# 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_xhl-12-12
_database_code_depnum_ccdc_archive 'CCDC 1522911'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_audit_creation_date             2016-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_weight         366.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   10.820(4)
_cell_length_b                   17.17(2)
_cell_length_c                   10.534(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.49(4)
_cell_angle_gamma                90
_cell_volume                     1886(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1087
_cell_measurement_temperature    290.55(10)
_cell_measurement_theta_max      24.5470
_cell_measurement_theta_min      3.9920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6890
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.369
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.55(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9629
_diffrn_measured_fraction_theta_max 0.7931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  -7.00   1.00   15.95    --   16.50 -57.00 150.00   40
  2  ω    -52.00  78.00   1.00   15.95    --   16.50   0.00 -30.00  130
  3  ω     57.00  89.00   1.00   15.95    --   16.50 178.00 -90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0518960000
_diffrn_orient_matrix_UB_12      0.0143941000
_diffrn_orient_matrix_UB_13      -0.0499049000
_diffrn_orient_matrix_UB_21      0.0385624000
_diffrn_orient_matrix_UB_22      0.0322917000
_diffrn_orient_matrix_UB_23      -0.0107537000
_diffrn_orient_matrix_UB_31      0.0196818000
_diffrn_orient_matrix_UB_32      -0.0228727000
_diffrn_orient_matrix_UB_33      -0.0467991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1995
_reflns_number_total             3716
_reflns_odcompleteness_completeness 96.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3716
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0760
_refine_ls_restrained_S_all      1.066
_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)+(0.1220P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2518
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C23, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.05
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.05
Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C23) \\sim Ueq: with sigma of 0.0025 and sigma for terminal atoms of 0.005
4.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.2430(4) 0.7123(2) 1.0475(3) 0.0727(9) Uani 1 1 d . U . . .
H1 H 0.1624 0.7056 1.0614 0.087 Uiso 1 1 calc R . . . .
C2 C 0.3095(4) 0.7798(2) 1.0972(3) 0.0747(10) Uani 1 1 d . U . . .
H2 H 0.2726 0.8154 1.1427 0.090 Uiso 1 1 calc R . . . .
C3 C 0.4268(4) 0.7946(2) 1.0806(3) 0.0657(9) Uani 1 1 d . U . . .
H3 H 0.479(3) 0.845(2) 1.118(3) 0.070(9) Uiso 1 1 d . . . . .
C4 C 0.4763(3) 0.73768(17) 1.0130(3) 0.0520(7) Uani 1 1 d . U . . .
C5 C 0.3983(3) 0.67057(16) 0.9687(2) 0.0467(7) Uani 1 1 d . U . . .
C6 C 0.5899(3) 0.72887(16) 0.9800(3) 0.0534(7) Uani 1 1 d . U . . .
H6 H 0.6580 0.7638 0.9966 0.064 Uiso 1 1 calc R . . . .
C7 C 0.5830(3) 0.65758(15) 0.9169(2) 0.0457(7) Uani 1 1 d . U . . .
C8 C 0.6700(3) 0.61859(16) 0.8602(3) 0.0468(7) Uani 1 1 d . U . . .
C9 C 0.6415(3) 0.54668(17) 0.8013(2) 0.0461(7) Uani 1 1 d . U . . .
C10 C 0.5216(2) 0.50914(16) 0.7961(2) 0.0433(6) Uani 1 1 d . U . . .
C11 C 0.4330(3) 0.54645(15) 0.8496(2) 0.0430(6) Uani 1 1 d . U . . .
C12 C 0.3193(3) 0.50969(17) 0.8464(3) 0.0516(7) Uani 1 1 d . U . . .
H12 H 0.2590 0.5347 0.8805 0.062 Uiso 1 1 calc R . . . .
C13 C 0.2935(3) 0.43565(18) 0.7930(3) 0.0592(8) Uani 1 1 d . U . . .
H13 H 0.2161 0.4118 0.7920 0.071 Uiso 1 1 calc R . . . .
C14 C 0.3795(3) 0.39727(18) 0.7419(3) 0.0594(8) Uani 1 1 d . U . . .
H14 H 0.3619 0.3475 0.7069 0.071 Uiso 1 1 calc R . . . .
C15 C 0.4910(3) 0.43326(17) 0.7432(3) 0.0523(7) Uani 1 1 d . U . . .
H15 H 0.5499 0.4074 0.7081 0.063 Uiso 1 1 calc R . . . .
C16 C 0.7342(3) 0.50717(17) 0.7426(3) 0.0502(7) Uani 1 1 d . U . . .
C17 C 0.7114(3) 0.5063(2) 0.6071(3) 0.0695(9) Uani 1 1 d . U . . .
H17 H 0.6381 0.5293 0.5536 0.083 Uiso 1 1 calc R . . . .
C18 C 0.7977(4) 0.4713(2) 0.5535(4) 0.0850(11) Uani 1 1 d . U . . .
H18 H 0.7845 0.4707 0.4626 0.102 Uiso 1 1 calc R . . . .
C19 C 0.9057(4) 0.4363(3) 0.6343(4) 0.0884(11) Uani 1 1 d . U . . .
H19 H 0.9638 0.4119 0.5964 0.106 Uiso 1 1 calc R . . . .
C20 C 0.9293(4) 0.4369(3) 0.7702(4) 0.0881(11) Uani 1 1 d . U . . .
H20 H 1.0027 0.4140 0.8238 0.106 Uiso 1 1 calc R . . . .
C21 C 0.8423(3) 0.4718(2) 0.8224(3) 0.0674(9) Uani 1 1 d . U . . .
H21 H 0.8552 0.4721 0.9133 0.081 Uiso 1 1 calc R . . . .
C22 C 0.7932(3) 0.65964(17) 0.8730(3) 0.0549(8) Uani 1 1 d . U . . .
C23 C 0.9175(5) 0.7203(3) 0.7528(4) 0.1041(13) Uani 1 1 d . U . . .
H23A H 0.9680 0.7334 0.8410 0.125 Uiso 1 1 calc R . . . .
H23B H 0.8984 0.7678 0.7016 0.125 Uiso 1 1 calc R . . . .
C24 C 0.9867(6) 0.6663(4) 0.6916(8) 0.170(3) Uani 1 1 d . U . . .
H24A H 0.9334 0.6513 0.6068 0.254 Uiso 1 1 calc GR . . . .
H24B H 1.0094 0.6209 0.7461 0.254 Uiso 1 1 calc GR . . . .
H24C H 1.0631 0.6909 0.6812 0.254 Uiso 1 1 calc GR . . . .
N1 N 0.2849(2) 0.65677(15) 0.9819(2) 0.0602(7) Uani 1 1 d . U . . .
N2 N 0.4658(2) 0.62128(13) 0.9069(2) 0.0443(6) Uani 1 1 d . U . . .
O1 O 0.8736(2) 0.67183(18) 0.9757(2) 0.0893(9) Uani 1 1 d . U . . .
O2 O 0.8014(2) 0.68153(17) 0.7574(2) 0.0905(9) Uani 1 1 d . 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
C1 C2 1.389(5) . ?
C1 N1 1.327(4) . ?
C2 C3 1.351(5) . ?
C3 C4 1.397(4) . ?
C4 C5 1.431(4) . ?
C4 C6 1.372(4) . ?
C5 N1 1.292(4) . ?
C5 N2 1.388(3) . ?
C6 C7 1.385(4) . ?
C7 C8 1.411(4) . ?
C7 N2 1.391(3) . ?
C8 C9 1.379(4) . ?
C8 C22 1.482(4) . ?
C9 C10 1.436(4) . ?
C9 C16 1.477(4) . ?
C10 C11 1.391(3) . ?
C10 C15 1.421(4) . ?
C11 C12 1.375(4) . ?
C11 N2 1.424(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.363(4) . ?
C14 C15 1.352(4) . ?
C16 C17 1.382(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.354(5) . ?
C18 C19 1.385(5) . ?
C19 C20 1.386(5) . ?
C20 C21 1.350(5) . ?
C22 O1 1.212(4) . ?
C22 O2 1.299(3) . ?
C23 C24 1.446(7) . ?
C23 O2 1.434(5) . ?

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
N1 C1 C2 125.5(3) . . ?
C3 C2 C1 121.2(3) . . ?
C2 C3 C4 115.8(3) . . ?
C3 C4 C5 117.1(3) . . ?
C6 C4 C3 134.2(3) . . ?
C6 C4 C5 108.6(3) . . ?
N1 C5 C4 127.3(3) . . ?
N1 C5 N2 124.9(3) . . ?
N2 C5 C4 107.8(2) . . ?
C4 C6 C7 106.4(3) . . ?
C6 C7 C8 131.7(3) . . ?
C6 C7 N2 111.3(2) . . ?
N2 C7 C8 117.0(2) . . ?
C7 C8 C22 114.9(3) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 C22 123.7(2) . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 C16 120.3(2) . . ?
C10 C9 C16 119.1(3) . . ?
C11 C10 C9 119.4(3) . . ?
C11 C10 C15 117.9(2) . . ?
C15 C10 C9 122.6(2) . . ?
C10 C11 N2 117.8(2) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 N2 123.0(2) . . ?
C11 C12 C13 120.8(3) . . ?
C14 C13 C12 121.2(3) . . ?
C15 C14 C13 118.5(3) . . ?
C14 C15 C10 122.4(3) . . ?
C17 C16 C9 119.0(3) . . ?
C17 C16 C21 120.7(3) . . ?
C21 C16 C9 120.4(2) . . ?
C18 C17 C16 118.9(3) . . ?
C17 C18 C19 119.9(3) . . ?
C20 C19 C18 121.6(3) . . ?
C21 C20 C19 117.9(3) . . ?
C20 C21 C16 121.0(3) . . ?
O1 C22 C8 125.2(3) . . ?
O1 C22 O2 125.0(3) . . ?
O2 C22 C8 109.7(3) . . ?
O2 C23 C24 106.3(4) . . ?
C5 N1 C1 113.0(3) . . ?
C5 N2 C7 106.0(2) . . ?
C5 N2 C11 130.2(2) . . ?
C7 N2 C11 123.7(2) . . ?
C22 O2 C23 116.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.779
_oxdiff_exptl_absorpt_empirical_full_min 0.388
