# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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#######################################################################

data_mo_170254LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1540298'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H32 N2 O3'
_chemical_formula_weight         540.63

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6369(10)
_cell_length_b                   12.1697(13)
_cell_length_c                   12.3161(12)
_cell_angle_alpha                86.914(3)
_cell_angle_beta                 73.831(3)
_cell_angle_gamma                85.494(3)
_cell_volume                     1382.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    6736
_cell_measurement_theta_min      2.3954
_cell_measurement_theta_max      26.4195

_exptl_crystal_description       lump
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9031
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            21891
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.679
_diffrn_reflns_theta_max         26.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5689
_reflns_number_gt                4683
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5689
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.71909(12) 0.56459(10) 0.33215(10) 0.0148(2) Uani 1 1 d . . . . .
C2 C 0.73115(13) 0.68797(10) 0.33765(10) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.6890 0.7133 0.4157 0.019 Uiso 1 1 calc R U . . .
H2B H 0.8335 0.7068 0.3113 0.019 Uiso 1 1 calc R U . . .
C3 C 0.64577(13) 0.73919(10) 0.25934(10) 0.0152(3) Uani 1 1 d . . . . .
H3 H 0.7125 0.7492 0.1817 0.018 Uiso 1 1 calc R U . . .
C4 C 0.74065(13) 0.50244(10) 0.43856(10) 0.0172(3) Uani 1 1 d . . . . .
H4A H 0.7977 0.5443 0.4757 0.021 Uiso 1 1 calc R U . . .
H4B H 0.6465 0.4881 0.4934 0.021 Uiso 1 1 calc R U . . .
C5 C 0.83747(13) 0.50370(10) 0.23535(10) 0.0150(2) Uani 1 1 d . . . . .
H5 H 0.7887 0.4542 0.1974 0.018 Uiso 1 1 calc R U . . .
C6 C 0.56395(12) 0.85005(10) 0.29781(10) 0.0145(2) Uani 1 1 d . . . . .
C7 C 0.67437(12) 0.93546(10) 0.29035(10) 0.0145(2) Uani 1 1 d . . . . .
C8 C 0.76612(13) 0.96333(11) 0.18507(10) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.7627 0.9259 0.1202 0.023 Uiso 1 1 calc R U . . .
C9 C 0.86211(14) 1.04464(11) 0.17361(11) 0.0211(3) Uani 1 1 d . . . . .
H9 H 0.9241 1.0628 0.1013 0.025 Uiso 1 1 calc R U . . .
C10 C 0.86776(13) 1.09973(11) 0.26781(11) 0.0209(3) Uani 1 1 d . . . . .
H10 H 0.9323 1.1566 0.2601 0.025 Uiso 1 1 calc R U . . .
C11 C 0.77896(13) 1.07140(11) 0.37304(11) 0.0200(3) Uani 1 1 d . . . . .
H11 H 0.7839 1.1081 0.4379 0.024 Uiso 1 1 calc R U . . .
C12 C 0.68241(13) 0.98952(10) 0.38452(10) 0.0168(3) Uani 1 1 d . . . . .
H12 H 0.6218 0.9706 0.4571 0.020 Uiso 1 1 calc R U . . .
C13 C 0.46254(13) 0.89239(10) 0.22619(10) 0.0154(2) Uani 1 1 d . . . . .
C14 C 0.47047(13) 0.85386(11) 0.12025(10) 0.0184(3) Uani 1 1 d . . . . .
H14 H 0.5429 0.7984 0.0879 0.022 Uiso 1 1 calc R U . . .
C15 C 0.37317(14) 0.89594(11) 0.06129(11) 0.0229(3) Uani 1 1 d . . . . .
H15 H 0.3799 0.8694 -0.0113 0.027 Uiso 1 1 calc R U . . .
C16 C 0.26654(14) 0.97627(11) 0.10787(11) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.1987 1.0036 0.0683 0.029 Uiso 1 1 calc R U . . .
C17 C 0.25916(14) 1.01661(11) 0.21235(12) 0.0230(3) Uani 1 1 d . . . . .
H17 H 0.1869 1.0724 0.2442 0.028 Uiso 1 1 calc R U . . .
C18 C 0.35685(13) 0.97578(10) 0.27043(11) 0.0192(3) Uani 1 1 d . . . . .
H18 H 0.3521 1.0048 0.3415 0.023 Uiso 1 1 calc R U . . .
C19 C 0.52333(13) 0.47109(10) 0.27636(10) 0.0169(3) Uani 1 1 d . . . . .
C20 C 0.46335(16) 0.48394(12) 0.18601(12) 0.0271(3) Uani 1 1 d . . . . .
H20 H 0.4552 0.5547 0.1510 0.033 Uiso 1 1 calc R U . . .
C21 C 0.41518(19) 0.39322(13) 0.14676(13) 0.0372(4) Uani 1 1 d . . . . .
H21 H 0.3747 0.4027 0.0846 0.045 Uiso 1 1 calc R U . . .
C22 C 0.42506(16) 0.28989(12) 0.19625(13) 0.0327(4) Uani 1 1 d . . . . .
H22 H 0.3922 0.2284 0.1685 0.039 Uiso 1 1 calc R U . . .
C23 C 0.48352(15) 0.27715(12) 0.28685(14) 0.0315(3) Uani 1 1 d . . . . .
H23 H 0.4915 0.2061 0.3213 0.038 Uiso 1 1 calc R U . . .
C24 C 0.53061(15) 0.36652(11) 0.32817(13) 0.0258(3) Uani 1 1 d . . . . .
H24 H 0.5680 0.3568 0.3920 0.031 Uiso 1 1 calc R U . . .
C25 C 0.88742(13) 0.33223(10) 0.46362(10) 0.0148(2) Uani 1 1 d . . . . .
C26 C 0.81013(13) 0.31334(10) 0.57655(10) 0.0173(3) Uani 1 1 d . . . . .
H26 H 0.7207 0.3540 0.6075 0.021 Uiso 1 1 calc R U . . .
C27 C 0.86392(13) 0.23549(11) 0.64303(11) 0.0191(3) Uani 1 1 d . . . . .
H27 H 0.8108 0.2226 0.7195 0.023 Uiso 1 1 calc R U . . .
C28 C 0.99489(14) 0.17592(11) 0.59905(11) 0.0205(3) Uani 1 1 d . . . . .
H28 H 1.0298 0.1206 0.6441 0.025 Uiso 1 1 calc R U . . .
C29 C 1.07395(14) 0.19838(11) 0.48857(11) 0.0210(3) Uani 1 1 d . . . . .
H29 H 1.1652 0.1597 0.4590 0.025 Uiso 1 1 calc R U . . .
C30 C 1.02219(13) 0.27624(10) 0.42039(10) 0.0177(3) Uani 1 1 d . . . . .
H30 H 1.0779 0.2913 0.3450 0.021 Uiso 1 1 calc R U . . .
C31 C 0.93560(13) 0.57322(10) 0.14640(10) 0.0166(3) Uani 1 1 d . . . . .
C32 C 1.07225(14) 0.59602(11) 0.15310(11) 0.0211(3) Uani 1 1 d . . . . .
H32 H 1.1041 0.5701 0.2168 0.025 Uiso 1 1 calc R U . . .
C33 C 1.16193(15) 0.65660(12) 0.06665(12) 0.0272(3) Uani 1 1 d . . . . .
H33 H 1.2555 0.6711 0.0712 0.033 Uiso 1 1 calc R U . . .
C34 C 1.11647(16) 0.69588(11) -0.02580(12) 0.0276(3) Uani 1 1 d . . . . .
H34 H 1.1784 0.7373 -0.0846 0.033 Uiso 1 1 calc R U . . .
C35 C 0.98005(16) 0.67454(11) -0.03240(11) 0.0260(3) Uani 1 1 d . . . . .
H35 H 0.9477 0.7024 -0.0953 0.031 Uiso 1 1 calc R U . . .
C36 C 0.89049(14) 0.61262(11) 0.05264(10) 0.0203(3) Uani 1 1 d . . . . .
H36 H 0.7978 0.5970 0.0469 0.024 Uiso 1 1 calc R U . . .
N1 N 0.56731(11) 0.56224(8) 0.32401(8) 0.0155(2) Uani 1 1 d . . . . .
N2 N 0.81982(10) 0.39956(8) 0.39438(8) 0.0158(2) Uani 1 1 d . . . . .
O1 O 0.54211(9) 0.66096(7) 0.25674(8) 0.0199(2) Uani 1 1 d . . . . .
O2 O 0.92557(9) 0.43706(7) 0.29342(7) 0.01768(19) Uani 1 1 d . . . . .
O3 O 0.48154(9) 0.83857(7) 0.41315(7) 0.01721(19) Uani 1 1 d . . . . .
H3A H 0.4136 0.7977 0.4178 0.026 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4963(15) . ?
C1 C2 1.5216(17) . ?
C1 C4 1.5339(17) . ?
C1 C5 1.5737(16) . ?
C2 C3 1.5140(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O1 1.4408(14) . ?
C3 C6 1.5362(17) . ?
C3 H3 1.0000 . ?
C4 N2 1.4620(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O2 1.4345(14) . ?
C5 C31 1.5030(17) . ?
C5 H5 1.0000 . ?
C6 O3 1.4268(13) . ?
C6 C7 1.5264(16) . ?
C6 C13 1.5333(17) . ?
C7 C12 1.3872(17) . ?
C7 C8 1.3927(17) . ?
C8 C9 1.3823(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3868(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.3825(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3913(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3903(17) . ?
C13 C18 1.3972(17) . ?
C14 C15 1.3902(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3814(18) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3865(18) . ?
C19 C24 1.3982(18) . ?
C19 N1 1.4272(16) . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.3962(17) . ?
C25 C26 1.3992(17) . ?
C25 N2 1.4048(15) . ?
C26 C27 1.3829(17) . ?
C26 H26 0.9500 . ?
C27 C28 1.3891(18) . ?
C27 H27 0.9500 . ?
C28 C29 1.3863(18) . ?
C28 H28 0.9500 . ?
C29 C30 1.3875(18) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.3922(18) . ?
C31 C36 1.3926(18) . ?
C32 C33 1.3883(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.3869(19) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 O1 1.4655(13) . ?
N2 O2 1.4488(12) . ?
O3 H3A 0.8400 . ?

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
N1 C1 C2 100.93(9) . . ?
N1 C1 C4 112.13(10) . . ?
C2 C1 C4 111.51(10) . . ?
N1 C1 C5 114.74(9) . . ?
C2 C1 C5 115.98(10) . . ?
C4 C1 C5 101.98(9) . . ?
C3 C2 C1 104.10(10) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
O1 C3 C2 105.85(9) . . ?
O1 C3 C6 108.72(9) . . ?
C2 C3 C6 114.27(10) . . ?
O1 C3 H3 109.3 . . ?
C2 C3 H3 109.3 . . ?
C6 C3 H3 109.3 . . ?
N2 C4 C1 103.08(9) . . ?
N2 C4 H4A 111.1 . . ?
C1 C4 H4A 111.1 . . ?
N2 C4 H4B 111.1 . . ?
C1 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
O2 C5 C31 107.85(9) . . ?
O2 C5 C1 104.46(9) . . ?
C31 C5 C1 117.89(10) . . ?
O2 C5 H5 108.8 . . ?
C31 C5 H5 108.8 . . ?
C1 C5 H5 108.8 . . ?
O3 C6 C7 108.08(9) . . ?
O3 C6 C13 109.10(9) . . ?
C7 C6 C13 108.65(10) . . ?
O3 C6 C3 109.13(9) . . ?
C7 C6 C3 108.62(9) . . ?
C13 C6 C3 113.15(10) . . ?
C12 C7 C8 118.83(11) . . ?
C12 C7 C6 122.07(11) . . ?
C8 C7 C6 119.04(11) . . ?
C9 C8 C7 120.93(12) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.92(12) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.63(12) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.41(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.25(12) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C18 118.42(11) . . ?
C14 C13 C6 124.13(11) . . ?
C18 C13 C6 117.44(11) . . ?
C15 C14 C13 120.50(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.27(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.74(12) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.03(12) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 121.00(12) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 C24 118.79(12) . . ?
C20 C19 N1 122.29(11) . . ?
C24 C19 N1 118.73(11) . . ?
C19 C20 C21 119.95(14) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 121.26(15) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 118.86(13) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C22 C23 C24 120.87(14) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 120.23(14) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C30 C25 C26 119.63(11) . . ?
C30 C25 N2 121.88(11) . . ?
C26 C25 N2 118.20(10) . . ?
C27 C26 C25 119.97(11) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 120.65(12) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C29 C28 C27 119.09(12) . . ?
C29 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C28 C29 C30 121.21(12) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C25 119.33(11) . . ?
C29 C30 H30 120.3 . . ?
C25 C30 H30 120.3 . . ?
C32 C31 C36 119.11(12) . . ?
C32 C31 C5 121.88(11) . . ?
C36 C31 C5 118.97(11) . . ?
C33 C32 C31 120.01(13) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 120.66(13) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.63(13) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.18(13) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.41(13) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C19 N1 O1 107.06(9) . . ?
C19 N1 C1 120.90(10) . . ?
O1 N1 C1 106.03(8) . . ?
C25 N2 O2 110.73(9) . . ?
C25 N2 C4 118.97(10) . . ?
O2 N2 C4 102.59(9) . . ?
C3 O1 N1 108.73(8) . . ?
C5 O2 N2 102.44(8) . . ?
C6 O3 H3A 109.5 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_d18485b
_database_code_depnum_ccdc_archive 'CCDC 1540300'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H30 N2 O4'
_chemical_formula_sum            'C32 H30 N2 O4'
_chemical_formula_weight         506.58

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'

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

_cell_length_a                   9.2140(3)
_cell_length_b                   10.2240(3)
_cell_length_c                   14.5971(5)
_cell_angle_alpha                100.1170(10)
_cell_angle_beta                 95.0210(10)
_cell_angle_gamma                94.0310(10)
_cell_volume                     1343.37(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9934
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      24.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9536
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34042
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         25.04
_reflns_number_total             4699
_reflns_number_gt                3972
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0413P)²+0.5265P] 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         4699
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
C1 C 1.02047(16) 0.25692(15) 0.25866(10) 0.0366(3) Uani 1 1 d . . .
C2 C 0.9946(2) 0.12402(17) 0.26644(12) 0.0482(4) Uani 1 1 d . . .
H2 H 0.9070 0.0740 0.2370 0.058 Uiso 1 1 calc R . .
C3 C 1.0966(3) 0.0646(2) 0.31705(14) 0.0656(6) Uani 1 1 d . . .
H3 H 1.0784 -0.0264 0.3220 0.079 Uiso 1 1 calc R . .
C4 C 1.2233(3) 0.1351(3) 0.35995(15) 0.0738(7) Uani 1 1 d . . .
H4 H 1.2911 0.0942 0.3963 0.089 Uiso 1 1 calc R . .
C5 C 1.2522(2) 0.2655(3) 0.35010(14) 0.0691(6) Uani 1 1 d . . .
H5 H 1.3411 0.3141 0.3788 0.083 Uiso 1 1 calc R . .
C6 C 1.15196(17) 0.3270(2) 0.29839(12) 0.0500(4) Uani 1 1 d . . .
H6 H 1.1735 0.4163 0.2904 0.060 Uiso 1 1 calc R . .
C7 C 0.80491(14) 0.39075(13) 0.26139(9) 0.0277(3) Uani 1 1 d . . .
C8 C 0.85735(15) 0.46259(13) 0.36367(9) 0.0285(3) Uani 1 1 d . . .
H8 H 0.9667 0.4742 0.3706 0.034 Uiso 1 1 calc R . .
C9 C 0.80880(15) 0.39110(14) 0.43965(9) 0.0302(3) Uani 1 1 d . . .
C10 C 0.89906(17) 0.30643(15) 0.47642(10) 0.0370(3) Uani 1 1 d . . .
H10 H 0.9939 0.2973 0.4565 0.044 Uiso 1 1 calc R . .
C11 C 0.8517(2) 0.23490(17) 0.54216(11) 0.0461(4) Uani 1 1 d . . .
H11 H 0.9137 0.1759 0.5664 0.055 Uiso 1 1 calc R . .
C12 C 0.7155(2) 0.24876(18) 0.57253(11) 0.0508(4) Uani 1 1 d . . .
H12 H 0.6834 0.1995 0.6176 0.061 Uiso 1 1 calc R . .
C13 C 0.6264(2) 0.33422(19) 0.53736(12) 0.0520(4) Uani 1 1 d . . .
H13 H 0.5326 0.3447 0.5587 0.062 Uiso 1 1 calc R . .
C14 C 0.67217(17) 0.40526(17) 0.47097(11) 0.0416(4) Uani 1 1 d . . .
H14 H 0.6096 0.4639 0.4468 0.050 Uiso 1 1 calc R . .
C15 C 0.64402(15) 0.71072(14) 0.29088(10) 0.0303(3) Uani 1 1 d . . .
C16 C 0.68347(18) 0.81940(15) 0.36210(11) 0.0405(4) Uani 1 1 d . . .
H16 H 0.7483 0.8111 0.4146 0.049 Uiso 1 1 calc R . .
C17 C 0.6275(2) 0.94084(16) 0.35614(13) 0.0491(4) Uani 1 1 d . . .
H17 H 0.6542 1.0152 0.4051 0.059 Uiso 1 1 calc R . .
C18 C 0.53395(18) 0.95492(16) 0.28038(12) 0.0454(4) Uani 1 1 d . . .
H18 H 0.4958 1.0381 0.2772 0.054 Uiso 1 1 calc R . .
C19 C 0.49623(17) 0.84714(16) 0.20928(12) 0.0433(4) Uani 1 1 d . . .
H19 H 0.4325 0.8564 0.1565 0.052 Uiso 1 1 calc R . .
C20 C 0.55018(17) 0.72563(16) 0.21403(11) 0.0394(4) Uani 1 1 d . . .
H20 H 0.5231 0.6518 0.1646 0.047 Uiso 1 1 calc R . .
C21 C 0.74836(15) 0.50600(13) 0.21547(9) 0.0280(3) Uani 1 1 d . . .
H21 H 0.6657 0.4679 0.1670 0.034 Uiso 1 1 calc R . .
C22 C 0.85963(16) 0.58160(13) 0.16996(10) 0.0311(3) Uani 1 1 d . . .
C23 C 0.98592(19) 0.65037(17) 0.21874(12) 0.0493(4) Uani 1 1 d . . .
H23 H 1.0031 0.6541 0.2843 0.059 Uiso 1 1 calc R . .
C24 C 1.0875(2) 0.71383(19) 0.17278(14) 0.0591(5) Uani 1 1 d . . .
H24 H 1.1737 0.7607 0.2070 0.071 Uiso 1 1 calc R . .
C25 C 1.0639(2) 0.70915(17) 0.07792(13) 0.0528(5) Uani 1 1 d . . .
H25 H 1.1338 0.7522 0.0465 0.063 Uiso 1 1 calc R . .
C26 C 0.9394(2) 0.64226(18) 0.02910(12) 0.0504(4) Uani 1 1 d . . .
H26 H 0.9228 0.6392 -0.0364 0.060 Uiso 1 1 calc R . .
C27 C 0.83693(18) 0.57865(16) 0.07467(11) 0.0396(4) Uani 1 1 d . . .
H27 H 0.7506 0.5327 0.0401 0.048 Uiso 1 1 calc R . .
C28 C 0.68531(15) 0.27642(14) 0.25333(10) 0.0313(3) Uani 1 1 d . . .
H28A H 0.7029 0.2235 0.3033 0.038 Uiso 1 1 calc R . .
H28B H 0.5874 0.3102 0.2564 0.038 Uiso 1 1 calc R . .
C29 C 0.69946(16) 0.19405(14) 0.15702(10) 0.0335(3) Uani 1 1 d . . .
H29 H 0.6977 0.0975 0.1615 0.040 Uiso 1 1 calc R . .
C30 C 0.58061(17) 0.21302(14) 0.08330(10) 0.0366(3) Uani 1 1 d . . .
C31 C 0.3308(2) 0.1549(2) 0.03174(15) 0.0618(5) Uani 1 1 d . . .
H31A H 0.3491 0.1327 -0.0348 0.074 Uiso 1 1 calc R . .
H31B H 0.3055 0.2484 0.0449 0.074 Uiso 1 1 calc R . .
C32 C 0.2095(2) 0.0641(2) 0.05099(16) 0.0623(5) Uani 1 1 d . . .
H32A H 0.1206 0.0734 0.0114 0.093 Uiso 1 1 calc R . .
H32B H 0.1922 0.0870 0.1170 0.093 Uiso 1 1 calc R . .
H32C H 0.2353 -0.0282 0.0373 0.093 Uiso 1 1 calc R . .
N1 N 0.92083(12) 0.32871(11) 0.20905(8) 0.0310(3) Uani 1 1 d . . .
N2 N 0.68679(12) 0.58174(11) 0.29669(8) 0.0293(3) Uani 1 1 d . . .
O1 O 0.83903(11) 0.23801(10) 0.13113(7) 0.0366(3) Uani 1 1 d . . .
O2 O 0.80376(10) 0.59240(9) 0.37268(6) 0.0321(2) Uani 1 1 d . . .
O3 O 0.59046(14) 0.28399(13) 0.02684(8) 0.0572(4) Uani 1 1 d . . .
O4 O 0.46014(12) 0.13869(11) 0.09157(8) 0.0477(3) Uani 1 1 d . . .


_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
C1 C6 1.388(2) . ?
C1 C2 1.389(2) . ?
C1 N1 1.4391(19) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.367(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.4814(17) . ?
C7 C28 1.5305(18) . ?
C7 C21 1.5531(19) . ?
C7 C8 1.5622(18) . ?
C8 O2 1.4369(16) . ?
C8 C9 1.5133(19) . ?
C8 H8 1.0000 . ?
C9 C10 1.384(2) . ?
C9 C14 1.385(2) . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.385(2) . ?
C15 C20 1.392(2) . ?
C15 N2 1.4170(18) . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N2 1.4779(17) . ?
C21 C22 1.5093(19) . ?
C21 H21 1.0000 . ?
C22 C27 1.383(2) . ?
C22 C23 1.385(2) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.366(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.390(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.5278(19) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 O1 1.4360(17) . ?
C29 C30 1.514(2) . ?
C29 H29 1.0000 . ?
C30 O3 1.1950(18) . ?
C30 O4 1.3271(18) . ?
C31 O4 1.452(2) . ?
C31 C32 1.480(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N1 O1 1.4502(15) . ?
N2 O2 1.4613(14) . ?

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 C1 C2 119.31(15) . . ?
C6 C1 N1 116.25(14) . . ?
C2 C1 N1 124.42(15) . . ?
C3 C2 C1 119.95(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.62(19) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.62(19) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N1 C7 C28 103.77(11) . . ?
N1 C7 C21 110.14(10) . . ?
C28 C7 C21 111.18(11) . . ?
N1 C7 C8 114.68(11) . . ?
C28 C7 C8 114.71(11) . . ?
C21 C7 C8 102.53(10) . . ?
O2 C8 C9 110.90(11) . . ?
O2 C8 C7 105.68(10) . . ?
C9 C8 C7 115.31(11) . . ?
O2 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C10 C9 C14 119.03(13) . . ?
C10 C9 C8 120.07(13) . . ?
C14 C9 C8 120.85(13) . . ?
C9 C10 C11 120.27(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.40(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.59(15) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.45(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.24(15) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C16 C15 C20 119.24(14) . . ?
C16 C15 N2 122.18(13) . . ?
C20 C15 N2 118.40(13) . . ?
C15 C16 C17 119.54(15) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 121.03(16) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.27(15) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.58(15) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.32(15) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
N2 C21 C22 116.80(11) . . ?
N2 C21 C7 98.90(10) . . ?
C22 C21 C7 115.89(11) . . ?
N2 C21 H21 108.2 . . ?
C22 C21 H21 108.2 . . ?
C7 C21 H21 108.2 . . ?
C27 C22 C23 118.42(14) . . ?
C27 C22 C21 118.55(13) . . ?
C23 C22 C21 123.00(13) . . ?
C24 C23 C22 120.65(16) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.25(17) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 119.67(15) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 120.44(16) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.57(16) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C29 C28 C7 102.63(11) . . ?
C29 C28 H28A 111.2 . . ?
C7 C28 H28A 111.2 . . ?
C29 C28 H28B 111.2 . . ?
C7 C28 H28B 111.2 . . ?
H28A C28 H28B 109.2 . . ?
O1 C29 C30 109.19(11) . . ?
O1 C29 C28 106.15(11) . . ?
C30 C29 C28 113.07(12) . . ?
O1 C29 H29 109.4 . . ?
C30 C29 H29 109.4 . . ?
C28 C29 H29 109.4 . . ?
O3 C30 O4 124.43(14) . . ?
O3 C30 C29 126.56(14) . . ?
O4 C30 C29 109.00(12) . . ?
O4 C31 C32 107.95(15) . . ?
O4 C31 H31A 110.1 . . ?
C32 C31 H31A 110.1 . . ?
O4 C31 H31B 110.1 . . ?
C32 C31 H31B 110.1 . . ?
H31A C31 H31B 108.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C1 N1 O1 109.70(11) . . ?
C1 N1 C7 116.91(11) . . ?
O1 N1 C7 103.27(10) . . ?
C15 N2 O2 109.20(10) . . ?
C15 N2 C21 118.27(11) . . ?
O2 N2 C21 103.48(9) . . ?
C29 O1 N1 110.14(9) . . ?
C8 O2 N2 105.58(9) . . ?
C30 O4 C31 116.14(13) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_160816LT_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1541215'
_audit_update_record             
;
2017-03-30 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O2'
_chemical_formula_weight         370.43

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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.7372(10)
_cell_length_b                   7.3706(5)
_cell_length_c                   19.7024(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.653(4)
_cell_angle_gamma                90
_cell_volume                     1911.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2578
_cell_measurement_theta_min      2.9669
_cell_measurement_theta_max      24.1276

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8028
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            11858
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.613
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3834
_reflns_number_gt                2468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0988P)²+0.7874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1968
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4388(2) 0.5212(4) 0.77715(13) 0.0326(7) Uani 1 1 d . . . . .
N2 N 0.39940(16) 0.8542(3) 0.65928(12) 0.0204(5) Uani 1 1 d . . . . .
O1 O 0.4180(5) 0.3497(8) 0.7816(3) 0.0244(7) Uani 0.306(3) 1 d . . P A 1
O1' O 0.5023(2) 0.3422(4) 0.79736(15) 0.0244(7) Uani 0.694(3) 1 d . . P A 2
O2 O 0.50299(13) 0.8259(3) 0.65381(10) 0.0254(5) Uani 1 1 d . . . . .
C1 C 0.4731(3) 0.2493(5) 0.73805(19) 0.0410(9) Uani 1 1 d . . . A 1
H1A H 0.4381 0.1362 0.7196 0.049 Uiso 1 1 d . U . B 1
H1B H 0.5412 0.2164 0.7657 0.049 Uiso 1 1 d . U . C 1
C2 C 0.4746(2) 0.3769(4) 0.67833(15) 0.0229(6) Uani 1 1 d . . . . .
H2 H 0.4214 0.3437 0.6337 0.028 Uiso 1 1 calc R U . A 1
C3 C 0.5773(2) 0.4002(4) 0.66567(15) 0.0249(7) Uani 1 1 d . . . . .
C4 C 0.6320(2) 0.2694(5) 0.64053(16) 0.0347(8) Uani 1 1 d . . . . .
H4 H 0.6045 0.1520 0.6274 0.042 Uiso 1 1 calc R U . . .
C5 C 0.7275(3) 0.3155(6) 0.63533(18) 0.0435(10) Uani 1 1 d . . . . .
H5 H 0.7657 0.2288 0.6181 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7679(2) 0.4866(6) 0.65494(17) 0.0398(9) Uani 1 1 d . . . . .
H6 H 0.8337 0.5149 0.6514 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7135(2) 0.6170(5) 0.67970(15) 0.0320(8) Uani 1 1 d . . . . .
H7 H 0.7416 0.7337 0.6937 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6167(2) 0.5718(4) 0.68337(14) 0.0231(7) Uani 1 1 d . . . . .
C9 C 0.54397(19) 0.6899(4) 0.70697(15) 0.0209(6) Uani 1 1 d . . . . .
H9 H 0.5756 0.7444 0.7547 0.025 Uiso 1 1 calc R U . . .
C10 C 0.45253(19) 0.5648(4) 0.70634(14) 0.0191(6) Uani 1 1 d . . . . .
C11 C 0.3619(2) 0.6643(4) 0.65535(16) 0.0236(7) Uani 1 1 d . . . . .
H11 H 0.3527 0.6175 0.6063 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2612(2) 0.6495(5) 0.6727(2) 0.0476(10) Uani 1 1 d . . . . .
H12A H 0.2676 0.7056 0.7189 0.071 Uiso 1 1 calc R U . . .
H12B H 0.2429 0.5214 0.6742 0.071 Uiso 1 1 calc R U . . .
H12C H 0.2082 0.7121 0.6362 0.071 Uiso 1 1 calc R U . . .
C13 C 0.4796(2) 0.6346(4) 0.83688(14) 0.0207(6) Uani 1 1 d . . . . .
C14 C 0.4591(2) 0.8198(4) 0.83216(15) 0.0204(6) Uani 1 1 d . . . . .
H14 H 0.4181 0.8701 0.7890 0.024 Uiso 1 1 calc R U . . .
C15 C 0.4985(2) 0.9309(4) 0.89024(15) 0.0240(7) Uani 1 1 d . . . . .
H15 H 0.4854 1.0576 0.8863 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5566(2) 0.8594(5) 0.95381(16) 0.0292(7) Uani 1 1 d . . . . .
H16 H 0.5841 0.9363 0.9934 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5743(2) 0.6758(5) 0.95912(16) 0.0326(8) Uani 1 1 d . . . . .
H17 H 0.6132 0.6258 1.0029 0.039 Uiso 1 1 calc R U . . .
C18 C 0.5360(2) 0.5624(4) 0.90150(16) 0.0288(7) Uani 1 1 d . . . . .
H18 H 0.5483 0.4355 0.9061 0.035 Uiso 1 1 calc R U . . .
C19 C 0.34799(19) 0.9721(4) 0.60224(14) 0.0200(6) Uani 1 1 d . . . . .
C20 C 0.3820(2) 1.0035(4) 0.54312(15) 0.0254(7) Uani 1 1 d . . . . .
H20 H 0.4384 0.9377 0.5370 0.030 Uiso 1 1 calc R U . . .
C21 C 0.3335(2) 1.1307(4) 0.49336(16) 0.0299(7) Uani 1 1 d . . . . .
H21 H 0.3570 1.1528 0.4532 0.036 Uiso 1 1 calc R U . . .
C22 C 0.2505(2) 1.2264(4) 0.50161(16) 0.0285(7) Uani 1 1 d . . . . .
H22 H 0.2181 1.3151 0.4677 0.034 Uiso 1 1 calc R U . . .
C23 C 0.2151(2) 1.1923(4) 0.55920(16) 0.0259(7) Uani 1 1 d . . . . .
H23 H 0.1570 1.2547 0.5640 0.031 Uiso 1 1 calc R U . . .
C24 C 0.2640(2) 1.0677(4) 0.61008(15) 0.0232(7) Uani 1 1 d . . . . .
H24 H 0.2404 1.0471 0.6503 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.305(7) . ?
N1 C13 1.421(4) . ?
N1 C10 1.496(4) . ?
N1 O1' 1.569(4) . ?
N2 C19 1.436(4) . ?
N2 O2 1.472(3) . ?
N2 C11 1.486(4) . ?
O1 C1 1.493(7) . ?
O2 C9 1.442(3) . ?
C1 C2 1.511(4) . ?
C1 H1A 0.9789 . ?
C1 H1B 0.9686 . ?
C2 C3 1.512(4) . ?
C2 C10 1.552(4) . ?
C2 H2 1.0000 . ?
C3 C8 1.381(4) . ?
C3 C4 1.398(4) . ?
C4 C5 1.387(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.496(4) . ?
C9 C10 1.556(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.543(4) . ?
C11 C12 1.521(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(4) . ?
C13 C18 1.393(4) . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.393(4) . ?
C19 C24 1.398(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(4) . ?
C23 H23 0.9500 . ?
C24 H24 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
O1 N1 C13 123.8(4) . . ?
O1 N1 C10 111.1(3) . . ?
C13 N1 C10 121.4(2) . . ?
C13 N1 O1' 103.0(2) . . ?
C10 N1 O1' 102.0(2) . . ?
C19 N2 O2 107.30(18) . . ?
C19 N2 C11 116.4(2) . . ?
O2 N2 C11 100.99(19) . . ?
N1 O1 C1 106.5(5) . . ?
C9 O2 N2 103.27(17) . . ?
O1 C1 C2 105.2(3) . . ?
O1 C1 H1A 111.1 . . ?
C2 C1 H1A 110.8 . . ?
O1 C1 H1B 111.6 . . ?
C2 C1 H1B 111.6 . . ?
H1A C1 H1B 106.7 . . ?
C1 C2 C3 114.9(2) . . ?
C1 C2 C10 103.4(2) . . ?
C3 C2 C10 104.1(2) . . ?
C1 C2 H2 111.3 . . ?
C3 C2 H2 111.3 . . ?
C10 C2 H2 111.3 . . ?
C8 C3 C4 120.7(3) . . ?
C8 C3 C2 112.3(2) . . ?
C4 C3 C2 127.1(3) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 118.0(3) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C3 C8 C7 121.1(3) . . ?
C3 C8 C9 111.3(2) . . ?
C7 C8 C9 127.5(3) . . ?
O2 C9 C8 109.6(2) . . ?
O2 C9 C10 105.1(2) . . ?
C8 C9 C10 105.2(2) . . ?
O2 C9 H9 112.2 . . ?
C8 C9 H9 112.2 . . ?
C10 C9 H9 112.2 . . ?
N1 C10 C11 114.5(2) . . ?
N1 C10 C2 103.3(2) . . ?
C11 C10 C2 113.3(2) . . ?
N1 C10 C9 115.9(2) . . ?
C11 C10 C9 102.9(2) . . ?
C2 C10 C9 107.0(2) . . ?
N2 C11 C12 112.3(2) . . ?
N2 C11 C10 102.2(2) . . ?
C12 C11 C10 115.8(2) . . ?
N2 C11 H11 108.7 . . ?
C12 C11 H11 108.7 . . ?
C10 C11 H11 108.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.0(3) . . ?
C14 C13 N1 119.8(3) . . ?
C18 C13 N1 121.1(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.2(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C24 119.6(3) . . ?
C20 C19 N2 123.2(2) . . ?
C24 C19 N2 117.1(2) . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.9(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.177

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_d18714
_database_code_depnum_ccdc_archive 'CCDC 1540301'
_audit_update_record             
;
2017-03-27 deposited with the CCDC.
2017-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H32 N2 O4'
_chemical_formula_sum            'C31 H32 N2 O4'
_chemical_formula_weight         496.59

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   'C 2/c'

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

_cell_length_a                   24.087(3)
_cell_length_b                   9.7374(11)
_cell_length_c                   23.807(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.805(4)
_cell_angle_gamma                90.00
_cell_volume                     5316.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2985
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      24.34

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale brown'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2112
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9918
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19936
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_sigmaI/netI    0.0673
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4704
_reflns_number_gt                2837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0694P)²+3.8630P] 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         4704
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
C1 C 0.53610(14) 0.2001(3) 0.55317(12) 0.0354(7) Uani 1 1 d . . .
C2 C 0.58337(13) 0.1043(3) 0.54818(12) 0.0337(7) Uani 1 1 d . . .
H2 H 0.5863 0.0227 0.5744 0.040 Uiso 1 1 calc R . .
C3 C 0.63749(13) 0.1919(3) 0.56907(12) 0.0318(7) Uani 1 1 d . . .
H3A H 0.6471 0.2317 0.5349 0.038 Uiso 1 1 calc R . .
H3B H 0.6710 0.1359 0.5922 0.038 Uiso 1 1 calc R . .
C4 C 0.62467(12) 0.3076(3) 0.60792(12) 0.0301(7) Uani 1 1 d . . .
C5 C 0.64820(13) 0.2685(3) 0.67488(12) 0.0312(7) Uani 1 1 d . . .
H5 H 0.6917 0.2667 0.6861 0.037 Uiso 1 1 calc R . .
C6 C 0.62819(13) 0.1258(3) 0.68653(12) 0.0334(7) Uani 1 1 d . . .
C7 C 0.57465(14) 0.1053(3) 0.69567(13) 0.0450(8) Uani 1 1 d . . .
H7 H 0.5522 0.1818 0.7009 0.054 Uiso 1 1 calc R . .
C8 C 0.55388(17) -0.0279(4) 0.69720(16) 0.0600(10) Uani 1 1 d . . .
H8 H 0.5165 -0.0416 0.7019 0.072 Uiso 1 1 calc R . .
C9 C 0.58672(19) -0.1395(4) 0.69201(15) 0.0609(11) Uani 1 1 d . . .
H9 H 0.5715 -0.2296 0.6916 0.073 Uiso 1 1 calc R . .
C10 C 0.64155(17) -0.1203(3) 0.68742(13) 0.0494(9) Uani 1 1 d . . .
H10 H 0.6653 -0.1973 0.6861 0.059 Uiso 1 1 calc R . .
C11 C 0.66222(15) 0.0114(3) 0.68467(12) 0.0404(8) Uani 1 1 d . . .
H11 H 0.7002 0.0239 0.6815 0.049 Uiso 1 1 calc R . .
C12 C 0.66612(13) 0.3963(3) 0.76904(12) 0.0332(7) Uani 1 1 d . . .
C13 C 0.69625(15) 0.2910(3) 0.80432(13) 0.0430(8) Uani 1 1 d . . .
H13 H 0.6966 0.2021 0.7880 0.052 Uiso 1 1 calc R . .
C14 C 0.72582(16) 0.3142(3) 0.86304(14) 0.0497(9) Uani 1 1 d . . .
H14 H 0.7460 0.2407 0.8869 0.060 Uiso 1 1 calc R . .
C15 C 0.72650(15) 0.4428(3) 0.88758(14) 0.0470(9) Uani 1 1 d . . .
H15 H 0.7466 0.4579 0.9281 0.056 Uiso 1 1 calc R . .
C16 C 0.69755(14) 0.5494(3) 0.85243(14) 0.0424(8) Uani 1 1 d . . .
H16 H 0.6982 0.6387 0.8687 0.051 Uiso 1 1 calc R . .
C17 C 0.66777(14) 0.5266(3) 0.79402(13) 0.0387(8) Uani 1 1 d . . .
H17 H 0.6480 0.6006 0.7703 0.046 Uiso 1 1 calc R . .
C18 C 0.65171(13) 0.4409(3) 0.59173(12) 0.0311(7) Uani 1 1 d . . .
H18 H 0.6305 0.4616 0.5495 0.037 Uiso 1 1 calc R . .
C19 C 0.71595(13) 0.4281(3) 0.59697(12) 0.0310(7) Uani 1 1 d . . .
C20 C 0.75910(14) 0.4434(3) 0.65087(13) 0.0356(7) Uani 1 1 d . . .
H20 H 0.7482 0.4560 0.6857 0.043 Uiso 1 1 calc R . .
C21 C 0.81753(14) 0.4405(3) 0.65483(14) 0.0426(8) Uani 1 1 d . . .
H21 H 0.8464 0.4504 0.6921 0.051 Uiso 1 1 calc R . .
C22 C 0.83389(15) 0.4230(3) 0.60407(15) 0.0431(8) Uani 1 1 d . . .
H22 H 0.8740 0.4213 0.6064 0.052 Uiso 1 1 calc R . .
C23 C 0.79174(15) 0.4081(3) 0.55070(14) 0.0428(8) Uani 1 1 d . . .
H23 H 0.8027 0.3956 0.5160 0.051 Uiso 1 1 calc R . .
C24 C 0.73326(15) 0.4113(3) 0.54694(13) 0.0388(8) Uani 1 1 d . . .
H24 H 0.7046 0.4018 0.5095 0.047 Uiso 1 1 calc R . .
C25 C 0.52040(13) 0.4141(3) 0.59712(13) 0.0346(7) Uani 1 1 d . . .
C26 C 0.51676(14) 0.5440(3) 0.57339(13) 0.0376(7) Uani 1 1 d . . .
H26 H 0.5409 0.5691 0.5501 0.045 Uiso 1 1 calc R . .
C27 C 0.47766(15) 0.6379(3) 0.58365(14) 0.0463(8) Uani 1 1 d . . .
H27 H 0.4757 0.7282 0.5680 0.056 Uiso 1 1 calc R . .
C28 C 0.44204(17) 0.6015(4) 0.61603(16) 0.0593(10) Uani 1 1 d . . .
H28 H 0.4164 0.6671 0.6243 0.071 Uiso 1 1 calc R . .
C29 C 0.44351(18) 0.4695(4) 0.63666(18) 0.0660(11) Uani 1 1 d . . .
H29 H 0.4173 0.4426 0.6575 0.079 Uiso 1 1 calc R . .
C30 C 0.48247(15) 0.3762(4) 0.62752(16) 0.0526(9) Uani 1 1 d . . .
H30 H 0.4833 0.2852 0.6422 0.063 Uiso 1 1 calc R . .
C31 C 0.3421(2) 0.2606(5) 0.5088(2) 0.0904(14) Uani 1 1 d . . .
H31A H 0.3427 0.1662 0.5233 0.136 Uiso 1 1 calc R . .
H31B H 0.3016 0.2897 0.4905 0.136 Uiso 1 1 calc R . .
H31C H 0.3608 0.3217 0.5419 0.136 Uiso 1 1 calc R . .
N1 N 0.55915(10) 0.3116(2) 0.58551(10) 0.0320(6) Uani 1 1 d . . .
N2 N 0.63211(11) 0.3758(2) 0.71011(10) 0.0364(6) Uani 1 1 d . . .
O1 O 0.48334(10) 0.1801(2) 0.53009(9) 0.0456(6) Uani 1 1 d . . .
O2 O 0.57451(10) 0.06268(19) 0.48905(9) 0.0425(6) Uani 1 1 d . . .
O3 O 0.64358(9) 0.55613(18) 0.62573(8) 0.0364(5) Uani 1 1 d . . .
O4 O 0.37220(11) 0.2666(3) 0.46733(11) 0.0694(8) Uani 1 1 d . . .
H2' H 0.6288 0.4650 0.6890 0.083 Uiso 1 1 d R . .
H2A H 0.5485 -0.0145 0.4881 0.083 Uiso 1 1 d R . .
H3' H 0.6367 0.6368 0.5996 0.083 Uiso 1 1 d R . .
H4' H 0.4076 0.2396 0.4873 0.083 Uiso 1 1 d 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
C1 O1 1.236(3) . ?
C1 N1 1.349(4) . ?
C1 C2 1.505(4) . ?
C2 O2 1.417(3) . ?
C2 C3 1.509(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.547(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.504(4) . ?
C4 C18 1.553(4) . ?
C4 C5 1.567(4) . ?
C5 N2 1.464(3) . ?
C5 C6 1.524(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.386(4) . ?
C6 C11 1.392(4) . ?
C7 C8 1.395(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.371(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.371(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 C17 1.396(4) . ?
C12 N2 1.406(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O3 1.432(3) . ?
C18 C19 1.519(4) . ?
C18 H18 1.0000 . ?
C19 C24 1.387(4) . ?
C19 C20 1.391(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.370(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.377(4) . ?
C25 C30 1.378(4) . ?
C25 N1 1.450(4) . ?
C26 C27 1.387(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.364(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.372(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.371(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 O4 1.394(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
N2 H2' 0.9945 . ?
O2 H2A 0.9747 . ?
O3 H3' 0.9833 . ?
O4 H4' 0.8805 . ?

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
O1 C1 N1 124.7(3) . . ?
O1 C1 C2 124.5(3) . . ?
N1 C1 C2 110.8(3) . . ?
O2 C2 C1 111.6(2) . . ?
O2 C2 C3 110.0(2) . . ?
C1 C2 C3 102.8(2) . . ?
O2 C2 H2 110.7 . . ?
C1 C2 H2 110.7 . . ?
C3 C2 H2 110.7 . . ?
C2 C3 C4 107.4(2) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N1 C4 C3 100.8(2) . . ?
N1 C4 C18 111.4(2) . . ?
C3 C4 C18 106.5(2) . . ?
N1 C4 C5 112.4(2) . . ?
C3 C4 C5 110.8(2) . . ?
C18 C4 C5 114.0(2) . . ?
N2 C5 C6 113.1(2) . . ?
N2 C5 C4 109.5(2) . . ?
C6 C5 C4 111.7(2) . . ?
N2 C5 H5 107.4 . . ?
C6 C5 H5 107.4 . . ?
C4 C5 H5 107.4 . . ?
C7 C6 C11 118.3(3) . . ?
C7 C6 C5 121.4(3) . . ?
C11 C6 C5 120.2(3) . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 120.9(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 N2 122.6(2) . . ?
C17 C12 N2 119.1(3) . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
O3 C18 C19 109.3(2) . . ?
O3 C18 C4 112.0(2) . . ?
C19 C18 C4 113.9(2) . . ?
O3 C18 H18 107.1 . . ?
C19 C18 H18 107.1 . . ?
C4 C18 H18 107.1 . . ?
C24 C19 C20 118.0(3) . . ?
C24 C19 C18 120.4(3) . . ?
C20 C19 C18 121.5(3) . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C26 C25 C30 119.5(3) . . ?
C26 C25 N1 121.2(3) . . ?
C30 C25 N1 119.0(3) . . ?
C25 C26 C27 119.7(3) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.6(3) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C30 C29 C28 120.6(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C25 120.1(3) . . ?
C29 C30 H30 120.0 . . ?
C25 C30 H30 120.0 . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 N1 C25 119.1(3) . . ?
C1 N1 C4 112.7(2) . . ?
C25 N1 C4 128.1(2) . . ?
C12 N2 C5 119.8(2) . . ?
C12 N2 H2' 108.2 . . ?
C5 N2 H2' 109.2 . . ?
C2 O2 H2A 98.2 . . ?
C18 O3 H3' 107.1 . . ?
C31 O4 H4' 103.4 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.054
