# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_d20848
_database_code_depnum_ccdc_archive 'CCDC 1981759'
loop_
_audit_author_name
_audit_author_address
'Balaji Ganesan'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-02-04 deposited with the CCDC.	2020-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O'
_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_weight         278.34

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   7.5891(3)
_cell_length_b                   10.7774(5)
_cell_length_c                   17.9836(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1470.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4043
_cell_measurement_theta_min      2.265
_cell_measurement_theta_max      24.716

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9256
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2560
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.2344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_number_reflns         2560
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3371(3) 0.10104(17) 0.61732(11) 0.0319(5) Uani 1 1 d . . .
H1 H 0.4438 0.0859 0.6487 0.038 Uiso 1 1 calc R . .
C2 C 0.1754(3) 0.05522(17) 0.65879(10) 0.0307(4) Uani 1 1 d . . .
C3 C 0.0640(3) -0.0322(2) 0.62898(12) 0.0432(6) Uani 1 1 d . . .
H3 H 0.0865 -0.0650 0.5809 0.052 Uiso 1 1 calc R . .
C4 C -0.0805(4) -0.0722(2) 0.66885(14) 0.0593(7) Uani 1 1 d . . .
H4 H -0.1560 -0.1334 0.6481 0.071 Uiso 1 1 calc R . .
C5 C -0.1168(4) -0.0248(2) 0.73829(14) 0.0573(7) Uani 1 1 d . . .
H5 H -0.2162 -0.0535 0.7654 0.069 Uiso 1 1 calc R . .
C6 C -0.0089(4) 0.0637(2) 0.76781(13) 0.0509(6) Uani 1 1 d . . .
H6 H -0.0340 0.0979 0.8153 0.061 Uiso 1 1 calc R . .
C7 C 0.1360(3) 0.1033(2) 0.72863(11) 0.0418(5) Uani 1 1 d . . .
H7 H 0.2108 0.1646 0.7497 0.050 Uiso 1 1 calc R . .
C8 C 0.3248(3) 0.23905(17) 0.59997(10) 0.0275(4) Uani 1 1 d . . .
C9 C 0.1783(3) 0.27774(18) 0.55753(11) 0.0303(4) Uani 1 1 d . . .
H9 H 0.0937 0.2162 0.5451 0.036 Uiso 1 1 calc R . .
C10 C 0.2708(3) 0.47910(17) 0.55190(10) 0.0289(5) Uani 1 1 d . . .
C11 C 0.2392(3) 0.60236(19) 0.52899(12) 0.0386(5) Uani 1 1 d . . .
H11 H 0.1361 0.6211 0.5012 0.046 Uiso 1 1 calc R . .
C12 C 0.3543(3) 0.69441(19) 0.54617(12) 0.0425(6) Uani 1 1 d . . .
H12 H 0.3314 0.7772 0.5308 0.051 Uiso 1 1 calc R . .
C13 C 0.5072(3) 0.66653(19) 0.58671(11) 0.0427(6) Uani 1 1 d . . .
H13 H 0.5881 0.7310 0.5982 0.051 Uiso 1 1 calc R . .
C14 C 0.5418(3) 0.5487(2) 0.60997(10) 0.0373(5) Uani 1 1 d . . .
H14 H 0.6460 0.5323 0.6376 0.045 Uiso 1 1 calc R . .
C15 C 0.4246(3) 0.45062(18) 0.59349(10) 0.0280(4) Uani 1 1 d . . .
C16 C 0.4501(3) 0.32592(19) 0.61898(10) 0.0283(4) Uani 1 1 d . . .
C17 C 0.7694(3) 0.2926(3) 0.62996(14) 0.0535(7) Uani 1 1 d . . .
H17A H 0.8013 0.2059 0.6207 0.080 Uiso 1 1 calc R . .
H17B H 0.8557 0.3301 0.6637 0.080 Uiso 1 1 calc R . .
H17C H 0.7684 0.3383 0.5828 0.080 Uiso 1 1 calc R . .
C18 C 0.5830(4) 0.2768(3) 0.73928(13) 0.0769(10) Uani 1 1 d . . .
H18A H 0.6684 0.3286 0.7660 0.115 Uiso 1 1 calc R . .
H18B H 0.6064 0.1892 0.7499 0.115 Uiso 1 1 calc R . .
H18C H 0.4635 0.2980 0.7556 0.115 Uiso 1 1 calc R . .
N1 N 0.1481(2) 0.39061(15) 0.53362(9) 0.0324(4) Uani 1 1 d . . .
N2 N 0.5983(2) 0.2979(2) 0.66303(10) 0.0472(5) Uani 1 1 d . . .
O1 O 0.3535(2) 0.03267(13) 0.55029(8) 0.0430(4) Uani 1 1 d . . .
H1A H 0.4465 0.0682 0.5194 0.052 Uiso 1 1 d R . .


_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
C1 O1 1.418(2) . ?
C1 C2 1.519(3) . ?
C1 C8 1.523(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.375(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.365(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.374(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C16 1.377(3) . ?
C8 C9 1.411(3) . ?
C9 N1 1.310(3) . ?
C9 H9 0.9500 . ?
C10 N1 1.373(2) . ?
C10 C11 1.411(3) . ?
C10 C15 1.420(3) . ?
C11 C12 1.357(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.413(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.433(3) . ?
C16 N2 1.409(2) . ?
C17 N2 1.429(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N2 1.395(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1 H1A 0.9759 . ?

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 C1 C2 108.62(16) . . ?
O1 C1 C8 109.80(15) . . ?
C2 C1 C8 111.62(16) . . ?
O1 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
C8 C1 H1 108.9 . . ?
C3 C2 C7 118.4(2) . . ?
C3 C2 C1 121.89(18) . . ?
C7 C2 C1 119.73(19) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C16 C8 C9 118.49(17) . . ?
C16 C8 C1 124.80(18) . . ?
C9 C8 C1 116.61(17) . . ?
N1 C9 C8 126.14(18) . . ?
N1 C9 H9 116.9 . . ?
C8 C9 H9 116.9 . . ?
N1 C10 C11 117.94(18) . . ?
N1 C10 C15 122.25(17) . . ?
C11 C10 C15 119.81(19) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 117.79(18) . . ?
C14 C15 C16 123.34(19) . . ?
C10 C15 C16 118.82(17) . . ?
C8 C16 N2 123.06(19) . . ?
C8 C16 C15 117.71(17) . . ?
N2 C16 C15 119.22(19) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 N1 C10 116.57(17) . . ?
C18 N2 C16 121.40(18) . . ?
C18 N2 C17 118.57(19) . . ?
C16 N2 C17 120.01(17) . . ?
C1 O1 H1A 110.1 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.033
