# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

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

data_cb71_0m
_database_code_depnum_ccdc_archive 'CCDC 2092049'
loop_
_audit_author_name
_audit_author_address
'Charlene Tsay'
;University of California Riverside
United States of America
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8 F2 O2'
_chemical_formula_weight         258.21

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   3.7462(11)
_cell_length_b                   9.557(3)
_cell_length_c                   29.904(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.357(5)
_cell_angle_gamma                90
_cell_volume                     1070.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3383
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.69

_exptl_crystal_description       'thin-needle frag'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   0.451
_exptl_transmission_factor_max   0.745
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13979
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0976
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.362
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1979
_reflns_number_gt                1318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1979
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6423(7) 0.5919(3) 0.05435(8) 0.0212(6) Uani 1 1 d . . . . .
H1 H 0.6958 0.6467 0.0287 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7232(7) 0.4528(3) 0.05448(8) 0.0232(6) Uani 1 1 d . . . . .
H2 H 0.8297 0.4129 0.0287 0.028 Uiso 1 1 calc R U . . .
C3 C 0.6536(7) 0.3658(3) 0.09179(9) 0.0242(6) Uani 1 1 d . . . . .
H3 H 0.7082 0.2688 0.0914 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5064(7) 0.4270(3) 0.12792(8) 0.0217(6) Uani 1 1 d . . . . .
F4 F 0.4393(4) 0.34828(16) 0.16521(5) 0.0317(4) Uani 1 1 d . . . . .
C4A C 0.4127(6) 0.5707(2) 0.13072(8) 0.0189(6) Uani 1 1 d . . . . .
C5 C 0.0257(7) 0.8307(3) 0.21007(8) 0.0216(6) Uani 1 1 d . . . . .
F5 F -0.0420(4) 0.74083(16) 0.24468(5) 0.0312(4) Uani 1 1 d . . . . .
C6 C -0.0560(7) 0.9670(3) 0.21417(8) 0.0244(6) Uani 1 1 d . . . . .
H6 H -0.1581 1.0025 0.2409 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0151(7) 1.0565(3) 0.17727(8) 0.0231(6) Uani 1 1 d . . . . .
H7 H -0.0393 1.1533 0.1795 0.028 Uiso 1 1 calc R U . . .
C8 C 0.1598(7) 1.0061(3) 0.13878(9) 0.0207(6) Uani 1 1 d . . . . .
H8 H 0.2028 1.0685 0.1147 0.025 Uiso 1 1 calc R U . . .
C8A C 0.2484(6) 0.8612(3) 0.13391(8) 0.0187(6) Uani 1 1 d . . . . .
C9 C 0.3874(6) 0.8011(3) 0.09442(8) 0.0184(6) Uani 1 1 d . . . . .
C9A C 0.4778(6) 0.6567(3) 0.09222(8) 0.0178(6) Uani 1 1 d . . . . .
C10 C 0.2610(7) 0.6280(3) 0.16913(8) 0.0208(6) Uani 1 1 d . . . . .
H10 H 0.2126 0.5693 0.1940 0.025 Uiso 1 1 calc R U . . .
C10A C 0.1798(7) 0.7700(3) 0.17144(8) 0.0198(6) Uani 1 1 d . . . . .
C11 C 0.4348(6) 0.8906(3) 0.05395(8) 0.0203(6) Uani 1 1 d . . . . .
O1 O 0.5982(5) 1.00330(18) 0.05454(6) 0.0245(5) Uani 1 1 d . . . . .
O2 O 0.2836(5) 0.84030(18) 0.01738(5) 0.0244(5) Uani 1 1 d . . . . .
H2A H 0.3274 0.8935 -0.0043 0.037 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
C1 C2 1.363(4) . ?
C1 C9A 1.434(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.349(4) . ?
C3 H3 0.9500 . ?
C4 F4 1.369(3) . ?
C4 C4A 1.420(3) . ?
C4A C10 1.397(3) . ?
C4A C9A 1.437(3) . ?
C5 C6 1.344(4) . ?
C5 F5 1.370(3) . ?
C5 C10A 1.419(4) . ?
C6 C7 1.422(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.363(4) . ?
C7 H7 0.9500 . ?
C8 C8A 1.432(3) . ?
C8 H8 0.9500 . ?
C8A C9 1.415(3) . ?
C8A C10A 1.445(3) . ?
C9 C9A 1.423(3) . ?
C9 C11 1.493(3) . ?
C10 C10A 1.393(4) . ?
C10 H10 0.9500 . ?
C11 O1 1.239(3) . ?
C11 O2 1.319(3) . ?
O2 H2A 0.8400 . ?

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 C9A 121.1(2) . . ?
C2 C1 H1 119.5 . . ?
C9A C1 H1 119.5 . . ?
C1 C2 C3 122.2(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 117.0(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 F4 119.5(2) . . ?
C3 C4 C4A 124.6(2) . . ?
F4 C4 C4A 115.9(2) . . ?
C10 C4A C4 122.0(2) . . ?
C10 C4A C9A 120.4(2) . . ?
C4 C4A C9A 117.6(2) . . ?
C6 C5 F5 119.7(2) . . ?
C6 C5 C10A 124.4(2) . . ?
F5 C5 C10A 115.9(2) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C8A 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C8A C8 H8 119.3 . . ?
C9 C8A C8 124.3(2) . . ?
C9 C8A C10A 118.1(2) . . ?
C8 C8A C10A 117.5(2) . . ?
C8A C9 C9A 121.4(2) . . ?
C8A C9 C11 119.4(2) . . ?
C9A C9 C11 119.2(2) . . ?
C9 C9A C1 124.0(2) . . ?
C9 C9A C4A 118.5(2) . . ?
C1 C9A C4A 117.5(2) . . ?
C10A C10 C4A 120.9(2) . . ?
C10A C10 H10 119.6 . . ?
C4A C10 H10 119.6 . . ?
C10 C10A C5 121.9(2) . . ?
C10 C10A C8A 120.6(2) . . ?
C5 C10A C8A 117.5(2) . . ?
O1 C11 O2 122.6(2) . . ?
O1 C11 C9 123.2(2) . . ?
O2 C11 C9 114.3(2) . . ?
C11 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 F4 -178.9(2) . . . . ?
C2 C3 C4 C4A 1.0(4) . . . . ?
C3 C4 C4A C10 -180.0(3) . . . . ?
F4 C4 C4A C10 -0.1(3) . . . . ?
C3 C4 C4A C9A 0.3(4) . . . . ?
F4 C4 C4A C9A -179.8(2) . . . . ?
F5 C5 C6 C7 -179.4(2) . . . . ?
C10A C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C6 C7 C8 C8A -0.4(4) . . . . ?
C7 C8 C8A C9 177.7(2) . . . . ?
C7 C8 C8A C10A -0.2(4) . . . . ?
C8 C8A C9 C9A 178.5(2) . . . . ?
C10A C8A C9 C9A -3.6(3) . . . . ?
C8 C8A C9 C11 -2.5(4) . . . . ?
C10A C8A C9 C11 175.3(2) . . . . ?
C8A C9 C9A C1 -175.5(2) . . . . ?
C11 C9 C9A C1 5.5(4) . . . . ?
C8A C9 C9A C4A 2.3(3) . . . . ?
C11 C9 C9A C4A -176.7(2) . . . . ?
C2 C1 C9A C9 179.8(2) . . . . ?
C2 C1 C9A C4A 2.0(3) . . . . ?
C10 C4A C9A C9 0.6(3) . . . . ?
C4 C4A C9A C9 -179.7(2) . . . . ?
C10 C4A C9A C1 178.5(2) . . . . ?
C4 C4A C9A C1 -1.8(3) . . . . ?
C4 C4A C10 C10A 178.4(2) . . . . ?
C9A C4A C10 C10A -1.9(4) . . . . ?
C4A C10 C10A C5 -180.0(2) . . . . ?
C4A C10 C10A C8A 0.5(4) . . . . ?
C6 C5 C10A C10 179.6(3) . . . . ?
F5 C5 C10A C10 -0.7(4) . . . . ?
C6 C5 C10A C8A -0.8(4) . . . . ?
F5 C5 C10A C8A 178.8(2) . . . . ?
C9 C8A C10A C10 2.3(4) . . . . ?
C8 C8A C10A C10 -179.7(2) . . . . ?
C9 C8A C10A C5 -177.3(2) . . . . ?
C8 C8A C10A C5 0.8(3) . . . . ?
C8A C9 C11 O1 52.0(3) . . . . ?
C9A C9 C11 O1 -128.9(3) . . . . ?
C8A C9 C11 O2 -127.1(2) . . . . ?
C9A C9 C11 O2 51.9(3) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4


_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_cb72_0m
_database_code_depnum_ccdc_archive 'CCDC 2092050'
loop_
_audit_author_name
_audit_author_address
'Charlene Tsay'
;University of California Riverside
United States of America
;
_audit_update_record             
;
2021-06-25 deposited with the CCDC.	2021-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H8.07 Cl1.93 O2'
_chemical_formula_weight         288.70

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   18.665(2)
_cell_length_b                   3.8338(4)
_cell_length_c                   33.213(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.3374(17)
_cell_angle_gamma                90
_cell_volume                     2366.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7386
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      31.51

_exptl_crystal_description       'thin-needle frag'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             1175
_exptl_transmission_factor_min   0.487
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.524
_shelx_estimated_absorpt_T_min   0.779
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30670
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3482
_reflns_number_gt                2910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+1.5249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3482
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26129(8) 0.8442(4) 0.62367(5) 0.0167(3) Uani 1 1 d . . . . .
H1 H 0.2349 0.9097 0.5990 0.020 Uiso 1 1 calc R U . . .
C2 C 0.23563(9) 0.9289(4) 0.65950(6) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.1914 1.0515 0.6594 0.022 Uiso 1 1 calc R U . . .
C3 C 0.27361(9) 0.8377(4) 0.69682(5) 0.0184(3) Uani 1 1 d . . . . .
H3 H 0.2547 0.8960 0.7215 0.022 Uiso 1 1 calc R U . . .
C4 C 0.33743(9) 0.6659(4) 0.69712(5) 0.0157(3) Uani 1 1 d . . . . .
H4 H 0.3627 0.6068 0.7223 0.019 Uiso 0.035(2) 1 calc R U P A 1
Cl4 Cl 0.38425(2) 0.55926(12) 0.74316(2) 0.01872(13) Uani 0.965(2) 1 d . . P A
2
C4A C 0.36772(8) 0.5712(4) 0.66041(5) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.53214(8) 0.1552(4) 0.62464(5) 0.0150(3) Uani 1 1 d . . . . .
H5 H 0.5567 0.0854 0.6497 0.018 Uiso 0.035(2) 1 calc R U P A 1
Cl5 Cl 0.57561(2) 0.02325(10) 0.67063(2) 0.01540(12) Uani 0.965(2) 1 d . . P A
2
C6 C 0.56334(8) 0.0918(4) 0.58986(5) 0.0169(3) Uani 1 1 d . . . . .
H6 H 0.6095 -0.0141 0.5907 0.020 Uiso 1 1 calc R U . . .
C7 C 0.52583(9) 0.1867(4) 0.55224(5) 0.0173(3) Uani 1 1 d . . . . .
H7 H 0.5475 0.1441 0.5279 0.021 Uiso 1 1 calc R U . . .
C8 C 0.45940(8) 0.3376(4) 0.55031(5) 0.0154(3) Uani 1 1 d . . . . .
H8 H 0.4351 0.3933 0.5247 0.018 Uiso 1 1 calc R U . . .
C8A C 0.42570(8) 0.4132(4) 0.58642(5) 0.0137(3) Uani 1 1 d . . . . .
C9 C 0.35699(8) 0.5674(4) 0.58642(5) 0.0140(3) Uani 1 1 d . . . . .
C9A C 0.32758(8) 0.6577(4) 0.62276(5) 0.0137(3) Uani 1 1 d . . . . .
C10 C 0.43348(8) 0.4002(4) 0.66061(5) 0.0138(3) Uani 1 1 d . . . . .
H10 H 0.4584 0.3343 0.6857 0.017 Uiso 1 1 calc R U . . .
C10A C 0.46357(8) 0.3236(4) 0.62470(5) 0.0135(3) Uani 1 1 d . . . . .
C11 C 0.31307(8) 0.6346(4) 0.54725(5) 0.0155(3) Uani 1 1 d . . . . .
O1 O 0.33471(6) 0.8048(3) 0.51941(4) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.24813(7) 0.4930(3) 0.54518(4) 0.0198(3) Uani 1 1 d . . . . .
H2O H 0.2205(16) 0.571(8) 0.5214(9) 0.049(8) Uiso 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 1.363(2) . ?
C1 C9A 1.432(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.413(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.360(2) . ?
C3 H3 0.9500 . ?
C4 C4A 1.438(2) . ?
C4 Cl4 1.7380(17) . ?
C4 H4 0.9500 . ?
C4A C10 1.391(2) . ?
C4A C9A 1.435(2) . ?
C5 C6 1.363(2) . ?
C5 C10A 1.434(2) . ?
C5 Cl5 1.7370(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.422(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.364(2) . ?
C7 H7 0.9500 . ?
C8 C8A 1.435(2) . ?
C8 H8 0.9500 . ?
C8A C9 1.412(2) . ?
C8A C10A 1.438(2) . ?
C9 C9A 1.415(2) . ?
C9 C11 1.494(2) . ?
C10 C10A 1.396(2) . ?
C10 H10 0.9500 . ?
C11 O1 1.230(2) . ?
C11 O2 1.3240(19) . ?
O2 H2O 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9A 120.80(16) . . ?
C2 C1 H1 119.6 . . ?
C9A C1 H1 119.6 . . ?
C1 C2 C3 121.24(15) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.58(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C4A 121.94(16) . . ?
C3 C4 Cl4 119.26(13) . . ?
C4A C4 Cl4 118.80(12) . . ?
C3 C4 H4 119.0 . . ?
C4A C4 H4 119.0 . . ?
C10 C4A C9A 120.12(15) . . ?
C10 C4A C4 122.09(15) . . ?
C9A C4A C4 117.79(14) . . ?
C6 C5 C10A 122.24(15) . . ?
C6 C5 Cl5 119.47(12) . . ?
C10A C5 Cl5 118.28(12) . . ?
C6 C5 H5 118.9 . . ?
C10A C5 H5 118.9 . . ?
C5 C6 C7 119.01(15) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 121.39(15) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C8A 120.90(15) . . ?
C7 C8 H8 119.5 . . ?
C8A C8 H8 119.5 . . ?
C9 C8A C8 123.59(15) . . ?
C9 C8A C10A 118.16(14) . . ?
C8 C8A C10A 118.24(14) . . ?
C8A C9 C9A 121.79(15) . . ?
C8A C9 C11 119.80(14) . . ?
C9A C9 C11 118.41(14) . . ?
C9 C9A C1 123.02(15) . . ?
C9 C9A C4A 118.32(14) . . ?
C1 C9A C4A 118.61(14) . . ?
C4A C10 C10A 121.33(15) . . ?
C4A C10 H10 119.3 . . ?
C10A C10 H10 119.3 . . ?
C10 C10A C5 121.75(14) . . ?
C10 C10A C8A 120.09(14) . . ?
C5 C10A C8A 118.16(14) . . ?
O1 C11 O2 122.79(15) . . ?
O1 C11 C9 123.63(14) . . ?
O2 C11 C9 113.58(14) . . ?
C11 O2 H2O 109.7(18) . . ?

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
C9A C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C4A -0.4(3) . . . . ?
C2 C3 C4 Cl4 179.28(12) . . . . ?
C3 C4 C4A C10 179.01(16) . . . . ?
Cl4 C4 C4A C10 -0.6(2) . . . . ?
C3 C4 C4A C9A -1.2(2) . . . . ?
Cl4 C4 C4A C9A 179.13(12) . . . . ?
C10A C5 C6 C7 -1.8(3) . . . . ?
Cl5 C5 C6 C7 177.18(13) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C8A 1.4(3) . . . . ?
C7 C8 C8A C9 -179.70(16) . . . . ?
C7 C8 C8A C10A -0.4(2) . . . . ?
C8 C8A C9 C9A -175.97(15) . . . . ?
C10A C8A C9 C9A 4.7(2) . . . . ?
C8 C8A C9 C11 4.9(2) . . . . ?
C10A C8A C9 C11 -174.44(14) . . . . ?
C8A C9 C9A C1 173.83(15) . . . . ?
C11 C9 C9A C1 -7.0(2) . . . . ?
C8A C9 C9A C4A -3.4(2) . . . . ?
C11 C9 C9A C4A 175.80(14) . . . . ?
C2 C1 C9A C9 -179.18(16) . . . . ?
C2 C1 C9A C4A -2.0(2) . . . . ?
C10 C4A C9A C9 -0.6(2) . . . . ?
C4 C4A C9A C9 179.69(14) . . . . ?
C10 C4A C9A C1 -177.90(15) . . . . ?
C4 C4A C9A C1 2.3(2) . . . . ?
C9A C4A C10 C10A 3.0(2) . . . . ?
C4 C4A C10 C10A -177.20(15) . . . . ?
C4A C10 C10A C5 178.43(15) . . . . ?
C4A C10 C10A C8A -1.6(2) . . . . ?
C6 C5 C10A C10 -177.29(16) . . . . ?
Cl5 C5 C10A C10 3.7(2) . . . . ?
C6 C5 C10A C8A 2.8(2) . . . . ?
Cl5 C5 C10A C8A -176.24(12) . . . . ?
C9 C8A C10A C10 -2.2(2) . . . . ?
C8 C8A C10A C10 178.46(14) . . . . ?
C9 C8A C10A C5 177.72(14) . . . . ?
C8 C8A C10A C5 -1.6(2) . . . . ?
C8A C9 C11 O1 -55.0(2) . . . . ?
C9A C9 C11 O1 125.81(18) . . . . ?
C8A C9 C11 O2 125.03(16) . . . . ?
C9A C9 C11 O2 -54.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.95(3) 1.69(3) 2.6415(18) 175(3) 7_566

_refine_diff_density_max         0.938
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.096

_shelxl_version_number           2013-4

