# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2282774'
loop_
_audit_author_name
_audit_author_address
'Baihui Zheng'
;Northeast Normal University
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-31
_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         'C12 H10 Cl2 N2'
_chemical_formula_sum            'C12 H10 Cl2 N2'
_chemical_formula_weight         253.12
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   7.8855(7)
_cell_length_b                   13.1039(9)
_cell_length_c                   11.2372(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1161.15(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    530
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5190
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.726
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.275
_diffrn_reflns_theta_min         3.519
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.762
_reflns_Friedel_fraction_max     0.579
_reflns_number_gt                1831
_reflns_number_total             2293
_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+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 614 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.062
_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)+(0.0360P)²+0.1660P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0934
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C9(H9)
;
_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
Cl1 Cl 0.06379(14) 0.28085(7) 0.61650(11) 0.0533(3) Uani 1 1 d . . . . .
Cl2 Cl 0.20369(14) 0.21084(7) 0.36700(10) 0.0572(3) Uani 1 1 d . . . . .
C1 C 0.1169(4) -0.0541(3) 0.5313(3) 0.0351(8) Uani 1 1 d . . . . .
N1 N 0.1935(4) -0.1957(2) 0.4057(3) 0.0479(9) Uani 1 1 d . . . . .
C3 C 0.1646(5) 0.0189(3) 0.4481(4) 0.0394(9) Uani 1 1 d . . . . .
H3 H 0.2092 -0.0013 0.3752 0.047 Uiso 1 1 calc R . . . .
C4 C 0.1460(4) 0.1215(3) 0.4735(4) 0.0372(9) Uani 1 1 d . . . . .
C5 C 0.0805(4) 0.1525(3) 0.5829(4) 0.0384(9) Uani 1 1 d . . . . .
C6 C 0.0868(6) -0.2451(3) 0.5930(4) 0.0511(11) Uani 1 1 d . . . . .
H6A H -0.0341 -0.2435 0.6089 0.061 Uiso 1 1 calc R . . . .
H6B H 0.1478 -0.2373 0.6674 0.061 Uiso 1 1 calc R . . . .
C7 C 0.0303(5) 0.0810(3) 0.6647(4) 0.0459(10) Uani 1 1 d . . . . .
H7 H -0.0164 0.1015 0.7369 0.055 Uiso 1 1 calc R . . . .
C8 C 0.1363(4) -0.1638(3) 0.5054(4) 0.0389(9) Uani 1 1 d . . . . .
C9 C 0.0495(4) -0.0222(3) 0.6393(4) 0.0433(10) Uani 1 1 d . . . . .
H9 H 0.0168 -0.0705 0.6954 0.052 Uiso 1 1 calc R . . . .
C10 C 0.1951(6) -0.3083(3) 0.4057(5) 0.0563(12) Uani 1 1 d . . . . .
H10A H 0.3084 -0.3332 0.3889 0.068 Uiso 1 1 calc R . . . .
H10B H 0.1187 -0.3342 0.3451 0.068 Uiso 1 1 calc R . . . .
C11 C 0.1374(6) -0.3443(3) 0.5298(5) 0.0566(12) Uani 1 1 d . . . . .
H11 H 0.2356 -0.3733 0.5712 0.068 Uiso 1 1 calc R . . . .
C12 C -0.0024(7) -0.4235(4) 0.5284(6) 0.0757(15) Uani 1 1 d . . . . .
H12A H -0.0988 -0.3967 0.4849 0.091 Uiso 1 1 calc R . . . .
H12B H 0.0375 -0.4838 0.4870 0.091 Uiso 1 1 calc R . . . .
C14 C -0.0563(7) -0.4519(4) 0.6472(7) 0.0781(17) Uani 1 1 d . . . . .
N2 N -0.1018(8) -0.4706(4) 0.7406(6) 0.1034(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.728(4) . ?
Cl2 C4 1.735(4) . ?
C1 C3 1.390(5) . ?
C1 C8 1.475(5) . ?
C1 C9 1.390(6) . ?
N1 C8 1.278(5) . ?
N1 C10 1.475(5) . ?
C3 C4 1.382(5) . ?
C4 C5 1.394(5) . ?
C5 C7 1.371(6) . ?
C6 C8 1.502(6) . ?
C6 C11 1.533(6) . ?
C7 C9 1.391(5) . ?
C10 C11 1.541(7) . ?
C11 C12 1.514(6) . ?
C12 C14 1.449(9) . ?
C14 N2 1.136(8) . ?

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
C3 C1 C8 120.7(3) . . ?
C9 C1 C3 118.9(3) . . ?
C9 C1 C8 120.4(3) . . ?
C8 N1 C10 109.3(3) . . ?
C4 C3 C1 120.1(4) . . ?
C3 C4 Cl2 119.1(3) . . ?
C3 C4 C5 120.4(4) . . ?
C5 C4 Cl2 120.5(3) . . ?
C4 C5 Cl1 120.3(3) . . ?
C7 C5 Cl1 119.7(3) . . ?
C7 C5 C4 119.9(4) . . ?
C8 C6 C11 103.3(4) . . ?
C5 C7 C9 119.7(4) . . ?
C1 C8 C6 122.3(3) . . ?
N1 C8 C1 121.9(4) . . ?
N1 C8 C6 115.7(3) . . ?
C1 C9 C7 120.9(4) . . ?
N1 C10 C11 107.7(3) . . ?
C6 C11 C10 103.7(3) . . ?
C12 C11 C6 113.3(4) . . ?
C12 C11 C10 114.5(4) . . ?
C14 C12 C11 112.4(5) . . ?
N2 C14 C12 177.3(7) . . ?

_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_20220718-02-lyy_auto
_database_code_depnum_ccdc_archive 'CCDC 2282777'
loop_
_audit_author_name
_audit_author_address
'Baihui Zheng'
;Northeast Normal University
China
;
_audit_update_record             
;
2023-07-19 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_audit_creation_date             2023-05-31
_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 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_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      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                   5.5922(6)
_cell_length_b                   6.7269(13)
_cell_length_c                   17.374(3)
_cell_angle_alpha                87.781(16)
_cell_angle_beta                 85.060(12)
_cell_angle_gamma                70.579(14)
_cell_volume                     614.08(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0911
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4360
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.293
_diffrn_reflns_theta_min         3.408
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -39.00   1.00    2.50    --   -9.76-178.00  60.00   60
  2  ω    -15.00  82.00   1.00    2.50    --   10.85  57.00  60.00   97
  3  ω    -57.00  35.00   1.00    2.50    --   10.85 -57.00 -90.00   92
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0032839000
_diffrn_orient_matrix_UB_12      -0.0923112000
_diffrn_orient_matrix_UB_13      0.0205847000
_diffrn_orient_matrix_UB_21      0.0362853000
_diffrn_orient_matrix_UB_22      -0.0581409000
_diffrn_orient_matrix_UB_23      -0.0347513000
_diffrn_orient_matrix_UB_31      0.1298848000
_diffrn_orient_matrix_UB_32      -0.0244881000
_diffrn_orient_matrix_UB_33      0.0069212000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1190
_reflns_number_total             2774
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_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         0.157
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1865
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.066
_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)+(0.0500P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1741
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 -0.0120(5) 0.1014(5) 0.34387(18) 0.0516(8) Uani 1 1 d . . . . .
C2 C -0.2357(5) 0.4461(5) 0.29437(18) 0.0524(8) Uani 1 1 d . . . . .
H2 H -0.3843 0.5613 0.2931 0.063 Uiso 1 1 calc R . . . .
C3 C -0.2326(5) 0.2739(5) 0.33986(19) 0.0549(9) Uani 1 1 d . . . . .
H3 H -0.3806 0.2727 0.3684 0.066 Uiso 1 1 calc R . . . .
C4 C -0.0174(5) 0.4489(5) 0.25020(17) 0.0471(8) Uani 1 1 d . . . . .
C5 C 0.2034(5) 0.2784(5) 0.25465(18) 0.0521(8) Uani 1 1 d . . . . .
H5 H 0.3510 0.2789 0.2256 0.063 Uiso 1 1 calc R . . . .
N2 N -0.1786(4) 0.8148(4) 0.21034(16) 0.0587(8) Uani 1 1 d . . . . .
C7 C -0.0223(5) 0.6288(5) 0.19831(18) 0.0485(8) Uani 1 1 d . . . . .
O2 O -0.2291(4) -0.0758(3) 0.42600(14) 0.0762(7) Uani 1 1 d . . . . .
C9 C 0.2068(5) 0.1075(5) 0.30179(19) 0.0557(9) Uani 1 1 d . . . . .
H9 H 0.3576 -0.0045 0.3052 0.067 Uiso 1 1 calc R . . . .
C10 C -0.0054(6) -0.0908(5) 0.3899(2) 0.0617(9) Uani 1 1 d . . . . .
O1 O 0.1800(4) -0.2453(4) 0.39204(18) 0.0977(10) Uani 1 1 d . . . . .
C12 C 0.1572(5) 0.6086(5) 0.12785(18) 0.0499(8) Uani 1 1 d . . . . .
C13 C 0.2280(6) 0.4251(6) 0.0798(2) 0.0649(10) Uani 1 1 d . . . . .
C14 C -0.1448(6) 0.9543(5) 0.1467(2) 0.0678(10) Uani 1 1 d . . . . .
H14A H -0.1183 1.0774 0.1667 0.081 Uiso 1 1 calc R . . . .
H14B H -0.2949 1.0009 0.1178 0.081 Uiso 1 1 calc R . . . .
C15 C 0.3294(6) 0.7407(5) 0.1304(2) 0.0678(10) Uani 1 1 d . . . . .
H15A H 0.3441 0.7948 0.1801 0.081 Uiso 1 1 calc R . . . .
H15B H 0.4839 0.7024 0.0962 0.081 Uiso 1 1 calc R . . . .
C16 C 0.0852(6) 0.8309(5) 0.0950(2) 0.0629(9) Uani 1 1 d . . . . .
H16 H 0.0848 0.8529 0.0390 0.075 Uiso 1 1 calc R . . . .
N1 N 0.2818(6) 0.2807(5) 0.0412(2) 0.0909(11) Uani 1 1 d . . . . .
C18 C -0.2450(7) -0.2571(6) 0.4713(2) 0.0849(12) Uani 1 1 d . . . . .
H18A H -0.1613 -0.3832 0.4423 0.127 Uiso 1 1 calc GR . . . .
H18B H -0.4204 -0.2439 0.4834 0.127 Uiso 1 1 calc GR . . . .
H18C H -0.1639 -0.2643 0.5184 0.127 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 C3 1.389(4) . ?
C1 C9 1.382(4) . ?
C1 C10 1.485(4) . ?
C2 C3 1.373(4) . ?
C2 C4 1.390(4) . ?
C4 C5 1.383(4) . ?
C4 C7 1.475(4) . ?
C5 C9 1.381(4) . ?
N2 C7 1.279(3) . ?
N2 C14 1.463(4) . ?
C7 C12 1.495(4) . ?
O2 C10 1.325(3) . ?
O2 C18 1.449(4) . ?
C10 O1 1.202(4) . ?
C12 C13 1.440(4) . ?
C12 C15 1.516(4) . ?
C12 C16 1.515(4) . ?
C13 N1 1.143(4) . ?
C14 C16 1.516(4) . ?
C15 C16 1.475(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C10 122.3(3) . . ?
C9 C1 C3 118.6(3) . . ?
C9 C1 C10 119.1(3) . . ?
C3 C2 C4 120.2(3) . . ?
C2 C3 C1 121.1(3) . . ?
C2 C4 C7 120.6(3) . . ?
C5 C4 C2 118.9(3) . . ?
C5 C4 C7 120.5(3) . . ?
C9 C5 C4 120.6(3) . . ?
C7 N2 C14 109.5(3) . . ?
C4 C7 C12 122.6(3) . . ?
N2 C7 C4 122.7(3) . . ?
N2 C7 C12 114.6(3) . . ?
C10 O2 C18 117.0(3) . . ?
C5 C9 C1 120.6(3) . . ?
O2 C10 C1 112.5(3) . . ?
O1 C10 C1 123.8(3) . . ?
O1 C10 O2 123.7(3) . . ?
C7 C12 C15 113.5(3) . . ?
C7 C12 C16 103.6(2) . . ?
C13 C12 C7 120.9(2) . . ?
C13 C12 C15 121.1(2) . . ?
C13 C12 C16 122.7(3) . . ?
C16 C12 C15 58.22(19) . . ?
N1 C13 C12 179.2(4) . . ?
N2 C14 C16 107.6(3) . . ?
C16 C15 C12 60.9(2) . . ?
C12 C16 C14 104.2(3) . . ?
C15 C16 C12 60.9(2) . . ?
C15 C16 C14 117.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.914
