# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_hs405
_database_code_depnum_ccdc_archive 'CCDC 2192543'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2022-07-25 deposited with the CCDC.	2023-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C14 H14 N2 O'
_chemical_formula_sum            'C14 H14 N2 O'
_chemical_formula_weight         226.27

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                   18.0753(4)
_cell_length_b                   6.58740(10)
_cell_length_c                   9.4903(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1130.00(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    5785
_cell_measurement_theta_min      6.77
_cell_measurement_theta_max      68.18

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7941
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.893
_diffrn_reflns_theta_max         66.586
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1985
_reflns_number_gt                1960
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0055(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1985
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.028

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 0.51847(8) 0.6372(2) 0.35000(17) 0.0353(4) Uani 1 1 d . . . . .
N1 N 0.69587(9) 0.0939(2) 0.3440(2) 0.0328(4) Uani 1 1 d . . . . .
N2 N 0.80032(10) 0.0958(3) 0.4842(2) 0.0388(5) Uani 1 1 d . . . . .
C1 C 0.73549(10) 0.1867(3) 0.4459(2) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.71203(11) 0.3694(3) 0.5083(2) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.742604 0.436855 0.574870 0.035 Uiso 1 1 calc R U . . .
C3 C 0.64413(10) 0.4495(3) 0.47174(18) 0.0258(4) Uani 1 1 d . . . . .
C4 C 0.60135(10) 0.3473(3) 0.3713(2) 0.0277(4) Uani 1 1 d . . . . .
C5 C 0.63040(11) 0.1758(3) 0.3104(2) 0.0310(5) Uani 1 1 d . . . . .
H5 H 0.602019 0.110635 0.239300 0.037 Uiso 1 1 calc R U . . .
C6 C 0.52409(11) 0.4202(3) 0.3436(3) 0.0339(5) Uani 1 1 d . . . . .
H6A H 0.508234 0.373315 0.249251 0.041 Uiso 1 1 calc R U . . .
H6B H 0.490247 0.359791 0.414130 0.041 Uiso 1 1 calc R U . . .
C7 C 0.55088(11) 0.7239(3) 0.4664(2) 0.0297(4) Uani 1 1 d . . . . .
C8 C 0.52101(12) 0.9058(3) 0.5137(2) 0.0358(5) Uani 1 1 d . . . . .
H8 H 0.478259 0.960611 0.469649 0.043 Uiso 1 1 calc R U . . .
C9 C 0.55374(13) 1.0069(3) 0.6252(2) 0.0388(5) Uani 1 1 d . . . . .
H9 H 0.533704 1.131925 0.657363 0.047 Uiso 1 1 calc R U . . .
C10 C 0.61567(13) 0.9260(3) 0.6899(2) 0.0381(5) Uani 1 1 d . . . . .
H10 H 0.637993 0.995567 0.766610 0.046 Uiso 1 1 calc R U . . .
C11 C 0.64522(11) 0.7442(3) 0.6435(2) 0.0331(4) Uani 1 1 d . . . . .
H11 H 0.687687 0.689767 0.688819 0.040 Uiso 1 1 calc R U . . .
C12 C 0.61326(11) 0.6394(3) 0.5305(2) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.84607(13) 0.1840(4) 0.5923(3) 0.0454(6) Uani 1 1 d . . . . .
H13A H 0.818931 0.185498 0.681698 0.068 Uiso 1 1 calc R U . . .
H13B H 0.859141 0.323290 0.565842 0.068 Uiso 1 1 calc R U . . .
H13C H 0.891274 0.103327 0.602972 0.068 Uiso 1 1 calc R U . . .
C14 C 0.81881(13) -0.1053(3) 0.4343(3) 0.0439(6) Uani 1 1 d . . . . .
H14A H 0.867045 -0.145542 0.472260 0.066 Uiso 0.5 1 calc R U P . .
H14B H 0.780980 -0.201754 0.465656 0.066 Uiso 0.5 1 calc R U P . .
H14C H 0.820954 -0.104783 0.331089 0.066 Uiso 0.5 1 calc R U P . .
H14D H 0.778941 -0.155844 0.373744 0.066 Uiso 0.5 1 calc R U P . .
H14E H 0.865006 -0.099632 0.380347 0.066 Uiso 0.5 1 calc R U P . .
H14F H 0.825032 -0.196603 0.514914 0.066 Uiso 0.5 1 calc R U P . .


_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 1.375(3) . ?
O1 C6 1.434(2) . ?
N1 C5 1.339(3) . ?
N1 C1 1.350(3) . ?
N2 C1 1.365(3) . ?
N2 C13 1.441(3) . ?
N2 C14 1.446(3) . ?
C1 C2 1.406(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.400(3) . ?
C3 C12 1.479(3) . ?
C4 C5 1.374(3) . ?
C4 C6 1.500(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.397(3) . ?
C8 C9 1.383(4) . ?
C9 C10 1.384(4) . ?
C10 C11 1.383(3) . ?
C11 C12 1.400(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
C7 O1 C6 114.69(16) . . ?
C5 N1 C1 117.18(16) . . ?
C1 N2 C13 120.35(18) . . ?
C1 N2 C14 120.89(18) . . ?
C13 N2 C14 118.04(17) . . ?
N1 C1 N2 116.56(17) . . ?
N1 C1 C2 121.96(17) . . ?
N2 C1 C2 121.47(18) . . ?
C3 C2 C1 119.31(18) . . ?
C2 C3 C4 118.57(17) . . ?
C2 C3 C12 124.37(17) . . ?
C4 C3 C12 117.06(17) . . ?
C5 C4 C3 118.11(17) . . ?
C5 C4 C6 123.04(18) . . ?
C3 C4 C6 118.67(18) . . ?
N1 C5 C4 124.67(18) . . ?
O1 C6 C4 112.18(16) . . ?
O1 C7 C8 116.91(17) . . ?
O1 C7 C12 121.87(17) . . ?
C8 C7 C12 121.14(19) . . ?
C9 C8 C7 119.8(2) . . ?
C8 C9 C10 120.0(2) . . ?
C11 C10 C9 120.3(2) . . ?
C10 C11 C12 120.8(2) . . ?
C7 C12 C11 118.03(18) . . ?
C7 C12 C3 118.54(18) . . ?
C11 C12 C3 123.37(18) . . ?

