# 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_dc
_database_code_depnum_ccdc_archive 'CCDC 1567078'
_audit_update_record             
;
2017-08-06 deposited with the CCDC.
2017-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N3 O'
_chemical_formula_sum            'C21 H21 N3 O'
_chemical_formula_weight         331.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.098(3)
_cell_length_b                   27.444(14)
_cell_length_c                   11.214(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.50(3)
_cell_angle_gamma                90.00
_cell_volume                     1824.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2442
_cell_measurement_theta_min      3.2010
_cell_measurement_theta_max      65.4600

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_min  0.73119
_exptl_absorpt_correction_T_max  1.23269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16506
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         66.02
_reflns_number_total             3134
_reflns_number_gt                1681
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0340P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3134
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
N1 N -0.4044(3) 0.73016(6) -0.26017(13) 0.0528(4) Uani 1 1 d . . .
O1S O 0.3411(3) 0.70430(6) 0.05547(17) 0.0716(5) Uani 1 1 d . . .
C1 C -0.0400(4) 0.76896(10) -0.2486(2) 0.0804(8) Uani 1 1 d . . .
H1A H 0.0036 0.7416 -0.2912 0.121 Uiso 1 1 calc R . .
H1B H 0.0908 0.7823 -0.1934 0.121 Uiso 1 1 calc R . .
H1C H -0.1079 0.7934 -0.3068 0.121 Uiso 1 1 calc R . .
N2 N 0.0120(3) 0.62558(6) 0.03974(14) 0.0505(4) Uani 1 1 d . . .
C2 C -0.2083(4) 0.75245(8) -0.17636(18) 0.0560(5) Uani 1 1 d . . .
N3 N -0.1076(3) 0.71482(6) -0.08851(13) 0.0520(4) Uani 1 1 d . . .
C3 C -0.2910(4) 0.79404(8) -0.1086(2) 0.0796(8) Uani 1 1 d . . .
H3A H -0.3918 0.7815 -0.0618 0.119 Uiso 1 1 calc R . .
H3B H -0.3690 0.8175 -0.1667 0.119 Uiso 1 1 calc R . .
H3C H -0.1646 0.8094 -0.0544 0.119 Uiso 1 1 calc R . .
C4 C -0.2337(3) 0.67674(7) -0.11428(16) 0.0459(5) Uani 1 1 d . . .
C5 C -0.4199(3) 0.68690(7) -0.22376(16) 0.0472(5) Uani 1 1 d . . .
C6 C -0.5961(3) 0.65293(7) -0.28889(16) 0.0479(5) Uani 1 1 d . . .
C7 C -0.5990(4) 0.63843(8) -0.40650(18) 0.0648(6) Uani 1 1 d . . .
H7A H -0.4872 0.6493 -0.4441 0.078 Uiso 1 1 calc R . .
C8 C -0.7664(5) 0.60794(9) -0.4692(2) 0.0752(7) Uani 1 1 d . . .
H8A H -0.7660 0.5980 -0.5484 0.090 Uiso 1 1 calc R . .
C9 C -0.9312(4) 0.59244(9) -0.4157(2) 0.0744(7) Uani 1 1 d . . .
H9A H -1.0448 0.5722 -0.4587 0.089 Uiso 1 1 calc R . .
C10 C -0.9316(4) 0.60647(9) -0.2986(2) 0.0716(7) Uani 1 1 d . . .
H10A H -1.0448 0.5957 -0.2620 0.086 Uiso 1 1 calc R . .
C11 C -0.7640(4) 0.63654(8) -0.23531(19) 0.0603(6) Uani 1 1 d . . .
H11A H -0.7639 0.6459 -0.1556 0.072 Uiso 1 1 calc R . .
C12 C -0.1834(3) 0.63113(8) -0.04915(16) 0.0488(5) Uani 1 1 d . . .
C13 C -0.2961(4) 0.58757(8) -0.05925(19) 0.0596(6) Uani 1 1 d . . .
C14 C -0.1653(4) 0.55520(8) 0.0247(2) 0.0627(6) Uani 1 1 d . . .
C15 C 0.0257(4) 0.57944(7) 0.08518(17) 0.0511(5) Uani 1 1 d . . .
C16 C 0.2193(4) 0.56201(7) 0.17672(16) 0.0513(5) Uani 1 1 d . . .
C17 C 0.4224(4) 0.58667(8) 0.20250(18) 0.0643(6) Uani 1 1 d . . .
H17A H 0.4349 0.6161 0.1635 0.077 Uiso 1 1 calc R . .
C18 C 0.6069(4) 0.56806(10) 0.2855(2) 0.0770(7) Uani 1 1 d . . .
H18A H 0.7427 0.5850 0.3020 0.092 Uiso 1 1 calc R . .
C19 C 0.5912(5) 0.52476(10) 0.3437(2) 0.0783(8) Uani 1 1 d . . .
H19A H 0.7163 0.5121 0.3988 0.094 Uiso 1 1 calc R . .
C20 C 0.3916(5) 0.50039(9) 0.3202(2) 0.0801(8) Uani 1 1 d . . .
H20A H 0.3799 0.4710 0.3597 0.096 Uiso 1 1 calc R . .
C21 C 0.2069(4) 0.51911(8) 0.23813(19) 0.0697(7) Uani 1 1 d . . .
H21A H 0.0707 0.5024 0.2239 0.084 Uiso 1 1 calc R . .
H2 H 0.124(3) 0.6494(7) 0.0602(16) 0.051(6) Uiso 1 1 d . . .
H14 H -0.202(4) 0.5231(8) 0.037(2) 0.076(7) Uiso 1 1 d . . .
H1SB H 0.209(5) 0.7185(10) 0.015(2) 0.091(9) Uiso 1 1 d . . .
H13 H -0.433(4) 0.5780(8) -0.116(2) 0.078(7) Uiso 1 1 d . . .
H1SA H 0.401(5) 0.7241(11) 0.103(3) 0.107(12) Uiso 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
N1 C5 1.266(3) . ?
N1 C2 1.471(3) . ?
O1S H1SB 0.91(3) . ?
O1S H1SA 0.79(3) . ?
C1 C2 1.517(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C15 1.360(3) . ?
N2 C12 1.372(2) . ?
N2 H2 0.94(2) . ?
C2 N3 1.460(3) . ?
C2 C3 1.522(3) . ?
N3 C4 1.290(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C12 1.445(3) . ?
C4 C5 1.491(3) . ?
C5 C6 1.480(3) . ?
C6 C7 1.374(3) . ?
C6 C11 1.378(3) . ?
C7 C8 1.379(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.354(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.369(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(3) . ?
C13 C14 1.400(3) . ?
C13 H13 0.96(2) . ?
C14 C15 1.375(3) . ?
C14 H14 0.93(2) . ?
C15 C16 1.453(3) . ?
C16 C21 1.375(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.380(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.359(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.377(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 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
C5 N1 C2 107.14(16) . . ?
H1SB O1S H1SA 105(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C15 N2 C12 110.03(17) . . ?
C15 N2 H2 125.5(12) . . ?
C12 N2 H2 124.2(12) . . ?
N3 C2 N1 106.74(16) . . ?
N3 C2 C1 109.95(18) . . ?
N1 C2 C1 109.48(18) . . ?
N3 C2 C3 109.25(17) . . ?
N1 C2 C3 108.43(19) . . ?
C1 C2 C3 112.8(2) . . ?
C4 N3 C2 106.70(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 C12 122.92(18) . . ?
N3 C4 C5 109.42(17) . . ?
C12 C4 C5 127.51(18) . . ?
N1 C5 C6 122.12(17) . . ?
N1 C5 C4 109.94(17) . . ?
C6 C5 C4 127.88(18) . . ?
C7 C6 C11 118.7(2) . . ?
C7 C6 C5 120.10(19) . . ?
C11 C6 C5 121.20(18) . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C10 C11 C6 120.6(2) . . ?
C10 C11 H11A 119.7 . . ?
C6 C11 H11A 119.7 . . ?
C13 C12 N2 107.27(18) . . ?
C13 C12 C4 132.11(18) . . ?
N2 C12 C4 120.60(18) . . ?
C12 C13 C14 107.6(2) . . ?
C12 C13 H13 129.3(14) . . ?
C14 C13 H13 122.9(14) . . ?
C15 C14 C13 108.0(2) . . ?
C15 C14 H14 126.3(14) . . ?
C13 C14 H14 125.7(14) . . ?
N2 C15 C14 107.15(18) . . ?
N2 C15 C16 122.67(19) . . ?
C14 C15 C16 130.1(2) . . ?
C21 C16 C17 117.79(19) . . ?
C21 C16 C15 120.3(2) . . ?
C17 C16 C15 121.84(19) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C19 C20 C21 120.1(2) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C16 C21 C20 121.5(2) . . ?
C16 C21 H21A 119.3 . . ?
C20 C21 H21A 119.3 . . ?

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
C5 N1 C2 N3 2.1(2) . . . . ?
C5 N1 C2 C1 121.0(2) . . . . ?
C5 N1 C2 C3 -115.5(2) . . . . ?
N1 C2 N3 C4 -2.5(2) . . . . ?
C1 C2 N3 C4 -121.2(2) . . . . ?
C3 C2 N3 C4 114.5(2) . . . . ?
C2 N3 C4 C12 177.84(18) . . . . ?
C2 N3 C4 C5 2.0(2) . . . . ?
C2 N1 C5 C6 -178.36(18) . . . . ?
C2 N1 C5 C4 -0.9(2) . . . . ?
N3 C4 C5 N1 -0.8(2) . . . . ?
C12 C4 C5 N1 -176.34(19) . . . . ?
N3 C4 C5 C6 176.52(19) . . . . ?
C12 C4 C5 C6 1.0(3) . . . . ?
N1 C5 C6 C7 64.2(3) . . . . ?
C4 C5 C6 C7 -112.8(2) . . . . ?
N1 C5 C6 C11 -113.6(2) . . . . ?
C4 C5 C6 C11 69.4(3) . . . . ?
C11 C6 C7 C8 -0.2(3) . . . . ?
C5 C6 C7 C8 -178.1(2) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C7 C6 C11 C10 -0.3(3) . . . . ?
C5 C6 C11 C10 177.5(2) . . . . ?
C15 N2 C12 C13 0.4(2) . . . . ?
C15 N2 C12 C4 -178.12(18) . . . . ?
N3 C4 C12 C13 177.8(2) . . . . ?
C5 C4 C12 C13 -7.2(4) . . . . ?
N3 C4 C12 N2 -4.0(3) . . . . ?
C5 C4 C12 N2 170.96(18) . . . . ?
N2 C12 C13 C14 -0.3(3) . . . . ?
C4 C12 C13 C14 178.0(2) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C12 N2 C15 C14 -0.4(2) . . . . ?
C12 N2 C15 C16 177.05(18) . . . . ?
C13 C14 C15 N2 0.2(3) . . . . ?
C13 C14 C15 C16 -177.0(2) . . . . ?
N2 C15 C16 C21 166.5(2) . . . . ?
C14 C15 C16 C21 -16.7(3) . . . . ?
N2 C15 C16 C17 -15.5(3) . . . . ?
C14 C15 C16 C17 161.2(2) . . . . ?
C21 C16 C17 C18 1.3(3) . . . . ?
C15 C16 C17 C18 -176.8(2) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C17 C16 C21 C20 -1.8(3) . . . . ?
C15 C16 C21 C20 176.3(2) . . . . ?
C19 C20 C21 C16 1.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        66.02
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.043
