# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2013296_0m
_database_code_depnum_ccdc_archive 'CCDC 1540588'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O2.50'
_chemical_formula_weight         364.41

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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'
'-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                   24.0516(14)
_cell_length_b                   8.6236(5)
_cell_length_c                   20.5558(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.207(3)
_cell_angle_gamma                90.00
_cell_volume                     4094.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.078
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15097
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3602
_reflns_number_gt                2662
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3602
_refine_ls_number_parameters     260
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1382
_refine_ls_R_factor_gt           0.1177
_refine_ls_wR_factor_ref         0.4122
_refine_ls_wR_factor_gt          0.3849
_refine_ls_goodness_of_fit_ref   1.768
_refine_ls_restrained_S_all      1.780
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.43434(16) 1.0834(4) 0.0140(3) 0.0907(15) Uani 1 1 d . . .
N1 N 0.26879(14) 1.0121(4) 0.03141(17) 0.0443(10) Uani 1 1 d . . .
N2 N 0.44991(17) 0.8358(5) -0.0054(2) 0.0731(14) Uani 1 1 d . . .
H2A H 0.4847 0.8541 -0.0068 0.088 Uiso 1 1 calc R . .
H2B H 0.4364 0.7429 -0.0110 0.088 Uiso 1 1 calc R . .
C18 C 0.0520(2) 0.9285(7) 0.1577(3) 0.0747(16) Uani 1 1 d . . .
H1 H 0.0231 0.9138 0.1792 0.090 Uiso 1 1 calc R . .
C17 C 0.0998(2) 0.8346(6) 0.1719(2) 0.0649(14) Uani 1 1 d . . .
H9 H 0.1037 0.7561 0.2038 0.078 Uiso 1 1 calc R . .
C16 C 0.14258(19) 0.8553(5) 0.1390(2) 0.0525(11) Uani 1 1 d . . .
H10 H 0.1746 0.7899 0.1490 0.063 Uiso 1 1 calc R . .
C15 C 0.13793(17) 0.9722(4) 0.0917(2) 0.0434(11) Uani 1 1 d . . .
C2 C 0.18248(18) 0.9966(4) 0.0553(2) 0.0431(10) Uani 1 1 d . . .
C1 C 0.24151(17) 0.9823(4) 0.08189(19) 0.0399(10) Uani 1 1 d . . .
C21 C 0.33041(18) 1.0369(5) 0.0398(2) 0.0482(11) Uani 1 1 d . . .
H16 H 0.3502 1.0461 0.0877 0.058 Uiso 1 1 calc R . .
H15 H 0.3355 1.1338 0.0182 0.058 Uiso 1 1 calc R . .
C22 C 0.3575(2) 0.9082(5) 0.0102(3) 0.0577(13) Uani 1 1 d . . .
H17 H 0.3330 0.8840 -0.0347 0.069 Uiso 1 1 calc R . .
H18 H 0.3600 0.8163 0.0381 0.069 Uiso 1 1 calc R . .
C23 C 0.41743(18) 0.9497(5) 0.0056(2) 0.0484(11) Uani 1 1 d . . .
C8 C 0.22692(19) 1.0480(4) -0.0269(2) 0.0454(11) Uani 1 1 d . . .
C3 C 0.17204(19) 1.0349(4) -0.0152(2) 0.0451(11) Uani 1 1 d . . .
C9 C 0.27563(17) 0.9407(4) 0.1519(2) 0.0433(10) Uani 1 1 d . . .
C14 C 0.2695(2) 1.0289(5) 0.2063(2) 0.0550(12) Uani 1 1 d . . .
H6 H 0.2459 1.1164 0.1986 0.066 Uiso 1 1 calc R . .
C13 C 0.2984(3) 0.9864(6) 0.2715(3) 0.0707(16) Uani 1 1 d . . .
H5 H 0.2936 1.0446 0.3076 0.085 Uiso 1 1 calc R . .
C12 C 0.3342(3) 0.8589(7) 0.2839(3) 0.0768(17) Uani 1 1 d . . .
H2 H 0.3545 0.8330 0.3281 0.092 Uiso 1 1 calc R . .
C11 C 0.3397(2) 0.7699(7) 0.2304(3) 0.0699(14) Uani 1 1 d . . .
H3 H 0.3633 0.6825 0.2385 0.084 Uiso 1 1 calc R . .
C10 C 0.3104(2) 0.8099(5) 0.1644(2) 0.0572(12) Uani 1 1 d . . .
H4 H 0.3140 0.7488 0.1285 0.069 Uiso 1 1 calc R . .
C19 C 0.0477(2) 1.0446(6) 0.1111(3) 0.0672(15) Uani 1 1 d . . .
H8 H 0.0156 1.1095 0.1014 0.081 Uiso 1 1 calc R . .
C20 C 0.08946(19) 1.0680(5) 0.0784(2) 0.0553(12) Uani 1 1 d . . .
H7 H 0.0854 1.1482 0.0472 0.066 Uiso 1 1 calc R . .
C4 C 0.1219(2) 1.0555(5) -0.0691(2) 0.0549(12) Uani 1 1 d . . .
H11 H 0.0853 1.0450 -0.0629 0.066 Uiso 1 1 calc R . .
C5 C 0.1291(2) 1.0922(6) -0.1323(2) 0.0628(13) Uani 1 1 d . . .
H14 H 0.0965 1.1039 -0.1690 0.075 Uiso 1 1 calc R . .
C6 C 0.1824(2) 1.1117(6) -0.1421(2) 0.0631(13) Uani 1 1 d . . .
H13 H 0.1851 1.1400 -0.1848 0.076 Uiso 1 1 calc R . .
C7 C 0.2329(2) 1.0902(5) -0.0900(2) 0.0557(12) Uani 1 1 d . . .
H12 H 0.2692 1.1035 -0.0970 0.067 Uiso 1 1 calc R . .
O1S O 0.5000 0.7556(6) 0.2500 0.109(3) Uani 1 2 d SD . .
O2S O 0.4702(3) 0.0558(7) 0.1854(3) 0.1209(19) Uani 1 1 d DU . .
H2' H 0.4904(4) -0.0063(10) 0.1693(5) -0.400(2) Uiso 1 1 d D . .
H3' H 0.4741(11) 0.7477(6) 0.2124(9) -0.002(8) Uiso 1 1 d D . .
H4' H 0.5000 0.8542(6) 0.2500 0.24(8) Uiso 1 2 d SD . .


_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 C23 1.219(5) . ?
N1 C8 1.369(5) . ?
N1 C1 1.398(5) . ?
N1 C21 1.459(5) . ?
N2 C23 1.312(5) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C18 C17 1.369(8) . ?
C18 C19 1.369(7) . ?
C18 H1 0.9300 . ?
C17 C16 1.391(6) . ?
C17 H9 0.9300 . ?
C16 C15 1.385(6) . ?
C16 H10 0.9300 . ?
C15 C20 1.392(6) . ?
C15 C2 1.483(6) . ?
C2 C1 1.377(6) . ?
C2 C3 1.438(6) . ?
C1 C9 1.488(5) . ?
C21 C22 1.499(6) . ?
C21 H16 0.9700 . ?
C21 H15 0.9700 . ?
C22 C23 1.513(6) . ?
C22 H17 0.9700 . ?
C22 H18 0.9700 . ?
C8 C7 1.393(6) . ?
C8 C3 1.411(6) . ?
C3 C4 1.402(6) . ?
C9 C10 1.385(6) . ?
C9 C14 1.394(6) . ?
C14 C13 1.375(7) . ?
C14 H6 0.9300 . ?
C13 C12 1.376(8) . ?
C13 H5 0.9300 . ?
C12 C11 1.378(8) . ?
C12 H2 0.9300 . ?
C11 C10 1.386(7) . ?
C11 H3 0.9300 . ?
C10 H4 0.9300 . ?
C19 C20 1.369(7) . ?
C19 H8 0.9300 . ?
C20 H7 0.9300 . ?
C4 C5 1.395(7) . ?
C4 H11 0.9300 . ?
C5 C6 1.363(8) . ?
C5 H14 0.9300 . ?
C6 C7 1.389(7) . ?
C6 H13 0.9300 . ?
C7 H12 0.9300 . ?
O1S H4' 0.8502(10) . ?
O1S H3' 0.8501(10) . ?
O1S H4' 0.8502(10) . ?
O2S H2' 0.8500(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 108.0(3) . . ?
C8 N1 C21 123.0(3) . . ?
C1 N1 C21 127.6(3) . . ?
C23 N2 H2A 120.0 . . ?
C23 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C17 C18 C19 118.4(5) . . ?
C17 C18 H1 120.8 . . ?
C19 C18 H1 120.8 . . ?
C18 C17 C16 120.8(5) . . ?
C18 C17 H9 119.6 . . ?
C16 C17 H9 119.6 . . ?
C15 C16 C17 120.6(4) . . ?
C15 C16 H10 119.7 . . ?
C17 C16 H10 119.7 . . ?
C16 C15 C20 117.9(4) . . ?
C16 C15 C2 122.0(4) . . ?
C20 C15 C2 120.0(4) . . ?
C1 C2 C3 107.0(4) . . ?
C1 C2 C15 126.6(4) . . ?
C3 C2 C15 126.4(4) . . ?
C2 C1 N1 109.5(3) . . ?
C2 C1 C9 129.4(4) . . ?
N1 C1 C9 121.1(3) . . ?
N1 C21 C22 112.7(3) . . ?
N1 C21 H16 109.0 . . ?
C22 C21 H16 109.0 . . ?
N1 C21 H15 109.0 . . ?
C22 C21 H15 109.0 . . ?
H16 C21 H15 107.8 . . ?
C21 C22 C23 112.4(4) . . ?
C21 C22 H17 109.1 . . ?
C23 C22 H17 109.1 . . ?
C21 C22 H18 109.1 . . ?
C23 C22 H18 109.1 . . ?
H17 C22 H18 107.9 . . ?
O1 C23 N2 122.8(4) . . ?
O1 C23 C22 120.0(4) . . ?
N2 C23 C22 117.2(4) . . ?
N1 C8 C7 129.3(4) . . ?
N1 C8 C3 109.1(4) . . ?
C7 C8 C3 121.7(4) . . ?
C4 C3 C8 119.6(4) . . ?
C4 C3 C2 134.0(4) . . ?
C8 C3 C2 106.4(4) . . ?
C10 C9 C14 119.3(4) . . ?
C10 C9 C1 121.1(4) . . ?
C14 C9 C1 119.4(4) . . ?
C13 C14 C9 119.9(5) . . ?
C13 C14 H6 120.1 . . ?
C9 C14 H6 120.1 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 H5 119.5 . . ?
C12 C13 H5 119.5 . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H2 120.3 . . ?
C11 C12 H2 120.3 . . ?
C12 C11 C10 120.4(5) . . ?
C12 C11 H3 119.8 . . ?
C10 C11 H3 119.8 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H4 120.0 . . ?
C11 C10 H4 120.0 . . ?
C20 C19 C18 121.9(5) . . ?
C20 C19 H8 119.1 . . ?
C18 C19 H8 119.1 . . ?
C19 C20 C15 120.4(4) . . ?
C19 C20 H7 119.8 . . ?
C15 C20 H7 119.8 . . ?
C5 C4 C3 117.5(5) . . ?
C5 C4 H11 121.3 . . ?
C3 C4 H11 121.3 . . ?
C6 C5 C4 122.2(5) . . ?
C6 C5 H14 118.9 . . ?
C4 C5 H14 118.9 . . ?
C5 C6 C7 121.7(4) . . ?
C5 C6 H13 119.2 . . ?
C7 C6 H13 119.2 . . ?
C6 C7 C8 117.2(5) . . ?
C6 C7 H12 121.4 . . ?
C8 C7 H12 121.4 . . ?
H4' O1S H3' 94.61(15) . . ?
H4' O1S H4' 0.000(2) . . ?
H3' O1S H4' 94.61(15) . . ?

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
C19 C18 C17 C16 -0.9(8) . . . . ?
C18 C17 C16 C15 0.5(7) . . . . ?
C17 C16 C15 C20 0.3(7) . . . . ?
C17 C16 C15 C2 -179.4(4) . . . . ?
C16 C15 C2 C1 -38.4(6) . . . . ?
C20 C15 C2 C1 141.9(4) . . . . ?
C16 C15 C2 C3 139.4(4) . . . . ?
C20 C15 C2 C3 -40.3(6) . . . . ?
C3 C2 C1 N1 0.8(4) . . . . ?
C15 C2 C1 N1 179.0(4) . . . . ?
C3 C2 C1 C9 -178.5(4) . . . . ?
C15 C2 C1 C9 -0.3(7) . . . . ?
C8 N1 C1 C2 1.0(4) . . . . ?
C21 N1 C1 C2 168.1(4) . . . . ?
C8 N1 C1 C9 -179.5(3) . . . . ?
C21 N1 C1 C9 -12.5(6) . . . . ?
C8 N1 C21 C22 -82.5(5) . . . . ?
C1 N1 C21 C22 112.3(5) . . . . ?
N1 C21 C22 C23 167.8(4) . . . . ?
C21 C22 C23 O1 -12.3(7) . . . . ?
C21 C22 C23 N2 165.5(4) . . . . ?
C1 N1 C8 C7 178.1(4) . . . . ?
C21 N1 C8 C7 10.3(7) . . . . ?
C1 N1 C8 C3 -2.6(4) . . . . ?
C21 N1 C8 C3 -170.3(3) . . . . ?
N1 C8 C3 C4 -175.5(4) . . . . ?
C7 C8 C3 C4 3.9(6) . . . . ?
N1 C8 C3 C2 3.0(4) . . . . ?
C7 C8 C3 C2 -177.5(4) . . . . ?
C1 C2 C3 C4 175.9(4) . . . . ?
C15 C2 C3 C4 -2.3(7) . . . . ?
C1 C2 C3 C8 -2.3(4) . . . . ?
C15 C2 C3 C8 179.5(4) . . . . ?
C2 C1 C9 C10 119.0(5) . . . . ?
N1 C1 C9 C10 -60.3(5) . . . . ?
C2 C1 C9 C14 -56.6(6) . . . . ?
N1 C1 C9 C14 124.1(4) . . . . ?
C10 C9 C14 C13 0.7(7) . . . . ?
C1 C9 C14 C13 176.4(4) . . . . ?
C9 C14 C13 C12 1.1(7) . . . . ?
C14 C13 C12 C11 -2.1(8) . . . . ?
C13 C12 C11 C10 1.2(8) . . . . ?
C14 C9 C10 C11 -1.5(7) . . . . ?
C1 C9 C10 C11 -177.2(4) . . . . ?
C12 C11 C10 C9 0.6(8) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C18 C19 C20 C15 0.3(8) . . . . ?
C16 C15 C20 C19 -0.7(7) . . . . ?
C2 C15 C20 C19 179.0(4) . . . . ?
C8 C3 C4 C5 -1.5(6) . . . . ?
C2 C3 C4 C5 -179.6(4) . . . . ?
C3 C4 C5 C6 -1.6(7) . . . . ?
C4 C5 C6 C7 2.4(8) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
N1 C8 C7 C6 176.2(4) . . . . ?
C3 C8 C7 C6 -3.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.751
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.134
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM-PE'
