# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20151010c_0m
_database_code_depnum_ccdc_archive 'CCDC 1469147'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.2347(10)
_cell_length_b                   15.8096(17)
_cell_length_c                   12.1270(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.975(6)
_cell_angle_gamma                90.00
_cell_volume                     1617.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4722
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.32

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_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 area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12870
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3183
_reflns_number_gt                2871
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.0650P)²+0.5662P] 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         3183
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
O1 O 0.96435(10) 0.86842(5) 0.04149(8) 0.0220(2) Uani 1 1 d . . .
O2 O 1.30832(10) 0.64189(5) 0.05270(9) 0.0253(2) Uani 1 1 d . . .
N1 N 0.86170(11) 0.57572(6) 0.21481(9) 0.0179(2) Uani 1 1 d . . .
C1 C 1.28869(14) 0.78824(7) -0.00932(11) 0.0201(3) Uani 1 1 d . . .
C2 C 1.40910(15) 0.79943(8) -0.04782(12) 0.0265(3) Uani 1 1 d . . .
H2 H 1.4748 0.7548 -0.0477 0.032 Uiso 1 1 calc R . .
C3 C 1.42890(16) 0.87994(9) -0.08700(13) 0.0294(3) Uani 1 1 d . . .
H3 H 1.5084 0.8890 -0.1142 0.035 Uiso 1 1 calc R . .
C4 C 1.33151(15) 0.94681(8) -0.08591(12) 0.0251(3) Uani 1 1 d . . .
H4 H 1.3477 1.0001 -0.1115 0.030 Uiso 1 1 calc R . .
C5 C 1.20985(14) 0.93514(8) -0.04691(10) 0.0204(3) Uani 1 1 d . . .
H5 H 1.1447 0.9797 -0.0459 0.025 Uiso 1 1 calc R . .
C6 C 1.18991(13) 0.85478(7) -0.00989(10) 0.0184(3) Uani 1 1 d . . .
C7 C 1.07082(13) 0.82322(7) 0.03547(10) 0.0174(2) Uani 1 1 d . . .
C8 C 1.10533(13) 0.73480(7) 0.06533(10) 0.0188(3) Uani 1 1 d . . .
C9 C 1.23977(14) 0.71072(7) 0.03917(11) 0.0192(3) Uani 1 1 d . . .
C10 C 1.02275(13) 0.68102(7) 0.11492(10) 0.0183(3) Uani 1 1 d . . .
C11 C 0.90818(14) 0.71249(7) 0.15429(11) 0.0196(3) Uani 1 1 d . . .
H11 H 0.8846 0.7700 0.1463 0.024 Uiso 1 1 calc R . .
C12 C 0.83096(14) 0.66104(8) 0.20374(10) 0.0192(3) Uani 1 1 d . . .
C13 C 0.96903(13) 0.54152(7) 0.17534(10) 0.0184(3) Uani 1 1 d . . .
C14 C 1.04907(14) 0.59284(7) 0.12781(10) 0.0190(3) Uani 1 1 d . . .
H14 H 1.1230 0.5688 0.1033 0.023 Uiso 1 1 calc R . .
C15 C 0.71172(15) 0.69708(8) 0.24596(12) 0.0234(3) Uani 1 1 d . . .
H15A H 0.6976 0.7563 0.2268 0.035 Uiso 1 1 calc R . .
H15B H 0.7490 0.6898 0.3317 0.035 Uiso 1 1 calc R . .
H15C H 0.6124 0.6683 0.2064 0.035 Uiso 1 1 calc R . .
C16 C 0.99794(15) 0.44793(7) 0.18613(11) 0.0218(3) Uani 1 1 d . . .
H16A H 1.0699 0.4331 0.1502 0.033 Uiso 1 1 calc R . .
H16B H 0.8994 0.4186 0.1453 0.033 Uiso 1 1 calc R . .
H16C H 1.0430 0.4322 0.2698 0.033 Uiso 1 1 calc R . .
C17 C 0.77383(14) 0.51962(7) 0.26452(11) 0.0198(3) Uani 1 1 d . . .
H17A H 0.7505 0.5503 0.3247 0.024 Uiso 1 1 calc R . .
H17B H 0.8396 0.4714 0.3038 0.024 Uiso 1 1 calc R . .
C18 C 0.61964(14) 0.48857(7) 0.16543(11) 0.0199(3) Uani 1 1 d . . .
H18A H 0.6427 0.4620 0.1023 0.024 Uiso 1 1 calc R . .
H18B H 0.5511 0.5367 0.1304 0.024 Uiso 1 1 calc R . .
C19 C 0.53278(15) 0.42553(8) 0.21193(11) 0.0240(3) Uani 1 1 d . . .
H19A H 0.5962 0.3747 0.2394 0.029 Uiso 1 1 calc R . .
H19B H 0.5178 0.4498 0.2800 0.029 Uiso 1 1 calc R . .
C20 C 0.37248(15) 0.40290(9) 0.11305(12) 0.0285(3) Uani 1 1 d . . .
H20A H 0.3086 0.4530 0.0876 0.043 Uiso 1 1 calc R . .
H20B H 0.3203 0.3625 0.1435 0.043 Uiso 1 1 calc R . .
H20C H 0.3874 0.3790 0.0457 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2414(14) . ?
O2 C9 1.2358(15) . ?
N1 C12 1.3737(15) . ?
N1 C13 1.3745(15) . ?
N1 C17 1.4852(14) . ?
C1 C2 1.3812(17) . ?
C1 C6 1.3906(16) . ?
C1 C9 1.5060(16) . ?
C2 C3 1.3962(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3916(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3971(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.3845(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.5009(16) . ?
C7 C8 1.4467(16) . ?
C8 C10 1.4279(16) . ?
C8 C9 1.4516(16) . ?
C10 C14 1.4130(16) . ?
C10 C11 1.4161(16) . ?
C11 C12 1.3701(17) . ?
C11 H11 0.9300 . ?
C12 C15 1.5025(16) . ?
C13 C14 1.3722(16) . ?
C13 C16 1.4999(16) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.5238(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.5239(16) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.5213(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C13 120.12(10) . . ?
C12 N1 C17 120.05(9) . . ?
C13 N1 C17 119.78(10) . . ?
C2 C1 C6 121.20(11) . . ?
C2 C1 C9 130.29(11) . . ?
C6 C1 C9 108.50(10) . . ?
C1 C2 C3 117.81(12) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.98(12) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.97(12) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.53(11) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C5 C6 C1 121.49(11) . . ?
C5 C6 C7 129.63(11) . . ?
C1 C6 C7 108.88(10) . . ?
O1 C7 C8 129.84(11) . . ?
O1 C7 C6 123.09(10) . . ?
C8 C7 C6 107.06(9) . . ?
C10 C8 C7 125.43(10) . . ?
C10 C8 C9 125.91(10) . . ?
C7 C8 C9 108.64(10) . . ?
O2 C9 C8 129.74(11) . . ?
O2 C9 C1 123.35(11) . . ?
C8 C9 C1 106.91(10) . . ?
C14 C10 C11 115.33(10) . . ?
C14 C10 C8 122.46(10) . . ?
C11 C10 C8 122.20(10) . . ?
C12 C11 C10 122.14(11) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 N1 120.14(10) . . ?
C11 C12 C15 120.51(11) . . ?
N1 C12 C15 119.34(10) . . ?
C14 C13 N1 120.10(11) . . ?
C14 C13 C16 120.85(10) . . ?
N1 C13 C16 119.05(10) . . ?
C13 C14 C10 122.14(11) . . ?
C13 C14 H14 118.9 . . ?
C10 C14 H14 118.9 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 111.22(9) . . ?
N1 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
N1 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 C19 112.50(10) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 110.61(10) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C6 C1 C2 C3 0.24(19) . . . . ?
C9 C1 C2 C3 -178.94(12) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 -0.16(18) . . . . ?
C4 C5 C6 C1 1.11(17) . . . . ?
C4 C5 C6 C7 -179.70(11) . . . . ?
C2 C1 C6 C5 -1.18(18) . . . . ?
C9 C1 C6 C5 178.16(10) . . . . ?
C2 C1 C6 C7 179.48(11) . . . . ?
C9 C1 C6 C7 -1.18(13) . . . . ?
C5 C6 C7 O1 2.86(19) . . . . ?
C1 C6 C7 O1 -177.86(11) . . . . ?
C5 C6 C7 C8 -178.22(12) . . . . ?
C1 C6 C7 C8 1.06(12) . . . . ?
O1 C7 C8 C10 -3.0(2) . . . . ?
C6 C7 C8 C10 178.18(11) . . . . ?
O1 C7 C8 C9 178.34(12) . . . . ?
C6 C7 C8 C9 -0.48(12) . . . . ?
C10 C8 C9 O2 0.4(2) . . . . ?
C7 C8 C9 O2 179.07(12) . . . . ?
C10 C8 C9 C1 -178.87(11) . . . . ?
C7 C8 C9 C1 -0.21(13) . . . . ?
C2 C1 C9 O2 0.8(2) . . . . ?
C6 C1 C9 O2 -178.45(11) . . . . ?
C2 C1 C9 C8 -179.86(13) . . . . ?
C6 C1 C9 C8 0.88(13) . . . . ?
C7 C8 C10 C14 171.78(11) . . . . ?
C9 C8 C10 C14 -9.78(19) . . . . ?
C7 C8 C10 C11 -8.01(18) . . . . ?
C9 C8 C10 C11 170.43(11) . . . . ?
C14 C10 C11 C12 1.32(17) . . . . ?
C8 C10 C11 C12 -178.87(11) . . . . ?
C10 C11 C12 N1 -1.03(18) . . . . ?
C10 C11 C12 C15 179.17(11) . . . . ?
C13 N1 C12 C11 -0.57(17) . . . . ?
C17 N1 C12 C11 -177.89(10) . . . . ?
C13 N1 C12 C15 179.22(10) . . . . ?
C17 N1 C12 C15 1.91(16) . . . . ?
C12 N1 C13 C14 1.80(16) . . . . ?
C17 N1 C13 C14 179.12(10) . . . . ?
C12 N1 C13 C16 -178.75(10) . . . . ?
C17 N1 C13 C16 -1.43(15) . . . . ?
N1 C13 C14 C10 -1.47(18) . . . . ?
C16 C13 C14 C10 179.09(11) . . . . ?
C11 C10 C14 C13 -0.07(17) . . . . ?
C8 C10 C14 C13 -179.88(11) . . . . ?
C12 N1 C17 C18 87.75(12) . . . . ?
C13 N1 C17 C18 -89.57(12) . . . . ?
N1 C17 C18 C19 175.64(10) . . . . ?
C17 C18 C19 C20 174.49(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.055
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1469148'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H29 N O2'
_chemical_formula_sum            'C24 H29 N O2'
_chemical_formula_weight         363.48

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           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                   7.9388(15)
_cell_length_b                   8.0318(15)
_cell_length_c                   17.599(3)
_cell_angle_alpha                82.094(3)
_cell_angle_beta                 88.252(3)
_cell_angle_gamma                65.864(3)
_cell_volume                     1013.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5007
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.26

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5661
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3835
_reflns_number_gt                3298
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.1798P)²+0.2722P] 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         3835
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2450
_refine_ls_wR_factor_gt          0.2329
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
O1 O 0.82883(19) 1.04225(19) 0.28484(8) 0.0250(4) Uani 1 1 d . . .
O2 O 0.7265(2) 1.59398(19) 0.38558(8) 0.0306(4) Uani 1 1 d . . .
N1 N 0.7624(2) 1.0249(2) 0.58920(9) 0.0200(4) Uani 1 1 d . . .
C1 C 0.7853(2) 1.5006(3) 0.25946(11) 0.0229(5) Uani 1 1 d . . .
C2 C 0.7950(3) 1.6529(3) 0.21426(12) 0.0266(5) Uani 1 1 d . . .
H2 H 0.7816 1.7580 0.2349 0.032 Uiso 1 1 calc R . .
C3 C 0.8259(3) 1.6393(3) 0.13607(12) 0.0323(5) Uani 1 1 d . . .
H3 H 0.8332 1.7380 0.1039 0.039 Uiso 1 1 calc R . .
C4 C 0.8457(3) 1.4826(3) 0.10556(12) 0.0346(5) Uani 1 1 d . . .
H4 H 0.8634 1.4790 0.0532 0.042 Uiso 1 1 calc R . .
C5 C 0.8395(3) 1.3294(3) 0.15222(12) 0.0293(5) Uani 1 1 d . . .
H5 H 0.8558 1.2228 0.1322 0.035 Uiso 1 1 calc R . .
C6 C 0.8081(3) 1.3430(3) 0.22975(11) 0.0232(5) Uani 1 1 d . . .
C7 C 0.8006(2) 1.2011(3) 0.29402(10) 0.0203(4) Uani 1 1 d . . .
C8 C 0.7637(3) 1.2879(3) 0.36309(11) 0.0205(4) Uani 1 1 d . . .
C9 C 0.7533(3) 1.4738(3) 0.34400(11) 0.0223(4) Uani 1 1 d . . .
C10 C 0.7559(2) 1.2015(3) 0.43915(11) 0.0198(4) Uani 1 1 d . . .
C11 C 0.7359(3) 1.2919(3) 0.50446(11) 0.0224(4) Uani 1 1 d . . .
H11 H 0.7178 1.4150 0.4975 0.027 Uiso 1 1 calc R . .
C12 C 0.7422(3) 1.2047(3) 0.57789(11) 0.0216(4) Uani 1 1 d . . .
C13 C 0.7744(2) 0.9329(2) 0.52753(11) 0.0205(4) Uani 1 1 d . . .
C14 C 0.7724(2) 1.0170(3) 0.45427(11) 0.0209(4) Uani 1 1 d . . .
H14 H 0.7821 0.9519 0.4134 0.025 Uiso 1 1 calc R . .
C15 C 0.7356(3) 1.3001(3) 0.64585(12) 0.0279(5) Uani 1 1 d . . .
H15A H 0.8542 1.2458 0.6718 0.042 Uiso 1 1 calc R . .
H15B H 0.6441 1.2873 0.6803 0.042 Uiso 1 1 calc R . .
H15C H 0.7041 1.4284 0.6291 0.042 Uiso 1 1 calc R . .
C16 C 0.7920(3) 0.7380(3) 0.54190(12) 0.0271(5) Uani 1 1 d . . .
H16A H 0.7860 0.6964 0.4939 0.041 Uiso 1 1 calc R . .
H16B H 0.6932 0.7321 0.5734 0.041 Uiso 1 1 calc R . .
H16C H 0.9082 0.6607 0.5677 0.041 Uiso 1 1 calc R . .
C17 C 0.7674(3) 0.9315(3) 0.66856(10) 0.0213(4) Uani 1 1 d . . .
H17A H 0.8247 0.9794 0.7028 0.026 Uiso 1 1 calc R . .
H17B H 0.8433 0.8008 0.6701 0.026 Uiso 1 1 calc R . .
C18 C 0.5771(3) 0.9573(3) 0.69723(11) 0.0244(5) Uani 1 1 d . . .
H18A H 0.5190 0.9095 0.6633 0.029 Uiso 1 1 calc R . .
H18B H 0.5009 1.0877 0.6965 0.029 Uiso 1 1 calc R . .
C19 C 0.5899(3) 0.8576(3) 0.77902(11) 0.0259(5) Uani 1 1 d . . .
H19A H 0.6728 0.8845 0.8097 0.031 Uiso 1 1 calc R . .
H19B H 0.4689 0.9057 0.8012 0.031 Uiso 1 1 calc R . .
C20 C 0.6585(3) 0.6485(3) 0.78344(11) 0.0248(5) Uani 1 1 d . . .
H20A H 0.5797 0.6211 0.7507 0.030 Uiso 1 1 calc R . .
H20B H 0.7826 0.5990 0.7641 0.030 Uiso 1 1 calc R . .
C21 C 0.6599(3) 0.5539(3) 0.86504(11) 0.0277(5) Uani 1 1 d . . .
H21A H 0.7546 0.5633 0.8955 0.033 Uiso 1 1 calc R . .
H21B H 0.5419 0.6183 0.8876 0.033 Uiso 1 1 calc R . .
C22 C 0.6954(3) 0.3516(3) 0.86897(12) 0.0300(5) Uani 1 1 d . . .
H22A H 0.5971 0.3423 0.8409 0.036 Uiso 1 1 calc R . .
H22B H 0.8104 0.2881 0.8442 0.036 Uiso 1 1 calc R . .
C23 C 0.7062(4) 0.2574(3) 0.95073(13) 0.0423(6) Uani 1 1 d . . .
H23A H 0.5969 0.3293 0.9771 0.051 Uiso 1 1 calc R . .
H23B H 0.8126 0.2557 0.9770 0.051 Uiso 1 1 calc R . .
C24 C 0.7211(5) 0.0614(4) 0.95632(17) 0.0565(8) Uani 1 1 d . . .
H24A H 0.6172 0.0612 0.9299 0.085 Uiso 1 1 calc R . .
H24B H 0.7224 0.0121 1.0093 0.085 Uiso 1 1 calc R . .
H24C H 0.8331 -0.0131 0.9333 0.085 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.235(2) . ?
O2 C9 1.236(3) . ?
N1 C12 1.373(2) . ?
N1 C13 1.374(3) . ?
N1 C17 1.485(2) . ?
C1 C6 1.377(3) . ?
C1 C2 1.393(2) . ?
C1 C9 1.503(3) . ?
C2 C3 1.402(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(2) . ?
C7 C8 1.447(3) . ?
C8 C10 1.432(2) . ?
C8 C9 1.454(2) . ?
C10 C11 1.413(3) . ?
C10 C14 1.421(2) . ?
C11 C12 1.375(3) . ?
C11 H11 0.9300 . ?
C12 C15 1.495(3) . ?
C13 C14 1.368(3) . ?
C13 C16 1.500(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.518(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.533(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.530(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.528(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.523(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.518(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.519(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C13 120.29(15) . . ?
C12 N1 C17 119.50(16) . . ?
C13 N1 C17 120.21(15) . . ?
C6 C1 C2 122.21(19) . . ?
C6 C1 C9 108.82(16) . . ?
C2 C1 C9 128.97(19) . . ?
C1 C2 C3 116.5(2) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 121.62(19) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C1 C6 C5 121.23(18) . . ?
C1 C6 C7 109.06(17) . . ?
C5 C6 C7 129.66(19) . . ?
O1 C7 C8 130.20(16) . . ?
O1 C7 C6 123.17(17) . . ?
C8 C7 C6 106.58(16) . . ?
C10 C8 C7 126.27(16) . . ?
C10 C8 C9 124.87(17) . . ?
C7 C8 C9 108.62(16) . . ?
O2 C9 C8 130.04(18) . . ?
O2 C9 C1 123.09(17) . . ?
C8 C9 C1 106.86(16) . . ?
C11 C10 C14 115.36(17) . . ?
C11 C10 C8 122.49(17) . . ?
C14 C10 C8 122.14(18) . . ?
C12 C11 C10 122.49(18) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
N1 C12 C11 119.59(18) . . ?
N1 C12 C15 119.36(16) . . ?
C11 C12 C15 121.00(17) . . ?
C14 C13 N1 120.60(16) . . ?
C14 C13 C16 120.51(17) . . ?
N1 C13 C16 118.88(16) . . ?
C13 C14 C10 121.58(18) . . ?
C13 C14 H14 119.2 . . ?
C10 C14 H14 119.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 112.96(14) . . ?
N1 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 110.92(14) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C18 113.83(17) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 112.69(17) . . ?
C21 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C22 C21 C20 113.47(17) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C21 112.73(19) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 C24 113.9(2) . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C6 C1 C2 C3 1.2(3) . . . . ?
C9 C1 C2 C3 -179.75(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C9 C1 C6 C5 179.79(17) . . . . ?
C2 C1 C6 C7 176.78(16) . . . . ?
C9 C1 C6 C7 -2.5(2) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 -177.67(18) . . . . ?
C1 C6 C7 O1 -175.24(16) . . . . ?
C5 C6 C7 O1 2.3(3) . . . . ?
C1 C6 C7 C8 2.5(2) . . . . ?
C5 C6 C7 C8 179.98(19) . . . . ?
O1 C7 C8 C10 1.6(3) . . . . ?
C6 C7 C8 C10 -175.95(16) . . . . ?
O1 C7 C8 C9 176.03(18) . . . . ?
C6 C7 C8 C9 -1.46(19) . . . . ?
C10 C8 C9 O2 -4.5(3) . . . . ?
C7 C8 C9 O2 -179.08(19) . . . . ?
C10 C8 C9 C1 174.63(16) . . . . ?
C7 C8 C9 C1 0.0(2) . . . . ?
C6 C1 C9 O2 -179.25(17) . . . . ?
C2 C1 C9 O2 1.6(3) . . . . ?
C6 C1 C9 C8 1.5(2) . . . . ?
C2 C1 C9 C8 -177.62(18) . . . . ?
C7 C8 C10 C11 173.98(17) . . . . ?
C9 C8 C10 C11 0.4(3) . . . . ?
C7 C8 C10 C14 -4.5(3) . . . . ?
C9 C8 C10 C14 -178.07(16) . . . . ?
C14 C10 C11 C12 3.5(3) . . . . ?
C8 C10 C11 C12 -175.05(17) . . . . ?
C13 N1 C12 C11 -0.6(3) . . . . ?
C17 N1 C12 C11 -179.45(15) . . . . ?
C13 N1 C12 C15 -178.02(17) . . . . ?
C17 N1 C12 C15 3.2(3) . . . . ?
C10 C11 C12 N1 -2.3(3) . . . . ?
C10 C11 C12 C15 175.09(18) . . . . ?
C12 N1 C13 C14 2.1(3) . . . . ?
C17 N1 C13 C14 -179.10(15) . . . . ?
C12 N1 C13 C16 -178.63(16) . . . . ?
C17 N1 C13 C16 0.2(3) . . . . ?
N1 C13 C14 C10 -0.7(3) . . . . ?
C16 C13 C14 C10 -179.97(16) . . . . ?
C11 C10 C14 C13 -2.0(3) . . . . ?
C8 C10 C14 C13 176.55(16) . . . . ?
C12 N1 C17 C18 88.7(2) . . . . ?
C13 N1 C17 C18 -90.1(2) . . . . ?
N1 C17 C18 C19 179.66(15) . . . . ?
C17 C18 C19 C20 -75.6(2) . . . . ?
C18 C19 C20 C21 -176.89(15) . . . . ?
C19 C20 C21 C22 170.00(16) . . . . ?
C20 C21 C22 C23 177.04(17) . . . . ?
C21 C22 C23 C24 173.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.083
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20151125d_0m
_database_code_depnum_ccdc_archive 'CCDC 1469149'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C34 H29 N O2), C H4 O'
_chemical_formula_sum            'C69 H62 N2 O5'
_chemical_formula_weight         999.21

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.9842(17)
_cell_length_b                   25.762(4)
_cell_length_c                   15.533(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.280(7)
_cell_angle_gamma                90.00
_cell_volume                     2970.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3818
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.31

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1060
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_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 area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18572
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5739
_reflns_number_gt                3144
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.1573P)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         5739
_refine_ls_number_parameters     357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1266
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2459
_refine_ls_wR_factor_gt          0.2046
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.6541(4) 0.82647(8) 1.00404(19) 0.0818(7) Uani 1 1 d . . .
O2 O 0.6974(4) 0.88554(8) 0.73055(18) 0.0824(7) Uani 1 1 d . . .
N1 N 0.7840(3) 1.02732(8) 1.00563(19) 0.0605(6) Uani 1 1 d U . .
C1 C 0.6463(4) 0.80187(11) 0.7785(2) 0.0599(7) Uani 1 1 d . . .
C2 C 0.6280(5) 0.76811(13) 0.7039(3) 0.0743(9) Uani 1 1 d . . .
H2 H 0.6377 0.7798 0.6506 0.089 Uiso 1 1 calc R . .
C3 C 0.5949(5) 0.71633(14) 0.7110(3) 0.0856(10) Uani 1 1 d . . .
H3 H 0.5832 0.6928 0.6621 0.103 Uiso 1 1 calc R . .
C4 C 0.5792(6) 0.69925(14) 0.7893(4) 0.0922(12) Uani 1 1 d . . .
H4 H 0.5550 0.6644 0.7918 0.111 Uiso 1 1 calc R . .
C5 C 0.5986(5) 0.73289(12) 0.8647(3) 0.0794(9) Uani 1 1 d . . .
H5 H 0.5886 0.7211 0.9178 0.095 Uiso 1 1 calc R . .
C6 C 0.6334(4) 0.78469(11) 0.8586(2) 0.0632(7) Uani 1 1 d . . .
C7 C 0.6563(4) 0.82990(11) 0.9257(2) 0.0611(7) Uani 1 1 d . . .
C8 C 0.6809(4) 0.87547(10) 0.8790(2) 0.0549(7) Uani 1 1 d . . .
C9 C 0.6778(4) 0.85956(11) 0.7897(2) 0.0593(7) Uani 1 1 d . . .
C10 C 0.7093(3) 0.92708(10) 0.9191(2) 0.0498(6) Uani 1 1 d . . .
C11 C 0.7109(4) 0.93926(11) 1.0083(2) 0.0545(7) Uani 1 1 d . . .
H11 H 0.6871 0.9130 1.0400 0.065 Uiso 1 1 calc R . .
C12 C 0.7462(4) 0.98813(11) 1.0501(2) 0.0553(7) Uani 1 1 d . . .
C13 C 0.7738(4) 1.01864(10) 0.9152(2) 0.0555(7) Uani 1 1 d . . .
C14 C 0.7370(4) 0.96962(10) 0.8725(2) 0.0538(7) Uani 1 1 d . . .
H14 H 0.7302 0.9644 0.8112 0.065 Uiso 1 1 calc R . .
C15 C 0.7415(4) 0.99911(12) 1.1417(2) 0.0613(7) Uani 1 1 d . . .
H15 H 0.7113 1.0324 1.1497 0.074 Uiso 1 1 calc R . .
C16 C 0.7779(4) 0.96403(12) 1.2128(2) 0.0609(7) Uani 1 1 d . . .
H16 H 0.8120 0.9315 1.2038 0.073 Uiso 1 1 calc R . .
C17 C 0.7712(4) 0.97023(11) 1.3043(2) 0.0566(7) Uani 1 1 d . . .
C18 C 0.8216(5) 0.92955(13) 1.3724(3) 0.0728(9) Uani 1 1 d . . .
H18 H 0.8594 0.8988 1.3591 0.087 Uiso 1 1 calc R . .
C19 C 0.8183(5) 0.93277(14) 1.4608(3) 0.0770(9) Uani 1 1 d . . .
H19 H 0.8515 0.9042 1.5046 0.092 Uiso 1 1 calc R . .
C20 C 0.7665(4) 0.97779(13) 1.4834(2) 0.0655(8) Uani 1 1 d . . .
C21 C 0.7124(5) 1.01876(13) 1.4148(3) 0.0703(8) Uani 1 1 d . . .
H21 H 0.6748 1.0494 1.4286 0.084 Uiso 1 1 calc R . .
C22 C 0.7125(4) 1.01550(12) 1.3260(2) 0.0664(8) Uani 1 1 d . . .
H22 H 0.6733 1.0436 1.2805 0.080 Uiso 1 1 calc R . .
C23 C 0.7655(5) 0.98190(16) 1.5810(3) 0.0851(10) Uani 1 1 d . . .
H23A H 0.7570 0.9478 1.6028 0.128 Uiso 1 1 calc R . .
H23B H 0.6641 1.0023 1.5661 0.128 Uiso 1 1 calc R . .
H23C H 0.8748 0.9982 1.6357 0.128 Uiso 1 1 calc R . .
C24 C 0.8088(4) 1.06177(11) 0.8676(2) 0.0604(7) Uani 1 1 d . . .
H24 H 0.8972 1.0856 0.9117 0.072 Uiso 1 1 calc R . .
C25 C 0.7222(4) 1.06911(11) 0.7649(2) 0.0593(7) Uani 1 1 d . . .
H25 H 0.6289 1.0464 0.7214 0.071 Uiso 1 1 calc R . .
C26 C 0.7619(4) 1.10980(10) 0.7157(2) 0.0579(7) Uani 1 1 d . . .
C27 C 0.6504(5) 1.11556(12) 0.6067(2) 0.0689(8) Uani 1 1 d . . .
H27 H 0.5517 1.0937 0.5678 0.083 Uiso 1 1 calc R . .
C28 C 0.6849(5) 1.15321(14) 0.5564(3) 0.0792(10) Uani 1 1 d . . .
H28 H 0.6093 1.1562 0.4843 0.095 Uiso 1 1 calc R . .
C29 C 0.8302(5) 1.18644(13) 0.6119(3) 0.0798(10) Uani 1 1 d . . .
C30 C 0.9388(5) 1.18054(13) 0.7189(3) 0.0805(10) Uani 1 1 d . . .
H30 H 1.0373 1.2025 0.7578 0.097 Uiso 1 1 calc R . .
C31 C 0.9063(4) 1.14336(11) 0.7699(3) 0.0672(8) Uani 1 1 d . . .
H31 H 0.9827 1.1408 0.8420 0.081 Uiso 1 1 calc R . .
C32 C 0.8678(8) 1.22752(19) 0.5569(4) 0.1206(16) Uani 1 1 d . . .
H32A H 0.7874 1.2230 0.4829 0.181 Uiso 1 1 calc R . .
H32B H 0.9900 1.2243 0.5772 0.181 Uiso 1 1 calc R . .
H32C H 0.8500 1.2613 0.5757 0.181 Uiso 1 1 calc R . .
C33 C 0.8477(5) 1.07889(12) 1.0581(3) 0.0768(9) Uani 1 1 d U . .
H33A H 0.8947 1.0753 1.1314 0.092 Uiso 1 1 calc R . .
H33B H 0.9442 1.0914 1.0529 0.092 Uiso 1 1 calc R . .
C34 C 0.6970(6) 1.11699(16) 1.0089(4) 0.1079(14) Uani 1 1 d . . .
H34A H 0.6532 1.1214 0.9369 0.162 Uiso 1 1 calc R . .
H34B H 0.7392 1.1497 1.0442 0.162 Uiso 1 1 calc R . .
H34C H 0.6013 1.1045 1.0137 0.162 Uiso 1 1 calc R . .
O3 O -0.069(2) 0.8634(5) 0.6755(14) 0.349(12) Uani 0.50 1 d P . .
H3A H -0.0035 0.8888 0.6924 0.523 Uiso 0.50 1 calc PR . .
C35 C 0.024(4) 0.8190(4) 0.6798(13) 0.277(14) Uani 0.50 1 d P . .
H35A H 0.0320 0.7951 0.7297 0.416 Uiso 0.50 1 calc PR . .
H35B H 0.1429 0.8285 0.7002 0.416 Uiso 0.50 1 calc PR . .
H35C H -0.0391 0.8028 0.6124 0.416 Uiso 0.50 1 calc PR . .


_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 C7 1.232(4) . ?
O2 C9 1.228(3) . ?
N1 C12 1.370(4) . ?
N1 C13 1.373(4) . ?
N1 C33 1.494(4) . ?
C1 C2 1.382(4) . ?
C1 C6 1.387(4) . ?
C1 C9 1.504(4) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(4) . ?
C7 C8 1.461(4) . ?
C8 C10 1.429(4) . ?
C8 C9 1.430(4) . ?
C10 C14 1.411(4) . ?
C10 C11 1.412(4) . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 C15 1.475(4) . ?
C13 C14 1.378(4) . ?
C13 C24 1.464(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.317(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.465(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(4) . ?
C17 C22 1.397(4) . ?
C18 C19 1.392(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(5) . ?
C20 C23 1.526(4) . ?
C21 C22 1.382(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.337(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.455(4) . ?
C25 H25 0.9300 . ?
C26 C31 1.382(4) . ?
C26 C27 1.407(4) . ?
C27 C28 1.386(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.383(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(5) . ?
C29 C32 1.513(5) . ?
C30 C31 1.375(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.488(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O3 C35 1.40(2) . ?
O3 H3A 0.8270 . ?
C35 H35A 0.9601 . ?
C35 H35B 0.9601 . ?
C35 H35C 0.9601 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C13 120.2(2) . . ?
C12 N1 C33 120.5(2) . . ?
C13 N1 C33 119.2(2) . . ?
C2 C1 C6 121.4(3) . . ?
C2 C1 C9 130.2(3) . . ?
C6 C1 C9 108.4(2) . . ?
C1 C2 C3 118.0(3) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 C7 130.5(3) . . ?
C1 C6 C7 109.2(2) . . ?
O1 C7 C8 129.8(3) . . ?
O1 C7 C6 124.0(3) . . ?
C8 C7 C6 106.2(2) . . ?
C10 C8 C9 126.2(2) . . ?
C10 C8 C7 124.8(2) . . ?
C9 C8 C7 109.0(2) . . ?
O2 C9 C8 129.5(3) . . ?
O2 C9 C1 123.2(3) . . ?
C8 C9 C1 107.2(2) . . ?
C14 C10 C11 115.0(2) . . ?
C14 C10 C8 122.5(2) . . ?
C11 C10 C8 122.4(2) . . ?
C12 C11 C10 122.8(2) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
N1 C12 C11 119.7(2) . . ?
N1 C12 C15 119.7(2) . . ?
C11 C12 C15 120.6(3) . . ?
N1 C13 C14 120.1(2) . . ?
N1 C13 C24 118.9(2) . . ?
C14 C13 C24 120.9(3) . . ?
C13 C14 C10 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C10 C14 H14 119.0 . . ?
C16 C15 C12 123.3(3) . . ?
C16 C15 H15 118.4 . . ?
C12 C15 H15 118.4 . . ?
C15 C16 C17 127.7(3) . . ?
C15 C16 H16 116.2 . . ?
C17 C16 H16 116.2 . . ?
C18 C17 C22 117.2(3) . . ?
C18 C17 C16 119.2(3) . . ?
C22 C17 C16 123.5(3) . . ?
C17 C18 C19 122.2(3) . . ?
C17 C18 H18 118.9 . . ?
C19 C18 H18 118.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 118.3(3) . . ?
C19 C20 C23 120.5(3) . . ?
C21 C20 C23 121.2(3) . . ?
C20 C21 C22 121.8(3) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C21 C22 C17 120.3(3) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C13 124.3(3) . . ?
C25 C24 H24 117.8 . . ?
C13 C24 H24 117.8 . . ?
C24 C25 C26 125.3(3) . . ?
C24 C25 H25 117.3 . . ?
C26 C25 H25 117.3 . . ?
C31 C26 C27 117.1(3) . . ?
C31 C26 C25 123.6(3) . . ?
C27 C26 C25 119.3(3) . . ?
C28 C27 C26 121.2(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C27 121.0(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C30 C29 C28 117.4(3) . . ?
C30 C29 C32 121.7(4) . . ?
C28 C29 C32 120.9(4) . . ?
C31 C30 C29 122.3(3) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C30 C31 C26 121.1(3) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N1 110.4(3) . . ?
C34 C33 H33A 109.6 . . ?
N1 C33 H33A 109.6 . . ?
C34 C33 H33B 109.6 . . ?
N1 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 O3 H3A 110.2 . . ?
O3 C35 H35A 109.4 . . ?
O3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 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
C6 C1 C2 C3 0.5(5) . . . . ?
C9 C1 C2 C3 -178.3(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C9 C1 C6 C5 178.0(3) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
C9 C1 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 O1 3.2(6) . . . . ?
C1 C6 C7 O1 -178.9(3) . . . . ?
C5 C6 C7 C8 -177.0(3) . . . . ?
C1 C6 C7 C8 0.9(3) . . . . ?
O1 C7 C8 C10 0.4(5) . . . . ?
C6 C7 C8 C10 -179.4(3) . . . . ?
O1 C7 C8 C9 178.5(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C10 C8 C9 O2 -0.2(5) . . . . ?
C7 C8 C9 O2 -178.2(3) . . . . ?
C10 C8 C9 C1 179.2(3) . . . . ?
C7 C8 C9 C1 1.1(3) . . . . ?
C2 C1 C9 O2 -2.2(5) . . . . ?
C6 C1 C9 O2 178.9(3) . . . . ?
C2 C1 C9 C8 178.3(3) . . . . ?
C6 C1 C9 C8 -0.6(3) . . . . ?
C9 C8 C10 C14 0.5(4) . . . . ?
C7 C8 C10 C14 178.3(3) . . . . ?
C9 C8 C10 C11 -179.7(3) . . . . ?
C7 C8 C10 C11 -1.9(4) . . . . ?
C14 C10 C11 C12 -3.3(4) . . . . ?
C8 C10 C11 C12 176.9(3) . . . . ?
C13 N1 C12 C11 4.7(4) . . . . ?
C33 N1 C12 C11 -171.5(3) . . . . ?
C13 N1 C12 C15 -174.5(3) . . . . ?
C33 N1 C12 C15 9.3(4) . . . . ?
C10 C11 C12 N1 -0.8(4) . . . . ?
C10 C11 C12 C15 178.4(3) . . . . ?
C12 N1 C13 C14 -4.2(4) . . . . ?
C33 N1 C13 C14 172.0(3) . . . . ?
C12 N1 C13 C24 177.9(3) . . . . ?
C33 N1 C13 C24 -5.9(4) . . . . ?
N1 C13 C14 C10 -0.2(4) . . . . ?
C24 C13 C14 C10 177.7(2) . . . . ?
C11 C10 C14 C13 3.8(4) . . . . ?
C8 C10 C14 C13 -176.4(3) . . . . ?
N1 C12 C15 C16 -152.0(3) . . . . ?
C11 C12 C15 C16 28.8(4) . . . . ?
C12 C15 C16 C17 -177.7(3) . . . . ?
C15 C16 C17 C18 -177.2(3) . . . . ?
C15 C16 C17 C22 4.0(5) . . . . ?
C22 C17 C18 C19 -1.0(5) . . . . ?
C16 C17 C18 C19 -179.9(3) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C18 C19 C20 C21 2.2(5) . . . . ?
C18 C19 C20 C23 -179.0(3) . . . . ?
C19 C20 C21 C22 -1.1(5) . . . . ?
C23 C20 C21 C22 -179.9(3) . . . . ?
C20 C21 C22 C17 -1.1(5) . . . . ?
C18 C17 C22 C21 2.1(5) . . . . ?
C16 C17 C22 C21 -179.0(3) . . . . ?
N1 C13 C24 C25 -143.8(3) . . . . ?
C14 C13 C24 C25 38.4(4) . . . . ?
C13 C24 C25 C26 -176.1(3) . . . . ?
C24 C25 C26 C31 6.0(5) . . . . ?
C24 C25 C26 C27 -174.9(3) . . . . ?
C31 C26 C27 C28 0.2(5) . . . . ?
C25 C26 C27 C28 -178.9(3) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
C27 C28 C29 C30 0.0(5) . . . . ?
C27 C28 C29 C32 180.0(4) . . . . ?
C28 C29 C30 C31 0.0(6) . . . . ?
C32 C29 C30 C31 -179.9(4) . . . . ?
C29 C30 C31 C26 0.1(5) . . . . ?
C27 C26 C31 C30 -0.2(5) . . . . ?
C25 C26 C31 C30 178.9(3) . . . . ?
C12 N1 C33 C34 -101.2(4) . . . . ?
C13 N1 C33 C34 82.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20151029c_0m
_database_code_depnum_ccdc_archive 'CCDC 1469150'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H32 N O2, C H Cl3, H2 O'
_chemical_formula_sum            'C37 H35 Cl3 N O3'
_chemical_formula_weight         648.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.5014(4)
_cell_length_b                   12.7359(6)
_cell_length_c                   16.5492(8)
_cell_angle_alpha                109.704(2)
_cell_angle_beta                 97.327(2)
_cell_angle_gamma                95.420(2)
_cell_volume                     1654.91(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8491
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      56.78

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             678
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5413
_exptl_absorpt_correction_T_max  0.6789
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12741
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0827
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         65.49
_reflns_number_total             5513
_reflns_number_gt                2562
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_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)+(0.1999P)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     SHELXL
_refine_ls_extinction_coef       0.0038(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5513
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1711
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.2588
_refine_ls_wR_factor_gt          0.2260
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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
Cl1 Cl 0.8078(4) 0.4001(2) 0.9146(2) 0.2361(13) Uani 1 1 d . . .
Cl2 Cl 0.7002(2) 0.58538(15) 1.02380(13) 0.1675(7) Uani 1 1 d . . .
Cl3 Cl 0.8037(3) 0.62049(19) 0.87813(14) 0.2092(11) Uani 1 1 d . . .
O1 O 0.1040(3) 0.16075(15) 0.50205(12) 0.0792(8) Uani 1 1 d . . .
O2 O 0.4496(3) 0.41770(16) 0.75017(13) 0.0813(8) Uani 1 1 d . . .
O3 O 0.9012(9) 0.4328(5) 0.8469(8) 0.277(5) Uani 1 1 d . . .
H3A H 0.9807 0.4292 0.8201 0.416 Uiso 1 1 d R . .
H3B H 0.8959 0.5014 0.8754 0.416 Uiso 1 1 d R . .
N1 N 0.2757(4) 0.56434(19) 0.48972(15) 0.0717(8) Uani 1 1 d . . .
C1 C 0.1914(4) 0.2077(2) 0.57347(15) 0.0564(8) Uani 1 1 d . . .
C2 C 0.2328(4) 0.1474(2) 0.63492(14) 0.0569(8) Uani 1 1 d . . .
C3 C 0.1928(4) 0.0353(2) 0.62569(18) 0.0735(10) Uani 1 1 d . . .
H3 H 0.1213 -0.0143 0.5777 0.088 Uiso 1 1 calc R . .
C4 C 0.2631(5) -0.0004(3) 0.6905(2) 0.0872(11) Uani 1 1 d . . .
H4 H 0.2374 -0.0748 0.6864 0.105 Uiso 1 1 calc R . .
C5 C 0.3717(5) 0.0741(3) 0.76168(19) 0.0874(12) Uani 1 1 d . . .
H5 H 0.4201 0.0484 0.8036 0.105 Uiso 1 1 calc R . .
C6 C 0.4078(5) 0.1850(2) 0.77036(18) 0.0769(10) Uani 1 1 d . . .
H6 H 0.4770 0.2352 0.8190 0.092 Uiso 1 1 calc R . .
C7 C 0.3400(4) 0.2213(2) 0.70602(15) 0.0585(8) Uani 1 1 d . . .
C8 C 0.3665(4) 0.3339(2) 0.69655(15) 0.0573(8) Uani 1 1 d . . .
C9 C 0.2705(3) 0.3219(2) 0.61285(15) 0.0514(7) Uani 1 1 d . . .
C10 C 0.2695(4) 0.4047(2) 0.57324(15) 0.0549(7) Uani 1 1 d . . .
C11 C 0.1746(4) 0.3871(2) 0.49209(15) 0.0581(8) Uani 1 1 d . . .
H11 H 0.1064 0.3191 0.4645 0.070 Uiso 1 1 calc R . .
C12 C 0.1777(4) 0.4643(2) 0.45225(16) 0.0595(8) Uani 1 1 d . . .
C13 C 0.0660(4) 0.4395(3) 0.36995(17) 0.0708(9) Uani 1 1 d . . .
H13 H 0.0320 0.4997 0.3563 0.085 Uiso 1 1 calc R . .
C14 C 0.0123(4) 0.3369(2) 0.31515(17) 0.0723(10) Uani 1 1 d . . .
H14 H 0.0535 0.2788 0.3289 0.087 Uiso 1 1 calc R . .
C15 C -0.1042(4) 0.3035(2) 0.23537(16) 0.0659(9) Uani 1 1 d . . .
C16 C -0.1398(5) 0.1909(2) 0.18291(18) 0.0780(11) Uani 1 1 d . . .
H16 H -0.0841 0.1393 0.1985 0.094 Uiso 1 1 calc R . .
C17 C -0.2522(6) 0.1525(3) 0.1098(2) 0.0944(12) Uani 1 1 d . . .
H17 H -0.2752 0.0755 0.0783 0.113 Uiso 1 1 calc R . .
C18 C -0.3339(5) 0.2263(3) 0.08099(19) 0.0883(11) Uani 1 1 d . . .
C19 C -0.2964(5) 0.3415(3) 0.1338(2) 0.0829(11) Uani 1 1 d . . .
H19 H -0.3475 0.3939 0.1167 0.100 Uiso 1 1 calc R . .
C20 C -0.1891(4) 0.3775(2) 0.20795(17) 0.0689(9) Uani 1 1 d . . .
H20 H -0.1708 0.4537 0.2419 0.083 Uiso 1 1 calc R . .
C21 C -0.4571(6) 0.1867(4) -0.0007(2) 0.1169(15) Uani 1 1 d . . .
H21A H -0.4119 0.2032 -0.0461 0.175 Uiso 1 1 calc R . .
H21B H -0.5487 0.2248 0.0102 0.175 Uiso 1 1 calc R . .
H21C H -0.4895 0.1069 -0.0183 0.175 Uiso 1 1 calc R . .
C22 C 0.3724(4) 0.5112(2) 0.60964(16) 0.0600(8) Uani 1 1 d . . .
H22 H 0.4408 0.5276 0.6623 0.072 Uiso 1 1 calc R . .
C23 C 0.3736(4) 0.5880(2) 0.57037(17) 0.0644(8) Uani 1 1 d . . .
C24 C 0.4809(4) 0.6966(2) 0.60966(19) 0.0709(9) Uani 1 1 d . . .
H24 H 0.5118 0.7326 0.5726 0.085 Uiso 1 1 calc R . .
C25 C 0.5353(5) 0.7455(3) 0.69246(19) 0.0785(10) Uani 1 1 d . . .
H25 H 0.4959 0.7101 0.7281 0.094 Uiso 1 1 calc R . .
C26 C 0.6465(4) 0.8453(2) 0.7359(2) 0.0726(10) Uani 1 1 d . . .
C27 C 0.6897(5) 0.8838(3) 0.8267(2) 0.0888(11) Uani 1 1 d . . .
H27 H 0.6418 0.8455 0.8582 0.107 Uiso 1 1 calc R . .
C28 C 0.8041(5) 0.9794(3) 0.8704(3) 0.1022(13) Uani 1 1 d . . .
H28 H 0.8288 1.0033 0.9308 0.123 Uiso 1 1 calc R . .
C29 C 0.8824(5) 1.0403(3) 0.8280(3) 0.0953(12) Uani 1 1 d . . .
C30 C 0.8393(5) 0.9993(3) 0.7403(3) 0.0975(12) Uani 1 1 d . . .
H30 H 0.8888 1.0380 0.7095 0.117 Uiso 1 1 calc R . .
C31 C 0.7294(5) 0.9062(3) 0.6928(2) 0.0839(11) Uani 1 1 d . . .
H31 H 0.7092 0.8829 0.6324 0.101 Uiso 1 1 calc R . .
C32 C 1.0029(7) 1.1406(4) 0.8780(5) 0.144(2) Uani 1 1 d . . .
H32A H 1.1056 1.1275 0.8616 0.216 Uiso 1 1 calc R . .
H32B H 1.0094 1.1546 0.9391 0.216 Uiso 1 1 calc R . .
H32C H 0.9718 1.2049 0.8656 0.216 Uiso 1 1 calc R . .
C33 C 0.3094(6) 0.6424(3) 0.4344(3) 0.1174(15) Uani 1 1 d . . .
H33A H 0.4216 0.6752 0.4478 0.141 Uiso 1 1 calc R . .
H33B H 0.2822 0.5991 0.3725 0.141 Uiso 1 1 calc R . .
C34 C 0.2152(6) 0.7237(5) 0.4576(3) 0.1260(17) Uani 1 1 d . . .
H34A H 0.2453 0.7697 0.5188 0.151 Uiso 1 1 calc R . .
H34B H 0.1032 0.6913 0.4462 0.151 Uiso 1 1 calc R . .
C35 C 0.2490(7) 0.7993(6) 0.3950(5) 0.154(3) Uani 1 1 d . . .
H35A H 0.2712 0.7509 0.3396 0.184 Uiso 1 1 calc R . .
H35B H 0.1550 0.8332 0.3838 0.184 Uiso 1 1 calc R . .
C36 C 0.3742(10) 0.8796(6) 0.4358(5) 0.160(2) Uani 1 1 d . . .
H36A H 0.4263 0.8855 0.4905 0.192 Uiso 1 1 calc R . .
H36B H 0.4092 0.9296 0.4097 0.192 Uiso 1 1 calc R . .
C37 C 0.7233(7) 0.5129(4) 0.9130(5) 0.182(4) Uani 1 1 d . . .
H37 H 0.6149 0.4843 0.8793 0.218 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 C37 1.672(6) . ?
Cl1 H3B 1.7766 . ?
Cl2 C37 1.800(9) . ?
Cl3 C37 1.771(8) . ?
Cl3 H3B 1.7618 . ?
O1 C1 1.234(3) . ?
O2 C8 1.218(3) . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8500 . ?
N1 C12 1.356(4) . ?
N1 C23 1.401(4) . ?
N1 C33 1.592(6) . ?
C1 C9 1.433(4) . ?
C1 C2 1.496(4) . ?
C2 C7 1.385(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.493(4) . ?
C8 C9 1.467(4) . ?
C9 C10 1.417(4) . ?
C10 C11 1.411(4) . ?
C10 C22 1.435(4) . ?
C11 C12 1.356(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.477(4) . ?
C13 C14 1.311(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.454(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(4) . ?
C15 C20 1.395(4) . ?
C16 C17 1.354(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.412(5) . ?
C18 C21 1.502(5) . ?
C19 C20 1.344(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.345(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.473(4) . ?
C24 C25 1.299(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.418(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.400(4) . ?
C26 C31 1.416(5) . ?
C27 C28 1.398(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.352(6) . ?
C29 C32 1.480(6) . ?
C30 C31 1.368(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.353(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.666(8) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.334(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9300 . ?
C36 H36B 0.9300 . ?
C37 H37 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
C37 Cl1 H3B 57.7 . . ?
C37 Cl3 H3B 56.3 . . ?
H3A O3 H3B 109.5 . . ?
C12 N1 C23 119.6(2) . . ?
C12 N1 C33 120.2(3) . . ?
C23 N1 C33 118.8(3) . . ?
O1 C1 C9 129.6(2) . . ?
O1 C1 C2 122.4(2) . . ?
C9 C1 C2 108.0(2) . . ?
C7 C2 C3 121.3(3) . . ?
C7 C2 C1 108.0(2) . . ?
C3 C2 C1 130.4(2) . . ?
C2 C3 C4 117.8(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 C8 130.0(2) . . ?
C2 C7 C8 109.6(2) . . ?
O2 C8 C9 128.6(2) . . ?
O2 C8 C7 125.2(2) . . ?
C9 C8 C7 106.2(2) . . ?
C10 C9 C1 125.5(2) . . ?
C10 C9 C8 126.0(2) . . ?
C1 C9 C8 108.1(2) . . ?
C11 C10 C9 123.0(2) . . ?
C11 C10 C22 114.1(2) . . ?
C9 C10 C22 122.8(2) . . ?
C12 C11 C10 123.3(3) . . ?
C12 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N1 C12 C11 120.4(2) . . ?
N1 C12 C13 120.9(2) . . ?
C11 C12 C13 118.6(3) . . ?
C14 C13 C12 123.4(3) . . ?
C14 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?
C13 C14 C15 127.5(3) . . ?
C13 C14 H14 116.2 . . ?
C15 C14 H14 116.2 . . ?
C16 C15 C20 116.1(2) . . ?
C16 C15 C14 119.4(3) . . ?
C20 C15 C14 124.5(3) . . ?
C17 C16 C15 122.9(3) . . ?
C17 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C16 C17 C18 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 116.1(3) . . ?
C17 C18 C21 122.5(3) . . ?
C19 C18 C21 121.4(4) . . ?
C20 C19 C18 121.9(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C15 121.8(3) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C10 122.3(3) . . ?
C23 C22 H22 118.8 . . ?
C10 C22 H22 118.8 . . ?
C22 C23 N1 120.2(3) . . ?
C22 C23 C24 120.9(3) . . ?
N1 C23 C24 118.9(2) . . ?
C25 C24 C23 124.6(3) . . ?
C25 C24 H24 117.7 . . ?
C23 C24 H24 117.7 . . ?
C24 C25 C26 128.9(3) . . ?
C24 C25 H25 115.5 . . ?
C26 C25 H25 115.5 . . ?
C27 C26 C31 116.0(3) . . ?
C27 C26 C25 119.8(3) . . ?
C31 C26 C25 124.0(3) . . ?
C28 C27 C26 120.6(4) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C27 123.2(4) . . ?
C29 C28 H28 118.4 . . ?
C27 C28 H28 118.4 . . ?
C30 C29 C28 114.4(3) . . ?
C30 C29 C32 125.0(5) . . ?
C28 C29 C32 120.6(5) . . ?
C29 C30 C31 126.0(4) . . ?
C29 C30 H30 117.0 . . ?
C31 C30 H30 117.0 . . ?
C30 C31 C26 119.8(4) . . ?
C30 C31 H31 120.1 . . ?
C26 C31 H31 120.1 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N1 105.6(4) . . ?
C34 C33 H33A 110.6 . . ?
N1 C33 H33A 110.6 . . ?
C34 C33 H33B 110.6 . . ?
N1 C33 H33B 110.6 . . ?
H33A C33 H33B 108.8 . . ?
C33 C34 C35 103.6(5) . . ?
C33 C34 H34A 111.0 . . ?
C35 C34 H34A 111.0 . . ?
C33 C34 H34B 111.0 . . ?
C35 C34 H34B 111.0 . . ?
H34A C34 H34B 109.0 . . ?
C36 C35 C34 108.9(5) . . ?
C36 C35 H35A 109.9 . . ?
C34 C35 H35A 109.9 . . ?
C36 C35 H35B 109.9 . . ?
C34 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
C35 C36 H36A 120.0 . . ?
C35 C36 H36B 120.0 . . ?
H36A C36 H36B 120.0 . . ?
Cl1 C37 Cl3 125.9(5) . . ?
Cl1 C37 Cl2 105.3(4) . . ?
Cl3 C37 Cl2 104.6(3) . . ?
Cl1 C37 H37 106.6 . . ?
Cl3 C37 H37 106.6 . . ?
Cl2 C37 H37 106.6 . . ?

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 C7 176.3(3) . . . . ?
C9 C1 C2 C7 -3.2(3) . . . . ?
O1 C1 C2 C3 2.8(5) . . . . ?
C9 C1 C2 C3 -176.7(3) . . . . ?
C7 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C4 173.1(3) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C3 C4 C5 C6 1.9(6) . . . . ?
C4 C5 C6 C7 -2.5(6) . . . . ?
C5 C6 C7 C2 2.1(5) . . . . ?
C5 C6 C7 C8 -175.7(4) . . . . ?
C3 C2 C7 C6 -1.1(5) . . . . ?
C1 C2 C7 C6 -175.2(3) . . . . ?
C3 C2 C7 C8 177.1(3) . . . . ?
C1 C2 C7 C8 2.9(3) . . . . ?
C6 C7 C8 O2 -5.1(6) . . . . ?
C2 C7 C8 O2 177.0(3) . . . . ?
C6 C7 C8 C9 176.4(3) . . . . ?
C2 C7 C8 C9 -1.6(3) . . . . ?
O1 C1 C9 C10 -3.5(5) . . . . ?
C2 C1 C9 C10 176.0(3) . . . . ?
O1 C1 C9 C8 -177.3(3) . . . . ?
C2 C1 C9 C8 2.2(3) . . . . ?
O2 C8 C9 C10 7.3(5) . . . . ?
C7 C8 C9 C10 -174.2(3) . . . . ?
O2 C8 C9 C1 -179.0(3) . . . . ?
C7 C8 C9 C1 -0.5(3) . . . . ?
C1 C9 C10 C11 6.9(4) . . . . ?
C8 C9 C10 C11 179.6(3) . . . . ?
C1 C9 C10 C22 -169.1(3) . . . . ?
C8 C9 C10 C22 3.6(5) . . . . ?
C9 C10 C11 C12 -177.3(3) . . . . ?
C22 C10 C11 C12 -1.0(4) . . . . ?
C23 N1 C12 C11 -0.3(5) . . . . ?
C33 N1 C12 C11 166.0(3) . . . . ?
C23 N1 C12 C13 176.3(3) . . . . ?
C33 N1 C12 C13 -17.4(5) . . . . ?
C10 C11 C12 N1 0.3(5) . . . . ?
C10 C11 C12 C13 -176.4(3) . . . . ?
N1 C12 C13 C14 154.8(3) . . . . ?
C11 C12 C13 C14 -28.6(5) . . . . ?
C12 C13 C14 C15 176.2(3) . . . . ?
C13 C14 C15 C16 176.3(3) . . . . ?
C13 C14 C15 C20 -5.7(6) . . . . ?
C20 C15 C16 C17 -1.3(5) . . . . ?
C14 C15 C16 C17 176.8(4) . . . . ?
C15 C16 C17 C18 3.1(6) . . . . ?
C16 C17 C18 C19 -2.1(6) . . . . ?
C16 C17 C18 C21 178.9(4) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C21 C18 C19 C20 178.5(4) . . . . ?
C18 C19 C20 C15 2.4(6) . . . . ?
C16 C15 C20 C19 -1.5(5) . . . . ?
C14 C15 C20 C19 -179.5(3) . . . . ?
C11 C10 C22 C23 1.9(4) . . . . ?
C9 C10 C22 C23 178.2(3) . . . . ?
C10 C22 C23 N1 -2.0(5) . . . . ?
C10 C22 C23 C24 180.0(3) . . . . ?
C12 N1 C23 C22 1.2(5) . . . . ?
C33 N1 C23 C22 -165.3(3) . . . . ?
C12 N1 C23 C24 179.2(3) . . . . ?
C33 N1 C23 C24 12.7(5) . . . . ?
C22 C23 C24 C25 -26.2(5) . . . . ?
N1 C23 C24 C25 155.8(3) . . . . ?
C23 C24 C25 C26 175.4(3) . . . . ?
C24 C25 C26 C27 -179.9(4) . . . . ?
C24 C25 C26 C31 -5.2(6) . . . . ?
C31 C26 C27 C28 2.2(6) . . . . ?
C25 C26 C27 C28 177.3(4) . . . . ?
C26 C27 C28 C29 -0.9(7) . . . . ?
C27 C28 C29 C30 -0.1(6) . . . . ?
C27 C28 C29 C32 -179.8(4) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C32 C29 C30 C31 179.4(4) . . . . ?
C29 C30 C31 C26 1.7(7) . . . . ?
C27 C26 C31 C30 -2.6(5) . . . . ?
C25 C26 C31 C30 -177.4(4) . . . . ?
C12 N1 C33 C34 101.3(4) . . . . ?
C23 N1 C33 C34 -92.3(4) . . . . ?
N1 C33 C34 C35 -177.6(3) . . . . ?
C33 C34 C35 C36 -88.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        65.49
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.078
