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

data_R20180410B1
_database_code_depnum_ccdc_archive 'CCDC 1838875'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 N2 O'
_chemical_formula_weight         290.35

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.268(2)
_cell_length_b                   16.335(3)
_cell_length_c                   9.5163(19)
_cell_angle_alpha                90
_cell_angle_beta                 114.91(3)
_cell_angle_gamma                90
_cell_volume                     1588.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3759
_cell_measurement_theta_min      1.9929
_cell_measurement_theta_max      27.8267

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8322
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18791
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         27.793
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3749
_reflns_number_gt                2722
_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       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0674P)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     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3749
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.84577(11) 0.14886(7) 0.28278(11) 0.0479(3) Uani 1 1 d . . . . .
N1 N 0.81451(12) 0.06891(8) 0.07440(14) 0.0327(3) Uani 1 1 d D . . . .
N2 N 0.80684(12) -0.05248(8) -0.11367(14) 0.0382(3) Uani 1 1 d . . . . .
C1 C 0.80281(16) -0.11143(11) -0.2109(2) 0.0483(5) Uani 1 1 d . . . . .
H1A H 0.7456 -0.1047 -0.3173 0.058 Uiso 1 1 calc R U . . .
C2 C 0.87798(17) -0.18331(12) -0.1664(2) 0.0525(5) Uani 1 1 d . . . . .
H2 H 0.8714 -0.2236 -0.2414 0.063 Uiso 1 1 calc R U . . .
C3 C 0.96005(17) -0.19461(11) -0.0153(2) 0.0484(4) Uani 1 1 d . . . . .
H3 H 1.0097 -0.2436 0.0170 0.058 Uiso 1 1 calc R U . . .
C4 C 0.97130(15) -0.13261(10) 0.09451(19) 0.0400(4) Uani 1 1 d . . . . .
C5 C 1.05611(17) -0.13764(11) 0.2534(2) 0.0500(5) Uani 1 1 d . . . . .
H5 H 1.1086 -0.1850 0.2930 0.060 Uiso 1 1 calc R U . . .
C6 C 1.06286(17) -0.07441(12) 0.3505(2) 0.0525(5) Uani 1 1 d . . . . .
H6 H 1.1213 -0.0783 0.4570 0.063 Uiso 1 1 calc R U . . .
C7 C 0.98516(15) -0.00331(11) 0.29654(18) 0.0427(4) Uani 1 1 d . . . . .
H7 H 0.9922 0.0401 0.3661 0.051 Uiso 1 1 calc R U . . .
C8 C 0.89940(14) 0.00262(9) 0.14284(16) 0.0327(4) Uani 1 1 d . . . . .
C9 C 0.89176(14) -0.06236(9) 0.03846(17) 0.0335(4) Uani 1 1 d . . . . .
C10 C 0.78961(15) 0.13549(9) 0.14317(16) 0.0339(4) Uani 1 1 d . . . . .
C11 C 0.68800(15) 0.19348(10) 0.03374(16) 0.0369(4) Uani 1 1 d . . . . .
H11A H 0.6215 0.1616 -0.0516 0.044 Uiso 1 1 calc R U . . .
H11B H 0.7307 0.2312 -0.0122 0.044 Uiso 1 1 calc R U . . .
C12 C 0.62051(15) 0.24315(10) 0.11313(17) 0.0369(4) Uani 1 1 d . . . . .
H12A H 0.6879 0.2705 0.2049 0.044 Uiso 1 1 calc R U . . .
H12B H 0.5709 0.2055 0.1502 0.044 Uiso 1 1 calc R U . . .
C13 C 0.52716(16) 0.30783(11) 0.00939(17) 0.0457(4) Uani 1 1 d . . . . .
H13A H 0.5742 0.3428 -0.0355 0.055 Uiso 1 1 calc R U . . .
H13B H 0.4543 0.2806 -0.0771 0.055 Uiso 1 1 calc R U . . .
C14 C 0.47228(15) 0.36072(10) 0.09806(17) 0.0387(4) Uani 1 1 d . . . . .
C15 C 0.53230(15) 0.43454(10) 0.16263(18) 0.0423(4) Uani 1 1 d . . . . .
H15 H 0.6056 0.4527 0.1464 0.051 Uiso 1 1 calc R U . . .
C16 C 0.48642(17) 0.48193(11) 0.2505(2) 0.0490(4) Uani 1 1 d . . . . .
H16 H 0.5283 0.5322 0.2940 0.059 Uiso 1 1 calc R U . . .
C17 C 0.37984(18) 0.45588(13) 0.2746(2) 0.0602(5) Uani 1 1 d . . . . .
H17 H 0.3484 0.4882 0.3348 0.072 Uiso 1 1 calc R U . . .
C18 C 0.31872(17) 0.38270(13) 0.2109(2) 0.0591(5) Uani 1 1 d . . . . .
H18 H 0.2451 0.3648 0.2267 0.071 Uiso 1 1 calc R U . . .
C19 C 0.36556(16) 0.33572(11) 0.12391(19) 0.0490(4) Uani 1 1 d . . . . .
H19 H 0.3237 0.2854 0.0812 0.059 Uiso 1 1 calc R U . . .
H1 H 0.7688(14) 0.0617(10) -0.0268(11) 0.044(5) Uiso 1 1 d 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 C10 1.2268(17) . ?
N1 C10 1.3581(18) . ?
N1 C8 1.4096(18) . ?
N1 H1 0.888(9) . ?
N2 C1 1.323(2) . ?
N2 C9 1.3677(19) . ?
C1 C2 1.405(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.356(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(2) . ?
C4 C9 1.415(2) . ?
C5 C6 1.366(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.431(2) . ?
C10 C11 1.513(2) . ?
C11 C12 1.514(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.510(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.386(2) . ?
C14 C15 1.393(2) . ?
C15 C16 1.389(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C10 N1 C8 129.07(12) . . ?
C10 N1 H1 119.0(11) . . ?
C8 N1 H1 111.8(11) . . ?
C1 N2 C9 117.20(14) . . ?
N2 C1 C2 123.98(16) . . ?
N2 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C3 C2 C1 119.27(16) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.51(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C9 119.13(15) . . ?
C5 C4 C3 123.84(15) . . ?
C9 C4 C3 117.03(15) . . ?
C6 C5 C4 120.03(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.74(16) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 119.59(16) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 N1 125.55(14) . . ?
C7 C8 C9 119.72(14) . . ?
N1 C8 C9 114.73(12) . . ?
N2 C9 C4 122.98(14) . . ?
N2 C9 C8 117.25(13) . . ?
C4 C9 C8 119.77(14) . . ?
O1 C10 N1 123.19(14) . . ?
O1 C10 C11 121.98(14) . . ?
N1 C10 C11 114.83(12) . . ?
C10 C11 C12 112.69(12) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 113.77(12) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 111.59(12) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C19 C14 C15 118.23(15) . . ?
C19 C14 C13 121.37(16) . . ?
C15 C14 C13 120.32(15) . . ?
C16 C15 C14 120.90(16) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.87(17) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.01(17) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 119.67(18) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 121.32(17) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 119.3 . . ?

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
C9 N2 C1 C2 1.3(2) . . . . ?
N2 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
C2 C3 C4 C5 -178.41(16) . . . . ?
C2 C3 C4 C9 1.6(2) . . . . ?
C9 C4 C5 C6 -1.4(2) . . . . ?
C3 C4 C5 C6 178.60(16) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 N1 178.61(14) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C10 N1 C8 C7 -6.7(2) . . . . ?
C10 N1 C8 C9 173.29(13) . . . . ?
C1 N2 C9 C4 -1.4(2) . . . . ?
C1 N2 C9 C8 177.96(14) . . . . ?
C5 C4 C9 N2 -179.98(14) . . . . ?
C3 C4 C9 N2 0.0(2) . . . . ?
C5 C4 C9 C8 0.7(2) . . . . ?
C3 C4 C9 C8 -179.39(13) . . . . ?
C7 C8 C9 N2 -178.65(13) . . . . ?
N1 C8 C9 N2 1.37(18) . . . . ?
C7 C8 C9 C4 0.8(2) . . . . ?
N1 C8 C9 C4 -179.22(12) . . . . ?
C8 N1 C10 O1 3.2(2) . . . . ?
C8 N1 C10 C11 -177.72(13) . . . . ?
O1 C10 C11 C12 -26.3(2) . . . . ?
N1 C10 C11 C12 154.69(13) . . . . ?
C10 C11 C12 C13 174.43(13) . . . . ?
C11 C12 C13 C14 -174.67(14) . . . . ?
C12 C13 C14 C19 -82.96(19) . . . . ?
C12 C13 C14 C15 93.89(18) . . . . ?
C19 C14 C15 C16 -0.1(2) . . . . ?
C13 C14 C15 C16 -177.00(14) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C15 C14 C19 C18 0.3(2) . . . . ?
C13 C14 C19 C18 177.24(15) . . . . ?

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 H1 N2 0.888(9) 2.156(16) 2.6481(18) 114.3(13) .
C7 H7 O1 0.95 2.32 2.914(2) 119.6 .
C7 H7 O1 0.95 2.32 2.914(2) 119.6 .

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.042

