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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_gd_hx_4_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H33 Cl N2 O6'
_chemical_formula_sum            'C38 H33 Cl N2 O6'
_chemical_formula_weight         649.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.5400(18)
_cell_length_b                   18.518(3)
_cell_length_c                   16.641(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.845(3)
_cell_angle_gamma                90.00
_cell_volume                     3209.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1907
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      20.62

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9602
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            34021
_diffrn_reflns_av_R_equivalents  0.1413
_diffrn_reflns_av_sigmaI/netI    0.1590
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         29.85
_reflns_number_total             9008
_reflns_number_gt                4109
_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)+(0.0916P)²+0.0000P] 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         9008
_refine_ls_number_parameters     428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1763
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2020
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.48776(8) 1.10330(5) 0.39307(5) 0.0350(2) Uani 1 1 d . . .
O1 O 0.3066(2) 0.66997(12) 0.38273(13) 0.0272(5) Uani 1 1 d . . .
O2 O 0.4183(2) 0.62674(13) 0.49991(14) 0.0320(6) Uani 1 1 d . . .
O3 O 0.0699(2) 0.71711(12) 0.39973(13) 0.0245(5) Uani 1 1 d . . .
O4 O 0.1183(2) 0.88905(14) 0.35089(14) 0.0369(6) Uani 1 1 d . . .
O5 O 0.2930(2) 0.84815(14) 0.43060(16) 0.0407(7) Uani 1 1 d . . .
O6 O 0.0226(2) 0.94428(12) 0.64695(14) 0.0292(5) Uani 1 1 d . . .
N1 N 0.2471(2) 0.70133(13) 0.50243(15) 0.0206(6) Uani 1 1 d . . .
N2 N 0.1733(3) 1.03281(15) 0.64353(15) 0.0243(6) Uani 1 1 d . . .
C1 C 0.5190(3) 0.6415(2) 0.3457(2) 0.0351(9) Uani 1 1 d . . .
H1A H 0.5348 0.6936 0.3458 0.053 Uiso 1 1 calc R . .
H1B H 0.5614 0.6185 0.3039 0.053 Uiso 1 1 calc R . .
H1C H 0.5532 0.6214 0.3991 0.053 Uiso 1 1 calc R . .
C2 C 0.3760(3) 0.62751(19) 0.3275(2) 0.0293(8) Uani 1 1 d . . .
C3 C 0.3330(3) 0.66119(17) 0.4627(2) 0.0236(7) Uani 1 1 d . . .
C4 C 0.1236(3) 0.72609(17) 0.46849(19) 0.0208(7) Uani 1 1 d . . .
C5 C 0.0659(3) 0.76538(17) 0.53673(18) 0.0199(6) Uani 1 1 d . . .
C6 C 0.0164(3) 0.84112(17) 0.50659(19) 0.0213(7) Uani 1 1 d . . .
H6A H -0.0444 0.8350 0.4555 0.026 Uiso 1 1 calc R . .
H6B H -0.0320 0.8621 0.5474 0.026 Uiso 1 1 calc R . .
C7 C 0.1186(3) 0.89402(17) 0.49151(18) 0.0213(7) Uani 1 1 d . . .
C8 C 0.1512(3) 0.95444(17) 0.53489(19) 0.0227(7) Uani 1 1 d . . .
C9 C 0.1035(3) 0.97328(17) 0.61316(19) 0.0233(7) Uani 1 1 d . . .
C10 C 0.1665(3) 1.06135(19) 0.72453(19) 0.0291(8) Uani 1 1 d . . .
H10A H 0.0769 1.0576 0.7353 0.035 Uiso 1 1 calc R . .
H10B H 0.1900 1.1131 0.7260 0.035 Uiso 1 1 calc R . .
C11 C 0.2539(3) 1.02216(17) 0.79095(19) 0.0242(7) Uani 1 1 d . . .
C12 C 0.3560(3) 0.97886(18) 0.7758(2) 0.0304(8) Uani 1 1 d . . .
H12 H 0.3738 0.9738 0.7218 0.036 Uiso 1 1 calc R . .
C13 C 0.4309(3) 0.94340(19) 0.8386(2) 0.0339(8) Uani 1 1 d . . .
H13 H 0.4992 0.9134 0.8274 0.041 Uiso 1 1 calc R . .
C14 C 0.4078(4) 0.9511(2) 0.9175(2) 0.0412(10) Uani 1 1 d . . .
H14 H 0.4605 0.9267 0.9606 0.049 Uiso 1 1 calc R . .
C15 C 0.3213(4) 0.6585(3) 0.2448(2) 0.0484(11) Uani 1 1 d . . .
H15A H 0.2274 0.6587 0.2386 0.073 Uiso 1 1 calc R . .
H15B H 0.3489 0.6287 0.2020 0.073 Uiso 1 1 calc R . .
H15C H 0.3526 0.7080 0.2406 0.073 Uiso 1 1 calc R . .
C16 C 0.1867(4) 0.87523(19) 0.4223(2) 0.0323(8) Uani 1 1 d . . .
C17 C 0.1852(5) 0.8643(3) 0.2846(3) 0.0587(13) Uani 1 1 d . . .
H17A H 0.2596 0.8955 0.2817 0.088 Uiso 1 1 calc R . .
H17B H 0.1265 0.8667 0.2329 0.088 Uiso 1 1 calc R . .
H17C H 0.2142 0.8144 0.2949 0.088 Uiso 1 1 calc R . .
C18 C 0.2449(3) 1.01083(17) 0.52303(18) 0.0214(7) Uani 1 1 d . . .
C19 C 0.2572(3) 1.05578(18) 0.59096(19) 0.0238(7) Uani 1 1 d . . .
C20 C 0.2305(4) 1.02987(19) 0.8709(2) 0.0325(8) Uani 1 1 d . . .
H20 H 0.1617 1.0594 0.8822 0.039 Uiso 1 1 calc R . .
C21 C 0.3078(4) 0.9943(2) 0.9339(2) 0.0395(9) Uani 1 1 d . . .
H21 H 0.2920 0.9998 0.9883 0.047 Uiso 1 1 calc R . .
C22 C 0.3412(3) 1.11371(18) 0.6004(2) 0.0282(8) Uani 1 1 d . . .
H22 H 0.3499 1.1431 0.6477 0.034 Uiso 1 1 calc R . .
C23 C 0.4125(3) 1.12755(18) 0.5383(2) 0.0292(8) Uani 1 1 d . . .
H23 H 0.4707 1.1670 0.5427 0.035 Uiso 1 1 calc R . .
C24 C 0.3984(3) 1.08396(18) 0.4703(2) 0.0272(8) Uani 1 1 d . . .
C25 C 0.3153(3) 1.02512(18) 0.46113(19) 0.0237(7) Uani 1 1 d . . .
H25 H 0.3072 0.9957 0.4139 0.028 Uiso 1 1 calc R . .
C26 C -0.0463(3) 0.71891(17) 0.55719(19) 0.0219(7) Uani 1 1 d . . .
C27 C -0.1729(3) 0.73428(19) 0.5254(2) 0.0302(8) Uani 1 1 d . . .
H27 H -0.1917 0.7747 0.4904 0.036 Uiso 1 1 calc R . .
C28 C -0.2725(3) 0.6915(2) 0.5440(2) 0.0362(9) Uani 1 1 d . . .
H28 H -0.3587 0.7033 0.5225 0.043 Uiso 1 1 calc R . .
C29 C -0.2471(3) 0.63192(19) 0.5933(2) 0.0320(8) Uani 1 1 d . . .
H29 H -0.3152 0.6023 0.6054 0.038 Uiso 1 1 calc R . .
C30 C -0.1208(3) 0.61564(18) 0.6253(2) 0.0317(8) Uani 1 1 d . . .
H30 H -0.1024 0.5746 0.6594 0.038 Uiso 1 1 calc R . .
C31 C -0.0224(3) 0.65873(18) 0.60790(19) 0.0258(7) Uani 1 1 d . . .
H31 H 0.0635 0.6474 0.6308 0.031 Uiso 1 1 calc R . .
C32 C 0.1776(3) 0.76548(16) 0.60515(18) 0.0201(7) Uani 1 1 d . . .
C33 C 0.1847(3) 0.79533(17) 0.68184(19) 0.0258(7) Uani 1 1 d . . .
H33 H 0.1144 0.8216 0.6966 0.031 Uiso 1 1 calc R . .
C34 C 0.2973(3) 0.78599(18) 0.73706(19) 0.0284(8) Uani 1 1 d . . .
H34 H 0.3038 0.8057 0.7903 0.034 Uiso 1 1 calc R . .
C35 C 0.3990(3) 0.74846(18) 0.7148(2) 0.0282(8) Uani 1 1 d . . .
H35 H 0.4757 0.7437 0.7527 0.034 Uiso 1 1 calc R . .
C36 C 0.3924(3) 0.71727(18) 0.63802(19) 0.0245(7) Uani 1 1 d . . .
H36 H 0.4624 0.6907 0.6233 0.029 Uiso 1 1 calc R . .
C37 C 0.2796(3) 0.72649(16) 0.58410(18) 0.0194(6) Uani 1 1 d . . .
C38 C 0.3447(4) 0.5490(2) 0.3350(3) 0.0556(13) Uani 1 1 d . . .
H38A H 0.3812 0.5317 0.3894 0.083 Uiso 1 1 calc R . .
H38B H 0.3811 0.5213 0.2939 0.083 Uiso 1 1 calc R . .
H38C H 0.2513 0.5427 0.3268 0.083 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
Cl1 C24 1.743(3) . ?
O1 C3 1.327(4) . ?
O1 C2 1.485(4) . ?
O2 C3 1.194(4) . ?
O3 C4 1.208(4) . ?
O4 C16 1.318(4) . ?
O4 C17 1.471(5) . ?
O5 C16 1.215(4) . ?
O6 C9 1.216(4) . ?
N1 C3 1.412(4) . ?
N1 C4 1.414(4) . ?
N1 C37 1.428(4) . ?
N2 C9 1.378(4) . ?
N2 C19 1.402(4) . ?
N2 C10 1.460(4) . ?
C1 C2 1.513(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C38 1.500(5) . ?
C2 C15 1.519(5) . ?
C4 C5 1.550(4) . ?
C5 C32 1.507(4) . ?
C5 C26 1.543(4) . ?
C5 C6 1.552(4) . ?
C6 C7 1.505(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.347(4) . ?
C7 C16 1.489(5) . ?
C8 C18 1.472(4) . ?
C8 C9 1.507(4) . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.396(5) . ?
C11 C20 1.397(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9500 . ?
C14 C21 1.385(6) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C25 1.385(4) . ?
C18 C19 1.394(4) . ?
C19 C22 1.384(4) . ?
C20 C21 1.391(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.391(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(4) . ?
C26 C31 1.397(4) . ?
C27 C28 1.387(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.377(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.375(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.382(4) . ?
C32 C37 1.384(4) . ?
C33 C34 1.396(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.385(4) . ?
C36 H36 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
C3 O1 C2 120.5(3) . . ?
C16 O4 C17 110.9(3) . . ?
C3 N1 C4 127.0(3) . . ?
C3 N1 C37 122.7(2) . . ?
C4 N1 C37 110.2(2) . . ?
C9 N2 C19 111.5(3) . . ?
C9 N2 C10 121.9(3) . . ?
C19 N2 C10 126.3(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C38 109.0(3) . . ?
O1 C2 C1 110.9(3) . . ?
C38 C2 C1 112.0(3) . . ?
O1 C2 C15 101.9(3) . . ?
C38 C2 C15 112.6(3) . . ?
C1 C2 C15 110.1(3) . . ?
O2 C3 O1 127.7(3) . . ?
O2 C3 N1 121.6(3) . . ?
O1 C3 N1 110.7(3) . . ?
O3 C4 N1 127.1(3) . . ?
O3 C4 C5 125.4(3) . . ?
N1 C4 C5 107.5(2) . . ?
C32 C5 C26 111.8(3) . . ?
C32 C5 C4 101.8(2) . . ?
C26 C5 C4 107.5(2) . . ?
C32 C5 C6 115.3(3) . . ?
C26 C5 C6 110.2(2) . . ?
C4 C5 C6 109.7(2) . . ?
C7 C6 C5 115.4(2) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C16 119.7(3) . . ?
C8 C7 C6 125.5(3) . . ?
C16 C7 C6 114.8(3) . . ?
C7 C8 C18 129.7(3) . . ?
C7 C8 C9 124.3(3) . . ?
C18 C8 C9 105.8(3) . . ?
O6 C9 N2 123.8(3) . . ?
O6 C9 C8 130.4(3) . . ?
N2 C9 C8 105.8(3) . . ?
N2 C10 C11 113.0(3) . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C20 119.0(3) . . ?
C12 C11 C10 122.9(3) . . ?
C20 C11 C10 118.1(3) . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C21 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C21 C14 H14 120.1 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 O4 123.3(3) . . ?
O5 C16 C7 123.7(3) . . ?
O4 C16 C7 113.0(3) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 C18 C19 119.7(3) . . ?
C25 C18 C8 133.1(3) . . ?
C19 C18 C8 107.2(3) . . ?
C22 C19 C18 122.2(3) . . ?
C22 C19 N2 128.2(3) . . ?
C18 C19 N2 109.6(3) . . ?
C21 C20 C11 120.1(4) . . ?
C21 C20 H20 120.0 . . ?
C11 C20 H20 120.0 . . ?
C14 C21 C20 120.0(4) . . ?
C14 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C19 C22 C23 117.9(3) . . ?
C19 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 122.3(3) . . ?
C23 C24 Cl1 118.9(3) . . ?
C25 C24 Cl1 118.8(3) . . ?
C18 C25 C24 117.9(3) . . ?
C18 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
C27 C26 C31 117.9(3) . . ?
C27 C26 C5 121.8(3) . . ?
C31 C26 C5 120.3(3) . . ?
C26 C27 C28 120.9(3) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 119.3(3) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.2(3) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C26 121.2(3) . . ?
C30 C31 H31 119.4 . . ?
C26 C31 H31 119.4 . . ?
C33 C32 C37 120.6(3) . . ?
C33 C32 C5 128.5(3) . . ?
C37 C32 C5 110.8(3) . . ?
C32 C33 C34 118.5(3) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
C35 C34 C33 120.3(3) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 121.7(3) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C37 C36 C35 117.4(3) . . ?
C37 C36 H36 121.3 . . ?
C35 C36 H36 121.3 . . ?
C32 C37 C36 121.5(3) . . ?
C32 C37 N1 109.2(2) . . ?
C36 C37 N1 129.3(3) . . ?
C2 C38 H38A 109.5 . . ?
C2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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 O1 C2 C38 64.3(4) . . . . ?
C3 O1 C2 C1 -59.4(4) . . . . ?
C3 O1 C2 C15 -176.5(3) . . . . ?
C2 O1 C3 O2 8.0(5) . . . . ?
C2 O1 C3 N1 -174.0(3) . . . . ?
C4 N1 C3 O2 -159.8(3) . . . . ?
C37 N1 C3 O2 24.3(5) . . . . ?
C4 N1 C3 O1 22.2(4) . . . . ?
C37 N1 C3 O1 -153.8(3) . . . . ?
C3 N1 C4 O3 0.2(5) . . . . ?
C37 N1 C4 O3 176.6(3) . . . . ?
C3 N1 C4 C5 178.4(3) . . . . ?
C37 N1 C4 C5 -5.3(3) . . . . ?
O3 C4 C5 C32 -175.5(3) . . . . ?
N1 C4 C5 C32 6.2(3) . . . . ?
O3 C4 C5 C26 66.9(4) . . . . ?
N1 C4 C5 C26 -111.3(3) . . . . ?
O3 C4 C5 C6 -52.9(4) . . . . ?
N1 C4 C5 C6 128.9(3) . . . . ?
C32 C5 C6 C7 47.3(4) . . . . ?
C26 C5 C6 C7 174.9(3) . . . . ?
C4 C5 C6 C7 -67.0(3) . . . . ?
C5 C6 C7 C8 -112.6(3) . . . . ?
C5 C6 C7 C16 67.1(4) . . . . ?
C16 C7 C8 C18 3.2(5) . . . . ?
C6 C7 C8 C18 -177.1(3) . . . . ?
C16 C7 C8 C9 -170.5(3) . . . . ?
C6 C7 C8 C9 9.2(5) . . . . ?
C19 N2 C9 O6 -178.5(3) . . . . ?
C10 N2 C9 O6 7.3(5) . . . . ?
C19 N2 C9 C8 2.4(3) . . . . ?
C10 N2 C9 C8 -171.7(3) . . . . ?
C7 C8 C9 O6 -7.6(5) . . . . ?
C18 C8 C9 O6 177.4(3) . . . . ?
C7 C8 C9 N2 171.3(3) . . . . ?
C18 C8 C9 N2 -3.7(3) . . . . ?
C9 N2 C10 C11 83.3(4) . . . . ?
C19 N2 C10 C11 -89.9(4) . . . . ?
N2 C10 C11 C12 17.7(5) . . . . ?
N2 C10 C11 C20 -162.2(3) . . . . ?
C20 C11 C12 C13 1.1(5) . . . . ?
C10 C11 C12 C13 -178.8(3) . . . . ?
C11 C12 C13 C14 -1.2(5) . . . . ?
C12 C13 C14 C21 0.5(5) . . . . ?
C17 O4 C16 O5 2.6(5) . . . . ?
C17 O4 C16 C7 -175.5(3) . . . . ?
C8 C7 C16 O5 78.3(4) . . . . ?
C6 C7 C16 O5 -101.5(4) . . . . ?
C8 C7 C16 O4 -103.6(3) . . . . ?
C6 C7 C16 O4 76.6(4) . . . . ?
C7 C8 C18 C25 9.3(6) . . . . ?
C9 C8 C18 C25 -176.1(3) . . . . ?
C7 C8 C18 C19 -171.0(3) . . . . ?
C9 C8 C18 C19 3.6(3) . . . . ?
C25 C18 C19 C22 -2.0(5) . . . . ?
C8 C18 C19 C22 178.2(3) . . . . ?
C25 C18 C19 N2 177.5(3) . . . . ?
C8 C18 C19 N2 -2.2(3) . . . . ?
C9 N2 C19 C22 179.3(3) . . . . ?
C10 N2 C19 C22 -6.8(5) . . . . ?
C9 N2 C19 C18 -0.2(4) . . . . ?
C10 N2 C19 C18 173.7(3) . . . . ?
C12 C11 C20 C21 -0.4(5) . . . . ?
C10 C11 C20 C21 179.5(3) . . . . ?
C13 C14 C21 C20 0.2(6) . . . . ?
C11 C20 C21 C14 -0.2(5) . . . . ?
C18 C19 C22 C23 1.6(5) . . . . ?
N2 C19 C22 C23 -177.9(3) . . . . ?
C19 C22 C23 C24 -0.2(5) . . . . ?
C22 C23 C24 C25 -0.6(5) . . . . ?
C22 C23 C24 Cl1 179.3(2) . . . . ?
C19 C18 C25 C24 1.1(4) . . . . ?
C8 C18 C25 C24 -179.2(3) . . . . ?
C23 C24 C25 C18 0.2(5) . . . . ?
Cl1 C24 C25 C18 -179.8(2) . . . . ?
C32 C5 C26 C27 150.5(3) . . . . ?
C4 C5 C26 C27 -98.6(3) . . . . ?
C6 C5 C26 C27 20.9(4) . . . . ?
C32 C5 C26 C31 -30.6(4) . . . . ?
C4 C5 C26 C31 80.3(3) . . . . ?
C6 C5 C26 C31 -160.2(3) . . . . ?
C31 C26 C27 C28 0.5(5) . . . . ?
C5 C26 C27 C28 179.4(3) . . . . ?
C26 C27 C28 C29 -1.2(6) . . . . ?
C27 C28 C29 C30 0.9(6) . . . . ?
C28 C29 C30 C31 0.1(5) . . . . ?
C29 C30 C31 C26 -0.8(5) . . . . ?
C27 C26 C31 C30 0.5(5) . . . . ?
C5 C26 C31 C30 -178.5(3) . . . . ?
C26 C5 C32 C33 -67.6(4) . . . . ?
C4 C5 C32 C33 178.0(3) . . . . ?
C6 C5 C32 C33 59.3(4) . . . . ?
C26 C5 C32 C37 109.2(3) . . . . ?
C4 C5 C32 C37 -5.3(3) . . . . ?
C6 C5 C32 C37 -124.0(3) . . . . ?
C37 C32 C33 C34 0.8(5) . . . . ?
C5 C32 C33 C34 177.2(3) . . . . ?
C32 C33 C34 C35 0.6(5) . . . . ?
C33 C34 C35 C36 -1.6(5) . . . . ?
C34 C35 C36 C37 1.0(5) . . . . ?
C33 C32 C37 C36 -1.3(5) . . . . ?
C5 C32 C37 C36 -178.3(3) . . . . ?
C33 C32 C37 N1 179.5(3) . . . . ?
C5 C32 C37 N1 2.5(3) . . . . ?
C35 C36 C37 C32 0.4(5) . . . . ?
C35 C36 C37 N1 179.5(3) . . . . ?
C3 N1 C37 C32 178.4(3) . . . . ?
C4 N1 C37 C32 1.9(3) . . . . ?
C3 N1 C37 C36 -0.7(5) . . . . ?
C4 N1 C37 C36 -177.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        29.85
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         1.271
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.078
_database_code_depnum_ccdc_archive 'CCDC 1007405'
#######################################################################
#
#                 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_mo_gd_hx16_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H29 F N2 O6'
_chemical_formula_sum            'C32 H29 F N2 O6'
_chemical_formula_weight         556.57

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2629(17)
_cell_length_b                   11.9759(19)
_cell_length_c                   12.3346(19)
_cell_angle_alpha                81.629(2)
_cell_angle_beta                 68.063(2)
_cell_angle_gamma                65.327(2)
_cell_volume                     1402.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3536
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9537
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13707
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6698
_reflns_number_gt                4236
_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)+(0.1002P)²+0.1442P] 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         6698
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1842
_refine_ls_wR_factor_gt          0.1595
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.3923(2) 0.6802(2) -0.00366(15) 0.1023(7) Uani 1 1 d . . .
O1 O 0.25430(14) 0.68037(15) 0.18452(13) 0.0665(4) Uani 1 1 d . . .
O2 O 0.74006(17) 0.90636(16) 0.30932(14) 0.0729(4) Uani 1 1 d . . .
O3 O 0.26274(14) 0.95066(14) 0.31071(11) 0.0596(4) Uani 1 1 d . . .
O4 O 0.22906(17) 0.90971(19) 0.49876(13) 0.0839(5) Uani 1 1 d . . .
O5 O 0.39136(15) 0.63580(14) 0.33659(12) 0.0624(4) Uani 1 1 d . . .
F1 F 0.82657(18) 0.92106(16) -0.05784(13) 0.0956(5) Uani 1 1 d . . .
N1 N 0.45397(16) 0.70432(16) 0.14492(13) 0.0507(4) Uani 1 1 d . . .
C21 C 0.58902(18) 0.69773(16) 0.25709(14) 0.0410(4) Uani 1 1 d . . .
C1 C 0.0407(3) 0.6613(3) 0.2750(3) 0.0934(9) Uani 1 1 d . . .
H1A H -0.0310 0.6427 0.2676 0.140 Uiso 1 1 calc R . .
H1B H 0.0006 0.7420 0.3085 0.140 Uiso 1 1 calc R . .
H1C H 0.0837 0.6021 0.3247 0.140 Uiso 1 1 calc R . .
C2 C 0.1496(2) 0.6566(3) 0.1554(2) 0.0848(8) Uani 1 1 d . . .
C3 C 0.3648(2) 0.6864(2) 0.09979(19) 0.0665(6) Uani 1 1 d . . .
C4 C 0.46383(18) 0.67491(17) 0.25620(15) 0.0449(4) Uani 1 1 d . . .
C5 C 0.5502(2) 0.77341(16) 0.36677(15) 0.0450(4) Uani 1 1 d . . .
H5A H 0.5100 0.7326 0.4356 0.054 Uiso 1 1 calc R . .
H5B H 0.6356 0.7711 0.3709 0.054 Uiso 1 1 calc R . .
C6 C 0.45078(19) 0.90560(16) 0.37245(14) 0.0455(4) Uani 1 1 d . . .
C7 C 0.4845(2) 1.00346(17) 0.36039(15) 0.0491(4) Uani 1 1 d . . .
C8 C 0.3967(2) 1.13570(18) 0.37045(16) 0.0557(5) Uani 1 1 d . . .
C9 C 0.4871(3) 1.1972(2) 0.33134(18) 0.0635(6) Uani 1 1 d . . .
C10 C 0.4397(4) 1.3235(2) 0.3322(2) 0.0843(8) Uani 1 1 d . . .
H10 H 0.5009 1.3630 0.3052 0.101 Uiso 1 1 calc R . .
C11 C 0.2991(4) 1.3877(3) 0.3743(3) 0.0959(9) Uani 1 1 d . . .
H11 H 0.2644 1.4731 0.3755 0.115 Uiso 1 1 calc R . .
C12 C 0.0882(4) 0.7607(5) 0.0802(3) 0.157(2) Uani 1 1 d . . .
H12A H 0.1590 0.7584 0.0058 0.235 Uiso 1 1 calc R . .
H12B H 0.0541 0.8380 0.1185 0.235 Uiso 1 1 calc R . .
H12C H 0.0129 0.7516 0.0690 0.235 Uiso 1 1 calc R . .
C13 C 0.2197(4) 0.5292(4) 0.0999(3) 0.1357(16) Uani 1 1 d . . .
H13A H 0.2841 0.5305 0.0227 0.203 Uiso 1 1 calc R . .
H13B H 0.1502 0.5053 0.0952 0.203 Uiso 1 1 calc R . .
H13C H 0.2689 0.4714 0.1466 0.203 Uiso 1 1 calc R . .
C14 C 0.54919(19) 0.75862(17) 0.07743(15) 0.0479(4) Uani 1 1 d . . .
C15 C 0.5655(2) 0.8093(2) -0.03299(18) 0.0653(6) Uani 1 1 d . . .
H15 H 0.5141 0.8066 -0.0759 0.078 Uiso 1 1 calc R . .
C16 C 0.6597(3) 0.8638(2) -0.07727(19) 0.0689(6) Uani 1 1 d . . .
H16 H 0.6729 0.8988 -0.1510 0.083 Uiso 1 1 calc R . .
C17 C 0.7335(2) 0.8661(2) -0.01275(18) 0.0619(5) Uani 1 1 d . . .
C18 C 0.7204(2) 0.81540(18) 0.09694(16) 0.0509(4) Uani 1 1 d . . .
H18 H 0.7729 0.8182 0.1387 0.061 Uiso 1 1 calc R . .
C19 C 0.62636(18) 0.76038(16) 0.14209(14) 0.0426(4) Uani 1 1 d . . .
C20 C 0.6323(2) 0.9953(2) 0.32155(17) 0.0563(5) Uani 1 1 d . . .
N2 N 0.6252(2) 1.11250(18) 0.29858(16) 0.0667(5) Uani 1 1 d . . .
C22 C 0.2064(3) 1.3317(2) 0.4152(3) 0.0933(9) Uani 1 1 d . . .
H22 H 0.1112 1.3791 0.4440 0.112 Uiso 1 1 calc R . .
C23 C 0.2554(3) 1.2026(2) 0.4133(2) 0.0732(6) Uani 1 1 d . . .
H23 H 0.1936 1.1637 0.4405 0.088 Uiso 1 1 calc R . .
C24 C 0.7469(3) 1.1437(3) 0.2494(2) 0.0929(9) Uani 1 1 d . . .
H24A H 0.7461 1.1929 0.3047 0.139 Uiso 1 1 calc R . .
H24B H 0.7445 1.1890 0.1788 0.139 Uiso 1 1 calc R . .
H24C H 0.8301 1.0697 0.2323 0.139 Uiso 1 1 calc R . .
C25 C 0.3022(2) 0.92328(17) 0.40343(16) 0.0496(4) Uani 1 1 d . . .
C26 C 0.1239(2) 0.9602(3) 0.3301(2) 0.0822(8) Uani 1 1 d . . .
H26A H 0.1160 0.8841 0.3604 0.123 Uiso 1 1 calc R . .
H26B H 0.1068 0.9774 0.2576 0.123 Uiso 1 1 calc R . .
H26C H 0.0567 1.0253 0.3853 0.123 Uiso 1 1 calc R . .
C27 C 0.70357(18) 0.57047(15) 0.26280(15) 0.0422(4) Uani 1 1 d . . .
C28 C 0.6878(2) 0.50203(18) 0.36462(18) 0.0625(6) Uani 1 1 d . . .
H28 H 0.6061 0.5324 0.4288 0.075 Uiso 1 1 calc R . .
C29 C 0.7906(3) 0.3904(2) 0.3722(2) 0.0736(7) Uani 1 1 d . . .
H29 H 0.7779 0.3467 0.4414 0.088 Uiso 1 1 calc R . .
C30 C 0.9115(3) 0.3429(2) 0.2788(2) 0.0685(6) Uani 1 1 d . . .
H30 H 0.9814 0.2678 0.2844 0.082 Uiso 1 1 calc R . .
C31 C 0.9280(2) 0.4074(2) 0.1775(2) 0.0708(6) Uani 1 1 d . . .
H31 H 1.0090 0.3753 0.1131 0.085 Uiso 1 1 calc R . .
C32 C 0.8252(2) 0.52044(19) 0.16940(18) 0.0574(5) Uani 1 1 d . . .
H32 H 0.8386 0.5633 0.0997 0.069 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
O6 C3 1.201(3) . ?
O1 C3 1.315(3) . ?
O1 C2 1.493(3) . ?
O2 C20 1.209(3) . ?
O3 C25 1.327(2) . ?
O3 C26 1.448(3) . ?
O4 C25 1.191(2) . ?
O5 C4 1.203(2) . ?
F1 C17 1.369(2) . ?
N1 C4 1.400(2) . ?
N1 C3 1.413(3) . ?
N1 C14 1.423(2) . ?
C21 C19 1.503(2) . ?
C21 C27 1.545(2) . ?
C21 C4 1.548(2) . ?
C21 C5 1.558(2) . ?
C1 C2 1.516(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C12 1.521(4) . ?
C2 C13 1.522(5) . ?
C5 C6 1.503(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.349(3) . ?
C6 C25 1.497(3) . ?
C7 C8 1.469(3) . ?
C7 C20 1.514(3) . ?
C8 C23 1.373(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.377(3) . ?
C9 N2 1.394(3) . ?
C10 C11 1.361(4) . ?
C10 H10 0.9300 . ?
C11 C22 1.374(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.387(3) . ?
C14 C19 1.389(2) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.358(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C20 N2 1.365(3) . ?
N2 C24 1.458(3) . ?
C22 C23 1.408(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C32 1.378(3) . ?
C27 C28 1.391(3) . ?
C28 C29 1.374(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.370(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.363(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.386(3) . ?
C31 H31 0.9300 . ?
C32 H32 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
C3 O1 C2 119.41(18) . . ?
C25 O3 C26 116.04(16) . . ?
C4 N1 C3 127.88(17) . . ?
C4 N1 C14 110.33(14) . . ?
C3 N1 C14 121.79(16) . . ?
C19 C21 C27 113.19(14) . . ?
C19 C21 C4 101.68(13) . . ?
C27 C21 C4 106.92(13) . . ?
C19 C21 C5 115.16(14) . . ?
C27 C21 C5 107.75(13) . . ?
C4 C21 C5 111.81(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C1 101.9(2) . . ?
O1 C2 C12 108.9(3) . . ?
C1 C2 C12 110.3(3) . . ?
O1 C2 C13 108.2(2) . . ?
C1 C2 C13 111.6(3) . . ?
C12 C2 C13 115.0(3) . . ?
O6 C3 O1 127.8(2) . . ?
O6 C3 N1 121.2(2) . . ?
O1 C3 N1 110.99(18) . . ?
O5 C4 N1 126.91(17) . . ?
O5 C4 C21 125.39(16) . . ?
N1 C4 C21 107.67(14) . . ?
C6 C5 C21 116.64(14) . . ?
C6 C5 H5A 108.1 . . ?
C21 C5 H5A 108.1 . . ?
C6 C5 H5B 108.1 . . ?
C21 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
C7 C6 C25 120.40(17) . . ?
C7 C6 C5 125.34(18) . . ?
C25 C6 C5 114.08(16) . . ?
C6 C7 C8 130.58(19) . . ?
C6 C7 C20 124.22(18) . . ?
C8 C7 C20 105.02(17) . . ?
C23 C8 C9 119.4(2) . . ?
C23 C8 C7 133.6(2) . . ?
C9 C8 C7 106.85(19) . . ?
C10 C9 N2 127.3(2) . . ?
C10 C9 C8 122.5(3) . . ?
N2 C9 C8 110.07(18) . . ?
C11 C10 C9 116.9(3) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
C10 C11 C22 122.7(3) . . ?
C10 C11 H11 118.6 . . ?
C22 C11 H11 118.6 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 121.75(18) . . ?
C15 C14 N1 129.01(18) . . ?
C19 C14 N1 109.18(15) . . ?
C16 C15 C14 118.1(2) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C17 C16 C15 119.63(19) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 F1 118.96(19) . . ?
C16 C17 C18 123.6(2) . . ?
F1 C17 C18 117.5(2) . . ?
C19 C18 C17 117.28(19) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C14 119.68(16) . . ?
C18 C19 C21 129.96(16) . . ?
C14 C19 C21 110.36(15) . . ?
O2 C20 N2 123.6(2) . . ?
O2 C20 C7 129.81(19) . . ?
N2 C20 C7 106.53(19) . . ?
C20 N2 C9 111.02(19) . . ?
C20 N2 C24 123.9(2) . . ?
C9 N2 C24 125.0(2) . . ?
C11 C22 C23 120.1(3) . . ?
C11 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C8 C23 C22 118.3(3) . . ?
C8 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 O3 123.60(19) . . ?
O4 C25 C6 124.41(18) . . ?
O3 C25 C6 111.92(15) . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 117.21(18) . . ?
C32 C27 C21 122.22(16) . . ?
C28 C27 C21 120.57(16) . . ?
C29 C28 C27 121.2(2) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 120.7(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C31 C30 C29 119.0(2) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 121.20(19) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C1 -178.2(2) . . . . ?
C3 O1 C2 C12 -61.6(3) . . . . ?
C3 O1 C2 C13 64.1(3) . . . . ?
C2 O1 C3 O6 3.5(4) . . . . ?
C2 O1 C3 N1 -177.6(2) . . . . ?
C4 N1 C3 O6 -157.4(2) . . . . ?
C14 N1 C3 O6 23.0(4) . . . . ?
C4 N1 C3 O1 23.6(3) . . . . ?
C14 N1 C3 O1 -156.02(18) . . . . ?
C3 N1 C4 O5 -5.1(3) . . . . ?
C14 N1 C4 O5 174.55(18) . . . . ?
C3 N1 C4 C21 173.13(19) . . . . ?
C14 N1 C4 C21 -7.3(2) . . . . ?
C19 C21 C4 O5 -173.09(18) . . . . ?
C27 C21 C4 O5 68.0(2) . . . . ?
C5 C21 C4 O5 -49.7(2) . . . . ?
C19 C21 C4 N1 8.68(18) . . . . ?
C27 C21 C4 N1 -110.22(15) . . . . ?
C5 C21 C4 N1 132.08(15) . . . . ?
C19 C21 C5 C6 46.4(2) . . . . ?
C27 C21 C5 C6 173.79(14) . . . . ?
C4 C21 C5 C6 -69.0(2) . . . . ?
C21 C5 C6 C7 -109.3(2) . . . . ?
C21 C5 C6 C25 75.56(19) . . . . ?
C25 C6 C7 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 -176.19(17) . . . . ?
C25 C6 C7 C20 -175.78(16) . . . . ?
C5 C6 C7 C20 9.4(3) . . . . ?
C6 C7 C8 C23 13.2(4) . . . . ?
C20 C7 C8 C23 -171.6(2) . . . . ?
C6 C7 C8 C9 -170.70(19) . . . . ?
C20 C7 C8 C9 4.51(19) . . . . ?
C23 C8 C9 C10 -1.2(3) . . . . ?
C7 C8 C9 C10 -177.9(2) . . . . ?
C23 C8 C9 N2 176.23(19) . . . . ?
C7 C8 C9 N2 -0.5(2) . . . . ?
N2 C9 C10 C11 -176.2(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C22 0.3(4) . . . . ?
C4 N1 C14 C15 -174.5(2) . . . . ?
C3 N1 C14 C15 5.1(3) . . . . ?
C4 N1 C14 C19 2.5(2) . . . . ?
C3 N1 C14 C19 -177.81(18) . . . . ?
C19 C14 C15 C16 -0.9(3) . . . . ?
N1 C14 C15 C16 175.9(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 F1 -179.8(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
F1 C17 C18 C19 179.88(18) . . . . ?
C17 C18 C19 C14 -0.4(3) . . . . ?
C17 C18 C19 C21 179.85(18) . . . . ?
C15 C14 C19 C18 1.0(3) . . . . ?
N1 C14 C19 C18 -176.32(16) . . . . ?
C15 C14 C19 C21 -179.18(18) . . . . ?
N1 C14 C19 C21 3.5(2) . . . . ?
C27 C21 C19 C18 -73.2(2) . . . . ?
C4 C21 C19 C18 172.43(18) . . . . ?
C5 C21 C19 C18 51.3(3) . . . . ?
C27 C21 C19 C14 106.98(17) . . . . ?
C4 C21 C19 C14 -7.35(18) . . . . ?
C5 C21 C19 C14 -128.43(17) . . . . ?
C6 C7 C20 O2 -10.2(3) . . . . ?
C8 C7 C20 O2 174.2(2) . . . . ?
C6 C7 C20 N2 168.62(17) . . . . ?
C8 C7 C20 N2 -6.98(19) . . . . ?
O2 C20 N2 C9 -174.16(19) . . . . ?
C7 C20 N2 C9 6.9(2) . . . . ?
O2 C20 N2 C24 4.2(3) . . . . ?
C7 C20 N2 C24 -174.68(19) . . . . ?
C10 C9 N2 C20 173.0(2) . . . . ?
C8 C9 N2 C20 -4.2(2) . . . . ?
C10 C9 N2 C24 -5.3(3) . . . . ?
C8 C9 N2 C24 177.42(19) . . . . ?
C10 C11 C22 C23 -0.7(5) . . . . ?
C9 C8 C23 C22 0.7(3) . . . . ?
C7 C8 C23 C22 176.4(2) . . . . ?
C11 C22 C23 C8 0.2(4) . . . . ?
C26 O3 C25 O4 -1.8(3) . . . . ?
C26 O3 C25 C6 175.40(19) . . . . ?
C7 C6 C25 O4 -101.6(2) . . . . ?
C5 C6 C25 O4 73.7(2) . . . . ?
C7 C6 C25 O3 81.2(2) . . . . ?
C5 C6 C25 O3 -103.43(18) . . . . ?
C19 C21 C27 C32 -1.5(2) . . . . ?
C4 C21 C27 C32 109.63(19) . . . . ?
C5 C21 C27 C32 -130.03(18) . . . . ?
C19 C21 C27 C28 177.72(17) . . . . ?
C4 C21 C27 C28 -71.1(2) . . . . ?
C5 C21 C27 C28 49.2(2) . . . . ?
C32 C27 C28 C29 1.3(3) . . . . ?
C21 C27 C28 C29 -178.0(2) . . . . ?
C27 C28 C29 C30 -0.5(4) . . . . ?
C28 C29 C30 C31 -0.7(4) . . . . ?
C29 C30 C31 C32 1.2(4) . . . . ?
C28 C27 C32 C31 -0.8(3) . . . . ?
C21 C27 C32 C31 178.43(19) . . . . ?
C30 C31 C32 C27 -0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 1007406'
