4) . . ?
C5 C6 N1 109.5(3) . . ?
O1 C8 N1 124.4(3) . . ?
O1 C8 C9 127.1(3) . . ?
N1 C8 C9 108.4(3) . . ?
C5 C9 C8 101.6(3) . . ?
C5 C9 C10 112.4(3) . . ?
C8 C9 C10 110.0(3) . . ?
C5 C9 C14 111.2(3) . . ?
C8 C9 C14 108.9(3) . . ?
C10 C9 C14 112.2(3) . . ?
C24 C10 C11 111.1(3) . . ?
C24 C10 C9 111.6(3) . . ?
C11 C10 C9 109.3(3) . . ?
N2 C11 C12 110.7(3) . . ?
N2 C11 C10 107.6(3) . . ?
C12 C11 C10 114.3(3) . . ?
C23 C12 C11 113.2(3) . . ?
C23 C12 C13 106.2(3) . . ?
C11 C12 C13 110.5(3) . . ?
C14 C13 C12 114.1(3) . . ?
C14 C13 C15 112.9(3) . . ?
C12 C13 C15 109.8(2) . . ?
O4 C14 C13 105.6(2) . . ?
O4 C14 C9 109.1(3) . . ?
C13 C14 C9 113.7(3) . . ?
O7 C15 C16 106.0(3) . . ?
O7 C15 C17 102.8(3) . . ?
C16 C15 C17 111.0(3) . . ?
O7 C15 C13 110.5(3) . . ?
C16 C15 C13 111.7(3) . . ?
C17 C15 C13 114.2(3) . . ?
C19 C18 O7 120.0(3) . . ?
C19 C18 C23 122.4(3) . . ?
O7 C18 C23 117.6(3) . . ?
C20 C19 C18 118.4(4) . . ?
C21 C20 C19 120.9(4) . . ?
C20 C21 C22 120.0(4) . . ?
C23 C22 C21 120.3(4) . . ?
C18 C23 C22 117.9(3) . . ?
C18 C23 C12 114.4(3) . . ?
C22 C23 C12 127.5(3) . . ?
O3 C24 O2 124.3(3) . . ?
O3 C24 C10 125.3(3) . . ?
O2 C24 C10 110.5(3) . . ?
C26 C25 C26' 75.4(10) . . ?
C26 C25 O2 110.5(7) . . ?
C26' C25 O2 111.2(7) . . ?
Cl3 C27 Cl2 112.6(5) . . ?
Cl3 C27 Cl1 111.2(4) . . ?
Cl2 C27 Cl1 109.1(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.048
