# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_190809-c17h15no2-173k-
_database_code_depnum_ccdc_archive 'CCDC 1958661'
loop_
_audit_author_name
_audit_author_address
'Biao Zhou'
;Nihon University
Japan
;
#Added by publCIF



_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;
_audit_creation_date             2019-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        C17H15NO2
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      173
_chemical_oxdiff_formula         C17H15NO2
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 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
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                   8.6977(4)
_cell_length_b                   14.9757(6)
_cell_length_c                   10.6125(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.554(5)
_cell_angle_gamma                90
_cell_volume                     1354.31(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8161
_cell_measurement_temperature    173
_cell_measurement_theta_max      32.5350
_cell_measurement_theta_min      2.4230
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66865
_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_primary    yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13830
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         2.385
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50    3.00    --  -15.00  45.00   0.00  360
  2  ω   -105.00  75.00   0.50    3.00    --  -15.00  45.00  90.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0255194000
_diffrn_orient_matrix_UB_12      0.0151038000
_diffrn_orient_matrix_UB_13      0.0641311000
_diffrn_orient_matrix_UB_21      -0.0510137000
_diffrn_orient_matrix_UB_22      0.0372482000
_diffrn_orient_matrix_UB_23      -0.0131171000
_diffrn_orient_matrix_UB_31      -0.0606302000
_diffrn_orient_matrix_UB_32      -0.0250097000
_diffrn_orient_matrix_UB_33      0.0192915000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2462
_reflns_number_total             3101
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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         0.245
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.3945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1124
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C2(H2), C5(H5), C13(H13), C4(H4), C15(H15), C16(H16), C3(H3)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), 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 0.42034(11) 0.70935(6) 0.82660(9) 0.0298(2) Uani 1 1 d . . . . .
O2 O 0.09440(13) 0.51843(7) 0.31263(10) 0.0450(3) Uani 1 1 d . . . . .
N1 N 0.55164(14) 0.64974(8) 1.08368(11) 0.0338(3) Uani 1 1 d . . . . .
C12 C 0.26730(16) 0.65341(9) 0.58612(13) 0.0310(3) Uani 1 1 d . . . . .
H12 H 0.264172 0.714070 0.611680 0.037 Uiso 1 1 calc R . . . .
C8 C 0.55059(15) 0.57295(9) 0.87910(14) 0.0316(3) Uani 1 1 d . . . . .
H8 H 0.580171 0.515902 0.852828 0.038 Uiso 1 1 calc R . . . .
C11 C 0.35981(15) 0.59261(9) 0.66823(13) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.39572(16) 0.68002(9) 1.04456(13) 0.0309(3) Uani 1 1 d . . . . .
C6 C 0.32937(16) 0.70972(8) 0.92107(13) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.30250(18) 0.68396(10) 1.13752(14) 0.0375(3) Uani 1 1 d . . . . .
H2 H 0.344737 0.665080 1.222897 0.045 Uiso 1 1 calc R . . . .
C7 C 0.44796(15) 0.62071(8) 0.79422(13) 0.0280(3) Uani 1 1 d . . . . .
C5 C 0.17772(16) 0.74243(9) 0.88976(14) 0.0331(3) Uani 1 1 d . . . . .
H5 H 0.135815 0.762963 0.805157 0.040 Uiso 1 1 calc R . . . .
C13 C 0.18053(17) 0.62699(9) 0.46876(14) 0.0343(3) Uani 1 1 d . . . . .
H13 H 0.118626 0.669375 0.414269 0.041 Uiso 1 1 calc R . . . .
C4 C 0.08817(18) 0.74472(10) 0.98369(15) 0.0394(4) Uani 1 1 d . . . . .
H4 H -0.016222 0.766875 0.963493 0.047 Uiso 1 1 calc R . . . .
C9 C 0.61995(16) 0.60254(9) 1.00903(14) 0.0328(3) Uani 1 1 d . . . . .
C14 C 0.18346(16) 0.53842(10) 0.43002(14) 0.0336(3) Uani 1 1 d . . . . .
C15 C 0.27337(19) 0.47685(10) 0.51052(15) 0.0403(4) Uani 1 1 d . . . . .
H15 H 0.275662 0.416155 0.484906 0.048 Uiso 1 1 calc R . . . .
C16 C 0.35956(18) 0.50401(10) 0.62801(15) 0.0392(4) Uani 1 1 d . . . . .
H16 H 0.420151 0.461259 0.682743 0.047 Uiso 1 1 calc R . . . .
C3 C 0.14975(19) 0.71491(10) 1.10709(15) 0.0412(4) Uani 1 1 d . . . . .
H3 H 0.087032 0.715745 1.170794 0.049 Uiso 1 1 calc R . . . .
C17 C 0.0835(2) 0.42705(11) 0.27518(16) 0.0458(4) Uani 1 1 d . . . . .
H17A H 0.014197 0.421415 0.190531 0.069 Uiso 1 1 calc GR . . . .
H17B H 0.040626 0.392268 0.338388 0.069 Uiso 1 1 calc GR . . . .
H17C H 0.188081 0.404543 0.270828 0.069 Uiso 1 1 calc GR . . . .
C10 C 0.78221(18) 0.56853(12) 1.06431(17) 0.0455(4) Uani 1 1 d . . . . .
H10A H 0.856913 0.593974 1.016241 0.068 Uiso 1 1 calc GR . . . .
H10B H 0.783497 0.503267 1.057859 0.068 Uiso 1 1 calc GR . . . .
H10C H 0.811899 0.586201 1.154842 0.068 Uiso 1 1 calc GR . . . .


_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 C6 1.3961(16) . ?
O1 C7 1.4039(15) . ?
O2 C14 1.3621(17) . ?
O2 C17 1.4228(19) . ?
N1 C1 1.4112(18) . ?
N1 C9 1.2919(19) . ?
C12 C11 1.3982(19) . ?
C12 C13 1.379(2) . ?
C8 C7 1.3408(19) . ?
C8 C9 1.4588(19) . ?
C11 C7 1.4637(19) . ?
C11 C16 1.3936(19) . ?
C1 C6 1.3948(19) . ?
C1 C2 1.398(2) . ?
C6 C5 1.3837(19) . ?
C2 C3 1.383(2) . ?
C5 C4 1.383(2) . ?
C13 C14 1.390(2) . ?
C4 C3 1.386(2) . ?
C9 C10 1.504(2) . ?
C14 C15 1.387(2) . ?
C15 C16 1.381(2) . ?

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
C6 O1 C7 109.20(9) . . ?
C14 O2 C17 117.44(12) . . ?
C9 N1 C1 121.89(12) . . ?
C13 C12 C11 121.24(13) . . ?
C7 C8 C9 124.51(13) . . ?
C12 C11 C7 120.85(12) . . ?
C16 C11 C12 117.63(13) . . ?
C16 C11 C7 121.46(12) . . ?
C6 C1 N1 124.84(13) . . ?
C6 C1 C2 117.41(13) . . ?
C2 C1 N1 117.70(13) . . ?
C1 C6 O1 119.09(12) . . ?
C5 C6 O1 118.62(12) . . ?
C5 C6 C1 122.25(13) . . ?
C3 C2 C1 121.01(14) . . ?
O1 C7 C11 114.30(11) . . ?
C8 C7 O1 117.62(12) . . ?
C8 C7 C11 128.08(12) . . ?
C4 C5 C6 118.89(13) . . ?
C12 C13 C14 120.12(13) . . ?
C5 C4 C3 120.42(14) . . ?
N1 C9 C8 126.29(13) . . ?
N1 C9 C10 117.18(13) . . ?
C8 C9 C10 116.35(13) . . ?
O2 C14 C13 116.06(13) . . ?
O2 C14 C15 124.36(13) . . ?
C15 C14 C13 119.57(13) . . ?
C16 C15 C14 119.82(13) . . ?
C15 C16 C11 121.61(13) . . ?
C2 C3 C4 120.01(14) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.149
_oxdiff_exptl_absorpt_empirical_full_min 0.676



_publcif_funding_html            
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