# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_d24730
_database_code_depnum_ccdc_archive 'CCDC 2301349'
loop_
_audit_author_name
_audit_author_address
'Lavanya Chandrasekar'
;Fu Jen Catholic University
Taiwan
;
_audit_update_record             
;
2023-10-15 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(1S,1aR,7bR)-1a-(4-chlorobenzoyl)-1-ethynyl-1a,7b-dihydrocyclopropa[c]chromen-2(1H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 Cl O3'
_chemical_formula_sum            'C19 H11 Cl O3'
_chemical_formula_weight         322.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.1577(3)
_cell_length_b                   19.5983(8)
_cell_length_c                   21.4037(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3002.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8129
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      66.80

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    2.363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2810
_exptl_absorpt_correction_T_max  0.8155
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9534
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.51
_diffrn_reflns_theta_max         66.80
_reflns_number_total             2623
_reflns_number_gt                2367
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0787P)²+1.8013P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2623
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1451
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8743(4) 0.62736(13) 0.64006(11) 0.0495(6) Uani 1 1 d . . .
C2 C 0.8523(3) 0.60748(11) 0.57888(11) 0.0443(6) Uani 1 1 d . . .
H2 H 0.9491 0.5837 0.5577 0.053 Uiso 1 1 calc R . .
C3 C 0.6863(3) 0.62272(10) 0.54877(10) 0.0361(5) Uani 1 1 d . . .
H3 H 0.6693 0.6091 0.5066 0.043 Uiso 1 1 calc R . .
C4 C 0.5431(3) 0.65786(10) 0.57946(10) 0.0360(5) Uani 1 1 d . . .
C5 C 0.5712(4) 0.67870(12) 0.64117(11) 0.0473(6) Uani 1 1 d . . .
H5 H 0.4763 0.7035 0.6623 0.057 Uiso 1 1 calc R . .
C6 C 0.7362(4) 0.66344(14) 0.67152(11) 0.0544(7) Uani 1 1 d . . .
H6 H 0.7551 0.6775 0.7135 0.065 Uiso 1 1 calc R . .
C7 C 0.3654(3) 0.67582(10) 0.54807(10) 0.0377(5) Uani 1 1 d . . .
C8 C 0.3207(3) 0.64229(9) 0.48654(9) 0.0325(5) Uani 1 1 d . . .
C9 C 0.3220(3) 0.56625(10) 0.48536(10) 0.0330(5) Uani 1 1 d . . .
C10 C 0.4284(3) 0.56825(11) 0.37822(10) 0.0362(5) Uani 1 1 d . . .
C11 C 0.4854(3) 0.52658(13) 0.32961(11) 0.0471(6) Uani 1 1 d . . .
H11 H 0.4753 0.4784 0.3328 0.056 Uiso 1 1 calc R . .
C12 C 0.5570(3) 0.55642(15) 0.27636(12) 0.0547(7) Uani 1 1 d . . .
H12 H 0.5952 0.5286 0.2424 0.066 Uiso 1 1 calc R . .
C13 C 0.5735(3) 0.62667(16) 0.27210(12) 0.0548(6) Uani 1 1 d . . .
H13 H 0.6243 0.6469 0.2355 0.066 Uiso 1 1 calc R . .
C14 C 0.5161(3) 0.66732(13) 0.32123(11) 0.0458(5) Uani 1 1 d . . .
H14 H 0.5290 0.7155 0.3184 0.055 Uiso 1 1 calc R . .
C15 C 0.4393(3) 0.63848(11) 0.37491(10) 0.0356(5) Uani 1 1 d . . .
C16 C 0.3695(3) 0.68040(10) 0.42707(10) 0.0357(5) Uani 1 1 d . . .
H16 H 0.4300 0.7260 0.4326 0.043 Uiso 1 1 calc R . .
C17 C 0.1675(3) 0.67517(10) 0.44715(10) 0.0373(5) Uani 1 1 d . . .
H17 H 0.1135 0.7180 0.4650 0.045 Uiso 1 1 calc R . .
C18 C 0.0361(3) 0.63244(12) 0.41477(11) 0.0414(5) Uani 1 1 d . . .
C19 C -0.0700(3) 0.59530(15) 0.38980(13) 0.0557(7) Uani 1 1 d . . .
H19 H -0.1554 0.5654 0.3697 0.067 Uiso 1 1 calc R . .
Cl1 Cl 1.07881(11) 0.60566(4) 0.67930(4) 0.0765(3) Uani 1 1 d . . .
O1 O 0.2617(3) 0.71918(8) 0.56940(9) 0.0554(5) Uani 1 1 d . . .
O2 O 0.2819(2) 0.53237(7) 0.52988(7) 0.0425(4) Uani 1 1 d . . .
O3 O 0.3617(2) 0.53423(7) 0.43107(7) 0.0379(4) 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
C1 C2 1.375(3) . ?
C1 C6 1.390(4) . ?
C1 Cl1 1.741(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 C7 1.481(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.217(3) . ?
C7 C8 1.506(3) . ?
C8 C9 1.490(3) . ?
C8 C16 1.517(3) . ?
C8 C17 1.526(3) . ?
C9 O2 1.197(3) . ?
C9 O3 1.351(2) . ?
C10 C15 1.380(3) . ?
C10 C11 1.384(3) . ?
C10 O3 1.397(3) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.474(3) . ?
C16 C17 1.512(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.437(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.180(4) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.6(2) . . ?
C2 C1 Cl1 119.1(2) . . ?
C6 C1 Cl1 119.26(19) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 118.9(2) . . ?
C3 C4 C7 122.23(19) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 C4 121.3(2) . . ?
O1 C7 C8 120.2(2) . . ?
C4 C7 C8 118.37(18) . . ?
C9 C8 C7 116.73(16) . . ?
C9 C8 C16 118.48(17) . . ?
C7 C8 C16 118.03(16) . . ?
C9 C8 C17 114.67(16) . . ?
C7 C8 C17 116.83(17) . . ?
C16 C8 C17 59.61(13) . . ?
O2 C9 O3 118.53(18) . . ?
O2 C9 C8 122.68(19) . . ?
O3 C9 C8 118.72(17) . . ?
C15 C10 C11 122.2(2) . . ?
C15 C10 O3 122.46(18) . . ?
C11 C10 O3 115.33(19) . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 118.0(2) . . ?
C10 C15 C16 119.86(18) . . ?
C14 C15 C16 122.2(2) . . ?
C15 C16 C17 120.11(18) . . ?
C15 C16 C8 116.06(17) . . ?
C17 C16 C8 60.50(13) . . ?
C15 C16 H16 116.2 . . ?
C17 C16 H16 116.2 . . ?
C8 C16 H16 116.2 . . ?
C18 C17 C16 121.89(19) . . ?
C18 C17 C8 119.38(17) . . ?
C16 C17 C8 59.89(13) . . ?
C18 C17 H17 114.9 . . ?
C16 C17 H17 114.9 . . ?
C8 C17 H17 114.9 . . ?
C19 C18 C17 177.3(3) . . ?
C18 C19 H19 180.0 . . ?
C9 O3 C10 123.13(16) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.80
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_d24731
_database_code_depnum_ccdc_archive 'CCDC 2301350'
loop_
_audit_author_name
_audit_author_address
'Lavanya Chandrasekar'
;Fu Jen Catholic University
Taiwan
;
_audit_update_record             
;
2023-10-15 deposited with the CCDC.	2024-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(1R,1aR,7bR)-1a-(4-chlorobenzoyl)-1-ethynyl-1a,7b-dihydrocyclopropa[c]chromen-2(1H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H11 Cl O3'
_chemical_formula_sum            'C19 H11 Cl O3'
_chemical_formula_weight         322.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5190(3)
_cell_length_b                   14.8049(4)
_cell_length_c                   21.6031(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.7470(10)
_cell_angle_gamma                90.00
_cell_volume                     3044.22(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9939
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      66.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3501
_exptl_absorpt_correction_T_max  0.7836
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16059
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         66.54
_reflns_number_total             5295
_reflns_number_gt                4702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1294P)²+12.9416P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5295
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1169
_refine_ls_goodness_of_fit_ref   0.440
_refine_ls_restrained_S_all      0.440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0133(2) 0.06638(15) 0.76044(10) 0.0422(5) Uani 1 1 d . . .
C2 C 0.0706(2) 0.13474(14) 0.72499(10) 0.0411(5) Uani 1 1 d . . .
H2 H 0.0130 0.1685 0.6972 0.049 Uiso 1 1 calc R . .
C3 C 0.2126(2) 0.15337(13) 0.73048(9) 0.0367(4) Uani 1 1 d . . .
H3 H 0.2524 0.2003 0.7064 0.044 Uiso 1 1 calc R . .
C4 C 0.2978(2) 0.10384(13) 0.77108(9) 0.0344(4) Uani 1 1 d . . .
C5 C 0.2376(2) 0.03364(13) 0.80470(9) 0.0373(4) Uani 1 1 d . . .
H5 H 0.2954 -0.0020 0.8313 0.045 Uiso 1 1 calc R . .
C6 C 0.0961(2) 0.01499(14) 0.79998(9) 0.0409(5) Uani 1 1 d . . .
H6 H 0.0561 -0.0324 0.8235 0.049 Uiso 1 1 calc R . .
C7 C 0.4465(2) 0.12735(14) 0.78518(9) 0.0369(4) Uani 1 1 d . . .
C8 C 0.52118(19) 0.19721(13) 0.74623(8) 0.0316(4) Uani 1 1 d . . .
C9 C 0.5474(2) 0.17262(14) 0.68082(9) 0.0354(4) Uani 1 1 d . . .
C10 C 0.7499(2) 0.27241(14) 0.67855(9) 0.0368(4) Uani 1 1 d . . .
C11 C 0.8560(2) 0.30339(15) 0.64097(10) 0.0456(5) Uani 1 1 d . . .
H11 H 0.8538 0.2917 0.5977 0.055 Uiso 1 1 calc R . .
C12 C 0.9654(2) 0.35163(16) 0.66757(12) 0.0521(6) Uani 1 1 d . . .
H12 H 1.0386 0.3742 0.6424 0.062 Uiso 1 1 calc R . .
C13 C 0.9688(2) 0.36726(16) 0.73094(12) 0.0518(6) Uani 1 1 d . . .
H13 H 1.0451 0.3996 0.7491 0.062 Uiso 1 1 calc R . .
C14 C 0.8611(2) 0.33574(15) 0.76761(10) 0.0456(5) Uani 1 1 d . . .
H14 H 0.8639 0.3467 0.8109 0.055 Uiso 1 1 calc R . .
C15 C 0.7487(2) 0.28819(13) 0.74167(9) 0.0362(4) Uani 1 1 d . . .
C16 C 0.6268(2) 0.25886(14) 0.77814(9) 0.0359(4) Uani 1 1 d . . .
H16 H 0.6433 0.2490 0.8234 0.043 Uiso 1 1 calc R . .
C17 C 0.4852(2) 0.29735(13) 0.75886(9) 0.0366(4) Uani 1 1 d . . .
H17 H 0.4862 0.3377 0.7217 0.044 Uiso 1 1 calc R . .
C18 C 0.3804(2) 0.31876(15) 0.80410(10) 0.0435(5) Uani 1 1 d . . .
C19 C 0.2931(3) 0.33814(19) 0.84007(12) 0.0584(6) Uani 1 1 d . . .
H19 H 0.2228 0.3537 0.8690 0.070 Uiso 1 1 calc R . .
C20 C -0.0348(3) 0.0894(2) 0.55028(14) 0.0680(9) Uani 1 1 d . . .
C21 C 0.1021(3) 0.08266(18) 0.57354(12) 0.0570(6) Uani 1 1 d . . .
H21 H 0.1246 0.0415 0.6059 0.068 Uiso 1 1 calc R . .
C22 C 0.2044(2) 0.13725(16) 0.54828(10) 0.0463(5) Uani 1 1 d . . .
H22 H 0.2977 0.1351 0.5644 0.056 Uiso 1 1 calc R . .
C23 C 0.1719(2) 0.19545(16) 0.49944(10) 0.0449(5) Uani 1 1 d . . .
C24 C 0.0341(2) 0.1988(2) 0.47631(12) 0.0612(7) Uani 1 1 d . . .
H24 H 0.0114 0.2377 0.4427 0.073 Uiso 1 1 calc R . .
C25 C -0.0684(3) 0.1462(2) 0.50185(14) 0.0739(9) Uani 1 1 d . . .
H25 H -0.1621 0.1488 0.4862 0.089 Uiso 1 1 calc R . .
C26 C 0.2797(2) 0.25076(14) 0.46867(10) 0.0413(5) Uani 1 1 d . . .
C27 C 0.4127(2) 0.27803(13) 0.50343(9) 0.0352(4) Uani 1 1 d . . .
C28 C 0.3961(2) 0.32546(14) 0.56394(9) 0.0390(4) Uani 1 1 d . . .
C29 C 0.6057(2) 0.41459(14) 0.54409(10) 0.0402(5) Uani 1 1 d . . .
C30 C 0.6867(2) 0.48534(16) 0.56700(12) 0.0515(6) Uani 1 1 d . . .
H30 H 0.6668 0.5118 0.6060 0.062 Uiso 1 1 calc R . .
C31 C 0.7967(3) 0.51632(16) 0.53185(13) 0.0546(6) Uani 1 1 d . . .
H31 H 0.8531 0.5648 0.5467 0.065 Uiso 1 1 calc R . .
C32 C 0.8257(3) 0.47759(17) 0.47524(12) 0.0564(6) Uani 1 1 d . . .
H32 H 0.9019 0.4992 0.4514 0.068 Uiso 1 1 calc R . .
C33 C 0.7432(3) 0.40710(16) 0.45337(11) 0.0491(5) Uani 1 1 d . . .
H33 H 0.7639 0.3802 0.4146 0.059 Uiso 1 1 calc R . .
C34 C 0.6306(2) 0.37526(13) 0.48732(9) 0.0386(4) Uani 1 1 d . . .
C35 C 0.5388(2) 0.30184(13) 0.46497(9) 0.0370(4) Uani 1 1 d . . .
H35 H 0.5244 0.2986 0.4191 0.044 Uiso 1 1 calc R . .
C36 C 0.5390(2) 0.21238(13) 0.49864(8) 0.0331(4) Uani 1 1 d . . .
H36 H 0.6017 0.2081 0.5360 0.040 Uiso 1 1 calc R . .
C37 C 0.5209(2) 0.13058(13) 0.46309(9) 0.0353(4) Uani 1 1 d . . .
C38 C 0.5088(2) 0.06437(14) 0.43295(10) 0.0435(5) Uani 1 1 d . . .
H38 H 0.4992 0.0111 0.4087 0.052 Uiso 1 1 calc R . .
Cl1 Cl -0.16596(6) 0.04445(5) 0.75644(3) 0.0656(2) Uani 1 1 d . . .
Cl2 Cl -0.16487(9) 0.02414(7) 0.58338(5) 0.1032(4) Uani 1 1 d . . .
O1 O 0.50789(17) 0.09531(13) 0.82969(8) 0.0588(5) Uani 1 1 d . . .
O2 O 0.48666(15) 0.11333(11) 0.65360(7) 0.0466(4) Uani 1 1 d . . .
O3 O 0.64420(15) 0.22090(10) 0.64918(6) 0.0409(3) Uani 1 1 d . . .
O4 O 0.26639(19) 0.27386(12) 0.41480(7) 0.0574(4) Uani 1 1 d . . .
O5 O 0.30000(17) 0.31454(12) 0.59862(7) 0.0552(4) Uani 1 1 d . . .
O6 O 0.49681(16) 0.38545(11) 0.58198(7) 0.0490(4) 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
C1 C2 1.385(3) . ?
C1 C6 1.383(3) . ?
C1 Cl1 1.738(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(3) . ?
C4 C7 1.486(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.215(2) . ?
C7 C8 1.516(3) . ?
C8 C9 1.484(3) . ?
C8 C16 1.517(3) . ?
C8 C17 1.547(3) . ?
C9 O2 1.201(2) . ?
C9 O3 1.358(2) . ?
C10 C15 1.384(3) . ?
C10 C11 1.383(3) . ?
C10 O3 1.407(2) . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.476(3) . ?
C16 C17 1.517(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.441(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.181(3) . ?
C19 H19 0.9500 . ?
C20 C25 1.376(5) . ?
C20 C21 1.395(4) . ?
C20 Cl2 1.732(3) . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.394(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.398(3) . ?
C23 C26 1.477(3) . ?
C24 C25 1.370(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 O4 1.218(3) . ?
C26 C27 1.518(3) . ?
C27 C28 1.494(3) . ?
C27 C35 1.511(3) . ?
C27 C36 1.551(3) . ?
C28 O5 1.201(3) . ?
C28 O6 1.360(2) . ?
C29 C30 1.388(3) . ?
C29 C34 1.381(3) . ?
C29 O6 1.397(3) . ?
C30 C31 1.380(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.472(3) . ?
C35 C36 1.511(3) . ?
C35 H35 1.0000 . ?
C36 C37 1.443(3) . ?
C36 H36 1.0000 . ?
C37 C38 1.182(3) . ?
C38 H38 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.19(19) . . ?
C2 C1 Cl1 120.16(17) . . ?
C6 C1 Cl1 118.65(16) . . ?
C3 C2 C1 119.32(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.56(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 118.69(18) . . ?
C3 C4 C7 123.38(18) . . ?
C5 C4 C7 117.65(17) . . ?
C6 C5 C4 121.21(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 118.99(19) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 C4 121.20(18) . . ?
O1 C7 C8 118.77(18) . . ?
C4 C7 C8 119.90(16) . . ?
C9 C8 C16 117.50(16) . . ?
C9 C8 C7 116.56(16) . . ?
C16 C8 C7 118.10(16) . . ?
C9 C8 C17 116.34(16) . . ?
C16 C8 C17 59.34(13) . . ?
C7 C8 C17 116.71(16) . . ?
O2 C9 O3 117.64(17) . . ?
O2 C9 C8 124.06(19) . . ?
O3 C9 C8 118.30(16) . . ?
C15 C10 C11 122.56(19) . . ?
C15 C10 O3 121.40(17) . . ?
C11 C10 O3 116.01(18) . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 117.77(19) . . ?
C10 C15 C16 119.53(17) . . ?
C14 C15 C16 122.62(18) . . ?
C15 C16 C8 117.09(16) . . ?
C15 C16 C17 116.41(17) . . ?
C8 C16 C17 61.31(12) . . ?
C15 C16 H16 116.8 . . ?
C8 C16 H16 116.8 . . ?
C17 C16 H16 116.8 . . ?
C18 C17 C16 121.13(17) . . ?
C18 C17 C8 119.17(18) . . ?
C16 C17 C8 59.35(12) . . ?
C18 C17 H17 115.3 . . ?
C16 C17 H17 115.3 . . ?
C8 C17 H17 115.3 . . ?
C19 C18 C17 178.1(3) . . ?
C18 C19 H19 180.0 . . ?
C25 C20 C21 121.6(3) . . ?
C25 C20 Cl2 119.6(2) . . ?
C21 C20 Cl2 118.7(3) . . ?
C22 C21 C20 118.4(3) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C23 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.3(2) . . ?
C22 C23 C26 122.32(19) . . ?
C24 C23 C26 118.3(2) . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 119.6(2) . . ?
C24 C25 H25 120.2 . . ?
C20 C25 H25 120.2 . . ?
O4 C26 C23 121.43(19) . . ?
O4 C26 C27 118.3(2) . . ?
C23 C26 C27 120.28(18) . . ?
C28 C27 C26 117.43(17) . . ?
C28 C27 C35 117.74(17) . . ?
C26 C27 C35 116.97(16) . . ?
C28 C27 C36 116.36(16) . . ?
C26 C27 C36 116.28(16) . . ?
C35 C27 C36 59.13(12) . . ?
O5 C28 O6 116.67(18) . . ?
O5 C28 C27 124.95(19) . . ?
O6 C28 C27 118.38(18) . . ?
C30 C29 C34 122.3(2) . . ?
C30 C29 O6 115.91(19) . . ?
C34 C29 O6 121.83(18) . . ?
C29 C30 C31 118.5(2) . . ?
C29 C30 H30 120.8 . . ?
C31 C30 H30 120.8 . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 119.7(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C32 C33 C34 120.9(2) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C29 C34 C33 117.9(2) . . ?
C29 C34 C35 119.65(19) . . ?
C33 C34 C35 122.42(19) . . ?
C34 C35 C27 117.68(17) . . ?
C34 C35 C36 119.49(16) . . ?
C27 C35 C36 61.75(13) . . ?
C34 C35 H35 115.7 . . ?
C27 C35 H35 115.7 . . ?
C36 C35 H35 115.7 . . ?
C37 C36 C35 118.69(16) . . ?
C37 C36 C27 118.30(16) . . ?
C35 C36 C27 59.11(13) . . ?
C37 C36 H36 116.2 . . ?
C35 C36 H36 116.2 . . ?
C27 C36 H36 116.2 . . ?
C38 C37 C36 178.2(2) . . ?
C37 C38 H38 180.0 . . ?
C9 O3 C10 122.97(15) . . ?
C28 O6 C29 124.00(16) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        66.54
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
