# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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-I
_database_code_depnum_ccdc_archive 'CCDC 2108380'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-07-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_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                   11.89630(10)
_cell_length_b                   7.77840(10)
_cell_length_c                   12.82620(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.1240(10)
_cell_angle_gamma                90
_cell_volume                     1182.12(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5756
_cell_measurement_temperature    299.87(10)
_cell_measurement_theta_max      77.1920
_cell_measurement_theta_min      5.3040
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.15
_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  0.0142
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7417
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.409
_diffrn_reflns_theta_min         6.663
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.87(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00 120.00   0.50    0.05    --   47.57  61.00-160.00  148
  2  ω    104.00 174.00   0.50    0.05    --  107.75  61.00-160.00  140
  3  ω    149.00 175.00   0.50    0.05    --  107.75  37.00 -90.00   52
  4  ω    102.00 139.00   0.50    0.05    --  107.75  37.00 -90.00   74
  5  ω    133.00 172.00   0.50    0.05    --  107.75  19.00 -30.00   78
  6  ω     95.00 128.00   0.50    0.05    --  107.75  19.00 -30.00   66
  7  ω    -19.00  38.00   0.50    0.05    --   47.57 -61.00  60.00  114
  8  ω    -15.00  11.00   0.50    0.05    --   47.57 -19.00  60.00   52
  9  ω     35.00  60.00   0.50    0.05    --  107.75 -57.00  90.00   50
 10  ω     35.00  63.00   0.50    0.05    --  107.75 -61.00  60.00   56
 11  ω     37.00  63.00   0.50    0.05    --  107.75 -57.00 -60.00   52
 12  ω    -27.00  21.00   0.50    0.05    --   47.57 -19.00 -90.00   96
 13  ω    -38.00  21.00   0.50    0.05    --  -47.57  61.00-160.00  118
 14  ω    -74.00 -30.00   0.50    0.05    -- -100.00  61.00-160.00   88
 15  ω    -69.00 -36.00   0.50    0.05    -- -100.00  57.00 -90.00   66
 16  ω    -62.00 -36.00   0.50    0.05    -- -100.00  57.00 -30.00   52
 17  ω    -66.00 -39.00   0.50    0.05    -- -100.00  57.00  30.00   54
 18  ω    -60.00 -28.00   0.50    0.05    -- -100.00 125.00 120.00   64
 19  ω   -104.00 -79.00   0.50    0.05    -- -100.00 125.00 120.00   50
 20  ω   -172.00 -85.00   0.50    0.05    -- -100.00 -57.00 120.00  174
 21  ω   -145.00-119.00   0.50    0.05    -- -100.00 -57.00 150.00   52
 22  ω   -165.00-138.00   0.50    0.05    -- -100.00 -61.00  60.00   54
 23  ω   -159.00 -88.00   0.50    0.05    -- -100.00-125.00-150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0684001000
_diffrn_orient_matrix_UB_12      -0.0914291000
_diffrn_orient_matrix_UB_13      -0.0801157000
_diffrn_orient_matrix_UB_21      0.1041720000
_diffrn_orient_matrix_UB_22      0.1088979000
_diffrn_orient_matrix_UB_23      0.0368754000
_diffrn_orient_matrix_UB_31      0.0370054000
_diffrn_orient_matrix_UB_32      -0.1378874000
_diffrn_orient_matrix_UB_33      0.0822682000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2149
_reflns_number_total             2322
_reflns_odcompleteness_completeness 98.20
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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         0.171
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.024
_refine_ls_extinction_coef       0.033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.058
_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)+(0.0654P)²+0.1241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1145
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.90307(8) 0.49615(11) 0.90347(6) 0.0646(3) Uani 1 1 d . . . . .
O2 O 0.99827(9) 0.26949(11) 0.96970(7) 0.0688(3) Uani 1 1 d . . . . .
H2 H 1.028810 0.343707 1.007805 0.103 Uiso 1 1 calc GR . . . .
N1 N 0.77881(9) 0.45875(13) 0.72251(8) 0.0609(3) Uani 1 1 d . . . . .
H1 H 0.804975 0.524248 0.772984 0.073 Uiso 1 1 calc R . . . .
C1 C 0.88070(9) 0.22678(13) 0.81545(8) 0.0484(3) Uani 1 1 d . . . . .
C2 C 0.80886(9) 0.28855(14) 0.72955(8) 0.0498(3) Uani 1 1 d . . . . .
C3 C 0.76782(10) 0.16842(16) 0.65331(10) 0.0597(3) Uani 1 1 d . . . . .
H3 H 0.720143 0.205407 0.596307 0.072 Uiso 1 1 calc R . . . .
C4 C 0.79665(11) -0.00161(16) 0.66139(10) 0.0629(3) Uani 1 1 d . . . . .
H4 H 0.768056 -0.078063 0.609932 0.075 Uiso 1 1 calc R . . . .
C5 C 0.86776(11) -0.06200(15) 0.74493(10) 0.0611(3) Uani 1 1 d . . . . .
H5 H 0.887142 -0.177747 0.749624 0.073 Uiso 1 1 calc R . . . .
C6 C 0.90897(10) 0.05178(15) 0.82044(9) 0.0546(3) Uani 1 1 d . . . . .
H6 H 0.956931 0.011925 0.876471 0.065 Uiso 1 1 calc R . . . .
C7 C 0.92706(9) 0.34226(15) 0.89873(8) 0.0527(3) Uani 1 1 d . . . . .
C8 C 0.70935(9) 0.53778(14) 0.64099(8) 0.0509(3) Uani 1 1 d . . . . .
C9 C 0.61790(10) 0.63324(13) 0.66630(9) 0.0524(3) Uani 1 1 d . . . . .
H9 H 0.602484 0.640760 0.735971 0.063 Uiso 1 1 calc R . . . .
C10 C 0.54821(10) 0.71847(14) 0.59033(9) 0.0567(3) Uani 1 1 d . . . . .
C11 C 0.57262(11) 0.70461(16) 0.48735(10) 0.0625(3) Uani 1 1 d . . . . .
H11 H 0.526316 0.758508 0.434944 0.075 Uiso 1 1 calc R . . . .
C12 C 0.66436(12) 0.61225(18) 0.46154(10) 0.0674(4) Uani 1 1 d . . . . .
H12 H 0.679937 0.605330 0.391887 0.081 Uiso 1 1 calc R . . . .
C13 C 0.73384(11) 0.52947(17) 0.53753(9) 0.0619(3) Uani 1 1 d . . . . .
H13 H 0.796546 0.468650 0.519453 0.074 Uiso 1 1 calc R . . . .
C14 C 0.44874(14) 0.8200(2) 0.62043(13) 0.0861(5) Uani 1 1 d . . . . .
H14A H 0.389641 0.742667 0.636123 0.129 Uiso 1 1 calc GR . . . .
H14B H 0.421939 0.893517 0.563436 0.129 Uiso 1 1 calc GR . . . .
H14C H 0.471030 0.888618 0.680963 0.129 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 C7 1.2333(14) . ?
O2 C7 1.3149(13) . ?
N1 C2 1.3721(15) . ?
N1 C8 1.4141(14) . ?
C1 C2 1.4167(15) . ?
C1 C6 1.4022(15) . ?
C1 C7 1.4652(15) . ?
C2 C3 1.4080(16) . ?
C3 C4 1.3679(18) . ?
C4 C5 1.3865(18) . ?
C5 C6 1.3700(17) . ?
C8 C9 1.3797(16) . ?
C8 C13 1.3853(16) . ?
C9 C10 1.3900(16) . ?
C10 C11 1.3816(18) . ?
C10 C14 1.5014(18) . ?
C11 C12 1.3716(19) . ?
C12 C13 1.3798(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
C2 N1 C8 126.85(9) . . ?
C2 C1 C7 121.38(10) . . ?
C6 C1 C2 119.36(10) . . ?
C6 C1 C7 119.25(10) . . ?
N1 C2 C1 120.93(10) . . ?
N1 C2 C3 121.50(10) . . ?
C3 C2 C1 117.56(10) . . ?
C4 C3 C2 121.33(11) . . ?
C3 C4 C5 121.18(11) . . ?
C6 C5 C4 118.85(11) . . ?
C5 C6 C1 121.71(11) . . ?
O1 C7 O2 121.42(10) . . ?
O1 C7 C1 123.86(10) . . ?
O2 C7 C1 114.71(10) . . ?
C9 C8 N1 118.75(10) . . ?
C9 C8 C13 119.22(10) . . ?
C13 C8 N1 121.94(11) . . ?
C8 C9 C10 121.69(10) . . ?
C9 C10 C14 120.33(12) . . ?
C11 C10 C9 118.02(11) . . ?
C11 C10 C14 121.64(12) . . ?
C12 C11 C10 120.75(11) . . ?
C11 C12 C13 120.88(12) . . ?
C12 C13 C8 119.40(12) . . ?

_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 1.759
_oxdiff_exptl_absorpt_empirical_full_min 0.559
####################################################################### 
# 
# 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_3-IV
_database_code_depnum_ccdc_archive 'CCDC 2108388'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-05-30
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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                   11.9463(5)
_cell_length_b                   14.7794(6)
_cell_length_c                   7.4808(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.083(4)
_cell_angle_gamma                90
_cell_volume                     1269.11(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2811
_cell_measurement_temperature    297.64(10)
_cell_measurement_theta_max      75.3940
_cell_measurement_theta_min      3.8490
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
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    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6797
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.577
_diffrn_reflns_theta_min         3.851
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.64(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     47.00 117.00   1.00    0.20    --   47.57  37.00  30.00   70
  2  ω     83.00 165.00   1.00    0.81    --  107.75 112.00 111.00   82
  3  ω    107.00 172.00   1.00    0.81    --  107.75  37.00 -90.00   65
  4  ω    142.00 168.00   1.00    0.81    --  107.75  19.00-150.00   26
  5  ω    103.00 128.00   1.00    0.81    --  107.75  19.00-150.00   25
  6  ω    -69.00 -38.00   1.00    0.81    -- -100.00  57.00-120.00   31
  7  ω    -67.00 -29.00   1.00    0.81    -- -100.00  57.00 -90.00   38
  8  ω    -69.00 -44.00   1.00    0.81    -- -100.00  57.00 -60.00   25
  9  ω    -65.00 -27.00   1.00    0.81    -- -100.00  57.00 -30.00   38
 10  ω    -79.00 -14.00   1.00    0.20    --  -47.57 112.00 111.00   65
 11  ω    -93.00 -58.00   1.00    0.81    -- -100.00 112.00 111.00   35
 12  ω   -135.00-109.00   1.00    0.81    -- -100.00-112.00  18.00   26
 13  ω     35.00  93.00   1.00    0.81    --  107.75 -77.00   0.00   58
 14  ω     78.00 103.00   1.00    0.81    --  107.75 -77.00  30.00   25
 15  ω     37.00  62.00   1.00    0.81    --  107.75 -77.00  30.00   25
 16  ω     35.00  60.00   1.00    0.81    --  107.75 -57.00  60.00   25
 17  ω     37.00  62.00   1.00    0.81    --  107.75 -57.00  30.00   25
 18  ω    -16.00  35.00   1.00    0.20    --   47.57 -37.00 -90.00   51
 19  ω    -27.00  22.00   1.00    0.20    --   47.57 -19.00-150.00   49
 20  ω     35.00  63.00   1.00    0.81    --  107.75 -99.00-180.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1214832000
_diffrn_orient_matrix_UB_12      0.0437198000
_diffrn_orient_matrix_UB_13      -0.0681072000
_diffrn_orient_matrix_UB_21      0.0570904000
_diffrn_orient_matrix_UB_22      0.0925716000
_diffrn_orient_matrix_UB_23      -0.0104121000
_diffrn_orient_matrix_UB_31      -0.0013927000
_diffrn_orient_matrix_UB_32      -0.0194058000
_diffrn_orient_matrix_UB_33      -0.2029638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1908
_reflns_number_total             2484
_reflns_odcompleteness_completeness 98.02
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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         0.162
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.058
_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)+(0.0757P)²+0.1566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1439
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.59653(11) 0.55535(10) 0.2020(2) 0.0630(4) Uani 1 1 d . . . . .
H1 H 0.593048 0.527958 0.105278 0.095 Uiso 1 1 calc GR . . . .
O2 O 0.40421(11) 0.54247(9) 0.09575(18) 0.0573(4) Uani 1 1 d . . . . .
N1 N 0.27524(13) 0.61020(12) 0.3039(2) 0.0599(4) Uani 1 1 d . . . . .
H1A H 0.280024 0.591185 0.197605 0.072 Uiso 1 1 calc R . . . .
C1 C 0.48625(14) 0.60632(10) 0.3967(2) 0.0438(4) Uani 1 1 d . . . . .
C2 C 0.37882(15) 0.62633(11) 0.4346(2) 0.0460(4) Uani 1 1 d . . . . .
C3 C 0.38448(16) 0.66097(12) 0.6123(3) 0.0525(4) Uani 1 1 d . . . . .
H3 H 0.315798 0.674232 0.642414 0.063 Uiso 1 1 calc R . . . .
C4 C 0.48885(18) 0.67545(12) 0.7411(3) 0.0532(4) Uani 1 1 d . . . . .
H4 H 0.488876 0.698130 0.857119 0.064 Uiso 1 1 calc R . . . .
C5 C 0.59549(16) 0.65761(11) 0.7060(3) 0.0509(4) Uani 1 1 d . . . . .
C6 C 0.59107(15) 0.62255(11) 0.5334(2) 0.0476(4) Uani 1 1 d . . . . .
H6 H 0.660731 0.609089 0.506547 0.057 Uiso 1 1 calc R . . . .
C7 C 0.49048(15) 0.56582(11) 0.2202(3) 0.0472(4) Uani 1 1 d . . . . .
C8 C 0.70914(19) 0.67364(16) 0.8504(3) 0.0700(6) Uani 1 1 d . . . . .
H8A H 0.715436 0.736411 0.884735 0.105 Uiso 1 1 calc GR . . . .
H8B H 0.772334 0.657429 0.800615 0.105 Uiso 1 1 calc GR . . . .
H8C H 0.712327 0.637342 0.958084 0.105 Uiso 1 1 calc GR . . . .
C9 C 0.16147(15) 0.62097(13) 0.3223(2) 0.0504(4) Uani 1 1 d . . . . .
C10 C 0.08353(15) 0.55001(13) 0.2693(2) 0.0516(4) Uani 1 1 d . . . . .
H10 H 0.108963 0.496541 0.227877 0.062 Uiso 1 1 calc R . . . .
C11 C -0.03126(15) 0.55599(14) 0.2759(2) 0.0547(5) Uani 1 1 d . . . . .
C12 C -0.06619(17) 0.63625(16) 0.3410(3) 0.0658(6) Uani 1 1 d . . . . .
H12 H -0.142204 0.642084 0.348795 0.079 Uiso 1 1 calc R . . . .
C13 C 0.01054(19) 0.70729(16) 0.3941(3) 0.0691(6) Uani 1 1 d . . . . .
H13 H -0.014534 0.760418 0.437399 0.083 Uiso 1 1 calc R . . . .
C14 C 0.12400(18) 0.70100(14) 0.3842(3) 0.0608(5) Uani 1 1 d . . . . .
H14 H 0.174672 0.749726 0.418621 0.073 Uiso 1 1 calc R . . . .
C15 C -0.11271(18) 0.47732(18) 0.2216(3) 0.0733(6) Uani 1 1 d . . . . .
H15A H -0.082138 0.435470 0.148879 0.110 Uiso 1 1 calc GR . . . .
H15B H -0.187576 0.498505 0.149471 0.110 Uiso 1 1 calc GR . . . .
H15C H -0.120597 0.447579 0.331516 0.110 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 C7 1.3203(19) . ?
O2 C7 1.231(2) . ?
N1 C2 1.369(2) . ?
N1 C9 1.412(2) . ?
C1 C2 1.420(2) . ?
C1 C6 1.401(2) . ?
C1 C7 1.463(2) . ?
C2 C3 1.408(3) . ?
C3 C4 1.365(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.379(3) . ?
C5 C8 1.501(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.389(3) . ?
C10 C11 1.389(2) . ?
C11 C12 1.390(3) . ?
C11 C15 1.498(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 127.92(15) . . ?
C2 C1 C7 121.64(16) . . ?
C6 C1 C2 119.54(15) . . ?
C6 C1 C7 118.78(14) . . ?
N1 C2 C1 120.59(15) . . ?
N1 C2 C3 122.36(15) . . ?
C3 C2 C1 117.04(16) . . ?
C4 C3 C2 121.27(16) . . ?
C3 C4 C5 122.70(16) . . ?
C4 C5 C8 121.71(17) . . ?
C6 C5 C4 116.58(17) . . ?
C6 C5 C8 121.70(17) . . ?
C5 C6 C1 122.86(15) . . ?
O1 C7 C1 114.52(16) . . ?
O2 C7 O1 121.01(15) . . ?
O2 C7 C1 124.47(15) . . ?
C10 C9 N1 118.39(16) . . ?
C10 C9 C14 119.14(16) . . ?
C14 C9 N1 122.43(17) . . ?
C9 C10 C11 122.26(17) . . ?
C10 C11 C12 117.53(18) . . ?
C10 C11 C15 120.96(18) . . ?
C12 C11 C15 121.47(17) . . ?
C13 C12 C11 120.74(17) . . ?
C12 C13 C14 121.18(19) . . ?
C13 C14 C9 119.1(2) . . ?

_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 1.993
_oxdiff_exptl_absorpt_empirical_full_min 0.615
####################################################################### 
# 
# 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 2108382'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-09-22 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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                   7.6873(3)
_cell_length_b                   9.8086(5)
_cell_length_c                   15.7011(7)
_cell_angle_alpha                97.313(4)
_cell_angle_beta                 93.706(3)
_cell_angle_gamma                94.222(4)
_cell_volume                     1167.78(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4794
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6570
_cell_measurement_theta_min      5.0180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11748
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.720
_diffrn_reflns_theta_min         4.561
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00 116.00   1.00    8.28    --   41.67  38.00 120.00   99
  2  ω     17.00 116.00   1.00    8.28    --   41.67  38.00-150.00   99
  3  ω     -3.00  96.00   1.00    8.28    --   41.67-125.00-120.00   99
  4  ω      9.00 118.00   1.00    8.28    --   41.67  77.00 -30.00  109
  5  ω     11.00 128.00   1.00   33.09    --   92.50 -86.00 -15.56  117
  6  ω     46.00 140.00   1.00   33.09    --   92.50 -15.00  90.00   94
  7  ω    124.00 150.00   1.00   33.09    --   92.50  61.00  90.00   26
  8  ω     13.00  39.00   1.00   33.09    --   92.50 -95.00  60.00   26
  9  ω     24.00  94.00   1.00   33.09    --   92.50 -85.00-117.78   70
 10  ω     53.00 128.00   1.00   33.09    --   92.50 -93.00  86.69   75
 11  ω     67.00 114.00   1.00   33.09    --   92.50 -61.00-120.00   47
 12  ω     68.00 112.00   1.00   33.09    --   92.50 -45.00  90.00   44
 13  ω     30.00  70.00   1.00   33.09    --   92.50 -77.00   0.00   40
 14  ω     15.00  41.00   1.00   33.09    --   92.50 -95.00-150.00   26
 15  ω     14.00  61.00   1.00   33.09    --   92.50 -95.00 120.00   47
 16  ω     84.00 109.00   1.00   33.09    --   92.50 -88.00 -84.06   25
 17  ω     59.00  84.00   1.00   33.09    --   92.50 -95.00-150.00   25
 18  ω     26.00  61.00   1.00   33.09    --   92.50 -88.00 -84.06   35
 19  ω     56.00  82.00   1.00   33.09    --   92.50 -95.00  60.00   26
 20  ω     45.00  78.00   1.00   33.09    --   92.50 -95.00 150.00   33
 21  ω     65.00 108.00   1.00   33.09    --   92.50  61.00 -60.00   43
 22  ω    117.00 142.00   1.00   33.09    --   92.50  61.00 -60.00   25
 23  ω     16.00  48.00   1.00   33.09    --   92.50 -77.00 150.00   32
 24  ω     44.00  90.00   1.00   33.09    --   92.50 -30.00  30.00   46
 25  ω     16.00 124.00   1.00   33.09    --   92.50 -15.00-120.00  108
 26  ω     88.00 133.00   1.00   33.09    --   92.50 125.00   0.00   45
 27  ω     67.00 100.00   1.00   33.09    --   92.50  61.00  60.00   33
 28  ω    108.00 164.00   1.00   33.09    --   92.50  61.00  60.00   56
 29  ω     93.00 120.00   1.00   33.09    --   92.50 -87.00 156.52   27
 30  ω     73.00 103.00   1.00   33.09    --   92.50  61.00  90.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022491000
_diffrn_orient_matrix_UB_12      -0.0512650000
_diffrn_orient_matrix_UB_13      -0.0968021000
_diffrn_orient_matrix_UB_21      -0.0198010000
_diffrn_orient_matrix_UB_22      -0.1503937000
_diffrn_orient_matrix_UB_23      0.0190156000
_diffrn_orient_matrix_UB_31      -0.2005263000
_diffrn_orient_matrix_UB_32      0.0010712000
_diffrn_orient_matrix_UB_33      -0.0104218000
_diffrn_radiation_monochromator  mirror
_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 Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3169
_reflns_number_total             4073
_reflns_odcompleteness_completeness 97.60
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.292
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.0038(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.046
_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)+(0.1254P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1856
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C30(H30), C26(H26), C9(H9), C29(H29), C20(H20), C27(H27), N24(H24), C13(H13),
 C19(H19), C10(H10), C12(H12), C22(H22), C5(H5), C28(H28), N7(H7), C6(H6),
 C3(H3), C11(H11)
2.b Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O15(H15), O32(H32)
;
_atom_sites_solution_hydrogens   geom
_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
O16 O 0.04253(17) 0.30670(14) 0.40600(8) 0.0567(4) Uani 1 1 d . . . . .
O15 O -0.16293(17) 0.37519(15) 0.49101(8) 0.0591(4) Uani 1 1 d . . . . .
H15 H -0.1199 0.3209 0.5202 0.089 Uiso 1 1 calc GR . . . .
C30 C 0.0249(2) 0.86236(19) 0.10167(11) 0.0544(5) Uani 1 1 d . . . . .
H30 H -0.0963 0.8526 0.1024 0.065 Uiso 1 1 calc R . . . .
C26 C 0.3083(2) 0.90198(17) 0.17574(11) 0.0505(4) Uani 1 1 d . . . . .
H26 H 0.3798 0.9202 0.2266 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2270(2) 0.27769(18) 0.15694(11) 0.0517(4) Uani 1 1 d . . . . .
H9 H 0.2197 0.2061 0.1905 0.062 Uiso 1 1 calc R . . . .
O33 O 0.04341(17) 0.80061(15) 0.40886(8) 0.0601(4) Uani 1 1 d . . . . .
C29 C 0.1009(3) 0.8479(2) 0.02450(12) 0.0630(5) Uani 1 1 d . . . . .
H29 H 0.0305 0.8299 -0.0267 0.076 Uiso 1 1 calc R . . . .
O32 O -0.17206(18) 0.85722(16) 0.49035(8) 0.0654(4) Uani 1 1 d . . . . .
H32 H -0.1243 0.8070 0.5209 0.098 Uiso 1 1 calc GR . . . .
C20 C -0.3059(2) 1.12888(19) 0.25763(11) 0.0506(4) Uani 1 1 d . . . . .
H20 H -0.3536 1.1876 0.2220 0.061 Uiso 1 1 calc R . . . .
C27 C 0.3825(2) 0.8855(2) 0.09763(13) 0.0609(5) Uani 1 1 d . . . . .
H27 H 0.5036 0.8920 0.0964 0.073 Uiso 1 1 calc R . . . .
N24 N 0.0580(2) 0.90450(17) 0.25941(9) 0.0558(4) Uani 1 1 d . . . . .
H24 H 0.1121 0.8671 0.2989 0.067 Uiso 1 1 calc R . . . .
C13 C 0.1567(3) 0.50041(19) 0.12849(13) 0.0603(5) Uani 1 1 d . . . . .
H13 H 0.1033 0.5814 0.1430 0.072 Uiso 1 1 calc R . . . .
C19 C -0.1658(2) 1.06002(18) 0.23226(11) 0.0494(4) Uani 1 1 d . . . . .
H19 H -0.1211 1.0733 0.1800 0.059 Uiso 1 1 calc R . . . .
C21 C -0.3802(2) 1.11406(18) 0.33543(11) 0.0502(4) Uani 1 1 d . . . . .
C10 C 0.3232(2) 0.2658(2) 0.08623(13) 0.0620(5) Uani 1 1 d . . . . .
H10 H 0.3811 0.1868 0.0726 0.074 Uiso 1 1 calc R . . . .
C23 C -0.1598(2) 0.95418(18) 0.36231(10) 0.0454(4) Uani 1 1 d . . . . .
C18 C -0.0875(2) 0.96998(17) 0.28286(10) 0.0450(4) Uani 1 1 d . . . . .
C12 C 0.2509(3) 0.4860(2) 0.05703(13) 0.0673(6) Uani 1 1 d . . . . .
H12 H 0.2579 0.5566 0.0228 0.081 Uiso 1 1 calc R . . . .
C2 C -0.1620(2) 0.45777(18) 0.35740(10) 0.0473(4) Uani 1 1 d . . . . .
C25 C 0.1287(2) 0.89154(16) 0.17869(10) 0.0445(4) Uani 1 1 d . . . . .
C22 C -0.3025(2) 1.02648(19) 0.38572(11) 0.0495(4) Uani 1 1 d . . . . .
H22 H -0.3479 1.0151 0.4381 0.059 Uiso 1 1 calc R . . . .
C31 C -0.0868(2) 0.86421(18) 0.42146(10) 0.0485(4) Uani 1 1 d . . . . .
C4 C -0.4031(2) 0.5953(2) 0.32253(12) 0.0581(5) Uani 1 1 d . . . . .
C5 C -0.3418(3) 0.5941(2) 0.24088(13) 0.0677(6) Uani 1 1 d . . . . .
H5 H -0.4028 0.6378 0.2005 0.081 Uiso 1 1 calc R . . . .
C14 C -0.0840(2) 0.37467(18) 0.41931(10) 0.0475(4) Uani 1 1 d . . . . .
C28 C 0.2796(3) 0.8599(2) 0.02220(13) 0.0662(5) Uani 1 1 d . . . . .
H28 H 0.3301 0.8506 -0.0303 0.079 Uiso 1 1 calc R . . . .
C34 C -0.5351(3) 1.1888(2) 0.36231(13) 0.0641(5) Uani 1 1 d . . . . .
H34A H -0.5399 1.2700 0.3343 0.096 Uiso 1 1 calc GR . . . .
H34B H -0.5243 1.2146 0.4236 0.096 Uiso 1 1 calc GR . . . .
H34C H -0.6402 1.1295 0.3463 0.096 Uiso 1 1 calc GR . . . .
N7 N 0.0504(2) 0.40016(18) 0.25384(10) 0.0592(4) Uani 1 1 d . . . . .
H7 H 0.0948 0.3566 0.2930 0.071 Uiso 1 1 calc R . . . .
C1 C -0.0979(2) 0.46362(18) 0.27509(11) 0.0498(4) Uani 1 1 d . . . . .
C6 C -0.1960(3) 0.5315(2) 0.21760(12) 0.0641(5) Uani 1 1 d . . . . .
H6 H -0.1609 0.5339 0.1622 0.077 Uiso 1 1 calc R . . . .
C8 C 0.1403(2) 0.39486(17) 0.17936(10) 0.0468(4) Uani 1 1 d . . . . .
C3 C -0.3101(2) 0.52504(19) 0.37881(11) 0.0525(4) Uani 1 1 d . . . . .
H3 H -0.3481 0.5225 0.4337 0.063 Uiso 1 1 calc R . . . .
C11 C 0.3347(3) 0.3700(2) 0.03527(14) 0.0665(5) Uani 1 1 d . . . . .
H11 H 0.3985 0.3614 -0.0132 0.080 Uiso 1 1 calc R . . . .
C17 C -0.5616(3) 0.6665(3) 0.34821(16) 0.0754(6) Uani 1 1 d . . . . .
H17A H -0.5277 0.7615 0.3695 0.113 Uiso 1 1 calc GR . . . .
H17B H -0.6144 0.6224 0.3924 0.113 Uiso 1 1 calc GR . . . .
H17C H -0.6441 0.6612 0.2991 0.113 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
O16 C14 1.233(2) . ?
O15 C14 1.3125(19) . ?
C30 C29 1.375(2) . ?
C30 C25 1.391(2) . ?
C26 C27 1.382(2) . ?
C26 C25 1.382(2) . ?
C9 C10 1.371(2) . ?
C9 C8 1.389(2) . ?
O33 C31 1.231(2) . ?
C29 C28 1.373(3) . ?
O32 C31 1.3072(19) . ?
C20 C19 1.367(2) . ?
C20 C21 1.401(2) . ?
C27 C28 1.366(3) . ?
N24 C18 1.378(2) . ?
N24 C25 1.405(2) . ?
C13 C12 1.373(3) . ?
C13 C8 1.389(2) . ?
C19 C18 1.403(2) . ?
C21 C22 1.380(2) . ?
C21 C34 1.499(3) . ?
C10 C11 1.377(3) . ?
C23 C18 1.419(2) . ?
C23 C22 1.394(2) . ?
C23 C31 1.473(2) . ?
C12 C11 1.365(3) . ?
C2 C14 1.472(2) . ?
C2 C1 1.419(2) . ?
C2 C3 1.395(3) . ?
C4 C5 1.393(3) . ?
C4 C3 1.383(3) . ?
C4 C17 1.500(3) . ?
C5 C6 1.366(3) . ?
N7 C1 1.378(2) . ?
N7 C8 1.394(2) . ?
C1 C6 1.402(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C29 C30 C25 120.15(16) . . ?
C27 C26 C25 120.39(16) . . ?
C10 C9 C8 121.08(16) . . ?
C28 C29 C30 120.78(18) . . ?
C19 C20 C21 122.26(16) . . ?
C28 C27 C26 120.61(17) . . ?
C18 N24 C25 127.80(14) . . ?
C12 C13 C8 120.46(17) . . ?
C20 C19 C18 121.83(15) . . ?
C20 C21 C34 121.91(16) . . ?
C22 C21 C20 116.04(15) . . ?
C22 C21 C34 122.05(16) . . ?
C9 C10 C11 120.48(18) . . ?
C18 C23 C31 121.75(15) . . ?
C22 C23 C18 119.38(15) . . ?
C22 C23 C31 118.86(15) . . ?
N24 C18 C19 122.17(14) . . ?
N24 C18 C23 120.87(15) . . ?
C19 C18 C23 116.89(15) . . ?
C11 C12 C13 121.26(17) . . ?
C1 C2 C14 121.85(15) . . ?
C3 C2 C14 118.48(15) . . ?
C3 C2 C1 119.55(15) . . ?
C30 C25 N24 122.53(15) . . ?
C26 C25 C30 118.63(15) . . ?
C26 C25 N24 118.78(15) . . ?
C21 C22 C23 123.59(16) . . ?
O33 C31 O32 121.74(15) . . ?
O33 C31 C23 124.14(15) . . ?
O32 C31 C23 114.12(15) . . ?
C5 C4 C17 122.51(17) . . ?
C3 C4 C5 115.90(17) . . ?
C3 C4 C17 121.59(18) . . ?
C6 C5 C4 122.77(17) . . ?
O16 C14 O15 121.36(15) . . ?
O16 C14 C2 124.16(15) . . ?
O15 C14 C2 114.46(14) . . ?
C27 C28 C29 119.42(17) . . ?
C1 N7 C8 130.73(15) . . ?
N7 C1 C2 120.12(15) . . ?
N7 C1 C6 123.13(16) . . ?
C6 C1 C2 116.71(16) . . ?
C5 C6 C1 121.67(17) . . ?
C9 C8 C13 117.75(16) . . ?
C9 C8 N7 117.24(15) . . ?
C13 C8 N7 124.93(16) . . ?
C4 C3 C2 123.29(16) . . ?
C12 C11 C10 118.94(18) . . ?

_olex2_date_sample_data_collection 2018-03-26
_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 8.767
_oxdiff_exptl_absorpt_empirical_full_min 0.532
####################################################################### 
# 
# 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_3-I
_database_code_depnum_ccdc_archive 'CCDC 2108383'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2019-10-16
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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'

_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                   12.0066(19)
_cell_length_b                   15.844(3)
_cell_length_c                   6.9519(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.663(2)
_cell_angle_gamma                90
_cell_volume                     1290.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3398
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.43
_cell_measurement_theta_min      3.10
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13843
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.053
_diffrn_reflns_theta_min         1.738
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2880
_reflns_number_total             4213
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         4213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.031
_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)+(0.0889P)²+0.1603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All N(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All O(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13), N1(H1) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_atom_sites_solution_hydrogens   geom
_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
C1 C 0.03652(16) 0.55590(12) 0.7954(3) 0.0603(5) Uani 1 1 d . . . . .
H1A H -0.0258 0.5171 0.7580 0.090 Uiso 1 1 calc GR . . . .
H1B H 0.0174 0.5977 0.8827 0.090 Uiso 1 1 calc GR . . . .
H1C H 0.1035 0.5258 0.8611 0.090 Uiso 1 1 calc GR . . . .
C2 C 0.05917(12) 0.59825(9) 0.6145(2) 0.0408(3) Uani 1 1 d . . . . .
C3 C 0.16692(11) 0.59439(8) 0.5718(2) 0.0383(3) Uani 1 1 d . . . . .
H3 H 0.2248 0.5648 0.6557 0.046 Uiso 1 1 calc R . . . .
C4 C 0.18968(10) 0.63397(8) 0.40562(19) 0.0343(3) Uani 1 1 d . . . . .
C5 C 0.10387(11) 0.67818(9) 0.2804(2) 0.0405(3) Uani 1 1 d . . . . .
H5 H 0.1187 0.7060 0.1708 0.049 Uiso 1 1 calc R . . . .
C6 C -0.00416(12) 0.68057(10) 0.3200(2) 0.0481(4) Uani 1 1 d . . . . .
H6 H -0.0625 0.7090 0.2344 0.058 Uiso 1 1 calc R . . . .
C7 C -0.02647(11) 0.64133(10) 0.4847(2) 0.0468(4) Uani 1 1 d . . . . .
H7 H -0.0995 0.6437 0.5090 0.056 Uiso 1 1 calc R . . . .
C8 C 0.40213(10) 0.63409(8) 0.48157(18) 0.0324(3) Uani 1 1 d . . . . .
C9 C 0.50340(10) 0.60492(7) 0.42964(18) 0.0312(2) Uani 1 1 d . . . . .
C10 C 0.60875(11) 0.61527(8) 0.5624(2) 0.0370(3) Uani 1 1 d . . . . .
H10 H 0.6744 0.5958 0.5267 0.044 Uiso 1 1 calc R . . . .
C11 C 0.61868(11) 0.65322(9) 0.7439(2) 0.0400(3) Uani 1 1 d . . . . .
C12 C 0.51843(12) 0.68272(8) 0.7919(2) 0.0391(3) Uani 1 1 d . . . . .
H12 H 0.5229 0.7091 0.9129 0.047 Uiso 1 1 calc R . . . .
C13 C 0.41368(11) 0.67392(8) 0.6661(2) 0.0381(3) Uani 1 1 d . . . . .
H13 H 0.3491 0.6947 0.7034 0.046 Uiso 1 1 calc R . . . .
C14 C 0.50013(10) 0.56300(8) 0.23974(18) 0.0337(3) Uani 1 1 d . . . . .
C15 C 0.73237(14) 0.66254(14) 0.8870(3) 0.0636(5) Uani 1 1 d . . . . .
H15A H 0.7788 0.6140 0.8781 0.095 Uiso 1 1 calc GR . . . .
H15B H 0.7204 0.6672 1.0187 0.095 Uiso 1 1 calc GR . . . .
H15C H 0.7701 0.7124 0.8552 0.095 Uiso 1 1 calc GR . . . .
N1 N 0.29754(9) 0.62666(9) 0.35521(17) 0.0438(3) Uani 1 1 d . . . . .
H1 H 0.2973 0.6166 0.2336 0.053 Uiso 1 1 calc R . . . .
O1 O 0.41201(8) 0.55153(7) 0.11190(14) 0.0443(3) Uani 1 1 d . . . . .
O2 O 0.60050(8) 0.53790(7) 0.21346(15) 0.0474(3) Uani 1 1 d . . . . .
H2 H 0.5915 0.5075 0.1158 0.071 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.502(2) . ?
C2 C3 1.3906(18) . ?
C2 C7 1.390(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.3934(19) . ?
C4 C5 1.3846(18) . ?
C4 N1 1.4185(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.3843(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.4194(16) . ?
C8 C13 1.4091(18) . ?
C8 N1 1.3707(16) . ?
C9 C10 1.4025(17) . ?
C9 C14 1.4706(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.3793(19) . ?
C11 C12 1.3981(19) . ?
C11 C15 1.510(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.3725(19) . ?
C13 H13 0.9300 . ?
C14 O1 1.2369(16) . ?
C14 O2 1.3192(14) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N1 H1 0.8600 . ?
O2 H2 0.8200 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.45(14) . . ?
C7 C2 C1 121.29(14) . . ?
C7 C2 C3 118.26(13) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.20(12) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 N1 121.58(12) . . ?
C5 C4 C3 119.67(11) . . ?
C5 C4 N1 118.67(12) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.30(13) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.89(13) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.65(12) . . ?
C6 C7 H7 119.7 . . ?
C13 C8 C9 117.29(11) . . ?
N1 C8 C9 121.64(11) . . ?
N1 C8 C13 121.03(11) . . ?
C8 C9 C14 121.30(11) . . ?
C10 C9 C8 119.60(11) . . ?
C10 C9 C14 119.10(11) . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.52(11) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 117.25(12) . . ?
C10 C11 C15 121.99(13) . . ?
C12 C11 C15 120.76(13) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 C11 122.04(12) . . ?
C13 C12 H12 119.0 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.29(11) . . ?
C12 C13 H13 119.4 . . ?
O1 C14 C9 124.17(11) . . ?
O1 C14 O2 121.31(11) . . ?
O2 C14 C9 114.52(11) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 N1 H1 116.8 . . ?
C8 N1 C4 126.33(11) . . ?
C8 N1 H1 116.8 . . ?
C14 O2 H2 109.5 . . ?

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
C1 C2 C3 C4 -179.40(13) . . . . ?
C1 C2 C7 C6 179.42(14) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 N1 -176.61(12) . . . . ?
C3 C2 C7 C6 -1.3(2) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C3 C4 N1 C8 -45.1(2) . . . . ?
C4 C5 C6 C7 1.6(2) . . . . ?
C5 C4 N1 C8 138.12(15) . . . . ?
C5 C6 C7 C2 -0.2(2) . . . . ?
C7 C2 C3 C4 1.3(2) . . . . ?
C8 C9 C10 C11 -0.10(19) . . . . ?
C8 C9 C14 O1 1.47(19) . . . . ?
C8 C9 C14 O2 -178.78(11) . . . . ?
C9 C8 C13 C12 -1.17(19) . . . . ?
C9 C8 N1 C4 163.59(13) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C9 C10 C11 C15 178.86(14) . . . . ?
C10 C9 C14 O1 -179.25(12) . . . . ?
C10 C9 C14 O2 0.50(17) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
C13 C8 C9 C10 1.07(17) . . . . ?
C13 C8 C9 C14 -179.65(11) . . . . ?
C13 C8 N1 C4 -18.7(2) . . . . ?
C14 C9 C10 C11 -179.40(12) . . . . ?
C15 C11 C12 C13 -178.95(15) . . . . ?
N1 C4 C5 C6 175.26(13) . . . . ?
N1 C8 C9 C10 178.85(12) . . . . ?
N1 C8 C9 C14 -1.88(18) . . . . ?
N1 C8 C13 C12 -178.96(12) . . . . ?

_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_3-II
_database_code_depnum_ccdc_archive 'CCDC 2108385'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_audit_creation_date             2021-05-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O2'
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_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                   7.2703(3)
_cell_length_b                   11.7920(5)
_cell_length_c                   15.9516(5)
_cell_angle_alpha                111.362(3)
_cell_angle_beta                 91.144(3)
_cell_angle_gamma                91.912(4)
_cell_volume                     1272.12(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5754
_cell_measurement_temperature    297.25(11)
_cell_measurement_theta_max      76.3310
_cell_measurement_theta_min      2.9640
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.103a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14470
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.589
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.25(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00  66.00   1.00    0.10    --   47.57  27.00-147.00   29
  2  ω     71.00 122.00   1.00    0.10    --   47.57  27.00-147.00   51
  3  ω     96.00 167.00   1.00    0.26    --  107.75  27.00-147.00   71
  4  ω    101.00 175.00   1.00    0.26    --  107.75  57.00 -60.00   74
  5  ω    100.00 171.00   1.00    0.26    --  107.75   0.00   0.00   71
  6  ω     36.00  71.00   1.00    0.26    --  107.75   0.00   0.00   35
  7  ω     -6.00  21.00   1.00    0.10    --   47.57 -27.00  50.00   27
  8  ω    -13.00  16.00   1.00    0.10    --   47.57 -19.00 -90.00   29
  9  ω    -15.00  17.00   1.00    0.10    --   47.57 -19.00-120.00   32
 10  ω    -25.00  20.00   1.00    0.10    --   47.57 -19.00-150.00   45
 11  ω     36.00  61.00   1.00    0.26    --  107.75 -57.00   0.00   25
 12  ω     51.00 102.00   1.00    0.26    --  107.75 -99.00  60.00   51
 13  ω     60.00  85.00   1.00    0.26    --  107.75 -77.00  90.00   25
 14  ω     71.00 106.00   1.00    0.26    --  107.75 -99.00   0.00   35
 15  ω     36.00  62.00   1.00    0.26    --  107.75 -99.00   0.00   26
 16  ω     49.00 112.00   1.00    0.26    --  107.75-125.00-120.00   63
 17  ω     40.00  98.00   1.00    0.26    --  107.75 -77.00-120.00   58
 18  ω     41.00  79.00   1.00    0.10    --   47.57 -99.00   0.00   38
 19  ω    -11.00  21.00   1.00    0.10    --   47.57 -99.00   0.00   32
 20  ω    -36.00  -1.00   1.00    0.10    --  -47.57  27.00-147.00   35
 21  ω    -60.00 -28.00   1.00    0.26    -- -100.00  77.00-120.00   32
 22  ω    -69.00 -37.00   1.00    0.26    -- -100.00  57.00-180.00   32
 23  ω   -107.00 -82.00   1.00    0.26    -- -100.00  77.00-120.00   25
 24  ω    -86.00 -34.00   1.00    0.26    -- -100.00  77.00 -60.00   52
 25  ω      3.00  28.00   1.00    0.10    --  -47.57  27.00-147.00   25
 26  ω    -65.00 -28.00   1.00    0.26    -- -100.00  57.00  60.00   37
 27  ω    -68.00 -30.00   1.00    0.26    -- -100.00  57.00 120.00   38
 28  ω    -69.00 -29.00   1.00    0.26    -- -100.00  57.00 150.00   40
 29  ω   -126.00-101.00   1.00    0.26    -- -100.00 144.00 153.54   25
 30  ω    -90.00 -56.00   1.00    0.26    -- -100.00 144.00 153.54   34
 31  ω    -55.00 -28.00   1.00    0.26    -- -100.00 125.00 120.00   27
 32  ω   -112.00 -61.00   1.00    0.26    -- -100.00 125.00 120.00   51
 33  ω    -84.00 -47.00   1.00    0.10    --  -47.57 125.00   0.00   37
 34  ω    -61.00 -35.00   1.00    0.26    -- -100.00 125.00 -30.00   26
 35  ω   -112.00 -35.00   1.00    0.26    -- -100.00 125.00 -60.00   77
 36  ω   -107.00 -80.00   1.00    0.26    -- -100.00 125.00 -30.00   27
 37  ω    -65.00 -38.00   1.00    0.10    --  -47.57 -27.00  50.00   27
 38  ω   -119.00 -74.00   1.00    0.10    --  -47.57 -27.00  50.00   45
 39  ω   -158.00-102.00   1.00    0.26    -- -100.00 -99.00 150.00   56
 40  ω   -173.00 -90.00   1.00    0.26    -- -100.00 -27.00  50.00   83
 41  ω   -120.00 -82.00   1.00    0.26    -- -100.00-125.00-180.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0176753000
_diffrn_orient_matrix_UB_12      -0.1390108000
_diffrn_orient_matrix_UB_13      -0.0245240000
_diffrn_orient_matrix_UB_21      -0.2033287000
_diffrn_orient_matrix_UB_22      0.0104785000
_diffrn_orient_matrix_UB_23      0.0261160000
_diffrn_orient_matrix_UB_31      -0.0578763000
_diffrn_orient_matrix_UB_32      -0.0168225000
_diffrn_orient_matrix_UB_33      -0.0973827000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3584
_reflns_number_total             5035
_reflns_odcompleteness_completeness 99.18
_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 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.103a (Rigaku OD, 2021)'
_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         0.225
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5035
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.096
_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)+(0.0975P)²+0.0477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C4(H4), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14),
 N2(H2), C18(H18), C20(H20), C21(H21), C25(H25), C27(H27), C28(H28), C29(H29)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3A)
;
_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 0.2577(3) 0.47629(12) 0.50234(9) 0.0889(5) Uani 1 1 d . . . . .
H1 H 0.244678 0.495995 0.556684 0.133 Uiso 1 1 calc GR . . . .
O2 O 0.2624(2) 0.67649(11) 0.54032(8) 0.0701(4) Uani 1 1 d . . . . .
N1 N 0.3046(2) 0.76536(12) 0.41019(9) 0.0595(4) Uani 1 1 d . . . . .
H1A H 0.290415 0.773755 0.465498 0.071 Uiso 1 1 calc R . . . .
C1 C 0.2778(3) 0.55052(15) 0.38495(10) 0.0528(4) Uani 1 1 d . . . . .
C2 C 0.2967(2) 0.64627(15) 0.35159(10) 0.0512(4) Uani 1 1 d . . . . .
C3 C 0.2997(3) 0.61191(17) 0.25734(11) 0.0616(5) Uani 1 1 d . . . . .
H3 H 0.309774 0.671893 0.232486 0.074 Uiso 1 1 calc R . . . .
C4 C 0.2879(3) 0.49150(18) 0.20146(11) 0.0661(5) Uani 1 1 d . . . . .
H4 H 0.290775 0.472704 0.139610 0.079 Uiso 1 1 calc R . . . .
C5 C 0.2720(3) 0.39650(17) 0.23307(11) 0.0613(5) Uani 1 1 d . . . . .
C6 C 0.2665(3) 0.42904(16) 0.32498(11) 0.0599(5) Uani 1 1 d . . . . .
H6 H 0.254839 0.367660 0.348399 0.072 Uiso 1 1 calc R . . . .
C7 C 0.2655(3) 0.57420(15) 0.48164(11) 0.0585(4) Uani 1 1 d . . . . .
C8 C 0.2593(4) 0.26466(19) 0.17083(14) 0.0797(6) Uani 1 1 d . . . . .
H8A H 0.380762 0.236987 0.154286 0.120 Uiso 1 1 calc GR . . . .
H8B H 0.187486 0.256699 0.117671 0.120 Uiso 1 1 calc GR . . . .
H8C H 0.201628 0.216359 0.200905 0.120 Uiso 1 1 calc GR . . . .
C9 C 0.3316(2) 0.87622(14) 0.39693(10) 0.0512(4) Uani 1 1 d . . . . .
C10 C 0.2603(3) 0.97811(15) 0.46186(10) 0.0524(4) Uani 1 1 d . . . . .
H10 H 0.193686 0.967733 0.507910 0.063 Uiso 1 1 calc R . . . .
C11 C 0.2851(3) 1.09418(15) 0.46032(11) 0.0554(4) Uani 1 1 d . . . . .
C12 C 0.3843(3) 1.10755(17) 0.39074(12) 0.0615(5) Uani 1 1 d . . . . .
H12 H 0.402066 1.184400 0.387689 0.074 Uiso 1 1 calc R . . . .
C13 C 0.4563(3) 1.00833(18) 0.32645(13) 0.0653(5) Uani 1 1 d . . . . .
H13 H 0.522178 1.019131 0.280336 0.078 Uiso 1 1 calc R . . . .
C14 C 0.4329(3) 0.89212(17) 0.32873(11) 0.0599(4) Uani 1 1 d . . . . .
H14 H 0.484298 0.825919 0.285280 0.072 Uiso 1 1 calc R . . . .
C15 C 0.2074(4) 1.20209(17) 0.53203(15) 0.0762(6) Uani 1 1 d . . . . .
H15A H 0.130186 1.244017 0.504358 0.114 Uiso 1 1 calc GR . . . .
H15B H 0.306262 1.256435 0.565939 0.114 Uiso 1 1 calc GR . . . .
H15C H 0.135957 1.174708 0.571560 0.114 Uiso 1 1 calc GR . . . .
O3 O 0.2723(3) 0.73072(11) 0.71612(8) 0.0798(5) Uani 1 1 d . . . . .
H3A H 0.267817 0.711162 0.661223 0.120 Uiso 1 1 calc GR . . . .
O4 O 0.2258(2) 0.53089(11) 0.67819(8) 0.0679(4) Uani 1 1 d . . . . .
N2 N 0.1938(2) 0.44401(13) 0.81053(9) 0.0614(4) Uani 1 1 d . . . . .
H2 H 0.176294 0.430398 0.754154 0.074 Uiso 1 1 calc R . . . .
C16 C 0.2009(3) 0.56453(15) 0.86719(11) 0.0534(4) Uani 1 1 d . . . . .
C17 C 0.2279(3) 0.65911(15) 0.83372(10) 0.0525(4) Uani 1 1 d . . . . .
C18 C 0.2365(3) 0.78051(16) 0.89362(11) 0.0577(4) Uani 1 1 d . . . . .
H18 H 0.256424 0.841677 0.870568 0.069 Uiso 1 1 calc R . . . .
C19 C 0.2167(3) 0.81357(17) 0.98489(11) 0.0614(5) Uani 1 1 d . . . . .
C20 C 0.1818(3) 0.71925(17) 1.01620(12) 0.0640(5) Uani 1 1 d . . . . .
H20 H 0.162783 0.738498 1.077229 0.077 Uiso 1 1 calc R . . . .
C21 C 0.1745(3) 0.59899(17) 0.96016(11) 0.0615(5) Uani 1 1 d . . . . .
H21 H 0.151606 0.539045 0.984125 0.074 Uiso 1 1 calc R . . . .
C22 C 0.2419(3) 0.63328(15) 0.73664(11) 0.0563(4) Uani 1 1 d . . . . .
C23 C 0.2322(4) 0.94438(19) 1.04808(13) 0.0818(6) Uani 1 1 d . . . . .
H23A H 0.111757 0.972262 1.066679 0.123 Uiso 1 1 calc GR . . . .
H23B H 0.287446 0.993444 1.017961 0.123 Uiso 1 1 calc GR . . . .
H23C H 0.307334 0.950977 1.099972 0.123 Uiso 1 1 calc GR . . . .
C24 C 0.2117(3) 0.34061(15) 0.83351(10) 0.0528(4) Uani 1 1 d . . . . .
C25 C 0.1206(2) 0.23250(15) 0.77933(10) 0.0514(4) Uani 1 1 d . . . . .
H25 H 0.044781 0.232411 0.731661 0.062 Uiso 1 1 calc R . . . .
C26 C 0.1394(3) 0.12503(15) 0.79422(11) 0.0551(4) Uani 1 1 d . . . . .
C27 C 0.2495(3) 0.12803(17) 0.86702(12) 0.0637(5) Uani 1 1 d . . . . .
H27 H 0.261835 0.057352 0.879351 0.076 Uiso 1 1 calc R . . . .
C28 C 0.3407(3) 0.23424(18) 0.92115(12) 0.0679(5) Uani 1 1 d . . . . .
H28 H 0.413796 0.234605 0.969779 0.081 Uiso 1 1 calc R . . . .
C29 C 0.3253(3) 0.34045(17) 0.90432(11) 0.0623(5) Uani 1 1 d . . . . .
H29 H 0.390553 0.411301 0.940181 0.075 Uiso 1 1 calc R . . . .
C30 C 0.0452(3) 0.00844(17) 0.73223(15) 0.0740(5) Uani 1 1 d . . . . .
H30A H -0.083596 0.020707 0.726393 0.111 Uiso 1 1 calc GR . . . .
H30B H 0.060245 -0.054219 0.756579 0.111 Uiso 1 1 calc GR . . . .
H30C H 0.098701 -0.015661 0.674106 0.111 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 C7 1.311(2) . ?
O2 C7 1.230(2) . ?
N1 C2 1.373(2) . ?
N1 C9 1.406(2) . ?
C1 C2 1.417(2) . ?
C1 C6 1.402(2) . ?
C1 C7 1.469(2) . ?
C2 C3 1.408(2) . ?
C3 C4 1.373(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.375(2) . ?
C5 C8 1.508(2) . ?
C9 C10 1.393(2) . ?
C9 C14 1.390(2) . ?
C10 C11 1.384(2) . ?
C11 C12 1.389(3) . ?
C11 C15 1.504(3) . ?
C12 C13 1.372(3) . ?
C13 C14 1.389(3) . ?
O3 C22 1.318(2) . ?
O4 C22 1.227(2) . ?
N2 C16 1.377(2) . ?
N2 C24 1.404(2) . ?
C16 C17 1.411(2) . ?
C16 C21 1.407(2) . ?
C17 C18 1.400(2) . ?
C17 C22 1.472(2) . ?
C18 C19 1.375(2) . ?
C19 C20 1.393(3) . ?
C19 C23 1.503(3) . ?
C20 C21 1.372(3) . ?
C24 C25 1.389(2) . ?
C24 C29 1.386(3) . ?
C25 C26 1.382(2) . ?
C26 C27 1.386(3) . ?
C26 C30 1.502(2) . ?
C27 C28 1.374(3) . ?
C28 C29 1.381(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 132.21(13) . . ?
C2 C1 C7 121.94(14) . . ?
C6 C1 C2 119.98(14) . . ?
C6 C1 C7 118.07(15) . . ?
N1 C2 C1 120.02(13) . . ?
N1 C2 C3 123.43(15) . . ?
C3 C2 C1 116.52(14) . . ?
C4 C3 C2 121.22(17) . . ?
C3 C4 C5 123.01(16) . . ?
C4 C5 C8 122.38(17) . . ?
C6 C5 C4 116.27(16) . . ?
C6 C5 C8 121.34(18) . . ?
C5 C6 C1 122.99(17) . . ?
O1 C7 C1 114.75(14) . . ?
O2 C7 O1 121.03(14) . . ?
O2 C7 C1 124.23(14) . . ?
C10 C9 N1 115.96(14) . . ?
C14 C9 N1 125.16(16) . . ?
C14 C9 C10 118.72(15) . . ?
C11 C10 C9 122.38(15) . . ?
C10 C11 C12 117.87(16) . . ?
C10 C11 C15 120.84(16) . . ?
C12 C11 C15 121.29(16) . . ?
C13 C12 C11 120.56(16) . . ?
C12 C13 C14 121.44(17) . . ?
C13 C14 C9 119.02(17) . . ?
C16 N2 C24 127.96(14) . . ?
N2 C16 C17 121.23(14) . . ?
N2 C16 C21 121.66(15) . . ?
C21 C16 C17 117.07(15) . . ?
C16 C17 C22 121.41(14) . . ?
C18 C17 C16 119.53(14) . . ?
C18 C17 C22 119.03(14) . . ?
C19 C18 C17 123.13(16) . . ?
C18 C19 C20 116.52(16) . . ?
C18 C19 C23 122.06(18) . . ?
C20 C19 C23 121.42(16) . . ?
C21 C20 C19 122.32(15) . . ?
C20 C21 C16 121.33(16) . . ?
O3 C22 C17 114.27(14) . . ?
O4 C22 O3 121.49(14) . . ?
O4 C22 C17 124.24(15) . . ?
C25 C24 N2 118.26(15) . . ?
C29 C24 N2 122.64(16) . . ?
C29 C24 C25 118.97(15) . . ?
C26 C25 C24 121.90(15) . . ?
C25 C26 C27 118.02(16) . . ?
C25 C26 C30 120.68(16) . . ?
C27 C26 C30 121.30(16) . . ?
C28 C27 C26 120.74(17) . . ?
C27 C28 C29 120.87(17) . . ?
C28 C29 C24 119.45(17) . . ?

_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 4.279
_oxdiff_exptl_absorpt_empirical_full_min 0.674
####################################################################### 
# 
# 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-II
_database_code_depnum_ccdc_archive 'CCDC 2108381'
loop_
_audit_author_name
_audit_author_address
'Yongliang Shao'
;Lanzhou University
China
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2018). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2021-09-08 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT110_1-II                
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: When this is repeated with "ADDSYM-EXACT", no such problems occur.
The question then becomes, what is the cause of this apparent effect.  In the 
asymmetric unit as given here, the two molecules have different dihedral 
angles between their rings, as follows (from the shelxl LST file):

  REM  Dihedral angles between benzene rings (rounded from LST file):
  REM    Molecule A: 60.07(6) degrees
  REM    Molecule B: 73.29(6) degrees

In this refinement, there are no correlation coefficients larger in magnitude 
than about 0.550 (actually negative), and the largest correlations seen are 
between parameters within individual molecules, not between the two molecules. 
If the suggestion of Platon were in fact correct, then there would be large 
correlation for corresponding parameters between the two molecules.  No such 
correlations are seen.  This combined with the quite distinct dihedral angles 
strongly suggest that the asymmetric unit does in fact contain two molecules, 
albeit with similar, conformations. 
;
_vrf_PLAT112_1-II                
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       b/2        100 %Fit  
RESPONSE: If the transformation suggested by Platon is taken at face value, 
then the asymmetric unit contains just one molecule.  Upon such a refinement, 
this averaged molecule (not surprisingly) has a dihedral between its rings 
that is the average for the two conformations in the model given here. Such 
a model refines quite well, but the ellipsoids of the ring become elongated 
in order to account for the electron density of the two different dihedrals 
found for the Z'=2 structure model.

There is, of course, a possibility that at some other (warmer) temperature, 
the two molecules coalesce.  To test this would require fresh crystals.
;
_vrf_PLAT113_1-II                
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group        P-1 Check 
RESPONSE: This suggestion is the same space group, not a "new" space group.
The reasons for not using it are given above.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3

_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6511(2)
_cell_length_b                   9.2344(2)
_cell_length_c                   15.2887(4)
_cell_angle_alpha                87.8734(10)
_cell_angle_beta                 80.979(1)
_cell_angle_gamma                69.9465(10)
_cell_volume                     1132.96(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    5064
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            24888
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.348
_diffrn_reflns_theta_max         27.573
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             5201
_reflns_number_gt                2958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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. 
;

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1054P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5201
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1A C 0.3792(2) 0.62840(18) 0.31423(10) 0.0219(4) Uani 1 1 d . . . . .
C2A C 0.2907(2) 0.57207(18) 0.38586(10) 0.0209(4) Uani 1 1 d . . . . .
C3A C 0.1181(2) 0.64369(19) 0.40761(10) 0.0240(4) Uani 1 1 d . . . . .
H3A H 0.059336 0.605038 0.455114 0.029 Uiso 1 1 calc R U . . .
C4A C 0.0314(2) 0.7688(2) 0.36183(11) 0.0272(4) Uani 1 1 d . . . . .
H4A H -0.085687 0.816291 0.377581 0.033 Uiso 1 1 calc R U . . .
C5A C 0.1184(2) 0.8246(2) 0.29192(11) 0.0270(4) Uani 1 1 d . . . . .
H5A H 0.059685 0.910835 0.259973 0.032 Uiso 1 1 calc R U . . .
C6A C 0.2875(2) 0.75679(19) 0.26858(11) 0.0261(4) Uani 1 1 d . . . . .
H6A H 0.343793 0.797100 0.220772 0.031 Uiso 1 1 calc R U . . .
N7A N 0.54862(18) 0.56446(17) 0.29259(9) 0.0263(4) Uani 1 1 d . . . . .
H7A H 0.597(2) 0.489(2) 0.3309(11) 0.032 Uiso 1 1 d . U . . .
C8A C 0.6474(2) 0.59889(19) 0.2171(1) 0.0240(4) Uani 1 1 d . . . . .
C9A C 0.6138(2) 0.5863(2) 0.13233(11) 0.0278(4) Uani 1 1 d . . . . .
H9A H 0.519262 0.560657 0.124945 0.033 Uiso 1 1 calc R U . . .
C10A C 0.7172(2) 0.61090(19) 0.05787(11) 0.0273(4) Uani 1 1 d . . . . .
C11A C 0.8562(2) 0.64629(19) 0.07006(11) 0.0278(4) Uani 1 1 d . . . . .
H11A H 0.928364 0.662487 0.020060 0.033 Uiso 1 1 calc R U . . .
C12A C 0.8903(2) 0.6581(2) 0.15460(11) 0.0302(4) Uani 1 1 d . . . . .
H12A H 0.985860 0.682128 0.162135 0.036 Uiso 1 1 calc R U . . .
C13A C 0.7860(2) 0.63521(19) 0.22818(11) 0.0264(4) Uani 1 1 d . . . . .
H13A H 0.809317 0.644342 0.286000 0.032 Uiso 1 1 calc R U . . .
C14A C 0.3773(2) 0.43918(19) 0.43686(10) 0.0212(4) Uani 1 1 d . . . . .
O15A O 0.52994(14) 0.37072(13) 0.42359(7) 0.0249(3) Uani 1 1 d . . . . .
O16A O 0.27981(14) 0.39639(13) 0.50040(7) 0.0258(3) Uani 1 1 d . . . . .
H16A H 0.344(2) 0.313(2) 0.5256(12) 0.039 Uiso 1 1 d . U . . .
C17A C 0.6842(2) 0.5896(2) -0.03394(11) 0.0394(5) Uani 1 1 d . . . . .
H17A H 0.755250 0.628948 -0.077546 0.059 Uiso 1 1 calc R U . . .
H17B H 0.567020 0.646295 -0.038126 0.059 Uiso 1 1 calc R U . . .
H17C H 0.709040 0.479742 -0.045800 0.059 Uiso 1 1 calc R U . . .
C1B C 0.5986(2) -0.11478(18) 0.68555(10) 0.0218(4) Uani 1 1 d . . . . .
C2B C 0.6885(2) -0.05992(18) 0.6138(1) 0.0218(4) Uani 1 1 d . . . . .
C3B C 0.8614(2) -0.13274(19) 0.5931(1) 0.0243(4) Uani 1 1 d . . . . .
H3B H 0.921137 -0.094746 0.545770 0.029 Uiso 1 1 calc R U . . .
C4B C 0.9469(2) -0.2574(2) 0.63918(11) 0.0286(4) Uani 1 1 d . . . . .
H4B H 1.063985 -0.305448 0.624063 0.034 Uiso 1 1 calc R U . . .
C5B C 0.8576(2) -0.3114(2) 0.70861(11) 0.0281(4) Uani 1 1 d . . . . .
H5B H 0.915257 -0.397521 0.741015 0.034 Uiso 1 1 calc R U . . .
C6B C 0.6890(2) -0.24357(19) 0.73127(10) 0.0260(4) Uani 1 1 d . . . . .
H6B H 0.631818 -0.283966 0.778643 0.031 Uiso 1 1 calc R U . . .
N7B N 0.42971(18) -0.04970(17) 0.70843(9) 0.0267(4) Uani 1 1 d . . . . .
H7B H 0.379(2) 0.023(2) 0.6742(11) 0.032 Uiso 1 1 d . U . . .
C8B C 0.3373(2) -0.08875(18) 0.78578(10) 0.0232(4) Uani 1 1 d . . . . .
C9B C 0.3570(2) -0.0497(2) 0.86894(11) 0.0292(4) Uani 1 1 d . . . . .
H9B H 0.432562 0.002656 0.873852 0.035 Uiso 1 1 calc R U . . .
C10B C 0.2679(2) -0.08589(19) 0.94541(11) 0.0272(4) Uani 1 1 d . . . . .
C11B C 0.1569(2) -0.16062(19) 0.93641(12) 0.0308(4) Uani 1 1 d . . . . .
H11B H 0.094585 -0.186054 0.987744 0.037 Uiso 1 1 calc R U . . .
C12B C 0.1360(2) -0.1985(2) 0.85359(12) 0.0395(5) Uani 1 1 d . . . . .
H12B H 0.058847 -0.249035 0.848447 0.047 Uiso 1 1 calc R U . . .
C13B C 0.2269(2) -0.1635(2) 0.77777(12) 0.0307(4) Uani 1 1 d . . . . .
H13B H 0.213123 -0.190758 0.720926 0.037 Uiso 1 1 calc R U . . .
C14B C 0.6035(2) 0.07346(19) 0.56294(10) 0.0223(4) Uani 1 1 d . . . . .
O15B O 0.45157(14) 0.14378(13) 0.57662(7) 0.0262(3) Uani 1 1 d . . . . .
O16B O 0.70206(14) 0.11524(13) 0.49901(7) 0.0263(3) Uani 1 1 d . . . . .
H16B H 0.634(2) 0.204(2) 0.4704(12) 0.039 Uiso 1 1 d . U . . .
C17B C 0.2920(2) -0.0449(2) 1.03525(11) 0.0403(5) Uani 1 1 d . . . . .
H17D H 0.197319 -0.047165 1.079198 0.060 Uiso 1 1 calc R U . . .
H17E H 0.299390 0.058691 1.034139 0.060 Uiso 1 1 calc R U . . .
H17F H 0.394908 -0.119540 1.051034 0.060 Uiso 1 1 calc R U . . .


_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
C1A N7A 1.369(2) . ?
C1A C6A 1.411(2) . ?
C1A C2A 1.423(2) . ?
C2A C3A 1.401(2) . ?
C2A C14A 1.469(2) . ?
C3A C4A 1.378(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.396(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.373(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
N7A C8A 1.419(2) . ?
N7A H7A 0.923(18) . ?
C8A C13A 1.386(2) . ?
C8A C9A 1.389(2) . ?
C9A C10A 1.396(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.389(2) . ?
C10A C17A 1.508(2) . ?
C11A C12A 1.387(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.386(2) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A O15A 1.2399(19) . ?
C14A O16A 1.3246(18) . ?
O16A H16A 0.897(19) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C1B N7B 1.368(2) . ?
C1B C6B 1.409(2) . ?
C1B C2B 1.424(2) . ?
C2B C3B 1.402(2) . ?
C2B C14B 1.466(2) . ?
C3B C4B 1.374(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.393(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.368(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
N7B C8B 1.427(2) . ?
N7B H7B 0.873(18) . ?
C8B C13B 1.378(2) . ?
C8B C9B 1.385(2) . ?
C9B C10B 1.392(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.385(2) . ?
C10B C17B 1.502(2) . ?
C11B C12B 1.381(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.388(2) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B O15B 1.2377(19) . ?
C14B O16B 1.3293(19) . ?
O16B H16B 0.967(19) . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?

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
N7A C1A C6A 120.99(15) . . ?
N7A C1A C2A 121.23(15) . . ?
C6A C1A C2A 117.73(15) . . ?
C3A C2A C1A 119.48(15) . . ?
C3A C2A C14A 119.47(15) . . ?
C1A C2A C14A 121.05(15) . . ?
C4A C3A C2A 121.62(16) . . ?
C4A C3A H3A 119.2 . . ?
C2A C3A H3A 119.2 . . ?
C3A C4A C5A 118.86(16) . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A H4A 120.6 . . ?
C6A C5A C4A 121.05(16) . . ?
C6A C5A H5A 119.5 . . ?
C4A C5A H5A 119.5 . . ?
C5A C6A C1A 121.24(16) . . ?
C5A C6A H6A 119.4 . . ?
C1A C6A H6A 119.4 . . ?
C1A N7A C8A 126.12(14) . . ?
C1A N7A H7A 113.6(11) . . ?
C8A N7A H7A 120.2(11) . . ?
C13A C8A C9A 119.76(15) . . ?
C13A C8A N7A 119.15(15) . . ?
C9A C8A N7A 120.94(15) . . ?
C8A C9A C10A 120.88(15) . . ?
C8A C9A H9A 119.6 . . ?
C10A C9A H9A 119.6 . . ?
C11A C10A C9A 118.66(15) . . ?
C11A C10A C17A 120.80(16) . . ?
C9A C10A C17A 120.43(16) . . ?
C12A C11A C10A 120.53(16) . . ?
C12A C11A H11A 119.7 . . ?
C10A C11A H11A 119.7 . . ?
C13A C12A C11A 120.40(16) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C12A C13A C8A 119.76(16) . . ?
C12A C13A H13A 120.1 . . ?
C8A C13A H13A 120.1 . . ?
O15A C14A O16A 121.12(15) . . ?
O15A C14A C2A 123.96(15) . . ?
O16A C14A C2A 114.92(14) . . ?
C14A O16A H16A 107.7(12) . . ?
C10A C17A H17A 109.5 . . ?
C10A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C10A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
N7B C1B C6B 120.30(15) . . ?
N7B C1B C2B 122.04(14) . . ?
C6B C1B C2B 117.62(15) . . ?
C3B C2B C1B 119.26(15) . . ?
C3B C2B C14B 119.79(15) . . ?
C1B C2B C14B 120.93(15) . . ?
C4B C3B C2B 122.01(16) . . ?
C4B C3B H3B 119.0 . . ?
C2B C3B H3B 119.0 . . ?
C3B C4B C5B 118.34(16) . . ?
C3B C4B H4B 120.8 . . ?
C5B C4B H4B 120.8 . . ?
C6B C5B C4B 121.61(16) . . ?
C6B C5B H5B 119.2 . . ?
C4B C5B H5B 119.2 . . ?
C5B C6B C1B 121.14(16) . . ?
C5B C6B H6B 119.4 . . ?
C1B C6B H6B 119.4 . . ?
C1B N7B C8B 123.86(14) . . ?
C1B N7B H7B 116.1(12) . . ?
C8B N7B H7B 119.9(12) . . ?
C13B C8B C9B 119.96(16) . . ?
C13B C8B N7B 120.04(15) . . ?
C9B C8B N7B 119.99(15) . . ?
C8B C9B C10B 121.16(16) . . ?
C8B C9B H9B 119.4 . . ?
C10B C9B H9B 119.4 . . ?
C11B C10B C9B 118.29(16) . . ?
C11B C10B C17B 121.03(16) . . ?
C9B C10B C17B 120.68(16) . . ?
C12B C11B C10B 120.68(16) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C11B C12B C13B 120.56(17) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B H12B 119.7 . . ?
C8B C13B C12B 119.35(16) . . ?
C8B C13B H13B 120.3 . . ?
C12B C13B H13B 120.3 . . ?
O15B C14B O16B 121.10(15) . . ?
O15B C14B C2B 123.89(15) . . ?
O16B C14B C2B 115.01(14) . . ?
C14B O16B H16B 108.4(11) . . ?
C10B C17B H17D 109.5 . . ?
C10B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C10B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?

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
N7A C1A C2A C3A 178.04(14) . . . . ?
C6A C1A C2A C3A 0.7(2) . . . . ?
N7A C1A C2A C14A -2.5(2) . . . . ?
C6A C1A C2A C14A -179.82(14) . . . . ?
C1A C2A C3A C4A -0.6(2) . . . . ?
C14A C2A C3A C4A 179.90(14) . . . . ?
C2A C3A C4A C5A 0.2(2) . . . . ?
C3A C4A C5A C6A 0.0(3) . . . . ?
C4A C5A C6A C1A 0.1(3) . . . . ?
N7A C1A C6A C5A -177.79(14) . . . . ?
C2A C1A C6A C5A -0.5(2) . . . . ?
C6A C1A N7A C8A -10.4(3) . . . . ?
C2A C1A N7A C8A 172.40(15) . . . . ?
C1A N7A C8A C13A 129.54(18) . . . . ?
C1A N7A C8A C9A -54.9(2) . . . . ?
C13A C8A C9A C10A -0.5(3) . . . . ?
N7A C8A C9A C10A -175.98(15) . . . . ?
C8A C9A C10A C11A 0.9(3) . . . . ?
C8A C9A C10A C17A 177.10(16) . . . . ?
C9A C10A C11A C12A -0.5(3) . . . . ?
C17A C10A C11A C12A -176.76(16) . . . . ?
C10A C11A C12A C13A -0.2(3) . . . . ?
C11A C12A C13A C8A 0.6(3) . . . . ?
C9A C8A C13A C12A -0.2(2) . . . . ?
N7A C8A C13A C12A 175.35(15) . . . . ?
C3A C2A C14A O15A -178.42(14) . . . . ?
C1A C2A C14A O15A 2.1(3) . . . . ?
C3A C2A C14A O16A 0.9(2) . . . . ?
C1A C2A C14A O16A -178.51(13) . . . . ?
N7B C1B C2B C3B -179.31(14) . . . . ?
C6B C1B C2B C3B -1.5(2) . . . . ?
N7B C1B C2B C14B 2.2(2) . . . . ?
C6B C1B C2B C14B 179.99(14) . . . . ?
C1B C2B C3B C4B 1.0(2) . . . . ?
C14B C2B C3B C4B 179.53(14) . . . . ?
C2B C3B C4B C5B -0.2(2) . . . . ?
C3B C4B C5B C6B 0.0(3) . . . . ?
C4B C5B C6B C1B -0.6(3) . . . . ?
N7B C1B C6B C5B 179.16(14) . . . . ?
C2B C1B C6B C5B 1.3(2) . . . . ?
C6B C1B N7B C8B 9.8(2) . . . . ?
C2B C1B N7B C8B -172.39(15) . . . . ?
C1B N7B C8B C13B -112.79(19) . . . . ?
C1B N7B C8B C9B 68.0(2) . . . . ?
C13B C8B C9B C10B 0.6(3) . . . . ?
N7B C8B C9B C10B 179.74(14) . . . . ?
C8B C9B C10B C11B -0.8(3) . . . . ?
C8B C9B C10B C17B 179.15(15) . . . . ?
C9B C10B C11B C12B 0.2(3) . . . . ?
C17B C10B C11B C12B -179.70(17) . . . . ?
C10B C11B C12B C13B 0.5(3) . . . . ?
C9B C8B C13B C12B 0.2(3) . . . . ?
N7B C8B C13B C12B -179.00(16) . . . . ?
C11B C12B C13B C8B -0.7(3) . . . . ?
C3B C2B C14B O15B 179.66(14) . . . . ?
C1B C2B C14B O15B -1.8(3) . . . . ?
C3B C2B C14B O16B 0.0(2) . . . . ?
C1B C2B C14B O16B 178.52(13) . . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2108287'
loop_
_audit_author_name
_audit_author_address
'Archishmati Dubey'
;Indian Institute of Technology Delhi
India
;
_audit_update_record             
;
2021-10-23 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N2 O9 Sn2, 4(H2 O)'
_chemical_formula_sum            'C24 H32 N2 O13 Sn2'
_chemical_formula_weight         793.89

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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1982(9)
_cell_length_b                   11.5288(10)
_cell_length_c                   13.5216(12)
_cell_angle_alpha                99.656(4)
_cell_angle_beta                 107.013(3)
_cell_angle_gamma                93.861(3)
_cell_volume                     1487.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.30

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    1.745
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_absorpt_special_details   
'Bruker AXS area detector scaling and absorption correction'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40694
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.606
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7335
_reflns_number_gt                6601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0870P)²+0.9257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7335
_refine_ls_number_parameters     395
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Sn1 Sn 0.39875(2) 0.10357(2) -0.19588(2) 0.01246(9) Uani 1 1 d . . . . .
Sn2 Sn 0.78993(2) 0.72309(2) 0.58619(2) 0.01534(9) Uani 1 1 d D . . . .
O1 O 0.4598(2) 0.16481(19) -0.03519(17) 0.0144(4) Uani 1 1 d . . . . .
O4 O 0.5836(2) 0.70554(19) 0.19971(18) 0.0151(4) Uani 1 1 d . . . . .
O8 O 0.5964(3) 0.0691(2) 0.15019(18) 0.0188(5) Uani 1 1 d . . . . .
O6 O 0.6841(3) 0.5635(2) 0.46385(18) 0.0206(5) Uani 1 1 d . . . . .
O7 O 0.6524(3) 0.1361(2) 0.32350(19) 0.0224(5) Uani 1 1 d . . . . .
O3 O 0.7383(2) 0.6647(2) 0.11422(18) 0.0183(5) Uani 1 1 d . . . . .
O5 O 0.7978(3) 0.6739(2) 0.38965(19) 0.0197(5) Uani 1 1 d . . . . .
O9 O 0.9118(3) 0.8972(2) 0.5623(2) 0.0230(5) Uani 1 1 d G . . . .
H9A H 0.870710 0.956258 0.540830 0.035 Uiso 1 1 d DG U . . .
H9B H 0.979079 0.893416 0.534912 0.035 Uiso 1 1 d DG U . . .
O2 O 0.6796(3) 0.2006(2) -0.02775(19) 0.0229(5) Uani 1 1 d . . . . .
O10 O 0.9415(3) 0.3410(3) 0.0309(3) 0.0382(7) Uani 1 1 d G . . . .
H10A H 0.957580 0.394715 0.087936 0.057 Uiso 1 1 d G U . . .
H10B H 0.865444 0.298628 0.026645 0.057 Uiso 1 1 d G U . . .
N1 N 0.7186(3) 0.6044(3) 0.6877(2) 0.0211(6) Uani 1 1 d . . . . .
O11 O 0.9876(3) 0.5815(3) 0.1360(2) 0.0329(6) Uani 1 1 d DG . . . .
H11D H 0.911992 0.613877 0.131291 0.049 Uiso 1 1 d DG U . . .
N2 N 0.8256(3) 0.8343(3) 0.7578(2) 0.0199(6) Uani 1 1 d . . . . .
O12 O 0.8534(3) 0.1111(2) 0.5044(2) 0.0293(6) Uani 1 1 d DG . . . .
O13 O 0.9414(3) 0.3196(2) 0.6444(2) 0.0357(7) Uani 1 1 d G . . . .
H13D H 1.028838 0.329869 0.650380 0.054 Uiso 1 1 d G U . . .
H13E H 0.936617 0.352881 0.705729 0.054 Uiso 1 1 d G U . . .
C3 C 0.7210(3) 0.5823(3) 0.3850(2) 0.0152(6) Uani 1 1 d . . . . .
C4 C 0.6629(3) 0.6385(3) 0.1658(2) 0.0123(5) Uani 1 1 d . . . . .
C1 C 0.5859(3) 0.2124(3) 0.0107(2) 0.0140(6) Uani 1 1 d . . . . .
C2 C 0.6259(3) 0.1530(3) 0.2311(3) 0.0160(6) Uani 1 1 d . . . . .
C5 C 0.6115(3) 0.3028(3) 0.1114(2) 0.0111(5) Uani 1 1 d . . . . .
C8 C 0.6734(3) 0.4876(3) 0.2872(2) 0.0125(5) Uani 1 1 d . . . . .
C9 C 0.6546(3) 0.5138(2) 0.1867(2) 0.0110(5) Uani 1 1 d . . . . .
C6 C 0.6291(3) 0.2767(3) 0.2117(2) 0.0129(5) Uani 1 1 d . . . . .
C20 C 0.7781(3) 0.7799(3) 0.8233(3) 0.0205(7) Uani 1 1 d . . . . .
C10 C 0.6244(3) 0.4209(3) 0.1003(2) 0.0123(5) Uani 1 1 d . . . . .
H10 H 0.612300 0.438118 0.032130 0.015 Uiso 1 1 calc R U . . .
C7 C 0.6599(3) 0.3707(3) 0.2986(2) 0.0132(6) Uani 1 1 d . . . . .
H7 H 0.671735 0.353760 0.366819 0.016 Uiso 1 1 calc R U . . .
C11 C 0.5522(4) 0.0869(3) -0.2717(3) 0.0213(7) Uani 1 1 d . . . . .
H11A H 0.628006 0.151305 -0.237528 0.032 Uiso 1 1 calc R U . . .
H11B H 0.512297 0.091324 -0.346078 0.032 Uiso 1 1 calc R U . . .
H11C H 0.587570 0.010488 -0.266646 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1806(4) 0.0828(3) -0.2503(3) 0.0233(7) Uani 1 1 d . . . . .
H12A H 0.145929 -0.000897 -0.280307 0.035 Uiso 1 1 calc R U . . .
H12B H 0.149194 0.130267 -0.304549 0.035 Uiso 1 1 calc R U . . .
H12C H 0.145427 0.109543 -0.191261 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6813(4) 0.4872(4) 0.6537(3) 0.0246(7) Uani 1 1 d . . . . .
H15 H 0.667884 0.454808 0.581593 0.029 Uiso 1 1 calc R U . . .
C18 C 0.7177(4) 0.5794(4) 0.8592(3) 0.0251(8) Uani 1 1 d . . . . .
H18 H 0.730139 0.613140 0.930879 0.030 Uiso 1 1 calc R U . . .
C24 C 0.8699(4) 0.9503(3) 0.7860(3) 0.0235(7) Uani 1 1 d . . . . .
H24 H 0.905707 0.987884 0.740290 0.028 Uiso 1 1 calc R U . . .
C19 C 0.7360(3) 0.6515(3) 0.7905(3) 0.0202(7) Uani 1 1 d . . . . .
C13 C 0.9865(4) 0.6638(3) 0.6236(3) 0.0248(7) Uani 1 1 d . . . . .
H13A H 1.035920 0.687613 0.576611 0.037 Uiso 1 1 calc R U . . .
H13B H 0.975791 0.577237 0.614739 0.037 Uiso 1 1 calc R U . . .
H13C H 1.039218 0.699113 0.696941 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6116(4) 0.8071(3) 0.5346(3) 0.0264(7) Uani 1 1 d . . . . .
H14A H 0.636091 0.893306 0.555156 0.040 Uiso 1 1 calc R U . . .
H14B H 0.542806 0.782345 0.566993 0.040 Uiso 1 1 calc R U . . .
H14C H 0.573041 0.784708 0.457647 0.040 Uiso 1 1 calc R U . . .
C16 C 0.6616(4) 0.4116(4) 0.7184(3) 0.0268(8) Uani 1 1 d . . . . .
H16 H 0.634977 0.329087 0.691567 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7691(4) 0.8429(4) 0.9190(3) 0.0269(8) Uani 1 1 d . . . . .
H21 H 0.734584 0.803595 0.964306 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6815(4) 0.4592(4) 0.8234(3) 0.0271(8) Uani 1 1 d . . . . .
H17 H 0.670364 0.409360 0.870404 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8653(4) 1.0180(4) 0.8803(3) 0.0289(8) Uani 1 1 d . . . . .
H23 H 0.898551 1.100164 0.899125 0.035 Uiso 1 1 calc R U . . .
C22 C 0.8120(4) 0.9639(4) 0.9456(3) 0.0315(9) Uani 1 1 d . . . . .
H22 H 0.804449 1.009159 1.008827 0.038 Uiso 1 1 calc R U . . .
H12D H 0.863(6) 0.175(3) 0.550(3) 0.048(15) Uiso 1 1 d D . . . .
H12E H 0.790(4) 0.119(5) 0.449(3) 0.048(16) Uiso 1 1 d D . . . .
H11E H 0.996(12) 0.575(11) 0.074(4) 0.19(5) Uiso 1 1 d 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
Sn1 O1 2.060(2) . ?
Sn1 C11 2.109(3) . ?
Sn1 C12 2.112(3) . ?
Sn1 O8 2.181(2) 2_655 ?
Sn1 O4 2.206(2) 2_665 ?
Sn2 C13 2.109(4) . ?
Sn2 C14 2.111(4) . ?
Sn2 O6 2.226(2) . ?
Sn2 N1 2.316(3) . ?
Sn2 N2 2.367(3) . ?
Sn2 O9 2.407(3) . ?
O1 C1 1.290(4) . ?
O4 C4 1.283(4) . ?
O8 C2 1.279(4) . ?
O6 C3 1.275(4) . ?
O7 C2 1.251(4) . ?
O3 C4 1.234(4) . ?
O5 C3 1.254(4) . ?
O9 H9A 0.8698 . ?
O9 H9B 0.8699 . ?
O2 C1 1.219(4) . ?
O10 H10A 0.8701 . ?
O10 H10B 0.8700 . ?
N1 C15 1.342(5) . ?
N1 C19 1.360(4) . ?
O11 H11D 0.8702 . ?
O11 H11E 0.86(2) . ?
N2 C24 1.336(5) . ?
N2 C20 1.346(5) . ?
O12 H12D 0.859(19) . ?
O12 H12E 0.862(19) . ?
O13 H13D 0.8699 . ?
O13 H13E 0.8703 . ?
C3 C8 1.499(4) . ?
C4 C9 1.512(4) . ?
C1 C5 1.512(4) . ?
C2 C6 1.493(4) . ?
C5 C10 1.395(4) . ?
C5 C6 1.402(4) . ?
C8 C7 1.384(4) . ?
C8 C9 1.402(4) . ?
C9 C10 1.391(4) . ?
C6 C7 1.401(4) . ?
C20 C21 1.405(4) . ?
C20 C19 1.468(5) . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 C16 1.379(5) . ?
C15 H15 0.9500 . ?
C18 C17 1.376(6) . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C24 C23 1.395(5) . ?
C24 H24 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.383(5) . ?
C16 H16 0.9500 . ?
C21 C22 1.387(6) . ?
C21 H21 0.9500 . ?
C17 H17 0.9500 . ?
C23 C22 1.373(6) . ?
C23 H23 0.9500 . ?
C22 H22 0.9500 . ?

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
O1 Sn1 C11 118.47(12) . . ?
O1 Sn1 C12 107.59(12) . . ?
C11 Sn1 C12 133.75(14) . . ?
O1 Sn1 O8 82.88(9) . 2_655 ?
C11 Sn1 O8 96.92(12) . 2_655 ?
C12 Sn1 O8 92.41(12) . 2_655 ?
O1 Sn1 O4 83.03(9) . 2_665 ?
C11 Sn1 O4 88.30(11) . 2_665 ?
C12 Sn1 O4 93.47(11) . 2_665 ?
O8 Sn1 O4 165.80(9) 2_655 2_665 ?
C13 Sn2 C14 168.30(15) . . ?
C13 Sn2 O6 95.49(13) . . ?
C14 Sn2 O6 88.38(12) . . ?
C13 Sn2 N1 91.19(13) . . ?
C14 Sn2 N1 100.39(13) . . ?
O6 Sn2 N1 79.17(9) . . ?
C13 Sn2 N2 94.43(12) . . ?
C14 Sn2 N2 87.98(13) . . ?
O6 Sn2 N2 148.05(10) . . ?
N1 Sn2 N2 70.32(11) . . ?
C13 Sn2 O9 83.89(13) . . ?
C14 Sn2 O9 84.99(13) . . ?
O6 Sn2 O9 127.26(9) . . ?
N1 Sn2 O9 153.40(10) . . ?
N2 Sn2 O9 83.98(10) . . ?
C1 O1 Sn1 118.02(19) . . ?
C4 O4 Sn1 120.64(19) . 2_665 ?
C2 O8 Sn1 111.08(19) . 2_655 ?
C3 O6 Sn2 102.14(19) . . ?
Sn2 O9 H9A 123.0 . . ?
Sn2 O9 H9B 122.2 . . ?
H9A O9 H9B 104.5 . . ?
H10A O10 H10B 104.5 . . ?
C15 N1 C19 118.6(3) . . ?
C15 N1 Sn2 122.2(2) . . ?
C19 N1 Sn2 118.4(2) . . ?
H11D O11 H11E 104.2 . . ?
C24 N2 C20 119.3(3) . . ?
C24 N2 Sn2 123.4(2) . . ?
C20 N2 Sn2 116.5(2) . . ?
H12D O12 H12E 106(5) . . ?
H13D O13 H13E 104.5 . . ?
O5 C3 O6 121.8(3) . . ?
O5 C3 C8 120.9(3) . . ?
O6 C3 C8 117.2(3) . . ?
O3 C4 O4 126.1(3) . . ?
O3 C4 C9 118.3(3) . . ?
O4 C4 C9 115.4(3) . . ?
O2 C1 O1 124.6(3) . . ?
O2 C1 C5 118.6(3) . . ?
O1 C1 C5 116.1(3) . . ?
O7 C2 O8 123.5(3) . . ?
O7 C2 C6 119.6(3) . . ?
O8 C2 C6 116.9(3) . . ?
C10 C5 C6 119.5(3) . . ?
C10 C5 C1 115.0(3) . . ?
C6 C5 C1 125.4(3) . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 C3 118.1(3) . . ?
C9 C8 C3 121.8(3) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 C4 117.3(3) . . ?
C8 C9 C4 123.8(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 C2 118.4(3) . . ?
C5 C6 C2 122.8(3) . . ?
N2 C20 C21 121.6(4) . . ?
N2 C20 C19 117.1(3) . . ?
C21 C20 C19 121.3(3) . . ?
C9 C10 C5 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
Sn1 C11 H11A 109.5 . . ?
Sn1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Sn1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Sn1 C12 H12A 109.5 . . ?
Sn1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
Sn1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C15 C16 123.2(3) . . ?
N1 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
N2 C24 C23 122.1(4) . . ?
N2 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
N1 C19 C18 120.6(3) . . ?
N1 C19 C20 116.1(3) . . ?
C18 C19 C20 123.2(3) . . ?
Sn2 C13 H13A 109.5 . . ?
Sn2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
Sn2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Sn2 C14 H14A 109.5 . . ?
Sn2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Sn2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 C16 C17 118.2(4) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C22 C21 C20 118.3(4) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C22 C23 C24 118.9(4) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C22 C21 119.7(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?

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
Sn2 O6 C3 O5 -0.5(4) . . . . ?
Sn2 O6 C3 C8 177.1(2) . . . . ?
Sn1 O4 C4 O3 -12.2(4) 2_665 . . . ?
Sn1 O4 C4 C9 171.72(19) 2_665 . . . ?
Sn1 O1 C1 O2 -17.4(4) . . . . ?
Sn1 O1 C1 C5 153.1(2) . . . . ?
Sn1 O8 C2 O7 -0.6(4) 2_655 . . . ?
Sn1 O8 C2 C6 178.9(2) 2_655 . . . ?
O2 C1 C5 C10 70.4(4) . . . . ?
O1 C1 C5 C10 -100.7(3) . . . . ?
O2 C1 C5 C6 -106.4(4) . . . . ?
O1 C1 C5 C6 82.5(4) . . . . ?
O5 C3 C8 C7 144.4(3) . . . . ?
O6 C3 C8 C7 -33.2(4) . . . . ?
O5 C3 C8 C9 -30.0(5) . . . . ?
O6 C3 C8 C9 152.5(3) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C3 C8 C9 C10 173.3(3) . . . . ?
C7 C8 C9 C4 178.1(3) . . . . ?
C3 C8 C9 C4 -7.7(5) . . . . ?
O3 C4 C9 C10 -52.1(4) . . . . ?
O4 C4 C9 C10 124.3(3) . . . . ?
O3 C4 C9 C8 128.8(3) . . . . ?
O4 C4 C9 C8 -54.7(4) . . . . ?
C10 C5 C6 C7 -0.3(4) . . . . ?
C1 C5 C6 C7 176.4(3) . . . . ?
C10 C5 C6 C2 -176.0(3) . . . . ?
C1 C5 C6 C2 0.7(5) . . . . ?
O7 C2 C6 C7 -1.0(5) . . . . ?
O8 C2 C6 C7 179.4(3) . . . . ?
O7 C2 C6 C5 174.7(3) . . . . ?
O8 C2 C6 C5 -4.8(5) . . . . ?
C24 N2 C20 C21 2.3(5) . . . . ?
Sn2 N2 C20 C21 -167.7(3) . . . . ?
C24 N2 C20 C19 -177.6(3) . . . . ?
Sn2 N2 C20 C19 12.4(4) . . . . ?
C8 C9 C10 C5 0.5(4) . . . . ?
C4 C9 C10 C5 -178.6(3) . . . . ?
C6 C5 C10 C9 0.1(4) . . . . ?
C1 C5 C10 C9 -176.9(3) . . . . ?
C9 C8 C7 C6 0.7(5) . . . . ?
C3 C8 C7 C6 -173.7(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C2 C6 C7 C8 175.8(3) . . . . ?
C19 N1 C15 C16 -1.0(6) . . . . ?
Sn2 N1 C15 C16 168.4(3) . . . . ?
C20 N2 C24 C23 -1.7(5) . . . . ?
Sn2 N2 C24 C23 167.6(3) . . . . ?
C15 N1 C19 C18 1.1(5) . . . . ?
Sn2 N1 C19 C18 -168.7(2) . . . . ?
C15 N1 C19 C20 179.4(3) . . . . ?
Sn2 N1 C19 C20 9.6(4) . . . . ?
C17 C18 C19 N1 -0.1(5) . . . . ?
C17 C18 C19 C20 -178.3(3) . . . . ?
N2 C20 C19 N1 -14.7(5) . . . . ?
C21 C20 C19 N1 165.4(3) . . . . ?
N2 C20 C19 C18 163.6(3) . . . . ?
C21 C20 C19 C18 -16.3(5) . . . . ?
N1 C15 C16 C17 -0.1(6) . . . . ?
N2 C20 C21 C22 -0.6(5) . . . . ?
C19 C20 C21 C22 179.4(3) . . . . ?
C19 C18 C17 C16 -1.0(5) . . . . ?
C15 C16 C17 C18 1.1(6) . . . . ?
N2 C24 C23 C22 -0.8(6) . . . . ?
C24 C23 C22 C21 2.6(6) . . . . ?
C20 C21 C22 C23 -1.9(6) . . . . ?

_refine_diff_density_max         0.932
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.185



