# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 2057801'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   12.5334(11)
_cell_length_b                   9.3516(8)
_cell_length_c                   17.8360(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2090.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1440
_cell_measurement_theta_min      3.5060
_cell_measurement_theta_max      25.7070

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.644
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            2325
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         28.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2325
_reflns_number_gt                1294
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details          'Refined as a 2-component twin.,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)+(0.0508P)²] 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_number_reflns         2325
_refine_ls_number_parameters     142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_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
N1 N 1.11276(10) 0.23882(13) 0.68093(7) 0.0329(4) Uani 1 1 d D . . . .
H1 H 1.1652(3) 0.2048(9) 0.7104(3) 0.051(5) Uiso 1 1 d D . . . .
C2 C 1.12862(13) 0.34006(16) 0.62587(9) 0.0298(4) Uani 1 1 d . . . . .
C3 C 1.03158(13) 0.37575(16) 0.59607(9) 0.0336(4) Uani 1 1 d . . . . .
H3A H 1.019480 0.444308 0.557696 0.040 Uiso 1 1 calc R U . . .
C4 C 0.95195(13) 0.29245(16) 0.63248(8) 0.0295(4) Uani 1 1 d . . . . .
C5 C 0.84098(13) 0.27832(16) 0.62364(9) 0.0328(4) Uani 1 1 d . . . . .
H5A H 0.803022 0.337100 0.589350 0.039 Uiso 1 1 calc R U . . .
C6 C 0.78891(13) 0.17727(17) 0.66590(9) 0.0330(4) Uani 1 1 d . . . . .
C7 C 0.84397(14) 0.09136(17) 0.71735(9) 0.0361(4) Uani 1 1 d . . . . .
H7A H 0.805569 0.022377 0.745644 0.043 Uiso 1 1 calc R U . . .
C8 C 0.95189(14) 0.10444(16) 0.72785(9) 0.0361(4) Uani 1 1 d . . . . .
H8A H 0.988752 0.046119 0.762936 0.043 Uiso 1 1 calc R U . . .
C9 C 1.00555(12) 0.20658(16) 0.68509(9) 0.0298(4) Uani 1 1 d . . . . .
C10 C 1.23377(13) 0.38709(17) 0.60372(9) 0.0335(4) Uani 1 1 d . . . . .
C11 C 1.33434(14) 0.3594(2) 0.62444(10) 0.0458(5) Uani 1 1 d . . . . .
H11A H 1.363747 0.304437 0.664176 0.055 Uiso 1 1 calc R U . . .
C12 C 1.38432(13) 0.4458(2) 0.56275(10) 0.0473(5) Uani 1 1 d . . . . .
H12A H 1.423264 0.388541 0.524940 0.057 Uiso 1 1 calc R U . . .
H12B H 1.427352 0.528051 0.580311 0.057 Uiso 1 1 calc R U . . .
C13 C 1.26819(14) 0.48401(18) 0.54054(10) 0.0437(5) Uani 1 1 d . . . . .
H13A H 1.249433 0.585876 0.547944 0.052 Uiso 1 1 calc R U . . .
H13B H 1.247016 0.450231 0.490084 0.052 Uiso 1 1 calc R U . . .
O14 O 0.68048(9) 0.15007(12) 0.66214(7) 0.0432(3) Uani 1 1 d . . . . .
C15 C 0.61795(13) 0.24008(19) 0.61456(11) 0.0468(5) Uani 1 1 d . . . . .
H15A H 0.643523 0.231808 0.562817 0.070 Uiso 1 1 calc R U . . .
H15B H 0.624467 0.339558 0.631225 0.070 Uiso 1 1 calc R U . . .
H15C H 0.543002 0.210602 0.617015 0.070 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
N1 C2 1.3785(19) . ?
N1 C9 1.3791(18) . ?
C2 C3 1.369(2) . ?
C2 C10 1.444(2) . ?
C3 C4 1.423(2) . ?
C4 C5 1.406(2) . ?
C4 C9 1.406(2) . ?
C5 C6 1.374(2) . ?
C6 O14 1.3843(18) . ?
C6 C7 1.401(2) . ?
C7 C8 1.371(2) . ?
C8 C9 1.395(2) . ?
C10 C11 1.339(2) . ?
C10 C13 1.509(2) . ?
C11 C12 1.502(2) . ?
C12 C13 1.550(2) . ?
O14 C15 1.429(2) . ?

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 N1 C9 109.21(12) . . ?
C3 C2 N1 108.43(14) . . ?
C3 C2 C10 129.07(15) . . ?
N1 C2 C10 122.38(14) . . ?
C2 C3 C4 108.21(14) . . ?
C5 C4 C9 119.60(15) . . ?
C5 C4 C3 133.96(15) . . ?
C9 C4 C3 106.39(14) . . ?
C6 C5 C4 118.23(15) . . ?
C5 C6 O14 124.49(15) . . ?
C5 C6 C7 121.32(16) . . ?
O14 C6 C7 114.19(14) . . ?
C8 C7 C6 121.61(15) . . ?
C7 C8 C9 117.52(15) . . ?
N1 C9 C8 130.45(15) . . ?
N1 C9 C4 107.74(14) . . ?
C8 C9 C4 121.70(15) . . ?
C11 C10 C2 136.44(16) . . ?
C11 C10 C13 93.04(14) . . ?
C2 C10 C13 130.39(15) . . ?
C10 C11 C12 94.96(15) . . ?
C11 C12 C13 85.38(13) . . ?
C10 C13 C12 86.52(13) . . ?
C6 O14 C15 117.31(13) . . ?

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
_geom_hbond_publ_flag
N1 H1 O14 0.9000(1) 2.337(4) 3.0404(18) 134.9(5) 6_657 yes

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037

