# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mo_yd_lj_b3_0m
_database_code_depnum_ccdc_archive 'CCDC 1547075'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H23 F N2 O4), H2 O'
_chemical_formula_sum            'C40 H48 F2 N4 O9'
_chemical_formula_weight         766.82
_chemical_absolute_configuration unk

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'

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

_cell_length_a                   12.3686(8)
_cell_length_b                   15.9846(11)
_cell_length_c                   9.9812(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.5910(10)
_cell_angle_gamma                90.00
_cell_volume                     1808.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8904
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      29.99

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9586
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19064
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         30.07
_reflns_number_total             9463
_reflns_number_gt                8786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0570P)²+0.1693P] 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   -0.2(4)
_refine_ls_number_reflns         9463
_refine_ls_number_parameters     500
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
F1 F 0.15664(10) 0.96013(6) -0.04095(11) 0.0294(2) Uani 1 1 d . . .
F2 F 0.56229(9) 0.44913(6) 0.58182(11) 0.0280(2) Uani 1 1 d . . .
O1 O -0.08807(10) 0.54126(7) 0.28338(12) 0.0225(2) Uani 1 1 d . . .
O1S O 0.99813(11) 0.61668(7) 0.92931(13) 0.0258(2) Uani 1 1 d . . .
H1SA H 0.9580 0.5750 0.8848 0.039 Uiso 1 1 d R . .
H1SB H 0.9466 0.6558 0.9199 0.039 Uiso 1 1 d R . .
O2 O 0.36444(9) 0.69761(7) 0.45252(12) 0.0192(2) Uani 1 1 d . . .
O3 O 0.11926(9) 0.78395(6) 0.67740(12) 0.0176(2) Uani 1 1 d . . .
O4 O -0.07955(9) 0.78553(6) 0.51652(11) 0.0172(2) Uani 1 1 d . . .
O5 O 0.47810(12) 0.93890(8) 0.71000(13) 0.0276(3) Uani 1 1 d . . .
O6 O 0.85777(10) 0.75081(7) 0.93665(12) 0.0202(2) Uani 1 1 d . . .
O7 O 0.60104(10) 0.74741(7) 1.19446(12) 0.0208(2) Uani 1 1 d . . .
O8 O 0.40733(10) 0.78584(7) 1.04447(13) 0.0207(2) Uani 1 1 d . . .
N1 N 0.13366(11) 0.60873(7) 0.63775(13) 0.0161(2) Uani 1 1 d . . .
N2 N 0.31241(11) 0.59347(8) 0.61619(14) 0.0176(2) Uani 1 1 d . . .
H2 H 0.3620 0.6124 0.5802 0.021 Uiso 1 1 calc R . .
N3 N 0.67679(11) 0.90305(8) 1.12426(14) 0.0175(2) Uani 1 1 d . . .
N4 N 0.84921(11) 0.87810(8) 1.08946(14) 0.0187(2) Uani 1 1 d . . .
H4 H 0.8861 0.8478 1.0471 0.022 Uiso 1 1 calc R . .
C1 C 0.17814(14) 0.90344(9) 0.06956(17) 0.0196(3) Uani 1 1 d . . .
C2 C 0.11926(14) 0.82835(10) 0.03888(17) 0.0209(3) Uani 1 1 d . . .
H2A H 0.0643 0.8155 -0.0572 0.025 Uiso 1 1 calc R . .
C3 C 0.14268(13) 0.77159(9) 0.15300(16) 0.0185(3) Uani 1 1 d . . .
H3 H 0.1025 0.7194 0.1347 0.022 Uiso 1 1 calc R . .
C4 C 0.22425(13) 0.79026(9) 0.29369(15) 0.0143(3) Uani 1 1 d . . .
C5 C 0.25908(13) 0.72417(8) 0.41182(15) 0.0145(2) Uani 1 1 d . . .
C6 C 0.17642(12) 0.69613(8) 0.46593(15) 0.0139(2) Uani 1 1 d . . .
C7 C 0.05598(12) 0.73604(9) 0.42165(15) 0.0144(2) Uani 1 1 d . . .
H7 H 0.0592 0.7937 0.3846 0.017 Uiso 1 1 calc R . .
C8 C -0.04668(13) 0.68770(9) 0.30210(16) 0.0169(3) Uani 1 1 d . . .
H8A H -0.1186 0.7229 0.2684 0.020 Uiso 1 1 calc R . .
H8B H -0.0260 0.6777 0.2173 0.020 Uiso 1 1 calc R . .
C9 C -0.07333(12) 0.60473(9) 0.35525(16) 0.0165(3) Uani 1 1 d . . .
C10 C 0.28340(14) 0.86637(9) 0.31980(17) 0.0207(3) Uani 1 1 d . . .
H10 H 0.3401 0.8791 0.4150 0.025 Uiso 1 1 calc R . .
C11 C 0.25985(15) 0.92391(9) 0.20705(18) 0.0232(3) Uani 1 1 d . . .
H11 H 0.2993 0.9763 0.2244 0.028 Uiso 1 1 calc R . .
C12 C 0.20785(12) 0.63152(8) 0.57554(15) 0.0146(3) Uani 1 1 d . . .
C13 C 0.16179(14) 0.53976(9) 0.74368(17) 0.0187(3) Uani 1 1 d . . .
H13A H 0.0880 0.5117 0.7354 0.022 Uiso 1 1 calc R . .
H13B H 0.2010 0.5623 0.8441 0.022 Uiso 1 1 calc R . .
C14 C 0.24195(14) 0.47705(9) 0.71616(18) 0.0198(3) Uani 1 1 d . . .
H14A H 0.1998 0.4493 0.6206 0.024 Uiso 1 1 calc R . .
H14B H 0.2663 0.4336 0.7933 0.024 Uiso 1 1 calc R . .
C15 C 0.34955(14) 0.52250(9) 0.71655(18) 0.0203(3) Uani 1 1 d . . .
H15A H 0.3983 0.5425 0.8165 0.024 Uiso 1 1 calc R . .
H15B H 0.3979 0.4838 0.6860 0.024 Uiso 1 1 calc R . .
C16 C 0.02423(12) 0.65432(9) 0.61373(15) 0.0154(3) Uani 1 1 d . . .
H16 H 0.0147 0.6579 0.7084 0.019 Uiso 1 1 calc R . .
C17 C -0.08163(13) 0.60673(9) 0.50237(16) 0.0176(3) Uani 1 1 d . . .
H17A H -0.0827 0.5489 0.5371 0.021 Uiso 1 1 calc R . .
H17B H -0.1559 0.6346 0.4928 0.021 Uiso 1 1 calc R . .
C18 C 0.03026(13) 0.74319(8) 0.55938(16) 0.0149(3) Uani 1 1 d . . .
C19 C 0.14888(14) 0.86607(9) 0.64533(18) 0.0220(3) Uani 1 1 d . . .
H19A H 0.0764 0.8976 0.5919 0.033 Uiso 1 1 calc R . .
H19B H 0.1949 0.8617 0.5854 0.033 Uiso 1 1 calc R . .
H19C H 0.1956 0.8951 0.7368 0.033 Uiso 1 1 calc R . .
C20 C -0.11694(15) 0.80206(11) 0.63284(18) 0.0238(3) Uani 1 1 d . . .
H20A H -0.0568 0.8355 0.7086 0.036 Uiso 1 1 calc R . .
H20B H -0.1279 0.7490 0.6750 0.036 Uiso 1 1 calc R . .
H20C H -0.1916 0.8329 0.5943 0.036 Uiso 1 1 calc R . .
C21 C 0.47454(13) 0.89546(9) 0.80844(17) 0.0186(3) Uani 1 1 d . . .
C22 C 0.46849(13) 0.80143(9) 0.79963(17) 0.0178(3) Uani 1 1 d . . .
H22A H 0.4869 0.7822 0.7168 0.021 Uiso 1 1 calc R . .
H22B H 0.3877 0.7826 0.7821 0.021 Uiso 1 1 calc R . .
C23 C 0.55746(13) 0.76283(9) 0.94362(16) 0.0155(3) Uani 1 1 d . . .
H23 H 0.5494 0.7006 0.9369 0.019 Uiso 1 1 calc R . .
C24 C 0.68436(13) 0.78576(8) 0.97386(16) 0.0148(3) Uani 1 1 d . . .
C25 C 0.75110(13) 0.73693(9) 0.91847(15) 0.0151(3) Uani 1 1 d . . .
C26 C 0.69586(12) 0.66007(9) 0.82900(15) 0.0149(3) Uani 1 1 d . . .
C27 C 0.71227(13) 0.58180(9) 0.89572(16) 0.0179(3) Uani 1 1 d . . .
H27 H 0.7541 0.5772 0.9986 0.022 Uiso 1 1 calc R . .
C28 C 0.66765(13) 0.51045(9) 0.81239(17) 0.0195(3) Uani 1 1 d . . .
H28 H 0.6779 0.4569 0.8572 0.023 Uiso 1 1 calc R . .
C29 C 0.60798(13) 0.51912(9) 0.66288(17) 0.0198(3) Uani 1 1 d . . .
C30 C 0.63467(13) 0.66665(9) 0.67769(16) 0.0178(3) Uani 1 1 d . . .
H30 H 0.6236 0.7200 0.6323 0.021 Uiso 1 1 calc R . .
C31 C 0.58971(13) 0.59545(9) 0.59275(16) 0.0183(3) Uani 1 1 d . . .
H31 H 0.5478 0.5994 0.4898 0.022 Uiso 1 1 calc R . .
C32 C 0.47270(14) 0.93420(9) 0.94646(17) 0.0190(3) Uani 1 1 d . . .
H32A H 0.3905 0.9345 0.9393 0.023 Uiso 1 1 calc R . .
H32B H 0.4993 0.9930 0.9533 0.023 Uiso 1 1 calc R . .
C33 C 0.55127(13) 0.88779(9) 1.08669(16) 0.0167(3) Uani 1 1 d . . .
H33 H 0.5317 0.9085 1.1689 0.020 Uiso 1 1 calc R . .
C34 C 0.73774(13) 0.85734(8) 1.06370(15) 0.0155(3) Uani 1 1 d . . .
C35 C 0.91413(14) 0.94722(9) 1.18259(17) 0.0205(3) Uani 1 1 d . . .
H35A H 0.9099 0.9971 1.1218 0.025 Uiso 1 1 calc R . .
H35B H 0.9981 0.9316 1.2349 0.025 Uiso 1 1 calc R . .
C36 C 0.86110(14) 0.96735(10) 1.29217(17) 0.0214(3) Uani 1 1 d . . .
H36A H 0.8782 0.9215 1.3644 0.026 Uiso 1 1 calc R . .
H36B H 0.8964 1.0195 1.3453 0.026 Uiso 1 1 calc R . .
C37 C 0.72869(14) 0.97807(10) 1.21176(19) 0.0229(3) Uani 1 1 d . . .
H37A H 0.6928 0.9874 1.2832 0.027 Uiso 1 1 calc R . .
H37B H 0.7119 1.0276 1.1470 0.027 Uiso 1 1 calc R . .
C38 C 0.52758(13) 0.79323(8) 1.07035(16) 0.0164(3) Uani 1 1 d . . .
C39 C 0.59007(17) 0.76793(12) 1.32748(19) 0.0296(4) Uani 1 1 d . . .
H39A H 0.5072 0.7633 1.3134 0.044 Uiso 1 1 calc R . .
H39B H 0.6175 0.8253 1.3558 0.044 Uiso 1 1 calc R . .
H39C H 0.6380 0.7293 1.4046 0.044 Uiso 1 1 calc R . .
C40 C 0.36089(16) 0.70252(10) 1.0205(2) 0.0295(4) Uani 1 1 d . . .
H40A H 0.4041 0.6682 1.1068 0.044 Uiso 1 1 calc R . .
H40B H 0.3697 0.6784 0.9352 0.044 Uiso 1 1 calc R . .
H40C H 0.2771 0.7039 1.0033 0.044 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
F1 C1 1.3688(17) . ?
F2 C29 1.3637(17) . ?
O1 C9 1.2133(18) . ?
O1S H1SA 0.8433 . ?
O1S H1SB 0.8705 . ?
O2 C5 1.2726(18) . ?
O3 C18 1.4093(17) . ?
O3 C19 1.4331(17) . ?
O4 C18 1.4215(17) . ?
O4 C20 1.4357(19) . ?
O5 C21 1.2182(19) . ?
O6 C25 1.2771(18) . ?
O7 C38 1.4126(18) . ?
O7 C39 1.426(2) . ?
O8 C38 1.4090(18) . ?
O8 C40 1.4322(19) . ?
N1 C12 1.3477(19) . ?
N1 C13 1.4697(17) . ?
N1 C16 1.4699(18) . ?
N2 C12 1.3368(18) . ?
N2 C15 1.4605(18) . ?
N2 H2 0.8800 . ?
N3 C34 1.3535(19) . ?
N3 C33 1.4645(19) . ?
N3 C37 1.4710(19) . ?
N4 C34 1.3392(19) . ?
N4 C35 1.4602(19) . ?
N4 H4 0.8800 . ?
C1 C2 1.374(2) . ?
C1 C11 1.379(2) . ?
C2 C3 1.393(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9500 . ?
C4 C10 1.389(2) . ?
C4 C5 1.5117(19) . ?
C5 C6 1.407(2) . ?
C6 C12 1.4403(18) . ?
C6 C7 1.5147(19) . ?
C7 C18 1.534(2) . ?
C7 C8 1.556(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.513(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.513(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.510(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.515(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.5329(19) . ?
C16 C17 1.537(2) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.506(2) . ?
C21 C32 1.519(2) . ?
C22 C23 1.546(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.520(2) . ?
C23 C38 1.532(2) . ?
C23 H23 1.0000 . ?
C24 C25 1.401(2) . ?
C24 C34 1.4406(19) . ?
C25 C26 1.5118(19) . ?
C26 C27 1.393(2) . ?
C26 C30 1.396(2) . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(2) . ?
C28 H28 0.9500 . ?
C29 C31 1.380(2) . ?
C30 C31 1.395(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.538(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C38 1.5359(19) . ?
C33 H33 1.0000 . ?
C35 C36 1.518(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.518(2) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?

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
H1SA O1S H1SB 105.0 . . ?
C18 O3 C19 114.89(11) . . ?
C18 O4 C20 114.99(11) . . ?
C38 O7 C39 115.46(12) . . ?
C38 O8 C40 115.60(11) . . ?
C12 N1 C13 121.69(12) . . ?
C12 N1 C16 122.90(11) . . ?
C13 N1 C16 115.25(11) . . ?
C12 N2 C15 124.20(12) . . ?
C12 N2 H2 117.9 . . ?
C15 N2 H2 117.9 . . ?
C34 N3 C33 121.24(12) . . ?
C34 N3 C37 121.10(13) . . ?
C33 N3 C37 116.99(12) . . ?
C34 N4 C35 124.83(13) . . ?
C34 N4 H4 117.6 . . ?
C35 N4 H4 117.6 . . ?
F1 C1 C2 118.96(14) . . ?
F1 C1 C11 118.27(14) . . ?
C2 C1 C11 122.77(14) . . ?
C1 C2 C3 117.95(14) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 C4 120.93(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C10 C4 C3 119.38(13) . . ?
C10 C4 C5 120.09(12) . . ?
C3 C4 C5 120.09(12) . . ?
O2 C5 C6 125.43(13) . . ?
O2 C5 C4 114.70(12) . . ?
C6 C5 C4 119.86(12) . . ?
C5 C6 C12 120.22(12) . . ?
C5 C6 C7 122.32(12) . . ?
C12 C6 C7 117.29(12) . . ?
C6 C7 C18 107.60(11) . . ?
C6 C7 C8 114.84(12) . . ?
C18 C7 C8 109.02(12) . . ?
C6 C7 H7 108.4 . . ?
C18 C7 H7 108.4 . . ?
C8 C7 H7 108.4 . . ?
C9 C8 C7 113.08(12) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
O1 C9 C17 122.62(13) . . ?
O1 C9 C8 121.86(13) . . ?
C17 C9 C8 115.52(12) . . ?
C4 C10 C11 120.21(14) . . ?
C4 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C1 C11 C10 118.75(14) . . ?
C1 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N2 C12 N1 119.45(12) . . ?
N2 C12 C6 119.40(12) . . ?
N1 C12 C6 121.14(13) . . ?
N1 C13 C14 110.53(12) . . ?
N1 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 108.74(12) . . ?
C13 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
N2 C15 C14 109.62(12) . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N1 C16 C18 110.19(11) . . ?
N1 C16 C17 109.56(11) . . ?
C18 C16 C17 110.53(11) . . ?
N1 C16 H16 108.8 . . ?
C18 C16 H16 108.8 . . ?
C17 C16 H16 108.8 . . ?
C9 C17 C16 110.07(12) . . ?
C9 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C9 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
O3 C18 O4 111.35(11) . . ?
O3 C18 C16 105.36(11) . . ?
O4 C18 C16 111.83(12) . . ?
O3 C18 C7 114.24(12) . . ?
O4 C18 C7 106.36(11) . . ?
C16 C18 C7 107.76(11) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 C22 122.60(15) . . ?
O5 C21 C32 121.17(14) . . ?
C22 C21 C32 116.20(13) . . ?
C21 C22 C23 110.11(12) . . ?
C21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C38 109.32(12) . . ?
C24 C23 C22 112.50(12) . . ?
C38 C23 C22 108.89(11) . . ?
C24 C23 H23 108.7 . . ?
C38 C23 H23 108.7 . . ?
C22 C23 H23 108.7 . . ?
C25 C24 C34 119.51(13) . . ?
C25 C24 C23 120.81(12) . . ?
C34 C24 C23 119.66(13) . . ?
O6 C25 C24 125.85(13) . . ?
O6 C25 C26 114.97(12) . . ?
C24 C25 C26 119.18(13) . . ?
C27 C26 C30 119.79(13) . . ?
C27 C26 C25 120.16(13) . . ?
C30 C26 C25 119.92(13) . . ?
C28 C27 C26 120.26(14) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 118.48(13) . . ?
C29 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
F2 C29 C31 118.67(13) . . ?
F2 C29 C28 118.28(13) . . ?
C31 C29 C28 123.02(14) . . ?
C31 C30 C26 120.51(13) . . ?
C31 C30 H30 119.7 . . ?
C26 C30 H30 119.7 . . ?
C29 C31 C30 117.94(13) . . ?
C29 C31 H31 121.0 . . ?
C30 C31 H31 121.0 . . ?
C21 C32 C33 113.29(12) . . ?
C21 C32 H32A 108.9 . . ?
C33 C32 H32A 108.9 . . ?
C21 C32 H32B 108.9 . . ?
C33 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
N3 C33 C38 109.19(11) . . ?
N3 C33 C32 111.82(12) . . ?
C38 C33 C32 110.73(12) . . ?
N3 C33 H33 108.3 . . ?
C38 C33 H33 108.3 . . ?
C32 C33 H33 108.3 . . ?
N4 C34 N3 119.68(13) . . ?
N4 C34 C24 119.76(13) . . ?
N3 C34 C24 120.55(13) . . ?
N4 C35 C36 109.45(13) . . ?
N4 C35 H35A 109.8 . . ?
C36 C35 H35A 109.8 . . ?
N4 C35 H35B 109.8 . . ?
C36 C35 H35B 109.8 . . ?
H35A C35 H35B 108.2 . . ?
C37 C36 C35 109.20(13) . . ?
C37 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
C37 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.3 . . ?
N3 C37 C36 110.13(12) . . ?
N3 C37 H37A 109.6 . . ?
C36 C37 H37A 109.6 . . ?
N3 C37 H37B 109.6 . . ?
C36 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?
O8 C38 O7 112.25(12) . . ?
O8 C38 C23 114.07(12) . . ?
O7 C38 C23 106.05(11) . . ?
O8 C38 C33 104.15(11) . . ?
O7 C38 C33 112.87(12) . . ?
C23 C38 C33 107.52(12) . . ?
O7 C39 H39A 109.5 . . ?
O7 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O7 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O8 C40 H40A 109.5 . . ?
O8 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O8 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 179.91(14) . . . . ?
C11 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C10 -0.4(2) . . . . ?
C2 C3 C4 C5 -172.79(14) . . . . ?
C10 C4 C5 O2 -61.73(18) . . . . ?
C3 C4 C5 O2 110.57(16) . . . . ?
C10 C4 C5 C6 119.21(16) . . . . ?
C3 C4 C5 C6 -68.48(18) . . . . ?
O2 C5 C6 C12 -0.7(2) . . . . ?
C4 C5 C6 C12 178.26(12) . . . . ?
O2 C5 C6 C7 174.55(14) . . . . ?
C4 C5 C6 C7 -6.5(2) . . . . ?
C5 C6 C7 C18 -138.32(13) . . . . ?
C12 C6 C7 C18 37.04(16) . . . . ?
C5 C6 C7 C8 100.11(15) . . . . ?
C12 C6 C7 C8 -84.53(15) . . . . ?
C6 C7 C8 C9 68.26(16) . . . . ?
C18 C7 C8 C9 -52.54(15) . . . . ?
C7 C8 C9 O1 -134.25(14) . . . . ?
C7 C8 C9 C17 46.43(17) . . . . ?
C3 C4 C10 C11 1.1(2) . . . . ?
C5 C4 C10 C11 173.46(15) . . . . ?
F1 C1 C11 C10 -179.26(15) . . . . ?
C2 C1 C11 C10 -0.3(3) . . . . ?
C4 C10 C11 C1 -0.7(2) . . . . ?
C15 N2 C12 N1 5.5(2) . . . . ?
C15 N2 C12 C6 -174.50(13) . . . . ?
C13 N1 C12 N2 -3.4(2) . . . . ?
C16 N1 C12 N2 171.87(13) . . . . ?
C13 N1 C12 C6 176.54(13) . . . . ?
C16 N1 C12 C6 -8.2(2) . . . . ?
C5 C6 C12 N2 -5.7(2) . . . . ?
C7 C6 C12 N2 178.82(13) . . . . ?
C5 C6 C12 N1 174.32(13) . . . . ?
C7 C6 C12 N1 -1.14(19) . . . . ?
C12 N1 C13 C14 -27.59(19) . . . . ?
C16 N1 C13 C14 156.78(13) . . . . ?
N1 C13 C14 C15 54.44(17) . . . . ?
C12 N2 C15 C14 23.7(2) . . . . ?
C13 C14 C15 N2 -52.11(17) . . . . ?
C12 N1 C16 C18 -20.23(18) . . . . ?
C13 N1 C16 C18 155.34(12) . . . . ?
C12 N1 C16 C17 101.57(15) . . . . ?
C13 N1 C16 C17 -82.86(15) . . . . ?
O1 C9 C17 C16 132.96(14) . . . . ?
C8 C9 C17 C16 -47.73(16) . . . . ?
N1 C16 C17 C9 -64.37(14) . . . . ?
C18 C16 C17 C9 57.23(15) . . . . ?
C19 O3 C18 O4 -64.95(15) . . . . ?
C19 O3 C18 C16 173.63(11) . . . . ?
C19 O3 C18 C7 55.55(15) . . . . ?
C20 O4 C18 O3 -52.14(16) . . . . ?
C20 O4 C18 C16 65.44(15) . . . . ?
C20 O4 C18 C7 -177.18(12) . . . . ?
N1 C16 C18 O3 -66.64(14) . . . . ?
C17 C16 C18 O3 172.12(11) . . . . ?
N1 C16 C18 O4 172.24(11) . . . . ?
C17 C16 C18 O4 51.01(15) . . . . ?
N1 C16 C18 C7 55.71(14) . . . . ?
C17 C16 C18 C7 -65.52(14) . . . . ?
C6 C7 C18 O3 53.14(15) . . . . ?
C8 C7 C18 O3 178.28(11) . . . . ?
C6 C7 C18 O4 176.39(10) . . . . ?
C8 C7 C18 O4 -58.48(13) . . . . ?
C6 C7 C18 C16 -63.56(14) . . . . ?
C8 C7 C18 C16 61.58(14) . . . . ?
O5 C21 C22 C23 134.02(15) . . . . ?
C32 C21 C22 C23 -47.55(17) . . . . ?
C21 C22 C23 C24 -62.02(16) . . . . ?
C21 C22 C23 C38 59.32(15) . . . . ?
C38 C23 C24 C25 150.92(13) . . . . ?
C22 C23 C24 C25 -87.99(16) . . . . ?
C38 C23 C24 C34 -27.47(17) . . . . ?
C22 C23 C24 C34 93.62(16) . . . . ?
C34 C24 C25 O6 -2.0(2) . . . . ?
C23 C24 C25 O6 179.61(14) . . . . ?
C34 C24 C25 C26 177.73(13) . . . . ?
C23 C24 C25 C26 -0.7(2) . . . . ?
O6 C25 C26 C27 84.97(17) . . . . ?
C24 C25 C26 C27 -94.78(17) . . . . ?
O6 C25 C26 C30 -90.87(17) . . . . ?
C24 C25 C26 C30 89.37(17) . . . . ?
C30 C26 C27 C28 -0.2(2) . . . . ?
C25 C26 C27 C28 -176.09(13) . . . . ?
C26 C27 C28 C29 0.5(2) . . . . ?
C27 C28 C29 F2 -178.72(14) . . . . ?
C27 C28 C29 C31 -0.6(2) . . . . ?
C27 C26 C30 C31 0.1(2) . . . . ?
C25 C26 C30 C31 175.93(14) . . . . ?
F2 C29 C31 C30 178.54(13) . . . . ?
C28 C29 C31 C30 0.5(2) . . . . ?
C26 C30 C31 C29 -0.2(2) . . . . ?
O5 C21 C32 C33 -138.73(15) . . . . ?
C22 C21 C32 C33 42.82(18) . . . . ?
C34 N3 C33 C38 38.44(18) . . . . ?
C37 N3 C33 C38 -150.91(13) . . . . ?
C34 N3 C33 C32 -84.45(16) . . . . ?
C37 N3 C33 C32 86.20(15) . . . . ?
C21 C32 C33 N3 73.23(15) . . . . ?
C21 C32 C33 C38 -48.78(17) . . . . ?
C35 N4 C34 N3 1.2(2) . . . . ?
C35 N4 C34 C24 -177.72(13) . . . . ?
C33 N3 C34 N4 173.58(13) . . . . ?
C37 N3 C34 N4 3.3(2) . . . . ?
C33 N3 C34 C24 -7.5(2) . . . . ?
C37 N3 C34 C24 -177.74(13) . . . . ?
C25 C24 C34 N4 2.2(2) . . . . ?
C23 C24 C34 N4 -179.43(13) . . . . ?
C25 C24 C34 N3 -176.77(13) . . . . ?
C23 C24 C34 N3 1.6(2) . . . . ?
C34 N4 C35 C36 23.8(2) . . . . ?
N4 C35 C36 C37 -50.80(17) . . . . ?
C34 N3 C37 C36 -32.5(2) . . . . ?
C33 N3 C37 C36 156.88(13) . . . . ?
C35 C36 C37 N3 55.52(17) . . . . ?
C40 O8 C38 O7 -59.37(17) . . . . ?
C40 O8 C38 C23 61.29(17) . . . . ?
C40 O8 C38 C33 178.20(14) . . . . ?
C39 O7 C38 O8 -56.64(17) . . . . ?
C39 O7 C38 C23 178.18(13) . . . . ?
C39 O7 C38 C33 60.70(17) . . . . ?
C24 C23 C38 O8 171.50(11) . . . . ?
C22 C23 C38 O8 48.24(15) . . . . ?
C24 C23 C38 O7 -64.44(14) . . . . ?
C22 C23 C38 O7 172.30(11) . . . . ?
C24 C23 C38 C33 56.56(14) . . . . ?
C22 C23 C38 C33 -66.70(14) . . . . ?
N3 C33 C38 O8 176.15(11) . . . . ?
C32 C33 C38 O8 -60.31(15) . . . . ?
N3 C33 C38 O7 54.13(16) . . . . ?
C32 C33 C38 O7 177.67(12) . . . . ?
N3 C33 C38 C23 -62.48(15) . . . . ?
C32 C33 C38 C23 61.06(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1S H1SA O1 0.84 2.08 2.8965(16) 161.7 2_665
O1S H1SB O6 0.87 1.92 2.7780(16) 168.0 .
N2 H2 O2 0.88 1.87 2.5875(16) 137.0 .
N4 H4 O6 0.88 1.85 2.5703(17) 137.3 .

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        30.07
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_mo_yd_lj2_0m
_database_code_depnum_ccdc_archive 'CCDC 1547076'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H25 Cl N2 O4), 3(H2 O)'
_chemical_formula_sum            'C42 H56 Cl2 N4 O11'
_chemical_formula_weight         863.81

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           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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'
'-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                   23.064(2)
_cell_length_b                   9.1067(9)
_cell_length_c                   19.757(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.558(2)
_cell_angle_gamma                90.00
_cell_volume                     4050.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.49

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1832
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8475
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18766
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4882
_reflns_number_gt                4403
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0902P)²+7.7654P] 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         4882
_refine_ls_number_parameters     280
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_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 0.14206(2) 0.83196(5) 0.42372(3) 0.02564(15) Uani 1 1 d . . .
O1S O 0.09458(8) 0.2216(3) 0.31915(15) 0.0611(7) Uani 1 1 d D . .
H1SB H 0.0879(18) 0.260(5) 0.3547(14) 0.092 Uiso 1 1 d D . .
H1SA H 0.1294(8) 0.195(5) 0.332(2) 0.092 Uiso 1 1 d D . .
O4 O 0.43691(7) 0.14324(18) 0.55584(8) 0.0299(3) Uani 1 1 d . . .
O2S O 0.0000 0.3487(8) 0.2500 0.142(2) Uani 1 2 d S . .
H2SA H 0.0301 0.3085 0.2720 0.213 Uiso 1 1 d R . .
O2 O 0.38382(6) 0.33731(14) 0.29251(7) 0.0189(3) Uani 1 1 d . . .
O3 O 0.44502(6) 0.46501(14) 0.38411(7) 0.0199(3) Uani 1 1 d . . .
O1 O 0.21489(6) 0.15526(16) 0.35978(9) 0.0268(3) Uani 1 1 d . . .
N1 N 0.39721(7) 0.07061(16) 0.37423(8) 0.0170(3) Uani 1 1 d . . .
N2 N 0.30103(7) -0.02367(17) 0.35784(8) 0.0186(3) Uani 1 1 d . . .
C3 C 0.17599(8) 0.6658(2) 0.41067(10) 0.0181(4) Uani 1 1 d . . .
C2 C 0.20915(8) 0.5921(2) 0.46777(9) 0.0191(4) Uani 1 1 d . . .
H2 H 0.2131 0.6310 0.5132 0.023 Uiso 1 1 calc R . .
C1 C 0.23652(8) 0.4603(2) 0.45723(9) 0.0185(4) Uani 1 1 d . . .
H1 H 0.2592 0.4087 0.4959 0.022 Uiso 1 1 calc R . .
C6 C 0.23109(7) 0.4033(2) 0.39078(9) 0.0167(3) Uani 1 1 d . . .
C7 C 0.25499(8) 0.2537(2) 0.37818(9) 0.0173(3) Uani 1 1 d . . .
C8 C 0.31589(7) 0.23100(19) 0.38645(9) 0.0153(3) Uani 1 1 d . . .
C9 C 0.36094(7) 0.35105(19) 0.40835(9) 0.0152(3) Uani 1 1 d . . .
H9 H 0.3402 0.4477 0.3987 0.018 Uiso 1 1 calc R . .
C14 C 0.39165(8) 0.3461(2) 0.48637(9) 0.0182(4) Uani 1 1 d . . .
H14A H 0.4131 0.4397 0.4992 0.022 Uiso 1 1 calc R . .
H14B H 0.3608 0.3377 0.5140 0.022 Uiso 1 1 calc R . .
C13 C 0.43485(8) 0.2207(2) 0.50494(10) 0.0196(4) Uani 1 1 d . . .
C5 C 0.19739(8) 0.4805(2) 0.33458(10) 0.0206(4) Uani 1 1 d . . .
H5 H 0.1933 0.4420 0.2891 0.025 Uiso 1 1 calc R . .
C4 C 0.16982(8) 0.6125(2) 0.34391(10) 0.0208(4) Uani 1 1 d . . .
H4 H 0.1473 0.6647 0.3054 0.025 Uiso 1 1 calc R . .
C15 C 0.33862(8) 0.09006(19) 0.37253(9) 0.0158(3) Uani 1 1 d . . .
C11 C 0.44169(8) 0.19321(19) 0.38079(9) 0.0162(3) Uani 1 1 d . . .
C10 C 0.40792(8) 0.34071(19) 0.36400(9) 0.0158(3) Uani 1 1 d . . .
C20 C 0.34447(9) 0.4551(2) 0.26528(10) 0.0229(4) Uani 1 1 d . . .
H20A H 0.3073 0.4446 0.2812 0.034 Uiso 1 1 calc R . .
H20B H 0.3360 0.4522 0.2145 0.034 Uiso 1 1 calc R . .
H20C H 0.3632 0.5490 0.2815 0.034 Uiso 1 1 calc R . .
C12 C 0.47680(8) 0.1979(2) 0.45663(9) 0.0187(4) Uani 1 1 d . . .
H12A H 0.4987 0.1046 0.4683 0.022 Uiso 1 1 calc R . .
H12B H 0.5061 0.2790 0.4625 0.022 Uiso 1 1 calc R . .
C21 C 0.48310(9) 0.5159(2) 0.34032(12) 0.0278(4) Uani 1 1 d . . .
H21A H 0.5235 0.4792 0.3581 0.042 Uiso 1 1 calc R . .
H21B H 0.4835 0.6235 0.3400 0.042 Uiso 1 1 calc R . .
H21C H 0.4683 0.4796 0.2930 0.042 Uiso 1 1 calc R . .
C19 C 0.48347(8) 0.1630(2) 0.33184(10) 0.0206(4) Uani 1 1 d . . .
H19A H 0.5055 0.0719 0.3458 0.031 Uiso 1 1 calc R . .
H19B H 0.5115 0.2447 0.3342 0.031 Uiso 1 1 calc R . .
H19C H 0.4602 0.1531 0.2843 0.031 Uiso 1 1 calc R . .
C18 C 0.41992(8) -0.0795(2) 0.36761(11) 0.0210(4) Uani 1 1 d . . .
H18A H 0.4616 -0.0864 0.3937 0.025 Uiso 1 1 calc R . .
H18B H 0.4190 -0.1007 0.3182 0.025 Uiso 1 1 calc R . .
C17 C 0.38231(8) -0.1920(2) 0.39547(10) 0.0211(4) Uani 1 1 d . . .
H17A H 0.3971 -0.2923 0.3899 0.025 Uiso 1 1 calc R . .
H17B H 0.3845 -0.1746 0.4454 0.025 Uiso 1 1 calc R . .
C16 C 0.31865(8) -0.17692(19) 0.35510(10) 0.0193(4) Uani 1 1 d . . .
H16A H 0.3156 -0.2074 0.3064 0.023 Uiso 1 1 calc R . .
H16B H 0.2922 -0.2405 0.3757 0.023 Uiso 1 1 calc R . .
H1A H 0.2670(13) -0.004(3) 0.3574(14) 0.028(7) Uiso 1 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 C3 1.7483(18) . ?
O1S H1SB 0.827(10) . ?
O1S H1SA 0.824(10) . ?
O4 C13 1.221(2) . ?
O2S H2SA 0.8205 . ?
O2 C10 1.401(2) . ?
O2 C20 1.432(2) . ?
O3 C10 1.423(2) . ?
O3 C21 1.437(2) . ?
O1 C7 1.283(2) . ?
N1 C15 1.356(2) . ?
N1 C18 1.480(2) . ?
N1 C11 1.503(2) . ?
N2 C15 1.341(2) . ?
N2 C16 1.458(2) . ?
N2 H1A 0.80(3) . ?
C3 C4 1.384(3) . ?
C3 C2 1.390(3) . ?
C2 C1 1.393(3) . ?
C2 H2 0.9500 . ?
C1 C6 1.392(2) . ?
C1 H1 0.9500 . ?
C6 C5 1.399(3) . ?
C6 C7 1.510(2) . ?
C7 C8 1.394(2) . ?
C8 C15 1.435(2) . ?
C8 C9 1.506(2) . ?
C9 C10 1.537(2) . ?
C9 C14 1.551(2) . ?
C9 H9 1.0000 . ?
C14 C13 1.508(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C13 C12 1.514(2) . ?
C5 C4 1.390(3) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C11 C19 1.531(2) . ?
C11 C12 1.541(3) . ?
C11 C10 1.552(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 C17 1.521(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C17 C16 1.517(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
H1SB O1S H1SA 102(2) . . ?
C10 O2 C20 116.25(14) . . ?
C10 O3 C21 119.84(15) . . ?
C15 N1 C18 119.24(15) . . ?
C15 N1 C11 124.27(14) . . ?
C18 N1 C11 116.48(14) . . ?
C15 N2 C16 125.10(16) . . ?
C15 N2 H1A 114(2) . . ?
C16 N2 H1A 120(2) . . ?
C4 C3 C2 121.91(17) . . ?
C4 C3 Cl1 119.20(14) . . ?
C2 C3 Cl1 118.88(14) . . ?
C3 C2 C1 118.81(17) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C6 C1 C2 120.78(17) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C6 C5 118.78(16) . . ?
C1 C6 C7 122.06(16) . . ?
C5 C6 C7 118.85(16) . . ?
O1 C7 C8 125.17(17) . . ?
O1 C7 C6 114.23(15) . . ?
C8 C7 C6 120.61(16) . . ?
C7 C8 C15 120.71(16) . . ?
C7 C8 C9 122.75(16) . . ?
C15 C8 C9 116.52(15) . . ?
C8 C9 C10 108.64(14) . . ?
C8 C9 C14 113.71(14) . . ?
C10 C9 C14 109.80(14) . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C14 C9 H9 108.2 . . ?
C13 C14 C9 113.50(14) . . ?
C13 C14 H14A 108.9 . . ?
C9 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C9 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
O4 C13 C14 122.92(17) . . ?
O4 C13 C12 121.63(17) . . ?
C14 C13 C12 115.44(16) . . ?
C4 C5 C6 121.38(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C3 C4 C5 118.33(17) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N2 C15 N1 119.88(16) . . ?
N2 C15 C8 119.09(16) . . ?
N1 C15 C8 121.03(16) . . ?
N1 C11 C19 108.89(14) . . ?
N1 C11 C12 108.00(14) . . ?
C19 C11 C12 110.45(14) . . ?
N1 C11 C10 108.85(13) . . ?
C19 C11 C10 112.08(14) . . ?
C12 C11 C10 108.48(14) . . ?
O2 C10 O3 112.45(14) . . ?
O2 C10 C9 113.68(14) . . ?
O3 C10 C9 104.35(14) . . ?
O2 C10 C11 105.49(14) . . ?
O3 C10 C11 112.67(14) . . ?
C9 C10 C11 108.32(14) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C12 C11 110.13(14) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C18 C17 110.46(14) . . ?
N1 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
N1 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C16 C17 C18 108.16(15) . . ?
C16 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
N2 C16 C17 108.25(15) . . ?
N2 C16 H16A 110.0 . . ?
C17 C16 H16A 110.0 . . ?
N2 C16 H16B 110.0 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C1 -0.5(3) . . . . ?
Cl1 C3 C2 C1 -179.53(14) . . . . ?
C3 C2 C1 C6 0.3(3) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 -173.80(16) . . . . ?
C1 C6 C7 O1 106.7(2) . . . . ?
C5 C6 C7 O1 -66.9(2) . . . . ?
C1 C6 C7 C8 -73.5(2) . . . . ?
C5 C6 C7 C8 113.0(2) . . . . ?
O1 C7 C8 C15 1.7(3) . . . . ?
C6 C7 C8 C15 -178.14(15) . . . . ?
O1 C7 C8 C9 -179.87(17) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 -137.38(17) . . . . ?
C15 C8 C9 C10 41.1(2) . . . . ?
C7 C8 C9 C14 100.04(19) . . . . ?
C15 C8 C9 C14 -81.45(19) . . . . ?
C8 C9 C14 C13 71.81(19) . . . . ?
C10 C9 C14 C13 -50.1(2) . . . . ?
C9 C14 C13 O4 -135.2(2) . . . . ?
C9 C14 C13 C12 45.8(2) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
C7 C6 C5 C4 174.17(17) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
Cl1 C3 C4 C5 179.68(14) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C16 N2 C15 N1 11.6(3) . . . . ?
C16 N2 C15 C8 -168.20(16) . . . . ?
C18 N1 C15 N2 -6.8(2) . . . . ?
C11 N1 C15 N2 171.62(16) . . . . ?
C18 N1 C15 C8 172.99(16) . . . . ?
C11 N1 C15 C8 -8.6(3) . . . . ?
C7 C8 C15 N2 -6.4(3) . . . . ?
C9 C8 C15 N2 175.11(15) . . . . ?
C7 C8 C15 N1 173.84(16) . . . . ?
C9 C8 C15 N1 -4.7(2) . . . . ?
C15 N1 C11 C19 -138.55(17) . . . . ?
C18 N1 C11 C19 39.9(2) . . . . ?
C15 N1 C11 C12 101.49(18) . . . . ?
C18 N1 C11 C12 -80.03(18) . . . . ?
C15 N1 C11 C10 -16.1(2) . . . . ?
C18 N1 C11 C10 162.38(15) . . . . ?
C20 O2 C10 O3 -63.77(19) . . . . ?
C20 O2 C10 C9 54.5(2) . . . . ?
C20 O2 C10 C11 173.05(14) . . . . ?
C21 O3 C10 O2 -38.3(2) . . . . ?
C21 O3 C10 C9 -161.94(15) . . . . ?
C21 O3 C10 C11 80.78(19) . . . . ?
C8 C9 C10 O2 52.20(18) . . . . ?
C14 C9 C10 O2 177.12(14) . . . . ?
C8 C9 C10 O3 175.06(13) . . . . ?
C14 C9 C10 O3 -60.02(17) . . . . ?
C8 C9 C10 C11 -64.69(17) . . . . ?
C14 C9 C10 C11 60.23(18) . . . . ?
N1 C11 C10 O2 -70.57(16) . . . . ?
C19 C11 C10 O2 49.94(19) . . . . ?
C12 C11 C10 O2 172.15(13) . . . . ?
N1 C11 C10 O3 166.40(14) . . . . ?
C19 C11 C10 O3 -73.10(19) . . . . ?
C12 C11 C10 O3 49.11(18) . . . . ?
N1 C11 C10 C9 51.49(18) . . . . ?
C19 C11 C10 C9 171.99(15) . . . . ?
C12 C11 C10 C9 -65.80(17) . . . . ?
O4 C13 C12 C11 130.81(19) . . . . ?
C14 C13 C12 C11 -50.2(2) . . . . ?
N1 C11 C12 C13 -58.39(18) . . . . ?
C19 C11 C12 C13 -177.36(15) . . . . ?
C10 C11 C12 C13 59.43(19) . . . . ?
C15 N1 C18 C17 -28.6(2) . . . . ?
C11 N1 C18 C17 152.81(16) . . . . ?
N1 C18 C17 C16 58.4(2) . . . . ?
C15 N2 C16 C17 20.1(2) . . . . ?
C18 C17 C16 N2 -52.97(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1A O1 0.80(3) 1.89(3) 2.576(2) 143(3) .
O2S H2SA O1S 0.82 1.76 2.582(4) 179.8 .
O1S H1SA O1 0.824(10) 1.962(12) 2.782(2) 173(5) .
O1S H1SB O4 0.827(10) 2.162(11) 2.987(3) 175(4) 7_556

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.707
_refine_diff_density_min         -1.290
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1547077'
_audit_update_record             
;
2017-05-01 deposited with the CCDC.
2017-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H52 N4 O8'
_chemical_formula_weight         740.88

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   14.6978(15)
_cell_length_b                   12.2595(12)
_cell_length_c                   21.830(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.6090(10)
_cell_angle_gamma                90.00
_cell_volume                     3727.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10383
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.15
_reflns_number_total             3342
_reflns_number_gt                2476
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker apex II'
_computing_cell_refinement       'Bruker apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.2933P] 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     SHELXL
_refine_ls_extinction_coef       0.0057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3342
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_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
N1 N 0.19584(11) 1.04251(12) 0.24252(7) 0.0366(4) Uani 1 1 d . . .
N2 N 0.13452(12) 0.88520(14) 0.27364(7) 0.0441(4) Uani 1 1 d . . .
H2A H 0.1021 0.8260 0.2624 0.053 Uiso 1 1 calc R . .
O1 O 0.05656(11) 0.73952(11) 0.18741(6) 0.0520(4) Uani 1 1 d . . .
O2 O 0.29487(8) 0.97965(11) 0.15291(6) 0.0407(4) Uani 1 1 d . . .
O3 O 0.22851(9) 1.13198(10) 0.09103(6) 0.0375(3) Uani 1 1 d . . .
O4 O -0.04468(10) 1.15422(15) 0.14454(8) 0.0669(5) Uani 1 1 d . . .
C1 C 0.13976(15) 0.73976(16) 0.05716(9) 0.0447(5) Uani 1 1 d . . .
H1 H 0.1996 0.7696 0.0789 0.054 Uiso 1 1 calc R . .
C2 C 0.12613(18) 0.68382(18) -0.00041(10) 0.0576(6) Uani 1 1 d . . .
H2 H 0.1766 0.6761 -0.0171 0.069 Uiso 1 1 calc R . .
C3 C 0.0376(2) 0.63979(18) -0.03271(11) 0.0641(7) Uani 1 1 d . . .
H3 H 0.0281 0.6025 -0.0713 0.077 Uiso 1 1 calc R . .
C4 C -0.03614(18) 0.6509(2) -0.00814(11) 0.0628(7) Uani 1 1 d . . .
H4 H -0.0959 0.6213 -0.0302 0.075 Uiso 1 1 calc R . .
C5 C -0.02279(15) 0.70547(17) 0.04898(9) 0.0480(5) Uani 1 1 d . . .
H5 H -0.0736 0.7116 0.0655 0.058 Uiso 1 1 calc R . .
C6 C 0.06521(13) 0.75155(14) 0.08247(8) 0.0360(4) Uani 1 1 d . . .
C7 C 0.07892(13) 0.80202(15) 0.14788(8) 0.0358(4) Uani 1 1 d . . .
C8 C 0.11670(12) 0.90774(15) 0.16170(8) 0.0330(4) Uani 1 1 d . . .
C9 C 0.12634(12) 0.98329(14) 0.10898(8) 0.0327(4) Uani 1 1 d . . .
H9 H 0.1322 0.9391 0.0730 0.039 Uiso 1 1 calc R . .
C10 C 0.21712(12) 1.05273(14) 0.13573(8) 0.0329(4) Uani 1 1 d . . .
C11 C 0.20644(12) 1.11793(14) 0.19285(8) 0.0341(4) Uani 1 1 d . . .
H11 H 0.2655 1.1600 0.2117 0.041 Uiso 1 1 calc R . .
C12 C 0.12174(13) 1.19943(15) 0.16995(9) 0.0385(5) Uani 1 1 d . . .
H12 H 0.1360 1.2467 0.1380 0.046 Uiso 1 1 calc R . .
C13 C 0.03015(14) 1.13886(16) 0.13413(9) 0.0408(5) Uani 1 1 d . . .
C14 C 0.03816(13) 1.05940(16) 0.08363(9) 0.0395(5) Uani 1 1 d . . .
H14A H 0.0430 1.0996 0.0465 0.047 Uiso 1 1 calc R . .
H14B H -0.0197 1.0155 0.0695 0.047 Uiso 1 1 calc R . .
C15 C 0.14838(12) 0.94657(15) 0.22662(8) 0.0344(4) Uani 1 1 d . . .
C16 C 0.16983(17) 0.91087(18) 0.34196(9) 0.0536(6) Uani 1 1 d . . .
H16A H 0.1854 0.8441 0.3670 0.064 Uiso 1 1 calc R . .
H16B H 0.1207 0.9491 0.3544 0.064 Uiso 1 1 calc R . .
C17 C 0.25781(17) 0.98107(18) 0.35552(9) 0.0556(6) Uani 1 1 d . . .
H17A H 0.3103 0.9386 0.3499 0.067 Uiso 1 1 calc R . .
H17B H 0.2768 1.0065 0.3999 0.067 Uiso 1 1 calc R . .
C18 C 0.23773(16) 1.07730(17) 0.31038(9) 0.0478(5) Uani 1 1 d . . .
H18A H 0.1937 1.1265 0.3214 0.057 Uiso 1 1 calc R . .
H18B H 0.2970 1.1165 0.3155 0.057 Uiso 1 1 calc R . .
C19 C 0.11085(16) 1.27471(18) 0.22267(10) 0.0521(6) Uani 1 1 d . . .
H19A H 0.0660 1.3317 0.2034 0.078 Uiso 1 1 calc R . .
H19B H 0.1720 1.3062 0.2457 0.078 Uiso 1 1 calc R . .
H19C H 0.0877 1.2337 0.2521 0.078 Uiso 1 1 calc R . .
C20 C 0.38747(14) 1.02583(19) 0.18442(11) 0.0539(6) Uani 1 1 d . . .
H20A H 0.3976 1.0869 0.1599 0.081 Uiso 1 1 calc R . .
H20B H 0.4361 0.9719 0.1875 0.081 Uiso 1 1 calc R . .
H20C H 0.3909 1.0497 0.2270 0.081 Uiso 1 1 calc R . .
C21 C 0.23537(16) 1.08885(18) 0.03201(9) 0.0495(5) Uani 1 1 d . . .
H21A H 0.2847 1.0343 0.0413 0.074 Uiso 1 1 calc R . .
H21B H 0.2509 1.1465 0.0073 0.074 Uiso 1 1 calc R . .
H21C H 0.1751 1.0567 0.0077 0.074 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
N1 C15 1.355(2) . ?
N1 C11 1.471(2) . ?
N1 C18 1.474(2) . ?
N2 C15 1.340(2) . ?
N2 C16 1.449(2) . ?
N2 H2A 0.8600 . ?
O1 C7 1.273(2) . ?
O2 C10 1.406(2) . ?
O2 C20 1.431(2) . ?
O3 C10 1.424(2) . ?
O3 C21 1.426(2) . ?
O4 C13 1.207(2) . ?
C1 C6 1.383(3) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(2) . ?
C7 C8 1.404(3) . ?
C8 C15 1.425(2) . ?
C8 C9 1.519(2) . ?
C9 C10 1.533(2) . ?
C9 C14 1.549(2) . ?
C9 H9 0.9800 . ?
C10 C11 1.531(2) . ?
C11 C12 1.549(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.518(3) . ?
C12 C19 1.523(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.504(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C16 C17 1.502(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.505(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C15 N1 C11 121.60(14) . . ?
C15 N1 C18 121.62(15) . . ?
C11 N1 C18 116.78(15) . . ?
C15 N2 C16 125.08(17) . . ?
C15 N2 H2A 117.5 . . ?
C16 N2 H2A 117.5 . . ?
C10 O2 C20 116.33(15) . . ?
C10 O3 C21 115.08(14) . . ?
C6 C1 C2 120.61(19) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.12(18) . . ?
C1 C6 C7 122.49(17) . . ?
C5 C6 C7 119.09(17) . . ?
O1 C7 C8 125.42(16) . . ?
O1 C7 C6 114.15(15) . . ?
C8 C7 C6 120.38(15) . . ?
C7 C8 C15 120.21(16) . . ?
C7 C8 C9 121.75(15) . . ?
C15 C8 C9 118.04(15) . . ?
C8 C9 C10 109.29(13) . . ?
C8 C9 C14 111.62(14) . . ?
C10 C9 C14 109.21(14) . . ?
C8 C9 H9 108.9 . . ?
C10 C9 H9 108.9 . . ?
C14 C9 H9 108.9 . . ?
O2 C10 O3 110.76(13) . . ?
O2 C10 C11 113.67(14) . . ?
O3 C10 C11 105.48(14) . . ?
O2 C10 C9 106.41(14) . . ?
O3 C10 C9 113.34(13) . . ?
C11 C10 C9 107.29(14) . . ?
N1 C11 C10 109.56(14) . . ?
N1 C11 C12 112.34(14) . . ?
C10 C11 C12 110.77(14) . . ?
N1 C11 H11 108.0 . . ?
C10 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C13 C12 C19 113.33(16) . . ?
C13 C12 C11 109.87(15) . . ?
C19 C12 C11 114.48(15) . . ?
C13 C12 H12 106.2 . . ?
C19 C12 H12 106.2 . . ?
C11 C12 H12 106.2 . . ?
O4 C13 C14 121.90(18) . . ?
O4 C13 C12 122.59(19) . . ?
C14 C13 C12 115.51(15) . . ?
C13 C14 C9 112.37(14) . . ?
C13 C14 H14A 109.1 . . ?
C9 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C9 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 N1 118.88(16) . . ?
N2 C15 C8 119.55(16) . . ?
N1 C15 C8 121.52(15) . . ?
N2 C16 C17 109.29(17) . . ?
N2 C16 H16A 109.8 . . ?
C17 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
C17 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C16 C17 C18 110.09(18) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
N1 C18 C17 111.29(16) . . ?
N1 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
N1 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C7 173.96(17) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 -174.65(19) . . . . ?
C1 C6 C7 O1 -121.05(19) . . . . ?
C5 C6 C7 O1 52.5(2) . . . . ?
C1 C6 C7 C8 56.8(3) . . . . ?
C5 C6 C7 C8 -129.71(19) . . . . ?
O1 C7 C8 C15 10.8(3) . . . . ?
C6 C7 C8 C15 -166.79(16) . . . . ?
O1 C7 C8 C9 -169.99(17) . . . . ?
C6 C7 C8 C9 12.5(3) . . . . ?
C7 C8 C9 C10 -144.96(17) . . . . ?
C15 C8 C9 C10 34.3(2) . . . . ?
C7 C8 C9 C14 94.1(2) . . . . ?
C15 C8 C9 C14 -86.61(19) . . . . ?
C20 O2 C10 O3 61.54(19) . . . . ?
C20 O2 C10 C11 -57.0(2) . . . . ?
C20 O2 C10 C9 -174.87(15) . . . . ?
C21 O3 C10 O2 59.39(19) . . . . ?
C21 O3 C10 C11 -177.21(15) . . . . ?
C21 O3 C10 C9 -60.12(19) . . . . ?
C8 C9 C10 O2 62.37(17) . . . . ?
C14 C9 C10 O2 -175.26(13) . . . . ?
C8 C9 C10 O3 -175.66(13) . . . . ?
C14 C9 C10 O3 -53.29(18) . . . . ?
C8 C9 C10 C11 -59.63(18) . . . . ?
C14 C9 C10 C11 62.74(17) . . . . ?
C15 N1 C11 C10 -34.8(2) . . . . ?
C18 N1 C11 C10 146.34(16) . . . . ?
C15 N1 C11 C12 88.78(19) . . . . ?
C18 N1 C11 C12 -90.10(19) . . . . ?
O2 C10 C11 N1 -57.51(18) . . . . ?
O3 C10 C11 N1 -179.04(13) . . . . ?
C9 C10 C11 N1 59.84(17) . . . . ?
O2 C10 C11 C12 178.01(14) . . . . ?
O3 C10 C11 C12 56.48(17) . . . . ?
C9 C10 C11 C12 -64.64(18) . . . . ?
N1 C11 C12 C13 -66.84(18) . . . . ?
C10 C11 C12 C13 56.05(18) . . . . ?
N1 C11 C12 C19 62.0(2) . . . . ?
C10 C11 C12 C19 -175.10(15) . . . . ?
C19 C12 C13 O4 3.8(3) . . . . ?
C11 C12 C13 O4 133.3(2) . . . . ?
C19 C12 C13 C14 -177.25(15) . . . . ?
C11 C12 C13 C14 -47.8(2) . . . . ?
O4 C13 C14 C9 -132.91(19) . . . . ?
C12 C13 C14 C9 48.2(2) . . . . ?
C8 C9 C14 C13 66.06(19) . . . . ?
C10 C9 C14 C13 -54.90(19) . . . . ?
C16 N2 C15 N1 -2.6(3) . . . . ?
C16 N2 C15 C8 174.81(18) . . . . ?
C11 N1 C15 N2 -174.83(16) . . . . ?
C18 N1 C15 N2 4.0(3) . . . . ?
C11 N1 C15 C8 7.8(3) . . . . ?
C18 N1 C15 C8 -173.34(17) . . . . ?
C7 C8 C15 N2 -5.6(3) . . . . ?
C9 C8 C15 N2 175.15(16) . . . . ?
C7 C8 C15 N1 171.74(16) . . . . ?
C9 C8 C15 N1 -7.5(3) . . . . ?
C15 N2 C16 C17 -26.3(3) . . . . ?
N2 C16 C17 C18 51.8(2) . . . . ?
C15 N1 C18 C17 23.8(3) . . . . ?
C11 N1 C18 C17 -157.30(18) . . . . ?
C16 C17 C18 N1 -51.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.046
