# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_dh_ap_01
_database_code_depnum_ccdc_archive 'CCDC 1011367'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H33 N3 O9'
_chemical_formula_sum            'C24 H33 N3 O9'
_chemical_formula_weight         507.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   17.7791(4)
_cell_length_b                   6.97030(10)
_cell_length_c                   20.0532(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.015(2)
_cell_angle_gamma                90.00
_cell_volume                     2475.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.191
_exptl_crystal_density_meas      1.362
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   '(SADABS; BRUKER, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12966
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5333
_reflns_number_gt                3837
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0975P)²+2.3623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5333
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1903
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.002

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 0.61281(11) -0.0998(3) 0.25812(11) 0.0266(5) Uani 1 1 d . . .
O2 O 0.21597(11) 1.0743(3) -0.00231(10) 0.0212(4) Uani 1 1 d . . .
O3 O -0.10642(15) 0.0171(4) 0.38018(15) 0.0541(9) Uani 1 1 d . . .
O4 O -0.02983(13) -0.1590(3) 0.44846(11) 0.0337(6) Uani 1 1 d . . .
O5 O 0.07264(10) 0.6958(2) 0.31812(9) 0.0152(4) Uani 1 1 d . . .
O6 O 0.41997(10) 0.6884(2) 0.36195(9) 0.0150(4) Uani 1 1 d . . .
O7 O 0.67871(11) 0.1258(3) 0.31667(12) 0.0339(6) Uani 1 1 d . . .
O8 O 0.26647(10) 0.6714(2) 0.07412(9) 0.0141(4) Uani 1 1 d . . .
O9 O 0.19115(11) 0.8555(3) -0.08378(9) 0.0230(5) Uani 1 1 d . . .
N1 N 0.45558(11) 0.4843(3) 0.28242(10) 0.0111(4) Uani 1 1 d . . .
H1 H 0.4418 0.4229 0.2462 0.013 Uiso 1 1 calc R . .
N2 N 0.16079(12) 0.4927(3) 0.07908(10) 0.0115(4) Uani 1 1 d . . .
H2 H 0.1334 0.4271 0.1041 0.014 Uiso 1 1 calc R . .
N3 N 0.12563(12) 0.4608(3) 0.38466(10) 0.0124(5) Uani 1 1 d . . .
H3 H 0.1629 0.3827 0.3917 0.015 Uiso 1 1 calc R . .
C1 C 0.68222(19) -0.1785(5) 0.23806(19) 0.0378(9) Uani 1 1 d . . .
H1A H 0.7108 -0.0789 0.2189 0.057 Uiso 1 1 calc R . .
H1B H 0.6711 -0.2776 0.2055 0.057 Uiso 1 1 calc R . .
H1C H 0.7111 -0.2314 0.2764 0.057 Uiso 1 1 calc R . .
C2 C 0.61951(15) 0.0514(4) 0.29906(14) 0.0187(6) Uani 1 1 d . . .
C3 C 0.54440(15) 0.1110(4) 0.32049(14) 0.0180(6) Uani 1 1 d . . .
H3A H 0.5265 0.0127 0.3495 0.022 Uiso 1 1 calc R . .
H3B H 0.5086 0.1200 0.2813 0.022 Uiso 1 1 calc R . .
C4 C 0.54671(15) 0.3036(4) 0.35755(13) 0.0182(6) Uani 1 1 d . . .
H4A H 0.5081 0.3043 0.3888 0.022 Uiso 1 1 calc R . .
H4B H 0.5953 0.3174 0.3831 0.022 Uiso 1 1 calc R . .
C5 C 0.53422(14) 0.4731(4) 0.31018(13) 0.0146(5) Uani 1 1 d . . .
H5A H 0.5478 0.5908 0.3341 0.018 Uiso 1 1 calc R . .
H5B H 0.5667 0.4603 0.2740 0.018 Uiso 1 1 calc R . .
C6 C 0.40459(13) 0.5876(3) 0.31195(12) 0.0103(5) Uani 1 1 d . . .
C7 C 0.32510(13) 0.5755(3) 0.28000(12) 0.0096(5) Uani 1 1 d . . .
C8 C 0.31040(14) 0.5709(3) 0.21082(12) 0.0099(5) Uani 1 1 d . . .
H8 H 0.3503 0.5694 0.1837 0.012 Uiso 1 1 calc R . .
C9 C 0.23610(13) 0.5683(3) 0.18167(12) 0.0092(5) Uani 1 1 d . . .
C10 C 0.22251(14) 0.5796(3) 0.10693(12) 0.0103(5) Uani 1 1 d . . .
C11 C 0.13819(15) 0.5055(4) 0.00739(12) 0.0130(5) Uani 1 1 d . . .
H11A H 0.1150 0.3854 -0.0078 0.016 Uiso 1 1 calc R . .
H11B H 0.1827 0.5248 -0.0165 0.016 Uiso 1 1 calc R . .
C12 C 0.08287(15) 0.6686(4) -0.00917(13) 0.0161(6) Uani 1 1 d . . .
H12A H 0.0382 0.6473 0.0143 0.019 Uiso 1 1 calc R . .
H12B H 0.0675 0.6659 -0.0568 0.019 Uiso 1 1 calc R . .
C13 C 0.11438(15) 0.8670(4) 0.00916(13) 0.0164(6) Uani 1 1 d . . .
H13A H 0.0740 0.9605 0.0025 0.020 Uiso 1 1 calc R . .
H13B H 0.1323 0.8681 0.0562 0.020 Uiso 1 1 calc R . .
C14 C 0.17774(15) 0.9252(4) -0.03128(13) 0.0164(6) Uani 1 1 d . . .
C15 C 0.27526(17) 1.1510(4) -0.03959(16) 0.0285(7) Uani 1 1 d . . .
H15A H 0.3088 1.0495 -0.0499 0.043 Uiso 1 1 calc R . .
H15B H 0.3029 1.2468 -0.0132 0.043 Uiso 1 1 calc R . .
H15C H 0.2534 1.2077 -0.0804 0.043 Uiso 1 1 calc R . .
C16 C -0.1663(2) -0.1167(6) 0.3942(2) 0.0536(12) Uani 1 1 d . . .
H16A H -0.1572 -0.2388 0.3743 0.080 Uiso 1 1 calc R . .
H16B H -0.2141 -0.0675 0.3757 0.080 Uiso 1 1 calc R . .
H16C H -0.1670 -0.1318 0.4417 0.080 Uiso 1 1 calc R . .
C17 C -0.04050(18) -0.0197(4) 0.41142(15) 0.0263(7) Uani 1 1 d . . .
C18 C 0.01855(16) 0.1218(4) 0.39643(15) 0.0228(6) Uani 1 1 d . . .
H18A H 0.0305 0.1024 0.3507 0.027 Uiso 1 1 calc R . .
H18B H 0.0639 0.0951 0.4254 0.027 Uiso 1 1 calc R . .
C19 C -0.00229(15) 0.3323(4) 0.40493(13) 0.0186(6) Uani 1 1 d . . .
H19A H -0.0402 0.3415 0.4367 0.022 Uiso 1 1 calc R . .
H19B H -0.0242 0.3818 0.3624 0.022 Uiso 1 1 calc R . .
C20 C 0.06574(15) 0.4563(4) 0.42939(13) 0.0159(5) Uani 1 1 d . . .
H20A H 0.0484 0.5864 0.4358 0.019 Uiso 1 1 calc R . .
H20B H 0.0864 0.4086 0.4726 0.019 Uiso 1 1 calc R . .
C21 C 0.12489(14) 0.5815(3) 0.33322(12) 0.0109(5) Uani 1 1 d . . .
C22 C 0.19105(13) 0.5724(3) 0.29211(12) 0.0092(5) Uani 1 1 d . . .
C23 C 0.26529(13) 0.5759(3) 0.32044(12) 0.0100(5) Uani 1 1 d . . .
H23 H 0.2751 0.5785 0.3668 0.012 Uiso 1 1 calc R . .
C24 C 0.17697(13) 0.5708(3) 0.22232(12) 0.0100(5) Uani 1 1 d . . .
H24 H 0.1275 0.5714 0.2031 0.012 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.335(3) . ?
O1 C1 1.440(4) . ?
O2 C14 1.346(3) . ?
O2 C15 1.447(4) . ?
O3 C17 1.305(4) . ?
O3 C16 1.461(4) . ?
O4 C17 1.227(4) . ?
O5 C21 1.241(3) . ?
O6 C6 1.235(3) . ?
O7 C2 1.198(3) . ?
O8 C10 1.242(3) . ?
O9 C14 1.202(3) . ?
N1 C6 1.336(3) . ?
N1 C5 1.461(3) . ?
N1 H1 0.8600 . ?
N2 C10 1.333(3) . ?
N2 C11 1.461(3) . ?
N2 H2 0.8600 . ?
N3 C21 1.330(3) . ?
N3 C20 1.451(3) . ?
N3 H3 0.8600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.497(4) . ?
C3 C4 1.534(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.520(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.502(3) . ?
C7 C8 1.389(3) . ?
C7 C23 1.393(4) . ?
C8 C9 1.397(3) . ?
C8 H8 0.9300 . ?
C9 C24 1.386(4) . ?
C9 C10 1.499(3) . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.500(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.490(4) . ?
C18 C19 1.526(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.532(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.496(4) . ?
C22 C23 1.391(3) . ?
C22 C24 1.400(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C2 O1 C1 116.1(2) . . ?
C14 O2 C15 115.2(2) . . ?
C17 O3 C16 114.9(3) . . ?
C6 N1 C5 121.6(2) . . ?
C6 N1 H1 119.2 . . ?
C5 N1 H1 119.2 . . ?
C10 N2 C11 122.0(2) . . ?
C10 N2 H2 119.0 . . ?
C11 N2 H2 119.0 . . ?
C21 N3 C20 122.3(2) . . ?
C21 N3 H3 118.8 . . ?
C20 N3 H3 118.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O7 C2 O1 123.5(3) . . ?
O7 C2 C3 125.3(3) . . ?
O1 C2 C3 111.2(2) . . ?
C2 C3 C4 113.3(2) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 112.4(2) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 111.2(2) . . ?
N1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O6 C6 N1 123.8(2) . . ?
O6 C6 C7 120.8(2) . . ?
N1 C6 C7 115.5(2) . . ?
C8 C7 C23 119.7(2) . . ?
C8 C7 C6 121.0(2) . . ?
C23 C7 C6 119.3(2) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C24 C9 C8 119.5(2) . . ?
C24 C9 C10 121.6(2) . . ?
C8 C9 C10 118.8(2) . . ?
O8 C10 N2 123.1(2) . . ?
O8 C10 C9 120.2(2) . . ?
N2 C10 C9 116.7(2) . . ?
N2 C11 C12 112.2(2) . . ?
N2 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 114.1(2) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 113.1(2) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O9 C14 O2 124.0(3) . . ?
O9 C14 C13 125.4(2) . . ?
O2 C14 C13 110.5(2) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O3 122.1(3) . . ?
O4 C17 C18 124.9(3) . . ?
O3 C17 C18 113.1(3) . . ?
C17 C18 C19 115.6(2) . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.4 . . ?
C18 C19 C20 112.7(2) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N3 C20 C19 114.6(2) . . ?
N3 C20 H20A 108.6 . . ?
C19 C20 H20A 108.6 . . ?
N3 C20 H20B 108.6 . . ?
C19 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
O5 C21 N3 123.5(2) . . ?
O5 C21 C22 120.1(2) . . ?
N3 C21 C22 116.5(2) . . ?
C23 C22 C24 119.3(2) . . ?
C23 C22 C21 122.6(2) . . ?
C24 C22 C21 118.1(2) . . ?
C22 C23 C7 120.5(2) . . ?
C22 C23 H23 119.7 . . ?
C7 C23 H23 119.7 . . ?
C9 C24 C22 120.6(2) . . ?
C9 C24 H24 119.7 . . ?
C22 C24 H24 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_btcbala
_database_code_depnum_ccdc_archive 'CCDC 1051708'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_audit_creation_date             2015-01-07
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H27 N3 O9'
_chemical_formula_sum            'C21 H27 N3 O9'
_chemical_formula_weight         465.46
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H27N3O9
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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x-y, x, z+5/6'
3 '-y, x-y, z+2/3'
4 '-x, -y, z+1/2'
5 '-x+y, -x, z+1/3'
6 'y, -x+y, z+1/6'

_cell_length_a                   23.9467(16)
_cell_length_b                   23.9467(16)
_cell_length_c                   21.2999(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     10577.9(11)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      23.6530
_cell_measurement_theta_min      1.9430
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             4428
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0902
_diffrn_reflns_av_unetI/netI     0.1847
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21489
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.70
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9912
_diffrn_measured_fraction_theta_max 0.9912
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   43.00  114.00   1.0000  220.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  178.0000  -60.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega   24.00  105.00   1.0000  220.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -19.0000  -90.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0205063000
_diffrn_orient_matrix_UB_12      -0.0338073000
_diffrn_orient_matrix_UB_13      -0.0028541000
_diffrn_orient_matrix_UB_21      0.0257441000
_diffrn_orient_matrix_UB_22      -0.0027021000
_diffrn_orient_matrix_UB_23      -0.0132535000
_diffrn_orient_matrix_UB_31      0.0093003000
_diffrn_orient_matrix_UB_32      -0.0043157000
_diffrn_orient_matrix_UB_33      0.0304076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5480
_reflns_number_total             10912
_reflns_odcompleteness_completeness 86.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.041(1)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_matrix_type           full
_refine_ls_number_parameters     793
_refine_ls_number_reflns         10912
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1671
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      0.937
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1678
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.0278(2) 0.4378(2) 0.46904(19) 0.0394(13) Uani 1 1 d . . .
O2 O 1.0128(2) 0.3737(2) 0.5505(2) 0.0391(13) Uani 1 1 d . . .
O3 O 0.7860(2) 0.2792(2) 0.65379(18) 0.0248(10) Uani 1 1 d . . .
O4 O 0.7359(2) 0.5050(2) 0.67027(17) 0.0249(8) Uani 1 1 d . . .
O5 O 0.7563(2) 0.6186(3) 0.4689(2) 0.0493(15) Uani 1 1 d . . .
O6 O 0.6509(2) 0.5528(2) 0.48728(18) 0.0364(12) Uani 1 1 d . . .
O7 O 0.5339(2) 0.1791(2) 0.58275(16) 0.0249(8) Uani 1 1 d . . .
O8 O 0.4457(2) 0.1748(2) 0.7895(2) 0.0424(13) Uani 1 1 d . . .
O9 O 0.3780(2) 0.2133(2) 0.79964(17) 0.0367(13) Uani 1 1 d . . .
O10 O 0.9288(2) 0.7029(2) 0.32404(17) 0.0284(11) Uani 1 1 d . . .
O11 O 0.9733(2) 0.6692(2) 0.39621(19) 0.0331(12) Uani 1 1 d . . .
O12 O 0.8311(2) 0.4501(2) 0.49115(17) 0.0269(11) Uani 1 1 d . . .
O13 O 0.6780(2) 0.2002(2) 0.40807(16) 0.0241(10) Uani 1 1 d . . .
O14 O 0.6137(2) 0.0987(2) 0.6037(2) 0.0426(13) Uani 1 1 d . . .
O15 O 0.5102(2) 0.0317(2) 0.6268(2) 0.0488(15) Uani 1 1 d . . .
O16 O 0.5541(2) 0.3974(2) 0.50801(17) 0.0267(11) Uani 1 1 d . . .
O17 O 0.4877(2) 0.4020(2) 0.3218(2) 0.0437(13) Uani 1 1 d . . .
O18 O 0.3964(2) 0.3369(2) 0.2707(2) 0.0436(13) Uani 1 1 d . . .
O19 O 0.3634(2) 0.1317(2) 0.49004(18) 0.0327(12) Uani 1 1 d . . .
O20 O 0.3392(2) 0.0493(2) 0.55517(18) 0.0301(11) Uani 1 1 d . . .
O21 O 0.12804(19) -0.03560(19) 0.67565(16) 0.0215(10) Uani 1 1 d . . .
O22 O -0.1236(2) -0.1595(2) 0.59649(17) 0.0238(11) Uani 1 1 d . . .
O23 O -0.2166(2) -0.1866(2) 0.80006(18) 0.0368(12) Uani 1 1 d . . .
O24 O -0.2867(2) -0.1512(2) 0.81521(18) 0.0343(12) Uani 1 1 d . . .
O25 O 0.0425(2) 0.1655(2) 0.69724(17) 0.0249(11) Uani 1 1 d . . .
O26 O 0.0640(3) 0.2588(3) 0.5087(2) 0.0503(15) Uani 1 1 d . . .
O27 O -0.0432(2) 0.2141(2) 0.51152(18) 0.0399(13) Uani 1 1 d . . .
N1 N 0.8338(2) 0.3620(2) 0.5843(2) 0.0218(13) Uani 1 1 d . . .
H1 H 0.8292 0.3894 0.5619 0.026 Uiso 1 1 calc R . .
N2 N 0.6524(2) 0.4809(2) 0.6053(2) 0.0233(13) Uani 1 1 d . . .
H2 H 0.6216 0.4525 0.5826 0.028 Uiso 1 1 calc R . .
N3 N 0.5022(2) 0.2261(2) 0.6544(2) 0.0263(13) Uani 1 1 d . . .
H3 H 0.5126 0.2595 0.6773 0.032 Uiso 1 1 calc R . .
N4 N 0.7968(2) 0.4989(2) 0.4228(2) 0.0244(13) Uani 1 1 d . . .
H4 H 0.7659 0.4951 0.3993 0.029 Uiso 1 1 calc R . .
N5 N 0.5985(2) 0.1638(2) 0.4807(2) 0.0241(13) Uani 1 1 d . . .
H5 H 0.5772 0.1726 0.5075 0.029 Uiso 1 1 calc R . .
N6 N 0.4995(2) 0.3215(2) 0.4330(2) 0.0223(13) Uani 1 1 d . . .
H6 H 0.5004 0.2942 0.4074 0.027 Uiso 1 1 calc R . .
N7 N 0.1684(2) 0.0475(2) 0.6061(2) 0.0211(12) Uani 1 1 d . . .
H7A H 0.1615 0.0737 0.5844 0.025 Uiso 1 1 calc R . .
N8 N -0.1676(2) -0.1240(2) 0.6682(2) 0.0237(13) Uani 1 1 d . . .
H8 H -0.1627 -0.0928 0.6919 0.028 Uiso 1 1 calc R . .
N9 N -0.0401(3) 0.1331(2) 0.6295(2) 0.0255(13) Uani 1 1 d . . .
H9 H -0.0659 0.1035 0.6040 0.031 Uiso 1 1 calc R . .
C1 C 1.0885(3) 0.4409(4) 0.4579(3) 0.041(2) Uani 1 1 d . . .
H1A H 1.1091 0.4677 0.4221 0.062 Uiso 1 1 calc R . .
H1B H 1.0813 0.3983 0.4502 0.062 Uiso 1 1 calc R . .
H1C H 1.1157 0.4588 0.4941 0.062 Uiso 1 1 calc R . .
C2 C 0.9940(3) 0.4016(3) 0.5179(3) 0.0205(15) Uani 1 1 d . . .
C3 C 0.9327(3) 0.4019(3) 0.5256(3) 0.0305(17) Uani 1 1 d . . .
H3A H 0.9073 0.3854 0.4876 0.037 Uiso 1 1 calc R . .
H3B H 0.9422 0.4460 0.5314 0.037 Uiso 1 1 calc R . .
C4 C 0.8934(3) 0.3616(3) 0.5810(3) 0.0219(15) Uani 1 1 d . . .
H4A H 0.8847 0.3176 0.5763 0.026 Uiso 1 1 calc R . .
H4B H 0.9175 0.3790 0.6196 0.026 Uiso 1 1 calc R . .
C5 C 0.7849(3) 0.3213(3) 0.6211(3) 0.0190(15) Uani 1 1 d . . .
C6 C 0.7273(3) 0.3306(3) 0.6208(2) 0.0188(7) Uani 1 1 d . . .
C7 C 0.7346(3) 0.3909(3) 0.6266(2) 0.0188(7) Uani 1 1 d . . .
H7 H 0.7758 0.4267 0.6300 0.023 Uiso 1 1 calc R . .
C8 C 0.6814(3) 0.3991(3) 0.6275(2) 0.0170(14) Uani 1 1 d . . .
C9 C 0.6922(3) 0.4654(3) 0.6357(2) 0.0209(15) Uani 1 1 d . . .
C10 C 0.6617(3) 0.5460(3) 0.6109(3) 0.0340(18) Uani 1 1 d . . .
H10A H 0.6672 0.5582 0.6548 0.041 Uiso 1 1 calc R . .
H10B H 0.6232 0.5455 0.5960 0.041 Uiso 1 1 calc R . .
C11 C 0.7186(3) 0.5955(3) 0.5747(3) 0.0327(18) Uani 1 1 d . . .
H11A H 0.7270 0.6379 0.5874 0.039 Uiso 1 1 calc R . .
H11B H 0.7560 0.5921 0.5863 0.039 Uiso 1 1 calc R . .
C12 C 0.7119(4) 0.5907(4) 0.5051(3) 0.0375(14) Uani 1 1 d . . .
C13 C 0.6379(4) 0.5474(3) 0.4203(3) 0.0375(14) Uani 1 1 d . . .
H13A H 0.6690 0.5403 0.3987 0.056 Uiso 1 1 calc R . .
H13B H 0.6405 0.5864 0.4052 0.056 Uiso 1 1 calc R . .
H13C H 0.5954 0.5117 0.4125 0.056 Uiso 1 1 calc R . .
C14 C 0.6198(3) 0.3457(3) 0.6237(2) 0.0185(14) Uani 1 1 d . . .
H14 H 0.5839 0.3511 0.6236 0.022 Uiso 1 1 calc R . .
C15 C 0.6118(3) 0.2841(3) 0.6203(2) 0.0188(7) Uani 1 1 d . . .
C16 C 0.6654(3) 0.2765(3) 0.6185(2) 0.0188(7) Uani 1 1 d . . .
H16 H 0.6603 0.2354 0.6159 0.023 Uiso 1 1 calc R . .
C17 C 0.5462(3) 0.2257(4) 0.6181(3) 0.0342(8) Uani 1 1 d . . .
C18 C 0.4368(3) 0.1723(3) 0.6575(3) 0.0342(8) Uani 1 1 d . . .
H18A H 0.4374 0.1349 0.6742 0.041 Uiso 1 1 calc R . .
H18B H 0.4190 0.1618 0.6154 0.041 Uiso 1 1 calc R . .
C19 C 0.3941(3) 0.1875(3) 0.6985(3) 0.0342(8) Uani 1 1 d . . .
H19A H 0.3986 0.2283 0.6854 0.041 Uiso 1 1 calc R . .
H19B H 0.3495 0.1544 0.6925 0.041 Uiso 1 1 calc R . .
C20 C 0.4108(3) 0.1913(4) 0.7671(3) 0.0342(8) Uani 1 1 d . . .
C21 C 0.3904(3) 0.2193(3) 0.8663(3) 0.0342(8) Uani 1 1 d . . .
H21A H 0.4358 0.2466 0.8735 0.051 Uiso 1 1 calc R . .
H21B H 0.3764 0.1774 0.8839 0.051 Uiso 1 1 calc R . .
H21C H 0.3673 0.2378 0.8858 0.051 Uiso 1 1 calc R . .
C22 C 0.9906(3) 0.7597(3) 0.3145(3) 0.0256(11) Uani 1 1 d . . .
H22A H 0.9862 0.7881 0.2857 0.038 Uiso 1 1 calc R . .
H22B H 1.0202 0.7476 0.2976 0.038 Uiso 1 1 calc R . .
H22C H 1.0067 0.7814 0.3539 0.038 Uiso 1 1 calc R . .
C23 C 0.9281(3) 0.6607(3) 0.3657(3) 0.0256(11) Uani 1 1 d . . .
C24 C 0.8618(3) 0.6015(3) 0.3696(3) 0.0249(16) Uani 1 1 d . . .
H24A H 0.8297 0.6145 0.3751 0.030 Uiso 1 1 calc R . .
H24B H 0.8524 0.5774 0.3308 0.030 Uiso 1 1 calc R . .
C25 C 0.8580(3) 0.5595(3) 0.4232(2) 0.0239(16) Uani 1 1 d . . .
H25A H 0.8932 0.5507 0.4204 0.029 Uiso 1 1 calc R . .
H25B H 0.8624 0.5820 0.4624 0.029 Uiso 1 1 calc R . .
C26 C 0.7880(3) 0.4493(3) 0.4584(3) 0.0210(15) Uani 1 1 d . . .
C27 C 0.7217(3) 0.3911(3) 0.4563(2) 0.0190(6) Uani 1 1 d . . .
C28 C 0.7140(3) 0.3303(3) 0.4523(2) 0.0190(6) Uani 1 1 d . . .
H28 H 0.7500 0.3252 0.4490 0.023 Uiso 1 1 calc R . .
C29 C 0.6522(3) 0.2761(3) 0.4532(2) 0.0190(6) Uani 1 1 d . . .
C30 C 0.6433(3) 0.2102(3) 0.4460(3) 0.0195(14) Uani 1 1 d . . .
C31 C 0.5851(3) 0.0974(3) 0.4737(3) 0.0300(17) Uani 1 1 d . . .
H31A H 0.6243 0.0958 0.4803 0.036 Uiso 1 1 calc R . .
H31B H 0.5697 0.0822 0.4316 0.036 Uiso 1 1 calc R . .
C32 C 0.5348(3) 0.0547(3) 0.5209(3) 0.0364(19) Uani 1 1 d . . .
H32A H 0.5191 0.0100 0.5098 0.044 Uiso 1 1 calc R . .
H32B H 0.4986 0.0623 0.5185 0.044 Uiso 1 1 calc R . .
C33 C 0.5593(4) 0.0656(4) 0.5877(3) 0.0461(15) Uani 1 1 d . . .
C34 C 0.5276(4) 0.0379(4) 0.6920(3) 0.0461(15) Uani 1 1 d . . .
H34A H 0.5572 0.0225 0.6986 0.069 Uiso 1 1 calc R . .
H34B H 0.4896 0.0130 0.7169 0.069 Uiso 1 1 calc R . .
H34C H 0.5476 0.0824 0.7042 0.069 Uiso 1 1 calc R . .
C35 C 0.5996(3) 0.2847(3) 0.4583(2) 0.0185(14) Uani 1 1 d . . .
H35 H 0.5585 0.2487 0.4590 0.022 Uiso 1 1 calc R . .
C36 C 0.6064(3) 0.3451(3) 0.4624(2) 0.0190(6) Uani 1 1 d . . .
C37 C 0.6684(3) 0.3988(3) 0.4613(2) 0.0190(6) Uani 1 1 d . . .
H37 H 0.6738 0.4400 0.4641 0.023 Uiso 1 1 calc R . .
C38 C 0.5505(3) 0.3561(3) 0.4694(2) 0.0190(6) Uani 1 1 d . . .
C39 C 0.4419(3) 0.3277(3) 0.4346(3) 0.0321(17) Uani 1 1 d . . .
H39A H 0.4542 0.3722 0.4433 0.039 Uiso 1 1 calc R . .
H39B H 0.4137 0.3011 0.4680 0.039 Uiso 1 1 calc R . .
C40 C 0.4061(3) 0.3072(4) 0.3723(3) 0.0331(18) Uani 1 1 d . . .
H40A H 0.4024 0.2666 0.3597 0.040 Uiso 1 1 calc R . .
H40B H 0.3627 0.2997 0.3786 0.040 Uiso 1 1 calc R . .
C41 C 0.4357(3) 0.3532(4) 0.3209(3) 0.0329(18) Uani 1 1 d . . .
C42 C 0.4200(4) 0.3819(4) 0.2182(3) 0.041(2) Uani 1 1 d . . .
H42A H 0.3872 0.3677 0.1865 0.062 Uiso 1 1 calc R . .
H42B H 0.4578 0.3835 0.2009 0.062 Uiso 1 1 calc R . .
H42C H 0.4305 0.4240 0.2326 0.062 Uiso 1 1 calc R . .
C43 C 0.4170(3) 0.1250(3) 0.4674(3) 0.0291(10) Uani 1 1 d . . .
H43A H 0.4362 0.1525 0.4317 0.044 Uiso 1 1 calc R . .
H43B H 0.4015 0.0810 0.4554 0.044 Uiso 1 1 calc R . .
H43C H 0.4485 0.1369 0.5001 0.044 Uiso 1 1 calc R . .
C44 C 0.3271(3) 0.0882(3) 0.5340(3) 0.0291(10) Uani 1 1 d . . .
C45 C 0.2699(3) 0.0958(3) 0.5511(3) 0.0291(10) Uani 1 1 d . . .
H45A H 0.2851 0.1399 0.5638 0.035 Uiso 1 1 calc R . .
H45B H 0.2427 0.0869 0.5144 0.035 Uiso 1 1 calc R . .
C46 C 0.2315(3) 0.0515(3) 0.6027(3) 0.0236(15) Uani 1 1 d . . .
H46A H 0.2257 0.0089 0.5952 0.028 Uiso 1 1 calc R . .
H46B H 0.2541 0.0673 0.6423 0.028 Uiso 1 1 calc R . .
C47 C 0.1216(3) 0.0036(3) 0.6427(2) 0.0153(14) Uani 1 1 d . . .
C48 C 0.0596(3) 0.0046(3) 0.6424(2) 0.0151(14) Uani 1 1 d . . .
C49 C 0.0023(3) -0.0530(3) 0.6376(2) 0.0194(15) Uani 1 1 d . . .
H49 H 0.0026 -0.0915 0.6333 0.023 Uiso 1 1 calc R . .
C50 C -0.0566(3) -0.0535(3) 0.6392(2) 0.0198(15) Uani 1 1 d . . .
C51 C -0.1180(3) -0.1164(3) 0.6336(3) 0.0196(15) Uani 1 1 d . . .
C52 C -0.2292(3) -0.1829(3) 0.6673(3) 0.0358(19) Uani 1 1 d . . .
H52A H -0.2235 -0.2188 0.6792 0.043 Uiso 1 1 calc R . .
H52B H -0.2467 -0.1907 0.6250 0.043 Uiso 1 1 calc R . .
C53 C -0.2762(3) -0.1787(3) 0.7119(3) 0.0302(17) Uani 1 1 d . . .
H53A H -0.3184 -0.2168 0.7070 0.036 Uiso 1 1 calc R . .
H53B H -0.2801 -0.1414 0.7011 0.036 Uiso 1 1 calc R . .
C54 C -0.2552(3) -0.1732(3) 0.7801(3) 0.0284(17) Uani 1 1 d . . .
C55 C -0.2671(4) -0.1392(4) 0.8804(3) 0.049(2) Uani 1 1 d . . .
H55A H -0.2215 -0.1099 0.8827 0.074 Uiso 1 1 calc R . .
H55B H -0.2772 -0.1791 0.9004 0.074 Uiso 1 1 calc R . .
H55C H -0.2895 -0.1206 0.9012 0.074 Uiso 1 1 calc R . .
C56 C -0.0563(3) 0.0044(3) 0.6452(2) 0.0158(14) Uani 1 1 d . . .
H56 H -0.0951 0.0044 0.6457 0.019 Uiso 1 1 calc R . .
C57 C 0.0014(3) 0.0623(3) 0.6506(2) 0.0193(15) Uani 1 1 d . . .
C58 C 0.0586(3) 0.0616(3) 0.6487(2) 0.0207(15) Uani 1 1 d . . .
H58 H 0.0974 0.1003 0.6517 0.025 Uiso 1 1 calc R . .
C59 C 0.0042(3) 0.1249(3) 0.6602(3) 0.0177(14) Uani 1 1 d . . .
C60 C -0.0464(3) 0.1904(3) 0.6377(3) 0.0330(18) Uani 1 1 d . . .
H60A H -0.0479 0.1984 0.6821 0.040 Uiso 1 1 calc R . .
H60B H -0.0864 0.1830 0.6188 0.040 Uiso 1 1 calc R . .
C61 C 0.0098(4) 0.2486(3) 0.6075(3) 0.039(2) Uani 1 1 d . . .
H61A H 0.0495 0.2560 0.6272 0.047 Uiso 1 1 calc R . .
H61B H 0.0055 0.2862 0.6155 0.047 Uiso 1 1 calc R . .
C62 C 0.0148(4) 0.2417(3) 0.5369(3) 0.0374(19) Uani 1 1 d . . .
C63 C -0.0444(4) 0.2064(4) 0.4438(3) 0.062(3) Uani 1 1 d . . .
H63A H -0.0334 0.2466 0.4239 0.093 Uiso 1 1 calc R . .
H63B H -0.0869 0.1740 0.4309 0.093 Uiso 1 1 calc R . .
H63C H -0.0139 0.1935 0.4318 0.093 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.438(7) . ?
O1 C2 1.337(7) . ?
O2 C2 1.195(7) . ?
O3 C5 1.237(7) . ?
O4 C9 1.243(7) . ?
O5 C12 1.209(8) . ?
O6 C12 1.331(8) . ?
O6 C13 1.453(6) . ?
O7 C17 1.252(7) . ?
O8 C20 1.187(8) . ?
O9 C20 1.338(8) . ?
O9 C21 1.442(6) . ?
O10 C22 1.439(7) . ?
O10 C23 1.339(7) . ?
O11 C23 1.190(7) . ?
O12 C26 1.238(7) . ?
O13 C30 1.264(7) . ?
O14 C33 1.188(8) . ?
O15 C33 1.333(8) . ?
O15 C34 1.437(7) . ?
O16 C38 1.256(6) . ?
O17 C41 1.209(8) . ?
O18 C41 1.347(7) . ?
O18 C42 1.456(7) . ?
O19 C43 1.454(7) . ?
O19 C44 1.348(7) . ?
O20 C44 1.192(7) . ?
O21 C47 1.243(6) . ?
O22 C51 1.252(7) . ?
O23 C54 1.197(8) . ?
O24 C54 1.344(8) . ?
O24 C55 1.448(7) . ?
O25 C59 1.232(6) . ?
O26 C62 1.198(8) . ?
O27 C62 1.318(8) . ?
O27 C63 1.452(7) . ?
N1 C4 1.435(7) . ?
N1 C5 1.339(7) . ?
N2 C9 1.349(7) . ?
N2 C10 1.465(8) . ?
N3 C17 1.310(8) . ?
N3 C18 1.448(8) . ?
N4 C25 1.458(7) . ?
N4 C26 1.335(7) . ?
N5 C30 1.319(7) . ?
N5 C31 1.462(8) . ?
N6 C38 1.329(7) . ?
N6 C39 1.459(7) . ?
N7 C46 1.467(7) . ?
N7 C47 1.338(7) . ?
N8 C51 1.331(7) . ?
N8 C52 1.445(8) . ?
N9 C59 1.342(7) . ?
N9 C60 1.463(8) . ?
C2 C3 1.482(9) . ?
C3 C4 1.518(8) . ?
C5 C6 1.502(8) . ?
C6 C7 1.371(8) . ?
C6 C16 1.399(8) . ?
C7 C8 1.382(8) . ?
C8 C9 1.485(8) . ?
C8 C14 1.391(8) . ?
C10 C11 1.498(9) . ?
C11 C12 1.489(8) . ?
C14 C15 1.392(8) . ?
C15 C16 1.383(8) . ?
C15 C17 1.493(9) . ?
C18 C19 1.521(8) . ?
C19 C20 1.506(8) . ?
C23 C24 1.513(9) . ?
C24 C25 1.492(8) . ?
C26 C27 1.500(8) . ?
C27 C28 1.376(8) . ?
C27 C37 1.384(8) . ?
C28 C29 1.397(8) . ?
C29 C30 1.490(8) . ?
C29 C35 1.379(8) . ?
C31 C32 1.508(8) . ?
C32 C33 1.512(9) . ?
C35 C36 1.374(8) . ?
C36 C37 1.396(8) . ?
C36 C38 1.495(8) . ?
C39 C40 1.523(8) . ?
C40 C41 1.460(9) . ?
C44 C45 1.512(9) . ?
C45 C46 1.486(8) . ?
C47 C48 1.496(8) . ?
C48 C49 1.379(8) . ?
C48 C58 1.383(8) . ?
C49 C50 1.406(8) . ?
C50 C51 1.493(8) . ?
C50 C56 1.388(8) . ?
C52 C53 1.515(8) . ?
C53 C54 1.522(8) . ?
C56 C57 1.389(8) . ?
C57 C58 1.380(8) . ?
C57 C59 1.479(8) . ?
C60 C61 1.514(9) . ?
C61 C62 1.525(9) . ?

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
C2 O1 C1 115.4(5) . . ?
C12 O6 C13 117.0(5) . . ?
C20 O9 C21 114.6(5) . . ?
C23 O10 C22 115.2(5) . . ?
C33 O15 C34 114.8(6) . . ?
C41 O18 C42 116.0(6) . . ?
C44 O19 C43 114.1(5) . . ?
C54 O24 C55 114.9(5) . . ?
C62 O27 C63 114.9(6) . . ?
C5 N1 C4 122.3(5) . . ?
C9 N2 C10 120.2(5) . . ?
C17 N3 C18 122.4(5) . . ?
C26 N4 C25 121.1(5) . . ?
C30 N5 C31 120.3(5) . . ?
C38 N6 C39 122.9(5) . . ?
C47 N7 C46 120.7(5) . . ?
C51 N8 C52 122.2(5) . . ?
C59 N9 C60 122.6(5) . . ?
O1 C2 C3 111.2(5) . . ?
O2 C2 O1 122.7(6) . . ?
O2 C2 C3 126.0(6) . . ?
C2 C3 C4 112.6(5) . . ?
N1 C4 C3 109.6(5) . . ?
O3 C5 N1 123.8(6) . . ?
O3 C5 C6 121.2(6) . . ?
N1 C5 C6 115.0(5) . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 C16 119.8(6) . . ?
C16 C6 C5 119.3(6) . . ?
C6 C7 C8 120.6(6) . . ?
C7 C8 C9 118.2(6) . . ?
C7 C8 C14 119.9(6) . . ?
C14 C8 C9 121.8(6) . . ?
O4 C9 N2 121.0(6) . . ?
O4 C9 C8 121.1(6) . . ?
N2 C9 C8 117.9(5) . . ?
N2 C10 C11 113.2(5) . . ?
C12 C11 C10 115.5(6) . . ?
O5 C12 O6 123.8(6) . . ?
O5 C12 C11 124.2(7) . . ?
O6 C12 C11 112.1(7) . . ?
C8 C14 C15 119.8(6) . . ?
C14 C15 C17 121.0(6) . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 C17 119.2(6) . . ?
C15 C16 C6 120.0(6) . . ?
O7 C17 N3 122.0(6) . . ?
O7 C17 C15 121.4(6) . . ?
N3 C17 C15 116.7(6) . . ?
N3 C18 C19 111.7(5) . . ?
C20 C19 C18 112.5(6) . . ?
O8 C20 O9 125.0(6) . . ?
O8 C20 C19 125.4(6) . . ?
O9 C20 C19 109.6(6) . . ?
O10 C23 C24 110.8(6) . . ?
O11 C23 O10 124.5(6) . . ?
O11 C23 C24 124.6(6) . . ?
C25 C24 C23 110.8(5) . . ?
N4 C25 C24 111.0(5) . . ?
O12 C26 N4 123.1(6) . . ?
O12 C26 C27 121.2(5) . . ?
N4 C26 C27 115.7(5) . . ?
C28 C27 C26 120.3(6) . . ?
C28 C27 C37 120.1(6) . . ?
C37 C27 C26 119.5(6) . . ?
C27 C28 C29 120.0(6) . . ?
C28 C29 C30 120.4(6) . . ?
C35 C29 C28 119.0(6) . . ?
C35 C29 C30 120.6(6) . . ?
O13 C30 N5 122.2(6) . . ?
O13 C30 C29 120.4(6) . . ?
N5 C30 C29 117.4(5) . . ?
N5 C31 C32 109.7(5) . . ?
C31 C32 C33 113.6(6) . . ?
O14 C33 O15 124.5(6) . . ?
O14 C33 C32 125.9(7) . . ?
O15 C33 C32 109.6(7) . . ?
C36 C35 C29 121.8(6) . . ?
C35 C36 C37 118.7(6) . . ?
C35 C36 C38 123.1(6) . . ?
C37 C36 C38 118.2(6) . . ?
C27 C37 C36 120.4(6) . . ?
O16 C38 N6 123.6(6) . . ?
O16 C38 C36 119.2(5) . . ?
N6 C38 C36 117.2(5) . . ?
N6 C39 C40 110.9(5) . . ?
C41 C40 C39 115.3(6) . . ?
O17 C41 O18 121.8(7) . . ?
O17 C41 C40 126.4(6) . . ?
O18 C41 C40 111.7(6) . . ?
O19 C44 C45 110.2(6) . . ?
O20 C44 O19 123.5(6) . . ?
O20 C44 C45 126.3(6) . . ?
C46 C45 C44 111.5(5) . . ?
N7 C46 C45 109.4(5) . . ?
O21 C47 N7 123.4(6) . . ?
O21 C47 C48 120.9(5) . . ?
N7 C47 C48 115.7(5) . . ?
C49 C48 C47 119.0(6) . . ?
C49 C48 C58 119.6(6) . . ?
C58 C48 C47 121.4(6) . . ?
C48 C49 C50 120.0(6) . . ?
C49 C50 C51 118.9(6) . . ?
C56 C50 C49 119.3(6) . . ?
C56 C50 C51 121.8(6) . . ?
O22 C51 N8 121.1(6) . . ?
O22 C51 C50 122.0(5) . . ?
N8 C51 C50 116.9(6) . . ?
N8 C52 C53 110.9(5) . . ?
C52 C53 C54 112.3(6) . . ?
O23 C54 O24 124.7(6) . . ?
O23 C54 C53 125.6(6) . . ?
O24 C54 C53 109.7(6) . . ?
C50 C56 C57 120.8(6) . . ?
C56 C57 C59 122.9(6) . . ?
C58 C57 C56 118.8(6) . . ?
C58 C57 C59 118.3(6) . . ?
C57 C58 C48 121.5(6) . . ?
O25 C59 N9 121.9(5) . . ?
O25 C59 C57 121.8(5) . . ?
N9 C59 C57 116.2(5) . . ?
N9 C60 C61 110.6(6) . . ?
C60 C61 C62 113.6(6) . . ?
O26 C62 O27 125.1(7) . . ?
O26 C62 C61 125.1(7) . . ?
O27 C62 C61 109.8(7) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.020 0.333 0.350 37.7 2.8 ?
2 -0.020 0.667 0.850 37.7 2.8 ?
3 0.058 0.725 0.528 7.0 0.5 ?
4 0.196 0.446 0.380 7.9 0.0 ?
5 0.313 0.980 0.683 37.7 2.8 ?
6 0.250 0.804 0.713 7.9 0.0 ?
7 0.275 0.333 0.194 7.0 0.5 ?
8 0.333 0.313 0.516 37.7 2.8 ?
9 0.333 0.058 0.361 7.0 0.5 ?
10 0.446 0.250 0.546 7.9 0.0 ?
11 0.554 0.750 0.046 7.9 0.0 ?
12 0.687 0.020 0.183 37.7 2.8 ?
13 0.667 0.687 0.016 37.7 2.8 ?
14 0.667 0.942 0.861 7.0 0.5 ?
15 0.725 0.667 0.694 7.0 0.5 ?
16 0.750 0.196 0.213 7.9 0.0 ?
17 0.804 0.554 0.880 7.9 0.0 ?
18 0.942 0.275 0.028 7.0 0.5 ?

