# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_fgw1602
_database_code_depnum_ccdc_archive 'CCDC 1850685'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Dept of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2018-06-20 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O'
_chemical_formula_sum            'C27 H21 N O'
_chemical_formula_weight         375.45

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                   14.8685(8)
_cell_length_b                   8.0336(4)
_cell_length_c                   16.4560(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.1431(7)
_cell_angle_gamma                90
_cell_volume                     1962.67(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5004
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      25.73

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9012
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14714
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.798
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4038
_reflns_number_gt                3140
_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    'SHELXD (Schneider & Sheldrick, 2002)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0809P)²+0.8151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4038
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
O O 0.12733(8) 0.16615(15) 0.48272(7) 0.0285(3) Uani 1 1 d . . . . .
N N 0.39612(14) -0.1294(3) 0.52544(13) 0.0578(6) Uani 1 1 d . . . . .
C1 C 0.30903(14) 0.2916(3) 0.38548(12) 0.0396(5) Uani 1 1 d . . . . .
H1 H 0.2915 0.3246 0.3315 0.047 Uiso 1 1 calc R U . . .
C2 C 0.39145(17) 0.3671(4) 0.42596(15) 0.0568(7) Uani 1 1 d . . . . .
H2A H 0.3885 0.4891 0.4178 0.068 Uiso 1 1 calc R U . . .
H2B H 0.4445 0.3259 0.3982 0.068 Uiso 1 1 calc R U . . .
C3 C 0.40635(14) 0.3337(3) 0.51482(13) 0.0430(5) Uani 1 1 d . . . . .
H3A H 0.4270 0.4377 0.5421 0.052 Uiso 1 1 calc R U . . .
H3B H 0.4552 0.2506 0.5227 0.052 Uiso 1 1 calc R U . . .
C4 C 0.32413(14) 0.2703(3) 0.55586(12) 0.0377(5) Uani 1 1 d . . . . .
H4A H 0.2794 0.3611 0.5588 0.045 Uiso 1 1 calc R U . . .
H4B H 0.3418 0.2350 0.6121 0.045 Uiso 1 1 calc R U . . .
C5 C 0.28197(13) 0.1245(3) 0.50916(11) 0.0345(4) Uani 1 1 d . . . . .
C6 C 0.18588(12) 0.0624(2) 0.53356(11) 0.0283(4) Uani 1 1 d . . . . .
C7 C 0.17075(14) -0.1058(2) 0.49067(12) 0.0353(4) Uani 1 1 d . . . . .
C8 C 0.16660(15) -0.2675(3) 0.51641(14) 0.0425(5) Uani 1 1 d . . . . .
H8 H 0.1732 -0.2947 0.5726 0.051 Uiso 1 1 calc R U . . .
C9 C 0.15235(15) -0.3918(3) 0.45727(14) 0.0437(5) Uani 1 1 d . . . . .
H9 H 0.1492 -0.5050 0.4736 0.052 Uiso 1 1 calc R U . . .
C10 C 0.14280(15) -0.3515(3) 0.37498(14) 0.0428(5) Uani 1 1 d . . . . .
H10 H 0.1349 -0.4375 0.3356 0.051 Uiso 1 1 calc R U . . .
C11 C 0.14471(13) -0.1846(2) 0.34977(13) 0.0358(4) Uani 1 1 d . . . . .
H11 H 0.1368 -0.1557 0.2939 0.043 Uiso 1 1 calc R U . . .
C12 C 0.15831(13) -0.0651(2) 0.40817(11) 0.0330(4) Uani 1 1 d . . . . .
C13 C 0.16217(12) 0.1243(2) 0.40351(10) 0.0276(4) Uani 1 1 d . . . . .
C14 C 0.25940(12) 0.1805(2) 0.42192(11) 0.0319(4) Uani 1 1 d . . . . .
C15 C 0.34703(14) -0.0185(3) 0.51652(12) 0.0406(5) Uani 1 1 d . . . . .
C16 C 0.16781(12) 0.0759(2) 0.62189(11) 0.0297(4) Uani 1 1 d . . . . .
C17 C 0.09843(13) 0.1729(3) 0.64883(12) 0.0359(4) Uani 1 1 d . . . . .
H17 H 0.0598 0.2312 0.6108 0.043 Uiso 1 1 calc R U . . .
C18 C 0.08543(15) 0.1849(3) 0.73168(13) 0.0441(5) Uani 1 1 d . . . . .
H18 H 0.0381 0.2524 0.7498 0.053 Uiso 1 1 calc R U . . .
C19 C 0.14030(15) 0.1001(3) 0.78776(13) 0.0444(5) Uani 1 1 d . . . . .
H19 H 0.1308 0.1087 0.8442 0.053 Uiso 1 1 calc R U . . .
C20 C 0.20952(16) 0.0020(3) 0.76106(13) 0.0448(5) Uani 1 1 d . . . . .
H20 H 0.2477 -0.0569 0.7993 0.054 Uiso 1 1 calc R U . . .
C21 C 0.22303(14) -0.0100(3) 0.67895(12) 0.0393(5) Uani 1 1 d . . . . .
H21 H 0.2705 -0.0775 0.6611 0.047 Uiso 1 1 calc R U . . .
C22 C 0.10887(13) 0.2045(2) 0.33437(11) 0.0311(4) Uani 1 1 d . . . . .
C23 C 0.02467(14) 0.2724(3) 0.34571(13) 0.0402(5) Uani 1 1 d . . . . .
H23 H -0.0004 0.2659 0.3975 0.048 Uiso 1 1 calc R U . . .
C24 C -0.02312(16) 0.3499(3) 0.28124(16) 0.0528(6) Uani 1 1 d . . . . .
H24 H -0.0808 0.3960 0.2892 0.063 Uiso 1 1 calc R U . . .
C25 C 0.01247(19) 0.3604(3) 0.20600(15) 0.0569(7) Uani 1 1 d . . . . .
H25 H -0.0198 0.4165 0.1628 0.068 Uiso 1 1 calc R U . . .
C26 C 0.09520(19) 0.2892(3) 0.19322(14) 0.0532(6) Uani 1 1 d . . . . .
H26 H 0.1194 0.2949 0.1410 0.064 Uiso 1 1 calc R U . . .
C27 C 0.14311(16) 0.2091(3) 0.25732(12) 0.0417(5) Uani 1 1 d . . . . .
H27 H 0.1992 0.1576 0.2483 0.050 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
O C6 1.440(2) . ?
O C13 1.468(2) . ?
N C15 1.156(3) . ?
C1 C14 1.323(3) . ?
C1 C2 1.491(3) . ?
C2 C3 1.491(3) . ?
C3 C4 1.517(3) . ?
C4 C5 1.518(3) . ?
C5 C15 1.502(3) . ?
C5 C14 1.524(3) . ?
C5 C6 1.585(3) . ?
C6 C16 1.496(2) . ?
C6 C7 1.535(3) . ?
C7 C8 1.369(3) . ?
C7 C12 1.399(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.392(3) . ?
C10 C11 1.405(3) . ?
C11 C12 1.366(3) . ?
C12 C13 1.525(3) . ?
C13 C22 1.496(2) . ?
C13 C14 1.529(3) . ?
C16 C17 1.385(3) . ?
C16 C21 1.395(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.378(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.380(3) . ?
C22 C23 1.388(3) . ?
C22 C27 1.392(3) . ?
C23 C24 1.391(3) . ?
C24 C25 1.375(4) . ?
C25 C26 1.383(4) . ?
C26 C27 1.397(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O C13 98.74(12) . . ?
C14 C1 C2 122.50(19) . . ?
C1 C2 C3 116.04(18) . . ?
C2 C3 C4 114.65(18) . . ?
C3 C4 C5 110.76(16) . . ?
C15 C5 C4 107.64(16) . . ?
C15 C5 C14 114.15(16) . . ?
C4 C5 C14 108.22(16) . . ?
C15 C5 C6 108.93(16) . . ?
C4 C5 C6 117.87(16) . . ?
C14 C5 C6 100.16(14) . . ?
O C6 C16 112.81(14) . . ?
O C6 C7 100.00(14) . . ?
C16 C6 C7 118.71(15) . . ?
O C6 C5 101.27(14) . . ?
C16 C6 C5 115.82(15) . . ?
C7 C6 C5 105.77(15) . . ?
C8 C7 C12 121.09(19) . . ?
C8 C7 C6 134.51(19) . . ?
C12 C7 C6 104.39(15) . . ?
C7 C8 C9 118.0(2) . . ?
C10 C9 C8 120.87(19) . . ?
C9 C10 C11 120.44(19) . . ?
C12 C11 C10 117.90(19) . . ?
C11 C12 C7 121.69(18) . . ?
C11 C12 C13 132.12(18) . . ?
C7 C12 C13 106.19(16) . . ?
O C13 C22 112.27(14) . . ?
O C13 C12 99.65(13) . . ?
C22 C13 C12 116.60(15) . . ?
O C13 C14 97.61(13) . . ?
C22 C13 C14 118.66(15) . . ?
C12 C13 C14 108.79(15) . . ?
C1 C14 C5 121.78(17) . . ?
C1 C14 C13 130.86(18) . . ?
C5 C14 C13 104.87(15) . . ?
N C15 C5 177.2(2) . . ?
C17 C16 C21 118.93(18) . . ?
C17 C16 C6 121.88(17) . . ?
C21 C16 C6 119.18(16) . . ?
C16 C17 C18 119.92(19) . . ?
C19 C18 C17 120.9(2) . . ?
C18 C19 C20 119.41(19) . . ?
C21 C20 C19 120.0(2) . . ?
C20 C21 C16 120.82(19) . . ?
C23 C22 C27 119.32(18) . . ?
C23 C22 C13 120.73(17) . . ?
C27 C22 C13 119.94(18) . . ?
C22 C23 C24 120.0(2) . . ?
C25 C24 C23 120.6(2) . . ?
C24 C25 C26 120.1(2) . . ?
C25 C26 C27 119.8(2) . . ?
C22 C27 C26 120.2(2) . . ?

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
C14 C1 C2 C3 -10.4(4) . . . . ?
C1 C2 C3 C4 -16.4(3) . . . . ?
C2 C3 C4 C5 50.5(3) . . . . ?
C3 C4 C5 C15 67.2(2) . . . . ?
C3 C4 C5 C14 -56.7(2) . . . . ?
C3 C4 C5 C6 -169.25(17) . . . . ?
C13 O C6 C16 179.91(14) . . . . ?
C13 O C6 C7 -52.98(15) . . . . ?
C13 O C6 C5 55.47(15) . . . . ?
C15 C5 C6 O -148.65(15) . . . . ?
C4 C5 C6 O 88.40(19) . . . . ?
C14 C5 C6 O -28.59(17) . . . . ?
C15 C5 C6 C16 88.97(19) . . . . ?
C4 C5 C6 C16 -34.0(2) . . . . ?
C14 C5 C6 C16 -150.97(16) . . . . ?
C15 C5 C6 C7 -44.75(19) . . . . ?
C4 C5 C6 C7 -167.69(16) . . . . ?
C14 C5 C6 C7 75.31(17) . . . . ?
O C6 C7 C8 -144.4(2) . . . . ?
C16 C6 C7 C8 -21.4(3) . . . . ?
C5 C6 C7 C8 110.7(3) . . . . ?
O C6 C7 C12 34.50(18) . . . . ?
C16 C6 C7 C12 157.55(16) . . . . ?
C5 C6 C7 C12 -70.33(18) . . . . ?
C12 C7 C8 C9 2.0(3) . . . . ?
C6 C7 C8 C9 -179.2(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -1.8(3) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C10 C11 C12 C13 -178.40(19) . . . . ?
C8 C7 C12 C11 -2.3(3) . . . . ?
C6 C7 C12 C11 178.55(17) . . . . ?
C8 C7 C12 C13 176.82(19) . . . . ?
C6 C7 C12 C13 -2.3(2) . . . . ?
C6 O C13 C22 175.38(14) . . . . ?
C6 O C13 C12 51.30(15) . . . . ?
C6 O C13 C14 -59.33(15) . . . . ?
C11 C12 C13 O 149.1(2) . . . . ?
C7 C12 C13 O -29.89(18) . . . . ?
C11 C12 C13 C22 28.1(3) . . . . ?
C7 C12 C13 C22 -150.89(17) . . . . ?
C11 C12 C13 C14 -109.3(2) . . . . ?
C7 C12 C13 C14 71.63(19) . . . . ?
C2 C1 C14 C5 1.5(3) . . . . ?
C2 C1 C14 C13 160.7(2) . . . . ?
C15 C5 C14 C1 -87.4(2) . . . . ?
C4 C5 C14 C1 32.5(3) . . . . ?
C6 C5 C14 C1 156.43(19) . . . . ?
C15 C5 C14 C13 108.73(18) . . . . ?
C4 C5 C14 C13 -131.44(16) . . . . ?
C6 C5 C14 C13 -7.47(18) . . . . ?
O C13 C14 C1 -121.7(2) . . . . ?
C22 C13 C14 C1 -1.1(3) . . . . ?
C12 C13 C14 C1 135.3(2) . . . . ?
O C13 C14 C5 40.11(17) . . . . ?
C22 C13 C14 C5 160.69(16) . . . . ?
C12 C13 C14 C5 -62.84(18) . . . . ?
O C6 C16 C17 3.0(2) . . . . ?
C7 C6 C16 C17 -113.4(2) . . . . ?
C5 C6 C16 C17 119.1(2) . . . . ?
O C6 C16 C21 -176.13(16) . . . . ?
C7 C6 C16 C21 67.4(2) . . . . ?
C5 C6 C16 C21 -60.1(2) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
C6 C16 C17 C18 -178.48(19) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C17 C16 C21 C20 -0.5(3) . . . . ?
C6 C16 C21 C20 178.72(19) . . . . ?
O C13 C22 C23 -15.1(2) . . . . ?
C12 C13 C22 C23 99.0(2) . . . . ?
C14 C13 C22 C23 -127.84(19) . . . . ?
O C13 C22 C27 165.94(16) . . . . ?
C12 C13 C22 C27 -80.0(2) . . . . ?
C14 C13 C22 C27 53.2(2) . . . . ?
C27 C22 C23 C24 -2.5(3) . . . . ?
C13 C22 C23 C24 178.48(19) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 1.9(4) . . . . ?
C24 C25 C26 C27 -1.0(4) . . . . ?
C23 C22 C27 C26 3.4(3) . . . . ?
C13 C22 C27 C26 -177.57(19) . . . . ?
C25 C26 C27 C22 -1.7(3) . . . . ?

_refine_diff_density_max         0.779
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_fgw1603
_database_code_depnum_ccdc_archive 'CCDC 1850686'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Dept of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2018-06-20 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O'
_chemical_formula_sum            'C27 H21 N O'
_chemical_formula_weight         375.45

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

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

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

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

_cell_length_a                   10.4535(9)
_cell_length_b                   11.5142(10)
_cell_length_c                   17.3923(14)
_cell_angle_alpha                71.1047(11)
_cell_angle_beta                 87.8758(11)
_cell_angle_gamma                89.5875(11)
_cell_volume                     1979.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5641
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.24

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8231
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15431
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8136
_reflns_number_gt                5553
_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    'SHELXD (Schneider & Sheldrick, 2002)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0798P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8136
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.32084(11) 0.30007(11) 0.34947(7) 0.0294(3) Uani 1 1 d . . . . .
N1A N 0.14271(18) 0.24811(16) 0.53516(11) 0.0465(5) Uani 1 1 d . . . . .
C1A C 0.15280(17) 0.16363(16) 0.36272(11) 0.0293(4) Uani 1 1 d . . . . .
C2A C 0.07751(18) 0.06953(17) 0.36727(12) 0.0349(4) Uani 1 1 d . . . . .
H2A H 0.1137 0.0017 0.3546 0.042 Uiso 1 1 calc R U . . .
C3A C -0.06261(18) 0.06473(18) 0.39148(14) 0.0428(5) Uani 1 1 d . . . . .
H3A H -0.0796 -0.0105 0.4383 0.051 Uiso 1 1 calc R U . . .
H3B H -0.1129 0.0588 0.3458 0.051 Uiso 1 1 calc R U . . .
C4A C -0.10861(18) 0.17559(17) 0.41441(13) 0.0399(5) Uani 1 1 d . . . . .
H4A H -0.0968 0.1591 0.4732 0.048 Uiso 1 1 calc R U . . .
H4B H -0.2013 0.1867 0.4048 0.048 Uiso 1 1 calc R U . . .
C5A C -0.03807(17) 0.29470(17) 0.36646(13) 0.0365(5) Uani 1 1 d . . . . .
H5A H -0.0709 0.3633 0.3841 0.044 Uiso 1 1 calc R U . . .
H5B H -0.0526 0.3147 0.3077 0.044 Uiso 1 1 calc R U . . .
C6A C 0.10551(17) 0.27742(16) 0.38186(11) 0.0295(4) Uani 1 1 d . . . . .
C7A C 0.20669(16) 0.37536(16) 0.32844(11) 0.0279(4) Uani 1 1 d . . . . .
C8A C 0.19400(17) 0.38232(16) 0.24007(11) 0.0302(4) Uani 1 1 d . . . . .
C9A C 0.14056(18) 0.46925(18) 0.17421(12) 0.0367(5) Uani 1 1 d . . . . .
H9A H 0.1013 0.5411 0.1795 0.044 Uiso 1 1 calc R U . . .
C10A C 0.1468(2) 0.4470(2) 0.09978(13) 0.0452(5) Uani 1 1 d . . . . .
H10A H 0.1136 0.5060 0.0531 0.054 Uiso 1 1 calc R U . . .
C11A C 0.2002(2) 0.3407(2) 0.09294(13) 0.0443(5) Uani 1 1 d . . . . .
H11A H 0.2031 0.3280 0.0416 0.053 Uiso 1 1 calc R U . . .
C12A C 0.25033(18) 0.25121(19) 0.16012(12) 0.0379(5) Uani 1 1 d . . . . .
H12A H 0.2848 0.1770 0.1556 0.045 Uiso 1 1 calc R U . . .
C13A C 0.24788(17) 0.27472(17) 0.23338(11) 0.0314(4) Uani 1 1 d . . . . .
C14A C 0.28438(17) 0.20005(16) 0.31981(11) 0.0295(4) Uani 1 1 d . . . . .
C15A C 0.12782(17) 0.26300(16) 0.46790(12) 0.0314(4) Uani 1 1 d . . . . .
C16A C 0.22020(17) 0.49341(16) 0.34635(11) 0.0301(4) Uani 1 1 d . . . . .
C17A C 0.33755(17) 0.52796(17) 0.36751(11) 0.0317(4) Uani 1 1 d . . . . .
H17A H 0.4086 0.4743 0.3735 0.038 Uiso 1 1 calc R U . . .
C18A C 0.35167(19) 0.64011(17) 0.37996(12) 0.0367(5) Uani 1 1 d . . . . .
H18A H 0.4324 0.6630 0.3941 0.044 Uiso 1 1 calc R U . . .
C19A C 0.2491(2) 0.71869(19) 0.37199(13) 0.0443(5) Uani 1 1 d . . . . .
H19A H 0.2590 0.7955 0.3805 0.053 Uiso 1 1 calc R U . . .
C20A C 0.1313(2) 0.68469(19) 0.35149(14) 0.0484(6) Uani 1 1 d . . . . .
H20A H 0.0603 0.7383 0.3463 0.058 Uiso 1 1 calc R U . . .
C21A C 0.11679(19) 0.57307(18) 0.33858(13) 0.0409(5) Uani 1 1 d . . . . .
H21A H 0.0359 0.5506 0.3244 0.049 Uiso 1 1 calc R U . . .
C22A C 0.38996(17) 0.10639(16) 0.33479(11) 0.0302(4) Uani 1 1 d . . . . .
C23A C 0.39171(19) 0.00826(18) 0.40625(12) 0.0379(5) Uani 1 1 d . . . . .
H23A H 0.3220 -0.0041 0.4447 0.045 Uiso 1 1 calc R U . . .
C24A C 0.4940(2) -0.07237(19) 0.42244(14) 0.0459(5) Uani 1 1 d . . . . .
H24A H 0.4940 -0.1398 0.4715 0.055 Uiso 1 1 calc R U . . .
C25A C 0.5966(2) -0.0541(2) 0.36665(14) 0.0469(5) Uani 1 1 d . . . . .
H25A H 0.6672 -0.1088 0.3777 0.056 Uiso 1 1 calc R U . . .
C26A C 0.5958(2) 0.0433(2) 0.29533(14) 0.0456(5) Uani 1 1 d . . . . .
H26A H 0.6658 0.0557 0.2571 0.055 Uiso 1 1 calc R U . . .
C27A C 0.49321(19) 0.12336(18) 0.27920(13) 0.0389(5) Uani 1 1 d . . . . .
H27A H 0.4933 0.1903 0.2299 0.047 Uiso 1 1 calc R U . . .
O1B O 0.20567(11) 0.38816(11) 0.86935(7) 0.0291(3) Uani 1 1 d . . . . .
N1B N 0.32261(17) 0.11407(16) 1.01204(11) 0.0471(5) Uani 1 1 d . . . . .
C1B C 0.42747(17) 0.37202(16) 0.85732(11) 0.0293(4) Uani 1 1 d . . . . .
C2B C 0.55337(17) 0.38714(18) 0.84885(11) 0.0344(4) Uani 1 1 d . . . . .
H2B H 0.5877 0.4658 0.8432 0.041 Uiso 1 1 calc R U . . .
C3B C 0.64413(18) 0.28669(18) 0.84779(12) 0.0407(5) Uani 1 1 d . . . . .
H3C H 0.7024 0.2729 0.8935 0.049 Uiso 1 1 calc R U . . .
H3D H 0.6970 0.3142 0.7967 0.049 Uiso 1 1 calc R U . . .
C4B C 0.58052(19) 0.16471(18) 0.85434(13) 0.0438(5) Uani 1 1 d . . . . .
H4C H 0.5715 0.1140 0.9124 0.053 Uiso 1 1 calc R U . . .
H4D H 0.6362 0.1199 0.8263 0.053 Uiso 1 1 calc R U . . .
C5B C 0.44825(18) 0.18203(18) 0.81699(12) 0.0375(5) Uani 1 1 d . . . . .
H5C H 0.4565 0.2288 0.7582 0.045 Uiso 1 1 calc R U . . .
H5D H 0.4096 0.1011 0.8233 0.045 Uiso 1 1 calc R U . . .
C6B C 0.36313(17) 0.25167(16) 0.86021(11) 0.0297(4) Uani 1 1 d . . . . .
C7B C 0.22849(17) 0.30301(16) 0.82448(11) 0.0292(4) Uani 1 1 d . . . . .
C8B C 0.25341(16) 0.39146(16) 0.73835(11) 0.0288(4) Uani 1 1 d . . . . .
C9B C 0.23818(18) 0.38329(18) 0.66181(11) 0.0335(4) Uani 1 1 d . . . . .
H9B H 0.2013 0.3123 0.6549 0.040 Uiso 1 1 calc R U . . .
C10B C 0.27860(19) 0.48249(18) 0.59470(12) 0.0375(5) Uani 1 1 d . . . . .
H10B H 0.2679 0.4796 0.5414 0.045 Uiso 1 1 calc R U . . .
C11B C 0.33440(18) 0.58554(18) 0.60508(12) 0.0362(5) Uani 1 1 d . . . . .
H11B H 0.3623 0.6516 0.5587 0.043 Uiso 1 1 calc R U . . .
C12B C 0.34992(17) 0.59328(17) 0.68252(11) 0.0315(4) Uani 1 1 d . . . . .
H12B H 0.3882 0.6635 0.6897 0.038 Uiso 1 1 calc R U . . .
C13B C 0.30802(16) 0.49604(16) 0.74836(11) 0.0284(4) Uani 1 1 d . . . . .
C14B C 0.31861(17) 0.46663(16) 0.84033(11) 0.0291(4) Uani 1 1 d . . . . .
C15B C 0.33875(17) 0.17473(17) 0.94560(12) 0.0331(4) Uani 1 1 d . . . . .
C16B C 0.12356(17) 0.20890(16) 0.83995(11) 0.0295(4) Uani 1 1 d . . . . .
C17B C 0.02732(18) 0.20032(17) 0.89854(12) 0.0359(5) Uani 1 1 d . . . . .
H17B H 0.0254 0.2563 0.9284 0.043 Uiso 1 1 calc R U . . .
C18B C -0.06671(18) 0.10969(18) 0.91364(13) 0.0420(5) Uani 1 1 d . . . . .
H18B H -0.1321 0.1037 0.9542 0.050 Uiso 1 1 calc R U . . .
C19B C -0.0653(2) 0.02888(19) 0.87017(13) 0.0452(5) Uani 1 1 d . . . . .
H19B H -0.1300 -0.0323 0.8804 0.054 Uiso 1 1 calc R U . . .
C20B C 0.0300(2) 0.03684(19) 0.81178(13) 0.0442(5) Uani 1 1 d . . . . .
H20B H 0.0309 -0.0188 0.7816 0.053 Uiso 1 1 calc R U . . .
C21B C 0.12480(19) 0.12615(17) 0.79695(12) 0.0382(5) Uani 1 1 d . . . . .
H21B H 0.1909 0.1306 0.7571 0.046 Uiso 1 1 calc R U . . .
C22B C 0.31384(18) 0.57187(16) 0.87313(11) 0.0314(4) Uani 1 1 d . . . . .
C23B C 0.4156(2) 0.60579(19) 0.91068(12) 0.0401(5) Uani 1 1 d . . . . .
H23B H 0.4920 0.5588 0.9188 0.048 Uiso 1 1 calc R U . . .
C24B C 0.4063(2) 0.7078(2) 0.93638(13) 0.0512(6) Uani 1 1 d . . . . .
H24B H 0.4772 0.7311 0.9608 0.061 Uiso 1 1 calc R U . . .
C25B C 0.2958(3) 0.7754(2) 0.92697(13) 0.0527(6) Uani 1 1 d . . . . .
H25B H 0.2906 0.8460 0.9439 0.063 Uiso 1 1 calc R U . . .
C26B C 0.1917(2) 0.7396(2) 0.89249(14) 0.0519(6) Uani 1 1 d . . . . .
H26B H 0.1136 0.7836 0.8880 0.062 Uiso 1 1 calc R U . . .
C27B C 0.2015(2) 0.64016(19) 0.86471(13) 0.0432(5) Uani 1 1 d . . . . .
H27B H 0.1308 0.6180 0.8395 0.052 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
O1A C7A 1.456(2) . ?
O1A C14A 1.464(2) . ?
N1A C15A 1.142(2) . ?
C1A C2A 1.323(2) . ?
C1A C6A 1.527(2) . ?
C1A C14A 1.534(2) . ?
C2A C3A 1.505(3) . ?
C3A C4A 1.525(3) . ?
C4A C5A 1.533(2) . ?
C5A C6A 1.535(2) . ?
C6A C15A 1.478(3) . ?
C6A C7A 1.587(2) . ?
C7A C16A 1.498(2) . ?
C7A C8A 1.523(3) . ?
C8A C9A 1.387(3) . ?
C8A C13A 1.394(3) . ?
C9A C10A 1.398(3) . ?
C10A C11A 1.379(3) . ?
C11A C12A 1.400(3) . ?
C12A C13A 1.385(3) . ?
C13A C14A 1.531(3) . ?
C14A C22A 1.507(2) . ?
C16A C17A 1.391(3) . ?
C16A C21A 1.394(3) . ?
C17A C18A 1.387(3) . ?
C18A C19A 1.380(3) . ?
C19A C20A 1.388(3) . ?
C20A C21A 1.385(3) . ?
C22A C23A 1.383(3) . ?
C22A C27A 1.393(3) . ?
C23A C24A 1.387(3) . ?
C24A C25A 1.389(3) . ?
C25A C26A 1.377(3) . ?
C26A C27A 1.385(3) . ?
O1B C7B 1.451(2) . ?
O1B C14B 1.463(2) . ?
N1B C15B 1.147(2) . ?
C1B C2B 1.325(2) . ?
C1B C6B 1.530(2) . ?
C1B C14B 1.539(2) . ?
C2B C3B 1.495(3) . ?
C3B C4B 1.527(3) . ?
C4B C5B 1.534(3) . ?
C5B C6B 1.527(3) . ?
C6B C15B 1.476(3) . ?
C6B C7B 1.591(3) . ?
C7B C16B 1.502(2) . ?
C7B C8B 1.528(2) . ?
C8B C9B 1.379(3) . ?
C8B C13B 1.400(2) . ?
C9B C10B 1.397(3) . ?
C10B C11B 1.392(3) . ?
C11B C12B 1.394(3) . ?
C12B C13B 1.377(2) . ?
C13B C14B 1.532(2) . ?
C14B C22B 1.497(3) . ?
C16B C17B 1.386(3) . ?
C16B C21B 1.388(3) . ?
C17B C18B 1.394(3) . ?
C18B C19B 1.376(3) . ?
C19B C20B 1.378(3) . ?
C20B C21B 1.389(3) . ?
C22B C23B 1.391(3) . ?
C22B C27B 1.394(3) . ?
C23B C24B 1.387(3) . ?
C24B C25B 1.374(3) . ?
C25B C26B 1.389(3) . ?
C26B C27B 1.381(3) . ?

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
C7A O1A C14A 98.84(12) . . ?
C2A C1A C6A 123.04(17) . . ?
C2A C1A C14A 130.20(17) . . ?
C6A C1A C14A 105.04(14) . . ?
C1A C2A C3A 123.24(18) . . ?
C2A C3A C4A 113.79(16) . . ?
C3A C4A C5A 113.27(16) . . ?
C4A C5A C6A 108.80(15) . . ?
C15A C6A C1A 109.69(15) . . ?
C15A C6A C5A 109.48(15) . . ?
C1A C6A C5A 109.77(15) . . ?
C15A C6A C7A 106.93(14) . . ?
C1A C6A C7A 99.71(13) . . ?
C5A C6A C7A 120.64(15) . . ?
O1A C7A C16A 111.39(14) . . ?
O1A C7A C8A 100.84(13) . . ?
C16A C7A C8A 117.89(15) . . ?
O1A C7A C6A 97.84(13) . . ?
C16A C7A C6A 118.00(14) . . ?
C8A C7A C6A 107.73(14) . . ?
C9A C8A C13A 121.55(18) . . ?
C9A C8A C7A 132.35(17) . . ?
C13A C8A C7A 106.08(15) . . ?
C8A C9A C10A 117.36(19) . . ?
C11A C10A C9A 121.2(2) . . ?
C10A C11A C12A 121.3(2) . . ?
C13A C12A C11A 117.61(19) . . ?
C12A C13A C8A 120.89(18) . . ?
C12A C13A C14A 133.77(18) . . ?
C8A C13A C14A 105.12(15) . . ?
O1A C14A C22A 109.57(14) . . ?
O1A C14A C13A 99.68(13) . . ?
C22A C14A C13A 121.26(15) . . ?
O1A C14A C1A 101.36(13) . . ?
C22A C14A C1A 119.62(15) . . ?
C13A C14A C1A 101.96(14) . . ?
N1A C15A C6A 177.6(2) . . ?
C17A C16A C21A 118.82(17) . . ?
C17A C16A C7A 120.55(16) . . ?
C21A C16A C7A 120.57(17) . . ?
C18A C17A C16A 120.55(18) . . ?
C19A C18A C17A 120.37(19) . . ?
C18A C19A C20A 119.54(19) . . ?
C21A C20A C19A 120.3(2) . . ?
C20A C21A C16A 120.37(19) . . ?
C23A C22A C27A 118.85(18) . . ?
C23A C22A C14A 121.04(17) . . ?
C27A C22A C14A 119.90(17) . . ?
C22A C23A C24A 120.80(19) . . ?
C23A C24A C25A 119.8(2) . . ?
C26A C25A C24A 119.8(2) . . ?
C25A C26A C27A 120.2(2) . . ?
C26A C27A C22A 120.50(19) . . ?
C7B O1B C14B 98.77(12) . . ?
C2B C1B C6B 121.94(17) . . ?
C2B C1B C14B 130.80(17) . . ?
C6B C1B C14B 104.70(14) . . ?
C1B C2B C3B 123.32(18) . . ?
C2B C3B C4B 114.80(16) . . ?
C3B C4B C5B 112.37(16) . . ?
C6B C5B C4B 108.83(17) . . ?
C15B C6B C5B 109.46(15) . . ?
C15B C6B C1B 109.72(15) . . ?
C5B C6B C1B 110.41(15) . . ?
C15B C6B C7B 107.07(14) . . ?
C5B C6B C7B 119.91(16) . . ?
C1B C6B C7B 99.67(13) . . ?
O1B C7B C16B 112.07(14) . . ?
O1B C7B C8B 101.18(13) . . ?
C16B C7B C8B 119.34(15) . . ?
O1B C7B C6B 98.37(13) . . ?
C16B C7B C6B 115.35(14) . . ?
C8B C7B C6B 107.66(13) . . ?
C9B C8B C13B 120.89(17) . . ?
C9B C8B C7B 133.75(17) . . ?
C13B C8B C7B 105.28(15) . . ?
C8B C9B C10B 118.06(18) . . ?
C11B C10B C9B 120.78(18) . . ?
C10B C11B C12B 120.97(17) . . ?
C13B C12B C11B 117.95(17) . . ?
C12B C13B C8B 121.34(17) . . ?
C12B C13B C14B 132.88(16) . . ?
C8B C13B C14B 105.49(15) . . ?
O1B C14B C22B 110.10(14) . . ?
O1B C14B C13B 100.11(13) . . ?
C22B C14B C13B 117.59(15) . . ?
O1B C14B C1B 101.90(13) . . ?
C22B C14B C1B 123.15(16) . . ?
C13B C14B C1B 100.65(14) . . ?
N1B C15B C6B 178.5(2) . . ?
C17B C16B C21B 119.11(16) . . ?
C17B C16B C7B 121.12(16) . . ?
C21B C16B C7B 119.73(16) . . ?
C16B C17B C18B 120.09(19) . . ?
C19B C18B C17B 120.35(19) . . ?
C18B C19B C20B 119.92(18) . . ?
C19B C20B C21B 120.1(2) . . ?
C16B C21B C20B 120.46(19) . . ?
C23B C22B C27B 118.39(18) . . ?
C23B C22B C14B 123.58(17) . . ?
C27B C22B C14B 118.03(17) . . ?
C24B C23B C22B 120.4(2) . . ?
C25B C24B C23B 120.8(2) . . ?
C24B C25B C26B 119.3(2) . . ?
C27B C26B C25B 120.2(2) . . ?
C26B C27B C22B 120.9(2) . . ?

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
C6A C1A C2A C3A 0.2(3) . . . . ?
C14A C1A C2A C3A -162.52(19) . . . . ?
C1A C2A C3A C4A -2.9(3) . . . . ?
C2A C3A C4A C5A 32.8(3) . . . . ?
C3A C4A C5A C6A -58.9(2) . . . . ?
C2A C1A C6A C15A 93.7(2) . . . . ?
C14A C1A C6A C15A -99.91(16) . . . . ?
C2A C1A C6A C5A -26.7(2) . . . . ?
C14A C1A C6A C5A 139.77(15) . . . . ?
C2A C1A C6A C7A -154.31(18) . . . . ?
C14A C1A C6A C7A 12.11(17) . . . . ?
C4A C5A C6A C15A -66.6(2) . . . . ?
C4A C5A C6A C1A 53.8(2) . . . . ?
C4A C5A C6A C7A 168.75(17) . . . . ?
C14A O1A C7A C16A -175.60(14) . . . . ?
C14A O1A C7A C8A -49.69(14) . . . . ?
C14A O1A C7A C6A 60.15(14) . . . . ?
C15A C6A C7A O1A 70.48(15) . . . . ?
C1A C6A C7A O1A -43.68(15) . . . . ?
C5A C6A C7A O1A -163.69(16) . . . . ?
C15A C6A C7A C16A -48.9(2) . . . . ?
C1A C6A C7A C16A -163.03(15) . . . . ?
C5A C6A C7A C16A 77.0(2) . . . . ?
C15A C6A C7A C8A 174.56(14) . . . . ?
C1A C6A C7A C8A 60.40(17) . . . . ?
C5A C6A C7A C8A -59.6(2) . . . . ?
O1A C7A C8A C9A -152.76(19) . . . . ?
C16A C7A C8A C9A -31.3(3) . . . . ?
C6A C7A C8A C9A 105.3(2) . . . . ?
O1A C7A C8A C13A 28.54(16) . . . . ?
C16A C7A C8A C13A 149.98(15) . . . . ?
C6A C7A C8A C13A -73.41(17) . . . . ?
C13A C8A C9A C10A -2.2(3) . . . . ?
C7A C8A C9A C10A 179.26(18) . . . . ?
C8A C9A C10A C11A 2.1(3) . . . . ?
C9A C10A C11A C12A 0.0(3) . . . . ?
C10A C11A C12A C13A -1.9(3) . . . . ?
C11A C12A C13A C8A 1.8(3) . . . . ?
C11A C12A C13A C14A 175.68(19) . . . . ?
C9A C8A C13A C12A 0.3(3) . . . . ?
C7A C8A C13A C12A 179.17(16) . . . . ?
C9A C8A C13A C14A -175.15(16) . . . . ?
C7A C8A C13A C14A 3.72(18) . . . . ?
C7A O1A C14A C22A 179.98(14) . . . . ?
C7A O1A C14A C13A 51.71(14) . . . . ?
C7A O1A C14A C1A -52.69(15) . . . . ?
C12A C13A C14A O1A 150.95(19) . . . . ?
C8A C13A C14A O1A -34.46(16) . . . . ?
C12A C13A C14A C22A 30.9(3) . . . . ?
C8A C13A C14A C22A -154.53(15) . . . . ?
C12A C13A C14A C1A -105.1(2) . . . . ?
C8A C13A C14A C1A 69.45(16) . . . . ?
C2A C1A C14A O1A -171.62(19) . . . . ?
C6A C1A C14A O1A 23.31(17) . . . . ?
C2A C1A C14A C22A -51.1(3) . . . . ?
C6A C1A C14A C22A 143.79(16) . . . . ?
C2A C1A C14A C13A 85.8(2) . . . . ?
C6A C1A C14A C13A -79.27(16) . . . . ?
O1A C7A C16A C17A 9.5(2) . . . . ?
C8A C7A C16A C17A -106.3(2) . . . . ?
C6A C7A C16A C17A 121.52(18) . . . . ?
O1A C7A C16A C21A -173.32(16) . . . . ?
C8A C7A C16A C21A 70.8(2) . . . . ?
C6A C7A C16A C21A -61.3(2) . . . . ?
C21A C16A C17A C18A -0.6(3) . . . . ?
C7A C16A C17A C18A 176.63(16) . . . . ?
C16A C17A C18A C19A 0.4(3) . . . . ?
C17A C18A C19A C20A 0.1(3) . . . . ?
C18A C19A C20A C21A -0.4(3) . . . . ?
C19A C20A C21A C16A 0.3(3) . . . . ?
C17A C16A C21A C20A 0.2(3) . . . . ?
C7A C16A C21A C20A -176.96(18) . . . . ?
O1A C14A C22A C23A 90.48(19) . . . . ?
C13A C14A C22A C23A -154.40(17) . . . . ?
C1A C14A C22A C23A -25.8(2) . . . . ?
O1A C14A C22A C27A -84.3(2) . . . . ?
C13A C14A C22A C27A 30.9(2) . . . . ?
C1A C14A C22A C27A 159.48(17) . . . . ?
C27A C22A C23A C24A -0.2(3) . . . . ?
C14A C22A C23A C24A -175.01(18) . . . . ?
C22A C23A C24A C25A 0.5(3) . . . . ?
C23A C24A C25A C26A -0.5(3) . . . . ?
C24A C25A C26A C27A 0.2(3) . . . . ?
C25A C26A C27A C22A 0.0(3) . . . . ?
C23A C22A C27A C26A 0.0(3) . . . . ?
C14A C22A C27A C26A 174.81(18) . . . . ?
C6B C1B C2B C3B -4.8(3) . . . . ?
C14B C1B C2B C3B -163.77(18) . . . . ?
C1B C2B C3B C4B 2.0(3) . . . . ?
C2B C3B C4B C5B 30.2(2) . . . . ?
C3B C4B C5B C6B -58.6(2) . . . . ?
C4B C5B C6B C15B -66.31(19) . . . . ?
C4B C5B C6B C1B 54.59(19) . . . . ?
C4B C5B C6B C7B 169.47(15) . . . . ?
C2B C1B C6B C15B 96.2(2) . . . . ?
C14B C1B C6B C15B -100.18(16) . . . . ?
C2B C1B C6B C5B -24.6(2) . . . . ?
C14B C1B C6B C5B 139.09(15) . . . . ?
C2B C1B C6B C7B -151.66(17) . . . . ?
C14B C1B C6B C7B 11.99(16) . . . . ?
C14B O1B C7B C16B -178.54(14) . . . . ?
C14B O1B C7B C8B -50.29(15) . . . . ?
C14B O1B C7B C6B 59.68(14) . . . . ?
C15B C6B C7B O1B 70.69(16) . . . . ?
C5B C6B C7B O1B -163.94(15) . . . . ?
C1B C6B C7B O1B -43.54(14) . . . . ?
C15B C6B C7B C16B -48.6(2) . . . . ?
C5B C6B C7B C16B 76.7(2) . . . . ?
C1B C6B C7B C16B -162.88(15) . . . . ?
C15B C6B C7B C8B 175.32(14) . . . . ?
C5B C6B C7B C8B -59.3(2) . . . . ?
C1B C6B C7B C8B 61.09(16) . . . . ?
O1B C7B C8B C9B -153.08(19) . . . . ?
C16B C7B C8B C9B -29.7(3) . . . . ?
C6B C7B C8B C9B 104.3(2) . . . . ?
O1B C7B C8B C13B 30.23(17) . . . . ?
C16B C7B C8B C13B 153.64(16) . . . . ?
C6B C7B C8B C13B -72.39(17) . . . . ?
C13B C8B C9B C10B -0.1(3) . . . . ?
C7B C8B C9B C10B -176.40(18) . . . . ?
C8B C9B C10B C11B 1.0(3) . . . . ?
C9B C10B C11B C12B -0.9(3) . . . . ?
C10B C11B C12B C13B -0.2(3) . . . . ?
C11B C12B C13B C8B 1.1(3) . . . . ?
C11B C12B C13B C14B 173.94(18) . . . . ?
C9B C8B C13B C12B -0.9(3) . . . . ?
C7B C8B C13B C12B 176.29(16) . . . . ?
C9B C8B C13B C14B -175.51(16) . . . . ?
C7B C8B C13B C14B 1.70(17) . . . . ?
C7B O1B C14B C22B 175.45(14) . . . . ?
C7B O1B C14B C13B 50.96(15) . . . . ?
C7B O1B C14B C1B -52.30(15) . . . . ?
C12B C13B C14B O1B 153.62(19) . . . . ?
C8B C13B C14B O1B -32.69(17) . . . . ?
C12B C13B C14B C22B 34.5(3) . . . . ?
C8B C13B C14B C22B -151.84(16) . . . . ?
C12B C13B C14B C1B -102.1(2) . . . . ?
C8B C13B C14B C1B 71.59(16) . . . . ?
C2B C1B C14B O1B -175.28(19) . . . . ?
C6B C1B C14B O1B 23.11(17) . . . . ?
C2B C1B C14B C22B -51.4(3) . . . . ?
C6B C1B C14B C22B 146.97(16) . . . . ?
C2B C1B C14B C13B 81.9(2) . . . . ?
C6B C1B C14B C13B -79.73(15) . . . . ?
O1B C7B C16B C17B -7.3(2) . . . . ?
C8B C7B C16B C17B -125.17(19) . . . . ?
C6B C7B C16B C17B 104.2(2) . . . . ?
O1B C7B C16B C21B 174.91(16) . . . . ?
C8B C7B C16B C21B 57.0(2) . . . . ?
C6B C7B C16B C21B -73.6(2) . . . . ?
C21B C16B C17B C18B -0.1(3) . . . . ?
C7B C16B C17B C18B -177.92(18) . . . . ?
C16B C17B C18B C19B -0.5(3) . . . . ?
C17B C18B C19B C20B 0.5(3) . . . . ?
C18B C19B C20B C21B 0.2(3) . . . . ?
C17B C16B C21B C20B 0.7(3) . . . . ?
C7B C16B C21B C20B 178.61(18) . . . . ?
C19B C20B C21B C16B -0.8(3) . . . . ?
O1B C14B C22B C23B 130.74(18) . . . . ?
C13B C14B C22B C23B -115.5(2) . . . . ?
C1B C14B C22B C23B 10.6(3) . . . . ?
O1B C14B C22B C27B -49.9(2) . . . . ?
C13B C14B C22B C27B 63.8(2) . . . . ?
C1B C14B C22B C27B -170.04(16) . . . . ?
C27B C22B C23B C24B -2.2(3) . . . . ?
C14B C22B C23B C24B 177.11(18) . . . . ?
C22B C23B C24B C25B 1.5(3) . . . . ?
C23B C24B C25B C26B 1.1(3) . . . . ?
C24B C25B C26B C27B -2.9(3) . . . . ?
C25B C26B C27B C22B 2.1(3) . . . . ?
C23B C22B C27B C26B 0.4(3) . . . . ?
C14B C22B C27B C26B -178.94(18) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049

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

data_fgw1903
_database_code_depnum_ccdc_archive 'CCDC 2017584'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 N O2'
_chemical_formula_sum            'C23 H29 N O2'
_chemical_formula_weight         351.47

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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.4338(3)
_cell_length_b                   8.3344(2)
_cell_length_c                   16.0463(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.5183(8)
_cell_angle_gamma                90
_cell_volume                     1933.12(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9802
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      74.17

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.259
_exptl_absorpt_coefficient_mu    0.593
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7950
_exptl_absorpt_correction_T_max  0.9621
_exptl_absorpt_process_details   'SADABS (version 2016/2)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            66578
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         74.967
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3902
_reflns_number_gt                3560
_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    'SHELXT (version 2014/5)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0673P)²+0.4530P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3902
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71104(5) 0.37267(10) 0.68193(5) 0.0344(2) Uani 1 1 d . . . . .
O2 O 0.53163(9) -0.12043(17) 0.69359(9) 0.0693(4) Uani 1 1 d . . . . .
N N 0.64683(7) 0.11503(13) 0.65666(7) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.78813(8) 0.34536(14) 0.75709(7) 0.0313(3) Uani 1 1 d . . . . .
C2 C 0.84835(8) 0.22543(14) 0.76283(7) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.92586(8) 0.18042(16) 0.84794(8) 0.0359(3) Uani 1 1 d . . . . .
H3A H 0.911935 0.221683 0.899722 0.043 Uiso 1 1 calc R U . . .
H3B H 0.984375 0.230072 0.848608 0.043 Uiso 1 1 calc R U . . .
C4 C 0.93700(10) -0.00132(17) 0.85492(9) 0.0436(3) Uani 1 1 d . . . . .
H4A H 0.988509 -0.029007 0.910321 0.052 Uiso 1 1 calc R U . . .
H4B H 0.879726 -0.050090 0.858032 0.052 Uiso 1 1 calc R U . . .
C5 C 0.95663(11) -0.0698(2) 0.77551(9) 0.0513(4) Uani 1 1 d . . . . .
H5A H 1.020473 -0.041585 0.780163 0.062 Uiso 1 1 calc R U . . .
H5B H 0.951860 -0.188206 0.775799 0.062 Uiso 1 1 calc R U . . .
C6 C 0.88951(9) -0.00518(17) 0.68988(9) 0.0410(3) Uani 1 1 d . . . . .
H6 H 0.882825 -0.061025 0.636365 0.049 Uiso 1 1 calc R U . . .
C7 C 0.83861(8) 0.12677(15) 0.68487(8) 0.0322(3) Uani 1 1 d . . . . .
C8 C 0.76949(8) 0.18703(14) 0.59835(8) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.7525(9) 0.0988(17) 0.5553(9) 0.032(3) Uiso 1 1 d . . . . .
C9 C 0.80872(9) 0.32148(17) 0.55623(8) 0.0397(3) Uani 1 1 d . . . . .
H9A H 0.831494 0.410015 0.599556 0.048 Uiso 1 1 calc R U . . .
H9B H 0.861746 0.279582 0.541682 0.048 Uiso 1 1 calc R U . . .
C10 C 0.73538(10) 0.38577(17) 0.47183(9) 0.0443(3) Uani 1 1 d . . . . .
H10A H 0.762351 0.471730 0.445949 0.053 Uiso 1 1 calc R U . . .
H10B H 0.714138 0.298513 0.427430 0.053 Uiso 1 1 calc R U . . .
C11 C 0.65370(11) 0.45178(17) 0.49318(9) 0.0472(3) Uani 1 1 d . . . . .
H11A H 0.605976 0.491397 0.437913 0.057 Uiso 1 1 calc R U . . .
H11B H 0.674382 0.543267 0.534817 0.057 Uiso 1 1 calc R U . . .
C12 C 0.61212(9) 0.32224(17) 0.53497(8) 0.0408(3) Uani 1 1 d . . . . .
H12A H 0.583924 0.238216 0.490014 0.049 Uiso 1 1 calc R U . . .
H12B H 0.562306 0.370314 0.552375 0.049 Uiso 1 1 calc R U . . .
C13 C 0.68338(8) 0.24444(14) 0.61675(8) 0.0325(3) Uani 1 1 d . . . . .
C21 C 0.79393(8) 0.46500(14) 0.82682(8) 0.0335(3) Uani 1 1 d . . . . .
C22 C 0.71454(10) 0.51525(16) 0.84195(9) 0.0411(3) Uani 1 1 d . . . . .
H22 H 0.656065 0.472472 0.806844 0.049 Uiso 1 1 calc R U . . .
C23 C 0.71993(12) 0.62699(18) 0.90769(10) 0.0509(4) Uani 1 1 d . . . . .
H23 H 0.665197 0.660810 0.916915 0.061 Uiso 1 1 calc R U . . .
C24 C 0.80441(12) 0.68916(16) 0.95970(9) 0.0516(4) Uani 1 1 d . . . . .
H24 H 0.808146 0.764063 1.005457 0.062 Uiso 1 1 calc R U . . .
C25 C 0.88332(12) 0.64203(17) 0.94491(9) 0.0500(4) Uani 1 1 d . . . . .
H25 H 0.941520 0.685228 0.980449 0.060 Uiso 1 1 calc R U . . .
C26 C 0.87858(10) 0.53197(16) 0.87855(9) 0.0423(3) Uani 1 1 d . . . . .
H26 H 0.933365 0.501997 0.868263 0.051 Uiso 1 1 calc R U . . .
C31 C 0.63129(10) -0.04054(16) 0.61192(9) 0.0424(3) Uani 1 1 d . . . . .
H31A H 0.687249 -0.073151 0.599509 0.051 Uiso 1 1 calc R U . . .
H31B H 0.579176 -0.032634 0.554524 0.051 Uiso 1 1 calc R U . . .
C32 C 0.60945(13) -0.1643(2) 0.67040(13) 0.0620(4) Uani 1 1 d . . . . .
H32A H 0.596963 -0.268553 0.638876 0.074 Uiso 1 1 calc R U . . .
H32B H 0.663981 -0.177973 0.725425 0.074 Uiso 1 1 calc R U . . .
C33 C 0.54912(12) 0.0305(3) 0.73736(11) 0.0661(5) Uani 1 1 d . . . . .
H33A H 0.604215 0.022045 0.792324 0.079 Uiso 1 1 calc R U . . .
H33B H 0.495682 0.061024 0.754519 0.079 Uiso 1 1 calc R U . . .
C34 C 0.56526(10) 0.1582(2) 0.67802(10) 0.0510(4) Uani 1 1 d . . . . .
H34A H 0.510609 0.166859 0.622690 0.061 Uiso 1 1 calc R U . . .
H34B H 0.575020 0.263268 0.708693 0.061 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3842(14) . ?
O1 C13 1.4510(14) . ?
O2 C33 1.420(2) . ?
O2 C32 1.424(2) . ?
N C31 1.4606(17) . ?
N C34 1.4608(17) . ?
N C13 1.4646(16) . ?
C1 C2 1.3458(17) . ?
C1 C21 1.4778(16) . ?
C2 C7 1.4601(16) . ?
C2 C3 1.5139(15) . ?
C3 C4 1.5241(19) . ?
C4 C5 1.5203(19) . ?
C5 C6 1.5011(19) . ?
C6 C7 1.3375(18) . ?
C7 C8 1.5097(16) . ?
C8 C13 1.5354(16) . ?
C8 C9 1.5381(17) . ?
C9 C10 1.5258(18) . ?
C10 C11 1.521(2) . ?
C11 C12 1.526(2) . ?
C12 C13 1.5299(16) . ?
C21 C22 1.3944(18) . ?
C21 C26 1.3954(18) . ?
C22 C23 1.3876(19) . ?
C23 C24 1.379(2) . ?
C24 C25 1.377(2) . ?
C25 C26 1.3878(19) . ?
C31 C32 1.510(2) . ?
C33 C34 1.506(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C13 116.92(9) . . ?
C33 O2 C32 108.97(12) . . ?
C31 N C34 109.11(10) . . ?
C31 N C13 117.44(10) . . ?
C34 N C13 114.65(11) . . ?
C2 C1 O1 122.94(10) . . ?
C2 C1 C21 126.32(11) . . ?
O1 C1 C21 110.74(10) . . ?
C1 C2 C7 119.90(10) . . ?
C1 C2 C3 123.65(11) . . ?
C7 C2 C3 116.41(10) . . ?
C2 C3 C4 110.22(10) . . ?
C5 C4 C3 111.21(12) . . ?
C6 C5 C4 110.88(11) . . ?
C7 C6 C5 123.52(12) . . ?
C6 C7 C2 121.99(11) . . ?
C6 C7 C8 122.65(11) . . ?
C2 C7 C8 115.33(10) . . ?
C7 C8 C13 107.88(9) . . ?
C7 C8 C9 112.73(10) . . ?
C13 C8 C9 110.98(10) . . ?
C10 C9 C8 111.23(10) . . ?
C11 C10 C9 110.04(11) . . ?
C10 C11 C12 110.65(11) . . ?
C11 C12 C13 112.96(11) . . ?
O1 C13 N 106.75(9) . . ?
O1 C13 C12 104.33(9) . . ?
N C13 C12 114.57(10) . . ?
O1 C13 C8 108.20(9) . . ?
N C13 C8 110.28(10) . . ?
C12 C13 C8 112.19(10) . . ?
C22 C21 C26 118.22(12) . . ?
C22 C21 C1 120.72(11) . . ?
C26 C21 C1 121.06(11) . . ?
C23 C22 C21 120.78(13) . . ?
C24 C23 C22 120.28(14) . . ?
C25 C24 C23 119.62(13) . . ?
C24 C25 C26 120.58(14) . . ?
C25 C26 C21 120.49(14) . . ?
N C31 C32 109.56(12) . . ?
O2 C32 C31 112.31(14) . . ?
O2 C33 C34 110.99(13) . . ?
N C34 C33 108.76(14) . . ?

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
C13 O1 C1 C2 15.13(16) . . . . ?
C13 O1 C1 C21 -165.38(9) . . . . ?
O1 C1 C2 C7 5.80(18) . . . . ?
C21 C1 C2 C7 -173.61(11) . . . . ?
O1 C1 C2 C3 -171.87(10) . . . . ?
C21 C1 C2 C3 8.72(19) . . . . ?
C1 C2 C3 C4 141.23(12) . . . . ?
C7 C2 C3 C4 -36.51(14) . . . . ?
C2 C3 C4 C5 58.16(15) . . . . ?
C3 C4 C5 C6 -48.56(17) . . . . ?
C4 C5 C6 C7 18.1(2) . . . . ?
C5 C6 C7 C2 3.7(2) . . . . ?
C5 C6 C7 C8 -178.21(13) . . . . ?
C1 C2 C7 C6 -171.78(12) . . . . ?
C3 C2 C7 C6 6.05(17) . . . . ?
C1 C2 C7 C8 10.02(16) . . . . ?
C3 C2 C7 C8 -172.15(10) . . . . ?
C6 C7 C8 C13 139.45(12) . . . . ?
C2 C7 C8 C13 -42.37(13) . . . . ?
C6 C7 C8 C9 -97.66(14) . . . . ?
C2 C7 C8 C9 80.52(13) . . . . ?
C7 C8 C9 C10 -176.78(10) . . . . ?
C13 C8 C9 C10 -55.64(13) . . . . ?
C8 C9 C10 C11 59.48(15) . . . . ?
C9 C10 C11 C12 -58.15(15) . . . . ?
C10 C11 C12 C13 54.43(15) . . . . ?
C1 O1 C13 N 70.33(12) . . . . ?
C1 O1 C13 C12 -167.99(10) . . . . ?
C1 O1 C13 C8 -48.36(13) . . . . ?
C31 N C13 O1 -168.06(10) . . . . ?
C34 N C13 O1 61.84(12) . . . . ?
C31 N C13 C12 76.98(14) . . . . ?
C34 N C13 C12 -53.12(14) . . . . ?
C31 N C13 C8 -50.74(13) . . . . ?
C34 N C13 C8 179.17(10) . . . . ?
C11 C12 C13 O1 65.94(13) . . . . ?
C11 C12 C13 N -177.70(10) . . . . ?
C11 C12 C13 C8 -50.96(14) . . . . ?
C7 C8 C13 O1 60.27(12) . . . . ?
C9 C8 C13 O1 -63.68(12) . . . . ?
C7 C8 C13 N -56.15(12) . . . . ?
C9 C8 C13 N 179.89(9) . . . . ?
C7 C8 C13 C12 174.83(10) . . . . ?
C9 C8 C13 C12 50.87(13) . . . . ?
C2 C1 C21 C22 -140.76(13) . . . . ?
O1 C1 C21 C22 39.77(15) . . . . ?
C2 C1 C21 C26 39.94(18) . . . . ?
O1 C1 C21 C26 -139.53(12) . . . . ?
C26 C21 C22 C23 -1.00(19) . . . . ?
C1 C21 C22 C23 179.68(12) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C25 1.2(2) . . . . ?
C23 C24 C25 C26 -0.4(2) . . . . ?
C24 C25 C26 C21 -1.2(2) . . . . ?
C22 C21 C26 C25 1.86(19) . . . . ?
C1 C21 C26 C25 -178.82(12) . . . . ?
C34 N C31 C32 -56.93(15) . . . . ?
C13 N C31 C32 170.44(12) . . . . ?
C33 O2 C32 C31 -57.80(19) . . . . ?
N C31 C32 O2 56.98(17) . . . . ?
C32 O2 C33 C34 59.97(19) . . . . ?
C31 N C34 C33 59.30(14) . . . . ?
C13 N C34 C33 -166.63(11) . . . . ?
O2 C33 C34 N -61.69(17) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Et2O, EtOAc'
