# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_db14
_database_code_depnum_ccdc_archive 'CCDC 2335536'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-02-26 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H13 N O2'
_chemical_formula_sum            'C20 H13 N O2'
_chemical_formula_weight         299.31

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   11.1186(11)
_cell_length_b                   33.698(4)
_cell_length_c                   3.8243(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1432.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3692
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      26.0

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.386
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5933
_diffrn_reflns_av_unetI/netI     0.1813
_diffrn_reflns_av_R_equivalents  0.1671
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.535
_diffrn_reflns_theta_max         25.763
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2681
_reflns_number_gt                1502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.956
_reflns_Friedel_fraction_full    0.990

_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+17.8335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
; 
 Flack x determined using 306 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2681
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2692
_refine_ls_R_factor_gt           0.1555
_refine_ls_wR_factor_ref         0.3433
_refine_ls_wR_factor_gt          0.2843
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.226
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3057(14) 0.5851(4) 0.446(4) 0.037(4) Uani 1 1 d . . . . .
O1 O 0.2002(9) 0.3565(3) 0.403(3) 0.027(3) Uani 1 1 d . . . . .
O2 O 0.4648(9) 0.3176(3) 0.796(4) 0.040(4) Uani 1 1 d . . . . .
C1 C 0.3142(13) 0.3622(5) 0.568(4) 0.020(4) Uani 1 1 d . . . . .
C2 C 0.3688(15) 0.3228(5) 0.640(5) 0.028(4) Uani 1 1 d . . . . .
C3 C 0.2833(14) 0.2944(4) 0.509(4) 0.023(4) Uani 1 1 d . . . . .
C4 C 0.2801(15) 0.2528(5) 0.494(5) 0.031(4) Uani 1 1 d . . . . .
H4 H 0.345453 0.237469 0.580181 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1815(15) 0.2347(5) 0.354(6) 0.034(5) Uani 1 1 d . . . . .
H5 H 0.177334 0.206579 0.351795 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0846(15) 0.2571(5) 0.210(5) 0.038(5) Uani 1 1 d . . . . .
H6 H 0.019124 0.243883 0.101076 0.046 Uiso 1 1 calc R U . . .
C7 C 0.0860(14) 0.2981(5) 0.229(5) 0.032(4) Uani 1 1 d . . . . .
H7 H 0.020444 0.313591 0.146999 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1854(14) 0.3150(4) 0.370(4) 0.022(4) Uani 1 1 d . . . . .
C9 C 0.3572(15) 0.3982(5) 0.648(4) 0.028(4) Uani 1 1 d . . . . .
H9 H 0.432584 0.397306 0.765089 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3127(16) 0.4382(5) 0.595(5) 0.032(4) Uani 1 1 d . . . . .
C12 C 0.3824(14) 0.4691(5) 0.726(4) 0.025(4) Uani 1 1 d . . . . .
H12 H 0.455467 0.463437 0.844868 0.030 Uiso 1 1 calc R U . . .
C13 C 0.3456(14) 0.5078(5) 0.684(5) 0.027(4) Uani 1 1 d . . . . .
H13 H 0.393300 0.528605 0.778061 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2430(14) 0.5170(5) 0.511(4) 0.024(4) Uani 1 1 d . . . . .
C15 C 0.1674(13) 0.4861(4) 0.392(5) 0.025(4) Uani 1 1 d . . . . .
H15 H 0.092640 0.492170 0.283847 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2035(13) 0.4464(4) 0.433(5) 0.022(4) Uani 1 1 d . . . . .
H16 H 0.153794 0.425425 0.351870 0.027 Uiso 1 1 calc R U . . .
C21 C 0.2117(14) 0.5592(5) 0.439(4) 0.022(4) Uani 1 1 d . . . . .
C22 C 0.0958(14) 0.5710(5) 0.364(5) 0.029(4) Uani 1 1 d . . . . .
H22 H 0.032020 0.552287 0.371504 0.035 Uiso 1 1 calc R U . . .
C23 C 0.0721(18) 0.6101(6) 0.279(6) 0.049(6) Uani 1 1 d . . . . .
H23 H -0.006839 0.618402 0.218066 0.059 Uiso 1 1 calc R U . . .
C24 C 0.1675(18) 0.6372(5) 0.284(5) 0.037(5) Uani 1 1 d . . . . .
H24 H 0.154384 0.664335 0.228914 0.045 Uiso 1 1 calc R U . . .
C25 C 0.2829(17) 0.6235(5) 0.371(7) 0.048(6) Uani 1 1 d . . . . .
H25 H 0.347418 0.641955 0.377249 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C25 1.35(2) . ?
N1 C21 1.361(19) . ?
O1 C8 1.415(17) . ?
O1 C1 1.429(17) . ?
O2 C2 1.236(19) . ?
C1 C9 1.34(2) . ?
C1 C2 1.48(2) . ?
C2 C3 1.44(2) . ?
C3 C8 1.40(2) . ?
C3 C4 1.40(2) . ?
C4 C5 1.36(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.43(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.38(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.36(2) . ?
C7 H7 0.9500 . ?
C9 C11 1.45(2) . ?
C9 H9 0.9500 . ?
C11 C16 1.39(2) . ?
C11 C12 1.39(2) . ?
C12 C13 1.38(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.35(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.41(2) . ?
C14 C21 1.49(2) . ?
C15 C16 1.41(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.38(2) . ?
C22 C23 1.38(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.40(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.40(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 N1 C21 117.8(16) . . ?
C8 O1 C1 105.9(12) . . ?
C9 C1 O1 122.6(13) . . ?
C9 C1 C2 128.4(13) . . ?
O1 C1 C2 109.0(13) . . ?
O2 C2 C3 130.0(16) . . ?
O2 C2 C1 124.8(15) . . ?
C3 C2 C1 105.1(13) . . ?
C8 C3 C4 117.4(15) . . ?
C8 C3 C2 108.5(13) . . ?
C4 C3 C2 134.1(15) . . ?
C5 C4 C3 118.8(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.6(15) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 120.0(16) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 116.7(16) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C8 C3 125.4(13) . . ?
C7 C8 O1 123.1(14) . . ?
C3 C8 O1 111.5(13) . . ?
C1 C9 C11 133.4(16) . . ?
C1 C9 H9 113.3 . . ?
C11 C9 H9 113.3 . . ?
C16 C11 C12 119.9(16) . . ?
C16 C11 C9 123.0(15) . . ?
C12 C11 C9 117.0(16) . . ?
C13 C12 C11 120.0(16) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 121.6(16) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.4(15) . . ?
C13 C14 C21 120.3(15) . . ?
C15 C14 C21 120.3(14) . . ?
C16 C15 C14 119.6(14) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C11 C16 C15 119.2(15) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N1 C21 C22 122.5(15) . . ?
N1 C21 C14 115.4(14) . . ?
C22 C21 C14 122.2(14) . . ?
C21 C22 C23 120.1(17) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 118.3(18) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C23 C24 C25 118.8(16) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
N1 C25 C24 122.5(16) . . ?
N1 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?

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 O1 C1 C9 -178.5(16) . . . . ?
C8 O1 C1 C2 -0.6(16) . . . . ?
C9 C1 C2 O2 1(3) . . . . ?
O1 C1 C2 O2 -176.4(17) . . . . ?
C9 C1 C2 C3 178.1(17) . . . . ?
O1 C1 C2 C3 0.4(18) . . . . ?
O2 C2 C3 C8 176.5(19) . . . . ?
C1 C2 C3 C8 -0.1(19) . . . . ?
O2 C2 C3 C4 -4(4) . . . . ?
C1 C2 C3 C4 179.7(18) . . . . ?
C8 C3 C4 C5 -1(3) . . . . ?
C2 C3 C4 C5 179(2) . . . . ?
C3 C4 C5 C6 3(3) . . . . ?
C4 C5 C6 C7 -4(3) . . . . ?
C5 C6 C7 C8 4(3) . . . . ?
C6 C7 C8 C3 -3(3) . . . . ?
C6 C7 C8 O1 179.2(16) . . . . ?
C4 C3 C8 C7 2(3) . . . . ?
C2 C3 C8 C7 -178.6(18) . . . . ?
C4 C3 C8 O1 179.8(15) . . . . ?
C2 C3 C8 O1 0(2) . . . . ?
C1 O1 C8 C7 178.9(17) . . . . ?
C1 O1 C8 C3 0.6(17) . . . . ?
O1 C1 C9 C11 -2(3) . . . . ?
C2 C1 C9 C11 -179.6(18) . . . . ?
C1 C9 C11 C16 1(3) . . . . ?
C1 C9 C11 C12 178.3(18) . . . . ?
C16 C11 C12 C13 -3(3) . . . . ?
C9 C11 C12 C13 179.9(16) . . . . ?
C11 C12 C13 C14 -1(3) . . . . ?
C12 C13 C14 C15 4(3) . . . . ?
C12 C13 C14 C21 -174.1(16) . . . . ?
C13 C14 C15 C16 -4(3) . . . . ?
C21 C14 C15 C16 174.3(16) . . . . ?
C12 C11 C16 C15 3(3) . . . . ?
C9 C11 C16 C15 -179.9(18) . . . . ?
C14 C15 C16 C11 1(3) . . . . ?
C25 N1 C21 C22 -1(3) . . . . ?
C25 N1 C21 C14 177.8(19) . . . . ?
C13 C14 C21 N1 22(2) . . . . ?
C15 C14 C21 N1 -156.9(16) . . . . ?
C13 C14 C21 C22 -159.8(16) . . . . ?
C15 C14 C21 C22 22(2) . . . . ?
N1 C21 C22 C23 2(3) . . . . ?
C14 C21 C22 C23 -176.0(18) . . . . ?
C21 C22 C23 C24 -2(3) . . . . ?
C22 C23 C24 C25 1(3) . . . . ?
C21 N1 C25 C24 -1(3) . . . . ?
C23 C24 C25 N1 1(3) . . . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.112

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

data_db8
_database_code_depnum_ccdc_archive 'CCDC 2335537'
loop_
_audit_author_name
_audit_author_address
'Michael Bolte'
;Goethe University Frankfurt
Germany
;
_audit_update_record             
;
2024-02-26 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38

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                   8.6748(8)
_cell_length_b                   16.7658(12)
_cell_length_c                   11.7777(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.695(8)
_cell_angle_gamma                90
_cell_volume                     1693.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6966
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      25.88

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6966
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.382
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2967
_reflns_number_gt                2209
_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       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
_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)+2.3747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         2967
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.0979
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   1.392
_refine_ls_restrained_S_all      1.392
_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 0.7467(3) 0.45667(16) 0.5082(2) 0.0298(7) Uani 1 1 d . . . . .
O2 O 0.5401(3) 0.27790(17) 0.5352(3) 0.0399(8) Uani 1 1 d . . . . .
O3 O 0.2816(3) 0.41481(17) 0.1965(2) 0.0389(8) Uani 1 1 d . . . . .
N1 N 0.4115(4) 0.6731(2) 0.0606(3) 0.0351(9) Uani 1 1 d . . . . .
C1 C 0.6212(4) 0.4054(2) 0.4704(3) 0.0270(9) Uani 1 1 d . . . . .
C2 C 0.6302(4) 0.3349(2) 0.5450(3) 0.0271(9) Uani 1 1 d . . . . .
C3 C 0.7695(4) 0.3487(2) 0.6298(3) 0.0257(9) Uani 1 1 d . . . . .
C4 C 0.8422(5) 0.3046(2) 0.7240(3) 0.0308(9) Uani 1 1 d . . . . .
H4 H 0.800934 0.254761 0.743162 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9752(5) 0.3352(3) 0.7881(4) 0.0351(10) Uani 1 1 d . . . . .
H5 H 1.026420 0.306617 0.852583 0.042 Uiso 1 1 calc R U . . .
C6 C 1.0343(5) 0.4085(3) 0.7581(4) 0.0391(11) Uani 1 1 d . . . . .
H6 H 1.126101 0.428689 0.803186 0.047 Uiso 1 1 calc R U . . .
C7 C 0.9650(4) 0.4526(3) 0.6658(4) 0.0378(11) Uani 1 1 d . . . . .
H7 H 1.006698 0.502266 0.646130 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8319(4) 0.4209(2) 0.6034(3) 0.0280(9) Uani 1 1 d . . . . .
C9 C 0.5124(5) 0.4201(2) 0.3806(3) 0.0297(9) Uani 1 1 d . . . . .
H9 H 0.435453 0.379542 0.366002 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4896(4) 0.4857(2) 0.3015(3) 0.0260(9) Uani 1 1 d . . . . .
C12 C 0.3702(4) 0.4827(2) 0.2059(3) 0.0280(9) Uani 1 1 d . . . . .
C13 C 0.3455(4) 0.5432(2) 0.1266(3) 0.0287(9) Uani 1 1 d . . . . .
H13 H 0.264543 0.538399 0.062961 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4394(4) 0.6125(2) 0.1386(3) 0.0289(9) Uani 1 1 d . . . . .
C15 C 0.5599(4) 0.6157(2) 0.2325(3) 0.0315(10) Uani 1 1 d . . . . .
H15 H 0.626725 0.660850 0.242243 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5826(4) 0.5544(2) 0.3102(3) 0.0295(9) Uani 1 1 d . . . . .
H16 H 0.665073 0.558734 0.372930 0.035 Uiso 1 1 calc R U . . .
C17 C 0.1666(6) 0.4054(3) 0.0974(4) 0.0534(14) Uani 1 1 d . . . . .
H17A H 0.088763 0.447961 0.095488 0.080 Uiso 1 1 calc R U . . .
H17B H 0.115517 0.353504 0.100373 0.080 Uiso 1 1 calc R U . . .
H17C H 0.216469 0.408383 0.028201 0.080 Uiso 1 1 calc R U . . .
C18 C 0.2768(5) 0.6726(3) -0.0306(4) 0.0376(11) Uani 1 1 d . . . . .
H18A H 0.248061 0.728240 -0.052517 0.045 Uiso 1 1 calc R U . . .
H18B H 0.187155 0.647771 -0.001166 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3090(6) 0.6273(3) -0.1362(4) 0.0599(15) Uani 1 1 d . . . . .
H19A H 0.216021 0.628490 -0.194841 0.090 Uiso 1 1 calc R U . . .
H19B H 0.396393 0.652310 -0.166584 0.090 Uiso 1 1 calc R U . . .
H19C H 0.335494 0.571851 -0.115239 0.090 Uiso 1 1 calc R U . . .
C20 C 0.5181(5) 0.7403(3) 0.0584(4) 0.0440(12) Uani 1 1 d . . . . .
H20A H 0.520344 0.755683 -0.022509 0.053 Uiso 1 1 calc R U . . .
H20B H 0.624529 0.723041 0.091646 0.053 Uiso 1 1 calc R U . . .
C21 C 0.4748(7) 0.8114(3) 0.1227(5) 0.0673(16) Uani 1 1 d . . . . .
H21A H 0.550570 0.854179 0.117965 0.101 Uiso 1 1 calc R U . . .
H21B H 0.370568 0.829737 0.089158 0.101 Uiso 1 1 calc R U . . .
H21C H 0.474845 0.797067 0.203413 0.101 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 C8 1.383(5) . ?
O1 C1 1.406(4) . ?
O2 C2 1.229(5) . ?
O3 C12 1.369(5) . ?
O3 C17 1.425(5) . ?
N1 C14 1.367(5) . ?
N1 C20 1.460(5) . ?
N1 C18 1.462(5) . ?
C1 C9 1.329(5) . ?
C1 C2 1.468(5) . ?
C2 C3 1.465(5) . ?
C3 C8 1.381(5) . ?
C3 C4 1.401(5) . ?
C4 C5 1.379(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(5) . ?
C7 H7 0.9500 . ?
C9 C11 1.437(5) . ?
C9 H9 0.9500 . ?
C11 C16 1.401(5) . ?
C11 C12 1.411(5) . ?
C12 C13 1.373(5) . ?
C13 C14 1.414(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.403(5) . ?
C15 C16 1.370(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.519(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.492(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C1 106.6(3) . . ?
C12 O3 C17 118.2(3) . . ?
C14 N1 C20 122.5(3) . . ?
C14 N1 C18 122.0(4) . . ?
C20 N1 C18 115.4(3) . . ?
C9 C1 O1 124.2(4) . . ?
C9 C1 C2 126.3(4) . . ?
O1 C1 C2 109.5(3) . . ?
O2 C2 C3 129.3(4) . . ?
O2 C2 C1 126.5(4) . . ?
C3 C2 C1 104.2(3) . . ?
C8 C3 C4 119.7(4) . . ?
C8 C3 C2 107.2(3) . . ?
C4 C3 C2 133.1(4) . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 122.6(4) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C8 116.4(4) . . ?
C6 C7 H7 121.8 . . ?
C8 C7 H7 121.8 . . ?
C7 C8 C3 122.9(4) . . ?
C7 C8 O1 124.5(4) . . ?
C3 C8 O1 112.5(3) . . ?
C1 C9 C11 132.0(4) . . ?
C1 C9 H9 114.0 . . ?
C11 C9 H9 114.0 . . ?
C16 C11 C12 115.7(4) . . ?
C16 C11 C9 124.1(3) . . ?
C12 C11 C9 120.2(4) . . ?
O3 C12 C13 122.1(3) . . ?
O3 C12 C11 115.5(3) . . ?
C13 C12 C11 122.4(4) . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
N1 C14 C15 122.5(4) . . ?
N1 C14 C13 120.2(3) . . ?
C15 C14 C13 117.3(4) . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 122.9(4) . . ?
C15 C16 H16 118.5 . . ?
C11 C16 H16 118.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 112.3(4) . . ?
N1 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 113.5(4) . . ?
N1 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
N1 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 C1 C9 179.5(4) . . . . ?
C8 O1 C1 C2 -0.4(4) . . . . ?
C9 C1 C2 O2 1.2(7) . . . . ?
O1 C1 C2 O2 -178.9(4) . . . . ?
C9 C1 C2 C3 -179.6(4) . . . . ?
O1 C1 C2 C3 0.4(4) . . . . ?
O2 C2 C3 C8 179.1(4) . . . . ?
C1 C2 C3 C8 -0.2(4) . . . . ?
O2 C2 C3 C4 -0.8(8) . . . . ?
C1 C2 C3 C4 179.9(4) . . . . ?
C8 C3 C4 C5 0.2(6) . . . . ?
C2 C3 C4 C5 -179.9(4) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 0.2(7) . . . . ?
C6 C7 C8 C3 -0.3(6) . . . . ?
C6 C7 C8 O1 180.0(4) . . . . ?
C4 C3 C8 C7 0.2(6) . . . . ?
C2 C3 C8 C7 -179.8(4) . . . . ?
C4 C3 C8 O1 179.9(3) . . . . ?
C2 C3 C8 O1 -0.1(4) . . . . ?
C1 O1 C8 C7 180.0(4) . . . . ?
C1 O1 C8 C3 0.3(4) . . . . ?
O1 C1 C9 C11 -0.1(7) . . . . ?
C2 C1 C9 C11 179.8(4) . . . . ?
C1 C9 C11 C16 -4.1(7) . . . . ?
C1 C9 C11 C12 174.1(4) . . . . ?
C17 O3 C12 C13 3.7(6) . . . . ?
C17 O3 C12 C11 -175.4(4) . . . . ?
C16 C11 C12 O3 178.8(3) . . . . ?
C9 C11 C12 O3 0.4(5) . . . . ?
C16 C11 C12 C13 -0.3(6) . . . . ?
C9 C11 C12 C13 -178.7(4) . . . . ?
O3 C12 C13 C14 -179.8(4) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C20 N1 C14 C15 9.4(6) . . . . ?
C18 N1 C14 C15 -174.1(4) . . . . ?
C20 N1 C14 C13 -170.4(4) . . . . ?
C18 N1 C14 C13 6.0(6) . . . . ?
C12 C13 C14 N1 -178.5(4) . . . . ?
C12 C13 C14 C15 1.6(6) . . . . ?
N1 C14 C15 C16 178.7(4) . . . . ?
C13 C14 C15 C16 -1.4(6) . . . . ?
C14 C15 C16 C11 0.3(6) . . . . ?
C12 C11 C16 C15 0.6(6) . . . . ?
C9 C11 C16 C15 178.9(4) . . . . ?
C14 N1 C18 C19 -85.8(5) . . . . ?
C20 N1 C18 C19 90.9(5) . . . . ?
C14 N1 C20 C21 -95.3(5) . . . . ?
C18 N1 C20 C21 88.1(5) . . . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.050

