# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2020

####################################################################### 
# 
# 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_e4622a_a
_database_code_depnum_ccdc_archive 'CCDC 2004107'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 N4 O4, C2 H2 Cl4'
_chemical_formula_sum            'C24 H28 Cl4 N4 O4'
_chemical_formula_weight         578.30

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.8228(4)
_cell_length_b                   15.9940(8)
_cell_length_c                   18.5143(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.008(2)
_cell_angle_gamma                90
_cell_volume                     2822.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2240
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.08


_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.456
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15222
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         28.809
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.809
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.809
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             5967
_reflns_number_gt                5011
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²+2.8186P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5967
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1511
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7925(2) 0.49821(13) 0.72255(13) 0.0308(5) Uani 1 1 d . . . . .
H1 H 0.7615 0.4393 0.7271 0.037 Uiso 1 1 calc R U . . .
C2 C 0.9298(3) 0.5131(3) 0.78027(17) 0.0599(9) Uani 1 1 d . . . . .
H2A H 0.9569 0.5719 0.7791 0.090 Uiso 1 1 calc R U . . .
H2B H 1.0033 0.4776 0.7690 0.090 Uiso 1 1 calc R U . . .
H2C H 0.9175 0.4992 0.8299 0.090 Uiso 1 1 calc R U . . .
C3 C 0.8120(3) 0.51161(19) 0.64442(15) 0.0459(6) Uani 1 1 d . . . . .
H3A H 0.7225 0.5026 0.6081 0.069 Uiso 1 1 calc R U . . .
H3B H 0.8819 0.4720 0.6350 0.069 Uiso 1 1 calc R U . . .
H3C H 0.8443 0.5689 0.6398 0.069 Uiso 1 1 calc R U . . .
C4 C 0.6815(2) 0.55705(12) 0.73698(12) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.6644(2) 0.62802(10) 0.71087(11) 0.0419(4) Uani 1 1 d . . . . .
N1 N 0.6054(2) 0.52707(11) 0.78256(11) 0.0293(4) Uani 1 1 d . . . . .
H1A H 0.6196 0.4761 0.8007 0.035 Uiso 1 1 calc R U . . .
N2 N 0.5041(2) 0.57781(10) 0.80044(11) 0.0280(4) Uani 1 1 d . . . . .
H2 H 0.5286 0.6259 0.8229 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3701(2) 0.55450(12) 0.78392(11) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.32810(18) 0.48452(9) 0.76061(10) 0.0350(4) Uani 1 1 d . . . . .
C6 C 0.2718(2) 0.62187(12) 0.79616(11) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.2090(2) 0.67377(12) 0.73622(12) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.1196(3) 0.73708(15) 0.74839(15) 0.0383(6) Uani 1 1 d . . . . .
H8 H 0.0776 0.7736 0.7088 0.046 Uiso 1 1 calc R U . . .
C9 C 0.0912(3) 0.74739(17) 0.81768(16) 0.0472(7) Uani 1 1 d . . . . .
H9 H 0.0295 0.7905 0.8251 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1523(3) 0.69525(16) 0.87608(15) 0.0417(6) Uani 1 1 d . . . . .
H10 H 0.1312 0.7020 0.9232 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2446(3) 0.63298(14) 0.86587(13) 0.0327(5) Uani 1 1 d . . . . .
H11 H 0.2889 0.5982 0.9063 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2322(2) 0.66199(12) 0.65991(11) 0.0228(4) Uani 1 1 d . . . . .
C13 C 0.3111(2) 0.71929(12) 0.62981(11) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.3239(3) 0.71098(14) 0.55698(12) 0.0314(5) Uani 1 1 d . . . . .
H14 H 0.3774 0.7504 0.5371 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2586(3) 0.64509(14) 0.51333(12) 0.0337(5) Uani 1 1 d . . . . .
H15 H 0.2670 0.6394 0.4635 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1813(3) 0.58765(14) 0.54268(13) 0.0314(5) Uani 1 1 d . . . . .
H16 H 0.1368 0.5424 0.5129 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1684(2) 0.59570(13) 0.61537(12) 0.0284(5) Uani 1 1 d . . . . .
H17 H 0.1156 0.5557 0.6350 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3821(2) 0.79085(12) 0.67666(11) 0.0245(4) Uani 1 1 d . . . . .
O3 O 0.33247(18) 0.86149(9) 0.67092(10) 0.0367(4) Uani 1 1 d . . . . .
N3 N 0.5018(2) 0.76861(10) 0.72421(10) 0.0282(4) Uani 1 1 d . . . . .
H3 H 0.5347 0.7176 0.7231 0.034 Uiso 1 1 calc R U . . .
N4 N 0.5746(2) 0.82643(11) 0.77559(10) 0.0314(4) Uani 1 1 d . . . . .
H4 H 0.5912 0.8771 0.7612 0.038 Uiso 1 1 calc R U . . .
C19 C 0.6191(2) 0.80394(13) 0.84738(12) 0.0291(5) Uani 1 1 d . . . . .
O4 O 0.6043(2) 0.73289(10) 0.86988(9) 0.0408(4) Uani 1 1 d . . . . .
C20 C 0.6861(2) 0.87431(13) 0.89878(12) 0.0310(5) Uani 1 1 d . . . . .
H20 H 0.7000 0.9236 0.8681 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5873(4) 0.8978(3) 0.9458(3) 0.0916(16) Uani 1 1 d . . . . .
H21A H 0.4949 0.9107 0.9136 0.137 Uiso 1 1 calc R U . . .
H21B H 0.6237 0.9470 0.9759 0.137 Uiso 1 1 calc R U . . .
H21C H 0.5788 0.8511 0.9786 0.137 Uiso 1 1 calc R U . . .
C22 C 0.8262(4) 0.8483(2) 0.9475(2) 0.0692(11) Uani 1 1 d . . . . .
H22A H 0.8137 0.7988 0.9764 0.104 Uiso 1 1 calc R U . . .
H22B H 0.8649 0.8940 0.9815 0.104 Uiso 1 1 calc R U . . .
H22C H 0.8908 0.8351 0.9162 0.104 Uiso 1 1 calc R U . . .
Cl1 Cl 0.75653(9) 0.78137(5) 0.62920(5) 0.0568(2) Uani 1 1 d . . . . .
Cl2 Cl 0.55815(7) 0.91026(4) 0.55484(5) 0.0512(2) Uani 1 1 d . . . . .
C23 C 0.7442(4) 0.8822(2) 0.58564(18) 0.0626(9) Uani 1 1 d . . . . .
H23 H 0.7959 0.9249 0.6214 0.075 Uiso 1 1 calc R U . . .
C24 C 0.7990(5) 0.8795(2) 0.51906(19) 0.0688(10) Uani 1 1 d . . . . .
H24 H 0.7470 0.8365 0.4838 0.083 Uiso 1 1 calc R U . . .
Cl3 Cl 0.78293(10) 0.97826(5) 0.47467(4) 0.0605(2) Uani 1 1 d . . . . .
Cl4 Cl 0.98262(8) 0.84907(5) 0.55083(5) 0.0589(2) Uani 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
C1 C4 1.512(3) . ?
C1 C3 1.520(3) . ?
C1 C2 1.523(4) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.229(3) . ?
C4 N1 1.344(3) . ?
N1 N2 1.384(3) . ?
N1 H1A 0.8800 . ?
N2 C5 1.331(3) . ?
N2 H2 0.8800 . ?
C5 O2 1.234(2) . ?
C5 C6 1.500(3) . ?
C6 C11 1.391(3) . ?
C6 C7 1.404(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.496(3) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.395(3) . ?
C12 C13 1.400(3) . ?
C13 C14 1.391(3) . ?
C13 C18 1.502(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O3 1.225(3) . ?
C18 N3 1.335(3) . ?
N3 N4 1.394(2) . ?
N3 H3 0.8800 . ?
N4 C19 1.344(3) . ?
N4 H4 0.8800 . ?
C19 O4 1.231(3) . ?
C19 C20 1.518(3) . ?
C20 C21 1.500(4) . ?
C20 C22 1.509(4) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 C23 1.794(3) . ?
Cl2 C23 1.833(4) . ?
C23 C24 1.461(5) . ?
C23 H23 1.0000 . ?
C24 Cl3 1.770(3) . ?
C24 Cl4 1.822(5) . ?
C24 H24 1.0000 . ?

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
C4 C1 C3 110.06(19) . . ?
C4 C1 C2 109.4(2) . . ?
C3 C1 C2 110.6(2) . . ?
C4 C1 H1 108.9 . . ?
C3 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N1 122.2(2) . . ?
O1 C4 C1 122.7(2) . . ?
N1 C4 C1 115.04(17) . . ?
C4 N1 N2 118.82(17) . . ?
C4 N1 H1A 120.6 . . ?
N2 N1 H1A 120.6 . . ?
C5 N2 N1 120.59(17) . . ?
C5 N2 H2 119.7 . . ?
N1 N2 H2 119.7 . . ?
O2 C5 N2 124.2(2) . . ?
O2 C5 C6 122.1(2) . . ?
N2 C5 C6 113.65(17) . . ?
C11 C6 C7 120.8(2) . . ?
C11 C6 C5 120.47(19) . . ?
C7 C6 C5 118.77(18) . . ?
C8 C7 C6 118.4(2) . . ?
C8 C7 C12 119.34(19) . . ?
C6 C7 C12 122.25(18) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C6 C11 H11 120.1 . . ?
C17 C12 C13 118.35(19) . . ?
C17 C12 C7 120.29(19) . . ?
C13 C12 C7 121.26(18) . . ?
C14 C13 C12 120.81(19) . . ?
C14 C13 C18 119.62(18) . . ?
C12 C13 C18 119.57(18) . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
O3 C18 N3 124.85(19) . . ?
O3 C18 C13 122.2(2) . . ?
N3 C18 C13 112.92(17) . . ?
C18 N3 N4 119.85(17) . . ?
C18 N3 H3 120.1 . . ?
N4 N3 H3 120.1 . . ?
C19 N4 N3 119.19(17) . . ?
C19 N4 H4 120.4 . . ?
N3 N4 H4 120.4 . . ?
O4 C19 N4 123.0(2) . . ?
O4 C19 C20 122.8(2) . . ?
N4 C19 C20 114.18(18) . . ?
C21 C20 C22 110.3(3) . . ?
C21 C20 C19 107.8(2) . . ?
C22 C20 C19 111.4(2) . . ?
C21 C20 H20 109.1 . . ?
C22 C20 H20 109.1 . . ?
C19 C20 H20 109.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 Cl1 110.7(3) . . ?
C24 C23 Cl2 106.8(3) . . ?
Cl1 C23 Cl2 108.29(19) . . ?
C24 C23 H23 110.3 . . ?
Cl1 C23 H23 110.3 . . ?
Cl2 C23 H23 110.3 . . ?
C23 C24 Cl3 110.8(3) . . ?
C23 C24 Cl4 105.9(3) . . ?
Cl3 C24 Cl4 111.0(2) . . ?
C23 C24 H24 109.7 . . ?
Cl3 C24 H24 109.7 . . ?
Cl4 C24 H24 109.7 . . ?

_refine_diff_density_max         1.352
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.064

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,1,2,2-Tetrachloroethane'
####################################################################### 
# 
# 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_e4700a_a
_database_code_depnum_ccdc_archive 'CCDC 2004108'
loop_
_audit_author_name
_audit_author_address
'Nathalie Gruber'
;University of Strasbourg
France
;
_audit_update_record             
;
2020-05-14 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H52 O12'
_chemical_formula_sum            'C48 H52 O12'
_chemical_formula_weight         820.89

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6496(5)
_cell_length_b                   12.0424(8)
_cell_length_c                   19.8345(13)
_cell_angle_alpha                81.278(2)
_cell_angle_beta                 82.463(2)
_cell_angle_gamma                70.074(2)
_cell_volume                     2134.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4439
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30510
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.811
_diffrn_reflns_theta_max         28.724
_diffrn_reflns_theta_full        25.142
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             10379
_reflns_number_gt                7939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0653P)²+0.5311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10379
_refine_ls_number_parameters     549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26867(18) 1.18868(15) 0.01038(8) 0.0396(4) Uani 1 1 d . . . . .
H1 H 0.317173 1.191124 0.051441 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1532(2) 1.31003(16) -0.00631(12) 0.0600(5) Uani 1 1 d . . . . .
H2A H 0.201558 1.371008 -0.015804 0.090 Uiso 1 1 calc R U . . .
H2B H 0.078999 1.328061 0.032764 0.090 Uiso 1 1 calc R U . . .
H2C H 0.105003 1.309000 -0.046612 0.090 Uiso 1 1 calc R U . . .
C3 C 0.3862(2) 1.15936(19) -0.04899(11) 0.0586(5) Uani 1 1 d . . . . .
H3A H 0.461403 1.082622 -0.036766 0.088 Uiso 1 1 calc R U . . .
H3B H 0.432670 1.221467 -0.059176 0.088 Uiso 1 1 calc R U . . .
H3C H 0.340469 1.155026 -0.089380 0.088 Uiso 1 1 calc R U . . .
C4 C 0.19222(16) 1.09614(12) 0.02745(7) 0.0288(3) Uani 1 1 d . . . . .
O1 O 0.18039(13) 1.03309(10) -0.01137(5) 0.0429(3) Uani 1 1 d . . . . .
O2 O 0.12990(11) 1.09716(8) 0.09247(5) 0.0299(2) Uani 1 1 d . . . . .
C5 C 0.05171(15) 1.01500(11) 0.11582(7) 0.0274(3) Uani 1 1 d . . . . .
H5A H 0.009199 0.999624 0.076797 0.033 Uiso 1 1 calc R U . . .
H5B H -0.030663 1.049524 0.149880 0.033 Uiso 1 1 calc R U . . .
C6 C 0.15569(15) 0.89878(11) 0.14812(6) 0.0245(3) Uani 1 1 d . . . . .
O3 O 0.28833(11) 0.87762(9) 0.14054(5) 0.0348(2) Uani 1 1 d . . . . .
C7 C 0.08664(14) 0.81298(11) 0.18912(7) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.16280(14) 0.72743(11) 0.24025(7) 0.0239(3) Uani 1 1 d . . . . .
C9 C 0.09744(15) 0.64562(12) 0.27478(7) 0.0281(3) Uani 1 1 d . . . . .
H9 H 0.147661 0.587526 0.309255 0.034 Uiso 1 1 calc R U . . .
C10 C -0.03913(16) 0.64768(13) 0.25968(8) 0.0323(3) Uani 1 1 d . . . . .
H10 H -0.081744 0.590971 0.283598 0.039 Uiso 1 1 calc R U . . .
C11 C -0.11430(16) 0.73211(13) 0.20977(8) 0.0334(3) Uani 1 1 d . . . . .
H11 H -0.208438 0.733612 0.199559 0.040 Uiso 1 1 calc R U . . .
C12 C -0.05136(15) 0.81436(12) 0.17483(7) 0.0293(3) Uani 1 1 d . . . . .
H12 H -0.103078 0.872384 0.140724 0.035 Uiso 1 1 calc R U . . .
C13 C 0.30568(15) 0.72283(11) 0.26401(6) 0.0249(3) Uani 1 1 d . . . . .
C14 C 0.43881(15) 0.62923(12) 0.25412(7) 0.0265(3) Uani 1 1 d . . . . .
C15 C 0.56150(16) 0.62125(14) 0.28720(8) 0.0350(3) Uani 1 1 d . . . . .
H15 H 0.650811 0.557060 0.280968 0.042 Uiso 1 1 calc R U . . .
C16 C 0.55497(18) 0.70519(15) 0.32883(8) 0.0398(4) Uani 1 1 d . . . . .
H16 H 0.639391 0.699373 0.350759 0.048 Uiso 1 1 calc R U . . .
C17 C 0.42461(19) 0.79772(15) 0.33830(8) 0.0405(4) Uani 1 1 d . . . . .
H17 H 0.419472 0.856065 0.366705 0.049 Uiso 1 1 calc R U . . .
C18 C 0.30134(17) 0.80594(13) 0.30664(8) 0.0336(3) Uani 1 1 d . . . . .
H18 H 0.212042 0.869548 0.314155 0.040 Uiso 1 1 calc R U . . .
C19 C 0.46008(15) 0.53461(12) 0.20898(7) 0.0279(3) Uani 1 1 d . . . . .
O4 O 0.54179(12) 0.43387(9) 0.22300(5) 0.0388(3) Uani 1 1 d . . . . .
C20 C 0.38736(16) 0.56791(12) 0.14209(7) 0.0317(3) Uani 1 1 d . . . . .
H20A H 0.278461 0.594893 0.151824 0.038 Uiso 1 1 calc R U . . .
H20B H 0.415077 0.634409 0.114955 0.038 Uiso 1 1 calc R U . . .
O5 O 0.43232(10) 0.46861(9) 0.10342(5) 0.0314(2) Uani 1 1 d . . . . .
C21 C 0.57428(15) 0.43744(12) 0.07541(7) 0.0280(3) Uani 1 1 d . . . . .
O6 O 0.64829(12) 0.50039(10) 0.07341(6) 0.0385(3) Uani 1 1 d . . . . .
C22 C 0.62060(16) 0.31941(13) 0.04762(7) 0.0326(3) Uani 1 1 d . . . . .
H22 H 0.551965 0.325257 0.012599 0.039 Uiso 1 1 calc R U . . .
C23 C 0.6083(2) 0.22143(14) 0.10460(9) 0.0482(4) Uani 1 1 d . . . . .
H23A H 0.672723 0.215798 0.140167 0.072 Uiso 1 1 calc R U . . .
H23B H 0.638667 0.145324 0.085611 0.072 Uiso 1 1 calc R U . . .
H23C H 0.505638 0.240387 0.124543 0.072 Uiso 1 1 calc R U . . .
C24 C 0.77708(18) 0.28964(16) 0.01276(9) 0.0468(4) Uani 1 1 d . . . . .
H24A H 0.784004 0.356030 -0.021285 0.070 Uiso 1 1 calc R U . . .
H24B H 0.800648 0.217800 -0.009962 0.070 Uiso 1 1 calc R U . . .
H24C H 0.847291 0.275928 0.047078 0.070 Uiso 1 1 calc R U . . .
C25 C 0.2115(2) 0.55542(15) 0.49161(9) 0.0450(4) Uani 1 1 d . . . . .
H25 H 0.140807 0.600129 0.456521 0.054 Uiso 1 1 calc R U . . .
C26 C 0.1218(3) 0.5447(2) 0.55940(13) 0.0788(7) Uani 1 1 d . . . . .
H26A H 0.071194 0.486820 0.558695 0.118 Uiso 1 1 calc R U . . .
H26B H 0.048329 0.622245 0.566929 0.118 Uiso 1 1 calc R U . . .
H26C H 0.187728 0.518010 0.596465 0.118 Uiso 1 1 calc R U . . .
C27 C 0.3130(3) 0.6245(2) 0.49491(15) 0.0870(9) Uani 1 1 d . . . . .
H27A H 0.380305 0.584751 0.530681 0.130 Uiso 1 1 calc R U . . .
H27B H 0.254506 0.705023 0.505557 0.130 Uiso 1 1 calc R U . . .
H27C H 0.370581 0.629055 0.450654 0.130 Uiso 1 1 calc R U . . .
C28 C 0.29665(17) 0.43474(13) 0.46899(7) 0.0326(3) Uani 1 1 d . . . . .
O7 O 0.30973(15) 0.34076(10) 0.50253(6) 0.0498(3) Uani 1 1 d . . . . .
O8 O 0.36207(13) 0.44481(9) 0.40507(5) 0.0365(2) Uani 1 1 d . . . . .
C29 C 0.44128(17) 0.33645(13) 0.37636(7) 0.0325(3) Uani 1 1 d . . . . .
H29A H 0.487042 0.273881 0.412922 0.039 Uiso 1 1 calc R U . . .
H29B H 0.521233 0.348369 0.342368 0.039 Uiso 1 1 calc R U . . .
C30 C 0.33641(16) 0.29730(12) 0.34193(7) 0.0284(3) Uani 1 1 d . . . . .
O9 O 0.20410(12) 0.34613(10) 0.35050(6) 0.0441(3) Uani 1 1 d . . . . .
C31 C 0.40287(14) 0.19727(12) 0.29889(7) 0.0255(3) Uani 1 1 d . . . . .
C32 C 0.31787(14) 0.17335(11) 0.25371(7) 0.0233(3) Uani 1 1 d . . . . .
C33 C 0.38033(15) 0.07335(12) 0.21906(7) 0.0286(3) Uani 1 1 d . . . . .
H33 H 0.323107 0.055108 0.189533 0.034 Uiso 1 1 calc R U . . .
C34 C 0.52503(17) -0.00039(13) 0.22686(8) 0.0354(3) Uani 1 1 d . . . . .
H34 H 0.565135 -0.069233 0.203500 0.043 Uiso 1 1 calc R U . . .
C35 C 0.61047(17) 0.02622(14) 0.26845(8) 0.0367(3) Uani 1 1 d . . . . .
H35 H 0.710821 -0.021944 0.272186 0.044 Uiso 1 1 calc R U . . .
C36 C 0.54881(16) 0.12372(13) 0.30473(7) 0.0319(3) Uani 1 1 d . . . . .
H36 H 0.607162 0.140805 0.334188 0.038 Uiso 1 1 calc R U . . .
C37 C 0.17160(15) 0.25820(11) 0.23277(7) 0.0250(3) Uani 1 1 d . . . . .
C38 C 0.03882(15) 0.23278(12) 0.24556(7) 0.0274(3) Uani 1 1 d . . . . .
C39 C -0.08760(17) 0.31049(14) 0.21561(8) 0.0373(3) Uani 1 1 d . . . . .
H39 H -0.177813 0.293366 0.224478 0.045 Uiso 1 1 calc R U . . .
C40 C -0.08297(18) 0.41146(14) 0.17347(9) 0.0426(4) Uani 1 1 d . . . . .
H40 H -0.169752 0.464321 0.154002 0.051 Uiso 1 1 calc R U . . .
C41 C 0.04831(18) 0.43513(14) 0.15980(8) 0.0403(4) Uani 1 1 d . . . . .
H41 H 0.052503 0.503840 0.130084 0.048 Uiso 1 1 calc R U . . .
C42 C 0.17451(16) 0.35937(12) 0.18912(8) 0.0318(3) Uani 1 1 d . . . . .
H42 H 0.264390 0.376859 0.179217 0.038 Uiso 1 1 calc R U . . .
C43 C 0.02114(15) 0.12724(13) 0.29113(7) 0.0297(3) Uani 1 1 d . . . . .
O10 O -0.04184(13) 0.06533(11) 0.27456(6) 0.0428(3) Uani 1 1 d . . . . .
C44 C 0.07580(18) 0.10432(14) 0.36173(7) 0.0349(3) Uani 1 1 d . . . . .
H44A H 0.184573 0.085389 0.357274 0.042 Uiso 1 1 calc R U . . .
H44B H 0.031449 0.177181 0.384944 0.042 Uiso 1 1 calc R U . . .
O11 O 0.03858(11) 0.00828(9) 0.40250(5) 0.0335(2) Uani 1 1 d . . . . .
C45 C -0.10764(16) 0.03089(13) 0.42218(7) 0.0296(3) Uani 1 1 d . . . . .
O12 O -0.19743(12) 0.12800(10) 0.41244(6) 0.0409(3) Uani 1 1 d . . . . .
C46 C -0.13734(17) -0.08012(13) 0.45674(7) 0.0341(3) Uani 1 1 d . . . . .
H46 H -0.066042 -0.117448 0.492533 0.041 Uiso 1 1 calc R U . . .
C47 C -0.2929(2) -0.04994(18) 0.49207(10) 0.0542(5) Uani 1 1 d . . . . .
H47A H -0.307317 0.009326 0.523437 0.081 Uiso 1 1 calc R U . . .
H47B H -0.306904 -0.121993 0.517908 0.081 Uiso 1 1 calc R U . . .
H47C H -0.364998 -0.017687 0.457648 0.081 Uiso 1 1 calc R U . . .
C48 C -0.1096(2) -0.16863(15) 0.40479(9) 0.0479(4) Uani 1 1 d . . . . .
H48A H -0.176233 -0.132944 0.368325 0.072 Uiso 1 1 calc R U . . .
H48B H -0.128116 -0.240892 0.427723 0.072 Uiso 1 1 calc R U . . .
H48C H -0.006768 -0.188811 0.385025 0.072 Uiso 1 1 calc R U . . .


_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
C1 C4 1.510(2) . ?
C1 C3 1.517(2) . ?
C1 C2 1.525(3) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.2007(17) . ?
C4 O2 1.3496(16) . ?
O2 C5 1.4285(16) . ?
C5 C6 1.5218(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.2101(16) . ?
C6 C7 1.4983(18) . ?
C7 C12 1.392(2) . ?
C7 C8 1.4116(18) . ?
C8 C9 1.3940(18) . ?
C8 C13 1.4956(19) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.3918(19) . ?
C13 C14 1.4047(18) . ?
C14 C15 1.396(2) . ?
C14 C19 1.4980(19) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O4 1.2141(16) . ?
C19 C20 1.518(2) . ?
C20 O5 1.4296(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
O5 C21 1.3562(17) . ?
C21 O6 1.1994(17) . ?
C21 C22 1.505(2) . ?
C22 C24 1.523(2) . ?
C22 C23 1.530(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C27 1.499(3) . ?
C25 C28 1.509(2) . ?
C25 C26 1.514(3) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O7 1.1982(18) . ?
C28 O8 1.3475(18) . ?
O8 C29 1.4292(17) . ?
C29 C30 1.522(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O9 1.2110(17) . ?
C30 C31 1.4942(18) . ?
C31 C36 1.3938(19) . ?
C31 C32 1.4110(19) . ?
C32 C33 1.3905(18) . ?
C32 C37 1.5003(18) . ?
C33 C34 1.390(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C42 1.3898(19) . ?
C37 C38 1.3994(19) . ?
C38 C39 1.400(2) . ?
C38 C43 1.490(2) . ?
C39 C40 1.378(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.375(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.386(2) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 O10 1.2119(17) . ?
C43 C44 1.514(2) . ?
C44 O11 1.4296(17) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
O11 C45 1.3576(17) . ?
C45 O12 1.2002(17) . ?
C45 C46 1.507(2) . ?
C46 C47 1.519(2) . ?
C46 C48 1.528(2) . ?
C46 H46 1.0000 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
C4 C1 C3 111.47(14) . . ?
C4 C1 C2 108.99(13) . . ?
C3 C1 C2 110.53(15) . . ?
C4 C1 H1 108.6 . . ?
C3 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 O2 123.19(13) . . ?
O1 C4 C1 125.94(13) . . ?
O2 C4 C1 110.78(12) . . ?
C4 O2 C5 117.21(10) . . ?
O2 C5 C6 110.15(11) . . ?
O2 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
O2 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O3 C6 C7 122.08(12) . . ?
O3 C6 C5 120.76(12) . . ?
C7 C6 C5 117.17(11) . . ?
C12 C7 C8 119.56(12) . . ?
C12 C7 C6 119.74(12) . . ?
C8 C7 C6 120.66(12) . . ?
C9 C8 C7 118.69(12) . . ?
C9 C8 C13 116.63(12) . . ?
C7 C8 C13 124.54(12) . . ?
C10 C9 C8 121.04(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.28(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.63(14) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 120.81(13) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C18 C13 C14 118.21(13) . . ?
C18 C13 C8 117.81(12) . . ?
C14 C13 C8 123.26(12) . . ?
C15 C14 C13 119.80(13) . . ?
C15 C14 C19 116.20(12) . . ?
C13 C14 C19 124.00(12) . . ?
C16 C15 C14 120.98(14) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.37(15) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.36(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 121.28(14) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
O4 C19 C14 120.96(13) . . ?
O4 C19 C20 119.68(13) . . ?
C14 C19 C20 119.19(11) . . ?
O5 C20 C19 110.72(11) . . ?
O5 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 O5 C20 115.36(11) . . ?
O6 C21 O5 121.82(13) . . ?
O6 C21 C22 126.59(13) . . ?
O5 C21 C22 111.58(12) . . ?
C21 C22 C24 110.67(13) . . ?
C21 C22 C23 110.57(12) . . ?
C24 C22 C23 110.97(13) . . ?
C21 C22 H22 108.2 . . ?
C24 C22 H22 108.2 . . ?
C23 C22 H22 108.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C25 C28 110.93(15) . . ?
C27 C25 C26 111.26(17) . . ?
C28 C25 C26 111.20(16) . . ?
C27 C25 H25 107.8 . . ?
C28 C25 H25 107.8 . . ?
C26 C25 H25 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O7 C28 O8 122.83(14) . . ?
O7 C28 C25 126.10(14) . . ?
O8 C28 C25 111.04(13) . . ?
C28 O8 C29 116.62(11) . . ?
O8 C29 C30 109.91(12) . . ?
O8 C29 H29A 109.7 . . ?
C30 C29 H29A 109.7 . . ?
O8 C29 H29B 109.7 . . ?
C30 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
O9 C30 C31 122.40(13) . . ?
O9 C30 C29 119.93(13) . . ?
C31 C30 C29 117.67(12) . . ?
C36 C31 C32 119.12(12) . . ?
C36 C31 C30 120.12(12) . . ?
C32 C31 C30 120.73(12) . . ?
C33 C32 C31 118.72(12) . . ?
C33 C32 C37 116.87(12) . . ?
C31 C32 C37 123.82(11) . . ?
C34 C33 C32 121.15(13) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C35 C34 C33 120.11(13) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 119.47(13) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 121.32(13) . . ?
C35 C36 H36 119.3 . . ?
C31 C36 H36 119.3 . . ?
C42 C37 C38 118.56(12) . . ?
C42 C37 C32 116.69(12) . . ?
C38 C37 C32 123.96(12) . . ?
C39 C38 C37 119.59(13) . . ?
C39 C38 C43 116.56(13) . . ?
C37 C38 C43 123.84(12) . . ?
C40 C39 C38 120.90(14) . . ?
C40 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C41 C40 C39 119.47(14) . . ?
C41 C40 H40 120.3 . . ?
C39 C40 H40 120.3 . . ?
C40 C41 C42 120.43(15) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C37 121.02(14) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?
O10 C43 C38 122.00(13) . . ?
O10 C43 C44 120.48(13) . . ?
C38 C43 C44 117.38(12) . . ?
O11 C44 C43 111.65(12) . . ?
O11 C44 H44A 109.3 . . ?
C43 C44 H44A 109.3 . . ?
O11 C44 H44B 109.3 . . ?
C43 C44 H44B 109.3 . . ?
H44A C44 H44B 108.0 . . ?
C45 O11 C44 115.23(12) . . ?
O12 C45 O11 122.50(13) . . ?
O12 C45 C46 126.54(14) . . ?
O11 C45 C46 110.96(12) . . ?
C45 C46 C47 110.67(13) . . ?
C45 C46 C48 109.93(12) . . ?
C47 C46 C48 112.14(15) . . ?
C45 C46 H46 108.0 . . ?
C47 C46 H46 108.0 . . ?
C48 C46 H46 108.0 . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C46 C48 H48A 109.5 . . ?
C46 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C46 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane, ethyl acetate'
