# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frm_0m
_audit_creation_date             2013-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8244(7)
_cell_length_b                   10.0482(8)
_cell_length_c                   20.7767(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1842.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.25
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.9363.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.100
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24125
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.96
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                3682
_reflns_number_total             3791
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      3.810
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0367P)²+0.3773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0724
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-H5
 1 with sigma of 0.005
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C22(H22A,H22B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C23(H23), C24(H24), C5(H5)
3.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0055(4) 0.9698(3) 0.24457(16) 0.0235(7) Uani 1 1 d . . .
O3 O 0.1954(4) 0.9430(3) 0.15401(16) 0.0235(7) Uani 1 1 d . . .
N4 N -0.0190(4) 0.8327(4) 0.25245(19) 0.0201(8) Uani 1 1 d . . .
C6 C 0.3148(5) 0.8051(4) 0.2361(2) 0.0188(9) Uani 1 1 d . . .
C7 C 0.3448(5) 0.6846(5) 0.2670(2) 0.0217(9) Uani 1 1 d . . .
H7 H 0.3107 0.6054 0.2490 0.026 Uiso 1 1 calc R . .
C8 C 0.4768(5) 0.8004(5) 0.3517(2) 0.0251(10) Uani 1 1 d . . .
H8 H 0.5273 0.7994 0.3910 0.030 Uiso 1 1 calc R . .
C9 C 0.3733(5) 0.9219(5) 0.2619(2) 0.0212(9) Uani 1 1 d . . .
H9 H 0.3595 1.0020 0.2402 0.025 Uiso 1 1 calc R . .
C11 C 0.2097(5) 0.8099(4) 0.1770(2) 0.0193(9) Uani 1 1 d . . .
C12 C 0.0370(5) 0.7870(4) 0.3155(2) 0.0211(9) Uani 1 1 d . . .
H12 H 0.0377 0.6963 0.3243 0.025 Uiso 1 1 calc R . .
C13 C 0.2774(5) 0.7272(5) 0.1221(2) 0.0218(9) Uani 1 1 d . . .
C14 C 0.4253(5) 0.6823(5) 0.3246(2) 0.0240(10) Uani 1 1 d . . .
H14 H 0.4446 0.6016 0.3449 0.029 Uiso 1 1 calc R . .
C15 C 0.4523(5) 0.9203(5) 0.3198(2) 0.0244(9) Uani 1 1 d . . .
H15 H 0.4888 0.9994 0.3372 0.029 Uiso 1 1 calc R . .
C16 C 0.2269(6) 0.5999(5) 0.1063(2) 0.0253(10) Uani 1 1 d . . .
H16 H 0.1492 0.5611 0.1299 0.030 Uiso 1 1 calc R . .
C17 C 0.4100(7) 0.5848(5) 0.0207(2) 0.0344(12) Uani 1 1 d . . .
H17 H 0.4532 0.5381 -0.0133 0.041 Uiso 1 1 calc R . .
C18 C 0.3981(6) 0.7813(5) 0.0873(2) 0.0284(10) Uani 1 1 d . . .
H18 H 0.4347 0.8653 0.0977 0.034 Uiso 1 1 calc R . .
C20 C -0.2197(6) 0.8101(6) 0.1766(3) 0.0341(12) Uani 1 1 d . . .
H20A H -0.2484 0.9010 0.1668 0.041 Uiso 1 1 calc R . .
H20B H -0.3012 0.7511 0.1637 0.041 Uiso 1 1 calc R . .
C21 C 0.0504(5) 0.7566(4) 0.1951(2) 0.0194(9) Uani 1 1 d . . .
H21 H 0.0587 0.6622 0.2065 0.023 Uiso 1 1 calc R . .
C22 C -0.1850(5) 0.7942(5) 0.2475(3) 0.0279(10) Uani 1 1 d . . .
H22A H -0.2008 0.7031 0.2613 0.034 Uiso 1 1 calc R . .
H22B H -0.2478 0.8528 0.2733 0.034 Uiso 1 1 calc R . .
C23 C 0.2919(6) 0.5300(5) 0.0552(2) 0.0294(11) Uani 1 1 d . . .
H23 H 0.2554 0.4462 0.0443 0.035 Uiso 1 1 calc R . .
C24 C 0.4641(7) 0.7104(6) 0.0371(2) 0.0359(12) Uani 1 1 d . . .
H24 H 0.5447 0.7471 0.0144 0.043 Uiso 1 1 calc R . .
C25 C -0.0707(5) 0.7727(5) 0.1424(2) 0.0255(10) Uani 1 1 d . . .
H25A H -0.0828 0.6902 0.1188 0.031 Uiso 1 1 calc R . .
H25B H -0.0414 0.8421 0.1125 0.031 Uiso 1 1 calc R . .
O2 O 0.1885(4) 0.9267(4) 0.45788(16) 0.0300(8) Uani 1 1 d . . .
O4 O 0.1267(5) 0.7116(4) 0.44294(17) 0.0363(9) Uani 1 1 d . . .
C3 C 0.2443(7) 0.8939(7) 0.5213(2) 0.0424(14) Uani 1 1 d . . .
H3A H 0.1653 0.8517 0.5456 0.064 Uiso 1 1 calc R . .
H3B H 0.2756 0.9738 0.5429 0.064 Uiso 1 1 calc R . .
H3C H 0.3290 0.8345 0.5176 0.064 Uiso 1 1 calc R . .
C2 C 0.1342(5) 0.8254(5) 0.4231(2) 0.0252(10) Uani 1 1 d D . .
C5 C 0.0861(5) 0.8706(4) 0.3598(2) 0.0220(9) Uani 1 1 d . . .
H5 H 0.0901 0.9610 0.3503 0.026 Uiso 1 1 calc RD . .
H3 H 0.127(8) 0.979(7) 0.183(3) 0.05(2) 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
O1 N4 1.392(4) . ?
O3 C11 1.426(5) . ?
N4 C12 1.473(6) . ?
N4 C21 1.542(5) . ?
N4 C22 1.519(6) . ?
C6 C7 1.395(6) . ?
C6 C9 1.390(6) . ?
C6 C11 1.540(6) . ?
C7 C14 1.392(6) . ?
C8 C14 1.391(7) . ?
C8 C15 1.393(7) . ?
C9 C15 1.390(6) . ?
C11 C13 1.531(6) . ?
C11 C21 1.551(6) . ?
C12 C5 1.320(6) . ?
C13 C16 1.394(6) . ?
C13 C18 1.398(7) . ?
C16 C23 1.396(7) . ?
C17 C23 1.378(8) . ?
C17 C24 1.392(8) . ?
C18 C24 1.390(7) . ?
C20 C22 1.512(7) . ?
C20 C25 1.541(7) . ?
C21 C25 1.538(6) . ?
O2 C3 1.445(6) . ?
O2 C2 1.337(6) . ?
O4 C2 1.218(6) . ?
C2 C5 1.454(6) . ?

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
O1 N4 C12 112.6(3) . . ?
O1 N4 C21 111.5(3) . . ?
O1 N4 C22 109.0(3) . . ?
C12 N4 C21 113.5(3) . . ?
C12 N4 C22 107.7(4) . . ?
C22 N4 C21 101.8(3) . . ?
C7 C6 C11 120.5(4) . . ?
C9 C6 C7 119.0(4) . . ?
C9 C6 C11 120.3(4) . . ?
C14 C7 C6 120.5(4) . . ?
C14 C8 C15 119.6(4) . . ?
C15 C9 C6 120.7(4) . . ?
O3 C11 C6 110.4(3) . . ?
O3 C11 C13 107.1(3) . . ?
O3 C11 C21 109.0(3) . . ?
C6 C11 C21 109.9(3) . . ?
C13 C11 C6 110.0(3) . . ?
C13 C11 C21 110.3(4) . . ?
C5 C12 N4 122.1(4) . . ?
C16 C13 C11 123.3(4) . . ?
C16 C13 C18 118.5(4) . . ?
C18 C13 C11 118.2(4) . . ?
C8 C14 C7 120.1(4) . . ?
C9 C15 C8 120.0(4) . . ?
C13 C16 C23 120.7(5) . . ?
C23 C17 C24 119.6(5) . . ?
C24 C18 C13 120.5(5) . . ?
C22 C20 C25 104.5(4) . . ?
N4 C21 C11 112.1(3) . . ?
C25 C21 N4 102.8(3) . . ?
C25 C21 C11 114.8(4) . . ?
C20 C22 N4 103.6(4) . . ?
C17 C23 C16 120.3(5) . . ?
C18 C24 C17 120.3(5) . . ?
C21 C25 C20 106.9(4) . . ?
C2 O2 C3 116.2(4) . . ?
O2 C2 C5 110.8(4) . . ?
O4 C2 O2 123.5(4) . . ?
O4 C2 C5 125.7(4) . . ?
C12 C5 C2 121.9(4) . . ?

_database_code_depnum_ccdc_archive 'CCDC 963296'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_frm_0m
_audit_creation_date             2013-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H29 N O6'
_chemical_formula_sum            'C25 H29 N O6'
_chemical_formula_weight         439.49
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   10.252(2)
_cell_length_b                   10.869(2)
_cell_length_c                   40.512(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4514.4(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.27
_cell_measurement_theta_min      2.23
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0496 after correction.
The Ratio of minimum to maximum transmission is 0.9060.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            26084
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         1.94
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                8480
_reflns_number_total             9101
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(5)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         9101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.6874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0874
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C40(H40), C33(H33)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C25(H25A,H25B), C39(H39A,H39B), C49(H49A,H49B), C31(H31A,
 H31B), C43(H43A,H43B), C48(H48A,H48B), C59(H59A,H59B), C10(H10A,H10B), C1(H1A,
 H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C24(H24), C27(H27), C32(H32), C46(H46), C53(H53), C56(H56),
 C58(H58), C60(H60), C62(H62), C22(H22), C28(H28), C29(H29), C35(H35), C37(H37),
  C41(H41), C45(H45), C47(H47), C52(H52), C54(H54), C55(H55), C3(H3)
2.d Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C51(H51A,H51B,H51C), C63(H63A,H63B,H63C), C2(H2A,H2B,H2C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22401(11) 0.42474(10) 0.77913(3) 0.0203(2) Uani 1 1 d . . .
O6 O 0.05632(11) 0.78225(10) 0.69972(3) 0.0211(2) Uani 1 1 d . . .
O10 O 0.19708(13) 0.50689(10) 0.82988(3) 0.0240(3) Uani 1 1 d . . .
C16 C 0.47825(16) 0.60153(15) 0.72569(4) 0.0212(3) Uani 1 1 d . . .
H16 H 0.5304 0.5345 0.7311 0.025 Uiso 1 1 calc R . .
C17 C 0.11843(15) 0.66714(14) 0.70572(4) 0.0167(3) Uani 1 1 d . . .
C20 C -0.04788(15) 0.62554(14) 0.78822(4) 0.0202(3) Uani 1 1 d . . .
H20A H -0.0347 0.5410 0.7951 0.024 Uiso 1 1 calc R . .
H20B H -0.0622 0.6763 0.8076 0.024 Uiso 1 1 calc R . .
C21 C 0.26591(15) 0.68462(14) 0.71202(4) 0.0164(3) Uani 1 1 d . . .
C23 C 0.19152(15) 0.64396(14) 0.78584(4) 0.0167(3) Uani 1 1 d . . .
C24 C 0.34564(16) 0.58423(15) 0.71948(4) 0.0188(3) Uani 1 1 d . . .
H24 H 0.3102 0.5055 0.7203 0.023 Uiso 1 1 calc R . .
C25 C -0.10077(15) 0.59385(14) 0.73112(4) 0.0204(3) Uani 1 1 d . . .
H25A H -0.1301 0.6468 0.7133 0.025 Uiso 1 1 calc R . .
H25B H -0.1269 0.5101 0.7262 0.025 Uiso 1 1 calc R . .
C27 C 0.45435(17) 0.81805(15) 0.71539(4) 0.0240(4) Uani 1 1 d . . .
H27 H 0.4907 0.8962 0.7136 0.029 Uiso 1 1 calc R . .
C32 C 0.32192(16) 0.80140(15) 0.70959(4) 0.0199(3) Uani 1 1 d . . .
H32 H 0.2702 0.8686 0.7041 0.024 Uiso 1 1 calc R . .
C39 C -0.16017(15) 0.63597(15) 0.76423(4) 0.0229(4) Uani 1 1 d . . .
H39A H -0.1913 0.7201 0.7628 0.027 Uiso 1 1 calc R . .
H39B H -0.2319 0.5830 0.7707 0.027 Uiso 1 1 calc R . .
C40 C 0.04965(15) 0.60188(13) 0.73487(4) 0.0157(3) Uani 1 1 d . . .
H40 H 0.0852 0.5186 0.7372 0.019 Uiso 1 1 calc R . .
C44 C 0.10550(15) 0.58928(14) 0.67424(4) 0.0187(3) Uani 1 1 d . . .
C46 C 0.53280(17) 0.71837(16) 0.72381(4) 0.0240(4) Uani 1 1 d . . .
H46 H 0.6210 0.7299 0.7281 0.029 Uiso 1 1 calc R . .
C49 C 0.2229(2) 0.38697(15) 0.84520(4) 0.0305(4) Uani 1 1 d . . .
H49A H 0.3104 0.3590 0.8400 0.037 Uiso 1 1 calc R . .
H49B H 0.1609 0.3260 0.8375 0.037 Uiso 1 1 calc R . .
C50 C 0.20747(15) 0.51163(14) 0.79728(4) 0.0171(3) Uani 1 1 d . . .
C53 C 0.08929(17) 0.46158(15) 0.67432(4) 0.0227(3) Uani 1 1 d . . .
H53 H 0.0769 0.4203 0.6942 0.027 Uiso 1 1 calc R . .
C56 C 0.12522(18) 0.58202(19) 0.61466(4) 0.0291(4) Uani 1 1 d . . .
H56 H 0.1376 0.6228 0.5947 0.035 Uiso 1 1 calc R . .
C58 C 0.09169(17) 0.39596(16) 0.64477(4) 0.0260(4) Uani 1 1 d . . .
H58 H 0.0807 0.3110 0.6451 0.031 Uiso 1 1 calc R . .
C60 C 0.12192(17) 0.64848(16) 0.64393(4) 0.0248(4) Uani 1 1 d . . .
H60 H 0.1308 0.7336 0.6433 0.030 Uiso 1 1 calc R . .
C62 C 0.11008(17) 0.45485(18) 0.61501(4) 0.0268(4) Uani 1 1 d . . .
H62 H 0.1123 0.4102 0.5954 0.032 Uiso 1 1 calc R . .
C64 C 0.2086(4) 0.4070(2) 0.88146(6) 0.0827(12) Uani 1 1 d . . .
H64A H 0.1267 0.4466 0.8858 0.124 Uiso 1 1 calc R . .
H64B H 0.2785 0.4582 0.8892 0.124 Uiso 1 1 calc R . .
H64C H 0.2113 0.3292 0.8927 0.124 Uiso 1 1 calc R . .
O3 O 0.97707(12) 0.66833(11) 0.93194(3) 0.0283(3) Uani 1 1 d . . .
O5 O 1.15957(10) 0.29965(10) 0.98921(3) 0.0195(2) Uani 1 1 d . . .
O7 O 0.77030(11) 0.46331(11) 0.96866(3) 0.0228(2) Uani 1 1 d . . .
O8 O 1.19737(11) 0.67384(10) 0.93440(3) 0.0233(2) Uani 1 1 d . . .
C14 C 1.08000(16) 0.62452(15) 0.94028(4) 0.0200(3) Uani 1 1 d . . .
C15 C 0.95131(16) 0.38649(14) 1.07838(4) 0.0195(3) Uani 1 1 d . . .
N18 N 1.02628(12) 0.31793(12) 0.98512(3) 0.0163(3) Uani 1 1 d . . .
C19 C 1.00154(15) 0.42952(14) 0.96468(4) 0.0178(3) Uani 1 1 d . . .
C22 C 0.81762(18) 0.40608(15) 1.08007(4) 0.0258(4) Uani 1 1 d . . .
H22 H 0.7695 0.4137 1.0607 0.031 Uiso 1 1 calc R . .
C26 C 0.86379(15) 0.44455(14) 0.95145(4) 0.0183(3) Uani 1 1 d . . .
C28 C 0.8250(2) 0.40183(16) 1.13935(5) 0.0348(5) Uani 1 1 d . . .
H28 H 0.7834 0.4091 1.1596 0.042 Uiso 1 1 calc R . .
C29 C 1.02022(19) 0.37095(16) 1.10768(4) 0.0282(4) Uani 1 1 d . . .
H29 H 1.1094 0.3554 1.1070 0.034 Uiso 1 1 calc R . .
C30 C 1.04392(16) 0.53138(14) 1.03748(4) 0.0177(3) Uani 1 1 d . . .
C31 C 0.97075(16) 0.20545(14) 0.96818(4) 0.0206(3) Uani 1 1 d . . .
H31A H 1.0238 0.1817 0.9494 0.025 Uiso 1 1 calc R . .
H31B H 0.8822 0.2202 0.9607 0.025 Uiso 1 1 calc R . .
C33 C 0.95563(14) 0.31703(13) 1.01911(4) 0.0151(3) Uani 1 1 d . . .
H33 H 0.8670 0.3493 1.0164 0.018 Uiso 1 1 calc R . .
C35 C 0.9573(2) 0.37845(18) 1.13800(5) 0.0350(5) Uani 1 1 d . . .
H35 H 1.0044 0.3677 1.1574 0.042 Uiso 1 1 calc R . .
C36 C 1.02796(15) 0.39298(14) 1.04583(4) 0.0172(3) Uani 1 1 d . . .
C37 C 0.93961(16) 0.60366(14) 1.02677(4) 0.0197(3) Uani 1 1 d . . .
H37 H 0.8586 0.5676 1.0231 0.024 Uiso 1 1 calc R . .
C41 C 1.17980(17) 0.71398(17) 1.03788(5) 0.0273(4) Uani 1 1 d . . .
H41 H 1.2604 0.7506 1.0417 0.033 Uiso 1 1 calc R . .
C43 C 0.94874(16) 0.17843(14) 1.02735(4) 0.0200(3) Uani 1 1 d . . .
H43A H 1.0140 0.1573 1.0437 0.024 Uiso 1 1 calc R . .
H43B H 0.8634 0.1577 1.0361 0.024 Uiso 1 1 calc R . .
C45 C 0.95602(18) 0.72960(15) 1.02149(4) 0.0243(4) Uani 1 1 d . . .
H45 H 0.8860 0.7768 1.0142 0.029 Uiso 1 1 calc R . .
C47 C 1.16381(16) 0.58795(16) 1.04309(4) 0.0216(3) Uani 1 1 d . . .
H47 H 1.2340 0.5412 1.0504 0.026 Uiso 1 1 calc R . .
C48 C 0.97432(17) 0.10766(15) 0.99497(4) 0.0245(4) Uani 1 1 d . . .
H48A H 1.0587 0.0674 0.9956 0.029 Uiso 1 1 calc R . .
H48B H 0.9074 0.0461 0.9913 0.029 Uiso 1 1 calc R . .
C51 C 1.19784(19) 0.75194(16) 0.87813(5) 0.0269(4) Uani 1 1 d . . .
H51A H 1.1994 0.8257 0.8651 0.040 Uiso 1 1 calc R . .
H51B H 1.1201 0.7062 0.8733 0.040 Uiso 1 1 calc R . .
H51C H 1.2730 0.7027 0.8730 0.040 Uiso 1 1 calc R . .
C52 C 0.7550(2) 0.41440(16) 1.11055(5) 0.0317(4) Uani 1 1 d . . .
H52 H 0.6656 0.4285 1.1114 0.038 Uiso 1 1 calc R . .
C54 C 1.09755(16) 0.50870(14) 0.95924(4) 0.0192(3) Uani 1 1 d . . .
H54 H 1.1798 0.4909 0.9677 0.023 Uiso 1 1 calc R . .
C55 C 1.07569(18) 0.78482(15) 1.02703(5) 0.0281(4) Uani 1 1 d . . .
H55 H 1.0862 0.8688 1.0235 0.034 Uiso 1 1 calc R . .
C59 C 1.19957(18) 0.78532(15) 0.91426(4) 0.0243(4) Uani 1 1 d . . .
H59A H 1.2775 0.8325 0.9192 0.029 Uiso 1 1 calc R . .
H59B H 1.1243 0.8358 0.9194 0.029 Uiso 1 1 calc R . .
C63 C 0.7722(2) 0.50724(19) 0.86853(5) 0.0401(5) Uani 1 1 d . . .
H63A H 0.6933 0.5216 0.8563 0.060 Uiso 1 1 calc R . .
H63B H 0.8253 0.4488 0.8569 0.060 Uiso 1 1 calc R . .
H63C H 0.8191 0.5832 0.8709 0.060 Uiso 1 1 calc R . .
O2 O 1.15234(11) 0.33805(11) 1.05109(3) 0.0216(2) Uani 1 1 d . . .
H2 H 1.1828 0.3158 1.0333 0.032 Uiso 1 1 calc R . .
O4 O 0.86276(11) 0.43071(12) 0.91891(3) 0.0253(3) Uani 1 1 d . . .
N6 N 0.06706(12) 0.67212(11) 0.76807(3) 0.0165(3) Uani 1 1 d . . .
C10 C 0.73904(19) 0.4575(2) 0.90204(5) 0.0346(4) Uani 1 1 d . . .
H10A H 0.6892 0.5175 0.9145 0.042 Uiso 1 1 calc R . .
H10B H 0.6874 0.3831 0.9000 0.042 Uiso 1 1 calc R . .
O9 O 0.05244(11) 0.79793(9) 0.76347(3) 0.0198(2) Uani 1 1 d . . .
O11 O 0.45294(11) 0.81945(10) 0.81875(3) 0.0233(3) Uani 1 1 d . . .
O12 O 0.45167(12) 0.61169(11) 0.81352(3) 0.0270(3) Uani 1 1 d . . .
C3 C 0.27570(16) 0.73363(14) 0.79199(4) 0.0181(3) Uani 1 1 d . . .
H3 H 0.2552 0.8133 0.7854 0.022 Uiso 1 1 calc R . .
C4 C 0.40181(16) 0.71126(15) 0.80907(4) 0.0202(3) Uani 1 1 d . . .
C1 C 0.57667(17) 0.81343(17) 0.83671(4) 0.0267(4) Uani 1 1 d . . .
H1A H 0.6221 0.8913 0.8345 0.032 Uiso 1 1 calc R . .
H1B H 0.6311 0.7498 0.8271 0.032 Uiso 1 1 calc R . .
C2 C 0.55518(19) 0.78605(18) 0.87272(5) 0.0319(4) Uani 1 1 d . . .
H2A H 0.5188 0.7051 0.8751 0.048 Uiso 1 1 calc R . .
H2B H 0.4961 0.8455 0.8819 0.048 Uiso 1 1 calc R . .
H2C H 0.6370 0.7901 0.8842 0.048 Uiso 1 1 calc R . .
H6 H 0.045(2) 0.808(2) 0.7193(6) 0.037(6) 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
O1 C50 1.2088(19) . ?
O6 C17 1.4247(18) . ?
O10 C49 1.4678(19) . ?
O10 C50 1.326(2) . ?
C16 C24 1.396(2) . ?
C16 C46 1.390(2) . ?
C17 C21 1.545(2) . ?
C17 C40 1.547(2) . ?
C17 C44 1.536(2) . ?
C20 C39 1.511(2) . ?
C20 N6 1.520(2) . ?
C21 C24 1.396(2) . ?
C21 C32 1.397(2) . ?
C23 C50 1.520(2) . ?
C23 N6 1.497(2) . ?
C23 C3 1.325(2) . ?
C25 C39 1.542(2) . ?
C25 C40 1.552(2) . ?
C27 C32 1.390(2) . ?
C27 C46 1.392(3) . ?
C40 N6 1.5570(19) . ?
C44 C53 1.398(2) . ?
C44 C60 1.396(2) . ?
C49 C64 1.492(3) . ?
C53 C58 1.394(2) . ?
C56 C60 1.389(3) . ?
C56 C62 1.391(3) . ?
C58 C62 1.378(3) . ?
O3 C14 1.206(2) . ?
O5 N18 1.3908(16) . ?
O7 C26 1.203(2) . ?
O8 C14 1.339(2) . ?
O8 C59 1.461(2) . ?
C14 C54 1.486(2) . ?
C15 C22 1.389(2) . ?
C15 C29 1.392(2) . ?
C15 C36 1.537(2) . ?
N18 C19 1.490(2) . ?
N18 C31 1.513(2) . ?
N18 C33 1.5559(19) . ?
C19 C26 1.519(2) . ?
C19 C54 1.326(2) . ?
C22 C52 1.395(3) . ?
C26 O4 1.327(2) . ?
C28 C35 1.381(3) . ?
C28 C52 1.377(3) . ?
C29 C35 1.390(3) . ?
C30 C36 1.550(2) . ?
C30 C37 1.396(2) . ?
C30 C47 1.393(2) . ?
C31 C48 1.520(2) . ?
C33 C36 1.550(2) . ?
C33 C43 1.545(2) . ?
C36 O2 1.4240(18) . ?
C37 C45 1.396(2) . ?
C41 C47 1.396(3) . ?
C41 C55 1.388(3) . ?
C43 C48 1.543(2) . ?
C45 C55 1.384(3) . ?
C51 C59 1.508(3) . ?
C63 C10 1.500(3) . ?
O4 C10 1.470(2) . ?
N6 O9 1.3882(16) . ?
O11 C4 1.346(2) . ?
O11 C1 1.464(2) . ?
O12 C4 1.210(2) . ?
C3 C4 1.486(2) . ?
C1 C2 1.505(3) . ?

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
C50 O10 C49 116.18(12) . . ?
C46 C16 C24 120.35(15) . . ?
O6 C17 C21 110.95(12) . . ?
O6 C17 C40 109.21(12) . . ?
O6 C17 C44 107.67(12) . . ?
C21 C17 C40 112.09(12) . . ?
C44 C17 C21 106.82(12) . . ?
C44 C17 C40 109.98(12) . . ?
C39 C20 N6 102.71(12) . . ?
C24 C21 C17 120.83(14) . . ?
C24 C21 C32 119.00(15) . . ?
C32 C21 C17 120.16(14) . . ?
N6 C23 C50 115.59(13) . . ?
C3 C23 C50 124.64(14) . . ?
C3 C23 N6 119.68(13) . . ?
C16 C24 C21 120.27(15) . . ?
C39 C25 C40 106.90(13) . . ?
C32 C27 C46 120.31(16) . . ?
C27 C32 C21 120.54(15) . . ?
C20 C39 C25 103.67(13) . . ?
C17 C40 C25 113.82(13) . . ?
C17 C40 N6 112.48(12) . . ?
C25 C40 N6 103.05(12) . . ?
C53 C44 C17 123.72(14) . . ?
C60 C44 C17 117.76(14) . . ?
C60 C44 C53 118.29(15) . . ?
C16 C46 C27 119.49(16) . . ?
O10 C49 C64 105.59(15) . . ?
O1 C50 O10 125.93(14) . . ?
O1 C50 C23 124.67(14) . . ?
O10 C50 C23 109.38(13) . . ?
C58 C53 C44 120.26(16) . . ?
C60 C56 C62 120.36(17) . . ?
C62 C58 C53 121.08(16) . . ?
C56 C60 C44 120.93(16) . . ?
C58 C62 C56 119.06(16) . . ?
C14 O8 C59 116.45(13) . . ?
O3 C14 O8 125.35(15) . . ?
O3 C14 C54 125.83(15) . . ?
O8 C14 C54 108.81(13) . . ?
C22 C15 C29 118.53(16) . . ?
C22 C15 C36 122.68(15) . . ?
C29 C15 C36 118.55(15) . . ?
O5 N18 C19 110.47(12) . . ?
O5 N18 C31 107.95(11) . . ?
O5 N18 C33 110.56(11) . . ?
C19 N18 C31 109.96(12) . . ?
C19 N18 C33 114.68(11) . . ?
C31 N18 C33 102.78(11) . . ?
N18 C19 C26 116.21(13) . . ?
C54 C19 N18 119.63(14) . . ?
C54 C19 C26 124.16(14) . . ?
C15 C22 C52 120.51(18) . . ?
O7 C26 C19 123.66(15) . . ?
O7 C26 O4 126.09(15) . . ?
O4 C26 C19 110.23(13) . . ?
C52 C28 C35 119.78(18) . . ?
C35 C29 C15 120.75(18) . . ?
C37 C30 C36 122.20(14) . . ?
C47 C30 C36 119.06(14) . . ?
C47 C30 C37 118.57(15) . . ?
N18 C31 C48 103.41(13) . . ?
C36 C33 N18 113.08(12) . . ?
C43 C33 N18 102.63(12) . . ?
C43 C33 C36 112.97(12) . . ?
C28 C35 C29 120.09(19) . . ?
C15 C36 C30 106.60(12) . . ?
C15 C36 C33 109.28(12) . . ?
C30 C36 C33 114.51(13) . . ?
O2 C36 C15 108.09(12) . . ?
O2 C36 C30 110.18(13) . . ?
O2 C36 C33 108.02(12) . . ?
C45 C37 C30 120.48(16) . . ?
C55 C41 C47 120.14(16) . . ?
C48 C43 C33 107.14(13) . . ?
C55 C45 C37 120.48(16) . . ?
C30 C47 C41 120.81(16) . . ?
C31 C48 C43 104.74(13) . . ?
C28 C52 C22 120.28(19) . . ?
C19 C54 C14 123.10(15) . . ?
C45 C55 C41 119.51(16) . . ?
O8 C59 C51 110.02(13) . . ?
C26 O4 C10 116.50(14) . . ?
C20 N6 C40 102.23(11) . . ?
C23 N6 C20 109.54(12) . . ?
C23 N6 C40 114.39(11) . . ?
O9 N6 C20 108.45(11) . . ?
O9 N6 C23 110.98(11) . . ?
O9 N6 C40 110.76(11) . . ?
O4 C10 C63 107.25(17) . . ?
C4 O11 C1 116.31(13) . . ?
C23 C3 C4 122.25(14) . . ?
O11 C4 C3 109.36(13) . . ?
O12 C4 O11 124.98(15) . . ?
O12 C4 C3 125.65(15) . . ?
O11 C1 C2 111.33(14) . . ?

_database_code_depnum_ccdc_archive 'CCDC 963298'
