# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2222087'
loop_
_audit_author_name
_audit_author_address
Zhou-a
;zhouch
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-05-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_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'

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

_cell_length_a                   8.7405(15)
_cell_length_b                   8.9958(14)
_cell_length_c                   9.1291(18)
_cell_angle_alpha                107.326(7)
_cell_angle_beta                 99.505(7)
_cell_angle_gamma                97.845(7)
_cell_volume                     662.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3262
_cell_measurement_temperature    273.15
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.34
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13541
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.394
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2188
_reflns_number_total             2946
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.101(18)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.073
_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)+(0.0955P)²+0.0359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1712
_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 Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C00B(H00C), C00D(H00D), C00F(H00F), C00H(H00I), C00I(H00J),
 C00J(H00K)
2.c Idealised Me refined as rotating group:
 C00G(H00E,H00G,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C001 C 0.46561(15) 0.70122(16) 0.45639(16) 0.0514(3) Uani 1 1 d . . . . .
C002 C 0.30070(14) 0.67962(15) 0.41161(16) 0.0498(3) Uani 1 1 d . . . . .
C003 C 0.21509(14) 0.77707(15) 0.52941(16) 0.0532(4) Uani 1 1 d . . . . .
C004 C 0.21756(15) 0.57393(17) 0.26802(17) 0.0558(4) Uani 1 1 d . . . . .
H004 H 0.108080 0.561940 0.242309 0.067 Uiso 1 1 calc R U . . .
C005 C 0.18456(16) 0.69310(16) 0.64203(18) 0.0606(4) Uani 1 1 d . . . . .
N006 N 0.16159(19) 0.63071(19) 0.7298(2) 0.0875(5) Uani 1 1 d . . . . .
C007 C 0.55341(16) 0.81758(17) 0.60798(17) 0.0554(4) Uani 1 1 d . . . . .
N008 N -0.05754(16) 0.80625(18) 0.3852(2) 0.0875(5) Uani 1 1 d . . . . .
C009 C 0.48133(17) 0.93820(17) 0.68799(18) 0.0599(4) Uani 1 1 d . . . . .
C00A C 0.31530(17) 0.94452(16) 0.61768(19) 0.0612(4) Uani 1 1 d . . . . .
H00A H 0.318287 1.004582 0.545489 0.073 Uiso 1 1 calc R U . . .
H00B H 0.266242 0.999093 0.700575 0.073 Uiso 1 1 calc R U . . .
C00B C 0.54078(16) 0.61104(18) 0.34744(18) 0.0604(4) Uani 1 1 d . . . . .
H00C H 0.650287 0.622862 0.372186 0.072 Uiso 1 1 calc R U . . .
C00C C 0.29368(17) 0.48497(18) 0.16093(17) 0.0610(4) Uani 1 1 d . . . . .
C00D C 0.45758(17) 0.50598(18) 0.20558(19) 0.0643(4) Uani 1 1 d . . . . .
H00D H 0.511815 0.447067 0.137172 0.077 Uiso 1 1 calc R U . . .
C00E C 0.05969(17) 0.79128(17) 0.4471(2) 0.0656(4) Uani 1 1 d . . . . .
C00F C 0.71028(18) 0.8170(2) 0.6728(2) 0.0706(4) Uani 1 1 d . . . . .
H00F H 0.758820 0.735811 0.623972 0.085 Uiso 1 1 calc R U . . .
C00G C 0.2025(2) 0.3732(2) 0.0043(2) 0.0833(5) Uani 1 1 d . . . . .
H00E H 0.095431 0.339683 0.010836 0.125 Uiso 1 1 calc R U . . .
H00G H 0.250687 0.282181 -0.025554 0.125 Uiso 1 1 calc R U . . .
H00H H 0.202714 0.426010 -0.072868 0.125 Uiso 1 1 calc R U . . .
C00H C 0.5665(2) 1.0545(2) 0.8253(2) 0.0816(5) Uani 1 1 d . . . . .
H00I H 0.518329 1.133895 0.878217 0.098 Uiso 1 1 calc R U . . .
C00I C 0.7221(3) 1.0538(3) 0.8845(2) 0.0963(6) Uani 1 1 d . . . . .
H00J H 0.778852 1.133416 0.975826 0.116 Uiso 1 1 calc R U . . .
C00J C 0.7931(2) 0.9354(3) 0.8081(2) 0.0906(6) Uani 1 1 d . . . . .
H00K H 0.898000 0.935195 0.848221 0.109 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
C001 C002 1.4015(18) . ?
C001 C007 1.472(2) . ?
C001 C00B 1.400(2) . ?
C002 C003 1.5389(17) . ?
C002 C004 1.380(2) . ?
C003 C005 1.4822(19) . ?
C003 C00A 1.5392(19) . ?
C003 C00E 1.4810(19) . ?
C004 H004 0.9300 . ?
C004 C00C 1.390(2) . ?
C005 N006 1.135(2) . ?
C007 C009 1.405(2) . ?
C007 C00F 1.402(2) . ?
N008 C00E 1.131(2) . ?
C009 C00A 1.503(2) . ?
C009 C00H 1.385(2) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00B H00C 0.9300 . ?
C00B C00D 1.368(2) . ?
C00C C00D 1.393(2) . ?
C00C C00G 1.497(2) . ?
C00D H00D 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00J 1.377(3) . ?
C00G H00E 0.9600 . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00H H00I 0.9300 . ?
C00H C00I 1.379(3) . ?
C00I H00J 0.9300 . ?
C00I C00J 1.373(3) . ?
C00J H00K 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C002 C001 C007 120.93(13) . . ?
C00B C001 C002 116.45(13) . . ?
C00B C001 C007 122.59(13) . . ?
C001 C002 C003 117.49(12) . . ?
C004 C002 C001 121.45(12) . . ?
C004 C002 C003 121.06(11) . . ?
C002 C003 C00A 110.56(10) . . ?
C005 C003 C002 109.09(10) . . ?
C005 C003 C00A 110.29(12) . . ?
C00E C003 C002 110.54(11) . . ?
C00E C003 C005 107.29(11) . . ?
C00E C003 C00A 109.01(11) . . ?
C002 C004 H004 119.2 . . ?
C002 C004 C00C 121.52(13) . . ?
C00C C004 H004 119.2 . . ?
N006 C005 C003 179.08(15) . . ?
C009 C007 C001 119.42(13) . . ?
C00F C007 C001 122.19(14) . . ?
C00F C007 C009 118.33(14) . . ?
C007 C009 C00A 119.21(13) . . ?
C00H C009 C007 119.86(16) . . ?
C00H C009 C00A 120.83(16) . . ?
C003 C00A H00A 109.3 . . ?
C003 C00A H00B 109.3 . . ?
C009 C00A C003 111.58(11) . . ?
C009 C00A H00A 109.3 . . ?
C009 C00A H00B 109.3 . . ?
H00A C00A H00B 108.0 . . ?
C001 C00B H00C 119.1 . . ?
C00D C00B C001 121.80(13) . . ?
C00D C00B H00C 119.1 . . ?
C004 C00C C00D 117.06(14) . . ?
C004 C00C C00G 120.98(14) . . ?
C00D C00C C00G 121.95(14) . . ?
C00B C00D C00C 121.71(13) . . ?
C00B C00D H00D 119.1 . . ?
C00C C00D H00D 119.1 . . ?
N008 C00E C003 178.20(16) . . ?
C007 C00F H00F 119.7 . . ?
C00J C00F C007 120.60(18) . . ?
C00J C00F H00F 119.7 . . ?
C00C C00G H00E 109.5 . . ?
C00C C00G H00G 109.5 . . ?
C00C C00G H00H 109.5 . . ?
H00E C00G H00G 109.5 . . ?
H00E C00G H00H 109.5 . . ?
H00G C00G H00H 109.5 . . ?
C009 C00H H00I 119.6 . . ?
C00I C00H C009 120.7(2) . . ?
C00I C00H H00I 119.6 . . ?
C00H C00I H00J 120.1 . . ?
C00J C00I C00H 119.86(18) . . ?
C00J C00I H00J 120.1 . . ?
C00F C00J H00K 119.7 . . ?
C00I C00J C00F 120.59(18) . . ?
C00I C00J H00K 119.7 . . ?

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
C001 C002 C003 C005 -84.60(14) . . . . ?
C001 C002 C003 C00A 36.85(16) . . . . ?
C001 C002 C003 C00E 157.66(12) . . . . ?
C001 C002 C004 C00C -0.4(2) . . . . ?
C001 C007 C009 C00A 0.68(19) . . . . ?
C001 C007 C009 C00H -175.67(13) . . . . ?
C001 C007 C00F C00J 174.54(14) . . . . ?
C001 C00B C00D C00C 1.0(2) . . . . ?
C002 C001 C007 C009 -18.15(19) . . . . ?
C002 C001 C007 C00F 164.81(12) . . . . ?
C002 C001 C00B C00D -0.8(2) . . . . ?
C002 C003 C00A C009 -51.57(16) . . . . ?
C002 C004 C00C C00D 0.6(2) . . . . ?
C002 C004 C00C C00G -178.75(13) . . . . ?
C003 C002 C004 C00C -179.81(12) . . . . ?
C004 C002 C003 C005 94.78(14) . . . . ?
C004 C002 C003 C00A -143.77(13) . . . . ?
C004 C002 C003 C00E -22.96(16) . . . . ?
C004 C00C C00D C00B -0.9(2) . . . . ?
C005 C003 C00A C009 69.17(15) . . . . ?
C007 C001 C002 C003 -2.35(18) . . . . ?
C007 C001 C002 C004 178.27(11) . . . . ?
C007 C001 C00B C00D -178.51(12) . . . . ?
C007 C009 C00A C003 34.34(18) . . . . ?
C007 C009 C00H C00I 0.3(3) . . . . ?
C007 C00F C00J C00I 1.8(3) . . . . ?
C009 C007 C00F C00J -2.5(2) . . . . ?
C009 C00H C00I C00J -1.0(3) . . . . ?
C00A C009 C00H C00I -176.02(16) . . . . ?
C00B C001 C002 C003 179.86(12) . . . . ?
C00B C001 C002 C004 0.48(19) . . . . ?
C00B C001 C007 C009 159.50(13) . . . . ?
C00B C001 C007 C00F -17.5(2) . . . . ?
C00E C003 C00A C009 -173.28(12) . . . . ?
C00F C007 C009 C00A 177.84(12) . . . . ?
C00F C007 C009 C00H 1.5(2) . . . . ?
C00G C00C C00D C00B 178.46(14) . . . . ?
C00H C009 C00A C003 -149.34(14) . . . . ?
C00H C00I C00J C00F 0.0(3) . . . . ?

_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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2222108'
loop_
_audit_author_name
_audit_author_address
Zhou
;z
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 Cl N2'
_chemical_formula_sum            'C16 H9 Cl N2'
_chemical_formula_weight         264.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.437(3)
_cell_length_b                   9.166(3)
_cell_length_c                   9.274(3)
_cell_angle_alpha                108.582(10)
_cell_angle_beta                 99.894(11)
_cell_angle_gamma                94.050(11)
_cell_volume                     663.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4479
_cell_measurement_temperature    297.0
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20898
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.366
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                2246
_reflns_number_total             2997
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.043
_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)+(0.0781P)²+0.0614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1470
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 Cl1-C11 \\sim Cl1A-C11
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Cl1A, Cl1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(Cl1A)=1-FVAR(1)
 Sof(Cl1)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C9(H9), C12(H12), C4(H4), C10(H10), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C15 C 0.14375(17) 0.17109(16) 0.56940(17) 0.0535(4) Uani 1 1 d . . . . .
C2 C 0.27291(18) 0.13768(16) 0.34230(16) 0.0509(3) Uani 1 1 d . . . . .
C8 C 0.52623(17) 0.26702(16) 0.54208(17) 0.0523(4) Uani 1 1 d . . . . .
C1 C 0.17879(17) 0.24227(16) 0.45301(17) 0.0519(4) Uani 1 1 d . . . . .
C7 C 0.44217(17) 0.15296(16) 0.39052(17) 0.0507(3) Uani 1 1 d . . . . .
N2 N 0.11992(18) 0.11860(18) 0.66083(18) 0.0714(4) Uani 1 1 d . . . . .
C13 C 0.44617(18) 0.38967(17) 0.61637(18) 0.0543(4) Uani 1 1 d . . . . .
N1 N -0.0949(2) 0.2852(2) 0.3009(2) 0.0848(5) Uani 1 1 d . . . . .
C16 C 0.0227(2) 0.26347(19) 0.36623(19) 0.0628(4) Uani 1 1 d . . . . .
C6 C 0.5267(2) 0.05629(19) 0.2896(2) 0.0629(4) Uani 1 1 d . . . . .
H6 H 0.639046 0.064173 0.317567 0.075 Uiso 1 1 calc R U . . .
C3 C 0.1935(2) 0.03009(19) 0.20121(18) 0.0622(4) Uani 1 1 d . . . . .
H3 H 0.081261 0.020997 0.171129 0.075 Uiso 1 1 calc R U . . .
C14 C 0.27930(19) 0.40403(17) 0.5391(2) 0.0596(4) Uani 1 1 d . . . . .
H14A H 0.287951 0.457984 0.465601 0.072 Uiso 1 1 calc R U . . .
H14B H 0.224252 0.464856 0.616741 0.072 Uiso 1 1 calc R U . . .
C9 C 0.6834(2) 0.2592(2) 0.6144(2) 0.0633(4) Uani 1 1 d . . . . .
H9 H 0.737490 0.177709 0.567599 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5234(2) 0.5003(2) 0.7572(2) 0.0689(4) Uani 1 1 d . . . . .
H12 H 0.470308 0.581576 0.806349 0.083 Uiso 1 1 calc R U . . .
C4 C 0.2810(3) -0.0636(2) 0.1053(2) 0.0732(5) Uani 1 1 d . . . . .
H4 H 0.227767 -0.135931 0.010483 0.088 Uiso 1 1 calc R U . . .
C10 C 0.7594(2) 0.3690(2) 0.7528(2) 0.0729(5) Uani 1 1 d . . . . .
H10 H 0.864528 0.362568 0.798769 0.087 Uiso 1 1 calc R U . . .
C11 C 0.6790(2) 0.4891(2) 0.8236(2) 0.0737(5) Uani 1 1 d D . . . .
C5 C 0.4462(3) -0.0503(2) 0.1496(2) 0.0724(5) Uani 1 1 d . . . . .
H5 H 0.504671 -0.113745 0.084476 0.087 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7775(4) 0.6353(4) 0.9978(3) 0.1031(9) Uani 0.72(3) 1 d D . P A 1
Cl1A Cl 0.7650(11) 0.6128(19) 1.0043(8) 0.155(5) Uani 0.28(3) 1 d D . P A 2


_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
C15 C1 1.486(2) . ?
C15 N2 1.138(2) . ?
C2 C1 1.5376(19) . ?
C2 C7 1.404(2) . ?
C2 C3 1.384(2) . ?
C8 C7 1.479(2) . ?
C8 C13 1.403(2) . ?
C8 C9 1.397(2) . ?
C1 C16 1.480(2) . ?
C1 C14 1.546(2) . ?
C7 C6 1.400(2) . ?
C13 C14 1.501(2) . ?
C13 C12 1.389(2) . ?
N1 C16 1.135(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.377(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C9 H9 0.9300 . ?
C9 C10 1.369(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C11 Cl1 1.760(3) . ?
C11 Cl1A 1.695(8) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C15 C1 178.46(16) . . ?
C7 C2 C1 117.69(13) . . ?
C3 C2 C1 121.26(13) . . ?
C3 C2 C7 121.04(13) . . ?
C13 C8 C7 118.94(13) . . ?
C9 C8 C7 122.85(13) . . ?
C9 C8 C13 118.20(15) . . ?
C15 C1 C2 110.06(11) . . ?
C15 C1 C14 108.98(12) . . ?
C2 C1 C14 110.27(12) . . ?
C16 C1 C15 108.38(12) . . ?
C16 C1 C2 110.87(12) . . ?
C16 C1 C14 108.23(12) . . ?
C2 C7 C8 120.82(12) . . ?
C6 C7 C2 117.29(15) . . ?
C6 C7 C8 121.89(14) . . ?
C8 C13 C14 119.43(14) . . ?
C12 C13 C8 120.19(15) . . ?
C12 C13 C14 120.33(14) . . ?
N1 C16 C1 177.54(18) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 121.08(16) . . ?
C5 C6 H6 119.5 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.94(16) . . ?
C4 C3 H3 120.0 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C13 C14 C1 110.92(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.42(15) . . ?
C10 C9 H9 119.3 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.71(16) . . ?
C11 C12 H12 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.04(17) . . ?
C5 C4 H4 120.0 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.50(16) . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.99(17) . . ?
C12 C11 Cl1 118.83(17) . . ?
C12 C11 Cl1A 119.4(4) . . ?
C10 C11 Cl1 120.15(16) . . ?
C10 C11 Cl1A 119.2(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.61(15) . . ?
C4 C5 H5 119.7 . . ?

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
C15 C1 C14 C13 68.13(15) . . . . ?
C2 C1 C14 C13 -52.79(17) . . . . ?
C2 C7 C6 C5 -0.6(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C8 C7 C6 C5 179.38(14) . . . . ?
C8 C13 C14 C1 37.04(19) . . . . ?
C8 C13 C12 C11 0.0(2) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C1 C2 C7 C8 -0.56(19) . . . . ?
C1 C2 C7 C6 179.44(13) . . . . ?
C1 C2 C3 C4 -179.10(14) . . . . ?
C7 C2 C1 C15 -84.28(15) . . . . ?
C7 C2 C1 C16 155.83(13) . . . . ?
C7 C2 C1 C14 35.99(17) . . . . ?
C7 C2 C3 C4 -0.3(2) . . . . ?
C7 C8 C13 C14 -1.3(2) . . . . ?
C7 C8 C13 C12 -178.64(13) . . . . ?
C7 C8 C9 C10 178.25(14) . . . . ?
C7 C6 C5 C4 0.3(3) . . . . ?
C13 C8 C7 C2 -18.7(2) . . . . ?
C13 C8 C7 C6 161.34(14) . . . . ?
C13 C8 C9 C10 -1.0(2) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C13 C12 C11 Cl1 177.3(2) . . . . ?
C13 C12 C11 Cl1A -173.4(7) . . . . ?
C16 C1 C14 C13 -174.21(13) . . . . ?
C3 C2 C1 C15 94.54(16) . . . . ?
C3 C2 C1 C16 -25.35(19) . . . . ?
C3 C2 C1 C14 -145.19(14) . . . . ?
C3 C2 C7 C8 -179.38(12) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C14 C13 C12 C11 -177.36(15) . . . . ?
C9 C8 C7 C2 162.05(14) . . . . ?
C9 C8 C7 C6 -18.0(2) . . . . ?
C9 C8 C13 C14 178.07(13) . . . . ?
C9 C8 C13 C12 0.7(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C10 C11 Cl1 -177.6(2) . . . . ?
C9 C10 C11 Cl1A 173.0(7) . . . . ?
C12 C13 C14 C1 -145.59(14) . . . . ?

_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_1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2222106'
loop_
_audit_author_name
_audit_author_address
Zhoub
;zhou
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 N2 O2'
_chemical_formula_sum            'C17 H10 N2 O2'
_chemical_formula_weight         274.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.4260(7)
_cell_length_b                   8.8146(8)
_cell_length_c                   8.9781(6)
_cell_angle_alpha                83.027(3)
_cell_angle_beta                 83.022(3)
_cell_angle_gamma                86.110(4)
_cell_volume                     656.03(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7495
_cell_measurement_temperature    297.0
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            22045
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.300
_diffrn_ambient_temperature      297.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                2627
_reflns_number_total             2994
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.057
_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)+(0.0721P)²+0.0763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1248
_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 Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00L(H00C,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.03166(12) 0.75593(13) 0.09316(12) 0.0720(3) Uani 1 1 d . . . . .
O002 O 0.16846(14) 0.87603(11) 0.24955(12) 0.0728(3) Uani 1 1 d . . . . .
C003 C 0.49257(13) 0.20216(11) 0.24084(11) 0.0372(2) Uani 1 1 d . . . . .
C004 C 0.34657(12) 0.44997(11) 0.15411(11) 0.0364(2) Uani 1 1 d . . . . .
C005 C 0.43333(13) 0.52527(11) 0.24377(11) 0.0361(2) Uani 1 1 d . . . . .
C006 C 0.62167(12) 0.29661(11) 0.28679(11) 0.0367(2) Uani 1 1 d . . . . .
C007 C 0.37409(14) 0.16381(12) 0.37444(12) 0.0434(3) Uani 1 1 d . . . . .
N008 N 0.62727(16) -0.04728(13) 0.14091(14) 0.0660(3) Uani 1 1 d . . . . .
N009 N 0.28297(15) 0.13983(14) 0.47745(13) 0.0631(3) Uani 1 1 d . . . . .
C00A C 0.58705(13) 0.45410(11) 0.28767(11) 0.0360(2) Uani 1 1 d . . . . .
C00B C 0.40734(13) 0.29442(12) 0.11249(11) 0.0390(2) Uani 1 1 d . . . . .
H00A H 0.481622 0.306053 0.020952 0.047 Uiso 1 1 calc R U . . .
H00B H 0.318304 0.238609 0.092570 0.047 Uiso 1 1 calc R U . . .
C00C C 0.56594(15) 0.05866(12) 0.18682(13) 0.0463(3) Uani 1 1 d . . . . .
C00D C 0.20833(14) 0.51951(14) 0.09702(13) 0.0456(3) Uani 1 1 d . . . . .
H00D H 0.151372 0.470508 0.036129 0.055 Uiso 1 1 calc R U . . .
C00E C 0.37773(15) 0.67061(12) 0.28440(12) 0.0444(3) Uani 1 1 d . . . . .
H00E H 0.431187 0.720695 0.347211 0.053 Uiso 1 1 calc R U . . .
C00F C 0.76565(14) 0.22948(14) 0.32793(14) 0.0482(3) Uani 1 1 d . . . . .
H00F H 0.785634 0.124267 0.329520 0.058 Uiso 1 1 calc R U . . .
C00G C 0.70522(15) 0.54177(14) 0.32593(13) 0.0472(3) Uani 1 1 d . . . . .
H00G H 0.686331 0.647004 0.325426 0.057 Uiso 1 1 calc R U . . .
C00H C 0.16103(14) 0.66295(14) 0.13509(13) 0.0494(3) Uani 1 1 d . . . . .
C00I C 0.24264(16) 0.73495(13) 0.22811(13) 0.0491(3) Uani 1 1 d . . . . .
C00J C 0.88001(15) 0.31869(17) 0.36675(15) 0.0571(3) Uani 1 1 d . . . . .
H00J H 0.976836 0.273699 0.394212 0.069 Uiso 1 1 calc R U . . .
C00K C 0.84951(15) 0.47407(16) 0.36443(15) 0.0554(3) Uani 1 1 d . . . . .
H00K H 0.926834 0.534240 0.389040 0.066 Uiso 1 1 calc R U . . .
C00L C 0.0213(2) 0.87692(19) 0.18651(19) 0.0765(5) Uani 1 1 d . . . . .
H00C H 0.001753 0.974388 0.127062 0.092 Uiso 1 1 calc R U . . .
H00H H -0.066520 0.862340 0.266482 0.092 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
O001 C00H 1.3803(14) . ?
O001 C00L 1.426(2) . ?
O002 C00I 1.3775(14) . ?
O002 C00L 1.423(2) . ?
C003 C006 1.5368(14) . ?
C003 C007 1.4853(14) . ?
C003 C00B 1.5490(14) . ?
C003 C00C 1.4790(14) . ?
C004 C005 1.4005(14) . ?
C004 C00B 1.5048(13) . ?
C004 C00D 1.4026(15) . ?
C005 C00A 1.4765(14) . ?
C005 C00E 1.4087(14) . ?
C006 C00A 1.3998(14) . ?
C006 C00F 1.3845(15) . ?
C007 N009 1.1364(15) . ?
N008 C00C 1.1336(15) . ?
C00A C00G 1.3995(15) . ?
C00B H00A 0.9700 . ?
C00B H00B 0.9700 . ?
C00D H00D 0.9300 . ?
C00D C00H 1.3704(16) . ?
C00E H00E 0.9300 . ?
C00E C00I 1.3621(17) . ?
C00F H00F 0.9300 . ?
C00F C00J 1.3854(18) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.3811(18) . ?
C00H C00I 1.3786(19) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.374(2) . ?
C00K H00K 0.9300 . ?
C00L H00C 0.9700 . ?
C00L H00H 0.9700 . ?

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
C00H O001 C00L 104.65(11) . . ?
C00I O002 C00L 104.76(11) . . ?
C006 C003 C00B 110.25(8) . . ?
C007 C003 C006 108.95(8) . . ?
C007 C003 C00B 109.77(9) . . ?
C00C C003 C006 110.19(9) . . ?
C00C C003 C007 109.00(9) . . ?
C00C C003 C00B 108.67(8) . . ?
C005 C004 C00B 119.21(9) . . ?
C005 C004 C00D 121.29(10) . . ?
C00D C004 C00B 119.43(9) . . ?
C004 C005 C00A 119.14(9) . . ?
C004 C005 C00E 119.96(10) . . ?
C00E C005 C00A 120.82(9) . . ?
C00A C006 C003 117.23(9) . . ?
C00F C006 C003 121.81(9) . . ?
C00F C006 C00A 120.95(10) . . ?
N009 C007 C003 177.55(12) . . ?
C006 C00A C005 120.79(9) . . ?
C00G C00A C005 121.46(10) . . ?
C00G C00A C006 117.71(10) . . ?
C003 C00B H00A 109.4 . . ?
C003 C00B H00B 109.4 . . ?
C004 C00B C003 111.16(8) . . ?
C004 C00B H00A 109.4 . . ?
C004 C00B H00B 109.4 . . ?
H00A C00B H00B 108.0 . . ?
N008 C00C C003 176.73(14) . . ?
C004 C00D H00D 121.5 . . ?
C00H C00D C004 116.94(11) . . ?
C00H C00D H00D 121.5 . . ?
C005 C00E H00E 121.3 . . ?
C00I C00E C005 117.41(10) . . ?
C00I C00E H00E 121.3 . . ?
C006 C00F H00F 119.9 . . ?
C006 C00F C00J 120.15(11) . . ?
C00J C00F H00F 119.9 . . ?
C00A C00G H00G 119.6 . . ?
C00K C00G C00A 120.87(11) . . ?
C00K C00G H00G 119.6 . . ?
C00D C00H O001 128.43(12) . . ?
C00D C00H C00I 121.90(11) . . ?
C00I C00H O001 109.67(11) . . ?
O002 C00I C00H 109.85(11) . . ?
C00E C00I O002 127.73(12) . . ?
C00E C00I C00H 122.41(10) . . ?
C00F C00J H00J 120.2 . . ?
C00K C00J C00F 119.60(11) . . ?
C00K C00J H00J 120.2 . . ?
C00G C00K H00K 119.7 . . ?
C00J C00K C00G 120.68(11) . . ?
C00J C00K H00K 119.7 . . ?
O001 C00L H00C 110.0 . . ?
O001 C00L H00H 110.0 . . ?
O002 C00L O001 108.38(11) . . ?
O002 C00L H00C 110.0 . . ?
O002 C00L H00H 110.0 . . ?
H00C C00L H00H 108.4 . . ?

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
O001 C00H C00I O002 0.21(15) . . . . ?
O001 C00H C00I C00E -178.71(11) . . . . ?
C003 C006 C00A C005 -0.90(14) . . . . ?
C003 C006 C00A C00G -178.55(9) . . . . ?
C003 C006 C00F C00J 179.15(10) . . . . ?
C004 C005 C00A C006 -21.62(14) . . . . ?
C004 C005 C00A C00G 155.94(10) . . . . ?
C004 C005 C00E C00I -2.65(16) . . . . ?
C004 C00D C00H O001 179.35(11) . . . . ?
C004 C00D C00H C00I -1.52(18) . . . . ?
C005 C004 C00B C003 33.47(13) . . . . ?
C005 C004 C00D C00H -1.03(16) . . . . ?
C005 C00A C00G C00K -178.95(10) . . . . ?
C005 C00E C00I O002 -178.57(11) . . . . ?
C005 C00E C00I C00H 0.15(18) . . . . ?
C006 C003 C00B C004 -52.56(11) . . . . ?
C006 C00A C00G C00K -1.31(16) . . . . ?
C006 C00F C00J C00K 0.13(19) . . . . ?
C007 C003 C006 C00A -83.05(11) . . . . ?
C007 C003 C006 C00F 96.01(11) . . . . ?
C007 C003 C00B C004 67.46(11) . . . . ?
C00A C005 C00E C00I 174.05(9) . . . . ?
C00A C006 C00F C00J -1.82(17) . . . . ?
C00A C00G C00K C00J -0.32(19) . . . . ?
C00B C003 C006 C00A 37.46(12) . . . . ?
C00B C003 C006 C00F -143.47(10) . . . . ?
C00B C004 C005 C00A 3.56(14) . . . . ?
C00B C004 C005 C00E -179.69(9) . . . . ?
C00B C004 C00D C00H -178.19(9) . . . . ?
C00C C003 C006 C00A 157.40(9) . . . . ?
C00C C003 C006 C00F -23.53(13) . . . . ?
C00C C003 C00B C004 -173.42(9) . . . . ?
C00D C004 C005 C00A -173.60(9) . . . . ?
C00D C004 C005 C00E 3.15(15) . . . . ?
C00D C004 C00B C003 -149.32(10) . . . . ?
C00D C00H C00I O002 -179.07(11) . . . . ?
C00D C00H C00I C00E 2.02(19) . . . . ?
C00E C005 C00A C006 161.65(10) . . . . ?
C00E C005 C00A C00G -20.79(15) . . . . ?
C00F C006 C00A C005 -179.97(9) . . . . ?
C00F C006 C00A C00G 2.38(15) . . . . ?
C00F C00J C00K C00G 0.9(2) . . . . ?
C00H O001 C00L O002 16.09(16) . . . . ?
C00I O002 C00L O001 -15.98(16) . . . . ?
C00L O001 C00H C00D 169.18(13) . . . . ?
C00L O001 C00H C00I -10.04(15) . . . . ?
C00L O002 C00I C00E -171.42(13) . . . . ?
C00L O002 C00I C00H 9.74(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
