# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1508996'
_audit_update_record             
;
2016-10-10 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26

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

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

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

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

_cell_length_a                   8.269(3)
_cell_length_b                   9.296(4)
_cell_length_c                   16.904(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.281(4)
_cell_angle_gamma                90
_cell_volume                     1297.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4201
_cell_measurement_theta_min      2.444
_cell_measurement_theta_max      25.562

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9395
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.414
_diffrn_reflns_theta_max         27.008
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2581
_reflns_number_gt                2113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0569P)²+0.1654P]
 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         2581
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.15174(10) 0.66026(9) 0.49535(5) 0.0473(2) Uani 1 1 d . . . . .
N1 N 0.27209(12) 0.89260(11) 0.49444(6) 0.0432(3) Uani 1 1 d . . . . .
C1 C 0.23688(14) 0.63224(14) 0.56638(7) 0.0430(3) Uani 1 1 d . . . . .
O3 O 0.39330(13) 0.98868(10) 0.60681(6) 0.0621(3) Uani 1 1 d . . . . .
C6 C 0.33816(15) 0.73605(14) 0.60239(7) 0.0448(3) Uani 1 1 d . . . . .
C7 C 0.34237(15) 0.88385(14) 0.56991(7) 0.0452(3) Uani 1 1 d . . . . .
C14 C 0.11015(16) 0.82088(16) 0.38245(7) 0.0520(3) Uani 1 1 d . . . . .
C2 C 0.21203(16) 0.50071(14) 0.60197(8) 0.0509(3) Uani 1 1 d . . . . .
H2 H 0.1417 0.4334 0.5781 0.061 Uiso 1 1 calc R U . . .
C8 C 0.21582(14) 1.01635(13) 0.45344(7) 0.0432(3) Uani 1 1 d . . . . .
C15 C 0.23046(15) 0.76285(13) 0.44819(7) 0.0444(3) Uani 1 1 d . . . . .
O2 O 0.03280(15) 0.74360(13) 0.33671(6) 0.0783(4) Uani 1 1 d . . . . .
C5 C 0.41962(17) 0.70227(16) 0.67455(8) 0.0556(4) Uani 1 1 d . . . . .
H5 H 0.4887 0.7696 0.6993 0.067 Uiso 1 1 calc R U . . .
C3 C 0.29378(18) 0.47133(16) 0.67369(8) 0.0575(4) Uani 1 1 d . . . . .
H3 H 0.2778 0.3834 0.6983 0.069 Uiso 1 1 calc R U . . .
C13 C 0.11921(15) 0.97720(15) 0.38650(7) 0.0473(3) Uani 1 1 d . . . . .
C16 C 0.37518(17) 0.69621(16) 0.41104(8) 0.0572(4) Uani 1 1 d . . . . .
H16A H 0.4468 0.6555 0.4518 0.086 Uiso 1 1 calc R U . . .
H16B H 0.4316 0.7689 0.3831 0.086 Uiso 1 1 calc R U . . .
H16C H 0.3389 0.6221 0.3747 0.086 Uiso 1 1 calc R U . . .
C4 C 0.39890(19) 0.57021(17) 0.70960(8) 0.0611(4) Uani 1 1 d . . . . .
H4 H 0.4554 0.5478 0.7572 0.073 Uiso 1 1 calc R U . . .
C9 C 0.24382(17) 1.16004(14) 0.47176(8) 0.0522(3) Uani 1 1 d . . . . .
H9 H 0.3059 1.1872 0.5169 0.063 Uiso 1 1 calc R U . . .
C12 C 0.05093(18) 1.08144(17) 0.33576(8) 0.0582(4) Uani 1 1 d . . . . .
H12 H -0.0144 1.0552 0.2915 0.070 Uiso 1 1 calc R U . . .
C11 C 0.08185(19) 1.22360(17) 0.35221(9) 0.0635(4) Uani 1 1 d . . . . .
H11 H 0.0402 1.2947 0.3181 0.076 Uiso 1 1 calc R U . . .
C10 C 0.17545(19) 1.26132(16) 0.41990(9) 0.0619(4) Uani 1 1 d . . . . .
H10 H 0.1929 1.3583 0.4308 0.074 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 1.3814(15) . ?
O1 C15 1.4242(15) . ?
N1 C7 1.3737(16) . ?
N1 C8 1.4083(16) . ?
N1 C15 1.4676(16) . ?
C1 C2 1.3832(19) . ?
C1 C6 1.3946(17) . ?
O3 C7 1.2190(15) . ?
C6 C5 1.3951(18) . ?
C6 C7 1.4807(18) . ?
C14 O2 1.2110(15) . ?
C14 C13 1.456(2) . ?
C14 C15 1.5456(18) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9300 . ?
C8 C9 1.3877(19) . ?
C8 C13 1.3956(17) . ?
C15 C16 1.5153(19) . ?
C5 C4 1.378(2) . ?
C5 H5 0.9300 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C13 C12 1.3921(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C4 H4 0.9300 . ?
C9 C10 1.385(2) . ?
C9 H9 0.9300 . ?
C12 C11 1.371(2) . ?
C12 H12 0.9300 . ?
C11 C10 1.389(2) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?

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 C15 112.73(9) . . ?
C7 N1 C8 128.00(10) . . ?
C7 N1 C15 121.34(10) . . ?
C8 N1 C15 110.38(10) . . ?
O1 C1 C2 117.62(11) . . ?
O1 C1 C6 120.82(11) . . ?
C2 C1 C6 121.49(12) . . ?
C1 C6 C5 118.28(12) . . ?
C1 C6 C7 120.43(11) . . ?
C5 C6 C7 120.84(12) . . ?
O3 C7 N1 122.91(12) . . ?
O3 C7 C6 124.52(12) . . ?
N1 C7 C6 112.43(10) . . ?
O2 C14 C13 130.22(13) . . ?
O2 C14 C15 123.14(13) . . ?
C13 C14 C15 106.57(10) . . ?
C1 C2 C3 118.63(13) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C9 C8 C13 120.82(12) . . ?
C9 C8 N1 129.07(11) . . ?
C13 C8 N1 110.10(11) . . ?
O1 C15 N1 110.66(10) . . ?
O1 C15 C16 110.82(11) . . ?
N1 C15 C16 112.96(10) . . ?
O1 C15 C14 109.89(10) . . ?
N1 C15 C14 102.59(10) . . ?
C16 C15 C14 109.63(11) . . ?
C4 C5 C6 120.71(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C3 C2 121.21(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C12 C13 C8 120.74(13) . . ?
C12 C13 C14 130.36(12) . . ?
C8 C13 C14 108.89(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C4 C3 119.63(13) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C10 C9 C8 117.15(13) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C11 C12 C13 118.79(13) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C11 C10 119.92(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C9 C10 C11 122.54(14) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?

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
C15 O1 C1 C2 -154.94(11) . . . . ?
C15 O1 C1 C6 28.02(16) . . . . ?
O1 C1 C6 C5 179.26(11) . . . . ?
C2 C1 C6 C5 2.34(19) . . . . ?
O1 C1 C6 C7 6.90(18) . . . . ?
C2 C1 C6 C7 -170.02(12) . . . . ?
C8 N1 C7 O3 -14.3(2) . . . . ?
C15 N1 C7 O3 172.35(12) . . . . ?
C8 N1 C7 C6 161.66(11) . . . . ?
C15 N1 C7 C6 -11.66(17) . . . . ?
C1 C6 C7 O3 160.76(13) . . . . ?
C5 C6 C7 O3 -11.4(2) . . . . ?
C1 C6 C7 N1 -15.15(17) . . . . ?
C5 C6 C7 N1 172.68(12) . . . . ?
O1 C1 C2 C3 -178.91(12) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C7 N1 C8 C9 13.6(2) . . . . ?
C15 N1 C8 C9 -172.50(13) . . . . ?
C7 N1 C8 C13 -166.03(12) . . . . ?
C15 N1 C8 C13 7.89(14) . . . . ?
C1 O1 C15 N1 -51.54(14) . . . . ?
C1 O1 C15 C16 74.57(12) . . . . ?
C1 O1 C15 C14 -164.12(10) . . . . ?
C7 N1 C15 O1 45.48(16) . . . . ?
C8 N1 C15 O1 -128.91(11) . . . . ?
C7 N1 C15 C16 -79.42(15) . . . . ?
C8 N1 C15 C16 106.19(12) . . . . ?
C7 N1 C15 C14 162.65(11) . . . . ?
C8 N1 C15 C14 -11.74(13) . . . . ?
O2 C14 C15 O1 -53.59(17) . . . . ?
C13 C14 C15 O1 129.12(11) . . . . ?
O2 C14 C15 N1 -171.31(13) . . . . ?
C13 C14 C15 N1 11.40(13) . . . . ?
O2 C14 C15 C16 68.43(17) . . . . ?
C13 C14 C15 C16 -108.86(12) . . . . ?
C1 C6 C5 C4 -0.7(2) . . . . ?
C7 C6 C5 C4 171.63(13) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C9 C8 C13 C12 1.12(19) . . . . ?
N1 C8 C13 C12 -179.23(11) . . . . ?
C9 C8 C13 C14 -179.59(12) . . . . ?
N1 C8 C13 C14 0.05(14) . . . . ?
O2 C14 C13 C12 -5.2(3) . . . . ?
C15 C14 C13 C12 171.79(14) . . . . ?
O2 C14 C13 C8 175.57(15) . . . . ?
C15 C14 C13 C8 -7.40(14) . . . . ?
C6 C5 C4 C3 -1.3(2) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C13 C8 C9 C10 -1.6(2) . . . . ?
N1 C8 C9 C10 178.84(13) . . . . ?
C8 C13 C12 C11 0.8(2) . . . . ?
C14 C13 C12 C11 -178.35(14) . . . . ?
C13 C12 C11 C10 -2.1(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C12 C11 C10 C9 1.6(2) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1508997'
_audit_update_record             
;
2016-10-10 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   8.874(6)
_cell_length_b                   13.733(9)
_cell_length_c                   27.215(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3317(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7968
_cell_measurement_theta_min      2.413
_cell_measurement_theta_max      26.081

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22971
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.496
_diffrn_reflns_theta_max         26.936
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3390
_reflns_number_gt                2726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0421P)²+0.6891P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0054(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3390
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21522(13) 0.37260(9) 0.16570(4) 0.0407(3) Uani 1 1 d . . . . .
C2 C 0.12571(15) 0.41825(10) 0.20056(5) 0.0512(3) Uani 1 1 d . . . . .
H2 H 0.0775 0.4767 0.1934 0.061 Uiso 1 1 calc R U . . .
C3 C 0.10964(19) 0.37498(12) 0.24610(5) 0.0652(4) Uani 1 1 d . . . . .
H3 H 0.0501 0.4048 0.2699 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1808(2) 0.28806(12) 0.25681(5) 0.0700(4) Uani 1 1 d . . . . .
H4 H 0.1692 0.2601 0.2877 0.084 Uiso 1 1 calc R U . . .
C5 C 0.26877(18) 0.24265(11) 0.22195(5) 0.0584(4) Uani 1 1 d . . . . .
H5 H 0.3156 0.1838 0.2293 0.070 Uiso 1 1 calc R U . . .
C6 C 0.28791(14) 0.28482(9) 0.17560(4) 0.0438(3) Uani 1 1 d . . . . .
C7 C 0.37067(14) 0.23301(9) 0.13627(5) 0.0451(3) Uani 1 1 d . . . . .
C8 C 0.42614(13) 0.25782(9) 0.04668(5) 0.0433(3) Uani 1 1 d . . . . .
C9 C 0.47512(15) 0.16736(10) 0.03055(6) 0.0540(3) Uani 1 1 d . . . . .
H9 H 0.4969 0.1173 0.0524 0.065 Uiso 1 1 calc R U . . .
C10 C 0.49004(17) 0.15534(12) -0.02003(6) 0.0641(4) Uani 1 1 d . . . . .
H10 H 0.5213 0.0953 -0.0322 0.077 Uiso 1 1 calc R U . . .
C11 C 0.45982(18) 0.22978(13) -0.05273(6) 0.0655(4) Uani 1 1 d . . . . .
H11 H 0.4705 0.2191 -0.0863 0.079 Uiso 1 1 calc R U . . .
C12 C 0.41383(16) 0.31995(11) -0.03598(5) 0.0565(4) Uani 1 1 d . . . . .
H12 H 0.3938 0.3702 -0.0580 0.068 Uiso 1 1 calc R U . . .
C13 C 0.39796(14) 0.33436(9) 0.01431(5) 0.0444(3) Uani 1 1 d . . . . .
C14 C 0.35386(13) 0.42135(9) 0.04179(4) 0.0403(3) Uani 1 1 d . . . . .
C15 C 0.31437(15) 0.50874(10) 0.02596(5) 0.0511(3) Uani 1 1 d . . . . .
H15A H 0.3119 0.5217 -0.0076 0.061 Uiso 1 1 calc R U . . .
H15B H 0.2890 0.5572 0.0483 0.061 Uiso 1 1 calc R U . . .
C16 C 0.49350(14) 0.45126(8) 0.12108(4) 0.0393(3) Uani 1 1 d . . . . .
C17 C 0.46445(16) 0.53788(9) 0.14587(4) 0.0466(3) Uani 1 1 d . . . . .
H17 H 0.3657 0.5592 0.1498 0.056 Uiso 1 1 calc R U . . .
C18 C 0.58278(18) 0.59232(11) 0.16468(5) 0.0592(4) Uani 1 1 d . . . . .
H18 H 0.5630 0.6495 0.1818 0.071 Uiso 1 1 calc R U . . .
C19 C 0.72993(19) 0.56205(13) 0.15806(6) 0.0684(4) Uani 1 1 d . . . . .
H19 H 0.8090 0.5991 0.1705 0.082 Uiso 1 1 calc R U . . .
C20 C 0.75914(17) 0.47711(12) 0.13314(5) 0.0647(4) Uani 1 1 d . . . . .
H20 H 0.8582 0.4571 0.1284 0.078 Uiso 1 1 calc R U . . .
C21 C 0.64181(15) 0.42109(10) 0.11496(5) 0.0501(3) Uani 1 1 d . . . . .
H21 H 0.6624 0.3631 0.0986 0.060 Uiso 1 1 calc R U . . .
C22 C 0.36589(13) 0.39508(8) 0.09626(4) 0.0376(3) Uani 1 1 d . . . . .
N1 N 0.39557(11) 0.28923(7) 0.09545(4) 0.0412(3) Uani 1 1 d . . . . .
O1 O 0.22563(9) 0.41512(6) 0.11982(3) 0.0405(2) Uani 1 1 d . . . . .
O2 O 0.40682(12) 0.14706(7) 0.13852(4) 0.0643(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3817(15) . ?
C1 C2 1.3871(18) . ?
C1 C6 1.3935(19) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3983(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4804(19) . ?
C7 O2 1.2247(16) . ?
C7 N1 1.3707(17) . ?
C8 C9 1.3875(19) . ?
C8 C13 1.3941(19) . ?
C8 N1 1.4217(17) . ?
C9 C10 1.393(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.4628(18) . ?
C14 C15 1.3225(19) . ?
C14 C22 1.5295(18) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 C21 1.3898(19) . ?
C16 C17 1.3916(18) . ?
C16 C22 1.5277(17) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(2) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 O1 1.4268(15) . ?
C22 N1 1.4775(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 117.74(12) . . ?
O1 C1 C6 120.62(11) . . ?
C2 C1 C6 121.59(12) . . ?
C3 C2 C1 118.56(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 120.91(14) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.32(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.16(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.45(12) . . ?
C1 C6 C7 120.37(11) . . ?
C5 C6 C7 120.90(12) . . ?
O2 C7 N1 122.76(12) . . ?
O2 C7 C6 123.85(12) . . ?
N1 C7 C6 113.29(11) . . ?
C9 C8 C13 122.10(13) . . ?
C9 C8 N1 128.81(12) . . ?
C13 C8 N1 109.09(11) . . ?
C8 C9 C10 116.65(14) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C11 C10 C9 122.04(14) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 120.53(14) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 118.85(15) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 119.78(13) . . ?
C12 C13 C14 130.30(13) . . ?
C8 C13 C14 109.91(11) . . ?
C15 C14 C13 130.20(12) . . ?
C15 C14 C22 123.26(11) . . ?
C13 C14 C22 106.52(10) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C21 C16 C17 119.23(12) . . ?
C21 C16 C22 119.89(11) . . ?
C17 C16 C22 120.58(11) . . ?
C18 C17 C16 119.96(13) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.34(14) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.86(14) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.38(15) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.21(13) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
O1 C22 N1 110.61(9) . . ?
O1 C22 C16 110.52(10) . . ?
N1 C22 C16 111.80(10) . . ?
O1 C22 C14 109.21(9) . . ?
N1 C22 C14 103.30(9) . . ?
C16 C22 C14 111.17(10) . . ?
C7 N1 C8 128.06(11) . . ?
C7 N1 C22 120.88(10) . . ?
C8 N1 C22 110.27(9) . . ?
C1 O1 C22 112.51(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 177.73(12) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
O1 C1 C6 C5 -177.34(11) . . . . ?
C2 C1 C6 C5 0.10(19) . . . . ?
O1 C1 C6 C7 -3.34(17) . . . . ?
C2 C1 C6 C7 174.10(12) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 -174.51(14) . . . . ?
C1 C6 C7 O2 -162.41(13) . . . . ?
C5 C6 C7 O2 11.4(2) . . . . ?
C1 C6 C7 N1 13.94(17) . . . . ?
C5 C6 C7 N1 -172.20(12) . . . . ?
C13 C8 C9 C10 -2.15(19) . . . . ?
N1 C8 C9 C10 177.36(12) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C8 -1.0(2) . . . . ?
C11 C12 C13 C14 179.00(13) . . . . ?
C9 C8 C13 C12 2.27(19) . . . . ?
N1 C8 C13 C12 -177.32(11) . . . . ?
C9 C8 C13 C14 -177.73(11) . . . . ?
N1 C8 C13 C14 2.67(14) . . . . ?
C12 C13 C14 C15 1.6(2) . . . . ?
C8 C13 C14 C15 -178.38(13) . . . . ?
C12 C13 C14 C22 -176.52(13) . . . . ?
C8 C13 C14 C22 3.49(13) . . . . ?
C21 C16 C17 C18 -0.83(19) . . . . ?
C22 C16 C17 C18 -174.59(11) . . . . ?
C16 C17 C18 C19 1.3(2) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C20 C21 C16 1.1(2) . . . . ?
C17 C16 C21 C20 -0.37(19) . . . . ?
C22 C16 C21 C20 173.44(12) . . . . ?
C21 C16 C22 O1 159.95(11) . . . . ?
C17 C16 C22 O1 -26.33(14) . . . . ?
C21 C16 C22 N1 36.27(15) . . . . ?
C17 C16 C22 N1 -150.00(11) . . . . ?
C21 C16 C22 C14 -78.60(14) . . . . ?
C17 C16 C22 C14 95.12(13) . . . . ?
C15 C14 C22 O1 56.11(15) . . . . ?
C13 C14 C22 O1 -125.60(10) . . . . ?
C15 C14 C22 N1 173.84(12) . . . . ?
C13 C14 C22 N1 -7.86(12) . . . . ?
C15 C14 C22 C16 -66.10(16) . . . . ?
C13 C14 C22 C16 112.19(11) . . . . ?
O2 C7 N1 C8 18.1(2) . . . . ?
C6 C7 N1 C8 -158.27(11) . . . . ?
O2 C7 N1 C22 -173.07(12) . . . . ?
C6 C7 N1 C22 10.53(16) . . . . ?
C9 C8 N1 C7 -17.9(2) . . . . ?
C13 C8 N1 C7 161.66(12) . . . . ?
C9 C8 N1 C22 172.33(12) . . . . ?
C13 C8 N1 C22 -8.11(13) . . . . ?
O1 C22 N1 C7 -44.11(14) . . . . ?
C16 C22 N1 C7 79.52(14) . . . . ?
C14 C22 N1 C7 -160.86(10) . . . . ?
O1 C22 N1 C8 126.51(10) . . . . ?
C16 C22 N1 C8 -109.86(11) . . . . ?
C14 C22 N1 C8 9.76(12) . . . . ?
C2 C1 O1 C22 151.10(11) . . . . ?
C6 C1 O1 C22 -31.36(14) . . . . ?
N1 C22 O1 C1 52.60(12) . . . . ?
C16 C22 O1 C1 -71.76(12) . . . . ?
C14 C22 O1 C1 165.64(9) . . . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-2



