# 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_20180717tongshuo
_database_code_depnum_ccdc_archive 'CCDC 1860475'
_audit_update_record             
;
2018-08-06 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H0.25 N O'
_chemical_formula_weight         234.43

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   6.22900(10)
_cell_length_b                   13.6065(2)
_cell_length_c                   14.6177(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1238.92(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            orange
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             469
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            8892
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.44
_diffrn_reflns_theta_max         71.47
_reflns_number_total             2376
_reflns_number_gt                2253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0405P)²+0.1237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.0(3)
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7555(2) 0.78108(8) 0.29560(8) 0.0559(3) Uani 1 1 d . . .
N1 N 0.7393(2) 0.62572(8) 0.22528(8) 0.0395(3) Uani 1 1 d . . .
C5 C 1.0301(2) 0.64274(11) 0.12861(10) 0.0416(3) Uani 1 1 d . . .
C4 C 0.8517(2) 0.58003(11) 0.15486(10) 0.0408(3) Uani 1 1 d . . .
C12 C 0.4199(2) 0.58499(11) 0.32820(11) 0.0438(3) Uani 1 1 d . . .
C6 C 1.0142(2) 0.72825(11) 0.18154(10) 0.0417(3) Uani 1 1 d . . .
C7 C 0.8254(2) 0.72102(10) 0.24236(10) 0.0413(3) Uani 1 1 d . . .
C1 C 0.5673(2) 0.56561(11) 0.25221(10) 0.0422(3) Uani 1 1 d . . .
C2 C 0.5772(3) 0.48444(11) 0.19683(11) 0.0481(4) Uani 1 1 d . . .
H2 H 0.4820 0.4318 0.1986 0.058 Uiso 1 1 calc R . .
C11 C 1.1990(3) 0.63094(13) 0.06835(11) 0.0492(4) Uani 1 1 d . . .
H11 H 1.2114 0.5745 0.0329 0.059 Uiso 1 1 calc R . .
C10 C 1.3494(3) 0.70572(14) 0.06224(12) 0.0557(4) Uani 1 1 d . . .
H10 H 1.4643 0.6988 0.0221 0.067 Uiso 1 1 calc R . .
C17 C 0.2196(3) 0.53921(13) 0.32852(12) 0.0537(4) Uani 1 1 d . . .
H17 H 0.1806 0.4988 0.2800 0.064 Uiso 1 1 calc R . .
C8 C 1.1642(3) 0.80255(13) 0.17500(11) 0.0512(4) Uani 1 1 d . . .
H8 H 1.1523 0.8592 0.2103 0.061 Uiso 1 1 calc R . .
C13 C 0.4761(3) 0.64307(12) 0.40339(11) 0.0530(4) Uani 1 1 d . . .
H13 H 0.6104 0.6729 0.4053 0.064 Uiso 1 1 calc R . .
C3 C 0.7545(3) 0.49277(12) 0.13642(11) 0.0475(4) Uani 1 1 d . . .
H3 H 0.7963 0.4472 0.0925 0.057 Uiso 1 1 calc R . .
C16 C 0.0782(3) 0.55335(14) 0.40050(14) 0.0619(5) Uani 1 1 d . . .
H16 H -0.0551 0.5225 0.3999 0.074 Uiso 1 1 calc R . .
C9 C 1.3331(3) 0.79038(14) 0.11427(12) 0.0573(4) Uani 1 1 d . . .
H9 H 1.4362 0.8394 0.1085 0.069 Uiso 1 1 calc R . .
C15 C 0.1341(3) 0.61291(14) 0.47306(14) 0.0626(5) Uani 1 1 d . . .
H15 H 0.0375 0.6236 0.5206 0.075 Uiso 1 1 calc R . .
C14 C 0.3342(3) 0.65657(13) 0.47483(13) 0.0624(5) Uani 1 1 d . . .
H14 H 0.3737 0.6953 0.5245 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0707(7) 0.0424(6) 0.0545(7) -0.0108(5) 0.0094(6) 0.0013(6)
N1 0.0442(6) 0.0358(6) 0.0384(6) -0.0015(5) -0.0021(5) 0.0015(5)
C5 0.0465(8) 0.0413(7) 0.0370(7) 0.0042(6) -0.0066(6) 0.0038(7)
C4 0.0476(7) 0.0403(7) 0.0345(7) -0.0006(6) -0.0034(6) 0.0050(6)
C12 0.0425(7) 0.0457(8) 0.0431(8) 0.0104(7) -0.0032(7) 0.0049(6)
C6 0.0454(8) 0.0438(8) 0.0360(7) 0.0013(6) -0.0033(7) 0.0010(6)
C7 0.0485(8) 0.0372(7) 0.0383(7) -0.0005(6) -0.0043(7) 0.0014(6)
C1 0.0438(8) 0.0428(8) 0.0401(7) 0.0051(6) -0.0054(7) 0.0036(6)
C2 0.0534(9) 0.0410(8) 0.0500(9) 0.0003(7) -0.0071(8) -0.0062(7)
C11 0.0538(9) 0.0493(8) 0.0444(8) 0.0040(7) 0.0017(7) 0.0116(7)
C10 0.0475(9) 0.0670(11) 0.0525(9) 0.0114(9) 0.0048(8) 0.0065(8)
C17 0.0497(9) 0.0588(10) 0.0525(9) 0.0120(8) -0.0086(8) 0.0003(8)
C8 0.0570(9) 0.0479(8) 0.0487(9) 0.0000(7) -0.0012(8) -0.0076(7)
C13 0.0536(9) 0.0527(9) 0.0527(9) -0.0021(8) 0.0089(8) -0.0037(8)
C3 0.0589(9) 0.0414(8) 0.0422(8) -0.0083(6) -0.0043(7) 0.0014(7)
C16 0.0446(9) 0.0699(11) 0.0712(12) 0.0237(10) 0.0035(9) 0.0014(8)
C9 0.0518(9) 0.0629(11) 0.0572(10) 0.0088(9) -0.0004(8) -0.0123(8)
C15 0.0633(11) 0.0569(10) 0.0677(12) 0.0168(9) 0.0235(9) 0.0111(9)
C14 0.0742(12) 0.0547(10) 0.0582(11) -0.0024(8) 0.0188(10) -0.0002(9)

_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 1.2097(18) . ?
N1 C4 1.3917(18) . ?
N1 C1 1.4042(19) . ?
N1 C7 1.4252(18) . ?
C5 C11 1.381(2) . ?
C5 C6 1.401(2) . ?
C5 C4 1.452(2) . ?
C4 C3 1.360(2) . ?
C12 C17 1.395(2) . ?
C12 C13 1.398(2) . ?
C12 C1 1.465(2) . ?
C6 C8 1.380(2) . ?
C6 C7 1.478(2) . ?
C1 C2 1.371(2) . ?
C2 C3 1.419(3) . ?
C11 C10 1.386(2) . ?
C10 C9 1.384(3) . ?
C17 C16 1.386(3) . ?
C8 C9 1.387(2) . ?
C13 C14 1.380(2) . ?
C16 C15 1.380(3) . ?
C15 C14 1.381(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
C4 N1 C1 109.34(12) . . ?
C4 N1 C7 110.28(12) . . ?
C1 N1 C7 140.17(13) . . ?
C11 C5 C6 120.17(15) . . ?
C11 C5 C4 133.05(14) . . ?
C6 C5 C4 106.74(13) . . ?
C3 C4 N1 108.20(14) . . ?
C3 C4 C5 143.25(15) . . ?
N1 C4 C5 108.54(12) . . ?
C17 C12 C13 118.27(15) . . ?
C17 C12 C1 118.87(15) . . ?
C13 C12 C1 122.75(14) . . ?
C8 C6 C5 121.49(14) . . ?
C8 C6 C7 129.01(14) . . ?
C5 C6 C7 109.46(13) . . ?
O1 C7 N1 126.29(14) . . ?
O1 C7 C6 128.95(14) . . ?
N1 C7 C6 104.76(12) . . ?
C2 C1 N1 105.63(13) . . ?
C2 C1 C12 128.39(15) . . ?
N1 C1 C12 125.86(13) . . ?
C1 C2 C3 109.77(14) . . ?
C5 C11 C10 118.07(16) . . ?
C9 C10 C11 121.75(16) . . ?
C16 C17 C12 120.63(18) . . ?
C6 C8 C9 118.08(15) . . ?
C14 C13 C12 120.65(17) . . ?
C4 C3 C2 107.05(14) . . ?
C15 C16 C17 120.31(17) . . ?
C10 C9 C8 120.44(16) . . ?
C16 C15 C14 119.67(17) . . ?
C13 C14 C15 120.42(19) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        71.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
