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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_scpc104
_audit_block_doi                 10.5517/cczx2vs
_database_code_depnum_ccdc_archive 'CCDC 920726'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C3CC40541A 2013
_audit_update_record             
;
2013-01-18 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;
#TrackingRef 'SCPC104.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H35 N O3'
_chemical_formula_weight         337.49

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   6.7242(3)
_cell_length_b                   15.1813(7)
_cell_length_c                   19.2667(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1966.79(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          1.09
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9227
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12156
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.08
_reflns_number_total             3453
_reflns_number_gt                3194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 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)+(0.0338P)²+0.3164P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_number_reflns         3453
_refine_ls_number_parameters     357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O2PD O 0.62821(17) 0.39545(7) 0.53771(6) 0.0200(3) Uani 1 1 d . . .
O3HF O 0.72769(18) 0.19430(8) 0.73062(6) 0.0243(3) Uani 1 1 d . . .
C00 C 0.9530(3) 0.43070(11) 0.49236(9) 0.0171(4) Uani 1 1 d . . .
N1 N 1.0281(2) 0.18690(9) 0.67900(7) 0.0193(3) Uani 1 1 d . . .
C02 C 0.5135(2) 0.62938(10) 0.56810(9) 0.0175(4) Uani 1 1 d . . .
C03 C 0.6475(2) 0.49808(11) 0.73694(9) 0.0178(4) Uani 1 1 d . . .
C04 C 1.1246(3) 0.39918(11) 0.53897(9) 0.0173(3) Uani 1 1 d . . .
C07 C 0.6586(3) 0.57296(11) 0.68352(9) 0.0180(4) Uani 1 1 d . . .
C08 C 1.2236(3) 0.22263(11) 0.66521(9) 0.0188(4) Uani 1 1 d . . .
C09 C 1.2557(3) 0.27336(10) 0.61065(8) 0.0177(4) Uani 1 1 d . . .
C0A C 0.9008(3) 0.22150(10) 0.72642(8) 0.0181(4) Uani 1 1 d . . .
C0B C 0.5999(2) 0.55103(10) 0.60946(8) 0.0155(4) Uani 1 1 d . . .
C0@ C 0.7678(2) 0.44559(10) 0.53571(8) 0.0153(3) Uani 1 1 d . . .
O1GK O 0.77900(16) 0.52029(7) 0.57272(6) 0.0158(3) Uani 1 1 d . . .
C20E C 0.9565(3) 0.11668(13) 0.63391(11) 0.0293(5) Uani 1 1 d . . .
C21E C 0.4337(3) 0.46387(13) 0.74454(10) 0.0231(4) Uani 1 1 d . . .
C22E C 1.0059(3) 0.51142(12) 0.44868(9) 0.0222(4) Uani 1 1 d . . .
C23E C 0.8269(3) 0.36435(11) 0.78739(9) 0.0209(4) Uani 1 1 d . . .
C24E C 0.6425(3) 0.71169(12) 0.57609(11) 0.0238(4) Uani 1 1 d . . .
C25E C 1.1006(3) 0.30339(11) 0.56038(9) 0.0191(4) Uani 1 1 d . . .
C26E C 0.3036(3) 0.64839(12) 0.59593(10) 0.0206(4) Uani 1 1 d . . .
C27E C 0.4990(3) 0.60599(12) 0.49110(9) 0.0212(4) Uani 1 1 d . . .
C28E C 0.7960(3) 0.42331(11) 0.72404(9) 0.0183(4) Uani 1 1 d . . .
C29E C 0.9782(3) 0.29151(11) 0.77494(9) 0.0199(4) Uani 1 1 d . . .
H1 H 0.873(3) 0.4019(11) 0.8265(9) 0.018(4) Uiso 1 1 d . . .
H2 H 0.573(3) 0.6212(11) 0.6992(8) 0.011(4) Uiso 1 1 d . . .
H3 H 0.750(2) 0.3878(11) 0.6840(9) 0.018(4) Uiso 1 1 d . . .
H4 H 1.032(3) 0.5632(12) 0.4801(9) 0.021(5) Uiso 1 1 d . . .
H5 H 0.422(3) 0.4212(12) 0.7839(9) 0.023(5) Uiso 1 1 d . . .
H6 H 0.922(2) 0.3850(11) 0.4632(8) 0.012(4) Uiso 1 1 d . . .
H7 H 0.257(3) 0.7002(11) 0.5702(9) 0.015(4) Uiso 1 1 d . . .
H8 H 0.432(3) 0.5467(12) 0.4824(8) 0.013(4) Uiso 1 1 d . . .
H9 H 0.391(3) 0.4286(13) 0.7017(10) 0.032(5) Uiso 1 1 d . . .
H10 H 0.426(3) 0.6492(12) 0.4650(9) 0.023(5) Uiso 1 1 d . . .
H11 H 0.642(3) 0.7323(12) 0.6247(10) 0.030(5) Uiso 1 1 d . . .
H12 H 1.002(2) 0.2617(11) 0.8175(9) 0.014(4) Uiso 1 1 d . . .
H13 H 0.780(4) 0.7008(14) 0.5637(11) 0.043(6) Uiso 1 1 d . . .
H14 H 1.390(3) 0.2937(11) 0.6020(8) 0.016(4) Uiso 1 1 d . . .
H15 H 0.632(3) 0.6040(12) 0.4672(10) 0.026(5) Uiso 1 1 d . . .
H16 H 0.686(2) 0.5237(11) 0.7810(9) 0.015(4) Uiso 1 1 d . . .
H17 H 0.598(3) 0.7584(13) 0.5456(9) 0.028(5) Uiso 1 1 d . . .
H18 H 1.106(3) 0.2691(12) 0.5196(9) 0.022(5) Uiso 1 1 d . . .
H19 H 0.971(3) 0.2942(12) 0.5823(9) 0.030(5) Uiso 1 1 d . . .
H20 H 0.702(3) 0.3365(12) 0.8017(10) 0.027(5) Uiso 1 1 d . . .
H21 H 0.304(3) 0.6636(11) 0.6454(10) 0.025(5) Uiso 1 1 d . . .
H22 H 1.118(3) 0.4996(12) 0.4171(10) 0.029(5) Uiso 1 1 d . . .
H23 H 0.793(3) 0.5986(12) 0.6843(9) 0.027(5) Uiso 1 1 d . . .
H24 H 0.888(3) 0.5292(12) 0.4166(10) 0.029(5) Uiso 1 1 d . . .
H25 H 0.508(2) 0.5002(10) 0.6062(8) 0.009(4) Uiso 1 1 d . . .
H26 H 1.325(3) 0.2054(12) 0.6976(10) 0.026(5) Uiso 1 1 d . . .
H27 H 1.128(3) 0.4356(12) 0.5813(9) 0.019(4) Uiso 1 1 d . . .
H28 H 1.102(3) 0.3164(12) 0.7565(9) 0.022(5) Uiso 1 1 d . . .
H29 H 0.214(3) 0.5955(12) 0.5893(9) 0.024(5) Uiso 1 1 d . . .
H30 H 0.913(3) 0.4480(11) 0.7117(9) 0.015(4) Uiso 1 1 d . . .
H31 H 1.247(3) 0.4058(11) 0.5122(9) 0.023(5) Uiso 1 1 d . . .
H32 H 0.340(3) 0.5125(14) 0.7522(10) 0.036(6) Uiso 1 1 d . . .
H33 H 0.929(4) 0.0656(18) 0.6585(14) 0.067(8) Uiso 1 1 d . . .
H34 H 1.020(5) 0.1142(19) 0.5924(17) 0.085(10) Uiso 1 1 d . . .
H35 H 0.825(6) 0.132(2) 0.6117(19) 0.110(12) 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
O2PD C0@ 1.2090(19) . ?
O3HF C0A 1.238(2) . ?
C00 C0@ 1.516(2) . ?
C00 C22E 1.529(2) . ?
C00 C04 1.538(2) . ?
C00 H6 0.918(17) . ?
N1 C0A 1.358(2) . ?
N1 C08 1.446(2) . ?
N1 C20E 1.457(2) . ?
C02 C27E 1.529(2) . ?
C02 C24E 1.529(2) . ?
C02 C26E 1.537(2) . ?
C02 C0B 1.545(2) . ?
C03 C28E 1.532(2) . ?
C03 C07 1.535(2) . ?
C03 C21E 1.536(2) . ?
C03 H16 0.970(17) . ?
C04 C25E 1.520(2) . ?
C04 H27 0.985(18) . ?
C04 H31 0.98(2) . ?
C07 C0B 1.517(2) . ?
C07 H2 0.979(17) . ?
C07 H23 0.982(19) . ?
C08 C09 1.321(2) . ?
C08 H26 0.96(2) . ?
C09 C25E 1.495(2) . ?
C09 H14 0.968(19) . ?
C0A C29E 1.508(2) . ?
C0B O1GK 1.4727(19) . ?
C0B H25 0.992(17) . ?
C0@ O1GK 1.3418(19) . ?
C20E H33 0.93(3) . ?
C20E H34 0.91(3) . ?
C20E H35 1.01(4) . ?
C21E H5 1.000(19) . ?
C21E H9 1.02(2) . ?
C21E H32 0.98(2) . ?
C22E H4 1.008(19) . ?
C22E H22 0.98(2) . ?
C22E H24 1.04(2) . ?
C23E C29E 1.522(2) . ?
C23E C28E 1.528(2) . ?
C23E H1 0.994(18) . ?
C23E H20 0.98(2) . ?
C24E H11 0.988(19) . ?
C24E H13 0.97(2) . ?
C24E H17 0.97(2) . ?
C25E H18 0.943(17) . ?
C25E H19 0.98(2) . ?
C26E H7 0.980(17) . ?
C26E H21 0.980(19) . ?
C26E H29 1.010(19) . ?
C27E H8 1.020(18) . ?
C27E H10 0.959(19) . ?
C27E H15 1.01(2) . ?
C28E H3 0.990(18) . ?
C28E H30 0.905(19) . ?
C29E H12 0.949(17) . ?
C29E H28 0.98(2) . ?

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
C0@ C00 C22E 112.02(14) . . ?
C0@ C00 C04 109.92(13) . . ?
C22E C00 C04 113.34(15) . . ?
C0@ C00 H6 105.1(10) . . ?
C22E C00 H6 108.9(10) . . ?
C04 C00 H6 107.1(10) . . ?
C0A N1 C08 123.47(14) . . ?
C0A N1 C20E 118.40(15) . . ?
C08 N1 C20E 117.72(15) . . ?
C27E C02 C24E 108.89(15) . . ?
C27E C02 C26E 108.89(14) . . ?
C24E C02 C26E 109.40(14) . . ?
C27E C02 C0B 110.23(13) . . ?
C24E C02 C0B 111.34(14) . . ?
C26E C02 C0B 108.06(14) . . ?
C28E C03 C07 114.09(14) . . ?
C28E C03 C21E 112.03(14) . . ?
C07 C03 C21E 111.08(14) . . ?
C28E C03 H16 105.4(10) . . ?
C07 C03 H16 106.1(9) . . ?
C21E C03 H16 107.6(10) . . ?
C25E C04 C00 112.11(14) . . ?
C25E C04 H27 108.3(10) . . ?
C00 C04 H27 109.1(11) . . ?
C25E C04 H31 109.3(10) . . ?
C00 C04 H31 107.0(10) . . ?
H27 C04 H31 111.0(15) . . ?
C0B C07 C03 117.09(14) . . ?
C0B C07 H2 107.6(9) . . ?
C03 C07 H2 108.5(9) . . ?
C0B C07 H23 109.9(11) . . ?
C03 C07 H23 109.1(11) . . ?
H2 C07 H23 103.7(14) . . ?
C09 C08 N1 120.91(16) . . ?
C09 C08 H26 124.0(11) . . ?
N1 C08 H26 115.1(11) . . ?
C08 C09 C25E 125.39(16) . . ?
C08 C09 H14 118.3(10) . . ?
C25E C09 H14 116.3(10) . . ?
O3HF C0A N1 120.53(15) . . ?
O3HF C0A C29E 121.27(15) . . ?
N1 C0A C29E 118.17(15) . . ?
O1GK C0B C07 108.00(13) . . ?
O1GK C0B C02 107.67(13) . . ?
C07 C0B C02 114.45(13) . . ?
O1GK C0B H25 103.6(9) . . ?
C07 C0B H25 113.1(9) . . ?
C02 C0B H25 109.3(9) . . ?
O2PD C0@ O1GK 123.97(15) . . ?
O2PD C0@ C00 124.14(14) . . ?
O1GK C0@ C00 111.87(13) . . ?
C0@ O1GK C0B 118.51(12) . . ?
N1 C20E H33 111.8(16) . . ?
N1 C20E H34 113.7(19) . . ?
H33 C20E H34 121(2) . . ?
N1 C20E H35 111.9(19) . . ?
H33 C20E H35 104(2) . . ?
H34 C20E H35 93(3) . . ?
C03 C21E H5 111.4(11) . . ?
C03 C21E H9 111.4(11) . . ?
H5 C21E H9 104.5(14) . . ?
C03 C21E H32 111.1(12) . . ?
H5 C21E H32 108.8(16) . . ?
H9 C21E H32 109.4(16) . . ?
C00 C22E H4 109.6(10) . . ?
C00 C22E H22 111.8(11) . . ?
H4 C22E H22 112.3(16) . . ?
C00 C22E H24 110.9(11) . . ?
H4 C22E H24 106.7(14) . . ?
H22 C22E H24 105.3(15) . . ?
C29E C23E C28E 112.99(14) . . ?
C29E C23E H1 109.2(10) . . ?
C28E C23E H1 108.2(10) . . ?
C29E C23E H20 107.7(11) . . ?
C28E C23E H20 111.2(11) . . ?
H1 C23E H20 107.5(15) . . ?
C02 C24E H11 110.6(11) . . ?
C02 C24E H13 112.1(13) . . ?
H11 C24E H13 107.2(18) . . ?
C02 C24E H17 111.3(12) . . ?
H11 C24E H17 110.0(15) . . ?
H13 C24E H17 105.5(18) . . ?
C09 C25E C04 113.17(15) . . ?
C09 C25E H18 110.3(11) . . ?
C04 C25E H18 107.4(11) . . ?
C09 C25E H19 107.5(11) . . ?
C04 C25E H19 110.3(11) . . ?
H18 C25E H19 108.2(16) . . ?
C02 C26E H7 105.4(10) . . ?
C02 C26E H21 112.3(11) . . ?
H7 C26E H21 107.7(14) . . ?
C02 C26E H29 110.7(10) . . ?
H7 C26E H29 112.6(14) . . ?
H21 C26E H29 108.2(15) . . ?
C02 C27E H8 113.1(9) . . ?
C02 C27E H10 112.4(11) . . ?
H8 C27E H10 107.2(15) . . ?
C02 C27E H15 113.2(11) . . ?
H8 C27E H15 106.8(14) . . ?
H10 C27E H15 103.5(15) . . ?
C23E C28E C03 113.14(14) . . ?
C23E C28E H3 110.2(9) . . ?
C03 C28E H3 109.0(10) . . ?
C23E C28E H30 109.5(11) . . ?
C03 C28E H30 107.7(11) . . ?
H3 C28E H30 107.0(15) . . ?
C0A C29E C23E 112.29(15) . . ?
C0A C29E H12 104.9(10) . . ?
C23E C29E H12 108.8(10) . . ?
C0A C29E H28 109.9(10) . . ?
C23E C29E H28 110.1(10) . . ?
H12 C29E H28 110.7(14) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_Compound_18
_database_code_depnum_ccdc_archive 'CCDC 1454803'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(14R,16R,E)-16-(tert-butyl)-14-methyl-1-oxa-8-azacyclohexadec-10-ene-2,9-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H33 N O3'
_chemical_formula_sum            'C19 H33 N O3'
_chemical_formula_weight         323.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.998(3)
_cell_length_b                   8.740(2)
_cell_length_c                   18.751(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.393(6)
_cell_angle_gamma                90
_cell_volume                     1904.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1600
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      19.64

_exptl_crystal_description       NEEDLES
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (BRUKER, 2006)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            36143
_diffrn_reflns_av_unetI/netI     0.1778
_diffrn_reflns_av_R_equivalents  0.1555
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.121
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9449
_reflns_number_gt                5015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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-2014/7 (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)+(0.0644P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.3(10)
_chemical_absolute_configuration SYN
_refine_ls_number_reflns         9449
_refine_ls_number_parameters     424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1757
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
O1A O 0.7186(4) 0.5581(5) 0.0429(2) 0.0434(11) Uani 1 1 d . . . . .
O2A O 0.9906(3) 0.2264(4) 0.28657(17) 0.0210(8) Uani 1 1 d . . . . .
O3A O 0.8129(3) 0.1970(4) 0.30361(19) 0.0290(9) Uani 1 1 d . . . . .
N1A N 0.6108(4) 0.3982(5) 0.0913(2) 0.0266(11) Uani 1 1 d . . . . .
H1A H 0.5812 0.3811 0.1278 0.032 Uiso 1 1 calc R U . . .
C1A C 0.6819(5) 0.5172(6) 0.0948(3) 0.0264(13) Uani 1 1 d . . . . .
C2A C 0.7160(5) 0.5857(7) 0.1710(4) 0.0424(16) Uani 1 1 d . . . . .
H2A H 0.6699 0.5663 0.2032 0.051 Uiso 1 1 calc R U . . .
C3A C 0.8046(6) 0.6685(8) 0.1931(4) 0.0444(17) Uani 1 1 d . . . . .
H3A H 0.8460 0.6953 0.1591 0.053 Uiso 1 1 calc R U . . .
C4A C 0.8473(5) 0.7267(7) 0.2709(3) 0.0390(16) Uani 1 1 d . . . . .
H4A1 H 0.7816 0.7509 0.2903 0.047 Uiso 1 1 calc R U . . .
H4A2 H 0.8902 0.8206 0.2701 0.047 Uiso 1 1 calc R U . . .
C5A C 0.9251(5) 0.6111(6) 0.3230(3) 0.0272(13) Uani 1 1 d . . . . .
H5A1 H 0.9538 0.6591 0.3707 0.033 Uiso 1 1 calc R U . . .
H5A2 H 0.8786 0.5241 0.3299 0.033 Uiso 1 1 calc R U . . .
C6A C 1.0276(4) 0.5528(6) 0.2959(3) 0.0231(11) Uani 1 1 d . . . . .
H6A H 0.9984 0.5031 0.2480 0.028 Uiso 1 1 calc R U . . .
C7A C 1.0978(4) 0.4360(6) 0.3492(3) 0.0230(12) Uani 1 1 d . . . . .
H7A1 H 1.1647 0.4081 0.3318 0.028 Uiso 1 1 calc R U . . .
H7A2 H 1.1254 0.4849 0.3968 0.028 Uiso 1 1 calc R U . . .
C8A C 1.0349(4) 0.2904(6) 0.3599(3) 0.0194(11) Uani 1 1 d . . . . .
H8A H 0.9696 0.3176 0.3801 0.023 Uiso 1 1 calc R U . . .
C9A C 0.8782(4) 0.1924(6) 0.2641(3) 0.0200(11) Uani 1 1 d . . . . .
C10A C 0.8442(4) 0.1524(6) 0.1835(3) 0.0241(12) Uani 1 1 d . . . . .
H10C H 0.9001 0.0816 0.1729 0.029 Uiso 1 1 calc R U . . .
H10D H 0.8456 0.2444 0.1548 0.029 Uiso 1 1 calc R U . . .
C11A C 0.7255(4) 0.0810(6) 0.1602(3) 0.0211(11) Uani 1 1 d . . . . .
H11C H 0.6703 0.1502 0.1731 0.025 Uiso 1 1 calc R U . . .
H11D H 0.7252 -0.0129 0.1877 0.025 Uiso 1 1 calc R U . . .
C12A C 0.6866(5) 0.0452(6) 0.0780(3) 0.0270(12) Uani 1 1 d . . . . .
H12C H 0.7411 -0.0265 0.0661 0.032 Uiso 1 1 calc R U . . .
H12D H 0.6128 -0.0063 0.0688 0.032 Uiso 1 1 calc R U . . .
C13A C 0.6747(5) 0.1803(6) 0.0249(3) 0.0260(12) Uani 1 1 d . . . . .
H13C H 0.7480 0.2332 0.0346 0.031 Uiso 1 1 calc R U . . .
H13D H 0.6593 0.1403 -0.0248 0.031 Uiso 1 1 calc R U . . .
C14A C 0.5817(5) 0.2968(6) 0.0282(3) 0.0291(13) Uani 1 1 d . . . . .
H14C H 0.5662 0.3581 -0.0163 0.035 Uiso 1 1 calc R U . . .
H14D H 0.5115 0.2424 0.0290 0.035 Uiso 1 1 calc R U . . .
C15A C 1.1057(5) 0.6852(7) 0.2862(4) 0.0405(15) Uani 1 1 d . . . . .
H15D H 1.0639 0.7537 0.2490 0.061 Uiso 1 1 calc R U . . .
H15E H 1.1713 0.6459 0.2715 0.061 Uiso 1 1 calc R U . . .
H15F H 1.1310 0.7393 0.3319 0.061 Uiso 1 1 calc R U . . .
C16A C 1.1083(4) 0.1682(6) 0.4104(3) 0.0245(12) Uani 1 1 d . . . . .
C17A C 1.2017(5) 0.1028(6) 0.3763(3) 0.0307(14) Uani 1 1 d . . . . .
H17D H 1.2525 0.1835 0.3697 0.046 Uiso 1 1 calc R U . . .
H17E H 1.1664 0.0578 0.3294 0.046 Uiso 1 1 calc R U . . .
H17F H 1.2446 0.0262 0.4083 0.046 Uiso 1 1 calc R U . . .
C18A C 1.1636(5) 0.2424(7) 0.4848(3) 0.0360(15) Uani 1 1 d . . . . .
H18D H 1.1968 0.1645 0.5197 0.054 Uiso 1 1 calc R U . . .
H18E H 1.1061 0.2970 0.5021 0.054 Uiso 1 1 calc R U . . .
H18F H 1.2226 0.3122 0.4791 0.054 Uiso 1 1 calc R U . . .
C19A C 1.0299(5) 0.0386(7) 0.4223(3) 0.0329(14) Uani 1 1 d . . . . .
H19D H 0.9963 -0.0101 0.3761 0.049 Uiso 1 1 calc R U . . .
H19E H 0.9700 0.0792 0.4426 0.049 Uiso 1 1 calc R U . . .
H19F H 1.0740 -0.0348 0.4558 0.049 Uiso 1 1 calc R U . . .
O1B O 0.0410(3) -0.0578(5) 0.1308(2) 0.0358(10) Uani 1 1 d . . . . .
O2B O 0.4318(3) 0.2305(4) 0.30056(17) 0.0183(8) Uani 1 1 d . . . . .
O3B O 0.4972(3) 0.2795(5) 0.20081(18) 0.0304(9) Uani 1 1 d . . . . .
N1B N 0.1387(4) 0.0612(5) 0.0583(2) 0.0256(10) Uani 1 1 d . . . . .
H1B H 0.1994 0.0613 0.0417 0.031 Uiso 1 1 calc R U . . .
C1B C 0.1282(5) -0.0453(6) 0.1077(3) 0.0240(12) Uani 1 1 d . . . . .
C2B C 0.2286(5) -0.1446(6) 0.1373(3) 0.0237(12) Uani 1 1 d . . . . .
H2B H 0.2133 -0.2417 0.1528 0.028 Uiso 1 1 calc R U . . .
C3B C 0.3373(5) -0.1100(6) 0.1441(3) 0.0214(12) Uani 1 1 d . . . . .
H3B H 0.3537 -0.0181 0.1238 0.026 Uiso 1 1 calc R U . . .
C4B C 0.4370(4) -0.2081(6) 0.1823(3) 0.0250(12) Uani 1 1 d . . . . .
H4B1 H 0.4834 -0.2317 0.1481 0.030 Uiso 1 1 calc R U . . .
H4B2 H 0.4080 -0.3037 0.1968 0.030 Uiso 1 1 calc R U . . .
C5B C 0.5128(4) -0.1304(6) 0.2505(3) 0.0224(12) Uani 1 1 d . . . . .
H5B1 H 0.5422 -0.0354 0.2357 0.027 Uiso 1 1 calc R U . . .
H5B2 H 0.5781 -0.1960 0.2710 0.027 Uiso 1 1 calc R U . . .
C6B C 0.4496(4) -0.0955(6) 0.3112(3) 0.0188(11) Uani 1 1 d . . . . .
H6B H 0.3764 -0.0460 0.2877 0.023 Uiso 1 1 calc R U . . .
C7B C 0.5181(4) 0.0139(5) 0.3695(3) 0.0211(12) Uani 1 1 d . . . . .
H7B1 H 0.4763 0.0272 0.4072 0.025 Uiso 1 1 calc R U . . .
H7B2 H 0.5910 -0.0343 0.3926 0.025 Uiso 1 1 calc R U . . .
C8B C 0.5427(4) 0.1706(6) 0.3426(3) 0.0182(11) Uani 1 1 d . . . . .
H8B H 0.5941 0.1596 0.3097 0.022 Uiso 1 1 calc R U . . .
C9B C 0.4194(4) 0.2763(6) 0.2308(3) 0.0193(11) Uani 1 1 d . . . . .
C10B C 0.2977(4) 0.3180(6) 0.1958(3) 0.0220(11) Uani 1 1 d . . . . .
H10E H 0.2749 0.4010 0.2235 0.026 Uiso 1 1 calc R U . . .
H10F H 0.2489 0.2309 0.1985 0.026 Uiso 1 1 calc R U . . .
C11B C 0.2781(5) 0.3666(6) 0.1160(3) 0.0258(12) Uani 1 1 d . . . . .
H11E H 0.2939 0.2805 0.0874 0.031 Uiso 1 1 calc R U . . .
H11F H 0.3319 0.4475 0.1127 0.031 Uiso 1 1 calc R U . . .
C12B C 0.1561(4) 0.4231(6) 0.0829(3) 0.0311(14) Uani 1 1 d . . . . .
H12E H 0.1441 0.5144 0.1094 0.037 Uiso 1 1 calc R U . . .
H12F H 0.1509 0.4532 0.0324 0.037 Uiso 1 1 calc R U . . .
C13B C 0.0581(4) 0.3134(6) 0.0826(3) 0.0241(12) Uani 1 1 d . . . . .
H13E H -0.0137 0.3696 0.0686 0.029 Uiso 1 1 calc R U . . .
H13F H 0.0662 0.2762 0.1324 0.029 Uiso 1 1 calc R U . . .
C14B C 0.0504(5) 0.1767(7) 0.0318(3) 0.0308(13) Uani 1 1 d . . . . .
H14E H -0.0246 0.1296 0.0253 0.037 Uiso 1 1 calc R U . . .
H14F H 0.0566 0.2124 -0.0161 0.037 Uiso 1 1 calc R U . . .
C15B C 0.4228(5) -0.2413(6) 0.3480(3) 0.0297(13) Uani 1 1 d . . . . .
H15A H 0.4932 -0.2859 0.3761 0.045 Uiso 1 1 calc R U . . .
H15B H 0.3843 -0.3125 0.3110 0.045 Uiso 1 1 calc R U . . .
H15C H 0.3740 -0.2175 0.3800 0.045 Uiso 1 1 calc R U . . .
C16B C 0.5944(4) 0.2888(6) 0.4030(3) 0.0216(11) Uani 1 1 d . . . . .
C17B C 0.5070(5) 0.3384(7) 0.4455(3) 0.0327(14) Uani 1 1 d . . . . .
H17A H 0.4785 0.2499 0.4656 0.049 Uiso 1 1 calc R U . . .
H17B H 0.4442 0.3906 0.4129 0.049 Uiso 1 1 calc R U . . .
H17C H 0.5435 0.4059 0.4848 0.049 Uiso 1 1 calc R U . . .
C18B C 0.7003(4) 0.2190(7) 0.4558(3) 0.0326(14) Uani 1 1 d . . . . .
H18A H 0.7500 0.1760 0.4281 0.049 Uiso 1 1 calc R U . . .
H18B H 0.6764 0.1402 0.4845 0.049 Uiso 1 1 calc R U . . .
H18C H 0.7408 0.2971 0.4881 0.049 Uiso 1 1 calc R U . . .
C19B C 0.6309(5) 0.4286(6) 0.3659(3) 0.0312(13) Uani 1 1 d . . . . .
H19A H 0.6627 0.5041 0.4025 0.047 Uiso 1 1 calc R U . . .
H19B H 0.5651 0.4706 0.3314 0.047 Uiso 1 1 calc R U . . .
H19C H 0.6877 0.3993 0.3405 0.047 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
O1A C1A 1.216(6) . ?
O2A C9A 1.343(6) . ?
O2A C8A 1.458(6) . ?
O3A C9A 1.205(6) . ?
N1A C1A 1.337(7) . ?
N1A C14A 1.449(7) . ?
C1A C2A 1.510(8) . ?
C2A C3A 1.268(9) . ?
C3A C4A 1.510(8) . ?
C4A C5A 1.548(7) . ?
C5A C6A 1.531(7) . ?
C6A C7A 1.527(7) . ?
C6A C15A 1.528(8) . ?
C7A C8A 1.519(7) . ?
C8A C16A 1.548(7) . ?
C9A C10A 1.505(7) . ?
C10A C11A 1.516(7) . ?
C11A C12A 1.529(7) . ?
C12A C13A 1.527(7) . ?
C13A C14A 1.524(7) . ?
C16A C19A 1.524(7) . ?
C16A C18A 1.532(8) . ?
C16A C17A 1.533(7) . ?
O1B C1B 1.233(6) . ?
O2B C9B 1.341(5) . ?
O2B C8B 1.465(6) . ?
O3B C9B 1.204(6) . ?
N1B C1B 1.342(7) . ?
N1B C14B 1.458(7) . ?
C1B C2B 1.476(8) . ?
C2B C3B 1.315(7) . ?
C3B C4B 1.501(7) . ?
C4B C5B 1.532(7) . ?
C5B C6B 1.546(7) . ?
C6B C15B 1.521(7) . ?
C6B C7B 1.530(7) . ?
C7B C8B 1.514(7) . ?
C8B C16B 1.545(7) . ?
C9B C10B 1.489(7) . ?
C10B C11B 1.517(7) . ?
C11B C12B 1.524(7) . ?
C12B C13B 1.516(7) . ?
C13B C14B 1.517(7) . ?
C16B C19B 1.522(8) . ?
C16B C17B 1.529(7) . ?
C16B C18B 1.530(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A O2A C8A 118.9(4) . . ?
C1A N1A C14A 122.5(5) . . ?
O1A C1A N1A 122.9(5) . . ?
O1A C1A C2A 125.0(5) . . ?
N1A C1A C2A 112.0(5) . . ?
C3A C2A C1A 122.9(6) . . ?
C2A C3A C4A 124.3(7) . . ?
C3A C4A C5A 113.4(5) . . ?
C6A C5A C4A 114.5(5) . . ?
C7A C6A C15A 109.2(4) . . ?
C7A C6A C5A 111.2(4) . . ?
C15A C6A C5A 110.8(5) . . ?
C8A C7A C6A 115.8(4) . . ?
O2A C8A C7A 105.9(4) . . ?
O2A C8A C16A 109.3(4) . . ?
C7A C8A C16A 115.6(4) . . ?
O3A C9A O2A 123.8(4) . . ?
O3A C9A C10A 124.7(4) . . ?
O2A C9A C10A 111.5(4) . . ?
C9A C10A C11A 112.7(4) . . ?
C10A C11A C12A 113.8(4) . . ?
C13A C12A C11A 117.0(4) . . ?
C14A C13A C12A 116.2(5) . . ?
N1A C14A C13A 114.3(4) . . ?
C19A C16A C18A 108.9(5) . . ?
C19A C16A C17A 109.0(5) . . ?
C18A C16A C17A 110.0(5) . . ?
C19A C16A C8A 108.9(4) . . ?
C18A C16A C8A 108.4(4) . . ?
C17A C16A C8A 111.5(4) . . ?
C9B O2B C8B 119.8(4) . . ?
C1B N1B C14B 122.1(4) . . ?
O1B C1B N1B 122.6(5) . . ?
O1B C1B C2B 120.0(5) . . ?
N1B C1B C2B 117.4(5) . . ?
C3B C2B C1B 126.8(5) . . ?
C2B C3B C4B 124.7(5) . . ?
C3B C4B C5B 112.5(4) . . ?
C4B C5B C6B 113.8(4) . . ?
C15B C6B C7B 109.6(4) . . ?
C15B C6B C5B 111.5(4) . . ?
C7B C6B C5B 112.0(4) . . ?
C8B C7B C6B 116.2(4) . . ?
O2B C8B C7B 106.0(4) . . ?
O2B C8B C16B 107.5(4) . . ?
C7B C8B C16B 115.9(4) . . ?
O3B C9B O2B 123.5(4) . . ?
O3B C9B C10B 125.3(4) . . ?
O2B C9B C10B 111.2(4) . . ?
C9B C10B C11B 113.4(4) . . ?
C10B C11B C12B 113.0(5) . . ?
C13B C12B C11B 117.5(4) . . ?
C12B C13B C14B 115.2(5) . . ?
N1B C14B C13B 113.9(4) . . ?
C19B C16B C17B 108.8(4) . . ?
C19B C16B C18B 109.2(4) . . ?
C17B C16B C18B 110.0(4) . . ?
C19B C16B C8B 108.1(4) . . ?
C17B C16B C8B 111.7(4) . . ?
C18B C16B C8B 109.0(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
C14A N1A C1A O1A 7.4(8) . . . . ?
C14A N1A C1A C2A -169.0(4) . . . . ?
O1A C1A C2A C3A -16.5(9) . . . . ?
N1A C1A C2A C3A 159.8(6) . . . . ?
C1A C2A C3A C4A -174.1(5) . . . . ?
C2A C3A C4A C5A 85.0(8) . . . . ?
C3A C4A C5A C6A 54.0(7) . . . . ?
C4A C5A C6A C7A -178.4(5) . . . . ?
C4A C5A C6A C15A 59.9(6) . . . . ?
C15A C6A C7A C8A -175.1(5) . . . . ?
C5A C6A C7A C8A 62.3(6) . . . . ?
C9A O2A C8A C7A -126.9(4) . . . . ?
C9A O2A C8A C16A 107.9(5) . . . . ?
C6A C7A C8A O2A 55.3(5) . . . . ?
C6A C7A C8A C16A 176.5(4) . . . . ?
C8A O2A C9A O3A -7.9(7) . . . . ?
C8A O2A C9A C10A 170.6(4) . . . . ?
O3A C9A C10A C11A -13.9(7) . . . . ?
O2A C9A C10A C11A 167.6(4) . . . . ?
C9A C10A C11A C12A 177.6(4) . . . . ?
C10A C11A C12A C13A -61.8(6) . . . . ?
C11A C12A C13A C14A -65.2(6) . . . . ?
C1A N1A C14A C13A 77.7(6) . . . . ?
C12A C13A C14A N1A 75.5(6) . . . . ?
O2A C8A C16A C19A -67.1(5) . . . . ?
C7A C8A C16A C19A 173.6(4) . . . . ?
O2A C8A C16A C18A 174.4(4) . . . . ?
C7A C8A C16A C18A 55.2(6) . . . . ?
O2A C8A C16A C17A 53.2(5) . . . . ?
C7A C8A C16A C17A -66.0(6) . . . . ?
C14B N1B C1B O1B 4.1(7) . . . . ?
C14B N1B C1B C2B -172.8(4) . . . . ?
O1B C1B C2B C3B -149.2(5) . . . . ?
N1B C1B C2B C3B 27.8(8) . . . . ?
C1B C2B C3B C4B 172.8(5) . . . . ?
C2B C3B C4B C5B -116.1(5) . . . . ?
C3B C4B C5B C6B 62.1(6) . . . . ?
C4B C5B C6B C15B 70.2(6) . . . . ?
C4B C5B C6B C7B -166.6(4) . . . . ?
C15B C6B C7B C8B -174.8(4) . . . . ?
C5B C6B C7B C8B 61.0(6) . . . . ?
C9B O2B C8B C7B -124.7(4) . . . . ?
C9B O2B C8B C16B 110.7(4) . . . . ?
C6B C7B C8B O2B 51.3(5) . . . . ?
C6B C7B C8B C16B 170.5(4) . . . . ?
C8B O2B C9B O3B -4.3(7) . . . . ?
C8B O2B C9B C10B 174.3(4) . . . . ?
O3B C9B C10B C11B 0.2(7) . . . . ?
O2B C9B C10B C11B -178.4(4) . . . . ?
C9B C10B C11B C12B -174.7(4) . . . . ?
C10B C11B C12B C13B -58.7(7) . . . . ?
C11B C12B C13B C14B -68.5(7) . . . . ?
C1B N1B C14B C13B 82.4(6) . . . . ?
C12B C13B C14B N1B 73.7(6) . . . . ?
O2B C8B C16B C19B -70.6(5) . . . . ?
C7B C8B C16B C19B 170.9(4) . . . . ?
O2B C8B C16B C17B 49.0(5) . . . . ?
C7B C8B C16B C17B -69.4(5) . . . . ?
O2B C8B C16B C18B 170.8(4) . . . . ?
C7B C8B C16B C18B 52.3(5) . . . . ?

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.099

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate-hexane'
####################################################################### 
# 
# 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_Compound_30
_database_code_depnum_ccdc_archive 'CCDC 1454804'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(3R,14R,16S,E)-16-(tert-butyl)-3,8,14-trimethyl-1-oxa-8-azacyclohexadec-10-ene-2,9-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H37 N O3'
_chemical_formula_sum            'C21 H37 N O3'
_chemical_formula_weight         351.51

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.615(3)
_cell_length_b                   10.654(5)
_cell_length_c                   35.955(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2151.0(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3113
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      23.29

_exptl_crystal_description       'THICK PLATE'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   SADABS(BRUKER,2006)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19159
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4182
_reflns_number_gt                3406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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-2014/7 (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)] 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_abs_structure_details 
;
 Flack x determined using 1205 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4182
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.618
_refine_ls_restrained_S_all      1.618
_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
O1 O -0.0339(3) 0.71049(15) 0.27682(5) 0.0267(5) Uani 1 1 d . . . . .
O2 O 0.2911(3) 0.46361(13) 0.42336(5) 0.0172(4) Uani 1 1 d . . . . .
O3 O 0.6084(3) 0.34523(17) 0.40762(5) 0.0314(5) Uani 1 1 d . . . . .
N1 N 0.2533(4) 0.58253(17) 0.25396(6) 0.0188(5) Uani 1 1 d . . . . .
C1 C 0.1774(5) 0.6756(2) 0.27634(8) 0.0203(7) Uani 1 1 d . . . . .
C2 C 0.3568(5) 0.7392(2) 0.30053(7) 0.0179(6) Uani 1 1 d . . . . .
H2 H 0.5180 0.7238 0.2967 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2914(5) 0.8168(2) 0.32729(8) 0.0195(6) Uani 1 1 d . . . . .
H3 H 0.1292 0.8305 0.3306 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4593(5) 0.8844(2) 0.35268(7) 0.0210(7) Uani 1 1 d . . . . .
H4B H 0.4318 0.9740 0.3507 0.025 Uiso 1 1 calc R U . . .
H4A H 0.6217 0.8678 0.3449 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4285(5) 0.8438(2) 0.39335(7) 0.0216(6) Uani 1 1 d . . . . .
H5B H 0.5351 0.8933 0.4087 0.026 Uiso 1 1 calc R U . . .
H5A H 0.2669 0.8626 0.4011 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4774(4) 0.7046(2) 0.40059(7) 0.0178(6) Uani 1 1 d . . . . .
H6 H 0.3778 0.6557 0.3835 0.021 Uiso 1 1 calc R U . . .
C7 C 0.4023(4) 0.6724(2) 0.44025(7) 0.0175(6) Uani 1 1 d . . . . .
H7B H 0.4975 0.7221 0.4573 0.021 Uiso 1 1 calc R U . . .
H7A H 0.2375 0.6974 0.4435 0.021 Uiso 1 1 calc R U . . .
C8 C 0.4257(5) 0.5347(2) 0.45121(7) 0.0160(6) Uani 1 1 d . . . . .
H8 H 0.5938 0.5104 0.4497 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4009(5) 0.3716(2) 0.40426(7) 0.0225(7) Uani 1 1 d . . . . .
C10 C 0.2256(5) 0.3045(2) 0.37929(8) 0.0268(7) Uani 1 1 d . . . . .
H10 H 0.0801 0.3550 0.3775 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3305(5) 0.2881(2) 0.34046(8) 0.0288(7) Uani 1 1 d . . . . .
H11B H 0.2259 0.2344 0.3261 0.035 Uiso 1 1 calc R U . . .
H11A H 0.4831 0.2460 0.3426 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3657(5) 0.4115(2) 0.31948(8) 0.0254(7) Uani 1 1 d . . . . .
H12B H 0.2159 0.4568 0.3190 0.031 Uiso 1 1 calc R U . . .
H12A H 0.4803 0.4626 0.3328 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4520(5) 0.3933(2) 0.27991(7) 0.0243(7) Uani 1 1 d . . . . .
H13B H 0.3409 0.3388 0.2670 0.029 Uiso 1 1 calc R U . . .
H13A H 0.6049 0.3510 0.2805 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4782(4) 0.5145(2) 0.25778(8) 0.0218(6) Uani 1 1 d . . . . .
H14B H 0.5935 0.5681 0.2701 0.026 Uiso 1 1 calc R U . . .
H14A H 0.5393 0.4948 0.2332 0.026 Uiso 1 1 calc R U . . .
C15 C 0.0821(5) 0.5262(2) 0.22861(8) 0.0324(8) Uani 1 1 d . . . . .
H15B H 0.0107 0.4543 0.2402 0.049 Uiso 1 1 calc R U . . .
H15A H 0.1619 0.5007 0.2062 0.049 Uiso 1 1 calc R U . . .
H15C H -0.0393 0.5863 0.2227 0.049 Uiso 1 1 calc R U . . .
C16 C 0.7390(4) 0.6714(2) 0.39266(8) 0.0292(7) Uani 1 1 d . . . . .
H16C H 0.8407 0.7205 0.4084 0.044 Uiso 1 1 calc R U . . .
H16A H 0.7750 0.6892 0.3671 0.044 Uiso 1 1 calc R U . . .
H16B H 0.7646 0.5838 0.3975 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3288(4) 0.4987(2) 0.48975(8) 0.0161(6) Uani 1 1 d . . . . .
C18 C 0.0575(4) 0.5073(2) 0.49113(7) 0.0234(7) Uani 1 1 d . . . . .
H18A H -0.0098 0.4513 0.4731 0.035 Uiso 1 1 calc R U . . .
H18B H 0.0089 0.5918 0.4857 0.035 Uiso 1 1 calc R U . . .
H18C H 0.0028 0.4844 0.5155 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4358(4) 0.5848(2) 0.51950(7) 0.0216(7) Uani 1 1 d . . . . .
H19B H 0.3977 0.5527 0.5437 0.032 Uiso 1 1 calc R U . . .
H19A H 0.3712 0.6677 0.5168 0.032 Uiso 1 1 calc R U . . .
H19C H 0.6057 0.5878 0.5166 0.032 Uiso 1 1 calc R U . . .
C20 C 0.4045(4) 0.3641(2) 0.49830(7) 0.0217(7) Uani 1 1 d . . . . .
H20B H 0.5748 0.3601 0.5002 0.033 Uiso 1 1 calc R U . . .
H20C H 0.3518 0.3097 0.4787 0.033 Uiso 1 1 calc R U . . .
H20A H 0.3344 0.3378 0.5214 0.033 Uiso 1 1 calc R U . . .
C21 C 0.1648(5) 0.1790(2) 0.39737(8) 0.0402(9) Uani 1 1 d . . . . .
H21A H 0.3081 0.1315 0.4011 0.060 Uiso 1 1 calc R U . . .
H21B H 0.0587 0.1330 0.3815 0.060 Uiso 1 1 calc R U . . .
H21C H 0.0893 0.1935 0.4209 0.060 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
O1 C1 1.243(3) . ?
O2 C9 1.346(3) . ?
O2 C8 1.465(3) . ?
O3 C9 1.204(3) . ?
N1 C1 1.346(3) . ?
N1 C15 1.454(3) . ?
N1 C14 1.463(3) . ?
C1 C2 1.493(3) . ?
C2 C3 1.321(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.496(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.535(3) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C5 C6 1.530(3) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 C7 1.526(3) . ?
C6 C16 1.537(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.525(3) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C8 C17 1.537(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.512(4) . ?
C10 C11 1.525(4) . ?
C10 C21 1.526(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.528(3) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 C13 1.516(3) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 C14 1.524(3) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
C15 H15B 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C17 C20 1.527(3) . ?
C17 C18 1.527(3) . ?
C17 C19 1.531(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20A 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
C9 O2 C8 119.2(2) . . ?
C1 N1 C15 118.0(2) . . ?
C1 N1 C14 125.6(2) . . ?
C15 N1 C14 115.1(2) . . ?
O1 C1 N1 122.0(3) . . ?
O1 C1 C2 120.0(2) . . ?
N1 C1 C2 117.9(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 124.8(2) . . ?
C2 C3 H3 117.6 . . ?
C4 C3 H3 117.6 . . ?
C3 C4 C5 112.0(2) . . ?
C3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
H4B C4 H4A 107.9 . . ?
C6 C5 C4 114.5(2) . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5A 108.6 . . ?
H5B C5 H5A 107.6 . . ?
C7 C6 C5 109.1(2) . . ?
C7 C6 C16 112.7(2) . . ?
C5 C6 C16 111.3(2) . . ?
C7 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C16 C6 H6 107.9 . . ?
C8 C7 C6 115.7(2) . . ?
C8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
H7B C7 H7A 107.4 . . ?
O2 C8 C7 106.03(19) . . ?
O2 C8 C17 107.75(19) . . ?
C7 C8 C17 116.2(2) . . ?
O2 C8 H8 108.9 . . ?
C7 C8 H8 108.9 . . ?
C17 C8 H8 108.9 . . ?
O3 C9 O2 124.2(3) . . ?
O3 C9 C10 125.4(3) . . ?
O2 C9 C10 110.4(2) . . ?
C9 C10 C11 110.2(2) . . ?
C9 C10 C21 107.9(2) . . ?
C11 C10 C21 112.1(2) . . ?
C9 C10 H10 108.9 . . ?
C11 C10 H10 108.9 . . ?
C21 C10 H10 108.9 . . ?
C10 C11 C12 113.8(2) . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
H11B C11 H11A 107.7 . . ?
C13 C12 C11 113.2(2) . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
H12B C12 H12A 107.7 . . ?
C12 C13 C14 114.4(2) . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
H13B C13 H13A 107.6 . . ?
N1 C14 C13 112.7(2) . . ?
N1 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
N1 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
H14B C14 H14A 107.8 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
C6 C16 H16C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C20 C17 C18 109.1(2) . . ?
C20 C17 C19 108.2(2) . . ?
C18 C17 C19 109.4(2) . . ?
C20 C17 C8 108.5(2) . . ?
C18 C17 C8 111.5(2) . . ?
C19 C17 C8 110.0(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
C10 C21 H21A 109.5 . . ?
C10 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C10 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
C15 N1 C1 O1 2.8(4) . . . . ?
C14 N1 C1 O1 -163.8(2) . . . . ?
C15 N1 C1 C2 -176.0(2) . . . . ?
C14 N1 C1 C2 17.4(4) . . . . ?
O1 C1 C2 C3 12.1(4) . . . . ?
N1 C1 C2 C3 -169.1(2) . . . . ?
C1 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -116.1(3) . . . . ?
C3 C4 C5 C6 61.3(3) . . . . ?
C4 C5 C6 C7 -170.9(2) . . . . ?
C4 C5 C6 C16 64.1(3) . . . . ?
C5 C6 C7 C8 176.5(2) . . . . ?
C16 C6 C7 C8 -59.4(3) . . . . ?
C9 O2 C8 C7 124.3(2) . . . . ?
C9 O2 C8 C17 -110.6(2) . . . . ?
C6 C7 C8 O2 -54.8(3) . . . . ?
C6 C7 C8 C17 -174.4(2) . . . . ?
C8 O2 C9 O3 -2.4(4) . . . . ?
C8 O2 C9 C10 175.7(2) . . . . ?
O3 C9 C10 C11 -48.3(4) . . . . ?
O2 C9 C10 C11 133.6(2) . . . . ?
O3 C9 C10 C21 74.4(4) . . . . ?
O2 C9 C10 C21 -103.7(2) . . . . ?
C9 C10 C11 C12 -66.9(3) . . . . ?
C21 C10 C11 C12 172.9(2) . . . . ?
C10 C11 C12 C13 -175.5(2) . . . . ?
C11 C12 C13 C14 177.5(2) . . . . ?
C1 N1 C14 C13 94.3(3) . . . . ?
C15 N1 C14 C13 -72.6(3) . . . . ?
C12 C13 C14 N1 -60.8(3) . . . . ?
O2 C8 C17 C20 70.5(2) . . . . ?
C7 C8 C17 C20 -170.7(2) . . . . ?
O2 C8 C17 C18 -49.7(2) . . . . ?
C7 C8 C17 C18 69.1(3) . . . . ?
O2 C8 C17 C19 -171.29(18) . . . . ?
C7 C8 C17 C19 -52.5(3) . . . . ?

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate-hexane-dichloromethane'
