# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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
_database_code_depnum_ccdc_archive 'CCDC 1569085'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   9.1390(16)
_cell_length_b                   8.2606(15)
_cell_length_c                   16.224(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.140(2)
_cell_angle_gamma                90
_cell_volume                     1192.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1386
_cell_measurement_theta_min      2.5784
_cell_measurement_theta_max      20.7097

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            PINK
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6363
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2084
_reflns_number_gt                1374
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0654P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2084
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 -0.04777(13) 0.47484(14) 0.15027(8) 0.0620(4) Uani 1 1 d . . . . .
H1 H -0.1186 0.4579 0.1100 0.093 Uiso 1 1 calc R U . . .
N1 N -0.17310(17) 0.2321(2) 0.06221(10) 0.0652(5) Uani 1 1 d . . . . .
C1 C 0.03056(18) 0.3273(2) 0.17497(11) 0.0483(5) Uani 1 1 d . . . . .
C2 C 0.18822(18) 0.3405(2) 0.15773(10) 0.0463(4) Uani 1 1 d . . . . .
C3 C 0.2138(2) 0.4427(2) 0.09464(11) 0.0570(5) Uani 1 1 d . . . . .
H3 H 0.1353 0.5050 0.0640 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3552(2) 0.4534(2) 0.07662(13) 0.0656(6) Uani 1 1 d . . . . .
H4 H 0.3705 0.5228 0.0342 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4720(2) 0.3623(3) 0.12089(13) 0.0662(6) Uani 1 1 d . . . . .
H5 H 0.5664 0.3696 0.1086 0.079 Uiso 1 1 calc R U . . .
C6 C 0.4494(2) 0.2600(2) 0.18347(13) 0.0637(5) Uani 1 1 d . . . . .
H6 H 0.5283 0.1975 0.2135 0.076 Uiso 1 1 calc R U . . .
C7 C 0.30917(19) 0.2498(2) 0.20188(11) 0.0556(5) Uani 1 1 d . . . . .
H7 H 0.2954 0.1807 0.2448 0.067 Uiso 1 1 calc R U . . .
C8 C -0.05374(18) 0.1882(2) 0.12158(10) 0.0478(5) Uani 1 1 d . . . . .
C9 C -0.0109(2) 0.0281(2) 0.13372(13) 0.0640(5) Uani 1 1 d . . . . .
H9 H 0.0736 0.0001 0.1751 0.077 Uiso 1 1 calc R U . . .
C10 C -0.0940(2) -0.0896(3) 0.08416(15) 0.0739(6) Uani 1 1 d . . . . .
H10 H -0.0674 -0.1981 0.0923 0.089 Uiso 1 1 calc R U . . .
C11 C -0.2160(3) -0.0452(3) 0.02295(14) 0.0773(7) Uani 1 1 d . . . . .
H11 H -0.2737 -0.1221 -0.0119 0.093 Uiso 1 1 calc R U . . .
C12 C -0.2507(3) 0.1153(3) 0.01434(14) 0.0834(7) Uani 1 1 d . . . . .
H12 H -0.3337 0.1455 -0.0275 0.100 Uiso 1 1 calc R U . . .
C13 C 0.0360(2) 0.2998(3) 0.26940(11) 0.0608(5) Uani 1 1 d . . . . .
H13A H 0.0898 0.2000 0.2872 0.073 Uiso 1 1 calc R U . . .
H13B H 0.0921 0.3875 0.3017 0.073 Uiso 1 1 calc R U . . .
C14 C -0.1186(2) 0.2902(3) 0.29014(14) 0.0834(7) Uani 1 1 d . . . . .
H14A H -0.1733 0.2003 0.2606 0.125 Uiso 1 1 calc R U . . .
H14B H -0.1728 0.3886 0.2728 0.125 Uiso 1 1 calc R U . . .
H14C H -0.1069 0.2757 0.3500 0.125 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 C1 1.4243(19) . ?
O1 H1 0.8200 . ?
N1 C8 1.331(2) . ?
N1 C12 1.337(3) . ?
C1 C2 1.533(2) . ?
C1 C8 1.537(2) . ?
C1 C13 1.538(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.380(2) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.364(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.527(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
C8 N1 C12 117.55(17) . . ?
O1 C1 C2 108.72(13) . . ?
O1 C1 C8 109.02(13) . . ?
C2 C1 C8 108.78(13) . . ?
O1 C1 C13 107.86(14) . . ?
C2 C1 C13 111.94(14) . . ?
C8 C1 C13 110.46(14) . . ?
C3 C2 C7 117.40(16) . . ?
C3 C2 C1 120.07(15) . . ?
C7 C2 C1 122.51(15) . . ?
C2 C3 C4 120.94(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.39(18) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.73(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 120.03(18) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 121.52(18) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C8 C9 121.60(17) . . ?
N1 C8 C1 115.30(15) . . ?
C9 C8 C1 123.11(16) . . ?
C10 C9 C8 119.51(19) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 118.0(2) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N1 C12 C11 124.2(2) . . ?
N1 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C14 C13 C1 113.91(16) . . ?
C14 C13 H13A 108.8 . . ?
C1 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O1 C1 C2 C3 -26.8(2) . . . . ?
C8 C1 C2 C3 91.76(18) . . . . ?
C13 C1 C2 C3 -145.89(16) . . . . ?
O1 C1 C2 C7 154.81(15) . . . . ?
C8 C1 C2 C7 -86.58(18) . . . . ?
C13 C1 C2 C7 35.8(2) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 -178.40(16) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C1 C2 C7 C6 177.97(17) . . . . ?
C12 N1 C8 C9 0.0(3) . . . . ?
C12 N1 C8 C1 -179.68(17) . . . . ?
O1 C1 C8 N1 3.5(2) . . . . ?
C2 C1 C8 N1 -114.92(16) . . . . ?
C13 C1 C8 N1 121.84(16) . . . . ?
O1 C1 C8 C9 -176.15(15) . . . . ?
C2 C1 C8 C9 65.4(2) . . . . ?
C13 C1 C8 C9 -57.8(2) . . . . ?
N1 C8 C9 C10 -0.8(3) . . . . ?
C1 C8 C9 C10 178.86(16) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C8 N1 C12 C11 0.5(3) . . . . ?
C10 C11 C12 N1 -0.2(4) . . . . ?
O1 C1 C13 C14 58.9(2) . . . . ?
C2 C1 C13 C14 178.50(16) . . . . ?
C8 C1 C13 C14 -60.1(2) . . . . ?

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
O1 H1 N1 0.82 2.04 2.575(2) 122.6 .

_refine_diff_density_max         0.117
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.031

_shelxl_version_number           2014-3



