# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_dm17402
_database_code_depnum_ccdc_archive 'CCDC 1818262'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N O2'
_chemical_formula_weight         453.51

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      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                   12.2322(13)
_cell_length_b                   15.6754(16)
_cell_length_c                   24.857(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4766.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5531
_cell_measurement_theta_min      4.531
_cell_measurement_theta_max      43.335

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             1904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6302
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31644
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4435
_reflns_number_gt                2793
_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-2013 (Sheldrick, 2013)'
_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)+(0.0538P)²+1.2184P] 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
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4435
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.59007(14) -0.10635(11) 0.46226(7) 0.0589(5) Uani 1 1 d . . . . .
O1 O 0.86255(12) 0.09596(10) 0.45935(7) 0.0697(5) Uani 1 1 d . . . . .
H1 H 0.8862 0.1374 0.4429 0.105 Uiso 1 1 calc R U . . .
O2 O 0.85330(12) 0.21930(10) 0.38971(7) 0.0756(5) Uani 1 1 d . . . . .
C1 C 0.67424(18) -0.12799(14) 0.49718(9) 0.0589(5) Uani 1 1 d . . . . .
C2 C 0.6832(2) -0.19906(15) 0.53072(10) 0.0716(7) Uani 1 1 d . . . . .
H2 H 0.6295 -0.2410 0.5315 0.086 Uiso 1 1 calc R U . . .
C3 C 0.7750(2) -0.20450(17) 0.56259(11) 0.0797(7) Uani 1 1 d . . . . .
H3 H 0.7826 -0.2510 0.5855 0.096 Uiso 1 1 calc R U . . .
C4 C 0.8564(2) -0.14315(17) 0.56173(10) 0.0755(7) Uani 1 1 d . . . . .
H4 H 0.9169 -0.1489 0.5841 0.091 Uiso 1 1 calc R U . . .
C5 C 0.84865(18) -0.07318(16) 0.52781(9) 0.0663(6) Uani 1 1 d . . . . .
H5 H 0.9041 -0.0326 0.5266 0.080 Uiso 1 1 calc R U . . .
C6 C 0.75579(17) -0.06501(13) 0.49555(8) 0.0555(5) Uani 1 1 d . . . . .
C7 C 0.71851(15) -0.00235(13) 0.45742(8) 0.0530(5) Uani 1 1 d . . . . .
C8 C 0.61668(16) -0.03012(13) 0.43704(8) 0.0525(5) Uani 1 1 d . . . . .
C9 C 0.56269(16) 0.01324(13) 0.39450(8) 0.0536(5) Uani 1 1 d . . . . .
C10 C 0.61045(15) 0.08853(13) 0.37621(8) 0.0530(5) Uani 1 1 d . . . . .
C11 C 0.70838(16) 0.12187(13) 0.39975(8) 0.0530(5) Uani 1 1 d . . . . .
C12 C 0.76436(15) 0.07279(13) 0.43842(8) 0.0540(5) Uani 1 1 d . . . . .
C13 C 0.75302(17) 0.20656(14) 0.38693(8) 0.0580(5) Uani 1 1 d . . . . .
C14 C 0.68089(17) 0.28104(14) 0.37681(9) 0.0592(6) Uani 1 1 d . . . . .
C15 C 0.7167(2) 0.34696(18) 0.34395(11) 0.0843(8) Uani 1 1 d . . . . .
H15 H 0.7828 0.3420 0.3257 0.101 Uiso 1 1 calc R U . . .
C16 C 0.6542(3) 0.42007(19) 0.33823(13) 0.0986(10) Uani 1 1 d . . . . .
H16 H 0.6783 0.4635 0.3156 0.118 Uiso 1 1 calc R U . . .
C17 C 0.5580(3) 0.42927(18) 0.36523(13) 0.0941(9) Uani 1 1 d . . . . .
H17 H 0.5164 0.4785 0.3610 0.113 Uiso 1 1 calc R U . . .
C18 C 0.5231(2) 0.36568(18) 0.39841(13) 0.0889(8) Uani 1 1 d . . . . .
H18 H 0.4582 0.3720 0.4175 0.107 Uiso 1 1 calc R U . . .
C19 C 0.58355(19) 0.29196(16) 0.40387(10) 0.0728(7) Uani 1 1 d . . . . .
H19 H 0.5581 0.2487 0.4262 0.087 Uiso 1 1 calc R U . . .
C20 C 0.56988(18) 0.12601(14) 0.32450(9) 0.0586(6) Uani 1 1 d . . . . .
C21 C 0.6371(2) 0.12102(16) 0.27995(10) 0.0738(7) Uani 1 1 d . . . . .
H21 H 0.7077 0.0997 0.2838 0.089 Uiso 1 1 calc R U . . .
C22 C 0.6014(3) 0.1472(2) 0.22956(11) 0.0976(9) Uani 1 1 d . . . . .
H22 H 0.6472 0.1425 0.1998 0.117 Uiso 1 1 calc R U . . .
C23 C 0.4986(3) 0.1797(2) 0.22400(14) 0.1056(10) Uani 1 1 d . . . . .
H23 H 0.4742 0.1969 0.1903 0.127 Uiso 1 1 calc R U . . .
C24 C 0.4312(3) 0.18726(19) 0.26761(15) 0.0967(9) Uani 1 1 d . . . . .
H24 H 0.3618 0.2107 0.2636 0.116 Uiso 1 1 calc R U . . .
C25 C 0.4664(2) 0.15981(16) 0.31799(11) 0.0789(7) Uani 1 1 d . . . . .
H25 H 0.4199 0.1643 0.3475 0.095 Uiso 1 1 calc R U . . .
C26 C 0.46513(16) -0.02417(13) 0.36663(8) 0.0552(5) Uani 1 1 d . . . . .
C27 C 0.4775(2) -0.07816(16) 0.32317(10) 0.0790(8) Uani 1 1 d . . . . .
H27 H 0.5472 -0.0903 0.3103 0.095 Uiso 1 1 calc R U . . .
C28 C 0.3876(3) -0.11434(19) 0.29864(13) 0.1003(10) Uani 1 1 d . . . . .
H28 H 0.3975 -0.1515 0.2699 0.120 Uiso 1 1 calc R U . . .
C29 C 0.2847(3) -0.09627(18) 0.31599(14) 0.0986(10) Uani 1 1 d . . . . .
H29 H 0.2244 -0.1212 0.2994 0.118 Uiso 1 1 calc R U . . .
C30 C 0.2710(2) -0.0418(2) 0.35749(13) 0.0997(10) Uani 1 1 d . . . . .
H30 H 0.2009 -0.0285 0.3692 0.120 Uiso 1 1 calc R U . . .
C31 C 0.36029(18) -0.00591(17) 0.38258(11) 0.0828(8) Uani 1 1 d . . . . .
H31 H 0.3492 0.0316 0.4110 0.099 Uiso 1 1 calc R U . . .
C32 C 0.48860(19) -0.15440(15) 0.45831(10) 0.0751(7) Uani 1 1 d . . . . .
H32A H 0.4959 -0.2073 0.4775 0.113 Uiso 1 1 calc R U . . .
H32B H 0.4729 -0.1659 0.4212 0.113 Uiso 1 1 calc R U . . .
H32C H 0.4300 -0.1217 0.4737 0.113 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.388(3) . ?
N1 C1 1.389(3) . ?
N1 C32 1.455(3) . ?
O1 C12 1.358(2) . ?
O1 H1 0.8200 . ?
O2 C13 1.245(2) . ?
C1 C2 1.396(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(3) . ?
C7 C12 1.387(3) . ?
C7 C8 1.413(3) . ?
C8 C9 1.420(3) . ?
C9 C10 1.393(3) . ?
C9 C26 1.499(3) . ?
C10 C11 1.432(3) . ?
C10 C20 1.498(3) . ?
C11 C12 1.409(3) . ?
C11 C13 1.470(3) . ?
C13 C14 1.485(3) . ?
C14 C19 1.378(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.385(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.382(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.389(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.367(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.393(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.373(3) . ?
C26 C27 1.381(3) . ?
C27 C28 1.379(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.361(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.349(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.378(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 108.58(17) . . ?
C8 N1 C32 127.96(19) . . ?
C1 N1 C32 123.24(19) . . ?
C12 O1 H1 109.5 . . ?
N1 C1 C2 128.8(2) . . ?
N1 C1 C6 109.69(19) . . ?
C2 C1 C6 121.5(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 122.3(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 134.3(2) . . ?
C1 C6 C7 105.89(18) . . ?
C12 C7 C8 119.72(19) . . ?
C12 C7 C6 132.49(19) . . ?
C8 C7 C6 107.76(18) . . ?
N1 C8 C7 108.05(18) . . ?
N1 C8 C9 129.74(18) . . ?
C7 C8 C9 121.97(19) . . ?
C10 C9 C8 116.97(18) . . ?
C10 C9 C26 120.95(19) . . ?
C8 C9 C26 121.81(18) . . ?
C9 C10 C11 121.77(19) . . ?
C9 C10 C20 118.26(18) . . ?
C11 C10 C20 118.99(18) . . ?
C12 C11 C10 119.09(18) . . ?
C12 C11 C13 117.41(18) . . ?
C10 C11 C13 123.48(19) . . ?
O1 C12 C7 117.00(19) . . ?
O1 C12 C11 123.03(19) . . ?
C7 C12 C11 119.96(18) . . ?
O2 C13 C11 119.9(2) . . ?
O2 C13 C14 117.96(19) . . ?
C11 C13 C14 121.73(18) . . ?
C19 C14 C15 117.9(2) . . ?
C19 C14 C13 121.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 121.3(2) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C25 C20 C21 118.2(2) . . ?
C25 C20 C10 123.7(2) . . ?
C21 C20 C10 117.9(2) . . ?
C20 C21 C22 121.3(3) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C20 C25 C24 120.5(3) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C31 C26 C27 117.1(2) . . ?
C31 C26 C9 121.91(19) . . ?
C27 C26 C9 120.95(19) . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C29 C28 C27 120.8(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C30 C29 C28 119.2(2) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C29 C30 C31 120.4(3) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C26 C31 C30 121.6(2) . . ?
C26 C31 H31 119.2 . . ?
C30 C31 H31 119.2 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C8 N1 C1 C2 -179.8(2) . . . . ?
C32 N1 C1 C2 5.2(3) . . . . ?
C8 N1 C1 C6 0.9(2) . . . . ?
C32 N1 C1 C6 -174.09(19) . . . . ?
N1 C1 C2 C3 -178.6(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 178.4(2) . . . . ?
N1 C1 C6 C5 179.68(18) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
N1 C1 C6 C7 -0.2(2) . . . . ?
C2 C1 C6 C7 -179.52(19) . . . . ?
C5 C6 C7 C12 1.4(4) . . . . ?
C1 C6 C7 C12 -178.8(2) . . . . ?
C5 C6 C7 C8 179.5(2) . . . . ?
C1 C6 C7 C8 -0.6(2) . . . . ?
C1 N1 C8 C7 -1.3(2) . . . . ?
C32 N1 C8 C7 173.4(2) . . . . ?
C1 N1 C8 C9 173.02(19) . . . . ?
C32 N1 C8 C9 -12.3(3) . . . . ?
C12 C7 C8 N1 179.63(17) . . . . ?
C6 C7 C8 N1 1.2(2) . . . . ?
C12 C7 C8 C9 4.8(3) . . . . ?
C6 C7 C8 C9 -173.68(18) . . . . ?
N1 C8 C9 C10 -178.36(19) . . . . ?
C7 C8 C9 C10 -4.7(3) . . . . ?
N1 C8 C9 C26 -4.3(3) . . . . ?
C7 C8 C9 C26 169.33(18) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C26 C9 C10 C11 -175.26(18) . . . . ?
C8 C9 C10 C20 167.41(18) . . . . ?
C26 C9 C10 C20 -6.7(3) . . . . ?
C9 C10 C11 C12 6.9(3) . . . . ?
C20 C10 C11 C12 -161.56(19) . . . . ?
C9 C10 C11 C13 -171.24(19) . . . . ?
C20 C10 C11 C13 20.3(3) . . . . ?
C8 C7 C12 O1 -179.70(18) . . . . ?
C6 C7 C12 O1 -1.7(3) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
C6 C7 C12 C11 179.2(2) . . . . ?
C10 C11 C12 O1 174.12(18) . . . . ?
C13 C11 C12 O1 -7.6(3) . . . . ?
C10 C11 C12 C7 -6.9(3) . . . . ?
C13 C11 C12 C7 171.40(18) . . . . ?
C12 C11 C13 O2 31.1(3) . . . . ?
C10 C11 C13 O2 -150.7(2) . . . . ?
C12 C11 C13 C14 -141.6(2) . . . . ?
C10 C11 C13 C14 36.6(3) . . . . ?
O2 C13 C14 C19 -137.9(2) . . . . ?
C11 C13 C14 C19 34.9(3) . . . . ?
O2 C13 C14 C15 34.6(3) . . . . ?
C11 C13 C14 C15 -152.6(2) . . . . ?
C19 C14 C15 C16 -1.3(4) . . . . ?
C13 C14 C15 C16 -174.1(2) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 -1.3(4) . . . . ?
C15 C14 C19 C18 0.3(4) . . . . ?
C13 C14 C19 C18 172.9(2) . . . . ?
C17 C18 C19 C14 1.0(4) . . . . ?
C9 C10 C20 C25 67.2(3) . . . . ?
C11 C10 C20 C25 -123.9(2) . . . . ?
C9 C10 C20 C21 -108.1(2) . . . . ?
C11 C10 C20 C21 60.8(3) . . . . ?
C25 C20 C21 C22 -1.6(4) . . . . ?
C10 C20 C21 C22 174.0(2) . . . . ?
C20 C21 C22 C23 1.1(4) . . . . ?
C21 C22 C23 C24 0.5(5) . . . . ?
C22 C23 C24 C25 -1.5(5) . . . . ?
C21 C20 C25 C24 0.6(4) . . . . ?
C10 C20 C25 C24 -174.7(2) . . . . ?
C23 C24 C25 C20 1.0(4) . . . . ?
C10 C9 C26 C31 -93.0(3) . . . . ?
C8 C9 C26 C31 93.2(3) . . . . ?
C10 C9 C26 C27 86.4(3) . . . . ?
C8 C9 C26 C27 -87.4(3) . . . . ?
C31 C26 C27 C28 -2.5(4) . . . . ?
C9 C26 C27 C28 178.1(2) . . . . ?
C26 C27 C28 C29 1.4(5) . . . . ?
C27 C28 C29 C30 0.4(5) . . . . ?
C28 C29 C30 C31 -1.0(5) . . . . ?
C27 C26 C31 C30 2.0(4) . . . . ?
C9 C26 C31 C30 -178.7(3) . . . . ?
C29 C30 C31 C26 -0.2(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 H1 O2 0.82 1.89 2.598(2) 144.3 .
O1 H1 O2 0.82 1.89 2.598(2) 144.3 .

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd17369
_database_code_depnum_ccdc_archive 'CCDC 1818281'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N O2'
_chemical_formula_weight         453.51

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                   12.3437(14)
_cell_length_b                   8.8269(10)
_cell_length_c                   21.695(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.191(3)
_cell_angle_gamma                90
_cell_volume                     2363.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2771
_cell_measurement_theta_min      4.982
_cell_measurement_theta_max      44.810

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13191
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.877
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4395
_reflns_number_gt                3194
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0666P)²+0.1550P] 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         4395
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.09852(11) 0.11926(15) 1.06620(6) 0.0451(3) Uani 1 1 d . . . . .
O1 O 0.32727(11) 0.07478(15) 1.04390(6) 0.0580(4) Uani 1 1 d . . . . .
O2 O 0.46442(11) 0.06109(18) 0.94301(8) 0.0829(5) Uani 1 1 d . . . . .
C1 C -0.00872(13) 0.15584(17) 1.05731(7) 0.0431(4) Uani 1 1 d . . . . .
C2 C -0.09566(14) 0.1314(2) 1.09663(8) 0.0505(4) Uani 1 1 d . . . . .
H2 H -0.0861 0.0831 1.1344 0.061 Uiso 1 1 calc R U . . .
C3 C -0.19527(16) 0.1804(2) 1.07827(9) 0.0582(5) Uani 1 1 d . . . . .
H3 H -0.2545 0.1650 1.1039 0.070 Uiso 1 1 calc R U . . .
C4 C -0.21030(15) 0.2526(2) 1.02215(9) 0.0583(5) Uani 1 1 d . . . . .
H4 H -0.2792 0.2853 1.0109 0.070 Uiso 1 1 calc R U . . .
C5 C -0.12505(13) 0.2767(2) 0.98302(8) 0.0500(4) Uani 1 1 d . . . . .
H5 H -0.1362 0.3248 0.9454 0.060 Uiso 1 1 calc R U . . .
C6 C -0.02171(13) 0.22866(17) 0.99996(7) 0.0414(4) Uani 1 1 d . . . . .
C7 C 0.08448(12) 0.23350(17) 0.97211(7) 0.0398(4) Uani 1 1 d . . . . .
C8 C 0.15494(13) 0.16418(17) 1.01446(7) 0.0409(4) Uani 1 1 d . . . . .
C9 C 0.26404(13) 0.14250(18) 1.00067(7) 0.0440(4) Uani 1 1 d . . . . .
C10 C 0.30218(13) 0.19685(18) 0.94477(8) 0.0445(4) Uani 1 1 d . . . . .
C11 C 0.23145(13) 0.26363(18) 0.90072(7) 0.0431(4) Uani 1 1 d . . . . .
C12 C 0.12238(13) 0.28233(17) 0.91418(7) 0.0409(4) Uani 1 1 d . . . . .
C13 C 0.04489(12) 0.34462(18) 0.86781(7) 0.0398(4) Uani 1 1 d . . . . .
C14 C 0.01751(14) 0.2624(2) 0.81596(7) 0.0472(4) Uani 1 1 d . . . . .
H14 H 0.0504 0.1691 0.8092 0.057 Uiso 1 1 calc R U . . .
C15 C -0.05707(15) 0.3153(2) 0.77415(8) 0.0571(5) Uani 1 1 d . . . . .
H15 H -0.0752 0.2573 0.7398 0.069 Uiso 1 1 calc R U . . .
C16 C -0.10477(15) 0.4537(2) 0.78306(9) 0.0609(5) Uani 1 1 d . . . . .
H16 H -0.1558 0.4899 0.7551 0.073 Uiso 1 1 calc R U . . .
C17 C -0.07664(15) 0.5382(2) 0.83349(10) 0.0601(5) Uani 1 1 d . . . . .
H17 H -0.1077 0.6332 0.8392 0.072 Uiso 1 1 calc R U . . .
C18 C -0.00290(14) 0.48450(19) 0.87586(8) 0.0522(4) Uani 1 1 d . . . . .
H18 H 0.0148 0.5428 0.9101 0.063 Uiso 1 1 calc R U . . .
C19 C 0.27659(13) 0.3068(2) 0.83955(8) 0.0486(4) Uani 1 1 d . . . . .
C20 C 0.33288(15) 0.2008(3) 0.80528(8) 0.0625(5) Uani 1 1 d . . . . .
H20 H 0.3373 0.1013 0.8192 0.075 Uiso 1 1 calc R U . . .
C21 C 0.38260(19) 0.2407(4) 0.75079(10) 0.0844(7) Uani 1 1 d . . . . .
H21 H 0.4216 0.1687 0.7288 0.101 Uiso 1 1 calc R U . . .
C22 C 0.3748(2) 0.3845(4) 0.72914(10) 0.0962(9) Uani 1 1 d . . . . .
H22 H 0.4085 0.4110 0.6924 0.115 Uiso 1 1 calc R U . . .
C23 C 0.3172(2) 0.4909(3) 0.76149(11) 0.0827(7) Uani 1 1 d . . . . .
H23 H 0.3112 0.5892 0.7464 0.099 Uiso 1 1 calc R U . . .
C24 C 0.26812(15) 0.4523(2) 0.81644(9) 0.0618(5) Uani 1 1 d . . . . .
H24 H 0.2290 0.5249 0.8381 0.074 Uiso 1 1 calc R U . . .
C25 C 0.42009(14) 0.1831(2) 0.93369(8) 0.0538(5) Uani 1 1 d . . . . .
C26 C 0.48572(14) 0.3174(3) 0.91695(8) 0.0578(5) Uani 1 1 d . . . . .
C27 C 0.58834(16) 0.2951(3) 0.89329(10) 0.0837(7) Uani 1 1 d . . . . .
H27 H 0.6133 0.1977 0.8852 0.100 Uiso 1 1 calc R U . . .
C28 C 0.6530(2) 0.4184(5) 0.88185(13) 0.1106(12) Uani 1 1 d . . . . .
H28 H 0.7218 0.4039 0.8656 0.133 Uiso 1 1 calc R U . . .
C29 C 0.6179(3) 0.5626(5) 0.89394(13) 0.1101(12) Uani 1 1 d . . . . .
H29 H 0.6632 0.6447 0.8865 0.132 Uiso 1 1 calc R U . . .
C30 C 0.5165(2) 0.5854(3) 0.91684(10) 0.0934(8) Uani 1 1 d . . . . .
H30 H 0.4923 0.6831 0.9248 0.112 Uiso 1 1 calc R U . . .
C31 C 0.44994(18) 0.4628(3) 0.92813(9) 0.0696(6) Uani 1 1 d . . . . .
H31 H 0.3805 0.4784 0.9434 0.084 Uiso 1 1 calc R U . . .
C32 C 0.13942(16) 0.0420(2) 1.12026(8) 0.0583(5) Uani 1 1 d . . . . .
H32A H 0.0923 0.0612 1.1545 0.087 Uiso 1 1 calc R U . . .
H32B H 0.2108 0.0784 1.1297 0.087 Uiso 1 1 calc R U . . .
H32C H 0.1423 -0.0650 1.1124 0.087 Uiso 1 1 calc R U . . .
H1 H 0.388(2) 0.044(3) 1.0261(11) 0.098(9) Uiso 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
N1 C1 1.375(2) . ?
N1 C8 1.381(2) . ?
N1 C32 1.446(2) . ?
O1 C9 1.3568(19) . ?
O1 H1 0.89(2) . ?
O2 C25 1.225(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.409(2) . ?
C2 C3 1.361(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.446(2) . ?
C7 C8 1.404(2) . ?
C7 C12 1.410(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.388(2) . ?
C10 C11 1.420(2) . ?
C10 C25 1.481(2) . ?
C11 C12 1.389(2) . ?
C11 C19 1.490(2) . ?
C12 C13 1.491(2) . ?
C13 C18 1.380(2) . ?
C13 C14 1.380(2) . ?
C14 C15 1.372(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.383(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.357(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.482(3) . ?
C26 C31 1.379(3) . ?
C26 C27 1.382(3) . ?
C27 C28 1.373(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.369(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.363(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 107.84(13) . . ?
C1 N1 C32 123.89(14) . . ?
C8 N1 C32 128.23(14) . . ?
C9 O1 H1 108.7(16) . . ?
N1 C1 C2 128.48(16) . . ?
N1 C1 C6 109.72(14) . . ?
C2 C1 C6 121.78(16) . . ?
C3 C2 C1 118.02(17) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.39(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.96(17) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.59(17) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 118.26(15) . . ?
C5 C6 C7 135.37(16) . . ?
C1 C6 C7 106.37(14) . . ?
C8 C7 C12 120.67(14) . . ?
C8 C7 C6 105.91(14) . . ?
C12 C7 C6 133.28(15) . . ?
N1 C8 C9 128.70(15) . . ?
N1 C8 C7 110.14(14) . . ?
C9 C8 C7 121.09(14) . . ?
O1 C9 C10 124.07(15) . . ?
O1 C9 C8 117.79(15) . . ?
C10 C9 C8 118.09(14) . . ?
C9 C10 C11 121.46(15) . . ?
C9 C10 C25 116.74(15) . . ?
C11 C10 C25 121.80(15) . . ?
C12 C11 C10 120.14(15) . . ?
C12 C11 C19 121.51(15) . . ?
C10 C11 C19 118.31(14) . . ?
C11 C12 C7 118.43(15) . . ?
C11 C12 C13 121.48(14) . . ?
C7 C12 C13 120.01(14) . . ?
C18 C13 C14 118.05(15) . . ?
C18 C13 C12 121.21(14) . . ?
C14 C13 C12 120.73(14) . . ?
C15 C14 C13 121.48(17) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 119.84(18) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.42(17) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.78(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.41(17) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C24 C19 C20 118.08(18) . . ?
C24 C19 C11 122.14(16) . . ?
C20 C19 C11 119.73(17) . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.0(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
O2 C25 C10 118.95(17) . . ?
O2 C25 C26 119.98(17) . . ?
C10 C25 C26 120.85(17) . . ?
C31 C26 C27 119.5(2) . . ?
C31 C26 C25 121.71(18) . . ?
C27 C26 C25 118.7(2) . . ?
C28 C27 C26 119.2(3) . . ?
C28 C27 H27 120.4 . . ?
C26 C27 H27 120.4 . . ?
C29 C28 C27 121.2(3) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 120.4(2) . . ?
C26 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C8 N1 C1 C2 179.53(16) . . . . ?
C32 N1 C1 C2 1.7(3) . . . . ?
C8 N1 C1 C6 -1.50(17) . . . . ?
C32 N1 C1 C6 -179.35(15) . . . . ?
N1 C1 C2 C3 178.80(16) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 179.97(17) . . . . ?
N1 C1 C6 C5 -179.06(14) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
N1 C1 C6 C7 1.13(17) . . . . ?
C2 C1 C6 C7 -179.82(14) . . . . ?
C5 C6 C7 C8 179.91(18) . . . . ?
C1 C6 C7 C8 -0.33(16) . . . . ?
C5 C6 C7 C12 -4.5(3) . . . . ?
C1 C6 C7 C12 175.26(16) . . . . ?
C1 N1 C8 C9 -175.65(16) . . . . ?
C32 N1 C8 C9 2.1(3) . . . . ?
C1 N1 C8 C7 1.29(17) . . . . ?
C32 N1 C8 C7 179.02(16) . . . . ?
C12 C7 C8 N1 -176.85(13) . . . . ?
C6 C7 C8 N1 -0.58(17) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C6 C7 C8 C9 176.63(14) . . . . ?
N1 C8 C9 O1 -3.4(3) . . . . ?
C7 C8 C9 O1 179.96(14) . . . . ?
N1 C8 C9 C10 179.16(15) . . . . ?
C7 C8 C9 C10 2.5(2) . . . . ?
O1 C9 C10 C11 178.52(15) . . . . ?
C8 C9 C10 C11 -4.2(2) . . . . ?
O1 C9 C10 C25 -2.1(2) . . . . ?
C8 C9 C10 C25 175.21(15) . . . . ?
C9 C10 C11 C12 3.0(2) . . . . ?
C25 C10 C11 C12 -176.34(16) . . . . ?
C9 C10 C11 C19 -174.62(15) . . . . ?
C25 C10 C11 C19 6.0(2) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C19 C11 C12 C7 177.52(14) . . . . ?
C10 C11 C12 C13 -176.79(14) . . . . ?
C19 C11 C12 C13 0.8(2) . . . . ?
C8 C7 C12 C11 -1.6(2) . . . . ?
C6 C7 C12 C11 -176.65(15) . . . . ?
C8 C7 C12 C13 175.19(14) . . . . ?
C6 C7 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C18 -112.38(18) . . . . ?
C7 C12 C13 C18 70.9(2) . . . . ?
C11 C12 C13 C14 68.7(2) . . . . ?
C7 C12 C13 C14 -107.94(18) . . . . ?
C18 C13 C14 C15 -1.7(2) . . . . ?
C12 C13 C14 C15 177.23(16) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C14 C13 C18 C17 0.8(2) . . . . ?
C12 C13 C18 C17 -178.09(16) . . . . ?
C12 C11 C19 C24 57.8(2) . . . . ?
C10 C11 C19 C24 -124.54(18) . . . . ?
C12 C11 C19 C20 -124.88(18) . . . . ?
C10 C11 C19 C20 52.8(2) . . . . ?
C24 C19 C20 C21 2.4(3) . . . . ?
C11 C19 C20 C21 -174.98(18) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?
C20 C19 C24 C23 -1.7(3) . . . . ?
C11 C19 C24 C23 175.61(18) . . . . ?
C9 C10 C25 O2 48.9(2) . . . . ?
C11 C10 C25 O2 -131.66(19) . . . . ?
C9 C10 C25 C26 -125.69(17) . . . . ?
C11 C10 C25 C26 53.7(2) . . . . ?
O2 C25 C26 C31 -155.39(19) . . . . ?
C10 C25 C26 C31 19.2(3) . . . . ?
O2 C25 C26 C27 20.3(3) . . . . ?
C10 C25 C26 C27 -165.18(17) . . . . ?
C31 C26 C27 C28 0.5(3) . . . . ?
C25 C26 C27 C28 -175.3(2) . . . . ?
C26 C27 C28 C29 0.6(4) . . . . ?
C27 C28 C29 C30 -1.1(4) . . . . ?
C28 C29 C30 C31 0.4(4) . . . . ?
C27 C26 C31 C30 -1.1(3) . . . . ?
C25 C26 C31 C30 174.52(17) . . . . ?
C29 C30 C31 C26 0.6(3) . . . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

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

data_mo_d8v17780_0m
_database_code_depnum_ccdc_archive 'CCDC 1818282'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 N O2'
_chemical_formula_weight         455.53

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.5424(4)
_cell_length_b                   9.1677(3)
_cell_length_c                   22.0679(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.0200(10)
_cell_angle_gamma                90
_cell_volume                     2461.89(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8600
_cell_measurement_theta_min      6.137
_cell_measurement_theta_max      49.125

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34826
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4819
_reflns_number_gt                3397
_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-2013 (Sheldrick, 2013)'
_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)+(0.0574P)²+0.3867P] 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
_refine_ls_extinction_coef       0.054(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4819
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58700(13) 0.54915(17) 0.71419(7) 0.0720(4) Uani 1 1 d . . . . .
O1 O 0.40296(11) 0.71518(19) 0.73001(6) 0.0956(5) Uani 1 1 d . . . . .
O2 O 0.21720(12) 0.8041(2) 0.68770(7) 0.0970(5) Uani 1 1 d . . . . .
H2 H 0.2754 0.7861 0.7129 0.145 Uiso 1 1 calc R U . . .
C1 C 0.68802(15) 0.54077(19) 0.70095(8) 0.0690(5) Uani 1 1 d . . . . .
C2 C 0.78168(19) 0.4617(2) 0.73049(10) 0.0873(6) Uani 1 1 d . . . . .
H2A H 0.7816 0.4007 0.7642 0.105 Uiso 1 1 calc R U . . .
C3 C 0.87326(19) 0.4776(3) 0.70790(13) 0.0983(7) Uani 1 1 d . . . . .
H3 H 0.9367 0.4266 0.7268 0.118 Uiso 1 1 calc R U . . .
C4 C 0.87429(17) 0.5678(3) 0.65751(13) 0.0939(7) Uani 1 1 d . . . . .
H4 H 0.9387 0.5774 0.6441 0.113 Uiso 1 1 calc R U . . .
C5 C 0.78281(15) 0.6427(2) 0.62718(10) 0.0780(5) Uani 1 1 d . . . . .
H5 H 0.7841 0.7016 0.5931 0.094 Uiso 1 1 calc R U . . .
C6 C 0.68685(13) 0.62869(18) 0.64871(8) 0.0643(4) Uani 1 1 d . . . . .
C7 C 0.57856(13) 0.68589(19) 0.62897(8) 0.0650(4) Uani 1 1 d . . . . .
H7 H 0.5524 0.7458 0.5946 0.078 Uiso 1 1 calc R U . . .
C8 C 0.52008(13) 0.6371(2) 0.66950(8) 0.0643(4) Uani 1 1 d . . . . .
C9 C 0.41060(14) 0.6837(2) 0.67505(8) 0.0696(5) Uani 1 1 d . . . . .
C10 C 0.31902(13) 0.69891(19) 0.62208(7) 0.0619(4) Uani 1 1 d . . . . .
C11 C 0.22263(15) 0.7594(2) 0.63194(8) 0.0704(5) Uani 1 1 d . . . . .
C12 C 0.11795(14) 0.7811(2) 0.58500(9) 0.0684(5) Uani 1 1 d . . . . .
C13 C 0.04818(16) 0.8931(2) 0.59452(10) 0.0846(6) Uani 1 1 d . . . . .
H13 H 0.0703 0.9548 0.6287 0.101 Uiso 1 1 calc R U . . .
C14 C -0.05258(17) 0.9130(3) 0.55393(12) 0.0935(7) Uani 1 1 d . . . . .
H14 H -0.0977 0.9888 0.5605 0.112 Uiso 1 1 calc R U . . .
C15 C -0.08700(16) 0.8224(3) 0.50399(12) 0.0911(6) Uani 1 1 d . . . . .
H15 H -0.1559 0.8353 0.4771 0.109 Uiso 1 1 calc R U . . .
C16 C -0.01968(15) 0.7121(2) 0.49360(11) 0.0869(6) Uani 1 1 d . . . . .
H16 H -0.0429 0.6509 0.4593 0.104 Uiso 1 1 calc R U . . .
C17 C 0.08238(14) 0.6914(2) 0.53374(10) 0.0760(5) Uani 1 1 d . . . . .
H17 H 0.1275 0.6165 0.5262 0.091 Uiso 1 1 calc R U . . .
C18 C 0.32944(12) 0.64868(19) 0.55936(7) 0.0583(4) Uani 1 1 d . . . . .
C19 C 0.35253(13) 0.50914(19) 0.54974(8) 0.0629(4) Uani 1 1 d . . . . .
H19 H 0.3666 0.4874 0.5113 0.076 Uiso 1 1 calc R U . . .
C20 C 0.35806(14) 0.38663(19) 0.59344(8) 0.0646(4) Uani 1 1 d . . . . .
C21 C 0.27649(16) 0.3613(2) 0.62501(9) 0.0767(5) Uani 1 1 d . . . . .
H21 H 0.2176 0.4255 0.6199 0.092 Uiso 1 1 calc R U . . .
C22 C 0.2816(2) 0.2422(3) 0.66387(10) 0.0913(7) Uani 1 1 d . . . . .
H22 H 0.2249 0.2248 0.6834 0.110 Uiso 1 1 calc R U . . .
C23 C 0.3704(2) 0.1491(3) 0.67378(11) 0.0972(7) Uani 1 1 d . . . . .
H23 H 0.3748 0.0702 0.7008 0.117 Uiso 1 1 calc R U . . .
C24 C 0.4517(2) 0.1734(2) 0.64367(11) 0.0931(6) Uani 1 1 d . . . . .
H24 H 0.5121 0.1114 0.6506 0.112 Uiso 1 1 calc R U . . .
C25 C 0.44520(17) 0.2891(2) 0.60322(9) 0.0778(5) Uani 1 1 d . . . . .
H25 H 0.5002 0.3021 0.5820 0.093 Uiso 1 1 calc R U . . .
C26 C 0.32140(12) 0.75982(18) 0.50928(7) 0.0579(4) Uani 1 1 d . . . . .
C27 C 0.35343(13) 0.90316(19) 0.52339(8) 0.0624(4) Uani 1 1 d . . . . .
H27 H 0.3777 0.9312 0.5650 0.075 Uiso 1 1 calc R U . . .
C28 C 0.34995(14) 1.0047(2) 0.47696(9) 0.0688(5) Uani 1 1 d . . . . .
H28 H 0.3733 1.0997 0.4874 0.083 Uiso 1 1 calc R U . . .
C29 C 0.31227(15) 0.9667(2) 0.41545(9) 0.0725(5) Uani 1 1 d . . . . .
H29 H 0.3101 1.0354 0.3842 0.087 Uiso 1 1 calc R U . . .
C30 C 0.27782(16) 0.8266(2) 0.40036(9) 0.0759(5) Uani 1 1 d . . . . .
H30 H 0.2514 0.8006 0.3587 0.091 Uiso 1 1 calc R U . . .
C31 C 0.28212(14) 0.7239(2) 0.44653(8) 0.0688(5) Uani 1 1 d . . . . .
H31 H 0.2584 0.6292 0.4356 0.083 Uiso 1 1 calc R U . . .
C32 C 0.5546(2) 0.4635(3) 0.76230(10) 0.0997(7) Uani 1 1 d . . . . .
H32A H 0.5931 0.3722 0.7674 0.150 Uiso 1 1 calc R U . . .
H32B H 0.4769 0.4457 0.7502 0.150 Uiso 1 1 calc R U . . .
H32C H 0.5723 0.5162 0.8011 0.150 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.370(2) . ?
N1 C8 1.388(2) . ?
N1 C32 1.455(2) . ?
O1 C9 1.273(2) . ?
O2 C11 1.314(2) . ?
O2 H2 0.8200 . ?
C1 C2 1.400(3) . ?
C1 C6 1.404(2) . ?
C2 C3 1.366(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.422(2) . ?
C7 C8 1.362(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.471(2) . ?
C9 C10 1.434(2) . ?
C10 C11 1.394(2) . ?
C10 C18 1.494(2) . ?
C11 C12 1.476(3) . ?
C12 C17 1.382(3) . ?
C12 C13 1.398(3) . ?
C13 C14 1.373(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.340(2) . ?
C18 C26 1.489(2) . ?
C19 C20 1.471(2) . ?
C19 H19 0.9300 . ?
C20 C25 1.388(3) . ?
C20 C21 1.390(2) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.375(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.387(2) . ?
C26 C31 1.392(2) . ?
C27 C28 1.377(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.370(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.370(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.379(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 108.21(15) . . ?
C1 N1 C32 124.19(17) . . ?
C8 N1 C32 127.15(17) . . ?
C11 O2 H2 109.5 . . ?
N1 C1 C2 130.16(19) . . ?
N1 C1 C6 108.47(15) . . ?
C2 C1 C6 121.4(2) . . ?
C3 C2 C1 117.3(2) . . ?
C3 C2 H2A 121.3 . . ?
C1 C2 H2A 121.3 . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.44(17) . . ?
C5 C6 C7 134.15(18) . . ?
C1 C6 C7 106.41(16) . . ?
C8 C7 C6 107.69(16) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 N1 109.16(16) . . ?
C7 C8 C9 128.41(16) . . ?
N1 C8 C9 121.69(16) . . ?
O1 C9 C10 121.63(17) . . ?
O1 C9 C8 115.64(15) . . ?
C10 C9 C8 122.68(15) . . ?
C11 C10 C9 117.73(16) . . ?
C11 C10 C18 122.75(15) . . ?
C9 C10 C18 119.52(15) . . ?
O2 C11 C10 120.91(17) . . ?
O2 C11 C12 112.11(16) . . ?
C10 C11 C12 126.99(16) . . ?
C17 C12 C13 118.06(18) . . ?
C17 C12 C11 123.40(17) . . ?
C13 C12 C11 118.44(18) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.53(19) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C19 C18 C26 120.95(15) . . ?
C19 C18 C10 120.78(16) . . ?
C26 C18 C10 118.13(14) . . ?
C18 C19 C20 127.08(16) . . ?
C18 C19 H19 116.5 . . ?
C20 C19 H19 116.5 . . ?
C25 C20 C21 117.50(18) . . ?
C25 C20 C19 120.28(16) . . ?
C21 C20 C19 122.20(17) . . ?
C22 C21 C20 121.0(2) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 119.5(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 121.2(2) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
C27 C26 C31 117.44(16) . . ?
C27 C26 C18 121.18(14) . . ?
C31 C26 C18 121.37(15) . . ?
C28 C27 C26 121.19(16) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C29 C28 C27 120.42(18) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 119.49(18) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C29 C30 C31 120.44(17) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 120.98(17) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C8 N1 C1 C2 -177.29(18) . . . . ?
C32 N1 C1 C2 -4.6(3) . . . . ?
C8 N1 C1 C6 2.24(19) . . . . ?
C32 N1 C1 C6 174.96(17) . . . . ?
N1 C1 C2 C3 -178.16(19) . . . . ?
C6 C1 C2 C3 2.4(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -178.63(19) . . . . ?
N1 C1 C6 C5 177.66(15) . . . . ?
C2 C1 C6 C5 -2.8(3) . . . . ?
N1 C1 C6 C7 -2.60(19) . . . . ?
C2 C1 C6 C7 176.98(16) . . . . ?
C5 C6 C7 C8 -178.32(19) . . . . ?
C1 C6 C7 C8 1.99(19) . . . . ?
C6 C7 C8 N1 -0.7(2) . . . . ?
C6 C7 C8 C9 169.49(16) . . . . ?
C1 N1 C8 C7 -1.0(2) . . . . ?
C32 N1 C8 C7 -173.42(18) . . . . ?
C1 N1 C8 C9 -171.91(15) . . . . ?
C32 N1 C8 C9 15.7(3) . . . . ?
C7 C8 C9 O1 -130.5(2) . . . . ?
N1 C8 C9 O1 38.5(2) . . . . ?
C7 C8 C9 C10 46.9(3) . . . . ?
N1 C8 C9 C10 -144.02(17) . . . . ?
O1 C9 C10 C11 4.4(3) . . . . ?
C8 C9 C10 C11 -172.89(17) . . . . ?
O1 C9 C10 C18 -174.87(17) . . . . ?
C8 C9 C10 C18 7.8(3) . . . . ?
C9 C10 C11 O2 1.6(3) . . . . ?
C18 C10 C11 O2 -179.09(17) . . . . ?
C9 C10 C11 C12 -177.97(17) . . . . ?
C18 C10 C11 C12 1.3(3) . . . . ?
O2 C11 C12 C17 -149.28(19) . . . . ?
C10 C11 C12 C17 30.4(3) . . . . ?
O2 C11 C12 C13 27.1(3) . . . . ?
C10 C11 C12 C13 -153.27(19) . . . . ?
C17 C12 C13 C14 -0.1(3) . . . . ?
C11 C12 C13 C14 -176.65(19) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C11 C12 C17 C16 175.92(19) . . . . ?
C11 C10 C18 C19 -119.57(19) . . . . ?
C9 C10 C18 C19 59.7(2) . . . . ?
C11 C10 C18 C26 64.7(2) . . . . ?
C9 C10 C18 C26 -116.01(17) . . . . ?
C26 C18 C19 C20 -176.95(15) . . . . ?
C10 C18 C19 C20 7.5(2) . . . . ?
C18 C19 C20 C25 -134.03(18) . . . . ?
C18 C19 C20 C21 47.7(3) . . . . ?
C25 C20 C21 C22 -0.9(3) . . . . ?
C19 C20 C21 C22 177.43(16) . . . . ?
C20 C21 C22 C23 2.4(3) . . . . ?
C21 C22 C23 C24 -1.6(3) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C23 C24 C25 C20 2.2(3) . . . . ?
C21 C20 C25 C24 -1.4(3) . . . . ?
C19 C20 C25 C24 -179.73(18) . . . . ?
C19 C18 C26 C27 -146.48(16) . . . . ?
C10 C18 C26 C27 29.2(2) . . . . ?
C19 C18 C26 C31 33.1(2) . . . . ?
C10 C18 C26 C31 -151.16(15) . . . . ?
C31 C26 C27 C28 -2.1(2) . . . . ?
C18 C26 C27 C28 177.49(14) . . . . ?
C26 C27 C28 C29 1.4(3) . . . . ?
C27 C28 C29 C30 0.1(3) . . . . ?
C28 C29 C30 C31 -0.8(3) . . . . ?
C29 C30 C31 C26 0.0(3) . . . . ?
C27 C26 C31 C30 1.5(2) . . . . ?
C18 C26 C31 C30 -178.18(15) . . . . ?

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 O1 0.82 1.68 2.431(2) 150.6 .

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v17687
_database_code_depnum_ccdc_archive 'CCDC 1818284'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 N O2'
_chemical_formula_weight         455.53

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                   13.1322(4)
_cell_length_b                   18.0792(5)
_cell_length_c                   11.7504(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.6540(10)
_cell_angle_gamma                90
_cell_volume                     2722.01(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      4.781
_cell_measurement_theta_max      54.976

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43554
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5345
_reflns_number_gt                4457
_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-2013 (Sheldrick, 2013)'
_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)+(0.1102P)²+1.1367P] 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
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5345
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1802
_refine_ls_wR_factor_gt          0.1729
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 0.500 282 86 ' '
2 0.500 0.000 0.000 282 86 ' '
_platon_squeeze_details          
;
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.52015(11) 0.31843(8) 0.14406(13) 0.0215(3) Uani 1 1 d . . . . .
O1 O 0.61273(10) 0.20697(7) 0.31629(12) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.81125(11) 0.21893(8) 0.53109(12) 0.0330(4) Uani 1 1 d . . . . .
C1 C 0.42436(14) 0.31183(10) 0.17709(16) 0.0232(4) Uani 1 1 d . . . . .
C2 C 0.33176(15) 0.28267(11) 0.11271(19) 0.0302(4) Uani 1 1 d . . . . .
H2 H 0.3273 0.2634 0.0366 0.036 Uiso 1 1 calc R U . . .
C3 C 0.24554(16) 0.28275(12) 0.1640(2) 0.0375(5) Uani 1 1 d . . . . .
H3 H 0.1816 0.2624 0.1220 0.045 Uiso 1 1 calc R U . . .
C4 C 0.25033(17) 0.31147(12) 0.2739(2) 0.0406(6) Uani 1 1 d . . . . .
H4 H 0.1903 0.3107 0.3066 0.049 Uiso 1 1 calc R U . . .
C5 C 0.34384(17) 0.34168(11) 0.3370(2) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.3476 0.3623 0.4121 0.040 Uiso 1 1 calc R U . . .
C6 C 0.43067(14) 0.34106(10) 0.28853(17) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.53907(14) 0.37055(10) 0.33294(15) 0.0226(4) Uani 1 1 d . . . . .
H7A H 0.5675 0.3549 0.4144 0.027 Uiso 1 1 calc R U . . .
H7B H 0.5404 0.4252 0.3286 0.027 Uiso 1 1 calc R U . . .
C8 C 0.60087(13) 0.33494(9) 0.24803(14) 0.0192(4) Uani 1 1 d . . . . .
C9 C 0.69385(13) 0.38152(10) 0.22382(15) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.7038 0.3667 0.1450 0.024 Uiso 1 1 calc R U . . .
C10 C 0.78683(14) 0.35154(10) 0.31253(15) 0.0223(4) Uani 1 1 d . . . . .
C11 C 0.76536(14) 0.28561(10) 0.35684(15) 0.0224(4) Uani 1 1 d . . . . .
C12 C 0.65533(14) 0.26589(9) 0.30925(14) 0.0197(4) Uani 1 1 d . . . . .
C13 C 0.83475(14) 0.23391(10) 0.43854(16) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.92610(14) 0.20007(10) 0.40357(16) 0.0239(4) Uani 1 1 d . . . . .
C15 C 0.99299(16) 0.15570(12) 0.48478(19) 0.0344(5) Uani 1 1 d . . . . .
H15 H 0.9804 0.1489 0.5607 0.041 Uiso 1 1 calc R U . . .
C16 C 1.07778(18) 0.12169(14) 0.4539(2) 0.0445(6) Uani 1 1 d . . . . .
H16 H 1.1230 0.0913 0.5089 0.053 Uiso 1 1 calc R U . . .
C17 C 1.09699(17) 0.13163(14) 0.3441(2) 0.0443(6) Uani 1 1 d . . . . .
H17 H 1.1551 0.1081 0.3235 0.053 Uiso 1 1 calc R U . . .
C18 C 1.03170(17) 0.17581(14) 0.2643(2) 0.0397(5) Uani 1 1 d . . . . .
H18 H 1.0456 0.1832 0.1891 0.048 Uiso 1 1 calc R U . . .
C19 C 0.94548(16) 0.20972(12) 0.29293(18) 0.0308(4) Uani 1 1 d . . . . .
H19 H 0.9001 0.2394 0.2370 0.037 Uiso 1 1 calc R U . . .
C20 C 0.88877(14) 0.38888(10) 0.33775(17) 0.0249(4) Uani 1 1 d . . . . .
C21 C 0.92191(16) 0.42845(11) 0.24991(19) 0.0317(5) Uani 1 1 d . . . . .
H21 H 0.8767 0.4339 0.1753 0.038 Uiso 1 1 calc R U . . .
C22 C 1.02053(17) 0.45953(12) 0.2718(2) 0.0383(5) Uani 1 1 d . . . . .
H22 H 1.0434 0.4853 0.2115 0.046 Uiso 1 1 calc R U . . .
C23 C 1.08620(17) 0.45337(13) 0.3810(2) 0.0418(6) Uani 1 1 d . . . . .
H23 H 1.1540 0.4745 0.3952 0.050 Uiso 1 1 calc R U . . .
C24 C 1.05303(18) 0.41651(13) 0.4690(2) 0.0404(5) Uani 1 1 d . . . . .
H24 H 1.0976 0.4131 0.5443 0.048 Uiso 1 1 calc R U . . .
C25 C 0.95468(16) 0.38438(11) 0.44785(18) 0.0311(4) Uani 1 1 d . . . . .
H25 H 0.9322 0.3592 0.5089 0.037 Uiso 1 1 calc R U . . .
C26 C 0.67586(14) 0.46413(9) 0.22028(16) 0.0210(4) Uani 1 1 d . . . . .
C27 C 0.63094(15) 0.49727(10) 0.11478(16) 0.0267(4) Uani 1 1 d . . . . .
H27 H 0.6164 0.4682 0.0457 0.032 Uiso 1 1 calc R U . . .
C28 C 0.60685(16) 0.57236(11) 0.10836(18) 0.0318(5) Uani 1 1 d . . . . .
H28 H 0.5762 0.5942 0.0353 0.038 Uiso 1 1 calc R U . . .
C29 C 0.62758(15) 0.61524(11) 0.20852(19) 0.0315(5) Uani 1 1 d . . . . .
H29 H 0.6102 0.6663 0.2049 0.038 Uiso 1 1 calc R U . . .
C30 C 0.67396(16) 0.58276(11) 0.31438(18) 0.0299(4) Uani 1 1 d . . . . .
H30 H 0.6894 0.6121 0.3831 0.036 Uiso 1 1 calc R U . . .
C31 C 0.69788(15) 0.50780(11) 0.32047(16) 0.0265(4) Uani 1 1 d . . . . .
H31 H 0.7294 0.4862 0.3934 0.032 Uiso 1 1 calc R U . . .
C32 C 0.54405(15) 0.26555(11) 0.05995(16) 0.0280(4) Uani 1 1 d . . . . .
H32A H 0.5343 0.2151 0.0863 0.042 Uiso 1 1 calc R U . . .
H32B H 0.6166 0.2720 0.0533 0.042 Uiso 1 1 calc R U . . .
H32C H 0.4973 0.2739 -0.0162 0.042 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.400(2) . ?
N1 C32 1.458(2) . ?
N1 C8 1.462(2) . ?
O1 C12 1.214(2) . ?
O2 C13 1.224(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(3) . ?
C7 C8 1.557(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C12 1.537(2) . ?
C8 C9 1.560(2) . ?
C9 C26 1.511(2) . ?
C9 C10 1.521(2) . ?
C9 H9 1.0000 . ?
C10 C11 1.355(3) . ?
C10 C20 1.470(3) . ?
C11 C12 1.474(2) . ?
C11 C13 1.497(2) . ?
C13 C14 1.483(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.399(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.392(3) . ?
C20 C21 1.401(3) . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.387(3) . ?
C26 C31 1.394(3) . ?
C27 C28 1.392(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C32 118.16(15) . . ?
C1 N1 C8 108.46(14) . . ?
C32 N1 C8 118.42(14) . . ?
C2 C1 C6 121.29(18) . . ?
C2 C1 N1 127.90(18) . . ?
C6 C1 N1 110.79(16) . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.29(18) . . ?
C5 C6 C7 131.19(18) . . ?
C1 C6 C7 108.47(15) . . ?
C6 C7 C8 102.59(14) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.2 . . ?
N1 C8 C12 113.77(14) . . ?
N1 C8 C7 103.63(14) . . ?
C12 C8 C7 106.88(13) . . ?
N1 C8 C9 114.26(14) . . ?
C12 C8 C9 102.79(13) . . ?
C7 C8 C9 115.62(14) . . ?
C26 C9 C10 117.92(15) . . ?
C26 C9 C8 114.49(14) . . ?
C10 C9 C8 103.03(14) . . ?
C26 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C8 C9 H9 106.9 . . ?
C11 C10 C20 125.69(17) . . ?
C11 C10 C9 111.93(15) . . ?
C20 C10 C9 122.22(16) . . ?
C10 C11 C12 109.64(15) . . ?
C10 C11 C13 130.30(16) . . ?
C12 C11 C13 120.03(16) . . ?
O1 C12 C11 127.89(16) . . ?
O1 C12 C8 124.77(16) . . ?
C11 C12 C8 107.34(14) . . ?
O2 C13 C14 122.12(17) . . ?
O2 C13 C11 118.11(17) . . ?
C14 C13 C11 119.71(16) . . ?
C19 C14 C15 119.59(18) . . ?
C19 C14 C13 122.19(17) . . ?
C15 C14 C13 118.21(18) . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 119.8(2) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C25 C20 C21 118.95(18) . . ?
C25 C20 C10 120.90(18) . . ?
C21 C20 C10 120.13(17) . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C27 C26 C31 118.63(17) . . ?
C27 C26 C9 119.00(16) . . ?
C31 C26 C9 122.29(16) . . ?
C26 C27 C28 121.11(18) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 119.97(18) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 119.34(18) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C31 C30 C29 120.53(18) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C26 120.41(17) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
C32 N1 C1 C2 -27.8(3) . . . . ?
C8 N1 C1 C2 -166.18(18) . . . . ?
C32 N1 C1 C6 153.60(16) . . . . ?
C8 N1 C1 C6 15.20(19) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
N1 C1 C2 C3 -179.30(18) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 178.23(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C5 178.52(16) . . . . ?
C2 C1 C6 C7 -177.89(16) . . . . ?
N1 C1 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C8 167.55(19) . . . . ?
C1 C6 C7 C8 -15.12(18) . . . . ?
C1 N1 C8 C12 91.82(17) . . . . ?
C32 N1 C8 C12 -46.5(2) . . . . ?
C1 N1 C8 C7 -23.86(17) . . . . ?
C32 N1 C8 C7 -162.14(15) . . . . ?
C1 N1 C8 C9 -150.54(15) . . . . ?
C32 N1 C8 C9 71.2(2) . . . . ?
C6 C7 C8 N1 23.13(17) . . . . ?
C6 C7 C8 C12 -97.34(15) . . . . ?
C6 C7 C8 C9 148.95(14) . . . . ?
N1 C8 C9 C26 85.02(18) . . . . ?
C12 C8 C9 C26 -151.22(14) . . . . ?
C7 C8 C9 C26 -35.2(2) . . . . ?
N1 C8 C9 C10 -145.66(14) . . . . ?
C12 C8 C9 C10 -21.90(16) . . . . ?
C7 C8 C9 C10 94.15(17) . . . . ?
C26 C9 C10 C11 143.71(16) . . . . ?
C8 C9 C10 C11 16.54(19) . . . . ?
C26 C9 C10 C20 -40.6(2) . . . . ?
C8 C9 C10 C20 -167.74(16) . . . . ?
C20 C10 C11 C12 -178.85(17) . . . . ?
C9 C10 C11 C12 -3.3(2) . . . . ?
C20 C10 C11 C13 -0.7(3) . . . . ?
C9 C10 C11 C13 174.87(17) . . . . ?
C10 C11 C12 O1 168.81(18) . . . . ?
C13 C11 C12 O1 -9.6(3) . . . . ?
C10 C11 C12 C8 -11.81(19) . . . . ?
C13 C11 C12 C8 169.80(15) . . . . ?
N1 C8 C12 O1 -35.4(2) . . . . ?
C7 C8 C12 O1 78.3(2) . . . . ?
C9 C8 C12 O1 -159.51(16) . . . . ?
N1 C8 C12 C11 145.17(15) . . . . ?
C7 C8 C12 C11 -101.08(16) . . . . ?
C9 C8 C12 C11 21.08(17) . . . . ?
C10 C11 C13 O2 120.9(2) . . . . ?
C12 C11 C13 O2 -61.1(2) . . . . ?
C10 C11 C13 C14 -61.8(3) . . . . ?
C12 C11 C13 C14 116.23(19) . . . . ?
O2 C13 C14 C19 171.79(18) . . . . ?
C11 C13 C14 C19 -5.4(3) . . . . ?
O2 C13 C14 C15 -6.7(3) . . . . ?
C11 C13 C14 C15 176.07(17) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C13 C14 C15 C16 178.4(2) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C13 C14 C19 C18 -179.11(18) . . . . ?
C17 C18 C19 C14 1.2(3) . . . . ?
C11 C10 C20 C25 -35.3(3) . . . . ?
C9 C10 C20 C25 149.58(18) . . . . ?
C11 C10 C20 C21 143.4(2) . . . . ?
C9 C10 C20 C21 -31.7(3) . . . . ?
C25 C20 C21 C22 2.8(3) . . . . ?
C10 C20 C21 C22 -175.88(19) . . . . ?
C20 C21 C22 C23 -1.5(3) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 1.2(4) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C21 C20 C25 C24 -2.1(3) . . . . ?
C10 C20 C25 C24 176.55(19) . . . . ?
C10 C9 C26 C27 148.64(17) . . . . ?
C8 C9 C26 C27 -89.9(2) . . . . ?
C10 C9 C26 C31 -34.7(2) . . . . ?
C8 C9 C26 C31 86.7(2) . . . . ?
C31 C26 C27 C28 -0.8(3) . . . . ?
C9 C26 C27 C28 175.96(17) . . . . ?
C26 C27 C28 C29 -0.1(3) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C28 C29 C30 C31 -1.1(3) . . . . ?
C29 C30 C31 C26 0.1(3) . . . . ?
C27 C26 C31 C30 0.8(3) . . . . ?
C9 C26 C31 C30 -175.87(17) . . . . ?

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
C32 H32B O2 0.98 2.63 3.609(2) 176.5 4_565
C9 H9 O2 1.00 2.65 3.512(2) 144.8 4_565

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.066

_shelxl_version_number           2013-4

