# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1993512'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H26 F3 N3 O'
_chemical_formula_weight         501.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.0809(7)
_cell_length_b                   10.9917(4)
_cell_length_c                   17.1659(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.846(5)
_cell_angle_gamma                90
_cell_volume                     2514.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    6785

_cell_measurement_theta_min      1.6430

_cell_measurement_theta_max      27.8020


_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10

_exptl_crystal_size_mid          0.10

_exptl_crystal_size_min          0.10

_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.80125

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 5.8140

_diffrn_reflns_number            13618
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.634
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4418
_reflns_number_gt                3506
_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       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_structure_solution    SHELXS

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0319P)²+3.3237P] 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         4418
_refine_ls_number_parameters     375
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.170
_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
C1 C 0.6751(2) 0.8799(3) 0.83784(17) 0.0308(6) Uani 1 1 d . . . . .
C2 C 0.5724(2) 0.9419(2) 0.78914(17) 0.0297(6) Uani 1 1 d . . . . .
H1 H 0.564193 1.026676 0.770548 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5237(2) 0.8841(2) 0.84998(16) 0.0279(6) Uani 1 1 d . . . . .
H2 H 0.480546 0.927910 0.875266 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6246(2) 0.8231(2) 0.89862(17) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.654138 0.822267 0.958729 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6439(2) 0.7651(3) 0.78113(16) 0.0273(6) Uani 1 1 d . . . . .
H4 H 0.688136 0.721870 0.756599 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5437(2) 0.8276(2) 0.73129(16) 0.0247(6) Uani 1 1 d . . . . .
C7 C 0.4904(2) 0.7705(2) 0.79324(16) 0.0243(6) Uani 1 1 d . . . . .
C8 C 0.5961(2) 0.7075(2) 0.84298(16) 0.0252(6) Uani 1 1 d . . . . .
C9 C 0.7729(2) 0.9369(3) 0.85934(18) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.8506(2) 0.9804(3) 0.87439(17) 0.0509(8) Uani 1 1 d . . . . .
C10 C 0.3832(2) 0.7285(2) 0.77278(16) 0.0265(6) Uani 1 1 d . . . . .
O1 O 0.32835(15) 0.78813(19) 0.80179(14) 0.0407(5) Uani 1 1 d . . . . .
N2 N 0.34839(16) 0.6321(2) 0.72246(13) 0.0254(5) Uani 1 1 d . . . . .
C11 C 0.4108(2) 0.5582(2) 0.68563(17) 0.0262(6) Uani 1 1 d . . . . .
H5 H 0.478656 0.592393 0.703951 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3721(2) 0.5626(3) 0.59173(17) 0.0340(7) Uani 1 1 d . . . . .
H6 H 0.309814 0.519132 0.571795 0.051 Uiso 1 1 calc R U . . .
H7 H 0.420503 0.525706 0.570487 0.051 Uiso 1 1 calc R U . . .
H8 H 0.361831 0.645740 0.573862 0.051 Uiso 1 1 calc R U . . .
C13 C 0.4178(2) 0.4265(2) 0.7163(2) 0.0356(7) Uani 1 1 d . . . . .
H9 H 0.441053 0.425751 0.775345 0.053 Uiso 1 1 calc R U . . .
H10 H 0.463938 0.382185 0.696283 0.053 Uiso 1 1 calc R U . . .
H11 H 0.352757 0.389182 0.696330 0.053 Uiso 1 1 calc R U . . .
C14 C 0.2406(2) 0.5983(3) 0.70052(18) 0.0315(7) Uani 1 1 d . . . . .
H12 H 0.230943 0.525508 0.665898 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1734(2) 0.6969(3) 0.6487(2) 0.0444(8) Uani 1 1 d . . . . .
H13 H 0.178445 0.769139 0.681172 0.067 Uiso 1 1 calc R U . . .
H14 H 0.105100 0.669044 0.630267 0.067 Uiso 1 1 calc R U . . .
H15 H 0.194190 0.714593 0.601852 0.067 Uiso 1 1 calc R U . . .
C16 C 0.2108(2) 0.5642(3) 0.7752(2) 0.0462(8) Uani 1 1 d . . . . .
H16 H 0.256774 0.504509 0.807267 0.069 Uiso 1 1 calc R U . . .
H17 H 0.144122 0.531298 0.757469 0.069 Uiso 1 1 calc R U . . .
H18 H 0.212816 0.635331 0.808212 0.069 Uiso 1 1 calc R U . . .
C17 C 0.50554(19) 0.8327(2) 0.64023(16) 0.0245(6) Uani 1 1 d . . . . .
C18 C 0.5531(2) 0.7673(3) 0.59419(17) 0.0302(6) Uani 1 1 d . . . . .
H19 H 0.609184 0.720628 0.621163 0.036 Uiso 1 1 calc R U . . .
C19 C 0.5190(2) 0.7703(3) 0.50944(18) 0.0345(7) Uani 1 1 d D . . . .
H20 H 0.551055 0.725072 0.479529 0.041 Uiso 1 1 calc R U . . .
C20 C 0.4362(2) 0.8415(3) 0.46904(16) 0.0300(6) Uani 1 1 d D . . . .
C21 C 0.3884(2) 0.9090(3) 0.51400(18) 0.0353(7) Uani 1 1 d D . . . .
H21 H 0.333425 0.957430 0.486982 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4227(2) 0.9038(3) 0.59872(17) 0.0314(6) Uani 1 1 d . . . . .
H22 H 0.390230 0.948334 0.628625 0.038 Uiso 1 1 calc R U . . .
C23 C 0.4005(2) 0.8424(3) 0.37956(19) 0.0386(7) Uani 1 1 d D . . . .
N3 N 0.3674(2) 0.8388(3) 0.30813(17) 0.0438(9) Uani 0.845(3) 1 d D . P A 1
F1 F 0.4914(7) 0.8468(10) 0.3552(7) 0.058(4) Uani 0.155(3) 1 d D . P A 2
F2 F 0.3585(8) 0.9430(9) 0.3467(8) 0.062(4) Uani 0.155(3) 1 d D . P A 2
F3 F 0.3600(10) 0.7445(9) 0.3426(8) 0.086(6) Uani 0.155(3) 1 d D . P A 2
C24 C 0.61486(19) 0.5809(2) 0.87556(16) 0.0257(6) Uani 1 1 d . . . . .
C25 C 0.6475(2) 0.4902(2) 0.83400(17) 0.0292(6) Uani 1 1 d . . . . .
H23 H 0.659217 0.508737 0.785028 0.035 Uiso 1 1 calc R U . . .
C26 C 0.6629(2) 0.3724(3) 0.86441(17) 0.0328(7) Uani 1 1 d D . . . .
H24 H 0.683580 0.312079 0.835494 0.039 Uiso 1 1 calc R U . . .
C27 C 0.6473(2) 0.3452(3) 0.93776(18) 0.0321(7) Uani 1 1 d D . . . .
C28 C 0.6178(2) 0.4349(3) 0.98215(18) 0.0331(7) Uani 1 1 d D . . . .
H25 H 0.609389 0.416491 1.032400 0.040 Uiso 1 1 calc R U . . .
C29 C 0.6010(2) 0.5523(3) 0.95070(17) 0.0308(6) Uani 1 1 d . . . . .
H26 H 0.580439 0.612510 0.979811 0.037 Uiso 1 1 calc R U . . .
C30 C 0.6639(3) 0.2192(3) 0.9728(2) 0.0465(8) Uani 1 1 d D . . . .
F4 F 0.6740(3) 0.1387(2) 0.92089(16) 0.0940(13) Uani 0.845(3) 1 d D . P A 1
F5 F 0.74868(18) 0.2141(2) 1.03882(15) 0.0595(8) Uani 0.845(3) 1 d D . P A 1
F6 F 0.5924(2) 0.1844(2) 1.00207(18) 0.0715(9) Uani 0.845(3) 1 d D . P A 1
N4 N 0.6489(19) 0.1107(6) 0.9808(11) 0.089(9) Uani 0.155(3) 1 d D . P A 2


_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 C9 1.448(4) . ?
C1 C5 1.567(4) . ?
C1 C4 1.570(4) . ?
C1 C2 1.573(4) . ?
C2 C3 1.558(4) . ?
C2 C6 1.571(4) . ?
C3 C4 1.549(4) . ?
C3 C7 1.559(4) . ?
C4 C8 1.562(4) . ?
C5 C6 1.554(4) . ?
C5 C8 1.563(4) . ?
C6 C17 1.481(4) . ?
C6 C7 1.613(4) . ?
C7 C10 1.508(4) . ?
C7 C8 1.613(4) . ?
C8 C24 1.491(4) . ?
C9 N1 1.144(4) . ?
C10 O1 1.233(3) . ?
C10 N2 1.355(3) . ?
N2 C11 1.480(3) . ?
N2 C14 1.487(3) . ?
C11 C12 1.526(4) . ?
C11 C13 1.532(4) . ?
C14 C16 1.520(4) . ?
C14 C15 1.522(4) . ?
C17 C18 1.390(4) . ?
C17 C22 1.393(4) . ?
C18 C19 1.377(4) . ?
C19 C20 1.388(4) . ?
C20 C21 1.392(4) . ?
C20 C23 1.454(4) . ?
C21 C22 1.378(4) . ?
C23 N3 1.163(4) . ?
C23 F3 1.285(8) . ?
C23 F2 1.294(7) . ?
C23 F1 1.470(7) . ?
C24 C25 1.388(4) . ?
C24 C29 1.401(4) . ?
C25 C26 1.387(4) . ?
C26 C27 1.379(4) . ?
C27 C28 1.388(4) . ?
C27 C30 1.498(4) . ?
C28 C29 1.390(4) . ?
C30 N4 1.226(7) . ?
C30 F4 1.296(4) . ?
C30 F6 1.319(4) . ?
C30 F5 1.356(4) . ?

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
C9 C1 C5 124.0(3) . . ?
C9 C1 C4 126.9(2) . . ?
C5 C1 C4 89.8(2) . . ?
C9 C1 C2 125.7(2) . . ?
C5 C1 C2 89.6(2) . . ?
C4 C1 C2 89.4(2) . . ?
C3 C2 C6 91.06(19) . . ?
C3 C2 C1 89.7(2) . . ?
C6 C2 C1 89.7(2) . . ?
C4 C3 C2 90.7(2) . . ?
C4 C3 C7 91.6(2) . . ?
C2 C3 C7 90.9(2) . . ?
C3 C4 C8 90.7(2) . . ?
C3 C4 C1 90.2(2) . . ?
C8 C4 C1 90.0(2) . . ?
C6 C5 C8 92.2(2) . . ?
C6 C5 C1 90.5(2) . . ?
C8 C5 C1 90.0(2) . . ?
C17 C6 C5 123.6(2) . . ?
C17 C6 C2 124.6(2) . . ?
C5 C6 C2 90.2(2) . . ?
C17 C6 C7 128.6(2) . . ?
C5 C6 C7 89.91(19) . . ?
C2 C6 C7 88.49(19) . . ?
C10 C7 C3 117.8(2) . . ?
C10 C7 C6 127.5(2) . . ?
C3 C7 C6 89.47(19) . . ?
C10 C7 C8 132.5(2) . . ?
C3 C7 C8 88.47(19) . . ?
C6 C7 C8 88.28(18) . . ?
C24 C8 C4 123.4(2) . . ?
C24 C8 C5 124.8(2) . . ?
C4 C8 C5 90.21(19) . . ?
C24 C8 C7 128.3(2) . . ?
C4 C8 C7 89.2(2) . . ?
C5 C8 C7 89.57(19) . . ?
N1 C9 C1 178.0(3) . . ?
O1 C10 N2 121.9(2) . . ?
O1 C10 C7 117.0(2) . . ?
N2 C10 C7 121.1(2) . . ?
C10 N2 C11 124.0(2) . . ?
C10 N2 C14 119.0(2) . . ?
C11 N2 C14 116.9(2) . . ?
N2 C11 C12 112.1(2) . . ?
N2 C11 C13 110.7(2) . . ?
C12 C11 C13 110.7(2) . . ?
N2 C14 C16 112.6(2) . . ?
N2 C14 C15 111.2(2) . . ?
C16 C14 C15 112.3(3) . . ?
C18 C17 C22 118.5(2) . . ?
C18 C17 C6 120.2(2) . . ?
C22 C17 C6 121.3(2) . . ?
C19 C18 C17 121.4(3) . . ?
C18 C19 C20 119.4(3) . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 C23 118.7(3) . . ?
C21 C20 C23 121.2(3) . . ?
C22 C21 C20 119.7(3) . . ?
C21 C22 C17 120.9(3) . . ?
F3 C23 F2 115.6(7) . . ?
N3 C23 C20 176.0(3) . . ?
F3 C23 C20 117.5(6) . . ?
F2 C23 C20 114.8(7) . . ?
F3 C23 F1 100.1(6) . . ?
F2 C23 F1 99.5(6) . . ?
C20 C23 F1 105.4(5) . . ?
C25 C24 C29 118.7(3) . . ?
C25 C24 C8 121.7(2) . . ?
C29 C24 C8 119.6(2) . . ?
C26 C25 C24 121.0(3) . . ?
C27 C26 C25 119.6(3) . . ?
C26 C27 C28 120.7(3) . . ?
C26 C27 C30 121.1(3) . . ?
C28 C27 C30 118.1(3) . . ?
C27 C28 C29 119.3(3) . . ?
C28 C29 C24 120.6(3) . . ?
F4 C30 F6 109.3(3) . . ?
F4 C30 F5 106.5(3) . . ?
F6 C30 F5 104.1(3) . . ?
N4 C30 C27 159.0(11) . . ?
F4 C30 C27 113.1(3) . . ?
F6 C30 C27 112.4(3) . . ?
F5 C30 C27 110.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -137.3(3) . . . . ?
C5 C1 C2 C3 89.55(19) . . . . ?
C4 C1 C2 C3 -0.22(19) . . . . ?
C9 C1 C2 C6 131.7(3) . . . . ?
C5 C1 C2 C6 -1.52(19) . . . . ?
C4 C1 C2 C6 -91.29(19) . . . . ?
C6 C2 C3 C4 89.9(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C6 C2 C3 C7 -1.8(2) . . . . ?
C1 C2 C3 C7 -91.4(2) . . . . ?
C2 C3 C4 C8 -90.2(2) . . . . ?
C7 C3 C4 C8 0.7(2) . . . . ?
C2 C3 C4 C1 -0.2(2) . . . . ?
C7 C3 C4 C1 90.7(2) . . . . ?
C9 C1 C4 C3 136.5(3) . . . . ?
C5 C1 C4 C3 -89.4(2) . . . . ?
C2 C1 C4 C3 0.2(2) . . . . ?
C9 C1 C4 C8 -132.8(3) . . . . ?
C5 C1 C4 C8 1.3(2) . . . . ?
C2 C1 C4 C8 90.9(2) . . . . ?
C9 C1 C5 C6 -132.9(3) . . . . ?
C4 C1 C5 C6 90.9(2) . . . . ?
C2 C1 C5 C6 1.5(2) . . . . ?
C9 C1 C5 C8 134.9(3) . . . . ?
C4 C1 C5 C8 -1.3(2) . . . . ?
C2 C1 C5 C8 -90.7(2) . . . . ?
C8 C5 C6 C17 -138.3(2) . . . . ?
C1 C5 C6 C17 131.6(2) . . . . ?
C8 C5 C6 C2 88.5(2) . . . . ?
C1 C5 C6 C2 -1.5(2) . . . . ?
C8 C5 C6 C7 0.01(19) . . . . ?
C1 C5 C6 C7 -90.02(19) . . . . ?
C3 C2 C6 C17 139.4(3) . . . . ?
C1 C2 C6 C17 -130.9(3) . . . . ?
C3 C2 C6 C5 -88.2(2) . . . . ?
C1 C2 C6 C5 1.53(19) . . . . ?
C3 C2 C6 C7 1.7(2) . . . . ?
C1 C2 C6 C7 91.44(19) . . . . ?
C4 C3 C7 C10 137.8(2) . . . . ?
C2 C3 C7 C10 -131.4(2) . . . . ?
C4 C3 C7 C6 -89.02(19) . . . . ?
C2 C3 C7 C6 1.7(2) . . . . ?
C4 C3 C7 C8 -0.73(19) . . . . ?
C2 C3 C7 C8 90.0(2) . . . . ?
C17 C6 C7 C10 -11.1(4) . . . . ?
C5 C6 C7 C10 -146.0(3) . . . . ?
C2 C6 C7 C10 123.8(3) . . . . ?
C17 C6 C7 C3 -136.6(3) . . . . ?
C5 C6 C7 C3 88.5(2) . . . . ?
C2 C6 C7 C3 -1.7(2) . . . . ?
C17 C6 C7 C8 134.9(3) . . . . ?
C5 C6 C7 C8 -0.01(19) . . . . ?
C2 C6 C7 C8 -90.18(19) . . . . ?
C3 C4 C8 C24 -137.9(3) . . . . ?
C1 C4 C8 C24 131.9(3) . . . . ?
C3 C4 C8 C5 88.8(2) . . . . ?
C1 C4 C8 C5 -1.3(2) . . . . ?
C3 C4 C8 C7 -0.72(19) . . . . ?
C1 C4 C8 C7 -90.9(2) . . . . ?
C6 C5 C8 C24 138.6(3) . . . . ?
C1 C5 C8 C24 -130.9(3) . . . . ?
C6 C5 C8 C4 -89.2(2) . . . . ?
C1 C5 C8 C4 1.3(2) . . . . ?
C6 C5 C8 C7 -0.01(19) . . . . ?
C1 C5 C8 C7 90.5(2) . . . . ?
C10 C7 C8 C24 6.9(4) . . . . ?
C3 C7 C8 C24 134.4(3) . . . . ?
C6 C7 C8 C24 -136.1(3) . . . . ?
C10 C7 C8 C4 -126.7(3) . . . . ?
C3 C7 C8 C4 0.72(19) . . . . ?
C6 C7 C8 C4 90.23(19) . . . . ?
C10 C7 C8 C5 143.0(3) . . . . ?
C3 C7 C8 C5 -89.50(19) . . . . ?
C6 C7 C8 C5 0.01(18) . . . . ?
C3 C7 C10 O1 0.8(4) . . . . ?
C6 C7 C10 O1 -112.3(3) . . . . ?
C8 C7 C10 O1 117.0(3) . . . . ?
C3 C7 C10 N2 178.6(2) . . . . ?
C6 C7 C10 N2 65.5(4) . . . . ?
C8 C7 C10 N2 -65.2(4) . . . . ?
O1 C10 N2 C11 179.6(2) . . . . ?
C7 C10 N2 C11 1.8(4) . . . . ?
O1 C10 N2 C14 1.0(4) . . . . ?
C7 C10 N2 C14 -176.7(2) . . . . ?
C10 N2 C11 C12 -118.8(3) . . . . ?
C14 N2 C11 C12 59.8(3) . . . . ?
C10 N2 C11 C13 117.1(3) . . . . ?
C14 N2 C11 C13 -64.4(3) . . . . ?
C10 N2 C14 C16 -61.1(3) . . . . ?
C11 N2 C14 C16 120.3(3) . . . . ?
C10 N2 C14 C15 66.0(3) . . . . ?
C11 N2 C14 C15 -112.6(3) . . . . ?
C5 C6 C17 C18 8.0(4) . . . . ?
C2 C6 C17 C18 125.6(3) . . . . ?
C7 C6 C17 C18 -113.8(3) . . . . ?
C5 C6 C17 C22 -171.0(2) . . . . ?
C2 C6 C17 C22 -53.4(4) . . . . ?
C7 C6 C17 C22 67.2(4) . . . . ?
C22 C17 C18 C19 -1.1(4) . . . . ?
C6 C17 C18 C19 179.8(3) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C18 C19 C20 C23 -179.3(3) . . . . ?
C19 C20 C21 C22 -0.8(4) . . . . ?
C23 C20 C21 C22 178.5(3) . . . . ?
C20 C21 C22 C17 0.6(4) . . . . ?
C18 C17 C22 C21 0.3(4) . . . . ?
C6 C17 C22 C21 179.3(3) . . . . ?
C19 C20 C23 F3 68.9(8) . . . . ?
C21 C20 C23 F3 -110.3(8) . . . . ?
C19 C20 C23 F2 -149.9(6) . . . . ?
C21 C20 C23 F2 30.8(6) . . . . ?
C19 C20 C23 F1 -41.5(5) . . . . ?
C21 C20 C23 F1 139.3(5) . . . . ?
C4 C8 C24 C25 -140.4(3) . . . . ?
C5 C8 C24 C25 -22.8(4) . . . . ?
C7 C8 C24 C25 99.7(3) . . . . ?
C4 C8 C24 C29 38.5(4) . . . . ?
C5 C8 C24 C29 156.1(3) . . . . ?
C7 C8 C24 C29 -81.4(3) . . . . ?
C29 C24 C25 C26 2.2(4) . . . . ?
C8 C24 C25 C26 -178.8(3) . . . . ?
C24 C25 C26 C27 -1.2(4) . . . . ?
C25 C26 C27 C28 -1.0(4) . . . . ?
C25 C26 C27 C30 -179.5(3) . . . . ?
C26 C27 C28 C29 2.0(4) . . . . ?
C30 C27 C28 C29 -179.5(3) . . . . ?
C27 C28 C29 C24 -0.8(4) . . . . ?
C25 C24 C29 C28 -1.2(4) . . . . ?
C8 C24 C29 C28 179.8(3) . . . . ?
C26 C27 C30 N4 -74(3) . . . . ?
C28 C27 C30 N4 108(3) . . . . ?
C26 C27 C30 F4 -12.7(5) . . . . ?
C28 C27 C30 F4 168.7(3) . . . . ?
C26 C27 C30 F6 -137.1(3) . . . . ?
C28 C27 C30 F6 44.3(4) . . . . ?
C26 C27 C30 F5 106.8(3) . . . . ?
C28 C27 C30 F5 -71.7(4) . . . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.051



_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1993514'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_audit_creation_date             2020-02-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H34 F9 N O'
_chemical_formula_sum            'C42 H34 F9 N O'
_chemical_formula_weight         739.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C42 H34 F9 N O'
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   37.6320(10)
_cell_length_b                   14.8891(4)
_cell_length_c                   13.0219(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7296.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.3190
_cell_measurement_theta_min      2.1160
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3056
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27734
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.888
_diffrn_reflns_theta_min         2.123
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.841
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -41.00   0.50   20.36    --   11.29 -57.00-120.00   56
  2  ω    -21.00  11.00   0.50   20.36    --   11.29 -57.00-120.00   64
  3  ω    -15.00  62.00   0.50   20.36    --   11.29 -99.00   0.00  154
  4  ω      2.00  39.00   0.50   20.36    --   11.29  77.00 146.00   74
  5  ω     60.00  86.00   0.50   20.36    --   11.29  77.00 146.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0186332000
_diffrn_orient_matrix_UB_12      -0.0040060000
_diffrn_orient_matrix_UB_13      -0.0066842000
_diffrn_orient_matrix_UB_21      0.0000624000
_diffrn_orient_matrix_UB_22      -0.0399691000
_diffrn_orient_matrix_UB_23      0.0296510000
_diffrn_orient_matrix_UB_31      -0.0028047000
_diffrn_orient_matrix_UB_32      0.0256134000
_diffrn_orient_matrix_UB_33      0.0452170000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5137
_reflns_number_total             7329
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         7329
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0697
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0659P)²+8.8591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1699
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1-C01C = F00X-C01C = F00Y-C01C = F01H-C01C = F01I-C01C = F01G-C01C
 1.35 with sigma of 0.01
 F00Y-C01C = F01H-C01C = F00X-C01C = F1-C01C = F01G-C01C = F01I-C01C
 1.35 with sigma of 0.01
 F1-F01I
 2.2 with sigma of 0.02
 F00Y-F1
 2.2 with sigma of 0.02
 F00X-F01H
 2.2 with sigma of 0.02
 F00Y-F01I
 2.2 with sigma of 0.02
 F01H-F01G
 2.2 with sigma of 0.02
 F00X-F01G
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F00X) \\sim Ueq, Uanis(F01G) \\sim Ueq, Uanis(F01H) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F00Y) \\sim Ueq, Uanis(F01I) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
4. Others
 Sof(F1)=Sof(F00Y)=Sof(F01I)=1-FVAR(1)
 Sof(F00X)=Sof(F01G)=Sof(F01H)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00M(H00M), C00Z(H00Z), C017(H017)
5.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00H(H00H), C00J(H00J), C00L(H00L), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00Y(H00Y), C012(H012), C013(H013),
 C014(H014), C018(H018), C01B(H01J), C01D(H01K), C01F(H01O)
5.c Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C), C019(H01D,H01E,H01F), C01A(H01G,H01H,H01I), C01E(H01L,
 H01M,H01N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
F001 F 0.66242(5) -0.09413(11) 0.40290(15) 0.0380(5) Uani 1 1 d . . . . .
F002 F 0.69711(5) -0.03586(13) 0.29135(15) 0.0450(5) Uani 1 1 d . . . . .
F003 F 0.70961(5) -0.02715(13) 0.45184(17) 0.0478(6) Uani 1 1 d . . . . .
O004 O 0.64620(5) 0.42268(14) 0.21737(15) 0.0282(5) Uani 1 1 d . . . . .
F005 F 0.51745(6) 0.46118(17) -0.14645(15) 0.0555(6) Uani 1 1 d . . . . .
F006 F 0.57278(6) 0.45561(19) -0.16593(16) 0.0669(8) Uani 1 1 d . . . . .
F007 F 0.54709(8) 0.57987(15) -0.12983(17) 0.0745(8) Uani 1 1 d . . . . .
N008 N 0.67926(6) 0.41611(15) 0.36141(17) 0.0178(5) Uani 1 1 d . . . . .
C009 C 0.61327(7) 0.52907(18) 0.5162(2) 0.0172(6) Uani 1 1 d . . . . .
C00A C 0.62415(7) 0.22259(17) 0.4131(2) 0.0165(6) Uani 1 1 d . . . . .
C00B C 0.63020(7) 0.16741(18) 0.4970(2) 0.0183(6) Uani 1 1 d . . . . .
H00B H 0.621018 0.184028 0.562276 0.022 Uiso 1 1 calc R U . . .
C00C C 0.64781(7) 0.41381(17) 0.3116(2) 0.0170(6) Uani 1 1 d . . . . .
C00D C 0.59806(7) 0.44874(17) 0.4655(2) 0.0161(6) Uani 1 1 d . . . . .
C00E C 0.60251(7) 0.30549(17) 0.4191(2) 0.0165(6) Uani 1 1 d . . . . .
C00F C 0.58768(7) 0.35640(17) 0.5155(2) 0.0175(6) Uani 1 1 d . . . . .
H00F H 0.592322 0.339199 0.588500 0.021 Uiso 1 1 calc R U . . .
C00G C 0.56069(7) 0.45302(18) 0.4126(2) 0.0169(6) Uani 1 1 d . . . . .
H00G H 0.545191 0.507544 0.410575 0.020 Uiso 1 1 calc R U . . .
C00H C 0.62833(7) 0.59797(18) 0.4580(2) 0.0205(6) Uani 1 1 d . . . . .
H00H H 0.629778 0.591798 0.385505 0.025 Uiso 1 1 calc R U . . .
C00I C 0.56682(7) 0.42838(18) 0.2070(2) 0.0185(6) Uani 1 1 d . . . . .
C00J C 0.64941(7) 0.08845(18) 0.4875(2) 0.0199(6) Uani 1 1 d . . . . .
H00J H 0.653402 0.051389 0.545762 0.024 Uiso 1 1 calc R U . . .
C00K C 0.57506(7) 0.40253(18) 0.3154(2) 0.0178(6) Uani 1 1 d . . . . .
C00L C 0.61095(8) 0.54018(19) 0.6220(2) 0.0226(6) Uani 1 1 d . . . . .
H00L H 0.600442 0.494365 0.662683 0.027 Uiso 1 1 calc R U . . .
C00M C 0.56496(7) 0.31161(18) 0.3667(2) 0.0182(6) Uani 1 1 d . . . . .
H00M H 0.552855 0.260752 0.330799 0.022 Uiso 1 1 calc R U . . .
C00N C 0.66274(7) 0.06401(18) 0.3925(2) 0.0196(6) Uani 1 1 d . . . . .
C00O C 0.55001(7) 0.36090(18) 0.4640(2) 0.0189(6) Uani 1 1 d . . . . .
C00P C 0.61338(7) 0.39848(17) 0.3682(2) 0.0159(6) Uani 1 1 d . . . . .
C00Q C 0.57732(7) 0.51131(19) 0.1675(2) 0.0231(6) Uani 1 1 d . . . . .
H00Q H 0.589212 0.553021 0.210683 0.028 Uiso 1 1 calc R U . . .
C00R C 0.63895(8) 0.68416(19) 0.6102(2) 0.0234(6) Uani 1 1 d . . . . .
C00S C 0.54836(7) 0.37055(19) 0.1435(2) 0.0228(6) Uani 1 1 d . . . . .
H00S H 0.540477 0.314459 0.169795 0.027 Uiso 1 1 calc R U . . .
C00T C 0.54110(8) 0.3927(2) 0.0420(2) 0.0249(7) Uani 1 1 d . . . . .
H00T H 0.528161 0.352329 -0.000318 0.030 Uiso 1 1 calc R U . . .
C00U C 0.64116(7) 0.67495(19) 0.5041(2) 0.0234(6) Uani 1 1 d . . . . .
H00U H 0.651426 0.721275 0.463646 0.028 Uiso 1 1 calc R U . . .
C00V C 0.65707(7) 0.11788(19) 0.3071(2) 0.0226(6) Uani 1 1 d . . . . .
H00V H 0.666244 0.100845 0.242026 0.027 Uiso 1 1 calc R U . . .
C00W C 0.51580(7) 0.34191(18) 0.5164(2) 0.0232(6) Uani 1 1 d . . . . .
F00X F 0.6546(3) 0.8375(5) 0.6034(6) 0.068(3) Uani 0.468(13) 1 d D U P A 1
C00Y C 0.63796(7) 0.19646(18) 0.3178(2) 0.0212(6) Uani 1 1 d . . . . .
H00Y H 0.634097 0.233478 0.259399 0.025 Uiso 1 1 calc R U . . .
C00Z C 0.68389(7) 0.39429(19) 0.4714(2) 0.0203(6) Uani 1 1 d . . . . .
H00Z H 0.659788 0.383817 0.501520 0.024 Uiso 1 1 calc R U . . .
C010 C 0.55273(7) 0.47358(19) 0.0029(2) 0.0229(6) Uani 1 1 d . . . . .
C011 C 0.68288(8) -0.0224(2) 0.3842(2) 0.0261(7) Uani 1 1 d . . . . .
C012 C 0.57065(8) 0.5336(2) 0.0663(2) 0.0250(7) Uani 1 1 d . . . . .
H012 H 0.578305 0.589833 0.039951 0.030 Uiso 1 1 calc R U . . .
C013 C 0.62372(8) 0.6169(2) 0.6687(2) 0.0266(7) Uani 1 1 d . . . . .
H013 H 0.622035 0.623471 0.741067 0.032 Uiso 1 1 calc R U . . .
C014 C 0.51219(8) 0.3522(2) 0.6220(2) 0.0277(7) Uani 1 1 d . . . . .
H014 H 0.531618 0.374243 0.661183 0.033 Uiso 1 1 calc R U . . .
C015 C 0.54790(8) 0.4934(2) -0.1080(2) 0.0298(7) Uani 1 1 d . . . . .
C016 C 0.70127(8) 0.4710(2) 0.5309(2) 0.0276(7) Uani 1 1 d . . . . .
H01A H 0.725940 0.478040 0.508118 0.041 Uiso 1 1 calc R U . . .
H01B H 0.700852 0.457275 0.604467 0.041 Uiso 1 1 calc R U . . .
H01C H 0.688197 0.526780 0.518153 0.041 Uiso 1 1 calc R U . . .
C017 C 0.71232(7) 0.4340(2) 0.3020(2) 0.0249(7) Uani 1 1 d . . . . .
H017 H 0.732323 0.432988 0.352504 0.030 Uiso 1 1 calc R U . . .
C018 C 0.48645(8) 0.3124(2) 0.4602(3) 0.0309(7) Uani 1 1 d . . . . .
H018 H 0.488153 0.306503 0.387700 0.037 Uiso 1 1 calc R U . . .
C019 C 0.70562(8) 0.3081(2) 0.4855(2) 0.0285(7) Uani 1 1 d . . . . .
H01D H 0.695431 0.260220 0.443073 0.043 Uiso 1 1 calc R U . . .
H01E H 0.705084 0.290043 0.557800 0.043 Uiso 1 1 calc R U . . .
H01F H 0.730256 0.319003 0.464447 0.043 Uiso 1 1 calc R U . . .
C01A C 0.71210(8) 0.5274(2) 0.2549(3) 0.0334(8) Uani 1 1 d . . . . .
H01G H 0.692995 0.531467 0.203961 0.050 Uiso 1 1 calc R U . . .
H01H H 0.734986 0.538853 0.221470 0.050 Uiso 1 1 calc R U . . .
H01I H 0.708169 0.572166 0.308914 0.050 Uiso 1 1 calc R U . . .
C01B C 0.48049(8) 0.3305(2) 0.6710(3) 0.0340(8) Uani 1 1 d . . . . .
H01J H 0.478506 0.337089 0.743322 0.041 Uiso 1 1 calc R U . . .
C01C C 0.65359(8) 0.76578(19) 0.6600(2) 0.0356(8) Uani 1 1 d D . . . .
C01D C 0.45187(9) 0.2995(2) 0.6148(3) 0.0385(9) Uani 1 1 d . . . . .
H01K H 0.430326 0.283677 0.648227 0.046 Uiso 1 1 calc R U . . .
C01E C 0.72013(8) 0.3606(2) 0.2236(3) 0.0354(8) Uani 1 1 d . . . . .
H01L H 0.718519 0.301687 0.256937 0.053 Uiso 1 1 calc R U . . .
H01M H 0.744112 0.368882 0.195863 0.053 Uiso 1 1 calc R U . . .
H01N H 0.702773 0.363863 0.167614 0.053 Uiso 1 1 calc R U . . .
C01F C 0.45494(8) 0.2917(2) 0.5092(3) 0.0389(9) Uani 1 1 d . . . . .
H01O H 0.435145 0.271874 0.470056 0.047 Uiso 1 1 calc R U . . .
F01G F 0.6318(3) 0.7911(6) 0.7394(7) 0.077(3) Uani 0.468(13) 1 d D U P A 1
F01H F 0.6837(2) 0.7525(5) 0.7070(11) 0.086(4) Uani 0.468(13) 1 d D U P A 1
F1 F 0.6382(2) 0.8397(4) 0.6268(7) 0.067(2) Uani 0.532(13) 1 d D U P A 2
F00Y F 0.68799(13) 0.7807(5) 0.6317(9) 0.081(3) Uani 0.532(13) 1 d D U P A 2
F01I F 0.6537(4) 0.7672(5) 0.7593(3) 0.080(3) Uani 0.532(13) 1 d D U P A 2


_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
F001 C011 1.339(3) . ?
F002 C011 1.338(3) . ?
F003 C011 1.339(3) . ?
O004 C00C 1.236(3) . ?
F005 C015 1.339(4) . ?
F006 C015 1.327(4) . ?
F007 C015 1.319(4) . ?
N008 C00C 1.350(3) . ?
N008 C00Z 1.480(3) . ?
N008 C017 1.489(3) . ?
C009 C00D 1.482(4) . ?
C009 C00H 1.396(4) . ?
C009 C00L 1.390(4) . ?
C00A C00B 1.386(4) . ?
C00A C00E 1.481(4) . ?
C00A C00Y 1.401(4) . ?
C00B H00B 0.9500 . ?
C00B C00J 1.386(4) . ?
C00C C00P 1.508(4) . ?
C00D C00F 1.571(4) . ?
C00D C00G 1.567(4) . ?
C00D C00P 1.581(4) . ?
C00E C00F 1.569(4) . ?
C00E C00M 1.572(4) . ?
C00E C00P 1.589(4) . ?
C00F H00F 1.0000 . ?
C00F C00O 1.570(4) . ?
C00G H00G 1.0000 . ?
C00G C00K 1.569(4) . ?
C00G C00O 1.578(4) . ?
C00H H00H 0.9500 . ?
C00H C00U 1.381(4) . ?
C00I C00K 1.496(4) . ?
C00I C00Q 1.395(4) . ?
C00I C00S 1.381(4) . ?
C00J H00J 0.9500 . ?
C00J C00N 1.383(4) . ?
C00K C00M 1.557(4) . ?
C00K C00P 1.598(4) . ?
C00L H00L 0.9500 . ?
C00L C013 1.380(4) . ?
C00M H00M 1.0000 . ?
C00M C00O 1.568(4) . ?
C00N C00V 1.388(4) . ?
C00N C011 1.497(4) . ?
C00O C00W 1.484(4) . ?
C00Q H00Q 0.9500 . ?
C00Q C012 1.382(4) . ?
C00R C00U 1.390(4) . ?
C00R C013 1.383(4) . ?
C00R C01C 1.484(4) . ?
C00S H00S 0.9500 . ?
C00S C00T 1.390(4) . ?
C00T H00T 0.9500 . ?
C00T C010 1.378(4) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C00Y 1.380(4) . ?
C00W C014 1.391(4) . ?
C00W C018 1.396(4) . ?
F00X C01C 1.298(5) . ?
C00Y H00Y 0.9500 . ?
C00Z H00Z 1.0000 . ?
C00Z C016 1.526(4) . ?
C00Z C019 1.532(4) . ?
C010 C012 1.390(4) . ?
C010 C015 1.486(4) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C014 H014 0.9500 . ?
C014 C01B 1.391(4) . ?
C016 H01A 0.9800 . ?
C016 H01B 0.9800 . ?
C016 H01C 0.9800 . ?
C017 H017 1.0000 . ?
C017 C01A 1.519(4) . ?
C017 C01E 1.525(4) . ?
C018 H018 0.9500 . ?
C018 C01F 1.382(4) . ?
C019 H01D 0.9800 . ?
C019 H01E 0.9800 . ?
C019 H01F 0.9800 . ?
C01A H01G 0.9800 . ?
C01A H01H 0.9800 . ?
C01A H01I 0.9800 . ?
C01B H01J 0.9500 . ?
C01B C01D 1.382(5) . ?
C01C F01G 1.373(5) . ?
C01C F01H 1.301(5) . ?
C01C F1 1.317(5) . ?
C01C F00Y 1.364(5) . ?
C01C F01I 1.293(5) . ?
C01D H01K 0.9500 . ?
C01D C01F 1.384(5) . ?
C01E H01L 0.9800 . ?
C01E H01M 0.9800 . ?
C01E H01N 0.9800 . ?
C01F H01O 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
C00C N008 C00Z 124.3(2) . . ?
C00C N008 C017 119.1(2) . . ?
C00Z N008 C017 116.4(2) . . ?
C00H C009 C00D 120.5(2) . . ?
C00L C009 C00D 120.9(2) . . ?
C00L C009 C00H 118.5(3) . . ?
C00B C00A C00E 122.9(2) . . ?
C00B C00A C00Y 118.2(2) . . ?
C00Y C00A C00E 118.8(2) . . ?
C00A C00B H00B 119.4 . . ?
C00J C00B C00A 121.2(3) . . ?
C00J C00B H00B 119.4 . . ?
O004 C00C N008 121.2(2) . . ?
O004 C00C C00P 117.3(2) . . ?
N008 C00C C00P 121.5(2) . . ?
C009 C00D C00F 128.2(2) . . ?
C009 C00D C00G 120.6(2) . . ?
C009 C00D C00P 126.8(2) . . ?
C00F C00D C00P 90.50(19) . . ?
C00G C00D C00F 89.69(19) . . ?
C00G C00D C00P 89.67(19) . . ?
C00A C00E C00F 129.8(2) . . ?
C00A C00E C00M 121.3(2) . . ?
C00A C00E C00P 124.3(2) . . ?
C00F C00E C00M 89.96(19) . . ?
C00F C00E C00P 90.26(19) . . ?
C00M C00E C00P 89.98(19) . . ?
C00D C00F H00F 125.1 . . ?
C00E C00F C00D 90.16(19) . . ?
C00E C00F H00F 125.1 . . ?
C00E C00F C00O 90.0(2) . . ?
C00O C00F C00D 90.58(19) . . ?
C00O C00F H00F 125.1 . . ?
C00D C00G H00G 124.6 . . ?
C00D C00G C00K 91.48(19) . . ?
C00D C00G C00O 90.42(19) . . ?
C00K C00G H00G 124.6 . . ?
C00K C00G C00O 90.8(2) . . ?
C00O C00G H00G 124.6 . . ?
C009 C00H H00H 119.5 . . ?
C00U C00H C009 121.0(3) . . ?
C00U C00H H00H 119.5 . . ?
C00Q C00I C00K 121.1(2) . . ?
C00S C00I C00K 120.6(2) . . ?
C00S C00I C00Q 118.3(3) . . ?
C00B C00J H00J 120.3 . . ?
C00N C00J C00B 119.5(3) . . ?
C00N C00J H00J 120.3 . . ?
C00G C00K C00P 88.97(19) . . ?
C00I C00K C00G 124.5(2) . . ?
C00I C00K C00M 125.3(2) . . ?
C00I C00K C00P 127.1(2) . . ?
C00M C00K C00G 89.2(2) . . ?
C00M C00K C00P 90.16(19) . . ?
C009 C00L H00L 119.6 . . ?
C013 C00L C009 120.9(3) . . ?
C013 C00L H00L 119.6 . . ?
C00E C00M H00M 124.7 . . ?
C00K C00M C00E 90.99(19) . . ?
C00K C00M H00M 124.7 . . ?
C00K C00M C00O 91.6(2) . . ?
C00O C00M C00E 89.97(19) . . ?
C00O C00M H00M 124.7 . . ?
C00J C00N C00V 120.6(3) . . ?
C00J C00N C011 118.3(3) . . ?
C00V C00N C011 121.1(3) . . ?
C00F C00O C00G 89.31(19) . . ?
C00M C00O C00F 90.05(19) . . ?
C00M C00O C00G 88.5(2) . . ?
C00W C00O C00F 125.4(2) . . ?
C00W C00O C00G 125.5(2) . . ?
C00W C00O C00M 126.4(2) . . ?
C00C C00P C00D 129.3(2) . . ?
C00C C00P C00E 123.8(2) . . ?
C00C C00P C00K 124.0(2) . . ?
C00D C00P C00E 89.07(19) . . ?
C00D C00P C00K 89.88(19) . . ?
C00E C00P C00K 88.87(19) . . ?
C00I C00Q H00Q 119.6 . . ?
C012 C00Q C00I 120.8(3) . . ?
C012 C00Q H00Q 119.6 . . ?
C00U C00R C01C 119.5(3) . . ?
C013 C00R C00U 120.0(3) . . ?
C013 C00R C01C 120.4(3) . . ?
C00I C00S H00S 119.3 . . ?
C00I C00S C00T 121.3(3) . . ?
C00T C00S H00S 119.3 . . ?
C00S C00T H00T 120.1 . . ?
C010 C00T C00S 119.7(3) . . ?
C010 C00T H00T 120.1 . . ?
C00H C00U C00R 119.5(3) . . ?
C00H C00U H00U 120.2 . . ?
C00R C00U H00U 120.2 . . ?
C00N C00V H00V 120.3 . . ?
C00Y C00V C00N 119.3(3) . . ?
C00Y C00V H00V 120.3 . . ?
C014 C00W C00O 121.2(3) . . ?
C014 C00W C018 118.4(3) . . ?
C018 C00W C00O 120.3(3) . . ?
C00A C00Y H00Y 119.4 . . ?
C00V C00Y C00A 121.2(3) . . ?
C00V C00Y H00Y 119.4 . . ?
N008 C00Z H00Z 107.9 . . ?
N008 C00Z C016 112.2(2) . . ?
N008 C00Z C019 111.2(2) . . ?
C016 C00Z H00Z 107.9 . . ?
C016 C00Z C019 109.7(2) . . ?
C019 C00Z H00Z 107.9 . . ?
C00T C010 C012 119.8(3) . . ?
C00T C010 C015 119.6(3) . . ?
C012 C010 C015 120.6(3) . . ?
F001 C011 C00N 112.4(2) . . ?
F002 C011 F001 105.9(2) . . ?
F002 C011 F003 106.6(2) . . ?
F002 C011 C00N 113.4(2) . . ?
F003 C011 F001 105.7(2) . . ?
F003 C011 C00N 112.3(2) . . ?
C00Q C012 C010 120.0(3) . . ?
C00Q C012 H012 120.0 . . ?
C010 C012 H012 120.0 . . ?
C00L C013 C00R 120.1(3) . . ?
C00L C013 H013 120.0 . . ?
C00R C013 H013 120.0 . . ?
C00W C014 H014 119.6 . . ?
C01B C014 C00W 120.8(3) . . ?
C01B C014 H014 119.6 . . ?
F005 C015 C010 113.4(3) . . ?
F006 C015 F005 103.8(3) . . ?
F006 C015 C010 112.5(2) . . ?
F007 C015 F005 104.4(3) . . ?
F007 C015 F006 107.9(3) . . ?
F007 C015 C010 114.0(3) . . ?
C00Z C016 H01A 109.5 . . ?
C00Z C016 H01B 109.5 . . ?
C00Z C016 H01C 109.5 . . ?
H01A C016 H01B 109.5 . . ?
H01A C016 H01C 109.5 . . ?
H01B C016 H01C 109.5 . . ?
N008 C017 H017 106.5 . . ?
N008 C017 C01A 111.7(2) . . ?
N008 C017 C01E 112.3(2) . . ?
C01A C017 H017 106.5 . . ?
C01A C017 C01E 112.8(3) . . ?
C01E C017 H017 106.5 . . ?
C00W C018 H018 119.8 . . ?
C01F C018 C00W 120.5(3) . . ?
C01F C018 H018 119.8 . . ?
C00Z C019 H01D 109.5 . . ?
C00Z C019 H01E 109.5 . . ?
C00Z C019 H01F 109.5 . . ?
H01D C019 H01E 109.5 . . ?
H01D C019 H01F 109.5 . . ?
H01E C019 H01F 109.5 . . ?
C017 C01A H01G 109.5 . . ?
C017 C01A H01H 109.5 . . ?
C017 C01A H01I 109.5 . . ?
H01G C01A H01H 109.5 . . ?
H01G C01A H01I 109.5 . . ?
H01H C01A H01I 109.5 . . ?
C014 C01B H01J 119.9 . . ?
C01D C01B C014 120.2(3) . . ?
C01D C01B H01J 119.9 . . ?
F00X C01C C00R 115.9(4) . . ?
F00X C01C F01G 102.6(5) . . ?
F00X C01C F01H 111.5(6) . . ?
F01G C01C C00R 109.4(4) . . ?
F01H C01C C00R 113.8(3) . . ?
F01H C01C F01G 102.0(5) . . ?
F1 C01C C00R 112.1(4) . . ?
F1 C01C F00Y 101.1(5) . . ?
F00Y C01C C00R 111.6(3) . . ?
F01I C01C C00R 116.9(4) . . ?
F01I C01C F1 108.5(5) . . ?
F01I C01C F00Y 105.4(5) . . ?
C01B C01D H01K 120.4 . . ?
C01B C01D C01F 119.3(3) . . ?
C01F C01D H01K 120.4 . . ?
C017 C01E H01L 109.5 . . ?
C017 C01E H01M 109.5 . . ?
C017 C01E H01N 109.5 . . ?
H01L C01E H01M 109.5 . . ?
H01L C01E H01N 109.5 . . ?
H01M C01E H01N 109.5 . . ?
C018 C01F C01D 120.8(3) . . ?
C018 C01F H01O 119.6 . . ?
C01D C01F H01O 119.6 . . ?

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
O004 C00C C00P C00D -129.5(3) . . . . ?
O004 C00C C00P C00E 108.9(3) . . . . ?
O004 C00C C00P C00K -6.1(4) . . . . ?
N008 C00C C00P C00D 51.7(4) . . . . ?
N008 C00C C00P C00E -69.9(3) . . . . ?
N008 C00C C00P C00K 175.1(2) . . . . ?
C009 C00D C00F C00E -140.6(3) . . . . ?
C009 C00D C00F C00O 129.4(3) . . . . ?
C009 C00D C00G C00K 134.3(2) . . . . ?
C009 C00D C00G C00O -134.9(2) . . . . ?
C009 C00D C00P C00C 6.5(4) . . . . ?
C009 C00D C00P C00E 141.5(3) . . . . ?
C009 C00D C00P C00K -129.7(3) . . . . ?
C009 C00H C00U C00R -0.2(4) . . . . ?
C009 C00L C013 C00R 0.2(4) . . . . ?
C00A C00B C00J C00N -0.2(4) . . . . ?
C00A C00E C00F C00D 137.9(3) . . . . ?
C00A C00E C00F C00O -131.6(3) . . . . ?
C00A C00E C00M C00K -130.9(2) . . . . ?
C00A C00E C00M C00O 137.5(2) . . . . ?
C00A C00E C00P C00C -2.7(4) . . . . ?
C00A C00E C00P C00D -141.5(3) . . . . ?
C00A C00E C00P C00K 128.6(3) . . . . ?
C00B C00A C00E C00F 10.7(4) . . . . ?
C00B C00A C00E C00M -109.7(3) . . . . ?
C00B C00A C00E C00P 135.8(3) . . . . ?
C00B C00A C00Y C00V 0.1(4) . . . . ?
C00B C00J C00N C00V 0.1(4) . . . . ?
C00B C00J C00N C011 -179.0(3) . . . . ?
C00C N008 C00Z C016 -123.8(3) . . . . ?
C00C N008 C00Z C019 112.9(3) . . . . ?
C00C N008 C017 C01A 64.0(3) . . . . ?
C00C N008 C017 C01E -63.9(3) . . . . ?
C00D C009 C00H C00U 177.1(2) . . . . ?
C00D C009 C00L C013 -177.1(3) . . . . ?
C00D C00F C00O C00G 0.71(19) . . . . ?
C00D C00F C00O C00M 89.2(2) . . . . ?
C00D C00F C00O C00W -134.1(3) . . . . ?
C00D C00G C00K C00I -136.4(3) . . . . ?
C00D C00G C00K C00M 89.74(19) . . . . ?
C00D C00G C00K C00P -0.44(19) . . . . ?
C00D C00G C00O C00F -0.71(19) . . . . ?
C00D C00G C00O C00M -90.79(19) . . . . ?
C00D C00G C00O C00W 133.9(3) . . . . ?
C00E C00A C00B C00J 177.4(2) . . . . ?
C00E C00A C00Y C00V -177.3(2) . . . . ?
C00E C00F C00O C00G -89.45(19) . . . . ?
C00E C00F C00O C00M -0.98(19) . . . . ?
C00E C00F C00O C00W 135.8(3) . . . . ?
C00E C00M C00O C00F 0.98(19) . . . . ?
C00E C00M C00O C00G 90.29(19) . . . . ?
C00E C00M C00O C00W -135.0(3) . . . . ?
C00F C00D C00G C00K -90.1(2) . . . . ?
C00F C00D C00G C00O 0.71(19) . . . . ?
C00F C00D C00P C00C -134.6(3) . . . . ?
C00F C00D C00P C00E 0.38(19) . . . . ?
C00F C00D C00P C00K 89.25(19) . . . . ?
C00F C00E C00M C00K 90.6(2) . . . . ?
C00F C00E C00M C00O -0.98(19) . . . . ?
C00F C00E C00P C00C 138.4(2) . . . . ?
C00F C00E C00P C00D -0.38(19) . . . . ?
C00F C00E C00P C00K -90.28(19) . . . . ?
C00F C00O C00W C014 25.4(4) . . . . ?
C00F C00O C00W C018 -154.0(3) . . . . ?
C00G C00D C00F C00E 89.29(19) . . . . ?
C00G C00D C00F C00O -0.72(19) . . . . ?
C00G C00D C00P C00C 135.7(3) . . . . ?
C00G C00D C00P C00E -89.31(19) . . . . ?
C00G C00D C00P C00K -0.43(19) . . . . ?
C00G C00K C00M C00E -89.29(19) . . . . ?
C00G C00K C00M C00O 0.70(19) . . . . ?
C00G C00K C00P C00C -139.3(2) . . . . ?
C00G C00K C00P C00D 0.43(19) . . . . ?
C00G C00K C00P C00E 89.51(19) . . . . ?
C00G C00O C00W C014 -93.9(3) . . . . ?
C00G C00O C00W C018 86.7(4) . . . . ?
C00H C009 C00D C00F 165.5(2) . . . . ?
C00H C009 C00D C00G -77.3(3) . . . . ?
C00H C009 C00D C00P 38.5(4) . . . . ?
C00H C009 C00L C013 -1.0(4) . . . . ?
C00I C00K C00M C00E 137.5(3) . . . . ?
C00I C00K C00M C00O -132.5(3) . . . . ?
C00I C00K C00P C00C -5.1(4) . . . . ?
C00I C00K C00P C00D 134.6(3) . . . . ?
C00I C00K C00P C00E -136.3(3) . . . . ?
C00I C00Q C012 C010 1.1(4) . . . . ?
C00I C00S C00T C010 0.6(4) . . . . ?
C00J C00N C00V C00Y 0.0(4) . . . . ?
C00J C00N C011 F001 65.2(3) . . . . ?
C00J C00N C011 F002 -174.7(2) . . . . ?
C00J C00N C011 F003 -53.8(4) . . . . ?
C00K C00G C00O C00F 90.77(19) . . . . ?
C00K C00G C00O C00M 0.69(19) . . . . ?
C00K C00G C00O C00W -134.6(3) . . . . ?
C00K C00I C00Q C012 177.8(3) . . . . ?
C00K C00I C00S C00T -178.7(3) . . . . ?
C00K C00M C00O C00F -90.01(19) . . . . ?
C00K C00M C00O C00G -0.70(19) . . . . ?
C00K C00M C00O C00W 134.0(3) . . . . ?
C00L C009 C00D C00F -18.5(4) . . . . ?
C00L C009 C00D C00G 98.7(3) . . . . ?
C00L C009 C00D C00P -145.5(3) . . . . ?
C00L C009 C00H C00U 1.0(4) . . . . ?
C00M C00E C00F C00D -89.60(19) . . . . ?
C00M C00E C00F C00O 0.98(19) . . . . ?
C00M C00E C00P C00C -131.7(3) . . . . ?
C00M C00E C00P C00D 89.58(19) . . . . ?
C00M C00E C00P C00K -0.32(19) . . . . ?
C00M C00K C00P C00C 131.5(2) . . . . ?
C00M C00K C00P C00D -88.8(2) . . . . ?
C00M C00K C00P C00E 0.32(19) . . . . ?
C00M C00O C00W C014 147.1(3) . . . . ?
C00M C00O C00W C018 -32.4(4) . . . . ?
C00N C00V C00Y C00A -0.1(4) . . . . ?
C00O C00G C00K C00I 133.1(3) . . . . ?
C00O C00G C00K C00M -0.70(19) . . . . ?
C00O C00G C00K C00P -90.87(19) . . . . ?
C00O C00W C014 C01B -177.2(3) . . . . ?
C00O C00W C018 C01F 177.7(3) . . . . ?
C00P C00D C00F C00E -0.38(19) . . . . ?
C00P C00D C00F C00O -90.39(19) . . . . ?
C00P C00D C00G C00K 0.44(19) . . . . ?
C00P C00D C00G C00O 91.21(19) . . . . ?
C00P C00E C00F C00D 0.38(19) . . . . ?
C00P C00E C00F C00O 90.96(19) . . . . ?
C00P C00E C00M C00K 0.3(2) . . . . ?
C00P C00E C00M C00O -91.25(19) . . . . ?
C00P C00K C00M C00E -0.33(19) . . . . ?
C00P C00K C00M C00O 89.67(19) . . . . ?
C00Q C00I C00K C00G 62.8(4) . . . . ?
C00Q C00I C00K C00M -179.3(3) . . . . ?
C00Q C00I C00K C00P -56.7(4) . . . . ?
C00Q C00I C00S C00T 1.6(4) . . . . ?
C00S C00I C00K C00G -116.8(3) . . . . ?
C00S C00I C00K C00M 1.0(4) . . . . ?
C00S C00I C00K C00P 123.7(3) . . . . ?
C00S C00I C00Q C012 -2.5(4) . . . . ?
C00S C00T C010 C012 -2.1(4) . . . . ?
C00S C00T C010 C015 174.3(3) . . . . ?
C00T C010 C012 C00Q 1.2(4) . . . . ?
C00T C010 C015 F005 36.4(4) . . . . ?
C00T C010 C015 F006 -81.0(4) . . . . ?
C00T C010 C015 F007 155.7(3) . . . . ?
C00U C00R C013 C00L 0.5(4) . . . . ?
C00U C00R C01C F00X 26.6(8) . . . . ?
C00U C00R C01C F01G 142.0(7) . . . . ?
C00U C00R C01C F01H -104.6(8) . . . . ?
C00U C00R C01C F1 59.9(6) . . . . ?
C00U C00R C01C F00Y -52.7(7) . . . . ?
C00U C00R C01C F01I -174.0(7) . . . . ?
C00V C00N C011 F001 -113.9(3) . . . . ?
C00V C00N C011 F002 6.2(4) . . . . ?
C00V C00N C011 F003 127.1(3) . . . . ?
C00W C014 C01B C01D -0.9(5) . . . . ?
C00W C018 C01F C01D -0.2(5) . . . . ?
C00Y C00A C00B C00J 0.1(4) . . . . ?
C00Y C00A C00E C00F -172.0(3) . . . . ?
C00Y C00A C00E C00M 67.6(3) . . . . ?
C00Y C00A C00E C00P -46.9(4) . . . . ?
C00Z N008 C00C O004 -171.6(2) . . . . ?
C00Z N008 C00C C00P 7.1(4) . . . . ?
C00Z N008 C017 C01A -120.9(3) . . . . ?
C00Z N008 C017 C01E 111.2(3) . . . . ?
C011 C00N C00V C00Y 179.2(3) . . . . ?
C012 C010 C015 F005 -147.3(3) . . . . ?
C012 C010 C015 F006 95.3(3) . . . . ?
C012 C010 C015 F007 -28.0(4) . . . . ?
C013 C00R C00U C00H -0.5(4) . . . . ?
C013 C00R C01C F00X -154.4(7) . . . . ?
C013 C00R C01C F01G -39.1(7) . . . . ?
C013 C00R C01C F01H 74.3(8) . . . . ?
C013 C00R C01C F1 -121.1(6) . . . . ?
C013 C00R C01C F00Y 126.2(6) . . . . ?
C013 C00R C01C F01I 5.0(8) . . . . ?
C014 C00W C018 C01F -1.7(4) . . . . ?
C014 C01B C01D C01F -1.1(5) . . . . ?
C015 C010 C012 C00Q -175.1(3) . . . . ?
C017 N008 C00C O004 3.0(4) . . . . ?
C017 N008 C00C C00P -178.3(2) . . . . ?
C017 N008 C00Z C016 61.5(3) . . . . ?
C017 N008 C00Z C019 -61.8(3) . . . . ?
C018 C00W C014 C01B 2.2(4) . . . . ?
C01B C01D C01F C018 1.6(5) . . . . ?
C01C C00R C00U C00H 178.4(3) . . . . ?
C01C C00R C013 C00L -178.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.666
####################################################################### 
# 
# 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_2e
_database_code_depnum_ccdc_archive 'CCDC 1993515'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C68 H84 N4 O4'
_chemical_formula_weight         1021.39

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                   13.5226(5)
_cell_length_b                   14.1690(5)
_cell_length_c                   17.1029(5)
_cell_angle_alpha                103.450(3)
_cell_angle_beta                 107.340(3)
_cell_angle_gamma                103.234(3)
_cell_volume                     2880.96(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    6543

_cell_measurement_theta_min      2.5440

_cell_measurement_theta_max      26.0350


_exptl_crystal_description       platelet

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.76321

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            31848
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             10091
_reflns_number_gt                5906
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    SIR97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0856P)²+2.5830P] 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         10091
_refine_ls_number_parameters     701
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0768
_refine_ls_wR_factor_ref         0.2124
_refine_ls_wR_factor_gt          0.1775
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
O1 O 0.3345(2) 0.9958(2) 0.10298(17) 0.0365(7) Uani 1 1 d . . . . .
C1 C 0.3458(3) 1.0880(3) 0.1242(2) 0.0279(9) Uani 1 1 d . . . . .
N1 N 0.4245(2) 1.1558(2) 0.19805(19) 0.0294(7) Uani 1 1 d . . . . .
C2 C 0.5010(3) 1.1193(3) 0.2565(2) 0.0325(9) Uani 1 1 d . . . . .
H10 H 0.551828 1.181297 0.306524 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4439(3) 1.0465(3) 0.2944(3) 0.0449(11) Uani 1 1 d . . . . .
H11 H 0.402018 1.079284 0.323204 0.067 Uiso 1 1 calc R U . . .
H12 H 0.498729 1.030111 0.336450 0.067 Uiso 1 1 calc R U . . .
H13 H 0.394285 0.983366 0.247777 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5719(3) 1.0755(3) 0.2145(3) 0.0467(11) Uani 1 1 d . . . . .
H14 H 0.526770 1.010416 0.168456 0.070 Uiso 1 1 calc R U . . .
H15 H 0.629481 1.063770 0.258073 0.070 Uiso 1 1 calc R U . . .
H16 H 0.605289 1.123907 0.189759 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4380(3) 1.2663(3) 0.2245(2) 0.0295(9) Uani 1 1 d . . . . .
H17 H 0.385607 1.278538 0.175736 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4076(3) 1.2975(3) 0.3027(2) 0.0398(10) Uani 1 1 d . . . . .
H18 H 0.331975 1.256820 0.289497 0.060 Uiso 1 1 calc R U . . .
H19 H 0.414364 1.370366 0.317593 0.060 Uiso 1 1 calc R U . . .
H20 H 0.456776 1.285460 0.351770 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5528(3) 1.3318(3) 0.2396(3) 0.0368(10) Uani 1 1 d . . . . .
H21 H 0.605190 1.329555 0.292374 0.055 Uiso 1 1 calc R U . . .
H22 H 0.554426 1.402810 0.246043 0.055 Uiso 1 1 calc R U . . .
H23 H 0.572423 1.305287 0.190130 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2715(3) 1.1252(3) 0.0629(2) 0.0269(9) Uani 1 1 d . . . . .
C9 C 0.3108(3) 1.1865(3) 0.0043(2) 0.0260(8) Uani 1 1 d . . . . .
C10 C 0.2346(3) 1.2518(3) 0.0161(2) 0.0261(8) Uani 1 1 d . . . . .
H24 H 0.256088 1.327865 0.029722 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1967(3) 1.1926(3) 0.0742(2) 0.0284(9) Uani 1 1 d . . . . .
H25 H 0.190242 1.225130 0.130148 0.034 Uiso 1 1 calc R U . . .
C12 C 0.1007(3) 1.1135(3) -0.0077(2) 0.0278(9) Uani 1 1 d . . . . .
H26 H 0.023371 1.087002 -0.012263 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1755(3) 1.0467(3) -0.0193(2) 0.0283(9) Uani 1 1 d . . . . .
H27 H 0.152948 0.970591 -0.032775 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2136(3) 1.1049(3) -0.0774(2) 0.0268(9) Uani 1 1 d . . . . .
H28 H 0.219540 1.071860 -0.133513 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1393(3) 1.1732(3) -0.0660(2) 0.0257(8) Uani 1 1 d . . . . .
C16 C 0.4244(3) 1.2228(3) 0.0085(2) 0.0243(8) Uani 1 1 d . . . . .
C17 C 0.4838(3) 1.1555(3) 0.0027(2) 0.0299(9) Uani 1 1 d . . . . .
H1 H 0.450692 1.085832 -0.003954 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5902(3) 1.1872(3) 0.0063(2) 0.0299(9) Uani 1 1 d . . . . .
H2 H 0.629019 1.139342 0.002581 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6414(3) 1.2895(3) 0.0153(2) 0.0245(8) Uani 1 1 d . . . . .
C20 C 0.5808(3) 1.3559(3) 0.0196(2) 0.0261(9) Uani 1 1 d . . . . .
H3 H 0.612779 1.425151 0.024481 0.031 Uiso 1 1 calc R U . . .
C21 C 0.4747(3) 1.3238(3) 0.0170(2) 0.0268(9) Uani 1 1 d . . . . .
H4 H 0.435838 1.371546 0.021024 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7564(3) 1.3236(3) 0.0207(2) 0.0266(9) Uani 1 1 d . . . . .
C23 C 0.8017(3) 1.2550(3) -0.0156(2) 0.0311(9) Uani 1 1 d . . . . .
H5 H 0.757864 1.185529 -0.045994 0.037 Uiso 1 1 calc R U . . .
C24 C 0.9103(3) 1.2866(3) -0.0081(2) 0.0341(10) Uani 1 1 d . . . . .
H6 H 0.940207 1.238451 -0.032870 0.041 Uiso 1 1 calc R U . . .
C25 C 0.9748(3) 1.3876(3) 0.0350(3) 0.0368(10) Uani 1 1 d . . . . .
H7 H 1.049108 1.408992 0.040445 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9306(3) 1.4568(3) 0.0700(2) 0.0353(10) Uani 1 1 d . . . . .
H8 H 0.974384 1.526577 0.098951 0.042 Uiso 1 1 calc R U . . .
C27 C 0.8228(3) 1.4258(3) 0.0635(2) 0.0297(9) Uani 1 1 d . . . . .
H9 H 0.793536 1.474554 0.088308 0.036 Uiso 1 1 calc R U . . .
C28 C 0.0713(3) 1.2091(3) -0.1329(2) 0.0261(9) Uani 1 1 d . . . . .
O2 O 0.09029(19) 1.3009(2) -0.12086(16) 0.0311(6) Uani 1 1 d . . . . .
N2 N -0.0079(2) 1.1367(2) -0.20507(18) 0.0277(7) Uani 1 1 d . . . . .
C29 C -0.0297(3) 1.0259(3) -0.2203(2) 0.0350(10) Uani 1 1 d . . . . .
H29 H 0.022749 1.018176 -0.168728 0.042 Uiso 1 1 calc R U . . .
C30 C -0.0059(4) 0.9757(3) -0.2986(3) 0.0502(12) Uani 1 1 d . . . . .
H30 H -0.054515 0.983164 -0.350564 0.075 Uiso 1 1 calc R U . . .
H31 H -0.018403 0.902704 -0.305843 0.075 Uiso 1 1 calc R U . . .
H32 H 0.070360 1.008788 -0.289797 0.075 Uiso 1 1 calc R U . . .
C31 C -0.1444(3) 0.9734(4) -0.2258(3) 0.0555(13) Uani 1 1 d . . . . .
H33 H -0.157822 1.012112 -0.176754 0.083 Uiso 1 1 calc R U . . .
H34 H -0.150987 0.903575 -0.224186 0.083 Uiso 1 1 calc R U . . .
H35 H -0.198294 0.970603 -0.280082 0.083 Uiso 1 1 calc R U . . .
C32 C -0.0775(3) 1.1680(3) -0.2731(2) 0.0319(9) Uani 1 1 d . . . . .
H36 H -0.128836 1.103478 -0.320195 0.038 Uiso 1 1 calc R U . . .
C33 C -0.1477(3) 1.2240(3) -0.2405(3) 0.0400(10) Uani 1 1 d . . . . .
H37 H -0.193724 1.180189 -0.219571 0.060 Uiso 1 1 calc R U . . .
H38 H -0.194187 1.240865 -0.287701 0.060 Uiso 1 1 calc R U . . .
H39 H -0.100479 1.287297 -0.193001 0.060 Uiso 1 1 calc R U . . .
C34 C -0.0100(3) 1.2275(3) -0.3135(3) 0.0402(10) Uani 1 1 d . . . . .
H40 H 0.036727 1.294542 -0.271042 0.060 Uiso 1 1 calc R U . . .
H41 H -0.059021 1.237026 -0.364165 0.060 Uiso 1 1 calc R U . . .
H42 H 0.035748 1.189199 -0.331458 0.060 Uiso 1 1 calc R U . . .
O3 O 0.5017(2) 0.4056(2) 0.64348(17) 0.0397(7) Uani 1 1 d . . . . .
C35 C 0.4190(3) 0.3711(3) 0.6575(2) 0.0318(9) Uani 1 1 d . . . . .
N3 N 0.4224(2) 0.3396(2) 0.72697(18) 0.0307(8) Uani 1 1 d . . . . .
C36 C 0.5289(3) 0.3521(3) 0.7926(2) 0.0368(10) Uani 1 1 d . . . . .
H52 H 0.511983 0.330865 0.840219 0.044 Uiso 1 1 calc R U . . .
C37 C 0.5856(4) 0.2812(4) 0.7589(3) 0.0624(15) Uani 1 1 d . . . . .
H53 H 0.534714 0.210974 0.732646 0.094 Uiso 1 1 calc R U . . .
H54 H 0.649147 0.284108 0.806783 0.094 Uiso 1 1 calc R U . . .
H55 H 0.609797 0.302586 0.715235 0.094 Uiso 1 1 calc R U . . .
C38 C 0.6029(3) 0.4625(3) 0.8335(3) 0.0458(11) Uani 1 1 d . . . . .
H56 H 0.630699 0.484122 0.791513 0.069 Uiso 1 1 calc R U . . .
H57 H 0.664455 0.468643 0.884501 0.069 Uiso 1 1 calc R U . . .
H58 H 0.561431 0.506284 0.850901 0.069 Uiso 1 1 calc R U . . .
C39 C 0.3235(3) 0.2990(3) 0.7444(2) 0.0390(10) Uani 1 1 d . . . . .
H59 H 0.259265 0.286817 0.691169 0.047 Uiso 1 1 calc R U . . .
C40 C 0.3156(4) 0.3773(4) 0.8171(3) 0.0483(12) Uani 1 1 d . . . . .
H60 H 0.378137 0.392581 0.870543 0.073 Uiso 1 1 calc R U . . .
H61 H 0.247535 0.350065 0.825588 0.073 Uiso 1 1 calc R U . . .
H62 H 0.316067 0.440253 0.802418 0.073 Uiso 1 1 calc R U . . .
C41 C 0.3152(4) 0.1964(3) 0.7592(3) 0.0594(14) Uani 1 1 d . . . . .
H63 H 0.327144 0.150545 0.712837 0.089 Uiso 1 1 calc R U . . .
H64 H 0.242361 0.165995 0.759036 0.089 Uiso 1 1 calc R U . . .
H65 H 0.370817 0.206419 0.815110 0.089 Uiso 1 1 calc R U . . .
C42 C 0.3093(3) 0.3600(3) 0.5930(2) 0.0325(9) Uani 1 1 d . . . . .
C43 C 0.2259(3) 0.2524(3) 0.5225(2) 0.0334(9) Uani 1 1 d . . . . .
C44 C 0.2236(3) 0.3027(3) 0.4501(2) 0.0321(9) Uani 1 1 d . . . . .
H66 H 0.230075 0.270660 0.393951 0.039 Uiso 1 1 calc R U . . .
C45 C 0.3028(3) 0.4072(3) 0.5189(2) 0.0379(10) Uani 1 1 d . . . . .
H67 H 0.366874 0.452459 0.512916 0.045 Uiso 1 1 calc R U . . .
C46 C 0.2029(3) 0.4384(3) 0.5288(3) 0.0420(11) Uani 1 1 d . . . . .
H68 H 0.193841 0.506914 0.531018 0.050 Uiso 1 1 calc R U . . .
C47 C 0.2074(4) 0.3904(3) 0.6015(3) 0.0433(11) Uani 1 1 d . . . . .
H69 H 0.200782 0.422962 0.657393 0.052 Uiso 1 1 calc R U . . .
C48 C 0.1275(3) 0.2856(3) 0.5326(2) 0.0371(10) Uani 1 1 d . . . . .
H70 H 0.062495 0.241244 0.538056 0.045 Uiso 1 1 calc R U . . .
C49 C 0.1233(3) 0.3342(3) 0.4591(2) 0.0327(9) Uani 1 1 d . . . . .
C50 C 0.2421(3) 0.1510(3) 0.5173(2) 0.0338(10) Uani 1 1 d . . . . .
C51 C 0.3308(3) 0.1309(3) 0.4989(3) 0.0399(10) Uani 1 1 d . . . . .
H43 H 0.380880 0.182524 0.490074 0.048 Uiso 1 1 calc R U . . .
C52 C 0.3465(3) 0.0379(3) 0.4935(3) 0.0370(10) Uani 1 1 d . . . . .
H44 H 0.406634 0.025914 0.479835 0.044 Uiso 1 1 calc R U . . .
C53 C 0.2764(3) -0.0400(3) 0.5077(2) 0.0355(10) Uani 1 1 d . . . . .
C54 C 0.1889(3) -0.0192(3) 0.5253(2) 0.0362(10) Uani 1 1 d . . . . .
H45 H 0.139192 -0.070773 0.534473 0.043 Uiso 1 1 calc R U . . .
C55 C 0.1710(3) 0.0739(3) 0.5301(2) 0.0358(10) Uani 1 1 d . . . . .
H46 H 0.109723 0.085081 0.542289 0.043 Uiso 1 1 calc R U . . .
C56 C 0.2957(3) -0.1398(3) 0.5034(2) 0.0276(9) Uani 1 1 d . . . . .
C57 C 0.3572(3) -0.1749(3) 0.4584(3) 0.0408(11) Uani 1 1 d . . . . .
H47 H 0.385457 -0.135910 0.426975 0.049 Uiso 1 1 calc R U . . .
C58 C 0.3781(3) -0.2668(3) 0.4588(3) 0.0429(11) Uani 1 1 d . . . . .
H48 H 0.421421 -0.289082 0.428400 0.052 Uiso 1 1 calc R U . . .
C59 C 0.3378(3) -0.3241(3) 0.5017(3) 0.0410(11) Uani 1 1 d . . . . .
H49 H 0.352366 -0.386629 0.501600 0.049 Uiso 1 1 calc R U . . .
C60 C 0.2740(4) -0.2908(3) 0.5465(3) 0.0438(11) Uani 1 1 d . . . . .
H50 H 0.244497 -0.330814 0.576679 0.053 Uiso 1 1 calc R U . . .
C61 C 0.2543(3) -0.1998(3) 0.5465(3) 0.0378(10) Uani 1 1 d . . . . .
H51 H 0.211109 -0.177638 0.577020 0.045 Uiso 1 1 calc R U . . .
C62 C 0.0178(3) 0.3092(3) 0.3849(2) 0.0343(10) Uani 1 1 d . . . . .
O4 O -0.0646(2) 0.2446(3) 0.38009(19) 0.0568(9) Uani 1 1 d . . . . .
N4 N 0.0190(2) 0.3510(2) 0.32130(19) 0.0312(8) Uani 1 1 d . . . . .
C63 C 0.1141(3) 0.4290(3) 0.3263(3) 0.0488(12) Uani 1 1 d . . . . .
H71 H 0.173168 0.443418 0.383359 0.059 Uiso 1 1 calc R U . . .
C64 C 0.1568(4) 0.3913(5) 0.2574(3) 0.083(2) Uani 1 1 d . . . . .
H72 H 0.164385 0.324024 0.256907 0.125 Uiso 1 1 calc R U . . .
H73 H 0.228246 0.439832 0.269466 0.125 Uiso 1 1 calc R U . . .
H74 H 0.105479 0.385360 0.200764 0.125 Uiso 1 1 calc R U . . .
C65 C 0.0886(5) 0.5284(4) 0.3266(4) 0.084(2) Uani 1 1 d . . . . .
H75 H 0.031262 0.517516 0.271289 0.126 Uiso 1 1 calc R U . . .
H76 H 0.154788 0.581877 0.334735 0.126 Uiso 1 1 calc R U . . .
H77 H 0.063466 0.549660 0.373945 0.126 Uiso 1 1 calc R U . . .
C66 C -0.0811(3) 0.3181(3) 0.2419(2) 0.0369(10) Uani 1 1 d . . . . .
H78 H -0.062030 0.355989 0.203130 0.044 Uiso 1 1 calc R U . . .
C67 C -0.1142(4) 0.2036(4) 0.1925(3) 0.0609(14) Uani 1 1 d . . . . .
H79 H -0.052196 0.188527 0.180148 0.091 Uiso 1 1 calc R U . . .
H80 H -0.175973 0.185778 0.137937 0.091 Uiso 1 1 calc R U . . .
H81 H -0.135696 0.163399 0.227698 0.091 Uiso 1 1 calc R U . . .
C68 C -0.1745(4) 0.3456(5) 0.2593(3) 0.0669(16) Uani 1 1 d . . . . .
H82 H -0.198842 0.306649 0.294339 0.100 Uiso 1 1 calc R U . . .
H83 H -0.234969 0.329059 0.204297 0.100 Uiso 1 1 calc R U . . .
H84 H -0.150847 0.419100 0.290673 0.100 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
O1 C1 1.232(4) . ?
C1 N1 1.348(5) . ?
C1 C8 1.503(5) . ?
N1 C5 1.476(5) . ?
N1 C2 1.485(4) . ?
C2 C4 1.515(6) . ?
C2 C3 1.525(5) . ?
C2 H10 1.0000 . ?
C3 H11 0.9800 . ?
C3 H12 0.9800 . ?
C3 H13 0.9800 . ?
C4 H14 0.9800 . ?
C4 H15 0.9800 . ?
C4 H16 0.9800 . ?
C5 C6 1.512(5) . ?
C5 C7 1.526(5) . ?
C5 H17 1.0000 . ?
C6 H18 0.9800 . ?
C6 H19 0.9800 . ?
C6 H20 0.9800 . ?
C7 H21 0.9800 . ?
C7 H22 0.9800 . ?
C7 H23 0.9800 . ?
C8 C13 1.556(5) . ?
C8 C11 1.564(5) . ?
C8 C9 1.597(5) . ?
C9 C16 1.478(5) . ?
C9 C10 1.559(5) . ?
C9 C14 1.573(5) . ?
C10 C15 1.552(5) . ?
C10 C11 1.563(5) . ?
C10 H24 1.0000 . ?
C11 C12 1.557(5) . ?
C11 H25 1.0000 . ?
C12 C13 1.558(5) . ?
C12 C15 1.574(5) . ?
C12 H26 1.0000 . ?
C13 C14 1.558(5) . ?
C13 H27 1.0000 . ?
C14 C15 1.568(5) . ?
C14 H28 1.0000 . ?
C15 C28 1.507(5) . ?
C16 C17 1.385(5) . ?
C16 C21 1.390(5) . ?
C17 C18 1.383(5) . ?
C17 H1 0.9500 . ?
C18 C19 1.406(5) . ?
C18 H2 0.9500 . ?
C19 C20 1.386(5) . ?
C19 C22 1.487(5) . ?
C20 C21 1.386(5) . ?
C20 H3 0.9500 . ?
C21 H4 0.9500 . ?
C22 C23 1.385(5) . ?
C22 C27 1.400(5) . ?
C23 C24 1.391(5) . ?
C23 H5 0.9500 . ?
C24 C25 1.381(6) . ?
C24 H6 0.9500 . ?
C25 C26 1.373(6) . ?
C25 H7 0.9500 . ?
C26 C27 1.385(5) . ?
C26 H8 0.9500 . ?
C27 H9 0.9500 . ?
C28 O2 1.222(4) . ?
C28 N2 1.357(4) . ?
N2 C29 1.474(5) . ?
N2 C32 1.489(4) . ?
C29 C30 1.523(6) . ?
C29 C31 1.524(6) . ?
C29 H29 1.0000 . ?
C30 H30 0.9800 . ?
C30 H31 0.9800 . ?
C30 H32 0.9800 . ?
C31 H33 0.9800 . ?
C31 H34 0.9800 . ?
C31 H35 0.9800 . ?
C32 C33 1.515(5) . ?
C32 C34 1.522(5) . ?
C32 H36 1.0000 . ?
C33 H37 0.9800 . ?
C33 H38 0.9800 . ?
C33 H39 0.9800 . ?
C34 H40 0.9800 . ?
C34 H41 0.9800 . ?
C34 H42 0.9800 . ?
O3 C35 1.229(4) . ?
C35 N3 1.356(5) . ?
C35 C42 1.510(5) . ?
N3 C39 1.475(5) . ?
N3 C36 1.480(5) . ?
C36 C37 1.508(6) . ?
C36 C38 1.516(6) . ?
C36 H52 1.0000 . ?
C37 H53 0.9800 . ?
C37 H54 0.9800 . ?
C37 H55 0.9800 . ?
C38 H56 0.9800 . ?
C38 H57 0.9800 . ?
C38 H58 0.9800 . ?
C39 C40 1.511(6) . ?
C39 C41 1.517(6) . ?
C39 H59 1.0000 . ?
C40 H60 0.9800 . ?
C40 H61 0.9800 . ?
C40 H62 0.9800 . ?
C41 H63 0.9800 . ?
C41 H64 0.9800 . ?
C41 H65 0.9800 . ?
C42 C45 1.554(5) . ?
C42 C47 1.571(6) . ?
C42 C43 1.612(5) . ?
C43 C50 1.489(5) . ?
C43 C48 1.552(5) . ?
C43 C44 1.562(5) . ?
C44 C49 1.561(5) . ?
C44 C45 1.561(6) . ?
C44 H66 1.0000 . ?
C45 C46 1.557(6) . ?
C45 H67 1.0000 . ?
C46 C47 1.541(6) . ?
C46 C49 1.564(6) . ?
C46 H68 1.0000 . ?
C47 C48 1.567(6) . ?
C47 H69 1.0000 . ?
C48 C49 1.560(5) . ?
C48 H70 1.0000 . ?
C49 C62 1.501(5) . ?
C50 C55 1.386(5) . ?
C50 C51 1.399(5) . ?
C51 C52 1.368(6) . ?
C51 H43 0.9500 . ?
C52 C53 1.399(5) . ?
C52 H44 0.9500 . ?
C53 C54 1.381(5) . ?
C53 C56 1.485(5) . ?
C54 C55 1.383(5) . ?
C54 H45 0.9500 . ?
C55 H46 0.9500 . ?
C56 C61 1.378(5) . ?
C56 C57 1.388(5) . ?
C57 C58 1.395(6) . ?
C57 H47 0.9500 . ?
C58 C59 1.345(6) . ?
C58 H48 0.9500 . ?
C59 C60 1.403(6) . ?
C59 H49 0.9500 . ?
C60 C61 1.375(6) . ?
C60 H50 0.9500 . ?
C61 H51 0.9500 . ?
C62 O4 1.237(5) . ?
C62 N4 1.356(5) . ?
N4 C63 1.457(5) . ?
N4 C66 1.487(5) . ?
C63 C64 1.504(7) . ?
C63 C65 1.524(7) . ?
C63 H71 1.0000 . ?
C64 H72 0.9800 . ?
C64 H73 0.9800 . ?
C64 H74 0.9800 . ?
C65 H75 0.9800 . ?
C65 H76 0.9800 . ?
C65 H77 0.9800 . ?
C66 C68 1.493(6) . ?
C66 C67 1.533(6) . ?
C66 H78 1.0000 . ?
C67 H79 0.9800 . ?
C67 H80 0.9800 . ?
C67 H81 0.9800 . ?
C68 H82 0.9800 . ?
C68 H83 0.9800 . ?
C68 H84 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
O1 C1 N1 122.3(3) . . ?
O1 C1 C8 117.9(3) . . ?
N1 C1 C8 119.7(3) . . ?
C1 N1 C5 122.7(3) . . ?
C1 N1 C2 119.5(3) . . ?
C5 N1 C2 117.8(3) . . ?
N1 C2 C4 112.2(3) . . ?
N1 C2 C3 113.0(3) . . ?
C4 C2 C3 112.3(3) . . ?
N1 C2 H10 106.2 . . ?
C4 C2 H10 106.2 . . ?
C3 C2 H10 106.2 . . ?
C2 C3 H11 109.5 . . ?
C2 C3 H12 109.5 . . ?
H11 C3 H12 109.5 . . ?
C2 C3 H13 109.5 . . ?
H11 C3 H13 109.5 . . ?
H12 C3 H13 109.5 . . ?
C2 C4 H14 109.5 . . ?
C2 C4 H15 109.5 . . ?
H14 C4 H15 109.5 . . ?
C2 C4 H16 109.5 . . ?
H14 C4 H16 109.5 . . ?
H15 C4 H16 109.5 . . ?
N1 C5 C6 111.1(3) . . ?
N1 C5 C7 112.0(3) . . ?
C6 C5 C7 111.7(3) . . ?
N1 C5 H17 107.3 . . ?
C6 C5 H17 107.3 . . ?
C7 C5 H17 107.3 . . ?
C5 C6 H18 109.5 . . ?
C5 C6 H19 109.5 . . ?
H18 C6 H19 109.5 . . ?
C5 C6 H20 109.5 . . ?
H18 C6 H20 109.5 . . ?
H19 C6 H20 109.5 . . ?
C5 C7 H21 109.5 . . ?
C5 C7 H22 109.5 . . ?
H21 C7 H22 109.5 . . ?
C5 C7 H23 109.5 . . ?
H21 C7 H23 109.5 . . ?
H22 C7 H23 109.5 . . ?
C1 C8 C13 119.9(3) . . ?
C1 C8 C11 133.2(3) . . ?
C13 C8 C11 89.6(3) . . ?
C1 C8 C9 123.1(3) . . ?
C13 C8 C9 89.9(3) . . ?
C11 C8 C9 89.2(3) . . ?
C16 C9 C10 127.6(3) . . ?
C16 C9 C14 123.9(3) . . ?
C10 C9 C14 89.7(3) . . ?
C16 C9 C8 125.6(3) . . ?
C10 C9 C8 89.6(3) . . ?
C14 C9 C8 88.7(2) . . ?
C15 C10 C9 90.6(3) . . ?
C15 C10 C11 90.7(3) . . ?
C9 C10 C11 90.6(3) . . ?
C15 C10 H24 124.8 . . ?
C9 C10 H24 124.8 . . ?
C11 C10 H24 124.8 . . ?
C12 C11 C10 89.7(3) . . ?
C12 C11 C8 90.2(3) . . ?
C10 C11 C8 90.7(3) . . ?
C12 C11 H25 125.1 . . ?
C10 C11 H25 125.1 . . ?
C8 C11 H25 125.1 . . ?
C11 C12 C13 89.8(3) . . ?
C11 C12 C15 90.1(3) . . ?
C13 C12 C15 90.2(3) . . ?
C11 C12 H26 125.2 . . ?
C13 C12 H26 125.2 . . ?
C15 C12 H26 125.2 . . ?
C8 C13 C14 90.7(3) . . ?
C8 C13 C12 90.4(3) . . ?
C14 C13 C12 90.1(3) . . ?
C8 C13 H27 125.0 . . ?
C14 C13 H27 125.0 . . ?
C12 C13 H27 125.0 . . ?
C13 C14 C15 90.5(3) . . ?
C13 C14 C9 90.7(3) . . ?
C15 C14 C9 89.5(3) . . ?
C13 C14 H28 125.1 . . ?
C15 C14 H28 125.1 . . ?
C9 C14 H28 125.1 . . ?
C28 C15 C10 120.5(3) . . ?
C28 C15 C14 128.1(3) . . ?
C10 C15 C14 90.1(3) . . ?
C28 C15 C12 127.9(3) . . ?
C10 C15 C12 89.5(3) . . ?
C14 C15 C12 89.2(3) . . ?
C17 C16 C21 117.7(3) . . ?
C17 C16 C9 120.4(3) . . ?
C21 C16 C9 121.9(3) . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H1 119.2 . . ?
C16 C17 H1 119.2 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H2 119.6 . . ?
C19 C18 H2 119.6 . . ?
C20 C19 C18 117.3(3) . . ?
C20 C19 C22 122.2(3) . . ?
C18 C19 C22 120.5(3) . . ?
C19 C20 C21 121.6(3) . . ?
C19 C20 H3 119.2 . . ?
C21 C20 H3 119.2 . . ?
C20 C21 C16 121.0(3) . . ?
C20 C21 H4 119.5 . . ?
C16 C21 H4 119.5 . . ?
C23 C22 C27 117.9(3) . . ?
C23 C22 C19 121.1(3) . . ?
C27 C22 C19 121.0(3) . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H5 119.5 . . ?
C24 C23 H5 119.5 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H6 119.8 . . ?
C23 C24 H6 119.8 . . ?
C26 C25 C24 119.4(4) . . ?
C26 C25 H7 120.3 . . ?
C24 C25 H7 120.3 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H8 119.7 . . ?
C27 C26 H8 119.7 . . ?
C26 C27 C22 120.8(4) . . ?
C26 C27 H9 119.6 . . ?
C22 C27 H9 119.6 . . ?
O2 C28 N2 122.9(3) . . ?
O2 C28 C15 119.2(3) . . ?
N2 C28 C15 117.8(3) . . ?
C28 N2 C29 123.0(3) . . ?
C28 N2 C32 120.0(3) . . ?
C29 N2 C32 117.0(3) . . ?
N2 C29 C30 111.2(3) . . ?
N2 C29 C31 111.8(3) . . ?
C30 C29 C31 112.8(4) . . ?
N2 C29 H29 106.9 . . ?
C30 C29 H29 106.9 . . ?
C31 C29 H29 106.9 . . ?
C29 C30 H30 109.5 . . ?
C29 C30 H31 109.5 . . ?
H30 C30 H31 109.5 . . ?
C29 C30 H32 109.5 . . ?
H30 C30 H32 109.5 . . ?
H31 C30 H32 109.5 . . ?
C29 C31 H33 109.5 . . ?
C29 C31 H34 109.5 . . ?
H33 C31 H34 109.5 . . ?
C29 C31 H35 109.5 . . ?
H33 C31 H35 109.5 . . ?
H34 C31 H35 109.5 . . ?
N2 C32 C33 112.1(3) . . ?
N2 C32 C34 111.5(3) . . ?
C33 C32 C34 112.9(3) . . ?
N2 C32 H36 106.7 . . ?
C33 C32 H36 106.7 . . ?
C34 C32 H36 106.7 . . ?
C32 C33 H37 109.5 . . ?
C32 C33 H38 109.5 . . ?
H37 C33 H38 109.5 . . ?
C32 C33 H39 109.5 . . ?
H37 C33 H39 109.5 . . ?
H38 C33 H39 109.5 . . ?
C32 C34 H40 109.5 . . ?
C32 C34 H41 109.5 . . ?
H40 C34 H41 109.5 . . ?
C32 C34 H42 109.5 . . ?
H40 C34 H42 109.5 . . ?
H41 C34 H42 109.5 . . ?
O3 C35 N3 122.5(3) . . ?
O3 C35 C42 118.5(3) . . ?
N3 C35 C42 118.9(4) . . ?
C35 N3 C39 122.6(3) . . ?
C35 N3 C36 120.2(3) . . ?
C39 N3 C36 117.0(3) . . ?
N3 C36 C37 112.5(3) . . ?
N3 C36 C38 112.9(3) . . ?
C37 C36 C38 112.3(4) . . ?
N3 C36 H52 106.1 . . ?
C37 C36 H52 106.1 . . ?
C38 C36 H52 106.1 . . ?
C36 C37 H53 109.5 . . ?
C36 C37 H54 109.5 . . ?
H53 C37 H54 109.5 . . ?
C36 C37 H55 109.5 . . ?
H53 C37 H55 109.5 . . ?
H54 C37 H55 109.5 . . ?
C36 C38 H56 109.5 . . ?
C36 C38 H57 109.5 . . ?
H56 C38 H57 109.5 . . ?
C36 C38 H58 109.5 . . ?
H56 C38 H58 109.5 . . ?
H57 C38 H58 109.5 . . ?
N3 C39 C40 110.9(3) . . ?
N3 C39 C41 112.2(4) . . ?
C40 C39 C41 112.9(4) . . ?
N3 C39 H59 106.8 . . ?
C40 C39 H59 106.8 . . ?
C41 C39 H59 106.8 . . ?
C39 C40 H60 109.5 . . ?
C39 C40 H61 109.5 . . ?
H60 C40 H61 109.5 . . ?
C39 C40 H62 109.5 . . ?
H60 C40 H62 109.5 . . ?
H61 C40 H62 109.5 . . ?
C39 C41 H63 109.5 . . ?
C39 C41 H64 109.5 . . ?
H63 C41 H64 109.5 . . ?
C39 C41 H65 109.5 . . ?
H63 C41 H65 109.5 . . ?
H64 C41 H65 109.5 . . ?
C35 C42 C45 120.3(3) . . ?
C35 C42 C47 133.8(3) . . ?
C45 C42 C47 89.3(3) . . ?
C35 C42 C43 123.5(3) . . ?
C45 C42 C43 89.3(3) . . ?
C47 C42 C43 88.3(3) . . ?
C50 C43 C48 128.0(3) . . ?
C50 C43 C44 123.6(3) . . ?
C48 C43 C44 90.0(3) . . ?
C50 C43 C42 124.8(3) . . ?
C48 C43 C42 90.1(3) . . ?
C44 C43 C42 88.8(3) . . ?
C49 C44 C45 90.2(3) . . ?
C49 C44 C43 89.9(3) . . ?
C45 C44 C43 90.9(3) . . ?
C49 C44 H66 125.0 . . ?
C45 C44 H66 125.0 . . ?
C43 C44 H66 125.0 . . ?
C42 C45 C46 90.2(3) . . ?
C42 C45 C44 91.0(3) . . ?
C46 C45 C44 89.9(3) . . ?
C42 C45 H67 125.0 . . ?
C46 C45 H67 125.0 . . ?
C44 C45 H67 125.0 . . ?
C47 C46 C45 90.3(3) . . ?
C47 C46 C49 90.8(3) . . ?
C45 C46 C49 90.2(3) . . ?
C47 C46 H68 125.0 . . ?
C45 C46 H68 125.0 . . ?
C49 C46 H68 125.0 . . ?
C46 C47 C48 89.9(3) . . ?
C46 C47 C42 90.2(3) . . ?
C48 C47 C42 91.1(3) . . ?
C46 C47 H69 125.0 . . ?
C48 C47 H69 125.0 . . ?
C42 C47 H69 125.0 . . ?
C43 C48 C49 90.3(3) . . ?
C43 C48 C47 90.6(3) . . ?
C49 C48 C47 90.0(3) . . ?
C43 C48 H70 125.1 . . ?
C49 C48 H70 125.1 . . ?
C47 C48 H70 125.1 . . ?
C62 C49 C48 120.8(3) . . ?
C62 C49 C44 124.1(3) . . ?
C48 C49 C44 89.8(3) . . ?
C62 C49 C46 131.5(3) . . ?
C48 C49 C46 89.3(3) . . ?
C44 C49 C46 89.7(3) . . ?
C55 C50 C51 117.9(4) . . ?
C55 C50 C43 121.8(4) . . ?
C51 C50 C43 120.3(4) . . ?
C52 C51 C50 121.0(4) . . ?
C52 C51 H43 119.5 . . ?
C50 C51 H43 119.5 . . ?
C51 C52 C53 121.7(4) . . ?
C51 C52 H44 119.1 . . ?
C53 C52 H44 119.1 . . ?
C54 C53 C52 116.6(4) . . ?
C54 C53 C56 122.2(4) . . ?
C52 C53 C56 121.2(4) . . ?
C53 C54 C55 122.5(4) . . ?
C53 C54 H45 118.7 . . ?
C55 C54 H45 118.7 . . ?
C54 C55 C50 120.3(4) . . ?
C54 C55 H46 119.9 . . ?
C50 C55 H46 119.9 . . ?
C61 C56 C57 117.8(4) . . ?
C61 C56 C53 120.2(4) . . ?
C57 C56 C53 122.0(3) . . ?
C56 C57 C58 120.7(4) . . ?
C56 C57 H47 119.7 . . ?
C58 C57 H47 119.7 . . ?
C59 C58 C57 120.9(4) . . ?
C59 C58 H48 119.6 . . ?
C57 C58 H48 119.6 . . ?
C58 C59 C60 119.3(4) . . ?
C58 C59 H49 120.3 . . ?
C60 C59 H49 120.3 . . ?
C61 C60 C59 119.6(4) . . ?
C61 C60 H50 120.2 . . ?
C59 C60 H50 120.2 . . ?
C60 C61 C56 121.8(4) . . ?
C60 C61 H51 119.1 . . ?
C56 C61 H51 119.1 . . ?
O4 C62 N4 122.4(3) . . ?
O4 C62 C49 118.8(3) . . ?
N4 C62 C49 118.6(3) . . ?
C62 N4 C63 123.4(3) . . ?
C62 N4 C66 119.7(3) . . ?
C63 N4 C66 116.9(3) . . ?
N4 C63 C64 111.8(4) . . ?
N4 C63 C65 110.1(4) . . ?
C64 C63 C65 113.7(4) . . ?
N4 C63 H71 107.0 . . ?
C64 C63 H71 107.0 . . ?
C65 C63 H71 107.0 . . ?
C63 C64 H72 109.5 . . ?
C63 C64 H73 109.5 . . ?
H72 C64 H73 109.5 . . ?
C63 C64 H74 109.5 . . ?
H72 C64 H74 109.5 . . ?
H73 C64 H74 109.5 . . ?
C63 C65 H75 109.5 . . ?
C63 C65 H76 109.5 . . ?
H75 C65 H76 109.5 . . ?
C63 C65 H77 109.5 . . ?
H75 C65 H77 109.5 . . ?
H76 C65 H77 109.5 . . ?
N4 C66 C68 113.2(3) . . ?
N4 C66 C67 111.5(3) . . ?
C68 C66 C67 111.4(4) . . ?
N4 C66 H78 106.8 . . ?
C68 C66 H78 106.8 . . ?
C67 C66 H78 106.8 . . ?
C66 C67 H79 109.5 . . ?
C66 C67 H80 109.5 . . ?
H79 C67 H80 109.5 . . ?
C66 C67 H81 109.5 . . ?
H79 C67 H81 109.5 . . ?
H80 C67 H81 109.5 . . ?
C66 C68 H82 109.5 . . ?
C66 C68 H83 109.5 . . ?
H82 C68 H83 109.5 . . ?
C66 C68 H84 109.5 . . ?
H82 C68 H84 109.5 . . ?
H83 C68 H84 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C5 -179.3(3) . . . . ?
C8 C1 N1 C5 3.5(5) . . . . ?
O1 C1 N1 C2 0.1(5) . . . . ?
C8 C1 N1 C2 -177.2(3) . . . . ?
C1 N1 C2 C4 64.4(4) . . . . ?
C5 N1 C2 C4 -116.3(4) . . . . ?
C1 N1 C2 C3 -63.8(5) . . . . ?
C5 N1 C2 C3 115.5(4) . . . . ?
C1 N1 C5 C6 110.6(4) . . . . ?
C2 N1 C5 C6 -68.7(4) . . . . ?
C1 N1 C5 C7 -123.7(4) . . . . ?
C2 N1 C5 C7 56.9(4) . . . . ?
O1 C1 C8 C13 6.8(5) . . . . ?
N1 C1 C8 C13 -175.8(3) . . . . ?
O1 C1 C8 C11 128.8(4) . . . . ?
N1 C1 C8 C11 -53.9(5) . . . . ?
O1 C1 C8 C9 -105.1(4) . . . . ?
N1 C1 C8 C9 72.2(5) . . . . ?
C1 C8 C9 C16 -6.2(5) . . . . ?
C13 C8 C9 C16 -132.7(4) . . . . ?
C11 C8 C9 C16 137.8(3) . . . . ?
C1 C8 C9 C10 -144.4(3) . . . . ?
C13 C8 C9 C10 89.1(3) . . . . ?
C11 C8 C9 C10 -0.5(2) . . . . ?
C1 C8 C9 C14 125.9(3) . . . . ?
C13 C8 C9 C14 -0.6(3) . . . . ?
C11 C8 C9 C14 -90.2(3) . . . . ?
C16 C9 C10 C15 133.0(4) . . . . ?
C14 C9 C10 C15 -1.5(3) . . . . ?
C8 C9 C10 C15 -90.2(3) . . . . ?
C16 C9 C10 C11 -136.4(4) . . . . ?
C14 C9 C10 C11 89.1(3) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 -90.7(3) . . . . ?
C15 C10 C11 C8 90.1(3) . . . . ?
C9 C10 C11 C8 -0.5(3) . . . . ?
C1 C8 C11 C12 -132.3(4) . . . . ?
C13 C8 C11 C12 0.3(3) . . . . ?
C9 C8 C11 C12 90.2(3) . . . . ?
C1 C8 C11 C10 137.9(4) . . . . ?
C13 C8 C11 C10 -89.4(3) . . . . ?
C9 C8 C11 C10 0.5(2) . . . . ?
C10 C11 C12 C13 90.3(3) . . . . ?
C8 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 C15 0.1(3) . . . . ?
C8 C11 C12 C15 -90.6(3) . . . . ?
C1 C8 C13 C14 -128.4(3) . . . . ?
C11 C8 C13 C14 89.8(3) . . . . ?
C9 C8 C13 C14 0.6(3) . . . . ?
C1 C8 C13 C12 141.5(3) . . . . ?
C11 C8 C13 C12 -0.3(3) . . . . ?
C9 C8 C13 C12 -89.5(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C15 C12 C13 C8 90.4(3) . . . . ?
C11 C12 C13 C14 -90.4(3) . . . . ?
C15 C12 C13 C14 -0.3(3) . . . . ?
C8 C13 C14 C15 -90.2(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C8 C13 C14 C9 -0.6(3) . . . . ?
C12 C13 C14 C9 89.8(3) . . . . ?
C16 C9 C14 C13 134.0(3) . . . . ?
C10 C9 C14 C13 -89.0(3) . . . . ?
C8 C9 C14 C13 0.6(3) . . . . ?
C16 C9 C14 C15 -135.6(3) . . . . ?
C10 C9 C14 C15 1.5(3) . . . . ?
C8 C9 C14 C15 91.1(3) . . . . ?
C9 C10 C15 C28 -134.3(3) . . . . ?
C11 C10 C15 C28 135.1(3) . . . . ?
C9 C10 C15 C14 1.5(3) . . . . ?
C11 C10 C15 C14 -89.1(3) . . . . ?
C9 C10 C15 C12 90.7(3) . . . . ?
C11 C10 C15 C12 0.1(3) . . . . ?
C13 C14 C15 C28 -140.5(4) . . . . ?
C9 C14 C15 C28 128.7(4) . . . . ?
C13 C14 C15 C10 89.2(3) . . . . ?
C9 C14 C15 C10 -1.5(3) . . . . ?
C13 C14 C15 C12 -0.3(3) . . . . ?
C9 C14 C15 C12 -91.0(3) . . . . ?
C11 C12 C15 C28 -129.6(4) . . . . ?
C13 C12 C15 C28 140.6(4) . . . . ?
C11 C12 C15 C10 -0.1(3) . . . . ?
C13 C12 C15 C10 -89.9(3) . . . . ?
C11 C12 C15 C14 90.1(3) . . . . ?
C13 C12 C15 C14 0.3(3) . . . . ?
C10 C9 C16 C17 175.3(3) . . . . ?
C14 C9 C16 C17 -64.0(5) . . . . ?
C8 C9 C16 C17 52.6(5) . . . . ?
C10 C9 C16 C21 -5.6(5) . . . . ?
C14 C9 C16 C21 115.1(4) . . . . ?
C8 C9 C16 C21 -128.4(4) . . . . ?
C21 C16 C17 C18 0.8(5) . . . . ?
C9 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C17 C18 C19 C22 178.9(3) . . . . ?
C18 C19 C20 C21 1.3(5) . . . . ?
C22 C19 C20 C21 -178.1(3) . . . . ?
C19 C20 C21 C16 -1.0(5) . . . . ?
C17 C16 C21 C20 -0.1(5) . . . . ?
C9 C16 C21 C20 -179.1(3) . . . . ?
C20 C19 C22 C23 -154.8(3) . . . . ?
C18 C19 C22 C23 25.8(5) . . . . ?
C20 C19 C22 C27 25.8(5) . . . . ?
C18 C19 C22 C27 -153.6(3) . . . . ?
C27 C22 C23 C24 1.3(5) . . . . ?
C19 C22 C23 C24 -178.1(3) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C26 -0.5(6) . . . . ?
C24 C25 C26 C27 1.0(6) . . . . ?
C25 C26 C27 C22 -0.4(5) . . . . ?
C23 C22 C27 C26 -0.8(5) . . . . ?
C19 C22 C27 C26 178.6(3) . . . . ?
C10 C15 C28 O2 -1.8(5) . . . . ?
C14 C15 C28 O2 -119.5(4) . . . . ?
C12 C15 C28 O2 114.6(4) . . . . ?
C10 C15 C28 N2 177.2(3) . . . . ?
C14 C15 C28 N2 59.6(5) . . . . ?
C12 C15 C28 N2 -66.3(5) . . . . ?
O2 C28 N2 C29 179.0(3) . . . . ?
C15 C28 N2 C29 0.0(5) . . . . ?
O2 C28 N2 C32 -1.1(5) . . . . ?
C15 C28 N2 C32 179.8(3) . . . . ?
C28 N2 C29 C30 -115.6(4) . . . . ?
C32 N2 C29 C30 64.5(4) . . . . ?
C28 N2 C29 C31 117.3(4) . . . . ?
C32 N2 C29 C31 -62.5(4) . . . . ?
C28 N2 C32 C33 -64.5(4) . . . . ?
C29 N2 C32 C33 115.4(4) . . . . ?
C28 N2 C32 C34 63.1(4) . . . . ?
C29 N2 C32 C34 -117.0(4) . . . . ?
O3 C35 N3 C39 179.4(4) . . . . ?
C42 C35 N3 C39 -2.8(5) . . . . ?
O3 C35 N3 C36 3.9(5) . . . . ?
C42 C35 N3 C36 -178.3(3) . . . . ?
C35 N3 C36 C37 -70.2(5) . . . . ?
C39 N3 C36 C37 114.0(4) . . . . ?
C35 N3 C36 C38 58.2(5) . . . . ?
C39 N3 C36 C38 -117.6(4) . . . . ?
C35 N3 C39 C40 -104.5(4) . . . . ?
C36 N3 C39 C40 71.2(4) . . . . ?
C35 N3 C39 C41 128.2(4) . . . . ?
C36 N3 C39 C41 -56.1(4) . . . . ?
O3 C35 C42 C45 -9.6(5) . . . . ?
N3 C35 C42 C45 172.6(3) . . . . ?
O3 C35 C42 C47 -132.1(4) . . . . ?
N3 C35 C42 C47 50.0(6) . . . . ?
O3 C35 C42 C43 102.1(4) . . . . ?
N3 C35 C42 C43 -75.7(5) . . . . ?
C35 C42 C43 C50 5.6(6) . . . . ?
C45 C42 C43 C50 132.2(4) . . . . ?
C47 C42 C43 C50 -138.5(4) . . . . ?
C35 C42 C43 C48 144.3(4) . . . . ?
C45 C42 C43 C48 -89.1(3) . . . . ?
C47 C42 C43 C48 0.2(3) . . . . ?
C35 C42 C43 C44 -125.7(4) . . . . ?
C45 C42 C43 C44 0.9(3) . . . . ?
C47 C42 C43 C44 90.2(3) . . . . ?
C50 C43 C44 C49 136.7(4) . . . . ?
C48 C43 C44 C49 -1.0(3) . . . . ?
C42 C43 C44 C49 -91.1(3) . . . . ?
C50 C43 C44 C45 -133.1(4) . . . . ?
C48 C43 C44 C45 89.2(3) . . . . ?
C42 C43 C44 C45 -0.9(3) . . . . ?
C35 C42 C45 C46 -141.7(4) . . . . ?
C47 C42 C45 C46 0.8(3) . . . . ?
C43 C42 C45 C46 89.1(3) . . . . ?
C35 C42 C45 C44 128.3(3) . . . . ?
C47 C42 C45 C44 -89.2(3) . . . . ?
C43 C42 C45 C44 -0.9(3) . . . . ?
C49 C44 C45 C42 90.8(3) . . . . ?
C43 C44 C45 C42 0.9(3) . . . . ?
C49 C44 C45 C46 0.6(3) . . . . ?
C43 C44 C45 C46 -89.3(3) . . . . ?
C42 C45 C46 C47 -0.8(3) . . . . ?
C44 C45 C46 C47 90.2(3) . . . . ?
C42 C45 C46 C49 -91.6(3) . . . . ?
C44 C45 C46 C49 -0.6(3) . . . . ?
C45 C46 C47 C48 -90.3(3) . . . . ?
C49 C46 C47 C48 -0.1(3) . . . . ?
C45 C46 C47 C42 0.8(3) . . . . ?
C49 C46 C47 C42 91.0(3) . . . . ?
C35 C42 C47 C46 132.5(4) . . . . ?
C45 C42 C47 C46 -0.8(3) . . . . ?
C43 C42 C47 C46 -90.1(3) . . . . ?
C35 C42 C47 C48 -137.6(4) . . . . ?
C45 C42 C47 C48 89.1(3) . . . . ?
C43 C42 C47 C48 -0.2(3) . . . . ?
C50 C43 C48 C49 -133.6(4) . . . . ?
C44 C43 C48 C49 1.0(3) . . . . ?
C42 C43 C48 C49 89.8(3) . . . . ?
C50 C43 C48 C47 136.4(4) . . . . ?
C44 C43 C48 C47 -89.0(3) . . . . ?
C42 C43 C48 C47 -0.2(3) . . . . ?
C46 C47 C48 C43 90.4(3) . . . . ?
C42 C47 C48 C43 0.2(3) . . . . ?
C46 C47 C48 C49 0.1(3) . . . . ?
C42 C47 C48 C49 -90.1(3) . . . . ?
C43 C48 C49 C62 129.5(4) . . . . ?
C47 C48 C49 C62 -139.9(4) . . . . ?
C43 C48 C49 C44 -1.0(3) . . . . ?
C47 C48 C49 C44 89.6(3) . . . . ?
C43 C48 C49 C46 -90.7(3) . . . . ?
C47 C48 C49 C46 -0.1(3) . . . . ?
C45 C44 C49 C62 142.1(4) . . . . ?
C43 C44 C49 C62 -126.9(4) . . . . ?
C45 C44 C49 C48 -89.9(3) . . . . ?
C43 C44 C49 C48 1.0(3) . . . . ?
C45 C44 C49 C46 -0.6(3) . . . . ?
C43 C44 C49 C46 90.3(3) . . . . ?
C47 C46 C49 C62 132.3(4) . . . . ?
C45 C46 C49 C62 -137.4(4) . . . . ?
C47 C46 C49 C48 0.1(3) . . . . ?
C45 C46 C49 C48 90.4(3) . . . . ?
C47 C46 C49 C44 -89.6(3) . . . . ?
C45 C46 C49 C44 0.6(3) . . . . ?
C48 C43 C50 C55 -6.7(6) . . . . ?
C44 C43 C50 C55 -128.0(4) . . . . ?
C42 C43 C50 C55 116.4(4) . . . . ?
C48 C43 C50 C51 173.2(4) . . . . ?
C44 C43 C50 C51 51.9(5) . . . . ?
C42 C43 C50 C51 -63.7(5) . . . . ?
C55 C50 C51 C52 0.2(6) . . . . ?
C43 C50 C51 C52 -179.7(4) . . . . ?
C50 C51 C52 C53 -1.2(6) . . . . ?
C51 C52 C53 C54 1.5(6) . . . . ?
C51 C52 C53 C56 -178.7(4) . . . . ?
C52 C53 C54 C55 -0.8(6) . . . . ?
C56 C53 C54 C55 179.4(3) . . . . ?
C53 C54 C55 C50 -0.2(6) . . . . ?
C51 C50 C55 C54 0.5(6) . . . . ?
C43 C50 C55 C54 -179.7(4) . . . . ?
C54 C53 C56 C61 -24.0(5) . . . . ?
C52 C53 C56 C61 156.2(4) . . . . ?
C54 C53 C56 C57 157.6(4) . . . . ?
C52 C53 C56 C57 -22.2(5) . . . . ?
C61 C56 C57 C58 -1.4(5) . . . . ?
C53 C56 C57 C58 177.1(4) . . . . ?
C56 C57 C58 C59 1.0(6) . . . . ?
C57 C58 C59 C60 0.0(6) . . . . ?
C58 C59 C60 C61 -0.5(6) . . . . ?
C59 C60 C61 C56 0.1(6) . . . . ?
C57 C56 C61 C60 0.9(6) . . . . ?
C53 C56 C61 C60 -177.6(4) . . . . ?
C48 C49 C62 O4 -4.3(6) . . . . ?
C44 C49 C62 O4 109.1(4) . . . . ?
C46 C49 C62 O4 -124.8(5) . . . . ?
C48 C49 C62 N4 -178.1(3) . . . . ?
C44 C49 C62 N4 -64.7(5) . . . . ?
C46 C49 C62 N4 61.4(6) . . . . ?
O4 C62 N4 C63 178.5(4) . . . . ?
C49 C62 N4 C63 -7.9(6) . . . . ?
O4 C62 N4 C66 -0.8(6) . . . . ?
C49 C62 N4 C66 172.7(3) . . . . ?
C62 N4 C63 C64 116.3(4) . . . . ?
C66 N4 C63 C64 -64.4(5) . . . . ?
C62 N4 C63 C65 -116.3(4) . . . . ?
C66 N4 C63 C65 63.0(5) . . . . ?
C62 N4 C66 C68 64.8(5) . . . . ?
C63 N4 C66 C68 -114.6(4) . . . . ?
C62 N4 C66 C67 -61.8(5) . . . . ?
C63 N4 C66 C67 118.8(4) . . . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.059



_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration unk
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1993516'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_audit_creation_date             2020-02-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.11.21 svn.r41b79517 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H29 F9 N2 O, C6 H6'
_chemical_formula_sum            'C43 H35 F9 N2 O'
_chemical_formula_weight         766.73
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.75710(10)
_cell_length_b                   10.10370(10)
_cell_length_c                   19.2300(3)
_cell_angle_alpha                86.6000(10)
_cell_angle_beta                 88.6120(10)
_cell_angle_gamma                81.4120(10)
_cell_volume                     1870.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19760
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.6980
_cell_measurement_theta_min      2.8570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            37233
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.766
_diffrn_reflns_theta_min         2.348
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   0.50    5.00    --  -13.00  45.00 264.00  360
  2  ω   -103.00  60.00   0.50    5.00    --  -13.00  45.00 122.00  326
  3  ω    -86.00  45.00   0.50    5.00    --  -13.00  45.00 158.00  262
  4  ω     16.00  61.00   0.50    5.00    --  -13.00  45.00 193.00   90
  5  ω      4.50  63.00   0.50    5.00    --  -13.00  45.00  16.00  117
  6  ω   -103.00  58.50   0.50    5.00    --  -13.00  45.00 -19.00  323
  7  ω    -71.00 -25.00   0.50    5.00    --  -13.00  45.00  51.00   92
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0564128000
_diffrn_orient_matrix_UB_12      0.0248757000
_diffrn_orient_matrix_UB_13      0.0218754000
_diffrn_orient_matrix_UB_21      0.0439861000
_diffrn_orient_matrix_UB_22      -0.0111114000
_diffrn_orient_matrix_UB_23      0.0292552000
_diffrn_orient_matrix_UB_31      0.0170087000
_diffrn_orient_matrix_UB_32      0.0656849000
_diffrn_orient_matrix_UB_33      -0.0055894000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7619
_reflns_number_total             9620
_reflns_odcompleteness_completeness 90.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.70
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         9620
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.6829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F7A-F9A
 2.2 with sigma of 0.01
 F9A-F8A
 2.2 with sigma of 0.01
 F8A-F7A
 2.2 with sigma of 0.01
 F9-C25 = F8A-C25 = F8-C25 = F7A-C25 = F7-C25 = F9A-C25
 1.35 with sigma of 0.01
 F9-F8
 2.2 with sigma of 0.01
 F8-F7
 2.2 with sigma of 0.01
 F7-F9
 2.2 with sigma of 0.01
 C51A-C50A = C55A-C50A = C55A-C54A = C54A-C53A = C53A-C52A = C52A-C51A
 1.39 with sigma of 0.01
 C55A-C53A
 2.42 with sigma of 0.01
 C53A-C51A
 2.42 with sigma of 0.01
 C55A-C51A
 2.42 with sigma of 0.01
 C50A-C52A
 2.42 with sigma of 0.01
 C52A-C54A
 2.42 with sigma of 0.01
 C54A-C50A
 2.42 with sigma of 0.01
 C52-C51 = C51-C50 = C55-C50 = C55-C54 = C54-C53 = C53-C52
 1.39 with sigma of 0.01
 C55-C51
 2.42 with sigma of 0.01
 C51-C53
 2.42 with sigma of 0.01
 C53-C55
 2.42 with sigma of 0.01
 C50-C54
 2.42 with sigma of 0.01
 C54-C52
 2.42 with sigma of 0.01
 C52-C50
 2.42 with sigma of 0.01
3. Restrained planarity
 C50A, C55A, C54A, C53A, C52A, C51A
 with sigma of 0.02
 C50, C51, C55, C52, C53, C54
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(F8A) \\sim Ueq, Uanis(F7A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
5. Others
 Sof(F8A)=Sof(F7A)=Sof(F9A)=1-FVAR(1)
 Sof(F7)=Sof(F9)=Sof(F8)=FVAR(1)
 Sof(C50A)=Sof(H50A)=Sof(C55A)=Sof(H55A)=Sof(C54A)=Sof(H54A)=Sof(C53A)=
 Sof(H53A)=Sof(C52A)=Sof(H52A)=Sof(C51A)=Sof(H51A)=1-FVAR(2)
 Sof(C50)=Sof(H50)=Sof(C51)=Sof(H51)=Sof(C55)=Sof(H55)=Sof(C52)=Sof(H52)=
 Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C2(H2), C6(H6), C41(H41), C43(H43)
6.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14), C30(H30), C24(H24), C23(H23), C11(H11),
 C31(H31), C20(H20), C34(H34), C33(H33), C21(H21), C50(H50), C51(H51), C55(H55),
  C52(H52), C53(H53), C54(H54), C50A(H50A), C55A(H55A), C54A(H54A), C53A(H53A),
 C52A(H52A), C51A(H51A)
6.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C42(H42A,H42B,H42C), C45(H45A,H45B,H45C), C44(H44A,H44B,
 H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O47 O 0.52715(10) 0.21514(10) 0.19373(6) 0.0324(2) Uani 1 1 d . . . . .
F1 F 1.34938(10) 0.29869(12) 0.01521(6) 0.0531(3) Uani 1 1 d . . . . .
F4 F 0.28107(11) -0.26556(11) 0.04504(7) 0.0619(4) Uani 1 1 d . . . . .
N40 N 0.66464(11) 0.36318(11) 0.22397(6) 0.0236(2) Uani 1 1 d . . . . .
F2 F 1.17960(13) 0.32002(15) -0.05274(5) 0.0696(4) Uani 1 1 d . . . . .
F3 F 1.19739(15) 0.47037(11) 0.01888(8) 0.0798(5) Uani 1 1 d . . . . .
F6 F 0.17619(14) -0.07003(12) 0.05346(8) 0.0803(5) Uani 1 1 d . . . . .
F7 F 0.5842(8) 0.4546(3) 0.5722(2) 0.0726(13) Uani 0.691(13) 1 d D . P A 1
F9 F 0.6524(4) 0.2677(5) 0.62407(16) 0.0635(10) Uani 0.691(13) 1 d D . P A 1
F8 F 0.4499(3) 0.3076(6) 0.5859(2) 0.0597(11) Uani 0.691(13) 1 d D . P A 1
F5 F 0.14875(13) -0.2193(2) 0.13244(8) 0.0944(5) Uani 1 1 d . . . . .
C9 C 0.97834(13) 0.14491(12) 0.16609(6) 0.0206(2) Uani 1 1 d . . . . .
C39 C 0.63621(13) 0.23761(13) 0.21793(6) 0.0214(2) Uani 1 1 d . . . . .
N49 N 1.06145(15) -0.33007(14) 0.32992(8) 0.0423(3) Uani 1 1 d . . . . .
C19 C 0.73366(13) 0.14618(13) 0.38250(6) 0.0210(2) Uani 1 1 d . . . . .
C7 C 0.70952(13) -0.03113(12) 0.23159(6) 0.0203(2) Uani 1 1 d . . . . .
C29 C 0.58915(13) -0.06950(12) 0.19620(7) 0.0216(2) Uani 1 1 d . . . . .
C5 C 0.78325(12) 0.07334(13) 0.31984(6) 0.0201(2) Uani 1 1 d . . . . .
C4 C 0.93674(13) 0.03166(13) 0.29544(7) 0.0213(2) Uani 1 1 d . . . . .
H4 H 1.018389 0.053299 0.318531 0.026 Uiso 1 1 calc R U . . .
C10 C 1.11351(13) 0.16309(14) 0.17928(7) 0.0243(3) Uani 1 1 d . . . . .
H10 H 1.152074 0.133581 0.222231 0.029 Uiso 1 1 calc R U . . .
C2 C 0.86340(13) -0.07154(13) 0.20761(7) 0.0218(2) Uani 1 1 d . . . . .
H2 H 0.893179 -0.124249 0.167316 0.026 Uiso 1 1 calc R U . . .
C6 C 0.75074(13) -0.07156(13) 0.30877(7) 0.0215(2) Uani 1 1 d . . . . .
H6 H 0.699035 -0.123915 0.341731 0.026 Uiso 1 1 calc R U . . .
C3 C 0.90560(13) -0.11401(13) 0.28503(7) 0.0226(3) Uani 1 1 d . . . . .
C12 C 1.13310(14) 0.26908(13) 0.06578(7) 0.0248(3) Uani 1 1 d . . . . .
C13 C 0.99824(14) 0.25165(14) 0.05155(7) 0.0264(3) Uani 1 1 d . . . . .
H13 H 0.959838 0.281626 0.008627 0.032 Uiso 1 1 calc R U . . .
C8 C 0.73940(12) 0.11736(12) 0.24173(6) 0.0190(2) Uani 1 1 d . . . . .
C1 C 0.89663(12) 0.07369(12) 0.21800(6) 0.0200(2) Uani 1 1 d . . . . .
C14 C 0.92111(13) 0.18938(14) 0.10160(7) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.830938 0.177248 0.092119 0.030 Uiso 1 1 calc R U . . .
C30 C 0.47685(14) -0.10676(14) 0.23416(7) 0.0269(3) Uani 1 1 d . . . . .
H30 H 0.477577 -0.109081 0.282575 0.032 Uiso 1 1 calc R U . . .
C24 C 0.82405(13) 0.18511(14) 0.42951(7) 0.0245(3) Uani 1 1 d . . . . .
H24 H 0.919037 0.170775 0.420514 0.029 Uiso 1 1 calc R U . . .
C23 C 0.77308(14) 0.24526(14) 0.48977(7) 0.0269(3) Uani 1 1 d . . . . .
H23 H 0.833803 0.270524 0.521309 0.032 Uiso 1 1 calc R U . . .
C22 C 0.63150(14) 0.26759(14) 0.50284(7) 0.0263(3) Uani 1 1 d . . . . .
C11 C 1.19201(14) 0.22469(14) 0.12931(7) 0.0265(3) Uani 1 1 d . . . . .
H11 H 1.282626 0.235878 0.138419 0.032 Uiso 1 1 calc R U . . .
C41 C 0.78951(14) 0.39557(14) 0.25720(7) 0.0253(3) Uani 1 1 d . . . . .
H41 H 0.846760 0.310712 0.271631 0.030 Uiso 1 1 calc R U . . .
C32 C 0.36269(14) -0.13750(14) 0.12892(8) 0.0296(3) Uani 1 1 d . . . . .
C48 C 0.99278(14) -0.23502(14) 0.30904(7) 0.0279(3) Uani 1 1 d . . . . .
C31 C 0.36350(14) -0.14061(15) 0.20074(8) 0.0308(3) Uani 1 1 d . . . . .
H31 H 0.288598 -0.165222 0.226581 0.037 Uiso 1 1 calc R U . . .
C20 C 0.59147(14) 0.17209(15) 0.39569(7) 0.0289(3) Uani 1 1 d . . . . .
H20 H 0.530277 0.148439 0.363899 0.035 Uiso 1 1 calc R U . . .
C34 C 0.58740(15) -0.06894(15) 0.12394(7) 0.0301(3) Uani 1 1 d . . . . .
H34 H 0.662816 -0.046011 0.097915 0.036 Uiso 1 1 calc R U . . .
C43 C 0.56184(15) 0.47802(14) 0.19766(8) 0.0309(3) Uani 1 1 d . . . . .
H43 H 0.599699 0.559628 0.207012 0.037 Uiso 1 1 calc R U . . .
C33 C 0.47448(16) -0.10220(16) 0.09035(8) 0.0333(3) Uani 1 1 d . . . . .
H33 H 0.473761 -0.100809 0.041956 0.040 Uiso 1 1 calc R U . . .
C25 C 0.57776(16) 0.32784(16) 0.56916(8) 0.0349(3) Uani 1 1 d D . . . .
C21 C 0.54025(14) 0.23272(16) 0.45563(8) 0.0311(3) Uani 1 1 d . . . . .
H21 H 0.445175 0.249848 0.464074 0.037 Uiso 1 1 calc R U . . .
C46 C 0.87677(16) 0.47329(15) 0.20699(8) 0.0325(3) Uani 1 1 d . . . . .
H46A H 0.895966 0.425933 0.165192 0.049 Uiso 1 1 calc R U . . .
H46B H 0.962396 0.481870 0.228638 0.049 Uiso 1 1 calc R U . . .
H46C H 0.826665 0.560807 0.195651 0.049 Uiso 1 1 calc R U . . .
C42 C 0.75164(17) 0.47329(15) 0.32258(8) 0.0330(3) Uani 1 1 d . . . . .
H42A H 0.704723 0.561301 0.309438 0.050 Uiso 1 1 calc R U . . .
H42B H 0.834531 0.480644 0.347050 0.050 Uiso 1 1 calc R U . . .
H42C H 0.691903 0.426667 0.352277 0.050 Uiso 1 1 calc R U . . .
C15 C 1.21371(16) 0.33969(16) 0.01201(8) 0.0340(3) Uani 1 1 d . . . . .
C35 C 0.24229(16) -0.17319(17) 0.09082(10) 0.0411(4) Uani 1 1 d . . . . .
C45 C 0.54781(18) 0.47847(17) 0.11920(9) 0.0422(4) Uani 1 1 d . . . . .
H45A H 0.637884 0.473648 0.097447 0.063 Uiso 1 1 calc R U . . .
H45B H 0.490669 0.559488 0.102838 0.063 Uiso 1 1 calc R U . . .
H45C H 0.506004 0.402552 0.107698 0.063 Uiso 1 1 calc R U . . .
C44 C 0.42384(17) 0.48529(16) 0.23699(10) 0.0411(4) Uani 1 1 d . . . . .
H44A H 0.379132 0.410693 0.226298 0.062 Uiso 1 1 calc R U . . .
H44B H 0.365672 0.567485 0.223309 0.062 Uiso 1 1 calc R U . . .
H44C H 0.439708 0.482275 0.286175 0.062 Uiso 1 1 calc R U . . .
C50 C 0.8578(15) 0.6299(13) 0.5510(8) 0.040(3) Uani 0.343(17) 1 d D . P B 2
H50 H 0.890075 0.543639 0.537682 0.048 Uiso 0.343(17) 1 calc R U P B 2
C51 C 0.8499(14) 0.737(2) 0.5023(5) 0.049(4) Uani 0.343(17) 1 d D . P B 2
H51 H 0.876406 0.723164 0.456185 0.058 Uiso 0.343(17) 1 calc R U P B 2
C55 C 0.8177(15) 0.6508(12) 0.6195(7) 0.042(3) Uani 0.343(17) 1 d D . P B 2
H55 H 0.823545 0.578559 0.652160 0.051 Uiso 0.343(17) 1 calc R U P B 2
C52 C 0.8027(15) 0.8651(16) 0.5223(9) 0.053(4) Uani 0.343(17) 1 d D . P B 2
H52 H 0.798231 0.937299 0.489739 0.064 Uiso 0.343(17) 1 calc R U P B 2
C53 C 0.7618(14) 0.8867(10) 0.5908(11) 0.048(4) Uani 0.343(17) 1 d D . P B 2
H53 H 0.729838 0.973150 0.603986 0.058 Uiso 0.343(17) 1 calc R U P B 2
C54 C 0.7686(13) 0.7793(16) 0.6397(6) 0.039(2) Uani 0.343(17) 1 d D . P B 2
H54 H 0.740642 0.793209 0.685609 0.047 Uiso 0.343(17) 1 calc R U P B 2
F8A F 0.6059(16) 0.2536(7) 0.6245(4) 0.078(3) Uani 0.309(13) 1 d D U P A 2
F7A F 0.4384(6) 0.3703(16) 0.5647(6) 0.079(3) Uani 0.309(13) 1 d D U P A 2
F9A F 0.6286(11) 0.4429(8) 0.5752(6) 0.065(3) Uani 0.309(13) 1 d D . P A 2
C50A C 0.8686(7) 0.6970(8) 0.5065(3) 0.0348(13) Uani 0.657(17) 1 d D . P B 1
H50A H 0.901382 0.654167 0.466620 0.042 Uiso 0.657(17) 1 calc R U P B 1
C55A C 0.8613(8) 0.6236(6) 0.5690(5) 0.0401(16) Uani 0.657(17) 1 d D . P B 1
H55A H 0.889368 0.531365 0.571058 0.048 Uiso 0.657(17) 1 calc R U P B 1
C54A C 0.8130(7) 0.6860(9) 0.6278(3) 0.0408(17) Uani 0.657(17) 1 d D . P B 1
H54A H 0.808742 0.636400 0.669933 0.049 Uiso 0.657(17) 1 calc R U P B 1
C53A C 0.7706(5) 0.8223(10) 0.6245(3) 0.0391(16) Uani 0.657(17) 1 d D . P B 1
H53A H 0.735857 0.864227 0.664332 0.047 Uiso 0.657(17) 1 calc R U P B 1
C52A C 0.7790(7) 0.8974(5) 0.5629(5) 0.0404(15) Uani 0.657(17) 1 d D . P B 1
H52A H 0.752623 0.989803 0.561160 0.048 Uiso 0.657(17) 1 calc R U P B 1
C51A C 0.8274(8) 0.8332(7) 0.5033(3) 0.0355(12) Uani 0.657(17) 1 d D . P B 1
H51A H 0.831986 0.882539 0.461086 0.043 Uiso 0.657(17) 1 calc R U P B 1


_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
O47 C39 1.2285(16) . ?
F1 C15 1.3285(19) . ?
F4 C35 1.3285(19) . ?
N40 C39 1.3507(17) . ?
N40 C41 1.4769(17) . ?
N40 C43 1.4885(17) . ?
F2 C15 1.3303(19) . ?
F3 C15 1.3203(19) . ?
F6 C35 1.323(2) . ?
F7 C25 1.296(3) . ?
F9 C25 1.358(3) . ?
F8 C25 1.324(3) . ?
F5 C35 1.319(2) . ?
C9 C10 1.3898(17) . ?
C9 C1 1.4823(17) . ?
C9 C14 1.3944(18) . ?
C39 C8 1.5134(17) . ?
N49 C48 1.1435(19) . ?
C19 C5 1.4825(17) . ?
C19 C24 1.3908(17) . ?
C19 C20 1.3928(18) . ?
C7 C29 1.4828(17) . ?
C7 C2 1.5618(17) . ?
C7 C6 1.5619(17) . ?
C7 C8 1.5944(17) . ?
C29 C30 1.3882(19) . ?
C29 C34 1.3899(19) . ?
C5 C4 1.5626(17) . ?
C5 C6 1.5711(17) . ?
C5 C8 1.5914(17) . ?
C4 H4 0.9800 . ?
C4 C3 1.5716(18) . ?
C4 C1 1.5666(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3905(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.5719(18) . ?
C2 C1 1.5742(17) . ?
C6 H6 0.9800 . ?
C6 C3 1.5722(18) . ?
C3 C48 1.4398(18) . ?
C12 C13 1.3891(19) . ?
C12 C11 1.3842(19) . ?
C12 C15 1.4958(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.3867(19) . ?
C8 C1 1.5951(17) . ?
C14 H14 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.3881(19) . ?
C24 H24 0.9300 . ?
C24 C23 1.3874(19) . ?
C23 H23 0.9300 . ?
C23 C22 1.3853(19) . ?
C22 C25 1.4954(19) . ?
C22 C21 1.3826(19) . ?
C11 H11 0.9300 . ?
C41 H41 0.9800 . ?
C41 C46 1.5309(19) . ?
C41 C42 1.5304(19) . ?
C32 C31 1.380(2) . ?
C32 C33 1.383(2) . ?
C32 C35 1.4988(19) . ?
C31 H31 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.3851(19) . ?
C34 H34 0.9300 . ?
C34 C33 1.384(2) . ?
C43 H43 0.9800 . ?
C43 C45 1.518(2) . ?
C43 C44 1.523(2) . ?
C33 H33 0.9300 . ?
C25 F8A 1.276(6) . ?
C25 F7A 1.366(6) . ?
C25 F9A 1.343(6) . ?
C21 H21 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C50 H50 0.9300 . ?
C50 C51 1.385(8) . ?
C50 C55 1.385(8) . ?
C51 H51 0.9300 . ?
C51 C52 1.380(8) . ?
C55 H55 0.9300 . ?
C55 C54 1.389(8) . ?
C52 H52 0.9300 . ?
C52 C53 1.387(7) . ?
C53 H53 0.9300 . ?
C53 C54 1.388(7) . ?
C54 H54 0.9300 . ?
C50A H50A 0.9300 . ?
C50A C55A 1.379(6) . ?
C50A C51A 1.373(6) . ?
C55A H55A 0.9300 . ?
C55A C54A 1.367(6) . ?
C54A H54A 0.9300 . ?
C54A C53A 1.376(6) . ?
C53A H53A 0.9300 . ?
C53A C52A 1.376(5) . ?
C52A H52A 0.9300 . ?
C52A C51A 1.388(5) . ?
C51A H51A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C39 N40 C41 124.50(11) . . ?
C39 N40 C43 118.42(11) . . ?
C41 N40 C43 117.05(11) . . ?
C10 C9 C1 121.19(11) . . ?
C10 C9 C14 119.19(12) . . ?
C14 C9 C1 119.56(11) . . ?
O47 C39 N40 122.48(12) . . ?
O47 C39 C8 117.05(11) . . ?
N40 C39 C8 120.47(11) . . ?
C24 C19 C5 122.34(11) . . ?
C24 C19 C20 119.14(12) . . ?
C20 C19 C5 118.47(11) . . ?
C29 C7 C2 123.89(11) . . ?
C29 C7 C6 125.42(11) . . ?
C29 C7 C8 126.68(10) . . ?
C2 C7 C6 90.12(9) . . ?
C2 C7 C8 89.72(9) . . ?
C6 C7 C8 89.87(9) . . ?
C30 C29 C7 121.03(12) . . ?
C30 C29 C34 118.82(12) . . ?
C34 C29 C7 120.15(12) . . ?
C19 C5 C4 127.38(10) . . ?
C19 C5 C6 121.88(10) . . ?
C19 C5 C8 125.90(11) . . ?
C4 C5 C6 90.56(9) . . ?
C4 C5 C8 90.49(9) . . ?
C6 C5 C8 89.65(9) . . ?
C5 C4 H4 125.1 . . ?
C5 C4 C3 89.79(9) . . ?
C5 C4 C1 90.69(9) . . ?
C3 C4 H4 125.1 . . ?
C1 C4 H4 125.1 . . ?
C1 C4 C3 90.08(9) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.07(12) . . ?
C11 C10 H10 119.5 . . ?
C7 C2 H2 124.9 . . ?
C7 C2 C3 90.26(9) . . ?
C7 C2 C1 91.48(9) . . ?
C3 C2 H2 124.9 . . ?
C3 C2 C1 89.80(9) . . ?
C1 C2 H2 124.9 . . ?
C7 C6 C5 91.20(9) . . ?
C7 C6 H6 125.0 . . ?
C7 C6 C3 90.24(9) . . ?
C5 C6 H6 125.0 . . ?
C5 C6 C3 89.46(9) . . ?
C3 C6 H6 125.0 . . ?
C4 C3 C2 90.01(9) . . ?
C4 C3 C6 90.19(9) . . ?
C2 C3 C6 89.38(9) . . ?
C48 C3 C4 124.56(11) . . ?
C48 C3 C2 126.56(12) . . ?
C48 C3 C6 124.97(11) . . ?
C13 C12 C15 119.13(12) . . ?
C11 C12 C13 120.88(12) . . ?
C11 C12 C15 119.98(12) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.74(12) . . ?
C14 C13 H13 120.1 . . ?
C39 C8 C7 120.72(10) . . ?
C39 C8 C5 126.58(10) . . ?
C39 C8 C1 130.07(10) . . ?
C7 C8 C1 89.53(9) . . ?
C5 C8 C7 89.28(9) . . ?
C5 C8 C1 88.62(9) . . ?
C9 C1 C4 126.48(10) . . ?
C9 C1 C2 122.16(10) . . ?
C9 C1 C8 127.33(10) . . ?
C4 C1 C2 90.11(9) . . ?
C4 C1 C8 90.20(9) . . ?
C2 C1 C8 89.26(9) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.20(12) . . ?
C13 C14 H14 119.9 . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.79(13) . . ?
C31 C30 H30 119.6 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.26(12) . . ?
C23 C24 H24 119.9 . . ?
C24 C23 H23 120.1 . . ?
C22 C23 C24 119.83(12) . . ?
C22 C23 H23 120.1 . . ?
C23 C22 C25 119.47(12) . . ?
C21 C22 C23 120.52(12) . . ?
C21 C22 C25 120.00(13) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.93(12) . . ?
C12 C11 H11 120.5 . . ?
N40 C41 H41 107.6 . . ?
N40 C41 C46 112.29(11) . . ?
N40 C41 C42 111.29(11) . . ?
C46 C41 H41 107.6 . . ?
C42 C41 H41 107.6 . . ?
C42 C41 C46 110.16(11) . . ?
C31 C32 C33 120.37(13) . . ?
C31 C32 C35 121.24(14) . . ?
C33 C32 C35 118.39(14) . . ?
N49 C48 C3 178.14(16) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 C30 119.56(13) . . ?
C32 C31 H31 120.2 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.70(12) . . ?
C21 C20 H20 119.6 . . ?
C29 C34 H34 119.7 . . ?
C33 C34 C29 120.61(13) . . ?
C33 C34 H34 119.7 . . ?
N40 C43 H43 106.5 . . ?
N40 C43 C45 111.16(12) . . ?
N40 C43 C44 112.21(12) . . ?
C45 C43 H43 106.5 . . ?
C45 C43 C44 113.42(14) . . ?
C44 C43 H43 106.5 . . ?
C32 C33 C34 119.83(13) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
F7 C25 F9 105.0(3) . . ?
F7 C25 F8 108.3(3) . . ?
F7 C25 C22 115.2(2) . . ?
F9 C25 C22 110.5(2) . . ?
F8 C25 F9 103.0(2) . . ?
F8 C25 C22 113.75(17) . . ?
F8A C25 C22 115.3(4) . . ?
F8A C25 F7A 110.8(4) . . ?
F8A C25 F9A 108.3(6) . . ?
F7A C25 C22 110.0(4) . . ?
F9A C25 C22 109.1(5) . . ?
F9A C25 F7A 102.5(5) . . ?
C22 C21 C20 119.51(13) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C41 C46 H46A 109.5 . . ?
C41 C46 H46B 109.5 . . ?
C41 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
F1 C15 F2 105.23(13) . . ?
F1 C15 C12 112.81(13) . . ?
F2 C15 C12 112.74(13) . . ?
F3 C15 F1 105.65(13) . . ?
F3 C15 F2 107.57(15) . . ?
F3 C15 C12 112.29(13) . . ?
F4 C35 C32 112.38(12) . . ?
F6 C35 F4 104.59(15) . . ?
F6 C35 C32 112.59(14) . . ?
F5 C35 F4 106.82(15) . . ?
F5 C35 F6 106.54(16) . . ?
F5 C35 C32 113.29(15) . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C51 C50 H50 119.9 . . ?
C55 C50 H50 119.9 . . ?
C55 C50 C51 120.1(6) . . ?
C50 C51 H51 120.1 . . ?
C52 C51 C50 119.7(6) . . ?
C52 C51 H51 120.1 . . ?
C50 C55 H55 119.9 . . ?
C50 C55 C54 120.3(6) . . ?
C54 C55 H55 119.9 . . ?
C51 C52 H52 119.8 . . ?
C51 C52 C53 120.5(6) . . ?
C53 C52 H52 119.8 . . ?
C52 C53 H53 120.0 . . ?
C52 C53 C54 120.0(6) . . ?
C54 C53 H53 120.0 . . ?
C55 C54 H54 120.3 . . ?
C53 C54 C55 119.5(7) . . ?
C53 C54 H54 120.3 . . ?
C55A C50A H50A 120.0 . . ?
C51A C50A H50A 120.0 . . ?
C51A C50A C55A 120.1(4) . . ?
C50A C55A H55A 119.9 . . ?
C54A C55A C50A 120.2(4) . . ?
C54A C55A H55A 119.9 . . ?
C55A C54A H54A 120.1 . . ?
C55A C54A C53A 119.8(4) . . ?
C53A C54A H54A 120.1 . . ?
C54A C53A H53A 119.6 . . ?
C52A C53A C54A 120.8(4) . . ?
C52A C53A H53A 119.6 . . ?
C53A C52A H52A 120.4 . . ?
C53A C52A C51A 119.1(4) . . ?
C51A C52A H52A 120.4 . . ?
C50A C51A C52A 120.0(4) . . ?
C50A C51A H51A 120.0 . . ?
C52A C51A H51A 120.0 . . ?

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
O47 C39 C8 C7 3.22(17) . . . . ?
O47 C39 C8 C5 -111.79(14) . . . . ?
O47 C39 C8 C1 122.39(14) . . . . ?
N40 C39 C8 C7 -177.20(11) . . . . ?
N40 C39 C8 C5 67.79(17) . . . . ?
N40 C39 C8 C1 -58.03(18) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C39 N40 C41 C46 120.44(14) . . . . ?
C39 N40 C41 C42 -115.55(14) . . . . ?
C39 N40 C43 C45 -65.04(16) . . . . ?
C39 N40 C43 C44 63.16(17) . . . . ?
C39 C8 C1 C9 0.6(2) . . . . ?
C39 C8 C1 C4 139.18(13) . . . . ?
C39 C8 C1 C2 -130.71(13) . . . . ?
C19 C5 C4 C3 131.63(13) . . . . ?
C19 C5 C4 C1 -138.29(13) . . . . ?
C19 C5 C6 C7 134.23(11) . . . . ?
C19 C5 C6 C3 -135.54(11) . . . . ?
C19 C5 C8 C39 -2.38(19) . . . . ?
C19 C5 C8 C7 -131.20(12) . . . . ?
C19 C5 C8 C1 139.26(12) . . . . ?
C19 C24 C23 C22 -0.5(2) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C7 C29 C30 C31 179.01(12) . . . . ?
C7 C29 C34 C33 -178.81(13) . . . . ?
C7 C2 C3 C4 -90.78(9) . . . . ?
C7 C2 C3 C6 -0.59(9) . . . . ?
C7 C2 C3 C48 134.28(13) . . . . ?
C7 C2 C1 C9 -135.75(11) . . . . ?
C7 C2 C1 C4 89.54(9) . . . . ?
C7 C2 C1 C8 -0.66(9) . . . . ?
C7 C6 C3 C4 90.60(9) . . . . ?
C7 C6 C3 C2 0.59(9) . . . . ?
C7 C6 C3 C48 -135.41(13) . . . . ?
C7 C8 C1 C9 131.92(12) . . . . ?
C7 C8 C1 C4 -89.46(9) . . . . ?
C7 C8 C1 C2 0.64(9) . . . . ?
C29 C7 C2 C3 -133.79(12) . . . . ?
C29 C7 C2 C1 136.40(12) . . . . ?
C29 C7 C6 C5 -137.84(12) . . . . ?
C29 C7 C6 C3 132.69(12) . . . . ?
C29 C7 C8 C39 3.67(18) . . . . ?
C29 C7 C8 C5 136.97(12) . . . . ?
C29 C7 C8 C1 -134.41(12) . . . . ?
C29 C30 C31 C32 0.2(2) . . . . ?
C29 C34 C33 C32 -0.6(2) . . . . ?
C5 C19 C24 C23 -175.76(12) . . . . ?
C5 C19 C20 C21 176.16(13) . . . . ?
C5 C4 C3 C2 89.98(9) . . . . ?
C5 C4 C3 C6 0.60(9) . . . . ?
C5 C4 C3 C48 -133.68(13) . . . . ?
C5 C4 C1 C9 139.36(12) . . . . ?
C5 C4 C1 C2 -89.08(9) . . . . ?
C5 C4 C1 C8 0.18(9) . . . . ?
C5 C6 C3 C4 -0.60(9) . . . . ?
C5 C6 C3 C2 -90.61(9) . . . . ?
C5 C6 C3 C48 133.40(13) . . . . ?
C5 C8 C1 C9 -138.79(12) . . . . ?
C5 C8 C1 C4 -0.17(9) . . . . ?
C5 C8 C1 C2 89.93(9) . . . . ?
C4 C5 C6 C7 -89.63(9) . . . . ?
C4 C5 C6 C3 0.60(9) . . . . ?
C4 C5 C8 C39 -141.46(12) . . . . ?
C4 C5 C8 C7 89.72(9) . . . . ?
C4 C5 C8 C1 0.17(9) . . . . ?
C10 C9 C1 C4 10.42(19) . . . . ?
C10 C9 C1 C2 -107.45(14) . . . . ?
C10 C9 C1 C8 135.13(13) . . . . ?
C10 C9 C14 C13 -0.4(2) . . . . ?
C2 C7 C29 C30 140.56(13) . . . . ?
C2 C7 C29 C34 -39.28(18) . . . . ?
C2 C7 C6 C5 88.87(9) . . . . ?
C2 C7 C6 C3 -0.59(9) . . . . ?
C2 C7 C8 C39 137.43(11) . . . . ?
C2 C7 C8 C5 -89.28(9) . . . . ?
C2 C7 C8 C1 -0.65(9) . . . . ?
C6 C7 C29 C30 21.82(19) . . . . ?
C6 C7 C29 C34 -158.01(13) . . . . ?
C6 C7 C2 C3 0.59(9) . . . . ?
C6 C7 C2 C1 -89.21(9) . . . . ?
C6 C7 C8 C39 -132.45(11) . . . . ?
C6 C7 C8 C5 0.84(9) . . . . ?
C6 C7 C8 C1 89.47(9) . . . . ?
C6 C5 C4 C3 -0.60(9) . . . . ?
C6 C5 C4 C1 89.47(9) . . . . ?
C6 C5 C8 C39 127.98(12) . . . . ?
C6 C5 C8 C7 -0.84(9) . . . . ?
C6 C5 C8 C1 -90.39(9) . . . . ?
C3 C4 C1 C9 -130.85(12) . . . . ?
C3 C4 C1 C2 0.71(9) . . . . ?
C3 C4 C1 C8 89.96(9) . . . . ?
C3 C2 C1 C9 134.00(11) . . . . ?
C3 C2 C1 C4 -0.71(9) . . . . ?
C3 C2 C1 C8 -90.91(9) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C13 C12 C11 C10 -0.6(2) . . . . ?
C13 C12 C15 F1 -150.68(14) . . . . ?
C13 C12 C15 F2 -31.6(2) . . . . ?
C13 C12 C15 F3 90.07(18) . . . . ?
C8 C7 C29 C30 -99.91(15) . . . . ?
C8 C7 C29 C34 80.25(17) . . . . ?
C8 C7 C2 C3 90.46(9) . . . . ?
C8 C7 C2 C1 0.66(9) . . . . ?
C8 C7 C6 C5 -0.85(9) . . . . ?
C8 C7 C6 C3 -90.32(9) . . . . ?
C8 C5 C4 C3 -90.26(9) . . . . ?
C8 C5 C4 C1 -0.18(9) . . . . ?
C8 C5 C6 C7 0.86(9) . . . . ?
C8 C5 C6 C3 91.09(9) . . . . ?
C1 C9 C10 C11 177.13(12) . . . . ?
C1 C9 C14 C13 -177.56(12) . . . . ?
C1 C4 C3 C2 -0.71(9) . . . . ?
C1 C4 C3 C6 -90.08(9) . . . . ?
C1 C4 C3 C48 135.63(13) . . . . ?
C1 C2 C3 C4 0.70(9) . . . . ?
C1 C2 C3 C6 90.89(9) . . . . ?
C1 C2 C3 C48 -134.24(13) . . . . ?
C14 C9 C10 C11 0.0(2) . . . . ?
C14 C9 C1 C4 -172.45(12) . . . . ?
C14 C9 C1 C2 69.67(16) . . . . ?
C14 C9 C1 C8 -47.74(18) . . . . ?
C30 C29 C34 C33 1.3(2) . . . . ?
C24 C19 C5 C4 -1.3(2) . . . . ?
C24 C19 C5 C6 118.05(14) . . . . ?
C24 C19 C5 C8 -125.76(14) . . . . ?
C24 C19 C20 C21 -1.6(2) . . . . ?
C24 C23 C22 C25 177.75(14) . . . . ?
C24 C23 C22 C21 -1.2(2) . . . . ?
C23 C22 C25 F7 73.4(4) . . . . ?
C23 C22 C25 F9 -45.4(3) . . . . ?
C23 C22 C25 F8 -160.6(3) . . . . ?
C23 C22 C25 F8A -68.0(8) . . . . ?
C23 C22 C25 F7A 165.8(8) . . . . ?
C23 C22 C25 F9A 54.1(6) . . . . ?
C23 C22 C21 C20 1.5(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C15 F1 30.72(19) . . . . ?
C11 C12 C15 F2 149.75(14) . . . . ?
C11 C12 C15 F3 -88.54(18) . . . . ?
C41 N40 C39 O47 175.45(12) . . . . ?
C41 N40 C39 C8 -4.11(19) . . . . ?
C41 N40 C43 C45 116.92(14) . . . . ?
C41 N40 C43 C44 -114.88(14) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C31 C32 C35 F4 -127.72(17) . . . . ?
C31 C32 C35 F6 114.47(18) . . . . ?
C31 C32 C35 F5 -6.5(2) . . . . ?
C20 C19 C5 C4 -179.01(12) . . . . ?
C20 C19 C5 C6 -59.68(17) . . . . ?
C20 C19 C5 C8 56.50(18) . . . . ?
C20 C19 C24 C23 2.0(2) . . . . ?
C34 C29 C30 C31 -1.2(2) . . . . ?
C43 N40 C39 O47 -2.43(19) . . . . ?
C43 N40 C39 C8 178.01(11) . . . . ?
C43 N40 C41 C46 -61.65(15) . . . . ?
C43 N40 C41 C42 62.36(15) . . . . ?
C33 C32 C31 C30 0.6(2) . . . . ?
C33 C32 C35 F4 51.7(2) . . . . ?
C33 C32 C35 F6 -66.1(2) . . . . ?
C33 C32 C35 F5 172.92(15) . . . . ?
C25 C22 C21 C20 -177.44(14) . . . . ?
C21 C22 C25 F7 -107.6(4) . . . . ?
C21 C22 C25 F9 133.6(3) . . . . ?
C21 C22 C25 F8 18.4(4) . . . . ?
C21 C22 C25 F8A 111.0(8) . . . . ?
C21 C22 C25 F7A -15.2(8) . . . . ?
C21 C22 C25 F9A -126.9(6) . . . . ?
C15 C12 C13 C14 -178.38(13) . . . . ?
C15 C12 C11 C10 177.99(13) . . . . ?
C35 C32 C31 C30 -179.94(13) . . . . ?
C35 C32 C33 C34 -179.88(14) . . . . ?
C50 C51 C52 C53 -0.6(10) . . . . ?
C50 C55 C54 C53 -0.8(11) . . . . ?
C51 C50 C55 C54 0.3(5) . . . . ?
C51 C52 C53 C54 0.2(13) . . . . ?
C55 C50 C51 C52 0.4(5) . . . . ?
C52 C53 C54 C55 0.5(13) . . . . ?
C50A C55A C54A C53A 0.5(3) . . . . ?
C55A C50A C51A C52A 0.3(7) . . . . ?
C55A C54A C53A C52A -1.4(6) . . . . ?
C54A C53A C52A C51A 1.8(8) . . . . ?
C53A C52A C51A C50A -1.2(8) . . . . ?
C51A C50A C55A C54A 0.1(4) . . . . ?

_olex2_exptl_crystal_mounting_method mesh
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.769
_oxdiff_exptl_absorpt_empirical_full_min 0.713
####################################################################### 
# 
# 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_2f
_database_code_depnum_ccdc_archive 'CCDC 1993518'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H42 N2 O4'
_chemical_formula_weight         506.66

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                   12.9747(2)
_cell_length_b                   12.3749(2)
_cell_length_c                   17.7595(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.9476(17)
_cell_angle_gamma                90
_cell_volume                     2789.71(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    19565

_cell_measurement_theta_min      2.7050

_cell_measurement_theta_max      30.5650


_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.83277

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            29403
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.344
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4911
_reflns_number_gt                4475
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    SIR97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0405P)²+1.1239P] 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         4911
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
O1 O 0.86761(8) 0.71570(8) 0.49159(7) 0.0437(3) Uani 1 1 d . . . . .
C1 C 0.79413(10) 0.65709(10) 0.46734(7) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.70299(7) 0.69093(7) 0.42462(5) 0.0288(2) Uani 1 1 d . . . . .
C2 C 0.68844(11) 0.80665(10) 0.41219(8) 0.0295(3) Uani 1 1 d . . . . .
H1 H 0.708045 0.827861 0.363261 0.035 Uiso 1 1 calc R U . . .
H2 H 0.733437 0.847178 0.454708 0.035 Uiso 1 1 calc R U . . .
C3 C 0.57616(12) 0.83101(12) 0.40922(12) 0.0520(5) Uani 1 1 d . . . . .
H3 H 0.532331 0.789177 0.367751 0.078 Uiso 1 1 calc R U . . .
H4 H 0.563503 0.908325 0.399500 0.078 Uiso 1 1 calc R U . . .
H5 H 0.558181 0.811684 0.458452 0.078 Uiso 1 1 calc R U . . .
C4 C 0.79325(9) 0.53836(9) 0.48188(6) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.70544(9) 0.47446(10) 0.45240(7) 0.0223(3) Uani 1 1 d . . . . .
H34 H 0.645178 0.505897 0.420338 0.027 Uiso 1 1 calc R U . . .
C6 C 0.70605(9) 0.36561(10) 0.46978(7) 0.0215(3) Uani 1 1 d . . . . .
H35 H 0.645807 0.322803 0.449828 0.026 Uiso 1 1 calc R U . . .
C7 C 0.79432(9) 0.31768(9) 0.51641(6) 0.0180(2) Uani 1 1 d . . . . .
C8 C 0.88230(9) 0.38144(10) 0.54431(6) 0.0197(2) Uani 1 1 d . . . . .
H36 H 0.943376 0.349709 0.575156 0.024 Uiso 1 1 calc R U . . .
C9 C 0.88156(9) 0.49104(10) 0.52745(6) 0.0208(3) Uani 1 1 d . . . . .
H37 H 0.941851 0.533887 0.547216 0.025 Uiso 1 1 calc R U . . .
C10 C 0.79115(9) 0.20184(9) 0.53654(6) 0.0173(2) Uani 1 1 d . . . . .
C11 C 0.74880(9) 0.10646(9) 0.47817(6) 0.0174(2) Uani 1 1 d . . . . .
C12 C 0.68132(9) 0.06258(9) 0.53490(6) 0.0191(2) Uani 1 1 d . . . . .
H38 H 0.606409 0.038177 0.519752 0.023 Uiso 1 1 calc R U . . .
C13 C 0.72149(9) 0.15628(9) 0.59234(6) 0.0188(2) Uani 1 1 d . . . . .
H39 H 0.676124 0.200994 0.619367 0.023 Uiso 1 1 calc R U . . .
C14 C 0.81693(9) 0.08463(9) 0.63334(6) 0.0181(2) Uani 1 1 d . . . . .
C15 C 0.77564(9) -0.00981(9) 0.57528(6) 0.0191(2) Uani 1 1 d . . . . .
H40 H 0.770269 -0.087438 0.589628 0.023 Uiso 1 1 calc R U . . .
C16 C 0.84439(9) 0.03450(9) 0.51944(6) 0.0184(2) Uani 1 1 d . . . . .
H41 H 0.889679 -0.010552 0.492568 0.022 Uiso 1 1 calc R U . . .
C17 C 0.88475(9) 0.12870(9) 0.57696(6) 0.0179(2) Uani 1 1 d . . . . .
H42 H 0.959788 0.152612 0.592379 0.021 Uiso 1 1 calc R U . . .
C18 C 0.70248(9) 0.11720(9) 0.39344(6) 0.0176(2) Uani 1 1 d . . . . .
O3 O 0.60802(6) 0.09737(7) 0.37044(5) 0.0248(2) Uani 1 1 d . . . . .
N1 N 0.76607(7) 0.14821(8) 0.34596(5) 0.0176(2) Uani 1 1 d . . . . .
C19 C 0.72394(9) 0.15333(10) 0.26168(6) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.783960 0.175198 0.237621 0.025 Uiso 1 1 calc R U . . .
C20 C 0.68779(12) 0.04298(11) 0.22893(7) 0.0341(3) Uani 1 1 d . . . . .
H7 H 0.746561 -0.008195 0.240834 0.051 Uiso 1 1 calc R U . . .
H8 H 0.663800 0.048496 0.172995 0.051 Uiso 1 1 calc R U . . .
H9 H 0.629699 0.017474 0.251853 0.051 Uiso 1 1 calc R U . . .
C21 C 0.63973(10) 0.23980(11) 0.24027(7) 0.0296(3) Uani 1 1 d . . . . .
H10 H 0.576837 0.218738 0.259191 0.044 Uiso 1 1 calc R U . . .
H11 H 0.621592 0.247689 0.184168 0.044 Uiso 1 1 calc R U . . .
H12 H 0.666490 0.308715 0.263636 0.044 Uiso 1 1 calc R U . . .
C22 C 0.87879(9) 0.17410(10) 0.37325(7) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.894035 0.170146 0.430731 0.025 Uiso 1 1 calc R U . . .
C23 C 0.94867(10) 0.09108(12) 0.34506(8) 0.0326(3) Uani 1 1 d . . . . .
H14 H 0.930646 0.018594 0.360454 0.049 Uiso 1 1 calc R U . . .
H15 H 1.022679 0.106466 0.367743 0.049 Uiso 1 1 calc R U . . .
H16 H 0.937687 0.094702 0.288839 0.049 Uiso 1 1 calc R U . . .
C24 C 0.90453(10) 0.28853(11) 0.35148(7) 0.0272(3) Uani 1 1 d . . . . .
H17 H 0.896323 0.293564 0.295479 0.041 Uiso 1 1 calc R U . . .
H18 H 0.977319 0.306046 0.376234 0.041 Uiso 1 1 calc R U . . .
H19 H 0.856495 0.339601 0.368706 0.041 Uiso 1 1 calc R U . . .
C25 C 0.86130(9) 0.07431(9) 0.71826(6) 0.0183(2) Uani 1 1 d . . . . .
O4 O 0.95367(6) 0.09909(7) 0.74336(5) 0.0255(2) Uani 1 1 d . . . . .
N2 N 0.79742(7) 0.03616(8) 0.76370(5) 0.0202(2) Uani 1 1 d . . . . .
C26 C 0.84013(10) 0.02038(10) 0.84706(6) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.780763 -0.007263 0.869681 0.029 Uiso 1 1 calc R U . . .
C27 C 0.87632(12) 0.12600(12) 0.88830(7) 0.0359(3) Uani 1 1 d . . . . .
H21 H 0.934475 0.156381 0.867617 0.054 Uiso 1 1 calc R U . . .
H22 H 0.900209 0.112181 0.943500 0.054 Uiso 1 1 calc R U . . .
H23 H 0.817555 0.177337 0.880317 0.054 Uiso 1 1 calc R U . . .
C28 C 0.92482(10) -0.06677(11) 0.86036(8) 0.0317(3) Uani 1 1 d . . . . .
H24 H 0.896256 -0.133503 0.834455 0.048 Uiso 1 1 calc R U . . .
H25 H 0.947508 -0.080238 0.915696 0.048 Uiso 1 1 calc R U . . .
H26 H 0.985205 -0.042654 0.839493 0.048 Uiso 1 1 calc R U . . .
C29 C 0.68661(9) 0.00567(11) 0.73382(7) 0.0248(3) Uani 1 1 d . . . . .
H27 H 0.671539 0.019107 0.677068 0.030 Uiso 1 1 calc R U . . .
C30 C 0.66669(11) -0.11377(12) 0.74525(8) 0.0352(3) Uani 1 1 d . . . . .
H28 H 0.716903 -0.157005 0.723697 0.053 Uiso 1 1 calc R U . . .
H29 H 0.594709 -0.132117 0.719048 0.053 Uiso 1 1 calc R U . . .
H30 H 0.675631 -0.129118 0.800354 0.053 Uiso 1 1 calc R U . . .
C31 C 0.61259(11) 0.07789(13) 0.76771(8) 0.0377(3) Uani 1 1 d . . . . .
H31 H 0.625743 0.067767 0.823613 0.057 Uiso 1 1 calc R U . . .
H32 H 0.539414 0.058710 0.745189 0.057 Uiso 1 1 calc R U . . .
H33 H 0.625002 0.153620 0.756114 0.057 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
O1 C1 1.2044(15) . ?
C1 O2 1.3334(15) . ?
C1 C4 1.4922(17) . ?
O2 C2 1.4553(14) . ?
C2 C3 1.478(2) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C3 H5 0.9800 . ?
C4 C9 1.3881(17) . ?
C4 C5 1.3967(17) . ?
C5 C6 1.3816(17) . ?
C5 H34 0.9500 . ?
C6 C7 1.3988(16) . ?
C6 H35 0.9500 . ?
C7 C8 1.3917(16) . ?
C7 C10 1.4799(16) . ?
C8 C9 1.3886(17) . ?
C8 H36 0.9500 . ?
C9 H37 0.9500 . ?
C10 C17 1.5647(15) . ?
C10 C13 1.5772(15) . ?
C10 C11 1.5918(15) . ?
C11 C18 1.5062(15) . ?
C11 C12 1.5627(15) . ?
C11 C16 1.5785(15) . ?
C12 C13 1.5610(16) . ?
C12 C15 1.5655(16) . ?
C12 H38 1.0000 . ?
C13 C14 1.5737(15) . ?
C13 H39 1.0000 . ?
C14 C25 1.5042(15) . ?
C14 C17 1.5618(15) . ?
C14 C15 1.5771(16) . ?
C15 C16 1.5640(15) . ?
C15 H40 1.0000 . ?
C16 C17 1.5670(16) . ?
C16 H41 1.0000 . ?
C17 H42 1.0000 . ?
C18 O3 1.2336(14) . ?
C18 N1 1.3517(15) . ?
N1 C22 1.4775(14) . ?
N1 C19 1.4848(14) . ?
C19 C20 1.5200(17) . ?
C19 C21 1.5203(17) . ?
C19 H6 1.0000 . ?
C20 H7 0.9800 . ?
C20 H8 0.9800 . ?
C20 H9 0.9800 . ?
C21 H10 0.9800 . ?
C21 H11 0.9800 . ?
C21 H12 0.9800 . ?
C22 C23 1.5219(17) . ?
C22 C24 1.5230(17) . ?
C22 H13 1.0000 . ?
C23 H14 0.9800 . ?
C23 H15 0.9800 . ?
C23 H16 0.9800 . ?
C24 H17 0.9800 . ?
C24 H18 0.9800 . ?
C24 H19 0.9800 . ?
C25 O4 1.2280(14) . ?
C25 N2 1.3557(15) . ?
N2 C29 1.4747(14) . ?
N2 C26 1.4823(14) . ?
C26 C28 1.5228(18) . ?
C26 C27 1.5241(18) . ?
C26 H20 1.0000 . ?
C27 H21 0.9800 . ?
C27 H22 0.9800 . ?
C27 H23 0.9800 . ?
C28 H24 0.9800 . ?
C28 H25 0.9800 . ?
C28 H26 0.9800 . ?
C29 C30 1.5213(19) . ?
C29 C31 1.5240(19) . ?
C29 H27 1.0000 . ?
C30 H28 0.9800 . ?
C30 H29 0.9800 . ?
C30 H30 0.9800 . ?
C31 H31 0.9800 . ?
C31 H32 0.9800 . ?
C31 H33 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
O1 C1 O2 123.88(11) . . ?
O1 C1 C4 124.40(12) . . ?
O2 C1 C4 111.72(10) . . ?
C1 O2 C2 117.86(10) . . ?
O2 C2 C3 107.58(11) . . ?
O2 C2 H1 110.2 . . ?
C3 C2 H1 110.2 . . ?
O2 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
H1 C2 H2 108.5 . . ?
C2 C3 H3 109.5 . . ?
C2 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
C2 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 109.5 . . ?
C9 C4 C5 119.38(11) . . ?
C9 C4 C1 118.77(11) . . ?
C5 C4 C1 121.84(11) . . ?
C6 C5 C4 120.12(11) . . ?
C6 C5 H34 119.9 . . ?
C4 C5 H34 119.9 . . ?
C5 C6 C7 120.79(11) . . ?
C5 C6 H35 119.6 . . ?
C7 C6 H35 119.6 . . ?
C8 C7 C6 118.75(11) . . ?
C8 C7 C10 121.66(10) . . ?
C6 C7 C10 119.57(10) . . ?
C9 C8 C7 120.56(11) . . ?
C9 C8 H36 119.7 . . ?
C7 C8 H36 119.7 . . ?
C4 C9 C8 120.38(11) . . ?
C4 C9 H37 119.8 . . ?
C8 C9 H37 119.8 . . ?
C7 C10 C17 127.83(10) . . ?
C7 C10 C13 123.10(9) . . ?
C17 C10 C13 89.79(8) . . ?
C7 C10 C11 125.73(9) . . ?
C17 C10 C11 90.02(8) . . ?
C13 C10 C11 88.78(8) . . ?
C18 C11 C12 120.92(9) . . ?
C18 C11 C16 128.78(9) . . ?
C12 C11 C16 89.76(8) . . ?
C18 C11 C10 126.71(9) . . ?
C12 C11 C10 90.10(8) . . ?
C16 C11 C10 89.08(8) . . ?
C13 C12 C11 90.42(8) . . ?
C13 C12 C15 90.13(8) . . ?
C11 C12 C15 90.29(8) . . ?
C13 C12 H38 125.1 . . ?
C11 C12 H38 125.1 . . ?
C15 C12 H38 125.1 . . ?
C12 C13 C14 90.46(8) . . ?
C12 C13 C10 90.70(8) . . ?
C14 C13 C10 89.64(8) . . ?
C12 C13 H39 125.1 . . ?
C14 C13 H39 125.1 . . ?
C10 C13 H39 125.1 . . ?
C25 C14 C17 121.53(9) . . ?
C25 C14 C13 127.80(9) . . ?
C17 C14 C13 90.02(8) . . ?
C25 C14 C15 126.89(9) . . ?
C17 C14 C15 89.99(8) . . ?
C13 C14 C15 89.24(8) . . ?
C16 C15 C12 90.19(8) . . ?
C16 C15 C14 89.64(8) . . ?
C12 C15 C14 90.17(8) . . ?
C16 C15 H40 125.3 . . ?
C12 C15 H40 125.3 . . ?
C14 C15 H40 125.3 . . ?
C15 C16 C17 90.28(8) . . ?
C15 C16 C11 89.76(8) . . ?
C17 C16 C11 90.43(8) . . ?
C15 C16 H41 125.2 . . ?
C17 C16 H41 125.2 . . ?
C11 C16 H41 125.2 . . ?
C14 C17 C10 90.54(8) . . ?
C14 C17 C16 90.09(8) . . ?
C10 C17 C16 90.48(8) . . ?
C14 C17 H42 125.0 . . ?
C10 C17 H42 125.0 . . ?
C16 C17 H42 125.0 . . ?
O3 C18 N1 122.88(10) . . ?
O3 C18 C11 118.48(10) . . ?
N1 C18 C11 118.64(10) . . ?
C18 N1 C22 123.20(9) . . ?
C18 N1 C19 119.74(9) . . ?
C22 N1 C19 117.02(9) . . ?
N1 C19 C20 111.56(10) . . ?
N1 C19 C21 112.19(10) . . ?
C20 C19 C21 112.82(11) . . ?
N1 C19 H6 106.6 . . ?
C20 C19 H6 106.6 . . ?
C21 C19 H6 106.6 . . ?
C19 C20 H7 109.5 . . ?
C19 C20 H8 109.5 . . ?
H7 C20 H8 109.5 . . ?
C19 C20 H9 109.5 . . ?
H7 C20 H9 109.5 . . ?
H8 C20 H9 109.5 . . ?
C19 C21 H10 109.5 . . ?
C19 C21 H11 109.5 . . ?
H10 C21 H11 109.5 . . ?
C19 C21 H12 109.5 . . ?
H10 C21 H12 109.5 . . ?
H11 C21 H12 109.5 . . ?
N1 C22 C23 111.24(10) . . ?
N1 C22 C24 111.87(9) . . ?
C23 C22 C24 111.55(10) . . ?
N1 C22 H13 107.3 . . ?
C23 C22 H13 107.3 . . ?
C24 C22 H13 107.3 . . ?
C22 C23 H14 109.5 . . ?
C22 C23 H15 109.5 . . ?
H14 C23 H15 109.5 . . ?
C22 C23 H16 109.5 . . ?
H14 C23 H16 109.5 . . ?
H15 C23 H16 109.5 . . ?
C22 C24 H17 109.5 . . ?
C22 C24 H18 109.5 . . ?
H17 C24 H18 109.5 . . ?
C22 C24 H19 109.5 . . ?
H17 C24 H19 109.5 . . ?
H18 C24 H19 109.5 . . ?
O4 C25 N2 122.81(10) . . ?
O4 C25 C14 119.01(10) . . ?
N2 C25 C14 118.17(10) . . ?
C25 N2 C29 123.06(9) . . ?
C25 N2 C26 119.48(9) . . ?
C29 N2 C26 117.43(9) . . ?
N2 C26 C28 110.91(10) . . ?
N2 C26 C27 112.42(10) . . ?
C28 C26 C27 113.09(11) . . ?
N2 C26 H20 106.6 . . ?
C28 C26 H20 106.6 . . ?
C27 C26 H20 106.6 . . ?
C26 C27 H21 109.5 . . ?
C26 C27 H22 109.5 . . ?
H21 C27 H22 109.5 . . ?
C26 C27 H23 109.5 . . ?
H21 C27 H23 109.5 . . ?
H22 C27 H23 109.5 . . ?
C26 C28 H24 109.5 . . ?
C26 C28 H25 109.5 . . ?
H24 C28 H25 109.5 . . ?
C26 C28 H26 109.5 . . ?
H24 C28 H26 109.5 . . ?
H25 C28 H26 109.5 . . ?
N2 C29 C30 112.36(10) . . ?
N2 C29 C31 110.79(11) . . ?
C30 C29 C31 112.25(11) . . ?
N2 C29 H27 107.0 . . ?
C30 C29 H27 107.0 . . ?
C31 C29 H27 107.0 . . ?
C29 C30 H28 109.5 . . ?
C29 C30 H29 109.5 . . ?
H28 C30 H29 109.5 . . ?
C29 C30 H30 109.5 . . ?
H28 C30 H30 109.5 . . ?
H29 C30 H30 109.5 . . ?
C29 C31 H31 109.5 . . ?
C29 C31 H32 109.5 . . ?
H31 C31 H32 109.5 . . ?
C29 C31 H33 109.5 . . ?
H31 C31 H33 109.5 . . ?
H32 C31 H33 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 O2 C2 -5.47(18) . . . . ?
C4 C1 O2 C2 173.99(10) . . . . ?
C1 O2 C2 C3 -145.52(13) . . . . ?
O1 C1 C4 C9 1.26(18) . . . . ?
O2 C1 C4 C9 -178.19(10) . . . . ?
O1 C1 C4 C5 179.79(12) . . . . ?
O2 C1 C4 C5 0.34(16) . . . . ?
C9 C4 C5 C6 1.22(17) . . . . ?
C1 C4 C5 C6 -177.29(11) . . . . ?
C4 C5 C6 C7 -0.48(17) . . . . ?
C5 C6 C7 C8 -0.79(17) . . . . ?
C5 C6 C7 C10 177.62(10) . . . . ?
C6 C7 C8 C9 1.32(16) . . . . ?
C10 C7 C8 C9 -177.05(10) . . . . ?
C5 C4 C9 C8 -0.69(17) . . . . ?
C1 C4 C9 C8 177.87(10) . . . . ?
C7 C8 C9 C4 -0.59(17) . . . . ?
C8 C7 C10 C17 -11.50(17) . . . . ?
C6 C7 C10 C17 170.14(10) . . . . ?
C8 C7 C10 C13 108.55(13) . . . . ?
C6 C7 C10 C13 -69.82(14) . . . . ?
C8 C7 C10 C11 -135.50(11) . . . . ?
C6 C7 C10 C11 46.14(15) . . . . ?
C7 C10 C11 C18 -1.61(17) . . . . ?
C17 C10 C11 C18 -140.71(11) . . . . ?
C13 C10 C11 C18 129.51(11) . . . . ?
C7 C10 C11 C12 -131.57(11) . . . . ?
C17 C10 C11 C12 89.34(8) . . . . ?
C13 C10 C11 C12 -0.45(8) . . . . ?
C7 C10 C11 C16 138.67(11) . . . . ?
C17 C10 C11 C16 -0.42(8) . . . . ?
C13 C10 C11 C16 -90.21(8) . . . . ?
C18 C11 C12 C13 -133.79(10) . . . . ?
C16 C11 C12 C13 89.53(8) . . . . ?
C10 C11 C12 C13 0.45(8) . . . . ?
C18 C11 C12 C15 136.08(10) . . . . ?
C16 C11 C12 C15 -0.60(8) . . . . ?
C10 C11 C12 C15 -89.67(8) . . . . ?
C11 C12 C13 C14 -90.11(8) . . . . ?
C15 C12 C13 C14 0.18(8) . . . . ?
C11 C12 C13 C10 -0.46(8) . . . . ?
C15 C12 C13 C10 89.83(8) . . . . ?
C7 C10 C13 C12 133.56(11) . . . . ?
C17 C10 C13 C12 -89.57(8) . . . . ?
C11 C10 C13 C12 0.45(8) . . . . ?
C7 C10 C13 C14 -135.98(11) . . . . ?
C17 C10 C13 C14 0.88(8) . . . . ?
C11 C10 C13 C14 90.91(8) . . . . ?
C12 C13 C14 C25 -138.73(11) . . . . ?
C10 C13 C14 C25 130.57(11) . . . . ?
C12 C13 C14 C17 89.81(8) . . . . ?
C10 C13 C14 C17 -0.89(8) . . . . ?
C12 C13 C14 C15 -0.18(8) . . . . ?
C10 C13 C14 C15 -90.88(8) . . . . ?
C13 C12 C15 C16 -89.82(8) . . . . ?
C11 C12 C15 C16 0.60(8) . . . . ?
C13 C12 C15 C14 -0.18(8) . . . . ?
C11 C12 C15 C14 90.24(8) . . . . ?
C25 C14 C15 C16 -130.48(11) . . . . ?
C17 C14 C15 C16 0.35(8) . . . . ?
C13 C14 C15 C16 90.37(8) . . . . ?
C25 C14 C15 C12 139.33(11) . . . . ?
C17 C14 C15 C12 -89.84(8) . . . . ?
C13 C14 C15 C12 0.18(8) . . . . ?
C12 C15 C16 C17 89.83(8) . . . . ?
C14 C15 C16 C17 -0.35(8) . . . . ?
C12 C15 C16 C11 -0.60(8) . . . . ?
C14 C15 C16 C11 -90.77(8) . . . . ?
C18 C11 C16 C15 -130.37(12) . . . . ?
C12 C11 C16 C15 0.60(8) . . . . ?
C10 C11 C16 C15 90.70(8) . . . . ?
C18 C11 C16 C17 139.34(11) . . . . ?
C12 C11 C16 C17 -89.68(8) . . . . ?
C10 C11 C16 C17 0.42(8) . . . . ?
C25 C14 C17 C10 -135.10(10) . . . . ?
C13 C14 C17 C10 0.89(8) . . . . ?
C15 C14 C17 C10 90.13(8) . . . . ?
C25 C14 C17 C16 134.42(10) . . . . ?
C13 C14 C17 C16 -89.58(8) . . . . ?
C15 C14 C17 C16 -0.35(8) . . . . ?
C7 C10 C17 C14 132.63(11) . . . . ?
C13 C10 C17 C14 -0.89(8) . . . . ?
C11 C10 C17 C14 -89.67(8) . . . . ?
C7 C10 C17 C16 -137.28(11) . . . . ?
C13 C10 C17 C16 89.20(8) . . . . ?
C11 C10 C17 C16 0.42(8) . . . . ?
C15 C16 C17 C14 0.35(8) . . . . ?
C11 C16 C17 C14 90.11(8) . . . . ?
C15 C16 C17 C10 -90.19(8) . . . . ?
C11 C16 C17 C10 -0.43(8) . . . . ?
C12 C11 C18 O3 4.73(16) . . . . ?
C16 C11 C18 O3 123.08(12) . . . . ?
C10 C11 C18 O3 -111.95(12) . . . . ?
C12 C11 C18 N1 -175.34(10) . . . . ?
C16 C11 C18 N1 -56.99(16) . . . . ?
C10 C11 C18 N1 67.98(14) . . . . ?
O3 C18 N1 C22 178.80(10) . . . . ?
C11 C18 N1 C22 -1.13(16) . . . . ?
O3 C18 N1 C19 -3.58(16) . . . . ?
C11 C18 N1 C19 176.49(9) . . . . ?
C18 N1 C19 C20 -62.04(14) . . . . ?
C22 N1 C19 C20 115.72(12) . . . . ?
C18 N1 C19 C21 65.66(13) . . . . ?
C22 N1 C19 C21 -116.58(11) . . . . ?
C18 N1 C22 C23 112.40(12) . . . . ?
C19 N1 C22 C23 -65.27(13) . . . . ?
C18 N1 C22 C24 -122.10(11) . . . . ?
C19 N1 C22 C24 60.23(13) . . . . ?
C17 C14 C25 O4 -1.53(16) . . . . ?
C13 C14 C25 O4 -119.98(13) . . . . ?
C15 C14 C25 O4 115.88(13) . . . . ?
C17 C14 C25 N2 179.50(10) . . . . ?
C13 C14 C25 N2 61.04(15) . . . . ?
C15 C14 C25 N2 -63.10(15) . . . . ?
O4 C25 N2 C29 -179.64(11) . . . . ?
C14 C25 N2 C29 -0.70(16) . . . . ?
O4 C25 N2 C26 -1.67(17) . . . . ?
C14 C25 N2 C26 177.26(10) . . . . ?
C25 N2 C26 C28 -64.73(14) . . . . ?
C29 N2 C26 C28 113.35(12) . . . . ?
C25 N2 C26 C27 62.98(14) . . . . ?
C29 N2 C26 C27 -118.94(12) . . . . ?
C25 N2 C29 C30 117.00(12) . . . . ?
C26 N2 C29 C30 -61.01(14) . . . . ?
C25 N2 C29 C31 -116.55(12) . . . . ?
C26 N2 C29 C31 65.45(14) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.036



_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_2k
_database_code_depnum_ccdc_archive 'CCDC 1993517'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H40 N2 O2'
_chemical_formula_weight         484.66

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                   10.4974(4)
_cell_length_b                   24.3000(6)
_cell_length_c                   11.3737(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.196(4)
_cell_angle_gamma                90
_cell_volume                     2739.97(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    13383

_cell_measurement_theta_min      2.6020

_cell_measurement_theta_max      30.5180


_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1

_exptl_crystal_size_mid          0.05

_exptl_crystal_size_min          0.01

_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.79595

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            29817
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4822
_reflns_number_gt                4097
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    SIR-97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0362P)²+1.0182P] 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         4822
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O1 O 0.15669(9) 0.35782(3) 0.36037(8) 0.0238(2) Uani 1 1 d . . . . .
C1 C 0.26334(12) 0.34324(5) 0.43959(11) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.35507(11) 0.37984(4) 0.50727(9) 0.0234(2) Uani 1 1 d . . . . .
C2 C 0.33315(14) 0.43970(5) 0.48168(12) 0.0284(3) Uani 1 1 d . . . . .
H1 H 0.414774 0.458782 0.538180 0.034 Uiso 1 1 calc R U . . .
C3 C 0.21336(16) 0.46128(6) 0.51523(14) 0.0375(4) Uani 1 1 d . . . . .
H2 H 0.130303 0.444111 0.461086 0.056 Uiso 1 1 calc R U . . .
H3 H 0.207193 0.501291 0.503961 0.056 Uiso 1 1 calc R U . . .
H4 H 0.225459 0.452332 0.602257 0.056 Uiso 1 1 calc R U . . .
C4 C 0.32523(16) 0.45446(6) 0.34904(13) 0.0345(3) Uani 1 1 d . . . . .
H5 H 0.405311 0.440373 0.332772 0.052 Uiso 1 1 calc R U . . .
H6 H 0.321135 0.494547 0.339133 0.052 Uiso 1 1 calc R U . . .
H7 H 0.244153 0.437927 0.290049 0.052 Uiso 1 1 calc R U . . .
C5 C 0.47740(13) 0.36332(6) 0.60983(12) 0.0289(3) Uani 1 1 d . . . . .
H8 H 0.471344 0.322700 0.621028 0.035 Uiso 1 1 calc R U . . .
C6 C 0.48355(16) 0.39037(6) 0.73281(13) 0.0387(4) Uani 1 1 d . . . . .
H9 H 0.493506 0.430263 0.726628 0.058 Uiso 1 1 calc R U . . .
H10 H 0.560855 0.375781 0.800005 0.058 Uiso 1 1 calc R U . . .
H11 H 0.400253 0.382420 0.750700 0.058 Uiso 1 1 calc R U . . .
C7 C 0.60390(15) 0.37370(7) 0.57565(16) 0.0421(4) Uani 1 1 d . . . . .
H12 H 0.599639 0.352131 0.501643 0.063 Uiso 1 1 calc R U . . .
H13 H 0.683547 0.362732 0.645156 0.063 Uiso 1 1 calc R U . . .
H14 H 0.609961 0.412923 0.558137 0.063 Uiso 1 1 calc R U . . .
C8 C 0.28747(12) 0.28255(5) 0.46210(11) 0.0198(3) Uani 1 1 d . . . . .
C9 C 0.19643(12) 0.23997(5) 0.36937(11) 0.0214(3) Uani 1 1 d . . . . .
H15 H 0.126563 0.249530 0.288128 0.026 Uiso 1 1 calc R U . . .
C10 C 0.32124(12) 0.20240(5) 0.38423(11) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.343223 0.184562 0.314025 0.025 Uiso 1 1 calc R U . . .
C11 C 0.41383(12) 0.24435(5) 0.47807(11) 0.0203(3) Uani 1 1 d . . . . .
H17 H 0.504181 0.257185 0.477633 0.024 Uiso 1 1 calc R U . . .
C12 C 0.38632(12) 0.21338(5) 0.58816(11) 0.0190(3) Uani 1 1 d . . . . .
H18 H 0.456819 0.203363 0.668686 0.023 Uiso 1 1 calc R U . . .
C13 C 0.29360(12) 0.17099(5) 0.49307(11) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.16767(12) 0.20922(5) 0.47826(11) 0.0203(3) Uani 1 1 d . . . . .
H19 H 0.077026 0.196352 0.477804 0.024 Uiso 1 1 calc R U . . .
C15 C 0.26161(12) 0.25099(5) 0.57517(11) 0.0189(3) Uani 1 1 d . . . . .
C16 C 0.22916(12) 0.27807(5) 0.67872(11) 0.0192(3) Uani 1 1 d . . . . .
C17 C 0.29414(12) 0.26370(5) 0.80043(11) 0.0210(3) Uani 1 1 d . . . . .
H20 H 0.362762 0.236439 0.818611 0.025 Uiso 1 1 calc R U . . .
C18 C 0.26150(12) 0.28849(5) 0.89984(11) 0.0214(3) Uani 1 1 d . . . . .
C19 C 0.32562(13) 0.27322(6) 1.02580(12) 0.0273(3) Uani 1 1 d . . . . .
H21 H 0.392364 0.245168 1.045635 0.033 Uiso 1 1 calc R U . . .
C20 C 0.29217(14) 0.29856(6) 1.11906(12) 0.0312(3) Uani 1 1 d . . . . .
H22 H 0.335806 0.287908 1.203096 0.037 Uiso 1 1 calc R U . . .
C21 C 0.19382(14) 0.34021(6) 1.09163(13) 0.0308(3) Uani 1 1 d . . . . .
H23 H 0.171957 0.357675 1.157244 0.037 Uiso 1 1 calc R U . . .
C22 C 0.12942(14) 0.35574(5) 0.97107(12) 0.0265(3) Uani 1 1 d . . . . .
H24 H 0.062801 0.383816 0.953519 0.032 Uiso 1 1 calc R U . . .
C23 C 0.16123(12) 0.33032(5) 0.87220(11) 0.0218(3) Uani 1 1 d . . . . .
C24 C 0.09556(13) 0.34473(5) 0.74564(12) 0.0227(3) Uani 1 1 d . . . . .
H25 H 0.027969 0.372435 0.725760 0.027 Uiso 1 1 calc R U . . .
C25 C 0.12790(12) 0.31946(5) 0.65219(11) 0.0216(3) Uani 1 1 d . . . . .
H26 H 0.082147 0.329641 0.568221 0.026 Uiso 1 1 calc R U . . .
C26 C 0.30273(12) 0.10941(5) 0.50515(11) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.33789(9) 0.08256(4) 0.42920(8) 0.0277(2) Uani 1 1 d . . . . .
N2 N 0.27343(10) 0.08563(4) 0.60090(10) 0.0231(2) Uani 1 1 d . . . . .
C27 C 0.22959(13) 0.11726(5) 0.69156(12) 0.0244(3) Uani 1 1 d . . . . .
H27 H 0.229814 0.156976 0.668571 0.029 Uiso 1 1 calc R U . . .
C28 C 0.32715(15) 0.11127(6) 0.82410(12) 0.0322(3) Uani 1 1 d . . . . .
H28 H 0.327821 0.072940 0.851058 0.048 Uiso 1 1 calc R U . . .
H29 H 0.298232 0.135211 0.879924 0.048 Uiso 1 1 calc R U . . .
H30 H 0.418058 0.121824 0.826448 0.048 Uiso 1 1 calc R U . . .
C29 C 0.08529(15) 0.10278(6) 0.68189(15) 0.0377(4) Uani 1 1 d . . . . .
H31 H 0.025836 0.108140 0.595964 0.057 Uiso 1 1 calc R U . . .
H32 H 0.055917 0.126623 0.737573 0.057 Uiso 1 1 calc R U . . .
H33 H 0.081285 0.064250 0.705897 0.057 Uiso 1 1 calc R U . . .
C30 C 0.28961(14) 0.02525(5) 0.62007(13) 0.0298(3) Uani 1 1 d . . . . .
H34 H 0.258216 0.016234 0.691846 0.036 Uiso 1 1 calc R U . . .
C31 C 0.43756(15) 0.00871(6) 0.65890(14) 0.0378(4) Uani 1 1 d . . . . .
H35 H 0.471752 0.015107 0.589593 0.057 Uiso 1 1 calc R U . . .
H36 H 0.446556 -0.030384 0.681291 0.057 Uiso 1 1 calc R U . . .
H37 H 0.489598 0.030754 0.730797 0.057 Uiso 1 1 calc R U . . .
C32 C 0.20098(15) -0.00761(6) 0.50945(16) 0.0403(4) Uani 1 1 d . . . . .
H38 H 0.109194 0.007357 0.482697 0.060 Uiso 1 1 calc R U . . .
H39 H 0.199036 -0.046219 0.533692 0.060 Uiso 1 1 calc R U . . .
H40 H 0.237640 -0.005124 0.440732 0.060 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
O1 C1 1.2359(15) . ?
C1 N1 1.3503(16) . ?
C1 C8 1.5038(17) . ?
N1 C5 1.4784(16) . ?
N1 C2 1.4866(16) . ?
C2 C3 1.522(2) . ?
C2 C4 1.5260(19) . ?
C2 H1 1.0000 . ?
C3 H2 0.9800 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C4 H7 0.9800 . ?
C5 C7 1.522(2) . ?
C5 C6 1.528(2) . ?
C5 H8 1.0000 . ?
C6 H9 0.9800 . ?
C6 H10 0.9800 . ?
C6 H11 0.9800 . ?
C7 H12 0.9800 . ?
C7 H13 0.9800 . ?
C7 H14 0.9800 . ?
C8 C9 1.5600(17) . ?
C8 C11 1.5798(16) . ?
C8 C15 1.5954(16) . ?
C9 C14 1.5586(17) . ?
C9 C10 1.5598(17) . ?
C9 H15 1.0000 . ?
C10 C13 1.5605(17) . ?
C10 C11 1.5623(17) . ?
C10 H16 1.0000 . ?
C11 C12 1.5670(16) . ?
C11 H17 1.0000 . ?
C12 C15 1.5633(16) . ?
C12 C13 1.5766(16) . ?
C12 H18 1.0000 . ?
C13 C26 1.5029(17) . ?
C13 C14 1.5788(16) . ?
C14 C15 1.5821(16) . ?
C14 H19 1.0000 . ?
C15 C16 1.4832(16) . ?
C16 C17 1.3721(17) . ?
C16 C25 1.4217(17) . ?
C17 C18 1.4189(17) . ?
C17 H20 0.9500 . ?
C18 C19 1.4174(18) . ?
C18 C23 1.4222(18) . ?
C19 C20 1.3684(19) . ?
C19 H21 0.9500 . ?
C20 C21 1.406(2) . ?
C20 H22 0.9500 . ?
C21 C22 1.368(2) . ?
C21 H23 0.9500 . ?
C22 C23 1.4158(17) . ?
C22 H24 0.9500 . ?
C23 C24 1.4202(18) . ?
C24 C25 1.3635(17) . ?
C24 H25 0.9500 . ?
C25 H26 0.9500 . ?
C26 O2 1.2320(15) . ?
C26 N2 1.3545(16) . ?
N2 C27 1.4758(16) . ?
N2 C30 1.4848(16) . ?
C27 C29 1.5235(19) . ?
C27 C28 1.5255(19) . ?
C27 H27 1.0000 . ?
C28 H28 0.9800 . ?
C28 H29 0.9800 . ?
C28 H30 0.9800 . ?
C29 H31 0.9800 . ?
C29 H32 0.9800 . ?
C29 H33 0.9800 . ?
C30 C32 1.522(2) . ?
C30 C31 1.522(2) . ?
C30 H34 1.0000 . ?
C31 H35 0.9800 . ?
C31 H36 0.9800 . ?
C31 H37 0.9800 . ?
C32 H38 0.9800 . ?
C32 H39 0.9800 . ?
C32 H40 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
O1 C1 N1 122.14(11) . . ?
O1 C1 C8 117.82(11) . . ?
N1 C1 C8 120.01(10) . . ?
C1 N1 C5 122.86(10) . . ?
C1 N1 C2 119.83(10) . . ?
C5 N1 C2 117.29(10) . . ?
N1 C2 C3 112.05(11) . . ?
N1 C2 C4 112.22(11) . . ?
C3 C2 C4 112.70(12) . . ?
N1 C2 H1 106.4 . . ?
C3 C2 H1 106.4 . . ?
C4 C2 H1 106.4 . . ?
C2 C3 H2 109.5 . . ?
C2 C3 H3 109.5 . . ?
H2 C3 H3 109.5 . . ?
C2 C3 H4 109.5 . . ?
H2 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
C2 C4 H5 109.5 . . ?
C2 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
C2 C4 H7 109.5 . . ?
H5 C4 H7 109.5 . . ?
H6 C4 H7 109.5 . . ?
N1 C5 C7 110.97(11) . . ?
N1 C5 C6 111.71(11) . . ?
C7 C5 C6 112.63(12) . . ?
N1 C5 H8 107.1 . . ?
C7 C5 H8 107.1 . . ?
C6 C5 H8 107.1 . . ?
C5 C6 H9 109.5 . . ?
C5 C6 H10 109.5 . . ?
H9 C6 H10 109.5 . . ?
C5 C6 H11 109.5 . . ?
H9 C6 H11 109.5 . . ?
H10 C6 H11 109.5 . . ?
C5 C7 H12 109.5 . . ?
C5 C7 H13 109.5 . . ?
H12 C7 H13 109.5 . . ?
C5 C7 H14 109.5 . . ?
H12 C7 H14 109.5 . . ?
H13 C7 H14 109.5 . . ?
C1 C8 C9 120.25(10) . . ?
C1 C8 C11 133.14(10) . . ?
C9 C8 C11 89.57(9) . . ?
C1 C8 C15 123.01(10) . . ?
C9 C8 C15 89.85(9) . . ?
C11 C8 C15 89.07(9) . . ?
C14 C9 C10 90.49(9) . . ?
C14 C9 C8 90.94(9) . . ?
C10 C9 C8 90.51(9) . . ?
C14 C9 H15 124.8 . . ?
C10 C9 H15 124.8 . . ?
C8 C9 H15 124.8 . . ?
C9 C10 C13 90.21(9) . . ?
C9 C10 C11 90.22(9) . . ?
C13 C10 C11 90.77(9) . . ?
C9 C10 H16 125.0 . . ?
C13 C10 H16 125.0 . . ?
C11 C10 H16 125.0 . . ?
C10 C11 C12 89.76(9) . . ?
C10 C11 C8 89.69(9) . . ?
C12 C11 C8 90.33(9) . . ?
C10 C11 H17 125.3 . . ?
C12 C11 H17 125.3 . . ?
C8 C11 H17 125.3 . . ?
C15 C12 C11 90.70(9) . . ?
C15 C12 C13 90.48(9) . . ?
C11 C12 C13 90.00(9) . . ?
C15 C12 H18 125.0 . . ?
C11 C12 H18 125.0 . . ?
C13 C12 H18 125.0 . . ?
C26 C13 C10 122.45(10) . . ?
C26 C13 C12 125.55(10) . . ?
C10 C13 C12 89.47(9) . . ?
C26 C13 C14 128.44(10) . . ?
C10 C13 C14 89.72(9) . . ?
C12 C13 C14 89.72(9) . . ?
C9 C14 C13 89.58(9) . . ?
C9 C14 C15 90.39(9) . . ?
C13 C14 C15 89.71(9) . . ?
C9 C14 H19 125.3 . . ?
C13 C14 H19 125.3 . . ?
C15 C14 H19 125.3 . . ?
C16 C15 C12 126.03(10) . . ?
C16 C15 C14 125.77(10) . . ?
C12 C15 C14 90.08(9) . . ?
C16 C15 C8 124.83(10) . . ?
C12 C15 C8 89.89(8) . . ?
C14 C15 C8 88.80(8) . . ?
C17 C16 C25 118.89(11) . . ?
C17 C16 C15 121.36(11) . . ?
C25 C16 C15 119.75(11) . . ?
C16 C17 C18 121.71(11) . . ?
C16 C17 H20 119.1 . . ?
C18 C17 H20 119.1 . . ?
C19 C18 C17 122.37(12) . . ?
C19 C18 C23 118.78(11) . . ?
C17 C18 C23 118.84(11) . . ?
C20 C19 C18 120.54(13) . . ?
C20 C19 H21 119.7 . . ?
C18 C19 H21 119.7 . . ?
C19 C20 C21 120.59(13) . . ?
C19 C20 H22 119.7 . . ?
C21 C20 H22 119.7 . . ?
C22 C21 C20 120.41(12) . . ?
C22 C21 H23 119.8 . . ?
C20 C21 H23 119.8 . . ?
C21 C22 C23 120.53(13) . . ?
C21 C22 H24 119.7 . . ?
C23 C22 H24 119.7 . . ?
C22 C23 C24 122.33(12) . . ?
C22 C23 C18 119.14(12) . . ?
C24 C23 C18 118.52(11) . . ?
C25 C24 C23 121.11(12) . . ?
C25 C24 H25 119.4 . . ?
C23 C24 H25 119.4 . . ?
C24 C25 C16 120.90(11) . . ?
C24 C25 H26 119.5 . . ?
C16 C25 H26 119.5 . . ?
O2 C26 N2 122.51(11) . . ?
O2 C26 C13 119.21(11) . . ?
N2 C26 C13 118.27(10) . . ?
C26 N2 C27 123.02(10) . . ?
C26 N2 C30 119.62(10) . . ?
C27 N2 C30 117.32(10) . . ?
N2 C27 C29 111.12(11) . . ?
N2 C27 C28 112.24(11) . . ?
C29 C27 C28 112.20(11) . . ?
N2 C27 H27 107.0 . . ?
C29 C27 H27 107.0 . . ?
C28 C27 H27 107.0 . . ?
C27 C28 H28 109.5 . . ?
C27 C28 H29 109.5 . . ?
H28 C28 H29 109.5 . . ?
C27 C28 H30 109.5 . . ?
H28 C28 H30 109.5 . . ?
H29 C28 H30 109.5 . . ?
C27 C29 H31 109.5 . . ?
C27 C29 H32 109.5 . . ?
H31 C29 H32 109.5 . . ?
C27 C29 H33 109.5 . . ?
H31 C29 H33 109.5 . . ?
H32 C29 H33 109.5 . . ?
N2 C30 C32 112.81(11) . . ?
N2 C30 C31 111.10(11) . . ?
C32 C30 C31 112.91(12) . . ?
N2 C30 H34 106.5 . . ?
C32 C30 H34 106.5 . . ?
C31 C30 H34 106.5 . . ?
C30 C31 H35 109.5 . . ?
C30 C31 H36 109.5 . . ?
H35 C31 H36 109.5 . . ?
C30 C31 H37 109.5 . . ?
H35 C31 H37 109.5 . . ?
H36 C31 H37 109.5 . . ?
C30 C32 H38 109.5 . . ?
C30 C32 H39 109.5 . . ?
H38 C32 H39 109.5 . . ?
C30 C32 H40 109.5 . . ?
H38 C32 H40 109.5 . . ?
H39 C32 H40 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C5 174.51(11) . . . . ?
C8 C1 N1 C5 -3.68(17) . . . . ?
O1 C1 N1 C2 -3.97(18) . . . . ?
C8 C1 N1 C2 177.84(11) . . . . ?
C1 N1 C2 C3 67.33(15) . . . . ?
C5 N1 C2 C3 -111.24(13) . . . . ?
C1 N1 C2 C4 -60.64(16) . . . . ?
C5 N1 C2 C4 120.80(13) . . . . ?
C1 N1 C5 C7 111.52(14) . . . . ?
C2 N1 C5 C7 -69.96(15) . . . . ?
C1 N1 C5 C6 -121.89(13) . . . . ?
C2 N1 C5 C6 56.63(15) . . . . ?
O1 C1 C8 C9 12.91(16) . . . . ?
N1 C1 C8 C9 -168.83(11) . . . . ?
O1 C1 C8 C11 135.24(13) . . . . ?
N1 C1 C8 C11 -46.50(18) . . . . ?
O1 C1 C8 C15 -99.14(13) . . . . ?
N1 C1 C8 C15 79.13(15) . . . . ?
C1 C8 C9 C14 -127.96(11) . . . . ?
C11 C8 C9 C14 90.10(9) . . . . ?
C15 C8 C9 C14 1.03(9) . . . . ?
C1 C8 C9 C10 141.54(11) . . . . ?
C11 C8 C9 C10 -0.40(9) . . . . ?
C15 C8 C9 C10 -89.47(9) . . . . ?
C14 C9 C10 C13 0.23(9) . . . . ?
C8 C9 C10 C13 91.17(9) . . . . ?
C14 C9 C10 C11 -90.54(9) . . . . ?
C8 C9 C10 C11 0.40(9) . . . . ?
C9 C10 C11 C12 89.94(9) . . . . ?
C13 C10 C11 C12 -0.28(9) . . . . ?
C9 C10 C11 C8 -0.40(9) . . . . ?
C13 C10 C11 C8 -90.61(9) . . . . ?
C1 C8 C11 C10 -132.73(13) . . . . ?
C9 C8 C11 C10 0.40(9) . . . . ?
C15 C8 C11 C10 90.25(9) . . . . ?
C1 C8 C11 C12 137.52(13) . . . . ?
C9 C8 C11 C12 -89.36(9) . . . . ?
C15 C8 C11 C12 0.50(9) . . . . ?
C10 C11 C12 C15 -90.20(9) . . . . ?
C8 C11 C12 C15 -0.51(9) . . . . ?
C10 C11 C12 C13 0.27(9) . . . . ?
C8 C11 C12 C13 89.97(9) . . . . ?
C9 C10 C13 C26 136.97(11) . . . . ?
C11 C10 C13 C26 -132.81(11) . . . . ?
C9 C10 C13 C12 -89.95(9) . . . . ?
C11 C10 C13 C12 0.27(9) . . . . ?
C9 C10 C13 C14 -0.22(9) . . . . ?
C11 C10 C13 C14 90.00(9) . . . . ?
C15 C12 C13 C26 -138.81(12) . . . . ?
C11 C12 C13 C26 130.49(12) . . . . ?
C15 C12 C13 C10 90.43(9) . . . . ?
C11 C12 C13 C10 -0.27(9) . . . . ?
C15 C12 C13 C14 0.70(9) . . . . ?
C11 C12 C13 C14 -89.99(9) . . . . ?
C10 C9 C14 C13 -0.22(9) . . . . ?
C8 C9 C14 C13 -90.74(9) . . . . ?
C10 C9 C14 C15 89.48(9) . . . . ?
C8 C9 C14 C15 -1.04(9) . . . . ?
C26 C13 C14 C9 -132.71(12) . . . . ?
C10 C13 C14 C9 0.22(9) . . . . ?
C12 C13 C14 C9 89.70(9) . . . . ?
C26 C13 C14 C15 136.89(12) . . . . ?
C10 C13 C14 C15 -90.17(9) . . . . ?
C12 C13 C14 C15 -0.70(9) . . . . ?
C11 C12 C15 C16 -134.32(11) . . . . ?
C13 C12 C15 C16 135.67(12) . . . . ?
C11 C12 C15 C14 89.31(9) . . . . ?
C13 C12 C15 C14 -0.70(9) . . . . ?
C11 C12 C15 C8 0.51(9) . . . . ?
C13 C12 C15 C8 -89.50(8) . . . . ?
C9 C14 C15 C16 134.57(12) . . . . ?
C13 C14 C15 C16 -135.85(12) . . . . ?
C9 C14 C15 C12 -88.88(9) . . . . ?
C13 C14 C15 C12 0.70(9) . . . . ?
C9 C14 C15 C8 1.01(9) . . . . ?
C13 C14 C15 C8 90.59(9) . . . . ?
C1 C8 C15 C16 -8.45(17) . . . . ?
C9 C8 C15 C16 -135.26(11) . . . . ?
C11 C8 C15 C16 135.17(11) . . . . ?
C1 C8 C15 C12 -144.12(11) . . . . ?
C9 C8 C15 C12 89.07(9) . . . . ?
C11 C8 C15 C12 -0.50(9) . . . . ?
C1 C8 C15 C14 125.80(11) . . . . ?
C9 C8 C15 C14 -1.01(9) . . . . ?
C11 C8 C15 C14 -90.59(9) . . . . ?
C12 C15 C16 C17 -12.84(18) . . . . ?
C14 C15 C16 C17 108.92(14) . . . . ?
C8 C15 C16 C17 -133.06(12) . . . . ?
C12 C15 C16 C25 167.77(11) . . . . ?
C14 C15 C16 C25 -70.48(16) . . . . ?
C8 C15 C16 C25 47.55(16) . . . . ?
C25 C16 C17 C18 0.89(18) . . . . ?
C15 C16 C17 C18 -178.51(11) . . . . ?
C16 C17 C18 C19 178.58(12) . . . . ?
C16 C17 C18 C23 -1.68(18) . . . . ?
C17 C18 C19 C20 179.32(12) . . . . ?
C23 C18 C19 C20 -0.42(18) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C20 C21 C22 0.5(2) . . . . ?
C20 C21 C22 C23 -0.30(19) . . . . ?
C21 C22 C23 C24 179.18(12) . . . . ?
C21 C22 C23 C18 -0.22(18) . . . . ?
C19 C18 C23 C22 0.57(17) . . . . ?
C17 C18 C23 C22 -179.18(11) . . . . ?
C19 C18 C23 C24 -178.85(11) . . . . ?
C17 C18 C23 C24 1.40(17) . . . . ?
C22 C23 C24 C25 -179.80(12) . . . . ?
C18 C23 C24 C25 -0.40(18) . . . . ?
C23 C24 C25 C16 -0.40(18) . . . . ?
C17 C16 C25 C24 0.16(18) . . . . ?
C15 C16 C25 C24 179.57(11) . . . . ?
C10 C13 C26 O2 2.63(17) . . . . ?
C12 C13 C26 O2 -113.54(13) . . . . ?
C14 C13 C26 O2 122.45(13) . . . . ?
C10 C13 C26 N2 -178.24(10) . . . . ?
C12 C13 C26 N2 65.59(16) . . . . ?
C14 C13 C26 N2 -58.42(17) . . . . ?
O2 C26 N2 C27 -179.21(11) . . . . ?
C13 C26 N2 C27 1.69(17) . . . . ?
O2 C26 N2 C30 2.86(18) . . . . ?
C13 C26 N2 C30 -176.24(11) . . . . ?
C26 N2 C27 C29 114.75(13) . . . . ?
C30 N2 C27 C29 -67.28(15) . . . . ?
C26 N2 C27 C28 -118.71(13) . . . . ?
C30 N2 C27 C28 59.26(14) . . . . ?
C26 N2 C30 C32 -60.56(16) . . . . ?
C27 N2 C30 C32 121.39(13) . . . . ?
C26 N2 C30 C31 67.39(15) . . . . ?
C27 N2 C30 C31 -110.66(13) . . . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.032



_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration unk
####################################################################### 
# 
# 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_2p
_database_code_depnum_ccdc_archive 'CCDC 1993513'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H39 N3 O2'
_chemical_formula_weight         485.65

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                   8.9740(2)
_cell_length_b                   11.7370(3)
_cell_length_c                   14.0121(3)
_cell_angle_alpha                113.955(2)
_cell_angle_beta                 97.7538(17)
_cell_angle_gamma                91.349(2)
_cell_volume                     1331.40(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    10951

_cell_measurement_theta_min      2.9030

_cell_measurement_theta_max      30.5110


_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.80601

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14591
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4665
_reflns_number_gt                4210
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    SIR97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0405P)²+0.6107P] 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         4665
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.21084(10) 0.17454(8) 0.31688(7) 0.0224(2) Uani 1 1 d . . . . .
C1 C 0.32744(13) 0.20078(11) 0.38159(9) 0.0173(3) Uani 1 1 d . . . . .
N1 N 0.46553(11) 0.21333(10) 0.35656(8) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.60644(14) 0.23449(12) 0.43098(10) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.579207 0.226704 0.495089 0.026 Uiso 1 1 calc R U . . .
C3 C 0.71476(16) 0.13510(14) 0.38475(12) 0.0313(3) Uani 1 1 d . . . . .
H16 H 0.660862 0.051744 0.357021 0.047 Uiso 1 1 calc R U . . .
H17 H 0.798537 0.142536 0.440184 0.047 Uiso 1 1 calc R U . . .
H18 H 0.754367 0.147270 0.327398 0.047 Uiso 1 1 calc R U . . .
C4 C 0.68177(16) 0.36607(13) 0.46689(12) 0.0302(3) Uani 1 1 d . . . . .
H19 H 0.705912 0.378201 0.405311 0.045 Uiso 1 1 calc R U . . .
H20 H 0.774825 0.376969 0.516316 0.045 Uiso 1 1 calc R U . . .
H21 H 0.612999 0.427646 0.502128 0.045 Uiso 1 1 calc R U . . .
C5 C 0.47807(16) 0.20718(13) 0.25005(10) 0.0256(3) Uani 1 1 d . . . . .
H13 H 0.587262 0.226927 0.250581 0.031 Uiso 1 1 calc R U . . .
C6 C 0.39364(18) 0.30666(16) 0.22826(13) 0.0374(4) Uani 1 1 d . . . . .
H22 H 0.284830 0.287329 0.221296 0.056 Uiso 1 1 calc R U . . .
H23 H 0.416954 0.308422 0.162506 0.056 Uiso 1 1 calc R U . . .
H24 H 0.424583 0.388538 0.286905 0.056 Uiso 1 1 calc R U . . .
C7 C 0.43443(19) 0.07573(15) 0.16351(11) 0.0390(4) Uani 1 1 d . . . . .
H25 H 0.495442 0.016136 0.180227 0.058 Uiso 1 1 calc R U . . .
H26 H 0.452549 0.073978 0.095524 0.058 Uiso 1 1 calc R U . . .
H27 H 0.327279 0.052664 0.159199 0.058 Uiso 1 1 calc R U . . .
C8 C 0.31420(13) 0.21709(11) 0.49230(9) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.15547(13) 0.22980(11) 0.52773(9) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.060213 0.234642 0.483902 0.020 Uiso 1 1 calc R U . . .
C10 C 0.22387(13) 0.33285(11) 0.63856(9) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.38558(13) 0.31935(11) 0.60503(9) 0.0181(3) Uani 1 1 d . . . . .
H8 H 0.460524 0.390603 0.618283 0.022 Uiso 1 1 calc R U . . .
C12 C 0.41267(13) 0.21519(11) 0.64659(9) 0.0181(3) Uani 1 1 d . . . . .
H9 H 0.507932 0.209716 0.690071 0.022 Uiso 1 1 calc R U . . .
C13 C 0.34310(13) 0.11283(11) 0.53504(9) 0.0173(3) Uani 1 1 d . . . . .
H10 H 0.386595 0.032016 0.496859 0.021 Uiso 1 1 calc R U . . .
C14 C 0.18311(13) 0.12546(11) 0.56874(9) 0.0165(3) Uani 1 1 d . . . . .
H11 H 0.108471 0.053809 0.554985 0.020 Uiso 1 1 calc R U . . .
C15 C 0.25362(13) 0.22686(11) 0.68161(9) 0.0164(3) Uani 1 1 d . . . . .
C16 C 0.23044(14) 0.22294(11) 0.78452(9) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.34107(10) 0.21389(9) 0.84295(7) 0.0256(2) Uani 1 1 d . . . . .
N2 N 0.08873(12) 0.22608(10) 0.80744(8) 0.0197(2) Uani 1 1 d . . . . .
C17 C 0.06115(16) 0.21737(14) 0.90658(11) 0.0277(3) Uani 1 1 d . . . . .
H14 H -0.049949 0.220694 0.907349 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1000(2) 0.09264(17) 0.90809(14) 0.0452(4) Uani 1 1 d . . . . .
H28 H 0.045828 0.024216 0.844403 0.068 Uiso 1 1 calc R U . . .
H29 H 0.070367 0.087023 0.970935 0.068 Uiso 1 1 calc R U . . .
H30 H 0.208990 0.086292 0.909886 0.068 Uiso 1 1 calc R U . . .
C19 C 0.13747(19) 0.33031(17) 1.00360(11) 0.0393(4) Uani 1 1 d . . . . .
H31 H 0.247240 0.327372 1.009492 0.059 Uiso 1 1 calc R U . . .
H32 H 0.104415 0.329040 1.067055 0.059 Uiso 1 1 calc R U . . .
H33 H 0.109883 0.407235 0.996730 0.059 Uiso 1 1 calc R U . . .
C20 C -0.04346(14) 0.23766(12) 0.73807(10) 0.0212(3) Uani 1 1 d . . . . .
H15 H -0.005906 0.243863 0.676174 0.025 Uiso 1 1 calc R U . . .
C21 C -0.15495(16) 0.12171(14) 0.69495(12) 0.0315(3) Uani 1 1 d . . . . .
H34 H -0.101968 0.046936 0.661787 0.047 Uiso 1 1 calc R U . . .
H35 H -0.234608 0.127537 0.642325 0.047 Uiso 1 1 calc R U . . .
H36 H -0.199970 0.116116 0.753020 0.047 Uiso 1 1 calc R U . . .
C22 C -0.12056(16) 0.35631(14) 0.79250(12) 0.0297(3) Uani 1 1 d . . . . .
H37 H -0.163660 0.351477 0.851536 0.045 Uiso 1 1 calc R U . . .
H38 H -0.201201 0.364551 0.741675 0.045 Uiso 1 1 calc R U . . .
H39 H -0.046384 0.429170 0.819289 0.045 Uiso 1 1 calc R U . . .
C23 C 0.16200(13) 0.45626(11) 0.68748(10) 0.0173(3) Uani 1 1 d . . . . .
N3 N 0.04897(12) 0.47743(10) 0.62733(8) 0.0210(2) Uani 1 1 d . . . . .
C24 C -0.00391(15) 0.59310(12) 0.66428(11) 0.0235(3) Uani 1 1 d . . . . .
H1 H -0.085305 0.608234 0.621277 0.028 Uiso 1 1 calc R U . . .
C25 C 0.05279(15) 0.68812(12) 0.75899(11) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.013117 0.767481 0.779853 0.028 Uiso 1 1 calc R U . . .
C26 C 0.17135(14) 0.66747(12) 0.82598(10) 0.0204(3) Uani 1 1 d . . . . .
C27 C 0.23569(15) 0.76076(12) 0.92677(10) 0.0249(3) Uani 1 1 d . . . . .
H3 H 0.200218 0.841799 0.951080 0.030 Uiso 1 1 calc R U . . .
C28 C 0.34805(16) 0.73460(13) 0.98877(10) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.389650 0.797435 1.056230 0.032 Uiso 1 1 calc R U . . .
C29 C 0.40297(15) 0.61531(13) 0.95373(10) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.480545 0.598120 0.998035 0.030 Uiso 1 1 calc R U . . .
C30 C 0.34543(14) 0.52389(12) 0.85628(10) 0.0214(3) Uani 1 1 d . . . . .
H6 H 0.384406 0.444174 0.832992 0.026 Uiso 1 1 calc R U . . .
C31 C 0.22805(13) 0.54759(11) 0.78999(10) 0.0184(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
O1 C1 1.2304(15) . ?
C1 N1 1.3532(16) . ?
C1 C8 1.5056(17) . ?
N1 C2 1.4721(16) . ?
N1 C5 1.4843(16) . ?
C2 C4 1.5242(19) . ?
C2 C3 1.5282(18) . ?
C2 H12 1.0000 . ?
C3 H16 0.9800 . ?
C3 H17 0.9800 . ?
C3 H18 0.9800 . ?
C4 H19 0.9800 . ?
C4 H20 0.9800 . ?
C4 H21 0.9800 . ?
C5 C6 1.516(2) . ?
C5 C7 1.526(2) . ?
C5 H13 1.0000 . ?
C6 H22 0.9800 . ?
C6 H23 0.9800 . ?
C6 H24 0.9800 . ?
C7 H25 0.9800 . ?
C7 H26 0.9800 . ?
C7 H27 0.9800 . ?
C8 C9 1.5616(16) . ?
C8 C13 1.5784(16) . ?
C8 C11 1.5803(16) . ?
C9 C10 1.5601(16) . ?
C9 C14 1.5617(17) . ?
C9 H7 1.0000 . ?
C10 C23 1.4868(17) . ?
C10 C11 1.5767(16) . ?
C10 C15 1.6014(16) . ?
C11 C12 1.5642(17) . ?
C11 H8 1.0000 . ?
C12 C15 1.5621(16) . ?
C12 C13 1.5661(16) . ?
C12 H9 1.0000 . ?
C13 C14 1.5628(16) . ?
C13 H10 1.0000 . ?
C14 C15 1.5761(16) . ?
C14 H11 1.0000 . ?
C15 C16 1.5030(17) . ?
C16 O2 1.2343(15) . ?
C16 N2 1.3508(16) . ?
N2 C20 1.4746(16) . ?
N2 C17 1.4860(16) . ?
C17 C18 1.521(2) . ?
C17 C19 1.522(2) . ?
C17 H14 1.0000 . ?
C18 H28 0.9800 . ?
C18 H29 0.9800 . ?
C18 H30 0.9800 . ?
C19 H31 0.9800 . ?
C19 H32 0.9800 . ?
C19 H33 0.9800 . ?
C20 C21 1.5242(19) . ?
C20 C22 1.5249(18) . ?
C20 H15 1.0000 . ?
C21 H34 0.9800 . ?
C21 H35 0.9800 . ?
C21 H36 0.9800 . ?
C22 H37 0.9800 . ?
C22 H38 0.9800 . ?
C22 H39 0.9800 . ?
C23 N3 1.3237(16) . ?
C23 C31 1.4331(17) . ?
N3 C24 1.3646(17) . ?
C24 C25 1.3612(19) . ?
C24 H1 0.9500 . ?
C25 C26 1.4139(18) . ?
C25 H2 0.9500 . ?
C26 C31 1.4212(18) . ?
C26 C27 1.4217(18) . ?
C27 C28 1.364(2) . ?
C27 H3 0.9500 . ?
C28 C29 1.408(2) . ?
C28 H4 0.9500 . ?
C29 C30 1.3698(18) . ?
C29 H5 0.9500 . ?
C30 C31 1.4175(18) . ?
C30 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 122.67(11) . . ?
O1 C1 C8 117.96(11) . . ?
N1 C1 C8 119.36(10) . . ?
C1 N1 C2 122.99(10) . . ?
C1 N1 C5 119.46(10) . . ?
C2 N1 C5 117.54(10) . . ?
N1 C2 C4 111.65(11) . . ?
N1 C2 C3 111.55(11) . . ?
C4 C2 C3 111.39(11) . . ?
N1 C2 H12 107.3 . . ?
C4 C2 H12 107.3 . . ?
C3 C2 H12 107.3 . . ?
C2 C3 H16 109.5 . . ?
C2 C3 H17 109.5 . . ?
H16 C3 H17 109.5 . . ?
C2 C3 H18 109.5 . . ?
H16 C3 H18 109.5 . . ?
H17 C3 H18 109.5 . . ?
C2 C4 H19 109.5 . . ?
C2 C4 H20 109.5 . . ?
H19 C4 H20 109.5 . . ?
C2 C4 H21 109.5 . . ?
H19 C4 H21 109.5 . . ?
H20 C4 H21 109.5 . . ?
N1 C5 C6 111.70(11) . . ?
N1 C5 C7 112.04(11) . . ?
C6 C5 C7 113.10(13) . . ?
N1 C5 H13 106.5 . . ?
C6 C5 H13 106.5 . . ?
C7 C5 H13 106.5 . . ?
C5 C6 H22 109.5 . . ?
C5 C6 H23 109.5 . . ?
H22 C6 H23 109.5 . . ?
C5 C6 H24 109.5 . . ?
H22 C6 H24 109.5 . . ?
H23 C6 H24 109.5 . . ?
C5 C7 H25 109.5 . . ?
C5 C7 H26 109.5 . . ?
H25 C7 H26 109.5 . . ?
C5 C7 H27 109.5 . . ?
H25 C7 H27 109.5 . . ?
H26 C7 H27 109.5 . . ?
C1 C8 C9 119.23(10) . . ?
C1 C8 C13 124.29(10) . . ?
C9 C8 C13 89.73(9) . . ?
C1 C8 C11 132.82(10) . . ?
C9 C8 C11 89.73(9) . . ?
C13 C8 C11 89.07(9) . . ?
C10 C9 C8 90.82(9) . . ?
C10 C9 C14 90.83(9) . . ?
C8 C9 C14 90.31(9) . . ?
C10 C9 H7 124.8 . . ?
C8 C9 H7 124.8 . . ?
C14 C9 H7 124.8 . . ?
C23 C10 C9 123.50(10) . . ?
C23 C10 C11 122.45(10) . . ?
C9 C10 C11 89.91(9) . . ?
C23 C10 C15 130.62(10) . . ?
C9 C10 C15 89.74(9) . . ?
C11 C10 C15 88.98(9) . . ?
C12 C11 C10 90.50(9) . . ?
C12 C11 C8 90.41(9) . . ?
C10 C11 C8 89.53(9) . . ?
C12 C11 H8 125.2 . . ?
C10 C11 H8 125.2 . . ?
C8 C11 H8 125.2 . . ?
C15 C12 C11 90.86(9) . . ?
C15 C12 C13 90.28(9) . . ?
C11 C12 C13 90.10(9) . . ?
C15 C12 H9 125.0 . . ?
C11 C12 H9 125.0 . . ?
C13 C12 H9 125.0 . . ?
C14 C13 C12 90.08(9) . . ?
C14 C13 C8 89.65(9) . . ?
C12 C13 C8 90.41(9) . . ?
C14 C13 H10 125.2 . . ?
C12 C13 H10 125.2 . . ?
C8 C13 H10 125.2 . . ?
C9 C14 C13 90.30(9) . . ?
C9 C14 C15 90.61(9) . . ?
C13 C14 C15 89.89(9) . . ?
C9 C14 H11 125.1 . . ?
C13 C14 H11 125.1 . . ?
C15 C14 H11 125.1 . . ?
C16 C15 C12 121.24(10) . . ?
C16 C15 C14 124.88(10) . . ?
C12 C15 C14 89.74(9) . . ?
C16 C15 C10 130.72(10) . . ?
C12 C15 C10 89.66(9) . . ?
C14 C15 C10 88.81(9) . . ?
O2 C16 N2 123.02(11) . . ?
O2 C16 C15 118.56(11) . . ?
N2 C16 C15 118.40(10) . . ?
C16 N2 C20 123.10(10) . . ?
C16 N2 C17 119.75(10) . . ?
C20 N2 C17 117.15(10) . . ?
N2 C17 C18 112.00(12) . . ?
N2 C17 C19 111.22(11) . . ?
C18 C17 C19 113.67(13) . . ?
N2 C17 H14 106.5 . . ?
C18 C17 H14 106.5 . . ?
C19 C17 H14 106.5 . . ?
C17 C18 H28 109.5 . . ?
C17 C18 H29 109.5 . . ?
H28 C18 H29 109.5 . . ?
C17 C18 H30 109.5 . . ?
H28 C18 H30 109.5 . . ?
H29 C18 H30 109.5 . . ?
C17 C19 H31 109.5 . . ?
C17 C19 H32 109.5 . . ?
H31 C19 H32 109.5 . . ?
C17 C19 H33 109.5 . . ?
H31 C19 H33 109.5 . . ?
H32 C19 H33 109.5 . . ?
N2 C20 C21 111.47(11) . . ?
N2 C20 C22 112.17(11) . . ?
C21 C20 C22 111.28(11) . . ?
N2 C20 H15 107.2 . . ?
C21 C20 H15 107.2 . . ?
C22 C20 H15 107.2 . . ?
C20 C21 H34 109.5 . . ?
C20 C21 H35 109.5 . . ?
H34 C21 H35 109.5 . . ?
C20 C21 H36 109.5 . . ?
H34 C21 H36 109.5 . . ?
H35 C21 H36 109.5 . . ?
C20 C22 H37 109.5 . . ?
C20 C22 H38 109.5 . . ?
H37 C22 H38 109.5 . . ?
C20 C22 H39 109.5 . . ?
H37 C22 H39 109.5 . . ?
H38 C22 H39 109.5 . . ?
N3 C23 C31 123.15(11) . . ?
N3 C23 C10 115.28(11) . . ?
C31 C23 C10 121.45(11) . . ?
C23 N3 C24 117.95(11) . . ?
C25 C24 N3 124.03(12) . . ?
C25 C24 H1 118.0 . . ?
N3 C24 H1 118.0 . . ?
C24 C25 C26 119.32(12) . . ?
C24 C25 H2 120.3 . . ?
C26 C25 H2 120.3 . . ?
C25 C26 C31 117.94(11) . . ?
C25 C26 C27 123.05(12) . . ?
C31 C26 C27 119.00(12) . . ?
C28 C27 C26 120.40(12) . . ?
C28 C27 H3 119.8 . . ?
C26 C27 H3 119.8 . . ?
C27 C28 C29 120.63(12) . . ?
C27 C28 H4 119.7 . . ?
C29 C28 H4 119.7 . . ?
C30 C29 C28 120.53(12) . . ?
C30 C29 H5 119.7 . . ?
C28 C29 H5 119.7 . . ?
C29 C30 C31 120.36(12) . . ?
C29 C30 H6 119.8 . . ?
C31 C30 H6 119.8 . . ?
C30 C31 C26 119.07(11) . . ?
C30 C31 C23 123.36(11) . . ?
C26 C31 C23 117.57(11) . . ?

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 N1 C2 -174.84(11) . . . . ?
C8 C1 N1 C2 4.07(17) . . . . ?
O1 C1 N1 C5 5.85(18) . . . . ?
C8 C1 N1 C5 -175.24(11) . . . . ?
C1 N1 C2 C4 -110.57(13) . . . . ?
C5 N1 C2 C4 68.76(14) . . . . ?
C1 N1 C2 C3 124.08(13) . . . . ?
C5 N1 C2 C3 -56.59(15) . . . . ?
C1 N1 C5 C6 58.61(16) . . . . ?
C2 N1 C5 C6 -120.74(13) . . . . ?
C1 N1 C5 C7 -69.46(15) . . . . ?
C2 N1 C5 C7 111.19(13) . . . . ?
O1 C1 C8 C9 -13.43(16) . . . . ?
N1 C1 C8 C9 167.61(10) . . . . ?
O1 C1 C8 C13 98.61(14) . . . . ?
N1 C1 C8 C13 -80.35(15) . . . . ?
O1 C1 C8 C11 -134.16(13) . . . . ?
N1 C1 C8 C11 46.88(18) . . . . ?
C1 C8 C9 C10 -139.81(11) . . . . ?
C13 C8 C9 C10 90.17(9) . . . . ?
C11 C8 C9 C10 1.09(9) . . . . ?
C1 C8 C9 C14 129.35(11) . . . . ?
C13 C8 C9 C14 -0.67(9) . . . . ?
C11 C8 C9 C14 -89.74(9) . . . . ?
C8 C9 C10 C23 128.88(11) . . . . ?
C14 C9 C10 C23 -140.80(11) . . . . ?
C8 C9 C10 C11 -1.10(9) . . . . ?
C14 C9 C10 C11 89.22(9) . . . . ?
C8 C9 C10 C15 -90.07(9) . . . . ?
C14 C9 C10 C15 0.25(8) . . . . ?
C23 C10 C11 C12 139.90(11) . . . . ?
C9 C10 C11 C12 -89.33(9) . . . . ?
C15 C10 C11 C12 0.41(9) . . . . ?
C23 C10 C11 C8 -129.69(11) . . . . ?
C9 C10 C11 C8 1.08(9) . . . . ?
C15 C10 C11 C8 90.82(9) . . . . ?
C1 C8 C11 C12 -139.19(13) . . . . ?
C9 C8 C11 C12 89.41(9) . . . . ?
C13 C8 C11 C12 -0.33(8) . . . . ?
C1 C8 C11 C10 130.31(13) . . . . ?
C9 C8 C11 C10 -1.08(9) . . . . ?
C13 C8 C11 C10 -90.82(9) . . . . ?
C10 C11 C12 C15 -0.42(9) . . . . ?
C8 C11 C12 C15 -89.95(9) . . . . ?
C10 C11 C12 C13 89.86(9) . . . . ?
C8 C11 C12 C13 0.33(8) . . . . ?
C15 C12 C13 C14 0.88(9) . . . . ?
C11 C12 C13 C14 -89.98(9) . . . . ?
C15 C12 C13 C8 90.53(9) . . . . ?
C11 C12 C13 C8 -0.33(8) . . . . ?
C1 C8 C13 C14 -125.34(11) . . . . ?
C9 C8 C13 C14 0.67(9) . . . . ?
C11 C8 C13 C14 90.40(8) . . . . ?
C1 C8 C13 C12 144.59(11) . . . . ?
C9 C8 C13 C12 -89.40(9) . . . . ?
C11 C8 C13 C12 0.33(8) . . . . ?
C10 C9 C14 C13 -90.14(9) . . . . ?
C8 C9 C14 C13 0.68(9) . . . . ?
C10 C9 C14 C15 -0.25(9) . . . . ?
C8 C9 C14 C15 90.57(9) . . . . ?
C12 C13 C14 C9 89.74(9) . . . . ?
C8 C13 C14 C9 -0.67(9) . . . . ?
C12 C13 C14 C15 -0.87(9) . . . . ?
C8 C13 C14 C15 -91.28(9) . . . . ?
C11 C12 C15 C16 -139.00(11) . . . . ?
C13 C12 C15 C16 130.89(11) . . . . ?
C11 C12 C15 C14 89.23(9) . . . . ?
C13 C12 C15 C14 -0.87(9) . . . . ?
C11 C12 C15 C10 0.42(9) . . . . ?
C13 C12 C15 C10 -89.68(9) . . . . ?
C9 C14 C15 C16 141.60(11) . . . . ?
C13 C14 C15 C16 -128.10(11) . . . . ?
C9 C14 C15 C12 -89.43(9) . . . . ?
C13 C14 C15 C12 0.87(9) . . . . ?
C9 C14 C15 C10 0.24(8) . . . . ?
C13 C14 C15 C10 90.54(9) . . . . ?
C23 C10 C15 C16 -1.4(2) . . . . ?
C9 C10 C15 C16 -137.71(12) . . . . ?
C11 C10 C15 C16 132.37(13) . . . . ?
C23 C10 C15 C12 -134.18(13) . . . . ?
C9 C10 C15 C12 89.50(9) . . . . ?
C11 C10 C15 C12 -0.41(9) . . . . ?
C23 C10 C15 C14 136.07(13) . . . . ?
C9 C10 C15 C14 -0.24(8) . . . . ?
C11 C10 C15 C14 -90.16(8) . . . . ?
C12 C15 C16 O2 2.08(17) . . . . ?
C14 C15 C16 O2 116.69(13) . . . . ?
C10 C15 C16 O2 -118.79(14) . . . . ?
C12 C15 C16 N2 -176.15(10) . . . . ?
C14 C15 C16 N2 -61.55(16) . . . . ?
C10 C15 C16 N2 62.98(17) . . . . ?
O2 C16 N2 C20 179.62(11) . . . . ?
C15 C16 N2 C20 -2.23(17) . . . . ?
O2 C16 N2 C17 -0.52(18) . . . . ?
C15 C16 N2 C17 177.63(11) . . . . ?
C16 N2 C17 C18 -63.49(16) . . . . ?
C20 N2 C17 C18 116.38(14) . . . . ?
C16 N2 C17 C19 64.93(16) . . . . ?
C20 N2 C17 C19 -115.20(13) . . . . ?
C16 N2 C20 C21 115.97(13) . . . . ?
C17 N2 C20 C21 -63.89(14) . . . . ?
C16 N2 C20 C22 -118.48(13) . . . . ?
C17 N2 C20 C22 61.66(15) . . . . ?
C9 C10 C23 N3 -4.33(17) . . . . ?
C11 C10 C23 N3 110.42(13) . . . . ?
C15 C10 C23 N3 -128.41(13) . . . . ?
C9 C10 C23 C31 179.46(10) . . . . ?
C11 C10 C23 C31 -65.79(16) . . . . ?
C15 C10 C23 C31 55.38(18) . . . . ?
C31 C23 N3 C24 1.68(18) . . . . ?
C10 C23 N3 C24 -174.46(11) . . . . ?
C23 N3 C24 C25 0.25(19) . . . . ?
N3 C24 C25 C26 -1.6(2) . . . . ?
C24 C25 C26 C31 1.04(18) . . . . ?
C24 C25 C26 C27 -179.04(12) . . . . ?
C25 C26 C27 C28 178.77(13) . . . . ?
C31 C26 C27 C28 -1.32(19) . . . . ?
C26 C27 C28 C29 0.5(2) . . . . ?
C27 C28 C29 C30 0.6(2) . . . . ?
C28 C29 C30 C31 -1.0(2) . . . . ?
C29 C30 C31 C26 0.15(18) . . . . ?
C29 C30 C31 C23 -179.64(12) . . . . ?
C25 C26 C31 C30 -179.10(11) . . . . ?
C27 C26 C31 C30 0.98(18) . . . . ?
C25 C26 C31 C23 0.71(17) . . . . ?
C27 C26 C31 C23 -179.21(11) . . . . ?
N3 C23 C31 C30 177.65(12) . . . . ?
C10 C23 C31 C30 -6.44(18) . . . . ?
N3 C23 C31 C26 -2.15(18) . . . . ?
C10 C23 C31 C26 173.76(11) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036



_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration unk
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1993519'
loop_
_audit_author_name
_audit_author_address
'Akiko Yagi'
;University
Japan
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H37 N3 O2'
_chemical_formula_weight         459.61

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.4161(9)
_cell_length_b                   12.4001(8)
_cell_length_c                   25.3104(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5152.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)

_cell_measurement_reflns_used    5269

_cell_measurement_theta_min      2.9400

_cell_measurement_theta_max      29.6580


_exptl_crystal_description       platelet

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             1984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.40848

_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            35337
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4538
_reflns_number_gt                2985
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    SIR97

_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0448P)²+1.5455P] 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         4538
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
O1 O 0.39820(8) 0.02181(11) 0.46721(6) 0.0273(4) Uani 1 1 d . . . . .
C1 C 0.37373(12) 0.11442(16) 0.47596(8) 0.0212(5) Uani 1 1 d . . . . .
N1 N 0.40083(9) 0.20153(12) 0.44883(6) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.45859(11) 0.18689(16) 0.40405(8) 0.0226(5) Uani 1 1 d . . . . .
H30 H 0.463885 0.258800 0.386497 0.027 Uiso 1 1 calc R U . . .
C3 C 0.42571(13) 0.10950(17) 0.36239(8) 0.0302(5) Uani 1 1 d . . . . .
H1 H 0.421881 0.036826 0.377403 0.045 Uiso 1 1 calc R U . . .
H2 H 0.462558 0.108524 0.331929 0.045 Uiso 1 1 calc R U . . .
H3 H 0.371556 0.133388 0.351053 0.045 Uiso 1 1 calc R U . . .
C4 C 0.54347(12) 0.15667(18) 0.42380(9) 0.0299(5) Uani 1 1 d . . . . .
H4 H 0.564218 0.214050 0.446777 0.045 Uiso 1 1 calc R U . . .
H5 H 0.580142 0.147555 0.393581 0.045 Uiso 1 1 calc R U . . .
H6 H 0.540508 0.089022 0.443728 0.045 Uiso 1 1 calc R U . . .
C5 C 0.37288(12) 0.31240(15) 0.46010(8) 0.0236(5) Uani 1 1 d . . . . .
H31 H 0.340940 0.309816 0.493714 0.028 Uiso 1 1 calc R U . . .
C6 C 0.31568(13) 0.35263(18) 0.41693(9) 0.0341(6) Uani 1 1 d . . . . .
H7 H 0.346471 0.363492 0.384183 0.051 Uiso 1 1 calc R U . . .
H8 H 0.291120 0.421083 0.427920 0.051 Uiso 1 1 calc R U . . .
H9 H 0.272685 0.299193 0.410926 0.051 Uiso 1 1 calc R U . . .
C7 C 0.44417(13) 0.38889(16) 0.46897(9) 0.0305(5) Uani 1 1 d . . . . .
H10 H 0.477624 0.362378 0.498295 0.046 Uiso 1 1 calc R U . . .
H11 H 0.423444 0.460926 0.477511 0.046 Uiso 1 1 calc R U . . .
H12 H 0.477326 0.392586 0.436823 0.046 Uiso 1 1 calc R U . . .
C8 C 0.31436(12) 0.12974(15) 0.52090(8) 0.0213(5) Uani 1 1 d . . . . .
C9 C 0.33997(11) 0.18000(15) 0.57672(8) 0.0206(5) Uani 1 1 d . . . . .
C10 C 0.30350(12) 0.07624(15) 0.60429(8) 0.0224(5) Uani 1 1 d . . . . .
H13 H 0.330622 0.034231 0.633069 0.027 Uiso 1 1 calc R U . . .
C11 C 0.27789(12) 0.02987(16) 0.54928(8) 0.0238(5) Uani 1 1 d . . . . .
H14 H 0.285811 -0.046587 0.537814 0.029 Uiso 1 1 calc R U . . .
C12 C 0.19342(12) 0.08761(16) 0.55424(8) 0.0246(5) Uani 1 1 d . . . . .
H15 H 0.139618 0.053700 0.546032 0.030 Uiso 1 1 calc R U . . .
C13 C 0.22930(11) 0.18880(16) 0.52555(8) 0.0223(5) Uani 1 1 d . . . . .
H16 H 0.201868 0.229835 0.496561 0.027 Uiso 1 1 calc R U . . .
C14 C 0.25506(11) 0.23654(16) 0.58035(8) 0.0207(5) Uani 1 1 d . . . . .
H17 H 0.246213 0.312956 0.591605 0.025 Uiso 1 1 calc R U . . .
C15 C 0.21829(12) 0.13472(15) 0.60914(8) 0.0214(5) Uani 1 1 d . . . . .
C16 C 0.42012(11) 0.22935(15) 0.58895(8) 0.0203(5) Uani 1 1 d . . . . .
C17 C 0.42589(12) 0.33226(16) 0.61067(8) 0.0210(5) Uani 1 1 d . . . . .
H34 H 0.377614 0.372561 0.616873 0.025 Uiso 1 1 calc R U . . .
C18 C 0.50080(12) 0.37703(16) 0.62341(8) 0.0228(5) Uani 1 1 d . . . . .
H35 H 0.503912 0.447348 0.638173 0.027 Uiso 1 1 calc R U . . .
C19 C 0.57127(12) 0.31766(16) 0.61430(8) 0.0229(5) Uani 1 1 d . . . . .
C20 C 0.56691(12) 0.21511(16) 0.59154(8) 0.0256(5) Uani 1 1 d . . . . .
H36 H 0.615338 0.175465 0.584821 0.031 Uiso 1 1 calc R U . . .
C21 C 0.49204(12) 0.17165(16) 0.57888(8) 0.0238(5) Uani 1 1 d . . . . .
H37 H 0.489133 0.102136 0.563212 0.029 Uiso 1 1 calc R U . . .
C22 C 0.64901(14) 0.36175(17) 0.62992(9) 0.0303(5) Uani 1 1 d . . . . .
N2 N 0.70984(12) 0.39751(16) 0.64379(9) 0.0453(6) Uani 1 1 d . . . . .
C23 C 0.16122(12) 0.13737(15) 0.65558(8) 0.0221(5) Uani 1 1 d . . . . .
O2 O 0.09113(8) 0.10259(11) 0.65006(6) 0.0299(4) Uani 1 1 d . . . . .
N3 N 0.18821(10) 0.18043(13) 0.70156(6) 0.0232(4) Uani 1 1 d . . . . .
C24 C 0.27245(12) 0.22090(17) 0.70843(9) 0.0299(5) Uani 1 1 d . . . . .
H32 H 0.301605 0.208311 0.674293 0.036 Uiso 1 1 calc R U . . .
C25 C 0.31766(15) 0.1566(2) 0.75078(10) 0.0485(7) Uani 1 1 d . . . . .
H18 H 0.291442 0.168036 0.785117 0.073 Uiso 1 1 calc R U . . .
H19 H 0.374418 0.180849 0.752528 0.073 Uiso 1 1 calc R U . . .
H20 H 0.316111 0.079733 0.741871 0.073 Uiso 1 1 calc R U . . .
C26 C 0.27454(15) 0.34167(18) 0.71882(10) 0.0441(7) Uani 1 1 d . . . . .
H21 H 0.244447 0.379328 0.690934 0.066 Uiso 1 1 calc R U . . .
H22 H 0.331186 0.366602 0.719112 0.066 Uiso 1 1 calc R U . . .
H23 H 0.249329 0.356889 0.753119 0.066 Uiso 1 1 calc R U . . .
C27 C 0.13250(13) 0.19203(16) 0.74756(8) 0.0262(5) Uani 1 1 d . . . . .
H33 H 0.165075 0.226275 0.776421 0.031 Uiso 1 1 calc R U . . .
C28 C 0.10344(15) 0.08431(18) 0.76874(10) 0.0400(6) Uani 1 1 d . . . . .
H24 H 0.071005 0.047571 0.741672 0.060 Uiso 1 1 calc R U . . .
H25 H 0.069930 0.096076 0.800260 0.060 Uiso 1 1 calc R U . . .
H26 H 0.150599 0.039673 0.777973 0.060 Uiso 1 1 calc R U . . .
C29 C 0.06277(13) 0.26868(18) 0.73550(9) 0.0338(6) Uani 1 1 d . . . . .
H27 H 0.084733 0.337542 0.722927 0.051 Uiso 1 1 calc R U . . .
H28 H 0.030747 0.280780 0.767631 0.051 Uiso 1 1 calc R U . . .
H29 H 0.027849 0.237166 0.708152 0.051 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
O1 C1 1.237(2) . ?
C1 N1 1.355(2) . ?
C1 C8 1.510(3) . ?
N1 C5 1.477(2) . ?
N1 C2 1.489(2) . ?
C2 C3 1.525(3) . ?
C2 C4 1.527(3) . ?
C2 H30 1.0000 . ?
C3 H1 0.9800 . ?
C3 H2 0.9800 . ?
C3 H3 0.9800 . ?
C4 H4 0.9800 . ?
C4 H5 0.9800 . ?
C4 H6 0.9800 . ?
C5 C7 1.523(3) . ?
C5 C6 1.525(3) . ?
C5 H31 1.0000 . ?
C6 H7 0.9800 . ?
C6 H8 0.9800 . ?
C6 H9 0.9800 . ?
C7 H10 0.9800 . ?
C7 H11 0.9800 . ?
C7 H12 0.9800 . ?
C8 C11 1.552(3) . ?
C8 C13 1.581(3) . ?
C8 C9 1.600(3) . ?
C9 C16 1.484(3) . ?
C9 C14 1.563(3) . ?
C9 C10 1.581(3) . ?
C10 C11 1.564(3) . ?
C10 C15 1.580(3) . ?
C10 H13 1.0000 . ?
C11 C12 1.566(3) . ?
C11 H14 1.0000 . ?
C12 C15 1.562(3) . ?
C12 C13 1.565(3) . ?
C12 H15 1.0000 . ?
C13 C14 1.566(3) . ?
C13 H16 1.0000 . ?
C14 C15 1.578(3) . ?
C14 H17 1.0000 . ?
C15 C23 1.504(3) . ?
C16 C17 1.393(3) . ?
C16 C21 1.404(3) . ?
C17 C18 1.387(3) . ?
C17 H34 0.9500 . ?
C18 C19 1.391(3) . ?
C18 H35 0.9500 . ?
C19 C20 1.398(3) . ?
C19 C22 1.444(3) . ?
C20 C21 1.380(3) . ?
C20 H36 0.9500 . ?
C21 H37 0.9500 . ?
C22 N2 1.148(3) . ?
C23 O2 1.237(2) . ?
C23 N3 1.355(2) . ?
N3 C24 1.481(3) . ?
N3 C27 1.488(3) . ?
C24 C26 1.521(3) . ?
C24 C25 1.528(3) . ?
C24 H32 1.0000 . ?
C25 H18 0.9800 . ?
C25 H19 0.9800 . ?
C25 H20 0.9800 . ?
C26 H21 0.9800 . ?
C26 H22 0.9800 . ?
C26 H23 0.9800 . ?
C27 C28 1.516(3) . ?
C27 C29 1.519(3) . ?
C27 H33 1.0000 . ?
C28 H24 0.9800 . ?
C28 H25 0.9800 . ?
C28 H26 0.9800 . ?
C29 H27 0.9800 . ?
C29 H28 0.9800 . ?
C29 H29 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
O1 C1 N1 122.88(18) . . ?
O1 C1 C8 117.48(18) . . ?
N1 C1 C8 119.57(17) . . ?
C1 N1 C5 122.83(16) . . ?
C1 N1 C2 119.85(16) . . ?
C5 N1 C2 117.27(15) . . ?
N1 C2 C3 112.20(16) . . ?
N1 C2 C4 111.21(16) . . ?
C3 C2 C4 113.27(17) . . ?
N1 C2 H30 106.6 . . ?
C3 C2 H30 106.6 . . ?
C4 C2 H30 106.6 . . ?
C2 C3 H1 109.5 . . ?
C2 C3 H2 109.5 . . ?
H1 C3 H2 109.5 . . ?
C2 C3 H3 109.5 . . ?
H1 C3 H3 109.5 . . ?
H2 C3 H3 109.5 . . ?
C2 C4 H4 109.5 . . ?
C2 C4 H5 109.5 . . ?
H4 C4 H5 109.5 . . ?
C2 C4 H6 109.5 . . ?
H4 C4 H6 109.5 . . ?
H5 C4 H6 109.5 . . ?
N1 C5 C7 111.68(16) . . ?
N1 C5 C6 110.95(17) . . ?
C7 C5 C6 112.03(17) . . ?
N1 C5 H31 107.3 . . ?
C7 C5 H31 107.3 . . ?
C6 C5 H31 107.3 . . ?
C5 C6 H7 109.5 . . ?
C5 C6 H8 109.5 . . ?
H7 C6 H8 109.5 . . ?
C5 C6 H9 109.5 . . ?
H7 C6 H9 109.5 . . ?
H8 C6 H9 109.5 . . ?
C5 C7 H10 109.5 . . ?
C5 C7 H11 109.5 . . ?
H10 C7 H11 109.5 . . ?
C5 C7 H12 109.5 . . ?
H10 C7 H12 109.5 . . ?
H11 C7 H12 109.5 . . ?
C1 C8 C11 119.83(17) . . ?
C1 C8 C13 133.18(17) . . ?
C11 C8 C13 89.69(15) . . ?
C1 C8 C9 122.98(16) . . ?
C11 C8 C9 90.20(14) . . ?
C13 C8 C9 89.20(14) . . ?
C16 C9 C14 126.41(16) . . ?
C16 C9 C10 125.39(17) . . ?
C14 C9 C10 90.08(14) . . ?
C16 C9 C8 125.30(16) . . ?
C14 C9 C8 89.56(14) . . ?
C10 C9 C8 88.47(14) . . ?
C11 C10 C15 89.99(15) . . ?
C11 C10 C9 90.46(15) . . ?
C15 C10 C9 89.77(14) . . ?
C11 C10 H13 125.2 . . ?
C15 C10 H13 125.2 . . ?
C9 C10 H13 125.2 . . ?
C8 C11 C10 90.86(14) . . ?
C8 C11 C12 90.79(15) . . ?
C10 C11 C12 89.92(15) . . ?
C8 C11 H14 124.9 . . ?
C10 C11 H14 124.9 . . ?
C12 C11 H14 124.9 . . ?
C15 C12 C13 90.84(14) . . ?
C15 C12 C11 90.62(15) . . ?
C13 C12 C11 89.77(14) . . ?
C15 C12 H15 125.0 . . ?
C13 C12 H15 125.0 . . ?
C11 C12 H15 125.0 . . ?
C12 C13 C14 89.63(15) . . ?
C12 C13 C8 89.75(15) . . ?
C14 C13 C8 90.15(14) . . ?
C12 C13 H16 125.4 . . ?
C14 C13 H16 125.4 . . ?
C8 C13 H16 125.4 . . ?
C9 C14 C13 91.09(14) . . ?
C9 C14 C15 90.53(14) . . ?
C13 C14 C15 90.19(14) . . ?
C9 C14 H17 124.8 . . ?
C13 C14 H17 124.8 . . ?
C15 C14 H17 124.8 . . ?
C23 C15 C12 122.74(16) . . ?
C23 C15 C14 125.58(17) . . ?
C12 C15 C14 89.34(14) . . ?
C23 C15 C10 128.48(17) . . ?
C12 C15 C10 89.47(14) . . ?
C14 C15 C10 89.59(14) . . ?
C17 C16 C21 118.78(18) . . ?
C17 C16 C9 121.37(17) . . ?
C21 C16 C9 119.85(17) . . ?
C18 C17 C16 121.25(19) . . ?
C18 C17 H34 119.4 . . ?
C16 C17 H34 119.4 . . ?
C17 C18 C19 119.14(19) . . ?
C17 C18 H35 120.4 . . ?
C19 C18 H35 120.4 . . ?
C18 C19 C20 120.50(18) . . ?
C18 C19 C22 119.31(18) . . ?
C20 C19 C22 120.17(19) . . ?
C21 C20 C19 119.77(19) . . ?
C21 C20 H36 120.1 . . ?
C19 C20 H36 120.1 . . ?
C20 C21 C16 120.53(19) . . ?
C20 C21 H37 119.7 . . ?
C16 C21 H37 119.7 . . ?
N2 C22 C19 178.0(3) . . ?
O2 C23 N3 122.60(18) . . ?
O2 C23 C15 118.93(18) . . ?
N3 C23 C15 118.45(17) . . ?
C23 N3 C24 122.66(17) . . ?
C23 N3 C27 120.62(16) . . ?
C24 N3 C27 116.69(16) . . ?
N3 C24 C26 112.02(18) . . ?
N3 C24 C25 111.04(18) . . ?
C26 C24 C25 112.42(19) . . ?
N3 C24 H32 107.0 . . ?
C26 C24 H32 107.0 . . ?
C25 C24 H32 107.0 . . ?
C24 C25 H18 109.5 . . ?
C24 C25 H19 109.5 . . ?
H18 C25 H19 109.5 . . ?
C24 C25 H20 109.5 . . ?
H18 C25 H20 109.5 . . ?
H19 C25 H20 109.5 . . ?
C24 C26 H21 109.5 . . ?
C24 C26 H22 109.5 . . ?
H21 C26 H22 109.5 . . ?
C24 C26 H23 109.5 . . ?
H21 C26 H23 109.5 . . ?
H22 C26 H23 109.5 . . ?
N3 C27 C28 112.64(17) . . ?
N3 C27 C29 111.50(17) . . ?
C28 C27 C29 112.66(18) . . ?
N3 C27 H33 106.5 . . ?
C28 C27 H33 106.5 . . ?
C29 C27 H33 106.5 . . ?
C27 C28 H24 109.5 . . ?
C27 C28 H25 109.5 . . ?
H24 C28 H25 109.5 . . ?
C27 C28 H26 109.5 . . ?
H24 C28 H26 109.5 . . ?
H25 C28 H26 109.5 . . ?
C27 C29 H27 109.5 . . ?
C27 C29 H28 109.5 . . ?
H27 C29 H28 109.5 . . ?
C27 C29 H29 109.5 . . ?
H27 C29 H29 109.5 . . ?
H28 C29 H29 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C5 -178.64(18) . . . . ?
C8 C1 N1 C5 -1.9(3) . . . . ?
O1 C1 N1 C2 4.1(3) . . . . ?
C8 C1 N1 C2 -179.25(17) . . . . ?
C1 N1 C2 C3 55.4(2) . . . . ?
C5 N1 C2 C3 -122.02(19) . . . . ?
C1 N1 C2 C4 -72.6(2) . . . . ?
C5 N1 C2 C4 109.96(19) . . . . ?
C1 N1 C5 C7 127.34(19) . . . . ?
C2 N1 C5 C7 -55.3(2) . . . . ?
C1 N1 C5 C6 -106.9(2) . . . . ?
C2 N1 C5 C6 70.5(2) . . . . ?
O1 C1 C8 C11 -7.9(3) . . . . ?
N1 C1 C8 C11 175.24(17) . . . . ?
O1 C1 C8 C13 -129.9(2) . . . . ?
N1 C1 C8 C13 53.3(3) . . . . ?
O1 C1 C8 C9 104.3(2) . . . . ?
N1 C1 C8 C9 -72.6(2) . . . . ?
C1 C8 C9 C16 8.0(3) . . . . ?
C11 C8 C9 C16 134.56(19) . . . . ?
C13 C8 C9 C16 -135.76(19) . . . . ?
C1 C8 C9 C14 144.23(18) . . . . ?
C11 C8 C9 C14 -89.24(14) . . . . ?
C13 C8 C9 C14 0.45(14) . . . . ?
C1 C8 C9 C10 -125.68(18) . . . . ?
C11 C8 C9 C10 0.85(14) . . . . ?
C13 C8 C9 C10 90.54(14) . . . . ?
C16 C9 C10 C11 -134.48(19) . . . . ?
C14 C9 C10 C11 88.71(15) . . . . ?
C8 C9 C10 C11 -0.84(14) . . . . ?
C16 C9 C10 C15 135.53(19) . . . . ?
C14 C9 C10 C15 -1.28(15) . . . . ?
C8 C9 C10 C15 -90.83(14) . . . . ?
C1 C8 C11 C10 128.15(18) . . . . ?
C13 C8 C11 C10 -90.06(14) . . . . ?
C9 C8 C11 C10 -0.86(14) . . . . ?
C1 C8 C11 C12 -141.91(18) . . . . ?
C13 C8 C11 C12 -0.12(15) . . . . ?
C9 C8 C11 C12 89.07(14) . . . . ?
C15 C10 C11 C8 90.64(15) . . . . ?
C9 C10 C11 C8 0.87(14) . . . . ?
C15 C10 C11 C12 -0.15(14) . . . . ?
C9 C10 C11 C12 -89.92(14) . . . . ?
C8 C11 C12 C15 -90.71(15) . . . . ?
C10 C11 C12 C15 0.15(15) . . . . ?
C8 C11 C12 C13 0.13(15) . . . . ?
C10 C11 C12 C13 90.99(14) . . . . ?
C15 C12 C13 C14 0.34(14) . . . . ?
C11 C12 C13 C14 -90.28(14) . . . . ?
C15 C12 C13 C8 90.49(14) . . . . ?
C11 C12 C13 C8 -0.12(15) . . . . ?
C1 C8 C13 C12 132.7(2) . . . . ?
C11 C8 C13 C12 0.12(15) . . . . ?
C9 C8 C13 C12 -90.08(14) . . . . ?
C1 C8 C13 C14 -137.6(2) . . . . ?
C11 C8 C13 C14 89.76(14) . . . . ?
C9 C8 C13 C14 -0.45(14) . . . . ?
C16 C9 C14 C13 135.0(2) . . . . ?
C10 C9 C14 C13 -88.92(15) . . . . ?
C8 C9 C14 C13 -0.45(14) . . . . ?
C16 C9 C14 C15 -134.8(2) . . . . ?
C10 C9 C14 C15 1.28(15) . . . . ?
C8 C9 C14 C15 89.74(14) . . . . ?
C12 C13 C14 C9 90.20(14) . . . . ?
C8 C13 C14 C9 0.46(15) . . . . ?
C12 C13 C14 C15 -0.34(14) . . . . ?
C8 C13 C14 C15 -90.08(14) . . . . ?
C13 C12 C15 C23 132.86(18) . . . . ?
C11 C12 C15 C23 -137.36(18) . . . . ?
C13 C12 C15 C14 -0.34(14) . . . . ?
C11 C12 C15 C14 89.44(14) . . . . ?
C13 C12 C15 C10 -89.93(14) . . . . ?
C11 C12 C15 C10 -0.15(14) . . . . ?
C9 C14 C15 C23 138.18(19) . . . . ?
C13 C14 C15 C23 -130.73(19) . . . . ?
C9 C14 C15 C12 -90.76(14) . . . . ?
C13 C14 C15 C12 0.34(14) . . . . ?
C9 C14 C15 C10 -1.28(15) . . . . ?
C13 C14 C15 C10 89.81(14) . . . . ?
C11 C10 C15 C23 133.3(2) . . . . ?
C9 C10 C15 C23 -136.3(2) . . . . ?
C11 C10 C15 C12 0.15(14) . . . . ?
C9 C10 C15 C12 90.61(14) . . . . ?
C11 C10 C15 C14 -89.19(14) . . . . ?
C9 C10 C15 C14 1.27(15) . . . . ?
C14 C9 C16 C17 6.6(3) . . . . ?
C10 C9 C16 C17 -115.1(2) . . . . ?
C8 C9 C16 C17 127.3(2) . . . . ?
C14 C9 C16 C21 -173.75(19) . . . . ?
C10 C9 C16 C21 64.5(3) . . . . ?
C8 C9 C16 C21 -53.1(3) . . . . ?
C21 C16 C17 C18 -1.4(3) . . . . ?
C9 C16 C17 C18 178.21(18) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 1.4(3) . . . . ?
C17 C18 C19 C22 -176.93(19) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C22 C19 C20 C21 177.14(19) . . . . ?
C19 C20 C21 C16 -0.4(3) . . . . ?
C17 C16 C21 C20 1.7(3) . . . . ?
C9 C16 C21 C20 -177.99(19) . . . . ?
C12 C15 C23 O2 -1.3(3) . . . . ?
C14 C15 C23 O2 115.0(2) . . . . ?
C10 C15 C23 O2 -121.1(2) . . . . ?
C12 C15 C23 N3 -179.64(17) . . . . ?
C14 C15 C23 N3 -63.3(3) . . . . ?
C10 C15 C23 N3 60.6(3) . . . . ?
O2 C23 N3 C24 179.23(18) . . . . ?
C15 C23 N3 C24 -2.5(3) . . . . ?
O2 C23 N3 C27 -2.6(3) . . . . ?
C15 C23 N3 C27 175.71(17) . . . . ?
C23 N3 C24 C26 116.0(2) . . . . ?
C27 N3 C24 C26 -62.3(2) . . . . ?
C23 N3 C24 C25 -117.4(2) . . . . ?
C27 N3 C24 C25 64.3(2) . . . . ?
C23 N3 C27 C28 64.5(2) . . . . ?
C24 N3 C27 C28 -117.3(2) . . . . ?
C23 N3 C27 C29 -63.3(2) . . . . ?
C24 N3 C27 C29 114.9(2) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.044



_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration unk
