# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_jm131
_database_code_depnum_ccdc_archive 'CCDC 1913301'
loop_
_audit_author_name
_audit_author_address
'Wan-chi Hsieh'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C26 H25 N3 O3'
_chemical_formula_sum            'C26 H25 N3 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         427.49

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                   6.5794(3)
_cell_length_b                   11.6584(6)
_cell_length_c                   14.6736(8)
_cell_angle_alpha                91.4149(17)
_cell_angle_beta                 101.2974(16)
_cell_angle_gamma                104.8661(16)
_cell_volume                     1063.45(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9945
_cell_measurement_theta_min      3.247
_cell_measurement_theta_max      27.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8930
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21868
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.247
_diffrn_reflns_theta_max         27.143
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4698
_reflns_number_gt                3997
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.4399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4698
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.05673(14) 0.08480(8) 0.90133(6) 0.0235(2) Uani 1 1 d . . . . .
O2 O 0.05216(15) -0.02150(8) 0.63278(6) 0.0250(2) Uani 1 1 d . . . . .
O3 O 0.39495(16) 0.18547(10) 0.92548(7) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.42345(18) 0.13057(10) 0.64586(8) 0.0224(2) Uani 1 1 d . . . . .
H1A H 0.313(3) 0.0594(18) 0.6200(14) 0.050(5) Uiso 1 1 d . . . . .
N2 N 0.91897(19) 0.38360(10) 0.40633(8) 0.0263(3) Uani 1 1 d . . . . .
N3 N 0.98683(19) 0.59895(10) 0.91145(8) 0.0269(3) Uani 1 1 d . . . . .
C1 C -0.12511(19) 0.00983(11) 0.84690(9) 0.0188(2) Uani 1 1 d . . . . .
C2 C -0.3014(2) -0.02633(12) 0.88852(9) 0.0238(3) Uani 1 1 d . . . . .
H2A H -0.2947 0.0020 0.9506 0.029 Uiso 1 1 calc R U . . .
C3 C -0.4862(2) -0.10421(12) 0.83776(10) 0.0269(3) Uani 1 1 d . . . . .
H3A H -0.6081 -0.1295 0.8652 0.032 Uiso 1 1 calc R U . . .
C4 C -0.4964(2) -0.14633(12) 0.74680(10) 0.0275(3) Uani 1 1 d . . . . .
H4A H -0.6241 -0.2008 0.7130 0.033 Uiso 1 1 calc R U . . .
C5 C -0.3216(2) -0.10917(11) 0.70587(9) 0.0235(3) Uani 1 1 d . . . . .
H5A H -0.3292 -0.1378 0.6438 0.028 Uiso 1 1 calc R U . . .
C6 C -0.13241(19) -0.02917(10) 0.75575(8) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.0549(2) 0.01663(10) 0.71350(8) 0.0185(2) Uani 1 1 d . . . . .
C8 C 0.23124(19) 0.10753(11) 0.76847(8) 0.0190(3) Uani 1 1 d . . . . .
C9 C 0.2420(2) 0.13136(11) 0.86747(9) 0.0219(3) Uani 1 1 d . . . . .
C10 C 0.40391(19) 0.17053(11) 0.72838(9) 0.0188(2) Uani 1 1 d . . . . .
C11 C 0.5542(2) 0.19661(11) 0.58713(9) 0.0202(3) Uani 1 1 d . . . . .
C12 C 0.7027(2) 0.14975(11) 0.55461(9) 0.0213(3) Uani 1 1 d . . . . .
H12A H 0.7212 0.0750 0.5733 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8244(2) 0.21071(11) 0.49515(9) 0.0209(3) Uani 1 1 d . . . . .
H13A H 0.9270 0.1778 0.4744 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7983(2) 0.32077(11) 0.46495(8) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.6445(2) 0.36566(12) 0.49785(9) 0.0237(3) Uani 1 1 d . . . . .
H15A H 0.6218 0.4393 0.4783 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5260(2) 0.30466(12) 0.55798(9) 0.0240(3) Uani 1 1 d . . . . .
H16A H 0.4240 0.3372 0.5796 0.029 Uiso 1 1 calc R U . . .
C17 C 1.0668(2) 0.33440(13) 0.36722(10) 0.0287(3) Uani 1 1 d . . . . .
H17A H 1.1376 0.3913 0.3277 0.043 Uiso 1 1 calc R U . . .
H17B H 1.1754 0.3187 0.4177 0.043 Uiso 1 1 calc R U . . .
H17C H 0.9876 0.2599 0.3298 0.043 Uiso 1 1 calc R U . . .
C18 C 0.8495(2) 0.47918(13) 0.35913(10) 0.0305(3) Uani 1 1 d . . . . .
H18A H 0.9509 0.5149 0.3203 0.046 Uiso 1 1 calc R U . . .
H18B H 0.7059 0.4473 0.3197 0.046 Uiso 1 1 calc R U . . .
H18C H 0.8447 0.5399 0.4055 0.046 Uiso 1 1 calc R U . . .
C19 C 0.55784(19) 0.28256(10) 0.77378(8) 0.0179(2) Uani 1 1 d . . . . .
C20 C 0.77866(19) 0.29456(11) 0.79569(9) 0.0189(2) Uani 1 1 d . . . . .
H20A H 0.8326 0.2305 0.7792 0.023 Uiso 1 1 calc R U . . .
C21 C 0.92019(19) 0.39823(11) 0.84101(9) 0.0197(3) Uani 1 1 d . . . . .
H21A H 1.0694 0.4031 0.8570 0.024 Uiso 1 1 calc R U . . .
C22 C 0.8478(2) 0.49680(11) 0.86399(8) 0.0198(3) Uani 1 1 d . . . . .
C23 C 0.6253(2) 0.48548(11) 0.83771(9) 0.0230(3) Uani 1 1 d . . . . .
H23A H 0.5712 0.5514 0.8490 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4849(2) 0.37961(11) 0.79578(9) 0.0220(3) Uani 1 1 d . . . . .
H24A H 0.3349 0.3729 0.7816 0.026 Uiso 1 1 calc R U . . .
C25 C 1.2172(2) 0.61477(13) 0.92766(10) 0.0292(3) Uani 1 1 d . . . . .
H25A H 1.2915 0.6920 0.9622 0.044 Uiso 1 1 calc R U . . .
H25B H 1.2547 0.5510 0.9640 0.044 Uiso 1 1 calc R U . . .
H25C H 1.2611 0.6121 0.8677 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9121(3) 0.70392(13) 0.92474(12) 0.0364(4) Uani 1 1 d . . . . .
H26A H 1.0316 0.7679 0.9598 0.055 Uiso 1 1 calc R U . . .
H26B H 0.8579 0.7299 0.8639 0.055 Uiso 1 1 calc R U . . .
H26C H 0.7965 0.6848 0.9596 0.055 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 1.3740(15) . ?
O1 C9 1.3925(15) . ?
O2 C7 1.2500(15) . ?
O3 C9 1.2029(16) . ?
N1 C10 1.3281(16) . ?
N1 C11 1.4348(16) . ?
N1 H1A 0.96(2) . ?
N2 C14 1.3811(16) . ?
N2 C17 1.4468(17) . ?
N2 C18 1.4513(18) . ?
N3 C22 1.3749(16) . ?
N3 C25 1.4493(18) . ?
N3 C26 1.4533(18) . ?
C1 C2 1.3913(18) . ?
C1 C6 1.3897(17) . ?
C2 C3 1.3795(19) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3781(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4030(17) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4717(17) . ?
C7 C8 1.4422(17) . ?
C8 C10 1.4252(17) . ?
C8 C9 1.4568(17) . ?
C10 C19 1.4796(17) . ?
C11 C12 1.3877(18) . ?
C11 C16 1.3855(18) . ?
C12 C13 1.3856(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.4085(17) . ?
C13 H13A 0.9500 . ?
C14 C15 1.4075(18) . ?
C15 C16 1.3813(18) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3944(17) . ?
C19 C24 1.3914(17) . ?
C20 C21 1.3821(17) . ?
C20 H20A 0.9500 . ?
C21 C22 1.4092(17) . ?
C21 H21A 0.9500 . ?
C22 C23 1.4093(18) . ?
C23 C24 1.3820(18) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C1 O1 C9 122.28(10) . . ?
C10 N1 C11 125.69(11) . . ?
C10 N1 H1A 113.2(12) . . ?
C11 N1 H1A 119.4(12) . . ?
C14 N2 C17 121.08(11) . . ?
C14 N2 C18 119.10(11) . . ?
C17 N2 C18 116.76(11) . . ?
C22 N3 C25 120.31(11) . . ?
C22 N3 C26 120.43(12) . . ?
C25 N3 C26 117.38(12) . . ?
O1 C1 C2 116.24(11) . . ?
O1 C1 C6 122.08(11) . . ?
C2 C1 C6 121.67(11) . . ?
C3 C2 C1 118.60(12) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 120.84(12) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 120.13(12) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.11(12) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 118.63(11) . . ?
C1 C6 C7 119.44(11) . . ?
C5 C6 C7 121.91(11) . . ?
O2 C7 C8 123.62(11) . . ?
O2 C7 C6 119.66(11) . . ?
C8 C7 C6 116.69(11) . . ?
C10 C8 C7 120.71(11) . . ?
C10 C8 C9 118.84(11) . . ?
C7 C8 C9 120.35(11) . . ?
O3 C9 O1 114.68(11) . . ?
O3 C9 C8 127.78(12) . . ?
O1 C9 C8 117.52(11) . . ?
N1 C10 C8 119.33(11) . . ?
N1 C10 C19 118.47(11) . . ?
C8 C10 C19 122.14(11) . . ?
C12 C11 C16 119.05(11) . . ?
C12 C11 N1 120.21(11) . . ?
C16 C11 N1 120.65(11) . . ?
C13 C12 C11 120.76(11) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C14 120.96(11) . . ?
C12 C13 H13A 119.5 . . ?
C14 C13 H13A 119.5 . . ?
N2 C14 C13 121.99(11) . . ?
N2 C14 C15 120.79(11) . . ?
C13 C14 C15 117.22(11) . . ?
C16 C15 C14 121.24(12) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C15 C16 C11 120.76(12) . . ?
C15 C16 H16A 119.6 . . ?
C11 C16 H16A 119.6 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 118.02(11) . . ?
C20 C19 C10 121.54(11) . . ?
C24 C19 C10 120.45(11) . . ?
C21 C20 C19 120.98(11) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C22 121.39(11) . . ?
C20 C21 H21A 119.3 . . ?
C22 C21 H21A 119.3 . . ?
N3 C22 C23 121.21(12) . . ?
N3 C22 C21 121.71(12) . . ?
C23 C22 C21 117.07(11) . . ?
C24 C23 C22 120.80(12) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C19 121.62(12) . . ?
C23 C24 H24A 119.2 . . ?
C19 C24 H24A 119.2 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C9 O1 C1 C2 -177.54(11) . . . . ?
C9 O1 C1 C6 3.26(18) . . . . ?
O1 C1 C2 C3 -178.26(11) . . . . ?
C6 C1 C2 C3 0.94(19) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
O1 C1 C6 C5 177.66(11) . . . . ?
C2 C1 C6 C5 -1.50(18) . . . . ?
O1 C1 C6 C7 -3.97(18) . . . . ?
C2 C1 C6 C7 176.88(11) . . . . ?
C4 C5 C6 C1 0.88(19) . . . . ?
C4 C5 C6 C7 -177.45(12) . . . . ?
C1 C6 C7 O2 177.34(11) . . . . ?
C5 C6 C7 O2 -4.34(18) . . . . ?
C1 C6 C7 C8 -4.52(17) . . . . ?
C5 C6 C7 C8 173.80(11) . . . . ?
O2 C7 C8 C10 8.05(19) . . . . ?
C6 C7 C8 C10 -170.01(11) . . . . ?
O2 C7 C8 C9 -168.23(12) . . . . ?
C6 C7 C8 C9 13.71(17) . . . . ?
C1 O1 C9 O3 -172.69(12) . . . . ?
C1 O1 C9 C8 5.98(18) . . . . ?
C10 C8 C9 O3 -12.5(2) . . . . ?
C7 C8 C9 O3 163.88(14) . . . . ?
C10 C8 C9 O1 169.07(11) . . . . ?
C7 C8 C9 O1 -14.59(18) . . . . ?
C11 N1 C10 C8 164.68(12) . . . . ?
C11 N1 C10 C19 -12.69(19) . . . . ?
C7 C8 C10 N1 -12.68(18) . . . . ?
C9 C8 C10 N1 163.64(12) . . . . ?
C7 C8 C10 C19 164.59(11) . . . . ?
C9 C8 C10 C19 -19.08(18) . . . . ?
C10 N1 C11 C12 126.75(14) . . . . ?
C10 N1 C11 C16 -56.79(19) . . . . ?
C16 C11 C12 C13 1.14(19) . . . . ?
N1 C11 C12 C13 177.66(11) . . . . ?
C11 C12 C13 C14 -1.02(19) . . . . ?
C17 N2 C14 C13 4.93(19) . . . . ?
C18 N2 C14 C13 164.49(12) . . . . ?
C17 N2 C14 C15 -175.78(12) . . . . ?
C18 N2 C14 C15 -16.23(19) . . . . ?
C12 C13 C14 N2 179.45(12) . . . . ?
C12 C13 C14 C15 0.13(18) . . . . ?
N2 C14 C15 C16 -178.70(12) . . . . ?
C13 C14 C15 C16 0.63(19) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
N1 C11 C16 C15 -176.88(12) . . . . ?
N1 C10 C19 C20 -59.34(16) . . . . ?
C8 C10 C19 C20 123.36(13) . . . . ?
N1 C10 C19 C24 120.59(13) . . . . ?
C8 C10 C19 C24 -56.71(17) . . . . ?
C24 C19 C20 C21 2.34(18) . . . . ?
C10 C19 C20 C21 -177.73(11) . . . . ?
C19 C20 C21 C22 -2.11(18) . . . . ?
C25 N3 C22 C23 -172.32(12) . . . . ?
C26 N3 C22 C23 -8.34(19) . . . . ?
C25 N3 C22 C21 8.89(19) . . . . ?
C26 N3 C22 C21 172.86(12) . . . . ?
C20 C21 C22 N3 178.09(11) . . . . ?
C20 C21 C22 C23 -0.75(18) . . . . ?
N3 C22 C23 C24 -175.49(12) . . . . ?
C21 C22 C23 C24 3.36(19) . . . . ?
C22 C23 C24 C19 -3.2(2) . . . . ?
C20 C19 C24 C23 0.30(19) . . . . ?
C10 C19 C24 C23 -179.63(12) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_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_bmk5735
_database_code_depnum_ccdc_archive 'CCDC 1953598'
loop_
_audit_author_name
_audit_author_address
'Kiran Basappa Manjaapa'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2019-09-14 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O2 S'
_chemical_formula_weight         339.44

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'
S S 0.1246 0.1234 '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                   10.3776(4)
_cell_length_b                   17.4561(5)
_cell_length_c                   10.9103(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.6742(13)
_cell_angle_gamma                90
_cell_volume                     1750.33(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      3.219
_cell_measurement_theta_max      27.881

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8762
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31618
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         27.879
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4149
_reflns_number_gt                3745
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1066P)²+5.6237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4149
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.2570
_refine_ls_wR_factor_gt          0.2513
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.007
_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
S S 1.01350(10) 0.08284(6) 0.66637(11) 0.0359(3) Uani 1 1 d . . . . .
O1 O 0.7231(3) 0.18273(14) 0.4736(2) 0.0266(5) Uani 1 1 d . . . . .
O2 O 0.6283(3) -0.04235(13) 0.2149(2) 0.0243(5) Uani 1 1 d . . . . .
N N 0.7056(3) -0.05394(16) 0.4740(3) 0.0206(6) Uani 1 1 d . . . . .
H0A H 0.663(5) -0.069(3) 0.397(5) 0.029(11) Uiso 1 1 d . . . . .
C1 C 0.7205(3) 0.14737(17) 0.3759(3) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.7155(4) 0.19068(19) 0.2536(3) 0.0256(7) Uani 1 1 d . . . . .
H2A H 0.8155 0.1942 0.2645 0.031 Uiso 1 1 calc R U . . .
H2B H 0.6811 0.2435 0.2544 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6172(4) 0.15410(19) 0.1136(3) 0.0221(6) Uani 1 1 d . . . . .
C4 C 0.6680(3) 0.07150(18) 0.1184(3) 0.0199(6) Uani 1 1 d . . . . .
H4A H 0.6037 0.0460 0.0297 0.024 Uiso 1 1 calc R U . . .
H4B H 0.7678 0.0718 0.1284 0.024 Uiso 1 1 calc R U . . .
C5 C 0.6674(3) 0.02578(18) 0.2357(3) 0.0183(6) Uani 1 1 d . . . . .
C6 C 0.7164(3) 0.06297(17) 0.3688(3) 0.0174(6) Uani 1 1 d . . . . .
C7 C 0.6286(5) 0.1976(2) -0.0027(4) 0.0356(9) Uani 1 1 d . . . . .
H7A H 0.5960 0.2505 -0.0053 0.053 Uiso 1 1 calc R U . . .
H7B H 0.7300 0.1975 0.0142 0.053 Uiso 1 1 calc R U . . .
H7C H 0.5672 0.1726 -0.0914 0.053 Uiso 1 1 calc R U . . .
C8 C 0.4585(4) 0.1550(2) 0.0843(4) 0.0300(8) Uani 1 1 d . . . . .
H8A H 0.4265 0.2081 0.0814 0.045 Uiso 1 1 calc R U . . .
H8B H 0.3981 0.1303 -0.0049 0.045 Uiso 1 1 calc R U . . .
H8C H 0.4489 0.1272 0.1577 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7475(3) 0.01892(18) 0.4881(3) 0.0182(6) Uani 1 1 d . . . . .
C10 C 0.7376(4) -0.11159(17) 0.5769(3) 0.0196(6) Uani 1 1 d . . . . .
C11 C 0.6230(4) -0.15724(19) 0.5644(4) 0.0256(7) Uani 1 1 d . . . . .
H11A H 0.5282 -0.1491 0.4905 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6473(5) -0.2151(2) 0.6607(4) 0.0318(8) Uani 1 1 d . . . . .
H12A H 0.5689 -0.2464 0.6526 0.038 Uiso 1 1 calc R U . . .
C13 C 0.7856(5) -0.2269(2) 0.7681(4) 0.0338(9) Uani 1 1 d . . . . .
H13A H 0.8020 -0.2660 0.8343 0.041 Uiso 1 1 calc R U . . .
C14 C 0.9002(4) -0.1817(2) 0.7789(4) 0.0303(8) Uani 1 1 d . . . . .
H14A H 0.9951 -0.1901 0.8526 0.036 Uiso 1 1 calc R U . . .
C15 C 0.8778(4) -0.12396(19) 0.6831(3) 0.0242(7) Uani 1 1 d . . . . .
H15A H 0.9568 -0.0935 0.6899 0.029 Uiso 1 1 calc R U . . .
C16 C 0.8366(4) 0.04922(19) 0.6293(3) 0.0254(7) Uani 1 1 d . . . . .
C17 C 1.0528(5) 0.0973(3) 0.8368(5) 0.0468(11) Uani 1 1 d . . . . .
H17A H 1.1434 0.1160 0.9060 0.056 Uiso 1 1 calc R U . . .
C18 C 0.9436(5) 0.0795(2) 0.8594(4) 0.0388(10) Uani 1 1 d . . . . .
H18A H 0.9452 0.0854 0.9467 0.047 Uiso 1 1 calc R U . . .
C19 C 0.8250(4) 0.0512(2) 0.7430(4) 0.0339(8) Uani 1 1 d D . . . .
C20 C 0.6894(3) 0.02888(18) 0.7378(3) 0.0284(8) Uani 1 1 d D . . . .
H20A H 0.6967 0.0332 0.8304 0.043 Uiso 1 1 calc R U . . .
H20B H 0.6116 0.0625 0.6737 0.043 Uiso 1 1 calc R U . . .
H20C H 0.6674 -0.0243 0.7059 0.043 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
S C17 1.727(5) . ?
S C16 1.785(4) . ?
O1 C1 1.221(4) . ?
O2 C5 1.243(4) . ?
N C9 1.330(4) . ?
N C10 1.427(4) . ?
N H0A 0.79(5) . ?
C1 C6 1.475(4) . ?
C1 C2 1.514(4) . ?
C2 C3 1.528(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.528(4) . ?
C3 C8 1.526(5) . ?
C3 C7 1.529(4) . ?
C4 C5 1.510(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.450(4) . ?
C6 C9 1.414(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C16 1.478(4) . ?
C10 C11 1.385(5) . ?
C10 C15 1.392(5) . ?
C11 C12 1.393(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.383(6) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.392(5) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C19 1.302(5) . ?
C17 C18 1.305(7) . ?
C17 H17A 0.9500 . ?
C18 C19 1.386(5) . ?
C18 H18A 0.9500 . ?
C19 C20 1.4347(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C17 S C16 89.8(2) . . ?
C9 N C10 129.7(3) . . ?
C9 N H0A 116(3) . . ?
C10 N H0A 114(3) . . ?
O1 C1 C6 122.7(3) . . ?
O1 C1 C2 119.7(3) . . ?
C6 C1 C2 117.6(3) . . ?
C1 C2 C3 114.0(3) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 107.5(3) . . ?
C4 C3 C8 109.8(3) . . ?
C2 C3 C8 111.1(3) . . ?
C4 C3 C7 109.8(3) . . ?
C2 C3 C7 110.4(3) . . ?
C8 C3 C7 108.2(3) . . ?
C5 C4 C3 113.0(3) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
O2 C5 C6 123.0(3) . . ?
O2 C5 C4 118.7(3) . . ?
C6 C5 C4 118.3(3) . . ?
C9 C6 C5 120.1(3) . . ?
C9 C6 C1 120.4(3) . . ?
C5 C6 C1 119.2(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N C9 C6 119.4(3) . . ?
N C9 C16 118.4(3) . . ?
C6 C9 C16 122.0(3) . . ?
C11 C10 C15 120.7(3) . . ?
C11 C10 N 116.9(3) . . ?
C15 C10 N 122.4(3) . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14A 119.6 . . ?
C15 C14 H14A 119.6 . . ?
C10 C15 C14 118.9(3) . . ?
C10 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C19 C16 C9 135.4(3) . . ?
C19 C16 S 108.4(3) . . ?
C9 C16 S 115.7(2) . . ?
C18 C17 S 112.2(3) . . ?
C18 C17 H17A 123.9 . . ?
S C17 H17A 123.9 . . ?
C17 C18 C19 113.1(4) . . ?
C17 C18 H18A 123.5 . . ?
C19 C18 H18A 123.5 . . ?
C20 C19 C16 118.6(3) . . ?
C20 C19 C18 124.8(4) . . ?
C16 C19 C18 116.5(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         2.277
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_jm150
_database_code_depnum_ccdc_archive 'CCDC 1913302'
loop_
_audit_author_name
_audit_author_address
'Wan-chi Hsieh'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2019-05-01 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H19 N3 O3'
_chemical_formula_sum            'C25 H19 N3 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            red
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         409.43

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   22.5681(16)
_cell_length_b                   11.6407(7)
_cell_length_c                   15.4198(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.255(3)
_cell_angle_gamma                90
_cell_volume                     4049.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      3.168
_cell_measurement_theta_max      27.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8963
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41104
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.225
_diffrn_reflns_theta_max         27.115
_diffrn_reflns_theta_full        25.242
_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             4471
_reflns_number_gt                3488
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+3.1513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4471
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.21172(5) 0.85697(9) 1.15554(6) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.22083(5) 1.07066(9) 0.94611(7) 0.0316(3) Uani 1 1 d . . . . .
O3 O 0.13989(5) 0.75517(9) 1.09743(7) 0.0333(3) Uani 1 1 d . . . . .
N1 N 0.15105(5) 0.93957(10) 0.86212(7) 0.0233(3) Uani 1 1 d . . . . .
H1A H 0.1713(8) 1.0068(17) 0.8743(12) 0.044(5) Uiso 1 1 d . . . . .
N2 N 0.05628(8) 0.89266(14) 0.44449(9) 0.0474(4) Uani 1 1 d . . . . .
N3 N 0.00142(6) 0.47853(11) 0.87565(10) 0.0376(3) Uani 1 1 d . . . . .
C1 C 0.24338(6) 0.95706(13) 1.16056(9) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.27039(7) 0.98208(14) 1.24062(10) 0.0318(4) Uani 1 1 d . . . . .
H2A H 0.2684 0.9293 1.2874 0.038 Uiso 1 1 calc R U . . .
C3 C 0.29992(7) 1.08468(15) 1.25038(11) 0.0366(4) Uani 1 1 d . . . . .
H3A H 0.3179 1.1035 1.3048 0.044 Uiso 1 1 calc R U . . .
C4 C 0.30391(7) 1.16157(15) 1.18130(11) 0.0365(4) Uani 1 1 d . . . . .
H4A H 0.3245 1.2322 1.1889 0.044 Uiso 1 1 calc R U . . .
C5 C 0.27804(6) 1.13501(14) 1.10204(10) 0.0302(3) Uani 1 1 d . . . . .
H5A H 0.2812 1.1869 1.0548 0.036 Uiso 1 1 calc R U . . .
C6 C 0.24718(6) 1.03153(12) 1.09107(9) 0.0240(3) Uani 1 1 d . . . . .
C7 C 0.21693(6) 1.00206(12) 1.00850(9) 0.0229(3) Uani 1 1 d . . . . .
C8 C 0.18265(6) 0.89761(11) 1.00550(8) 0.0205(3) Uani 1 1 d . . . . .
C9 C 0.17481(6) 0.83088(12) 1.08467(9) 0.0235(3) Uani 1 1 d . . . . .
C10 C 0.14939(6) 0.86660(11) 0.92860(8) 0.0195(3) Uani 1 1 d . . . . .
C11 C 0.12881(6) 0.92256(12) 0.77601(9) 0.0228(3) Uani 1 1 d . . . . .
C12 C 0.09397(7) 1.00898(13) 0.73938(9) 0.0280(3) Uani 1 1 d . . . . .
H12A H 0.0836 1.0742 0.7728 0.034 Uiso 1 1 calc R U . . .
C13 C 0.07446(7) 0.99950(14) 0.65389(10) 0.0313(4) Uani 1 1 d . . . . .
H13A H 0.0500 1.0575 0.6286 0.038 Uiso 1 1 calc R U . . .
C14 C 0.09085(7) 0.90469(14) 0.60544(9) 0.0299(3) Uani 1 1 d . . . . .
C15 C 0.12622(7) 0.81844(13) 0.64227(9) 0.0293(3) Uani 1 1 d . . . . .
H15A H 0.1374 0.7540 0.6086 0.035 Uiso 1 1 calc R U . . .
C16 C 0.14492(6) 0.82714(13) 0.72805(9) 0.0259(3) Uani 1 1 d . . . . .
H16A H 0.1686 0.7683 0.7539 0.031 Uiso 1 1 calc R U . . .
C17 C 0.07158(8) 0.89725(15) 0.51554(10) 0.0362(4) Uani 1 1 d . . . . .
C18 C 0.11187(6) 0.76436(11) 0.91796(8) 0.0189(3) Uani 1 1 d . . . . .
C19 C 0.05400(6) 0.77687(12) 0.88535(9) 0.0217(3) Uani 1 1 d . . . . .
H19A H 0.0394 0.8517 0.8725 0.026 Uiso 1 1 calc R U . . .
C20 C 0.01761(6) 0.68376(12) 0.87136(9) 0.0242(3) Uani 1 1 d . . . . .
H20A H -0.0217 0.6955 0.8497 0.029 Uiso 1 1 calc R U . . .
C21 C 0.03751(6) 0.57118(12) 0.88859(9) 0.0247(3) Uani 1 1 d . . . . .
C22 C 0.09662(6) 0.55879(12) 0.91993(9) 0.0251(3) Uani 1 1 d . . . . .
H22A H 0.1121 0.4841 0.9306 0.030 Uiso 1 1 calc R U . . .
C23 C 0.13192(6) 0.65314(12) 0.93509(8) 0.0222(3) Uani 1 1 d . . . . .
H23A H 0.1710 0.6424 0.9578 0.027 Uiso 1 1 calc R U . . .
C24 C -0.05943(7) 0.49313(15) 0.84586(12) 0.0407(4) Uani 1 1 d . . . . .
H24A H -0.0785 0.4177 0.8403 0.061 Uiso 1 1 calc R U . . .
H24B H -0.0808 0.5398 0.8878 0.061 Uiso 1 1 calc R U . . .
H24C H -0.0602 0.5317 0.7894 0.061 Uiso 1 1 calc R U . . .
C25 C 0.02197(9) 0.36318(14) 0.89427(13) 0.0440(4) Uani 1 1 d . . . . .
H25A H -0.0099 0.3083 0.8810 0.066 Uiso 1 1 calc R U . . .
H25B H 0.0563 0.3458 0.8586 0.066 Uiso 1 1 calc R U . . .
H25C H 0.0335 0.3573 0.9558 0.066 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 1.3681(18) . ?
O1 C9 1.3931(16) . ?
O2 C7 1.2548(17) . ?
O3 C9 1.2013(18) . ?
N1 C10 1.3325(17) . ?
N1 C11 1.4230(17) . ?
N1 H1A 0.92(2) . ?
N2 C17 1.143(2) . ?
N3 C21 1.3634(19) . ?
N3 C24 1.449(2) . ?
N3 C25 1.447(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.3954(19) . ?
C2 C3 1.374(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.396(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4719(18) . ?
C7 C8 1.4414(19) . ?
C8 C10 1.4355(18) . ?
C8 C9 1.4609(19) . ?
C10 C18 1.4677(18) . ?
C11 C12 1.389(2) . ?
C11 C16 1.387(2) . ?
C12 C13 1.385(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.387(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.396(2) . ?
C14 C17 1.446(2) . ?
C15 C16 1.383(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C18 C23 1.3948(18) . ?
C18 C19 1.3968(18) . ?
C19 C20 1.374(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.409(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.416(2) . ?
C22 C23 1.374(2) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C1 O1 C9 122.19(11) . . ?
C10 N1 C11 127.87(12) . . ?
C10 N1 H1A 113.9(11) . . ?
C11 N1 H1A 118.1(11) . . ?
C21 N3 C24 120.84(13) . . ?
C21 N3 C25 121.14(13) . . ?
C24 N3 C25 117.98(13) . . ?
O1 C1 C6 122.09(12) . . ?
O1 C1 C2 116.44(13) . . ?
C6 C1 C2 121.44(14) . . ?
C3 C2 C1 118.66(15) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 120.86(14) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 119.99(15) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 120.01(16) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 119.01(13) . . ?
C1 C6 C7 119.27(13) . . ?
C5 C6 C7 121.67(13) . . ?
O2 C7 C8 123.98(12) . . ?
O2 C7 C6 118.42(13) . . ?
C8 C7 C6 117.56(12) . . ?
C7 C8 C10 120.61(12) . . ?
C7 C8 C9 119.77(12) . . ?
C10 C8 C9 119.07(12) . . ?
O3 C9 O1 114.49(12) . . ?
O3 C9 C8 128.23(13) . . ?
O1 C9 C8 117.28(12) . . ?
N1 C10 C8 116.89(12) . . ?
N1 C10 C18 117.18(11) . . ?
C8 C10 C18 125.88(12) . . ?
C12 C11 C16 121.05(13) . . ?
C12 C11 N1 117.61(13) . . ?
C16 C11 N1 121.16(13) . . ?
C11 C12 C13 119.64(14) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C14 C13 C12 119.53(14) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C13 C14 C15 120.66(13) . . ?
C13 C14 C17 119.05(15) . . ?
C15 C14 C17 120.28(15) . . ?
C16 C15 C14 119.75(14) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C11 119.35(14) . . ?
C15 C16 H16A 120.3 . . ?
C11 C16 H16A 120.3 . . ?
N2 C17 C14 179.2(2) . . ?
C23 C18 C19 117.50(12) . . ?
C23 C18 C10 123.20(12) . . ?
C19 C18 C10 119.23(12) . . ?
C20 C19 C18 121.69(13) . . ?
C20 C19 H19A 119.2 . . ?
C18 C19 H19A 119.2 . . ?
C19 C20 C21 121.15(12) . . ?
C19 C20 H20A 119.4 . . ?
C21 C20 H20A 119.4 . . ?
N3 C21 C22 121.63(13) . . ?
N3 C21 C20 121.43(13) . . ?
C22 C21 C20 116.94(12) . . ?
C23 C22 C21 120.99(13) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C18 121.70(12) . . ?
C22 C23 H23A 119.1 . . ?
C18 C23 H23A 119.1 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C9 O1 C1 C6 -8.9(2) . . . . ?
C9 O1 C1 C2 169.21(12) . . . . ?
O1 C1 C2 C3 -176.41(13) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
O1 C1 C6 C5 177.02(12) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
O1 C1 C6 C7 -0.8(2) . . . . ?
C2 C1 C6 C7 -178.85(13) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 177.53(14) . . . . ?
C1 C6 C7 O2 179.98(13) . . . . ?
C5 C6 C7 O2 2.2(2) . . . . ?
C1 C6 C7 C8 2.28(19) . . . . ?
C5 C6 C7 C8 -175.48(13) . . . . ?
O2 C7 C8 C10 -0.9(2) . . . . ?
C6 C7 C8 C10 176.64(12) . . . . ?
O2 C7 C8 C9 -172.27(13) . . . . ?
C6 C7 C8 C9 5.29(19) . . . . ?
C1 O1 C9 O3 -163.47(13) . . . . ?
C1 O1 C9 C8 16.20(18) . . . . ?
C7 C8 C9 O3 165.42(14) . . . . ?
C10 C8 C9 O3 -6.1(2) . . . . ?
C7 C8 C9 O1 -14.21(19) . . . . ?
C10 C8 C9 O1 174.31(11) . . . . ?
C11 N1 C10 C8 171.05(13) . . . . ?
C11 N1 C10 C18 -11.4(2) . . . . ?
C7 C8 C10 N1 -1.27(19) . . . . ?
C9 C8 C10 N1 170.14(12) . . . . ?
C7 C8 C10 C18 -178.58(12) . . . . ?
C9 C8 C10 C18 -7.2(2) . . . . ?
C10 N1 C11 C12 131.63(15) . . . . ?
C10 N1 C11 C16 -53.1(2) . . . . ?
C16 C11 C12 C13 0.6(2) . . . . ?
N1 C11 C12 C13 175.94(13) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C12 C13 C14 C17 -178.30(14) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C17 C14 C15 C16 179.28(14) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
N1 C11 C16 C15 -174.78(13) . . . . ?
N1 C10 C18 C23 129.43(14) . . . . ?
C8 C10 C18 C23 -53.27(19) . . . . ?
N1 C10 C18 C19 -47.48(17) . . . . ?
C8 C10 C18 C19 129.82(14) . . . . ?
C23 C18 C19 C20 0.7(2) . . . . ?
C10 C18 C19 C20 177.81(12) . . . . ?
C18 C19 C20 C21 -0.7(2) . . . . ?
C24 N3 C21 C22 178.26(15) . . . . ?
C25 N3 C21 C22 0.6(2) . . . . ?
C24 N3 C21 C20 -1.7(2) . . . . ?
C25 N3 C21 C20 -179.41(15) . . . . ?
C19 C20 C21 N3 179.35(14) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
N3 C21 C22 C23 -178.06(14) . . . . ?
C20 C21 C22 C23 1.9(2) . . . . ?
C21 C22 C23 C18 -1.9(2) . . . . ?
C19 C18 C23 C22 0.6(2) . . . . ?
C10 C18 C23 C22 -176.38(13) . . . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   C2/c
_symmetry_int_tables_number      ?
_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_bmk58893
_database_code_depnum_ccdc_archive 'CCDC 1953599'
loop_
_audit_author_name
_audit_author_address
'Kiran Basappa Manjaapa'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2019-09-14 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         337.36

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   24.7105(17)
_cell_length_b                   7.8341(5)
_cell_length_c                   19.1111(12)
_cell_angle_alpha                90
_cell_angle_beta                 111.589(3)
_cell_angle_gamma                90
_cell_volume                     3440.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9607
_cell_measurement_theta_min      3.100
_cell_measurement_theta_max      27.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8196
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69585
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.745
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_full        25.242
_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             8166
_reflns_number_gt                6436
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²+2.2013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8166
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 -0.01362(6) 0.28171(17) 0.54287(7) 0.0337(3) Uani 1 1 d . . . . .
O2 O -0.08651(5) 0.17230(15) 0.44279(6) 0.0286(3) Uani 1 1 d . . . . .
O3 O 0.07523(5) 0.28969(16) 0.38894(6) 0.0291(3) Uani 1 1 d . . . . .
O4 O 0.18388(6) 0.5493(2) 0.43638(9) 0.0581(5) Uani 1 1 d . . . . .
N1 N -0.03411(6) 0.04376(17) 0.30166(7) 0.0237(3) Uani 1 1 d . . . . .
C1 C -0.02746(7) 0.2214(2) 0.48022(9) 0.0258(3) Uani 1 1 d . . . . .
C2 C -0.09193(7) 0.1079(2) 0.37396(9) 0.0247(3) Uani 1 1 d . . . . .
C3 C -0.14259(7) 0.0566(2) 0.31979(10) 0.0279(3) Uani 1 1 d . . . . .
C4 C -0.13676(8) -0.0071(2) 0.25373(10) 0.0314(4) Uani 1 1 d . . . . .
H4A H -0.1704 -0.0451 0.2134 0.038 Uiso 1 1 calc R U . . .
C5 C -0.08418(8) -0.0152(2) 0.24660(9) 0.0293(3) Uani 1 1 d . . . . .
H5A H -0.0819 -0.0632 0.2021 0.035 Uiso 1 1 calc R U . . .
C6 C -0.03733(7) 0.11207(19) 0.36562(8) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.00322(7) 0.18944(19) 0.43053(8) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.05893(7) 0.26510(19) 0.44163(8) 0.0224(3) Uani 1 1 d . . . . .
C9 C 0.09717(7) 0.3233(2) 0.51995(9) 0.0266(3) Uani 1 1 d . . . . .
H9A H 0.1015 0.2283 0.5557 0.032 Uiso 1 1 calc R U . . .
H9B H 0.0778 0.4189 0.5353 0.032 Uiso 1 1 calc R U . . .
C10 C 0.15754(7) 0.3811(2) 0.52498(9) 0.0297(4) Uani 1 1 d . . . . .
C11 C 0.18853(9) 0.4609(3) 0.60327(11) 0.0436(5) Uani 1 1 d . . . . .
H11A H 0.1940 0.3738 0.6421 0.065 Uiso 1 1 calc R U . . .
H11B H 0.2265 0.5054 0.6069 0.065 Uiso 1 1 calc R U . . .
H11C H 0.1648 0.5543 0.6107 0.065 Uiso 1 1 calc R U . . .
C12 C 0.19412(9) 0.2360(3) 0.51214(12) 0.0429(5) Uani 1 1 d . . . . .
H12A H 0.1980 0.1450 0.5489 0.064 Uiso 1 1 calc R U . . .
H12B H 0.1750 0.1906 0.4611 0.064 Uiso 1 1 calc R U . . .
H12C H 0.2328 0.2792 0.5181 0.064 Uiso 1 1 calc R U . . .
C13 C 0.15092(8) 0.5235(3) 0.46879(11) 0.0365(4) Uani 1 1 d . . . . .
H13A H 0.1185 0.5979 0.4583 0.044 Uiso 1 1 calc R U . . .
C14 C -0.20066(8) 0.0718(3) 0.32736(13) 0.0370(4) Uani 1 1 d . . . . .
H14A H -0.2218(12) -0.033(4) 0.3155(14) 0.059(7) Uiso 1 1 d . . . . .
H14B H -0.2231(12) 0.158(4) 0.2928(15) 0.062(8) Uiso 1 1 d . . . . .
H14C H -0.1986(10) 0.108(3) 0.3770(14) 0.048(6) Uiso 1 1 d . . . . .
C15 C 0.02006(7) 0.0173(2) 0.28997(9) 0.0235(3) Uani 1 1 d . . . . .
C16 C 0.02388(8) 0.0669(2) 0.22231(9) 0.0273(3) Uani 1 1 d . . . . .
H16A H -0.0080 0.1213 0.1847 0.033 Uiso 1 1 calc R U . . .
C17 C 0.07499(8) 0.0359(2) 0.21042(10) 0.0319(4) Uani 1 1 d . . . . .
H17A H 0.0783 0.0704 0.1645 0.038 Uiso 1 1 calc R U . . .
C18 C 0.12105(8) -0.0445(2) 0.26466(10) 0.0329(4) Uani 1 1 d . . . . .
H18A H 0.1561 -0.0643 0.2562 0.039 Uiso 1 1 calc R U . . .
C19 C 0.11646(8) -0.0966(2) 0.33167(10) 0.0309(4) Uani 1 1 d . . . . .
H19A H 0.1481 -0.1536 0.3686 0.037 Uiso 1 1 calc R U . . .
C20 C 0.06560(7) -0.0655(2) 0.34460(9) 0.0267(3) Uani 1 1 d . . . . .
H20A H 0.0621 -0.1006 0.3903 0.032 Uiso 1 1 calc R U . . .
O5 O 0.49813(6) 0.2043(2) 0.55080(7) 0.0404(3) Uani 1 1 d . . . . .
O6 O 0.57157(5) 0.31458(17) 0.52210(7) 0.0339(3) Uani 1 1 d . . . . .
O7 O 0.41263(5) 0.18609(16) 0.31086(6) 0.0317(3) Uani 1 1 d . . . . .
O8 O 0.29782(7) -0.0907(2) 0.26148(9) 0.0621(5) Uani 1 1 d . . . . .
N2 N 0.52228(7) 0.43723(19) 0.33074(8) 0.0304(3) Uani 1 1 d . . . . .
C21 C 0.51261(7) 0.2623(2) 0.50167(10) 0.0307(4) Uani 1 1 d . . . . .
C22 C 0.57786(7) 0.3782(2) 0.45918(10) 0.0308(4) Uani 1 1 d . . . . .
C23 C 0.62843(8) 0.4383(2) 0.45555(12) 0.0371(4) Uani 1 1 d . . . . .
C24 C 0.62410(9) 0.4982(3) 0.38450(13) 0.0430(5) Uani 1 1 d . . . . .
H24A H 0.6581 0.5386 0.3777 0.052 Uiso 1 1 calc R U . . .
C25 C 0.57278(9) 0.4999(2) 0.32528(12) 0.0398(4) Uani 1 1 d . . . . .
H25A H 0.5715 0.5455 0.2786 0.048 Uiso 1 1 calc R U . . .
C26 C 0.52431(7) 0.3682(2) 0.39709(9) 0.0264(3) Uani 1 1 d . . . . .
C27 C 0.48339(7) 0.2897(2) 0.42213(9) 0.0254(3) Uani 1 1 d . . . . .
C28 C 0.42782(7) 0.2128(2) 0.37888(9) 0.0243(3) Uani 1 1 d . . . . .
C29 C 0.38899(7) 0.1572(2) 0.42026(9) 0.0266(3) Uani 1 1 d . . . . .
H29A H 0.3844 0.2541 0.4509 0.032 Uiso 1 1 calc R U . . .
H29B H 0.4085 0.0635 0.4552 0.032 Uiso 1 1 calc R U . . .
C30 C 0.32857(7) 0.0965(2) 0.36879(9) 0.0299(4) Uani 1 1 d . . . . .
C31 C 0.29800(9) 0.0224(3) 0.41929(13) 0.0467(5) Uani 1 1 d . . . . .
H31A H 0.2930 0.1126 0.4519 0.070 Uiso 1 1 calc R U . . .
H31B H 0.2598 -0.0227 0.3877 0.070 Uiso 1 1 calc R U . . .
H31C H 0.3218 -0.0696 0.4503 0.070 Uiso 1 1 calc R U . . .
C32 C 0.29129(9) 0.2379(3) 0.31867(11) 0.0423(5) Uani 1 1 d . . . . .
H32A H 0.2877 0.3326 0.3502 0.063 Uiso 1 1 calc R U . . .
H32B H 0.3098 0.2787 0.2844 0.063 Uiso 1 1 calc R U . . .
H32C H 0.2525 0.1928 0.2894 0.063 Uiso 1 1 calc R U . . .
C33 C 0.33441(8) -0.0504(2) 0.32078(11) 0.0369(4) Uani 1 1 d . . . . .
H33A H 0.3693 -0.1152 0.3386 0.044 Uiso 1 1 calc R U . . .
C34 C 0.68448(9) 0.4378(3) 0.52175(14) 0.0513(6) Uani 1 1 d . . . . .
H34A H 0.7153 0.4863 0.5071 0.077 Uiso 1 1 calc R U . . .
H34B H 0.6803 0.5064 0.5623 0.077 Uiso 1 1 calc R U . . .
H34C H 0.6946 0.3203 0.5393 0.077 Uiso 1 1 calc R U . . .
C35 C 0.46850(8) 0.4678(2) 0.26793(10) 0.0308(4) Uani 1 1 d . . . . .
C36 C 0.46431(10) 0.4216(2) 0.19628(11) 0.0385(4) Uani 1 1 d . . . . .
H36A H 0.4956 0.3650 0.1885 0.046 Uiso 1 1 calc R U . . .
C37 C 0.41384(11) 0.4592(3) 0.13632(11) 0.0454(5) Uani 1 1 d . . . . .
H37A H 0.4103 0.4280 0.0868 0.054 Uiso 1 1 calc R U . . .
C38 C 0.36839(11) 0.5417(3) 0.14772(11) 0.0460(5) Uani 1 1 d . . . . .
H38A H 0.3336 0.5652 0.1061 0.055 Uiso 1 1 calc R U . . .
C39 C 0.37336(9) 0.5906(3) 0.21982(11) 0.0394(4) Uani 1 1 d . . . . .
H39A H 0.3422 0.6487 0.2274 0.047 Uiso 1 1 calc R U . . .
C40 C 0.42384(8) 0.5542(2) 0.28041(10) 0.0332(4) Uani 1 1 d . . . . .
H40A H 0.4279 0.5878 0.3298 0.040 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 1.214(2) . ?
O2 C2 1.3687(19) . ?
O2 C1 1.421(2) . ?
O3 C8 1.2293(18) . ?
O4 C13 1.208(2) . ?
N1 C6 1.3632(19) . ?
N1 C5 1.376(2) . ?
N1 C15 1.451(2) . ?
C1 C7 1.438(2) . ?
C2 C3 1.359(2) . ?
C2 C6 1.416(2) . ?
C3 C4 1.413(2) . ?
C3 C14 1.499(2) . ?
C4 C5 1.357(2) . ?
C4 H4A 0.9500 . ?
C5 H5A 0.9500 . ?
C6 C7 1.413(2) . ?
C7 C8 1.441(2) . ?
C8 C9 1.517(2) . ?
C9 C10 1.528(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.515(2) . ?
C10 C12 1.528(3) . ?
C10 C11 1.540(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.95(3) . ?
C14 H14B 0.96(3) . ?
C14 H14C 0.97(2) . ?
C15 C16 1.386(2) . ?
C15 C20 1.383(2) . ?
C16 C17 1.384(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.378(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
O5 C21 1.209(2) . ?
O6 C22 1.362(2) . ?
O6 C21 1.423(2) . ?
O7 C28 1.2309(19) . ?
O8 C33 1.203(2) . ?
N2 C26 1.362(2) . ?
N2 C25 1.380(2) . ?
N2 C35 1.446(2) . ?
C21 C27 1.439(2) . ?
C22 C23 1.361(2) . ?
C22 C26 1.418(2) . ?
C23 C24 1.403(3) . ?
C23 C34 1.493(3) . ?
C24 C25 1.354(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C27 1.409(2) . ?
C27 C28 1.448(2) . ?
C28 C29 1.515(2) . ?
C29 C30 1.530(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C33 1.511(3) . ?
C30 C32 1.531(3) . ?
C30 C31 1.541(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.383(2) . ?
C35 C40 1.388(3) . ?
C36 C37 1.380(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.381(3) . ?
C37 H37A 0.9500 . ?
C38 C39 1.391(3) . ?
C38 H38A 0.9500 . ?
C39 C40 1.384(3) . ?
C39 H39A 0.9500 . ?
C40 H40A 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
C2 O2 C1 107.61(12) . . ?
C6 N1 C5 119.00(14) . . ?
C6 N1 C15 123.76(13) . . ?
C5 N1 C15 117.08(13) . . ?
O1 C1 O2 117.78(14) . . ?
O1 C1 C7 133.92(16) . . ?
O2 C1 C7 108.28(13) . . ?
C3 C2 O2 125.31(15) . . ?
C3 C2 C6 124.75(15) . . ?
O2 C2 C6 109.84(13) . . ?
C2 C3 C4 114.63(15) . . ?
C2 C3 C14 123.32(16) . . ?
C4 C3 C14 122.02(16) . . ?
C5 C4 C3 121.49(16) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 N1 122.16(15) . . ?
C4 C5 H5A 118.9 . . ?
N1 C5 H5A 118.9 . . ?
N1 C6 C7 134.37(15) . . ?
N1 C6 C2 117.66(14) . . ?
C7 C6 C2 107.96(13) . . ?
C6 C7 C1 106.17(14) . . ?
C6 C7 C8 129.52(14) . . ?
C1 C7 C8 122.57(14) . . ?
O3 C8 C7 121.80(14) . . ?
O3 C8 C9 119.23(14) . . ?
C7 C8 C9 118.91(13) . . ?
C8 C9 C10 112.99(13) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C13 C10 C9 109.00(14) . . ?
C13 C10 C12 110.50(15) . . ?
C9 C10 C12 113.01(16) . . ?
C13 C10 C11 105.97(16) . . ?
C9 C10 C11 107.84(14) . . ?
C12 C10 C11 110.25(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 C10 124.70(18) . . ?
O4 C13 H13A 117.6 . . ?
C10 C13 H13A 117.6 . . ?
C3 C14 H14A 111.7(16) . . ?
C3 C14 H14B 108.7(16) . . ?
H14A C14 H14B 108(2) . . ?
C3 C14 H14C 114.1(14) . . ?
H14A C14 H14C 108(2) . . ?
H14B C14 H14C 106(2) . . ?
C16 C15 C20 121.34(15) . . ?
C16 C15 N1 119.12(14) . . ?
C20 C15 N1 119.43(14) . . ?
C15 C16 C17 118.89(16) . . ?
C15 C16 H16A 120.6 . . ?
C17 C16 H16A 120.6 . . ?
C18 C17 C16 120.51(16) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C17 C18 C19 120.22(16) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
C18 C19 C20 119.94(16) . . ?
C18 C19 H19A 120.0 . . ?
C20 C19 H19A 120.0 . . ?
C15 C20 C19 119.09(15) . . ?
C15 C20 H20A 120.5 . . ?
C19 C20 H20A 120.5 . . ?
C22 O6 C21 107.52(13) . . ?
C26 N2 C25 119.13(16) . . ?
C26 N2 C35 123.12(14) . . ?
C25 N2 C35 117.31(15) . . ?
O5 C21 O6 117.43(15) . . ?
O5 C21 C27 134.39(16) . . ?
O6 C21 C27 108.17(14) . . ?
C23 C22 O6 125.22(17) . . ?
C23 C22 C26 124.62(18) . . ?
O6 C22 C26 110.13(14) . . ?
C22 C23 C24 114.87(18) . . ?
C22 C23 C34 122.59(19) . . ?
C24 C23 C34 122.54(18) . . ?
C25 C24 C23 121.79(17) . . ?
C25 C24 H24A 119.1 . . ?
C23 C24 H24A 119.1 . . ?
C24 C25 N2 121.89(18) . . ?
C24 C25 H25A 119.1 . . ?
N2 C25 H25A 119.1 . . ?
N2 C26 C27 134.75(16) . . ?
N2 C26 C22 117.42(15) . . ?
C27 C26 C22 107.77(15) . . ?
C26 C27 C21 106.27(14) . . ?
C26 C27 C28 129.50(15) . . ?
C21 C27 C28 122.86(14) . . ?
O7 C28 C27 122.01(14) . . ?
O7 C28 C29 119.81(15) . . ?
C27 C28 C29 118.13(13) . . ?
C28 C29 C30 114.16(13) . . ?
C28 C29 H29A 108.7 . . ?
C30 C29 H29A 108.7 . . ?
C28 C29 H29B 108.7 . . ?
C30 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
C33 C30 C32 109.93(15) . . ?
C33 C30 C29 109.78(14) . . ?
C32 C30 C29 113.43(15) . . ?
C33 C30 C31 105.77(16) . . ?
C32 C30 C31 110.08(16) . . ?
C29 C30 C31 107.54(14) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O8 C33 C30 124.43(18) . . ?
O8 C33 H33A 117.8 . . ?
C30 C33 H33A 117.8 . . ?
C23 C34 H34A 109.5 . . ?
C23 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C23 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C40 121.54(18) . . ?
C36 C35 N2 119.32(16) . . ?
C40 C35 N2 118.97(15) . . ?
C37 C36 C35 118.82(19) . . ?
C37 C36 H36A 120.6 . . ?
C35 C36 H36A 120.6 . . ?
C36 C37 C38 120.53(18) . . ?
C36 C37 H37A 119.7 . . ?
C38 C37 H37A 119.7 . . ?
C37 C38 C39 120.3(2) . . ?
C37 C38 H38A 119.9 . . ?
C39 C38 H38A 119.9 . . ?
C40 C39 C38 119.73(19) . . ?
C40 C39 H39A 120.1 . . ?
C38 C39 H39A 120.1 . . ?
C39 C40 C35 119.05(17) . . ?
C39 C40 H40A 120.5 . . ?
C35 C40 H40A 120.5 . . ?

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
C2 O2 C1 O1 -179.80(15) . . . . ?
C2 O2 C1 C7 1.79(17) . . . . ?
C1 O2 C2 C3 -175.90(15) . . . . ?
C1 O2 C2 C6 0.56(17) . . . . ?
O2 C2 C3 C4 -179.35(15) . . . . ?
C6 C2 C3 C4 4.7(2) . . . . ?
O2 C2 C3 C14 2.9(3) . . . . ?
C6 C2 C3 C14 -173.02(16) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C14 C3 C4 C5 177.87(17) . . . . ?
C3 C4 C5 N1 -2.6(3) . . . . ?
C6 N1 C5 C4 0.3(2) . . . . ?
C15 N1 C5 C4 175.78(16) . . . . ?
C5 N1 C6 C7 -176.83(17) . . . . ?
C15 N1 C6 C7 8.0(3) . . . . ?
C5 N1 C6 C2 4.2(2) . . . . ?
C15 N1 C6 C2 -171.02(14) . . . . ?
C3 C2 C6 N1 -7.0(2) . . . . ?
O2 C2 C6 N1 176.51(13) . . . . ?
C3 C2 C6 C7 173.76(15) . . . . ?
O2 C2 C6 C7 -2.72(17) . . . . ?
N1 C6 C7 C1 -175.36(17) . . . . ?
C2 C6 C7 C1 3.70(17) . . . . ?
N1 C6 C7 C8 19.7(3) . . . . ?
C2 C6 C7 C8 -161.26(16) . . . . ?
O1 C1 C7 C6 178.55(19) . . . . ?
O2 C1 C7 C6 -3.40(17) . . . . ?
O1 C1 C7 C8 -15.2(3) . . . . ?
O2 C1 C7 C8 162.86(14) . . . . ?
C6 C7 C8 O3 9.3(3) . . . . ?
C1 C7 C8 O3 -153.47(16) . . . . ?
C6 C7 C8 C9 -173.56(15) . . . . ?
C1 C7 C8 C9 23.6(2) . . . . ?
O3 C8 C9 C10 -9.6(2) . . . . ?
C7 C8 C9 C10 173.19(14) . . . . ?
C8 C9 C10 C13 57.25(19) . . . . ?
C8 C9 C10 C12 -66.01(19) . . . . ?
C8 C9 C10 C11 171.87(15) . . . . ?
C9 C10 C13 O4 -148.0(2) . . . . ?
C12 C10 C13 O4 -23.2(3) . . . . ?
C11 C10 C13 O4 96.2(2) . . . . ?
C6 N1 C15 C16 -133.75(16) . . . . ?
C5 N1 C15 C16 51.0(2) . . . . ?
C6 N1 C15 C20 49.9(2) . . . . ?
C5 N1 C15 C20 -125.38(17) . . . . ?
C20 C15 C16 C17 -1.5(2) . . . . ?
N1 C15 C16 C17 -177.77(15) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C16 C15 C20 C19 1.1(2) . . . . ?
N1 C15 C20 C19 177.38(15) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C22 O6 C21 O5 -178.78(17) . . . . ?
C22 O6 C21 C27 2.57(19) . . . . ?
C21 O6 C22 C23 -178.66(17) . . . . ?
C21 O6 C22 C26 -0.41(19) . . . . ?
O6 C22 C23 C24 -179.73(16) . . . . ?
C26 C22 C23 C24 2.3(3) . . . . ?
O6 C22 C23 C34 1.3(3) . . . . ?
C26 C22 C23 C34 -176.70(18) . . . . ?
C22 C23 C24 C25 1.9(3) . . . . ?
C34 C23 C24 C25 -179.1(2) . . . . ?
C23 C24 C25 N2 -2.4(3) . . . . ?
C26 N2 C25 C24 -1.5(3) . . . . ?
C35 N2 C25 C24 171.09(18) . . . . ?
C25 N2 C26 C27 -177.74(18) . . . . ?
C35 N2 C26 C27 10.2(3) . . . . ?
C25 N2 C26 C22 5.3(2) . . . . ?
C35 N2 C26 C22 -166.81(15) . . . . ?
C23 C22 C26 N2 -5.9(3) . . . . ?
O6 C22 C26 N2 175.79(14) . . . . ?
C23 C22 C26 C27 176.32(17) . . . . ?
O6 C22 C26 C27 -1.95(19) . . . . ?
N2 C26 C27 C21 -173.74(18) . . . . ?
C22 C26 C27 C21 3.43(19) . . . . ?
N2 C26 C27 C28 19.6(3) . . . . ?
C22 C26 C27 C28 -163.27(17) . . . . ?
O5 C21 C27 C26 178.0(2) . . . . ?
O6 C21 C27 C26 -3.71(19) . . . . ?
O5 C21 C27 C28 -14.2(3) . . . . ?
O6 C21 C27 C28 164.09(15) . . . . ?
C26 C27 C28 O7 10.4(3) . . . . ?
C21 C27 C28 O7 -154.37(17) . . . . ?
C26 C27 C28 C29 -172.35(16) . . . . ?
C21 C27 C28 C29 22.9(2) . . . . ?
O7 C28 C29 C30 -9.3(2) . . . . ?
C27 C28 C29 C30 173.35(15) . . . . ?
C28 C29 C30 C33 57.84(19) . . . . ?
C28 C29 C30 C32 -65.6(2) . . . . ?
C28 C29 C30 C31 172.46(15) . . . . ?
C32 C30 C33 O8 -31.3(3) . . . . ?
C29 C30 C33 O8 -156.7(2) . . . . ?
C31 C30 C33 O8 87.5(2) . . . . ?
C26 N2 C35 C36 -134.73(18) . . . . ?
C25 N2 C35 C36 53.0(2) . . . . ?
C26 N2 C35 C40 49.9(2) . . . . ?
C25 N2 C35 C40 -122.34(18) . . . . ?
C40 C35 C36 C37 -1.5(3) . . . . ?
N2 C35 C36 C37 -176.79(17) . . . . ?
C35 C36 C37 C38 0.1(3) . . . . ?
C36 C37 C38 C39 1.1(3) . . . . ?
C37 C38 C39 C40 -0.8(3) . . . . ?
C38 C39 C40 C35 -0.5(3) . . . . ?
C36 C35 C40 C39 1.8(3) . . . . ?
N2 C35 C40 C39 177.03(16) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.046

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

