# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc1z9w05
_database_code_depnum_ccdc_archive 'CCDC 1826737'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.7913(7)
_cell_length_b                   10.4651(8)
_cell_length_c                   13.1287(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1207.86(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1880
_cell_measurement_theta_min      5.3810
_cell_measurement_theta_max      60.8740

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.635
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5013
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.405
_diffrn_reflns_theta_max         61.123
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.841
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.840
_reflns_number_total             1764
_reflns_number_gt                1610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.839

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.1456P] 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 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1764
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
O1 O 0.1683(3) 0.1339(3) 0.34556(19) 0.0645(7) Uani 1 1 d . . . . .
C7 C 0.0495(4) 0.1820(3) 0.3168(2) 0.0519(8) Uani 1 1 d . . . . .
N2 N 0.0087(3) 0.2765(3) 0.4768(2) 0.0547(7) Uani 1 1 d . . . . .
C9 C -0.0450(4) 0.3669(3) 0.6398(3) 0.0547(8) Uani 1 1 d . . . . .
C8 C -0.0818(4) 0.3421(3) 0.5322(3) 0.0568(9) Uani 1 1 d . . . . .
H8A H -0.1713 0.3742 0.5044 0.068 Uiso 1 1 calc R U . . .
N1 N -0.0401(4) 0.2534(3) 0.3779(2) 0.0549(7) Uani 1 1 d . . . . .
C6 C -0.0049(4) 0.1642(3) 0.2089(2) 0.0521(8) Uani 1 1 d . . . . .
C1 C -0.1018(4) 0.2481(4) 0.1605(3) 0.0620(9) Uani 1 1 d . . . . .
H1B H -0.1399 0.3187 0.1951 0.074 Uiso 1 1 calc R U . . .
C14 C 0.0774(5) 0.3088(4) 0.6863(3) 0.0757(11) Uani 1 1 d . . . . .
H14A H 0.1403 0.2554 0.6485 0.091 Uiso 1 1 calc R U . . .
C11 C -0.1062(6) 0.4651(4) 0.7999(3) 0.0789(12) Uani 1 1 d . . . . .
H11A H -0.1686 0.5183 0.8383 0.095 Uiso 1 1 calc R U . . .
C10 C -0.1369(5) 0.4459(4) 0.6968(3) 0.0676(10) Uani 1 1 d . . . . .
H10A H -0.2195 0.4865 0.6666 0.081 Uiso 1 1 calc R U . . .
C5 C 0.0515(4) 0.0598(3) 0.1567(3) 0.0659(9) Uani 1 1 d . . . . .
H5A H 0.1171 0.0032 0.1891 0.079 Uiso 1 1 calc R U . . .
C12 C 0.0145(5) 0.4063(4) 0.8445(3) 0.0819(12) Uani 1 1 d . . . . .
H12A H 0.0342 0.4187 0.9134 0.098 Uiso 1 1 calc R U . . .
C4 C 0.0104(5) 0.0390(4) 0.0559(3) 0.0767(11) Uani 1 1 d . . . . .
H4A H 0.0487 -0.0310 0.0206 0.092 Uiso 1 1 calc R U . . .
C3 C -0.0868(5) 0.1222(5) 0.0088(3) 0.0790(12) Uani 1 1 d . . . . .
H3A H -0.1153 0.1076 -0.0585 0.095 Uiso 1 1 calc R U . . .
C2 C -0.1425(5) 0.2264(4) 0.0591(3) 0.0775(12) Uani 1 1 d . . . . .
H2A H -0.2074 0.2829 0.0260 0.093 Uiso 1 1 calc R U . . .
C13 C 0.1076(6) 0.3286(5) 0.7876(3) 0.0908(14) Uani 1 1 d . . . . .
H13A H 0.1911 0.2893 0.8178 0.109 Uiso 1 1 calc R U . . .
H1A H -0.142(5) 0.286(4) 0.359(3) 0.084(13) Uiso 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
O1 C7 1.219(4) . ?
C7 N1 1.350(4) . ?
C7 C6 1.506(5) . ?
N2 C8 1.278(4) . ?
N2 N1 1.389(4) . ?
C9 C10 1.378(5) . ?
C9 C14 1.378(5) . ?
C9 C8 1.472(5) . ?
C8 H8A 0.9300 . ?
N1 H1A 0.99(5) . ?
C6 C1 1.379(5) . ?
C6 C5 1.382(5) . ?
C1 C2 1.396(5) . ?
C1 H1B 0.9300 . ?
C14 C13 1.372(6) . ?
C14 H14A 0.9300 . ?
C11 C12 1.359(7) . ?
C11 C10 1.395(6) . ?
C11 H11A 0.9300 . ?
C10 H10A 0.9300 . ?
C5 C4 1.389(6) . ?
C5 H5A 0.9300 . ?
C12 C13 1.374(7) . ?
C12 H12A 0.9300 . ?
C4 C3 1.367(6) . ?
C4 H4A 0.9300 . ?
C3 C2 1.367(6) . ?
C3 H3A 0.9300 . ?
C2 H2A 0.9300 . ?
C13 H13A 0.9300 . ?

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
O1 C7 N1 122.9(3) . . ?
O1 C7 C6 120.8(3) . . ?
N1 C7 C6 116.3(3) . . ?
C8 N2 N1 115.7(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 C8 119.9(3) . . ?
C14 C9 C8 121.2(3) . . ?
N2 C8 C9 120.3(3) . . ?
N2 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C7 N1 N2 118.2(3) . . ?
C7 N1 H1A 125(3) . . ?
N2 N1 H1A 117(3) . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 C7 123.4(3) . . ?
C5 C6 C7 116.8(3) . . ?
C6 C1 C2 119.6(4) . . ?
C6 C1 H1B 120.2 . . ?
C2 C1 H1B 120.2 . . ?
C13 C14 C9 120.9(4) . . ?
C13 C14 H14A 119.5 . . ?
C9 C14 H14A 119.5 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/6

