# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_aw73m
_database_code_depnum_ccdc_archive 'CCDC 1053805'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2015-07-17 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 H11 N O2'
_chemical_formula_sum            'C12 H11 N O2'
_chemical_formula_weight         201.22

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   7.7718(8)
_cell_length_b                   5.5207(5)
_cell_length_c                   11.7443(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.969(2)
_cell_angle_gamma                90
_cell_volume                     503.60(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4155
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_process_details   'SABABS; Bruker,2001'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5315
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.735
_diffrn_reflns_theta_max         26.244
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2019
_reflns_number_gt                1968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.995

_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014/7
_computing_molecular_graphics    SHELXL-2014
_computing_publication_material  SHELXL-2014

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.0387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2019
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_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
C1 C 0.2581(2) 0.9514(3) 0.47653(14) 0.0351(4) Uani 1 1 d . . . . .
C2 C 0.3177(2) 1.1348(4) 0.54879(15) 0.0452(4) Uani 1 1 d . . . . .
H2 H 0.3832 1.2600 0.5199 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2806(3) 1.1336(4) 0.66313(16) 0.0506(5) Uani 1 1 d . . . . .
H3 H 0.3226 1.2572 0.7102 0.061 Uiso 1 1 calc R U . . .
C4 C 0.1829(3) 0.9525(4) 0.70808(16) 0.0473(5) Uani 1 1 d . . . . .
H4 H 0.1576 0.9537 0.7849 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1224(3) 0.7683(4) 0.63767(16) 0.0488(5) Uani 1 1 d . . . . .
H5 H 0.0566 0.6442 0.6673 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1597(2) 0.7679(3) 0.52294(15) 0.0438(4) Uani 1 1 d . . . . .
H6 H 0.1183 0.6431 0.4764 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2980(2) 0.9499(3) 0.35466(14) 0.0359(4) Uani 1 1 d . . . . .
C8 C 0.3983(2) 1.1180(3) 0.29905(15) 0.0418(4) Uani 1 1 d . . . . .
H8 H 0.4505 1.2534 0.3323 0.050 Uiso 1 1 calc R U . . .
C9 C 0.3144(2) 0.8442(4) 0.17053(15) 0.0411(4) Uani 1 1 d . . . . .
C10 C 0.2452(2) 0.7772(4) 0.27205(14) 0.0401(4) Uani 1 1 d . . . . .
H10 H 0.1762 0.6426 0.2841 0.048 Uiso 1 1 calc R U . . .
C11 C 0.3046(2) 0.7314(4) 0.05864(15) 0.0428(4) Uani 1 1 d . . . . .
C12 C 0.1849(3) 0.4066(5) -0.0488(2) 0.0647(6) Uani 1 1 d . . . . .
H12A H 0.2918 0.3286 -0.0647 0.097 Uiso 1 1 calc R U . . .
H12B H 0.1547 0.5174 -0.1093 0.097 Uiso 1 1 calc R U . . .
H12C H 0.0961 0.2866 -0.0431 0.097 Uiso 1 1 calc R U . . .
N1 N 0.4073(2) 1.0519(3) 0.18869(13) 0.0434(4) Uani 1 1 d . . . . .
H1N H 0.462(3) 1.127(5) 0.136(2) 0.061(7) Uiso 1 1 d . . . . .
O1 O 0.3790(2) 0.8057(3) -0.02364(11) 0.0541(4) Uani 1 1 d . . . . .
O2 O 0.20274(19) 0.5371(3) 0.05708(12) 0.0560(4) Uani 1 1 d . . . . .


_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 1.390(2) . ?
C1 C6 1.392(3) . ?
C1 C7 1.475(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.389(2) . ?
C7 C10 1.411(2) . ?
C8 N1 1.351(2) . ?
C8 H8 0.9300 . ?
C9 N1 1.367(3) . ?
C9 C10 1.376(2) . ?
C9 C11 1.454(2) . ?
C10 H10 0.9300 . ?
C11 O1 1.214(2) . ?
C11 O2 1.333(3) . ?
C12 O2 1.440(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1N 0.87(3) . ?

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
C2 C1 C6 117.84(16) . . ?
C2 C1 C7 121.32(15) . . ?
C6 C1 C7 120.84(15) . . ?
C3 C2 C1 120.87(18) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.91(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.13(17) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.27(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.98(17) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C10 106.41(15) . . ?
C8 C7 C1 126.33(16) . . ?
C10 C7 C1 127.25(15) . . ?
N1 C8 C7 108.60(17) . . ?
N1 C8 H8 125.7 . . ?
C7 C8 H8 125.7 . . ?
N1 C9 C10 108.07(16) . . ?
N1 C9 C11 120.74(16) . . ?
C10 C9 C11 131.18(18) . . ?
C9 C10 C7 107.54(17) . . ?
C9 C10 H10 126.2 . . ?
C7 C10 H10 126.2 . . ?
O1 C11 O2 124.04(17) . . ?
O1 C11 C9 124.26(19) . . ?
O2 C11 C9 111.70(15) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 N1 C9 109.38(16) . . ?
C8 N1 H1N 126.7(18) . . ?
C9 N1 H1N 124.0(17) . . ?
C11 O2 C12 117.01(17) . . ?

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
C6 C1 C2 C3 0.3(3) . . . . ?
C7 C1 C2 C3 -179.51(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 179.78(16) . . . . ?
C2 C1 C7 C8 1.7(3) . . . . ?
C6 C1 C7 C8 -178.08(19) . . . . ?
C2 C1 C7 C10 -179.49(19) . . . . ?
C6 C1 C7 C10 0.7(3) . . . . ?
C10 C7 C8 N1 -0.2(2) . . . . ?
C1 C7 C8 N1 178.76(15) . . . . ?
N1 C9 C10 C7 -0.1(2) . . . . ?
C11 C9 C10 C7 178.85(18) . . . . ?
C8 C7 C10 C9 0.2(2) . . . . ?
C1 C7 C10 C9 -178.79(15) . . . . ?
N1 C9 C11 O1 2.1(3) . . . . ?
C10 C9 C11 O1 -176.7(2) . . . . ?
N1 C9 C11 O2 -177.42(16) . . . . ?
C10 C9 C11 O2 3.8(3) . . . . ?
C7 C8 N1 C9 0.2(2) . . . . ?
C10 C9 N1 C8 -0.1(2) . . . . ?
C11 C9 N1 C8 -179.13(16) . . . . ?
O1 C11 O2 C12 1.6(3) . . . . ?
C9 C11 O2 C12 -178.93(19) . . . . ?

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
N1 H1N O1 0.87(3) 2.09(3) 2.950(2) 173(2) 2_655

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.035

