# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_180615_wsf_1
_database_code_depnum_ccdc_archive 'CCDC 2010209'
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_audit_creation_date             2019-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 Cl N O'
_chemical_formula_sum            'C17 H10 Cl N O'
_chemical_formula_weight         279.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o cl'
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'
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                   6.8033(7)
_cell_length_b                   7.2202(5)
_cell_length_c                   13.3326(12)
_cell_angle_alpha                84.038(7)
_cell_angle_beta                 89.246(8)
_cell_angle_gamma                82.696(7)
_cell_volume                     646.09(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2954
_cell_measurement_theta_min      3.3762
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3930
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         3.383
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -69.00   21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -38.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000 -150.0000 83
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0968102000
_diffrn_orient_matrix_UB_12      0.0257688000
_diffrn_orient_matrix_UB_13      0.0028303000
_diffrn_orient_matrix_UB_21      -0.0081643000
_diffrn_orient_matrix_UB_22      -0.0044266000
_diffrn_orient_matrix_UB_23      0.0532635000
_diffrn_orient_matrix_UB_31      0.0401171000
_diffrn_orient_matrix_UB_32      -0.0960782000
_diffrn_orient_matrix_UB_33      0.0040169000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1719
_reflns_number_total             2357
_reflns_odcompleteness_completeness 99.47
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.033
_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)+(0.0632P)²+0.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1264
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.00390(10) 0.86868(9) 0.14182(5) 0.0753(3) Uani 1 1 d . . . . .
O1 O 0.4554(2) 0.77433(17) 0.59233(10) 0.0453(4) Uani 1 1 d . . . . .
N1 N 0.7223(3) 0.6809(2) 0.50037(13) 0.0502(5) Uani 1 1 d . . . . .
C1 C 0.4461(3) 0.7876(3) 0.81998(16) 0.0576(6) Uani 1 1 d . . . . .
H1 H 0.323724 0.825819 0.789148 0.069 Uiso 1 1 calc R . . . .
C2 C 0.4641(4) 0.7853(4) 0.92167(19) 0.0746(8) Uani 1 1 d . . . . .
H2 H 0.353458 0.821631 0.960104 0.089 Uiso 1 1 calc R . . . .
C3 C 0.6467(4) 0.7291(4) 0.96872(19) 0.0792(8) Uani 1 1 d . . . . .
H3 H 0.656385 0.727146 1.038342 0.095 Uiso 1 1 calc R . . . .
C4 C 0.8105(4) 0.6773(3) 0.91431(18) 0.0655(7) Uani 1 1 d . . . . .
H4 H 0.931505 0.642960 0.947022 0.079 Uiso 1 1 calc R . . . .
C5 C 0.8003(3) 0.6745(3) 0.80837(16) 0.0493(5) Uani 1 1 d . . . . .
C6 C 0.6124(3) 0.7323(3) 0.76172(15) 0.0458(5) Uani 1 1 d . . . . .
C7 C 0.6135(3) 0.7265(2) 0.65701(15) 0.0426(5) Uani 1 1 d . . . . .
C8 C 0.7765(3) 0.6698(3) 0.60151(16) 0.0460(5) Uani 1 1 d . . . . .
C9 C 0.9605(3) 0.6114(3) 0.64926(18) 0.0542(6) Uani 1 1 d . . . . .
H9 H 1.072413 0.571020 0.612744 0.065 Uiso 1 1 calc R . . . .
C10 C 0.9685(3) 0.6163(3) 0.75043(18) 0.0557(6) Uani 1 1 d . . . . .
H10 H 1.089296 0.579974 0.783118 0.067 Uiso 1 1 calc R . . . .
C11 C 0.5354(3) 0.7424(3) 0.49954(15) 0.0439(5) Uani 1 1 d . . . . .
C12 C 0.4029(3) 0.7779(2) 0.41283(15) 0.0432(5) Uani 1 1 d . . . . .
C13 C 0.4772(3) 0.7422(3) 0.31809(16) 0.0537(6) Uani 1 1 d . . . . .
H13 H 0.610674 0.698650 0.310670 0.064 Uiso 1 1 calc R . . . .
C14 C 0.3546(4) 0.7709(3) 0.23550(17) 0.0597(6) Uani 1 1 d . . . . .
H14 H 0.404568 0.745912 0.172375 0.072 Uiso 1 1 calc R . . . .
C15 C 0.1580(4) 0.8366(3) 0.24639(16) 0.0514(5) Uani 1 1 d . . . . .
C16 C 0.0802(3) 0.8738(3) 0.33911(17) 0.0537(6) Uani 1 1 d . . . . .
H16 H -0.053332 0.917819 0.345945 0.064 Uiso 1 1 calc R . . . .
C17 C 0.2043(3) 0.8444(3) 0.42144(16) 0.0491(5) Uani 1 1 d . . . . .
H17 H 0.153473 0.869862 0.484332 0.059 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.734(2) . ?
O1 C7 1.374(2) . ?
O1 C11 1.375(2) . ?
N1 C8 1.394(3) . ?
N1 C11 1.292(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.417(3) . ?
C5 C6 1.424(3) . ?
C5 C10 1.416(3) . ?
C6 C7 1.401(3) . ?
C7 C8 1.368(3) . ?
C8 C9 1.408(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.355(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.456(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?
C15 C16 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.376(3) . ?
C17 H17 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
C7 O1 C11 103.62(15) . . ?
C11 N1 C8 104.33(16) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.9(2) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 117.2(2) . . ?
C10 C5 C4 122.0(2) . . ?
C10 C5 C6 120.8(2) . . ?
C1 C6 C5 120.3(2) . . ?
C7 C6 C1 125.6(2) . . ?
C7 C6 C5 114.08(19) . . ?
O1 C7 C6 127.08(18) . . ?
C8 C7 O1 108.09(17) . . ?
C8 C7 C6 124.8(2) . . ?
N1 C8 C9 130.80(19) . . ?
C7 C8 N1 109.02(18) . . ?
C7 C8 C9 120.2(2) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 C8 117.5(2) . . ?
C10 C9 H9 121.3 . . ?
C5 C10 H10 118.7 . . ?
C9 C10 C5 122.6(2) . . ?
C9 C10 H10 118.7 . . ?
O1 C11 C12 117.55(17) . . ?
N1 C11 O1 114.93(19) . . ?
N1 C11 C12 127.51(18) . . ?
C13 C12 C11 119.24(19) . . ?
C17 C12 C11 122.22(18) . . ?
C17 C12 C13 118.5(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.77(19) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 Cl1 119.30(17) . . ?
C14 C15 C16 121.2(2) . . ?
C16 C15 Cl1 119.46(19) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.5(2) . . ?
C17 C16 H16 120.7 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.54(19) . . ?
C16 C17 H17 119.2 . . ?

_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_zyb-1
_database_code_depnum_ccdc_archive 'CCDC 2010211'
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2022-05-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H15 N O'
_chemical_formula_sum            'C23 H15 N O'
_chemical_formula_weight         321.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.962(9)
_cell_length_b                   15.52(3)
_cell_length_c                   17.60(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.36(6)
_cell_angle_gamma                90.00
_cell_volume                     1607(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.35
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strips
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.1264
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13371
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.35
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2221
_reflns_number_total             2816
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0903P)²+0.1421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1595
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H17(0.039) H12(0.046) H11(0.042) H13(0.045) H14(0.039) H23(0.042)
 H5(0.045) H22(0.047) H2(0.055) H1(0.049) H19(0.05) H21(0.053) H3(0.054)
 H4(0.052) H20(0.057)
 Fixed X: H17(0.4373) H12(-0.1245) H11(0.215) H13(-0.3374) H14(-0.2048) H23(-
 0.0197) H5(1.1019) H22(-0.2154) H2(1.1044) H1(0.8028) H19(0.0915) H21(-0.2589)
 H3(1.4068) H4(1.4046) H20(-0.1008)
 Fixed Y: H17(0.1979) H12(0.1036) H11(0.0518) H13(0.1978) H14(0.2442)
 H23(0.1994) H5(0.0031) H22(0.3007) H2(-0.1832) H1(-0.0902) H19(0.3734)
 H21(0.4392) H3(-0.1813) H4(-0.0882) H20(0.4748)
 Fixed Z: H17(0.4598) H12(0.0948) H11(0.1576) H13(0.1567) H14(0.2782)
 H23(0.4941) H5(0.4447) H22(0.5525) H2(0.2406) H1(0.2411) H19(0.3369)
 H21(0.5028) H3(0.3404) H4(0.4423) H20(0.3967)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56844(19) 0.02997(7) 0.28146(7) 0.0317(4) Uani 1 1 d . . .
N1 N 0.7029(2) 0.07437(9) 0.40157(9) 0.0336(4) Uani 1 1 d . . .
C15 C 0.0934(3) 0.17903(11) 0.29496(10) 0.0299(4) Uani 1 1 d . . .
C10 C 0.2182(3) 0.11841(11) 0.25731(10) 0.0299(5) Uani 1 1 d . . .
C17 C 0.3812(3) 0.17856(11) 0.41033(11) 0.0326(5) Uani 1 1 d . . .
H17 H 0.4373 0.1979 0.4598 0.039 Uiso 1 1 calc R . .
C9 C 0.4208(3) 0.08982(11) 0.30174(11) 0.0296(4) Uani 1 1 d . . .
C8 C 0.5015(3) 0.11696(11) 0.37435(10) 0.0302(4) Uani 1 1 d . . .
C12 C -0.0704(3) 0.12114(12) 0.14496(11) 0.0383(5) Uani 1 1 d . . .
H12 H -0.1245 0.1036 0.0948 0.046 Uiso 1 1 calc R . .
C18 C 0.0549(3) 0.27491(11) 0.40888(10) 0.0312(4) Uani 1 1 d . . .
C6 C 0.9217(3) -0.03431(11) 0.34326(11) 0.0328(5) Uani 1 1 d . . .
C11 C 0.1326(3) 0.09088(12) 0.18213(11) 0.0347(5) Uani 1 1 d . . .
H11 H 0.2150 0.0518 0.1576 0.042 Uiso 1 1 calc R . .
C7 C 0.7342(3) 0.02476(11) 0.34548(11) 0.0315(4) Uani 1 1 d . . .
C13 C -0.1973(3) 0.17841(12) 0.18190(11) 0.0372(5) Uani 1 1 d . . .
H13 H -0.3374 0.1978 0.1567 0.045 Uiso 1 1 calc R . .
C14 C -0.1173(3) 0.20615(11) 0.25460(11) 0.0329(5) Uani 1 1 d . . .
H14 H -0.2048 0.2442 0.2782 0.039 Uiso 1 1 calc R . .
C16 C 0.1813(3) 0.20933(11) 0.37144(10) 0.0303(4) Uani 1 1 d . . .
C23 C -0.0370(3) 0.25475(12) 0.47387(11) 0.0349(5) Uani 1 1 d . . .
H23 H -0.0197 0.1994 0.4941 0.042 Uiso 1 1 calc R . .
C5 C 1.1023(3) -0.03409(12) 0.40328(12) 0.0376(5) Uani 1 1 d . . .
H5 H 1.1019 0.0031 0.4447 0.045 Uiso 1 1 calc R . .
C22 C -0.1536(3) 0.31529(13) 0.50900(11) 0.0393(5) Uani 1 1 d . . .
H22 H -0.2154 0.3007 0.5525 0.047 Uiso 1 1 calc R . .
C2 C 1.1042(3) -0.14522(13) 0.28142(13) 0.0460(6) Uani 1 1 d . . .
H2 H 1.1044 -0.1832 0.2406 0.055 Uiso 1 1 calc R . .
C1 C 0.9234(3) -0.09003(12) 0.28188(12) 0.0406(5) Uani 1 1 d . . .
H1 H 0.8028 -0.0902 0.2411 0.049 Uiso 1 1 calc R . .
C19 C 0.0299(3) 0.35838(12) 0.38031(12) 0.0414(5) Uani 1 1 d . . .
H19 H 0.0915 0.3734 0.3369 0.050 Uiso 1 1 calc R . .
C21 C -0.1790(3) 0.39813(13) 0.47954(12) 0.0439(5) Uani 1 1 d . . .
H21 H -0.2589 0.4392 0.5028 0.053 Uiso 1 1 calc R . .
C3 C 1.2843(3) -0.14438(12) 0.34112(13) 0.0452(6) Uani 1 1 d . . .
H3 H 1.4068 -0.1813 0.3404 0.054 Uiso 1 1 calc R . .
C4 C 1.2827(3) -0.08875(13) 0.40190(13) 0.0433(5) Uani 1 1 d . . .
H4 H 1.4046 -0.0882 0.4423 0.052 Uiso 1 1 calc R . .
C20 C -0.0859(4) 0.41893(13) 0.41611(13) 0.0475(6) Uani 1 1 d . . .
H20 H -0.1008 0.4748 0.3967 0.057 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.366(3) . ?
O1 C7 1.375(3) . ?
N1 C8 1.386(3) . ?
N1 C7 1.289(3) . ?
C15 C10 1.428(3) . ?
C15 C14 1.403(3) . ?
C15 C16 1.441(3) . ?
C10 C9 1.400(3) . ?
C10 C11 1.405(3) . ?
C17 H17 0.9300 . ?
C17 C8 1.406(3) . ?
C17 C16 1.361(3) . ?
C9 C8 1.357(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.362(3) . ?
C12 C13 1.395(3) . ?
C18 C16 1.483(3) . ?
C18 C23 1.382(3) . ?
C18 C19 1.389(3) . ?
C6 C7 1.451(3) . ?
C6 C5 1.381(3) . ?
C6 C1 1.385(3) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.361(3) . ?
C14 H14 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.373(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.385(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.378(3) . ?
C2 C3 1.375(3) . ?
C1 H1 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.378(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C20 H20 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
C9 O1 C7 103.51(16) . . ?
C7 N1 C8 104.20(18) . . ?
C10 C15 C16 120.71(17) . . ?
C14 C15 C10 116.99(19) . . ?
C14 C15 C16 122.30(18) . . ?
C9 C10 C15 114.65(19) . . ?
C9 C10 C11 125.30(19) . . ?
C11 C10 C15 120.04(18) . . ?
C8 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C8 118.77(19) . . ?
O1 C9 C10 127.12(18) . . ?
C8 C9 O1 108.19(17) . . ?
C8 C9 C10 124.68(18) . . ?
N1 C8 C17 130.18(18) . . ?
C9 C8 N1 109.39(17) . . ?
C9 C8 C17 120.43(17) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C23 C18 C16 120.72(18) . . ?
C23 C18 C19 118.50(17) . . ?
C19 C18 C16 120.77(19) . . ?
C5 C6 C7 119.10(19) . . ?
C5 C6 C1 119.64(19) . . ?
C1 C6 C7 121.26(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.38(19) . . ?
C12 C11 H11 119.8 . . ?
O1 C7 C6 117.98(18) . . ?
N1 C7 O1 114.71(18) . . ?
N1 C7 C6 127.31(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.43(19) . . ?
C14 C13 H13 119.8 . . ?
C15 C14 H14 119.0 . . ?
C13 C14 C15 121.94(19) . . ?
C13 C14 H14 119.0 . . ?
C15 C16 C18 120.34(17) . . ?
C17 C16 C15 120.71(18) . . ?
C17 C16 C18 118.95(18) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 120.0 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C22 C21 H21 120.3 . . ?
C20 C21 C22 119.45(18) . . ?
C20 C21 H21 120.3 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?

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
O1 C9 C8 N1 -0.1(2) . . . . ?
O1 C9 C8 C17 -179.43(14) . . . . ?
C15 C10 C9 O1 177.44(15) . . . . ?
C15 C10 C9 C8 -1.3(3) . . . . ?
C15 C10 C11 C12 -0.6(3) . . . . ?
C10 C15 C14 C13 -2.0(3) . . . . ?
C10 C15 C16 C17 -2.3(3) . . . . ?
C10 C15 C16 C18 177.55(15) . . . . ?
C10 C9 C8 N1 178.86(15) . . . . ?
C10 C9 C8 C17 -0.5(3) . . . . ?
C9 O1 C7 N1 0.04(19) . . . . ?
C9 O1 C7 C6 -179.95(14) . . . . ?
C9 C10 C11 C12 178.02(16) . . . . ?
C8 N1 C7 O1 -0.1(2) . . . . ?
C8 N1 C7 C6 179.90(16) . . . . ?
C8 C17 C16 C15 0.4(3) . . . . ?
C8 C17 C16 C18 -179.43(16) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C18 C23 C22 C21 -0.4(3) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C11 C10 C9 O1 -1.2(3) . . . . ?
C11 C10 C9 C8 -179.98(17) . . . . ?
C11 C12 C13 C14 1.6(3) . . . . ?
C7 O1 C9 C10 -178.89(17) . . . . ?
C7 O1 C9 C8 0.03(17) . . . . ?
C7 N1 C8 C17 179.36(18) . . . . ?
C7 N1 C8 C9 0.1(2) . . . . ?
C7 C6 C5 C4 -179.22(16) . . . . ?
C7 C6 C1 C2 179.86(17) . . . . ?
C13 C12 C11 C10 -1.3(3) . . . . ?
C14 C15 C10 C9 -176.53(15) . . . . ?
C14 C15 C10 C11 2.2(2) . . . . ?
C14 C15 C16 C17 176.84(16) . . . . ?
C14 C15 C16 C18 -3.3(3) . . . . ?
C16 C15 C10 C9 2.6(2) . . . . ?
C16 C15 C10 C11 -178.65(16) . . . . ?
C16 C15 C14 C13 178.83(16) . . . . ?
C16 C17 C8 N1 -178.21(17) . . . . ?
C16 C17 C8 C9 1.0(3) . . . . ?
C16 C18 C23 C22 179.78(16) . . . . ?
C16 C18 C19 C20 -179.34(17) . . . . ?
C23 C18 C16 C15 114.5(2) . . . . ?
C23 C18 C16 C17 -65.6(2) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
C23 C22 C21 C20 -0.6(3) . . . . ?
C5 C6 C7 O1 173.10(15) . . . . ?
C5 C6 C7 N1 -6.9(3) . . . . ?
C5 C6 C1 C2 0.5(3) . . . . ?
C22 C21 C20 C19 1.0(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C1 C6 C7 O1 -6.2(2) . . . . ?
C1 C6 C7 N1 173.76(18) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C19 C18 C16 C15 -66.7(2) . . . . ?
C19 C18 C16 C17 113.1(2) . . . . ?
C19 C18 C23 C22 1.0(3) . . . . ?
C3 C2 C1 C6 -0.9(3) . . . . ?

