# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_xcf4085_0m
_database_code_depnum_ccdc_archive 'CCDC 1817960'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   10.4481(12)
_cell_length_b                   7.0131(8)
_cell_length_c                   13.7142(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.787(2)
_cell_angle_gamma                90
_cell_volume                     990.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7425
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   0.3956
_exptl_transmission_factor_max   0.4335
_exptl_crystal_size_max          1.150
_exptl_crystal_size_mid          1.050
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10505
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         30.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2948
_reflns_number_gt                2724
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0555P)²+0.2717P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.076(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_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_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 0.54019(6) 0.25024(10) 0.55026(4) 0.01811(15) Uani 1 1 d . . . . .
N1 N -0.12705(8) 0.25956(14) 0.37847(7) 0.0284(2) Uani 1 1 d . . . . .
N2 N 0.18853(6) 0.18315(10) 0.35918(5) 0.01098(15) Uani 1 1 d . . . . .
C1 C -0.04213(8) 0.22397(13) 0.33843(7) 0.01749(18) Uani 1 1 d . . . . .
C2 C 0.06763(7) 0.17644(12) 0.28812(6) 0.01330(16) Uani 1 1 d . . . . .
H12 H 0.0553 0.0473 0.2589 0.016 Uiso 1 1 calc R U . . .
H11 H 0.0716 0.2685 0.2340 0.016 Uiso 1 1 calc R U . . .
C3 C 0.30463(7) 0.19107(11) 0.32190(5) 0.00985(15) Uani 1 1 d . . . . .
C4 C 0.42439(7) 0.21465(11) 0.38742(5) 0.01036(15) Uani 1 1 d . . . . .
C5 C 0.54096(7) 0.20084(11) 0.35030(6) 0.01223(16) Uani 1 1 d . . . . .
H6 H 0.6210 0.2102 0.3948 0.015 Uiso 1 1 calc R U . . .
C6 C 0.54259(8) 0.17381(12) 0.25035(6) 0.01377(17) Uani 1 1 d . . . . .
H1 H 0.6225 0.1633 0.2265 0.017 Uiso 1 1 calc R U . . .
C7 C 0.19159(7) 0.07562(11) 0.45223(5) 0.01229(16) Uani 1 1 d . . . . .
H10 H 0.2616 -0.0209 0.4586 0.015 Uiso 1 1 calc R U . . .
H9 H 0.1081 0.0078 0.4503 0.015 Uiso 1 1 calc R U . . .
C8 C 0.21468(8) 0.20790(12) 0.54187(6) 0.01485(17) Uani 1 1 d . . . . .
H3 H 0.2419 0.1320 0.6027 0.018 Uiso 1 1 calc R U . . .
H2 H 0.1330 0.2747 0.5480 0.018 Uiso 1 1 calc R U . . .
C9 C 0.32041(8) 0.35496(12) 0.53084(6) 0.01407(16) Uani 1 1 d . . . . .
H8 H 0.2825 0.4552 0.4838 0.017 Uiso 1 1 calc R U . . .
H7 H 0.3503 0.4164 0.5957 0.017 Uiso 1 1 calc R U . . .
C10 C 0.43581(8) 0.26731(11) 0.49437(5) 0.01198(16) Uani 1 1 d . . . . .
C11 C 0.42428(8) 0.16226(12) 0.18528(6) 0.01353(16) Uani 1 1 d . . . . .
H4 H 0.4241 0.1487 0.1163 0.016 Uiso 1 1 calc R U . . .
C12 C 0.30698(8) 0.17032(11) 0.22002(5) 0.01196(16) Uani 1 1 d . . . . .
H5 H 0.2276 0.1618 0.1747 0.014 Uiso 1 1 calc R 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
O1 C10 1.2276(10) . ?
N1 C1 1.1475(12) . ?
N2 C3 1.3953(9) . ?
N2 C2 1.4591(10) . ?
N2 C7 1.4779(9) . ?
C1 C2 1.4735(12) . ?
C2 H12 0.9900 . ?
C2 H11 0.9900 . ?
C3 C12 1.4092(10) . ?
C3 C4 1.4206(10) . ?
C4 C5 1.4010(10) . ?
C4 C10 1.4975(11) . ?
C5 C6 1.3868(11) . ?
C5 H6 0.9500 . ?
C6 C11 1.3986(11) . ?
C6 H1 0.9500 . ?
C7 C8 1.5262(11) . ?
C7 H10 0.9900 . ?
C7 H9 0.9900 . ?
C8 C9 1.5374(12) . ?
C8 H3 0.9900 . ?
C8 H2 0.9900 . ?
C9 C10 1.5122(11) . ?
C9 H8 0.9900 . ?
C9 H7 0.9900 . ?
C11 C12 1.3895(11) . ?
C11 H4 0.9500 . ?
C12 H5 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
C3 N2 C2 117.67(6) . . ?
C3 N2 C7 116.37(6) . . ?
C2 N2 C7 116.71(6) . . ?
N1 C1 C2 179.21(10) . . ?
N2 C2 C1 109.53(7) . . ?
N2 C2 H12 109.8 . . ?
C1 C2 H12 109.8 . . ?
N2 C2 H11 109.8 . . ?
C1 C2 H11 109.8 . . ?
H12 C2 H11 108.2 . . ?
N2 C3 C12 121.46(7) . . ?
N2 C3 C4 120.00(6) . . ?
C12 C3 C4 118.51(7) . . ?
C5 C4 C3 119.26(7) . . ?
C5 C4 C10 116.33(7) . . ?
C3 C4 C10 124.28(7) . . ?
C6 C5 C4 121.74(7) . . ?
C6 C5 H6 119.1 . . ?
C4 C5 H6 119.1 . . ?
C5 C6 C11 118.73(7) . . ?
C5 C6 H1 120.6 . . ?
C11 C6 H1 120.6 . . ?
N2 C7 C8 111.26(7) . . ?
N2 C7 H10 109.4 . . ?
C8 C7 H10 109.4 . . ?
N2 C7 H9 109.4 . . ?
C8 C7 H9 109.4 . . ?
H10 C7 H9 108.0 . . ?
C7 C8 C9 110.26(6) . . ?
C7 C8 H3 109.6 . . ?
C9 C8 H3 109.6 . . ?
C7 C8 H2 109.6 . . ?
C9 C8 H2 109.6 . . ?
H3 C8 H2 108.1 . . ?
C10 C9 C8 112.74(7) . . ?
C10 C9 H8 109.0 . . ?
C8 C9 H8 109.0 . . ?
C10 C9 H7 109.0 . . ?
C8 C9 H7 109.0 . . ?
H8 C9 H7 107.8 . . ?
O1 C10 C4 120.13(7) . . ?
O1 C10 C9 120.45(7) . . ?
C4 C10 C9 119.27(6) . . ?
C12 C11 C6 120.95(7) . . ?
C12 C11 H4 119.5 . . ?
C6 C11 H4 119.5 . . ?
C11 C12 C3 120.61(7) . . ?
C11 C12 H5 119.7 . . ?
C3 C12 H5 119.7 . . ?

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
C3 N2 C2 C1 -163.82(7) . . . . ?
C7 N2 C2 C1 50.57(9) . . . . ?
C2 N2 C3 C12 -7.48(11) . . . . ?
C7 N2 C3 C12 138.25(7) . . . . ?
C2 N2 C3 C4 174.49(7) . . . . ?
C7 N2 C3 C4 -39.78(10) . . . . ?
N2 C3 C4 C5 172.86(7) . . . . ?
C12 C3 C4 C5 -5.23(11) . . . . ?
N2 C3 C4 C10 -11.52(11) . . . . ?
C12 C3 C4 C10 170.39(7) . . . . ?
C3 C4 C5 C6 3.14(12) . . . . ?
C10 C4 C5 C6 -172.81(7) . . . . ?
C4 C5 C6 C11 0.70(12) . . . . ?
C3 N2 C7 C8 95.61(8) . . . . ?
C2 N2 C7 C8 -118.33(7) . . . . ?
N2 C7 C8 C9 -42.71(9) . . . . ?
C7 C8 C9 C10 -44.08(9) . . . . ?
C5 C4 C10 O1 -17.97(11) . . . . ?
C3 C4 C10 O1 166.30(8) . . . . ?
C5 C4 C10 C9 157.58(7) . . . . ?
C3 C4 C10 C9 -18.16(11) . . . . ?
C8 C9 C10 O1 -108.64(9) . . . . ?
C8 C9 C10 C4 75.83(9) . . . . ?
C5 C6 C11 C12 -2.42(12) . . . . ?
C6 C11 C12 C3 0.23(12) . . . . ?
N2 C3 C12 C11 -174.46(7) . . . . ?
C4 C3 C12 C11 3.61(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H5 O1 0.95 2.45 3.3607(10) 161.1 4_565
C7 H10 O1 0.99 2.64 3.6207(10) 170.5 3_656
C2 H11 O1 0.99 2.49 3.2665(11) 135.2 4_565
C12 H5 O1 0.95 2.45 3.3607(10) 161.1 4_565
C2 H11 O1 0.99 2.49 3.2665(11) 135.2 4_565
C2 H11 O1 0.99 2.49 3.2665(11) 135.2 4_565
C12 H5 O1 0.95 2.45 3.3607(10) 161.1 4_565
C2 H11 O1 0.99 2.49 3.2665(11) 135.2 4_565
C7 H10 O1 0.99 2.64 3.6207(10) 170.5 3_656
C12 H5 O1 0.95 2.45 3.3607(10) 161.1 4_565

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.060

