# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1587031'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C38 H31 N O4'
_chemical_formula_sum            'C38 H31 N O4'
_chemical_formula_weight         565.64

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

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

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

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

_cell_length_a                   9.8430(9)
_cell_length_b                   12.3941(11)
_cell_length_c                   13.6713(14)
_cell_angle_alpha                75.947(6)
_cell_angle_beta                 81.791(6)
_cell_angle_gamma                66.836(5)
_cell_volume                     1485.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4066
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             596
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19767
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.254
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6858
_reflns_number_gt                3751
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0646P)²+0.2005P] 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         6858
_refine_ls_number_parameters     390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.1139(2) 0.78063(18) 0.38373(15) 0.0340(5) Uani 1 1 d . . . . .
C2 C 0.0037(2) 0.7951(2) 0.46026(16) 0.0423(5) Uani 1 1 d . . . . .
H2 H -0.0150 0.8521 0.4989 0.051 Uiso 1 1 calc R U . . .
C3 C -0.0778(2) 0.7228(2) 0.47799(19) 0.0532(6) Uani 1 1 d . . . . .
H3 H -0.1511 0.7308 0.5299 0.064 Uiso 1 1 calc R U . . .
C4 C -0.0526(3) 0.6385(2) 0.4199(2) 0.0598(7) Uani 1 1 d . . . . .
H4 H -0.1101 0.5919 0.4326 0.072 Uiso 1 1 calc R U . . .
C5 C 0.0563(3) 0.6236(2) 0.3442(2) 0.0561(7) Uani 1 1 d . . . . .
H5 H 0.0736 0.5671 0.3051 0.067 Uiso 1 1 calc R U . . .
C6 C 0.1401(2) 0.69436(19) 0.32706(16) 0.0413(5) Uani 1 1 d . . . . .
C7 C 0.2632(2) 0.69629(19) 0.25158(17) 0.0417(5) Uani 1 1 d . . . . .
C8 C 0.3377(2) 0.76889(17) 0.28322(14) 0.0327(5) Uani 1 1 d . . . . .
H8 H 0.3735 0.8149 0.2238 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2105(2) 0.85371(17) 0.34146(14) 0.0310(5) Uani 1 1 d . . . . .
C10 C 0.4665(2) 0.68212(17) 0.34962(14) 0.0315(5) Uani 1 1 d . . . . .
H10 H 0.4314 0.6216 0.3927 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6055(2) 0.61350(18) 0.29189(16) 0.0363(5) Uani 1 1 d . . . . .
C12 C 0.6408(3) 0.6546(2) 0.19242(18) 0.0596(7) Uani 1 1 d . . . . .
H12 H 0.5751 0.7261 0.1573 0.071 Uiso 1 1 calc R U . . .
C13 C 0.7726(3) 0.5921(3) 0.1427(2) 0.0694(8) Uani 1 1 d . . . . .
C14 C 0.8049(4) 0.6406(4) 0.0331(3) 0.1337(17) Uani 1 1 d . . . . .
H14A H 0.9019 0.6436 0.0250 0.200 Uiso 1 1 calc R U . . .
H14B H 0.7328 0.7197 0.0124 0.200 Uiso 1 1 calc R U . . .
H14C H 0.8006 0.5891 -0.0077 0.200 Uiso 1 1 calc R U . . .
C15 C 0.8683(3) 0.4864(2) 0.1962(2) 0.0623(8) Uani 1 1 d . . . . .
H15 H 0.9562 0.4431 0.1645 0.075 Uiso 1 1 calc R U . . .
C16 C 0.8357(3) 0.4444(2) 0.2950(2) 0.0551(7) Uani 1 1 d . . . . .
H16 H 0.9020 0.3733 0.3301 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7050(2) 0.50674(19) 0.34300(18) 0.0434(6) Uani 1 1 d . . . . .
H17 H 0.6835 0.4770 0.4101 0.052 Uiso 1 1 calc R U . . .
C18 C 0.7840(3) 0.9422(2) 0.19811(19) 0.0533(6) Uani 1 1 d . . . . .
H18 H 0.8162 0.9176 0.2635 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8852(3) 0.9156(3) 0.1186(2) 0.0677(8) Uani 1 1 d . . . . .
H19 H 0.9845 0.8713 0.1307 0.081 Uiso 1 1 calc R U . . .
C20 C 0.8404(4) 0.9540(3) 0.0221(2) 0.0734(9) Uani 1 1 d . . . . .
H20 H 0.9096 0.9377 -0.0316 0.088 Uiso 1 1 calc R U . . .
C21 C 0.6945(4) 1.0163(3) 0.0043(2) 0.0761(9) Uani 1 1 d . . . . .
H21 H 0.6637 1.0417 -0.0614 0.091 Uiso 1 1 calc R U . . .
C22 C 0.5926(3) 1.0415(2) 0.0843(2) 0.0632(7) Uani 1 1 d . . . . .
H22 H 0.4931 1.0841 0.0717 0.076 Uiso 1 1 calc R U . . .
C23 C 0.6354(2) 1.0047(2) 0.18253(17) 0.0444(6) Uani 1 1 d . . . . .
C24 C 0.5222(3) 1.0363(2) 0.26774(18) 0.0517(6) Uani 1 1 d . . . . .
H24A H 0.5678 1.0484 0.3205 0.062 Uiso 1 1 calc R U . . .
H24B H 0.4426 1.1113 0.2433 0.062 Uiso 1 1 calc R U . . .
C25 C 0.3257(2) 0.99322(18) 0.37351(16) 0.0389(5) Uani 1 1 d . . . . .
H25A H 0.2542 1.0615 0.3324 0.047 Uiso 1 1 calc R U . . .
H25B H 0.3497 1.0211 0.4268 0.047 Uiso 1 1 calc R U . . .
C26 C 0.2573(2) 0.89949(17) 0.42053(14) 0.0308(5) Uani 1 1 d . . . . .
H26 H 0.1701 0.9353 0.4634 0.037 Uiso 1 1 calc R U . . .
C27 C 0.3711(2) 0.79900(17) 0.48572(14) 0.0300(5) Uani 1 1 d . . . . .
C28 C 0.5069(2) 0.74221(18) 0.42216(15) 0.0327(5) Uani 1 1 d . . . . .
H28 H 0.5812 0.6798 0.4670 0.039 Uiso 1 1 calc R U . . .
C29 C 0.5683(2) 0.83867(19) 0.36961(16) 0.0399(5) Uani 1 1 d . . . . .
H29A H 0.6032 0.8633 0.4202 0.048 Uiso 1 1 calc R U . . .
H29B H 0.6525 0.8046 0.3251 0.048 Uiso 1 1 calc R U . . .
C30 C 0.3591(2) 0.76838(18) 0.58692(15) 0.0339(5) Uani 1 1 d . . . . .
C31 C 0.2292(2) 0.82276(19) 0.65434(16) 0.0377(5) Uani 1 1 d . . . . .
C32 C 0.2701(2) 0.76679(19) 0.75897(15) 0.0394(5) Uani 1 1 d . . . . .
C33 C 0.1869(3) 0.7871(2) 0.84743(16) 0.0522(6) Uani 1 1 d . . . . .
H33 H 0.0886 0.8396 0.8463 0.063 Uiso 1 1 calc R U . . .
C34 C 0.2526(3) 0.7281(2) 0.93700(18) 0.0644(8) Uani 1 1 d . . . . .
H34 H 0.1985 0.7408 0.9975 0.077 Uiso 1 1 calc R U . . .
C35 C 0.3995(4) 0.6494(2) 0.93844(19) 0.0711(8) Uani 1 1 d . . . . .
H35 H 0.4427 0.6115 1.0001 0.085 Uiso 1 1 calc R U . . .
C36 C 0.4826(3) 0.6263(2) 0.85058(18) 0.0633(7) Uani 1 1 d . . . . .
H36 H 0.5802 0.5722 0.8520 0.076 Uiso 1 1 calc R U . . .
C37 C 0.4161(3) 0.68602(19) 0.76033(16) 0.0427(6) Uani 1 1 d . . . . .
C38 C 0.4773(3) 0.6803(2) 0.65565(17) 0.0462(6) Uani 1 1 d . . . . .
N1 N 0.45987(18) 0.94396(15) 0.31101(13) 0.0381(4) Uani 1 1 d . . . . .
O1 O 0.29946(18) 0.64896(15) 0.17936(13) 0.0611(5) Uani 1 1 d . . . . .
O2 O 0.13166(15) 0.95270(12) 0.26497(10) 0.0397(4) Uani 1 1 d . . . . .
H2A H 0.0576 0.9979 0.2909 0.060 Uiso 1 1 calc R U . . .
O3 O 0.10914(17) 0.90033(15) 0.62994(11) 0.0534(4) Uani 1 1 d . . . . .
O4 O 0.60139(19) 0.61531(18) 0.63253(13) 0.0815(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(3) . ?
C1 C6 1.392(3) . ?
C1 C9 1.525(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.479(3) . ?
C7 O1 1.209(2) . ?
C7 C8 1.527(3) . ?
C8 C10 1.540(3) . ?
C8 C9 1.547(2) . ?
C8 H8 0.9800 . ?
C9 O2 1.436(2) . ?
C9 C26 1.532(3) . ?
C10 C11 1.523(2) . ?
C10 C28 1.549(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.378(3) . ?
C11 C17 1.388(3) . ?
C12 C13 1.400(3) . ?
C12 H12 0.9300 . ?
C13 C15 1.378(4) . ?
C13 C14 1.511(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 C23 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.503(3) . ?
C24 N1 1.469(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 N1 1.464(2) . ?
C25 C26 1.531(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.499(3) . ?
C26 H26 0.9800 . ?
C27 C30 1.344(3) . ?
C27 C28 1.504(2) . ?
C28 C29 1.529(3) . ?
C28 H28 0.9800 . ?
C29 N1 1.458(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.491(3) . ?
C30 C38 1.498(3) . ?
C31 O3 1.223(2) . ?
C31 C32 1.467(3) . ?
C32 C33 1.378(3) . ?
C32 C37 1.391(3) . ?
C33 C34 1.368(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.390(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.377(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.380(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.478(3) . ?
C38 O4 1.217(2) . ?
O2 H2A 0.8200 . ?

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 C1 C6 119.67(19) . . ?
C2 C1 C9 129.99(18) . . ?
C6 C1 C9 110.12(17) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 C7 129.5(2) . . ?
C1 C6 C7 109.01(18) . . ?
O1 C7 C6 127.1(2) . . ?
O1 C7 C8 126.4(2) . . ?
C6 C7 C8 106.54(17) . . ?
C7 C8 C10 108.66(16) . . ?
C7 C8 C9 102.79(15) . . ?
C10 C8 C9 113.13(15) . . ?
C7 C8 H8 110.7 . . ?
C10 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
O2 C9 C1 108.08(15) . . ?
O2 C9 C26 110.03(15) . . ?
C1 C9 C26 114.54(15) . . ?
O2 C9 C8 104.94(14) . . ?
C1 C9 C8 102.54(15) . . ?
C26 C9 C8 115.93(16) . . ?
C11 C10 C8 114.78(16) . . ?
C11 C10 C28 109.90(16) . . ?
C8 C10 C28 113.29(15) . . ?
C11 C10 H10 106.0 . . ?
C8 C10 H10 106.0 . . ?
C28 C10 H10 106.0 . . ?
C12 C11 C17 118.13(19) . . ?
C12 C11 C10 123.27(19) . . ?
C17 C11 C10 118.53(18) . . ?
C11 C12 C13 122.0(2) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C15 C13 C12 118.1(2) . . ?
C15 C13 C14 122.2(2) . . ?
C12 C13 C14 119.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 120.9(2) . . ?
C16 C15 H15 119.5 . . ?
C13 C15 H15 119.5 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C11 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C11 C17 H17 119.7 . . ?
C19 C18 C23 121.1(2) . . ?
C19 C18 H18 119.5 . . ?
C23 C18 H18 119.5 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 121.3(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C18 117.6(2) . . ?
C22 C23 C24 120.0(2) . . ?
C18 C23 C24 122.4(2) . . ?
N1 C24 C23 113.16(18) . . ?
N1 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
N1 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.8 . . ?
N1 C25 C26 111.50(15) . . ?
N1 C25 H25A 109.3 . . ?
C26 C25 H25A 109.3 . . ?
N1 C25 H25B 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C27 C26 C25 106.57(16) . . ?
C27 C26 C9 111.02(15) . . ?
C25 C26 C9 112.90(16) . . ?
C27 C26 H26 108.7 . . ?
C25 C26 H26 108.7 . . ?
C9 C26 H26 108.7 . . ?
C30 C27 C26 125.47(17) . . ?
C30 C27 C28 124.26(18) . . ?
C26 C27 C28 110.13(16) . . ?
C27 C28 C29 107.99(15) . . ?
C27 C28 C10 109.01(15) . . ?
C29 C28 C10 114.56(16) . . ?
C27 C28 H28 108.4 . . ?
C29 C28 H28 108.4 . . ?
C10 C28 H28 108.4 . . ?
N1 C29 C28 113.24(16) . . ?
N1 C29 H29A 108.9 . . ?
C28 C29 H29A 108.9 . . ?
N1 C29 H29B 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C27 C30 C31 126.92(19) . . ?
C27 C30 C38 127.10(18) . . ?
C31 C30 C38 105.80(17) . . ?
O3 C31 C32 124.47(19) . . ?
O3 C31 C30 127.89(19) . . ?
C32 C31 C30 107.64(18) . . ?
C33 C32 C37 121.0(2) . . ?
C33 C32 C31 129.1(2) . . ?
C37 C32 C31 109.84(18) . . ?
C34 C33 C32 118.4(2) . . ?
C34 C33 H33 120.8 . . ?
C32 C33 H33 120.8 . . ?
C33 C34 C35 120.7(2) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C36 C35 C34 121.5(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 117.8(2) . . ?
C35 C36 H36 121.1 . . ?
C37 C36 H36 121.1 . . ?
C36 C37 C32 120.7(2) . . ?
C36 C37 C38 129.8(2) . . ?
C32 C37 C38 109.5(2) . . ?
O4 C38 C37 124.9(2) . . ?
O4 C38 C30 128.0(2) . . ?
C37 C38 C30 107.12(18) . . ?
C29 N1 C25 110.87(16) . . ?
C29 N1 C24 110.70(17) . . ?
C25 N1 C24 109.79(15) . . ?
C9 O2 H2A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.82 2.00 2.8111(19) 172.8 2_576

_refine_diff_density_max         0.166
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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 1814879'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-05-22 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         'C29 H27 N O3'
_chemical_formula_sum            'C29 H27 N O3'
_chemical_formula_weight         437.51

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                   8.9074(18)
_cell_length_b                   24.060(5)
_cell_length_c                   11.549(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.68
_cell_angle_gamma                90
_cell_volume                     2283.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      20.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10817
_diffrn_reflns_av_unetI/netI     0.1989
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.090
_diffrn_reflns_theta_max         24.705
_diffrn_reflns_theta_full        24.705
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measured_fraction_theta_full 0.826
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_Laue_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_point_group_measured_fraction_full 0.826
_reflns_number_total             3226
_reflns_number_gt                1538
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+15.0000P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.19(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3226
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2624
_refine_ls_R_factor_gt           0.1687
_refine_ls_wR_factor_ref         0.4641
_refine_ls_wR_factor_gt          0.4176
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 -0.1521(16) 0.1772(5) 0.4631(11) 0.046(3) Uani 1 1 d . . . . .
H1 H -0.2550 0.1816 0.4002 0.055 Uiso 1 1 calc R U . . .
C2 C -0.1400(18) 0.1650(5) 0.5819(13) 0.055(4) Uani 1 1 d . . . . .
H2 H -0.2335 0.1631 0.5993 0.065 Uiso 1 1 calc R U . . .
C3 C 0.008(2) 0.1557(6) 0.6751(11) 0.059(4) Uani 1 1 d . . . . .
H3 H 0.0161 0.1459 0.7552 0.071 Uiso 1 1 calc R U . . .
C4 C 0.147(2) 0.1610(6) 0.6489(12) 0.070(5) Uani 1 1 d . . . . .
H4 H 0.2485 0.1556 0.7126 0.084 Uiso 1 1 calc R U . . .
C5 C 0.1356(18) 0.1737(5) 0.5326(12) 0.055(3) Uani 1 1 d . . . . .
H5 H 0.2302 0.1764 0.5169 0.066 Uiso 1 1 calc R U . . .
C6 C -0.0174(14) 0.1832(4) 0.4328(11) 0.039(3) Uani 1 1 d . . . . .
C7 C -0.0278(16) 0.1993(4) 0.3054(10) 0.039(3) Uani 1 1 d . . . . .
H7A H -0.1418 0.2031 0.2514 0.047 Uiso 1 1 calc R U . . .
H7B H 0.0220 0.2356 0.3115 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0402(14) 0.1884(4) 0.1306(10) 0.040(3) Uani 1 1 d . . . . .
H8A H 0.0879 0.2252 0.1492 0.048 Uiso 1 1 calc R U . . .
H8B H -0.0723 0.1922 0.0729 0.048 Uiso 1 1 calc R U . . .
C9 C 0.1359(15) 0.1522(4) 0.0685(10) 0.040(3) Uani 1 1 d . . . . .
H9 H 0.1297 0.1709 -0.0087 0.049 Uiso 1 1 calc R U . . .
C10 C 0.0447(13) 0.0985(4) 0.0332(10) 0.035(2) Uani 1 1 d . . . . .
C11 C 0.0410(13) 0.0692(4) 0.1450(9) 0.034(2) Uani 1 1 d . . . . .
H11 H -0.0293 0.0365 0.1167 0.040 Uiso 1 1 calc R U . . .
C12 C -0.0324(14) 0.1084(4) 0.2179(10) 0.037(3) Uani 1 1 d . . . . .
H12A H -0.1475 0.1136 0.1684 0.045 Uiso 1 1 calc R U . . .
H12B H -0.0219 0.0907 0.2961 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2171(15) 0.0492(4) 0.2207(11) 0.042(3) Uani 1 1 d . . . . .
C14 C 0.2389(11) 0.0297(4) 0.3533(9) 0.029(2) Uani 1 1 d . . . . .
C15 C 0.1696(17) -0.0165(5) 0.3832(11) 0.051(3) Uani 1 1 d . . . . .
H15 H 0.1057 -0.0408 0.3211 0.061 Uiso 1 1 calc R U . . .
C16 C 0.1977(18) -0.0257(5) 0.5073(12) 0.057(4) Uani 1 1 d . . . . .
H16 H 0.1490 -0.0558 0.5293 0.068 Uiso 1 1 calc R U . . .
C17 C 0.299(2) 0.0101(5) 0.6016(12) 0.066(4) Uani 1 1 d . . . . .
H17 H 0.3171 0.0031 0.6851 0.080 Uiso 1 1 calc R U . . .
C18 C 0.3741(18) 0.0565(6) 0.5707(12) 0.061(4) Uani 1 1 d . . . . .
H18 H 0.4431 0.0800 0.6321 0.073 Uiso 1 1 calc R U . . .
C19 C 0.3390(15) 0.0652(4) 0.4427(11) 0.044(3) Uani 1 1 d . . . . .
C20 C 0.3920(13) 0.1097(5) 0.3807(11) 0.044(3) Uani 1 1 d . . . . .
C21 C 0.3450(14) 0.0950(4) 0.2430(10) 0.039(3) Uani 1 1 d . . . . .
H21 H 0.4405 0.0761 0.2392 0.047 Uiso 1 1 calc R U . . .
C22 C 0.3170(14) 0.1460(4) 0.1551(10) 0.040(3) Uani 1 1 d . . . . .
H22 H 0.3486 0.1792 0.2081 0.048 Uiso 1 1 calc R U . . .
C23 C 0.4145(14) 0.1457(4) 0.0717(10) 0.040(3) Uani 1 1 d . . . . .
C24 C 0.4632(18) 0.1958(6) 0.0427(14) 0.065(4) Uani 1 1 d . . . . .
H24 H 0.4441 0.2275 0.0812 0.077 Uiso 1 1 calc R U . . .
C25 C 0.5385(16) 0.2020(5) -0.0395(11) 0.047(3) Uani 1 1 d . . . . .
H25 H 0.5646 0.2374 -0.0584 0.057 Uiso 1 1 calc R U . . .
C26 C 0.5762(14) 0.1559(5) -0.0947(11) 0.049(3) Uani 1 1 d . . . . .
C27 C 0.6562(17) 0.1638(8) -0.1908(13) 0.070(4) Uani 1 1 d . . . . .
H27A H 0.5735 0.1713 -0.2720 0.105 Uiso 1 1 calc R U . . .
H27B H 0.7138 0.1306 -0.1946 0.105 Uiso 1 1 calc R U . . .
H27C H 0.7308 0.1945 -0.1655 0.105 Uiso 1 1 calc R U . . .
C28 C 0.5297(16) 0.1040(5) -0.0667(13) 0.055(3) Uani 1 1 d . . . . .
H28 H 0.5506 0.0723 -0.1040 0.066 Uiso 1 1 calc R U . . .
C29 C 0.4519(17) 0.0994(5) 0.0171(11) 0.051(3) Uani 1 1 d . . . . .
H29 H 0.4244 0.0644 0.0367 0.061 Uiso 1 1 calc R U . . .
N1 N 0.0470(11) 0.1620(4) 0.2447(8) 0.039(2) Uani 1 1 d . . . . .
O1 O -0.0177(11) 0.0800(3) -0.0717(7) 0.053(2) Uani 1 1 d . . . . .
O2 O 0.2523(10) 0.0072(3) 0.1450(7) 0.045(2) Uani 1 1 d . . . . .
H2A H 0.1701 -0.0111 0.1078 0.067 Uiso 1 1 calc R U . . .
O3 O 0.4631(11) 0.1535(3) 0.4339(8) 0.059(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.367(18) . ?
C1 C6 1.381(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.36(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.344(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.424(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(14) . ?
C7 N1 1.449(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.443(13) . ?
C8 C9 1.571(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.497(15) . ?
C9 C22 1.544(18) . ?
C9 H9 0.9800 . ?
C10 O1 1.207(13) . ?
C10 C11 1.483(14) . ?
C11 C13 1.549(16) . ?
C11 C12 1.565(14) . ?
C11 H11 0.9800 . ?
C12 N1 1.448(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.449(12) . ?
C13 C21 1.533(16) . ?
C13 C14 1.541(14) . ?
C14 C19 1.371(15) . ?
C14 C15 1.378(15) . ?
C15 C16 1.375(17) . ?
C15 H15 0.9300 . ?
C16 C17 1.41(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.42(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.404(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.463(15) . ?
C20 O3 1.260(14) . ?
C20 C21 1.522(16) . ?
C21 C22 1.550(15) . ?
C21 H21 0.9800 . ?
C22 C23 1.526(15) . ?
C22 H22 0.9800 . ?
C23 C24 1.365(17) . ?
C23 C29 1.382(15) . ?
C24 C25 1.365(15) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(17) . ?
C25 H25 0.9300 . ?
C26 C28 1.392(18) . ?
C26 C27 1.544(16) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C29 1.395(16) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O2 H2A 0.8200 . ?

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 C1 C6 122.5(13) . . ?
C2 C1 H1 118.7 . . ?
C6 C1 H1 118.7 . . ?
C3 C2 C1 120.4(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.1(11) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.7(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.6(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 115.6(10) . . ?
C1 C6 C7 123.3(11) . . ?
C5 C6 C7 121.1(10) . . ?
N1 C7 C6 116.8(8) . . ?
N1 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
N1 C7 H7B 108.1 . . ?
C6 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
N1 C8 C9 109.6(8) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C22 114.4(9) . . ?
C10 C9 C8 105.6(8) . . ?
C22 C9 C8 111.9(9) . . ?
C10 C9 H9 108.2 . . ?
C22 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
O1 C10 C11 122.9(9) . . ?
O1 C10 C9 125.7(9) . . ?
C11 C10 C9 111.4(8) . . ?
C10 C11 C13 106.4(8) . . ?
C10 C11 C12 109.7(8) . . ?
C13 C11 C12 115.2(8) . . ?
C10 C11 H11 108.5 . . ?
C13 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
N1 C12 C11 112.4(8) . . ?
N1 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
O2 C13 C21 106.4(8) . . ?
O2 C13 C14 114.4(8) . . ?
C21 C13 C14 104.6(9) . . ?
O2 C13 C11 106.5(9) . . ?
C21 C13 C11 113.4(8) . . ?
C14 C13 C11 111.6(8) . . ?
C19 C14 C15 122.6(10) . . ?
C19 C14 C13 110.7(9) . . ?
C15 C14 C13 126.7(10) . . ?
C16 C15 C14 118.1(12) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 120.9(12) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 120.7(12) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 116.6(13) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C14 C19 C18 121.1(11) . . ?
C14 C19 C20 109.1(9) . . ?
C18 C19 C20 129.8(12) . . ?
O3 C20 C19 124.7(11) . . ?
O3 C20 C21 126.0(10) . . ?
C19 C20 C21 109.3(9) . . ?
C20 C21 C13 103.3(8) . . ?
C20 C21 C22 114.2(9) . . ?
C13 C21 C22 122.5(10) . . ?
C20 C21 H21 105.1 . . ?
C13 C21 H21 105.1 . . ?
C22 C21 H21 105.1 . . ?
C23 C22 C9 107.3(8) . . ?
C23 C22 C21 115.0(8) . . ?
C9 C22 C21 111.4(9) . . ?
C23 C22 H22 107.6 . . ?
C9 C22 H22 107.6 . . ?
C21 C22 H22 107.6 . . ?
C24 C23 C29 116.4(11) . . ?
C24 C23 C22 117.6(10) . . ?
C29 C23 C22 126.0(10) . . ?
C23 C24 C25 123.7(12) . . ?
C23 C24 H24 118.2 . . ?
C25 C24 H24 118.2 . . ?
C24 C25 C26 120.2(11) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C28 117.8(9) . . ?
C25 C26 C27 119.5(11) . . ?
C28 C26 C27 122.6(12) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 C29 120.2(11) . . ?
C26 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C23 C29 C28 121.6(11) . . ?
C23 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C8 N1 C12 110.6(8) . . ?
C8 N1 C7 107.8(8) . . ?
C12 N1 C7 112.2(8) . . ?
C13 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.1(18) . . . . ?
C1 C2 C3 C4 2.6(19) . . . . ?
C2 C3 C4 C5 -2(2) . . . . ?
C3 C4 C5 C6 1(2) . . . . ?
C2 C1 C6 C5 2.4(16) . . . . ?
C2 C1 C6 C7 -176.7(10) . . . . ?
C4 C5 C6 C1 -1.4(16) . . . . ?
C4 C5 C6 C7 177.8(11) . . . . ?
C1 C6 C7 N1 -123.9(12) . . . . ?
C5 C6 C7 N1 57.0(14) . . . . ?
N1 C8 C9 C10 64.3(11) . . . . ?
N1 C8 C9 C22 -60.9(11) . . . . ?
C22 C9 C10 O1 -117.0(12) . . . . ?
C8 C9 C10 O1 119.4(11) . . . . ?
C22 C9 C10 C11 62.3(11) . . . . ?
C8 C9 C10 C11 -61.2(11) . . . . ?
O1 C10 C11 C13 109.9(12) . . . . ?
C9 C10 C11 C13 -69.5(10) . . . . ?
O1 C10 C11 C12 -124.9(11) . . . . ?
C9 C10 C11 C12 55.7(11) . . . . ?
C10 C11 C12 N1 -51.7(12) . . . . ?
C13 C11 C12 N1 68.2(11) . . . . ?
C10 C11 C13 O2 -67.2(9) . . . . ?
C12 C11 C13 O2 171.1(8) . . . . ?
C10 C11 C13 C21 49.5(11) . . . . ?
C12 C11 C13 C21 -72.2(11) . . . . ?
C10 C11 C13 C14 167.3(8) . . . . ?
C12 C11 C13 C14 45.6(11) . . . . ?
O2 C13 C14 C19 127.1(10) . . . . ?
C21 C13 C14 C19 11.1(11) . . . . ?
C11 C13 C14 C19 -111.9(10) . . . . ?
O2 C13 C14 C15 -53.2(14) . . . . ?
C21 C13 C14 C15 -169.3(9) . . . . ?
C11 C13 C14 C15 67.8(12) . . . . ?
C19 C14 C15 C16 2.6(17) . . . . ?
C13 C14 C15 C16 -177.0(11) . . . . ?
C14 C15 C16 C17 -2.2(19) . . . . ?
C15 C16 C17 C18 0(2) . . . . ?
C16 C17 C18 C19 1.3(19) . . . . ?
C15 C14 C19 C18 -1.0(16) . . . . ?
C13 C14 C19 C18 178.6(10) . . . . ?
C15 C14 C19 C20 180.0(9) . . . . ?
C13 C14 C19 C20 -0.4(12) . . . . ?
C17 C18 C19 C14 -1.0(17) . . . . ?
C17 C18 C19 C20 177.8(12) . . . . ?
C14 C19 C20 O3 168.1(11) . . . . ?
C18 C19 C20 O3 -11(2) . . . . ?
C14 C19 C20 C21 -10.9(12) . . . . ?
C18 C19 C20 C21 170.3(12) . . . . ?
O3 C20 C21 C13 -161.9(10) . . . . ?
C19 C20 C21 C13 17.1(11) . . . . ?
O3 C20 C21 C22 -26.6(16) . . . . ?
C19 C20 C21 C22 152.4(9) . . . . ?
O2 C13 C21 C20 -137.8(8) . . . . ?
C14 C13 C21 C20 -16.4(10) . . . . ?
C11 C13 C21 C20 105.4(10) . . . . ?
O2 C13 C21 C22 91.6(10) . . . . ?
C14 C13 C21 C22 -146.9(9) . . . . ?
C11 C13 C21 C22 -25.1(12) . . . . ?
C10 C9 C22 C23 95.4(9) . . . . ?
C8 C9 C22 C23 -144.5(8) . . . . ?
C10 C9 C22 C21 -31.4(11) . . . . ?
C8 C9 C22 C21 88.8(10) . . . . ?
C20 C21 C22 C23 126.7(10) . . . . ?
C13 C21 C22 C23 -107.6(11) . . . . ?
C20 C21 C22 C9 -110.9(10) . . . . ?
C13 C21 C22 C9 14.9(12) . . . . ?
C9 C22 C23 C24 87.9(12) . . . . ?
C21 C22 C23 C24 -147.5(12) . . . . ?
C9 C22 C23 C29 -88.7(13) . . . . ?
C21 C22 C23 C29 35.9(16) . . . . ?
C29 C23 C24 C25 3(2) . . . . ?
C22 C23 C24 C25 -174.1(12) . . . . ?
C23 C24 C25 C26 -3(2) . . . . ?
C24 C25 C26 C28 2.2(18) . . . . ?
C24 C25 C26 C27 178.0(12) . . . . ?
C25 C26 C28 C29 -1.7(19) . . . . ?
C27 C26 C28 C29 -177.4(12) . . . . ?
C24 C23 C29 C28 -2.3(19) . . . . ?
C22 C23 C29 C28 174.3(12) . . . . ?
C26 C28 C29 C23 2(2) . . . . ?
C9 C8 N1 C12 -62.8(12) . . . . ?
C9 C8 N1 C7 174.2(9) . . . . ?
C11 C12 N1 C8 56.1(11) . . . . ?
C11 C12 N1 C7 176.5(8) . . . . ?
C6 C7 N1 C8 -173.3(10) . . . . ?
C6 C7 N1 C12 64.7(13) . . . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.142

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1587035'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C27 H24 N2 O3, C H2 Cl2'
_chemical_formula_sum            'C28 H26 Cl2 N2 O3'
_chemical_formula_weight         509.41

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'
Cl Cl 0.1484 0.1585 '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                   15.2237(16)
_cell_length_b                   12.7126(13)
_cell_length_c                   15.0411(15)
_cell_angle_alpha                90
_cell_angle_beta                 119.60
_cell_angle_gamma                90
_cell_volume                     2531.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3987
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.77

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10626
_diffrn_reflns_av_unetI/netI     0.1090
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.221
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measured_fraction_theta_full 0.837
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.837
_reflns_number_total             4980
_reflns_number_gt                2482
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.1063P)²] 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         4980
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1740
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      0.973
_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 0.9726(3) 0.9863(5) 0.3106(4) 0.0931(15) Uani 1 1 d . . . . .
H1 H 0.9654 1.0558 0.2887 0.112 Uiso 1 1 calc R U . . .
C2 C 1.0331(4) 0.9203(8) 0.2922(5) 0.129(3) Uani 1 1 d . . . . .
H2 H 1.0671 0.9453 0.2593 0.155 Uiso 1 1 calc R U . . .
C3 C 1.0432(4) 0.8167(9) 0.3229(6) 0.131(3) Uani 1 1 d . . . . .
H3 H 1.0817 0.7707 0.3081 0.157 Uiso 1 1 calc R U . . .
C4 C 0.9967(4) 0.7819(5) 0.3749(6) 0.111(2) Uani 1 1 d . . . . .
H4 H 1.0051 0.7127 0.3975 0.134 Uiso 1 1 calc R U . . .
C5 C 0.9356(3) 0.8514(4) 0.3944(4) 0.0820(13) Uani 1 1 d . . . . .
H5 H 0.9045 0.8279 0.4306 0.098 Uiso 1 1 calc R U . . .
C6 C 0.9221(2) 0.9533(3) 0.3603(3) 0.0574(10) Uani 1 1 d . . . . .
C7 C 0.8544(2) 1.0256(3) 0.3766(3) 0.0588(10) Uani 1 1 d . . . . .
H7A H 0.8759 1.0277 0.4490 0.071 Uiso 1 1 calc R U . . .
H7B H 0.8612 1.0961 0.3559 0.071 Uiso 1 1 calc R U . . .
C8 C 0.7074(2) 0.9940(2) 0.2097(2) 0.0390(7) Uani 1 1 d . . . . .
H8A H 0.7468 0.9458 0.1935 0.047 Uiso 1 1 calc R U . . .
H8B H 0.7145 1.0638 0.1880 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5970(2) 0.9617(2) 0.1507(2) 0.0353(7) Uani 1 1 d . . . . .
H9 H 0.5726 0.9691 0.0773 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5347(2) 1.0303(2) 0.1795(2) 0.0382(7) Uani 1 1 d . . . . .
C11 C 0.5771(2) 1.0337(2) 0.2936(2) 0.0380(7) Uani 1 1 d . . . . .
H11 H 0.5396 1.0863 0.3092 0.046 Uiso 1 1 calc R U . . .
C12 C 0.6875(2) 1.0670(2) 0.3441(2) 0.0445(8) Uani 1 1 d . . . . .
H12A H 0.6919 1.1372 0.3212 0.053 Uiso 1 1 calc R U . . .
H12B H 0.7153 1.0694 0.4177 0.053 Uiso 1 1 calc R U . . .
C13 C 0.56006(19) 0.9239(2) 0.3279(2) 0.0312(6) Uani 1 1 d . . . . .
C14 C 0.62957(19) 0.9055(2) 0.4409(2) 0.0336(7) Uani 1 1 d . . . . .
C15 C 0.6292(2) 0.9559(3) 0.5218(2) 0.0432(7) Uani 1 1 d . . . . .
H15 H 0.5834 1.0097 0.5103 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6978(3) 0.9254(3) 0.6201(2) 0.0553(9) Uani 1 1 d . . . . .
H16 H 0.6967 0.9580 0.6750 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7676(3) 0.8478(3) 0.6386(2) 0.0586(10) Uani 1 1 d . . . . .
H17 H 0.8125 0.8279 0.7055 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7718(2) 0.7989(3) 0.5583(2) 0.0482(8) Uani 1 1 d . . . . .
H18 H 0.8199 0.7474 0.5704 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7022(2) 0.8291(2) 0.4594(2) 0.0362(7) Uani 1 1 d . . . . .
C20 C 0.6853(2) 0.7866(2) 0.3615(2) 0.0335(7) Uani 1 1 d . . . . .
C21 C 0.58570(19) 0.8309(2) 0.27783(19) 0.0297(6) Uani 1 1 d . . . . .
H21 H 0.5353 0.7767 0.2661 0.036 Uiso 1 1 calc R U . . .
C22 C 0.58080(19) 0.8453(2) 0.17389(19) 0.0309(6) Uani 1 1 d . . . . .
H22 H 0.6369 0.8045 0.1772 0.037 Uiso 1 1 calc R U . . .
C23 C 0.4909(2) 0.7602(2) 0.0018(2) 0.0364(8) Uani 1 1 d . . . . .
H23 H 0.5538 0.7596 0.0058 0.044 Uiso 1 1 calc R U . . .
C24 C 0.48513(19) 0.8026(2) 0.08347(19) 0.0305(6) Uani 1 1 d . . . . .
C25 C 0.3906(2) 0.8057(2) 0.0747(2) 0.0402(7) Uani 1 1 d . . . . .
H25 H 0.3821 0.8345 0.1268 0.048 Uiso 1 1 calc R U . . .
C26 C 0.3088(2) 0.7656(3) -0.0120(3) 0.0453(9) Uani 1 1 d . . . . .
H26 H 0.2446 0.7670 -0.0189 0.054 Uiso 1 1 calc R U . . .
C27 C 0.3230(2) 0.7243(3) -0.0868(3) 0.0426(8) Uani 1 1 d . . . . .
H27 H 0.2672 0.6974 -0.1446 0.051 Uiso 1 1 calc R U . . .
C28 C 0.2073(4) 0.9947(4) 0.0911(4) 0.0951(16) Uani 1 1 d . . . . .
H28A H 0.1876 1.0525 0.1195 0.114 Uiso 1 1 calc R U . . .
H28B H 0.2796 0.9998 0.1176 0.114 Uiso 1 1 calc R U . . .
Cl1 Cl 0.18114(10) 0.87657(10) 0.13183(9) 0.0936(4) Uani 1 1 d . . . . .
Cl2 Cl 0.14683(19) 1.00723(13) -0.03889(12) 0.1626(9) Uani 1 1 d . . . . .
N1 N 0.74738(16) 0.99458(19) 0.31972(18) 0.0380(6) Uani 1 1 d . . . . .
N2 N 0.41325(19) 0.7200(2) -0.08221(19) 0.0422(6) Uani 1 1 d . . . . .
O1 O 0.45854(17) 1.07633(19) 0.11835(18) 0.0590(7) Uani 1 1 d . . . . .
O2 O 0.45573(13) 0.92492(16) 0.30055(15) 0.0394(5) Uani 1 1 d . . . . .
H2A H 0.4447 0.8770 0.3302 0.059 Uiso 1 1 calc R U . . .
O3 O 0.73869(17) 0.72482(18) 0.34811(17) 0.0467(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.372(8) . ?
C1 C6 1.376(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.362(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.490(5) . ?
C7 N1 1.471(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.453(4) . ?
C8 C9 1.518(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.501(4) . ?
C9 C22 1.568(4) . ?
C9 H9 0.9800 . ?
C10 O1 1.216(3) . ?
C10 C11 1.507(4) . ?
C11 C12 1.523(4) . ?
C11 C13 1.555(4) . ?
C11 H11 0.9800 . ?
C12 N1 1.464(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.430(3) . ?
C13 C14 1.512(4) . ?
C13 C21 1.552(4) . ?
C14 C15 1.378(4) . ?
C14 C19 1.392(4) . ?
C15 C16 1.379(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.467(4) . ?
C20 O3 1.217(4) . ?
C20 C21 1.521(4) . ?
C21 C22 1.539(4) . ?
C21 H21 0.9800 . ?
C22 C24 1.519(4) . ?
C22 H22 0.9800 . ?
C23 N2 1.334(4) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(4) . ?
C25 C26 1.382(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.352(5) . ?
C26 H26 0.9300 . ?
C27 N2 1.342(4) . ?
C27 H27 0.9300 . ?
C28 Cl2 1.708(5) . ?
C28 Cl1 1.740(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
O2 H2A 0.8200 . ?

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 C1 C6 122.3(6) . . ?
C2 C1 H1 118.8 . . ?
C6 C1 H1 118.8 . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.9(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.3(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 C7 120.7(4) . . ?
C1 C6 C7 121.3(4) . . ?
N1 C7 C6 113.3(3) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 C9 112.8(2) . . ?
N1 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 110.4(2) . . ?
C10 C9 C22 107.0(2) . . ?
C8 C9 C22 112.1(2) . . ?
C10 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
C22 C9 H9 109.1 . . ?
O1 C10 C9 124.3(3) . . ?
O1 C10 C11 124.0(3) . . ?
C9 C10 C11 111.6(2) . . ?
C10 C11 C12 108.8(3) . . ?
C10 C11 C13 107.7(2) . . ?
C12 C11 C13 114.1(2) . . ?
C10 C11 H11 108.7 . . ?
C12 C11 H11 108.7 . . ?
C13 C11 H11 108.7 . . ?
N1 C12 C11 111.7(2) . . ?
N1 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
O2 C13 C14 112.7(2) . . ?
O2 C13 C21 112.1(2) . . ?
C14 C13 C21 102.9(2) . . ?
O2 C13 C11 103.9(2) . . ?
C14 C13 C11 111.9(2) . . ?
C21 C13 C11 113.6(2) . . ?
C15 C14 C19 119.8(3) . . ?
C15 C14 C13 127.9(3) . . ?
C19 C14 C13 112.2(2) . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 118.0(3) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
C18 C19 C14 121.2(3) . . ?
C18 C19 C20 129.5(3) . . ?
C14 C19 C20 109.2(2) . . ?
O3 C20 C19 127.2(3) . . ?
O3 C20 C21 125.2(3) . . ?
C19 C20 C21 107.6(2) . . ?
C20 C21 C22 114.4(2) . . ?
C20 C21 C13 105.5(2) . . ?
C22 C21 C13 120.3(2) . . ?
C20 C21 H21 105.1 . . ?
C22 C21 H21 105.1 . . ?
C13 C21 H21 105.1 . . ?
C24 C22 C21 114.3(2) . . ?
C24 C22 C9 109.0(2) . . ?
C21 C22 C9 113.8(2) . . ?
C24 C22 H22 106.4 . . ?
C21 C22 H22 106.4 . . ?
C9 C22 H22 106.4 . . ?
N2 C23 C24 125.1(3) . . ?
N2 C23 H23 117.4 . . ?
C24 C23 H23 117.4 . . ?
C25 C24 C23 116.5(3) . . ?
C25 C24 C22 124.7(2) . . ?
C23 C24 C22 118.7(2) . . ?
C24 C25 C26 119.4(3) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 119.2(3) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
N2 C27 C26 123.6(3) . . ?
N2 C27 H27 118.2 . . ?
C26 C27 H27 118.2 . . ?
Cl2 C28 Cl1 113.3(3) . . ?
Cl2 C28 H28A 108.9 . . ?
Cl1 C28 H28A 108.9 . . ?
Cl2 C28 H28B 108.9 . . ?
Cl1 C28 H28B 108.9 . . ?
H28A C28 H28B 107.7 . . ?
C8 N1 C12 109.0(2) . . ?
C8 N1 C7 112.6(3) . . ?
C12 N1 C7 109.4(2) . . ?
C23 N2 C27 116.0(3) . . ?
C13 O2 H2A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A N2 0.82 2.03 2.837(3) 169.5 4_576

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1587036'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C27 H24 N2 O3'
_chemical_formula_sum            'C27 H24 N2 O3'
_chemical_formula_weight         424.48

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

_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                   7.3088(4)
_cell_length_b                   12.2040(6)
_cell_length_c                   12.7704(6)
_cell_angle_alpha                110.5634(15)
_cell_angle_beta                 96.8007(14)
_cell_angle_gamma                96.6011(16)
_cell_volume                     1043.87(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6955
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16464
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.808
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4820
_reflns_number_gt                3574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0495P)²+0.3040P] 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         4820
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.1715(3) 1.10361(17) 0.63419(16) 0.0504(5) Uani 1 1 d . . . . .
H1 H 0.2872 1.1000 0.6109 0.061 Uiso 1 1 calc R U . . .
C2 C 0.0542(3) 1.1702(2) 0.6009(2) 0.0662(6) Uani 1 1 d . . . . .
H2 H 0.0919 1.2123 0.5568 0.079 Uiso 1 1 calc R U . . .
C3 C -0.1178(3) 1.1744(2) 0.6327(2) 0.0666(6) Uani 1 1 d . . . . .
H3 H -0.1972 1.2195 0.6104 0.080 Uiso 1 1 calc R U . . .
C4 C -0.1732(3) 1.11192(18) 0.69764(18) 0.0575(5) Uani 1 1 d . . . . .
H4 H -0.2910 1.1136 0.7181 0.069 Uiso 1 1 calc R U . . .
C5 C -0.0545(2) 1.04655(16) 0.73261(15) 0.0436(4) Uani 1 1 d . . . . .
H5 H -0.0925 1.0053 0.7773 0.052 Uiso 1 1 calc R U . . .
C6 C 0.1207(2) 1.04190(13) 0.70167(13) 0.0340(3) Uani 1 1 d . . . . .
C7 C 0.2625(2) 0.97568(14) 0.73866(15) 0.0374(4) Uani 1 1 d . . . . .
H7A H 0.3254 0.9413 0.6750 0.045 Uiso 1 1 calc R U . . .
H7B H 0.3558 1.0341 0.7986 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1664(2) 0.91701(13) 0.89489(12) 0.0338(3) Uani 1 1 d . . . . .
H8A H 0.0439 0.9400 0.8979 0.041 Uiso 1 1 calc R U . . .
H8B H 0.2587 0.9849 0.9440 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1752(2) 0.81315(13) 0.93702(12) 0.0294(3) Uani 1 1 d . . . . .
H9 H 0.1368 0.8354 1.0117 0.035 Uiso 1 1 calc R U . . .
C10 C 0.03512(19) 0.71021(13) 0.85317(13) 0.0294(3) Uani 1 1 d . . . . .
C11 C 0.08044(19) 0.67386(12) 0.73536(12) 0.0270(3) Uani 1 1 d . . . . .
H11 H -0.0156 0.6077 0.6845 0.032 Uiso 1 1 calc R U . . .
C12 C 0.0686(2) 0.78146(13) 0.70003(12) 0.0295(3) Uani 1 1 d . . . . .
H12A H 0.0958 0.7629 0.6237 0.035 Uiso 1 1 calc R U . . .
H12B H -0.0565 0.8006 0.7006 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5938(2) 0.70867(15) 1.06107(13) 0.0368(4) Uani 1 1 d . . . . .
H13 H 0.6909 0.7487 1.0406 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6328(3) 0.64477(16) 1.12837(14) 0.0435(4) Uani 1 1 d . . . . .
H14 H 0.7575 0.6430 1.1519 0.052 Uiso 1 1 calc R U . . .
C15 C 0.3259(3) 0.59038(16) 1.12659(15) 0.0459(4) Uani 1 1 d . . . . .
H15 H 0.2317 0.5499 1.1487 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2739(2) 0.65279(15) 1.05865(13) 0.0384(4) Uani 1 1 d . . . . .
H16 H 0.1483 0.6537 1.0368 0.046 Uiso 1 1 calc R U . . .
C17 C 0.4103(2) 0.71347(13) 1.02387(11) 0.0283(3) Uani 1 1 d . . . . .
C18 C 0.37339(19) 0.78235(12) 0.94684(11) 0.0261(3) Uani 1 1 d . . . . .
H18 H 0.4594 0.8582 0.9814 0.031 Uiso 1 1 calc R U . . .
C19 C 0.27266(19) 0.63182(12) 0.73341(11) 0.0251(3) Uani 1 1 d . . . . .
C20 C 0.34708(19) 0.63436(12) 0.62829(11) 0.0262(3) Uani 1 1 d . . . . .
C21 C 0.2848(2) 0.55723(14) 0.51675(12) 0.0324(3) Uani 1 1 d . . . . .
H21 H 0.1934 0.4909 0.4995 0.039 Uiso 1 1 calc R U . . .
C22 C 0.3620(2) 0.58149(15) 0.43195(13) 0.0378(4) Uani 1 1 d . . . . .
H22 H 0.3223 0.5305 0.3568 0.045 Uiso 1 1 calc R U . . .
C23 C 0.4977(2) 0.68059(15) 0.45695(13) 0.0375(4) Uani 1 1 d . . . . .
H23 H 0.5470 0.6953 0.3984 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5605(2) 0.75764(14) 0.56781(13) 0.0337(3) Uani 1 1 d . . . . .
H24 H 0.6512 0.8242 0.5847 0.040 Uiso 1 1 calc R U . . .
C25 C 0.48396(19) 0.73271(13) 0.65339(12) 0.0272(3) Uani 1 1 d . . . . .
C26 C 0.52748(19) 0.79744(13) 0.77820(12) 0.0285(3) Uani 1 1 d . . . . .
C27 C 0.42777(18) 0.71786(12) 0.83033(11) 0.0255(3) Uani 1 1 d . . . . .
H27 H 0.5180 0.6688 0.8439 0.031 Uiso 1 1 calc R U . . .
N1 N 0.20257(16) 0.88176(10) 0.77886(10) 0.0286(3) Uani 1 1 d . . . . .
N2 N 0.5019(2) 0.58502(13) 1.16187(11) 0.0437(4) Uani 1 1 d . . . . .
O1 O -0.10648(16) 0.66828(11) 0.87592(10) 0.0476(3) Uani 1 1 d . . . . .
O2 O 0.23470(15) 0.51691(9) 0.73699(9) 0.0358(3) Uani 1 1 d . . . . .
H2A H 0.3321 0.4987 0.7596 0.054 Uiso 1 1 calc R U . . .
O3 O 0.63504(15) 0.88942(10) 0.83001(9) 0.0407(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.375(3) . ?
C1 C6 1.384(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.515(2) . ?
C7 N1 1.4563(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.4565(18) . ?
C8 C9 1.546(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.507(2) . ?
C9 C18 1.540(2) . ?
C9 H9 0.9800 . ?
C10 O1 1.2129(17) . ?
C10 C11 1.501(2) . ?
C11 C12 1.539(2) . ?
C11 C19 1.550(2) . ?
C11 H11 0.9800 . ?
C12 N1 1.4476(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.375(2) . ?
C13 C17 1.384(2) . ?
C13 H13 0.9300 . ?
C14 N2 1.336(2) . ?
C14 H14 0.9300 . ?
C15 N2 1.329(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.5222(19) . ?
C18 C27 1.5429(18) . ?
C18 H18 0.9800 . ?
C19 O2 1.4158(16) . ?
C19 C20 1.5156(19) . ?
C19 C27 1.5494(19) . ?
C20 C25 1.386(2) . ?
C20 C21 1.389(2) . ?
C21 C22 1.382(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.4844(19) . ?
C26 O3 1.2117(17) . ?
C26 C27 1.524(2) . ?
C27 H27 0.9800 . ?
O2 H2A 0.8200 . ?

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 C1 C6 121.32(18) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 120.00(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.82(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.27(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.60(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.97(15) . . ?
C1 C6 C7 117.61(14) . . ?
C5 C6 C7 124.41(14) . . ?
N1 C7 C6 120.14(13) . . ?
N1 C7 H7A 107.3 . . ?
C6 C7 H7A 107.3 . . ?
N1 C7 H7B 107.3 . . ?
C6 C7 H7B 107.3 . . ?
H7A C7 H7B 106.9 . . ?
N1 C8 C9 110.20(12) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C18 111.93(12) . . ?
C10 C9 C8 106.07(12) . . ?
C18 C9 C8 111.79(12) . . ?
C10 C9 H9 109.0 . . ?
C18 C9 H9 109.0 . . ?
C8 C9 H9 109.0 . . ?
O1 C10 C11 123.59(14) . . ?
O1 C10 C9 123.95(14) . . ?
C11 C10 C9 112.17(12) . . ?
C10 C11 C12 106.07(12) . . ?
C10 C11 C19 110.05(11) . . ?
C12 C11 C19 114.68(11) . . ?
C10 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C19 C11 H11 108.6 . . ?
N1 C12 C11 109.00(11) . . ?
N1 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
N1 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C17 120.06(15) . . ?
C14 C13 H13 120.0 . . ?
C17 C13 H13 120.0 . . ?
N2 C14 C13 123.78(16) . . ?
N2 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
N2 C15 C16 124.03(16) . . ?
N2 C15 H15 118.0 . . ?
C16 C15 H15 118.0 . . ?
C17 C16 C15 119.46(16) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C13 116.65(14) . . ?
C16 C17 C18 125.05(14) . . ?
C13 C17 C18 118.29(13) . . ?
C17 C18 C9 114.59(11) . . ?
C17 C18 C27 109.87(11) . . ?
C9 C18 C27 112.80(11) . . ?
C17 C18 H18 106.3 . . ?
C9 C18 H18 106.3 . . ?
C27 C18 H18 106.3 . . ?
O2 C19 C20 114.09(11) . . ?
O2 C19 C27 113.85(11) . . ?
C20 C19 C27 102.29(11) . . ?
O2 C19 C11 103.88(11) . . ?
C20 C19 C11 109.70(11) . . ?
C27 C19 C11 113.30(11) . . ?
C25 C20 C21 120.54(13) . . ?
C25 C20 C19 111.59(12) . . ?
C21 C20 C19 127.69(13) . . ?
C22 C21 C20 118.31(14) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C23 121.16(14) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 120.82(14) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 118.07(14) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C20 C25 C24 121.09(13) . . ?
C20 C25 C26 109.31(12) . . ?
C24 C25 C26 129.59(13) . . ?
O3 C26 C25 127.44(13) . . ?
O3 C26 C27 125.88(13) . . ?
C25 C26 C27 106.31(12) . . ?
C26 C27 C18 115.72(12) . . ?
C26 C27 C19 105.05(11) . . ?
C18 C27 C19 118.22(11) . . ?
C26 C27 H27 105.6 . . ?
C18 C27 H27 105.6 . . ?
C19 C27 H27 105.6 . . ?
C12 N1 C7 116.70(12) . . ?
C12 N1 C8 112.86(11) . . ?
C7 N1 C8 117.58(12) . . ?
C15 N2 C14 116.01(14) . . ?
C19 O2 H2A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A N2 0.82 2.06 2.8306(17) 156.8 2_667

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 1587037'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C21 H20 N2 O3'
_chemical_formula_sum            'C21 H20 N2 O3'
_chemical_formula_weight         348.39

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      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                   12.2787(15)
_cell_length_b                   8.6166(11)
_cell_length_c                   16.4475(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.030(5)
_cell_angle_gamma                90
_cell_volume                     1695.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6266
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      27.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17502
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         27.551
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3893
_reflns_number_gt                2721
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0538P)²+0.3308P] 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         3893
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.13790(12) 0.08624(19) 0.05103(10) 0.0356(4) Uani 1 1 d . . . . .
C2 C 0.20088(13) -0.01698(19) 0.00680(9) 0.0345(4) Uani 1 1 d . . . . .
C3 C 0.19765(15) -0.0256(2) -0.07809(10) 0.0468(4) Uani 1 1 d . . . . .
H3 H 0.1505 0.0384 -0.1160 0.056 Uiso 1 1 calc R U . . .
C4 C 0.26606(16) -0.1315(2) -0.10445(11) 0.0539(5) Uani 1 1 d . . . . .
H4 H 0.2662 -0.1382 -0.1609 0.065 Uiso 1 1 calc R U . . .
C5 C 0.33460(15) -0.2279(2) -0.04799(12) 0.0505(5) Uani 1 1 d . . . . .
H5 H 0.3792 -0.3000 -0.0673 0.061 Uiso 1 1 calc R U . . .
C6 C 0.33846(13) -0.2196(2) 0.03666(11) 0.0423(4) Uani 1 1 d . . . . .
H6 H 0.3849 -0.2847 0.0743 0.051 Uiso 1 1 calc R U . . .
C7 C 0.27088(12) -0.11120(18) 0.06359(9) 0.0323(3) Uani 1 1 d . . . . .
C8 C 0.26947(12) -0.06840(17) 0.15285(9) 0.0311(3) Uani 1 1 d . . . . .
C9 C 0.16259(12) 0.03232(18) 0.14186(9) 0.0307(3) Uani 1 1 d . . . . .
H9 H 0.1022 -0.0397 0.1458 0.037 Uiso 1 1 calc R U . . .
C10 C 0.15830(12) 0.16215(18) 0.20561(9) 0.0335(4) Uani 1 1 d . . . . .
H10 H 0.1124 0.2452 0.1745 0.040 Uiso 1 1 calc R U . . .
C11 C -0.00440(13) 0.1714(2) 0.27314(10) 0.0428(4) Uani 1 1 d . . . . .
H11 H -0.0351 0.2415 0.2312 0.051 Uiso 1 1 calc R U . . .
C12 C 0.10007(12) 0.11280(18) 0.27337(9) 0.0336(4) Uani 1 1 d . . . . .
C13 C 0.14380(14) 0.0093(2) 0.33672(10) 0.0428(4) Uani 1 1 d . . . . .
H13 H 0.2140 -0.0340 0.3401 0.051 Uiso 1 1 calc R U . . .
C14 C 0.08314(14) -0.0294(2) 0.39483(10) 0.0443(4) Uani 1 1 d . . . . .
H14 H 0.1118 -0.0988 0.4376 0.053 Uiso 1 1 calc R U . . .
C15 C -0.01993(14) 0.0361(2) 0.38834(10) 0.0436(4) Uani 1 1 d . . . . .
H15 H -0.0603 0.0097 0.4278 0.052 Uiso 1 1 calc R U . . .
C16 C 0.31137(15) 0.3402(2) 0.17833(12) 0.0491(5) Uani 1 1 d . . . . .
H16A H 0.2543 0.4178 0.1586 0.059 Uiso 1 1 calc R U . . .
H16B H 0.3798 0.3935 0.2046 0.059 Uiso 1 1 calc R U . . .
C17 C 0.27450(13) 0.2351(2) 0.24251(11) 0.0434(4) Uani 1 1 d . . . . .
H17 H 0.2702 0.2968 0.2917 0.052 Uiso 1 1 calc R U . . .
C18 C 0.36161(13) 0.1111(2) 0.26755(10) 0.0443(4) Uani 1 1 d . . . . .
C19 C 0.37827(12) 0.0191(2) 0.19388(10) 0.0366(4) Uani 1 1 d . . . . .
H19 H 0.4380 -0.0569 0.2129 0.044 Uiso 1 1 calc R U . . .
C20 C 0.41669(13) 0.1359(2) 0.13560(10) 0.0401(4) Uani 1 1 d . . . . .
H20A H 0.4846 0.1871 0.1649 0.048 Uiso 1 1 calc R U . . .
H20B H 0.4325 0.0821 0.0877 0.048 Uiso 1 1 calc R U . . .
C21 C 0.34957(17) 0.3457(2) 0.03991(13) 0.0613(5) Uani 1 1 d . . . . .
H21A H 0.4154 0.4074 0.0593 0.092 Uiso 1 1 calc R U . . .
H21B H 0.2865 0.4126 0.0206 0.092 Uiso 1 1 calc R U . . .
H21C H 0.3598 0.2804 -0.0051 0.092 Uiso 1 1 calc R U . . .
N1 N 0.32972(11) 0.24961(16) 0.10809(8) 0.0402(3) Uani 1 1 d . . . . .
N2 N -0.06511(11) 0.13503(19) 0.32872(9) 0.0471(4) Uani 1 1 d . . . . .
O1 O 0.07246(10) 0.18734(15) 0.02103(7) 0.0523(3) Uani 1 1 d . . . . .
O2 O 0.26897(9) -0.19864(13) 0.20583(7) 0.0402(3) Uani 1 1 d . . . . .
H2 H 0.2121 -0.2498 0.1886 0.060 Uiso 1 1 calc R U . . .
O3 O 0.41654(11) 0.0936(2) 0.33814(8) 0.0723(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2121(19) . ?
C1 C2 1.474(2) . ?
C1 C9 1.528(2) . ?
C2 C7 1.381(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.518(2) . ?
C8 O2 1.4217(17) . ?
C8 C9 1.550(2) . ?
C8 C19 1.550(2) . ?
C9 C10 1.542(2) . ?
C9 H9 0.9800 . ?
C10 C12 1.514(2) . ?
C10 C17 1.552(2) . ?
C10 H10 0.9800 . ?
C11 N2 1.341(2) . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(2) . ?
C13 C14 1.379(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(2) . ?
C14 H14 0.9300 . ?
C15 N2 1.323(2) . ?
C15 H15 0.9300 . ?
C16 N1 1.453(2) . ?
C16 C17 1.535(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.502(3) . ?
C17 H17 0.9800 . ?
C18 O3 1.2134(19) . ?
C18 C19 1.500(2) . ?
C19 C20 1.536(2) . ?
C19 H19 0.9800 . ?
C20 N1 1.445(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 N1 1.458(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O2 H2 0.8200 . ?

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 C2 127.32(15) . . ?
O1 C1 C9 125.71(14) . . ?
C2 C1 C9 106.77(13) . . ?
C7 C2 C3 121.35(15) . . ?
C7 C2 C1 109.68(13) . . ?
C3 C2 C1 128.96(16) . . ?
C4 C3 C2 118.12(17) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.66(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.51(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C7 117.95(17) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C2 C7 C6 120.38(15) . . ?
C2 C7 C8 111.73(13) . . ?
C6 C7 C8 127.65(14) . . ?
O2 C8 C7 113.81(12) . . ?
O2 C8 C9 113.15(11) . . ?
C7 C8 C9 102.55(11) . . ?
O2 C8 C19 103.85(11) . . ?
C7 C8 C19 110.04(12) . . ?
C9 C8 C19 113.75(12) . . ?
C1 C9 C10 114.49(13) . . ?
C1 C9 C8 105.10(12) . . ?
C10 C9 C8 119.00(12) . . ?
C1 C9 H9 105.7 . . ?
C10 C9 H9 105.7 . . ?
C8 C9 H9 105.7 . . ?
C12 C10 C9 113.01(13) . . ?
C12 C10 C17 111.77(12) . . ?
C9 C10 C17 112.97(12) . . ?
C12 C10 H10 106.1 . . ?
C9 C10 H10 106.1 . . ?
C17 C10 H10 106.1 . . ?
N2 C11 C12 124.97(16) . . ?
N2 C11 H11 117.5 . . ?
C12 C11 H11 117.5 . . ?
C11 C12 C13 116.16(14) . . ?
C11 C12 C10 119.27(14) . . ?
C13 C12 C10 124.57(13) . . ?
C14 C13 C12 119.95(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 118.74(16) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
N2 C15 C14 123.35(15) . . ?
N2 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N1 C16 C17 110.65(14) . . ?
N1 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 107.83(13) . . ?
C18 C17 C10 110.75(14) . . ?
C16 C17 C10 110.96(13) . . ?
C18 C17 H17 109.1 . . ?
C16 C17 H17 109.1 . . ?
C10 C17 H17 109.1 . . ?
O3 C18 C19 124.02(17) . . ?
O3 C18 C17 123.96(17) . . ?
C19 C18 C17 111.88(13) . . ?
C18 C19 C20 105.96(14) . . ?
C18 C19 C8 110.33(12) . . ?
C20 C19 C8 113.76(12) . . ?
C18 C19 H19 108.9 . . ?
C20 C19 H19 108.9 . . ?
C8 C19 H19 108.9 . . ?
N1 C20 C19 109.31(12) . . ?
N1 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
N1 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 N1 C16 110.57(13) . . ?
C20 N1 C21 112.71(14) . . ?
C16 N1 C21 112.91(15) . . ?
C15 N2 C11 116.82(14) . . ?
C8 O2 H2 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N2 0.82 2.02 2.8285(18) 167.2 2_545

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 1814881'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-05-22 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         'C28 H24 N2 O5'
_chemical_formula_sum            'C28 H24 N2 O5'
_chemical_formula_weight         468.49

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      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                   17.485(5)
_cell_length_b                   23.214(7)
_cell_length_c                   13.752(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.437(13)
_cell_angle_gamma                90
_cell_volume                     5582(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1568
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      20.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11540
_diffrn_reflns_av_unetI/netI     0.2537
_diffrn_reflns_av_R_equivalents  0.1669
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.458
_diffrn_reflns_theta_max         24.710
_diffrn_reflns_theta_full        24.710
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             4642
_reflns_number_gt                1731
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²] 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         4642
_refine_ls_number_parameters     320
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2778
_refine_ls_R_factor_gt           0.1179
_refine_ls_wR_factor_ref         0.3805
_refine_ls_wR_factor_gt          0.2924
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.0856(5) -0.1392(3) 0.6254(7) 0.065(3) Uani 1 1 d . . . . .
H1 H 0.0749 -0.1062 0.6611 0.078 Uiso 1 1 calc R U . . .
C2 C 0.0296(6) -0.1820(5) 0.6154(8) 0.087(3) Uani 1 1 d . . . . .
H2 H -0.0187 -0.1763 0.6417 0.105 Uiso 1 1 calc R U . . .
C3 C 0.0452(6) -0.2312(4) 0.5679(10) 0.109(4) Uani 1 1 d . . . . .
H3 H 0.0084 -0.2600 0.5622 0.130 Uiso 1 1 calc R U . . .
C4 C 0.1147(6) -0.2384(4) 0.5287(10) 0.109(4) Uani 1 1 d . . . . .
H4 H 0.1255 -0.2725 0.4961 0.131 Uiso 1 1 calc R U . . .
C5 C 0.1717(6) -0.1956(3) 0.5356(8) 0.088(4) Uani 1 1 d . . . . .
H5 H 0.2194 -0.2018 0.5081 0.105 Uiso 1 1 calc R U . . .
C6 C 0.1569(4) -0.1453(3) 0.5826(6) 0.051(2) Uani 1 1 d . . . . .
C7 C 0.2168(4) -0.0979(3) 0.5892(6) 0.051(2) Uani 1 1 d . . . . .
H7A H 0.2127 -0.0796 0.6524 0.061 Uiso 1 1 calc R U . . .
H7B H 0.2670 -0.1156 0.5861 0.061 Uiso 1 1 calc R U . . .
C8 C 0.1467(5) -0.0155(3) 0.5213(6) 0.056(2) Uani 1 1 d . . . . .
H8A H 0.1409 -0.0028 0.5881 0.067 Uiso 1 1 calc R U . . .
H8B H 0.1009 -0.0366 0.5029 0.067 Uiso 1 1 calc R U . . .
C9 C 0.1551(4) 0.0371(3) 0.4553(6) 0.054(2) Uani 1 1 d . . . . .
H9 H 0.1074 0.0591 0.4564 0.065 Uiso 1 1 calc R U . . .
C10 C 0.1672(5) 0.0139(3) 0.3522(6) 0.045(2) Uani 1 1 d . . . . .
C11 C 0.2353(4) -0.0230(3) 0.3467(5) 0.0413(19) Uani 1 1 d . . . . .
H11 H 0.2402 -0.0376 0.2801 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2214(4) -0.0745(3) 0.4163(5) 0.049(2) Uani 1 1 d . . . . .
H12A H 0.1757 -0.0952 0.3964 0.059 Uiso 1 1 calc R U . . .
H12B H 0.2643 -0.1009 0.4138 0.059 Uiso 1 1 calc R U . . .
C13 C 0.3112(4) 0.0102(3) 0.3757(5) 0.0364(18) Uani 1 1 d . . . . .
C14 C 0.3732(4) -0.0294(2) 0.4065(6) 0.0383(19) Uani 1 1 d . . . . .
C15 C 0.4179(5) -0.0665(3) 0.3502(7) 0.066(3) Uani 1 1 d . . . . .
H15 H 0.4113 -0.0678 0.2830 0.079 Uiso 1 1 calc R U . . .
C16 C 0.4708(5) -0.1003(3) 0.3943(7) 0.058(2) Uani 1 1 d . . . . .
H16 H 0.5006 -0.1246 0.3565 0.070 Uiso 1 1 calc R U . . .
C17 C 0.4817(5) -0.0996(3) 0.4929(7) 0.062(2) Uani 1 1 d . . . . .
H17 H 0.5180 -0.1236 0.5218 0.075 Uiso 1 1 calc R U . . .
C18 C 0.4377(5) -0.0625(3) 0.5494(6) 0.053(2) Uani 1 1 d . . . . .
H18 H 0.4440 -0.0620 0.6166 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3870(4) -0.0279(3) 0.5076(6) 0.0382(19) Uani 1 1 d . . . . .
C20 C 0.3331(4) 0.0159(3) 0.5465(6) 0.0378(19) Uani 1 1 d . . . . .
C21 C 0.3006(4) 0.0503(3) 0.4650(5) 0.0369(18) Uani 1 1 d . . . . .
H21 H 0.3354 0.0829 0.4556 0.044 Uiso 1 1 calc R U . . .
C22 C 0.2211(4) 0.0767(3) 0.4867(5) 0.0409(19) Uani 1 1 d . . . . .
H22 H 0.2179 0.0806 0.5575 0.049 Uiso 1 1 calc R U . . .
C23 C 0.2095(4) 0.1366(3) 0.4446(6) 0.052(2) Uani 1 1 d . . . . .
C24 C 0.2343(6) 0.1524(3) 0.3530(7) 0.079(3) Uani 1 1 d . . . . .
H24 H 0.2610 0.1263 0.3148 0.095 Uiso 1 1 calc R U . . .
C25 C 0.2191(7) 0.2071(3) 0.3189(7) 0.087(3) Uani 1 1 d . . . . .
H25 H 0.2349 0.2173 0.2567 0.104 Uiso 1 1 calc R U . . .
C26 C 0.1824(5) 0.2459(3) 0.3729(9) 0.081(3) Uani 1 1 d . . . . .
C27 C 0.1596(5) 0.2328(3) 0.4674(9) 0.077(3) Uani 1 1 d . . . . .
H27 H 0.1366 0.2603 0.5067 0.093 Uiso 1 1 calc R U . . .
C28 C 0.1727(4) 0.1773(3) 0.5001(7) 0.066(3) Uani 1 1 d . . . . .
H28 H 0.1561 0.1670 0.5618 0.080 Uiso 1 1 calc R U . . .
N1 N 0.2125(3) -0.0531(2) 0.5146(4) 0.0426(16) Uani 1 1 d . . . . .
N2 N 0.1700(6) 0.3050(3) 0.3335(9) 0.107(4) Uani 1 1 d . . . . .
O1 O 0.1234(3) 0.0238(2) 0.2851(5) 0.0692(17) Uani 1 1 d . . . . .
O2 O 0.3311(3) 0.04554(18) 0.2923(3) 0.0466(14) Uani 1 1 d D . . . .
O3 O 0.3244(3) 0.02557(19) 0.6342(4) 0.0545(15) Uani 1 1 d . . . . .
O4 O 0.1335(5) 0.3372(3) 0.3827(9) 0.153(4) Uani 1 1 d . . . . .
O5 O 0.2043(8) 0.3189(3) 0.2601(8) 0.177(5) Uani 1 1 d . . . . .
H2A H 0.382(2) 0.062(4) 0.297(7) 0.11(4) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.390(10) . ?
C1 C2 1.401(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.344(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.522(10) . ?
C7 N1 1.463(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.448(9) . ?
C8 C9 1.529(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.532(11) . ?
C9 C22 1.534(10) . ?
C9 H9 0.9800 . ?
C10 O1 1.216(9) . ?
C10 C11 1.469(10) . ?
C11 C12 1.553(9) . ?
C11 C13 1.583(10) . ?
C11 H11 0.9800 . ?
C12 N1 1.450(9) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.454(8) . ?
C13 C14 1.481(9) . ?
C13 C21 1.553(9) . ?
C14 C15 1.402(9) . ?
C14 C19 1.409(10) . ?
C15 C16 1.353(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(12) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.325(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.489(9) . ?
C20 O3 1.237(8) . ?
C20 C21 1.485(10) . ?
C21 C22 1.550(9) . ?
C21 H21 0.9800 . ?
C22 C23 1.520(9) . ?
C22 H22 0.9800 . ?
C23 C28 1.376(9) . ?
C23 C24 1.385(11) . ?
C24 C25 1.379(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.334(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.396(14) . ?
C26 N2 1.490(12) . ?
C27 C28 1.385(11) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
N2 O4 1.196(10) . ?
N2 O5 1.222(12) . ?
O2 H2A 0.971(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.0(8) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.4(9) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.1(9) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.9(9) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.0(8) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 117.6(7) . . ?
C5 C6 C7 121.0(7) . . ?
C1 C6 C7 121.4(7) . . ?
N1 C7 C6 116.2(6) . . ?
N1 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
N1 C7 H7B 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 C9 111.2(5) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 C10 106.5(6) . . ?
C8 C9 C22 112.8(7) . . ?
C10 C9 C22 111.2(5) . . ?
C8 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C22 C9 H9 108.7 . . ?
O1 C10 C11 125.2(7) . . ?
O1 C10 C9 123.0(7) . . ?
C11 C10 C9 111.7(7) . . ?
C10 C11 C12 106.7(5) . . ?
C10 C11 C13 112.4(5) . . ?
C12 C11 C13 110.8(6) . . ?
C10 C11 H11 109.0 . . ?
C12 C11 H11 109.0 . . ?
C13 C11 H11 109.0 . . ?
N1 C12 C11 109.2(5) . . ?
N1 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
O2 C13 C14 113.4(5) . . ?
O2 C13 C21 108.5(4) . . ?
C14 C13 C21 103.7(6) . . ?
O2 C13 C11 106.3(6) . . ?
C14 C13 C11 112.3(5) . . ?
C21 C13 C11 112.7(5) . . ?
C15 C14 C19 117.9(7) . . ?
C15 C14 C13 129.3(7) . . ?
C19 C14 C13 112.8(6) . . ?
C16 C15 C14 119.4(9) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 121.9(8) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 119.0(8) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 120.2(8) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 121.5(7) . . ?
C18 C19 C20 133.0(7) . . ?
C14 C19 C20 105.5(7) . . ?
O3 C20 C21 126.1(6) . . ?
O3 C20 C19 123.9(7) . . ?
C21 C20 C19 109.6(6) . . ?
C20 C21 C22 114.0(5) . . ?
C20 C21 C13 103.2(5) . . ?
C22 C21 C13 120.1(6) . . ?
C20 C21 H21 106.2 . . ?
C22 C21 H21 106.2 . . ?
C13 C21 H21 106.2 . . ?
C23 C22 C9 110.1(6) . . ?
C23 C22 C21 114.0(5) . . ?
C9 C22 C21 112.5(5) . . ?
C23 C22 H22 106.6 . . ?
C9 C22 H22 106.6 . . ?
C21 C22 H22 106.6 . . ?
C28 C23 C24 118.3(7) . . ?
C28 C23 C22 118.6(7) . . ?
C24 C23 C22 123.1(6) . . ?
C25 C24 C23 119.5(8) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 121.6(9) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C27 120.9(8) . . ?
C25 C26 N2 119.2(10) . . ?
C27 C26 N2 119.7(9) . . ?
C28 C27 C26 117.2(8) . . ?
C28 C27 H27 121.4 . . ?
C26 C27 H27 121.4 . . ?
C23 C28 C27 122.4(8) . . ?
C23 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C8 N1 C12 111.0(6) . . ?
C8 N1 C7 114.9(5) . . ?
C12 N1 C7 113.8(5) . . ?
O4 N2 O5 124.6(9) . . ?
O4 N2 C26 116.6(10) . . ?
O5 N2 C26 118.2(9) . . ?
C13 O2 H2A 113(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
C6 C1 C2 C3 3.2(16) . . . . ?
C1 C2 C3 C4 -1.2(19) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 -0.3(18) . . . . ?
C4 C5 C6 C1 2.2(15) . . . . ?
C4 C5 C6 C7 -178.6(9) . . . . ?
C2 C1 C6 C5 -3.6(13) . . . . ?
C2 C1 C6 C7 177.2(8) . . . . ?
C5 C6 C7 N1 94.4(9) . . . . ?
C1 C6 C7 N1 -86.4(9) . . . . ?
N1 C8 C9 C10 56.8(9) . . . . ?
N1 C8 C9 C22 -65.5(8) . . . . ?
C8 C9 C10 O1 118.4(8) . . . . ?
C22 C9 C10 O1 -118.4(8) . . . . ?
C8 C9 C10 C11 -59.1(8) . . . . ?
C22 C9 C10 C11 64.2(7) . . . . ?
O1 C10 C11 C12 -116.2(8) . . . . ?
C9 C10 C11 C12 61.1(7) . . . . ?
O1 C10 C11 C13 122.2(8) . . . . ?
C9 C10 C11 C13 -60.5(7) . . . . ?
C10 C11 C12 N1 -61.2(8) . . . . ?
C13 C11 C12 N1 61.4(7) . . . . ?
C10 C11 C13 O2 -77.2(6) . . . . ?
C12 C11 C13 O2 163.6(5) . . . . ?
C10 C11 C13 C14 158.2(6) . . . . ?
C12 C11 C13 C14 39.0(7) . . . . ?
C10 C11 C13 C21 41.5(8) . . . . ?
C12 C11 C13 C21 -77.7(6) . . . . ?
O2 C13 C14 C15 -47.5(9) . . . . ?
C21 C13 C14 C15 -165.0(6) . . . . ?
C11 C13 C14 C15 73.0(8) . . . . ?
O2 C13 C14 C19 132.4(6) . . . . ?
C21 C13 C14 C19 14.9(7) . . . . ?
C11 C13 C14 C19 -107.1(6) . . . . ?
C19 C14 C15 C16 1.7(10) . . . . ?
C13 C14 C15 C16 -178.4(7) . . . . ?
C14 C15 C16 C17 0.4(12) . . . . ?
C15 C16 C17 C18 -0.8(12) . . . . ?
C16 C17 C18 C19 -1.0(11) . . . . ?
C17 C18 C19 C14 3.1(10) . . . . ?
C17 C18 C19 C20 -179.4(6) . . . . ?
C15 C14 C19 C18 -3.5(10) . . . . ?
C13 C14 C19 C18 176.6(6) . . . . ?
C15 C14 C19 C20 178.5(5) . . . . ?
C13 C14 C19 C20 -1.5(7) . . . . ?
C18 C19 C20 O3 -3.9(11) . . . . ?
C14 C19 C20 O3 173.8(6) . . . . ?
C18 C19 C20 C21 168.6(7) . . . . ?
C14 C19 C20 C21 -13.6(7) . . . . ?
O3 C20 C21 C22 -33.6(9) . . . . ?
C19 C20 C21 C22 154.0(5) . . . . ?
O3 C20 C21 C13 -165.5(6) . . . . ?
C19 C20 C21 C13 22.2(7) . . . . ?
O2 C13 C21 C20 -142.6(5) . . . . ?
C14 C13 C21 C20 -21.7(6) . . . . ?
C11 C13 C21 C20 100.0(6) . . . . ?
O2 C13 C21 C22 89.3(7) . . . . ?
C14 C13 C21 C22 -149.9(5) . . . . ?
C11 C13 C21 C22 -28.2(8) . . . . ?
C8 C9 C22 C23 -159.3(6) . . . . ?
C10 C9 C22 C23 81.0(7) . . . . ?
C8 C9 C22 C21 72.4(7) . . . . ?
C10 C9 C22 C21 -47.2(8) . . . . ?
C20 C21 C22 C23 142.6(6) . . . . ?
C13 C21 C22 C23 -94.4(7) . . . . ?
C20 C21 C22 C9 -91.2(7) . . . . ?
C13 C21 C22 C9 31.9(8) . . . . ?
C9 C22 C23 C28 93.4(9) . . . . ?
C21 C22 C23 C28 -139.1(8) . . . . ?
C9 C22 C23 C24 -86.7(9) . . . . ?
C21 C22 C23 C24 40.8(11) . . . . ?
C28 C23 C24 C25 -2.4(15) . . . . ?
C22 C23 C24 C25 177.7(9) . . . . ?
C23 C24 C25 C26 1.5(17) . . . . ?
C24 C25 C26 C27 1.6(17) . . . . ?
C24 C25 C26 N2 177.9(10) . . . . ?
C25 C26 C27 C28 -3.7(15) . . . . ?
N2 C26 C27 C28 -179.9(8) . . . . ?
C24 C23 C28 C27 0.2(14) . . . . ?
C22 C23 C28 C27 -179.9(8) . . . . ?
C26 C27 C28 C23 2.7(14) . . . . ?
C9 C8 N1 C12 -61.1(8) . . . . ?
C9 C8 N1 C7 168.0(7) . . . . ?
C11 C12 N1 C8 62.0(7) . . . . ?
C11 C12 N1 C7 -166.5(6) . . . . ?
C6 C7 N1 C8 68.9(8) . . . . ?
C6 C7 N1 C12 -60.6(8) . . . . ?
C25 C26 N2 O4 176.4(11) . . . . ?
C27 C26 N2 O4 -7.3(15) . . . . ?
C25 C26 N2 O5 -11.7(17) . . . . ?
C27 C26 N2 O5 164.7(13) . . . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.122





#======================================================================================
####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 1587033'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C37 H28 Cl N O4'
_chemical_formula_sum            'C37 H28 Cl N O4'
_chemical_formula_weight         586.05

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'
Cl Cl 0.1484 0.1585 '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                   14.5654(7)
_cell_length_b                   22.6550(11)
_cell_length_c                   8.9813(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.5598(15)
_cell_angle_gamma                90
_cell_volume                     2881.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44788
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6642
_reflns_number_gt                4052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0518P)²+1.2560P] 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         6642
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.57481(15) 0.34472(11) 1.1193(3) 0.0499(6) Uani 1 1 d . . . . .
H1 H 0.5788 0.3843 1.1478 0.060 Uiso 1 1 calc R U . . .
C2 C 0.49209(16) 0.31372(13) 1.1120(3) 0.0613(7) Uani 1 1 d . . . . .
C3 C 0.48312(19) 0.25558(14) 1.0698(3) 0.0743(9) Uani 1 1 d . . . . .
H3 H 0.4269 0.2354 1.0647 0.089 Uiso 1 1 calc R U . . .
C4 C 0.5596(2) 0.22765(13) 1.0349(3) 0.0732(8) Uani 1 1 d . . . . .
H4 H 0.5549 0.1882 1.0055 0.088 Uiso 1 1 calc R U . . .
C5 C 0.64279(17) 0.25771(11) 1.0432(3) 0.0558(6) Uani 1 1 d . . . . .
H5 H 0.6940 0.2381 1.0209 0.067 Uiso 1 1 calc R U . . .
C6 C 0.65141(14) 0.31696(9) 1.0843(2) 0.0403(5) Uani 1 1 d . . . . .
C7 C 0.74473(12) 0.34767(8) 1.0869(2) 0.0332(4) Uani 1 1 d . . . . .
H7 H 0.7936 0.3238 1.1540 0.040 Uiso 1 1 calc R U . . .
C8 C 0.75407(13) 0.41030(9) 1.1566(2) 0.0344(4) Uani 1 1 d . . . . .
H8 H 0.6939 0.4314 1.1265 0.041 Uiso 1 1 calc R U . . .
C9 C 0.78275(15) 0.40262(10) 1.3305(2) 0.0436(5) Uani 1 1 d . . . . .
C10 C 0.88601(14) 0.41253(9) 1.3783(2) 0.0396(5) Uani 1 1 d . . . . .
C11 C 0.94706(16) 0.40275(11) 1.5198(3) 0.0518(6) Uani 1 1 d . . . . .
H11 H 0.9253 0.3867 1.6005 0.062 Uiso 1 1 calc R U . . .
C12 C 1.04093(16) 0.41742(11) 1.5376(3) 0.0547(6) Uani 1 1 d . . . . .
H12 H 1.0832 0.4112 1.6314 0.066 Uiso 1 1 calc R U . . .
C13 C 1.07271(15) 0.44122(10) 1.4175(3) 0.0495(6) Uani 1 1 d . . . . .
H13 H 1.1362 0.4511 1.4318 0.059 Uiso 1 1 calc R U . . .
C14 C 1.01205(13) 0.45068(9) 1.2764(2) 0.0402(5) Uani 1 1 d . . . . .
H14 H 1.0340 0.4665 1.1958 0.048 Uiso 1 1 calc R U . . .
C15 C 0.91750(13) 0.43600(8) 1.2577(2) 0.0336(4) Uani 1 1 d . . . . .
C16 C 0.83490(12) 0.44791(8) 1.1211(2) 0.0313(4) Uani 1 1 d . . . . .
C17 C 0.94074(14) 0.27628(9) 0.8837(3) 0.0427(5) Uani 1 1 d . . . . .
C18 C 1.03549(14) 0.26460(9) 0.8537(2) 0.0437(5) Uani 1 1 d . . . . .
C19 C 1.07133(18) 0.21267(11) 0.8108(3) 0.0617(7) Uani 1 1 d . . . . .
H19 H 1.0356 0.1782 0.7959 0.074 Uiso 1 1 calc R U . . .
C20 C 1.1628(2) 0.21388(14) 0.7908(3) 0.0745(8) Uani 1 1 d . . . . .
H20 H 1.1887 0.1797 0.7607 0.089 Uiso 1 1 calc R U . . .
C21 C 1.21620(18) 0.26466(14) 0.8146(3) 0.0732(8) Uani 1 1 d . . . . .
H21 H 1.2774 0.2640 0.8005 0.088 Uiso 1 1 calc R U . . .
C22 C 1.18077(15) 0.31649(12) 0.8588(3) 0.0580(6) Uani 1 1 d . . . . .
H22 H 1.2172 0.3506 0.8758 0.070 Uiso 1 1 calc R U . . .
C23 C 1.08909(14) 0.31589(10) 0.8772(2) 0.0413(5) Uani 1 1 d . . . . .
C24 C 1.03281(13) 0.36482(9) 0.9194(2) 0.0364(5) Uani 1 1 d . . . . .
C25 C 0.93749(12) 0.34067(8) 0.9193(2) 0.0333(4) Uani 1 1 d . . . . .
C26 C 0.69351(13) 0.37582(9) 0.7989(2) 0.0356(5) Uani 1 1 d . . . . .
H26A H 0.7080 0.3678 0.7008 0.043 Uiso 1 1 calc R U . . .
H26B H 0.6312 0.3599 0.7958 0.043 Uiso 1 1 calc R U . . .
C27 C 0.76591(12) 0.34459(8) 0.9251(2) 0.0318(4) Uani 1 1 d . . . . .
H27 H 0.7686 0.3030 0.8967 0.038 Uiso 1 1 calc R U . . .
C28 C 0.86140(12) 0.37136(8) 0.9371(2) 0.0305(4) Uani 1 1 d . . . . .
C29 C 0.85876(12) 0.43655(8) 0.9654(2) 0.0310(4) Uani 1 1 d . . . . .
H29 H 0.9210 0.4534 0.9673 0.037 Uiso 1 1 calc R U . . .
C30 C 0.78594(13) 0.46389(9) 0.8322(2) 0.0373(5) Uani 1 1 d . . . . .
H30A H 0.7842 0.5063 0.8466 0.045 Uiso 1 1 calc R U . . .
H30B H 0.8048 0.4566 0.7372 0.045 Uiso 1 1 calc R U . . .
C31 C 0.62462(14) 0.46831(10) 0.6954(3) 0.0473(5) Uani 1 1 d . . . . .
H31A H 0.6413 0.4591 0.5996 0.057 Uiso 1 1 calc R U . . .
H31B H 0.6291 0.5107 0.7097 0.057 Uiso 1 1 calc R U . . .
C32 C 0.52469(14) 0.44925(10) 0.6856(3) 0.0452(5) Uani 1 1 d . . . . .
C33 C 0.48383(18) 0.45977(15) 0.8064(3) 0.0759(8) Uani 1 1 d . . . . .
H33 H 0.5189 0.4781 0.8941 0.091 Uiso 1 1 calc R U . . .
C34 C 0.3922(2) 0.44364(18) 0.7994(4) 0.0956(11) Uani 1 1 d . . . . .
H34 H 0.3654 0.4510 0.8819 0.115 Uiso 1 1 calc R U . . .
C35 C 0.34022(19) 0.41662(16) 0.6704(4) 0.0884(11) Uani 1 1 d . . . . .
H35 H 0.2779 0.4059 0.6652 0.106 Uiso 1 1 calc R U . . .
C36 C 0.37956(19) 0.40547(13) 0.5497(4) 0.0720(8) Uani 1 1 d . . . . .
H36 H 0.3445 0.3867 0.4627 0.086 Uiso 1 1 calc R U . . .
C37 C 0.47191(16) 0.42225(10) 0.5573(3) 0.0518(6) Uani 1 1 d . . . . .
H37 H 0.4984 0.4151 0.4744 0.062 Uiso 1 1 calc R U . . .
Cl1 Cl 0.39740(5) 0.34958(5) 1.16062(11) 0.1018(3) Uani 1 1 d . . . . .
N1 N 0.69209(11) 0.43942(7) 0.82157(18) 0.0366(4) Uani 1 1 d . . . . .
O1 O 0.73133(12) 0.38980(9) 1.41353(19) 0.0698(5) Uani 1 1 d . . . . .
O2 O 0.80619(9) 0.50801(6) 1.13042(17) 0.0400(3) Uani 1 1 d . . . . .
H2 H 0.8463 0.5301 1.1104 0.060 Uiso 1 1 calc R U . . .
O3 O 0.88066(11) 0.23926(7) 0.8801(2) 0.0727(6) Uani 1 1 d . . . . .
O4 O 1.06075(10) 0.41524(7) 0.94574(19) 0.0513(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.380(3) . ?
C1 C2 1.383(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(4) . ?
C2 Cl1 1.742(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.522(3) . ?
C7 C8 1.544(3) . ?
C7 C27 1.556(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.529(3) . ?
C8 C16 1.546(2) . ?
C8 H8 0.9800 . ?
C9 O1 1.210(2) . ?
C9 C10 1.481(3) . ?
C10 C15 1.379(3) . ?
C10 C11 1.388(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.527(3) . ?
C16 O2 1.433(2) . ?
C16 C29 1.540(3) . ?
C17 O3 1.207(2) . ?
C17 C18 1.490(3) . ?
C17 C25 1.497(3) . ?
C18 C19 1.378(3) . ?
C18 C23 1.388(3) . ?
C19 C20 1.386(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.480(3) . ?
C24 O4 1.217(2) . ?
C24 C25 1.492(3) . ?
C25 C28 1.349(3) . ?
C26 N1 1.456(3) . ?
C26 C27 1.529(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.498(2) . ?
C27 H27 0.9800 . ?
C28 C29 1.501(3) . ?
C29 C30 1.531(3) . ?
C29 H29 0.9800 . ?
C30 N1 1.457(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 N1 1.468(3) . ?
C31 C32 1.501(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C37 1.370(3) . ?
C32 C33 1.375(3) . ?
C33 C34 1.371(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.364(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.384(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
O2 H2 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.0(2) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 Cl1 119.25(19) . . ?
C1 C2 Cl1 118.9(2) . . ?
C2 C3 C4 118.3(2) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.25(19) . . ?
C1 C6 C7 123.71(19) . . ?
C5 C6 C7 118.0(2) . . ?
C6 C7 C8 114.81(16) . . ?
C6 C7 C27 109.72(15) . . ?
C8 C7 C27 113.71(15) . . ?
C6 C7 H7 105.9 . . ?
C8 C7 H7 105.9 . . ?
C27 C7 H7 105.9 . . ?
C9 C8 C7 106.66(16) . . ?
C9 C8 C16 103.55(15) . . ?
C7 C8 C16 114.96(15) . . ?
C9 C8 H8 110.5 . . ?
C7 C8 H8 110.5 . . ?
C16 C8 H8 110.5 . . ?
O1 C9 C10 126.2(2) . . ?
O1 C9 C8 126.63(19) . . ?
C10 C9 C8 107.13(16) . . ?
C15 C10 C11 121.45(19) . . ?
C15 C10 C9 109.44(17) . . ?
C11 C10 C9 129.09(19) . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C10 C15 C14 120.04(18) . . ?
C10 C15 C16 110.78(16) . . ?
C14 C15 C16 128.86(18) . . ?
O2 C16 C15 107.87(15) . . ?
O2 C16 C29 110.06(15) . . ?
C15 C16 C29 113.37(14) . . ?
O2 C16 C8 105.37(14) . . ?
C15 C16 C8 103.40(15) . . ?
C29 C16 C8 116.11(15) . . ?
O3 C17 C18 124.63(19) . . ?
O3 C17 C25 128.59(19) . . ?
C18 C17 C25 106.78(17) . . ?
C19 C18 C23 121.4(2) . . ?
C19 C18 C17 129.0(2) . . ?
C23 C18 C17 109.61(18) . . ?
C18 C19 C20 117.3(2) . . ?
C18 C19 H19 121.4 . . ?
C20 C19 H19 121.4 . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 121.4(2) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C23 117.6(2) . . ?
C21 C22 H22 121.2 . . ?
C23 C22 H22 121.2 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 C24 129.1(2) . . ?
C18 C23 C24 109.89(17) . . ?
O4 C24 C23 124.94(18) . . ?
O4 C24 C25 127.80(18) . . ?
C23 C24 C25 107.24(17) . . ?
C28 C25 C24 126.95(18) . . ?
C28 C25 C17 126.55(17) . . ?
C24 C25 C17 106.36(16) . . ?
N1 C26 C27 112.58(15) . . ?
N1 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
N1 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C28 C27 C26 109.47(15) . . ?
C28 C27 C7 107.38(15) . . ?
C26 C27 C7 114.74(15) . . ?
C28 C27 H27 108.4 . . ?
C26 C27 H27 108.4 . . ?
C7 C27 H27 108.4 . . ?
C25 C28 C27 123.89(17) . . ?
C25 C28 C29 125.56(16) . . ?
C27 C28 C29 110.52(15) . . ?
C28 C29 C30 107.84(15) . . ?
C28 C29 C16 109.78(15) . . ?
C30 C29 C16 112.30(15) . . ?
C28 C29 H29 109.0 . . ?
C30 C29 H29 109.0 . . ?
C16 C29 H29 109.0 . . ?
N1 C30 C29 111.39(15) . . ?
N1 C30 H30A 109.4 . . ?
C29 C30 H30A 109.4 . . ?
N1 C30 H30B 109.4 . . ?
C29 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
N1 C31 C32 112.42(17) . . ?
N1 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
N1 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
C37 C32 C33 118.7(2) . . ?
C37 C32 C31 121.5(2) . . ?
C33 C32 C31 119.8(2) . . ?
C34 C33 C32 121.0(3) . . ?
C34 C33 H33 119.5 . . ?
C32 C33 H33 119.5 . . ?
C35 C34 C33 119.8(3) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C36 C35 C34 120.2(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C37 119.6(3) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C32 C37 C36 120.8(2) . . ?
C32 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C26 N1 C30 109.97(15) . . ?
C26 N1 C31 111.22(16) . . ?
C30 N1 C31 109.20(15) . . ?
C16 O2 H2 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O4 0.82 1.99 2.8051(19) 177.5 3_767

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_2b_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1814880'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-05-22 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         'C22 H20 Br N O3'
_chemical_formula_sum            'C22 H20 Br N O3'
_chemical_formula_weight         426.30

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'
Br Br -0.2901 2.4595 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.7048(8)
_cell_length_b                   19.6596(19)
_cell_length_c                   22.0693(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3776.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6157
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.199
_shelx_estimated_absorpt_T_min   0.620
_shelx_estimated_absorpt_T_max   0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26253
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4332
_reflns_number_gt                2506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0718P)²] 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         4332
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.58143(6) 1.02271(2) 0.71425(2) 0.0749(2) Uani 1 1 d . . . . .
C1 C 1.1745(4) 0.7816(2) 0.36510(16) 0.0610(10) Uani 1 1 d . . . . .
H1A H 1.2367 0.8099 0.3395 0.091 Uiso 1 1 calc R U . . .
H1B H 1.1329 0.7447 0.3417 0.091 Uiso 1 1 calc R U . . .
H1C H 1.2364 0.7637 0.3974 0.091 Uiso 1 1 calc R U . . .
C2 C 0.9548(3) 0.85280(16) 0.34406(13) 0.0415(8) Uani 1 1 d . . . . .
H2A H 0.9232 0.8184 0.3151 0.050 Uiso 1 1 calc R U . . .
H2B H 1.0141 0.8869 0.3226 0.050 Uiso 1 1 calc R U . . .
C3 C 0.8123(3) 0.88595(15) 0.37239(13) 0.0382(7) Uani 1 1 d . . . . .
H3 H 0.7523 0.9080 0.3404 0.046 Uiso 1 1 calc R U . . .
C4 C 0.8661(3) 0.93907(17) 0.41651(15) 0.0422(8) Uani 1 1 d . . . . .
C5 C 0.9725(3) 0.90964(15) 0.46329(13) 0.0380(7) Uani 1 1 d . . . . .
H5 H 1.0135 0.9467 0.4882 0.046 Uiso 1 1 calc R U . . .
C6 C 1.1055(3) 0.87381(17) 0.43174(14) 0.0421(8) Uani 1 1 d . . . . .
H6A H 1.1657 0.9068 0.4093 0.051 Uiso 1 1 calc R U . . .
H6B H 1.1718 0.8530 0.4618 0.051 Uiso 1 1 calc R U . . .
C7 C 0.6647(4) 0.93654(16) 0.54671(14) 0.0455(8) Uani 1 1 d . . . . .
H7 H 0.6173 0.9364 0.5089 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6002(4) 0.97341(17) 0.59326(15) 0.0464(8) Uani 1 1 d . . . . .
H8 H 0.5110 0.9985 0.5870 0.056 Uiso 1 1 calc R U . . .
C9 C 0.6695(4) 0.97260(16) 0.64911(14) 0.0436(8) Uani 1 1 d . . . . .
C10 C 0.8021(4) 0.93688(19) 0.65872(14) 0.0567(10) Uani 1 1 d . . . . .
H10 H 0.8489 0.9371 0.6966 0.068 Uiso 1 1 calc R U . . .
C11 C 0.8650(4) 0.90076(19) 0.61166(14) 0.0487(9) Uani 1 1 d . . . . .
H11 H 0.9550 0.8764 0.6183 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7988(3) 0.89955(14) 0.55487(12) 0.0340(7) Uani 1 1 d . . . . .
C13 C 0.8806(3) 0.86026(15) 0.50462(12) 0.0323(7) Uani 1 1 d . . . . .
H13 H 0.9569 0.8314 0.5248 0.039 Uiso 1 1 calc R U . . .
C14 C 0.7758(3) 0.81192(13) 0.46843(11) 0.0288(6) Uani 1 1 d . . . . .
H14 H 0.6867 0.8037 0.4946 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8443(3) 0.74248(14) 0.45649(12) 0.0323(7) Uani 1 1 d . . . . .
C16 C 0.7810(3) 0.71735(15) 0.39886(13) 0.0356(7) Uani 1 1 d . . . . .
C17 C 0.7947(4) 0.65290(17) 0.37284(16) 0.0515(9) Uani 1 1 d . . . . .
H17 H 0.8522 0.6189 0.3915 0.062 Uiso 1 1 calc R U . . .
C18 C 0.7207(4) 0.6413(2) 0.31892(18) 0.0637(11) Uani 1 1 d . . . . .
H18 H 0.7288 0.5990 0.3004 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6344(5) 0.6918(2) 0.29202(16) 0.0667(12) Uani 1 1 d . . . . .
H19 H 0.5845 0.6826 0.2557 0.080 Uiso 1 1 calc R U . . .
C20 C 0.6201(4) 0.7555(2) 0.31757(14) 0.0531(9) Uani 1 1 d . . . . .
H20 H 0.5615 0.7891 0.2989 0.064 Uiso 1 1 calc R U . . .
C21 C 0.6955(3) 0.76828(15) 0.37185(13) 0.0361(7) Uani 1 1 d . . . . .
C22 C 0.7082(3) 0.83447(14) 0.40627(12) 0.0312(7) Uani 1 1 d . . . . .
N1 N 1.0491(3) 0.82185(13) 0.39054(11) 0.0373(6) Uani 1 1 d . . . . .
O1 O 0.8270(3) 0.99828(13) 0.41459(12) 0.0658(7) Uani 1 1 d . . . . .
O2 O 0.9239(2) 0.71097(11) 0.49198(10) 0.0447(5) Uani 1 1 d . . . . .
O3 O 0.5647(2) 0.86892(11) 0.41205(9) 0.0406(5) Uani 1 1 d . . . . .
H3A H 0.5070 0.8466 0.4336 0.061 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
Br1 C9 1.904(3) . ?
C1 N1 1.461(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.447(4) . ?
C2 C3 1.534(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.503(4) . ?
C3 C22 1.551(4) . ?
C3 H3 0.9800 . ?
C4 O1 1.214(4) . ?
C4 C5 1.503(4) . ?
C5 C6 1.524(4) . ?
C5 C13 1.554(4) . ?
C5 H5 0.9800 . ?
C6 N1 1.453(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.377(4) . ?
C7 C12 1.387(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(5) . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.528(4) . ?
C13 C14 1.541(4) . ?
C13 H13 0.9800 . ?
C14 C15 1.513(4) . ?
C14 C22 1.557(4) . ?
C14 H14 0.9800 . ?
C15 O2 1.216(3) . ?
C15 C16 1.472(4) . ?
C16 C21 1.382(4) . ?
C16 C17 1.396(4) . ?
C17 C18 1.372(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.511(4) . ?
C22 O3 1.427(3) . ?
O3 H3A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.4(2) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 C22 108.8(2) . . ?
C2 C3 C22 113.1(2) . . ?
C4 C3 H3 109.0 . . ?
C2 C3 H3 109.0 . . ?
C22 C3 H3 109.0 . . ?
O1 C4 C5 124.5(3) . . ?
O1 C4 C3 123.8(3) . . ?
C5 C4 C3 111.7(3) . . ?
C4 C5 C6 109.4(3) . . ?
C4 C5 C13 109.1(2) . . ?
C6 C5 C13 111.8(2) . . ?
C4 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C13 C5 H5 108.9 . . ?
N1 C6 C5 110.7(2) . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C12 121.5(3) . . ?
C8 C7 H7 119.3 . . ?
C12 C7 H7 119.3 . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 Br1 119.2(2) . . ?
C8 C9 Br1 119.7(3) . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 122.0(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C11 C12 C7 117.4(3) . . ?
C11 C12 C13 118.3(3) . . ?
C7 C12 C13 124.3(2) . . ?
C12 C13 C14 114.3(2) . . ?
C12 C13 C5 110.5(2) . . ?
C14 C13 C5 112.7(2) . . ?
C12 C13 H13 106.2 . . ?
C14 C13 H13 106.2 . . ?
C5 C13 H13 106.2 . . ?
C15 C14 C13 114.4(2) . . ?
C15 C14 C22 104.6(2) . . ?
C13 C14 C22 120.3(2) . . ?
C15 C14 H14 105.4 . . ?
C13 C14 H14 105.4 . . ?
C22 C14 H14 105.4 . . ?
O2 C15 C16 126.8(3) . . ?
O2 C15 C14 124.9(3) . . ?
C16 C15 C14 107.8(2) . . ?
C21 C16 C17 121.7(3) . . ?
C21 C16 C15 109.3(3) . . ?
C17 C16 C15 128.9(3) . . ?
C18 C17 C16 117.9(3) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C17 C18 C19 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 121.8(3) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C21 118.3(4) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C16 C21 C20 119.7(3) . . ?
C16 C21 C22 111.6(2) . . ?
C20 C21 C22 128.6(3) . . ?
O3 C22 C21 113.0(2) . . ?
O3 C22 C3 104.2(2) . . ?
C21 C22 C3 111.2(2) . . ?
O3 C22 C14 112.8(2) . . ?
C21 C22 C14 103.0(2) . . ?
C3 C22 C14 112.9(2) . . ?
C2 N1 C6 109.9(2) . . ?
C2 N1 C1 112.3(2) . . ?
C6 N1 C1 111.6(2) . . ?
C22 O3 H3A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.82 2.12 2.908(3) 160.8 4_466

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1587032'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C38 H31 N O5'
_chemical_formula_sum            'C38 H31 N O5'
_chemical_formula_weight         581.64

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                   12.6224(6)
_cell_length_b                   13.4198(5)
_cell_length_c                   18.6280(7)
_cell_angle_alpha                69.6950(10)
_cell_angle_beta                 86.7670(10)
_cell_angle_gamma                88.2990(10)
_cell_volume                     2954.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9611
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41997
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.167
_diffrn_reflns_theta_max         26.000
_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             11596
_reflns_number_gt                6037
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²+3.5000P] 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         11596
_refine_ls_number_parameters     797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2026
_refine_ls_R_factor_gt           0.1272
_refine_ls_wR_factor_ref         0.3784
_refine_ls_wR_factor_gt          0.3182
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.3510(4) 0.3059(4) 0.4908(3) 0.0424(12) Uani 1 1 d . . . . .
C2 C 0.2439(4) 0.3283(4) 0.4598(3) 0.0364(11) Uani 1 1 d . . . . .
C3 C 0.1538(4) 0.3661(4) 0.4884(3) 0.0469(13) Uani 1 1 d . . . . .
H3 H 0.1537 0.3780 0.5346 0.056 Uiso 1 1 calc R U . . .
C4 C 0.0644(4) 0.3854(5) 0.4464(4) 0.0612(16) Uani 1 1 d . . . . .
H4 H 0.0037 0.4129 0.4637 0.073 Uiso 1 1 calc R U . . .
C5 C 0.0636(4) 0.3646(5) 0.3787(4) 0.0633(17) Uani 1 1 d . . . . .
H5 H 0.0020 0.3775 0.3516 0.076 Uiso 1 1 calc R U . . .
C6 C 0.1529(4) 0.3248(5) 0.3507(3) 0.0536(14) Uani 1 1 d . . . . .
H6 H 0.1516 0.3093 0.3058 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2435(4) 0.3088(4) 0.3911(3) 0.0372(11) Uani 1 1 d . . . . .
C8 C 0.3514(4) 0.2764(4) 0.3717(3) 0.0371(11) Uani 1 1 d . . . . .
C9 C 0.4208(3) 0.2781(4) 0.4328(2) 0.0337(11) Uani 1 1 d . . . . .
C10 C 0.6775(3) 0.3369(3) 0.3413(2) 0.0298(10) Uani 1 1 d . . . . .
C11 C 0.6310(4) 0.4447(4) 0.2948(2) 0.0363(11) Uani 1 1 d . . . . .
C12 C 0.5537(4) 0.4683(4) 0.2426(3) 0.0469(13) Uani 1 1 d . . . . .
H12 H 0.5163 0.4147 0.2345 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5327(5) 0.5754(5) 0.2018(3) 0.0660(19) Uani 1 1 d . . . . .
H13 H 0.4816 0.5930 0.1652 0.079 Uiso 1 1 calc R U . . .
C14 C 0.5855(7) 0.6549(5) 0.2145(4) 0.076(2) Uani 1 1 d . . . . .
H14 H 0.5681 0.7254 0.1877 0.091 Uiso 1 1 calc R U . . .
C15 C 0.6636(6) 0.6318(4) 0.2659(3) 0.072(2) Uani 1 1 d . . . . .
H15 H 0.7011 0.6857 0.2734 0.086 Uiso 1 1 calc R U . . .
C16 C 0.6854(4) 0.5254(4) 0.3069(3) 0.0439(13) Uani 1 1 d . . . . .
C17 C 0.7648(4) 0.4791(4) 0.3641(3) 0.0457(13) Uani 1 1 d . . . . .
C18 C 0.7364(4) 0.3633(4) 0.4030(2) 0.0339(11) Uani 1 1 d . . . . .
H18 H 0.8006 0.3193 0.4163 0.041 Uiso 1 1 calc R U . . .
C19 C 0.6651(4) 0.3528(4) 0.4761(2) 0.0352(11) Uani 1 1 d . . . . .
H19 H 0.6186 0.4157 0.4625 0.042 Uiso 1 1 calc R U . . .
C20 C 0.7284(5) 0.3560(4) 0.5441(3) 0.0471(14) Uani 1 1 d . . . . .
C21 C 0.6831(5) 0.4021(4) 0.5943(3) 0.0527(14) Uani 1 1 d . . . . .
H21 H 0.6158 0.4328 0.5867 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7412(5) 0.4022(4) 0.6586(3) 0.0496(14) Uani 1 1 d . . . . .
C23 C 0.7361(7) 0.4413(7) 0.7744(4) 0.109(3) Uani 1 1 d . . . . .
H23A H 0.7414 0.3680 0.8064 0.163 Uiso 1 1 calc R U . . .
H23B H 0.6930 0.4793 0.8007 0.163 Uiso 1 1 calc R U . . .
H23C H 0.8057 0.4715 0.7631 0.163 Uiso 1 1 calc R U . . .
C24 C 0.8380(6) 0.3567(7) 0.6689(4) 0.096(2) Uani 1 1 d . . . . .
H24 H 0.8707 0.3536 0.7131 0.115 Uiso 1 1 calc R U . . .
C25 C 0.8916(8) 0.3154(7) 0.6223(4) 0.106(3) Uani 1 1 d . . . . .
H25 H 0.9615 0.2917 0.6286 0.127 Uiso 1 1 calc R U . . .
C26 C 0.8278(5) 0.3114(6) 0.5593(4) 0.073(2) Uani 1 1 d . . . . .
H26 H 0.8570 0.2762 0.5277 0.088 Uiso 1 1 calc R U . . .
C27 C 0.6511(4) 0.1361(4) 0.4029(3) 0.0397(11) Uani 1 1 d . . . . .
H27A H 0.5978 0.0811 0.4198 0.048 Uiso 1 1 calc R U . . .
H27B H 0.6960 0.1238 0.3627 0.048 Uiso 1 1 calc R U . . .
C28 C 0.5966(3) 0.2456(3) 0.3712(2) 0.0298(10) Uani 1 1 d . . . . .
H28 H 0.5530 0.2467 0.3289 0.036 Uiso 1 1 calc R U . . .
C29 C 0.5257(4) 0.2605(3) 0.4341(2) 0.0325(10) Uani 1 1 d . . . . .
C30 C 0.5910(3) 0.2556(4) 0.5013(2) 0.0343(11) Uani 1 1 d . . . . .
H30 H 0.5426 0.2599 0.5431 0.041 Uiso 1 1 calc R U . . .
C31 C 0.6488(4) 0.1473(4) 0.5283(3) 0.0446(12) Uani 1 1 d . . . . .
H31A H 0.6929 0.1435 0.5702 0.053 Uiso 1 1 calc R U . . .
H31B H 0.5969 0.0911 0.5473 0.053 Uiso 1 1 calc R U . . .
C32 C 0.7740(5) 0.0302(5) 0.4949(3) 0.0652(17) Uani 1 1 d . . . . .
H32A H 0.7249 -0.0283 0.5077 0.078 Uiso 1 1 calc R U . . .
H32B H 0.8078 0.0261 0.5414 0.078 Uiso 1 1 calc R U . . .
C33 C 0.8579(5) 0.0187(4) 0.4369(3) 0.0577(16) Uani 1 1 d . . . . .
C34 C 0.9324(6) 0.0914(7) 0.4030(5) 0.096(3) Uani 1 1 d . . . . .
H34 H 0.9320 0.1537 0.4143 0.115 Uiso 1 1 calc R U . . .
C35 C 1.0097(6) 0.0771(7) 0.3521(5) 0.103(3) Uani 1 1 d . . . . .
H35 H 1.0599 0.1298 0.3305 0.123 Uiso 1 1 calc R U . . .
C36 C 1.0150(8) -0.0080(8) 0.3328(5) 0.107(3) Uani 1 1 d . . . . .
H36 H 1.0689 -0.0185 0.2999 0.129 Uiso 1 1 calc R U . . .
C37 C 0.9372(13) -0.0798(8) 0.3637(7) 0.178(7) Uani 1 1 d . . . . .
H37 H 0.9371 -0.1400 0.3498 0.213 Uiso 1 1 calc R U . . .
C38 C 0.8564(9) -0.0685(6) 0.4158(5) 0.133(4) Uani 1 1 d . . . . .
H38 H 0.8036 -0.1191 0.4350 0.159 Uiso 1 1 calc R U . . .
C39 C 0.6589(4) 0.2126(4) 0.0087(3) 0.0402(12) Uani 1 1 d . . . . .
C40 C 0.7642(4) 0.1813(4) 0.0409(3) 0.0373(11) Uani 1 1 d . . . . .
C41 C 0.8518(4) 0.1413(4) 0.0106(3) 0.0442(12) Uani 1 1 d . . . . .
H41 H 0.8506 0.1326 -0.0367 0.053 Uiso 1 1 calc R U . . .
C42 C 0.9406(4) 0.1150(4) 0.0536(4) 0.0544(15) Uani 1 1 d . . . . .
H42 H 0.9998 0.0864 0.0355 0.065 Uiso 1 1 calc R U . . .
C43 C 0.9433(4) 0.1303(5) 0.1232(4) 0.0549(15) Uani 1 1 d . . . . .
H43 H 1.0052 0.1139 0.1500 0.066 Uiso 1 1 calc R U . . .
C44 C 0.8564(4) 0.1692(4) 0.1540(3) 0.0500(13) Uani 1 1 d . . . . .
H44 H 0.8581 0.1780 0.2013 0.060 Uiso 1 1 calc R U . . .
C45 C 0.7667(4) 0.1947(4) 0.1117(3) 0.0366(11) Uani 1 1 d . . . . .
C46 C 0.6621(4) 0.2324(4) 0.1317(3) 0.0373(11) Uani 1 1 d . . . . .
C47 C 0.5903(4) 0.2369(4) 0.0699(3) 0.0357(11) Uani 1 1 d . . . . .
C48 C 0.3405(3) 0.1613(3) 0.1679(2) 0.0314(10) Uani 1 1 d . . . . .
C49 C 0.3985(4) 0.0575(4) 0.2135(2) 0.0392(12) Uani 1 1 d . . . . .
C50 C 0.4788(4) 0.0415(4) 0.2639(3) 0.0471(13) Uani 1 1 d . . . . .
H50 H 0.5097 0.0984 0.2720 0.057 Uiso 1 1 calc R U . . .
C51 C 0.5124(6) -0.0630(5) 0.3022(3) 0.0688(19) Uani 1 1 d . . . . .
H51 H 0.5670 -0.0753 0.3359 0.083 Uiso 1 1 calc R U . . .
C52 C 0.4668(6) -0.1468(5) 0.2913(3) 0.071(2) Uani 1 1 d . . . . .
H52 H 0.4914 -0.2153 0.3171 0.085 Uiso 1 1 calc R U . . .
C53 C 0.3849(6) -0.1326(4) 0.2428(3) 0.069(2) Uani 1 1 d . . . . .
H53 H 0.3534 -0.1905 0.2365 0.083 Uiso 1 1 calc R U . . .
C54 C 0.3501(5) -0.0284(4) 0.2031(3) 0.0470(13) Uani 1 1 d . . . . .
C55 C 0.2659(5) 0.0117(4) 0.1475(3) 0.0500(14) Uani 1 1 d . . . . .
C56 C 0.2848(4) 0.1303(3) 0.1075(3) 0.0337(11) Uani 1 1 d . . . . .
H56 H 0.2176 0.1693 0.0946 0.040 Uiso 1 1 calc R U . . .
C57 C 0.3563(3) 0.1436(3) 0.0351(2) 0.0320(10) Uani 1 1 d . . . . .
H57 H 0.4109 0.0879 0.0512 0.038 Uiso 1 1 calc R U . . .
C58 C 0.3063(4) 0.1261(4) -0.0297(3) 0.0371(11) Uani 1 1 d . . . . .
C59 C 0.2060(4) 0.1601(4) -0.0492(3) 0.0476(13) Uani 1 1 d . . . . .
H59 H 0.1650 0.1926 -0.0202 0.057 Uiso 1 1 calc R U . . .
C60 C 0.1644(4) 0.1460(5) -0.1136(3) 0.0572(15) Uani 1 1 d . . . . .
C61 C 0.0204(6) 0.1819(7) -0.1952(5) 0.111(3) Uani 1 1 d . . . . .
H61A H 0.0599 0.2304 -0.2380 0.166 Uiso 1 1 calc R U . . .
H61B H -0.0524 0.2050 -0.1958 0.166 Uiso 1 1 calc R U . . .
H61C H 0.0243 0.1121 -0.1985 0.166 Uiso 1 1 calc R U . . .
C62 C 0.2279(5) 0.0990(4) -0.1566(3) 0.0479(14) Uani 1 1 d . . . . .
H62 H 0.2025 0.0931 -0.2009 0.058 Uiso 1 1 calc R U . . .
C63 C 0.3251(5) 0.0623(5) -0.1352(3) 0.0579(15) Uani 1 1 d . . . . .
H63 H 0.3653 0.0277 -0.1630 0.069 Uiso 1 1 calc R U . . .
C64 C 0.3653(4) 0.0755(4) -0.0730(3) 0.0486(13) Uani 1 1 d . . . . .
H64 H 0.4333 0.0503 -0.0591 0.058 Uiso 1 1 calc R U . . .
C65 C 0.3494(4) 0.3502(4) -0.0193(3) 0.0392(11) Uani 1 1 d . . . . .
H65A H 0.3950 0.4113 -0.0414 0.047 Uiso 1 1 calc R U . . .
H65B H 0.3038 0.3473 -0.0587 0.047 Uiso 1 1 calc R U . . .
C66 C 0.4176(3) 0.2498(3) 0.0061(2) 0.0329(10) Uani 1 1 d . . . . .
H66 H 0.4655 0.2499 -0.0372 0.039 Uiso 1 1 calc R U . . .
C67 C 0.4832(3) 0.2495(3) 0.0703(2) 0.0299(10) Uani 1 1 d . . . . .
C68 C 0.4135(3) 0.2593(3) 0.1358(2) 0.0313(10) Uani 1 1 d . . . . .
H68 H 0.4582 0.2623 0.1764 0.038 Uiso 1 1 calc R U . . .
C69 C 0.3489(4) 0.3633(4) 0.1059(3) 0.0367(11) Uani 1 1 d . . . . .
H69A H 0.3037 0.3714 0.1475 0.044 Uiso 1 1 calc R U . . .
H69B H 0.3968 0.4230 0.0878 0.044 Uiso 1 1 calc R U . . .
C70 C 0.2173(4) 0.4604(4) 0.0170(3) 0.0516(14) Uani 1 1 d . . . . .
H70A H 0.1862 0.4631 -0.0301 0.062 Uiso 1 1 calc R U . . .
H70B H 0.2626 0.5218 0.0049 0.062 Uiso 1 1 calc R U . . .
C71 C 0.1298(4) 0.4692(4) 0.0722(3) 0.0428(12) Uani 1 1 d . . . . .
C72 C 0.0805(5) 0.3824(5) 0.1264(4) 0.0693(18) Uani 1 1 d . . . . .
H72 H 0.1048 0.3144 0.1310 0.083 Uiso 1 1 calc R U . . .
C73 C -0.0030(5) 0.3940(6) 0.1734(4) 0.0725(19) Uani 1 1 d . . . . .
H73 H -0.0346 0.3340 0.2088 0.087 Uiso 1 1 calc R U . . .
C74 C -0.0401(5) 0.4920(6) 0.1688(4) 0.0737(19) Uani 1 1 d . . . . .
H74 H -0.0972 0.4996 0.2003 0.088 Uiso 1 1 calc R U . . .
C75 C 0.0071(7) 0.5768(6) 0.1182(6) 0.101(3) Uani 1 1 d . . . . .
H75 H -0.0169 0.6443 0.1150 0.121 Uiso 1 1 calc R U . . .
C76 C 0.0912(6) 0.5662(5) 0.0703(4) 0.081(2) Uani 1 1 d . . . . .
H76 H 0.1226 0.6271 0.0357 0.097 Uiso 1 1 calc R U . . .
N1 N 0.7149(3) 0.1306(3) 0.4667(2) 0.0419(10) Uani 1 1 d . . . . .
N2 N 0.2839(3) 0.3637(3) 0.0440(2) 0.0357(9) Uani 1 1 d . . . . .
O1 O 0.3744(3) 0.3106(4) 0.5519(2) 0.0814(15) Uani 1 1 d . . . . .
O2 O 0.3745(3) 0.2503(3) 0.3160(2) 0.0546(10) Uani 1 1 d . . . . .
O3 O 0.7599(2) 0.3111(3) 0.29439(18) 0.0373(8) Uani 1 1 d . . . . .
H3A H 0.7334 0.2961 0.2603 0.056 Uiso 1 1 calc R U . . .
O4 O 0.8385(3) 0.5250(3) 0.3780(2) 0.0658(12) Uani 1 1 d . . . . .
O5 O 0.6880(4) 0.4492(4) 0.7032(3) 0.0878(15) Uani 1 1 d . . . . .
O6 O 0.6356(3) 0.2177(4) -0.0544(2) 0.0726(13) Uani 1 1 d . . . . .
O7 O 0.6405(3) 0.2572(3) 0.1876(2) 0.0559(10) Uani 1 1 d . . . . .
O8 O 0.2571(2) 0.1811(3) 0.21687(18) 0.0384(8) Uani 1 1 d . . . . .
H8 H 0.2826 0.1888 0.2541 0.058 Uiso 1 1 calc R U . . .
O9 O 0.1946(4) -0.0390(3) 0.1351(2) 0.0741(13) Uani 1 1 d . . . . .
O10 O 0.0647(4) 0.1794(4) -0.1246(3) 0.0804(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.216(6) . ?
C1 C2 1.481(7) . ?
C1 C9 1.495(6) . ?
C2 C3 1.385(6) . ?
C2 C7 1.392(6) . ?
C3 C4 1.376(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.482(6) . ?
C8 O2 1.222(5) . ?
C8 C9 1.482(6) . ?
C9 C29 1.338(6) . ?
C10 O3 1.432(5) . ?
C10 C11 1.525(6) . ?
C10 C18 1.546(6) . ?
C10 C28 1.547(6) . ?
C11 C12 1.368(7) . ?
C11 C16 1.388(7) . ?
C12 C13 1.399(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.466(8) . ?
C17 O4 1.217(6) . ?
C17 C18 1.514(7) . ?
C18 C19 1.556(6) . ?
C18 H18 0.9800 . ?
C19 C20 1.548(7) . ?
C19 C30 1.549(6) . ?
C19 H19 0.9800 . ?
C20 C26 1.375(8) . ?
C20 C21 1.381(7) . ?
C21 C22 1.440(7) . ?
C21 H21 0.9300 . ?
C22 C24 1.343(9) . ?
C22 O5 1.347(6) . ?
C23 O5 1.459(7) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.328(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.476(10) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N1 1.453(6) . ?
C27 C28 1.538(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.500(6) . ?
C28 H28 0.9800 . ?
C29 C30 1.518(6) . ?
C30 C31 1.539(7) . ?
C30 H30 0.9800 . ?
C31 N1 1.458(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N1 1.463(6) . ?
C32 C33 1.513(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.340(10) . ?
C33 C38 1.359(9) . ?
C34 C35 1.379(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.309(11) . ?
C35 H35 0.9300 . ?
C36 C37 1.354(15) . ?
C36 H36 0.9300 . ?
C37 C38 1.409(14) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 O6 1.206(6) . ?
C39 C40 1.478(7) . ?
C39 C47 1.512(6) . ?
C40 C41 1.391(6) . ?
C40 C45 1.394(6) . ?
C41 C42 1.380(8) . ?
C41 H41 0.9300 . ?
C42 C43 1.383(8) . ?
C42 H42 0.9300 . ?
C43 C44 1.381(7) . ?
C43 H43 0.9300 . ?
C44 C45 1.381(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.475(6) . ?
C46 O7 1.213(5) . ?
C46 C47 1.488(7) . ?
C47 C67 1.357(6) . ?
C48 O8 1.433(5) . ?
C48 C56 1.537(6) . ?
C48 C49 1.544(6) . ?
C48 C68 1.550(6) . ?
C49 C50 1.381(7) . ?
C49 C54 1.397(7) . ?
C50 C51 1.400(8) . ?
C50 H50 0.9300 . ?
C51 C52 1.360(9) . ?
C51 H51 0.9300 . ?
C52 C53 1.375(10) . ?
C52 H52 0.9300 . ?
C53 C54 1.406(8) . ?
C53 H53 0.9300 . ?
C54 C55 1.483(8) . ?
C55 O9 1.222(6) . ?
C55 C56 1.524(7) . ?
C56 C57 1.540(6) . ?
C56 H56 0.9800 . ?
C57 C58 1.483(6) . ?
C57 C66 1.552(6) . ?
C57 H57 0.9800 . ?
C58 C59 1.358(7) . ?
C58 C64 1.398(6) . ?
C59 C60 1.409(7) . ?
C59 H59 0.9300 . ?
C60 O10 1.327(7) . ?
C60 C62 1.388(8) . ?
C61 O10 1.446(8) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 C63 1.339(8) . ?
C62 H62 0.9300 . ?
C63 C64 1.358(7) . ?
C63 H63 0.9300 . ?
C64 H64 0.9300 . ?
C65 N2 1.462(6) . ?
C65 C66 1.521(6) . ?
C65 H65A 0.9700 . ?
C65 H65B 0.9700 . ?
C66 C67 1.491(6) . ?
C66 H66 0.9800 . ?
C67 C68 1.505(6) . ?
C68 C69 1.538(6) . ?
C68 H68 0.9800 . ?
C69 N2 1.450(6) . ?
C69 H69A 0.9700 . ?
C69 H69B 0.9700 . ?
C70 N2 1.475(6) . ?
C70 C71 1.496(7) . ?
C70 H70A 0.9700 . ?
C70 H70B 0.9700 . ?
C71 C76 1.365(7) . ?
C71 C72 1.385(8) . ?
C72 C73 1.372(8) . ?
C72 H72 0.9300 . ?
C73 C74 1.359(9) . ?
C73 H73 0.9300 . ?
C74 C75 1.330(10) . ?
C74 H74 0.9300 . ?
C75 C76 1.384(10) . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?
O3 H3A 0.8200 . ?
O8 H8 0.8200 . ?

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 C2 124.8(4) . . ?
O1 C1 C9 128.3(4) . . ?
C2 C1 C9 106.9(4) . . ?
C3 C2 C7 120.9(4) . . ?
C3 C2 C1 129.4(4) . . ?
C7 C2 C1 109.6(4) . . ?
C4 C3 C2 118.2(5) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.9(5) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 118.1(5) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 120.7(4) . . ?
C6 C7 C8 129.7(4) . . ?
C2 C7 C8 109.5(4) . . ?
O2 C8 C7 124.3(4) . . ?
O2 C8 C9 128.3(4) . . ?
C7 C8 C9 107.3(4) . . ?
C29 C9 C8 126.1(4) . . ?
C29 C9 C1 127.4(4) . . ?
C8 C9 C1 106.5(4) . . ?
O3 C10 C11 107.6(3) . . ?
O3 C10 C18 104.8(3) . . ?
C11 C10 C18 102.2(3) . . ?
O3 C10 C28 110.1(3) . . ?
C11 C10 C28 115.1(4) . . ?
C18 C10 C28 116.2(3) . . ?
C12 C11 C16 120.5(5) . . ?
C12 C11 C10 129.3(4) . . ?
C16 C11 C10 110.0(4) . . ?
C11 C12 C13 117.9(6) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 121.5(6) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.3(6) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C11 C16 C15 121.0(6) . . ?
C11 C16 C17 109.6(4) . . ?
C15 C16 C17 129.4(5) . . ?
O4 C17 C16 126.8(5) . . ?
O4 C17 C18 126.8(5) . . ?
C16 C17 C18 106.4(4) . . ?
C17 C18 C10 103.5(4) . . ?
C17 C18 C19 108.2(3) . . ?
C10 C18 C19 113.1(4) . . ?
C17 C18 H18 110.6 . . ?
C10 C18 H18 110.6 . . ?
C19 C18 H18 110.6 . . ?
C20 C19 C30 110.9(4) . . ?
C20 C19 C18 113.3(4) . . ?
C30 C19 C18 113.6(4) . . ?
C20 C19 H19 106.1 . . ?
C30 C19 H19 106.1 . . ?
C18 C19 H19 106.1 . . ?
C26 C20 C21 117.1(5) . . ?
C26 C20 C19 123.3(4) . . ?
C21 C20 C19 119.6(5) . . ?
C20 C21 C22 119.4(5) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C24 C22 O5 127.2(6) . . ?
C24 C22 C21 119.4(5) . . ?
O5 C22 C21 113.4(5) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C22 126.5(7) . . ?
C25 C24 H24 116.8 . . ?
C22 C24 H24 116.8 . . ?
C24 C25 C26 112.6(8) . . ?
C24 C25 H25 123.7 . . ?
C26 C25 H25 123.7 . . ?
C20 C26 C25 124.7(6) . . ?
C20 C26 H26 117.6 . . ?
C25 C26 H26 117.6 . . ?
N1 C27 C28 110.5(4) . . ?
N1 C27 H27A 109.6 . . ?
C28 C27 H27A 109.6 . . ?
N1 C27 H27B 109.6 . . ?
C28 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
C29 C28 C27 108.1(4) . . ?
C29 C28 C10 110.0(3) . . ?
C27 C28 C10 112.2(4) . . ?
C29 C28 H28 108.9 . . ?
C27 C28 H28 108.9 . . ?
C10 C28 H28 108.9 . . ?
C9 C29 C28 126.7(4) . . ?
C9 C29 C30 123.4(4) . . ?
C28 C29 C30 109.9(4) . . ?
C29 C30 C31 108.0(4) . . ?
C29 C30 C19 108.6(4) . . ?
C31 C30 C19 114.5(4) . . ?
C29 C30 H30 108.5 . . ?
C31 C30 H30 108.5 . . ?
C19 C30 H30 108.5 . . ?
N1 C31 C30 111.8(4) . . ?
N1 C31 H31A 109.3 . . ?
C30 C31 H31A 109.3 . . ?
N1 C31 H31B 109.3 . . ?
C30 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?
N1 C32 C33 112.5(5) . . ?
N1 C32 H32A 109.1 . . ?
C33 C32 H32A 109.1 . . ?
N1 C32 H32B 109.1 . . ?
C33 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
C34 C33 C38 117.5(7) . . ?
C34 C33 C32 123.8(6) . . ?
C38 C33 C32 118.7(7) . . ?
C33 C34 C35 122.4(7) . . ?
C33 C34 H34 118.8 . . ?
C35 C34 H34 118.8 . . ?
C36 C35 C34 122.4(9) . . ?
C36 C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
C35 C36 C37 115.9(9) . . ?
C35 C36 H36 122.0 . . ?
C37 C36 H36 122.0 . . ?
C36 C37 C38 123.7(9) . . ?
C36 C37 H37 118.2 . . ?
C38 C37 H37 118.2 . . ?
C33 C38 C37 118.0(9) . . ?
C33 C38 H38 121.0 . . ?
C37 C38 H38 121.0 . . ?
O6 C39 C40 125.4(4) . . ?
O6 C39 C47 128.5(4) . . ?
C40 C39 C47 106.2(4) . . ?
C41 C40 C45 121.1(5) . . ?
C41 C40 C39 128.8(4) . . ?
C45 C40 C39 110.2(4) . . ?
C42 C41 C40 117.4(5) . . ?
C42 C41 H41 121.3 . . ?
C40 C41 H41 121.3 . . ?
C41 C42 C43 121.3(5) . . ?
C41 C42 H42 119.3 . . ?
C43 C42 H42 119.3 . . ?
C44 C43 C42 121.7(5) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 117.4(5) . . ?
C43 C44 H44 121.3 . . ?
C45 C44 H44 121.3 . . ?
C44 C45 C40 121.2(4) . . ?
C44 C45 C46 129.1(4) . . ?
C40 C45 C46 109.7(4) . . ?
O7 C46 C45 125.6(4) . . ?
O7 C46 C47 127.1(4) . . ?
C45 C46 C47 107.3(4) . . ?
C67 C47 C46 127.8(4) . . ?
C67 C47 C39 125.7(4) . . ?
C46 C47 C39 106.2(4) . . ?
O8 C48 C56 105.6(3) . . ?
O8 C48 C49 108.2(3) . . ?
C56 C48 C49 102.9(3) . . ?
O8 C48 C68 109.9(3) . . ?
C56 C48 C68 115.4(3) . . ?
C49 C48 C68 114.1(4) . . ?
C50 C49 C54 120.8(5) . . ?
C50 C49 C48 129.8(4) . . ?
C54 C49 C48 109.2(5) . . ?
C49 C50 C51 118.1(6) . . ?
C49 C50 H50 120.9 . . ?
C51 C50 H50 120.9 . . ?
C52 C51 C50 121.3(6) . . ?
C52 C51 H51 119.4 . . ?
C50 C51 H51 119.4 . . ?
C51 C52 C53 121.4(6) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 H52 119.3 . . ?
C52 C53 C54 118.5(6) . . ?
C52 C53 H53 120.8 . . ?
C54 C53 H53 120.8 . . ?
C49 C54 C53 119.9(6) . . ?
C49 C54 C55 109.3(4) . . ?
C53 C54 C55 130.9(5) . . ?
O9 C55 C54 127.6(5) . . ?
O9 C55 C56 125.8(6) . . ?
C54 C55 C56 106.6(4) . . ?
C55 C56 C48 103.0(4) . . ?
C55 C56 C57 107.4(3) . . ?
C48 C56 C57 112.8(4) . . ?
C55 C56 H56 111.1 . . ?
C48 C56 H56 111.1 . . ?
C57 C56 H56 111.1 . . ?
C58 C57 C56 116.8(4) . . ?
C58 C57 C66 110.1(3) . . ?
C56 C57 C66 113.1(3) . . ?
C58 C57 H57 105.3 . . ?
C56 C57 H57 105.3 . . ?
C66 C57 H57 105.3 . . ?
C59 C58 C64 119.1(5) . . ?
C59 C58 C57 122.0(4) . . ?
C64 C58 C57 118.8(5) . . ?
C58 C59 C60 119.5(5) . . ?
C58 C59 H59 120.2 . . ?
C60 C59 H59 120.2 . . ?
O10 C60 C62 127.6(6) . . ?
O10 C60 C59 113.3(5) . . ?
C62 C60 C59 119.1(5) . . ?
O10 C61 H61A 109.5 . . ?
O10 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O10 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C63 C62 C60 120.8(5) . . ?
C63 C62 H62 119.6 . . ?
C60 C62 H62 119.6 . . ?
C62 C63 C64 120.2(5) . . ?
C62 C63 H63 119.9 . . ?
C64 C63 H63 119.9 . . ?
C63 C64 C58 121.1(5) . . ?
C63 C64 H64 119.4 . . ?
C58 C64 H64 119.4 . . ?
N2 C65 C66 112.4(4) . . ?
N2 C65 H65A 109.1 . . ?
C66 C65 H65A 109.1 . . ?
N2 C65 H65B 109.1 . . ?
C66 C65 H65B 109.1 . . ?
H65A C65 H65B 107.9 . . ?
C67 C66 C65 109.9(4) . . ?
C67 C66 C57 106.2(3) . . ?
C65 C66 C57 115.7(4) . . ?
C67 C66 H66 108.3 . . ?
C65 C66 H66 108.3 . . ?
C57 C66 H66 108.3 . . ?
C47 C67 C66 123.9(4) . . ?
C47 C67 C68 125.6(4) . . ?
C66 C67 C68 110.4(4) . . ?
C67 C68 C69 108.1(3) . . ?
C67 C68 C48 109.4(3) . . ?
C69 C68 C48 111.6(4) . . ?
C67 C68 H68 109.2 . . ?
C69 C68 H68 109.2 . . ?
C48 C68 H68 109.2 . . ?
N2 C69 C68 111.1(3) . . ?
N2 C69 H69A 109.4 . . ?
C68 C69 H69A 109.4 . . ?
N2 C69 H69B 109.4 . . ?
C68 C69 H69B 109.4 . . ?
H69A C69 H69B 108.0 . . ?
N2 C70 C71 115.3(4) . . ?
N2 C70 H70A 108.5 . . ?
C71 C70 H70A 108.5 . . ?
N2 C70 H70B 108.5 . . ?
C71 C70 H70B 108.5 . . ?
H70A C70 H70B 107.5 . . ?
C76 C71 C72 115.5(5) . . ?
C76 C71 C70 120.8(5) . . ?
C72 C71 C70 123.7(4) . . ?
C73 C72 C71 121.8(6) . . ?
C73 C72 H72 119.1 . . ?
C71 C72 H72 119.1 . . ?
C74 C73 C72 120.9(7) . . ?
C74 C73 H73 119.6 . . ?
C72 C73 H73 119.6 . . ?
C75 C74 C73 118.6(6) . . ?
C75 C74 H74 120.7 . . ?
C73 C74 H74 120.7 . . ?
C74 C75 C76 121.1(6) . . ?
C74 C75 H75 119.4 . . ?
C76 C75 H75 119.4 . . ?
C71 C76 C75 122.2(7) . . ?
C71 C76 H76 118.9 . . ?
C75 C76 H76 118.9 . . ?
C27 N1 C31 110.5(4) . . ?
C27 N1 C32 112.0(4) . . ?
C31 N1 C32 110.7(4) . . ?
C69 N2 C65 110.9(4) . . ?
C69 N2 C70 112.0(4) . . ?
C65 N2 C70 110.9(4) . . ?
C10 O3 H3A 109.5 . . ?
C22 O5 C23 116.6(6) . . ?
C48 O8 H8 109.5 . . ?
C60 O10 C61 117.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 5.8(9) . . . . ?
C9 C1 C2 C3 -173.9(5) . . . . ?
O1 C1 C2 C7 -176.2(5) . . . . ?
C9 C1 C2 C7 4.0(5) . . . . ?
C7 C2 C3 C4 -1.0(8) . . . . ?
C1 C2 C3 C4 176.8(5) . . . . ?
C2 C3 C4 C5 2.0(9) . . . . ?
C3 C4 C5 C6 -0.7(10) . . . . ?
C4 C5 C6 C7 -1.5(9) . . . . ?
C5 C6 C7 C2 2.4(8) . . . . ?
C5 C6 C7 C8 -174.3(5) . . . . ?
C3 C2 C7 C6 -1.2(8) . . . . ?
C1 C2 C7 C6 -179.4(5) . . . . ?
C3 C2 C7 C8 176.1(4) . . . . ?
C1 C2 C7 C8 -2.1(6) . . . . ?
C6 C7 C8 O2 -5.9(9) . . . . ?
C2 C7 C8 O2 177.1(5) . . . . ?
C6 C7 C8 C9 176.3(5) . . . . ?
C2 C7 C8 C9 -0.7(5) . . . . ?
O2 C8 C9 C29 6.9(8) . . . . ?
C7 C8 C9 C29 -175.4(5) . . . . ?
O2 C8 C9 C1 -174.6(5) . . . . ?
C7 C8 C9 C1 3.1(5) . . . . ?
O1 C1 C9 C29 -5.6(9) . . . . ?
C2 C1 C9 C29 174.2(5) . . . . ?
O1 C1 C9 C8 175.9(6) . . . . ?
C2 C1 C9 C8 -4.3(5) . . . . ?
O3 C10 C11 C12 84.8(5) . . . . ?
C18 C10 C11 C12 -165.2(4) . . . . ?
C28 C10 C11 C12 -38.4(6) . . . . ?
O3 C10 C11 C16 -90.1(4) . . . . ?
C18 C10 C11 C16 19.9(4) . . . . ?
C28 C10 C11 C16 146.7(4) . . . . ?
C16 C11 C12 C13 0.7(7) . . . . ?
C10 C11 C12 C13 -173.7(4) . . . . ?
C11 C12 C13 C14 -1.5(8) . . . . ?
C12 C13 C14 C15 2.2(9) . . . . ?
C13 C14 C15 C16 -2.1(9) . . . . ?
C12 C11 C16 C15 -0.7(7) . . . . ?
C10 C11 C16 C15 174.7(4) . . . . ?
C12 C11 C16 C17 -178.9(4) . . . . ?
C10 C11 C16 C17 -3.5(5) . . . . ?
C14 C15 C16 C11 1.3(8) . . . . ?
C14 C15 C16 C17 179.1(5) . . . . ?
C11 C16 C17 O4 165.5(5) . . . . ?
C15 C16 C17 O4 -12.6(8) . . . . ?
C11 C16 C17 C18 -15.1(5) . . . . ?
C15 C16 C17 C18 166.9(5) . . . . ?
O4 C17 C18 C10 -153.7(5) . . . . ?
C16 C17 C18 C10 26.8(4) . . . . ?
O4 C17 C18 C19 86.0(6) . . . . ?
C16 C17 C18 C19 -93.5(4) . . . . ?
O3 C10 C18 C17 84.5(4) . . . . ?
C11 C10 C18 C17 -27.7(4) . . . . ?
C28 C10 C18 C17 -153.8(4) . . . . ?
O3 C10 C18 C19 -158.6(3) . . . . ?
C11 C10 C18 C19 89.2(4) . . . . ?
C28 C10 C18 C19 -36.9(5) . . . . ?
C17 C18 C19 C20 -77.9(5) . . . . ?
C10 C18 C19 C20 168.0(4) . . . . ?
C17 C18 C19 C30 154.4(4) . . . . ?
C10 C18 C19 C30 40.3(5) . . . . ?
C30 C19 C20 C26 92.9(6) . . . . ?
C18 C19 C20 C26 -36.2(7) . . . . ?
C30 C19 C20 C21 -84.8(5) . . . . ?
C18 C19 C20 C21 146.1(4) . . . . ?
C26 C20 C21 C22 0.5(8) . . . . ?
C19 C20 C21 C22 178.3(4) . . . . ?
C20 C21 C22 C24 -0.6(9) . . . . ?
C20 C21 C22 O5 -179.7(5) . . . . ?
O5 C22 C24 C25 -176.4(8) . . . . ?
C21 C22 C24 C25 4.7(12) . . . . ?
C22 C24 C25 C26 -7.4(13) . . . . ?
C21 C20 C26 C25 -4.0(10) . . . . ?
C19 C20 C26 C25 178.3(6) . . . . ?
C24 C25 C26 C20 7.2(12) . . . . ?
N1 C27 C28 C29 -60.8(5) . . . . ?
N1 C27 C28 C10 60.6(5) . . . . ?
O3 C10 C28 C29 166.8(3) . . . . ?
C11 C10 C28 C29 -71.4(5) . . . . ?
C18 C10 C28 C29 47.9(5) . . . . ?
O3 C10 C28 C27 46.5(5) . . . . ?
C11 C10 C28 C27 168.3(3) . . . . ?
C18 C10 C28 C27 -72.4(4) . . . . ?
C8 C9 C29 C28 6.2(8) . . . . ?
C1 C9 C29 C28 -172.1(4) . . . . ?
C8 C9 C29 C30 -175.4(4) . . . . ?
C1 C9 C29 C30 6.3(8) . . . . ?
C27 C28 C29 C9 -121.2(5) . . . . ?
C10 C28 C29 C9 116.0(5) . . . . ?
C27 C28 C29 C30 60.2(5) . . . . ?
C10 C28 C29 C30 -62.6(4) . . . . ?
C9 C29 C30 C31 123.1(5) . . . . ?
C28 C29 C30 C31 -58.2(5) . . . . ?
C9 C29 C30 C19 -112.1(5) . . . . ?
C28 C29 C30 C19 66.6(4) . . . . ?
C20 C19 C30 C29 176.3(4) . . . . ?
C18 C19 C30 C29 -54.8(5) . . . . ?
C20 C19 C30 C31 -62.9(5) . . . . ?
C18 C19 C30 C31 66.0(5) . . . . ?
C29 C30 C31 N1 57.1(5) . . . . ?
C19 C30 C31 N1 -64.1(5) . . . . ?
N1 C32 C33 C34 53.2(9) . . . . ?
N1 C32 C33 C38 -124.7(7) . . . . ?
C38 C33 C34 C35 -4.1(12) . . . . ?
C32 C33 C34 C35 178.0(7) . . . . ?
C33 C34 C35 C36 0.6(14) . . . . ?
C34 C35 C36 C37 2.5(15) . . . . ?
C35 C36 C37 C38 -2.3(19) . . . . ?
C34 C33 C38 C37 4.2(13) . . . . ?
C32 C33 C38 C37 -177.8(9) . . . . ?
C36 C37 C38 C33 -1.1(19) . . . . ?
O6 C39 C40 C41 -7.7(9) . . . . ?
C47 C39 C40 C41 172.9(5) . . . . ?
O6 C39 C40 C45 173.8(5) . . . . ?
C47 C39 C40 C45 -5.7(5) . . . . ?
C45 C40 C41 C42 0.4(7) . . . . ?
C39 C40 C41 C42 -178.1(5) . . . . ?
C40 C41 C42 C43 -1.6(8) . . . . ?
C41 C42 C43 C44 2.1(9) . . . . ?
C42 C43 C44 C45 -1.3(8) . . . . ?
C43 C44 C45 C40 0.1(8) . . . . ?
C43 C44 C45 C46 176.8(5) . . . . ?
C41 C40 C45 C44 0.4(7) . . . . ?
C39 C40 C45 C44 179.0(5) . . . . ?
C41 C40 C45 C46 -176.9(4) . . . . ?
C39 C40 C45 C46 1.8(5) . . . . ?
C44 C45 C46 O7 7.5(9) . . . . ?
C40 C45 C46 O7 -175.6(5) . . . . ?
C44 C45 C46 C47 -174.0(5) . . . . ?
C40 C45 C46 C47 2.9(5) . . . . ?
O7 C46 C47 C67 -13.7(9) . . . . ?
C45 C46 C47 C67 167.8(5) . . . . ?
O7 C46 C47 C39 172.2(5) . . . . ?
C45 C46 C47 C39 -6.2(5) . . . . ?
O6 C39 C47 C67 13.5(9) . . . . ?
C40 C39 C47 C67 -167.0(5) . . . . ?
O6 C39 C47 C46 -172.2(5) . . . . ?
C40 C39 C47 C46 7.2(5) . . . . ?
O8 C48 C49 C50 -83.9(5) . . . . ?
C56 C48 C49 C50 164.6(4) . . . . ?
C68 C48 C49 C50 38.8(6) . . . . ?
O8 C48 C49 C54 90.2(4) . . . . ?
C56 C48 C49 C54 -21.3(4) . . . . ?
C68 C48 C49 C54 -147.2(4) . . . . ?
C54 C49 C50 C51 1.9(7) . . . . ?
C48 C49 C50 C51 175.4(4) . . . . ?
C49 C50 C51 C52 -0.8(8) . . . . ?
C50 C51 C52 C53 -0.8(9) . . . . ?
C51 C52 C53 C54 1.2(9) . . . . ?
C50 C49 C54 C53 -1.5(7) . . . . ?
C48 C49 C54 C53 -176.2(4) . . . . ?
C50 C49 C54 C55 178.9(4) . . . . ?
C48 C49 C54 C55 4.3(5) . . . . ?
C52 C53 C54 C49 0.0(8) . . . . ?
C52 C53 C54 C55 179.4(5) . . . . ?
C49 C54 C55 O9 -165.1(5) . . . . ?
C53 C54 C55 O9 15.4(9) . . . . ?
C49 C54 C55 C56 15.0(5) . . . . ?
C53 C54 C55 C56 -164.5(5) . . . . ?
O9 C55 C56 C48 152.5(5) . . . . ?
C54 C55 C56 C48 -27.5(4) . . . . ?
O9 C55 C56 C57 -88.2(6) . . . . ?
C54 C55 C56 C57 91.7(4) . . . . ?
O8 C48 C56 C55 -84.5(4) . . . . ?
C49 C48 C56 C55 28.9(4) . . . . ?
C68 C48 C56 C55 153.9(4) . . . . ?
O8 C48 C56 C57 160.1(3) . . . . ?
C49 C48 C56 C57 -86.5(4) . . . . ?
C68 C48 C56 C57 38.5(5) . . . . ?
C55 C56 C57 C58 73.2(5) . . . . ?
C48 C56 C57 C58 -174.0(4) . . . . ?
C55 C56 C57 C66 -157.6(4) . . . . ?
C48 C56 C57 C66 -44.8(5) . . . . ?
C56 C57 C58 C59 39.5(6) . . . . ?
C66 C57 C58 C59 -91.2(5) . . . . ?
C56 C57 C58 C64 -142.2(4) . . . . ?
C66 C57 C58 C64 87.1(5) . . . . ?
C64 C58 C59 C60 -1.4(7) . . . . ?
C57 C58 C59 C60 176.9(5) . . . . ?
C58 C59 C60 O10 177.8(5) . . . . ?
C58 C59 C60 C62 -1.1(8) . . . . ?
O10 C60 C62 C63 -175.2(6) . . . . ?
C59 C60 C62 C63 3.6(8) . . . . ?
C60 C62 C63 C64 -3.4(9) . . . . ?
C62 C63 C64 C58 0.8(8) . . . . ?
C59 C58 C64 C63 1.7(7) . . . . ?
C57 C58 C64 C63 -176.7(5) . . . . ?
N2 C65 C66 C67 -55.1(5) . . . . ?
N2 C65 C66 C57 65.0(5) . . . . ?
C58 C57 C66 C67 -168.2(4) . . . . ?
C56 C57 C66 C67 59.2(5) . . . . ?
C58 C57 C66 C65 69.6(5) . . . . ?
C56 C57 C66 C65 -63.0(5) . . . . ?
C46 C47 C67 C66 -178.2(4) . . . . ?
C39 C47 C67 C66 -5.2(7) . . . . ?
C46 C47 C67 C68 -1.5(8) . . . . ?
C39 C47 C67 C68 171.5(4) . . . . ?
C65 C66 C67 C47 -126.1(5) . . . . ?
C57 C66 C67 C47 108.1(5) . . . . ?
C65 C66 C67 C68 56.8(5) . . . . ?
C57 C66 C67 C68 -69.0(4) . . . . ?
C47 C67 C68 C69 124.4(5) . . . . ?
C66 C67 C68 C69 -58.6(5) . . . . ?
C47 C67 C68 C48 -113.9(5) . . . . ?
C66 C67 C68 C48 63.1(5) . . . . ?
O8 C48 C68 C67 -166.0(3) . . . . ?
C56 C48 C68 C67 -46.7(5) . . . . ?
C49 C48 C68 C67 72.2(4) . . . . ?
O8 C48 C68 C69 -46.4(5) . . . . ?
C56 C48 C68 C69 72.9(4) . . . . ?
C49 C48 C68 C69 -168.2(3) . . . . ?
C67 C68 C69 N2 59.5(5) . . . . ?
C48 C68 C69 N2 -60.8(5) . . . . ?
N2 C70 C71 C76 153.3(6) . . . . ?
N2 C70 C71 C72 -28.6(8) . . . . ?
C76 C71 C72 C73 1.6(9) . . . . ?
C70 C71 C72 C73 -176.7(6) . . . . ?
C71 C72 C73 C74 -0.6(10) . . . . ?
C72 C73 C74 C75 -0.7(11) . . . . ?
C73 C74 C75 C76 0.9(13) . . . . ?
C72 C71 C76 C75 -1.4(11) . . . . ?
C70 C71 C76 C75 176.9(7) . . . . ?
C74 C75 C76 C71 0.2(13) . . . . ?
C28 C27 N1 C31 60.0(5) . . . . ?
C28 C27 N1 C32 -176.0(4) . . . . ?
C30 C31 N1 C27 -58.7(5) . . . . ?
C30 C31 N1 C32 176.5(4) . . . . ?
C33 C32 N1 C27 66.3(6) . . . . ?
C33 C32 N1 C31 -169.8(5) . . . . ?
C68 C69 N2 C65 -58.3(5) . . . . ?
C68 C69 N2 C70 177.2(4) . . . . ?
C66 C65 N2 C69 56.1(5) . . . . ?
C66 C65 N2 C70 -178.8(4) . . . . ?
C71 C70 N2 C69 -69.1(6) . . . . ?
C71 C70 N2 C65 166.5(4) . . . . ?
C24 C22 O5 C23 -6.1(10) . . . . ?
C21 C22 O5 C23 172.9(6) . . . . ?
C62 C60 O10 C61 -9.6(10) . . . . ?
C59 C60 O10 C61 171.5(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8 O2 0.82 2.06 2.838(5) 159.4 .
O3 H3A O7 0.82 2.05 2.856(5) 168.9 .

_refine_diff_density_max         1.550
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.125

####################################################################### 
# 
# 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_1i
_database_code_depnum_ccdc_archive 'CCDC 1587034'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.
2018-05-22 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         'C36 H28 N2 O4'
_chemical_formula_sum            'C36 H28 N2 O4'
_chemical_formula_weight         552.60

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                   9.215(2)
_cell_length_b                   22.358(6)
_cell_length_c                   17.565(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.492(11)
_cell_angle_gamma                90
_cell_volume                     3367.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5778
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      21.91

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33533
_diffrn_reflns_av_unetI/netI     0.1635
_diffrn_reflns_av_R_equivalents  0.1059
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.543
_diffrn_reflns_theta_max         28.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7913
_reflns_number_gt                3249
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1553P)²] 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         7913
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2268
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.3002
_refine_ls_wR_factor_gt          0.2453
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.7864(7) 0.8887(2) 0.2655(4) 0.1047(17) Uani 1 1 d . . . . .
H1 H 0.8911 0.8993 0.2827 0.126 Uiso 1 1 calc R U . . .
C2 C 0.6772(10) 0.9195(3) 0.2009(4) 0.128(2) Uani 1 1 d . . . . .
H2 H 0.7093 0.9497 0.1743 0.154 Uiso 1 1 calc R U . . .
C3 C 0.5222(10) 0.9052(4) 0.1766(4) 0.132(2) Uani 1 1 d . . . . .
H3 H 0.4486 0.9259 0.1338 0.159 Uiso 1 1 calc R U . . .
C4 C 0.4748(7) 0.8588(3) 0.2169(5) 0.127(2) Uani 1 1 d . . . . .
H4 H 0.3702 0.8483 0.2011 0.153 Uiso 1 1 calc R U . . .
C5 C 0.5847(6) 0.8301(2) 0.2788(3) 0.0916(15) Uani 1 1 d . . . . .
H5 H 0.5531 0.8001 0.3059 0.110 Uiso 1 1 calc R U . . .
C6 C 0.7417(5) 0.84287(19) 0.3041(3) 0.0697(12) Uani 1 1 d . . . . .
C7 C 0.8621(5) 0.8081(2) 0.3715(3) 0.0746(12) Uani 1 1 d . . . . .
H7A H 0.9423 0.8353 0.4050 0.090 Uiso 1 1 calc R U . . .
H7B H 0.8132 0.7899 0.4061 0.090 Uiso 1 1 calc R U . . .
C8 C 1.0753(4) 0.73887(17) 0.4014(2) 0.0575(10) Uani 1 1 d . . . . .
H8A H 1.0489 0.7210 0.4450 0.069 Uiso 1 1 calc R U . . .
H8B H 1.1463 0.7718 0.4245 0.069 Uiso 1 1 calc R U . . .
C9 C 1.1555(4) 0.69262(15) 0.36712(18) 0.0432(9) Uani 1 1 d . . . . .
H9 H 1.2471 0.6773 0.4118 0.052 Uiso 1 1 calc R U . . .
C10 C 1.0424(4) 0.64203(16) 0.33358(19) 0.0442(8) Uani 1 1 d . . . . .
C11 C 0.8975(4) 0.66456(15) 0.26651(19) 0.0438(9) Uani 1 1 d . . . . .
H11 H 0.8236 0.6313 0.2478 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8246(4) 0.71272(17) 0.3023(2) 0.0572(10) Uani 1 1 d . . . . .
H12A H 0.7325 0.7284 0.2595 0.069 Uiso 1 1 calc R U . . .
H12B H 0.7923 0.6951 0.3440 0.069 Uiso 1 1 calc R U . . .
C13 C 1.2081(4) 0.71727(15) 0.29965(19) 0.0436(9) Uani 1 1 d . . . . .
C14 C 1.3094(4) 0.67524(15) 0.2725(2) 0.0456(9) Uani 1 1 d . . . . .
C15 C 1.4196(4) 0.63472(18) 0.3164(2) 0.0626(11) Uani 1 1 d . . . . .
H15 H 1.4396 0.6277 0.3715 0.075 Uiso 1 1 calc R U . . .
C16 C 1.5008(5) 0.6045(2) 0.2751(3) 0.0761(13) Uani 1 1 d . . . . .
H16 H 1.5755 0.5766 0.3041 0.091 Uiso 1 1 calc R U . . .
C17 C 1.4772(5) 0.6133(2) 0.1951(3) 0.0836(14) Uani 1 1 d . . . . .
H17 H 1.5342 0.5916 0.1705 0.100 Uiso 1 1 calc R U . . .
C18 C 1.3671(5) 0.6550(2) 0.1499(3) 0.0764(13) Uani 1 1 d . . . . .
H18 H 1.3504 0.6625 0.0953 0.092 Uiso 1 1 calc R U . . .
C19 C 1.2829(4) 0.68512(18) 0.1897(2) 0.0571(10) Uani 1 1 d . . . . .
C20 C 1.1532(4) 0.72708(18) 0.1560(2) 0.0576(10) Uani 1 1 d . . . . .
C21 C 1.0743(4) 0.73258(15) 0.21796(18) 0.0423(8) Uani 1 1 d . . . . .
H21 H 1.0335 0.7730 0.2187 0.051 Uiso 1 1 calc R U . . .
C22 C 0.9437(4) 0.68543(14) 0.19352(18) 0.0435(8) Uani 1 1 d . . . . .
H22 H 0.9865 0.6501 0.1762 0.052 Uiso 1 1 calc R U . . .
C23 C 0.8000(4) 0.70336(15) 0.12059(19) 0.0446(9) Uani 1 1 d . . . . .
C24 C 0.7324(4) 0.75903(17) 0.1103(2) 0.0593(10) Uani 1 1 d . . . . .
H24 H 0.7760 0.7889 0.1487 0.071 Uiso 1 1 calc R U . . .
C25 C 0.5985(5) 0.77060(19) 0.0421(2) 0.0702(12) Uani 1 1 d . . . . .
H25 H 0.5556 0.8087 0.0363 0.084 Uiso 1 1 calc R U . . .
C26 C 0.5939(4) 0.67684(19) -0.0041(2) 0.0616(11) Uani 1 1 d . . . . .
H26 H 0.5480 0.6475 -0.0430 0.074 Uiso 1 1 calc R U . . .
C27 C 0.7255(4) 0.66162(16) 0.0614(2) 0.0557(10) Uani 1 1 d . . . . .
H27 H 0.7646 0.6229 0.0659 0.067 Uiso 1 1 calc R U . . .
C28 C 1.2001(4) 0.56219(16) 0.4322(2) 0.0525(9) Uani 1 1 d . . . . .
C29 C 1.1634(4) 0.49910(16) 0.4455(2) 0.0523(9) Uani 1 1 d . . . . .
C30 C 1.2531(6) 0.45854(19) 0.5028(3) 0.0743(12) Uani 1 1 d . . . . .
H30 H 1.3508 0.4689 0.5404 0.089 Uiso 1 1 calc R U . . .
C31 C 1.1919(7) 0.40198(19) 0.5019(3) 0.0844(14) Uani 1 1 d . . . . .
H31 H 1.2490 0.3738 0.5401 0.101 Uiso 1 1 calc R U . . .
C32 C 1.0495(6) 0.38675(19) 0.4461(3) 0.0830(14) Uani 1 1 d . . . . .
H32 H 1.0120 0.3482 0.4469 0.100 Uiso 1 1 calc R U . . .
C33 C 0.9599(5) 0.42679(19) 0.3887(3) 0.0784(13) Uani 1 1 d . . . . .
H33 H 0.8630 0.4160 0.3506 0.094 Uiso 1 1 calc R U . . .
C34 C 1.0195(4) 0.48423(15) 0.3895(2) 0.0557(10) Uani 1 1 d . . . . .
C35 C 0.9499(5) 0.53526(16) 0.3347(3) 0.0583(10) Uani 1 1 d . . . . .
C36 C 1.0631(4) 0.58601(15) 0.3632(2) 0.0465(9) Uani 1 1 d . . . . .
N1 N 0.9335(3) 0.76168(13) 0.33814(17) 0.0542(8) Uani 1 1 d . . . . .
N2 N 0.5282(3) 0.72999(16) -0.01555(17) 0.0605(9) Uani 1 1 d . . . . .
O1 O 1.2907(3) 0.77177(10) 0.32643(14) 0.0570(7) Uani 1 1 d . . . . .
H1A H 1.3540 0.7677 0.3732 0.085 Uiso 1 1 calc R U . . .
O2 O 1.1120(4) 0.75183(15) 0.08957(17) 0.0943(11) Uani 1 1 d . . . . .
O3 O 1.3219(3) 0.58681(13) 0.47144(16) 0.0781(9) Uani 1 1 d . . . . .
O4 O 0.8236(3) 0.53507(12) 0.2779(2) 0.0913(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.373(6) . ?
C1 C2 1.391(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.412(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.346(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.507(6) . ?
C7 N1 1.462(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.463(5) . ?
C8 C9 1.518(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.505(5) . ?
C9 C13 1.537(4) . ?
C9 H9 0.9800 . ?
C10 C36 1.343(5) . ?
C10 C11 1.507(4) . ?
C11 C12 1.522(5) . ?
C11 C22 1.563(5) . ?
C11 H11 0.9800 . ?
C12 N1 1.462(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O1 1.422(4) . ?
C13 C14 1.519(5) . ?
C13 C21 1.549(4) . ?
C14 C15 1.369(5) . ?
C14 C19 1.401(5) . ?
C15 C16 1.394(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.393(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.463(5) . ?
C20 O2 1.219(4) . ?
C20 C21 1.520(5) . ?
C21 C22 1.538(4) . ?
C21 H21 0.9800 . ?
C22 C23 1.521(4) . ?
C22 H22 0.9800 . ?
C23 C24 1.374(5) . ?
C23 C27 1.378(5) . ?
C24 C25 1.393(5) . ?
C24 H24 0.9300 . ?
C25 N2 1.337(5) . ?
C25 H25 0.9300 . ?
C26 N2 1.315(5) . ?
C26 C27 1.374(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O3 1.213(4) . ?
C28 C29 1.489(5) . ?
C28 C36 1.492(5) . ?
C29 C34 1.371(5) . ?
C29 C30 1.381(5) . ?
C30 C31 1.382(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.362(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.395(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.479(5) . ?
C35 O4 1.225(4) . ?
C35 C36 1.497(5) . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.9(5) . . ?
C6 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 119.9(6) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 123.6(5) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
C1 C6 C5 117.6(5) . . ?
C1 C6 C7 120.3(5) . . ?
C5 C6 C7 122.0(4) . . ?
N1 C7 C6 111.2(3) . . ?
N1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C9 111.4(3) . . ?
N1 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 107.4(3) . . ?
C10 C9 C13 109.7(2) . . ?
C8 C9 C13 113.5(3) . . ?
C10 C9 H9 108.7 . . ?
C8 C9 H9 108.7 . . ?
C13 C9 H9 108.7 . . ?
C36 C10 C9 124.7(3) . . ?
C36 C10 C11 125.0(3) . . ?
C9 C10 C11 110.1(3) . . ?
C10 C11 C12 108.2(3) . . ?
C10 C11 C22 108.2(3) . . ?
C12 C11 C22 114.9(3) . . ?
C10 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C22 C11 H11 108.5 . . ?
N1 C12 C11 111.7(3) . . ?
N1 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
O1 C13 C14 108.5(3) . . ?
O1 C13 C9 109.5(3) . . ?
C14 C13 C9 115.0(3) . . ?
O1 C13 C21 105.4(2) . . ?
C14 C13 C21 102.6(3) . . ?
C9 C13 C21 115.1(3) . . ?
C15 C14 C19 120.0(3) . . ?
C15 C14 C13 130.4(3) . . ?
C19 C14 C13 109.5(3) . . ?
C14 C15 C16 117.2(4) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 H15 121.4 . . ?
C17 C16 C15 123.8(4) . . ?
C17 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 117.4(4) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 H18 121.3 . . ?
C18 C19 C14 121.8(3) . . ?
C18 C19 C20 128.9(3) . . ?
C14 C19 C20 109.1(3) . . ?
O2 C20 C19 126.9(4) . . ?
O2 C20 C21 125.9(3) . . ?
C19 C20 C21 107.2(3) . . ?
C20 C21 C22 106.0(3) . . ?
C20 C21 C13 102.6(3) . . ?
C22 C21 C13 112.5(2) . . ?
C20 C21 H21 111.7 . . ?
C22 C21 H21 111.7 . . ?
C13 C21 H21 111.7 . . ?
C23 C22 C21 113.9(3) . . ?
C23 C22 C11 110.8(3) . . ?
C21 C22 C11 113.3(2) . . ?
C23 C22 H22 106.0 . . ?
C21 C22 H22 106.0 . . ?
C11 C22 H22 106.0 . . ?
C24 C23 C27 116.0(3) . . ?
C24 C23 C22 124.2(3) . . ?
C27 C23 C22 119.7(3) . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
N2 C25 C24 123.8(4) . . ?
N2 C25 H25 118.1 . . ?
C24 C25 H25 118.1 . . ?
N2 C26 C27 124.6(4) . . ?
N2 C26 H26 117.7 . . ?
C27 C26 H26 117.7 . . ?
C26 C27 C23 120.4(3) . . ?
C26 C27 H27 119.8 . . ?
C23 C27 H27 119.8 . . ?
O3 C28 C29 123.8(3) . . ?
O3 C28 C36 129.2(3) . . ?
C29 C28 C36 107.0(3) . . ?
C34 C29 C30 121.8(4) . . ?
C34 C29 C28 109.4(3) . . ?
C30 C29 C28 128.8(4) . . ?
C29 C30 C31 117.3(4) . . ?
C29 C30 H30 121.3 . . ?
C31 C30 H30 121.3 . . ?
C32 C31 C30 121.2(4) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C33 121.8(4) . . ?
C31 C32 H32 119.1 . . ?
C33 C32 H32 119.1 . . ?
C32 C33 C34 117.6(4) . . ?
C32 C33 H33 121.2 . . ?
C34 C33 H33 121.2 . . ?
C29 C34 C33 120.3(4) . . ?
C29 C34 C35 110.8(3) . . ?
C33 C34 C35 128.9(4) . . ?
O4 C35 C34 125.7(3) . . ?
O4 C35 C36 127.8(3) . . ?
C34 C35 C36 106.5(3) . . ?
C10 C36 C28 127.3(3) . . ?
C10 C36 C35 126.5(3) . . ?
C28 C36 C35 106.2(3) . . ?
C7 N1 C12 111.5(3) . . ?
C7 N1 C8 110.6(3) . . ?
C12 N1 C8 110.3(3) . . ?
C26 N2 C25 115.4(3) . . ?
C13 O1 H1A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N2 0.82 2.02 2.836(4) 170.2 4_676

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055


