# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_sp_1
_database_code_depnum_ccdc_archive 'CCDC 1427013'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.7059(3)
_cell_length_b                   15.7541(4)
_cell_length_c                   10.5250(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.513(2)
_cell_angle_gamma                90.00
_cell_volume                     1601.91(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_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            21958
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2701
_reflns_number_gt                2317
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0557P)²+0.2191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2701
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C11 C 0.56692(14) 0.11376(8) 0.30234(12) 0.0427(3) Uani 1 1 d . . .
C16 C 0.56981(14) 0.17416(8) 0.20492(12) 0.0408(3) Uani 1 1 d . . .
C12 C 0.48659(16) 0.04101(8) 0.27850(14) 0.0512(4) Uani 1 1 d . . .
H12 H 0.4863 -0.0006 0.3411 0.061 Uiso 1 1 calc R . .
C20 C 0.62211(16) 0.32782(8) 0.18145(14) 0.0497(4) Uani 1 1 d . . .
H20 H 0.5348 0.3453 0.1473 0.060 Uiso 1 1 calc R . .
C15 C 0.48951(15) 0.16229(9) 0.08983(13) 0.0492(4) Uani 1 1 d . . .
H15 H 0.4910 0.2027 0.0256 0.059 Uiso 1 1 calc R . .
C19 C 0.73574(16) 0.37806(9) 0.20114(15) 0.0542(4) Uani 1 1 d . . .
H19 H 0.7402 0.4358 0.1836 0.065 Uiso 1 1 calc R . .
C17 C 0.79578(15) 0.24662(9) 0.26343(13) 0.0490(4) Uani 1 1 d . . .
H17 H 0.8465 0.1997 0.2944 0.059 Uiso 1 1 calc R . .
C18 C 0.84565(16) 0.32660(9) 0.25291(14) 0.0524(4) Uani 1 1 d . . .
H18 H 0.9361 0.3442 0.2758 0.063 Uiso 1 1 calc R . .
C14 C 0.40756(16) 0.09099(9) 0.06986(14) 0.0551(4) Uani 1 1 d . . .
H14 H 0.3524 0.0842 -0.0067 0.066 Uiso 1 1 calc R . .
C13 C 0.40763(16) 0.02979(9) 0.16370(15) 0.0558(4) Uani 1 1 d . . .
H13 H 0.3544 -0.0190 0.1495 0.067 Uiso 1 1 calc R . .
C9 C 0.62552(13) 0.29583(8) 0.66700(12) 0.0400(3) Uani 1 1 d . . .
N1 N 0.54135(12) 0.34380(7) 0.58428(11) 0.0488(3) Uani 1 1 d . . .
C1 C 0.66869(13) 0.21497(8) 0.62358(11) 0.0393(3) Uani 1 1 d . . .
C5 C 0.66927(14) 0.32207(9) 0.79358(13) 0.0460(3) Uani 1 1 d . . .
C6 C 0.62284(17) 0.40214(10) 0.83188(15) 0.0590(4) Uani 1 1 d . . .
H6 H 0.6503 0.4226 0.9132 0.071 Uiso 1 1 calc R . .
C4 C 0.75502(16) 0.26776(10) 0.87387(14) 0.0538(4) Uani 1 1 d . . .
H4 H 0.7850 0.2845 0.9566 0.065 Uiso 1 1 calc R . .
C8 C 0.49920(17) 0.41728(9) 0.62689(16) 0.0587(4) Uani 1 1 d . . .
H8 H 0.4400 0.4500 0.5721 0.070 Uiso 1 1 calc R . .
C7 C 0.53795(18) 0.44908(10) 0.74950(16) 0.0637(4) Uani 1 1 d . . .
H7 H 0.5059 0.5016 0.7740 0.076 Uiso 1 1 calc R . .
N3 N 0.65754(11) 0.24690(6) 0.22042(10) 0.0415(3) Uani 1 1 d . . .
C10 C 0.64347(15) 0.12139(8) 0.43281(13) 0.0468(3) Uani 1 1 d . . .
N2 N 0.61896(12) 0.19324(7) 0.49805(10) 0.0442(3) Uani 1 1 d . . .
H2N H 0.5663 0.2301 0.4574 0.053 Uiso 1 1 calc R . .
O1 O 0.71664(15) 0.06372(7) 0.47740(11) 0.0799(4) Uani 1 1 d . . .
C2 C 0.75074(14) 0.16380(9) 0.70513(13) 0.0460(3) Uani 1 1 d . . .
H2 H 0.7781 0.1108 0.6777 0.055 Uiso 1 1 calc R . .
C3 C 0.79339(15) 0.19111(10) 0.82975(14) 0.0538(4) Uani 1 1 d . . .
H3 H 0.8494 0.1558 0.8835 0.065 Uiso 1 1 calc R . .


_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
C11 C12 1.3952(19) . ?
C11 C16 1.4011(18) . ?
C11 C10 1.5020(19) . ?
C16 C15 1.3886(19) . ?
C16 N3 1.4276(16) . ?
C12 C13 1.379(2) . ?
C20 C19 1.357(2) . ?
C20 N3 1.3727(16) . ?
C15 C14 1.381(2) . ?
C19 C18 1.407(2) . ?
C17 C18 1.3580(19) . ?
C17 N3 1.3743(19) . ?
C14 C13 1.380(2) . ?
C9 N1 1.3638(17) . ?
C9 C5 1.4202(18) . ?
C9 C1 1.4297(18) . ?
N1 C8 1.3205(18) . ?
C1 C2 1.3746(18) . ?
C1 N2 1.4048(16) . ?
C5 C6 1.411(2) . ?
C5 C4 1.416(2) . ?
C6 C7 1.357(2) . ?
C4 C3 1.359(2) . ?
C8 C7 1.402(2) . ?
C10 O1 1.2189(16) . ?
C10 N2 1.3568(16) . ?
C2 C3 1.404(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
C12 C11 C16 118.45(13) . . ?
C12 C11 C10 116.67(12) . . ?
C16 C11 C10 124.87(12) . . ?
C15 C16 C11 119.86(12) . . ?
C15 C16 N3 119.11(11) . . ?
C11 C16 N3 121.01(12) . . ?
C13 C12 C11 121.13(13) . . ?
C19 C20 N3 108.63(13) . . ?
C14 C15 C16 120.61(13) . . ?
C20 C19 C18 107.32(13) . . ?
C18 C17 N3 108.34(13) . . ?
C17 C18 C19 107.65(13) . . ?
C13 C14 C15 119.91(14) . . ?
C12 C13 C14 119.97(13) . . ?
N1 C9 C5 122.98(12) . . ?
N1 C9 C1 117.75(11) . . ?
C5 C9 C1 119.26(12) . . ?
C8 N1 C9 117.07(12) . . ?
C2 C1 N2 124.78(12) . . ?
C2 C1 C9 119.54(12) . . ?
N2 C1 C9 115.66(11) . . ?
C6 C5 C4 123.73(13) . . ?
C6 C5 C9 116.95(13) . . ?
C4 C5 C9 119.32(13) . . ?
C7 C6 C5 119.71(14) . . ?
C3 C4 C5 119.86(13) . . ?
N1 C8 C7 124.16(15) . . ?
C6 C7 C8 119.11(14) . . ?
C20 N3 C17 108.06(11) . . ?
C20 N3 C16 125.57(12) . . ?
C17 N3 C16 126.00(11) . . ?
O1 C10 N2 123.43(13) . . ?
O1 C10 C11 120.74(12) . . ?
N2 C10 C11 115.72(11) . . ?
C10 N2 C1 128.19(11) . . ?
C1 C2 C3 120.30(13) . . ?
C4 C3 C2 121.71(14) . . ?

_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.956
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.073
