# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1Me
_database_code_depnum_ccdc_archive 'CCDC 1945530'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_yan_exp421_0ma_a

_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            'C14 H17 Br O4'
_chemical_formula_weight         329.18

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   21.874(5)
_cell_length_b                   15.366(3)
_cell_length_c                   8.915(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2996.4(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.596
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.336
_exptl_absorpt_coefficient_mu    2.750
_shelx_estimated_absorpt_T_min   0.291
_shelx_estimated_absorpt_T_max   0.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33840
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3737
_reflns_number_gt                3279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+1.7946P] 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         3737
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.31356(2) 0.68218(2) 0.56528(2) 0.03584(7) Uani 1 1 d . . . . .
O1 O 0.39211(6) 0.54864(8) 0.32176(18) 0.0448(3) Uani 1 1 d . . . . .
O2 O 0.28402(6) 0.87983(9) 0.56954(13) 0.0394(3) Uani 1 1 d . . . . .
O3 O 0.23097(6) 0.89726(10) 0.35791(16) 0.0467(3) Uani 1 1 d . . . . .
C3 C 0.41738(7) 0.73899(11) 0.18849(18) 0.0286(3) Uani 1 1 d . . . . .
H3 H 0.4497 0.7112 0.1356 0.034 Uiso 1 1 calc R U . . .
O4 O 0.46707(9) 0.61325(11) 0.4465(3) 0.0831(7) Uani 1 1 d . . . . .
C4 C 0.39460(7) 0.70051(11) 0.31768(19) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.41505(10) 0.46361(13) 0.3670(3) 0.0545(6) Uani 1 1 d . . . . .
H1A H 0.4551 0.4536 0.3210 0.082 Uiso 1 1 calc R U . . .
H1AB H 0.3865 0.4184 0.3339 0.082 Uiso 1 1 calc R U . . .
H1AC H 0.4190 0.4616 0.4764 0.082 Uiso 1 1 calc R U . . .
C2 C 0.42239(8) 0.61646(12) 0.3696(2) 0.0342(4) Uani 1 1 d . . . . .
C6 C 0.27423(8) 0.86861(11) 0.42393(18) 0.0301(3) Uani 1 1 d . . . . .
C5 C 0.34778(7) 0.74069(11) 0.39788(18) 0.0279(3) Uani 1 1 d . . . . .
C7 C 0.23419(10) 0.92094(15) 0.6506(2) 0.0489(5) Uani 1 1 d . . . . .
H7A H 0.2282 0.9802 0.6128 0.073 Uiso 1 1 calc R U . . .
H7AB H 0.2441 0.9231 0.7577 0.073 Uiso 1 1 calc R U . . .
H7AC H 0.1966 0.8873 0.6359 0.073 Uiso 1 1 calc R U . . .
C8 C 0.32481(8) 0.81981(10) 0.34830(19) 0.0276(3) Uani 1 1 d . . . . .
C10 C 0.39405(7) 0.81750(10) 0.13416(18) 0.0273(3) Uani 1 1 d . . . . .
C9 C 0.41929(8) 0.85588(11) -0.01190(19) 0.0325(3) Uani 1 1 d . . . . .
C11 C 0.38743(11) 0.94125(16) -0.0540(2) 0.0521(6) Uani 1 1 d . . . . .
H11A H 0.4046 0.9634 -0.1482 0.078 Uiso 1 1 calc R U . . .
H11B H 0.3938 0.9842 0.0258 0.078 Uiso 1 1 calc R U . . .
H11C H 0.3435 0.9308 -0.0666 0.078 Uiso 1 1 calc R U . . .
C12 C 0.48749(9) 0.87495(14) 0.0077(3) 0.0471(5) Uani 1 1 d . . . . .
H12A H 0.5095 0.8204 0.0262 0.071 Uiso 1 1 calc R U . . .
H12B H 0.4933 0.9143 0.0931 0.071 Uiso 1 1 calc R U . . .
H12C H 0.5034 0.9024 -0.0835 0.071 Uiso 1 1 calc R U . . .
C15 C 0.34763(7) 0.85654(10) 0.21626(18) 0.0278(3) Uani 1 1 d . . . . .
H15 H 0.3308 0.9099 0.1816 0.033 Uiso 1 1 calc R U . . .
C14 C 0.41022(16) 0.78957(17) -0.1378(2) 0.0678(8) Uani 1 1 d . . . . .
H14A H 0.3667 0.7753 -0.1464 0.102 Uiso 1 1 calc R U . . .
H14B H 0.4334 0.7367 -0.1149 0.102 Uiso 1 1 calc R U . . .
H14C H 0.4247 0.8143 -0.2326 0.102 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
Br1 C5 1.8962(16) . ?
O1 C2 1.306(2) . ?
O1 C1 1.456(2) . ?
O2 C6 1.327(2) . ?
O2 C7 1.452(2) . ?
O3 C6 1.198(2) . ?
C3 C4 1.387(2) . ?
C3 C10 1.397(2) . ?
C3 H3 0.9500 . ?
O4 C2 1.195(2) . ?
C4 C5 1.393(2) . ?
C4 C2 1.501(2) . ?
C1 H1A 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1AC 0.9800 . ?
C6 C8 1.497(2) . ?
C5 C8 1.388(2) . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C7 H7AC 0.9800 . ?
C8 C15 1.398(2) . ?
C10 C15 1.388(2) . ?
C10 C9 1.532(2) . ?
C9 C14 1.528(3) . ?
C9 C12 1.530(3) . ?
C9 C11 1.532(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 116.79(14) . . ?
C6 O2 C7 114.96(15) . . ?
C4 C3 C10 121.66(15) . . ?
C4 C3 H3 119.2 . . ?
C10 C3 H3 119.2 . . ?
C3 C4 C5 120.07(15) . . ?
C3 C4 C2 118.51(15) . . ?
C5 C4 C2 121.40(15) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1AB 109.5 . . ?
H1A C1 H1AB 109.5 . . ?
O1 C1 H1AC 109.5 . . ?
H1A C1 H1AC 109.5 . . ?
H1AB C1 H1AC 109.5 . . ?
O4 C2 O1 124.68(17) . . ?
O4 C2 C4 122.94(17) . . ?
O1 C2 C4 112.38(14) . . ?
O3 C6 O2 124.08(16) . . ?
O3 C6 C8 123.13(15) . . ?
O2 C6 C8 112.72(15) . . ?
C8 C5 C4 119.40(15) . . ?
C8 C5 Br1 121.54(13) . . ?
C4 C5 Br1 118.93(12) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7AB 109.5 . . ?
H7A C7 H7AB 109.5 . . ?
O2 C7 H7AC 109.5 . . ?
H7A C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
C5 C8 C15 119.53(15) . . ?
C5 C8 C6 124.27(15) . . ?
C15 C8 C6 116.16(14) . . ?
C15 C10 C3 117.25(15) . . ?
C15 C10 C9 123.04(14) . . ?
C3 C10 C9 119.71(15) . . ?
C14 C9 C12 109.75(19) . . ?
C14 C9 C11 109.38(19) . . ?
C12 C9 C11 107.91(16) . . ?
C14 C9 C10 108.69(15) . . ?
C12 C9 C10 109.13(15) . . ?
C11 C9 C10 111.97(15) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C15 C8 122.06(15) . . ?
C10 C15 H15 119.0 . . ?
C8 C15 H15 119.0 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C3 C4 C5 -0.8(2) . . . . ?
C10 C3 C4 C2 -179.54(15) . . . . ?
C1 O1 C2 O4 0.2(3) . . . . ?
C1 O1 C2 C4 -179.51(18) . . . . ?
C3 C4 C2 O4 85.4(3) . . . . ?
C5 C4 C2 O4 -93.4(3) . . . . ?
C3 C4 C2 O1 -94.91(19) . . . . ?
C5 C4 C2 O1 86.4(2) . . . . ?
C7 O2 C6 O3 7.4(3) . . . . ?
C7 O2 C6 C8 -175.49(16) . . . . ?
C3 C4 C5 C8 -0.8(2) . . . . ?
C2 C4 C5 C8 177.92(15) . . . . ?
C3 C4 C5 Br1 175.33(12) . . . . ?
C2 C4 C5 Br1 -6.0(2) . . . . ?
C4 C5 C8 C15 2.0(2) . . . . ?
Br1 C5 C8 C15 -173.99(12) . . . . ?
C4 C5 C8 C6 179.32(15) . . . . ?
Br1 C5 C8 C6 3.3(2) . . . . ?
O3 C6 C8 C5 -131.27(19) . . . . ?
O2 C6 C8 C5 51.6(2) . . . . ?
O3 C6 C8 C15 46.1(2) . . . . ?
O2 C6 C8 C15 -131.04(16) . . . . ?
C4 C3 C10 C15 1.1(2) . . . . ?
C4 C3 C10 C9 -177.96(15) . . . . ?
C15 C10 C9 C14 -120.7(2) . . . . ?
C3 C10 C9 C14 58.3(2) . . . . ?
C15 C10 C9 C12 119.62(18) . . . . ?
C3 C10 C9 C12 -61.4(2) . . . . ?
C15 C10 C9 C11 0.2(2) . . . . ?
C3 C10 C9 C11 179.21(17) . . . . ?
C3 C10 C15 C8 0.2(2) . . . . ?
C9 C10 C15 C8 179.22(15) . . . . ?
C5 C8 C15 C10 -1.8(2) . . . . ?
C6 C8 C15 C10 -179.28(15) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_3Me_a
_database_code_depnum_ccdc_archive 'CCDC 1945533'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_yan_exp369_3m

_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            'C26 H25 Cl8 N O4 Sb'
_chemical_formula_weight         820.82

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'
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   11.6398(8)
_cell_length_b                   18.4868(13)
_cell_length_c                   16.2027(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.070(3)
_cell_angle_gamma                90
_cell_volume                     3295.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      24.73

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             1628
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.794
_exptl_crystal_size_mid          0.727
_exptl_crystal_size_min          0.473
_exptl_absorpt_coefficient_mu    1.518
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_T_max  0.534
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15559
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.727
_diffrn_reflns_theta_max         24.729
_diffrn_reflns_theta_full        24.729
_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             5614
_reflns_number_gt                5196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+5.1831P] 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         5614
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.003
_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
Sb1 Sb -0.04770(2) 0.74903(2) 0.60006(2) 0.02458(8) Uani 1 1 d . . . . .
Cl1 Cl 0.62987(7) 1.08272(4) 0.49989(5) 0.03365(17) Uani 1 1 d . . . . .
Cl2 Cl 0.12172(7) 0.76560(5) 0.55234(6) 0.0419(2) Uani 1 1 d . . . . .
Cl3 Cl -0.06715(9) 0.87529(5) 0.61272(10) 0.0733(4) Uani 1 1 d . . . . .
Cl4 Cl -0.21653(7) 0.73052(5) 0.65072(5) 0.03866(19) Uani 1 1 d . . . . .
Cl5 Cl 0.08033(9) 0.74514(6) 0.74642(6) 0.0609(3) Uani 1 1 d . . . . .
Cl6 Cl -0.18021(9) 0.75204(7) 0.45586(7) 0.0673(4) Uani 1 1 d . . . . .
C1 C 0.4757(3) 0.64057(15) 0.7749(2) 0.0315(7) Uani 1 1 d . . . . .
Cl7 Cl -0.02640(8) 0.62294(4) 0.58980(6) 0.0435(2) Uani 1 1 d . . . . .
C8 C 0.3388(3) 0.63562(16) 0.7435(2) 0.0334(7) Uani 1 1 d . . . . .
H8A H 0.3059 0.6605 0.6872 0.050 Uiso 1 1 calc R U . . .
H8AB H 0.3073 0.6585 0.7863 0.050 Uiso 1 1 calc R U . . .
H8AC H 0.3142 0.5847 0.7366 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5280(4) 0.6078(2) 0.7101(4) 0.0855(19) Uani 1 1 d . . . . .
H9A H 0.4945 0.6325 0.6538 0.128 Uiso 1 1 calc R U . . .
H9AB H 0.5069 0.5563 0.7029 0.128 Uiso 1 1 calc R U . . .
H9AC H 0.6166 0.6131 0.7314 0.128 Uiso 1 1 calc R U . . .
C10 C 0.5218(2) 0.71881(14) 0.79165(18) 0.0224(6) Uani 1 1 d . . . . .
C11 C 0.4463(2) 0.77840(15) 0.76253(18) 0.0220(6) Uani 1 1 d . . . . .
H11 H 0.3621 0.7710 0.7328 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4916(2) 0.84872(14) 0.77616(17) 0.0197(5) Uani 1 1 d . . . . .
C13 C 0.6155(2) 0.86012(13) 0.81915(16) 0.0179(5) Uani 1 1 d . . . . .
C14 C 0.6931(2) 0.80113(15) 0.84900(17) 0.0202(5) Uani 1 1 d . . . . .
C15 C 0.6442(2) 0.73194(15) 0.83531(18) 0.0223(6) Uani 1 1 d . . . . .
H15 H 0.6966 0.6919 0.8567 0.027 Uiso 1 1 calc R U . . .
C16 C 0.8278(2) 0.81103(14) 0.88970(19) 0.0248(6) Uani 1 1 d . . . . .
C17 C 1.0126(3) 0.75474(18) 0.9671(3) 0.0555(12) Uani 1 1 d . . . . .
H17A H 1.0490 0.7738 0.9249 0.083 Uiso 1 1 calc R U . . .
H17B H 1.0447 0.7062 0.9855 0.083 Uiso 1 1 calc R U . . .
H17C H 1.0325 0.7867 1.0180 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4070(2) 0.91198(14) 0.75010(17) 0.0205(6) Uani 1 1 d . . . . .
C23 C 0.6394(2) 1.03869(15) 0.59613(17) 0.0228(6) Uani 1 1 d . . . . .
C22 C 0.6155(3) 1.07713(15) 0.66219(18) 0.0254(6) Uani 1 1 d . . . . .
H22 H 0.5931 1.1267 0.6545 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6248(2) 1.04214(14) 0.73921(18) 0.0239(6) Uani 1 1 d . . . . .
H21 H 0.6098 1.0676 0.7856 0.029 Uiso 1 1 calc R U . . .
C20 C 0.6564(2) 0.96896(14) 0.74866(17) 0.0189(5) Uani 1 1 d . . . . .
C25 C 0.6790(2) 0.93080(15) 0.68139(17) 0.0230(6) Uani 1 1 d . . . . .
H25 H 0.6996 0.8809 0.6881 0.028 Uiso 1 1 calc R U . . .
C26 C 0.7074(2) 0.96637(13) 0.90647(16) 0.0182(5) Uani 1 1 d . . . . .
C27 C 0.8012(3) 1.01772(15) 0.92029(18) 0.0250(6) Uani 1 1 d . . . . .
H27 H 0.8330 1.0287 0.8747 0.030 Uiso 1 1 calc R U . . .
C28 C 0.8463(3) 1.05176(15) 0.99908(18) 0.0265(6) Uani 1 1 d . . . . .
H28 H 0.9107 1.0857 1.0092 0.032 Uiso 1 1 calc R U . . .
C29 C 0.7968(2) 1.03596(14) 1.06426(17) 0.0233(6) Uani 1 1 d . . . . .
C30 C 0.7059(3) 0.98448(14) 1.05274(17) 0.0231(6) Uani 1 1 d . . . . .
H30 H 0.6742 0.9743 1.0985 0.028 Uiso 1 1 calc R U . . .
C31 C 0.6625(2) 0.94855(14) 0.97450(17) 0.0205(5) Uani 1 1 d . . . . .
H31 H 0.6026 0.9119 0.9664 0.025 Uiso 1 1 calc R U . . .
C32 C 0.5199(3) 0.59699(19) 0.8627(3) 0.0589(12) Uani 1 1 d . . . . .
H32A H 0.4951 0.5463 0.8515 0.088 Uiso 1 1 calc R U . . .
H32B H 0.4835 0.6177 0.9041 0.088 Uiso 1 1 calc R U . . .
H32C H 0.6087 0.5998 0.8875 0.088 Uiso 1 1 calc R U . . .
O33 O 0.8809(2) 0.75092(11) 0.92648(19) 0.0444(7) Uani 1 1 d . . . . .
O34 O 0.88150(18) 0.86578(11) 0.88701(17) 0.0431(6) Uani 1 1 d . . . . .
O35 O 0.41690(17) 0.96649(11) 0.79219(14) 0.0305(5) Uani 1 1 d . . . . .
O36 O 0.31898(17) 0.89949(10) 0.67485(12) 0.0263(4) Uani 1 1 d . . . . .
C37 C 0.2307(3) 0.95697(17) 0.6443(2) 0.0329(7) Uani 1 1 d . . . . .
H37A H 0.2721 1.0013 0.6366 0.049 Uiso 1 1 calc R U . . .
H37B H 0.1892 0.9655 0.6872 0.049 Uiso 1 1 calc R U . . .
H37C H 0.1709 0.9430 0.5883 0.049 Uiso 1 1 calc R U . . .
N38 N 0.66180(19) 0.93292(11) 0.82650(14) 0.0176(4) Uani 1 1 d . . . . .
Cl39 Cl 0.85260(7) 1.08158(4) 1.16145(5) 0.03679(19) Uani 1 1 d . . . . .
C24 C 0.6710(3) 0.96644(16) 0.60504(18) 0.0266(6) Uani 1 1 d . . . . .
H24 H 0.6872 0.9414 0.5588 0.032 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
Sb1 Cl6 2.3423(10) . ?
Sb1 Cl5 2.3537(9) . ?
Sb1 Cl7 2.3558(8) . ?
Sb1 Cl3 2.3605(9) . ?
Sb1 Cl2 2.3615(8) . ?
Sb1 Cl4 2.3889(8) . ?
Cl1 C23 1.730(3) . ?
C1 C9 1.502(5) . ?
C1 C8 1.510(4) . ?
C1 C10 1.536(4) . ?
C1 C32 1.569(5) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C8 H8AC 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C10 C15 1.389(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(4) . ?
C12 C18 1.498(4) . ?
C13 C14 1.398(4) . ?
C13 N38 1.440(3) . ?
C14 C15 1.388(4) . ?
C14 C16 1.500(4) . ?
C15 H15 0.9500 . ?
C16 O34 1.198(3) . ?
C16 O33 1.316(3) . ?
C17 O33 1.459(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O35 1.201(3) . ?
C18 O36 1.331(3) . ?
C23 C24 1.380(4) . ?
C23 C22 1.387(4) . ?
C22 C21 1.378(4) . ?
C22 H22 0.9500 . ?
C21 C20 1.397(4) . ?
C21 H21 0.9500 . ?
C20 C25 1.394(4) . ?
C20 N38 1.409(3) . ?
C25 C24 1.378(4) . ?
C25 H25 0.9500 . ?
C26 N38 1.376(3) . ?
C26 C31 1.405(4) . ?
C26 C27 1.408(4) . ?
C27 C28 1.365(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.389(4) . ?
C29 Cl39 1.716(3) . ?
C30 C31 1.373(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O36 C37 1.449(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C24 H24 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
Cl6 Sb1 Cl5 178.23(4) . . ?
Cl6 Sb1 Cl7 90.19(4) . . ?
Cl5 Sb1 Cl7 89.68(4) . . ?
Cl6 Sb1 Cl3 90.72(5) . . ?
Cl5 Sb1 Cl3 89.42(5) . . ?
Cl7 Sb1 Cl3 179.09(5) . . ?
Cl6 Sb1 Cl2 91.06(4) . . ?
Cl5 Sb1 Cl2 90.71(4) . . ?
Cl7 Sb1 Cl2 89.25(3) . . ?
Cl3 Sb1 Cl2 90.82(3) . . ?
Cl6 Sb1 Cl4 89.92(3) . . ?
Cl5 Sb1 Cl4 88.31(3) . . ?
Cl7 Sb1 Cl4 89.99(3) . . ?
Cl3 Sb1 Cl4 89.93(3) . . ?
Cl2 Sb1 Cl4 178.76(3) . . ?
C9 C1 C8 111.4(3) . . ?
C9 C1 C10 107.9(3) . . ?
C8 C1 C10 112.7(2) . . ?
C9 C1 C32 109.8(4) . . ?
C8 C1 C32 105.8(3) . . ?
C10 C1 C32 109.3(3) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8AB 109.5 . . ?
H8A C8 H8AB 109.5 . . ?
C1 C8 H8AC 109.5 . . ?
H8A C8 H8AC 109.5 . . ?
H8AB C8 H8AC 109.5 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
C1 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C15 C10 C11 117.6(2) . . ?
C15 C10 C1 119.7(2) . . ?
C11 C10 C1 122.7(2) . . ?
C10 C11 C12 121.3(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 119.7(2) . . ?
C11 C12 C18 120.2(2) . . ?
C13 C12 C18 120.0(2) . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 N38 118.7(2) . . ?
C14 C13 N38 121.2(2) . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 C16 119.8(2) . . ?
C13 C14 C16 121.4(2) . . ?
C14 C15 C10 122.7(3) . . ?
C14 C15 H15 118.6 . . ?
C10 C15 H15 118.6 . . ?
O34 C16 O33 123.8(3) . . ?
O34 C16 C14 124.8(3) . . ?
O33 C16 C14 111.4(2) . . ?
O33 C17 H17A 109.5 . . ?
O33 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O33 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O35 C18 O36 124.6(2) . . ?
O35 C18 C12 124.2(2) . . ?
O36 C18 C12 111.2(2) . . ?
C24 C23 C22 121.9(3) . . ?
C24 C23 Cl1 119.1(2) . . ?
C22 C23 Cl1 119.0(2) . . ?
C21 C22 C23 118.8(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C22 C21 C20 119.6(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C25 C20 C21 121.0(2) . . ?
C25 C20 N38 119.7(2) . . ?
C21 C20 N38 119.3(2) . . ?
C24 C25 C20 119.1(3) . . ?
C24 C25 H25 120.5 . . ?
C20 C25 H25 120.5 . . ?
N38 C26 C31 120.3(2) . . ?
N38 C26 C27 119.6(2) . . ?
C31 C26 C27 120.1(2) . . ?
C28 C27 C26 120.1(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.0(2) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C30 C29 C28 121.9(2) . . ?
C30 C29 Cl39 120.2(2) . . ?
C28 C29 Cl39 117.9(2) . . ?
C31 C30 C29 119.3(2) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C26 119.5(2) . . ?
C30 C31 H31 120.3 . . ?
C26 C31 H31 120.3 . . ?
C1 C32 H32A 109.5 . . ?
C1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C16 O33 C17 115.6(2) . . ?
C18 O36 C37 115.7(2) . . ?
O36 C37 H37A 109.5 . . ?
O36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C26 N38 C20 121.4(2) . . ?
C26 N38 C13 121.1(2) . . ?
C20 N38 C13 117.5(2) . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?

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
C9 C1 C10 C15 -68.2(4) . . . . ?
C8 C1 C10 C15 168.5(3) . . . . ?
C32 C1 C10 C15 51.2(4) . . . . ?
C9 C1 C10 C11 109.9(4) . . . . ?
C8 C1 C10 C11 -13.5(4) . . . . ?
C32 C1 C10 C11 -130.8(3) . . . . ?
C15 C10 C11 C12 0.3(4) . . . . ?
C1 C10 C11 C12 -177.7(3) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C10 C11 C12 C18 -175.4(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C18 C12 C13 C14 175.4(2) . . . . ?
C11 C12 C13 N38 175.3(2) . . . . ?
C18 C12 C13 N38 -8.7(4) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
N38 C13 C14 C15 -176.1(2) . . . . ?
C12 C13 C14 C16 175.6(2) . . . . ?
N38 C13 C14 C16 -0.2(4) . . . . ?
C13 C14 C15 C10 1.3(4) . . . . ?
C16 C14 C15 C10 -174.7(3) . . . . ?
C11 C10 C15 C14 -1.3(4) . . . . ?
C1 C10 C15 C14 176.8(3) . . . . ?
C15 C14 C16 O34 162.8(3) . . . . ?
C13 C14 C16 O34 -13.1(4) . . . . ?
C15 C14 C16 O33 -15.0(4) . . . . ?
C13 C14 C16 O33 169.1(3) . . . . ?
C11 C12 C18 O35 140.5(3) . . . . ?
C13 C12 C18 O35 -35.6(4) . . . . ?
C11 C12 C18 O36 -38.9(3) . . . . ?
C13 C12 C18 O36 145.0(2) . . . . ?
C24 C23 C22 C21 0.6(4) . . . . ?
Cl1 C23 C22 C21 -179.1(2) . . . . ?
C23 C22 C21 C20 -0.8(4) . . . . ?
C22 C21 C20 C25 0.2(4) . . . . ?
C22 C21 C20 N38 -177.9(2) . . . . ?
C21 C20 C25 C24 0.6(4) . . . . ?
N38 C20 C25 C24 178.7(2) . . . . ?
N38 C26 C27 C28 179.4(3) . . . . ?
C31 C26 C27 C28 -1.8(4) . . . . ?
C26 C27 C28 C29 -1.2(4) . . . . ?
C27 C28 C29 C30 2.6(4) . . . . ?
C27 C28 C29 Cl39 -178.2(2) . . . . ?
C28 C29 C30 C31 -0.7(4) . . . . ?
Cl39 C29 C30 C31 -180.0(2) . . . . ?
C29 C30 C31 C26 -2.4(4) . . . . ?
N38 C26 C31 C30 -177.6(2) . . . . ?
C27 C26 C31 C30 3.6(4) . . . . ?
O34 C16 O33 C17 1.4(5) . . . . ?
C14 C16 O33 C17 179.2(3) . . . . ?
O35 C18 O36 C37 -0.3(4) . . . . ?
C12 C18 O36 C37 179.1(2) . . . . ?
C31 C26 N38 C20 148.9(2) . . . . ?
C27 C26 N38 C20 -32.3(4) . . . . ?
C31 C26 N38 C13 -29.9(4) . . . . ?
C27 C26 N38 C13 148.9(2) . . . . ?
C25 C20 N38 C26 143.0(2) . . . . ?
C21 C20 N38 C26 -38.9(3) . . . . ?
C25 C20 N38 C13 -38.2(3) . . . . ?
C21 C20 N38 C13 139.9(2) . . . . ?
C12 C13 N38 C26 114.1(3) . . . . ?
C14 C13 N38 C26 -70.0(3) . . . . ?
C12 C13 N38 C20 -64.6(3) . . . . ?
C14 C13 N38 C20 111.2(3) . . . . ?
C20 C25 C24 C23 -0.8(4) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
Cl1 C23 C24 C25 180.0(2) . . . . ?

_refine_diff_density_max         0.876
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_2Me_a
_database_code_depnum_ccdc_archive 'CCDC 1945531'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_20180811_yan_exp389_0ma

_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            'C26 H25 Cl2 N O4'
_chemical_formula_weight         486.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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                   18.3830(16)
_cell_length_b                   13.3271(12)
_cell_length_c                   20.1022(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4924.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      24.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.6324
_shelx_estimated_absorpt_T_max   0.7451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6324
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44338
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.026
_diffrn_reflns_theta_max         24.830
_diffrn_reflns_theta_full        24.830
_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             4249
_reflns_number_gt                3744
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+3.2032P] 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         4249
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cl1 Cl 0.50101(3) 0.01474(5) 0.09340(3) 0.0679(2) Uani 1 1 d . . . . .
Cl2 Cl 0.20848(4) 0.48044(6) -0.22414(3) 0.0767(2) Uani 1 1 d . . . . .
O1 O 0.13629(7) 0.07979(10) -0.03060(6) 0.0396(3) Uani 1 1 d . . . . .
O2 O 0.02251(8) 0.13664(13) -0.02749(8) 0.0604(5) Uani 1 1 d . . . . .
O3 O 0.29318(7) 0.30053(12) 0.19818(6) 0.0498(4) Uani 1 1 d . . . . .
O4 O 0.29128(6) 0.37460(9) 0.09872(6) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.23058(7) 0.22510(10) 0.01619(6) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.03596(15) 0.2782(3) 0.28653(13) 0.0905(11) Uani 1 1 d . . . . .
H5 H 0.0489 0.3491 0.2815 0.136 Uiso 1 1 calc R U . . .
H1 H 0.0789 0.2401 0.3005 0.136 Uiso 1 1 calc R U . . .
H6 H -0.0023 0.2715 0.3202 0.136 Uiso 1 1 calc R U . . .
C2 C 0.00895(10) 0.23815(18) 0.22132(10) 0.0453(5) Uani 1 1 d . . . . .
C3 C 0.06795(9) 0.23836(14) 0.16737(9) 0.0335(4) Uani 1 1 d . . . . .
C4 C 0.13813(9) 0.27390(13) 0.17807(8) 0.0320(4) Uani 1 1 d . . . . .
H14 H 0.1506 0.2992 0.2208 0.038 Uiso 1 1 calc R U . . .
C5 C 0.19076(9) 0.27360(12) 0.12818(8) 0.0273(4) Uani 1 1 d . . . . .
C6 C 0.17571(9) 0.23158(12) 0.06596(8) 0.0255(3) Uani 1 1 d . . . . .
C7 C 0.29543(8) 0.17439(12) 0.03234(8) 0.0258(4) Uani 1 1 d . . . . .
C8 C 0.36250(9) 0.20307(14) 0.00624(9) 0.0342(4) Uani 1 1 d . . . . .
H24 H 0.3650 0.2571 -0.0245 0.041 Uiso 1 1 calc R U . . .
C9 C 0.42536(10) 0.15368(15) 0.02461(10) 0.0409(5) Uani 1 1 d . . . . .
H25 H 0.4708 0.1726 0.0059 0.049 Uiso 1 1 calc R U . . .
C10 C 0.42187(10) 0.07687(15) 0.07023(9) 0.0387(4) Uani 1 1 d . . . . .
C11 C -0.05655(14) 0.2955(3) 0.19755(15) 0.0993(12) Uani 1 1 d . . . . .
H3 H -0.0960 0.2887 0.2301 0.149 Uiso 1 1 calc R U . . .
H2 H -0.0725 0.2686 0.1546 0.149 Uiso 1 1 calc R U . . .
H4 H -0.0439 0.3665 0.1925 0.149 Uiso 1 1 calc R U . . .
C12 C -0.0138(2) 0.1282(3) 0.23350(15) 0.1014(12) Uani 1 1 d . . . . .
H7 H -0.0519 0.1260 0.2676 0.152 Uiso 1 1 calc R U . . .
H9 H 0.0284 0.0895 0.2486 0.152 Uiso 1 1 calc R U . . .
H8 H -0.0325 0.0993 0.1921 0.152 Uiso 1 1 calc R U . . .
C13 C 0.05323(9) 0.20025(13) 0.10445(8) 0.0319(4) Uani 1 1 d . . . . .
H13 H 0.0052 0.1782 0.0949 0.038 Uiso 1 1 calc R U . . .
C14 C 0.10576(9) 0.19307(12) 0.05487(8) 0.0279(4) Uani 1 1 d . . . . .
C15 C 0.08339(9) 0.13648(13) -0.00608(9) 0.0325(4) Uani 1 1 d . . . . .
C16 C 0.11666(13) 0.01639(18) -0.08608(11) 0.0544(6) Uani 1 1 d . . . . .
H11 H 0.0748 -0.0252 -0.0738 0.082 Uiso 1 1 calc R U . . .
H10 H 0.1579 -0.0269 -0.0976 0.082 Uiso 1 1 calc R U . . .
H12 H 0.1040 0.0583 -0.1244 0.082 Uiso 1 1 calc R U . . .
C17 C 0.26369(9) 0.31586(13) 0.14595(8) 0.0288(4) Uani 1 1 d . . . . .
C18 C 0.36384(9) 0.41225(15) 0.11094(9) 0.0384(4) Uani 1 1 d . . . . .
H17 H 0.3640 0.4521 0.1519 0.058 Uiso 1 1 calc R U . . .
H16 H 0.3792 0.4544 0.0735 0.058 Uiso 1 1 calc R U . . .
H15 H 0.3976 0.3557 0.1157 0.058 Uiso 1 1 calc R U . . .
C19 C 0.22309(9) 0.28358(12) -0.04208(8) 0.0273(4) Uani 1 1 d . . . . .
C20 C 0.19059(9) 0.37745(13) -0.03911(9) 0.0320(4) Uani 1 1 d . . . . .
H21 H 0.1721 0.4013 0.0021 0.038 Uiso 1 1 calc R U . . .
C21 C 0.18478(10) 0.43657(15) -0.09517(9) 0.0394(4) Uani 1 1 d . . . . .
H20 H 0.1620 0.5005 -0.0928 0.047 Uiso 1 1 calc R U . . .
C22 C 0.21228(11) 0.40215(17) -0.15473(9) 0.0438(5) Uani 1 1 d . . . . .
C23 C 0.24369(11) 0.30865(17) -0.15955(9) 0.0444(5) Uani 1 1 d . . . . .
H19 H 0.2620 0.2854 -0.2010 0.053 Uiso 1 1 calc R U . . .
C24 C 0.24830(10) 0.24880(15) -0.10328(8) 0.0366(4) Uani 1 1 d . . . . .
H18 H 0.2688 0.1835 -0.1065 0.044 Uiso 1 1 calc R U . . .
C25 C 0.29348(9) 0.09595(13) 0.07806(9) 0.0324(4) Uani 1 1 d . . . . .
H22 H 0.2482 0.0751 0.0961 0.039 Uiso 1 1 calc R U . . .
C26 C 0.35658(10) 0.04818(14) 0.09749(9) 0.0381(4) Uani 1 1 d . . . . .
H23 H 0.3549 -0.0042 0.1295 0.046 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 C10 1.7376(18) . ?
Cl2 C22 1.7437(19) . ?
O1 C15 1.326(2) . ?
O1 C16 1.445(2) . ?
O2 C15 1.199(2) . ?
O3 C17 1.199(2) . ?
O4 C17 1.331(2) . ?
O4 C18 1.446(2) . ?
N1 C7 1.408(2) . ?
N1 C19 1.414(2) . ?
N1 C6 1.423(2) . ?
C1 C2 1.500(3) . ?
C1 H5 0.9800 . ?
C1 H1 0.9800 . ?
C1 H6 0.9800 . ?
C2 C11 1.504(3) . ?
C2 C3 1.534(2) . ?
C2 C12 1.544(4) . ?
C3 C13 1.390(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.393(2) . ?
C4 H14 0.9500 . ?
C5 C6 1.398(2) . ?
C5 C17 1.497(2) . ?
C6 C14 1.402(2) . ?
C7 C25 1.392(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.380(3) . ?
C8 H24 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H25 0.9500 . ?
C10 C26 1.374(3) . ?
C11 H3 0.9800 . ?
C11 H2 0.9800 . ?
C11 H4 0.9800 . ?
C12 H7 0.9800 . ?
C12 H9 0.9800 . ?
C12 H8 0.9800 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.496(2) . ?
C16 H11 0.9800 . ?
C16 H10 0.9800 . ?
C16 H12 0.9800 . ?
C18 H17 0.9800 . ?
C18 H16 0.9800 . ?
C18 H15 0.9800 . ?
C19 C20 1.388(2) . ?
C19 C24 1.394(2) . ?
C20 C21 1.379(3) . ?
C20 H21 0.9500 . ?
C21 C22 1.378(3) . ?
C21 H20 0.9500 . ?
C22 C23 1.377(3) . ?
C23 C24 1.387(3) . ?
C23 H19 0.9500 . ?
C24 H18 0.9500 . ?
C25 C26 1.380(2) . ?
C25 H22 0.9500 . ?
C26 H23 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
C15 O1 C16 115.89(15) . . ?
C17 O4 C18 115.75(13) . . ?
C7 N1 C19 122.55(13) . . ?
C7 N1 C6 117.84(13) . . ?
C19 N1 C6 118.68(13) . . ?
C2 C1 H5 109.5 . . ?
C2 C1 H1 109.5 . . ?
H5 C1 H1 109.5 . . ?
C2 C1 H6 109.5 . . ?
H5 C1 H6 109.5 . . ?
H1 C1 H6 109.5 . . ?
C1 C2 C11 111.2(2) . . ?
C1 C2 C3 112.53(17) . . ?
C11 C2 C3 109.91(17) . . ?
C1 C2 C12 106.8(2) . . ?
C11 C2 C12 108.4(3) . . ?
C3 C2 C12 107.80(19) . . ?
C13 C3 C4 116.47(15) . . ?
C13 C3 C2 120.35(16) . . ?
C4 C3 C2 123.18(16) . . ?
C3 C4 C5 122.12(16) . . ?
C3 C4 H14 118.9 . . ?
C5 C4 H14 118.9 . . ?
C4 C5 C6 120.51(15) . . ?
C4 C5 C17 116.67(14) . . ?
C6 C5 C17 122.76(14) . . ?
C5 C6 C14 118.04(14) . . ?
C5 C6 N1 120.86(14) . . ?
C14 C6 N1 121.06(14) . . ?
C25 C7 C8 118.50(15) . . ?
C25 C7 N1 119.38(14) . . ?
C8 C7 N1 122.05(15) . . ?
C9 C8 C7 120.62(17) . . ?
C9 C8 H24 119.7 . . ?
C7 C8 H24 119.7 . . ?
C10 C9 C8 119.61(17) . . ?
C10 C9 H25 120.2 . . ?
C8 C9 H25 120.2 . . ?
C26 C10 C9 120.91(16) . . ?
C26 C10 Cl1 119.48(16) . . ?
C9 C10 Cl1 119.61(15) . . ?
C2 C11 H3 109.5 . . ?
C2 C11 H2 109.5 . . ?
H3 C11 H2 109.5 . . ?
C2 C11 H4 109.5 . . ?
H3 C11 H4 109.5 . . ?
H2 C11 H4 109.5 . . ?
C2 C12 H7 109.5 . . ?
C2 C12 H9 109.5 . . ?
H7 C12 H9 109.5 . . ?
C2 C12 H8 109.5 . . ?
H7 C12 H8 109.5 . . ?
H9 C12 H8 109.5 . . ?
C3 C13 C14 122.83(16) . . ?
C3 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C6 119.83(15) . . ?
C13 C14 C15 115.51(15) . . ?
C6 C14 C15 124.51(15) . . ?
O2 C15 O1 123.50(17) . . ?
O2 C15 C14 123.33(16) . . ?
O1 C15 C14 112.95(14) . . ?
O1 C16 H11 109.5 . . ?
O1 C16 H10 109.5 . . ?
H11 C16 H10 109.5 . . ?
O1 C16 H12 109.5 . . ?
H11 C16 H12 109.5 . . ?
H10 C16 H12 109.5 . . ?
O3 C17 O4 123.53(16) . . ?
O3 C17 C5 123.34(15) . . ?
O4 C17 C5 113.10(14) . . ?
O4 C18 H17 109.5 . . ?
O4 C18 H16 109.5 . . ?
H17 C18 H16 109.5 . . ?
O4 C18 H15 109.5 . . ?
H17 C18 H15 109.5 . . ?
H16 C18 H15 109.5 . . ?
C20 C19 C24 118.74(16) . . ?
C20 C19 N1 120.22(14) . . ?
C24 C19 N1 121.04(15) . . ?
C21 C20 C19 120.88(16) . . ?
C21 C20 H21 119.6 . . ?
C19 C20 H21 119.6 . . ?
C22 C21 C20 119.42(18) . . ?
C22 C21 H20 120.3 . . ?
C20 C21 H20 120.3 . . ?
C23 C22 C21 121.07(17) . . ?
C23 C22 Cl2 120.14(15) . . ?
C21 C22 Cl2 118.77(16) . . ?
C22 C23 C24 119.27(17) . . ?
C22 C23 H19 120.4 . . ?
C24 C23 H19 120.4 . . ?
C23 C24 C19 120.56(18) . . ?
C23 C24 H18 119.7 . . ?
C19 C24 H18 119.7 . . ?
C26 C25 C7 120.78(16) . . ?
C26 C25 H22 119.6 . . ?
C7 C25 H22 119.6 . . ?
C10 C26 C25 119.55(17) . . ?
C10 C26 H23 120.2 . . ?
C25 C26 H23 120.2 . . ?

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
C1 C2 C3 C13 177.6(2) . . . . ?
C11 C2 C3 C13 -57.9(3) . . . . ?
C12 C2 C3 C13 60.1(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C11 C2 C3 C4 123.3(3) . . . . ?
C12 C2 C3 C4 -118.7(2) . . . . ?
C13 C3 C4 C5 1.3(3) . . . . ?
C2 C3 C4 C5 -179.79(18) . . . . ?
C3 C4 C5 C6 -3.8(3) . . . . ?
C3 C4 C5 C17 178.84(16) . . . . ?
C4 C5 C6 C14 2.0(2) . . . . ?
C17 C5 C6 C14 179.25(15) . . . . ?
C4 C5 C6 N1 -175.90(15) . . . . ?
C17 C5 C6 N1 1.3(2) . . . . ?
C7 N1 C6 C5 56.3(2) . . . . ?
C19 N1 C6 C5 -112.95(17) . . . . ?
C7 N1 C6 C14 -121.54(17) . . . . ?
C19 N1 C6 C14 69.2(2) . . . . ?
C19 N1 C7 C25 -160.97(15) . . . . ?
C6 N1 C7 C25 30.2(2) . . . . ?
C19 N1 C7 C8 22.0(2) . . . . ?
C6 N1 C7 C8 -146.82(16) . . . . ?
C25 C7 C8 C9 1.0(3) . . . . ?
N1 C7 C8 C9 178.05(16) . . . . ?
C7 C8 C9 C10 -1.4(3) . . . . ?
C8 C9 C10 C26 0.4(3) . . . . ?
C8 C9 C10 Cl1 -179.96(14) . . . . ?
C4 C3 C13 C14 2.8(3) . . . . ?
C2 C3 C13 C14 -176.10(17) . . . . ?
C3 C13 C14 C6 -4.5(3) . . . . ?
C3 C13 C14 C15 171.25(16) . . . . ?
C5 C6 C14 C13 2.0(2) . . . . ?
N1 C6 C14 C13 179.87(15) . . . . ?
C5 C6 C14 C15 -173.39(15) . . . . ?
N1 C6 C14 C15 4.5(2) . . . . ?
C16 O1 C15 O2 0.1(3) . . . . ?
C16 O1 C15 C14 174.84(16) . . . . ?
C13 C14 C15 O2 33.7(3) . . . . ?
C6 C14 C15 O2 -150.80(19) . . . . ?
C13 C14 C15 O1 -141.06(16) . . . . ?
C6 C14 C15 O1 34.5(2) . . . . ?
C18 O4 C17 O3 6.0(2) . . . . ?
C18 O4 C17 C5 -175.94(14) . . . . ?
C4 C5 C17 O3 41.1(2) . . . . ?
C6 C5 C17 O3 -136.21(19) . . . . ?
C4 C5 C17 O4 -136.90(16) . . . . ?
C6 C5 C17 O4 45.8(2) . . . . ?
C7 N1 C19 C20 -135.15(17) . . . . ?
C6 N1 C19 C20 33.6(2) . . . . ?
C7 N1 C19 C24 44.5(2) . . . . ?
C6 N1 C19 C24 -146.75(16) . . . . ?
C24 C19 C20 C21 -1.6(3) . . . . ?
N1 C19 C20 C21 178.12(16) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C23 1.8(3) . . . . ?
C20 C21 C22 Cl2 -176.87(14) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
Cl2 C22 C23 C24 177.93(15) . . . . ?
C22 C23 C24 C19 -1.6(3) . . . . ?
C20 C19 C24 C23 2.7(3) . . . . ?
N1 C19 C24 C23 -177.02(16) . . . . ?
C8 C7 C25 C26 0.5(3) . . . . ?
N1 C7 C25 C26 -176.65(15) . . . . ?
C9 C10 C26 C25 1.1(3) . . . . ?
Cl1 C10 C26 C25 -178.58(14) . . . . ?
C7 C25 C26 C10 -1.5(3) . . . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_2iPr_b
_database_code_depnum_ccdc_archive 'CCDC 1945535'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_exp302_2_1m

_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            'C32 H33 F6 N O4'
_chemical_formula_weight         609.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   10.0890(4)
_cell_length_b                   11.8293(5)
_cell_length_c                   13.7884(6)
_cell_angle_alpha                97.5670(10)
_cell_angle_beta                 107.7540(10)
_cell_angle_gamma                95.2740(10)
_cell_volume                     1538.29(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   0.00087
_exptl_transmission_factor_max   0.00150
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.163
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.4319
_shelx_estimated_absorpt_T_max   0.7457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4319
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18837
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.754
_diffrn_reflns_theta_max         28.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7482
_reflns_number_gt                6554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.4645P] 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         7482
_refine_ls_number_parameters     451
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.035
_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
F1 F 0.1687(10) 0.6061(5) 0.2659(7) 0.0529(18) Uani 0.41(2) 1 d . U P A 1
F2 F 0.1981(9) 0.7754(8) 0.2431(7) 0.067(3) Uani 0.41(2) 1 d . U P A 1
F7 F 0.3109(9) 0.6586(10) 0.1950(6) 0.069(2) Uani 0.41(2) 1 d . U P A 1
F1A F 0.1382(9) 0.6308(10) 0.2840(7) 0.082(2) Uani 0.59(2) 1 d . U P A 2
F2A F 0.1975(4) 0.7851(5) 0.2367(4) 0.0307(9) Uani 0.59(2) 1 d . U P A 2
F7A F 0.2871(9) 0.6328(7) 0.2017(4) 0.0808(19) Uani 0.59(2) 1 d . U P A 2
F3 F 0.6076(6) 1.1516(7) 1.0119(7) 0.0534(15) Uani 0.50(3) 1 d . U P B 3
F4 F 0.8165(14) 1.2136(9) 1.0268(10) 0.074(2) Uani 0.50(3) 1 d . U P B 3
F5 F 0.7404(12) 1.0634(11) 1.0921(8) 0.0602(18) Uani 0.50(3) 1 d . U P B 3
F3A F 0.6117(8) 1.1654(9) 0.9996(8) 0.078(2) Uani 0.50(3) 1 d . U P B 4
F4A F 0.8334(12) 1.2010(11) 1.0402(10) 0.078(3) Uani 0.50(3) 1 d . U P B 4
F5A F 0.777(2) 1.0749(13) 1.0981(9) 0.089(3) Uani 0.50(3) 1 d . U P B 4
O1 O 0.84871(8) 0.64389(7) 0.88576(6) 0.02379(17) Uani 1 1 d . . . . .
O2 O 0.65073(8) 0.61803(7) 0.74931(6) 0.02281(17) Uani 1 1 d . . . . .
O3 O 0.82514(10) 0.95389(7) 0.54311(7) 0.02869(19) Uani 1 1 d . . . . .
O4 O 0.87589(9) 0.82449(7) 0.42913(6) 0.02308(17) Uani 1 1 d . . . . .
N1 N 0.70307(9) 0.80763(8) 0.65267(7) 0.01794(18) Uani 1 1 d . . . . .
C1 C 0.25506(13) 0.69337(10) 0.27280(10) 0.0314(3) Uani 1 1 d . . . . .
C2 C 0.37000(11) 0.72389(9) 0.37383(8) 0.0211(2) Uani 1 1 d . . . . .
C3 C 0.38472(11) 0.82929(9) 0.43696(9) 0.0212(2) Uani 1 1 d . . . . .
H3 H 0.3201 0.8820 0.4164 0.025 Uiso 1 1 calc R U . . .
C4 C 0.49363(11) 0.85750(9) 0.52984(8) 0.0200(2) Uani 1 1 d . . . . .
H4 H 0.5042 0.9300 0.5723 0.024 Uiso 1 1 calc R U . . .
C5 C 0.58792(10) 0.77981(9) 0.56138(8) 0.0176(2) Uani 1 1 d . . . . .
C6 C 0.82637(10) 0.75531(9) 0.65719(8) 0.0169(2) Uani 1 1 d . . . . .
C7 C 0.86910(10) 0.67912(9) 0.72632(8) 0.0173(2) Uani 1 1 d . . . . .
C8 C 0.99203(10) 0.63142(9) 0.73314(8) 0.0178(2) Uani 1 1 d . . . . .
H8 H 1.0234 0.5837 0.7835 0.021 Uiso 1 1 calc R U . . .
C9 C 1.07065(10) 0.65196(9) 0.66767(8) 0.0173(2) Uani 1 1 d . . . . .
C10 C 1.20263(11) 0.59413(9) 0.67539(8) 0.0191(2) Uani 1 1 d . . . . .
C11 C 1.26684(13) 0.61846(11) 0.59184(10) 0.0290(3) Uani 1 1 d . . . . .
H11A H 1.1990 0.5872 0.5236 0.043 Uiso 1 1 calc R U . . .
H11B H 1.3522 0.5820 0.6010 0.043 Uiso 1 1 calc R U . . .
H11C H 1.2905 0.7018 0.5974 0.043 Uiso 1 1 calc R U . . .
C12 C 0.72899(16) 1.11826(12) 1.01168(10) 0.0369(3) Uani 1 1 d . . . . .
C13 C 0.72108(13) 1.03747(10) 0.91673(9) 0.0255(2) Uani 1 1 d . . . . .
C14 C 0.59349(13) 0.97470(10) 0.85494(9) 0.0259(2) Uani 1 1 d . . . . .
H14 H 0.5109 0.9837 0.8729 0.031 Uiso 1 1 calc R U . . .
C15 C 0.58591(12) 0.89885(10) 0.76706(8) 0.0227(2) Uani 1 1 d . . . . .
H15 H 0.4982 0.8559 0.7252 0.027 Uiso 1 1 calc R U . . .
C16 C 0.70671(11) 0.88550(9) 0.74000(8) 0.0186(2) Uani 1 1 d . . . . .
C17 C 0.90534(11) 0.77931(9) 0.59344(8) 0.0179(2) Uani 1 1 d . . . . .
C18 C 1.02422(11) 0.72562(9) 0.59742(8) 0.0180(2) Uani 1 1 d . . . . .
H18 H 1.0745 0.7397 0.5511 0.022 Uiso 1 1 calc R U . . .
C19 C 0.77621(11) 0.64388(9) 0.78689(8) 0.0179(2) Uani 1 1 d . . . . .
C20 C 0.76466(13) 0.61700(11) 0.95212(9) 0.0268(2) Uani 1 1 d . . . . .
H20 H 0.6841 0.5557 0.9128 0.032 Uiso 1 1 calc R U . . .
C21 C 0.70944(17) 0.72527(13) 0.98509(11) 0.0399(3) Uani 1 1 d . . . . .
H21A H 0.6475 0.7499 0.9240 0.060 Uiso 1 1 calc R U . . .
H21B H 0.7884 0.7864 1.0206 0.060 Uiso 1 1 calc R U . . .
H21C H 0.6566 0.7097 1.0320 0.060 Uiso 1 1 calc R U . . .
C22 C 0.86096(18) 0.57294(17) 1.04137(12) 0.0488(4) Uani 1 1 d . . . . .
H22A H 0.8889 0.5006 1.0160 0.073 Uiso 1 1 calc R U . . .
H22B H 0.8120 0.5595 1.0911 0.073 Uiso 1 1 calc R U . . .
H22C H 0.9448 0.6300 1.0752 0.073 Uiso 1 1 calc R U . . .
C23 C 1.16517(13) 0.46346(10) 0.66324(10) 0.0280(2) Uani 1 1 d . . . . .
H23A H 1.0946 0.4345 0.5956 0.042 Uiso 1 1 calc R U . . .
H23B H 1.1272 0.4455 0.7178 0.042 Uiso 1 1 calc R U . . .
H23C H 1.2497 0.4267 0.6685 0.042 Uiso 1 1 calc R U . . .
C24 C 1.31206(12) 0.63959(11) 0.78176(9) 0.0288(3) Uani 1 1 d . . . . .
H24A H 1.3972 0.6036 0.7874 0.043 Uiso 1 1 calc R U . . .
H24B H 1.2736 0.6209 0.8359 0.043 Uiso 1 1 calc R U . . .
H24C H 1.3352 0.7233 0.7899 0.043 Uiso 1 1 calc R U . . .
C25 C 0.86386(11) 0.86347(9) 0.52109(8) 0.0199(2) Uani 1 1 d . . . . .
C26 C 0.82969(13) 0.89401(11) 0.34775(9) 0.0280(2) Uani 1 1 d . . . . .
H26 H 0.8547 0.9778 0.3779 0.034 Uiso 1 1 calc R U . . .
C27 C 0.67212(16) 0.86402(18) 0.29962(13) 0.0517(4) Uani 1 1 d . . . . .
H27A H 0.6387 0.9085 0.2440 0.078 Uiso 1 1 calc R U . . .
H27B H 0.6270 0.8825 0.3523 0.078 Uiso 1 1 calc R U . . .
H27C H 0.6484 0.7816 0.2714 0.078 Uiso 1 1 calc R U . . .
C28 C 0.90839(15) 0.86377(12) 0.27345(10) 0.0344(3) Uani 1 1 d . . . . .
H28A H 0.8854 0.7812 0.2457 0.052 Uiso 1 1 calc R U . . .
H28B H 1.0097 0.8827 0.3096 0.052 Uiso 1 1 calc R U . . .
H28C H 0.8815 0.9077 0.2167 0.052 Uiso 1 1 calc R U . . .
C29 C 0.46252(11) 0.64561(9) 0.40486(8) 0.0220(2) Uani 1 1 d . . . . .
H29 H 0.4520 0.5734 0.3620 0.026 Uiso 1 1 calc R U . . .
C30 C 0.56992(11) 0.67296(9) 0.49817(8) 0.0203(2) Uani 1 1 d . . . . .
H30 H 0.6321 0.6188 0.5196 0.024 Uiso 1 1 calc R U . . .
C31 C 0.83530(12) 0.94785(9) 0.80372(8) 0.0219(2) Uani 1 1 d . . . . .
H31 H 0.9185 0.9384 0.7867 0.026 Uiso 1 1 calc R U . . .
C32 C 0.84201(12) 1.02327(10) 0.89155(9) 0.0255(2) Uani 1 1 d . . . . .
H32 H 0.9297 1.0653 0.9345 0.031 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
F1 C1 1.262(8) . ?
F2 C1 1.226(10) . ?
F7 C1 1.390(6) . ?
F1A C1 1.394(7) . ?
F2A C1 1.358(5) . ?
F7A C1 1.277(6) . ?
F3 C12 1.322(6) . ?
F4 C12 1.318(10) . ?
F5 C12 1.337(10) . ?
F3A C12 1.328(7) . ?
F4A C12 1.295(9) . ?
F5A C12 1.331(11) . ?
O1 C19 1.3361(12) . ?
O1 C20 1.4690(13) . ?
O2 C19 1.2048(13) . ?
O3 C25 1.2053(13) . ?
O4 C25 1.3360(13) . ?
O4 C26 1.4653(13) . ?
N1 C5 1.4040(13) . ?
N1 C16 1.4051(13) . ?
N1 C6 1.4279(12) . ?
C1 C2 1.4904(15) . ?
C2 C29 1.3898(15) . ?
C2 C3 1.3912(15) . ?
C3 C4 1.3859(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3973(14) . ?
C4 H4 0.9500 . ?
C5 C30 1.4005(14) . ?
C6 C17 1.3925(15) . ?
C6 C7 1.3978(14) . ?
C7 C8 1.3917(14) . ?
C7 C19 1.4989(14) . ?
C8 C9 1.4007(15) . ?
C8 H8 0.9500 . ?
C9 C18 1.3920(14) . ?
C9 C10 1.5337(14) . ?
C10 C11 1.5289(15) . ?
C10 C23 1.5318(16) . ?
C10 C24 1.5346(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.4921(16) . ?
C13 C32 1.3849(17) . ?
C13 C14 1.3868(18) . ?
C14 C15 1.3869(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3953(15) . ?
C15 H15 0.9500 . ?
C16 C31 1.3990(15) . ?
C17 C18 1.3978(14) . ?
C17 C25 1.4984(14) . ?
C18 H18 0.9500 . ?
C20 C22 1.5043(17) . ?
C20 C21 1.5131(18) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 C28 1.5032(18) . ?
C26 C27 1.512(2) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.3819(15) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.3862(15) . ?
C31 H31 0.9500 . ?
C32 H32 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
C19 O1 C20 115.79(8) . . ?
C25 O4 C26 117.00(8) . . ?
C5 N1 C16 124.47(8) . . ?
C5 N1 C6 118.24(8) . . ?
C16 N1 C6 117.28(8) . . ?
F2 C1 F1 113.1(5) . . ?
F7A C1 F2A 109.5(4) . . ?
F2 C1 F7 102.1(5) . . ?
F1 C1 F7 101.9(5) . . ?
F7A C1 F1A 106.5(4) . . ?
F2A C1 F1A 100.3(5) . . ?
F2 C1 C2 113.9(4) . . ?
F1 C1 C2 114.5(4) . . ?
F7A C1 C2 114.8(3) . . ?
F2A C1 C2 114.0(2) . . ?
F7 C1 C2 109.7(4) . . ?
F1A C1 C2 110.5(3) . . ?
C29 C2 C3 120.08(10) . . ?
C29 C2 C1 119.30(10) . . ?
C3 C2 C1 120.62(10) . . ?
C4 C3 C2 120.05(10) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.33(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C30 119.00(10) . . ?
C4 C5 N1 121.80(9) . . ?
C30 C5 N1 119.15(9) . . ?
C17 C6 C7 119.26(9) . . ?
C17 C6 N1 120.79(9) . . ?
C7 C6 N1 119.95(9) . . ?
C8 C7 C6 119.81(9) . . ?
C8 C7 C19 120.91(9) . . ?
C6 C7 C19 119.15(9) . . ?
C7 C8 C9 121.68(9) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C18 C9 C8 117.54(9) . . ?
C18 C9 C10 122.59(9) . . ?
C8 C9 C10 119.88(9) . . ?
C11 C10 C23 107.96(9) . . ?
C11 C10 C9 112.25(9) . . ?
C23 C10 C9 109.62(9) . . ?
C11 C10 C24 108.82(9) . . ?
C23 C10 C24 109.45(9) . . ?
C9 C10 C24 108.71(8) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F4 C12 F3 105.8(6) . . ?
F4A C12 F3A 107.8(7) . . ?
F4A C12 F5A 92.8(15) . . ?
F3A C12 F5A 116.2(13) . . ?
F4 C12 F5 117.4(9) . . ?
F3 C12 F5 93.7(7) . . ?
F4A C12 C13 114.0(6) . . ?
F4 C12 C13 112.7(6) . . ?
F3 C12 C13 114.2(3) . . ?
F3A C12 C13 111.3(4) . . ?
F5A C12 C13 113.3(6) . . ?
F5 C12 C13 111.6(5) . . ?
C32 C13 C14 119.94(10) . . ?
C32 C13 C12 119.89(12) . . ?
C14 C13 C12 120.15(11) . . ?
C13 C14 C15 120.32(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 120.17(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C31 119.07(10) . . ?
C15 C16 N1 121.55(10) . . ?
C31 C16 N1 119.33(9) . . ?
C6 C17 C18 120.05(9) . . ?
C6 C17 C25 120.11(9) . . ?
C18 C17 C25 119.83(9) . . ?
C9 C18 C17 121.51(9) . . ?
C9 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
O2 C19 O1 124.64(10) . . ?
O2 C19 C7 123.08(9) . . ?
O1 C19 C7 112.27(9) . . ?
O1 C20 C22 106.22(10) . . ?
O1 C20 C21 108.42(10) . . ?
C22 C20 C21 113.08(12) . . ?
O1 C20 H20 109.7 . . ?
C22 C20 H20 109.7 . . ?
C21 C20 H20 109.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 O4 124.82(10) . . ?
O3 C25 C17 124.50(10) . . ?
O4 C25 C17 110.68(9) . . ?
O4 C26 C28 105.65(9) . . ?
O4 C26 C27 107.88(10) . . ?
C28 C26 C27 113.25(12) . . ?
O4 C26 H26 110.0 . . ?
C28 C26 H26 110.0 . . ?
C27 C26 H26 110.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C2 119.92(10) . . ?
C30 C29 H29 120.0 . . ?
C2 C29 H29 120.0 . . ?
C29 C30 C5 120.60(9) . . ?
C29 C30 H30 119.7 . . ?
C5 C30 H30 119.7 . . ?
C32 C31 C16 120.38(10) . . ?
C32 C31 H31 119.8 . . ?
C16 C31 H31 119.8 . . ?
C13 C32 C31 120.09(11) . . ?
C13 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?

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
F2 C1 C2 C29 -165.9(5) . . . . ?
F1 C1 C2 C29 61.7(5) . . . . ?
F7A C1 C2 C29 -34.7(6) . . . . ?
F2A C1 C2 C29 -162.11(19) . . . . ?
F7 C1 C2 C29 -52.1(5) . . . . ?
F1A C1 C2 C29 85.8(7) . . . . ?
F2 C1 C2 C3 14.4(5) . . . . ?
F1 C1 C2 C3 -118.0(5) . . . . ?
F7A C1 C2 C3 145.6(6) . . . . ?
F2A C1 C2 C3 18.2(2) . . . . ?
F7 C1 C2 C3 128.1(5) . . . . ?
F1A C1 C2 C3 -93.9(7) . . . . ?
C29 C2 C3 C4 1.47(17) . . . . ?
C1 C2 C3 C4 -178.79(11) . . . . ?
C2 C3 C4 C5 -0.95(17) . . . . ?
C3 C4 C5 C30 -0.51(16) . . . . ?
C3 C4 C5 N1 177.08(10) . . . . ?
C16 N1 C5 C4 28.22(16) . . . . ?
C6 N1 C5 C4 -150.56(10) . . . . ?
C16 N1 C5 C30 -154.19(10) . . . . ?
C6 N1 C5 C30 27.02(14) . . . . ?
C5 N1 C6 C17 65.27(13) . . . . ?
C16 N1 C6 C17 -113.60(11) . . . . ?
C5 N1 C6 C7 -114.82(11) . . . . ?
C16 N1 C6 C7 66.31(13) . . . . ?
C17 C6 C7 C8 2.18(15) . . . . ?
N1 C6 C7 C8 -177.73(9) . . . . ?
C17 C6 C7 C19 -173.69(9) . . . . ?
N1 C6 C7 C19 6.40(14) . . . . ?
C6 C7 C8 C9 -4.06(15) . . . . ?
C19 C7 C8 C9 171.73(9) . . . . ?
C7 C8 C9 C18 2.28(15) . . . . ?
C7 C8 C9 C10 -177.83(9) . . . . ?
C18 C9 C10 C11 -5.09(14) . . . . ?
C8 C9 C10 C11 175.03(10) . . . . ?
C18 C9 C10 C23 -125.06(11) . . . . ?
C8 C9 C10 C23 55.06(12) . . . . ?
C18 C9 C10 C24 115.34(11) . . . . ?
C8 C9 C10 C24 -64.54(12) . . . . ?
F4A C12 C13 C32 26.4(8) . . . . ?
F4 C12 C13 C32 39.6(7) . . . . ?
F3 C12 C13 C32 160.4(5) . . . . ?
F3A C12 C13 C32 148.6(7) . . . . ?
F5A C12 C13 C32 -78.1(11) . . . . ?
F5 C12 C13 C32 -94.9(5) . . . . ?
F4A C12 C13 C14 -155.1(8) . . . . ?
F4 C12 C13 C14 -141.8(7) . . . . ?
F3 C12 C13 C14 -21.0(5) . . . . ?
F3A C12 C13 C14 -32.8(7) . . . . ?
F5A C12 C13 C14 100.4(11) . . . . ?
F5 C12 C13 C14 83.7(5) . . . . ?
C32 C13 C14 C15 -0.93(18) . . . . ?
C12 C13 C14 C15 -179.50(11) . . . . ?
C13 C14 C15 C16 -0.23(17) . . . . ?
C14 C15 C16 C31 1.23(16) . . . . ?
C14 C15 C16 N1 178.66(10) . . . . ?
C5 N1 C16 C15 32.49(15) . . . . ?
C6 N1 C16 C15 -148.72(10) . . . . ?
C5 N1 C16 C31 -150.08(10) . . . . ?
C6 N1 C16 C31 28.71(14) . . . . ?
C7 C6 C17 C18 1.33(15) . . . . ?
N1 C6 C17 C18 -178.76(9) . . . . ?
C7 C6 C17 C25 -178.13(9) . . . . ?
N1 C6 C17 C25 1.78(15) . . . . ?
C8 C9 C18 C17 1.33(15) . . . . ?
C10 C9 C18 C17 -178.56(9) . . . . ?
C6 C17 C18 C9 -3.14(15) . . . . ?
C25 C17 C18 C9 176.33(9) . . . . ?
C20 O1 C19 O2 -3.97(15) . . . . ?
C20 O1 C19 C7 176.50(9) . . . . ?
C8 C7 C19 O2 -132.17(11) . . . . ?
C6 C7 C19 O2 43.65(15) . . . . ?
C8 C7 C19 O1 47.37(13) . . . . ?
C6 C7 C19 O1 -136.81(10) . . . . ?
C19 O1 C20 C22 156.55(12) . . . . ?
C19 O1 C20 C21 -81.63(13) . . . . ?
C26 O4 C25 O3 -4.14(16) . . . . ?
C26 O4 C25 C17 175.92(9) . . . . ?
C6 C17 C25 O3 42.24(16) . . . . ?
C18 C17 C25 O3 -137.23(12) . . . . ?
C6 C17 C25 O4 -137.82(10) . . . . ?
C18 C17 C25 O4 42.71(13) . . . . ?
C25 O4 C26 C28 156.05(10) . . . . ?
C25 O4 C26 C27 -82.54(14) . . . . ?
C3 C2 C29 C30 -0.51(17) . . . . ?
C1 C2 C29 C30 179.75(11) . . . . ?
C2 C29 C30 C5 -0.96(17) . . . . ?
C4 C5 C30 C29 1.47(16) . . . . ?
N1 C5 C30 C29 -176.18(10) . . . . ?
C15 C16 C31 C32 -1.08(16) . . . . ?
N1 C16 C31 C32 -178.57(10) . . . . ?
C14 C13 C32 C31 1.09(18) . . . . ?
C12 C13 C32 C31 179.65(11) . . . . ?
C16 C31 C32 C13 -0.07(17) . . . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_ak246_a
_database_code_depnum_ccdc_archive 'CCDC 1988910'
loop_
_audit_author_name
_audit_author_address
'chenting yan'
;Hiroshima University
Japan
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H31 N O6'
_chemical_formula_weight         477.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   10.3036(6)
_cell_length_b                   18.9257(11)
_cell_length_c                   13.0352(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.843(2)
_cell_angle_gamma                90
_cell_volume                     2532.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9281
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.05

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26160
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.137
_diffrn_reflns_theta_max         27.482
_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             5792
_reflns_number_gt                4146
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1046P)²+8.4575P] 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         5792
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   0.597
_refine_ls_restrained_S_all      0.597
_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
O1 O 0.87158(13) 0.32684(8) 0.28564(11) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.52917(15) 0.25403(9) 0.30446(13) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.62374(18) 0.20107(10) 0.29629(15) 0.0236(4) Uani 1 1 d . . . . .
O2 O 0.71565(15) 0.31311(8) 0.15612(12) 0.0334(4) Uani 1 1 d . . . . .
C2 C 0.74948(18) 0.21901(10) 0.27127(15) 0.0236(4) Uani 1 1 d . . . . .
C3 C 0.84603(18) 0.16796(11) 0.26984(15) 0.0257(4) Uani 1 1 d . . . . .
H3 H 0.931989 0.182080 0.258024 0.031 Uiso 1 1 calc R U . . .
O3 O 0.45229(15) 0.14126(8) 0.44200(12) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.82057(19) 0.09668(11) 0.28520(15) 0.0264(4) Uani 1 1 d . . . . .
O4 O 0.4174(2) 0.05317(11) 0.32937(18) 0.0640(6) Uani 1 1 d . . . . .
O5 O 0.69710(18) 0.48862(9) 0.53650(14) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.69471(19) 0.07894(11) 0.30613(16) 0.0278(4) Uani 1 1 d . . . . .
H5 H 0.673061 0.030550 0.313923 0.033 Uiso 1 1 calc R U . . .
C6 C 0.59939(18) 0.13001(11) 0.31602(15) 0.0261(4) Uani 1 1 d . . . . .
O6 O 0.02782(14) 0.25344(9) 0.10599(12) 0.0362(4) Uani 1 1 d . . . . .
C7 C 0.9302(2) 0.04217(12) 0.28162(19) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.9920(3) 0.04815(16) 0.1791(3) 0.0577(8) Uani 1 1 d . . . . .
H9A H 0.924938 0.041327 0.122052 0.087 Uiso 1 1 calc R U . . .
H9B H 1.059477 0.011895 0.175948 0.087 Uiso 1 1 calc R U . . .
H9C H 1.031186 0.095049 0.173706 0.087 Uiso 1 1 calc R U . . .
C8 C 1.0335(3) 0.05861(17) 0.3699(3) 0.0711(11) Uani 1 1 d . . . . .
H8A H 1.105551 0.024919 0.368537 0.107 Uiso 1 1 calc R U . . .
H8B H 0.994637 0.054699 0.435778 0.107 Uiso 1 1 calc R U . . .
H8C H 1.066362 0.106716 0.361966 0.107 Uiso 1 1 calc R U . . .
C10 C 0.8820(3) -0.03295(13) 0.2914(3) 0.0506(7) Uani 1 1 d . . . . .
H10A H 0.812647 -0.042338 0.236898 0.076 Uiso 1 1 calc R U . . .
H10B H 0.847878 -0.039193 0.358755 0.076 Uiso 1 1 calc R U . . .
H10C H 0.954141 -0.065909 0.284834 0.076 Uiso 1 1 calc R U . . .
C11 C 0.56568(17) 0.31581(10) 0.36248(15) 0.0238(4) Uani 1 1 d . . . . .
C12 C 0.5465(2) 0.38277(11) 0.32155(16) 0.0296(4) Uani 1 1 d . . . . .
H12 H 0.503860 0.388037 0.254468 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5883(2) 0.44234(11) 0.37666(17) 0.0308(5) Uani 1 1 d . . . . .
H13 H 0.574441 0.488078 0.347781 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6505(2) 0.43438(11) 0.47434(17) 0.0296(4) Uani 1 1 d . . . . .
C15 C 0.6680(2) 0.36747(11) 0.51727(16) 0.0303(4) Uani 1 1 d . . . . .
H15 H 0.709391 0.362254 0.584768 0.036 Uiso 1 1 calc R U . . .
C16 C 0.62498(18) 0.30842(11) 0.46158(15) 0.0254(4) Uani 1 1 d . . . . .
H16 H 0.636079 0.262738 0.491253 0.030 Uiso 1 1 calc R U . . .
C17 C 0.7011(3) 0.55659(12) 0.4912(2) 0.0449(6) Uani 1 1 d . . . . .
H17A H 0.747489 0.553934 0.428696 0.067 Uiso 1 1 calc R U . . .
H17B H 0.746536 0.589400 0.540079 0.067 Uiso 1 1 calc R U . . .
H17C H 0.612081 0.573411 0.473497 0.067 Uiso 1 1 calc R U . . .
C18 C 0.40272(18) 0.24915(10) 0.25343(15) 0.0235(4) Uani 1 1 d . . . . .
C19 C 0.29719(19) 0.27886(12) 0.29850(16) 0.0292(4) Uani 1 1 d . . . . .
H19 H 0.310390 0.299070 0.365276 0.035 Uiso 1 1 calc R U . . .
C20 C 0.17423(19) 0.27938(12) 0.24778(16) 0.0297(4) Uani 1 1 d . . . . .
H20 H 0.103871 0.300387 0.279277 0.036 Uiso 1 1 calc R U . . .
C21 C 0.15323(18) 0.24929(11) 0.15095(15) 0.0257(4) Uani 1 1 d . . . . .
C22 C 0.2560(2) 0.21762(12) 0.10639(16) 0.0296(4) Uani 1 1 d . . . . .
H22 H 0.241540 0.195406 0.041069 0.036 Uiso 1 1 calc R U . . .
C23 C 0.38033(19) 0.21833(11) 0.15733(16) 0.0289(4) Uani 1 1 d . . . . .
H23 H 0.450659 0.197391 0.125704 0.035 Uiso 1 1 calc R U . . .
C24 C 0.0030(2) 0.22744(16) 0.00354(19) 0.0437(6) Uani 1 1 d . . . . .
H24A H -0.089158 0.234254 -0.019442 0.066 Uiso 1 1 calc R U . . .
H24B H 0.024180 0.176991 0.001960 0.066 Uiso 1 1 calc R U . . .
H24C H 0.056995 0.253210 -0.042307 0.066 Uiso 1 1 calc R U . . .
C25 C 0.7500(3) 0.38176(13) 0.1176(2) 0.0463(6) Uani 1 1 d . . . . .
H25A H 0.841345 0.381341 0.101775 0.069 Uiso 1 1 calc R U . . .
H25B H 0.737924 0.417768 0.169974 0.069 Uiso 1 1 calc R U . . .
H25C H 0.694157 0.392630 0.055017 0.069 Uiso 1 1 calc R U . . .
C26 C 0.78618(18) 0.29245(11) 0.24189(15) 0.0245(4) Uani 1 1 d . . . . .
C27 C 0.4780(2) 0.10398(12) 0.35925(18) 0.0330(5) Uani 1 1 d . . . . .
C28 C 0.3480(3) 0.11521(16) 0.4989(2) 0.0535(7) Uani 1 1 d . . . . .
H28A H 0.264642 0.121643 0.457809 0.080 Uiso 1 1 calc R U . . .
H28B H 0.346776 0.141418 0.563607 0.080 Uiso 1 1 calc R U . . .
H28C H 0.361590 0.064871 0.513754 0.080 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
O1 C26 1.199(2) . ?
N1 C1 1.408(2) . ?
N1 C18 1.415(2) . ?
N1 C11 1.426(2) . ?
C1 C6 1.396(3) . ?
C1 C2 1.404(3) . ?
O2 C26 1.339(2) . ?
O2 C25 1.448(3) . ?
C2 C3 1.388(3) . ?
C2 C26 1.499(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
O3 C27 1.334(3) . ?
O3 C28 1.443(3) . ?
C4 C5 1.389(3) . ?
C4 C7 1.533(3) . ?
O4 C27 1.194(3) . ?
O5 C14 1.369(3) . ?
O5 C17 1.417(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C27 1.498(3) . ?
O6 C21 1.375(2) . ?
O6 C24 1.426(3) . ?
C7 C10 1.515(3) . ?
C7 C8 1.532(4) . ?
C7 C9 1.533(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.383(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.383(3) . ?
C18 C19 1.397(3) . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C22 C23 1.393(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 N1 C18 122.24(16) . . ?
C1 N1 C11 118.07(15) . . ?
C18 N1 C11 119.62(16) . . ?
C6 C1 C2 117.36(17) . . ?
C6 C1 N1 122.38(17) . . ?
C2 C1 N1 120.21(18) . . ?
C26 O2 C25 114.83(17) . . ?
C3 C2 C1 120.74(19) . . ?
C3 C2 C26 116.46(17) . . ?
C1 C2 C26 122.78(17) . . ?
C2 C3 C4 121.91(18) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C27 O3 C28 116.24(18) . . ?
C5 C4 C3 116.94(18) . . ?
C5 C4 C7 123.07(19) . . ?
C3 C4 C7 119.97(18) . . ?
C14 O5 C17 117.06(19) . . ?
C4 C5 C6 121.89(19) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 120.85(18) . . ?
C5 C6 C27 115.12(18) . . ?
C1 C6 C27 123.71(18) . . ?
C21 O6 C24 117.84(17) . . ?
C10 C7 C8 109.8(2) . . ?
C10 C7 C9 107.8(2) . . ?
C8 C7 C9 109.1(3) . . ?
C10 C7 C4 112.41(19) . . ?
C8 C7 C4 107.9(2) . . ?
C9 C7 C4 109.78(19) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 119.26(18) . . ?
C12 C11 N1 121.61(18) . . ?
C16 C11 N1 119.11(18) . . ?
C11 C12 C13 121.16(19) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 119.20(19) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O5 C14 C13 125.1(2) . . ?
O5 C14 C15 114.70(19) . . ?
C13 C14 C15 120.23(19) . . ?
C16 C15 C14 119.96(19) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.16(19) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.31(18) . . ?
C23 C18 N1 121.99(17) . . ?
C19 C18 N1 119.64(17) . . ?
C20 C19 C18 121.17(19) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.04(19) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
O6 C21 C20 115.71(18) . . ?
O6 C21 C22 124.72(18) . . ?
C20 C21 C22 119.58(18) . . ?
C21 C22 C23 120.04(19) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.81(19) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O1 C26 O2 124.27(19) . . ?
O1 C26 C2 124.94(18) . . ?
O2 C26 C2 110.69(16) . . ?
O4 C27 O3 123.7(2) . . ?
O4 C27 C6 125.0(2) . . ?
O3 C27 C6 111.08(17) . . ?
O3 C28 H28A 109.5 . . ?
O3 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O3 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 N1 C1 C6 -52.5(3) . . . . ?
C11 N1 C1 C6 130.5(2) . . . . ?
C18 N1 C1 C2 129.9(2) . . . . ?
C11 N1 C1 C2 -47.1(3) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
N1 C1 C2 C3 175.60(18) . . . . ?
C6 C1 C2 C26 176.02(18) . . . . ?
N1 C1 C2 C26 -6.3(3) . . . . ?
C1 C2 C3 C4 4.9(3) . . . . ?
C26 C2 C3 C4 -173.28(18) . . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
C2 C3 C4 C7 179.27(19) . . . . ?
C3 C4 C5 C6 -2.8(3) . . . . ?
C7 C4 C5 C6 175.4(2) . . . . ?
C4 C5 C6 C1 5.7(3) . . . . ?
C4 C5 C6 C27 -168.14(19) . . . . ?
C2 C1 C6 C5 -3.1(3) . . . . ?
N1 C1 C6 C5 179.31(18) . . . . ?
C2 C1 C6 C27 170.19(19) . . . . ?
N1 C1 C6 C27 -7.4(3) . . . . ?
C5 C4 C7 C10 6.4(3) . . . . ?
C3 C4 C7 C10 -175.4(2) . . . . ?
C5 C4 C7 C8 -114.8(3) . . . . ?
C3 C4 C7 C8 63.4(3) . . . . ?
C5 C4 C7 C9 126.4(2) . . . . ?
C3 C4 C7 C9 -55.4(3) . . . . ?
C1 N1 C11 C12 127.2(2) . . . . ?
C18 N1 C11 C12 -49.9(3) . . . . ?
C1 N1 C11 C16 -51.2(3) . . . . ?
C18 N1 C11 C16 131.74(19) . . . . ?
C16 C11 C12 C13 1.7(3) . . . . ?
N1 C11 C12 C13 -176.68(19) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C17 O5 C14 C13 -10.9(3) . . . . ?
C17 O5 C14 C15 170.1(2) . . . . ?
C12 C13 C14 O5 179.6(2) . . . . ?
C12 C13 C14 C15 -1.5(3) . . . . ?
O5 C14 C15 C16 -179.92(19) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C12 C11 C16 C15 -2.0(3) . . . . ?
N1 C11 C16 C15 176.34(18) . . . . ?
C1 N1 C18 C23 -35.0(3) . . . . ?
C11 N1 C18 C23 142.0(2) . . . . ?
C1 N1 C18 C19 147.9(2) . . . . ?
C11 N1 C18 C19 -35.2(3) . . . . ?
C23 C18 C19 C20 -1.7(3) . . . . ?
N1 C18 C19 C20 175.5(2) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C24 O6 C21 C20 175.9(2) . . . . ?
C24 O6 C21 C22 -4.3(3) . . . . ?
C19 C20 C21 O6 -179.0(2) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
O6 C21 C22 C23 177.9(2) . . . . ?
C20 C21 C22 C23 -2.2(3) . . . . ?
C19 C18 C23 C22 0.7(3) . . . . ?
N1 C18 C23 C22 -176.50(19) . . . . ?
C21 C22 C23 C18 1.3(3) . . . . ?
C25 O2 C26 O1 0.2(3) . . . . ?
C25 O2 C26 C2 -176.11(19) . . . . ?
C3 C2 C26 O1 -59.8(3) . . . . ?
C1 C2 C26 O1 122.0(2) . . . . ?
C3 C2 C26 O2 116.49(19) . . . . ?
C1 C2 C26 O2 -61.7(2) . . . . ?
C28 O3 C27 O4 2.7(4) . . . . ?
C28 O3 C27 C6 -171.9(2) . . . . ?
C5 C6 C27 O4 -49.8(3) . . . . ?
C1 C6 C27 O4 136.6(3) . . . . ?
C5 C6 C27 O3 124.6(2) . . . . ?
C1 C6 C27 O3 -49.0(3) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_2Me_b
_database_code_depnum_ccdc_archive 'CCDC 1945532'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_yan_exp302_1_0m

_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            'C28 H25 F6 N O4'
_chemical_formula_weight         553.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.7241(3)
_cell_length_b                   12.3047(3)
_cell_length_c                   18.3432(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.0770(10)
_cell_angle_gamma                90
_cell_volume                     2605.40(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6921
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      23.91

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.204
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12410
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.920
_diffrn_reflns_theta_max         24.865
_diffrn_reflns_theta_full        24.865
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4485
_reflns_number_gt                4012
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+1.3487P] 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         4485
_refine_ls_number_parameters     413
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.139
_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
F1 F 0.3179(12) 0.4547(9) 0.3361(4) 0.076(2) Uani 0.472(18) 1 d . U P A 1
F2 F 0.4834(7) 0.4261(10) 0.3111(6) 0.073(2) Uani 0.472(18) 1 d . U P A 1
F3 F 0.3549(9) 0.3080(6) 0.2850(5) 0.0625(19) Uani 0.472(18) 1 d . U P A 1
F1A F 0.2814(6) 0.4255(8) 0.3259(5) 0.0648(16) Uani 0.528(18) 1 d . U P A 2
F2A F 0.4582(10) 0.4598(9) 0.3254(5) 0.085(2) Uani 0.528(18) 1 d . U P A 2
F3A F 0.3872(9) 0.3090(6) 0.2876(4) 0.0584(17) Uani 0.528(18) 1 d . U P A 2
F4 F 0.1499(5) 0.4000(4) -0.3222(2) 0.0857(16) Uani 0.594(6) 1 d . U P B 3
F5 F 0.1255(3) 0.2639(3) -0.2568(2) 0.0460(8) Uani 0.594(6) 1 d . U P B 3
F6 F -0.0091(3) 0.3763(3) -0.28373(18) 0.0779(13) Uani 0.594(6) 1 d . U P B 3
F4A F 0.0791(7) 0.2863(6) -0.2652(4) 0.089(2) Uani 0.406(6) 1 d . U P B 4
F5A F 0.0406(5) 0.4425(5) -0.3134(2) 0.0805(17) Uani 0.406(6) 1 d . U P B 4
F6A F 0.2043(4) 0.3789(5) -0.3105(3) 0.0484(11) Uani 0.406(6) 1 d . U P B 4
C23 C 0.36825(15) 0.41432(14) 0.28601(9) 0.0349(4) Uani 1 1 d . . . . .
C24 C 0.11102(18) 0.37638(17) -0.26649(10) 0.0462(5) Uani 1 1 d . . . . .
O1 O 0.48259(9) 0.75469(9) 0.14591(5) 0.0273(2) Uani 1 1 d . . . . .
O2 O 0.51225(9) 0.66037(8) 0.04619(6) 0.0306(3) Uani 1 1 d . . . . .
O3 O 0.00948(9) 0.65198(8) -0.04186(6) 0.0284(3) Uani 1 1 d . . . . .
O4 O 0.01090(9) 0.75687(9) -0.14170(6) 0.0290(3) Uani 1 1 d . . . . .
N1 N 0.25885(10) 0.60648(9) 0.00107(6) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.25786(11) 0.72196(11) -0.00181(7) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.35114(12) 0.78168(11) 0.03583(7) 0.0182(3) Uani 1 1 d . . . . .
C3 C 0.34802(12) 0.89521(11) 0.03568(7) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.4097 0.9343 0.0647 0.022 Uiso 1 1 calc R U . . .
C4 C 0.25700(11) 0.95229(11) -0.00586(7) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.16624(12) 0.89158(11) -0.04544(7) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.1045 0.9284 -0.0760 0.022 Uiso 1 1 calc R U . . .
C6 C 0.16337(12) 0.77893(11) -0.04146(7) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.25345(11) 1.07675(11) -0.01030(7) 0.0202(3) Uani 1 1 d . . . . .
C8 C 0.13685(13) 1.11855(12) 0.00535(9) 0.0285(3) Uani 1 1 d . . . . .
H8A H 0.1356 1.1981 0.0029 0.043 Uiso 1 1 calc R U . . .
H8AB H 0.1265 1.0951 0.0548 0.043 Uiso 1 1 calc R U . . .
H8AC H 0.0740 1.0891 -0.0317 0.043 Uiso 1 1 calc R U . . .
C9 C 0.26731(14) 1.11160(12) -0.08843(8) 0.0289(3) Uani 1 1 d . . . . .
H9A H 0.2046 1.0801 -0.1246 0.043 Uiso 1 1 calc R U . . .
H9AB H 0.3421 1.0860 -0.0986 0.043 Uiso 1 1 calc R U . . .
H9AC H 0.2641 1.1910 -0.0920 0.043 Uiso 1 1 calc R U . . .
C10 C 0.34985(14) 1.12899(12) 0.04550(9) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.4253 1.1056 0.0351 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3423 1.1066 0.0957 0.046 Uiso 1 1 calc R U . . .
H10C H 0.3438 1.2083 0.0415 0.046 Uiso 1 1 calc R U . . .
C11 C 0.28118(12) 0.55471(11) 0.07099(7) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.35183(12) 0.46309(11) 0.08175(8) 0.0212(3) Uani 1 1 d . . . . .
H12 H 0.3817 0.4325 0.0414 0.025 Uiso 1 1 calc R U . . .
C13 C 0.37833(13) 0.41682(11) 0.15136(8) 0.0240(3) Uani 1 1 d . . . . .
H13 H 0.4262 0.3541 0.1588 0.029 Uiso 1 1 calc R U . . .
C14 C 0.33519(13) 0.46184(12) 0.21056(8) 0.0242(3) Uani 1 1 d . . . . .
C15 C 0.26385(13) 0.55236(12) 0.19968(8) 0.0254(3) Uani 1 1 d . . . . .
H15 H 0.2339 0.5828 0.2400 0.031 Uiso 1 1 calc R U . . .
C16 C 0.23628(13) 0.59826(11) 0.12999(8) 0.0230(3) Uani 1 1 d . . . . .
H16 H 0.1866 0.6597 0.1224 0.028 Uiso 1 1 calc R U . . .
C17 C 0.22755(12) 0.54590(11) -0.06470(7) 0.0184(3) Uani 1 1 d . . . . .
C18 C 0.16012(12) 0.45252(11) -0.06527(8) 0.0214(3) Uani 1 1 d . . . . .
H18 H 0.1390 0.4268 -0.0206 0.026 Uiso 1 1 calc R U . . .
C19 C 0.12403(13) 0.39748(12) -0.13067(8) 0.0255(3) Uani 1 1 d . . . . .
H19 H 0.0785 0.3336 -0.1309 0.031 Uiso 1 1 calc R U . . .
C20 C 0.15381(14) 0.43485(12) -0.19626(8) 0.0280(3) Uani 1 1 d . . . . .
C21 C 0.22154(14) 0.52750(12) -0.19583(8) 0.0284(3) Uani 1 1 d . . . . .
H21 H 0.2421 0.5532 -0.2406 0.034 Uiso 1 1 calc R U . . .
C22 C 0.25918(13) 0.58245(12) -0.13018(8) 0.0238(3) Uani 1 1 d . . . . .
H22 H 0.3066 0.6451 -0.1298 0.029 Uiso 1 1 calc R U . . .
C25 C 0.57908(14) 0.69773(15) 0.18969(9) 0.0373(4) Uani 1 1 d . . . . .
H25A H 0.5572 0.6220 0.1963 0.056 Uiso 1 1 calc R U . . .
H25B H 0.5995 0.7328 0.2382 0.056 Uiso 1 1 calc R U . . .
H25C H 0.6458 0.6999 0.1642 0.056 Uiso 1 1 calc R U . . .
C26 C 0.45693(12) 0.72446(11) 0.07473(8) 0.0206(3) Uani 1 1 d . . . . .
C27 C 0.05464(12) 0.72057(11) -0.07360(8) 0.0205(3) Uani 1 1 d . . . . .
C28 C -0.09530(15) 0.70421(16) -0.17619(10) 0.0416(4) Uani 1 1 d . . . . .
H28A H -0.1179 0.7311 -0.2270 0.062 Uiso 1 1 calc R U . . .
H28B H -0.1568 0.7204 -0.1479 0.062 Uiso 1 1 calc R U . . .
H28C H -0.0831 0.6255 -0.1771 0.062 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
F1 C23 1.277(9) . ?
F2 C23 1.356(8) . ?
F3 C23 1.317(8) . ?
F1A C23 1.361(7) . ?
F2A C23 1.296(8) . ?
F3A C23 1.315(7) . ?
F4 C24 1.224(4) . ?
F5 C24 1.402(4) . ?
F6 C24 1.388(4) . ?
F4A C24 1.172(7) . ?
F5A C24 1.355(5) . ?
F6A C24 1.469(6) . ?
C23 C14 1.490(2) . ?
C24 C20 1.484(2) . ?
O1 C26 1.3403(18) . ?
O1 C25 1.4484(18) . ?
O2 C26 1.1980(17) . ?
O3 C27 1.1998(17) . ?
O4 C27 1.3411(18) . ?
O4 C28 1.4474(18) . ?
N1 C17 1.4110(17) . ?
N1 C11 1.4150(17) . ?
N1 C1 1.4218(18) . ?
C1 C2 1.3958(19) . ?
C1 C6 1.4021(19) . ?
C2 C3 1.3974(19) . ?
C2 C26 1.4945(19) . ?
C3 C4 1.3886(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3953(19) . ?
C4 C7 1.5338(18) . ?
C5 C6 1.3887(19) . ?
C5 H5 0.9500 . ?
C6 C27 1.4917(19) . ?
C7 C10 1.528(2) . ?
C7 C9 1.5315(19) . ?
C7 C8 1.5339(19) . ?
C8 H8A 0.9800 . ?
C8 H8AB 0.9800 . ?
C8 H8AC 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.3910(19) . ?
C11 C12 1.3924(19) . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3922(19) . ?
C17 C18 1.394(2) . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
F2A C23 F3A 107.2(5) . . ?
F1 C23 F3 109.1(6) . . ?
F1 C23 F2 105.8(5) . . ?
F3 C23 F2 102.7(5) . . ?
F2A C23 F1A 105.6(5) . . ?
F3A C23 F1A 103.2(5) . . ?
F1 C23 C14 116.0(4) . . ?
F2A C23 C14 113.8(4) . . ?
F3A C23 C14 115.0(3) . . ?
F3 C23 C14 111.4(4) . . ?
F2 C23 C14 110.8(4) . . ?
F1A C23 C14 111.3(4) . . ?
F4A C24 F5A 114.8(4) . . ?
F4 C24 F6 108.7(3) . . ?
F4 C24 F5 106.6(3) . . ?
F6 C24 F5 97.1(3) . . ?
F4A C24 F6A 107.6(5) . . ?
F5A C24 F6A 93.9(3) . . ?
F4A C24 C20 120.1(4) . . ?
F4 C24 C20 119.4(2) . . ?
F5A C24 C20 109.7(2) . . ?
F6 C24 C20 111.93(18) . . ?
F5 C24 C20 110.7(2) . . ?
F6A C24 C20 107.2(2) . . ?
C26 O1 C25 115.23(12) . . ?
C27 O4 C28 114.68(12) . . ?
C17 N1 C11 121.09(11) . . ?
C17 N1 C1 119.81(10) . . ?
C11 N1 C1 118.85(10) . . ?
C2 C1 C6 118.22(13) . . ?
C2 C1 N1 120.48(12) . . ?
C6 C1 N1 121.29(12) . . ?
C1 C2 C3 120.49(12) . . ?
C1 C2 C26 120.07(12) . . ?
C3 C2 C26 119.41(12) . . ?
C4 C3 C2 121.60(12) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 117.23(12) . . ?
C3 C4 C7 123.04(12) . . ?
C5 C4 C7 119.72(12) . . ?
C6 C5 C4 122.02(12) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 120.14(12) . . ?
C5 C6 C27 119.12(12) . . ?
C1 C6 C27 120.49(12) . . ?
C10 C7 C9 108.78(12) . . ?
C10 C7 C4 112.00(11) . . ?
C9 C7 C4 108.84(11) . . ?
C10 C7 C8 108.21(12) . . ?
C9 C7 C8 108.97(12) . . ?
C4 C7 C8 109.98(11) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8AB 109.5 . . ?
H8A C8 H8AB 109.5 . . ?
C7 C8 H8AC 109.5 . . ?
H8A C8 H8AC 109.5 . . ?
H8AB C8 H8AC 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9AB 109.5 . . ?
H9A C9 H9AB 109.5 . . ?
C7 C9 H9AC 109.5 . . ?
H9A C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 119.89(13) . . ?
C16 C11 N1 119.78(12) . . ?
C12 C11 N1 120.27(12) . . ?
C13 C12 C11 119.75(13) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.22(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.02(13) . . ?
C15 C14 C23 120.09(14) . . ?
C13 C14 C23 119.86(14) . . ?
C16 C15 C14 119.91(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.18(13) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C22 C17 C18 119.75(13) . . ?
C22 C17 N1 119.89(12) . . ?
C18 C17 N1 120.29(12) . . ?
C19 C18 C17 119.94(13) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.40(14) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 119.82(13) . . ?
C19 C20 C24 119.57(15) . . ?
C21 C20 C24 120.60(15) . . ?
C22 C21 C20 120.06(14) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 120.02(14) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O2 C26 O1 124.19(13) . . ?
O2 C26 C2 124.68(13) . . ?
O1 C26 C2 111.13(11) . . ?
O3 C27 O4 123.84(13) . . ?
O3 C27 C6 124.47(13) . . ?
O4 C27 C6 111.65(11) . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_2iPr_a
_database_code_depnum_ccdc_archive 'CCDC 1945534'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_1001

_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            'C30 H33 Cl2 N O4'
_chemical_formula_weight         542.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.840(2)
_cell_length_b                   14.543(3)
_cell_length_c                   18.231(3)
_cell_angle_alpha                97.047(3)
_cell_angle_beta                 105.059(3)
_cell_angle_gamma                102.364(3)
_cell_volume                     2907.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2083
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      22.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.257
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7932
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14070
_diffrn_reflns_av_unetI/netI     0.0994
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.843
_diffrn_reflns_theta_max         25.073
_diffrn_reflns_theta_full        25.073
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             10099
_reflns_number_gt                5356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1575P)²+2.5272P] 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         10099
_refine_ls_number_parameters     689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.2302
_refine_ls_wR_factor_gt          0.1674
_refine_ls_goodness_of_fit_ref   0.782
_refine_ls_restrained_S_all      0.782
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.002

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 0.31716(14) -0.16609(10) 0.63555(10) 0.0758(5) Uani 1 1 d . . . . .
Cl2 Cl -0.36064(14) 0.19076(14) 0.63467(12) 0.0955(6) Uani 1 1 d . . . . .
Cl3 Cl -0.56920(13) 0.75277(12) 0.95865(11) 0.0868(6) Uani 1 1 d . . . . .
Cl4 Cl 0.37162(13) 0.94707(15) 1.18758(8) 0.0917(6) Uani 1 1 d . . . . .
O1 O 0.1646(3) 0.4204(2) 0.79263(15) 0.0379(7) Uani 1 1 d . . . . .
O2 O 0.1289(3) 0.1601(2) 0.48104(16) 0.0447(8) Uani 1 1 d . . . . .
O3 O 0.3243(3) 0.1974(2) 0.48548(17) 0.0475(8) Uani 1 1 d . . . . .
O4 O -0.1518(3) 0.5620(2) 0.94711(16) 0.0482(8) Uani 1 1 d . . . . .
O5 O 0.1784(3) 0.8885(2) 0.86045(18) 0.0471(8) Uani 1 1 d . . . . .
O6 O -0.2930(3) 0.4952(2) 0.83368(15) 0.0397(7) Uani 1 1 d . . . . .
O7 O 0.2140(3) 0.2814(2) 0.80698(17) 0.0466(8) Uani 1 1 d . . . . .
O8 O 0.0074(3) 0.9273(2) 0.8632(2) 0.0693(11) Uani 1 1 d . . . . .
N2 N 0.1419(3) 0.1862(2) 0.64290(19) 0.0342(8) Uani 1 1 d . . . . .
N3 N -0.0786(3) 0.7615(2) 0.93448(18) 0.0350(8) Uani 1 1 d . . . . .
C1 C 0.3117(4) 0.4423(3) 0.6960(2) 0.0305(9) Uani 1 1 d . . . . .
H1 H 0.3225 0.4961 0.7349 0.037 Uiso 1 1 calc R U . . .
C4 C -0.0502(4) 0.6236(3) 0.7226(2) 0.0297(9) Uani 1 1 d . . . . .
C5 C 0.3659(3) 0.4554(3) 0.6374(2) 0.0294(9) Uani 1 1 d . . . . .
C6 C 0.3425(4) 0.3741(3) 0.5799(2) 0.0310(9) Uani 1 1 d . . . . .
H6 H 0.3795 0.3792 0.5397 0.037 Uiso 1 1 calc R U . . .
C7 C 0.2426(3) 0.3542(3) 0.7000(2) 0.0294(9) Uani 1 1 d . . . . .
C8 C -0.0367(4) 0.5764(3) 0.6458(2) 0.0344(10) Uani 1 1 d . . . . .
C9 C 0.2170(4) 0.2747(3) 0.6409(2) 0.0300(9) Uani 1 1 d . . . . .
C10 C 0.2673(4) 0.2869(3) 0.5799(2) 0.0304(9) Uani 1 1 d . . . . .
C11 C 0.0271(4) 0.8048(3) 0.9960(2) 0.0320(9) Uani 1 1 d . . . . .
C12 C 0.0012(4) 0.7645(3) 0.8233(2) 0.0346(10) Uani 1 1 d . . . . .
C14 C -0.1226(4) 0.5757(3) 0.7618(2) 0.0323(9) Uani 1 1 d . . . . .
H14 H -0.1685 0.5116 0.7399 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4453(4) 0.5515(3) 0.6339(2) 0.0357(10) Uani 1 1 d . . . . .
C16 C 0.0621(4) 0.8692(3) 0.8511(2) 0.0384(10) Uani 1 1 d . . . . .
C17 C -0.1303(4) 0.6189(3) 0.8327(2) 0.0320(9) Uani 1 1 d . . . . .
C18 C 0.0134(4) 0.7187(3) 0.7553(2) 0.0329(9) Uani 1 1 d . . . . .
H18 H 0.0660 0.7527 0.7306 0.040 Uiso 1 1 calc R U . . .
C19 C 0.2310(4) 0.2073(3) 0.5111(2) 0.0334(10) Uani 1 1 d . . . . .
C20 C 0.2044(4) 0.3450(3) 0.7716(2) 0.0346(10) Uani 1 1 d . . . . .
C21 C 0.1836(4) 0.1026(3) 0.6388(2) 0.0333(9) Uani 1 1 d . . . . .
C22 C -0.2218(4) 0.7524(3) 1.0099(3) 0.0419(11) Uani 1 1 d . . . . .
H22 H -0.1609 0.7466 1.0535 0.050 Uiso 1 1 calc R U . . .
C23 C 0.3068(4) 0.1086(3) 0.6627(2) 0.0397(10) Uani 1 1 d . . . . .
H23 H 0.3633 0.1695 0.6814 0.048 Uiso 1 1 calc R U . . .
C24 C -0.2824(4) 0.7758(3) 0.8793(3) 0.0465(12) Uani 1 1 d . . . . .
H24 H -0.2640 0.7861 0.8328 0.056 Uiso 1 1 calc R U . . .
C25 C -0.1938(4) 0.7637(3) 0.9411(2) 0.0357(10) Uani 1 1 d . . . . .
C26 C -0.1910(4) 0.5578(3) 0.8791(2) 0.0350(10) Uani 1 1 d . . . . .
C27 C 0.1357(4) 0.4276(3) 0.8669(2) 0.0393(11) Uani 1 1 d . . . . .
H27 H 0.1915 0.4006 0.9044 0.047 Uiso 1 1 calc R U . . .
C28 C -0.0697(4) 0.7151(3) 0.8636(2) 0.0331(9) Uani 1 1 d . . . . .
C29 C 0.0203(4) 0.1836(3) 0.6402(2) 0.0372(10) Uani 1 1 d . . . . .
C30 C -0.0474(4) 0.2248(3) 0.5860(3) 0.0451(11) Uani 1 1 d . . . . .
H30 H -0.0129 0.2526 0.5497 0.054 Uiso 1 1 calc R U . . .
C31 C 0.0366(4) 0.8890(3) 1.0454(2) 0.0408(11) Uani 1 1 d . . . . .
H31 H -0.0298 0.9174 1.0383 0.049 Uiso 1 1 calc R U . . .
C32 C 0.1030(4) 0.0123(3) 0.6105(2) 0.0381(10) Uani 1 1 d . . . . .
H32 H 0.0187 0.0071 0.5916 0.046 Uiso 1 1 calc R U . . .
C33 C 0.2975(5) 0.1188(4) 0.4188(3) 0.0565(14) Uani 1 1 d . . . . .
H33 H 0.2327 0.0646 0.4229 0.068 Uiso 1 1 calc R U . . .
C34 C 0.2301(4) 0.8077(4) 1.0662(3) 0.0489(12) Uani 1 1 d . . . . .
H34 H 0.2970 0.7799 1.0735 0.059 Uiso 1 1 calc R U . . .
C35 C -0.1650(4) 0.2261(3) 0.5840(3) 0.0532(13) Uani 1 1 d . . . . .
H35 H -0.2109 0.2546 0.5467 0.064 Uiso 1 1 calc R U . . .
C36 C 0.1251(4) 0.7647(3) 1.0078(2) 0.0402(11) Uani 1 1 d . . . . .
H36 H 0.1196 0.7068 0.9751 0.048 Uiso 1 1 calc R U . . .
C37 C 0.2663(5) -0.0614(3) 0.6343(3) 0.0472(12) Uani 1 1 d . . . . .
C38 C 0.1578(5) 0.5328(3) 0.8956(3) 0.0477(12) Uani 1 1 d . . . . .
H38A H 0.1068 0.5599 0.8571 0.072 Uiso 1 1 calc R U . . .
H38B H 0.2431 0.5646 0.9041 0.072 Uiso 1 1 calc R U . . .
H38C H 0.1378 0.5428 0.9444 0.072 Uiso 1 1 calc R U . . .
C39 C 0.1441(4) -0.0693(3) 0.6096(3) 0.0434(11) Uani 1 1 d . . . . .
H39 H 0.0884 -0.1307 0.5920 0.052 Uiso 1 1 calc R U . . .
C40 C 0.0070(4) 0.3721(4) 0.8530(3) 0.0511(12) Uani 1 1 d . . . . .
H40A H -0.0467 0.3949 0.8127 0.077 Uiso 1 1 calc R U . . .
H40B H -0.0155 0.3814 0.9010 0.077 Uiso 1 1 calc R U . . .
H40C H -0.0008 0.3038 0.8362 0.077 Uiso 1 1 calc R U . . .
C41 C -0.3362(5) 0.7495(3) 1.0157(3) 0.0489(12) Uani 1 1 d . . . . .
H41 H -0.3545 0.7414 1.0626 0.059 Uiso 1 1 calc R U . . .
C42 C -0.2141(5) 0.1857(4) 0.6364(3) 0.0596(14) Uani 1 1 d . . . . .
C43 C 0.4657(5) 0.6282(3) 0.7056(3) 0.0505(12) Uani 1 1 d . . . . .
H43A H 0.5170 0.6886 0.7013 0.076 Uiso 1 1 calc R U . . .
H43B H 0.5056 0.6069 0.7522 0.076 Uiso 1 1 calc R U . . .
H43C H 0.3876 0.6378 0.7089 0.076 Uiso 1 1 calc R U . . .
C44 C 0.1414(4) 0.9315(4) 1.1043(3) 0.0521(13) Uani 1 1 d . . . . .
H44 H 0.1472 0.9886 1.1381 0.063 Uiso 1 1 calc R U . . .
C45 C 0.3838(5) 0.5872(3) 0.5629(3) 0.0518(13) Uani 1 1 d . . . . .
H45A H 0.3657 0.5381 0.5166 0.078 Uiso 1 1 calc R U . . .
H45B H 0.4376 0.6460 0.5580 0.078 Uiso 1 1 calc R U . . .
H45C H 0.3083 0.6006 0.5683 0.078 Uiso 1 1 calc R U . . .
C46 C 0.2467(5) 0.9895(3) 0.8893(3) 0.0556(13) Uani 1 1 d . . . . .
C47 C 0.3481(4) 0.0257(3) 0.6592(3) 0.0480(12) Uani 1 1 d . . . . .
H47 H 0.4324 0.0300 0.6741 0.058 Uiso 1 1 calc R U . . .
C48 C -0.3979(4) 0.7728(4) 0.8847(3) 0.0592(15) Uani 1 1 d . . . . .
H48 H -0.4588 0.7806 0.8420 0.071 Uiso 1 1 calc R U . . .
C49 C -0.0320(4) 0.1414(3) 0.6918(3) 0.0487(12) Uani 1 1 d . . . . .
H49 H 0.0126 0.1116 0.7286 0.058 Uiso 1 1 calc R U . . .
C50 C -0.4278(5) 0.3400(4) 0.8088(3) 0.0574(13) Uani 1 1 d . . . . .
H50A H -0.4877 0.3582 0.7689 0.086 Uiso 1 1 calc R U . . .
H50B H -0.4691 0.2901 0.8313 0.086 Uiso 1 1 calc R U . . .
H50C H -0.3716 0.3156 0.7855 0.086 Uiso 1 1 calc R U . . .
C51 C 0.0974(4) 0.5869(4) 0.6542(3) 0.0528(13) Uani 1 1 d . . . . .
H51A H 0.1065 0.5567 0.6057 0.079 Uiso 1 1 calc R U . . .
H51B H 0.1319 0.5557 0.6962 0.079 Uiso 1 1 calc R U . . .
H51C H 0.1400 0.6551 0.6661 0.079 Uiso 1 1 calc R U . . .
C52 C -0.0899(5) 0.6275(4) 0.5818(2) 0.0499(12) Uani 1 1 d . . . . .
H52A H -0.0858 0.5961 0.5321 0.075 Uiso 1 1 calc R U . . .
H52B H -0.0436 0.6947 0.5933 0.075 Uiso 1 1 calc R U . . .
H52C H -0.1745 0.6244 0.5788 0.075 Uiso 1 1 calc R U . . .
C53 C -0.3589(4) 0.4261(3) 0.8709(3) 0.0471(12) Uani 1 1 d . . . . .
H53 H -0.2994 0.4070 0.9122 0.057 Uiso 1 1 calc R U . . .
C54 C -0.4232(4) 0.7586(3) 0.9526(3) 0.0533(13) Uani 1 1 d . . . . .
C55 C -0.1019(5) 0.4701(3) 0.6240(3) 0.0505(12) Uani 1 1 d . . . . .
H55A H -0.1884 0.4623 0.6176 0.076 Uiso 1 1 calc R U . . .
H55B H -0.0683 0.4372 0.6649 0.076 Uiso 1 1 calc R U . . .
H55C H -0.0909 0.4425 0.5753 0.076 Uiso 1 1 calc R U . . .
C56 C 0.2381(4) 0.8910(4) 1.1142(3) 0.0551(14) Uani 1 1 d . . . . .
C57 C 0.5685(4) 0.5382(4) 0.6309(3) 0.0588(14) Uani 1 1 d . . . . .
H57A H 0.5579 0.4906 0.5850 0.088 Uiso 1 1 calc R U . . .
H57B H 0.6068 0.5161 0.6774 0.088 Uiso 1 1 calc R U . . .
H57C H 0.6199 0.5995 0.6282 0.088 Uiso 1 1 calc R U . . .
C58 C -0.1500(5) 0.1431(4) 0.6893(3) 0.0592(14) Uani 1 1 d . . . . .
H58 H -0.1860 0.1144 0.7246 0.071 Uiso 1 1 calc R U . . .
C59 C -0.4378(5) 0.4738(4) 0.9066(3) 0.0626(14) Uani 1 1 d . . . . .
H59A H -0.4955 0.4932 0.8663 0.094 Uiso 1 1 calc R U . . .
H59B H -0.3872 0.5305 0.9453 0.094 Uiso 1 1 calc R U . . .
H59C H -0.4819 0.4288 0.9317 0.094 Uiso 1 1 calc R U . . .
C60 C 0.2519(9) 0.1522(5) 0.3452(4) 0.118(3) Uani 1 1 d . . . . .
H60A H 0.2273 0.0982 0.3017 0.176 Uiso 1 1 calc R U . . .
H60B H 0.3162 0.2026 0.3387 0.176 Uiso 1 1 calc R U . . .
H60C H 0.1823 0.1777 0.3470 0.176 Uiso 1 1 calc R U . . .
C61 C 0.4116(7) 0.0871(7) 0.4290(6) 0.162(5) Uani 1 1 d . . . . .
H61A H 0.4003 0.0346 0.3865 0.243 Uiso 1 1 calc R U . . .
H61B H 0.4319 0.0650 0.4783 0.243 Uiso 1 1 calc R U . . .
H61C H 0.4774 0.1410 0.4290 0.243 Uiso 1 1 calc R U . . .
C62 C 0.2329(13) 1.0410(7) 0.8262(6) 0.113(4) Uani 0.658(12) 1 d . . P A 1
H62A H 0.2531 1.0070 0.7835 0.169 Uiso 0.658(12) 1 calc R U P A 1
H62B H 0.2873 1.1056 0.8436 0.169 Uiso 0.658(12) 1 calc R U P A 1
H62C H 0.1490 1.0454 0.8084 0.169 Uiso 0.658(12) 1 calc R U P A 1
C63 C 0.3704(13) 0.9875(7) 0.9352(7) 0.113(4) Uani 0.658(12) 1 d . . P A 1
H63A H 0.4111 0.9606 0.9006 0.169 Uiso 0.658(12) 1 calc R U P A 1
H63B H 0.3638 0.9477 0.9743 0.169 Uiso 0.658(12) 1 calc R U P A 1
H63C H 0.4174 1.0529 0.9607 0.169 Uiso 0.658(12) 1 calc R U P A 1
C64 C 0.2868(18) 0.9980(13) 0.9707(11) 0.089(7) Uani 0.342(12) 1 d . . P A 2
H64A H 0.2668 0.9438 0.9936 0.106 Uiso 0.342(12) 1 calc R U P A 2
H64B H 0.3336 1.0578 1.0025 0.106 Uiso 0.342(12) 1 calc R U P A 2
C65 C 0.3580(19) 0.9940(13) 0.8588(12) 0.089(7) Uani 0.342(12) 1 d . . P A 2
H65A H 0.3782 0.9320 0.8573 0.133 Uiso 0.342(12) 1 calc R U P A 2
H65B H 0.4271 1.0442 0.8933 0.133 Uiso 0.342(12) 1 calc R U P A 2
H65C H 0.3391 1.0087 0.8066 0.133 Uiso 0.342(12) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C37 1.753(5) . ?
Cl2 C42 1.744(5) . ?
Cl3 C54 1.745(5) . ?
Cl4 C56 1.742(5) . ?
O1 C20 1.336(5) . ?
O1 C27 1.478(5) . ?
O2 C19 1.201(5) . ?
O3 C19 1.333(5) . ?
O3 C33 1.479(5) . ?
O4 C26 1.194(5) . ?
O5 C16 1.305(5) . ?
O5 C46 1.474(6) . ?
O6 C26 1.341(5) . ?
O6 C53 1.478(5) . ?
O7 C20 1.199(5) . ?
O8 C16 1.203(5) . ?
N2 C21 1.408(5) . ?
N2 C9 1.409(5) . ?
N2 C29 1.420(5) . ?
N3 C11 1.407(5) . ?
N3 C25 1.408(5) . ?
N3 C28 1.422(5) . ?
C1 C5 1.395(5) . ?
C1 C7 1.386(6) . ?
C4 C14 1.384(6) . ?
C4 C18 1.397(6) . ?
C4 C8 1.545(5) . ?
C5 C6 1.407(5) . ?
C5 C15 1.526(6) . ?
C6 C10 1.385(6) . ?
C7 C9 1.402(5) . ?
C7 C20 1.500(6) . ?
C8 C55 1.524(6) . ?
C8 C51 1.527(6) . ?
C8 C52 1.531(6) . ?
C9 C10 1.403(5) . ?
C10 C19 1.499(5) . ?
C11 C31 1.394(6) . ?
C11 C36 1.386(5) . ?
C12 C18 1.390(5) . ?
C12 C28 1.398(6) . ?
C12 C16 1.498(6) . ?
C14 C17 1.400(5) . ?
C15 C57 1.526(6) . ?
C15 C45 1.521(6) . ?
C15 C43 1.540(6) . ?
C17 C28 1.398(6) . ?
C17 C26 1.500(6) . ?
C21 C32 1.393(6) . ?
C21 C23 1.391(6) . ?
C22 C41 1.378(6) . ?
C22 C25 1.398(6) . ?
C23 C47 1.394(6) . ?
C24 C48 1.389(7) . ?
C24 C25 1.384(6) . ?
C27 C38 1.498(6) . ?
C27 C40 1.503(6) . ?
C29 C49 1.387(6) . ?
C29 C30 1.385(6) . ?
C30 C35 1.387(6) . ?
C31 C44 1.376(6) . ?
C32 C39 1.376(6) . ?
C33 C61 1.493(8) . ?
C33 C60 1.491(8) . ?
C34 C36 1.373(6) . ?
C34 C56 1.375(7) . ?
C35 C42 1.369(7) . ?
C37 C39 1.374(6) . ?
C37 C47 1.362(7) . ?
C41 C54 1.371(7) . ?
C42 C58 1.364(8) . ?
C44 C56 1.377(6) . ?
C46 C64 1.42(2) . ?
C46 C62 1.441(11) . ?
C46 C63 1.494(14) . ?
C46 C65 1.549(19) . ?
C48 C54 1.378(7) . ?
C49 C58 1.392(7) . ?
C50 C53 1.499(7) . ?
C53 C59 1.504(7) . ?

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
C20 O1 C27 117.1(3) . . ?
C19 O3 C33 116.0(4) . . ?
C16 O5 C46 116.6(4) . . ?
C26 O6 C53 117.1(3) . . ?
C21 N2 C9 120.2(3) . . ?
C21 N2 C29 122.0(3) . . ?
C9 N2 C29 117.3(3) . . ?
C11 N3 C25 121.4(3) . . ?
C11 N3 C28 119.8(3) . . ?
C25 N3 C28 118.8(3) . . ?
C5 C1 C7 122.8(3) . . ?
C14 C4 C18 117.6(4) . . ?
C14 C4 C8 123.0(4) . . ?
C18 C4 C8 119.5(4) . . ?
C1 C5 C6 115.9(4) . . ?
C1 C5 C15 123.1(3) . . ?
C6 C5 C15 121.0(3) . . ?
C10 C6 C5 122.3(4) . . ?
C9 C7 C1 120.4(3) . . ?
C9 C7 C20 121.3(4) . . ?
C1 C7 C20 118.2(3) . . ?
C55 C8 C51 108.6(4) . . ?
C55 C8 C52 109.2(4) . . ?
C51 C8 C52 109.6(4) . . ?
C55 C8 C4 111.7(3) . . ?
C51 C8 C4 109.2(3) . . ?
C52 C8 C4 108.6(3) . . ?
C7 C9 C10 117.8(4) . . ?
C7 C9 N2 120.5(3) . . ?
C10 C9 N2 121.7(3) . . ?
C6 C10 C9 120.6(3) . . ?
C6 C10 C19 119.7(3) . . ?
C9 C10 C19 119.5(4) . . ?
C31 C11 C36 118.6(4) . . ?
C31 C11 N3 121.2(4) . . ?
C36 C11 N3 120.3(4) . . ?
C18 C12 C28 120.9(4) . . ?
C18 C12 C16 118.6(4) . . ?
C28 C12 C16 120.5(4) . . ?
C4 C14 C17 122.0(4) . . ?
C5 C15 C57 108.8(3) . . ?
C5 C15 C45 109.3(3) . . ?
C57 C15 C45 111.0(4) . . ?
C5 C15 C43 111.8(3) . . ?
C57 C15 C43 108.0(4) . . ?
C45 C15 C43 107.9(4) . . ?
O8 C16 O5 125.1(4) . . ?
O8 C16 C12 122.3(4) . . ?
O5 C16 C12 112.6(4) . . ?
C28 C17 C14 120.0(4) . . ?
C28 C17 C26 120.6(3) . . ?
C14 C17 C26 119.0(4) . . ?
C12 C18 C4 121.2(4) . . ?
O2 C19 O3 123.9(4) . . ?
O2 C19 C10 123.8(4) . . ?
O3 C19 C10 112.3(4) . . ?
O7 C20 O1 124.9(4) . . ?
O7 C20 C7 124.7(4) . . ?
O1 C20 C7 110.3(3) . . ?
C32 C21 N2 121.1(4) . . ?
C32 C21 C23 118.5(4) . . ?
N2 C21 C23 120.4(4) . . ?
C41 C22 C25 121.1(5) . . ?
C47 C23 C21 120.4(4) . . ?
C48 C24 C25 120.5(5) . . ?
C24 C25 C22 118.6(4) . . ?
C24 C25 N3 120.7(4) . . ?
C22 C25 N3 120.7(4) . . ?
O4 C26 O6 124.4(4) . . ?
O4 C26 C17 124.6(4) . . ?
O6 C26 C17 111.0(3) . . ?
O1 C27 C38 105.2(3) . . ?
O1 C27 C40 108.9(3) . . ?
C38 C27 C40 113.5(4) . . ?
C17 C28 C12 118.2(4) . . ?
C17 C28 N3 121.2(4) . . ?
C12 C28 N3 120.6(4) . . ?
C49 C29 C30 119.1(4) . . ?
C49 C29 N2 121.1(4) . . ?
C30 C29 N2 119.8(4) . . ?
C29 C30 C35 120.8(5) . . ?
C44 C31 C11 120.4(4) . . ?
C21 C32 C39 120.7(4) . . ?
O3 C33 C61 105.0(4) . . ?
O3 C33 C60 109.9(4) . . ?
C61 C33 C60 116.3(6) . . ?
C36 C34 C56 119.7(4) . . ?
C42 C35 C30 119.2(5) . . ?
C34 C36 C11 120.9(4) . . ?
C39 C37 C47 121.4(4) . . ?
C39 C37 Cl1 119.0(4) . . ?
C47 C37 Cl1 119.6(4) . . ?
C37 C39 C32 119.6(4) . . ?
C54 C41 C22 119.0(5) . . ?
C58 C42 C35 121.0(5) . . ?
C58 C42 Cl2 120.4(4) . . ?
C35 C42 Cl2 118.6(5) . . ?
C56 C44 C31 119.8(4) . . ?
C64 C46 O5 104.5(8) . . ?
O5 C46 C62 109.5(5) . . ?
O5 C46 C63 105.8(5) . . ?
C62 C46 C63 119.7(8) . . ?
C64 C46 C65 107.9(13) . . ?
O5 C46 C65 102.1(7) . . ?
C37 C47 C23 119.4(4) . . ?
C24 C48 C54 119.2(5) . . ?
C58 C49 C29 119.6(5) . . ?
O6 C53 C59 108.6(4) . . ?
O6 C53 C50 106.3(4) . . ?
C59 C53 C50 113.9(4) . . ?
C41 C54 C48 121.5(4) . . ?
C41 C54 Cl3 119.4(4) . . ?
C48 C54 Cl3 119.1(4) . . ?
C44 C56 C34 120.5(5) . . ?
C44 C56 Cl4 119.4(4) . . ?
C34 C56 Cl4 120.1(4) . . ?
C42 C58 C49 120.2(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
C7 C1 C5 C6 2.5(6) . . . . ?
C7 C1 C5 C15 -178.1(4) . . . . ?
C1 C5 C6 C10 1.9(6) . . . . ?
C15 C5 C6 C10 -177.6(4) . . . . ?
C5 C1 C7 C9 -4.7(6) . . . . ?
C5 C1 C7 C20 170.9(4) . . . . ?
C14 C4 C8 C55 -5.6(5) . . . . ?
C18 C4 C8 C55 173.9(4) . . . . ?
C14 C4 C8 C51 -125.7(4) . . . . ?
C18 C4 C8 C51 53.8(5) . . . . ?
C14 C4 C8 C52 114.9(4) . . . . ?
C18 C4 C8 C52 -65.6(5) . . . . ?
C1 C7 C9 C10 2.4(6) . . . . ?
C20 C7 C9 C10 -173.0(3) . . . . ?
C1 C7 C9 N2 -176.9(3) . . . . ?
C20 C7 C9 N2 7.7(6) . . . . ?
C21 N2 C9 C7 -124.7(4) . . . . ?
C29 N2 C9 C7 62.3(5) . . . . ?
C21 N2 C9 C10 56.0(5) . . . . ?
C29 N2 C9 C10 -116.9(4) . . . . ?
C5 C6 C10 C9 -4.0(6) . . . . ?
C5 C6 C10 C19 170.8(4) . . . . ?
C7 C9 C10 C6 1.8(6) . . . . ?
N2 C9 C10 C6 -178.9(3) . . . . ?
C7 C9 C10 C19 -173.0(3) . . . . ?
N2 C9 C10 C19 6.3(6) . . . . ?
C25 N3 C11 C31 -34.9(6) . . . . ?
C28 N3 C11 C31 144.5(4) . . . . ?
C25 N3 C11 C36 146.1(4) . . . . ?
C28 N3 C11 C36 -34.6(6) . . . . ?
C18 C4 C14 C17 -1.8(6) . . . . ?
C8 C4 C14 C17 177.7(3) . . . . ?
C1 C5 C15 C57 123.9(4) . . . . ?
C6 C5 C15 C57 -56.7(5) . . . . ?
C1 C5 C15 C45 -114.8(4) . . . . ?
C6 C5 C15 C45 64.6(5) . . . . ?
C1 C5 C15 C43 4.6(5) . . . . ?
C6 C5 C15 C43 -175.9(4) . . . . ?
C46 O5 C16 O8 1.1(6) . . . . ?
C46 O5 C16 C12 -178.8(3) . . . . ?
C18 C12 C16 O8 123.8(5) . . . . ?
C28 C12 C16 O8 -54.0(6) . . . . ?
C18 C12 C16 O5 -56.3(5) . . . . ?
C28 C12 C16 O5 125.9(4) . . . . ?
C4 C14 C17 C28 4.1(6) . . . . ?
C4 C14 C17 C26 -168.4(4) . . . . ?
C28 C12 C18 C4 3.8(6) . . . . ?
C16 C12 C18 C4 -174.0(4) . . . . ?
C14 C4 C18 C12 -2.2(6) . . . . ?
C8 C4 C18 C12 178.3(3) . . . . ?
C33 O3 C19 O2 -3.8(6) . . . . ?
C33 O3 C19 C10 178.5(4) . . . . ?
C6 C10 C19 O2 -133.0(4) . . . . ?
C9 C10 C19 O2 41.9(6) . . . . ?
C6 C10 C19 O3 44.8(5) . . . . ?
C9 C10 C19 O3 -140.4(4) . . . . ?
C27 O1 C20 O7 3.0(6) . . . . ?
C27 O1 C20 C7 -173.6(3) . . . . ?
C9 C7 C20 O7 43.5(6) . . . . ?
C1 C7 C20 O7 -132.1(5) . . . . ?
C9 C7 C20 O1 -139.9(4) . . . . ?
C1 C7 C20 O1 44.5(5) . . . . ?
C9 N2 C21 C32 -154.3(4) . . . . ?
C29 N2 C21 C32 18.3(6) . . . . ?
C9 N2 C21 C23 25.3(5) . . . . ?
C29 N2 C21 C23 -162.1(4) . . . . ?
C32 C21 C23 C47 -1.0(6) . . . . ?
N2 C21 C23 C47 179.4(4) . . . . ?
C48 C24 C25 C22 -2.5(7) . . . . ?
C48 C24 C25 N3 176.5(4) . . . . ?
C41 C22 C25 C24 2.4(6) . . . . ?
C41 C22 C25 N3 -176.6(4) . . . . ?
C11 N3 C25 C24 141.5(4) . . . . ?
C28 N3 C25 C24 -37.8(6) . . . . ?
C11 N3 C25 C22 -39.4(6) . . . . ?
C28 N3 C25 C22 141.2(4) . . . . ?
C53 O6 C26 O4 -1.3(6) . . . . ?
C53 O6 C26 C17 176.4(3) . . . . ?
C28 C17 C26 O4 -37.9(6) . . . . ?
C14 C17 C26 O4 134.6(4) . . . . ?
C28 C17 C26 O6 144.4(4) . . . . ?
C14 C17 C26 O6 -43.1(5) . . . . ?
C20 O1 C27 C38 151.1(4) . . . . ?
C20 O1 C27 C40 -86.9(4) . . . . ?
C14 C17 C28 C12 -2.4(6) . . . . ?
C26 C17 C28 C12 170.0(4) . . . . ?
C14 C17 C28 N3 178.3(3) . . . . ?
C26 C17 C28 N3 -9.3(6) . . . . ?
C18 C12 C28 C17 -1.4(6) . . . . ?
C16 C12 C28 C17 176.3(4) . . . . ?
C18 C12 C28 N3 177.9(4) . . . . ?
C16 C12 C28 N3 -4.4(6) . . . . ?
C11 N3 C28 C17 123.4(4) . . . . ?
C25 N3 C28 C17 -57.2(5) . . . . ?
C11 N3 C28 C12 -55.9(5) . . . . ?
C25 N3 C28 C12 123.5(4) . . . . ?
C21 N2 C29 C49 55.1(5) . . . . ?
C9 N2 C29 C49 -132.1(4) . . . . ?
C21 N2 C29 C30 -125.8(4) . . . . ?
C9 N2 C29 C30 47.0(5) . . . . ?
C49 C29 C30 C35 1.4(7) . . . . ?
N2 C29 C30 C35 -177.7(4) . . . . ?
C36 C11 C31 C44 0.3(7) . . . . ?
N3 C11 C31 C44 -178.7(4) . . . . ?
N2 C21 C32 C39 -177.3(4) . . . . ?
C23 C21 C32 C39 3.1(6) . . . . ?
C19 O3 C33 C61 -149.2(6) . . . . ?
C19 O3 C33 C60 85.1(6) . . . . ?
C29 C30 C35 C42 -0.1(7) . . . . ?
C56 C34 C36 C11 0.7(7) . . . . ?
C31 C11 C36 C34 -0.9(6) . . . . ?
N3 C11 C36 C34 178.1(4) . . . . ?
C47 C37 C39 C32 -0.6(7) . . . . ?
Cl1 C37 C39 C32 178.1(3) . . . . ?
C21 C32 C39 C37 -2.3(7) . . . . ?
C25 C22 C41 C54 -0.4(7) . . . . ?
C30 C35 C42 C58 -1.2(8) . . . . ?
C30 C35 C42 Cl2 178.3(4) . . . . ?
C11 C31 C44 C56 0.6(8) . . . . ?
C16 O5 C46 C64 92.2(10) . . . . ?
C16 O5 C46 C62 -80.6(8) . . . . ?
C16 O5 C46 C63 149.1(7) . . . . ?
C16 O5 C46 C65 -155.4(10) . . . . ?
C39 C37 C47 C23 2.6(7) . . . . ?
Cl1 C37 C47 C23 -176.1(4) . . . . ?
C21 C23 C47 C37 -1.8(7) . . . . ?
C25 C24 C48 C54 0.5(7) . . . . ?
C30 C29 C49 C58 -1.3(7) . . . . ?
N2 C29 C49 C58 177.7(4) . . . . ?
C26 O6 C53 C59 83.6(5) . . . . ?
C26 O6 C53 C50 -153.5(4) . . . . ?
C22 C41 C54 C48 -1.7(7) . . . . ?
C22 C41 C54 Cl3 178.8(3) . . . . ?
C24 C48 C54 C41 1.6(8) . . . . ?
C24 C48 C54 Cl3 -178.9(4) . . . . ?
C31 C44 C56 C34 -0.9(8) . . . . ?
C31 C44 C56 Cl4 178.4(4) . . . . ?
C36 C34 C56 C44 0.3(8) . . . . ?
C36 C34 C56 Cl4 -179.0(4) . . . . ?
C35 C42 C58 C49 1.2(8) . . . . ?
Cl2 C42 C58 C49 -178.3(4) . . . . ?
C29 C49 C58 C42 0.1(8) . . . . ?

_refine_diff_density_max         0.434
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_3iPr_a
_database_code_depnum_ccdc_archive 'CCDC 1945536'
loop_
_audit_author_name
_audit_author_address
'Rong Shang'
;Hiroshima University
Japan
;
_audit_update_record             
;
2019-08-05 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
#data_exp017

_audit_creation_method           SHELXL-2014/5
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H33 Cl8 N O4 Sb'
_chemical_formula_weight         876.92

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'
N N 0.0061 0.0033 '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'
Sb Sb -0.5866 1.5461 '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                   12.156(3)
_cell_length_b                   15.548(3)
_cell_length_c                   19.482(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.770(4)
_cell_angle_gamma                90
_cell_volume                     3681.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1967
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      21.77

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.365
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7748
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20884
_diffrn_reflns_av_unetI/netI     0.1375
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.676
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8431
_reflns_number_gt                4448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR-2004
_computing_structure_refinement  'SHELXL-2014/5 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8431
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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
Sb1 Sb 0.42174(3) 0.22453(2) 0.68147(2) 0.02851(11) Uani 1 1 d . . . . .
Cl11 Cl 0.52693(11) 0.15898(9) 0.76962(7) 0.0414(4) Uani 1 1 d . . . . .
Cl12 Cl 0.31446(13) 0.28606(12) 0.59316(8) 0.0605(5) Uani 1 1 d . . . . .
Cl13 Cl 0.28009(11) 0.12223(11) 0.69977(8) 0.0540(5) Uani 1 1 d . . . . .
Cl14 Cl 0.56564(12) 0.32358(9) 0.66384(8) 0.0445(4) Uani 1 1 d . . . . .
Cl15 Cl 0.50038(11) 0.13017(9) 0.59986(8) 0.0458(4) Uani 1 1 d . . . . .
Cl16 Cl 0.34430(13) 0.31767(10) 0.76246(8) 0.0530(4) Uani 1 1 d . . . . .
Cl1 Cl 0.07622(13) 0.01047(10) 0.89527(9) 0.0612(5) Uani 1 1 d . . . . .
Cl2 Cl 0.37265(13) 0.48400(10) 1.24384(8) 0.0494(4) Uani 1 1 d . . . . .
O1 O 0.3549(2) 0.37730(19) 0.93507(17) 0.0254(8) Uani 1 1 d . . . . .
O2 O 0.4952(3) 0.4642(2) 0.9101(2) 0.0511(12) Uani 1 1 d . . . . .
O3 O 0.6242(3) 0.0354(2) 1.01564(19) 0.0432(10) Uani 1 1 d . . . . .
O4 O 0.5091(3) 0.1137(2) 1.07922(17) 0.0317(9) Uani 1 1 d . . . . .
N1 N 0.4076(3) 0.2421(2) 1.0139(2) 0.0198(9) Uani 1 1 d . . . . .
C1 C 0.5114(4) 0.2468(3) 0.9779(2) 0.0216(12) Uani 1 1 d . . . . .
C2 C 0.5356(4) 0.3199(3) 0.9394(2) 0.0222(11) Uani 1 1 d . . . . .
C3 C 0.6359(4) 0.3241(3) 0.9065(3) 0.0283(12) Uani 1 1 d . . . . .
H3 H 0.6527 0.3743 0.8809 0.034 Uiso 1 1 calc R U . . .
C4 C 0.7126(4) 0.2585(3) 0.9093(3) 0.0276(13) Uani 1 1 d . . . . .
C5 C 0.6840(4) 0.1858(3) 0.9462(2) 0.0282(12) Uani 1 1 d . . . . .
H5 H 0.7335 0.1385 0.9473 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5857(4) 0.1792(3) 0.9817(2) 0.0201(11) Uani 1 1 d . . . . .
C7 C 0.8221(4) 0.2674(4) 0.8729(3) 0.0340(13) Uani 1 1 d . . . . .
C11 C 0.3262(4) 0.1900(3) 0.9862(2) 0.0221(11) Uani 1 1 d . . . . .
C12 C 0.2429(4) 0.1558(3) 1.0278(3) 0.0307(13) Uani 1 1 d . . . . .
H12 H 0.2403 0.1700 1.0752 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1661(4) 0.1022(3) 0.9993(3) 0.0381(14) Uani 1 1 d . . . . .
H13 H 0.1099 0.0786 1.0270 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1697(4) 0.0819(3) 0.9301(3) 0.0338(14) Uani 1 1 d . . . . .
C15 C 0.2485(4) 0.1157(3) 0.8886(3) 0.0333(13) Uani 1 1 d . . . . .
H15 H 0.2485 0.1024 0.8410 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3279(4) 0.1691(3) 0.9162(3) 0.0279(12) Uani 1 1 d . . . . .
H16 H 0.3838 0.1918 0.8879 0.033 Uiso 1 1 calc R U . . .
C17 C 0.3965(4) 0.2942(3) 1.0719(2) 0.0213(11) Uani 1 1 d . . . . .
C18 C 0.4902(4) 0.3172(3) 1.1102(2) 0.0257(12) Uani 1 1 d . . . . .
H18 H 0.5597 0.2939 1.0985 0.031 Uiso 1 1 calc R U . . .
C19 C 0.4827(4) 0.3725(3) 1.1643(3) 0.0286(13) Uani 1 1 d . . . . .
H19 H 0.5461 0.3871 1.1908 0.034 Uiso 1 1 calc R U . . .
C20 C 0.3807(4) 0.4071(3) 1.1798(3) 0.0301(13) Uani 1 1 d . . . . .
C21 C 0.2871(4) 0.3839(3) 1.1437(3) 0.0331(13) Uani 1 1 d . . . . .
H21 H 0.2177 0.4068 1.1563 0.040 Uiso 1 1 calc R U . . .
C22 C 0.2943(4) 0.3278(3) 1.0898(3) 0.0276(12) Uani 1 1 d . . . . .
H22 H 0.2300 0.3119 1.0646 0.033 Uiso 1 1 calc R U . . .
C23 C 0.4599(4) 0.3957(3) 0.9266(3) 0.0279(12) Uani 1 1 d . . . . .
C24 C 0.2761(4) 0.4461(3) 0.9162(3) 0.0322(13) Uani 1 1 d . . . . .
H24 H 0.3005 0.4739 0.8727 0.039 Uiso 1 1 calc R U . . .
C25 C 0.1678(4) 0.4012(3) 0.9030(3) 0.0421(15) Uani 1 1 d . . . . .
H25A H 0.1128 0.4433 0.8875 0.063 Uiso 1 1 calc R U . . .
H25B H 0.1431 0.3740 0.9455 0.063 Uiso 1 1 calc R U . . .
H25C H 0.1771 0.3573 0.8676 0.063 Uiso 1 1 calc R U . . .
C26 C 0.2718(5) 0.5128(3) 0.9716(3) 0.0449(16) Uani 1 1 d . . . . .
H26A H 0.3457 0.5361 0.9798 0.067 Uiso 1 1 calc R U . . .
H26B H 0.2447 0.4866 1.0138 0.067 Uiso 1 1 calc R U . . .
H26C H 0.2222 0.5594 0.9572 0.067 Uiso 1 1 calc R U . . .
C27 C 0.5753(4) 0.1002(3) 1.0262(3) 0.0255(12) Uani 1 1 d . . . . .
C28 C 0.5061(4) 0.0472(3) 1.1335(3) 0.0348(14) Uani 1 1 d . . . . .
H28 H 0.5245 -0.0103 1.1138 0.042 Uiso 1 1 calc R U . . .
C29 C 0.3881(5) 0.0477(4) 1.1582(3) 0.0521(17) Uani 1 1 d . . . . .
H29A H 0.3674 0.1063 1.1712 0.078 Uiso 1 1 calc R U . . .
H29B H 0.3818 0.0097 1.1981 0.078 Uiso 1 1 calc R U . . .
H29C H 0.3391 0.0273 1.1213 0.078 Uiso 1 1 calc R U . . .
C30 C 0.5885(5) 0.0712(4) 1.1875(3) 0.0570(19) Uani 1 1 d . . . . .
H30A H 0.6626 0.0687 1.1684 0.086 Uiso 1 1 calc R U . . .
H30B H 0.5834 0.0310 1.2261 0.086 Uiso 1 1 calc R U . . .
H30C H 0.5736 0.1298 1.2036 0.086 Uiso 1 1 calc R U . . .
C8 C 0.7989(8) 0.2716(8) 0.7948(5) 0.044(2) Uani 0.67(2) 1 d . . P A 1
H8A H 0.8687 0.2736 0.7703 0.066 Uiso 0.67(2) 1 calc R U P A 1
H8B H 0.7559 0.3233 0.7841 0.066 Uiso 0.67(2) 1 calc R U P A 1
H8C H 0.7573 0.2205 0.7804 0.066 Uiso 0.67(2) 1 calc R U P A 1
C9 C 0.9001(8) 0.1903(8) 0.8888(6) 0.044(2) Uani 0.67(2) 1 d . . P A 1
H9A H 0.8653 0.1368 0.8732 0.066 Uiso 0.67(2) 1 calc R U P A 1
H9B H 0.9144 0.1872 0.9384 0.066 Uiso 0.67(2) 1 calc R U P A 1
H9C H 0.9697 0.1984 0.8648 0.066 Uiso 0.67(2) 1 calc R U P A 1
C10 C 0.8765(8) 0.3516(7) 0.8952(6) 0.044(2) Uani 0.67(2) 1 d . . P A 1
H10A H 0.9462 0.3585 0.8711 0.066 Uiso 0.67(2) 1 calc R U P A 1
H10B H 0.8906 0.3504 0.9448 0.066 Uiso 0.67(2) 1 calc R U P A 1
H10C H 0.8277 0.3998 0.8839 0.066 Uiso 0.67(2) 1 calc R U P A 1
C8A C 0.9207(15) 0.237(2) 0.9170(15) 0.070(6) Uani 0.33(2) 1 d . . P A 2
H8AA H 0.9882 0.2421 0.8903 0.104 Uiso 0.33(2) 1 calc R U P A 2
H8AB H 0.9098 0.1774 0.9307 0.104 Uiso 0.33(2) 1 calc R U P A 2
H8AC H 0.9270 0.2736 0.9581 0.104 Uiso 0.33(2) 1 calc R U P A 2
C9A C 0.8536(17) 0.3658(17) 0.8577(17) 0.070(6) Uani 0.33(2) 1 d . . P A 2
H9AA H 0.8121 0.3861 0.8175 0.104 Uiso 0.33(2) 1 calc R U P A 2
H9AB H 0.9326 0.3700 0.8489 0.104 Uiso 0.33(2) 1 calc R U P A 2
H9AC H 0.8354 0.4012 0.8976 0.104 Uiso 0.33(2) 1 calc R U P A 2
C10A C 0.8199(18) 0.231(2) 0.8039(13) 0.070(6) Uani 0.33(2) 1 d . . P A 2
H10D H 0.8858 0.2488 0.7793 0.104 Uiso 0.33(2) 1 calc R U P A 2
H10E H 0.7542 0.2509 0.7791 0.104 Uiso 0.33(2) 1 calc R U P A 2
H10F H 0.8183 0.1678 0.8070 0.104 Uiso 0.33(2) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl16 2.3479(15) . ?
Sb1 Cl12 2.3485(15) . ?
Sb1 Cl11 2.3589(14) . ?
Sb1 Cl14 2.3590(15) . ?
Sb1 Cl15 2.3738(15) . ?
Sb1 Cl13 2.3746(15) . ?
Cl1 C14 1.722(5) . ?
Cl2 C20 1.732(5) . ?
O1 C23 1.321(5) . ?
O1 C24 1.480(5) . ?
O2 C23 1.195(5) . ?
O3 C27 1.188(5) . ?
O4 C27 1.335(6) . ?
O4 C28 1.479(6) . ?
N1 C11 1.383(5) . ?
N1 C17 1.397(6) . ?
N1 C1 1.454(6) . ?
C1 C6 1.387(6) . ?
C1 C2 1.395(6) . ?
C2 C3 1.387(6) . ?
C2 C23 1.513(6) . ?
C3 C4 1.383(6) . ?
C4 C5 1.385(7) . ?
C4 C7 1.523(6) . ?
C5 C6 1.393(6) . ?
C6 C27 1.510(6) . ?
C7 C10A 1.46(3) . ?
C7 C10 1.526(11) . ?
C7 C8A 1.54(2) . ?
C7 C8 1.546(12) . ?
C7 C9 1.557(11) . ?
C7 C9A 1.60(3) . ?
C11 C16 1.401(6) . ?
C11 C12 1.409(6) . ?
C12 C13 1.365(7) . ?
C13 C14 1.386(7) . ?
C14 C15 1.366(7) . ?
C15 C16 1.377(6) . ?
C17 C22 1.396(6) . ?
C17 C18 1.401(6) . ?
C18 C19 1.364(6) . ?
C19 C20 1.389(7) . ?
C20 C21 1.377(6) . ?
C21 C22 1.370(7) . ?
C24 C26 1.498(7) . ?
C24 C25 1.509(7) . ?
C28 C30 1.491(7) . ?
C28 C29 1.519(7) . ?

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
Cl16 Sb1 Cl12 91.00(6) . . ?
Cl16 Sb1 Cl11 89.74(6) . . ?
Cl12 Sb1 Cl11 178.37(6) . . ?
Cl16 Sb1 Cl14 89.99(6) . . ?
Cl12 Sb1 Cl14 91.89(6) . . ?
Cl11 Sb1 Cl14 89.56(5) . . ?
Cl16 Sb1 Cl15 179.82(6) . . ?
Cl12 Sb1 Cl15 89.18(6) . . ?
Cl11 Sb1 Cl15 90.08(5) . . ?
Cl14 Sb1 Cl15 90.00(5) . . ?
Cl16 Sb1 Cl13 90.81(6) . . ?
Cl12 Sb1 Cl13 89.21(6) . . ?
Cl11 Sb1 Cl13 89.33(5) . . ?
Cl14 Sb1 Cl13 178.63(6) . . ?
Cl15 Sb1 Cl13 89.19(5) . . ?
C23 O1 C24 115.9(4) . . ?
C27 O4 C28 117.6(4) . . ?
C11 N1 C17 125.4(4) . . ?
C11 N1 C1 117.5(4) . . ?
C17 N1 C1 117.0(4) . . ?
C6 C1 C2 120.3(4) . . ?
C6 C1 N1 120.3(4) . . ?
C2 C1 N1 119.4(4) . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 C23 115.1(5) . . ?
C1 C2 C23 126.2(4) . . ?
C4 C3 C2 122.9(5) . . ?
C3 C4 C5 116.7(5) . . ?
C3 C4 C7 120.4(5) . . ?
C5 C4 C7 122.9(5) . . ?
C4 C5 C6 122.7(5) . . ?
C1 C6 C5 118.7(4) . . ?
C1 C6 C27 126.0(4) . . ?
C5 C6 C27 115.1(4) . . ?
C10A C7 C4 112.8(9) . . ?
C4 C7 C10 109.0(5) . . ?
C10A C7 C8A 113.6(12) . . ?
C4 C7 C8A 113.1(8) . . ?
C4 C7 C8 108.2(5) . . ?
C10 C7 C8 108.4(6) . . ?
C4 C7 C9 111.8(5) . . ?
C10 C7 C9 110.1(6) . . ?
C8 C7 C9 109.3(6) . . ?
C10A C7 C9A 101.8(13) . . ?
C4 C7 C9A 112.7(9) . . ?
C8A C7 C9A 101.9(11) . . ?
N1 C11 C16 119.8(4) . . ?
N1 C11 C12 120.8(4) . . ?
C16 C11 C12 119.5(5) . . ?
C13 C12 C11 119.3(5) . . ?
C12 C13 C14 120.2(5) . . ?
C15 C14 C13 121.3(5) . . ?
C15 C14 Cl1 118.6(4) . . ?
C13 C14 Cl1 120.0(4) . . ?
C14 C15 C16 119.6(5) . . ?
C15 C16 C11 120.0(5) . . ?
C22 C17 N1 121.0(4) . . ?
C22 C17 C18 119.4(4) . . ?
N1 C17 C18 119.5(4) . . ?
C19 C18 C17 120.7(4) . . ?
C18 C19 C20 118.8(5) . . ?
C21 C20 C19 121.5(5) . . ?
C21 C20 Cl2 119.6(4) . . ?
C19 C20 Cl2 118.9(4) . . ?
C22 C21 C20 119.8(5) . . ?
C21 C22 C17 119.8(5) . . ?
O2 C23 O1 125.3(5) . . ?
O2 C23 C2 121.2(4) . . ?
O1 C23 C2 113.4(4) . . ?
O1 C24 C26 110.5(4) . . ?
O1 C24 C25 105.6(4) . . ?
C26 C24 C25 113.8(5) . . ?
O3 C27 O4 125.1(5) . . ?
O3 C27 C6 123.0(5) . . ?
O4 C27 C6 111.8(4) . . ?
O4 C28 C30 107.9(4) . . ?
O4 C28 C29 104.8(4) . . ?
C30 C28 C29 113.7(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
C11 N1 C1 C6 -75.1(6) . . . . ?
C17 N1 C1 C6 108.0(5) . . . . ?
C11 N1 C1 C2 104.6(5) . . . . ?
C17 N1 C1 C2 -72.3(5) . . . . ?
C6 C1 C2 C3 -1.5(7) . . . . ?
N1 C1 C2 C3 178.7(4) . . . . ?
C6 C1 C2 C23 175.5(5) . . . . ?
N1 C1 C2 C23 -4.2(7) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C23 C2 C3 C4 -176.4(5) . . . . ?
C2 C3 C4 C5 1.1(8) . . . . ?
C2 C3 C4 C7 -179.1(5) . . . . ?
C3 C4 C5 C6 -2.9(7) . . . . ?
C7 C4 C5 C6 177.4(5) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
N1 C1 C6 C5 179.6(4) . . . . ?
C2 C1 C6 C27 174.1(4) . . . . ?
N1 C1 C6 C27 -6.2(7) . . . . ?
C4 C5 C6 C1 2.4(7) . . . . ?
C4 C5 C6 C27 -172.4(4) . . . . ?
C3 C4 C7 C10A -93.7(15) . . . . ?
C5 C4 C7 C10A 86.1(15) . . . . ?
C3 C4 C7 C10 52.5(8) . . . . ?
C5 C4 C7 C10 -127.8(7) . . . . ?
C3 C4 C7 C8A 135.7(16) . . . . ?
C5 C4 C7 C8A -44.6(17) . . . . ?
C3 C4 C7 C8 -65.3(8) . . . . ?
C5 C4 C7 C8 114.5(7) . . . . ?
C3 C4 C7 C9 174.3(7) . . . . ?
C5 C4 C7 C9 -5.9(9) . . . . ?
C3 C4 C7 C9A 20.8(14) . . . . ?
C5 C4 C7 C9A -159.4(13) . . . . ?
C17 N1 C11 C16 153.9(4) . . . . ?
C1 N1 C11 C16 -22.7(6) . . . . ?
C17 N1 C11 C12 -27.6(7) . . . . ?
C1 N1 C11 C12 155.8(4) . . . . ?
N1 C11 C12 C13 -177.7(4) . . . . ?
C16 C11 C12 C13 0.8(7) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C12 C13 C14 Cl1 177.1(4) . . . . ?
C13 C14 C15 C16 1.8(8) . . . . ?
Cl1 C14 C15 C16 -176.3(4) . . . . ?
C14 C15 C16 C11 -1.3(7) . . . . ?
N1 C11 C16 C15 178.6(4) . . . . ?
C12 C11 C16 C15 0.1(7) . . . . ?
C11 N1 C17 C22 -28.4(7) . . . . ?
C1 N1 C17 C22 148.2(4) . . . . ?
C11 N1 C17 C18 155.4(4) . . . . ?
C1 N1 C17 C18 -28.1(6) . . . . ?
C22 C17 C18 C19 -0.7(7) . . . . ?
N1 C17 C18 C19 175.6(4) . . . . ?
C17 C18 C19 C20 -1.3(7) . . . . ?
C18 C19 C20 C21 2.8(8) . . . . ?
C18 C19 C20 Cl2 -174.8(4) . . . . ?
C19 C20 C21 C22 -2.4(8) . . . . ?
Cl2 C20 C21 C22 175.3(4) . . . . ?
C20 C21 C22 C17 0.3(8) . . . . ?
N1 C17 C22 C21 -175.1(4) . . . . ?
C18 C17 C22 C21 1.2(7) . . . . ?
C24 O1 C23 O2 5.7(8) . . . . ?
C24 O1 C23 C2 -173.7(4) . . . . ?
C3 C2 C23 O2 -23.9(7) . . . . ?
C1 C2 C23 O2 159.0(5) . . . . ?
C3 C2 C23 O1 155.6(4) . . . . ?
C1 C2 C23 O1 -21.6(7) . . . . ?
C23 O1 C24 C26 -78.4(6) . . . . ?
C23 O1 C24 C25 158.2(4) . . . . ?
C28 O4 C27 O3 7.6(7) . . . . ?
C28 O4 C27 C6 -169.8(4) . . . . ?
C1 C6 C27 O3 160.5(5) . . . . ?
C5 C6 C27 O3 -25.0(7) . . . . ?
C1 C6 C27 O4 -22.0(7) . . . . ?
C5 C6 C27 O4 152.5(4) . . . . ?
C27 O4 C28 C30 92.5(5) . . . . ?
C27 O4 C28 C29 -145.9(5) . . . . ?

_refine_diff_density_max         0.849
_refine_diff_density_min         -0.848
_refine_diff_density_rms         0.117

_shelxl_version_number           2014/5

