# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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_120913_s2_ydb
#TrackingRef 'BDPH-SQ.cif'

_audit_creation_date             2012-09-17
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C37 H44 N2 O4, C H4 O'
_chemical_formula_sum            'C38 H48 N2 O5'
_chemical_formula_weight         612.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O3
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.5029(4)
_cell_length_b                   16.1542(5)
_cell_length_c                   15.0028(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.744(3)
_cell_angle_gamma                90.00
_cell_volume                     3347.68(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3760
_cell_measurement_temperature    143.05(10)
_cell_measurement_theta_max      29.0983
_cell_measurement_theta_min      2.8911
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14519
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      143.05(10)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -17.00 23.30 0.6500 30.0000
omega____ theta____ kappa____ phi______ frames
- -16.7361 -99.0000 30.0000 62

#__ type_ start__ end____ width___ exp.time_
2 omega -78.00 47.45 0.6500 30.0000
omega____ theta____ kappa____ phi______ frames
- -16.7361 0.0000 30.0000 193

#__ type_ start__ end____ width___ exp.time_
3 omega 0.00 61.10 0.6500 30.0000
omega____ theta____ kappa____ phi______ frames
- 19.8611 -99.0000 -150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0019686000
_diffrn_orient_matrix_UB_12      -0.0422657000
_diffrn_orient_matrix_UB_13      0.0133111000
_diffrn_orient_matrix_UB_21      -0.0302205000
_diffrn_orient_matrix_UB_22      0.0085945000
_diffrn_orient_matrix_UB_23      0.0281643000
_diffrn_orient_matrix_UB_31      -0.0414695000
_diffrn_orient_matrix_UB_32      -0.0082647000
_diffrn_orient_matrix_UB_33      -0.0386438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4482
_reflns_number_total             6829
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_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    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0425P)^2^+0.3166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.50719(9) 0.40521(9) 0.12293(9) 0.0300(3) Uani 1 1 d . . .
O4 O 0.65538(8) 0.30378(9) 0.14844(10) 0.0294(3) Uani 1 1 d . . .
H4 H 0.6096 0.3375 0.1413 0.044 Uiso 1 1 calc R . .
O1 O 0.69388(9) 0.63428(9) 0.15297(10) 0.0332(4) Uani 1 1 d . . .
O3 O 0.85130(9) 0.55125(9) 0.16825(10) 0.0320(4) Uani 1 1 d . . .
H3 H 0.7995 0.5761 0.1651 0.048 Uiso 1 1 calc R . .
N1 N 0.32454(10) 0.69749(11) 0.09513(10) 0.0228(4) Uani 1 1 d . . .
N2 N 0.99365(10) 0.28551(11) 0.20252(10) 0.0254(4) Uani 1 1 d . . .
C28 C 0.91758(12) 0.42035(13) 0.18354(12) 0.0227(4) Uani 1 1 d . . .
H28 H 0.9786 0.4460 0.1918 0.027 Uiso 1 1 calc R . .
C16 C 0.21361(13) 0.61232(14) 0.15509(13) 0.0277(5) Uani 1 1 d . . .
H16A H 0.2023 0.6612 0.1901 0.033 Uiso 1 1 calc R . .
H16B H 0.2675 0.5800 0.1971 0.033 Uiso 1 1 calc R . .
C30 C 0.74298(12) 0.43388(12) 0.15645(12) 0.0199(4) Uani 1 1 d . . .
C26 C 0.81981(12) 0.29723(13) 0.17221(11) 0.0222(4) Uani 1 1 d . . .
H26 H 0.8136 0.2387 0.1719 0.027 Uiso 1 1 calc R . .
C29 C 0.83669(13) 0.46852(13) 0.16897(12) 0.0225(4) Uani 1 1 d . . .
C2 C 0.22821(13) 0.82508(14) 0.10178(12) 0.0276(5) Uani 1 1 d . . .
H2 H 0.1701 0.7958 0.0969 0.033 Uiso 1 1 calc R . .
C9 C 0.40566(14) 0.91000(14) 0.11920(13) 0.0279(5) Uani 1 1 d . . .
C1 C 0.31310(13) 0.78365(13) 0.10252(12) 0.0239(5) Uani 1 1 d . . .
C27 C 0.91207(12) 0.33301(13) 0.18646(12) 0.0211(4) Uani 1 1 d . . .
C12 C 0.41822(12) 0.67771(13) 0.10816(12) 0.0222(4) Uani 1 1 d . . .
C19 C 0.44655(12) 0.59468(13) 0.11030(12) 0.0235(5) Uani 1 1 d . . .
H19 H 0.3946 0.5565 0.1004 0.028 Uiso 1 1 calc R . .
C10 C 0.40009(13) 0.82226(13) 0.11417(12) 0.0245(5) Uani 1 1 d . . .
C22 C 0.65925(12) 0.48411(13) 0.14328(12) 0.0210(4) Uani 1 1 d . . .
C35 C 0.98822(13) 0.19516(13) 0.20566(13) 0.0263(5) Uani 1 1 d . . .
H35A H 0.9417 0.1797 0.2393 0.032 Uiso 1 1 calc R . .
H35B H 1.0525 0.1734 0.2421 0.032 Uiso 1 1 calc R . .
C4 C 0.31840(15) 0.95376(14) 0.11441(12) 0.0297(5) Uani 1 1 d . . .
C11 C 0.47722(12) 0.75704(13) 0.12138(12) 0.0237(5) Uani 1 1 d . . .
C21 C 0.55700(13) 0.46947(13) 0.12823(12) 0.0226(4) Uani 1 1 d . . .
C25 C 0.73888(12) 0.34584(13) 0.15881(12) 0.0202(4) Uani 1 1 d . . .
O5 O 0.31498(10) 0.42204(11) 0.12139(13) 0.0522(5) Uani 1 1 d . . .
H5A H 0.3741 0.4182 0.1265 0.078 Uiso 1 1 calc R . .
C15 C 0.24157(12) 0.64082(13) 0.07062(12) 0.0250(5) Uani 1 1 d . . .
H15A H 0.2575 0.5918 0.0385 0.030 Uiso 1 1 calc R . .
H15B H 0.1855 0.6689 0.0263 0.030 Uiso 1 1 calc R . .
C14 C 0.52576(13) 0.76497(14) 0.04340(13) 0.0274(5) Uani 1 1 d . . .
H14A H 0.4758 0.7681 -0.0176 0.041 Uiso 1 1 calc R . .
H14B H 0.5669 0.7166 0.0448 0.041 Uiso 1 1 calc R . .
H14C H 0.5654 0.8153 0.0535 0.041 Uiso 1 1 calc R . .
C20 C 0.53560(12) 0.55797(13) 0.12406(12) 0.0223(4) Uani 1 1 d . . .
C3 C 0.23237(14) 0.90969(15) 0.10838(13) 0.0325(5) Uani 1 1 d . . .
H3A H 0.1761 0.9395 0.1089 0.039 Uiso 1 1 calc R . .
C31 C 1.08995(12) 0.32287(13) 0.22036(13) 0.0267(5) Uani 1 1 d . . .
H31A H 1.0850 0.3692 0.1760 0.032 Uiso 1 1 calc R . .
H31B H 1.1339 0.2810 0.2072 0.032 Uiso 1 1 calc R . .
C33 C 1.15263(15) 0.28686(15) 0.39177(14) 0.0368(6) Uani 1 1 d . . .
H33A H 1.1976 0.2462 0.3798 0.055 Uiso 1 1 calc R . .
H33B H 1.0911 0.2597 0.3879 0.055 Uiso 1 1 calc R . .
H33C H 1.1805 0.3104 0.4544 0.055 Uiso 1 1 calc R . .
C36 C 0.95745(14) 0.15362(14) 0.10964(13) 0.0288(5) Uani 1 1 d . . .
H36 H 0.8944 0.1784 0.0720 0.035 Uiso 1 1 calc R . .
C13 C 0.55112(13) 0.75878(13) 0.22020(12) 0.0275(5) Uani 1 1 d . . .
H13A H 0.5995 0.7152 0.2253 0.041 Uiso 1 1 calc R . .
H13B H 0.5175 0.7494 0.2669 0.041 Uiso 1 1 calc R . .
H13C H 0.5833 0.8128 0.2312 0.041 Uiso 1 1 calc R . .
C8 C 0.49046(16) 0.95676(15) 0.12714(14) 0.0365(6) Uani 1 1 d . . .
H8 H 0.5498 0.9290 0.1330 0.044 Uiso 1 1 calc R . .
C32 C 1.13519(13) 0.35530(14) 0.31951(13) 0.0279(5) Uani 1 1 d . . .
H32 H 1.0901 0.3967 0.3333 0.034 Uiso 1 1 calc R . .
C23 C 0.64042(13) 0.57276(14) 0.14155(13) 0.0249(5) Uani 1 1 d . . .
C5 C 0.32000(17) 1.04173(15) 0.11477(14) 0.0386(6) Uani 1 1 d . . .
H5 H 0.2627 1.0715 0.1119 0.046 Uiso 1 1 calc R . .
C18 C 0.03378(13) 0.60223(15) 0.06201(14) 0.0365(6) Uani 1 1 d . . .
H18A H 0.0263 0.6566 0.0880 0.055 Uiso 1 1 calc R . .
H18B H -0.0238 0.5686 0.0568 0.055 Uiso 1 1 calc R . .
H18C H 0.0417 0.6093 -0.0001 0.055 Uiso 1 1 calc R . .
C17 C 0.12259(13) 0.55913(14) 0.12614(14) 0.0318(5) Uani 1 1 d . . .
H17A H 0.1359 0.5090 0.0941 0.038 Uiso 1 1 calc R . .
H17B H 0.1078 0.5408 0.1833 0.038 Uiso 1 1 calc R . .
C39 C 0.26518(15) 0.35438(16) 0.07031(15) 0.0445(6) Uani 1 1 d . . .
H39A H 0.2921 0.3412 0.0195 0.067 Uiso 1 1 calc R . .
H39B H 0.1964 0.3683 0.0440 0.067 Uiso 1 1 calc R . .
H39C H 0.2722 0.3064 0.1118 0.067 Uiso 1 1 calc R . .
C7 C 0.48794(17) 1.04139(15) 0.12639(15) 0.0426(6) Uani 1 1 d . . .
H7 H 0.5453 1.0717 0.1309 0.051 Uiso 1 1 calc R . .
C37 C 0.94170(17) 0.06189(15) 0.12083(15) 0.0439(6) Uani 1 1 d . . .
H37A H 0.8902 0.0542 0.1499 0.066 Uiso 1 1 calc R . .
H37B H 1.0018 0.0369 0.1606 0.066 Uiso 1 1 calc R . .
H37C H 0.9229 0.0352 0.0592 0.066 Uiso 1 1 calc R . .
C38 C 1.03031(15) 0.16759(16) 0.05732(15) 0.0430(6) Uani 1 1 d . . .
H38A H 1.0928 0.1438 0.0931 0.064 Uiso 1 1 calc R . .
H38B H 1.0378 0.2271 0.0491 0.064 Uiso 1 1 calc R . .
H38C H 1.0075 0.1408 -0.0041 0.064 Uiso 1 1 calc R . .
C34 C 1.23043(14) 0.39872(16) 0.32577(15) 0.0411(6) Uani 1 1 d . . .
H34A H 1.2185 0.4433 0.2794 0.062 Uiso 1 1 calc R . .
H34B H 1.2758 0.3587 0.3134 0.062 Uiso 1 1 calc R . .
H34C H 1.2581 0.4220 0.3886 0.062 Uiso 1 1 calc R . .
C6 C 0.40214(18) 1.08376(15) 0.11917(14) 0.0438(6) Uani 1 1 d . . .
H6 H 0.4013 1.1425 0.1173 0.053 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0235(7) 0.0231(9) 0.0450(8) -0.0034(7) 0.0130(6) -0.0039(6)
O4 0.0217(7) 0.0192(8) 0.0480(8) -0.0002(7) 0.0119(6) -0.0017(6)
O1 0.0229(7) 0.0201(9) 0.0578(9) -0.0024(7) 0.0141(6) -0.0032(7)
O3 0.0209(7) 0.0170(8) 0.0574(9) 0.0008(7) 0.0108(7) -0.0004(6)
N1 0.0208(8) 0.0241(10) 0.0244(8) 0.0006(7) 0.0081(6) 0.0011(8)
N2 0.0233(8) 0.0210(10) 0.0317(9) 0.0021(8) 0.0078(7) 0.0024(8)
C28 0.0168(9) 0.0230(12) 0.0282(10) 0.0004(9) 0.0067(8) -0.0024(9)
C16 0.0270(10) 0.0302(13) 0.0265(10) 0.0022(9) 0.0089(8) 0.0005(10)
C30 0.0207(9) 0.0192(11) 0.0200(9) -0.0024(8) 0.0067(8) -0.0004(9)
C26 0.0256(10) 0.0179(11) 0.0240(10) 0.0033(8) 0.0090(8) -0.0007(9)
C29 0.0260(10) 0.0176(11) 0.0229(10) 0.0016(8) 0.0059(8) -0.0023(9)
C2 0.0260(10) 0.0334(14) 0.0240(10) 0.0024(10) 0.0083(8) 0.0065(10)
C9 0.0353(11) 0.0237(12) 0.0217(10) 0.0001(9) 0.0045(9) 0.0013(10)
C1 0.0257(10) 0.0252(12) 0.0207(10) 0.0026(9) 0.0067(8) 0.0039(9)
C27 0.0234(9) 0.0216(11) 0.0188(9) 0.0008(8) 0.0073(8) 0.0027(9)
C12 0.0214(9) 0.0239(12) 0.0225(10) -0.0002(9) 0.0087(8) 0.0003(9)
C19 0.0204(9) 0.0218(12) 0.0291(10) -0.0007(9) 0.0087(8) -0.0040(9)
C10 0.0262(10) 0.0255(12) 0.0202(10) 0.0016(9) 0.0047(8) 0.0022(9)
C22 0.0233(9) 0.0200(11) 0.0205(9) -0.0011(8) 0.0080(8) -0.0026(9)
C35 0.0285(10) 0.0215(12) 0.0295(11) 0.0048(9) 0.0099(8) 0.0068(9)
C4 0.0410(12) 0.0272(13) 0.0186(10) -0.0001(9) 0.0056(9) 0.0087(11)
C11 0.0223(10) 0.0204(12) 0.0280(10) 0.0007(9) 0.0070(8) 0.0001(9)
C21 0.0217(9) 0.0238(12) 0.0236(10) -0.0019(9) 0.0089(8) -0.0006(9)
C25 0.0205(9) 0.0213(11) 0.0190(9) -0.0021(8) 0.0062(7) -0.0059(9)
O5 0.0307(8) 0.0361(11) 0.0934(13) -0.0132(10) 0.0243(9) -0.0029(8)
C15 0.0208(9) 0.0277(13) 0.0267(10) -0.0007(9) 0.0077(8) -0.0015(9)
C14 0.0273(10) 0.0242(12) 0.0314(11) 0.0016(9) 0.0097(9) -0.0034(9)
C20 0.0231(10) 0.0208(11) 0.0241(10) 0.0009(9) 0.0089(8) -0.0004(9)
C3 0.0341(11) 0.0350(14) 0.0278(11) 0.0022(10) 0.0084(9) 0.0151(11)
C31 0.0209(9) 0.0262(12) 0.0347(11) 0.0049(10) 0.0109(8) 0.0047(9)
C33 0.0442(12) 0.0350(14) 0.0321(12) -0.0014(11) 0.0129(10) 0.0045(11)
C36 0.0341(11) 0.0242(12) 0.0270(11) 0.0019(9) 0.0078(9) 0.0038(10)
C13 0.0261(10) 0.0262(12) 0.0288(11) -0.0008(9) 0.0061(9) 0.0006(9)
C8 0.0433(13) 0.0266(13) 0.0366(12) 0.0009(10) 0.0075(10) -0.0018(11)
C32 0.0223(10) 0.0260(13) 0.0361(11) -0.0005(10) 0.0098(8) 0.0052(9)
C23 0.0225(10) 0.0250(12) 0.0286(11) -0.0002(9) 0.0097(8) 0.0019(9)
C5 0.0546(14) 0.0288(14) 0.0303(12) 0.0016(10) 0.0096(10) 0.0143(12)
C18 0.0263(10) 0.0481(16) 0.0368(12) 0.0027(11) 0.0121(9) -0.0002(11)
C17 0.0297(11) 0.0327(14) 0.0354(12) 0.0046(10) 0.0136(9) -0.0019(10)
C39 0.0367(12) 0.0511(18) 0.0454(14) -0.0079(13) 0.0120(10) -0.0069(12)
C7 0.0545(15) 0.0272(14) 0.0421(14) -0.0027(11) 0.0090(11) -0.0069(12)
C37 0.0636(15) 0.0265(14) 0.0369(13) -0.0023(11) 0.0083(11) -0.0033(12)
C38 0.0514(14) 0.0426(16) 0.0403(13) -0.0043(12) 0.0219(11) 0.0038(13)
C34 0.0288(11) 0.0448(16) 0.0460(13) 0.0058(12) 0.0058(10) -0.0021(11)
C6 0.0718(17) 0.0202(13) 0.0355(13) -0.0045(10) 0.0106(12) 0.0017(13)

_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
O2 C21 1.253(2) . ?
O4 H4 0.8400 . ?
O4 C25 1.356(2) . ?
O1 C23 1.240(2) . ?
O3 H3 0.8400 . ?
O3 C29 1.354(2) . ?
N1 C1 1.410(3) . ?
N1 C12 1.351(2) . ?
N1 C15 1.467(2) . ?
N2 C27 1.369(2) . ?
N2 C35 1.463(3) . ?
N2 C31 1.469(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.369(3) . ?
C28 C27 1.415(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.515(3) . ?
C16 C17 1.523(3) . ?
C30 C29 1.428(2) . ?
C30 C22 1.423(3) . ?
C30 C25 1.424(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.413(2) . ?
C26 C25 1.375(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.398(3) . ?
C2 C3 1.370(3) . ?
C9 C10 1.420(3) . ?
C9 C4 1.432(3) . ?
C9 C8 1.417(3) . ?
C1 C10 1.370(3) . ?
C12 C19 1.400(3) . ?
C12 C11 1.520(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(2) . ?
C10 C11 1.516(3) . ?
C22 C21 1.450(2) . ?
C22 C23 1.457(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.527(3) . ?
C4 C3 1.415(3) . ?
C4 C5 1.421(3) . ?
C11 C14 1.544(3) . ?
C11 C13 1.542(2) . ?
C21 C20 1.460(3) . ?
C21 C23 2.035(3) . ?
O5 H5A 0.8400 . ?
O5 C39 1.402(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C20 C23 1.481(2) . ?
C3 H3A 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.524(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33 C32 1.515(3) . ?
C36 H36 1.0000 . ?
C36 C37 1.517(3) . ?
C36 C38 1.513(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.368(3) . ?
C32 H32 1.0000 . ?
C32 C34 1.526(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.355(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C17 1.521(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.395(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C6 H6 0.9500 . ?

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
C25 O4 H4 109.5 . . ?
C29 O3 H3 109.5 . . ?
C1 N1 C15 121.91(15) . . ?
C12 N1 C1 111.07(16) . . ?
C12 N1 C15 126.93(17) . . ?
C27 N2 C35 120.86(16) . . ?
C27 N2 C31 121.64(17) . . ?
C35 N2 C31 117.47(15) . . ?
C29 C28 H28 119.4 . . ?
C29 C28 C27 121.22(17) . . ?
C27 C28 H28 119.4 . . ?
H16A C16 H16B 108.0 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C15 C16 C17 111.26(15) . . ?
C17 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C22 C30 C29 122.15(18) . . ?
C22 C30 C25 122.17(17) . . ?
C25 C30 C29 115.68(17) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.02(19) . . ?
O3 C29 C28 115.72(16) . . ?
O3 C29 C30 122.06(17) . . ?
C28 C29 C30 122.22(19) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C3 C2 C1 117.2(2) . . ?
C10 C9 C4 117.06(19) . . ?
C8 C9 C10 124.77(19) . . ?
C8 C9 C4 118.2(2) . . ?
C2 C1 N1 126.60(18) . . ?
C10 C1 N1 109.48(16) . . ?
C10 C1 C2 123.9(2) . . ?
N2 C27 C28 120.71(17) . . ?
N2 C27 C26 121.69(18) . . ?
C26 C27 C28 117.60(17) . . ?
N1 C12 C19 120.34(18) . . ?
N1 C12 C11 108.71(17) . . ?
C19 C12 C11 130.92(16) . . ?
C12 C19 H19 113.9 . . ?
C20 C19 C12 132.11(19) . . ?
C20 C19 H19 113.9 . . ?
C9 C10 C11 131.36(18) . . ?
C1 C10 C9 119.76(18) . . ?
C1 C10 C11 108.87(18) . . ?
C30 C22 C21 135.85(19) . . ?
C30 C22 C23 135.27(17) . . ?
C21 C22 C23 88.87(15) . . ?
N2 C35 H35A 108.7 . . ?
N2 C35 H35B 108.7 . . ?
N2 C35 C36 114.27(16) . . ?
H35A C35 H35B 107.6 . . ?
C36 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C3 C4 C9 120.2(2) . . ?
C3 C4 C5 121.1(2) . . ?
C5 C4 C9 118.7(2) . . ?
C12 C11 C14 109.86(16) . . ?
C12 C11 C13 109.84(16) . . ?
C10 C11 C12 101.70(14) . . ?
C10 C11 C14 112.65(16) . . ?
C10 C11 C13 109.72(16) . . ?
C13 C11 C14 112.53(15) . . ?
O2 C21 C22 133.43(19) . . ?
O2 C21 C20 134.21(17) . . ?
O2 C21 C23 178.00(16) . . ?
C22 C21 C20 92.35(16) . . ?
C22 C21 C23 45.70(11) . . ?
C20 C21 C23 46.66(11) . . ?
O4 C25 C30 122.70(17) . . ?
O4 C25 C26 115.05(17) . . ?
C26 C25 C30 122.25(17) . . ?
C39 O5 H5A 109.5 . . ?
N1 C15 C16 112.84(15) . . ?
N1 C15 H15A 109.0 . . ?
N1 C15 H15B 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C20 C21 127.23(18) . . ?
C19 C20 C23 145.2(2) . . ?
C21 C20 C23 87.54(15) . . ?
C2 C3 C4 121.66(19) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
N2 C31 H31A 108.5 . . ?
N2 C31 H31B 108.5 . . ?
N2 C31 C32 114.93(15) . . ?
H31A C31 H31B 107.5 . . ?
C32 C31 H31A 108.5 . . ?
C32 C31 H31B 108.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
C35 C36 H36 108.1 . . ?
C37 C36 C35 109.60(16) . . ?
C37 C36 H36 108.1 . . ?
C38 C36 C35 111.98(17) . . ?
C38 C36 H36 108.1 . . ?
C38 C36 C37 110.8(2) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C31 C32 H32 108.5 . . ?
C31 C32 C34 109.29(16) . . ?
C33 C32 C31 112.09(18) . . ?
C33 C32 H32 108.5 . . ?
C33 C32 C34 109.92(16) . . ?
C34 C32 H32 108.5 . . ?
O1 C23 C22 132.81(17) . . ?
O1 C23 C21 177.35(17) . . ?
O1 C23 C20 135.94(19) . . ?
C22 C23 C21 45.43(11) . . ?
C22 C23 C20 91.22(16) . . ?
C20 C23 C21 45.81(11) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 C16 114.54(18) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
O5 C39 H39A 109.5 . . ?
O5 C39 H39B 109.5 . . ?
O5 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C8 C7 H7 119.6 . . ?
C8 C7 C6 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O2 0.84 1.80 2.6361(18) 176.8 .
O3 H3 O1 0.84 1.76 2.5970(18) 175.4 .
O5 H5A O2 0.84 1.96 2.7939(19) 173.3 .

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
O2 C21 C20 C19 -1.4(3) . . . . ?
O2 C21 C20 C23 177.5(2) . . . . ?
O2 C21 C23 O1 16(7) . . . . ?
O2 C21 C23 C22 65(5) . . . . ?
O2 C21 C23 C20 -116(5) . . . . ?
N1 C1 C10 C9 177.25(16) . . . . ?
N1 C1 C10 C11 -3.9(2) . . . . ?
N1 C12 C19 C20 -178.52(18) . . . . ?
N1 C12 C11 C10 0.49(18) . . . . ?
N1 C12 C11 C14 -119.05(16) . . . . ?
N1 C12 C11 C13 116.65(16) . . . . ?
N2 C35 C36 C37 -172.69(17) . . . . ?
N2 C35 C36 C38 63.9(2) . . . . ?
N2 C31 C32 C33 62.7(2) . . . . ?
N2 C31 C32 C34 -175.21(17) . . . . ?
C30 C22 C21 O2 1.2(4) . . . . ?
C30 C22 C21 C20 179.9(2) . . . . ?
C30 C22 C21 C23 178.7(3) . . . . ?
C30 C22 C23 O1 -1.4(4) . . . . ?
C30 C22 C23 C21 -178.7(3) . . . . ?
C30 C22 C23 C20 -179.9(2) . . . . ?
C29 C28 C27 N2 -178.98(16) . . . . ?
C29 C28 C27 C26 1.1(3) . . . . ?
C29 C30 C22 C21 179.32(19) . . . . ?
C29 C30 C22 C23 -2.6(3) . . . . ?
C29 C30 C25 O4 179.69(15) . . . . ?
C29 C30 C25 C26 0.0(3) . . . . ?
C2 C1 C10 C9 -4.8(3) . . . . ?
C2 C1 C10 C11 174.06(16) . . . . ?
C9 C10 C11 C12 -179.21(19) . . . . ?
C9 C10 C11 C14 -61.7(3) . . . . ?
C9 C10 C11 C13 64.5(3) . . . . ?
C9 C4 C3 C2 -3.6(3) . . . . ?
C9 C4 C5 C6 0.3(3) . . . . ?
C9 C8 C7 C6 0.9(3) . . . . ?
C1 N1 C12 C19 175.47(16) . . . . ?
C1 N1 C12 C11 -2.8(2) . . . . ?
C1 N1 C15 C16 -87.1(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C10 C11 C12 2.07(19) . . . . ?
C1 C10 C11 C14 119.61(17) . . . . ?
C1 C10 C11 C13 -114.19(17) . . . . ?
C27 N2 C35 C36 81.3(2) . . . . ?
C27 N2 C31 C32 78.8(2) . . . . ?
C27 C28 C29 O3 179.58(16) . . . . ?
C27 C28 C29 C30 0.3(3) . . . . ?
C27 C26 C25 O4 -178.32(15) . . . . ?
C27 C26 C25 C30 1.4(3) . . . . ?
C12 N1 C1 C2 -173.54(17) . . . . ?
C12 N1 C1 C10 4.3(2) . . . . ?
C12 N1 C15 C16 96.8(2) . . . . ?
C12 C19 C20 C21 177.54(19) . . . . ?
C12 C19 C20 C23 -0.5(4) . . . . ?
C19 C12 C11 C10 -177.59(18) . . . . ?
C19 C12 C11 C14 62.9(2) . . . . ?
C19 C12 C11 C13 -61.4(3) . . . . ?
C19 C20 C23 O1 1.3(4) . . . . ?
C19 C20 C23 C22 179.6(3) . . . . ?
C19 C20 C23 C21 178.5(3) . . . . ?
C10 C9 C4 C3 2.2(3) . . . . ?
C10 C9 C4 C5 -177.08(17) . . . . ?
C10 C9 C8 C7 176.39(19) . . . . ?
C22 C30 C29 O3 -0.6(3) . . . . ?
C22 C30 C29 C28 178.65(17) . . . . ?
C22 C30 C25 O4 0.2(3) . . . . ?
C22 C30 C25 C26 -179.52(16) . . . . ?
C22 C21 C20 C19 179.92(18) . . . . ?
C22 C21 C20 C23 -1.18(14) . . . . ?
C22 C21 C23 O1 -49(4) . . . . ?
C22 C21 C23 C20 178.3(2) . . . . ?
C35 N2 C27 C28 179.95(16) . . . . ?
C35 N2 C27 C26 -0.1(3) . . . . ?
C35 N2 C31 C32 -99.2(2) . . . . ?
C4 C9 C10 C1 1.8(3) . . . . ?
C4 C9 C10 C11 -176.80(17) . . . . ?
C4 C9 C8 C7 -2.6(3) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
C11 C12 C19 C20 -0.6(3) . . . . ?
C21 C22 C23 O1 177.3(2) . . . . ?
C21 C22 C23 C20 -1.19(14) . . . . ?
C21 C20 C23 O1 -177.2(2) . . . . ?
C21 C20 C23 C22 1.18(14) . . . . ?
C25 C30 C29 O3 179.94(16) . . . . ?
C25 C30 C29 C28 -0.8(3) . . . . ?
C25 C30 C22 C21 -1.2(3) . . . . ?
C25 C30 C22 C23 176.85(19) . . . . ?
C25 C26 C27 N2 178.12(16) . . . . ?
C25 C26 C27 C28 -1.9(3) . . . . ?
C15 N1 C1 C2 9.9(3) . . . . ?
C15 N1 C1 C10 -172.29(15) . . . . ?
C15 N1 C12 C19 -8.1(3) . . . . ?
C15 N1 C12 C11 173.54(15) . . . . ?
C15 C16 C17 C18 -59.7(2) . . . . ?
C20 C21 C23 O1 132(4) . . . . ?
C20 C21 C23 C22 -178.3(2) . . . . ?
C3 C2 C1 N1 -178.99(17) . . . . ?
C3 C2 C1 C10 3.5(3) . . . . ?
C3 C4 C5 C6 -179.02(18) . . . . ?
C31 N2 C27 C28 2.1(3) . . . . ?
C31 N2 C27 C26 -177.99(16) . . . . ?
C31 N2 C35 C36 -100.76(19) . . . . ?
C8 C9 C10 C1 -177.19(18) . . . . ?
C8 C9 C10 C11 4.2(3) . . . . ?
C8 C9 C4 C3 -178.70(17) . . . . ?
C8 C9 C4 C5 2.0(3) . . . . ?
C8 C7 C6 C5 1.4(3) . . . . ?
C23 C22 C21 O2 -177.5(2) . . . . ?
C23 C22 C21 C20 1.20(14) . . . . ?
C23 C21 C20 C19 -178.9(2) . . . . ?
C5 C4 C3 C2 175.65(18) . . . . ?
C17 C16 C15 N1 175.55(17) . . . . ?



_database_code_depnum_ccdc_archive 'CCDC 925658'
#######################################################################
#
#                 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_dm13139

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H38 N2 O5'
_chemical_formula_weight         650.74

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   19.297(2)
_cell_length_b                   14.3767(17)
_cell_length_c                   24.546(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6809.6(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    7603
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.01

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2752
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65056
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         30.57
_reflns_number_total             10416
_reflns_number_gt                6004
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0793P)^2^+1.7374P] where P=(Fo^2^+2Fc^2^)/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         10416
_refine_ls_number_parameters     449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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
O1 O 0.33314(7) 0.94734(12) 0.21166(7) 0.0552(5) Uani 1 1 d . . .
O2 O 0.11248(6) 0.95436(10) 0.15040(6) 0.0374(3) Uani 1 1 d . . .
O3 O 0.35895(6) 0.78513(9) 0.17244(5) 0.0333(3) Uani 1 1 d . . .
H3 H 0.3511 0.8394 0.1835 0.050 Uiso 1 1 calc R . .
O4 O 0.13442(6) 0.81039(9) 0.08338(5) 0.0309(3) Uani 1 1 d . . .
H4 H 0.1279 0.8534 0.1060 0.046 Uiso 1 1 calc R . .
O5 O 0.01275(8) 1.05007(12) 0.21489(7) 0.0546(4) Uani 1 1 d . . .
H5 H 0.0391 1.0319 0.1898 0.082 Uiso 1 1 calc R . .
N1 N 0.29616(7) 0.57621(10) 0.03258(6) 0.0259(3) Uani 1 1 d . . .
N2 N 0.18943(7) 1.21687(10) 0.29691(6) 0.0257(3) Uani 1 1 d . . .
C1 C 0.27186(9) 0.94994(14) 0.19641(8) 0.0340(4) Uani 1 1 d . . .
C2 C 0.21143(9) 1.01185(13) 0.20672(7) 0.0287(4) Uani 1 1 d . . .
C3 C 0.17263(8) 0.95186(13) 0.16863(7) 0.0281(4) Uani 1 1 d . . .
C4 C 0.23152(8) 0.89112(12) 0.16076(7) 0.0254(3) Uani 1 1 d . . .
C5 C 0.24579(8) 0.80841(12) 0.13021(6) 0.0227(3) Uani 1 1 d . . .
C6 C 0.30985(8) 0.76015(12) 0.13592(7) 0.0245(3) Uani 1 1 d . . .
C7 C 0.32451(8) 0.68246(12) 0.10512(7) 0.0258(3) Uani 1 1 d . . .
H7 H 0.3672 0.6506 0.1100 0.031 Uiso 1 1 calc R . .
C8 C 0.27690(8) 0.65066(12) 0.06698(7) 0.0248(3) Uani 1 1 d . . .
C9 C 0.21288(8) 0.69407(12) 0.06109(7) 0.0248(3) Uani 1 1 d . . .
H9 H 0.1801 0.6708 0.0357 0.030 Uiso 1 1 calc R . .
C10 C 0.19719(8) 0.77116(12) 0.09231(7) 0.0234(3) Uani 1 1 d . . .
C11 C 0.35878(8) 0.57073(12) 0.00319(7) 0.0251(3) Uani 1 1 d . . .
C12 C 0.41298(9) 0.63443(13) 0.00002(7) 0.0289(4) Uani 1 1 d . . .
H12 H 0.4126 0.6900 0.0209 0.035 Uiso 1 1 calc R . .
C13 C 0.46732(9) 0.61384(14) -0.03462(8) 0.0337(4) Uani 1 1 d . . .
H13 H 0.5048 0.6564 -0.0377 0.040 Uiso 1 1 calc R . .
C14 C 0.46838(9) 0.53166(15) -0.06525(8) 0.0363(4) Uani 1 1 d . . .
H14 H 0.5065 0.5191 -0.0886 0.044 Uiso 1 1 calc R . .
C15 C 0.41465(9) 0.46904(14) -0.06180(7) 0.0320(4) Uani 1 1 d . . .
H15 H 0.4156 0.4131 -0.0824 0.038 Uiso 1 1 calc R . .
C16 C 0.35856(8) 0.48857(12) -0.02761(7) 0.0255(3) Uani 1 1 d . . .
C17 C 0.29319(9) 0.44217(12) -0.01749(7) 0.0255(3) Uani 1 1 d . . .
C18 C 0.26283(9) 0.36080(12) -0.03736(7) 0.0297(4) Uani 1 1 d . . .
H18 H 0.2871 0.3223 -0.0624 0.036 Uiso 1 1 calc R . .
C19 C 0.19719(10) 0.33718(13) -0.02015(8) 0.0340(4) Uani 1 1 d . . .
H19 H 0.1759 0.2824 -0.0339 0.041 Uiso 1 1 calc R . .
C20 C 0.16162(10) 0.39232(13) 0.01708(8) 0.0331(4) Uani 1 1 d . . .
H20 H 0.1166 0.3740 0.0286 0.040 Uiso 1 1 calc R . .
C21 C 0.19030(9) 0.47376(13) 0.03791(7) 0.0291(4) Uani 1 1 d . . .
H21 H 0.1661 0.5109 0.0636 0.035 Uiso 1 1 calc R . .
C22 C 0.25583(9) 0.49835(12) 0.01951(7) 0.0246(3) Uani 1 1 d . . .
C23 C 0.18790(9) 1.08749(13) 0.23507(7) 0.0286(4) Uani 1 1 d . . .
H23 H 0.1400 1.1003 0.2305 0.034 Uiso 1 1 calc R . .
C24 C 0.22281(8) 1.14946(12) 0.26990(7) 0.0253(3) Uani 1 1 d . . .
C25 C 0.29980(8) 1.15458(12) 0.28356(7) 0.0243(3) Uani 1 1 d . . .
C26 C 0.30210(8) 1.23834(12) 0.32115(7) 0.0240(3) Uani 1 1 d . . .
C27 C 0.35790(8) 1.27989(12) 0.34942(7) 0.0264(3) Uani 1 1 d . . .
C28 C 0.42828(9) 1.25142(13) 0.34521(8) 0.0323(4) Uani 1 1 d . . .
H28 H 0.4404 1.2017 0.3216 0.039 Uiso 1 1 calc R . .
C29 C 0.47870(10) 1.29489(15) 0.37485(9) 0.0422(5) Uani 1 1 d . . .
H29 H 0.5255 1.2749 0.3717 0.051 Uiso 1 1 calc R . .
C30 C 0.46220(11) 1.36894(16) 0.41003(10) 0.0476(5) Uani 1 1 d . . .
H30 H 0.4979 1.3985 0.4303 0.057 Uiso 1 1 calc R . .
C31 C 0.39532(11) 1.39868(15) 0.41525(9) 0.0420(5) Uani 1 1 d . . .
H31 H 0.3849 1.4488 0.4391 0.050 Uiso 1 1 calc R . .
C32 C 0.34142(9) 1.35554(13) 0.38546(8) 0.0305(4) Uani 1 1 d . . .
C33 C 0.27168(10) 1.38423(13) 0.39202(8) 0.0327(4) Uani 1 1 d . . .
H33 H 0.2618 1.4337 0.4165 0.039 Uiso 1 1 calc R . .
C34 C 0.21801(9) 1.34349(12) 0.36450(7) 0.0298(4) Uani 1 1 d . . .
H34 H 0.1714 1.3635 0.3691 0.036 Uiso 1 1 calc R . .
C35 C 0.23567(8) 1.27016(12) 0.32895(7) 0.0250(3) Uani 1 1 d . . .
C36 C 0.11382(8) 1.22974(13) 0.29989(7) 0.0296(4) Uani 1 1 d . . .
H36A H 0.0924 1.2099 0.2651 0.036 Uiso 1 1 calc R . .
H36B H 0.1031 1.2964 0.3055 0.036 Uiso 1 1 calc R . .
C37 C 0.08361(9) 1.17284(15) 0.34669(8) 0.0354(4) Uani 1 1 d . . .
H37A H 0.0926 1.1060 0.3400 0.043 Uiso 1 1 calc R . .
H37B H 0.1071 1.1903 0.3810 0.043 Uiso 1 1 calc R . .
C38 C 0.00649(9) 1.18816(17) 0.35283(10) 0.0465(5) Uani 1 1 d . . .
H38A H -0.0022 1.2545 0.3613 0.056 Uiso 1 1 calc R . .
H38B H -0.0167 1.1739 0.3178 0.056 Uiso 1 1 calc R . .
C39 C -0.02463(14) 1.1286(2) 0.39709(14) 0.0740(9) Uani 1 1 d . . .
H39A H -0.0171 1.0628 0.3885 0.111 Uiso 1 1 calc R . .
H39B H -0.0745 1.1409 0.3996 0.111 Uiso 1 1 calc R . .
H39C H -0.0026 1.1434 0.4320 0.111 Uiso 1 1 calc R . .
C40 C 0.31971(9) 1.06666(13) 0.31586(7) 0.0302(4) Uani 1 1 d . . .
H40A H 0.3694 1.0680 0.3240 0.045 Uiso 1 1 calc R . .
H40B H 0.3090 1.0113 0.2941 0.045 Uiso 1 1 calc R . .
H40C H 0.2934 1.0648 0.3500 0.045 Uiso 1 1 calc R . .
C41 C 0.34370(9) 1.16838(14) 0.23195(7) 0.0324(4) Uani 1 1 d . . .
H41A H 0.3332 1.2292 0.2159 0.049 Uiso 1 1 calc R . .
H41B H 0.3329 1.1192 0.2056 0.049 Uiso 1 1 calc R . .
H41C H 0.3930 1.1655 0.2415 0.049 Uiso 1 1 calc R . .
C42 C 0.00162(14) 0.9766(2) 0.25220(13) 0.0698(8) Uani 1 1 d . . .
H42A H 0.0451 0.9621 0.2710 0.105 Uiso 1 1 calc R . .
H42B H -0.0146 0.9215 0.2325 0.105 Uiso 1 1 calc R . .
H42C H -0.0334 0.9954 0.2790 0.105 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0260(7) 0.0620(10) 0.0777(11) -0.0414(9) -0.0181(7) 0.0132(7)
O2 0.0213(6) 0.0456(8) 0.0454(8) -0.0155(6) -0.0070(5) 0.0073(6)
O3 0.0249(6) 0.0365(7) 0.0384(7) -0.0090(6) -0.0092(5) 0.0062(5)
O4 0.0185(5) 0.0367(7) 0.0373(7) -0.0105(6) -0.0043(5) 0.0049(5)
O5 0.0357(8) 0.0630(11) 0.0650(11) -0.0155(9) 0.0049(7) 0.0112(7)
N1 0.0207(7) 0.0264(7) 0.0305(7) -0.0029(6) 0.0045(5) 0.0003(6)
N2 0.0203(6) 0.0289(8) 0.0279(7) -0.0024(6) 0.0008(5) 0.0042(6)
C1 0.0234(8) 0.0392(11) 0.0395(10) -0.0129(8) -0.0025(7) 0.0042(8)
C2 0.0231(8) 0.0319(9) 0.0311(9) -0.0044(7) -0.0012(6) 0.0032(7)
C3 0.0213(8) 0.0331(10) 0.0299(9) -0.0036(7) 0.0018(6) 0.0023(7)
C4 0.0188(7) 0.0299(9) 0.0276(8) -0.0028(7) 0.0011(6) 0.0006(6)
C5 0.0185(7) 0.0274(8) 0.0222(7) -0.0021(7) 0.0021(6) 0.0001(6)
C6 0.0196(7) 0.0294(9) 0.0244(8) 0.0008(7) -0.0011(6) -0.0011(6)
C7 0.0196(7) 0.0298(9) 0.0279(8) -0.0004(7) 0.0019(6) 0.0039(7)
C8 0.0231(8) 0.0259(8) 0.0254(8) 0.0002(7) 0.0046(6) 0.0004(6)
C9 0.0186(7) 0.0299(9) 0.0258(8) -0.0013(7) 0.0013(6) -0.0015(6)
C10 0.0165(7) 0.0284(9) 0.0252(8) -0.0001(7) 0.0022(6) -0.0006(6)
C11 0.0209(8) 0.0296(9) 0.0249(8) 0.0022(7) 0.0014(6) 0.0035(7)
C12 0.0252(8) 0.0286(9) 0.0327(9) 0.0009(8) 0.0020(7) 0.0012(7)
C13 0.0231(8) 0.0415(11) 0.0365(10) 0.0060(9) 0.0032(7) 0.0013(8)
C14 0.0254(9) 0.0522(13) 0.0313(10) 0.0009(9) 0.0066(7) 0.0084(8)
C15 0.0294(9) 0.0394(11) 0.0271(9) -0.0037(8) 0.0001(7) 0.0093(8)
C16 0.0234(8) 0.0284(9) 0.0246(8) 0.0028(7) -0.0013(6) 0.0058(7)
C17 0.0268(8) 0.0263(9) 0.0235(8) 0.0021(7) -0.0032(6) 0.0040(7)
C18 0.0363(10) 0.0254(9) 0.0275(9) 0.0005(7) -0.0037(7) 0.0030(7)
C19 0.0400(10) 0.0266(9) 0.0354(10) 0.0020(8) -0.0088(8) -0.0049(8)
C20 0.0297(9) 0.0314(10) 0.0382(10) 0.0048(8) -0.0024(8) -0.0059(8)
C21 0.0260(8) 0.0297(9) 0.0316(9) 0.0016(7) 0.0025(7) -0.0006(7)
C22 0.0253(8) 0.0217(8) 0.0268(8) 0.0019(7) -0.0025(6) 0.0001(6)
C23 0.0233(8) 0.0325(9) 0.0301(9) -0.0045(7) -0.0009(7) 0.0038(7)
C24 0.0233(8) 0.0273(9) 0.0251(8) 0.0000(7) 0.0016(6) 0.0040(7)
C25 0.0207(7) 0.0269(9) 0.0253(8) -0.0007(7) 0.0026(6) 0.0037(6)
C26 0.0237(8) 0.0227(8) 0.0257(8) 0.0019(7) 0.0014(6) 0.0012(6)
C27 0.0237(8) 0.0247(8) 0.0308(9) 0.0014(7) 0.0017(7) -0.0015(7)
C28 0.0258(8) 0.0310(10) 0.0402(10) -0.0007(8) 0.0018(7) -0.0022(7)
C29 0.0251(9) 0.0454(12) 0.0561(13) 0.0003(10) -0.0029(9) -0.0035(8)
C30 0.0340(10) 0.0423(12) 0.0666(15) -0.0088(11) -0.0091(10) -0.0088(9)
C31 0.0369(11) 0.0378(11) 0.0514(12) -0.0119(10) -0.0040(9) -0.0062(9)
C32 0.0303(9) 0.0261(9) 0.0353(9) -0.0015(8) -0.0005(7) -0.0018(7)
C33 0.0344(10) 0.0269(9) 0.0368(10) -0.0072(8) -0.0001(8) 0.0034(8)
C34 0.0267(8) 0.0274(9) 0.0354(9) -0.0033(8) 0.0027(7) 0.0057(7)
C35 0.0241(8) 0.0245(8) 0.0262(8) -0.0009(7) 0.0010(6) 0.0020(6)
C36 0.0199(8) 0.0361(10) 0.0329(9) -0.0055(8) -0.0013(6) 0.0071(7)
C37 0.0219(8) 0.0469(12) 0.0375(10) -0.0011(9) 0.0002(7) 0.0036(8)
C38 0.0241(9) 0.0497(13) 0.0656(14) -0.0062(11) 0.0096(9) 0.0040(9)
C39 0.0454(14) 0.0556(16) 0.121(3) 0.0165(17) 0.0439(15) 0.0095(12)
C40 0.0316(9) 0.0275(9) 0.0316(9) -0.0003(7) -0.0026(7) 0.0028(7)
C41 0.0264(8) 0.0419(11) 0.0289(9) 0.0007(8) 0.0045(7) 0.0036(8)
C42 0.0539(16) 0.0593(17) 0.096(2) -0.0116(16) 0.0248(14) -0.0091(13)

_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 1.241(2) . ?
O2 C3 1.244(2) . ?
O3 C6 1.3531(19) . ?
O3 H3 0.8400 . ?
O4 C10 1.3539(19) . ?
O4 H4 0.8400 . ?
O5 C42 1.414(3) . ?
O5 H5 0.8400 . ?
N1 C22 1.401(2) . ?
N1 C11 1.410(2) . ?
N1 C8 1.413(2) . ?
N2 C24 1.339(2) . ?
N2 C35 1.415(2) . ?
N2 C36 1.472(2) . ?
C1 C4 1.445(2) . ?
C1 C2 1.489(2) . ?
C1 C3 2.033(2) . ?
C2 C23 1.369(2) . ?
C2 C3 1.476(2) . ?
C3 C4 1.446(2) . ?
C4 C5 1.432(2) . ?
C5 C6 1.424(2) . ?
C5 C10 1.425(2) . ?
C6 C7 1.378(2) . ?
C7 C8 1.389(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.392(2) . ?
C11 C16 1.402(2) . ?
C12 C13 1.382(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.448(2) . ?
C17 C18 1.396(2) . ?
C17 C22 1.413(2) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.389(2) . ?
C21 H21 0.9500 . ?
C23 C24 1.406(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.525(2) . ?
C25 C26 1.518(2) . ?
C25 C41 1.537(2) . ?
C25 C40 1.541(2) . ?
C26 C35 1.374(2) . ?
C26 C27 1.414(2) . ?
C27 C28 1.422(2) . ?
C27 C32 1.438(2) . ?
C28 C29 1.366(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.407(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.366(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.415(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.417(3) . ?
C33 C34 1.368(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.410(2) . ?
C34 H34 0.9500 . ?
C36 C37 1.526(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.512(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.508(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C6 O3 H3 109.5 . . ?
C10 O4 H4 109.5 . . ?
C42 O5 H5 109.5 . . ?
C22 N1 C11 108.32(14) . . ?
C22 N1 C8 126.60(13) . . ?
C11 N1 C8 125.00(14) . . ?
C24 N2 C35 111.32(14) . . ?
C24 N2 C36 126.30(15) . . ?
C35 N2 C36 121.96(14) . . ?
O1 C1 C4 132.73(17) . . ?
O1 C1 C2 135.50(17) . . ?
C4 C1 C2 91.77(14) . . ?
O1 C1 C3 177.75(17) . . ?
C4 C1 C3 45.34(10) . . ?
C2 C1 C3 46.45(10) . . ?
C23 C2 C3 128.18(16) . . ?
C23 C2 C1 145.22(17) . . ?
C3 C2 C1 86.58(14) . . ?
O2 C3 C4 134.62(17) . . ?
O2 C3 C2 133.15(16) . . ?
C4 C3 C2 92.23(13) . . ?
O2 C3 C1 178.28(17) . . ?
C4 C3 C1 45.29(10) . . ?
C2 C3 C1 46.97(10) . . ?
C5 C4 C1 134.38(15) . . ?
C5 C4 C3 136.24(15) . . ?
C1 C4 C3 89.37(14) . . ?
C6 C5 C10 116.89(15) . . ?
C6 C5 C4 121.32(14) . . ?
C10 C5 C4 121.79(14) . . ?
O3 C6 C7 115.78(15) . . ?
O3 C6 C5 122.93(15) . . ?
C7 C6 C5 121.27(15) . . ?
C6 C7 C8 120.05(15) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.63(16) . . ?
C7 C8 N1 118.57(14) . . ?
C9 C8 N1 120.73(15) . . ?
C10 C9 C8 119.79(15) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O4 C10 C9 116.14(14) . . ?
O4 C10 C5 122.54(15) . . ?
C9 C10 C5 121.29(14) . . ?
C12 C11 C16 121.75(15) . . ?
C12 C11 N1 129.48(16) . . ?
C16 C11 N1 108.68(14) . . ?
C13 C12 C11 117.61(17) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C12 C13 C14 121.47(18) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 120.52(17) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.28(18) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C11 119.37(16) . . ?
C15 C16 C17 133.22(17) . . ?
C11 C16 C17 107.34(14) . . ?
C18 C17 C22 119.29(16) . . ?
C18 C17 C16 133.74(16) . . ?
C22 C17 C16 106.94(15) . . ?
C19 C18 C17 119.02(17) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 120.98(17) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 121.62(17) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 117.17(17) . . ?
C22 C21 H21 121.4 . . ?
C20 C21 H21 121.4 . . ?
C21 C22 N1 129.41(16) . . ?
C21 C22 C17 121.88(16) . . ?
N1 C22 C17 108.70(14) . . ?
C2 C23 C24 130.81(16) . . ?
C2 C23 H23 114.6 . . ?
C24 C23 H23 114.6 . . ?
N2 C24 C23 121.93(15) . . ?
N2 C24 C25 108.95(14) . . ?
C23 C24 C25 129.11(15) . . ?
C26 C25 C24 101.57(13) . . ?
C26 C25 C41 112.49(14) . . ?
C24 C25 C41 111.23(14) . . ?
C26 C25 C40 109.31(14) . . ?
C24 C25 C40 108.46(14) . . ?
C41 C25 C40 113.12(14) . . ?
C35 C26 C27 120.09(16) . . ?
C35 C26 C25 108.75(14) . . ?
C27 C26 C25 131.01(15) . . ?
C26 C27 C28 124.76(16) . . ?
C26 C27 C32 116.96(15) . . ?
C28 C27 C32 118.28(16) . . ?
C29 C28 C27 120.65(18) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C30 120.77(19) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C31 C30 C29 120.55(19) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.6(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C31 C32 C33 120.80(17) . . ?
C31 C32 C27 119.15(17) . . ?
C33 C32 C27 120.03(16) . . ?
C34 C33 C32 122.56(17) . . ?
C34 C33 H33 118.7 . . ?
C32 C33 H33 118.7 . . ?
C33 C34 C35 116.27(16) . . ?
C33 C34 H34 121.9 . . ?
C35 C34 H34 121.9 . . ?
C26 C35 C34 124.08(16) . . ?
C26 C35 N2 109.31(14) . . ?
C34 C35 N2 126.60(15) . . ?
N2 C36 C37 110.39(14) . . ?
N2 C36 H36A 109.6 . . ?
C37 C36 H36A 109.6 . . ?
N2 C36 H36B 109.6 . . ?
C37 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
C38 C37 C36 111.90(16) . . ?
C38 C37 H37A 109.2 . . ?
C36 C37 H37A 109.2 . . ?
C38 C37 H37B 109.2 . . ?
C36 C37 H37B 109.2 . . ?
H37A C37 H37B 107.9 . . ?
C39 C38 C37 112.4(2) . . ?
C39 C38 H38A 109.1 . . ?
C37 C38 H38A 109.1 . . ?
C39 C38 H38B 109.1 . . ?
C37 C38 H38B 109.1 . . ?
H38A C38 H38B 107.9 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C25 C40 H40A 109.5 . . ?
C25 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C25 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C25 C41 H41A 109.5 . . ?
C25 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C25 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O5 C42 H42A 109.5 . . ?
O5 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O5 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
O1 C1 C2 C23 -3.3(5) . . . . ?
C4 C1 C2 C23 176.5(3) . . . . ?
C3 C1 C2 C23 178.3(4) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
C4 C1 C2 C3 -1.75(15) . . . . ?
C23 C2 C3 O2 3.6(4) . . . . ?
C1 C2 C3 O2 -177.6(2) . . . . ?
C23 C2 C3 C4 -177.02(19) . . . . ?
C1 C2 C3 C4 1.75(14) . . . . ?
C23 C2 C3 C1 -178.8(3) . . . . ?
O1 C1 C3 O2 -56(9) . . . . ?
C4 C1 C3 O2 -88(6) . . . . ?
C2 C1 C3 O2 95(6) . . . . ?
O1 C1 C3 C4 32(5) . . . . ?
C2 C1 C3 C4 -177.5(2) . . . . ?
O1 C1 C3 C2 -151(5) . . . . ?
C4 C1 C3 C2 177.5(2) . . . . ?
O1 C1 C4 C5 0.7(4) . . . . ?
C2 C1 C4 C5 -179.1(2) . . . . ?
C3 C1 C4 C5 179.1(3) . . . . ?
O1 C1 C4 C3 -178.4(3) . . . . ?
C2 C1 C4 C3 1.78(15) . . . . ?
O2 C3 C4 C5 -1.5(4) . . . . ?
C2 C3 C4 C5 179.2(2) . . . . ?
C1 C3 C4 C5 -179.0(3) . . . . ?
O2 C3 C4 C1 177.6(2) . . . . ?
C2 C3 C4 C1 -1.80(15) . . . . ?
C1 C4 C5 C6 7.4(3) . . . . ?
C3 C4 C5 C6 -173.93(19) . . . . ?
C1 C4 C5 C10 -171.82(19) . . . . ?
C3 C4 C5 C10 6.8(3) . . . . ?
C10 C5 C6 O3 -176.42(15) . . . . ?
C4 C5 C6 O3 4.3(3) . . . . ?
C10 C5 C6 C7 1.6(2) . . . . ?
C4 C5 C6 C7 -177.69(16) . . . . ?
O3 C6 C7 C8 179.20(15) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 -2.9(3) . . . . ?
C6 C7 C8 N1 174.17(15) . . . . ?
C22 N1 C8 C7 135.14(17) . . . . ?
C11 N1 C8 C7 -48.4(2) . . . . ?
C22 N1 C8 C9 -47.8(2) . . . . ?
C11 N1 C8 C9 128.66(18) . . . . ?
C7 C8 C9 C10 1.9(3) . . . . ?
N1 C8 C9 C10 -175.08(15) . . . . ?
C8 C9 C10 O4 178.76(15) . . . . ?
C8 C9 C10 C5 0.9(3) . . . . ?
C6 C5 C10 O4 179.71(15) . . . . ?
C4 C5 C10 O4 -1.0(3) . . . . ?
C6 C5 C10 C9 -2.5(2) . . . . ?
C4 C5 C10 C9 176.71(16) . . . . ?
C22 N1 C11 C12 175.42(17) . . . . ?
C8 N1 C11 C12 -1.6(3) . . . . ?
C22 N1 C11 C16 -1.12(18) . . . . ?
C8 N1 C11 C16 -178.15(15) . . . . ?
C16 C11 C12 C13 -0.3(3) . . . . ?
N1 C11 C12 C13 -176.41(17) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C14 C15 C16 C17 175.16(18) . . . . ?
C12 C11 C16 C15 1.1(2) . . . . ?
N1 C11 C16 C15 177.92(15) . . . . ?
C12 C11 C16 C17 -176.11(16) . . . . ?
N1 C11 C16 C17 0.75(18) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C11 C16 C17 C18 177.79(18) . . . . ?
C15 C16 C17 C22 -176.72(18) . . . . ?
C11 C16 C17 C22 -0.10(18) . . . . ?
C22 C17 C18 C19 -0.3(2) . . . . ?
C16 C17 C18 C19 -177.94(18) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C20 C21 C22 N1 178.79(17) . . . . ?
C20 C21 C22 C17 -1.9(3) . . . . ?
C11 N1 C22 C21 -179.57(17) . . . . ?
C8 N1 C22 C21 -2.6(3) . . . . ?
C11 N1 C22 C17 1.05(19) . . . . ?
C8 N1 C22 C17 178.02(15) . . . . ?
C18 C17 C22 C21 1.7(3) . . . . ?
C16 C17 C22 C21 179.98(15) . . . . ?
C18 C17 C22 N1 -178.83(14) . . . . ?
C16 C17 C22 N1 -0.58(18) . . . . ?
C3 C2 C23 C24 -176.88(18) . . . . ?
C1 C2 C23 C24 5.3(4) . . . . ?
C35 N2 C24 C23 -179.68(16) . . . . ?
C36 N2 C24 C23 7.6(3) . . . . ?
C35 N2 C24 C25 -0.06(19) . . . . ?
C36 N2 C24 C25 -172.76(15) . . . . ?
C2 C23 C24 N2 -175.74(19) . . . . ?
C2 C23 C24 C25 4.7(3) . . . . ?
N2 C24 C25 C26 -1.73(17) . . . . ?
C23 C24 C25 C26 177.86(17) . . . . ?
N2 C24 C25 C41 -121.62(16) . . . . ?
C23 C24 C25 C41 58.0(2) . . . . ?
N2 C24 C25 C40 113.37(16) . . . . ?
C23 C24 C25 C40 -67.0(2) . . . . ?
C24 C25 C26 C35 2.96(17) . . . . ?
C41 C25 C26 C35 121.95(16) . . . . ?
C40 C25 C26 C35 -111.51(15) . . . . ?
C24 C25 C26 C27 178.39(17) . . . . ?
C41 C25 C26 C27 -62.6(2) . . . . ?
C40 C25 C26 C27 63.9(2) . . . . ?
C35 C26 C27 C28 178.77(17) . . . . ?
C25 C26 C27 C28 3.8(3) . . . . ?
C35 C26 C27 C32 -0.4(2) . . . . ?
C25 C26 C27 C32 -175.38(16) . . . . ?
C26 C27 C28 C29 -178.94(19) . . . . ?
C32 C27 C28 C29 0.2(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C31 0.1(4) . . . . ?
C29 C30 C31 C32 0.1(4) . . . . ?
C30 C31 C32 C33 178.0(2) . . . . ?
C30 C31 C32 C27 -0.1(3) . . . . ?
C26 C27 C32 C31 179.19(17) . . . . ?
C28 C27 C32 C31 0.0(3) . . . . ?
C26 C27 C32 C33 1.0(3) . . . . ?
C28 C27 C32 C33 -178.17(17) . . . . ?
C31 C32 C33 C34 -179.15(19) . . . . ?
C27 C32 C33 C34 -1.0(3) . . . . ?
C32 C33 C34 C35 0.3(3) . . . . ?
C27 C26 C35 C34 -0.4(3) . . . . ?
C25 C26 C35 C34 175.67(16) . . . . ?
C27 C26 C35 N2 -179.20(15) . . . . ?
C25 C26 C35 N2 -3.17(19) . . . . ?
C33 C34 C35 C26 0.4(3) . . . . ?
C33 C34 C35 N2 179.04(17) . . . . ?
C24 N2 C35 C26 2.1(2) . . . . ?
C36 N2 C35 C26 175.15(15) . . . . ?
C24 N2 C35 C34 -176.72(17) . . . . ?
C36 N2 C35 C34 -3.7(3) . . . . ?
C24 N2 C36 C37 87.1(2) . . . . ?
C35 N2 C36 C37 -84.8(2) . . . . ?
N2 C36 C37 C38 177.07(16) . . . . ?
C36 C37 C38 C39 177.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.57
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 944996'