# 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 
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data_mo_cxy0266_0m
_database_code_depnum_ccdc_archive 'CCDC 1867201'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;
_audit_creation_date             2017-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O'
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_weight         276.33
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   14.2864(13)
_cell_length_b                   5.3688(5)
_cell_length_c                   19.4632(16)
_cell_angle_alpha                90
_cell_angle_beta                 108.952(3)
_cell_angle_gamma                90
_cell_volume                     1411.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1097 before and 0.0686 after correction. The Ratio of minimum to maximum transmission is 0.9399. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17531
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2698
_reflns_number_total             3204
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.6730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1067
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.52865(7) -0.18572(19) 0.43311(5) 0.0241(2) Uani 1 1 d . . . . .
N1 N 0.81416(8) 0.2830(2) 0.51256(6) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.75201(8) 0.34182(19) 0.44414(5) 0.0143(2) Uani 1 1 d . . . . .
C1 C 0.78837(9) 0.5175(2) 0.40339(6) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.72598(10) 0.6844(2) 0.35567(7) 0.0175(3) Uani 1 1 d . . . . .
H2 H 0.6568 0.6821 0.3481 0.021 Uiso 1 1 calc R . . . .
C3 C 0.76584(10) 0.8555(2) 0.31902(7) 0.0200(3) Uani 1 1 d . . . . .
H3 H 0.7232 0.9657 0.2847 0.024 Uiso 1 1 calc R . . . .
C4 C 0.86695(10) 0.8665(2) 0.33203(7) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.8938 0.9876 0.3081 0.025 Uiso 1 1 calc R . . . .
C5 C 0.92887(10) 0.7001(3) 0.38020(7) 0.0222(3) Uani 1 1 d . . . . .
H5 H 0.9983 0.7076 0.3893 0.027 Uiso 1 1 calc R . . . .
C6 C 0.88989(9) 0.5225(3) 0.41521(7) 0.0192(3) Uani 1 1 d . . . . .
H6 H 0.9322 0.4052 0.4470 0.023 Uiso 1 1 calc R . . . .
C7 C 0.58715(10) 0.2313(3) 0.35387(7) 0.0185(3) Uani 1 1 d . . . . .
H7A H 0.5418 0.3646 0.3569 0.028 Uiso 1 1 calc GR . . . .
H7B H 0.5507 0.0740 0.3419 0.028 Uiso 1 1 calc GR . . . .
H7C H 0.6162 0.2716 0.3160 0.028 Uiso 1 1 calc GR . . . .
C8 C 0.66739(9) 0.2063(2) 0.42509(7) 0.0138(3) Uani 1 1 d . . . . .
C9 C 0.67372(9) 0.0505(2) 0.48381(6) 0.0138(3) Uani 1 1 d . . . . .
C10 C 0.60156(9) -0.1432(2) 0.48602(7) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.61996(10) -0.2928(3) 0.55439(7) 0.0215(3) Uani 1 1 d . . . . .
H11A H 0.5664 -0.4137 0.5478 0.032 Uiso 1 1 calc GR . . . .
H11B H 0.6224 -0.1811 0.5948 0.032 Uiso 1 1 calc GR . . . .
H11C H 0.6831 -0.3811 0.5652 0.032 Uiso 1 1 calc GR . . . .
C12 C 0.76673(9) 0.1090(2) 0.53654(6) 0.0140(3) Uani 1 1 d . . . . .
C13 C 0.81404(9) 0.0128(2) 0.61152(6) 0.0146(3) Uani 1 1 d . . . . .
C14 C 0.79363(10) 0.1270(3) 0.66931(7) 0.0209(3) Uani 1 1 d . . . . .
H14 H 0.7503 0.2662 0.6605 0.025 Uiso 1 1 calc R . . . .
C15 C 0.83608(11) 0.0394(3) 0.73954(7) 0.0234(3) Uani 1 1 d . . . . .
H15 H 0.8219 0.1190 0.7786 0.028 Uiso 1 1 calc R . . . .
C16 C 0.89913(10) -0.1641(3) 0.75290(7) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.9275 -0.2257 0.8010 0.026 Uiso 1 1 calc R . . . .
C17 C 0.92064(10) -0.2771(3) 0.69578(8) 0.0233(3) Uani 1 1 d . . . . .
H17 H 0.9644 -0.4155 0.7049 0.028 Uiso 1 1 calc R . . . .
C18 C 0.87849(10) -0.1893(3) 0.62514(7) 0.0204(3) Uani 1 1 d . . . . .
H18 H 0.8937 -0.2672 0.5862 0.024 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 C10 1.2250(15) . ?
N1 N2 1.3760(14) . ?
N1 C12 1.3250(16) . ?
N2 C1 1.4338(15) . ?
N2 C8 1.3553(16) . ?
C1 C2 1.3866(18) . ?
C1 C6 1.3931(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3930(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3894(18) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.4905(17) . ?
C8 C9 1.3954(17) . ?
C9 C10 1.4746(17) . ?
C9 C12 1.4253(17) . ?
C10 C11 1.5028(17) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.4875(17) . ?
C13 C14 1.3928(18) . ?
C13 C18 1.3915(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3852(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.3919(18) . ?
C18 H18 0.9500 . ?

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 N1 N2 105.04(10) . . ?
N1 N2 C1 116.77(10) . . ?
C8 N2 N1 112.30(10) . . ?
C8 N2 C1 130.76(10) . . ?
C2 C1 N2 121.75(11) . . ?
C2 C1 C6 120.42(11) . . ?
C6 C1 N2 117.79(11) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.24(12) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.69(12) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.66(12) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.32(12) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.60(12) . . ?
C5 C6 H6 120.2 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
N2 C8 C7 123.68(11) . . ?
N2 C8 C9 106.44(10) . . ?
C9 C8 C7 129.89(11) . . ?
C8 C9 C10 125.92(11) . . ?
C8 C9 C12 104.77(11) . . ?
C12 C9 C10 129.16(11) . . ?
O1 C10 C9 121.25(11) . . ?
O1 C10 C11 120.07(11) . . ?
C9 C10 C11 118.67(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C9 111.45(11) . . ?
N1 C12 C13 117.97(11) . . ?
C9 C12 C13 130.55(11) . . ?
C14 C13 C12 119.46(11) . . ?
C18 C13 C12 121.30(11) . . ?
C18 C13 C14 119.25(11) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.53(13) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.16(13) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.65(12) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.42(13) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.98(12) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
