# 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_20
_database_code_depnum_ccdc_archive 'CCDC 1476590'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.9419(18)
_cell_length_b                   20.446(4)
_cell_length_c                   7.9832(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.874(3)
_cell_angle_gamma                90
_cell_volume                     1354.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5541
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.58
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic light orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.992
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2064
_reflns_number_total             2481
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+1.0201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1873
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.1035(3) 0.92181(11) 0.4711(3) 0.0734(7) Uani 1 1 d . . . . .
O2 O 0.4316(2) 0.69124(11) 0.7389(3) 0.0649(6) Uani 1 1 d . . . . .
N1 N -0.0892(3) 0.78821(11) 0.7047(3) 0.0514(6) Uani 1 1 d . . . . .
C1 C -0.2566(4) 0.98924(14) 0.6657(5) 0.0623(8) Uani 1 1 d . . . . .
H1 H -0.2786 1.0018 0.5470 0.075 Uiso 1 1 calc R . . . .
C2 C -0.3185(5) 1.02455(17) 0.7697(6) 0.0801(10) Uani 1 1 d . . . . .
H2 H -0.3823 1.0610 0.7214 0.096 Uiso 1 1 calc R . . . .
C3 C -0.2871(5) 1.00672(19) 0.9447(6) 0.0829(11) Uani 1 1 d . . . . .
H3 H -0.3300 1.0309 1.0148 0.100 Uiso 1 1 calc R . . . .
C4 C -0.1911(5) 0.95251(19) 1.0180(5) 0.0775(10) Uani 1 1 d . . . . .
H4 H -0.1692 0.9404 1.1371 0.093 Uiso 1 1 calc R . . . .
C5 C -0.1289(4) 0.91684(15) 0.9123(4) 0.0577(7) Uani 1 1 d . . . . .
H5 H -0.0646 0.8806 0.9608 0.069 Uiso 1 1 calc R . . . .
C6 C -0.1610(3) 0.93446(12) 0.7354(3) 0.0458(6) Uani 1 1 d . . . . .
C7 C -0.0907(3) 0.90050(13) 0.6184(3) 0.0478(6) Uani 1 1 d . . . . .
C8 C -0.0018(3) 0.83627(12) 0.6785(3) 0.0444(6) Uani 1 1 d . . . . .
C9 C -0.0211(3) 0.72764(13) 0.7374(4) 0.0523(7) Uani 1 1 d . . . . .
H9 H -0.0810 0.6935 0.7577 0.063 Uiso 1 1 calc R . . . .
C10 C 0.1293(3) 0.71415(13) 0.7422(4) 0.0477(6) Uani 1 1 d . . . . .
H10 H 0.1687 0.6716 0.7621 0.057 Uiso 1 1 calc R . . . .
C11 C 0.2248(3) 0.76490(12) 0.7170(3) 0.0424(6) Uani 1 1 d . . . . .
C12 C 0.3833(3) 0.75471(14) 0.7195(4) 0.0483(6) Uani 1 1 d . . . . .
C13 C 0.4725(3) 0.80666(16) 0.7010(4) 0.0597(8) Uani 1 1 d . . . . .
H13 H 0.5768 0.8000 0.7052 0.072 Uiso 1 1 calc R . . . .
C14 C 0.4071(4) 0.86975(16) 0.6758(4) 0.0640(8) Uani 1 1 d . . . . .
H14 H 0.4697 0.9046 0.6651 0.077 Uiso 1 1 calc R . . . .
C15 C 0.2543(4) 0.88157(14) 0.6664(4) 0.0558(7) Uani 1 1 d . . . . .
H15 H 0.2127 0.9238 0.6468 0.067 Uiso 1 1 calc R . . . .
C16 C 0.1595(3) 0.82894(12) 0.6867(3) 0.0432(6) Uani 1 1 d . . . . .
C17 C 0.5879(4) 0.6776(2) 0.7385(6) 0.0841(11) Uani 1 1 d . . . . .
H17A H 0.5931 0.6915 0.6258 0.126 Uiso 1 1 calc GR . . . .
H17B H 0.6084 0.6314 0.7534 0.126 Uiso 1 1 calc GR . . . .
H17C H 0.6675 0.7007 0.8358 0.126 Uiso 1 1 calc GR . . . .


_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 C7 1.219(3) . ?
O2 C12 1.358(3) . ?
O2 C17 1.427(3) . ?
N1 C8 1.320(3) . ?
N1 C9 1.362(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(5) . ?
C1 C6 1.393(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C6 C7 1.478(4) . ?
C7 C8 1.518(4) . ?
C8 C16 1.427(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.359(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.405(4) . ?
C11 C12 1.426(4) . ?
C11 C16 1.417(4) . ?
C12 C13 1.369(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.400(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.361(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.416(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 O2 C17 117.2(2) . . ?
C8 N1 C9 117.3(2) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.7(3) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 117.9(3) . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 C7 123.3(3) . . ?
O1 C7 C6 122.2(3) . . ?
O1 C7 C8 117.6(2) . . ?
C6 C7 C8 120.2(2) . . ?
N1 C8 C7 115.0(2) . . ?
N1 C8 C16 124.3(2) . . ?
C16 C8 C7 120.5(2) . . ?
N1 C9 H9 118.1 . . ?
C10 C9 N1 123.9(2) . . ?
C10 C9 H9 118.1 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 123.0(2) . . ?
C10 C11 C16 118.2(2) . . ?
C16 C11 C12 118.8(2) . . ?
O2 C12 C11 114.4(2) . . ?
O2 C12 C13 125.5(3) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 C8 116.7(2) . . ?
C15 C16 C8 123.6(2) . . ?
C15 C16 C11 119.7(2) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O1 C7 C8 N1 -117.8(3) . . . . ?
O1 C7 C8 C16 56.3(4) . . . . ?
O2 C12 C13 C14 177.8(3) . . . . ?
N1 C8 C16 C11 3.0(4) . . . . ?
N1 C8 C16 C15 -177.0(3) . . . . ?
N1 C9 C10 C11 1.7(4) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C6 C7 O1 5.9(4) . . . . ?
C1 C6 C7 C8 -172.9(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C1 C6 C7 -176.8(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C4 C5 C6 C7 176.5(3) . . . . ?
C5 C6 C7 O1 -170.3(3) . . . . ?
C5 C6 C7 C8 10.9(4) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C6 C7 C8 N1 61.0(3) . . . . ?
C6 C7 C8 C16 -124.8(3) . . . . ?
C7 C8 C16 C11 -170.6(2) . . . . ?
C7 C8 C16 C15 9.4(4) . . . . ?
C8 N1 C9 C10 -0.8(4) . . . . ?
C9 N1 C8 C7 172.3(2) . . . . ?
C9 N1 C8 C16 -1.6(4) . . . . ?
C9 C10 C11 C12 -179.7(3) . . . . ?
C9 C10 C11 C16 -0.2(4) . . . . ?
C10 C11 C12 O2 3.2(4) . . . . ?
C10 C11 C12 C13 -177.5(3) . . . . ?
C10 C11 C16 C8 -2.0(3) . . . . ?
C10 C11 C16 C15 178.1(2) . . . . ?
C11 C12 C13 C14 -1.4(4) . . . . ?
C12 C11 C16 C8 177.6(2) . . . . ?
C12 C11 C16 C15 -2.3(4) . . . . ?
C12 C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 C16 1.5(5) . . . . ?
C14 C15 C16 C8 -179.8(3) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C16 C11 C12 O2 -176.3(2) . . . . ?
C16 C11 C12 C13 3.0(4) . . . . ?
C17 O2 C12 C11 178.7(3) . . . . ?
C17 O2 C12 C13 -0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
