# Electronic Supplementary Material (ESI) for ChemComm.
# 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_trimer8
_database_code_depnum_ccdc_archive 'CCDC 1443114'
_audit_update_record             
;
2015-12-17 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_date             2015-08-20T11:25:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C27 H43 N3 O5'
_chemical_formula_weight         489.64

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0838(3)
_cell_length_b                   50.0332(9)
_cell_length_c                   10.6703(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.010(3)
_cell_angle_gamma                90
_cell_volume                     5658.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    56220
_cell_measurement_theta_min      3.533
_cell_measurement_theta_max      76.913

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_density_diffrn    1.15
_exptl_crystal_F_000             2128
_exptl_crystal_colour            colourless
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  
;
Dual Wavelength Diffractometer from Agilent
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_number            56220
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_k_max       62
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.533
_diffrn_reflns_theta_max         76.913
_diffrn_reflns_theta_full        70
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.969
_reflns_Friedel_coverage         0
_reflns_number_total             11576
_reflns_number_gt                10149
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
'CrysAlis CCD (Oxford Diffraction, 2009)'
;
_computing_cell_refinement       
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_structure_solution    'SIR2008 (Burla et al., 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
'WinGX (Farrugia, 2012) and enCIFer (Allen et al., 2004)'
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+17.6029P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11576
_refine_ls_number_parameters     651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0995
_refine_ls_wR_factor_ref         0.2193
_refine_ls_wR_factor_gt          0.2141
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.4879(3) 0.54450(5) 0.2647(3) 0.0379(6) Uani 1 1 d . . . . .
O2 O 0.3113(2) 0.61286(5) 0.3264(2) 0.0304(5) Uani 1 1 d . . . . .
O3 O 0.5053(2) 0.67512(5) 0.3371(2) 0.0298(5) Uani 1 1 d . . . . .
O4 O 0.3862(3) 0.73762(5) 0.0814(3) 0.0387(6) Uani 1 1 d . . . . .
O5 O 0.3630(2) 0.72827(5) -0.1298(2) 0.0328(6) Uani 1 1 d . . . . .
N1 N 0.5070(3) 0.58974(6) 0.2615(3) 0.0276(6) Uani 1 1 d . . . . .
N2 N 0.2946(3) 0.64929(5) 0.1952(3) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.5510(3) 0.69477(5) 0.1633(3) 0.0265(6) Uani 1 1 d . . . . .
C1 C 0.3334(4) 0.56700(7) 0.0982(4) 0.0355(8) Uani 1 1 d . . . . .
H1A H 0.3582 0.5718 0.0202 0.053 Uiso 1 1 calc R U . . .
H1B H 0.2741 0.5803 0.1127 0.053 Uiso 1 1 calc R U . . .
H1C H 0.2929 0.5494 0.0854 0.053 Uiso 1 1 calc R U . . .
C2 C 0.4490(4) 0.56616(7) 0.2159(4) 0.0304(7) Uani 1 1 d . . . . .
C3 C 0.6217(3) 0.58981(7) 0.3804(4) 0.0308(7) Uani 1 1 d . . . . .
C4 C 0.5915(4) 0.57619(8) 0.4960(4) 0.0344(8) Uani 1 1 d . . . . .
H4A H 0.5206 0.5854 0.5146 0.052 Uiso 1 1 calc R U . . .
H4B H 0.6656 0.577 0.5733 0.052 Uiso 1 1 calc R U . . .
H4C H 0.5691 0.5575 0.474 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7296(4) 0.57551(9) 0.3455(4) 0.0425(9) Uani 1 1 d . . . . .
H5A H 0.704 0.5572 0.3176 0.064 Uiso 1 1 calc R U . . .
H5B H 0.8041 0.5751 0.4225 0.064 Uiso 1 1 calc R U . . .
H5C H 0.7498 0.5851 0.2741 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6634(4) 0.61825(8) 0.4214(4) 0.0428(9) Uani 1 1 d . . . . .
H6A H 0.696 0.6265 0.3546 0.064 Uiso 1 1 calc R U . . .
H6B H 0.7299 0.618 0.5054 0.064 Uiso 1 1 calc R U . . .
H6C H 0.5913 0.6286 0.4305 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4551(3) 0.61471(6) 0.1979(3) 0.0253(7) Uani 1 1 d . . . . .
H7A H 0.4225 0.6117 0.1022 0.03 Uiso 1 1 calc R U . . .
H7B H 0.5237 0.6281 0.2132 0.03 Uiso 1 1 calc R U . . .
C8 C 0.3483(3) 0.62606(6) 0.2473(3) 0.0239(6) Uani 1 1 d . . . . .
C9 C 0.1834(3) 0.66048(7) 0.2339(3) 0.0272(7) Uani 1 1 d . . . . .
C10 C 0.0769(3) 0.63974(8) 0.2007(4) 0.0392(9) Uani 1 1 d . . . . .
H10A H 0.0545 0.6354 0.1071 0.059 Uiso 1 1 calc R U . . .
H10B H 0.0029 0.6471 0.2213 0.059 Uiso 1 1 calc R U . . .
H10C H 0.105 0.6235 0.2524 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1332(4) 0.68552(8) 0.1530(4) 0.0428(10) Uani 1 1 d . . . . .
H11A H 0.1995 0.6992 0.1708 0.064 Uiso 1 1 calc R U . . .
H11B H 0.0602 0.6924 0.1769 0.064 Uiso 1 1 calc R U . . .
H11C H 0.1079 0.681 0.0596 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2220(4) 0.66772(7) 0.3783(4) 0.0336(8) Uani 1 1 d . . . . .
H12A H 0.2487 0.6516 0.4309 0.05 Uiso 1 1 calc R U . . .
H12B H 0.1502 0.6758 0.4002 0.05 Uiso 1 1 calc R U . . .
H12C H 0.292 0.6805 0.3969 0.05 Uiso 1 1 calc R U . . .
C13 C 0.3626(3) 0.66585(6) 0.1251(3) 0.0246(7) Uani 1 1 d . . . . .
H13A H 0.305 0.6797 0.0746 0.03 Uiso 1 1 calc R U . . .
H13B H 0.39 0.6546 0.0622 0.03 Uiso 1 1 calc R U . . .
C14 C 0.4790(3) 0.67942(6) 0.2195(3) 0.0244(7) Uani 1 1 d . . . . .
C15 C 0.6661(3) 0.70899(7) 0.2503(3) 0.0297(7) Uani 1 1 d . . . . .
C16 C 0.7607(4) 0.68841(8) 0.3286(4) 0.0376(9) Uani 1 1 d . . . . .
H16A H 0.7249 0.6793 0.3907 0.056 Uiso 1 1 calc R U . . .
H16B H 0.8389 0.6975 0.3766 0.056 Uiso 1 1 calc R U . . .
H16C H 0.779 0.6753 0.2684 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6273(4) 0.72841(8) 0.3428(4) 0.0366(8) Uani 1 1 d . . . . .
H17A H 0.5684 0.7417 0.2912 0.055 Uiso 1 1 calc R U . . .
H17B H 0.7024 0.7375 0.3982 0.055 Uiso 1 1 calc R U . . .
H17C H 0.5864 0.7185 0.3983 0.055 Uiso 1 1 calc R U . . .
C18 C 0.7312(4) 0.72472(9) 0.1651(4) 0.0431(10) Uani 1 1 d . . . . .
H18A H 0.7549 0.7125 0.1046 0.065 Uiso 1 1 calc R U . . .
H18B H 0.807 0.7334 0.2213 0.065 Uiso 1 1 calc R U . . .
H18C H 0.6732 0.7383 0.1149 0.065 Uiso 1 1 calc R U . . .
C19 C 0.5023(3) 0.70112(6) 0.0250(3) 0.0268(7) Uani 1 1 d . . . . .
H19A H 0.4587 0.6852 -0.0226 0.032 Uiso 1 1 calc R U . . .
H19B H 0.5739 0.7054 -0.0096 0.032 Uiso 1 1 calc R U . . .
C20 C 0.4114(3) 0.72449(7) -0.0016(4) 0.0279(7) Uani 1 1 d . . . . .
C21 C 0.2700(4) 0.74987(7) -0.1671(4) 0.0354(8) Uani 1 1 d . . . . .
H21A H 0.2568 0.7545 -0.2603 0.042 Uiso 1 1 calc R U . . .
H21B H 0.3028 0.7659 -0.1137 0.042 Uiso 1 1 calc R U . . .
C22 C 0.1466(4) 0.74191(7) -0.1473(4) 0.0323(8) Uani 1 1 d . . . . .
C23 C 0.0759(4) 0.72154(7) -0.2199(4) 0.0382(9) Uani 1 1 d . . . . .
H23 H 0.105 0.7129 -0.2847 0.046 Uiso 1 1 calc R U . . .
C24 C -0.0378(4) 0.71338(7) -0.2002(4) 0.0390(9) Uani 1 1 d . . . . .
H24 H -0.0859 0.6995 -0.252 0.047 Uiso 1 1 calc R U . . .
C25 C -0.0797(4) 0.72571(7) -0.1050(4) 0.0372(9) Uani 1 1 d . . . . .
H25 H -0.1564 0.7201 -0.0903 0.045 Uiso 1 1 calc R U . . .
C26 C -0.0102(4) 0.74621(8) -0.0310(4) 0.0386(9) Uani 1 1 d . . . . .
H26 H -0.0393 0.7547 0.0343 0.046 Uiso 1 1 calc R U . . .
C27 C 0.1022(4) 0.75434(7) -0.0521(4) 0.0350(8) Uani 1 1 d . . . . .
H27 H 0.1493 0.7685 -0.0013 0.042 Uiso 1 1 calc R U . . .
O1' O 0.2975(3) 0.31896(6) 0.1590(3) 0.0472(7) Uani 1 1 d . . . . .
O2' O 0.6304(2) 0.35236(5) 0.1539(3) 0.0330(6) Uani 1 1 d . . . . .
O3' O 0.6550(2) 0.42659(5) 0.2235(2) 0.0286(5) Uani 1 1 d . . . . .
O4' O 0.9542(2) 0.45073(6) 0.5501(3) 0.0412(6) Uani 1 1 d . . . . .
O5' O 0.9146(2) 0.45456(5) 0.7436(2) 0.0332(6) Uani 1 1 d . . . . .
N1' N 0.4091(3) 0.35740(6) 0.2133(3) 0.0304(6) Uani 1 1 d . . . . .
N2' N 0.7461(2) 0.37864(5) 0.3202(3) 0.0219(5) Uani 1 1 d . . . . .
N3' N 0.6931(3) 0.44775(5) 0.4207(3) 0.0241(6) Uani 1 1 d . . . . .
C1' C 0.4863(4) 0.31579(8) 0.3340(4) 0.0426(9) Uani 1 1 d . . . . .
H1'1 H 0.4817 0.3217 0.4201 0.064 Uiso 1 1 calc R U . . .
H1'2 H 0.5711 0.3193 0.3269 0.064 Uiso 1 1 calc R U . . .
H1'3 H 0.4684 0.2966 0.3239 0.064 Uiso 1 1 calc R U . . .
C2' C 0.3906(4) 0.33090(8) 0.2282(4) 0.0360(8) Uani 1 1 d . . . . .
C3' C 0.3175(3) 0.37301(8) 0.1058(4) 0.0347(8) Uani 1 1 d . . . . .
C4' C 0.3035(4) 0.35982(9) -0.0271(4) 0.0397(9) Uani 1 1 d . . . . .
H4'1 H 0.3867 0.3581 -0.0411 0.06 Uiso 1 1 calc R U . . .
H4'2 H 0.2488 0.3708 -0.0968 0.06 Uiso 1 1 calc R U . . .
H4'3 H 0.266 0.342 -0.0285 0.06 Uiso 1 1 calc R U . . .
C5' C 0.1897(4) 0.37417(11) 0.1332(5) 0.0525(12) Uani 1 1 d . . . . .
H5'1 H 0.1571 0.356 0.1344 0.079 Uiso 1 1 calc R U . . .
H5'2 H 0.1303 0.3846 0.0643 0.079 Uiso 1 1 calc R U . . .
H5'3 H 0.1997 0.3827 0.2183 0.079 Uiso 1 1 calc R U . . .
C6' C 0.3633(4) 0.40156(9) 0.0988(5) 0.0476(10) Uani 1 1 d . . . . .
H6'1 H 0.3663 0.411 0.1802 0.071 Uiso 1 1 calc R U . . .
H6'2 H 0.3052 0.4108 0.0245 0.071 Uiso 1 1 calc R U . . .
H6'3 H 0.4478 0.4012 0.0874 0.071 Uiso 1 1 calc R U . . .
C7' C 0.5209(3) 0.37048(7) 0.2978(3) 0.0281(7) Uani 1 1 d . . . . .
H7'1 H 0.5389 0.3632 0.3876 0.034 Uiso 1 1 calc R U . . .
H7'2 H 0.5038 0.3898 0.3019 0.034 Uiso 1 1 calc R U . . .
C8' C 0.6378(3) 0.36666(6) 0.2494(3) 0.0253(7) Uani 1 1 d . . . . .
C9' C 0.8662(3) 0.37511(7) 0.2822(3) 0.0264(7) Uani 1 1 d . . . . .
C10' C 0.8488(3) 0.38610(7) 0.1444(3) 0.0298(7) Uani 1 1 d . . . . .
H10D H 0.7813 0.3762 0.0815 0.045 Uiso 1 1 calc R U . . .
H10E H 0.9276 0.3841 0.1213 0.045 Uiso 1 1 calc R U . . .
H10F H 0.8262 0.4051 0.142 0.045 Uiso 1 1 calc R U . . .
C11' C 0.8991(4) 0.34547(8) 0.2895(4) 0.0411(9) Uani 1 1 d . . . . .
H11D H 0.9079 0.3388 0.3781 0.062 Uiso 1 1 calc R U . . .
H11E H 0.9788 0.3429 0.2686 0.062 Uiso 1 1 calc R U . . .
H11F H 0.8318 0.3356 0.2264 0.062 Uiso 1 1 calc R U . . .
C12' C 0.9744(3) 0.39009(9) 0.3780(4) 0.0366(8) Uani 1 1 d . . . . .
H12D H 0.9536 0.4091 0.3768 0.055 Uiso 1 1 calc R U . . .
H12E H 1.0516 0.3878 0.3521 0.055 Uiso 1 1 calc R U . . .
H12F H 0.9875 0.383 0.4665 0.055 Uiso 1 1 calc R U . . .
C13' C 0.7387(3) 0.39953(6) 0.4136(3) 0.0228(6) Uani 1 1 d . . . . .
H13C H 0.823 0.4021 0.4772 0.027 Uiso 1 1 calc R U . . .
H13D H 0.68 0.3938 0.4628 0.027 Uiso 1 1 calc R U . . .
C14' C 0.6926(3) 0.42619(6) 0.3430(3) 0.0233(6) Uani 1 1 d . . . . .
C15' C 0.6552(3) 0.47478(7) 0.3577(4) 0.0303(7) Uani 1 1 d . . . . .
C16' C 0.7402(4) 0.48241(8) 0.2740(5) 0.0422(9) Uani 1 1 d . . . . .
H16D H 0.8286 0.4817 0.3276 0.063 Uiso 1 1 calc R U . . .
H16E H 0.7198 0.5006 0.24 0.063 Uiso 1 1 calc R U . . .
H16F H 0.7269 0.4699 0.2007 0.063 Uiso 1 1 calc R U . . .
C17' C 0.5171(4) 0.47401(7) 0.2761(4) 0.0359(8) Uani 1 1 d . . . . .
H17D H 0.5066 0.4611 0.2045 0.054 Uiso 1 1 calc R U . . .
H17E H 0.4911 0.4918 0.2396 0.054 Uiso 1 1 calc R U . . .
H17F H 0.4649 0.4686 0.3316 0.054 Uiso 1 1 calc R U . . .
C18' C 0.6699(5) 0.49609(7) 0.4647(4) 0.0460(10) Uani 1 1 d . . . . .
H18D H 0.6155 0.4916 0.5194 0.069 Uiso 1 1 calc R U . . .
H18E H 0.6457 0.5136 0.4238 0.069 Uiso 1 1 calc R U . . .
H18F H 0.758 0.4967 0.5192 0.069 Uiso 1 1 calc R U . . .
C19' C 0.7414(3) 0.44533(6) 0.5621(3) 0.0253(7) Uani 1 1 d . . . . .
H19C H 0.7239 0.4271 0.5881 0.03 Uiso 1 1 calc R U . . .
H19D H 0.696 0.4581 0.6031 0.03 Uiso 1 1 calc R U . . .
C20' C 0.8815(3) 0.45067(7) 0.6140(3) 0.0281(7) Uani 1 1 d . . . . .
C21' C 1.0484(4) 0.45953(11) 0.8053(4) 0.0485(11) Uani 1 1 d . . . . .
H21C H 1.0746 0.4759 0.7681 0.058 Uiso 1 1 calc R U . . .
H21D H 1.0987 0.4443 0.7883 0.058 Uiso 1 1 calc R U . . .
C22' C 1.0712(3) 0.46286(8) 0.9495(4) 0.0354(8) Uani 1 1 d . . . . .
C23' C 1.0180(4) 0.44590(9) 1.0218(4) 0.0468(10) Uani 1 1 d . . . . .
H23' H 0.9639 0.4318 0.9791 0.056 Uiso 1 1 calc R U . . .
C24' C 1.0429(5) 0.44936(10) 1.1544(5) 0.0611(14) Uani 1 1 d . . . . .
H24' H 1.0045 0.4378 1.2022 0.073 Uiso 1 1 calc R U . . .
C25' C 1.1225(5) 0.46922(9) 1.2194(4) 0.0487(11) Uani 1 1 d . . . . .
H25' H 1.1398 0.4713 1.3115 0.058 Uiso 1 1 calc R U . . .
C26' C 1.1768(4) 0.48607(8) 1.1500(4) 0.0414(9) Uani 1 1 d . . . . .
H26' H 1.2325 0.4998 1.194 0.05 Uiso 1 1 calc R U . . .
C27' C 1.1503(4) 0.48307(8) 1.0156(4) 0.0409(9) Uani 1 1 d . . . . .
H27' H 1.1868 0.495 0.9679 0.049 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.225(4) . ?
O2 C8 1.232(4) . ?
O3 C14 1.222(4) . ?
O4 C20 1.200(4) . ?
O5 C20 1.328(4) . ?
O5 C21 1.465(4) . ?
N1 C2 1.364(5) . ?
N1 C7 1.457(4) . ?
N1 C3 1.511(5) . ?
N2 C8 1.350(4) . ?
N2 C13 1.464(4) . ?
N2 C9 1.516(4) . ?
N3 C14 1.366(4) . ?
N3 C19 1.451(4) . ?
N3 C15 1.517(4) . ?
C1 C2 1.509(5) . ?
C3 C6 1.520(5) . ?
C3 C4 1.529(5) . ?
C3 C5 1.531(5) . ?
C7 C8 1.539(4) . ?
C9 C12 1.517(5) . ?
C9 C11 1.531(5) . ?
C9 C10 1.534(5) . ?
C13 C14 1.543(4) . ?
C15 C16 1.531(5) . ?
C15 C17 1.533(5) . ?
C15 C18 1.534(5) . ?
C19 C20 1.516(5) . ?
C21 C22 1.498(5) . ?
C22 C23 1.378(6) . ?
C22 C27 1.397(5) . ?
C23 C24 1.397(6) . ?
C24 C25 1.380(6) . ?
C25 C26 1.383(6) . ?
C26 C27 1.390(6) . ?
O1' C2' 1.233(5) . ?
O2' C8' 1.227(4) . ?
O3' C14' 1.220(4) . ?
O4' C20' 1.198(4) . ?
O5' C20' 1.337(4) . ?
O5' C21' 1.457(4) . ?
N1' C2' 1.358(5) . ?
N1' C7' 1.457(4) . ?
N1' C3' 1.509(5) . ?
N2' C8' 1.357(4) . ?
N2' C13' 1.462(4) . ?
N2' C9' 1.512(4) . ?
N3' C14' 1.359(4) . ?
N3' C19' 1.452(4) . ?
N3' C15' 1.514(4) . ?
C1' C2' 1.507(6) . ?
C3' C6' 1.525(6) . ?
C3' C5' 1.530(5) . ?
C3' C4' 1.530(5) . ?
C7' C8' 1.540(5) . ?
C9' C11' 1.524(5) . ?
C9' C12' 1.526(5) . ?
C9' C10' 1.528(5) . ?
C13' C14' 1.543(4) . ?
C15' C17' 1.524(5) . ?
C15' C16' 1.525(5) . ?
C15' C18' 1.535(5) . ?
C19' C20' 1.512(5) . ?
C21' C22' 1.494(6) . ?
C22' C27' 1.388(5) . ?
C22' C23' 1.389(6) . ?
C23' C24' 1.370(7) . ?
C24' C25' 1.375(6) . ?
C25' C26' 1.372(6) . ?
C26' C27' 1.385(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
C20 O5 C21 115.1(3) . . ?
C2 N1 C7 119.7(3) . . ?
C2 N1 C3 119.7(3) . . ?
C7 N1 C3 120.6(3) . . ?
C8 N2 C13 117.8(3) . . ?
C8 N2 C9 120.1(3) . . ?
C13 N2 C9 120.7(2) . . ?
C14 N3 C19 118.6(3) . . ?
C14 N3 C15 119.3(3) . . ?
C19 N3 C15 121.0(3) . . ?
O1 C2 N1 122.9(4) . . ?
O1 C2 C1 119.1(3) . . ?
N1 C2 C1 118.0(3) . . ?
N1 C3 C6 110.8(3) . . ?
N1 C3 C4 110.4(3) . . ?
C6 C3 C4 107.8(3) . . ?
N1 C3 C5 108.7(3) . . ?
C6 C3 C5 108.3(3) . . ?
C4 C3 C5 111.0(3) . . ?
N1 C7 C8 113.3(3) . . ?
O2 C8 N2 123.3(3) . . ?
O2 C8 C7 118.7(3) . . ?
N2 C8 C7 117.9(3) . . ?
N2 C9 C12 110.8(3) . . ?
N2 C9 C11 109.8(3) . . ?
C12 C9 C11 109.0(3) . . ?
N2 C9 C10 108.6(3) . . ?
C12 C9 C10 111.4(3) . . ?
C11 C9 C10 107.2(3) . . ?
N2 C13 C14 111.9(3) . . ?
O3 C14 N3 123.8(3) . . ?
O3 C14 C13 119.7(3) . . ?
N3 C14 C13 116.4(3) . . ?
N3 C15 C16 109.7(3) . . ?
N3 C15 C17 110.3(3) . . ?
C16 C15 C17 110.6(3) . . ?
N3 C15 C18 109.6(3) . . ?
C16 C15 C18 107.6(3) . . ?
C17 C15 C18 109.0(3) . . ?
N3 C19 C20 112.9(3) . . ?
O4 C20 O5 124.8(3) . . ?
O4 C20 C19 124.8(3) . . ?
O5 C20 C19 110.4(3) . . ?
O5 C21 C22 111.3(3) . . ?
C23 C22 C27 118.3(4) . . ?
C23 C22 C21 120.7(4) . . ?
C27 C22 C21 121.0(4) . . ?
C22 C23 C24 121.5(4) . . ?
C25 C24 C23 119.5(4) . . ?
C24 C25 C26 120.0(4) . . ?
C25 C26 C27 120.0(4) . . ?
C26 C27 C22 120.7(4) . . ?
C20' O5' C21' 115.3(3) . . ?
C2' N1' C7' 119.8(3) . . ?
C2' N1' C3' 120.2(3) . . ?
C7' N1' C3' 120.0(3) . . ?
C8' N2' C13' 118.6(3) . . ?
C8' N2' C9' 120.2(3) . . ?
C13' N2' C9' 119.7(3) . . ?
C14' N3' C19' 120.1(3) . . ?
C14' N3' C15' 119.2(3) . . ?
C19' N3' C15' 120.4(3) . . ?
O1' C2' N1' 122.1(4) . . ?
O1' C2' C1' 119.2(4) . . ?
N1' C2' C1' 118.7(3) . . ?
N1' C3' C6' 111.2(3) . . ?
N1' C3' C5' 109.2(3) . . ?
C6' C3' C5' 108.3(4) . . ?
N1' C3' C4' 110.2(3) . . ?
C6' C3' C4' 107.7(3) . . ?
C5' C3' C4' 110.2(3) . . ?
N1' C7' C8' 112.5(3) . . ?
O2' C8' N2' 123.6(3) . . ?
O2' C8' C7' 119.5(3) . . ?
N2' C8' C7' 116.9(3) . . ?
N2' C9' C11' 108.5(3) . . ?
N2' C9' C12' 110.1(3) . . ?
C11' C9' C12' 108.3(3) . . ?
N2' C9' C10' 110.0(3) . . ?
C11' C9' C10' 111.1(3) . . ?
C12' C9' C10' 108.7(3) . . ?
N2' C13' C14' 111.2(3) . . ?
O3' C14' N3' 124.3(3) . . ?
O3' C14' C13' 119.1(3) . . ?
N3' C14' C13' 116.5(3) . . ?
N3' C15' C17' 109.4(3) . . ?
N3' C15' C16' 110.1(3) . . ?
C17' C15' C16' 111.2(3) . . ?
N3' C15' C18' 109.6(3) . . ?
C17' C15' C18' 108.3(3) . . ?
C16' C15' C18' 108.2(3) . . ?
N3' C19' C20' 113.1(3) . . ?
O4' C20' O5' 124.2(3) . . ?
O4' C20' C19' 125.6(3) . . ?
O5' C20' C19' 110.3(3) . . ?
O5' C21' C22' 109.2(3) . . ?
C27' C22' C23' 118.1(4) . . ?
C27' C22' C21' 119.7(4) . . ?
C23' C22' C21' 122.2(4) . . ?
C24' C23' C22' 120.4(4) . . ?
C23' C24' C25' 121.2(4) . . ?
C26' C25' C24' 119.4(4) . . ?
C25' C26' C27' 119.9(4) . . ?
C26' C27' C22' 121.1(4) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# 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_20151116_GA104_0m
_database_code_depnum_ccdc_archive 'CCDC 1445400'
_audit_update_record             
;
2016-01-05 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7


_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        GA104
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H64 N5 O6'
_chemical_formula_weight         674.93

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                   11.1490(10)
_cell_length_b                   17.2409(15)
_cell_length_c                   11.1991(10)
_cell_angle_alpha                90
_cell_angle_beta                 116.772(4)
_cell_angle_gamma                90
_cell_volume                     1921.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    14827
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      33.283

_exptl_crystal_description       'broken block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_F_000             738
_exptl_crystal_size_max          0.531
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.261
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Version 2.03'
_exptl_absorpt_correction_T_min  0.97176
_exptl_absorpt_correction_T_max  0.98483
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 APEX II'
_diffrn_radiation_source         'fine-focus X-ray tube'
_diffrn_measurement_method       'full sphere'
_diffrn_reflns_number            185889
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         33.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             14705
_reflns_number_gt                13380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.999

_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.


 Crystal was cleaned with ethanol prior to data collection
 Solvent traces would explain residual density close to O1
;

_computing_data_collection       'Bruker APEX2 v2014.11'
_computing_cell_refinement       'Bruker APEX2 v2014.11'
_computing_data_reduction        'Bruker SAINT software package'
_computing_structure_solution    'SIR2002 (Burla, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0779P)²+0.3819P] 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 6014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         14705
_refine_ls_number_parameters     448
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 1.05730(15) 0.43852(8) 0.07141(15) 0.0251(3) Uani 1 1 d . . . . .
O2 O 0.99222(19) 0.56282(9) 0.01639(16) 0.0307(3) Uani 1 1 d . . . . .
O3 O 1.03846(13) 0.72566(7) 0.26995(14) 0.0198(2) Uani 1 1 d . . . . .
O4 O 0.75153(13) 0.78035(7) 0.31537(13) 0.0192(2) Uani 1 1 d . . . . .
O5 O 1.00983(14) 0.86222(8) 0.68546(14) 0.0216(2) Uani 1 1 d . . . . .
O6 O 1.16982(12) 1.01090(7) 0.51241(13) 0.0190(2) Uani 1 1 d . . . . .
N1 N 0.93201(15) 1.01042(9) 0.30321(15) 0.0208(3) Uani 1 1 d . . . . .
H01 H 0.9892 1.0398 0.2895 0.025 Uiso 1 1 calc R U . . .
N2 N 1.17260(13) 0.88360(8) 0.56714(14) 0.0142(2) Uani 1 1 d . . . . .
N3 N 0.91652(13) 0.74892(8) 0.57605(13) 0.0132(2) Uani 1 1 d . . . . .
N4 N 0.79865(13) 0.66927(8) 0.23161(13) 0.0141(2) Uani 1 1 d . . . . .
N5 N 1.13902(14) 0.60840(8) 0.28358(14) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.7456(2) 1.03793(17) 0.3635(2) 0.0374(5) Uani 1 1 d . . . . .
H1 H 0.7474 0.9861 0.4000 0.056 Uiso 1 1 calc R U . . .
H41 H 0.6541 1.0588 0.3263 0.056 Uiso 1 1 calc R U . . .
H40 H 0.8067 1.0722 0.4348 0.056 Uiso 1 1 calc R U . . .
C2 C 0.79031(17) 1.03292(10) 0.25340(18) 0.0209(3) Uani 1 1 d . . . . .
C3 C 0.97366(16) 0.93749(10) 0.37622(17) 0.0200(3) Uani 1 1 d . . . . .
H43 H 0.9744 0.8959 0.3156 0.024 Uiso 1 1 calc R U . . .
H44 H 0.9095 0.9227 0.4110 0.024 Uiso 1 1 calc R U . . .
C4 C 1.11389(15) 0.94701(9) 0.49205(15) 0.0147(2) Uani 1 1 d . . . . .
C5 C 1.09486(15) 0.81219(9) 0.53900(15) 0.0139(2) Uani 1 1 d . . . . .
H45 H 1.1571 0.7675 0.5704 0.017 Uiso 1 1 calc R U . . .
H46 H 1.0400 0.8069 0.4411 0.017 Uiso 1 1 calc R U . . .
C6 C 1.00176(15) 0.81014(9) 0.60693(15) 0.0140(2) Uani 1 1 d . . . . .
C7 C 0.91056(14) 0.69354(9) 0.47520(14) 0.0127(2) Uani 1 1 d . . . . .
H56 H 0.8806 0.6426 0.4929 0.015 Uiso 1 1 calc R U . . .
H57 H 1.0017 0.6868 0.4823 0.015 Uiso 1 1 calc R U . . .
C8 C 0.81417(15) 0.71972(9) 0.33211(15) 0.0138(2) Uani 1 1 d . . . . .
C9 C 0.90537(15) 0.61385(9) 0.25606(15) 0.0137(2) Uani 1 1 d . . . . .
H59 H 0.8744 0.5758 0.1819 0.016 Uiso 1 1 calc R U . . .
H58 H 0.9263 0.5852 0.3398 0.016 Uiso 1 1 calc R U . . .
C10 C 1.03383(15) 0.65433(9) 0.26781(15) 0.0135(2) Uani 1 1 d . . . . .
C11 C 1.11292(19) 0.52641(9) 0.25013(19) 0.0207(3) Uani 1 1 d . . . . .
H60 H 1.0538 0.5061 0.2875 0.025 Uiso 1 1 calc R U . . .
H61 H 1.1988 0.4975 0.2920 0.025 Uiso 1 1 calc R U . . .
C12 C 1.0458(2) 0.51241(11) 0.09774(19) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.9872(2) 0.41812(12) -0.0699(2) 0.0270(4) Uani 1 1 d . . . . .
H62 H 1.0185 0.3666 -0.0833 0.032 Uiso 1 1 calc R U . . .
H63 H 1.0099 0.4564 -0.1224 0.032 Uiso 1 1 calc R U . . .
C14 C 0.8376(2) 0.41606(12) -0.12085(19) 0.0249(3) Uani 1 1 d . . . . .
C15 C 0.7529(3) 0.4431(2) -0.2469(3) 0.0501(8) Uani 1 1 d . . . . .
H3 H 0.7895 0.4683 -0.2985 0.060 Uiso 1 1 calc R U . . .
C16 C 0.6143(3) 0.4339(3) -0.2996(3) 0.0632(11) Uani 1 1 d . . . . .
H64 H 0.5573 0.4520 -0.3871 0.076 Uiso 1 1 calc R U . . .
C17 C 0.5598(3) 0.3986(2) -0.2253(3) 0.0472(7) Uani 1 1 d . . . . .
H2 H 0.4655 0.3912 -0.2616 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7805(2) 0.38255(13) -0.0462(2) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.8366 0.3650 0.0420 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6429(2) 0.37433(15) -0.0984(2) 0.0341(5) Uani 1 1 d . . . . .
H4 H 0.6056 0.3515 -0.0454 0.041 Uiso 1 1 calc R U . . .
C20 C 1.26501(17) 0.64563(10) 0.29150(19) 0.0200(3) Uani 1 1 d . . . . .
C21 C 1.3249(2) 0.69953(14) 0.4131(2) 0.0313(4) Uani 1 1 d . . . . .
H8 H 1.2630 0.7427 0.4002 0.047 Uiso 1 1 calc R U . . .
H6 H 1.4111 0.7199 0.4235 0.047 Uiso 1 1 calc R U . . .
H7 H 1.3388 0.6705 0.4936 0.047 Uiso 1 1 calc R U . . .
C22 C 1.2335(2) 0.69143(16) 0.1636(2) 0.0343(4) Uani 1 1 d . . . . .
H10 H 1.1939 0.6566 0.0863 0.052 Uiso 1 1 calc R U . . .
H9 H 1.3165 0.7139 0.1690 0.052 Uiso 1 1 calc R U . . .
H11 H 1.1698 0.7331 0.1537 0.052 Uiso 1 1 calc R U . . .
C23 C 1.3699(2) 0.58355(14) 0.3108(3) 0.0392(6) Uani 1 1 d . . . . .
H12 H 1.3880 0.5532 0.3912 0.059 Uiso 1 1 calc R U . . .
H14 H 1.4530 0.6084 0.3210 0.059 Uiso 1 1 calc R U . . .
H13 H 1.3359 0.5492 0.2328 0.059 Uiso 1 1 calc R U . . .
C24 C 0.69647(16) 0.68751(10) 0.09034(16) 0.0177(3) Uani 1 1 d . . . . .
C25 C 0.55837(18) 0.69364(14) 0.08891(19) 0.0274(4) Uani 1 1 d . . . . .
H17 H 0.5346 0.6435 0.1135 0.041 Uiso 1 1 calc R U . . .
H15 H 0.4907 0.7082 -0.0009 0.041 Uiso 1 1 calc R U . . .
H16 H 0.5618 0.7332 0.1532 0.041 Uiso 1 1 calc R U . . .
C26 C 0.7331(2) 0.76233(11) 0.04159(18) 0.0251(3) Uani 1 1 d . . . . .
H18 H 0.7315 0.8058 0.0973 0.038 Uiso 1 1 calc R U . . .
H19 H 0.6681 0.7718 -0.0516 0.038 Uiso 1 1 calc R U . . .
H20 H 0.8233 0.7574 0.0478 0.038 Uiso 1 1 calc R U . . .
C27 C 0.6886(2) 0.62188(12) -0.00476(18) 0.0277(4) Uani 1 1 d . . . . .
H22 H 0.7745 0.6178 -0.0086 0.042 Uiso 1 1 calc R U . . .
H21 H 0.6167 0.6329 -0.0943 0.042 Uiso 1 1 calc R U . . .
H23 H 0.6696 0.5729 0.0277 0.042 Uiso 1 1 calc R U . . .
C28 C 1.31018(16) 0.88978(9) 0.68392(17) 0.0176(3) Uani 1 1 d . . . . .
C29 C 1.31301(18) 0.95322(10) 0.78089(18) 0.0224(3) Uani 1 1 d . . . . .
H26 H 1.2989 1.0039 0.7370 0.034 Uiso 1 1 calc R U . . .
H24 H 1.4003 0.9527 0.8605 0.034 Uiso 1 1 calc R U . . .
H25 H 1.2416 0.9436 0.8073 0.034 Uiso 1 1 calc R U . . .
C30 C 1.41203(18) 0.90736(12) 0.6309(2) 0.0258(4) Uani 1 1 d . . . . .
H27 H 1.4084 0.8664 0.5686 0.039 Uiso 1 1 calc R U . . .
H28 H 1.5025 0.9095 0.7058 0.039 Uiso 1 1 calc R U . . .
H29 H 1.3904 0.9574 0.5843 0.039 Uiso 1 1 calc R U . . .
C31 C 1.34904(19) 0.81292(11) 0.7609(2) 0.0246(3) Uani 1 1 d . . . . .
H32 H 1.2796 0.7982 0.7875 0.037 Uiso 1 1 calc R U . . .
H31 H 1.4352 0.8190 0.8409 0.037 Uiso 1 1 calc R U . . .
H30 H 1.3572 0.7724 0.7036 0.037 Uiso 1 1 calc R U . . .
C32 C 0.7799(2) 1.11318(13) 0.1920(3) 0.0383(5) Uani 1 1 d . . . . .
H34 H 0.8402 1.1491 0.2607 0.057 Uiso 1 1 calc R U . . .
H36 H 0.6873 1.1319 0.1567 0.057 Uiso 1 1 calc R U . . .
H35 H 0.8058 1.1100 0.1193 0.057 Uiso 1 1 calc R U . . .
C33 C 0.7027(2) 0.97547(12) 0.1465(2) 0.0263(4) Uani 1 1 d . . . . .
H38 H 0.7318 0.9730 0.0761 0.039 Uiso 1 1 calc R U . . .
H39 H 0.6088 0.9924 0.1079 0.039 Uiso 1 1 calc R U . . .
H37 H 0.7111 0.9240 0.1867 0.039 Uiso 1 1 calc R U . . .
C34 C 0.81851(16) 0.74386(10) 0.63444(17) 0.0176(3) Uani 1 1 d . . . . .
C35 C 0.7298(2) 0.81626(13) 0.5974(2) 0.0298(4) Uani 1 1 d . . . . .
H47 H 0.7856 0.8620 0.6380 0.045 Uiso 1 1 calc R U . . .
H48 H 0.6625 0.8110 0.6306 0.045 Uiso 1 1 calc R U . . .
H49 H 0.6845 0.8222 0.4999 0.045 Uiso 1 1 calc R U . . .
C36 C 0.7277(2) 0.67314(13) 0.5789(3) 0.0309(4) Uani 1 1 d . . . . .
H51 H 0.6802 0.6765 0.4811 0.046 Uiso 1 1 calc R U . . .
H50 H 0.6623 0.6716 0.6149 0.046 Uiso 1 1 calc R U . . .
H52 H 0.7824 0.6259 0.6050 0.046 Uiso 1 1 calc R U . . .
C37 C 0.8969(2) 0.73533(15) 0.7865(2) 0.0316(4) Uani 1 1 d . . . . .
H55 H 0.9578 0.6908 0.8079 0.047 Uiso 1 1 calc R U . . .
H54 H 0.8340 0.7271 0.8243 0.047 Uiso 1 1 calc R U . . .
H53 H 0.9492 0.7826 0.8245 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
O1 C12 1.327(2) . ?
O1 C13 1.458(2) . ?
O2 C12 1.205(2) . ?
O3 C10 1.2307(18) . ?
O4 C8 1.2238(19) . ?
O5 C6 1.2314(19) . ?
O6 C4 1.2354(19) . ?
N1 C3 1.457(2) . ?
N1 C2 1.471(2) . ?
N1 H01 0.8800 . ?
N2 C4 1.355(2) . ?
N2 C5 1.4560(19) . ?
N2 C28 1.506(2) . ?
N3 C6 1.357(2) . ?
N3 C7 1.4575(19) . ?
N3 C34 1.508(2) . ?
N4 C8 1.3704(19) . ?
N4 C9 1.453(2) . ?
N4 C24 1.509(2) . ?
N5 C10 1.359(2) . ?
N5 C11 1.458(2) . ?
N5 C20 1.510(2) . ?
C1 C2 1.526(3) . ?
C1 H1 0.9800 . ?
C1 H41 0.9800 . ?
C1 H40 0.9800 . ?
C2 C33 1.521(3) . ?
C2 C32 1.526(3) . ?
C3 C4 1.525(2) . ?
C3 H43 0.9900 . ?
C3 H44 0.9900 . ?
C5 C6 1.539(2) . ?
C5 H45 0.9900 . ?
C5 H46 0.9900 . ?
C7 C8 1.541(2) . ?
C7 H56 0.9900 . ?
C7 H57 0.9900 . ?
C9 C10 1.545(2) . ?
C9 H59 0.9900 . ?
C9 H58 0.9900 . ?
C11 C12 1.543(3) . ?
C11 H60 0.9900 . ?
C11 H61 0.9900 . ?
C13 C14 1.501(3) . ?
C13 H62 0.9900 . ?
C13 H63 0.9900 . ?
C14 C15 1.379(3) . ?
C14 C18 1.385(3) . ?
C15 C16 1.393(4) . ?
C15 H3 0.9500 . ?
C16 C17 1.373(5) . ?
C16 H64 0.9500 . ?
C17 C19 1.366(4) . ?
C17 H2 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H5 0.9500 . ?
C19 H4 0.9500 . ?
C20 C23 1.527(3) . ?
C20 C22 1.531(3) . ?
C20 C21 1.532(3) . ?
C21 H8 0.9800 . ?
C21 H6 0.9800 . ?
C21 H7 0.9800 . ?
C22 H10 0.9800 . ?
C22 H9 0.9800 . ?
C22 H11 0.9800 . ?
C23 H12 0.9800 . ?
C23 H14 0.9800 . ?
C23 H13 0.9800 . ?
C24 C26 1.526(3) . ?
C24 C27 1.529(3) . ?
C24 C25 1.536(3) . ?
C25 H17 0.9800 . ?
C25 H15 0.9800 . ?
C25 H16 0.9800 . ?
C26 H18 0.9800 . ?
C26 H19 0.9800 . ?
C26 H20 0.9800 . ?
C27 H22 0.9800 . ?
C27 H21 0.9800 . ?
C27 H23 0.9800 . ?
C28 C30 1.530(3) . ?
C28 C29 1.532(2) . ?
C28 C31 1.533(2) . ?
C29 H26 0.9800 . ?
C29 H24 0.9800 . ?
C29 H25 0.9800 . ?
C30 H27 0.9800 . ?
C30 H28 0.9800 . ?
C30 H29 0.9800 . ?
C31 H32 0.9800 . ?
C31 H31 0.9800 . ?
C31 H30 0.9800 . ?
C32 H34 0.9800 . ?
C32 H36 0.9800 . ?
C32 H35 0.9800 . ?
C33 H38 0.9800 . ?
C33 H39 0.9800 . ?
C33 H37 0.9800 . ?
C34 C36 1.527(3) . ?
C34 C35 1.529(3) . ?
C34 C37 1.531(3) . ?
C35 H47 0.9800 . ?
C35 H48 0.9800 . ?
C35 H49 0.9800 . ?
C36 H51 0.9800 . ?
C36 H50 0.9800 . ?
C36 H52 0.9800 . ?
C37 H55 0.9800 . ?
C37 H54 0.9800 . ?
C37 H53 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
C12 O1 C13 114.50(16) . . ?
C3 N1 C2 117.18(14) . . ?
C3 N1 H01 121.4 . . ?
C2 N1 H01 121.4 . . ?
C4 N2 C5 118.29(13) . . ?
C4 N2 C28 120.02(13) . . ?
C5 N2 C28 121.47(12) . . ?
C6 N3 C7 119.30(13) . . ?
C6 N3 C34 119.72(13) . . ?
C7 N3 C34 120.62(12) . . ?
C8 N4 C9 118.23(13) . . ?
C8 N4 C24 119.03(13) . . ?
C9 N4 C24 120.15(13) . . ?
C10 N5 C11 118.10(13) . . ?
C10 N5 C20 119.03(13) . . ?
C11 N5 C20 120.00(13) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H41 109.5 . . ?
H1 C1 H41 109.5 . . ?
C2 C1 H40 109.5 . . ?
H1 C1 H40 109.5 . . ?
H41 C1 H40 109.5 . . ?
N1 C2 C33 109.02(15) . . ?
N1 C2 C1 113.22(16) . . ?
C33 C2 C1 110.19(18) . . ?
N1 C2 C32 105.09(16) . . ?
C33 C2 C32 110.15(16) . . ?
C1 C2 C32 109.05(19) . . ?
N1 C3 C4 109.26(14) . . ?
N1 C3 H43 109.8 . . ?
C4 C3 H43 109.8 . . ?
N1 C3 H44 109.8 . . ?
C4 C3 H44 109.8 . . ?
H43 C3 H44 108.3 . . ?
O6 C4 N2 122.86(14) . . ?
O6 C4 C3 119.45(14) . . ?
N2 C4 C3 117.69(14) . . ?
N2 C5 C6 112.38(12) . . ?
N2 C5 H45 109.1 . . ?
C6 C5 H45 109.1 . . ?
N2 C5 H46 109.1 . . ?
C6 C5 H46 109.1 . . ?
H45 C5 H46 107.9 . . ?
O5 C6 N3 124.52(15) . . ?
O5 C6 C5 119.18(14) . . ?
N3 C6 C5 116.29(13) . . ?
N3 C7 C8 112.39(12) . . ?
N3 C7 H56 109.1 . . ?
C8 C7 H56 109.1 . . ?
N3 C7 H57 109.1 . . ?
C8 C7 H57 109.1 . . ?
H56 C7 H57 107.9 . . ?
O4 C8 N4 124.34(14) . . ?
O4 C8 C7 119.47(14) . . ?
N4 C8 C7 116.04(13) . . ?
N4 C9 C10 111.60(12) . . ?
N4 C9 H59 109.3 . . ?
C10 C9 H59 109.3 . . ?
N4 C9 H58 109.3 . . ?
C10 C9 H58 109.3 . . ?
H59 C9 H58 108.0 . . ?
O3 C10 N5 123.61(14) . . ?
O3 C10 C9 118.83(14) . . ?
N5 C10 C9 117.42(13) . . ?
N5 C11 C12 112.16(14) . . ?
N5 C11 H60 109.2 . . ?
C12 C11 H60 109.2 . . ?
N5 C11 H61 109.2 . . ?
C12 C11 H61 109.2 . . ?
H60 C11 H61 107.9 . . ?
O2 C12 O1 126.10(18) . . ?
O2 C12 C11 123.49(17) . . ?
O1 C12 C11 110.42(15) . . ?
O1 C13 C14 112.27(15) . . ?
O1 C13 H62 109.1 . . ?
C14 C13 H62 109.1 . . ?
O1 C13 H63 109.1 . . ?
C14 C13 H63 109.1 . . ?
H62 C13 H63 107.9 . . ?
C15 C14 C18 118.0(2) . . ?
C15 C14 C13 120.8(2) . . ?
C18 C14 C13 121.00(18) . . ?
C14 C15 C16 120.8(3) . . ?
C14 C15 H3 119.6 . . ?
C16 C15 H3 119.6 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H64 119.9 . . ?
C15 C16 H64 119.9 . . ?
C19 C17 C16 119.2(2) . . ?
C19 C17 H2 120.4 . . ?
C16 C17 H2 120.4 . . ?
C19 C18 C14 120.8(2) . . ?
C19 C18 H5 119.6 . . ?
C14 C18 H5 119.6 . . ?
C17 C19 C18 120.8(2) . . ?
C17 C19 H4 119.6 . . ?
C18 C19 H4 119.6 . . ?
N5 C20 C23 110.05(15) . . ?
N5 C20 C22 110.40(15) . . ?
C23 C20 C22 109.44(18) . . ?
N5 C20 C21 109.34(14) . . ?
C23 C20 C21 107.46(18) . . ?
C22 C20 C21 110.10(17) . . ?
C20 C21 H8 109.5 . . ?
C20 C21 H6 109.5 . . ?
H8 C21 H6 109.5 . . ?
C20 C21 H7 109.5 . . ?
H8 C21 H7 109.5 . . ?
H6 C21 H7 109.5 . . ?
C20 C22 H10 109.5 . . ?
C20 C22 H9 109.5 . . ?
H10 C22 H9 109.5 . . ?
C20 C22 H11 109.5 . . ?
H10 C22 H11 109.5 . . ?
H9 C22 H11 109.5 . . ?
C20 C23 H12 109.5 . . ?
C20 C23 H14 109.5 . . ?
H12 C23 H14 109.5 . . ?
C20 C23 H13 109.5 . . ?
H12 C23 H13 109.5 . . ?
H14 C23 H13 109.5 . . ?
N4 C24 C26 110.72(13) . . ?
N4 C24 C27 110.82(14) . . ?
C26 C24 C27 108.47(15) . . ?
N4 C24 C25 107.77(13) . . ?
C26 C24 C25 111.51(16) . . ?
C27 C24 C25 107.51(15) . . ?
C24 C25 H17 109.5 . . ?
C24 C25 H15 109.5 . . ?
H17 C25 H15 109.5 . . ?
C24 C25 H16 109.5 . . ?
H17 C25 H16 109.5 . . ?
H15 C25 H16 109.5 . . ?
C24 C26 H18 109.5 . . ?
C24 C26 H19 109.5 . . ?
H18 C26 H19 109.5 . . ?
C24 C26 H20 109.5 . . ?
H18 C26 H20 109.5 . . ?
H19 C26 H20 109.5 . . ?
C24 C27 H22 109.5 . . ?
C24 C27 H21 109.5 . . ?
H22 C27 H21 109.5 . . ?
C24 C27 H23 109.5 . . ?
H22 C27 H23 109.5 . . ?
H21 C27 H23 109.5 . . ?
N2 C28 C30 108.70(14) . . ?
N2 C28 C29 110.73(13) . . ?
C30 C28 C29 110.61(15) . . ?
N2 C28 C31 110.27(13) . . ?
C30 C28 C31 108.56(15) . . ?
C29 C28 C31 107.95(15) . . ?
C28 C29 H26 109.5 . . ?
C28 C29 H24 109.5 . . ?
H26 C29 H24 109.5 . . ?
C28 C29 H25 109.5 . . ?
H26 C29 H25 109.5 . . ?
H24 C29 H25 109.5 . . ?
C28 C30 H27 109.5 . . ?
C28 C30 H28 109.5 . . ?
H27 C30 H28 109.5 . . ?
C28 C30 H29 109.5 . . ?
H27 C30 H29 109.5 . . ?
H28 C30 H29 109.5 . . ?
C28 C31 H32 109.5 . . ?
C28 C31 H31 109.5 . . ?
H32 C31 H31 109.5 . . ?
C28 C31 H30 109.5 . . ?
H32 C31 H30 109.5 . . ?
H31 C31 H30 109.5 . . ?
C2 C32 H34 109.5 . . ?
C2 C32 H36 109.5 . . ?
H34 C32 H36 109.5 . . ?
C2 C32 H35 109.5 . . ?
H34 C32 H35 109.5 . . ?
H36 C32 H35 109.5 . . ?
C2 C33 H38 109.5 . . ?
C2 C33 H39 109.5 . . ?
H38 C33 H39 109.5 . . ?
C2 C33 H37 109.5 . . ?
H38 C33 H37 109.5 . . ?
H39 C33 H37 109.5 . . ?
N3 C34 C36 110.27(13) . . ?
N3 C34 C35 109.97(14) . . ?
C36 C34 C35 108.21(16) . . ?
N3 C34 C37 109.00(14) . . ?
C36 C34 C37 108.55(17) . . ?
C35 C34 C37 110.83(16) . . ?
C34 C35 H47 109.5 . . ?
C34 C35 H48 109.5 . . ?
H47 C35 H48 109.5 . . ?
C34 C35 H49 109.5 . . ?
H47 C35 H49 109.5 . . ?
H48 C35 H49 109.5 . . ?
C34 C36 H51 109.5 . . ?
C34 C36 H50 109.5 . . ?
H51 C36 H50 109.5 . . ?
C34 C36 H52 109.5 . . ?
H51 C36 H52 109.5 . . ?
H50 C36 H52 109.5 . . ?
C34 C37 H55 109.5 . . ?
C34 C37 H54 109.5 . . ?
H55 C37 H54 109.5 . . ?
C34 C37 H53 109.5 . . ?
H55 C37 H53 109.5 . . ?
H54 C37 H53 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
C3 N1 C2 C33 -66.2(2) . . . . ?
C3 N1 C2 C1 56.9(2) . . . . ?
C3 N1 C2 C32 175.77(17) . . . . ?
C2 N1 C3 C4 -141.55(15) . . . . ?
C5 N2 C4 O6 176.73(15) . . . . ?
C28 N2 C4 O6 2.0(2) . . . . ?
C5 N2 C4 C3 -4.4(2) . . . . ?
C28 N2 C4 C3 -179.17(14) . . . . ?
N1 C3 C4 O6 2.5(2) . . . . ?
N1 C3 C4 N2 -176.40(15) . . . . ?
C4 N2 C5 C6 -82.96(17) . . . . ?
C28 N2 C5 C6 91.71(16) . . . . ?
C7 N3 C6 O5 176.22(15) . . . . ?
C34 N3 C6 O5 3.1(2) . . . . ?
C7 N3 C6 C5 -4.75(19) . . . . ?
C34 N3 C6 C5 -177.87(13) . . . . ?
N2 C5 C6 O5 -6.8(2) . . . . ?
N2 C5 C6 N3 174.09(13) . . . . ?
C6 N3 C7 C8 -85.10(16) . . . . ?
C34 N3 C7 C8 87.97(16) . . . . ?
C9 N4 C8 O4 160.64(15) . . . . ?
C24 N4 C8 O4 -1.2(2) . . . . ?
C9 N4 C8 C7 -23.73(19) . . . . ?
C24 N4 C8 C7 174.45(13) . . . . ?
N3 C7 C8 O4 -1.6(2) . . . . ?
N3 C7 C8 N4 -177.45(13) . . . . ?
C8 N4 C9 C10 -68.51(17) . . . . ?
C24 N4 C9 C10 93.09(16) . . . . ?
C11 N5 C10 O3 -166.74(16) . . . . ?
C20 N5 C10 O3 -5.9(2) . . . . ?
C11 N5 C10 C9 17.4(2) . . . . ?
C20 N5 C10 C9 178.28(14) . . . . ?
N4 C9 C10 O3 7.4(2) . . . . ?
N4 C9 C10 N5 -176.54(13) . . . . ?
C10 N5 C11 C12 76.53(18) . . . . ?
C20 N5 C11 C12 -84.10(19) . . . . ?
C13 O1 C12 O2 -5.4(3) . . . . ?
C13 O1 C12 C11 175.15(15) . . . . ?
N5 C11 C12 O2 -16.8(3) . . . . ?
N5 C11 C12 O1 162.68(15) . . . . ?
C12 O1 C13 C14 -72.6(2) . . . . ?
O1 C13 C14 C15 141.4(3) . . . . ?
O1 C13 C14 C18 -42.8(3) . . . . ?
C18 C14 C15 C16 -2.7(5) . . . . ?
C13 C14 C15 C16 173.3(3) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C19 1.4(6) . . . . ?
C15 C14 C18 C19 2.0(4) . . . . ?
C13 C14 C18 C19 -174.0(2) . . . . ?
C16 C17 C19 C18 -2.1(5) . . . . ?
C14 C18 C19 C17 0.4(4) . . . . ?
C10 N5 C20 C23 179.30(18) . . . . ?
C11 N5 C20 C23 -20.2(2) . . . . ?
C10 N5 C20 C22 -59.8(2) . . . . ?
C11 N5 C20 C22 100.66(19) . . . . ?
C10 N5 C20 C21 61.5(2) . . . . ?
C11 N5 C20 C21 -138.06(17) . . . . ?
C8 N4 C24 C26 63.14(19) . . . . ?
C9 N4 C24 C26 -98.32(17) . . . . ?
C8 N4 C24 C27 -176.44(15) . . . . ?
C9 N4 C24 C27 22.1(2) . . . . ?
C8 N4 C24 C25 -59.06(19) . . . . ?
C9 N4 C24 C25 139.48(16) . . . . ?
C4 N2 C28 C30 -66.60(19) . . . . ?
C5 N2 C28 C30 118.82(16) . . . . ?
C4 N2 C28 C29 55.1(2) . . . . ?
C5 N2 C28 C29 -119.48(16) . . . . ?
C4 N2 C28 C31 174.50(15) . . . . ?
C5 N2 C28 C31 -0.1(2) . . . . ?
C6 N3 C34 C36 176.44(16) . . . . ?
C7 N3 C34 C36 3.4(2) . . . . ?
C6 N3 C34 C35 57.2(2) . . . . ?
C7 N3 C34 C35 -115.83(17) . . . . ?
C6 N3 C34 C37 -64.5(2) . . . . ?
C7 N3 C34 C37 122.48(17) . . . . ?

_refine_diff_density_max         0.873
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.061



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
