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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2003314'
loop_
_audit_author_name
_audit_author_address
'Antonio LLamas'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-06-23 downloaded from the CCDC.
;

_audit_creation_date             2015-06-21T18:34:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C25 H19 N O2'
_chemical_formula_sum            'C25 H19 N O2'
_chemical_formula_weight         365.41
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
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'

_cell_length_a                   5.2753(2)
_cell_length_b                   8.2287(2)
_cell_length_c                   45.0822(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1956.97(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7950
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.02
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.991
_shelx_estimated_absorpt_T_min   0.96
_shelx_estimated_absorpt_T_max   0.996

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      -0.12947
_diffrn_orient_matrix_ub_12      -0.088748
_diffrn_orient_matrix_ub_13      -0.000317
_diffrn_orient_matrix_ub_21      0.138017
_diffrn_orient_matrix_ub_22      -0.082911
_diffrn_orient_matrix_ub_23      0.001475
_diffrn_orient_matrix_ub_31      -0.011053
_diffrn_orient_matrix_ub_32      0.004253
_diffrn_orient_matrix_ub_33      0.02213
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_number            28768
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.689
_reflns_number_total             4486
_reflns_number_gt                3752
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.3837P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4486
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.5771(4) 0.7277(2) 0.13088(4) 0.0174(4) Uani 1 1 d . . . . .
H1 H 0.731(6) 0.741(3) 0.1383(6) 0.046(8) Uiso 1 1 d . . . . .
C2 C 0.3704(4) 0.7584(2) 0.14797(4) 0.0165(4) Uani 1 1 d . . . . .
O3 O 0.1507(3) 0.74903(19) 0.13986(3) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.4303(4) 0.8044(3) 0.18021(4) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.3096 0.8912 0.1867 0.023 Uiso 1 1 calc R U . . .
O5 O 0.6823(3) 0.86173(18) 0.18428(3) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.7167(5) 1.0237(3) 0.17395(5) 0.0312(6) Uani 1 1 d . . . . .
H6A H 0.7006 1.0261 0.1523 0.047 Uiso 1 1 calc R U . . .
H6B H 0.8855 1.0623 0.1797 0.047 Uiso 1 1 calc R U . . .
H6C H 0.5875 1.0943 0.1828 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3972(4) 0.6584(3) 0.20016(4) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.5778(4) 0.5354(3) 0.20017(5) 0.0223(5) Uani 1 1 d . . . . .
H12 H 0.7179 0.541 0.187 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5543(5) 0.4045(3) 0.21940(5) 0.0281(5) Uani 1 1 d . . . . .
H13 H 0.6793 0.3214 0.2195 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3479(5) 0.3949(3) 0.23847(5) 0.0289(6) Uani 1 1 d . . . . .
H14 H 0.3316 0.3056 0.2517 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1667(4) 0.5158(3) 0.23813(5) 0.0299(6) Uani 1 1 d . . . . .
H15 H 0.0244 0.5086 0.251 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1906(4) 0.6475(3) 0.21919(5) 0.0239(5) Uani 1 1 d . . . . .
H16 H 0.0655 0.7305 0.2192 0.029 Uiso 1 1 calc R U . . .
C21 C 0.5714(4) 0.6792(2) 0.10070(4) 0.0156(4) Uani 1 1 d . . . . .
C22 C 0.3791(4) 0.5814(2) 0.08955(4) 0.0177(5) Uani 1 1 d . . . . .
H22 H 0.245 0.5469 0.1021 0.021 Uiso 1 1 calc R U . . .
C23 C 0.3830(4) 0.5346(3) 0.06020(4) 0.0181(4) Uani 1 1 d . . . . .
H23 H 0.2511 0.4676 0.0527 0.022 Uiso 1 1 calc R U . . .
C24 C 0.5779(4) 0.5841(2) 0.04131(4) 0.0173(4) Uani 1 1 d . . . . .
C25 C 0.7705(4) 0.6829(3) 0.05274(4) 0.0185(5) Uani 1 1 d . . . . .
H25 H 0.9043 0.718 0.0402 0.022 Uiso 1 1 calc R U . . .
C26 C 0.7674(4) 0.7296(3) 0.08215(4) 0.0179(4) Uani 1 1 d . . . . .
H26 H 0.8992 0.7964 0.0898 0.021 Uiso 1 1 calc R U . . .
C27 C 0.5812(4) 0.5306(3) 0.01097(5) 0.0192(5) Uani 1 1 d . . . . .
C28 C 0.5800(4) 0.4798(3) -0.01382(5) 0.0193(4) Uani 1 1 d . . . . .
C31 C 0.5825(4) 0.4210(2) -0.04380(4) 0.0174(4) Uani 1 1 d . . . . .
C32 C 0.3973(4) 0.3125(3) -0.05405(5) 0.0200(5) Uani 1 1 d . . . . .
H32 H 0.2656 0.2783 -0.0411 0.024 Uiso 1 1 calc R U . . .
C33 C 0.4050(4) 0.2551(3) -0.08279(5) 0.0208(5) Uani 1 1 d . . . . .
H33 H 0.2779 0.182 -0.0895 0.025 Uiso 1 1 calc R U . . .
C34 C 0.5980(4) 0.3033(3) -0.10216(4) 0.0198(5) Uani 1 1 d . . . . .
C35 C 0.7807(4) 0.4135(3) -0.09205(5) 0.0215(5) Uani 1 1 d . . . . .
H35 H 0.9112 0.4488 -0.1051 0.026 Uiso 1 1 calc R U . . .
C36 C 0.7727(4) 0.4712(3) -0.06342(5) 0.0203(5) Uani 1 1 d . . . . .
H36 H 0.8979 0.546 -0.0569 0.024 Uiso 1 1 calc R U . . .
C37 C 0.6153(5) 0.2353(3) -0.13155(5) 0.0241(5) Uani 1 1 d . . . . .
C38 C 0.6341(5) 0.1757(3) -0.15536(5) 0.0291(6) Uani 1 1 d . . . . .
H38 H 0.6492 0.1279 -0.1745 0.035 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C2 1.359(3) . ?
N1 C21 1.418(3) . ?
N1 H1 0.88(3) . ?
C2 O3 1.218(2) . ?
C2 C4 1.535(3) . ?
C4 O5 1.422(2) . ?
C4 C11 1.511(3) . ?
C4 H4 1 . ?
O5 C6 1.423(3) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C11 C12 1.390(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.95 . ?
C13 C14 1.390(3) . ?
C13 H13 0.95 . ?
C14 C15 1.379(3) . ?
C14 H14 0.95 . ?
C15 C16 1.385(3) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C21 C22 1.389(3) . ?
C21 C26 1.393(3) . ?
C22 C23 1.378(3) . ?
C22 H22 0.95 . ?
C23 C24 1.396(3) . ?
C23 H23 0.95 . ?
C24 C25 1.400(3) . ?
C24 C27 1.437(3) . ?
C25 C26 1.381(3) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 C28 1.193(3) . ?
C28 C31 1.436(3) . ?
C31 C36 1.400(3) . ?
C31 C32 1.401(3) . ?
C32 C33 1.380(3) . ?
C32 H32 0.95 . ?
C33 C34 1.399(3) . ?
C33 H33 0.95 . ?
C34 C35 1.400(3) . ?
C34 C37 1.441(3) . ?
C35 C36 1.375(3) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C37 C38 1.184(3) . ?
C38 H38 0.95 . ?

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 N1 C21 125.40(18) . . ?
C2 N1 H1 119.9(18) . . ?
C21 N1 H1 114.7(18) . . ?
O3 C2 N1 125.58(19) . . ?
O3 C2 C4 119.71(18) . . ?
N1 C2 C4 114.69(17) . . ?
O5 C4 C11 107.13(17) . . ?
O5 C4 C2 113.35(16) . . ?
C11 C4 C2 110.10(17) . . ?
O5 C4 H4 108.7 . . ?
C11 C4 H4 108.7 . . ?
C2 C4 H4 108.7 . . ?
C4 O5 C6 112.78(17) . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 C16 119.4(2) . . ?
C12 C11 C4 120.01(18) . . ?
C16 C11 C4 120.6(2) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C21 C26 119.83(18) . . ?
C22 C21 N1 121.73(18) . . ?
C26 C21 N1 118.43(18) . . ?
C23 C22 C21 119.88(19) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 118.65(19) . . ?
C23 C24 C27 120.0(2) . . ?
C25 C24 C27 121.3(2) . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C21 120.1(2) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C28 C27 C24 177.2(2) . . ?
C27 C28 C31 178.9(2) . . ?
C36 C31 C32 118.64(19) . . ?
C36 C31 C28 120.1(2) . . ?
C32 C31 C28 121.2(2) . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.7(2) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C35 118.79(19) . . ?
C33 C34 C37 120.7(2) . . ?
C35 C34 C37 120.5(2) . . ?
C36 C35 C34 120.5(2) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 120.9(2) . . ?
C35 C36 H36 119.6 . . ?
C31 C36 H36 119.6 . . ?
C38 C37 C34 178.0(2) . . ?
C37 C38 H38 180 . . ?

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
C21 N1 C2 O3 -0.1(3) . . . . ?
C21 N1 C2 C4 178.37(18) . . . . ?
O3 C2 C4 O5 -160.76(19) . . . . ?
N1 C2 C4 O5 20.6(3) . . . . ?
O3 C2 C4 C11 79.3(2) . . . . ?
N1 C2 C4 C11 -99.3(2) . . . . ?
C11 C4 O5 C6 -162.44(17) . . . . ?
C2 C4 O5 C6 75.9(2) . . . . ?
O5 C4 C11 C12 -48.7(2) . . . . ?
C2 C4 C11 C12 75.0(2) . . . . ?
O5 C4 C11 C16 129.6(2) . . . . ?
C2 C4 C11 C16 -106.7(2) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C4 C11 C12 C13 177.13(19) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 0.5(3) . . . . ?
C4 C11 C16 C15 -177.8(2) . . . . ?
C2 N1 C21 C22 -33.5(3) . . . . ?
C2 N1 C21 C26 147.5(2) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
N1 C21 C22 C23 -178.86(19) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C22 C23 C24 C27 178.48(19) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C27 C24 C25 C26 -178.30(19) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
N1 C21 C26 C25 179.06(19) . . . . ?
C36 C31 C32 C33 0.8(3) . . . . ?
C28 C31 C32 C33 -178.9(2) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 -1.3(3) . . . . ?
C32 C33 C34 C37 176.0(2) . . . . ?
C33 C34 C35 C36 1.1(3) . . . . ?
C37 C34 C35 C36 -176.2(2) . . . . ?
C34 C35 C36 C31 0.0(3) . . . . ?
C32 C31 C36 C35 -1.0(3) . . . . ?
C28 C31 C36 C35 178.7(2) . . . . ?

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2003315'
loop_
_audit_author_name
_audit_author_address
'Antonio LLamas'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2020-06-23 downloaded from the CCDC.
;

_audit_creation_date             2019-06-12T09:05:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C33 H23 N O2'
_chemical_formula_sum            'C33 H23 N O2'
_chemical_formula_weight         465.52
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.3349(2)
_cell_length_b                   8.0996(4)
_cell_length_c                   58.179(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2513.94(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1556
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      74.14
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS-2016/2'
_exptl_absorpt_correction_T_min  0.7979
_exptl_absorpt_correction_T_max  0.9705
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.988

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'Incoatec multilayer mirror'
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.1376
_diffrn_reflns_av_unetI/netI     0.1064
_diffrn_reflns_number            22404
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -72
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         74.776
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_coverage         0.681
_reflns_number_total             5141
_reflns_number_gt                2954
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX3v2018.7-2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0920P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5141
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.3541(14) 0.9728(9) 0.67577(13) 0.0504(17) Uani 1 1 d . . . . .
C2 C 0.3738(14) 0.9115(9) 0.65715(12) 0.0453(16) Uani 1 1 d . . . . .
C3 C 0.3938(12) 0.8429(8) 0.63430(10) 0.0382(14) Uani 1 1 d . . . . .
C4 C 0.2131(13) 0.7357(8) 0.62601(11) 0.0396(15) Uani 1 1 d . . . . .
H4 H 0.079117 0.702427 0.635719 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2253(11) 0.6767(8) 0.60384(11) 0.0385(14) Uani 1 1 d . . . . .
H5 H 0.10103 0.60194 0.598498 0.046 Uiso 1 1 calc R U . . .
C6 C 0.4192(12) 0.7258(7) 0.58906(10) 0.0342(13) Uani 1 1 d . . . . .
C7 C 0.6019(11) 0.8346(8) 0.59752(11) 0.0369(13) Uani 1 1 d . . . . .
H7 H 0.734632 0.869304 0.587767 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5909(12) 0.8914(8) 0.61976(11) 0.0406(14) Uani 1 1 d . . . . .
H8 H 0.717156 0.963825 0.625337 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4265(11) 0.6676(8) 0.56590(10) 0.0353(13) Uani 1 1 d . . . . .
C10 C 0.4265(12) 0.6157(8) 0.54637(10) 0.0356(13) Uani 1 1 d . . . . .
C11 C 0.4201(11) 0.5568(8) 0.52324(10) 0.0338(13) Uani 1 1 d . . . . .
C12 C 0.2274(11) 0.4524(8) 0.51565(10) 0.0357(13) Uani 1 1 d . . . . .
H12 H 0.100496 0.41886 0.526114 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2196(11) 0.3982(8) 0.49335(10) 0.0345(13) Uani 1 1 d . . . . .
H13 H 0.086587 0.328592 0.488457 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4063(11) 0.4446(7) 0.47773(10) 0.0324(12) Uani 1 1 d . . . . .
C15 C 0.5988(12) 0.5486(8) 0.48523(10) 0.0358(13) Uani 1 1 d . . . . .
H15 H 0.725091 0.582534 0.474737 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6071(11) 0.6023(7) 0.50769(10) 0.0346(13) Uani 1 1 d . . . . .
H16 H 0.741083 0.670912 0.512626 0.042 Uiso 1 1 calc R U . . .
C17 C 0.4016(11) 0.3829(8) 0.45462(10) 0.0345(13) Uani 1 1 d . . . . .
C18 C 0.4021(11) 0.3292(8) 0.43544(10) 0.0347(13) Uani 1 1 d . . . . .
C19 C 0.4089(11) 0.2716(7) 0.41213(9) 0.0321(13) Uani 1 1 d . . . . .
C20 C 0.2183(10) 0.1721(8) 0.40317(10) 0.0339(12) Uani 1 1 d . . . . .
H20 H 0.083452 0.138333 0.412751 0.041 Uiso 1 1 calc R U . . .
C21 C 0.2250(11) 0.1224(8) 0.38039(10) 0.0340(13) Uani 1 1 d . . . . .
H21 H 0.094183 0.055466 0.374408 0.041 Uiso 1 1 calc R U . . .
C22 C 0.4226(11) 0.1700(8) 0.36623(10) 0.0352(13) Uani 1 1 d . . . . .
C23 C 0.6128(12) 0.2674(7) 0.37487(10) 0.0356(13) Uani 1 1 d . . . . .
H23 H 0.748224 0.299472 0.365249 0.043 Uiso 1 1 calc R U . . .
C24 C 0.6060(11) 0.3187(8) 0.39766(10) 0.0353(13) Uani 1 1 d . . . . .
H24 H 0.736644 0.386462 0.403493 0.042 Uiso 1 1 calc R U . . .
C25 C 0.6229(11) 0.0887(8) 0.32970(10) 0.0369(14) Uani 1 1 d . . . . .
C26 C 0.5654(12) 0.0418(8) 0.30454(11) 0.0398(14) Uani 1 1 d . . . . .
H26 H 0.683595 -0.047261 0.299623 0.048 Uiso 1 1 calc R U . . .
C27 C 0.5990(12) 0.1885(9) 0.28901(10) 0.0401(14) Uani 1 1 d . . . . .
C28 C 0.4241(13) 0.3125(9) 0.28839(11) 0.0442(15) Uani 1 1 d . . . . .
H28 H 0.283355 0.307779 0.298369 0.053 Uiso 1 1 calc R U . . .
C29 C 0.4496(14) 0.4445(10) 0.27343(13) 0.0523(18) Uani 1 1 d . . . . .
H29 H 0.326293 0.529137 0.273077 0.063 Uiso 1 1 calc R U . . .
C30 C 0.6566(13) 0.4527(10) 0.25892(12) 0.0504(18) Uani 1 1 d . . . . .
H30 H 0.674729 0.542549 0.24856 0.06 Uiso 1 1 calc R U . . .
C31 C 0.8346(14) 0.3303(10) 0.25965(12) 0.0542(18) Uani 1 1 d . . . . .
H31 H 0.976826 0.33629 0.249858 0.065 Uiso 1 1 calc R U . . .
C32 C 0.8080(12) 0.1980(9) 0.27455(11) 0.0441(15) Uani 1 1 d . . . . .
H32 H 0.931867 0.11381 0.27496 0.053 Uiso 1 1 calc R U . . .
C33 C 0.2752(14) -0.1776(9) 0.30954(13) 0.0541(18) Uani 1 1 d . . . . .
H33A H 0.394515 -0.252053 0.302018 0.081 Uiso 1 1 calc R U . . .
H33B H 0.103753 -0.211743 0.305796 0.081 Uiso 1 1 calc R U . . .
H33C H 0.299549 -0.182014 0.32622 0.081 Uiso 1 1 calc R U . . .
N1 N 0.4198(10) 0.1198(6) 0.34280(8) 0.0344(11) Uani 1 1 d . . . . .
O1 O 0.8416(8) 0.0996(6) 0.33604(7) 0.0419(11) Uani 1 1 d . . . . .
O2 O 0.3149(8) -0.0157(6) 0.30177(7) 0.0417(10) Uani 1 1 d . . . . .
H1 H 0.316(14) 1.025(10) 0.6896(14) 0.06(2) Uiso 1 1 d . . . . .
H1N H 0.257(17) 0.118(11) 0.3349(15) 0.07(2) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.196(10) . ?
C1 H1 0.93(8) . ?
C2 C3 1.445(9) . ?
C3 C4 1.384(10) . ?
C3 C8 1.406(10) . ?
C4 C5 1.377(9) . ?
C4 H4 0.95 . ?
C5 C6 1.403(9) . ?
C5 H5 0.95 . ?
C6 C7 1.403(9) . ?
C6 C9 1.428(9) . ?
C7 C8 1.375(9) . ?
C7 H7 0.95 . ?
C8 H8 0.95 . ?
C9 C10 1.212(9) . ?
C10 C11 1.428(9) . ?
C11 C16 1.396(9) . ?
C11 C12 1.403(9) . ?
C12 C13 1.370(9) . ?
C12 H12 0.95 . ?
C13 C14 1.400(9) . ?
C13 H13 0.95 . ?
C14 C15 1.398(9) . ?
C14 C17 1.435(8) . ?
C15 C16 1.378(9) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C18 1.197(8) . ?
C18 C19 1.435(8) . ?
C19 C20 1.399(9) . ?
C19 C24 1.400(9) . ?
C20 C21 1.385(9) . ?
C20 H20 0.95 . ?
C21 C22 1.393(9) . ?
C21 H21 0.95 . ?
C22 C23 1.380(9) . ?
C22 N1 1.422(8) . ?
C23 C24 1.390(8) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C25 O1 1.227(8) . ?
C25 N1 1.348(8) . ?
C25 C26 1.543(8) . ?
C26 O2 1.424(8) . ?
C26 C27 1.503(10) . ?
C26 H26 1 . ?
C27 C28 1.371(10) . ?
C27 C32 1.399(9) . ?
C28 C29 1.386(10) . ?
C28 H28 0.95 . ?
C29 C30 1.391(11) . ?
C29 H29 0.95 . ?
C30 C31 1.374(11) . ?
C30 H30 0.95 . ?
C31 C32 1.385(11) . ?
C31 H31 0.95 . ?
C32 H32 0.95 . ?
C33 O2 1.403(9) . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
N1 H1N 0.98(9) . ?

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 H1 172(5) . . ?
C1 C2 C3 177.9(7) . . ?
C4 C3 C8 119.1(6) . . ?
C4 C3 C2 120.7(6) . . ?
C8 C3 C2 120.1(6) . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.7(6) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 118.4(6) . . ?
C5 C6 C9 120.3(6) . . ?
C7 C6 C9 121.3(6) . . ?
C8 C7 C6 120.7(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C3 120.3(6) . . ?
C7 C8 H8 119.9 . . ?
C3 C8 H8 119.9 . . ?
C10 C9 C6 178.1(7) . . ?
C9 C10 C11 178.4(7) . . ?
C16 C11 C12 118.6(5) . . ?
C16 C11 C10 120.4(6) . . ?
C12 C11 C10 121.0(6) . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.5(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 118.8(5) . . ?
C15 C14 C17 121.0(5) . . ?
C13 C14 C17 120.2(5) . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.5(6) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C18 C17 C14 178.6(7) . . ?
C17 C18 C19 177.3(7) . . ?
C20 C19 C24 118.6(5) . . ?
C20 C19 C18 121.4(5) . . ?
C24 C19 C18 119.9(6) . . ?
C21 C20 C19 120.3(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.4(6) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C21 119.9(6) . . ?
C23 C22 N1 121.4(5) . . ?
C21 C22 N1 118.7(5) . . ?
C22 C23 C24 119.9(6) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C23 C24 C19 120.8(6) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
O1 C25 N1 125.5(5) . . ?
O1 C25 C26 119.5(5) . . ?
N1 C25 C26 115.0(5) . . ?
O2 C26 C27 107.6(5) . . ?
O2 C26 C25 112.0(5) . . ?
C27 C26 C25 110.6(5) . . ?
O2 C26 H26 108.9 . . ?
C27 C26 H26 108.9 . . ?
C25 C26 H26 108.9 . . ?
C28 C27 C32 119.1(6) . . ?
C28 C27 C26 120.9(6) . . ?
C32 C27 C26 120.0(6) . . ?
C27 C28 C29 121.0(7) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C28 C29 C30 119.7(7) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 119.7(7) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.4(7) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 120.0(7) . . ?
C31 C32 H32 120 . . ?
C27 C32 H32 120 . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C25 N1 C22 125.9(5) . . ?
C25 N1 H1N 116(5) . . ?
C22 N1 H1N 117(5) . . ?
C33 O2 C26 114.3(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 C3 C4 C5 0.1(10) . . . . ?
C2 C3 C4 C5 176.7(6) . . . . ?
C3 C4 C5 C6 -0.9(10) . . . . ?
C4 C5 C6 C7 0.9(9) . . . . ?
C4 C5 C6 C9 -178.3(6) . . . . ?
C5 C6 C7 C8 0.0(9) . . . . ?
C9 C6 C7 C8 179.1(6) . . . . ?
C6 C7 C8 C3 -0.9(9) . . . . ?
C4 C3 C8 C7 0.8(10) . . . . ?
C2 C3 C8 C7 -175.9(6) . . . . ?
C16 C11 C12 C13 -1.1(9) . . . . ?
C10 C11 C12 C13 179.0(6) . . . . ?
C11 C12 C13 C14 0.8(9) . . . . ?
C12 C13 C14 C15 -0.7(9) . . . . ?
C12 C13 C14 C17 177.9(6) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
C17 C14 C15 C16 -177.6(6) . . . . ?
C14 C15 C16 C11 -1.4(9) . . . . ?
C12 C11 C16 C15 1.4(9) . . . . ?
C10 C11 C16 C15 -178.6(6) . . . . ?
C24 C19 C20 C21 -0.4(9) . . . . ?
C18 C19 C20 C21 177.9(6) . . . . ?
C19 C20 C21 C22 0.5(9) . . . . ?
C20 C21 C22 C23 -0.1(9) . . . . ?
C20 C21 C22 N1 -178.5(6) . . . . ?
C21 C22 C23 C24 -0.4(9) . . . . ?
N1 C22 C23 C24 178.0(6) . . . . ?
C22 C23 C24 C19 0.5(9) . . . . ?
C20 C19 C24 C23 -0.1(9) . . . . ?
C18 C19 C24 C23 -178.4(6) . . . . ?
O1 C25 C26 O2 161.5(6) . . . . ?
N1 C25 C26 O2 -20.6(8) . . . . ?
O1 C25 C26 C27 -78.5(8) . . . . ?
N1 C25 C26 C27 99.4(7) . . . . ?
O2 C26 C27 C28 47.1(8) . . . . ?
C25 C26 C27 C28 -75.5(7) . . . . ?
O2 C26 C27 C32 -131.5(6) . . . . ?
C25 C26 C27 C32 105.9(7) . . . . ?
C32 C27 C28 C29 1.2(10) . . . . ?
C26 C27 C28 C29 -177.4(6) . . . . ?
C27 C28 C29 C30 -0.6(10) . . . . ?
C28 C29 C30 C31 -0.4(11) . . . . ?
C29 C30 C31 C32 0.6(11) . . . . ?
C30 C31 C32 C27 0.0(10) . . . . ?
C28 C27 C32 C31 -0.9(9) . . . . ?
C26 C27 C32 C31 177.7(6) . . . . ?
O1 C25 N1 C22 -0.2(10) . . . . ?
C26 C25 N1 C22 -178.0(6) . . . . ?
C23 C22 N1 C25 32.6(9) . . . . ?
C21 C22 N1 C25 -149.1(6) . . . . ?
C27 C26 O2 C33 161.9(5) . . . . ?
C25 C26 O2 C33 -76.4(7) . . . . ?

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
_geom_hbond_publ_flag
C23 H23 O1 0.95 2.4 2.905(7) 113 . yes
C21 H21 O1 0.95 2.63 3.298(7) 127.6 1_455 yes

