# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_180717xj
_database_code_depnum_ccdc_archive 'CCDC 1859558'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_audit_creation_date             2018-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N2 O2'
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36
_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 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   6.1601(7)
_cell_length_b                   16.0224(18)
_cell_length_c                   16.6437(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.193(2)
_cell_angle_gamma                90
_cell_volume                     1621.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3047
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.333
_cell_measurement_theta_min      2.542
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0565 before and 0.0355 after correction. The Ratio of minimum to maximum transmission is 0.9218. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         1.775
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2614
_reflns_number_total             3656
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0182(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.3199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.3792(2) 0.49081(7) 0.64599(7) 0.0602(3) Uani 1 1 d . . . . .
O2 O -0.54594(18) 0.69352(8) 0.53213(6) 0.0568(3) Uani 1 1 d . . . . .
N1 N 0.2735(2) 0.60787(8) 0.70892(7) 0.0436(3) Uani 1 1 d . . . . .
H1 H 0.317053 0.640777 0.749087 0.052 Uiso 1 1 calc R . . . .
N2 N 0.62092(19) 0.59512(7) 0.82535(7) 0.0401(3) Uani 1 1 d . . . . .
C1 C 0.4097(2) 0.54362(9) 0.70009(9) 0.0407(3) Uani 1 1 d . . . . .
C2 C 0.0698(2) 0.62860(9) 0.66151(8) 0.0393(3) Uani 1 1 d . . . . .
C3 C -0.0594(2) 0.69311(8) 0.69110(8) 0.0360(3) Uani 1 1 d . . . . .
C4 C -0.2698(2) 0.71215(8) 0.64560(8) 0.0370(3) Uani 1 1 d . . . . .
C5 C -0.3435(2) 0.66927(10) 0.57131(9) 0.0424(4) Uani 1 1 d . . . . .
C6 C -0.6305(3) 0.65274(14) 0.45778(11) 0.0715(6) Uani 1 1 d . . . . .
H6A H -0.534406 0.662680 0.418705 0.107 Uiso 1 1 calc GR . . . .
H6B H -0.774202 0.674187 0.437286 0.107 Uiso 1 1 calc GR . . . .
H6C H -0.639945 0.593828 0.467161 0.107 Uiso 1 1 calc GR . . . .
C7 C -0.2149(3) 0.60947(10) 0.54386(9) 0.0493(4) Uani 1 1 d . . . . .
H7 H -0.263195 0.582304 0.494889 0.059 Uiso 1 1 calc R . . . .
C8 C -0.0095(3) 0.58896(10) 0.58965(9) 0.0492(4) Uani 1 1 d . . . . .
H8 H 0.074874 0.547411 0.570709 0.059 Uiso 1 1 calc R . . . .
C9 C -0.4034(2) 0.77292(9) 0.67590(9) 0.0437(4) Uani 1 1 d . . . . .
H9 H -0.541906 0.784711 0.646918 0.052 Uiso 1 1 calc R . . . .
C10 C -0.3322(3) 0.81434(10) 0.74678(9) 0.0475(4) Uani 1 1 d . . . . .
H10 H -0.422041 0.853848 0.765931 0.057 Uiso 1 1 calc R . . . .
C11 C -0.1230(3) 0.79724(10) 0.79079(9) 0.0483(4) Uani 1 1 d . . . . .
H11 H -0.074092 0.826214 0.838675 0.058 Uiso 1 1 calc R . . . .
C12 C 0.0094(2) 0.73848(9) 0.76402(9) 0.0425(3) Uani 1 1 d . . . . .
H12 H 0.147339 0.727997 0.794136 0.051 Uiso 1 1 calc R . . . .
C13 C 0.6120(2) 0.54171(9) 0.76441(9) 0.0385(3) Uani 1 1 d . . . . .
C14 C 0.8076(2) 0.59655(9) 0.88230(8) 0.0393(3) Uani 1 1 d . . . . .
C15 C 0.9890(2) 0.54328(9) 0.87736(9) 0.0412(3) Uani 1 1 d . . . . .
C16 C 0.9677(3) 0.48589(10) 0.81250(10) 0.0477(4) Uani 1 1 d . . . . .
H16 H 1.081355 0.448798 0.808086 0.057 Uiso 1 1 calc R . . . .
C17 C 0.7814(2) 0.48457(10) 0.75626(9) 0.0455(4) Uani 1 1 d . . . . .
H17 H 0.765927 0.446767 0.713327 0.055 Uiso 1 1 calc R . . . .
C18 C 1.1815(3) 0.55122(11) 0.93607(10) 0.0527(4) Uani 1 1 d . . . . .
H18 H 1.301782 0.516983 0.933016 0.063 Uiso 1 1 calc R . . . .
C19 C 1.1918(3) 0.60833(12) 0.99672(11) 0.0610(5) Uani 1 1 d . . . . .
H19 H 1.319653 0.613417 1.034528 0.073 Uiso 1 1 calc R . . . .
C20 C 1.0104(3) 0.65991(12) 1.00285(10) 0.0602(5) Uani 1 1 d . . . . .
H20 H 1.018997 0.698338 1.045119 0.072 Uiso 1 1 calc R . . . .
C21 C 0.8221(3) 0.65424(10) 0.94754(10) 0.0516(4) Uani 1 1 d . . . . .
H21 H 0.702893 0.688329 0.952626 0.062 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
O1 C1 1.2281(17) . ?
O2 C5 1.3682(18) . ?
O2 C6 1.423(2) . ?
N1 C1 1.3508(18) . ?
N1 C2 1.4109(18) . ?
N2 C13 1.3215(18) . ?
N2 C14 1.3686(18) . ?
C1 C13 1.508(2) . ?
C2 C3 1.439(2) . ?
C2 C8 1.373(2) . ?
C3 C4 1.4258(19) . ?
C3 C12 1.4202(19) . ?
C4 C5 1.424(2) . ?
C4 C9 1.418(2) . ?
C5 C7 1.367(2) . ?
C7 C8 1.408(2) . ?
C9 C10 1.364(2) . ?
C10 C11 1.404(2) . ?
C11 C12 1.366(2) . ?
C13 C17 1.411(2) . ?
C14 C15 1.419(2) . ?
C14 C21 1.418(2) . ?
C15 C16 1.408(2) . ?
C15 C18 1.416(2) . ?
C16 C17 1.361(2) . ?
C18 C19 1.356(2) . ?
C19 C20 1.406(3) . ?
C20 C21 1.364(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
C5 O2 C6 117.61(13) . . ?
C1 N1 C2 129.12(13) . . ?
C13 N2 C14 118.02(12) . . ?
O1 C1 N1 125.45(14) . . ?
O1 C1 C13 121.25(13) . . ?
N1 C1 C13 113.30(12) . . ?
N1 C2 C3 117.96(12) . . ?
C8 C2 N1 122.61(14) . . ?
C8 C2 C3 119.42(13) . . ?
C4 C3 C2 118.53(12) . . ?
C12 C3 C2 123.66(13) . . ?
C12 C3 C4 117.80(13) . . ?
C5 C4 C3 119.63(13) . . ?
C9 C4 C3 119.20(13) . . ?
C9 C4 C5 121.16(13) . . ?
O2 C5 C4 114.62(13) . . ?
C7 C5 O2 124.92(13) . . ?
C7 C5 C4 120.46(14) . . ?
C5 C7 C8 120.08(14) . . ?
C2 C8 C7 121.83(14) . . ?
C10 C9 C4 121.13(14) . . ?
C9 C10 C11 119.87(15) . . ?
C12 C11 C10 120.71(14) . . ?
C11 C12 C3 121.26(14) . . ?
N2 C13 C1 117.41(12) . . ?
N2 C13 C17 123.58(14) . . ?
C17 C13 C1 119.01(13) . . ?
N2 C14 C15 122.16(13) . . ?
N2 C14 C21 118.98(13) . . ?
C21 C14 C15 118.85(14) . . ?
C16 C15 C14 117.34(14) . . ?
C16 C15 C18 123.56(14) . . ?
C18 C15 C14 119.09(14) . . ?
C17 C16 C15 120.17(14) . . ?
C16 C17 C13 118.66(14) . . ?
C19 C18 C15 120.56(16) . . ?
C18 C19 C20 120.48(17) . . ?
C21 C20 C19 120.78(16) . . ?
C20 C21 C14 120.21(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
O1 C1 C13 N2 -172.81(13) . . . . ?
O1 C1 C13 C17 8.0(2) . . . . ?
O2 C5 C7 C8 -179.45(14) . . . . ?
N1 C1 C13 N2 7.46(18) . . . . ?
N1 C1 C13 C17 -171.76(13) . . . . ?
N1 C2 C3 C4 -177.30(12) . . . . ?
N1 C2 C3 C12 1.8(2) . . . . ?
N1 C2 C8 C7 178.86(14) . . . . ?
N2 C13 C17 C16 -2.2(2) . . . . ?
N2 C14 C15 C16 -2.2(2) . . . . ?
N2 C14 C15 C18 176.68(13) . . . . ?
N2 C14 C21 C20 -176.71(15) . . . . ?
C1 N1 C2 C3 170.65(13) . . . . ?
C1 N1 C2 C8 -8.4(2) . . . . ?
C1 C13 C17 C16 176.96(13) . . . . ?
C2 N1 C1 O1 1.3(2) . . . . ?
C2 N1 C1 C13 -178.96(13) . . . . ?
C2 C3 C4 C5 -2.04(19) . . . . ?
C2 C3 C4 C9 177.15(12) . . . . ?
C2 C3 C12 C11 -177.76(14) . . . . ?
C3 C2 C8 C7 -0.2(2) . . . . ?
C3 C4 C5 O2 -178.95(12) . . . . ?
C3 C4 C5 C7 0.7(2) . . . . ?
C3 C4 C9 C10 1.2(2) . . . . ?
C4 C3 C12 C11 1.4(2) . . . . ?
C4 C5 C7 C8 0.9(2) . . . . ?
C4 C9 C10 C11 0.3(2) . . . . ?
C5 C4 C9 C10 -179.58(14) . . . . ?
C5 C7 C8 C2 -1.2(2) . . . . ?
C6 O2 C5 C4 -179.51(14) . . . . ?
C6 O2 C5 C7 0.9(2) . . . . ?
C8 C2 C3 C4 1.8(2) . . . . ?
C8 C2 C3 C12 -179.10(14) . . . . ?
C9 C4 C5 O2 1.88(19) . . . . ?
C9 C4 C5 C7 -178.47(14) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C10 C11 C12 C3 0.1(2) . . . . ?
C12 C3 C4 C5 178.80(12) . . . . ?
C12 C3 C4 C9 -2.02(19) . . . . ?
C13 N2 C14 C15 0.3(2) . . . . ?
C13 N2 C14 C21 179.05(13) . . . . ?
C14 N2 C13 C1 -177.23(12) . . . . ?
C14 N2 C13 C17 2.0(2) . . . . ?
C14 C15 C16 C17 1.9(2) . . . . ?
C14 C15 C18 C19 0.7(2) . . . . ?
C15 C14 C21 C20 2.1(2) . . . . ?
C15 C16 C17 C13 0.2(2) . . . . ?
C15 C18 C19 C20 0.8(3) . . . . ?
C16 C15 C18 C19 179.46(16) . . . . ?
C18 C15 C16 C17 -176.93(15) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C14 -0.7(3) . . . . ?
C21 C14 C15 C16 179.06(14) . . . . ?
C21 C14 C15 C18 -2.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
