# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_m20190311c
_database_code_depnum_ccdc_archive 'CCDC 1906915'
loop_
_audit_author_name
_audit_author_address
'lingang Wu'
;Nankai university
China
;
_audit_update_record             
;
2019-04-01 deposited with the CCDC.	2019-06-18 downloaded from the CCDC.
;
_audit_creation_date             2019-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N O'
_chemical_formula_sum            'C16 H15 N O'
_chemical_formula_weight         237.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H15NO
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.7435(14)
_cell_length_b                   7.1127(9)
_cell_length_c                   15.6205(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.141(9)
_cell_angle_gamma                90
_cell_volume                     1299.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2897
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      28.7080
_cell_measurement_theta_min      3.8770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19218
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         3.352
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -84.00 94.00 0.50 40.00 -- 5.00 45.00 150.00 356 2 ω -97.00 81.00 0.50 40.00 -- -8.10 45.00 0.00 356 3 ω -78.00 -53.00 0.50 40.00 -- -8.10 45.00 90.00 50 4 ω -5.00 43.00 0.50 40.00 -- -8.10 45.00 90.00 96 5 ω -97.00 -84.50 0.50 40.00 -- -8.10 45.00 171.65 25'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058045000
_diffrn_orient_matrix_UB_12      0.0892697000
_diffrn_orient_matrix_UB_13      0.0201569000
_diffrn_orient_matrix_UB_21      0.0411275000
_diffrn_orient_matrix_UB_22      0.0259929000
_diffrn_orient_matrix_UB_23      -0.0284243000
_diffrn_orient_matrix_UB_31      -0.0441749000
_diffrn_orient_matrix_UB_32      0.0360414000
_diffrn_orient_matrix_UB_33      -0.0294119000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1791
_reflns_number_total             3232
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²+0.2324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1472
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57350(12) 0.7814(2) 0.46449(8) 0.0752(5) Uani 1 1 d . . . . .
N1 N 0.54017(11) 0.6503(2) 0.33348(8) 0.0459(4) Uani 1 1 d . . . . .
C1 C 0.51460(15) 0.7736(3) 0.39632(11) 0.0516(4) Uani 1 1 d . . . . .
C2 C 0.40965(16) 0.8901(3) 0.37644(11) 0.0579(5) Uani 1 1 d . . . . .
H2A H 0.414589 1.001538 0.412364 0.069 Uiso 1 1 calc R . . . .
H2B H 0.343318 0.818735 0.390248 0.069 Uiso 1 1 calc R . . . .
C3 C 0.39383(17) 0.9489(3) 0.28316(11) 0.0581(5) Uani 1 1 d . . . . .
H3A H 0.319606 1.007876 0.271430 0.070 Uiso 1 1 calc R . . . .
H3B H 0.451871 1.040448 0.271931 0.070 Uiso 1 1 calc R . . . .
C4 C 0.40228(13) 0.7826(2) 0.22462(10) 0.0443(4) Uani 1 1 d . . . . .
C5 C 0.47490(13) 0.6362(2) 0.25238(10) 0.0424(4) Uani 1 1 d . . . . .
C6 C 0.48642(16) 0.4792(3) 0.20045(11) 0.0535(5) Uani 1 1 d . . . . .
H6 H 0.534089 0.380564 0.219514 0.064 Uiso 1 1 calc R . . . .
C7 C 0.42620(17) 0.4718(3) 0.12026(12) 0.0604(5) Uani 1 1 d . . . . .
H7 H 0.433204 0.367252 0.085349 0.072 Uiso 1 1 calc R . . . .
C8 C 0.35609(16) 0.6178(3) 0.09184(11) 0.0596(5) Uani 1 1 d . . . . .
H8 H 0.316997 0.611657 0.037442 0.072 Uiso 1 1 calc R . . . .
C9 C 0.34274(15) 0.7739(3) 0.14290(11) 0.0526(5) Uani 1 1 d . . . . .
C10 C 0.26529(19) 0.9318(4) 0.10996(14) 0.0795(7) Uani 1 1 d . . . . .
H10A H 0.204448 0.945939 0.146611 0.119 Uiso 1 1 calc GR . . . .
H10B H 0.233756 0.903533 0.052577 0.119 Uiso 1 1 calc GR . . . .
H10C H 0.308302 1.046541 0.109716 0.119 Uiso 1 1 calc GR . . . .
C11 C 0.63643(15) 0.5266(3) 0.35383(10) 0.0493(4) Uani 1 1 d . . . . .
C12 C 0.62053(19) 0.3555(3) 0.39200(12) 0.0644(5) Uani 1 1 d . . . . .
H12 H 0.547938 0.317798 0.404298 0.077 Uiso 1 1 calc R . . . .
C13 C 0.7141(3) 0.2404(4) 0.41182(13) 0.0857(8) Uani 1 1 d . . . . .
H13 H 0.704142 0.123655 0.436909 0.103 Uiso 1 1 calc R . . . .
C14 C 0.8208(3) 0.2968(5) 0.39485(16) 0.0991(10) Uani 1 1 d . . . . .
H14 H 0.883263 0.218650 0.408490 0.119 Uiso 1 1 calc R . . . .
C15 C 0.8359(2) 0.4682(5) 0.35777(17) 0.0985(9) Uani 1 1 d . . . . .
H15 H 0.908836 0.507330 0.347162 0.118 Uiso 1 1 calc R . . . .
C16 C 0.74323(17) 0.5831(4) 0.33610(13) 0.0715(6) Uani 1 1 d . . . . .
H16 H 0.753239 0.698296 0.309609 0.086 Uiso 1 1 calc 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
O1 C1 1.218(2) . ?
N1 C1 1.369(2) . ?
N1 C5 1.424(2) . ?
N1 C11 1.445(2) . ?
C1 C2 1.494(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.511(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.504(2) . ?
C4 C5 1.390(2) . ?
C4 C9 1.401(2) . ?
C5 C6 1.394(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(3) . ?
C9 C10 1.506(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.375(3) . ?
C11 C16 1.369(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.368(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9300 . ?

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 N1 C5 123.19(14) . . ?
C1 N1 C11 116.72(13) . . ?
C5 N1 C11 120.06(13) . . ?
O1 C1 N1 120.80(16) . . ?
O1 C1 C2 123.33(16) . . ?
N1 C1 C2 115.84(14) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.43(14) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.07(16) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C5 C4 C3 118.12(14) . . ?
C5 C4 C9 119.57(16) . . ?
C9 C4 C3 122.27(16) . . ?
C4 C5 N1 119.42(14) . . ?
C4 C5 C6 120.47(15) . . ?
C6 C5 N1 120.09(15) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.30(18) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.42(18) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.05(16) . . ?
C9 C8 H8 119.5 . . ?
C4 C9 C10 121.01(17) . . ?
C8 C9 C4 119.16(18) . . ?
C8 C9 C10 119.83(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N1 120.00(17) . . ?
C16 C11 N1 119.33(17) . . ?
C16 C11 C12 120.66(19) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(2) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 119.6(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?

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 144.9(2) . . . . ?
N1 C1 C2 C3 -37.0(2) . . . . ?
N1 C5 C6 C7 -177.14(16) . . . . ?
N1 C11 C12 C13 -179.25(16) . . . . ?
N1 C11 C16 C15 178.02(19) . . . . ?
C1 N1 C5 C4 18.2(2) . . . . ?
C1 N1 C5 C6 -163.59(16) . . . . ?
C1 N1 C11 C12 88.8(2) . . . . ?
C1 N1 C11 C16 -90.0(2) . . . . ?
C1 C2 C3 C4 50.8(2) . . . . ?
C2 C3 C4 C5 -32.2(2) . . . . ?
C2 C3 C4 C9 149.91(16) . . . . ?
C3 C4 C5 N1 -1.4(2) . . . . ?
C3 C4 C5 C6 -179.64(16) . . . . ?
C3 C4 C9 C8 178.89(17) . . . . ?
C3 C4 C9 C10 -0.8(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 N1 C1 O1 -179.47(18) . . . . ?
C5 N1 C1 C2 2.4(2) . . . . ?
C5 N1 C11 C12 -89.23(19) . . . . ?
C5 N1 C11 C16 91.9(2) . . . . ?
C5 C4 C9 C8 1.0(2) . . . . ?
C5 C4 C9 C10 -178.67(17) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C7 C8 C9 C10 179.99(19) . . . . ?
C9 C4 C5 N1 176.50(15) . . . . ?
C9 C4 C5 C6 -1.7(2) . . . . ?
C11 N1 C1 O1 2.5(3) . . . . ?
C11 N1 C1 C2 -175.60(16) . . . . ?
C11 N1 C5 C4 -163.89(15) . . . . ?
C11 N1 C5 C6 14.3(2) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C11 C16 C15 -0.8(3) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C11 1.6(4) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.065
_oxdiff_exptl_absorpt_empirical_full_min 0.379
