# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1891866'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Cl4 Mo O'
_chemical_formula_weight         497.05

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'
Mo Mo -1.6832 0.6857 '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                   8.9934(15)
_cell_length_b                   19.335(3)
_cell_length_c                   11.3379(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.547(2)
_cell_angle_gamma                90
_cell_volume                     1949.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.521
_cell_measurement_theta_max      28.726

_exptl_crystal_description       prism
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.225
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1948
_exptl_absorpt_correction_T_max  0.3347
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.15280 (selected reflections only, before parameter refinement)
 R(int) =  0.0403(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21352
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4254
_reflns_number_gt                4088
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0252P)²+1.4733P] 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         4254
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0553
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.61038(19) 0.27232(9) 0.41660(15) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.66739(19) 0.20413(9) 0.44966(15) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.73536(19) 0.16482(9) 0.36762(16) 0.0162(3) Uani 1 1 d . . . . .
H3 H 0.7483 0.1844 0.2930 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7834(2) 0.09792(9) 0.39492(17) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.8266 0.0712 0.3384 0.023 Uiso 1 1 calc R U . . .
C5 C 0.7680(2) 0.06996(9) 0.50552(17) 0.0196(4) Uani 1 1 d . . . . .
H5 H 0.8004 0.0240 0.5242 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7054(2) 0.10902(9) 0.58932(16) 0.0176(4) Uani 1 1 d . . . . .
H6 H 0.6980 0.0899 0.6654 0.021 Uiso 1 1 calc R U . . .
C7 C 0.65435(19) 0.17514(9) 0.56204(15) 0.0149(3) Uani 1 1 d . . . . .
H7 H 0.6103 0.2012 0.6189 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6860(2) 0.31434(9) 0.33712(15) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.8447(2) 0.31612(9) 0.35178(16) 0.0172(3) Uani 1 1 d . . . . .
H9 H 0.9018 0.2873 0.4095 0.021 Uiso 1 1 calc R U . . .
C10 C 0.9169(2) 0.35983(10) 0.28199(17) 0.0203(4) Uani 1 1 d . . . . .
H10 H 1.0235 0.3627 0.2946 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8340(2) 0.39963(10) 0.19347(18) 0.0229(4) Uani 1 1 d . . . . .
H11 H 0.8842 0.4292 0.1453 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6775(2) 0.39620(10) 0.17517(17) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.6215 0.4222 0.1126 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6031(2) 0.35507(9) 0.24780(16) 0.0179(4) Uani 1 1 d . . . . .
H13 H 0.4963 0.3544 0.2372 0.021 Uiso 1 1 calc R U . . .
C14 C 0.48022(19) 0.29970(9) 0.46097(15) 0.0143(3) Uani 1 1 d . . . . .
C15 C 0.4616(2) 0.37218(9) 0.47016(15) 0.0168(3) Uani 1 1 d . . . . .
H15 H 0.5357 0.4026 0.4482 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3357(2) 0.39870(9) 0.51110(16) 0.0190(4) Uani 1 1 d . . . . .
H16 H 0.3241 0.4473 0.5177 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2262(2) 0.35448(10) 0.54253(16) 0.0193(4) Uani 1 1 d . . . . .
H17 H 0.1394 0.3731 0.5695 0.023 Uiso 1 1 calc R U . . .
C18 C 0.2430(2) 0.28294(10) 0.53477(16) 0.0183(4) Uani 1 1 d . . . . .
H18 H 0.1682 0.2530 0.5572 0.022 Uiso 1 1 calc R U . . .
C19 C 0.36821(19) 0.25565(9) 0.49455(15) 0.0155(3) Uani 1 1 d . . . . .
H19 H 0.3792 0.2069 0.4894 0.019 Uiso 1 1 calc R U . . .
Cl2 Cl 0.39726(5) 0.19739(2) 0.17812(4) 0.01824(9) Uani 1 1 d . . . . .
Cl3 Cl 0.08891(5) 0.01676(2) 0.22649(4) 0.01875(9) Uani 1 1 d . . . . .
Cl4 Cl 0.08831(5) 0.17904(2) 0.28053(4) 0.01949(10) Uani 1 1 d . . . . .
Cl5 Cl 0.39791(6) 0.03586(3) 0.11923(6) 0.03748(14) Uani 1 1 d . . . . .
Mo1 Mo 0.27877(2) 0.10116(2) 0.25069(2) 0.01400(5) Uani 1 1 d . . . . .
O1 O 0.37364(16) 0.08593(7) 0.38472(13) 0.0251(3) 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 C14 1.442(2) . ?
C1 C2 1.444(2) . ?
C1 C8 1.455(2) . ?
C2 C3 1.409(2) . ?
C2 C7 1.413(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.406(2) . ?
C8 C9 1.412(2) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.414(2) . ?
C14 C15 1.417(2) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
Cl2 Mo1 2.3527(5) . ?
Cl3 Mo1 2.3484(5) . ?
Cl4 Mo1 2.3427(5) . ?
Cl5 Mo1 2.3320(6) . ?
Mo1 O1 1.6549(14) . ?

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
C14 C1 C2 121.35(15) . . ?
C14 C1 C8 119.31(15) . . ?
C2 C1 C8 119.34(15) . . ?
C3 C2 C7 118.92(16) . . ?
C3 C2 C1 119.57(16) . . ?
C7 C2 C1 121.51(15) . . ?
C4 C3 C2 120.53(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.70(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.48(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.25(17) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.06(16) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C13 C8 C9 119.30(16) . . ?
C13 C8 C1 120.81(16) . . ?
C9 C8 C1 119.86(16) . . ?
C10 C9 C8 119.96(17) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.26(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.18(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.31(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C8 119.87(17) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C19 C14 C15 118.64(16) . . ?
C19 C14 C1 121.37(15) . . ?
C15 C14 C1 119.98(16) . . ?
C16 C15 C14 120.16(17) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.27(17) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.41(16) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.03(17) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.49(16) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
O1 Mo1 Cl5 105.51(6) . . ?
O1 Mo1 Cl4 105.66(5) . . ?
Cl5 Mo1 Cl4 148.82(2) . . ?
O1 Mo1 Cl3 104.49(5) . . ?
Cl5 Mo1 Cl3 86.80(2) . . ?
Cl4 Mo1 Cl3 85.93(2) . . ?
O1 Mo1 Cl2 105.27(5) . . ?
Cl5 Mo1 Cl2 85.97(2) . . ?
Cl4 Mo1 Cl2 85.47(2) . . ?
Cl3 Mo1 Cl2 150.226(17) . . ?

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
C14 C1 C2 C3 147.44(17) . . . . ?
C8 C1 C2 C3 -32.7(2) . . . . ?
C14 C1 C2 C7 -31.4(2) . . . . ?
C8 C1 C2 C7 148.43(17) . . . . ?
C7 C2 C3 C4 2.4(3) . . . . ?
C1 C2 C3 C4 -176.46(16) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C3 C2 C7 C6 -1.0(3) . . . . ?
C1 C2 C7 C6 177.83(16) . . . . ?
C14 C1 C8 C13 -39.7(2) . . . . ?
C2 C1 C8 C13 140.45(17) . . . . ?
C14 C1 C8 C9 138.32(17) . . . . ?
C2 C1 C8 C9 -41.5(2) . . . . ?
C13 C8 C9 C10 2.7(3) . . . . ?
C1 C8 C9 C10 -175.34(16) . . . . ?
C8 C9 C10 C11 -3.1(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 2.4(3) . . . . ?
C11 C12 C13 C8 -2.7(3) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C1 C8 C13 C12 178.22(17) . . . . ?
C2 C1 C14 C19 -26.8(2) . . . . ?
C8 C1 C14 C19 153.39(16) . . . . ?
C2 C1 C14 C15 154.08(16) . . . . ?
C8 C1 C14 C15 -25.8(2) . . . . ?
C19 C14 C15 C16 -0.1(3) . . . . ?
C1 C14 C15 C16 179.07(16) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C14 0.0(3) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C1 C14 C19 C18 -178.79(16) . . . . ?

_refine_diff_density_max         0.528
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1891867'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 F6 Nb'
_chemical_formula_weight         450.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nb Nb -2.0727 0.6215 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5095(15)
_cell_length_b                   12.681(2)
_cell_length_c                   16.036(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.183(2)
_cell_angle_gamma                90
_cell_volume                     1725.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8252
_cell_measurement_theta_min      2.400
_cell_measurement_theta_max      28.260

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1263 (selected reflections only, before parameter refinement)
 R(int) =  0.0486(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18372
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3763
_reflns_number_gt                3246
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0275P)²+1.2217P] 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         3763
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.9503(2) 0.59173(16) 0.31567(12) 0.0160(4) Uani 1 1 d . . . . .
C2 C 1.1070(2) 0.56188(16) 0.34828(12) 0.0155(4) Uani 1 1 d . . . . .
C3 C 1.2109(3) 0.64065(17) 0.38205(13) 0.0194(4) Uani 1 1 d . . . . .
H3 H 1.1742 0.7107 0.3887 0.023 Uiso 1 1 calc R U . . .
C4 C 1.3660(3) 0.61542(18) 0.40540(13) 0.0226(5) Uani 1 1 d . . . . .
H4 H 1.4371 0.6686 0.4261 0.027 Uiso 1 1 calc R U . . .
C5 C 1.4175(3) 0.51168(19) 0.39851(13) 0.0233(5) Uani 1 1 d . . . . .
H5 H 1.5242 0.4947 0.4145 0.028 Uiso 1 1 calc R U . . .
C6 C 1.3154(3) 0.43287(18) 0.36859(13) 0.0213(5) Uani 1 1 d . . . . .
H6 H 1.3515 0.3621 0.3659 0.026 Uiso 1 1 calc R U . . .
C7 C 1.1611(3) 0.45728(17) 0.34273(12) 0.0184(4) Uani 1 1 d . . . . .
H7 H 1.0916 0.4036 0.3212 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8786(2) 0.54327(15) 0.24110(13) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.9727(2) 0.49882(16) 0.18132(13) 0.0167(4) Uani 1 1 d . . . . .
H9 H 1.0842 0.4993 0.1910 0.020 Uiso 1 1 calc R U . . .
C10 C 0.9044(3) 0.45480(17) 0.10900(13) 0.0201(4) Uani 1 1 d . . . . .
H10 H 0.9686 0.4241 0.0695 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7415(3) 0.45537(17) 0.09388(14) 0.0207(5) Uani 1 1 d . . . . .
H11 H 0.6946 0.4245 0.0441 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6468(2) 0.50065(17) 0.15098(13) 0.0196(4) Uani 1 1 d . . . . .
H12 H 0.5357 0.5024 0.1394 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7131(2) 0.54314(16) 0.22438(13) 0.0172(4) Uani 1 1 d . . . . .
H13 H 0.6475 0.5724 0.2639 0.021 Uiso 1 1 calc R U . . .
C14 C 0.8686(2) 0.67473(16) 0.35743(12) 0.0163(4) Uani 1 1 d . . . . .
C15 C 0.8828(2) 0.68282(17) 0.44522(13) 0.0195(4) Uani 1 1 d . . . . .
H15 H 0.9484 0.6351 0.4774 0.023 Uiso 1 1 calc R U . . .
C16 C 0.8009(3) 0.76053(17) 0.48466(14) 0.0227(5) Uani 1 1 d . . . . .
H16 H 0.8083 0.7648 0.5440 0.027 Uiso 1 1 calc R U . . .
C17 C 0.7081(2) 0.83211(18) 0.43774(14) 0.0231(5) Uani 1 1 d . . . . .
H17 H 0.6524 0.8852 0.4653 0.028 Uiso 1 1 calc R U . . .
C18 C 0.6957(2) 0.82704(17) 0.35094(13) 0.0213(5) Uani 1 1 d . . . . .
H18 H 0.6339 0.8773 0.3192 0.026 Uiso 1 1 calc R U . . .
C19 C 0.7741(2) 0.74812(16) 0.31096(13) 0.0183(4) Uani 1 1 d . . . . .
H19 H 0.7639 0.7435 0.2517 0.022 Uiso 1 1 calc R U . . .
F1 F 0.40309(17) 0.80535(12) 0.22512(9) 0.0362(4) Uani 1 1 d . . . . .
F2 F 0.31641(15) 0.60891(10) 0.18651(8) 0.0268(3) Uani 1 1 d . . . . .
F3 F 0.09440(16) 0.75451(10) 0.20713(9) 0.0271(3) Uani 1 1 d . . . . .
F4 F 0.13909(16) 0.68062(12) 0.05572(8) 0.0350(3) Uani 1 1 d . . . . .
F5 F 0.21861(16) 0.87931(11) 0.09670(8) 0.0315(3) Uani 1 1 d . . . . .
F6 F 0.43976(16) 0.73151(11) 0.07303(9) 0.0302(3) Uani 1 1 d . . . . .
Nb1 Nb 0.26874(2) 0.74425(2) 0.14115(2) 0.01506(7) 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 C8 1.440(3) . ?
C1 C2 1.447(3) . ?
C1 C14 1.452(3) . ?
C2 C7 1.409(3) . ?
C2 C3 1.415(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.411(3) . ?
C8 C13 1.414(3) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.407(3) . ?
C14 C15 1.408(3) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
F1 Nb1 1.8698(13) . ?
F2 Nb1 1.8963(13) . ?
F3 Nb1 1.8885(13) . ?
F4 Nb1 1.8774(13) . ?
F5 Nb1 1.8919(14) . ?
F6 Nb1 1.8892(13) . ?

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
C8 C1 C2 120.79(18) . . ?
C8 C1 C14 120.29(18) . . ?
C2 C1 C14 118.87(18) . . ?
C7 C2 C3 119.38(19) . . ?
C7 C2 C1 121.34(19) . . ?
C3 C2 C1 119.17(19) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 119.9(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 C8 C13 118.53(19) . . ?
C9 C8 C1 120.51(19) . . ?
C13 C8 C1 120.90(18) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.19(19) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C19 C14 C15 119.04(19) . . ?
C19 C14 C1 120.63(18) . . ?
C15 C14 C1 120.32(19) . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
F1 Nb1 F4 178.25(6) . . ?
F1 Nb1 F3 91.83(7) . . ?
F4 Nb1 F3 89.69(6) . . ?
F1 Nb1 F6 89.74(7) . . ?
F4 Nb1 F6 88.73(6) . . ?
F3 Nb1 F6 178.39(6) . . ?
F1 Nb1 F5 90.31(7) . . ?
F4 Nb1 F5 90.56(6) . . ?
F3 Nb1 F5 89.08(6) . . ?
F6 Nb1 F5 91.24(6) . . ?
F1 Nb1 F2 89.79(6) . . ?
F4 Nb1 F2 89.36(6) . . ?
F3 Nb1 F2 90.13(5) . . ?
F6 Nb1 F2 89.55(6) . . ?
F5 Nb1 F2 179.20(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
C8 C1 C2 C7 -35.1(3) . . . . ?
C14 C1 C2 C7 147.41(19) . . . . ?
C8 C1 C2 C3 141.2(2) . . . . ?
C14 C1 C2 C3 -36.3(3) . . . . ?
C7 C2 C3 C4 3.1(3) . . . . ?
C1 C2 C3 C4 -173.26(19) . . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 1.9(3) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
C3 C2 C7 C6 -1.3(3) . . . . ?
C1 C2 C7 C6 174.99(19) . . . . ?
C2 C1 C8 C9 -24.6(3) . . . . ?
C14 C1 C8 C9 152.82(19) . . . . ?
C2 C1 C8 C13 158.15(19) . . . . ?
C14 C1 C8 C13 -24.4(3) . . . . ?
C13 C8 C9 C10 -1.1(3) . . . . ?
C1 C8 C9 C10 -178.37(19) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 C8 1.6(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C1 C8 C13 C12 177.08(19) . . . . ?
C8 C1 C14 C19 -35.4(3) . . . . ?
C2 C1 C14 C19 142.1(2) . . . . ?
C8 C1 C14 C15 144.6(2) . . . . ?
C2 C1 C14 C15 -38.0(3) . . . . ?
C19 C14 C15 C16 1.7(3) . . . . ?
C1 C14 C15 C16 -178.22(19) . . . . ?
C14 C15 C16 C17 -1.7(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C15 C14 C19 C18 -0.2(3) . . . . ?
C1 C14 C19 C18 179.76(19) . . . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_A1
_database_code_depnum_ccdc_archive 'CCDC 1891871'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Br O2'
_chemical_formula_weight         319.19

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   14.500(3)
_cell_length_b                   26.776(6)
_cell_length_c                   7.1309(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2768.6(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6615
_cell_measurement_theta_min      2.680
_cell_measurement_theta_max      26.6555

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale blue-green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    2.964
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3753
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1458 (selected reflections only, before parameter refinement)
 R(int) =  0.0840(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17881
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.597
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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             2442
_reflns_number_gt                2088
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0318P)²+14.1475P] 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         2442
_refine_ls_number_parameters     173
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_restrained_S_all      1.244
_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
Br1 Br 0.65986(4) 0.55153(2) 0.73759(7) 0.01828(19) Uani 1 1 d . . . . .
C1 C 0.5095(3) 0.55895(17) 0.1488(6) 0.0080(10) Uani 1 1 d . U . . .
C2 C 0.5241(3) 0.60887(18) 0.2515(7) 0.0116(10) Uani 1 1 d . . . . .
C3 C 0.5951(3) 0.60130(19) 0.4111(7) 0.0108(11) Uani 1 1 d . . . . .
H3A H 0.6503 0.5844 0.3598 0.013 Uiso 1 1 calc R U . . .
H3B H 0.6146 0.6344 0.4590 0.013 Uiso 1 1 calc R U . . .
C4 C 0.5571(3) 0.5706(2) 0.5728(7) 0.0123(11) Uani 1 1 d . U . . .
H4A H 0.5261 0.5403 0.5240 0.015 Uiso 1 1 calc R U . . .
H4B H 0.5112 0.5904 0.6439 0.015 Uiso 1 1 calc R U . . .
C5 C 0.5607(3) 0.64541(18) 0.1021(7) 0.0100(10) Uani 1 1 d . U . . .
C6 C 0.5012(4) 0.66636(19) -0.0292(7) 0.0132(11) Uani 1 1 d . . . . .
H6 H 0.4374 0.6582 -0.0258 0.016 Uiso 1 1 calc R U . . .
C7 C 0.5335(4) 0.6987(2) -0.1641(7) 0.0180(12) Uani 1 1 d . . . . .
H7 H 0.4919 0.7126 -0.2530 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6256(4) 0.71114(19) -0.1713(7) 0.0149(11) Uani 1 1 d . U . . .
H8 H 0.6472 0.7341 -0.2631 0.018 Uiso 1 1 calc R U . . .
C9 C 0.6860(4) 0.69034(19) -0.0457(7) 0.0145(11) Uani 1 1 d . . . . .
H9 H 0.7497 0.6984 -0.0517 0.017 Uiso 1 1 calc R U . . .
C10 C 0.6539(3) 0.65715(18) 0.0916(7) 0.0108(10) Uani 1 1 d . . . . .
H10 H 0.6961 0.6426 0.1778 0.013 Uiso 1 1 calc R U . . .
C11 C 0.4330(3) 0.62757(19) 0.3391(7) 0.0115(11) Uani 1 1 d . . . . .
C12 C 0.4247(4) 0.67782(19) 0.3865(7) 0.0136(11) Uani 1 1 d . . . . .
H12 H 0.4722 0.7005 0.3526 0.016 Uiso 1 1 calc R U . . .
C13 C 0.3485(4) 0.6951(2) 0.4819(7) 0.0183(12) Uani 1 1 d . . . . .
H13 H 0.3443 0.7295 0.5140 0.022 Uiso 1 1 calc R U . . .
C14 C 0.2784(4) 0.6631(2) 0.5308(8) 0.0205(13) Uani 1 1 d . . . . .
H14 H 0.2259 0.6750 0.5965 0.025 Uiso 1 1 calc R U . . .
C15 C 0.2857(4) 0.6127(2) 0.4826(7) 0.0218(13) Uani 1 1 d . . . . .
H15 H 0.2377 0.5902 0.5154 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3623(3) 0.5954(2) 0.3877(7) 0.0138(11) Uani 1 1 d . . . . .
H16 H 0.3664 0.5611 0.3553 0.017 Uiso 1 1 calc R U . . .
O1 O 0.4462(2) 0.56052(12) 0.0186(5) 0.0123(8) Uani 1 1 d . . . . .
H1 H 0.4430 0.5327 -0.0351 0.018 Uiso 1 1 calc R U . . .
O2 O 0.5563(2) 0.52207(13) 0.1828(5) 0.0124(8) 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
Br1 C4 1.965(5) . ?
C1 O2 1.222(6) . ?
C1 O1 1.307(6) . ?
C1 C2 1.539(6) . ?
C2 C5 1.541(7) . ?
C2 C11 1.544(7) . ?
C2 C3 1.548(7) . ?
C3 C4 1.520(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.389(7) . ?
C5 C6 1.392(7) . ?
C6 C7 1.377(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.372(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.402(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.383(7) . ?
C11 C12 1.393(7) . ?
C12 C13 1.377(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O1 H1 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
O2 C1 O1 123.9(4) . . ?
O2 C1 C2 122.1(4) . . ?
O1 C1 C2 114.0(4) . . ?
C1 C2 C5 105.7(4) . . ?
C1 C2 C11 110.9(4) . . ?
C5 C2 C11 111.6(4) . . ?
C1 C2 C3 109.1(4) . . ?
C5 C2 C3 111.2(4) . . ?
C11 C2 C3 108.3(4) . . ?
C4 C3 C2 112.8(4) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 Br1 108.6(3) . . ?
C3 C4 H4A 110.0 . . ?
Br1 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
Br1 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C10 C5 C6 118.4(5) . . ?
C10 C5 C2 121.1(4) . . ?
C6 C5 C2 120.5(4) . . ?
C7 C6 C5 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.5(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.1(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.2(5) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C16 C11 C12 118.4(5) . . ?
C16 C11 C2 122.3(5) . . ?
C12 C11 C2 119.1(4) . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.0(5) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 120.4(5) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.7(5) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C1 O1 H1 109.5 . . ?

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
O1 H1 O2 0.84 1.80 2.637(5) 170.8 5_665
C4 H4A O2 0.99 2.52 3.069(6) 114.8 .
C3 H3A Br1 0.99 3.02 3.992(5) 167.9 8_755

_refine_diff_density_max         0.867
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1891870'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H5 Cl O2'
_chemical_formula_weight         120.53

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           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                   5.387(15)
_cell_length_b                   9.02(3)
_cell_length_c                   11.16(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.87(5)
_cell_angle_gamma                90
_cell_volume                     531(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    735
_cell_measurement_theta_min      2.929
_cell_measurement_theta_max      25.698

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.597
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.1119
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1986 (selected reflections only, before parameter refinement)
 R(int) =  0.0823(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3721
_diffrn_reflns_av_unetI/netI     0.1627
_diffrn_reflns_av_R_equivalents  0.2230
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             925
_reflns_number_gt                523
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.1081P)²+3.9525P] 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         925
_refine_ls_number_parameters     66
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2203
_refine_ls_R_factor_gt           0.1338
_refine_ls_wR_factor_ref         0.3275
_refine_ls_wR_factor_gt          0.2851
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Cl1 Cl 0.6516(5) 0.1966(4) 0.4294(3) 0.0603(12) Uani 1 1 d . . . . .
O2 O 0.2277(13) 0.3986(9) 0.4589(8) 0.050(2) Uani 1 1 d . . . . .
O1 O 0.1522(14) 0.4300(9) 0.6454(7) 0.054(2) Uani 1 1 d . . . . .
H1 H 0.2041 0.3932 0.7131 0.080 Uiso 1 1 calc R U . . .
C4 C 0.8373(17) 0.0874(11) 0.6551(11) 0.044(3) Uani 1 1 d . . . . .
H4A H 0.8308 0.0954 0.7402 0.066 Uiso 1 1 calc R U . . .
H4B H 1.0034 0.1144 0.6440 0.066 Uiso 1 1 calc R U . . .
H4C H 0.8011 -0.0129 0.6283 0.066 Uiso 1 1 calc R U . . .
C1 C 0.2782(16) 0.3702(12) 0.5642(13) 0.040(3) Uani 1 1 d . . . . .
C3 C 0.6447(17) 0.1891(11) 0.5817(10) 0.037(3) Uani 1 1 d . . . . .
C2 C 0.4810(17) 0.2673(11) 0.6306(11) 0.042(3) Uani 1 1 d . . . . .
H2 H 0.4929 0.2573 0.7146 0.050 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
Cl1 C3 1.709(12) . ?
O2 C1 1.179(13) . ?
O1 C1 1.351(13) . ?
O1 H1 0.8200 . ?
C4 C3 1.496(14) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C1 C2 1.507(15) . ?
C3 C2 1.331(14) . ?
C2 H2 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
C1 O1 H1 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C1 O1 122.5(10) . . ?
O2 C1 C2 128.3(10) . . ?
O1 C1 C2 109.2(11) . . ?
C2 C3 C4 122.9(11) . . ?
C2 C3 Cl1 122.6(9) . . ?
C4 C3 Cl1 114.5(8) . . ?
C3 C2 C1 126.8(11) . . ?
C3 C2 H2 116.6 . . ?
C1 C2 H2 116.6 . . ?

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
C4 H4C Cl1 0.96 2.91 3.656(13) 135.4 3_656
C4 H4A O2 0.96 2.61 3.561(18) 169.6 4_666
O1 H1 Cl1 0.82 2.62 3.370(12) 153.5 4_566
C4 H4C Cl1 0.96 2.91 3.656(13) 135.4 3_656
C4 H4A O2 0.96 2.61 3.561(18) 169.6 4_666
O1 H1 Cl1 0.82 2.62 3.370(12) 153.5 4_566
C4 H4C Cl1 0.96 2.91 3.656(13) 135.4 3_656
C4 H4A O2 0.96 2.61 3.561(18) 169.6 4_666
O1 H1 Cl1 0.82 2.62 3.370(12) 153.5 4_566
C4 H4C Cl1 0.96 2.91 3.656(13) 135.4 3_656
C4 H4A O2 0.96 2.61 3.561(18) 169.6 4_666
O1 H1 Cl1 0.82 2.62 3.370(12) 153.5 4_566

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.130

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1891869'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 O2'
_chemical_formula_weight         238.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -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'

_cell_length_a                   7.3476(6)
_cell_length_b                   15.2022(11)
_cell_length_c                   10.9707(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.960(3)
_cell_angle_gamma                90
_cell_volume                     1224.71(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6377
_cell_measurement_theta_min      2.290
_cell_measurement_theta_max      26.4735

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1236 (selected reflections only, before parameter refinement)
 R(int) =  0.0584(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14249
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.339
_diffrn_reflns_theta_max         25.998
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4780
_reflns_number_gt                4163
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0438P)²+0.2676P] 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_abs_structure_details 
;
 Flack x determined using 1699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4780
_refine_ls_number_parameters     325
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.1150(5) 0.2839(2) 0.8552(3) 0.0236(8) Uani 1 1 d . . . . .
C2 C 0.2017(4) 0.2498(2) 0.7386(3) 0.0182(7) Uani 1 1 d . . . . .
C3 C 0.0318(4) 0.2174(2) 0.6655(3) 0.0257(8) Uani 1 1 d . . . . .
H3A H 0.0488 0.2218 0.5765 0.031 Uiso 1 1 calc R U . . .
H3B H 0.0020 0.1558 0.6863 0.031 Uiso 1 1 calc R U . . .
C4 C -0.1135(5) 0.2800(2) 0.7063(4) 0.0337(9) Uani 1 1 d . . . . .
H4A H -0.1146 0.3345 0.6567 0.040 Uiso 1 1 calc R U . . .
H4B H -0.2354 0.2523 0.6995 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3382(4) 0.1749(2) 0.7611(3) 0.0174(7) Uani 1 1 d . . . . .
C6 C 0.4561(4) 0.1538(2) 0.6698(3) 0.0191(7) Uani 1 1 d . . . . .
H6 H 0.4536 0.1873 0.5966 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5780(4) 0.0844(2) 0.6840(3) 0.0213(8) Uani 1 1 d . . . . .
H7 H 0.6584 0.0707 0.6207 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5824(5) 0.0353(2) 0.7900(3) 0.0239(8) Uani 1 1 d . . . . .
H8 H 0.6667 -0.0117 0.8004 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4634(5) 0.0550(2) 0.8805(3) 0.0245(8) Uani 1 1 d . . . . .
H9 H 0.4646 0.0208 0.9529 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3420(4) 0.1244(2) 0.8668(3) 0.0212(7) Uani 1 1 d . . . . .
H10 H 0.2610 0.1375 0.9300 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2966(4) 0.3300(2) 0.6830(3) 0.0174(7) Uani 1 1 d . . . . .
C12 C 0.4272(4) 0.3751(2) 0.7543(3) 0.0241(8) Uani 1 1 d . . . . .
H12 H 0.4539 0.3564 0.8356 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5187(5) 0.4470(2) 0.7074(4) 0.0296(9) Uani 1 1 d . . . . .
H13 H 0.6057 0.4778 0.7572 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4837(5) 0.4736(2) 0.5894(4) 0.0299(9) Uani 1 1 d . . . . .
H14 H 0.5470 0.5225 0.5575 0.036 Uiso 1 1 calc R U . . .
C15 C 0.3568(5) 0.4294(2) 0.5176(3) 0.0263(8) Uani 1 1 d . . . . .
H15 H 0.3331 0.4477 0.4358 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2636(4) 0.3584(2) 0.5636(3) 0.0215(7) Uani 1 1 d . . . . .
H16 H 0.1758 0.3287 0.5132 0.026 Uiso 1 1 calc R U . . .
C21 C 0.6041(5) 0.2060(2) 0.3357(3) 0.0215(7) Uani 1 1 d . . . . .
C22 C 0.7074(4) 0.2369(2) 0.2249(3) 0.0172(7) Uani 1 1 d . . . . .
C23 C 0.5473(4) 0.2537(2) 0.1330(3) 0.0247(8) Uani 1 1 d . . . . .
H23A H 0.5777 0.2998 0.0733 0.030 Uiso 1 1 calc R U . . .
H23B H 0.5114 0.1993 0.0888 0.030 Uiso 1 1 calc R U . . .
C24 C 0.3996(5) 0.2841(3) 0.2160(4) 0.0306(9) Uani 1 1 d . . . . .
H24A H 0.4090 0.3481 0.2313 0.037 Uiso 1 1 calc R U . . .
H24B H 0.2774 0.2710 0.1795 0.037 Uiso 1 1 calc R U . . .
C25 C 0.8453(4) 0.1677(2) 0.1881(3) 0.0169(7) Uani 1 1 d . . . . .
C26 C 0.8340(5) 0.1240(2) 0.0774(3) 0.0245(8) Uani 1 1 d . . . . .
H26 H 0.7394 0.1384 0.0196 0.029 Uiso 1 1 calc R U . . .
C27 C 0.9586(5) 0.0594(2) 0.0499(4) 0.0339(9) Uani 1 1 d . . . . .
H27 H 0.9482 0.0295 -0.0260 0.041 Uiso 1 1 calc R U . . .
C28 C 1.0977(5) 0.0383(2) 0.1320(4) 0.0379(11) Uani 1 1 d . . . . .
H28 H 1.1818 -0.0068 0.1135 0.045 Uiso 1 1 calc R U . . .
C29 C 1.1142(5) 0.0829(3) 0.2409(4) 0.0350(10) Uani 1 1 d . . . . .
H29 H 1.2116 0.0695 0.2969 0.042 Uiso 1 1 calc R U . . .
C30 C 0.9895(5) 0.1472(2) 0.2691(3) 0.0260(8) Uani 1 1 d . . . . .
H30 H 1.0021 0.1777 0.3444 0.031 Uiso 1 1 calc R U . . .
C31 C 0.8047(4) 0.3238(2) 0.2582(3) 0.0171(7) Uani 1 1 d . . . . .
C32 C 0.7876(4) 0.3653(2) 0.3705(3) 0.0204(7) Uani 1 1 d . . . . .
H32 H 0.7112 0.3404 0.4295 0.024 Uiso 1 1 calc R U . . .
C33 C 0.8812(5) 0.4426(2) 0.3967(4) 0.0291(9) Uani 1 1 d . . . . .
H33 H 0.8691 0.4701 0.4738 0.035 Uiso 1 1 calc R U . . .
C34 C 0.9908(4) 0.4795(2) 0.3122(4) 0.0331(10) Uani 1 1 d . . . . .
H34 H 1.0546 0.5325 0.3304 0.040 Uiso 1 1 calc R U . . .
C35 C 1.0081(5) 0.4393(2) 0.2006(4) 0.0324(10) Uani 1 1 d . . . . .
H35 H 1.0848 0.4647 0.1421 0.039 Uiso 1 1 calc R U . . .
C36 C 0.9146(4) 0.3623(2) 0.1728(3) 0.0236(8) Uani 1 1 d . . . . .
H36 H 0.9258 0.3358 0.0951 0.028 Uiso 1 1 calc R U . . .
O1 O 0.1865(4) 0.29892(18) 0.9515(2) 0.0361(7) Uani 1 1 d . . . . .
O2 O -0.0628(3) 0.29894(17) 0.8329(3) 0.0343(7) Uani 1 1 d . . . . .
O3 O 0.6606(4) 0.16403(16) 0.4207(2) 0.0311(6) Uani 1 1 d . . . . .
O4 O 0.4312(3) 0.23493(16) 0.3278(2) 0.0288(6) 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 O1 1.187(4) . ?
C1 O2 1.341(4) . ?
C1 C2 1.538(5) . ?
C2 C5 1.532(4) . ?
C2 C11 1.540(5) . ?
C2 C3 1.541(4) . ?
C3 C4 1.510(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O2 1.454(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.384(5) . ?
C5 C10 1.390(5) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.392(5) . ?
C11 C12 1.396(4) . ?
C12 C13 1.392(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.371(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 O3 1.193(4) . ?
C21 O4 1.345(4) . ?
C21 C22 1.529(5) . ?
C22 C25 1.524(4) . ?
C22 C31 1.541(4) . ?
C22 C23 1.544(4) . ?
C23 C24 1.512(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O4 1.448(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.385(5) . ?
C25 C30 1.395(5) . ?
C26 C27 1.382(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.382(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.387(5) . ?
C31 C32 1.393(5) . ?
C32 C33 1.386(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.370(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(5) . ?
C35 H35 0.9500 . ?
C36 H36 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
O1 C1 O2 121.9(3) . . ?
O1 C1 C2 128.5(3) . . ?
O2 C1 C2 109.6(3) . . ?
C5 C2 C1 113.8(3) . . ?
C5 C2 C11 110.5(3) . . ?
C1 C2 C11 105.6(3) . . ?
C5 C2 C3 111.1(3) . . ?
C1 C2 C3 100.9(3) . . ?
C11 C2 C3 114.6(3) . . ?
C4 C3 C2 102.3(3) . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
O2 C4 C3 104.3(3) . . ?
O2 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
O2 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C10 118.7(3) . . ?
C6 C5 C2 118.5(3) . . ?
C10 C5 C2 122.7(3) . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C16 C11 C12 117.9(3) . . ?
C16 C11 C2 123.5(3) . . ?
C12 C11 C2 118.6(3) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O3 C21 O4 121.9(3) . . ?
O3 C21 C22 128.1(3) . . ?
O4 C21 C22 110.0(3) . . ?
C25 C22 C21 110.6(3) . . ?
C25 C22 C31 110.3(2) . . ?
C21 C22 C31 108.2(3) . . ?
C25 C22 C23 116.1(3) . . ?
C21 C22 C23 100.5(3) . . ?
C31 C22 C23 110.5(3) . . ?
C24 C23 C22 101.8(3) . . ?
C24 C23 H23A 111.4 . . ?
C22 C23 H23A 111.4 . . ?
C24 C23 H23B 111.4 . . ?
C22 C23 H23B 111.4 . . ?
H23A C23 H23B 109.3 . . ?
O4 C24 C23 104.8(3) . . ?
O4 C24 H24A 110.8 . . ?
C23 C24 H24A 110.8 . . ?
O4 C24 H24B 110.8 . . ?
C23 C24 H24B 110.8 . . ?
H24A C24 H24B 108.9 . . ?
C26 C25 C30 118.2(3) . . ?
C26 C25 C22 122.9(3) . . ?
C30 C25 C22 118.9(3) . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 119.6(3) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C28 C29 C30 120.2(4) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 120.7(3) . . ?
C29 C30 H30 119.6 . . ?
C25 C30 H30 119.6 . . ?
C36 C31 C32 118.6(3) . . ?
C36 C31 C22 118.5(3) . . ?
C32 C31 C22 122.9(3) . . ?
C33 C32 C31 120.6(3) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 120.4(4) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 119.6(3) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 120.6(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C31 120.2(4) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C1 O2 C4 110.9(3) . . ?
C21 O4 C24 110.3(3) . . ?

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 C1 C2 C5 43.5(5) . . . . ?
O2 C1 C2 C5 -138.9(3) . . . . ?
O1 C1 C2 C11 -77.8(4) . . . . ?
O2 C1 C2 C11 99.8(3) . . . . ?
O1 C1 C2 C3 162.6(4) . . . . ?
O2 C1 C2 C3 -19.8(3) . . . . ?
C5 C2 C3 C4 152.7(3) . . . . ?
C1 C2 C3 C4 31.7(3) . . . . ?
C11 C2 C3 C4 -81.2(4) . . . . ?
C2 C3 C4 O2 -33.6(3) . . . . ?
C1 C2 C5 C6 -164.4(3) . . . . ?
C11 C2 C5 C6 -45.9(4) . . . . ?
C3 C2 C5 C6 82.5(4) . . . . ?
C1 C2 C5 C10 19.0(4) . . . . ?
C11 C2 C5 C10 137.5(3) . . . . ?
C3 C2 C5 C10 -94.1(4) . . . . ?
C10 C5 C6 C7 -0.9(4) . . . . ?
C2 C5 C6 C7 -177.7(3) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C5 0.3(5) . . . . ?
C6 C5 C10 C9 0.7(5) . . . . ?
C2 C5 C10 C9 177.3(3) . . . . ?
C5 C2 C11 C16 111.1(3) . . . . ?
C1 C2 C11 C16 -125.4(3) . . . . ?
C3 C2 C11 C16 -15.3(4) . . . . ?
C5 C2 C11 C12 -66.6(4) . . . . ?
C1 C2 C11 C12 56.8(4) . . . . ?
C3 C2 C11 C12 166.9(3) . . . . ?
C16 C11 C12 C13 1.1(5) . . . . ?
C2 C11 C12 C13 178.9(3) . . . . ?
C11 C12 C13 C14 -1.1(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C11 -0.4(5) . . . . ?
C12 C11 C16 C15 -0.3(5) . . . . ?
C2 C11 C16 C15 -178.1(3) . . . . ?
O3 C21 C22 C25 36.0(5) . . . . ?
O4 C21 C22 C25 -145.3(3) . . . . ?
O3 C21 C22 C31 -85.0(4) . . . . ?
O4 C21 C22 C31 93.7(3) . . . . ?
O3 C21 C22 C23 159.2(3) . . . . ?
O4 C21 C22 C23 -22.1(3) . . . . ?
C25 C22 C23 C24 152.2(3) . . . . ?
C21 C22 C23 C24 32.9(3) . . . . ?
C31 C22 C23 C24 -81.2(3) . . . . ?
C22 C23 C24 O4 -33.8(3) . . . . ?
C21 C22 C25 C26 115.8(3) . . . . ?
C31 C22 C25 C26 -124.4(3) . . . . ?
C23 C22 C25 C26 2.2(5) . . . . ?
C21 C22 C25 C30 -64.1(4) . . . . ?
C31 C22 C25 C30 55.7(4) . . . . ?
C23 C22 C25 C30 -177.7(3) . . . . ?
C30 C25 C26 C27 2.3(5) . . . . ?
C22 C25 C26 C27 -177.6(3) . . . . ?
C25 C26 C27 C28 -0.7(5) . . . . ?
C26 C27 C28 C29 -1.2(6) . . . . ?
C27 C28 C29 C30 1.5(6) . . . . ?
C28 C29 C30 C25 0.1(5) . . . . ?
C26 C25 C30 C29 -2.0(5) . . . . ?
C22 C25 C30 C29 177.9(3) . . . . ?
C25 C22 C31 C36 55.9(4) . . . . ?
C21 C22 C31 C36 177.1(3) . . . . ?
C23 C22 C31 C36 -73.8(4) . . . . ?
C25 C22 C31 C32 -123.9(3) . . . . ?
C21 C22 C31 C32 -2.7(4) . . . . ?
C23 C22 C31 C32 106.4(3) . . . . ?
C36 C31 C32 C33 -1.1(5) . . . . ?
C22 C31 C32 C33 178.7(3) . . . . ?
C31 C32 C33 C34 0.4(5) . . . . ?
C32 C33 C34 C35 -0.1(5) . . . . ?
C33 C34 C35 C36 0.5(5) . . . . ?
C34 C35 C36 C31 -1.2(5) . . . . ?
C32 C31 C36 C35 1.5(5) . . . . ?
C22 C31 C36 C35 -178.3(3) . . . . ?
O1 C1 O2 C4 176.5(3) . . . . ?
C2 C1 O2 C4 -1.2(4) . . . . ?
C3 C4 O2 C1 22.5(4) . . . . ?
O3 C21 O4 C24 179.9(3) . . . . ?
C22 C21 O4 C24 1.1(4) . . . . ?
C23 C24 O4 C21 21.2(4) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_A2
_database_code_depnum_ccdc_archive 'CCDC 1891872'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29

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'

_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                   9.062(9)
_cell_length_b                   14.647(14)
_cell_length_c                   9.918(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.13(2)
_cell_angle_gamma                90
_cell_volume                     1309(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.5085
_cell_measurement_theta_max      30.961

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6332
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1454 (selected reflections only, before parameter refinement)
 R(int) =  0.0496(selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14653
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.490
_diffrn_reflns_theta_max         27.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3146
_reflns_number_gt                2848
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0470P)²+0.7828P] 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         3146
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.90562(13) 0.57628(8) 0.62694(12) 0.0122(2) Uani 1 1 d . . . . .
C2 C 0.84212(13) 0.64533(8) 0.72320(11) 0.0106(2) Uani 1 1 d . . . . .
C3 C 0.87380(14) 0.61035(8) 0.87236(12) 0.0136(2) Uani 1 1 d . . . . .
H3A H 0.9825 0.6095 0.8975 0.016 Uiso 1 1 calc R U . . .
H3B H 0.8305 0.6541 0.9332 0.016 Uiso 1 1 calc R U . . .
C4 C 0.81180(15) 0.51482(9) 0.89650(14) 0.0187(3) Uani 1 1 d . . . . .
H4A H 0.7037 0.5153 0.8752 0.028 Uiso 1 1 calc R U . . .
H4B H 0.8369 0.4976 0.9917 0.028 Uiso 1 1 calc R U . . .
H4C H 0.8553 0.4706 0.8380 0.028 Uiso 1 1 calc R U . . .
C5 C 0.92919(13) 0.73436(8) 0.69852(12) 0.0113(2) Uani 1 1 d . . . . .
C6 C 1.01141(13) 0.78208(8) 0.80408(12) 0.0144(2) Uani 1 1 d . . . . .
H6 H 1.0175 0.7593 0.8942 0.017 Uiso 1 1 calc R U . . .
C7 C 1.08461(14) 0.86337(9) 0.77659(13) 0.0176(3) Uani 1 1 d . . . . .
H7 H 1.1390 0.8957 0.8486 0.021 Uiso 1 1 calc R U . . .
C8 C 1.07839(14) 0.89710(9) 0.64492(14) 0.0178(3) Uani 1 1 d . . . . .
H8 H 1.1287 0.9520 0.6272 0.021 Uiso 1 1 calc R U . . .
C9 C 0.99745(15) 0.84969(9) 0.53843(13) 0.0173(3) Uani 1 1 d . . . . .
H9 H 0.9935 0.8721 0.4483 0.021 Uiso 1 1 calc R U . . .
C10 C 0.92273(14) 0.76941(8) 0.56547(12) 0.0145(2) Uani 1 1 d . . . . .
H10 H 0.8668 0.7380 0.4933 0.017 Uiso 1 1 calc R U . . .
C11 C 0.67364(13) 0.66249(8) 0.69094(11) 0.0109(2) Uani 1 1 d . . . . .
C12 C 0.57264(13) 0.59342(8) 0.64607(12) 0.0133(2) Uani 1 1 d . . . . .
H12 H 0.6086 0.5344 0.6269 0.016 Uiso 1 1 calc R U . . .
C13 C 0.41917(13) 0.61043(9) 0.62914(12) 0.0147(3) Uani 1 1 d . . . . .
H13 H 0.3526 0.5630 0.5982 0.018 Uiso 1 1 calc R U . . .
C14 C 0.36329(14) 0.69702(9) 0.65757(13) 0.0168(3) Uani 1 1 d . . . . .
H14 H 0.2595 0.7084 0.6461 0.020 Uiso 1 1 calc R U . . .
C15 C 0.46318(14) 0.76651(9) 0.70317(12) 0.0156(3) Uani 1 1 d . . . . .
H15 H 0.4271 0.8254 0.7230 0.019 Uiso 1 1 calc R U . . .
C16 C 0.61611(14) 0.74907(8) 0.71949(12) 0.0138(2) Uani 1 1 d . . . . .
H16 H 0.6826 0.7966 0.7505 0.017 Uiso 1 1 calc R U . . .
O1 O 1.03862(10) 0.54471(7) 0.67469(9) 0.0188(2) Uani 1 1 d . . . . .
H1 H 1.0706 0.5100 0.6170 0.028 Uiso 1 1 calc R U . . .
O2 O 0.84472(10) 0.55524(6) 0.51409(9) 0.0168(2) 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 O2 1.2330(18) . ?
C1 O1 1.3300(18) . ?
C1 C2 1.5436(18) . ?
C2 C11 1.547(2) . ?
C2 C5 1.557(2) . ?
C2 C3 1.563(2) . ?
C3 C4 1.536(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.4047(18) . ?
C5 C10 1.411(2) . ?
C6 C7 1.404(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.4043(19) . ?
C11 C16 1.411(2) . ?
C12 C13 1.405(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.405(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O1 H1 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
O2 C1 O1 122.48(11) . . ?
O2 C1 C2 124.40(12) . . ?
O1 C1 C2 113.02(11) . . ?
C1 C2 C11 113.79(10) . . ?
C1 C2 C5 102.88(11) . . ?
C11 C2 C5 109.70(10) . . ?
C1 C2 C3 109.13(11) . . ?
C11 C2 C3 109.07(9) . . ?
C5 C2 C3 112.23(10) . . ?
C4 C3 C2 114.38(10) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 118.79(12) . . ?
C6 C5 C2 122.48(11) . . ?
C10 C5 C2 118.72(10) . . ?
C7 C6 C5 120.09(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.71(12) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.73(13) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.80(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 120.86(11) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
C12 C11 C16 117.95(12) . . ?
C12 C11 C2 122.96(11) . . ?
C16 C11 C2 118.82(10) . . ?
C11 C12 C13 120.89(12) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 120.61(11) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.01(13) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 120.03(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 121.50(11) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C1 O1 H1 109.5 . . ?

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
O1 H1 O2 0.84 1.85 2.681(2) 173.3 3_766

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.233
_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_4
_database_code_depnum_ccdc_archive 'CCDC 1891868'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universit? di Bologna
Italy
;
_audit_update_record             
;
2019-01-18 deposited with the CCDC.	2019-03-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H34 Cl12 O2 Ti2'
_chemical_formula_weight         1079.88

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'
Ti Ti 0.2776 0.4457 '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                   17.897(3)
_cell_length_b                   10.5524(18)
_cell_length_c                   25.825(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.889(2)
_cell_angle_gamma                90
_cell_volume                     4666.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      2.291
_cell_measurement_theta_max      26.2325

_exptl_crystal_description       plate
_exptl_crystal_colour            bright-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             2176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2808
_exptl_absorpt_correction_T_max  0.4296
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1333 (selected reflections only, before parameter refinement)
 R(int) =  0.0727 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43028
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.234
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8248
_reflns_number_gt                6428
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.1030P)²+17.1211P] 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         8248
_refine_ls_number_parameters     512
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1896
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.055
_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
Ti1 Ti -0.12160(5) 0.49428(8) 0.20633(4) 0.0180(2) Uani 1 1 d . . . . .
Ti2 Ti 0.08779(5) 0.54989(8) 0.21457(4) 0.0176(2) Uani 1 1 d . . . . .
Cl1 Cl -0.18609(8) 0.55245(14) 0.12169(5) 0.0308(3) Uani 1 1 d . . . . .
Cl2 Cl -0.18966(7) 0.60988(13) 0.24829(5) 0.0258(3) Uani 1 1 d . . . . .
Cl3 Cl -0.18191(7) 0.30769(12) 0.20363(5) 0.0268(3) Uani 1 1 d . . . . .
Cl4 Cl 0.08340(8) 0.63048(13) 0.13349(5) 0.0267(3) Uani 1 1 d . . . . .
Cl5 Cl 0.16075(8) 0.70259(12) 0.26331(5) 0.0260(3) Uani 1 1 d . . . . .
Cl6 Cl 0.17754(7) 0.40460(13) 0.21334(5) 0.0254(3) Uani 1 1 d . . . . .
Cl7 Cl -0.02977(7) 0.67433(11) 0.21513(5) 0.0216(3) Uani 1 1 d . . . . .
Cl8 Cl -0.01856(7) 0.39613(11) 0.17108(5) 0.0204(3) Uani 1 1 d . . . . .
C1 C 0.0231(3) 0.4340(4) 0.3021(2) 0.0154(10) Uani 1 1 d . . . . .
O1 O 0.07584(19) 0.4724(3) 0.28239(14) 0.0190(7) Uani 1 1 d . . . . .
O2 O -0.04807(19) 0.4411(3) 0.27765(14) 0.0198(8) Uani 1 1 d . . . . .
C2 C 0.0501(3) 0.3802(5) 0.3598(2) 0.0185(10) Uani 1 1 d . . . . .
C3 C -0.0217(3) 0.3514(5) 0.3799(2) 0.0193(11) Uani 1 1 d . . . . .
C4 C -0.0769(3) 0.2639(5) 0.3517(2) 0.0230(11) Uani 1 1 d . . . . .
H4 H -0.0709 0.2254 0.3199 0.028 Uiso 1 1 calc R U . . .
C5 C -0.1403(3) 0.2325(6) 0.3696(2) 0.0315(13) Uani 1 1 d . . . . .
H5 H -0.1776 0.1728 0.3500 0.038 Uiso 1 1 calc R U . . .
C6 C -0.1494(4) 0.2872(7) 0.4154(3) 0.0430(17) Uani 1 1 d . . . . .
H6 H -0.1934 0.2668 0.4273 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0945(4) 0.3720(8) 0.4441(3) 0.0486(19) Uani 1 1 d . . . . .
H7 H -0.0999 0.4081 0.4765 0.058 Uiso 1 1 calc R U . . .
C8 C -0.0311(3) 0.4052(6) 0.4259(2) 0.0329(14) Uani 1 1 d . . . . .
H8 H 0.0058 0.4655 0.4455 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1023(3) 0.4832(5) 0.3941(2) 0.0209(11) Uani 1 1 d . . . . .
C10 C 0.0796(3) 0.6092(5) 0.3854(2) 0.0287(13) Uani 1 1 d . . . . .
H10 H 0.0324 0.6296 0.3584 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1246(4) 0.7061(6) 0.4154(3) 0.0371(15) Uani 1 1 d . . . . .
H11 H 0.1082 0.7918 0.4088 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1931(4) 0.6777(6) 0.4547(2) 0.0323(14) Uani 1 1 d . . . . .
H12 H 0.2244 0.7433 0.4753 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2156(3) 0.5532(6) 0.4638(2) 0.0338(14) Uani 1 1 d . . . . .
H13 H 0.2624 0.5331 0.4912 0.041 Uiso 1 1 calc R U . . .
C14 C 0.1710(3) 0.4566(5) 0.4337(2) 0.0247(12) Uani 1 1 d . . . . .
H14 H 0.1879 0.3712 0.4403 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0959(3) 0.2541(5) 0.3607(2) 0.0209(11) Uani 1 1 d . . . . .
C16 C 0.1329(3) 0.2227(6) 0.3222(2) 0.0316(13) Uani 1 1 d . . . . .
H16 H 0.1292 0.2782 0.2926 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1758(4) 0.1098(6) 0.3264(3) 0.0398(15) Uani 1 1 d . . . . .
H17 H 0.2006 0.0898 0.2995 0.048 Uiso 1 1 calc R U . . .
C18 C 0.1822(4) 0.0289(6) 0.3683(3) 0.0409(16) Uani 1 1 d . . . . .
H18 H 0.2111 -0.0476 0.3705 0.049 Uiso 1 1 calc R U . . .
C19 C 0.1463(4) 0.0587(6) 0.4079(3) 0.0408(16) Uani 1 1 d . . . . .
H19 H 0.1515 0.0034 0.4378 0.049 Uiso 1 1 calc R U . . .
C20 C 0.1030(4) 0.1694(5) 0.4037(2) 0.0325(13) Uani 1 1 d . . . . .
H20 H 0.0777 0.1881 0.4304 0.039 Uiso 1 1 calc R U . . .
C31 C 0.9605(3) 0.0817(5) 0.1236(2) 0.0201(11) Uani 1 1 d . . . . .
C32 C 0.9154(3) 0.1394(5) 0.0735(2) 0.0212(11) Uani 1 1 d . . . . .
C33 C 0.9380(3) 0.1224(5) 0.0259(2) 0.0237(11) Uani 1 1 d . . . . .
H33 H 0.9829 0.0731 0.0272 0.028 Uiso 1 1 calc R U . . .
C34 C 0.8959(3) 0.1765(5) -0.0222(2) 0.0273(12) Uani 1 1 d . . . . .
H34 H 0.9104 0.1613 -0.0542 0.033 Uiso 1 1 calc R U . . .
C35 C 0.8322(3) 0.2535(6) -0.0239(2) 0.0317(13) Uani 1 1 d . . . . .
H35 H 0.8040 0.2928 -0.0569 0.038 Uiso 1 1 calc R U . . .
C36 C 0.8097(3) 0.2729(5) 0.0223(2) 0.0308(13) Uani 1 1 d . . . . .
H36 H 0.7665 0.3264 0.0210 0.037 Uiso 1 1 calc R U . . .
C37 C 0.8497(3) 0.2148(5) 0.0706(2) 0.0283(12) Uani 1 1 d . . . . .
H37 H 0.8325 0.2261 0.1018 0.034 Uiso 1 1 calc R U . . .
C38 C 0.9245(3) 0.0391(5) 0.1633(2) 0.0209(11) Uani 1 1 d . . . . .
C39 C 0.8476(3) -0.0073(5) 0.1484(2) 0.0286(13) Uani 1 1 d . . . . .
H39 H 0.8178 -0.0085 0.1114 0.034 Uiso 1 1 calc R U . . .
C40 C 0.8155(4) -0.0508(6) 0.1871(3) 0.0369(15) Uani 1 1 d . . . . .
H40 H 0.7635 -0.0824 0.1767 0.044 Uiso 1 1 calc R U . . .
C41 C 0.8576(4) -0.0491(5) 0.2408(3) 0.0371(15) Uani 1 1 d . . . . .
H41 H 0.8344 -0.0793 0.2672 0.045 Uiso 1 1 calc R U . . .
C42 C 0.9345(4) -0.0034(5) 0.2572(2) 0.0324(14) Uani 1 1 d . . . . .
H42 H 0.9634 -0.0025 0.2944 0.039 Uiso 1 1 calc R U . . .
C43 C 0.9675(3) 0.0402(5) 0.2186(2) 0.0257(12) Uani 1 1 d . . . . .
H43 H 1.0195 0.0713 0.2292 0.031 Uiso 1 1 calc R U . . .
C44 C 1.0442(3) 0.0666(5) 0.1334(2) 0.0193(11) Uani 1 1 d . . . . .
C45 C 1.0873(3) 0.1570(5) 0.1143(2) 0.0230(11) Uani 1 1 d . . . . .
H45 H 1.0621 0.2305 0.0961 0.028 Uiso 1 1 calc R U . . .
C46 C 1.1664(3) 0.1395(5) 0.1218(2) 0.0265(12) Uani 1 1 d . . . . .
H46 H 1.1958 0.2017 0.1096 0.032 Uiso 1 1 calc R U . . .
C47 C 1.2025(3) 0.0306(5) 0.1472(2) 0.0252(12) Uani 1 1 d . . . . .
H47 H 1.2566 0.0176 0.1518 0.030 Uiso 1 1 calc R U . . .
C48 C 1.1605(3) -0.0594(5) 0.1660(2) 0.0240(11) Uani 1 1 d . . . . .
H48 H 1.1858 -0.1338 0.1833 0.029 Uiso 1 1 calc R U . . .
C49 C 1.0825(3) -0.0415(5) 0.1598(2) 0.0226(11) Uani 1 1 d . . . . .
H49 H 1.0542 -0.1028 0.1735 0.027 Uiso 1 1 calc R U . . .
C101 C 0.8792(12) 0.7620(17) 0.3930(6) 0.109(5) Uiso 0.659(12) 1 d D U P A 1
H10A H 0.8280 0.7820 0.3669 0.131 Uiso 0.659(12) 1 calc R U P A 1
H10B H 0.9033 0.6957 0.3759 0.131 Uiso 0.659(12) 1 calc R U P A 1
Cl21 Cl 0.9362(5) 0.8958(10) 0.3976(4) 0.174(4) Uiso 0.659(12) 1 d D U P A 1
Cl22 Cl 0.8603(4) 0.6945(6) 0.4463(2) 0.1001(19) Uiso 0.659(12) 1 d D U P A 1
C111 C 0.8694(19) 0.700(2) 0.3904(8) 0.090(6) Uiso 0.341(12) 1 d D U P A 2
H11A H 0.8124 0.7038 0.3726 0.108 Uiso 0.341(12) 1 calc R U P A 2
H11B H 0.8903 0.6187 0.3818 0.108 Uiso 0.341(12) 1 calc R U P A 2
Cl25 Cl 0.9171(5) 0.8282(9) 0.3719(4) 0.087(4) Uiso 0.341(12) 1 d D U P A 2
Cl26 Cl 0.8909(13) 0.723(2) 0.4591(7) 0.183(7) Uiso 0.341(12) 1 d D U P A 2
C201 C 0.9241(4) 0.6320(6) 0.0297(2) 0.0390(15) Uani 1 1 d . . . . .
H20A H 0.9805 0.6219 0.0338 0.047 Uiso 1 1 calc R U . . .
H20B H 0.9116 0.5804 0.0581 0.047 Uiso 1 1 calc R U . . .
Cl31 Cl 0.87144(15) 0.57510(17) -0.03298(7) 0.0668(6) Uani 1 1 d . U . . .
Cl32 Cl 0.90503(9) 0.79214(15) 0.03983(7) 0.0396(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
Ti1 O2 2.008(3) . ?
Ti1 Cl2 2.2165(15) . ?
Ti1 Cl3 2.2368(16) . ?
Ti1 Cl1 2.2406(16) . ?
Ti1 Cl7 2.4790(15) . ?
Ti1 Cl8 2.5054(15) . ?
Ti2 O1 2.000(3) . ?
Ti2 Cl5 2.2205(16) . ?
Ti2 Cl6 2.2273(15) . ?
Ti2 Cl4 2.2402(16) . ?
Ti2 Cl7 2.4836(15) . ?
Ti2 Cl8 2.5050(15) . ?
C1 O2 1.249(6) . ?
C1 O1 1.262(6) . ?
C1 C2 1.534(7) . ?
C2 C9 1.536(7) . ?
C2 C3 1.550(7) . ?
C2 C15 1.559(7) . ?
C3 C8 1.370(8) . ?
C3 C4 1.392(7) . ?
C4 C5 1.384(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(8) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.380(8) . ?
C9 C10 1.390(8) . ?
C10 C11 1.391(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.386(8) . ?
C15 C20 1.401(8) . ?
C16 C17 1.404(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.355(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(9) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C31 C38 1.432(7) . ?
C31 C32 1.446(7) . ?
C31 C44 1.454(7) . ?
C32 C37 1.403(8) . ?
C32 C33 1.413(7) . ?
C33 C34 1.376(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.388(8) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.406(7) . ?
C38 C43 1.410(8) . ?
C39 C40 1.369(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.374(9) . ?
C40 H40 0.9500 . ?
C41 C42 1.402(9) . ?
C41 H41 0.9500 . ?
C42 C43 1.378(8) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C49 1.401(7) . ?
C44 C45 1.404(7) . ?
C45 C46 1.383(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.387(8) . ?
C46 H46 0.9500 . ?
C47 C48 1.383(8) . ?
C47 H47 0.9500 . ?
C48 C49 1.372(7) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C101 Cl22 1.671(11) . ?
C101 Cl21 1.725(11) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C111 Cl26 1.717(13) . ?
C111 Cl25 1.736(13) . ?
C111 H11A 0.9900 . ?
C111 H11B 0.9900 . ?
C201 Cl31 1.728(6) . ?
C201 Cl32 1.758(6) . ?
C201 H20A 0.9900 . ?
C201 H20B 0.9900 . ?

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
O2 Ti1 Cl2 90.70(11) . . ?
O2 Ti1 Cl3 87.96(11) . . ?
Cl2 Ti1 Cl3 99.85(6) . . ?
O2 Ti1 Cl1 170.42(11) . . ?
Cl2 Ti1 Cl1 97.22(6) . . ?
Cl3 Ti1 Cl1 95.95(6) . . ?
O2 Ti1 Cl7 83.66(11) . . ?
Cl2 Ti1 Cl7 88.70(5) . . ?
Cl3 Ti1 Cl7 168.12(6) . . ?
Cl1 Ti1 Cl7 91.11(6) . . ?
O2 Ti1 Cl8 82.08(11) . . ?
Cl2 Ti1 Cl8 166.45(6) . . ?
Cl3 Ti1 Cl8 91.38(5) . . ?
Cl1 Ti1 Cl8 89.07(5) . . ?
Cl7 Ti1 Cl8 79.15(5) . . ?
O1 Ti2 Cl5 89.74(11) . . ?
O1 Ti2 Cl6 89.53(11) . . ?
Cl5 Ti2 Cl6 101.52(6) . . ?
O1 Ti2 Cl4 171.96(11) . . ?
Cl5 Ti2 Cl4 96.29(6) . . ?
Cl6 Ti2 Cl4 94.45(6) . . ?
O1 Ti2 Cl7 84.54(10) . . ?
Cl5 Ti2 Cl7 88.44(6) . . ?
Cl6 Ti2 Cl7 168.41(6) . . ?
Cl4 Ti2 Cl7 90.29(5) . . ?
O1 Ti2 Cl8 82.35(11) . . ?
Cl5 Ti2 Cl8 165.76(6) . . ?
Cl6 Ti2 Cl8 90.28(6) . . ?
Cl4 Ti2 Cl8 90.64(5) . . ?
Cl7 Ti2 Cl8 79.07(5) . . ?
Ti1 Cl7 Ti2 97.73(5) . . ?
Ti2 Cl8 Ti1 96.49(5) . . ?
O2 C1 O1 123.2(5) . . ?
O2 C1 C2 120.1(4) . . ?
O1 C1 C2 116.7(4) . . ?
C1 O1 Ti2 140.1(3) . . ?
C1 O2 Ti1 141.4(3) . . ?
C1 C2 C9 105.4(4) . . ?
C1 C2 C3 109.8(4) . . ?
C9 C2 C3 111.7(4) . . ?
C1 C2 C15 110.3(4) . . ?
C9 C2 C15 111.5(4) . . ?
C3 C2 C15 108.1(4) . . ?
C8 C3 C4 118.7(5) . . ?
C8 C3 C2 122.1(5) . . ?
C4 C3 C2 119.1(4) . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 119.7(6) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C7 C8 120.4(6) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C3 C8 C7 120.3(5) . . ?
C3 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C14 C9 C10 118.1(5) . . ?
C14 C9 C2 123.0(5) . . ?
C10 C9 C2 118.9(5) . . ?
C9 C10 C11 121.2(5) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.9(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.0(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 120.7(5) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C20 117.6(5) . . ?
C16 C15 C2 123.5(5) . . ?
C20 C15 C2 118.9(5) . . ?
C15 C16 C17 120.8(6) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 121.0(6) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.5(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 119.8(6) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 121.3(6) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C38 C31 C32 121.5(5) . . ?
C38 C31 C44 119.8(5) . . ?
C32 C31 C44 118.7(5) . . ?
C37 C32 C33 118.2(5) . . ?
C37 C32 C31 121.9(5) . . ?
C33 C32 C31 119.9(5) . . ?
C34 C33 C32 120.8(5) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 120.0(5) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C36 C35 C34 120.1(5) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 120.6(5) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C36 C37 C32 120.2(5) . . ?
C36 C37 H37 119.9 . . ?
C32 C37 H37 119.9 . . ?
C39 C38 C43 118.9(5) . . ?
C39 C38 C31 121.4(5) . . ?
C43 C38 C31 119.7(5) . . ?
C40 C39 C38 120.1(6) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 120.7(6) . . ?
C39 C40 H40 119.7 . . ?
C41 C40 H40 119.7 . . ?
C40 C41 C42 120.8(6) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C43 C42 C41 119.1(6) . . ?
C43 C42 H42 120.5 . . ?
C41 C42 H42 120.5 . . ?
C42 C43 C38 120.5(5) . . ?
C42 C43 H43 119.7 . . ?
C38 C43 H43 119.7 . . ?
C49 C44 C45 119.0(5) . . ?
C49 C44 C31 120.4(5) . . ?
C45 C44 C31 120.6(5) . . ?
C46 C45 C44 120.2(5) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C45 C46 C47 119.6(5) . . ?
C45 C46 H46 120.2 . . ?
C47 C46 H46 120.2 . . ?
C48 C47 C46 120.6(5) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C49 C48 C47 120.2(5) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C48 C49 C44 120.4(5) . . ?
C48 C49 H49 119.8 . . ?
C44 C49 H49 119.8 . . ?
Cl22 C101 Cl21 123.4(11) . . ?
Cl22 C101 H10A 106.5 . . ?
Cl21 C101 H10A 106.5 . . ?
Cl22 C101 H10B 106.5 . . ?
Cl21 C101 H10B 106.5 . . ?
H10A C101 H10B 106.5 . . ?
Cl26 C111 Cl25 101.2(12) . . ?
Cl26 C111 H11A 111.5 . . ?
Cl25 C111 H11A 111.5 . . ?
Cl26 C111 H11B 111.5 . . ?
Cl25 C111 H11B 111.5 . . ?
H11A C111 H11B 109.3 . . ?
Cl31 C201 Cl32 113.4(3) . . ?
Cl31 C201 H20A 108.9 . . ?
Cl32 C201 H20A 108.9 . . ?
Cl31 C201 H20B 108.9 . . ?
Cl32 C201 H20B 108.9 . . ?
H20A C201 H20B 107.7 . . ?

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
O2 C1 O1 Ti2 -1.8(8) . . . . ?
C2 C1 O1 Ti2 -179.9(3) . . . . ?
O1 C1 O2 Ti1 3.2(8) . . . . ?
C2 C1 O2 Ti1 -178.7(3) . . . . ?
O2 C1 C2 C9 -124.8(5) . . . . ?
O1 C1 C2 C9 53.4(5) . . . . ?
O2 C1 C2 C3 -4.3(6) . . . . ?
O1 C1 C2 C3 173.9(4) . . . . ?
O2 C1 C2 C15 114.7(5) . . . . ?
O1 C1 C2 C15 -67.1(5) . . . . ?
C1 C2 C3 C8 -122.2(5) . . . . ?
C9 C2 C3 C8 -5.6(7) . . . . ?
C15 C2 C3 C8 117.4(6) . . . . ?
C1 C2 C3 C4 60.7(6) . . . . ?
C9 C2 C3 C4 177.3(4) . . . . ?
C15 C2 C3 C4 -59.7(6) . . . . ?
C8 C3 C4 C5 0.4(8) . . . . ?
C2 C3 C4 C5 177.7(5) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C4 C5 C6 C7 -1.1(10) . . . . ?
C5 C6 C7 C8 1.9(12) . . . . ?
C4 C3 C8 C7 0.4(9) . . . . ?
C2 C3 C8 C7 -176.7(6) . . . . ?
C6 C7 C8 C3 -1.6(11) . . . . ?
C1 C2 C9 C14 -139.1(5) . . . . ?
C3 C2 C9 C14 101.7(6) . . . . ?
C15 C2 C9 C14 -19.4(7) . . . . ?
C1 C2 C9 C10 41.3(6) . . . . ?
C3 C2 C9 C10 -77.9(6) . . . . ?
C15 C2 C9 C10 161.0(5) . . . . ?
C14 C9 C10 C11 0.2(8) . . . . ?
C2 C9 C10 C11 179.8(5) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C10 C11 C12 C13 -0.4(9) . . . . ?
C11 C12 C13 C14 0.8(9) . . . . ?
C10 C9 C14 C13 0.2(8) . . . . ?
C2 C9 C14 C13 -179.4(5) . . . . ?
C12 C13 C14 C9 -0.8(8) . . . . ?
C1 C2 C15 C16 23.5(7) . . . . ?
C9 C2 C15 C16 -93.2(6) . . . . ?
C3 C2 C15 C16 143.6(5) . . . . ?
C1 C2 C15 C20 -159.1(5) . . . . ?
C9 C2 C15 C20 84.2(6) . . . . ?
C3 C2 C15 C20 -39.0(6) . . . . ?
C20 C15 C16 C17 0.1(8) . . . . ?
C2 C15 C16 C17 177.6(5) . . . . ?
C15 C16 C17 C18 -0.2(10) . . . . ?
C16 C17 C18 C19 -0.5(10) . . . . ?
C17 C18 C19 C20 1.3(10) . . . . ?
C18 C19 C20 C15 -1.5(9) . . . . ?
C16 C15 C20 C19 0.8(8) . . . . ?
C2 C15 C20 C19 -176.8(5) . . . . ?
C38 C31 C32 C37 33.6(7) . . . . ?
C44 C31 C32 C37 -146.7(5) . . . . ?
C38 C31 C32 C33 -147.7(5) . . . . ?
C44 C31 C32 C33 32.0(7) . . . . ?
C37 C32 C33 C34 -1.2(8) . . . . ?
C31 C32 C33 C34 -180.0(5) . . . . ?
C32 C33 C34 C35 2.8(8) . . . . ?
C33 C34 C35 C36 -1.8(8) . . . . ?
C34 C35 C36 C37 -0.8(9) . . . . ?
C35 C36 C37 C32 2.4(8) . . . . ?
C33 C32 C37 C36 -1.4(8) . . . . ?
C31 C32 C37 C36 177.3(5) . . . . ?
C32 C31 C38 C39 31.6(7) . . . . ?
C44 C31 C38 C39 -148.0(5) . . . . ?
C32 C31 C38 C43 -150.0(5) . . . . ?
C44 C31 C38 C43 30.3(7) . . . . ?
C43 C38 C39 C40 -0.2(8) . . . . ?
C31 C38 C39 C40 178.1(5) . . . . ?
C38 C39 C40 C41 0.3(9) . . . . ?
C39 C40 C41 C42 -0.3(9) . . . . ?
C40 C41 C42 C43 0.1(9) . . . . ?
C41 C42 C43 C38 0.1(8) . . . . ?
C39 C38 C43 C42 0.0(8) . . . . ?
C31 C38 C43 C42 -178.4(5) . . . . ?
C38 C31 C44 C49 36.9(7) . . . . ?
C32 C31 C44 C49 -142.7(5) . . . . ?
C38 C31 C44 C45 -146.0(5) . . . . ?
C32 C31 C44 C45 34.3(7) . . . . ?
C49 C44 C45 C46 -0.4(7) . . . . ?
C31 C44 C45 C46 -177.5(5) . . . . ?
C44 C45 C46 C47 1.5(8) . . . . ?
C45 C46 C47 C48 -1.2(8) . . . . ?
C46 C47 C48 C49 -0.2(8) . . . . ?
C47 C48 C49 C44 1.4(8) . . . . ?
C45 C44 C49 C48 -1.1(7) . . . . ?
C31 C44 C49 C48 176.0(5) . . . . ?

_refine_diff_density_max         2.805
_refine_diff_density_min         -1.361
_refine_diff_density_rms         0.135

