# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1829569'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        'Compound 1'
_chemical_formula_moiety         'C H Cl3, C35 H41 N O5'
_chemical_formula_sum            'C36 H42 Cl3 N O5'
_chemical_formula_weight         675.06
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 'x+1/2, -y+1/2, -z'
4 '-x+1/2, y+1/2, -z'

_cell_length_a                   15.04610(10)
_cell_length_b                   28.6830(2)
_cell_length_c                   7.87240(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3397.47(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7240
_cell_measurement_theta_min      4.2370
_exptl_absorpt_coefficient_mu    2.788
_exptl_absorpt_correction_T_max  0.8506
_exptl_absorpt_correction_T_min  0.2139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25248
_diffrn_reflns_theta_full        74.12
_diffrn_reflns_theta_max         74.12
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6540
_reflns_number_total             6774
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(13)
_refine_ls_extinction_coef       0.00086(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0641P)²+1.4806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1137
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1'(H1'), C17(H17), C12(H12), C13(H13), C9(H9), C15(H15), C6(H6), C18(H18),
 C14(H14), C11(H11), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C31(H31), C4(H4), C22(H22), C28(H28), C30(H30), C2(H2), C27(H27)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl -0.25254(5) -0.13601(3) -0.29154(9) 0.04563(18) Uani 1 d . . .
Cl2 Cl -0.19499(6) -0.21679(3) -0.47541(13) 0.0608(2) Uani 1 d . . .
Cl3 Cl -0.11104(7) -0.12825(3) -0.53581(13) 0.0722(3) Uani 1 d . . .
C1' C -0.16070(17) -0.16408(9) -0.3855(3) 0.0314(5) Uani 1 d . . .
H1' H -0.1170 -0.1709 -0.2965 0.038 Uiso 1 calc . . R
O1 O -0.67598(9) -0.10775(5) -0.0882(2) 0.0204(3) Uani 1 d . . .
O4 O -0.95413(10) -0.32668(5) -0.0039(2) 0.0208(3) Uani 1 d . . .
O3 O -0.96571(12) -0.26319(6) 0.5316(2) 0.0289(4) Uani 1 d . . .
O5 O -1.05002(10) -0.18157(5) -0.0656(2) 0.0244(3) Uani 1 d . . .
O2 O -0.85244(11) -0.17650(6) 0.3414(2) 0.0273(4) Uani 1 d . . .
C17 C -0.95851(13) -0.21271(7) 0.1648(2) 0.0156(4) Uani 1 d . . .
H17 H -1.0072 -0.2131 0.2474 0.019 Uiso 1 calc . . R
N1 N -0.97161(11) -0.24915(6) -0.1008(2) 0.0186(4) Uani 1 d . . .
H1 H -0.9887 -0.2543 -0.2034 0.022 Uiso 1 calc . . R
C12 C -0.72613(13) -0.03354(7) 0.0383(3) 0.0177(4) Uani 1 d . . .
H12 H -0.7791 -0.0140 0.0246 0.021 Uiso 1 calc . . R
C13 C -0.75331(13) -0.08180(7) -0.0240(3) 0.0172(4) Uani 1 d . . .
H13 H -0.7981 -0.0789 -0.1137 0.021 Uiso 1 calc . . R
C9 C -0.63712(15) 0.04115(7) 0.2256(3) 0.0238(5) Uani 1 d . . .
H9 H -0.5800 0.0272 0.2568 0.029 Uiso 1 calc . . R
C15 C -0.88505(13) -0.12941(7) 0.0990(2) 0.0154(4) Uani 1 d . . .
H15 H -0.8843 -0.1405 -0.0187 0.019 Uiso 1 calc . . R
C23 C -0.99926(13) -0.21138(7) -0.0116(3) 0.0170(4) Uani 1 d . . .
C16 C -0.89499(13) -0.17217(7) 0.2133(3) 0.0165(4) Uani 1 d . . .
C34 C -0.62500(14) -0.06336(8) 0.2766(3) 0.0216(4) Uani 1 d . . .
H34A H -0.6273 -0.0948 0.2352 0.032 Uiso 1 calc . . GR
H34B H -0.6174 -0.0636 0.3977 0.032 Uiso 1 calc . . GR
H34C H -0.5759 -0.0474 0.2249 0.032 Uiso 1 calc . . GR
C8 C -0.71144(15) 0.01154(7) 0.3040(3) 0.0199(4) Uani 1 d . . .
H8A H -0.7033 0.0101 0.4261 0.024 Uiso 1 calc . . R
H8B H -0.7683 0.0262 0.2818 0.024 Uiso 1 calc . . R
C19 C -0.96420(13) -0.29805(7) 0.2644(3) 0.0169(4) Uani 1 d . . .
C6 C -0.78913(13) -0.07201(7) 0.2860(3) 0.0160(4) Uani 1 d . . .
H6 H -0.7664 -0.0901 0.3821 0.019 Uiso 1 calc . . R
C26 C -0.77339(13) -0.24291(7) -0.1271(3) 0.0191(4) Uani 1 d . . .
C31 C -0.70905(13) -0.23186(7) -0.0071(3) 0.0218(4) Uani 1 d . . .
H31 H -0.6904 -0.2543 0.0702 0.026 Uiso 1 calc . . R
C4 C -0.95395(14) -0.06403(7) 0.2688(3) 0.0213(4) Uani 1 d . . .
H4 H -1.0055 -0.0516 0.3158 0.026 Uiso 1 calc . . R
C22 C -0.98376(14) -0.33256(7) 0.1551(3) 0.0193(4) Uani 1 d . . .
H22 H -1.0158 -0.3588 0.1877 0.023 Uiso 1 calc . . R
C24 C -0.91241(13) -0.27980(7) -0.0142(3) 0.0173(4) Uani 1 d . . .
C7 C -0.71226(13) -0.03810(7) 0.2316(3) 0.0161(4) Uani 1 d . . .
C18 C -0.91122(13) -0.26083(7) 0.1727(2) 0.0154(4) Uani 1 d . . .
H18 H -0.8506 -0.2582 0.2173 0.018 Uiso 1 calc . . R
C29 C -0.70054(13) -0.15406(7) -0.1165(3) 0.0197(4) Uani 1 d . . .
C5 C -0.87774(15) -0.05231(7) 0.3420(3) 0.0194(4) Uani 1 d . . .
C20 C -0.98967(14) -0.29584(7) 0.4424(3) 0.0205(4) Uani 1 d . . .
C28 C -0.75747(14) -0.16596(7) -0.2479(3) 0.0213(4) Uani 1 d . . .
H28 H -0.7710 -0.1444 -0.3321 0.026 Uiso 1 calc . . R
C30 C -0.67245(13) -0.18737(8) -0.0019(3) 0.0205(4) Uani 1 d . . .
H30 H -0.6293 -0.1801 0.0784 0.025 Uiso 1 calc . . R
C10 C -0.64424(16) 0.04133(8) 0.0316(3) 0.0252(5) Uani 1 d . . .
H10A H -0.5925 0.0570 -0.0145 0.030 Uiso 1 calc . . R
H10B H -0.6962 0.0593 -0.0005 0.030 Uiso 1 calc . . R
C32 C -0.6669(2) -0.00225(10) -0.2414(3) 0.0340(6) Uani 1 d . . .
H32A H -0.6703 -0.0327 -0.2919 0.051 Uiso 1 calc . . GR
H32B H -0.6187 0.0148 -0.2915 0.051 Uiso 1 calc . . GR
H32C H -0.7217 0.0141 -0.2607 0.051 Uiso 1 calc . . GR
C14 C -0.79447(13) -0.10612(7) 0.1334(3) 0.0155(4) Uani 1 d . . .
H14 H -0.7538 -0.1317 0.1612 0.019 Uiso 1 calc . . R
C2 C -0.98215(16) -0.06675(8) -0.0395(3) 0.0262(5) Uani 1 d . . .
H2 H -0.9362 -0.0479 -0.0788 0.031 Uiso 1 calc . . R
C33 C -0.6394(2) 0.09063(9) 0.2945(4) 0.0381(6) Uani 1 d . . .
H33A H -0.6964 0.1043 0.2713 0.057 Uiso 1 calc . . GR
H33B H -0.5938 0.1088 0.2407 0.057 Uiso 1 calc . . GR
H33C H -0.6295 0.0901 0.4149 0.057 Uiso 1 calc . . GR
C25 C -0.82497(14) -0.28771(7) -0.1098(3) 0.0198(4) Uani 1 d . . .
H25A H -0.7893 -0.3104 -0.0491 0.024 Uiso 1 calc . . R
H25B H -0.8376 -0.3001 -0.2218 0.024 Uiso 1 calc . . R
C11 C -0.65110(15) -0.00709(8) -0.0499(3) 0.0230(5) Uani 1 d . . .
H11 H -0.5952 -0.0238 -0.0314 0.028 Uiso 1 calc . . R
C3 C -0.96514(13) -0.09557(7) 0.1167(3) 0.0191(4) Uani 1 d . . .
H3 H -1.0182 -0.1146 0.1366 0.023 Uiso 1 calc . . R
C35 C -0.87910(16) -0.02533(8) 0.5064(3) 0.0272(5) Uani 1 d . . .
H35A H -0.8398 -0.0399 0.5866 0.041 Uiso 1 calc . . GR
H35B H -0.9384 -0.0251 0.5514 0.041 Uiso 1 calc . . GR
H35C H -0.8600 0.0061 0.4859 0.041 Uiso 1 calc . . GR
C27 C -0.79412(14) -0.21035(7) -0.2530(3) 0.0204(4) Uani 1 d . . .
H27 H -0.8326 -0.2185 -0.3406 0.025 Uiso 1 calc . . R
C1 C -1.0572(2) -0.06629(10) -0.1241(4) 0.0381(6) Uani 1 d . . .
C21 C -1.04799(17) -0.33366(8) 0.5145(3) 0.0307(5) Uani 1 d . . .
H21A H -1.0422 -0.3342 0.6359 0.046 Uiso 1 calc . . GR
H21B H -1.0302 -0.3633 0.4689 0.046 Uiso 1 calc . . GR
H21C H -1.1088 -0.3276 0.4846 0.046 Uiso 1 calc . . GR
H1A H -1.108(2) -0.0862(11) -0.086(4) 0.040(8) Uiso 1 d . . .
H1B H -1.066(2) -0.0462(12) -0.229(5) 0.055(10) Uiso 1 d . . .


_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 C1' 1.762(3) . ?
Cl2 C1' 1.747(3) . ?
Cl3 C1' 1.736(3) . ?
O1 C13 1.471(2) . ?
O1 C29 1.397(3) . ?
O4 C22 1.339(3) . ?
O4 C24 1.486(2) . ?
O3 C20 1.225(3) . ?
O5 C23 1.223(3) . ?
O2 C16 1.201(3) . ?
C17 C23 1.518(3) . ?
C17 C16 1.553(3) . ?
C17 C18 1.554(3) . ?
N1 C23 1.357(3) . ?
N1 C24 1.425(3) . ?
C12 C13 1.524(3) . ?
C12 C7 1.542(3) . ?
C12 C11 1.527(3) . ?
C13 C14 1.551(3) . ?
C9 C8 1.534(3) . ?
C9 C10 1.531(3) . ?
C9 C33 1.520(3) . ?
C15 C16 1.529(3) . ?
C15 C14 1.542(3) . ?
C15 C3 1.554(3) . ?
C34 C7 1.541(3) . ?
C8 C7 1.534(3) . ?
C19 C22 1.344(3) . ?
C19 C18 1.515(3) . ?
C19 C20 1.454(3) . ?
C6 C7 1.571(3) . ?
C6 C5 1.514(3) . ?
C6 C14 1.551(3) . ?
C26 C31 1.389(3) . ?
C26 C25 1.507(3) . ?
C26 C27 1.397(3) . ?
C31 C30 1.390(3) . ?
C4 C5 1.326(3) . ?
C4 C3 1.510(3) . ?
C24 C18 1.569(3) . ?
C24 C25 1.533(3) . ?
C29 C28 1.386(3) . ?
C29 C30 1.380(3) . ?
C5 C35 1.509(3) . ?
C20 C21 1.506(3) . ?
C28 C27 1.388(3) . ?
C10 C11 1.533(3) . ?
C32 C11 1.533(3) . ?
C2 C3 1.504(3) . ?
C2 C1 1.311(4) . ?

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
Cl2 C1' Cl1 109.50(14) . . ?
Cl3 C1' Cl1 110.68(15) . . ?
Cl3 C1' Cl2 111.29(15) . . ?
C29 O1 C13 109.08(14) . . ?
C22 O4 C24 107.78(15) . . ?
C23 C17 C16 117.06(16) . . ?
C23 C17 C18 104.12(16) . . ?
C16 C17 C18 111.92(16) . . ?
C23 N1 C24 115.87(17) . . ?
C13 C12 C7 106.06(16) . . ?
C13 C12 C11 120.23(18) . . ?
C11 C12 C7 113.00(17) . . ?
O1 C13 C12 110.97(16) . . ?
O1 C13 C14 111.29(15) . . ?
C12 C13 C14 105.00(16) . . ?
C10 C9 C8 110.62(17) . . ?
C33 C9 C8 110.9(2) . . ?
C33 C9 C10 110.5(2) . . ?
C16 C15 C14 109.33(16) . . ?
C16 C15 C3 111.87(15) . . ?
C14 C15 C3 113.53(16) . . ?
O5 C23 C17 125.99(19) . . ?
O5 C23 N1 124.75(19) . . ?
N1 C23 C17 109.25(17) . . ?
O2 C16 C17 117.22(18) . . ?
O2 C16 C15 121.67(18) . . ?
C15 C16 C17 121.08(17) . . ?
C7 C8 C9 111.76(17) . . ?
C22 C19 C18 109.19(18) . . ?
C22 C19 C20 126.27(19) . . ?
C20 C19 C18 124.53(18) . . ?
C5 C6 C7 119.79(16) . . ?
C5 C6 C14 114.54(17) . . ?
C14 C6 C7 102.58(15) . . ?
C31 C26 C25 119.5(2) . . ?
C31 C26 C27 119.0(2) . . ?
C27 C26 C25 121.26(19) . . ?
C26 C31 C30 120.4(2) . . ?
C5 C4 C3 126.33(19) . . ?
O4 C22 C19 115.65(18) . . ?
O4 C24 C18 105.52(15) . . ?
O4 C24 C25 104.79(15) . . ?
N1 C24 O4 108.67(15) . . ?
N1 C24 C18 104.01(16) . . ?
N1 C24 C25 113.13(17) . . ?
C25 C24 C18 120.15(17) . . ?
C12 C7 C6 102.81(16) . . ?
C34 C7 C12 112.45(17) . . ?
C34 C7 C6 105.89(16) . . ?
C8 C7 C12 106.80(16) . . ?
C8 C7 C34 110.15(17) . . ?
C8 C7 C6 118.67(17) . . ?
C17 C18 C24 105.37(15) . . ?
C19 C18 C17 113.83(16) . . ?
C19 C18 C24 101.33(15) . . ?
C28 C29 O1 121.1(2) . . ?
C30 C29 O1 118.23(19) . . ?
C30 C29 C28 120.5(2) . . ?
C4 C5 C6 122.71(19) . . ?
C4 C5 C35 119.4(2) . . ?
C35 C5 C6 116.96(19) . . ?
O3 C20 C19 120.55(19) . . ?
O3 C20 C21 120.4(2) . . ?
C19 C20 C21 119.02(19) . . ?
C29 C28 C27 119.5(2) . . ?
C29 C30 C31 119.7(2) . . ?
C9 C10 C11 114.77(18) . . ?
C13 C14 C6 108.31(15) . . ?
C15 C14 C13 114.08(16) . . ?
C15 C14 C6 117.05(16) . . ?
C1 C2 C3 124.6(2) . . ?
C26 C25 C24 111.10(17) . . ?
C12 C11 C10 108.04(18) . . ?
C12 C11 C32 112.15(19) . . ?
C32 C11 C10 109.87(19) . . ?
C4 C3 C15 111.02(17) . . ?
C2 C3 C15 113.72(17) . . ?
C2 C3 C4 109.75(17) . . ?
C28 C27 C26 120.3(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_compound_source        'Ascidian-derived fungi'
