 
data_A094O_019
 
_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
 'C23 H36 B F3 N2 O6 S' 
_chemical_formula_weight          536.41

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'
 'B'  'B'   0.0013   0.0007
 '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'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.2674(5)
_cell_length_b                    10.7476(7)
_cell_length_c                    28.5667(16)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2845.3(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used      9984
_cell_measurement_theta_min        2.99
_cell_measurement_theta_max       28.31
 
_exptl_crystal_description        'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.252          
_exptl_crystal_F_000              1136
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.302
_exptl_crystal_size_mid           0.226
_exptl_crystal_size_min           0.098
_exptl_absorpt_coefficient_mu     0.171
_shelx_estimated_absorpt_T_min    0.950
_shelx_estimated_absorpt_T_max    0.983
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.6905
_exptl_absorpt_correction_T_max   0.7457
_exptl_absorpt_process_details    SADABS 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'
_diffrn_measurement_device_type   'Photon 100 CMOS detector'  
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             18760
_diffrn_reflns_av_unetI/netI      0.0620
_diffrn_reflns_av_R_equivalents   0.0477
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -35
_diffrn_reflns_limit_l_max        37
_diffrn_reflns_theta_min          3.234
_diffrn_reflns_theta_max          28.000
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.994
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.994
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.995
_reflns_number_total              6845
_reflns_number_gt                 5137
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.771
_reflns_Friedel_fraction_max      0.995
_reflns_Friedel_fraction_full     0.996
 
_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 APEXIII' 
_computing_cell_refinement        'Bruker APEXIII' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     SHELXS
_computing_structure_refinement   SHELXL
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0472P)²+0.4695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1783 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.04(4)
_chemical_absolute_configuration  syn
_refine_ls_number_reflns          6845
_refine_ls_number_parameters      369
_refine_ls_number_restraints      420
_refine_ls_R_factor_all           0.0816
_refine_ls_R_factor_gt            0.0493
_refine_ls_wR_factor_ref          0.1112
_refine_ls_wR_factor_gt           0.0983
_refine_ls_goodness_of_fit_ref    1.041
_refine_ls_restrained_S_all       1.051
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.6363(3) 0.9253(3) 0.67310(9) 0.0256(6) Uani 1 1 d . U . . .
C2 C 0.5755(3) 1.0265(3) 0.64051(9) 0.0294(6) Uani 1 1 d . U . . .
C3 C 0.6607(4) 1.0749(3) 0.60498(12) 0.0458(8) Uani 1 1 d . U . . .
H3 H 0.758464 1.049323 0.602112 0.055 Uiso 1 1 calc R U . . .
C4 C 0.6038(4) 1.1610(4) 0.57344(12) 0.0551(10) Uani 1 1 d . U . . .
H4 H 0.662548 1.192702 0.548931 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4644(4) 1.1998(3) 0.57761(12) 0.0478(9) Uani 1 1 d . U . . .
C6 C 0.3799(4) 1.1543(4) 0.61298(12) 0.0494(9) Uani 1 1 d . U . . .
H6 H 0.283070 1.182176 0.616055 0.059 Uiso 1 1 calc R U . . .
C7 C 0.4344(4) 1.0678(3) 0.64434(11) 0.0394(7) Uani 1 1 d . U . . .
H7 H 0.374574 1.036619 0.668654 0.047 Uiso 1 1 calc R U . . .
C8 C 0.4053(6) 1.2931(5) 0.54354(15) 0.0728(13) Uani 1 1 d . U . . .
F1 F 0.4239(9) 1.2623(6) 0.50014(14) 0.106(2) Uani 0.769(11) 1 d . U P A 1
F2 F 0.2671(6) 1.3171(8) 0.5490(2) 0.125(3) Uani 0.769(11) 1 d . U P A 1
F3 F 0.4666(10) 1.4048(5) 0.5498(2) 0.127(3) Uani 0.769(11) 1 d . U P A 1
F1B F 0.502(2) 1.324(2) 0.5096(7) 0.103(6) Uani 0.231(11) 1 d . U P A 2
F2B F 0.296(3) 1.2333(17) 0.5194(7) 0.111(7) Uani 0.231(11) 1 d . U P A 2
F3B F 0.359(3) 1.3843(18) 0.5586(5) 0.088(6) Uani 0.231(11) 1 d . U P A 2
N1 N 0.5468(3) 0.9248(2) 0.71602(8) 0.0263(5) Uani 1 1 d . U . . .
H1N H 0.543(4) 0.990(3) 0.7295(12) 0.039 Uiso 1 1 d . U . . .
S1 S 0.57838(8) 0.81777(6) 0.75655(2) 0.02904(17) Uani 1 1 d . U . . .
O1 O 0.7282(2) 0.7906(2) 0.75819(8) 0.0418(5) Uani 1 1 d . U . . .
O2 O 0.4824(3) 0.71632(18) 0.74805(8) 0.0442(6) Uani 1 1 d . U . . .
N2 N 0.5333(3) 0.8831(2) 0.80501(8) 0.0359(6) Uani 1 1 d . U . . .
C9 C 0.6324(4) 0.9736(3) 0.82518(12) 0.0503(9) Uani 1 1 d . U . . .
H9A H 0.617634 0.977768 0.859109 0.075 Uiso 1 1 calc R U . . .
H9B H 0.614338 1.055611 0.811365 0.075 Uiso 1 1 calc R U . . .
H9C H 0.732022 0.948365 0.818625 0.075 Uiso 1 1 calc R U . . .
C10 C 0.3815(4) 0.9015(5) 0.81537(15) 0.0679(12) Uani 1 1 d . U . . .
H10A H 0.349770 0.981338 0.802409 0.102 Uiso 1 1 calc R U . . .
H10B H 0.367227 0.901515 0.849360 0.102 Uiso 1 1 calc R U . . .
H10C H 0.325095 0.833992 0.801338 0.102 Uiso 1 1 calc R U . . .
C11 C 0.7940(3) 0.9605(3) 0.68458(11) 0.0298(6) Uani 1 1 d . U . . .
O3 O 0.8010(2) 1.05075(18) 0.71605(8) 0.0341(5) Uani 1 1 d . U . . .
O4 O 0.8942(2) 0.9130(2) 0.66486(8) 0.0440(6) Uani 1 1 d . U . . .
C12 C 0.9407(3) 1.1150(3) 0.72649(12) 0.0402(8) Uani 1 1 d . U . . .
C13 C 0.8998(4) 1.1991(3) 0.76691(13) 0.0527(9) Uani 1 1 d . U . . .
H13A H 0.867899 1.148297 0.793462 0.079 Uiso 1 1 calc R U . . .
H13B H 0.821385 1.254538 0.757226 0.079 Uiso 1 1 calc R U . . .
H13C H 0.983723 1.248759 0.776202 0.079 Uiso 1 1 calc R U . . .
C14 C 0.9834(4) 1.1875(4) 0.68341(14) 0.0542(9) Uani 1 1 d . U . . .
H14A H 0.903181 1.241055 0.673762 0.081 Uiso 1 1 calc R U . . .
H14B H 1.006874 1.129578 0.658024 0.081 Uiso 1 1 calc R U . . .
H14C H 1.067992 1.238933 0.690466 0.081 Uiso 1 1 calc R U . . .
C15 C 1.0558(4) 1.0240(3) 0.74208(18) 0.0634(12) Uani 1 1 d . U . . .
H15A H 1.088320 0.974922 0.715156 0.095 Uiso 1 1 calc R U . . .
H15B H 1.015792 0.968203 0.765933 0.095 Uiso 1 1 calc R U . . .
H15C H 1.137641 1.069821 0.755251 0.095 Uiso 1 1 calc R U . . .
C16 C 0.6350(3) 0.7957(3) 0.64893(10) 0.0308(6) Uani 1 1 d . U . . .
H16 H 0.648(4) 0.732(3) 0.6738(12) 0.046 Uiso 1 1 d . U . . .
B1 B 0.7670(4) 0.7664(4) 0.61549(13) 0.0386(9) Uani 1 1 d . U . . .
O5 O 0.7970(2) 0.8220(3) 0.57379(8) 0.0506(6) Uani 1 1 d . U . . .
O6 O 0.8465(3) 0.6609(3) 0.62276(8) 0.0569(7) Uani 1 1 d . U . . .
C17 C 0.4913(4) 0.7695(3) 0.62408(13) 0.0431(8) Uani 1 1 d . U . . .
H17A H 0.479980 0.827000 0.597702 0.065 Uiso 1 1 calc R U . . .
H17B H 0.411558 0.781186 0.646164 0.065 Uiso 1 1 calc R U . . .
H17C H 0.490731 0.683688 0.612502 0.065 Uiso 1 1 calc R U . . .
C18 C 0.9294(5) 0.7651(5) 0.55586(13) 0.0662(11) Uani 1 1 d . U . . .
C19 C 0.9267(5) 0.6375(4) 0.57976(15) 0.0715(12) Uani 1 1 d . U . . .
C20 C 0.9236(6) 0.7648(6) 0.50286(14) 0.0959(18) Uani 1 1 d . U . . .
H20A H 0.912483 0.850294 0.491470 0.144 Uiso 1 1 calc R U . . .
H20B H 0.841493 0.714579 0.492394 0.144 Uiso 1 1 calc R U . . .
H20C H 1.013214 0.729383 0.490421 0.144 Uiso 1 1 calc R U . . .
C21 C 1.0547(5) 0.8483(6) 0.57167(19) 0.102(2) Uani 1 1 d . U . . .
H21A H 1.059673 0.848809 0.605938 0.152 Uiso 1 1 calc R U . . .
H21B H 1.039025 0.933241 0.560283 0.152 Uiso 1 1 calc R U . . .
H21C H 1.145373 0.815985 0.558897 0.152 Uiso 1 1 calc R U . . .
C22 C 0.8376(8) 0.5415(6) 0.5528(2) 0.120(2) Uani 1 1 d . U . . .
H22A H 0.739876 0.573729 0.547769 0.181 Uiso 1 1 calc R U . . .
H22B H 0.832612 0.464021 0.570782 0.181 Uiso 1 1 calc R U . . .
H22C H 0.883225 0.525213 0.522422 0.181 Uiso 1 1 calc R U . . .
C23 C 1.0732(7) 0.5852(7) 0.5930(2) 0.139(3) Uani 1 1 d . U . . .
H23A H 1.060810 0.503409 0.607592 0.208 Uiso 1 1 calc R U . . .
H23B H 1.120761 0.641635 0.615049 0.208 Uiso 1 1 calc R U . . .
H23C H 1.132664 0.576759 0.564773 0.208 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 N1 1.481(4) . ?
C1 C2 1.539(4) . ?
C1 C11 1.545(4) . ?
C1 C16 1.555(4) . ?
C2 C7 1.385(5) . ?
C2 C3 1.388(4) . ?
C3 C4 1.395(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(5) . ?
C5 C8 1.500(5) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 F3B 1.153(15) . ?
C8 F1 1.295(6) . ?
C8 F2 1.316(7) . ?
C8 F3 1.340(7) . ?
C8 F1B 1.360(16) . ?
C8 F2B 1.382(18) . ?
N1 S1 1.658(2) . ?
N1 H1N 0.80(3) . ?
S1 O1 1.420(2) . ?
S1 O2 1.428(2) . ?
S1 N2 1.608(3) . ?
N2 C10 1.451(5) . ?
N2 C9 1.457(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.200(4) . ?
C11 O3 1.324(4) . ?
O3 C12 1.497(3) . ?
C12 C14 1.510(5) . ?
C12 C15 1.514(4) . ?
C12 C13 1.515(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.535(4) . ?
C16 B1 1.583(5) . ?
C16 H16 0.99(4) . ?
B1 O5 1.362(4) . ?
B1 O6 1.368(5) . ?
O5 C18 1.464(4) . ?
O6 C19 1.457(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.515(5) . ?
C18 C19 1.533(7) . ?
C18 C21 1.533(7) . ?
C19 C23 1.517(7) . ?
C19 C22 1.530(7) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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 . ?
 
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
N1 C1 C2 107.3(2) . . ?
N1 C1 C11 110.8(2) . . ?
C2 C1 C11 107.6(2) . . ?
N1 C1 C16 111.1(2) . . ?
C2 C1 C16 111.2(2) . . ?
C11 C1 C16 108.7(2) . . ?
C7 C2 C3 118.3(3) . . ?
C7 C2 C1 121.6(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 C8 119.6(4) . . ?
C6 C5 C8 120.6(4) . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 120.5(3) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
F1 C8 F2 107.0(6) . . ?
F1 C8 F3 107.4(6) . . ?
F2 C8 F3 102.7(6) . . ?
F3B C8 F1B 107.4(14) . . ?
F3B C8 F2B 108.1(15) . . ?
F1B C8 F2B 103.8(13) . . ?
F3B C8 C5 117.5(8) . . ?
F1 C8 C5 113.7(4) . . ?
F2 C8 C5 114.2(4) . . ?
F3 C8 C5 111.0(4) . . ?
F1B C8 C5 112.8(8) . . ?
F2B C8 C5 106.3(7) . . ?
C1 N1 S1 118.78(19) . . ?
C1 N1 H1N 115(2) . . ?
S1 N1 H1N 106(2) . . ?
O1 S1 O2 117.27(14) . . ?
O1 S1 N2 108.38(14) . . ?
O2 S1 N2 108.55(15) . . ?
O1 S1 N1 109.77(13) . . ?
O2 S1 N1 107.52(13) . . ?
N2 S1 N1 104.61(13) . . ?
C10 N2 C9 116.1(3) . . ?
C10 N2 S1 119.1(2) . . ?
C9 N2 S1 117.9(2) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O3 126.4(3) . . ?
O4 C11 C1 121.9(3) . . ?
O3 C11 C1 111.7(2) . . ?
C11 O3 C12 121.0(2) . . ?
O3 C12 C14 107.6(3) . . ?
O3 C12 C15 111.7(2) . . ?
C14 C12 C15 112.9(3) . . ?
O3 C12 C13 102.2(3) . . ?
C14 C12 C13 112.3(3) . . ?
C15 C12 C13 109.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C1 112.1(3) . . ?
C17 C16 B1 110.8(3) . . ?
C1 C16 B1 116.1(3) . . ?
C17 C16 H16 108(2) . . ?
C1 C16 H16 107.4(19) . . ?
B1 C16 H16 102(2) . . ?
O5 B1 O6 112.7(3) . . ?
O5 B1 C16 126.8(3) . . ?
O6 B1 C16 119.3(3) . . ?
B1 O5 C18 107.1(3) . . ?
B1 O6 C19 106.9(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 C20 108.7(4) . . ?
O5 C18 C19 101.8(3) . . ?
C20 C18 C19 116.3(4) . . ?
O5 C18 C21 106.8(3) . . ?
C20 C18 C21 108.8(4) . . ?
C19 C18 C21 113.8(4) . . ?
O6 C19 C23 108.1(4) . . ?
O6 C19 C22 105.5(4) . . ?
C23 C19 C22 111.0(5) . . ?
O6 C19 C18 103.2(3) . . ?
C23 C19 C18 115.3(5) . . ?
C22 C19 C18 112.8(4) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
N1 C1 C2 C7 -22.7(4) . . . . ?
C11 C1 C2 C7 -142.0(3) . . . . ?
C16 C1 C2 C7 99.1(3) . . . . ?
N1 C1 C2 C3 160.0(3) . . . . ?
C11 C1 C2 C3 40.8(4) . . . . ?
C16 C1 C2 C3 -78.2(3) . . . . ?
C7 C2 C3 C4 -1.4(5) . . . . ?
C1 C2 C3 C4 176.0(3) . . . . ?
C2 C3 C4 C5 1.0(6) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C3 C4 C5 C8 179.6(4) . . . . ?
C4 C5 C6 C7 -0.7(6) . . . . ?
C8 C5 C6 C7 179.8(4) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
C1 C2 C7 C6 -176.5(3) . . . . ?
C5 C6 C7 C2 0.3(5) . . . . ?
C4 C5 C8 F3B -122.7(18) . . . . ?
C6 C5 C8 F3B 56.8(19) . . . . ?
C4 C5 C8 F1 52.3(8) . . . . ?
C6 C5 C8 F1 -128.2(7) . . . . ?
C4 C5 C8 F2 175.5(6) . . . . ?
C6 C5 C8 F2 -5.0(8) . . . . ?
C4 C5 C8 F3 -68.9(7) . . . . ?
C6 C5 C8 F3 110.6(7) . . . . ?
C4 C5 C8 F1B 3.1(15) . . . . ?
C6 C5 C8 F1B -177.4(14) . . . . ?
C4 C5 C8 F2B 116.2(13) . . . . ?
C6 C5 C8 F2B -64.3(13) . . . . ?
C2 C1 N1 S1 175.53(18) . . . . ?
C11 C1 N1 S1 -67.3(3) . . . . ?
C16 C1 N1 S1 53.7(3) . . . . ?
C1 N1 S1 O1 34.1(2) . . . . ?
C1 N1 S1 O2 -94.5(2) . . . . ?
C1 N1 S1 N2 150.2(2) . . . . ?
O1 S1 N2 C10 -169.9(3) . . . . ?
O2 S1 N2 C10 -41.5(3) . . . . ?
N1 S1 N2 C10 73.1(3) . . . . ?
O1 S1 N2 C9 40.2(3) . . . . ?
O2 S1 N2 C9 168.6(2) . . . . ?
N1 S1 N2 C9 -76.9(3) . . . . ?
N1 C1 C11 O4 142.9(3) . . . . ?
C2 C1 C11 O4 -100.0(3) . . . . ?
C16 C1 C11 O4 20.5(4) . . . . ?
N1 C1 C11 O3 -40.1(3) . . . . ?
C2 C1 C11 O3 76.9(3) . . . . ?
C16 C1 C11 O3 -162.6(2) . . . . ?
O4 C11 O3 C12 7.3(5) . . . . ?
C1 C11 O3 C12 -169.4(2) . . . . ?
C11 O3 C12 C14 67.1(3) . . . . ?
C11 O3 C12 C15 -57.3(4) . . . . ?
C11 O3 C12 C13 -174.6(3) . . . . ?
N1 C1 C16 C17 73.9(3) . . . . ?
C2 C1 C16 C17 -45.6(3) . . . . ?
C11 C1 C16 C17 -163.9(2) . . . . ?
N1 C1 C16 B1 -157.4(3) . . . . ?
C2 C1 C16 B1 83.1(3) . . . . ?
C11 C1 C16 B1 -35.2(3) . . . . ?
C17 C16 B1 O5 61.3(5) . . . . ?
C1 C16 B1 O5 -68.0(4) . . . . ?
C17 C16 B1 O6 -105.1(4) . . . . ?
C1 C16 B1 O6 125.6(3) . . . . ?
O6 B1 O5 C18 -13.1(4) . . . . ?
C16 B1 O5 C18 179.7(3) . . . . ?
O5 B1 O6 C19 -6.1(4) . . . . ?
C16 B1 O6 C19 162.2(3) . . . . ?
B1 O5 C18 C20 148.5(4) . . . . ?
B1 O5 C18 C19 25.3(4) . . . . ?
B1 O5 C18 C21 -94.3(4) . . . . ?
B1 O6 C19 C23 144.1(5) . . . . ?
B1 O6 C19 C22 -97.1(4) . . . . ?
B1 O6 C19 C18 21.5(4) . . . . ?
O5 C18 C19 O6 -28.0(4) . . . . ?
C20 C18 C19 O6 -146.0(4) . . . . ?
C21 C18 C19 O6 86.4(4) . . . . ?
O5 C18 C19 C23 -145.7(4) . . . . ?
C20 C18 C19 C23 96.4(5) . . . . ?
C21 C18 C19 C23 -31.2(5) . . . . ?
O5 C18 C19 C22 85.3(4) . . . . ?
C20 C18 C19 C22 -32.6(6) . . . . ?
C21 C18 C19 C22 -160.2(4) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag
N1 H1N O2  0.80(3) 2.53(4) 3.308(3) 165(3) 3_656 yes
 
_refine_diff_density_max    0.218
_refine_diff_density_min   -0.347
_refine_diff_density_rms    0.047






















