# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mashq_1205
_database_code_depnum_ccdc_archive 'CCDC 2007713'
loop_
_audit_author_name
_audit_author_address
'Shiqiang Ma'
;Lanzhou University
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2018-12-07
_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_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_melting_point          ?
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'
H H 0.0000 0.0000 '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'

_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   25.4782(8)
_cell_length_b                   13.9470(4)
_cell_length_c                   7.1727(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2548.79(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2227
_cell_measurement_temperature    292.60(10)
_cell_measurement_theta_max      69.6900
_cell_measurement_theta_min      6.3330
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5439
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         6.347
_diffrn_ambient_temperature      292.60(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -86.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega   55.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega   68.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega  105.00  170.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 11 omega   66.00   92.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   75.00  100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   43.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -120.0000 133
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0100384000
_diffrn_orient_matrix_UB_12      0.1088559000
_diffrn_orient_matrix_UB_13      -0.0082603000
_diffrn_orient_matrix_UB_21      0.0512812000
_diffrn_orient_matrix_UB_22      -0.0135860000
_diffrn_orient_matrix_UB_23      0.1106903000
_diffrn_orient_matrix_UB_31      0.0304239000
_diffrn_orient_matrix_UB_32      -0.0130790000
_diffrn_orient_matrix_UB_33      -0.1838324000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1883
_reflns_number_total             2188
_reflns_odcompleteness_completeness 95.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.041
_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)+(0.0950P)²+0.4954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1683
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C6(H6), C11(H11), C12(H12), C14(H14), C16(H16)
2.c X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.51598(6) 0.11805(10) -0.0021(3) 0.0747(5) Uani 1 1 d . . . . .
C2 C 0.73663(8) 0.32150(13) -0.1074(2) 0.0553(5) Uani 1 1 d . . . . .
O3 O 0.55820(6) -0.00431(11) -0.1322(3) 0.0746(5) Uani 1 1 d . . . . .
N4 N 0.69610(6) 0.26781(12) -0.0384(2) 0.0609(5) Uani 1 1 d . . . . .
H4 H 0.699280 0.222346 0.041815 0.073 Uiso 1 1 calc R . . . .
C5 C 0.64950(8) 0.29741(15) -0.1164(3) 0.0608(5) Uani 1 1 d . . . . .
C6 C 0.78977(9) 0.31817(16) -0.0680(3) 0.0648(5) Uani 1 1 d . . . . .
H6 H 0.803148 0.274744 0.018199 0.078 Uiso 1 1 calc R . . . .
C7 C 0.55377(7) 0.08544(14) -0.0889(3) 0.0561(5) Uani 1 1 d . . . . .
C8 C 0.65924(9) 0.37096(13) -0.2370(3) 0.0643(5) Uani 1 1 d . . . . .
C9 C 0.71494(9) 0.38688(12) -0.2351(3) 0.0580(5) Uani 1 1 d . . . . .
C10 C 0.59999(8) 0.24628(16) -0.0664(4) 0.0697(6) Uani 1 1 d . . . . .
H10A H 0.570151 0.284011 -0.107263 0.084 Uiso 1 1 calc R . . . .
H10B H 0.597898 0.239709 0.068006 0.084 Uiso 1 1 calc R . . . .
C11 C 0.82209(10) 0.38105(17) -0.1601(3) 0.0740(7) Uani 1 1 d . . . . .
H11 H 0.857984 0.379940 -0.136657 0.089 Uiso 1 1 calc R . . . .
C12 C 0.80219(10) 0.44570(17) -0.2866(3) 0.0764(7) Uani 1 1 d . . . . .
H12 H 0.824996 0.487457 -0.347116 0.092 Uiso 1 1 calc R . . . .
C13 C 0.59742(8) 0.14749(16) -0.1557(3) 0.0649(5) Uani 1 1 d . . . . .
H13A H 0.594006 0.155404 -0.289495 0.078 Uiso 1 1 calc R . . . .
H13B H 0.630363 0.114722 -0.132497 0.078 Uiso 1 1 calc R . . . .
C14 C 0.74948(12) 0.45005(15) -0.3258(3) 0.0755(7) Uani 1 1 d . . . . .
H14 H 0.736777 0.494397 -0.411425 0.091 Uiso 1 1 calc R . . . .
C15 C 0.61983(13) 0.42435(18) -0.3546(5) 0.0943(9) Uani 1 1 d . . . . .
H15A H 0.591044 0.444705 -0.275464 0.113 Uiso 1 1 calc R . . . .
H15B H 0.636421 0.481566 -0.404002 0.113 Uiso 1 1 calc R . . . .
C16 C 0.59864(15) 0.3692(3) -0.5088(5) 0.1090(11) Uani 1 1 d . . . . .
H16 H 0.622852 0.345781 -0.594544 0.131 Uiso 1 1 calc R . . . .
C17 C 0.55022(19) 0.3489(5) -0.5405(8) 0.185(3) Uani 1 1 d . . . . .
H17A H 0.524299 0.370490 -0.459345 0.222 Uiso 1 1 calc R . . . .
H17B H 0.541108 0.312779 -0.644484 0.222 Uiso 1 1 calc R . . . .
H3 H 0.5317(18) -0.042(3) -0.077(6) 0.161(17) Uiso 1 1 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 C7 1.234(2) . ?
C2 N4 1.368(2) . ?
C2 C6 1.384(3) . ?
C2 C9 1.405(3) . ?
O3 C7 1.295(3) . ?
O3 H3 0.94(5) . ?
N4 H4 0.8600 . ?
N4 C5 1.376(3) . ?
C5 C8 1.364(3) . ?
C5 C10 1.493(3) . ?
C6 H6 0.9300 . ?
C6 C11 1.372(3) . ?
C7 C13 1.488(3) . ?
C8 C9 1.437(3) . ?
C8 C15 1.508(3) . ?
C9 C14 1.405(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C13 1.521(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C12 C14 1.373(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.452(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.286(5) . ?
C17 H17A 0.9300 . ?
C17 H17B 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
N4 C2 C6 130.23(18) . . ?
N4 C2 C9 107.10(17) . . ?
C6 C2 C9 122.67(18) . . ?
C7 O3 H3 112(2) . . ?
C2 N4 H4 125.1 . . ?
C2 N4 C5 109.86(17) . . ?
C5 N4 H4 125.1 . . ?
N4 C5 C10 119.21(19) . . ?
C8 C5 N4 109.05(19) . . ?
C8 C5 C10 131.7(2) . . ?
C2 C6 H6 121.1 . . ?
C11 C6 C2 117.8(2) . . ?
C11 C6 H6 121.1 . . ?
O1 C7 O3 123.06(19) . . ?
O1 C7 C13 122.10(19) . . ?
O3 C7 C13 114.84(17) . . ?
C5 C8 C9 106.86(19) . . ?
C5 C8 C15 127.2(2) . . ?
C9 C8 C15 125.9(2) . . ?
C2 C9 C8 107.11(16) . . ?
C14 C9 C2 117.5(2) . . ?
C14 C9 C8 135.4(2) . . ?
C5 C10 H10A 109.3 . . ?
C5 C10 H10B 109.3 . . ?
C5 C10 C13 111.59(18) . . ?
H10A C10 H10B 108.0 . . ?
C13 C10 H10A 109.3 . . ?
C13 C10 H10B 109.3 . . ?
C6 C11 H11 119.5 . . ?
C6 C11 C12 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.2 . . ?
C14 C12 C11 121.60(19) . . ?
C14 C12 H12 119.2 . . ?
C7 C13 C10 115.06(17) . . ?
C7 C13 H13A 108.5 . . ?
C7 C13 H13B 108.5 . . ?
C10 C13 H13A 108.5 . . ?
C10 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C9 C14 H14 120.3 . . ?
C12 C14 C9 119.4(2) . . ?
C12 C14 H14 120.3 . . ?
C8 C15 H15A 108.7 . . ?
C8 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C8 114.3(2) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16 116.3 . . ?
C17 C16 C15 127.4(5) . . ?
C17 C16 H16 116.3 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?

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 C7 C13 C10 15.9(3) . . . . ?
C2 N4 C5 C8 -0.1(2) . . . . ?
C2 N4 C5 C10 177.79(18) . . . . ?
C2 C6 C11 C12 0.4(3) . . . . ?
C2 C9 C14 C12 -0.1(3) . . . . ?
O3 C7 C13 C10 -165.3(2) . . . . ?
N4 C2 C6 C11 179.6(2) . . . . ?
N4 C2 C9 C8 1.0(2) . . . . ?
N4 C2 C9 C14 -179.68(17) . . . . ?
N4 C5 C8 C9 0.7(2) . . . . ?
N4 C5 C8 C15 179.2(2) . . . . ?
N4 C5 C10 C13 -72.6(3) . . . . ?
C5 C8 C9 C2 -1.1(2) . . . . ?
C5 C8 C9 C14 179.8(2) . . . . ?
C5 C8 C15 C16 -71.3(4) . . . . ?
C5 C10 C13 C7 170.47(19) . . . . ?
C6 C2 N4 C5 179.2(2) . . . . ?
C6 C2 C9 C8 -178.74(19) . . . . ?
C6 C2 C9 C14 0.6(3) . . . . ?
C6 C11 C12 C14 0.0(4) . . . . ?
C8 C5 C10 C13 104.8(3) . . . . ?
C8 C9 C14 C12 179.0(2) . . . . ?
C8 C15 C16 C17 121.6(5) . . . . ?
C9 C2 N4 C5 -0.5(2) . . . . ?
C9 C2 C6 C11 -0.8(3) . . . . ?
C9 C8 C15 C16 106.9(3) . . . . ?
C10 C5 C8 C9 -176.8(2) . . . . ?
C10 C5 C8 C15 1.7(4) . . . . ?
C11 C12 C14 C9 -0.2(3) . . . . ?
C15 C8 C9 C2 -179.6(2) . . . . ?
C15 C8 C9 C14 1.2(4) . . . . ?

_olex2_date_sample_data_collection 2018-12-06
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mashq_0912
_database_code_depnum_ccdc_archive 'CCDC 2007714'
loop_
_audit_author_name
_audit_author_address
'Shiqiang Ma'
;Lanzhou University
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;
_audit_creation_date             2018-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.8(C15 H15 N O)'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.1714(6)
_cell_length_b                   14.8338(9)
_cell_length_c                   9.4775(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.911(7)
_cell_angle_gamma                90.00
_cell_volume                     1219.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3990
_cell_measurement_theta_min      3.6010
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             455
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4748
_diffrn_reflns_theta_full        28.54
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.889
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   71.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   77.0000 -120.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0624917000
_diffrn_orient_matrix_UB_12      -0.0280626000
_diffrn_orient_matrix_UB_13      -0.0003883000
_diffrn_orient_matrix_UB_21      -0.0369650000
_diffrn_orient_matrix_UB_22      -0.0091955000
_diffrn_orient_matrix_UB_23      -0.0767692000
_diffrn_orient_matrix_UB_31      0.0375725000
_diffrn_orient_matrix_UB_32      0.0376148000
_diffrn_orient_matrix_UB_33      -0.0190764000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1559
_reflns_number_total             2772
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0620
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0670P)²+0.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1753
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C11(H11a,H11b), C9(H9a,H9b), C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C14(H14), C3(H3), C4(H4)
2.c X=CH2 refined with riding coordinates:
 C15(H15a,H15b)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.73100(17) 0.10371(11) 0.55181(19) 0.0457(5) Uani 1 d . . .
O1 O 0.47076(16) 0.11044(11) 0.48809(19) 0.0662(5) Uani 1 d . . .
C12 C 0.5937(2) 0.09544(15) 0.5827(3) 0.0516(6) Uani 1 d . . .
C8 C 0.8791(2) 0.08765(14) 0.6552(2) 0.0468(5) Uani 1 d . . .
C1 C 0.7488(2) 0.13036(13) 0.4163(2) 0.0452(5) Uani 1 d . . .
C7 C 0.9866(2) 0.10171(14) 0.5888(2) 0.0478(5) Uani 1 d . . .
C6 C 0.9080(2) 0.12952(13) 0.4380(2) 0.0469(5) Uani 1 d . . .
C13 C 1.1585(2) 0.09404(16) 0.6612(3) 0.0598(7) Uani 1 d . . .
H13A H 1.1807 0.0436 0.7300 0.072 Uiso 1 calc . . R
H13B H 1.2053 0.0814 0.5850 0.072 Uiso 1 calc . . R
C2 C 0.6412(3) 0.15315(15) 0.2802(3) 0.0584(6) Uani 1 d . . .
H2 H 0.5362 0.1532 0.2666 0.070 Uiso 1 calc . . R
C5 C 0.9593(3) 0.15362(15) 0.3196(3) 0.0616(7) Uani 1 d . . .
H5 H 1.0640 0.1544 0.3315 0.074 Uiso 1 calc . . R
C11 C 0.6089(3) 0.06991(18) 0.7397(3) 0.0666(7) Uani 1 d . . .
H11A H 0.5188 0.0354 0.7387 0.080 Uiso 1 calc . . R
H11B H 0.6100 0.1245 0.7963 0.080 Uiso 1 calc . . R
C9 C 0.8946(3) 0.06209(18) 0.8104(2) 0.0644(7) Uani 1 d . . .
H9A H 0.9135 0.1157 0.8722 0.077 Uiso 1 calc . . R
H9B H 0.9823 0.0222 0.8489 0.077 Uiso 1 calc . . R
C14 C 1.2294(3) 0.17718(19) 0.7434(4) 0.0718(8) Uani 1 d . . .
H14 H 1.2191 0.2293 0.6865 0.086 Uiso 1 calc . . R
C3 C 0.6967(3) 0.17571(18) 0.1659(3) 0.0709(7) Uani 1 d . . .
H3 H 0.6273 0.1910 0.0733 0.085 Uiso 1 calc . . R
C10 C 0.7513(3) 0.0156(2) 0.8188(3) 0.0760(8) Uani 1 d . . .
H10A H 0.7586 0.0076 0.9225 0.091 Uiso 1 calc . . R
H10B H 0.7431 -0.0436 0.7734 0.091 Uiso 1 calc . . R
C4 C 0.8527(4) 0.17615(17) 0.1854(3) 0.0717(8) Uani 1 d . . .
H4 H 0.8860 0.1920 0.1059 0.086 Uiso 1 calc . . R
C15 C 1.3006(3) 0.1851(3) 0.8790(4) 0.1059(12) Uani 1 d . . .
H15A H 1.3145 0.1352 0.9414 0.127 Uiso 1 calc . . R
H15B H 1.3400 0.2408 0.9179 0.127 Uiso 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
N1 C12 1.388(3) . ?
N1 C8 1.414(2) . ?
N1 C1 1.402(3) . ?
O1 C12 1.212(2) . ?
C12 C11 1.497(3) . ?
C8 C7 1.347(3) . ?
C8 C9 1.481(3) . ?
C1 C6 1.407(3) . ?
C1 C2 1.389(3) . ?
C7 C6 1.437(3) . ?
C7 C13 1.506(3) . ?
C6 C5 1.397(3) . ?
C13 C14 1.491(3) . ?
C2 C3 1.378(3) . ?
C5 C4 1.371(3) . ?
C11 C10 1.510(3) . ?
C9 C10 1.510(3) . ?
C14 C15 1.244(4) . ?
C3 C4 1.382(4) . ?

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
C12 N1 C8 124.96(19) . . ?
C12 N1 C1 126.92(18) . . ?
C1 N1 C8 108.12(16) . . ?
N1 C12 C11 115.65(19) . . ?
O1 C12 N1 121.2(2) . . ?
O1 C12 C11 123.1(2) . . ?
N1 C8 C9 119.51(18) . . ?
C7 C8 N1 109.57(19) . . ?
C7 C8 C9 130.90(19) . . ?
N1 C1 C6 106.68(18) . . ?
C2 C1 N1 131.4(2) . . ?
C2 C1 C6 121.9(2) . . ?
C8 C7 C6 107.55(18) . . ?
C8 C7 C13 126.3(2) . . ?
C6 C7 C13 126.1(2) . . ?
C1 C6 C7 108.07(19) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 133.0(2) . . ?
C14 C13 C7 112.97(19) . . ?
C3 C2 C1 117.2(2) . . ?
C4 C5 C6 118.9(2) . . ?
C12 C11 C10 114.57(19) . . ?
C8 C9 C10 111.41(19) . . ?
C15 C14 C13 127.7(3) . . ?
C2 C3 C4 121.7(3) . . ?
C9 C10 C11 110.9(2) . . ?
C5 C4 C3 121.3(2) . . ?


_olex2_date_sample_data_collection 2018-09-12
_olex2_submission_special_instructions 'No special instructions were received'
