# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2105086'
loop_
_audit_author_name
_audit_author_address
'Chen Zijian'
;South China University of technology
China
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_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         'C8 H7 N O'
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15
_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      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7910(3)
_cell_length_b                   8.12373(15)
_cell_length_c                   13.4636(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.515(3)
_cell_angle_gamma                90
_cell_volume                     1301.54(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4169
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1610
_cell_measurement_theta_min      3.7120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5857
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.042
_diffrn_reflns_theta_max         67.042
_diffrn_reflns_theta_min         3.714
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -35.00   0.50    0.50    --    0.00 -19.00-150.00  104
  2  ω    -31.00  13.00   0.50    0.50    --    0.00 -19.00 -90.00   88
  3  ω    -77.00 -49.00   0.50    0.50    --    5.00 -37.00  30.00   56
  4  ω    -32.00  18.00   0.50    0.50    --    5.00 -37.00  30.00  100
  5  ω   -187.00-161.00   0.50    0.50    --  -98.80 -72.00-180.00   52
  6  ω   -101.00 -10.00   0.50    0.50    --  -98.80  19.00  60.00  182
  7  ω   -113.00 -82.00   0.50    0.50    --  -98.80  57.00  60.00   62
  8  ω   -181.00 -88.00   0.50    0.50    --  -98.80 -37.00 -90.00  186
  9  ω   -102.00 -18.00   0.50    0.50    --  -98.80  72.00  60.00  168
 10  ω    -58.00  -9.00   0.50    0.50    --  -98.80  72.00 150.00   98
 11  ω    -57.00 -32.00   0.50    0.50    --  -98.80  57.00  60.00   50
 12  ω   -134.00-108.00   0.50    0.50    --  -98.80 -72.00-180.00   52
 13  ω    -58.00 -13.00   0.50    0.50    --  -98.80   0.00-180.00   90
 14  ω   -188.00 -76.00   0.50    0.50    --  -98.80   0.00-180.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611950000
_diffrn_orient_matrix_UB_12      0.1669626000
_diffrn_orient_matrix_UB_13      -0.0183498000
_diffrn_orient_matrix_UB_21      0.0070629000
_diffrn_orient_matrix_UB_22      0.0111120000
_diffrn_orient_matrix_UB_23      -0.1114974000
_diffrn_orient_matrix_UB_31      -0.1138948000
_diffrn_orient_matrix_UB_32      -0.0894627000
_diffrn_orient_matrix_UB_33      -0.0484885000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2116
_reflns_number_total             2320
_reflns_odcompleteness_completeness 99.96
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.170
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.076
_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)+(0.0601P)²+0.3053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1066
_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:
 C00A(H00D,H00E), C00D(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C009(H009), C00C(H00C), C00E(H00G), C00F(H00F),
 C00G(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
;
_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
O001 O 0.67104(8) 0.42864(13) 0.67196(8) 0.0341(3) Uani 1 1 d . . . . .
O002 O 0.66447(8) 0.47056(13) 0.39478(7) 0.0329(3) Uani 1 1 d . . . . .
N003 N 0.54160(9) 0.31404(14) 0.52018(8) 0.0261(3) Uani 1 1 d . . . . .
H003 H 0.565119 0.357794 0.474050 0.031 Uiso 1 1 calc R . . . .
N004 N 0.79686(9) 0.54712(14) 0.55551(9) 0.0270(3) Uani 1 1 d . . . . .
H004 H 0.765399 0.505214 0.596196 0.032 Uiso 1 1 calc R . . . .
C005 C 0.58917(11) 0.33974(17) 0.62694(10) 0.0264(3) Uani 1 1 d . . . . .
C006 C 0.75412(11) 0.53697(17) 0.44786(10) 0.0265(3) Uani 1 1 d . . . . .
C007 C 0.44882(10) 0.20672(16) 0.49420(10) 0.0241(3) Uani 1 1 d . . . . .
C008 C 0.43480(11) 0.15947(17) 0.58838(10) 0.0260(3) Uani 1 1 d . . . . .
C009 C 1.06442(11) 0.75811(18) 0.71349(11) 0.0311(3) Uani 1 1 d . . . . .
H009 H 1.111621 0.783838 0.782753 0.037 Uiso 1 1 calc R . . . .
C00A C 0.83609(11) 0.62092(18) 0.40616(10) 0.0296(3) Uani 1 1 d . . . . .
H00D H 0.866238 0.543562 0.368692 0.036 Uiso 1 1 calc R . . . .
H00E H 0.800385 0.711146 0.358634 0.036 Uiso 1 1 calc R . . . .
C00B C 0.89858(10) 0.63405(16) 0.59301(10) 0.0241(3) Uani 1 1 d . . . . .
C00C C 0.37884(11) 0.15227(18) 0.39562(10) 0.0287(3) Uani 1 1 d . . . . .
H00C H 0.388554 0.186179 0.333591 0.034 Uiso 1 1 calc R . . . .
C00D C 0.52348(11) 0.24301(18) 0.68017(10) 0.0291(3) Uani 1 1 d . . . . .
H00A H 0.570956 0.163184 0.730026 0.035 Uiso 1 1 calc R . . . .
H00B H 0.490182 0.315290 0.717795 0.035 Uiso 1 1 calc R . . . .
C00E C 0.96620(11) 0.66978(17) 0.69715(10) 0.0279(3) Uani 1 1 d . . . . .
H00G H 0.946853 0.636113 0.754181 0.033 Uiso 1 1 calc R . . . .
C00F C 0.34929(12) 0.05274(19) 0.58382(12) 0.0324(3) Uani 1 1 d . . . . .
H00F H 0.339082 0.020030 0.645843 0.039 Uiso 1 1 calc R . . . .
C00G C 1.09307(12) 0.8082(2) 0.62877(12) 0.0360(4) Uani 1 1 d . . . . .
H00H H 1.159059 0.867193 0.641534 0.043 Uiso 1 1 calc R . . . .
C00H C 0.92647(11) 0.68260(17) 0.50643(10) 0.0267(3) Uani 1 1 d . . . . .
C00I C 0.29288(12) 0.04453(19) 0.39189(12) 0.0340(3) Uani 1 1 d . . . . .
H00I H 0.244393 0.005277 0.326276 0.041 Uiso 1 1 calc R . . . .
C00J C 0.27851(12) -0.0051(2) 0.48450(12) 0.0361(4) Uani 1 1 d . . . . .
H00J H 0.220916 -0.077863 0.480314 0.043 Uiso 1 1 calc R . . . .
C00K C 1.02357(12) 0.7709(2) 0.52406(11) 0.0346(3) Uani 1 1 d . . . . .
H00K H 1.042592 0.805269 0.466976 0.042 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
O001 C005 1.2329(17) . ?
O002 C006 1.2312(17) . ?
N003 C005 1.3559(17) . ?
N003 C007 1.4094(17) . ?
N004 C006 1.3510(17) . ?
N004 C00B 1.4016(17) . ?
C005 C00D 1.5096(18) . ?
C006 C00A 1.5202(19) . ?
C007 C008 1.3980(17) . ?
C007 C00C 1.3737(18) . ?
C008 C00D 1.4987(19) . ?
C008 C00F 1.379(2) . ?
C009 C00E 1.3925(19) . ?
C009 C00G 1.381(2) . ?
C00A C00H 1.5051(18) . ?
C00B C00E 1.3816(18) . ?
C00B C00H 1.3953(18) . ?
C00C C00I 1.392(2) . ?
C00F C00J 1.393(2) . ?
C00G C00K 1.397(2) . ?
C00H C00K 1.377(2) . ?
C00I C00J 1.385(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
C005 N003 C007 111.59(10) . . ?
C006 N004 C00B 111.97(11) . . ?
O001 C005 N003 125.55(12) . . ?
O001 C005 C00D 126.29(12) . . ?
N003 C005 C00D 108.16(11) . . ?
O002 C006 N004 125.02(13) . . ?
O002 C006 C00A 127.15(12) . . ?
N004 C006 C00A 107.84(11) . . ?
C008 C007 N003 108.73(11) . . ?
C00C C007 N003 129.05(11) . . ?
C00C C007 C008 122.21(12) . . ?
C007 C008 C00D 108.28(11) . . ?
C00F C008 C007 119.71(12) . . ?
C00F C008 C00D 132.02(12) . . ?
C00G C009 C00E 121.25(13) . . ?
C00H C00A C006 103.00(10) . . ?
C00E C00B N004 128.63(12) . . ?
C00E C00B C00H 122.12(12) . . ?
C00H C00B N004 109.24(11) . . ?
C007 C00C C00I 117.62(12) . . ?
C008 C00D C005 103.23(10) . . ?
C00B C00E C009 117.47(12) . . ?
C008 C00F C00J 118.71(13) . . ?
C009 C00G C00K 120.41(13) . . ?
C00B C00H C00A 107.91(11) . . ?
C00K C00H C00A 132.49(12) . . ?
C00K C00H C00B 119.60(12) . . ?
C00J C00I C00C 120.96(14) . . ?
C00I C00J C00F 120.78(14) . . ?
C00H C00K C00G 119.14(13) . . ?

_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.730
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2105088'
loop_
_audit_author_name
_audit_author_address
'Chen Zijian'
;South China University of technology
China
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_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         'C10 H11 N O'
_chemical_formula_sum            'C10 H11 N O'
_chemical_formula_weight         161.20
_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 0.0181 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9081(4)
_cell_length_b                   9.5740(4)
_cell_length_c                   11.0310(4)
_cell_angle_alpha                88.063(3)
_cell_angle_beta                 72.538(4)
_cell_angle_gamma                68.658(4)
_cell_volume                     832.87(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5641
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.2650
_cell_measurement_theta_min      4.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7634
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  13.00   0.50    0.50    --    0.00 -48.00  66.00  204
  2  ω     28.00  55.00   0.50    0.50    --    5.00  48.00-144.00   54
  3  ω    -57.00 -32.00   0.50    0.50    --    5.00 -48.00  66.00   50
  4  ω   -174.00 -86.00   0.50    0.50    --  -98.80 -48.00  66.00  176
  5  ω    -66.00 -40.00   0.50    0.50    --  -98.80  48.00-144.00   52
  6  ω    -37.00 -12.00   0.50    0.50    --    0.00 -57.00-180.00   50
  7  ω    -12.00  13.00   0.50    0.50    --    0.00 -37.00-120.00   50
  8  ω    -85.00 -31.00   0.50    0.50    --    0.00 -37.00-120.00  108
  9  ω    -88.00  -5.00   0.50    0.50    --    0.00 -72.00   0.00  166
 10  ω   -113.00 -48.00   0.50    0.50    --  -98.80  72.00 -90.00  130
 11  ω   -143.00-117.00   0.50    0.50    --  -98.80 -57.00-150.00   52
 12  ω   -187.00-132.00   0.50    0.50    --  -98.80 -37.00 120.00  110
 13  ω   -158.00 -87.00   0.50    0.50    --  -98.80 -37.00 150.00  142
 14  ω   -113.00 -50.00   0.50    0.50    --  -98.80  72.00 120.00  126
 15  ω   -113.00 -19.00   0.50    0.50    --  -98.80  72.00-150.00  188
 16  ω   -111.00 -61.00   0.50    0.50    --  -98.80  72.00 -60.00  100
 17  ω    -56.00 -10.00   0.50    0.50    --  -98.80  72.00 -60.00   92
 18  ω    -81.00 -32.00   0.50    0.50    --  -98.80  72.00  60.00   98
 19  ω   -108.00  -9.00   0.50    0.50    --  -98.80  57.00  30.00  198
 20  ω    -97.00 -43.00   0.50    0.50    --  -98.80  72.00 150.00  108
 21  ω   -182.00 -86.00   0.50    0.50    --  -98.80 -37.00  90.00  192
 22  ω   -112.00 -87.00   0.50    0.50    --  -98.80 -37.00 120.00   50
 23  ω    -34.00  -9.00   0.50    0.50    --  -98.80  72.00   0.00   50
 24  ω   -188.00 -93.00   0.50    0.50    --  -98.80 -57.00   0.00  190
 25  ω   -100.00 -55.00   0.50    0.50    --  -98.80  72.00  30.00   90
 26  ω   -112.00 -86.00   0.50    0.50    --  -98.80  72.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1232766000
_diffrn_orient_matrix_UB_12      -0.1560390000
_diffrn_orient_matrix_UB_13      -0.0665982000
_diffrn_orient_matrix_UB_21      -0.1395212000
_diffrn_orient_matrix_UB_22      -0.0644631000
_diffrn_orient_matrix_UB_23      0.0548208000
_diffrn_orient_matrix_UB_31      -0.0587665000
_diffrn_orient_matrix_UB_32      0.0394754000
_diffrn_orient_matrix_UB_33      -0.1189508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2742
_reflns_number_total             2938
_reflns_odcompleteness_completeness 98.46
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.148
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.077
_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)+(0.0391P)²+0.2347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0876
_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:
 C00D(H00J,H00K), C00E(H00A,H00C), C00F(H00M,H00N), C00K(H00D,H00E), C00M(H00S,
 H00T), C00N(H00F,H00G)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C00B(H00B), C00C(H00I), C00G(H00P), C00H(H00H),
 C00I(H00Q), C00J(H00R), C00L(H00L), C00O(H00O)
;
_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
O001 O 0.68393(11) 0.13857(10) 0.46168(8) 0.0318(2) Uani 1 1 d . . . . .
O002 O 0.86729(10) 0.10578(10) 0.71386(8) 0.0322(2) Uani 1 1 d . . . . .
N003 N 0.59404(12) 0.15208(11) 0.73333(9) 0.0258(2) Uani 1 1 d . . . . .
H003 H 0.616861 0.159899 0.652503 0.031 Uiso 1 1 calc R . . . .
N004 N 0.89605(12) 0.21301(11) 0.46435(9) 0.0264(2) Uani 1 1 d . . . . .
H004 H 0.890048 0.181931 0.539084 0.032 Uiso 1 1 calc R . . . .
C005 C 0.42321(14) 0.17597(12) 0.80311(11) 0.0236(2) Uani 1 1 d . . . . .
C006 C 0.72417(14) 0.11819(13) 0.78216(11) 0.0252(3) Uani 1 1 d . . . . .
C007 C 1.01544(14) 0.28242(13) 0.41210(11) 0.0245(2) Uani 1 1 d . . . . .
C008 C 0.96583(15) 0.41860(13) 0.35690(11) 0.0261(3) Uani 1 1 d . . . . .
C009 C 0.79167(14) 0.19195(12) 0.40646(11) 0.0259(3) Uani 1 1 d . . . . .
C00A C 0.34275(14) 0.26910(12) 0.91720(11) 0.0242(3) Uani 1 1 d . . . . .
C00B C 1.17732(15) 0.21762(14) 0.42347(12) 0.0288(3) Uani 1 1 d . . . . .
H00B H 1.207773 0.128050 0.462009 0.035 Uiso 1 1 calc R . . . .
C00C C 0.33433(15) 0.11367(13) 0.75168(12) 0.0276(3) Uani 1 1 d . . . . .
H00I H 0.388929 0.052214 0.675744 0.033 Uiso 1 1 calc R . . . .
C00D C 0.68676(15) 0.09172(14) 0.92160(11) 0.0282(3) Uani 1 1 d . . . . .
H00J H 0.793239 0.044145 0.939776 0.034 Uiso 1 1 calc R . . . .
H00K H 0.627778 0.022222 0.938849 0.034 Uiso 1 1 calc R . . . .
C00E C 0.81391(16) 0.23477(13) 0.27155(11) 0.0282(3) Uani 1 1 d . . . . .
H00A H 0.757690 0.188629 0.232041 0.034 Uiso 1 1 calc R . . . .
H00C H 0.933661 0.195314 0.223837 0.034 Uiso 1 1 calc R . . . .
C00F C 0.43770(15) 0.34420(13) 0.96614(12) 0.0278(3) Uani 1 1 d . . . . .
H00M H 0.358217 0.418048 1.036066 0.033 Uiso 1 1 calc R . . . .
H00N H 0.486061 0.397442 0.898687 0.033 Uiso 1 1 calc R . . . .
C00G C 0.17254(15) 0.29490(13) 0.97903(12) 0.0288(3) Uani 1 1 d . . . . .
H00P H 0.117578 0.354419 1.055964 0.035 Uiso 1 1 calc R . . . .
C00H C 1.29343(15) 0.28667(15) 0.37729(12) 0.0326(3) Uani 1 1 d . . . . .
H00H H 1.401940 0.243419 0.384518 0.039 Uiso 1 1 calc R . . . .
C00I C 0.16418(15) 0.14352(13) 0.81401(13) 0.0307(3) Uani 1 1 d . . . . .
H00Q H 0.104172 0.103147 0.779305 0.037 Uiso 1 1 calc R . . . .
C00J C 0.08383(15) 0.23333(14) 0.92776(13) 0.0317(3) Uani 1 1 d . . . . .
H00R H -0.029946 0.252460 0.969953 0.038 Uiso 1 1 calc R . . . .
C00K C 0.78617(15) 0.49162(13) 0.35378(13) 0.0307(3) Uani 1 1 d . . . . .
H00D H 0.768056 0.592729 0.327740 0.037 Uiso 1 1 calc R . . . .
H00E H 0.709561 0.499889 0.439274 0.037 Uiso 1 1 calc R . . . .
C00L C 1.24708(16) 0.42011(15) 0.32044(12) 0.0339(3) Uani 1 1 d . . . . .
H00L H 1.324974 0.466139 0.288605 0.041 Uiso 1 1 calc R . . . .
C00M C 0.57958(15) 0.23492(15) 1.01224(12) 0.0313(3) Uani 1 1 d . . . . .
H00S H 0.530169 0.206860 1.095772 0.038 Uiso 1 1 calc R . . . .
H00T H 0.652788 0.285534 1.021053 0.038 Uiso 1 1 calc R . . . .
C00N C 0.74217(16) 0.40567(14) 0.26350(12) 0.0304(3) Uani 1 1 d . . . . .
H00F H 0.786816 0.427983 0.176657 0.036 Uiso 1 1 calc R . . . .
H00G H 0.619927 0.440155 0.284346 0.036 Uiso 1 1 calc R . . . .
C00O C 1.08498(16) 0.48534(14) 0.31083(12) 0.0313(3) Uani 1 1 d . . . . .
H00O H 1.055086 0.575404 0.272897 0.038 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
O001 C009 1.2404(14) . ?
O002 C006 1.2355(14) . ?
N003 C005 1.4199(14) . ?
N003 C006 1.3522(15) . ?
N004 C007 1.4232(15) . ?
N004 C009 1.3470(15) . ?
C005 C00A 1.4006(17) . ?
C005 C00C 1.3932(16) . ?
C006 C00D 1.5062(17) . ?
C007 C008 1.3981(16) . ?
C007 C00B 1.3900(16) . ?
C008 C00K 1.5061(16) . ?
C008 C00O 1.3932(17) . ?
C009 C00E 1.5043(16) . ?
C00A C00F 1.5057(16) . ?
C00A C00G 1.3940(16) . ?
C00B C00H 1.3875(18) . ?
C00C C00I 1.3872(17) . ?
C00D C00M 1.5355(18) . ?
C00E C00N 1.5351(16) . ?
C00F C00M 1.5290(17) . ?
C00G C00J 1.3862(17) . ?
C00H C00L 1.3832(19) . ?
C00I C00J 1.3828(19) . ?
C00K C00N 1.5319(17) . ?
C00L C00O 1.3847(18) . ?

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
C006 N003 C005 126.05(10) . . ?
C009 N004 C007 125.42(10) . . ?
C00A C005 N003 120.28(10) . . ?
C00C C005 N003 118.78(11) . . ?
C00C C005 C00A 120.79(10) . . ?
O002 C006 N003 120.98(11) . . ?
O002 C006 C00D 122.24(10) . . ?
N003 C006 C00D 116.75(10) . . ?
C008 C007 N004 119.78(10) . . ?
C00B C007 N004 119.14(10) . . ?
C00B C007 C008 120.98(11) . . ?
C007 C008 C00K 119.88(10) . . ?
C00O C008 C007 117.92(11) . . ?
C00O C008 C00K 122.14(11) . . ?
O001 C009 N004 121.41(11) . . ?
O001 C009 C00E 121.94(10) . . ?
N004 C009 C00E 116.65(10) . . ?
C005 C00A C00F 119.90(10) . . ?
C00G C00A C005 118.14(10) . . ?
C00G C00A C00F 121.89(11) . . ?
C00H C00B C007 119.95(11) . . ?
C00I C00C C005 119.84(11) . . ?
C006 C00D C00M 114.32(10) . . ?
C009 C00E C00N 112.82(10) . . ?
C00A C00F C00M 113.75(10) . . ?
C00J C00G C00A 121.11(11) . . ?
C00L C00H C00B 119.71(11) . . ?
C00J C00I C00C 119.97(11) . . ?
C00I C00J C00G 120.13(11) . . ?
C008 C00K C00N 113.65(10) . . ?
C00H C00L C00O 120.16(11) . . ?
C00F C00M C00D 112.99(10) . . ?
C00K C00N C00E 112.52(10) . . ?
C00L C00O C008 121.25(11) . . ?

_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 1.808
_oxdiff_exptl_absorpt_empirical_full_min 0.566
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2105087'
loop_
_audit_author_name
_audit_author_address
'Chen Zijian'
;South China University of technology
China
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_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         'C9 H9 N O'
_chemical_formula_sum            'C9 H8 N O'
_chemical_formula_weight         146.16
_chemical_absolute_configuration ?
_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   7.5949(2)
_cell_length_b                   7.59466(19)
_cell_length_c                   12.7739(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     736.81(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3282
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3800
_cell_measurement_theta_min      6.7500
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
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    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.841
_diffrn_reflns_theta_min         6.782
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  43.00   0.50    0.50    --    5.00  39.00  71.00   50
  2  ω   -141.00 -85.00   0.50    0.50    --  -98.80 -39.00 -82.00  112
  3  ω    -74.00 -48.00   0.50    0.50    --  -98.80  39.00  71.00   52
  4  ω   -182.00-145.00   0.50    0.50    --  -98.80 -39.00 -82.00   74
  5  ω    -81.00 -15.00   0.50    0.50    --    5.00 -57.00  60.00  132
  6  ω    -35.00  -9.00   0.50    0.50    --    5.00 -39.00 -82.00   52
  7  ω    -61.00 -35.00   0.50    0.50    --  -98.80  37.00-120.00   52
  8  ω   -155.00 -95.00   0.50    0.50    --  -98.80 -19.00 120.00  120
  9  ω   -188.00 -93.00   0.50    0.50    --  -98.80 -37.00-120.00  190
 10  ω   -107.00 -74.00   0.50    0.50    --  -98.80  37.00-120.00   66
 11  ω   -166.00-140.00   0.50    0.50    --  -98.80 -39.00 -82.00   52
 12  ω    -47.00  11.00   0.50    0.50    --    0.00 -19.00  90.00  116
 13  ω   -110.00 -85.00   0.50    0.50    --  -98.80 -19.00   0.00   50
 14  ω   -100.00 -17.00   0.50    0.50    --  -98.80  19.00-150.00  166
 15  ω   -156.00-131.00   0.50    0.50    --  -98.80 -19.00   0.00   50
 16  ω   -141.00-113.00   0.50    0.50    --  -98.80 -72.00  60.00   56
 17  ω   -111.00 -13.00   0.50    0.50    --  -98.80  72.00-150.00  196
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0993182000
_diffrn_orient_matrix_UB_12      -0.0412416000
_diffrn_orient_matrix_UB_13      -0.1020709000
_diffrn_orient_matrix_UB_21      0.0095261000
_diffrn_orient_matrix_UB_22      0.1955089000
_diffrn_orient_matrix_UB_23      -0.0312696000
_diffrn_orient_matrix_UB_31      0.1768033000
_diffrn_orient_matrix_UB_32      -0.0341110000
_diffrn_orient_matrix_UB_33      -0.0560812000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                1437
_reflns_number_total             1450
_reflns_odcompleteness_completeness 100.00
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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         0.212
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.130
_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)+(0.0549P)²+0.0768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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:
 C00A(H00A,H00B), C00B(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), C006(H006), C007(H007), C008(H008), C009(H009)
;
_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
O001 O 0.56992(14) 0.70453(16) 0.47807(8) 0.0277(3) Uani 1 1 d . . . . .
N002 N 0.39536(17) 0.70198(18) 0.62031(10) 0.0221(3) Uani 1 1 d . . . . .
H002 H 0.309307 0.740263 0.582931 0.026 Uiso 1 1 calc R . . . .
C003 C 0.5519(2) 0.6759(2) 0.57257(12) 0.0220(3) Uani 1 1 d . . . . .
C004 C 0.3639(2) 0.6704(2) 0.72764(12) 0.0211(3) Uani 1 1 d . . . . .
C005 C 0.5060(2) 0.6504(2) 0.79583(11) 0.0218(4) Uani 1 1 d . . . . .
C006 C 0.2998(2) 0.6113(2) 0.93848(12) 0.0295(4) Uani 1 1 d . . . . .
H006 H 0.278653 0.591395 1.009208 0.035 Uiso 1 1 calc R . . . .
C007 C 0.1600(2) 0.6327(2) 0.86992(13) 0.0286(4) Uani 1 1 d . . . . .
H007 H 0.045004 0.627360 0.894771 0.034 Uiso 1 1 calc R . . . .
C008 C 0.1910(2) 0.6622(2) 0.76431(12) 0.0253(4) Uani 1 1 d . . . . .
H008 H 0.097244 0.676476 0.718270 0.030 Uiso 1 1 calc R . . . .
C009 C 0.4713(2) 0.6195(2) 0.90143(12) 0.0262(4) Uani 1 1 d . . . . .
H009 H 0.564572 0.604227 0.947735 0.031 Uiso 1 1 calc R . . . .
C00A C 0.6977(2) 0.6036(2) 0.63921(12) 0.0248(4) Uani 1 1 d . . . . .
H00A H 0.809829 0.638248 0.609221 0.030 Uiso 1 1 calc R . . . .
H00B H 0.691965 0.476059 0.638189 0.030 Uiso 1 1 calc R . . . .
C00B C 0.6897(2) 0.6668(2) 0.75263(12) 0.0254(4) Uani 1 1 d . . . . .
H00C H 0.769893 0.597308 0.794927 0.031 Uiso 1 1 calc R . . . .
H00D H 0.727069 0.788747 0.756201 0.031 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
O001 C003 1.2341(18) . ?
N002 C003 1.3510(19) . ?
N002 C004 1.4121(19) . ?
C003 C00A 1.501(2) . ?
C004 C005 1.395(2) . ?
C004 C008 1.395(2) . ?
C005 C009 1.394(2) . ?
C005 C00B 1.506(2) . ?
C006 C007 1.386(2) . ?
C006 C009 1.387(2) . ?
C007 C008 1.388(2) . ?
C00A C00B 1.527(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
C003 N002 C004 124.20(13) . . ?
O001 C003 N002 120.87(14) . . ?
O001 C003 C00A 122.52(14) . . ?
N002 C003 C00A 116.55(13) . . ?
C005 C004 N002 119.60(14) . . ?
C005 C004 C008 120.88(14) . . ?
C008 C004 N002 119.51(13) . . ?
C004 C005 C00B 118.62(13) . . ?
C009 C005 C004 118.46(15) . . ?
C009 C005 C00B 122.91(14) . . ?
C007 C006 C009 119.91(14) . . ?
C006 C007 C008 120.20(15) . . ?
C007 C008 C004 119.57(15) . . ?
C006 C009 C005 120.98(15) . . ?
C003 C00A C00B 113.20(13) . . ?
C005 C00B C00A 111.01(13) . . ?

_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.760
