 
data_DAS-VI-88
 
_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
 'C23 H28 Br Cl N3 O1.50' 
_chemical_formula_weight          485.84

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'
 'Br'  'Br'  -0.2901   2.4595
 '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'
 '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            5
_space_group_name_H-M_alt         'C 2'
_space_group_name_Hall            'C 2y'
 
_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'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'
 
_cell_length_a                    31.216(3)
_cell_length_b                    8.4388(8)
_cell_length_c                    8.5385(8)
_cell_angle_alpha                 90
_cell_angle_beta                  93.3905(17)
_cell_angle_gamma                 90
_cell_volume                      2245.4(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9965 
_cell_measurement_theta_min       2.50
_cell_measurement_theta_max       27.1
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.437          
_exptl_crystal_F_000              1004
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.140
_exptl_crystal_size_mid           0.120
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     1.972
_shelx_estimated_absorpt_T_min    0.770
_shelx_estimated_absorpt_T_max    0.891
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6160                    
_exptl_absorpt_correction_T_max   0.7455    
_exptl_absorpt_process_details    twinabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)  
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'I\mS microfocus tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   
;
Bruker D8 goniometer with CCD area detector  
; 
_diffrn_measurement_method        'omega and phi scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6527
_diffrn_reflns_av_unetI/netI      0.0409
_diffrn_reflns_av_R_equivalents   0.0318
_diffrn_reflns_limit_h_min        -39
_diffrn_reflns_limit_h_max        39
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          1.307
_diffrn_reflns_theta_max          27.118
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              6527
_reflns_number_gt                 6120
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.867
_reflns_Friedel_fraction_max      0.994
_reflns_Friedel_fraction_full     0.999
 
_reflns_special_details
;
 _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_cell_refinement        'SAINT 8.37A (Bruker-AXS, 2015)' 
_computing_data_reduction         'SAINT 8.37A (Bruker-AXS, 2015)' 
_computing_structure_solution     'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics     'Bruker SHELXTL (Sheldrick, 2015)' 
_computing_publication_material   'Bruker SHELXTL (Sheldrick, 2015)' 
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. All non-H atoms, including 
 the disorder fragments were located in difference-Fourier maps, and then 
 refined anisotropically. The restraints on bond lengths and atomic 
 displacement parameters of disorder fragments (SAME and RIGU instructions 
 of SHELXL-2014) have been applied for the disorder refinement.  

 The crystal is non-merohedrol twin, but we have well refined the structure 
 by using reflections in hkl5 format that is created by Cell_Now/Twinabs.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0261P)²+1.5025P] 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 1947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.006(3)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          6527
_refine_ls_number_parameters      301
_refine_ls_number_restraints      25
_refine_ls_R_factor_all           0.0377
_refine_ls_R_factor_gt            0.0327
_refine_ls_wR_factor_ref          0.0636
_refine_ls_wR_factor_gt           0.0621
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_restrained_S_all       1.041
_refine_ls_shift/su_max           0.002
_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 -0.50372(2) -0.40509(8) -0.23031(6) 0.03901(16) Uani 1 1 d . . . . .
O1 O -0.76380(12) -0.5504(4) -0.5127(4) 0.0279(8) Uani 1 1 d . . . . .
H1 H -0.7782(17) -0.521(6) -0.425(6) 0.038(16) Uiso 1 1 d . . . . .
N1 N -0.72332(11) -0.5306(4) -0.7959(4) 0.0150(8) Uani 1 1 d . . . . .
N2 N -0.72254(11) -0.3753(4) -0.8208(4) 0.0156(8) Uani 1 1 d . . . . .
N3 N -0.68677(12) -0.3290(5) -0.7444(4) 0.0168(8) Uani 1 1 d . . . . .
H3 H -0.6813(18) -0.234(7) -0.745(7) 0.05(2) Uiso 1 1 d . . . . .
C1 C -0.81994(14) -0.4610(5) -0.7848(5) 0.0233(10) Uani 1 1 d . . . . .
H1A H -0.8056 -0.3886 -0.7070 0.028 Uiso 1 1 calc R U . . .
H1B H -0.8158 -0.4180 -0.8907 0.028 Uiso 1 1 calc R U . . .
C2 C -0.86796(14) -0.4674(5) -0.7581(5) 0.0224(10) Uani 1 1 d . . . . .
H2A H -0.8724 -0.5144 -0.6541 0.027 Uiso 1 1 calc R U . . .
H2B H -0.8800 -0.3588 -0.7601 0.027 Uiso 1 1 calc R U . . .
C3 C -0.89076(15) -0.5672(5) -0.8864(5) 0.0225(11) Uani 1 1 d . . . . .
H3A H -0.9212 -0.5806 -0.8630 0.027 Uiso 1 1 calc R U . . .
H3B H -0.8898 -0.5115 -0.9881 0.027 Uiso 1 1 calc R U . . .
C4 C -0.86999(15) -0.7288(5) -0.8987(5) 0.0166(10) Uani 1 1 d . . . . .
C5 C -0.89370(17) -0.8523(5) -0.9690(6) 0.0205(11) Uani 1 1 d . . . . .
H5 H -0.9216 -0.8296 -1.0134 0.025 Uiso 1 1 calc R U . . .
C6 C -0.87862(17) -1.0073(5) -0.9777(6) 0.0202(11) Uani 1 1 d . . . . .
C7 C -0.83777(16) -1.0364(6) -0.9093(5) 0.0191(10) Uani 1 1 d . . . . .
H7 H -0.8266 -1.1411 -0.9084 0.023 Uiso 1 1 calc R U . . .
C8 C -0.81301(12) -0.9129(6) -0.8419(4) 0.0188(9) Uani 1 1 d . . . . .
H8 H -0.7851 -0.9353 -0.7973 0.023 Uiso 1 1 calc R U . . .
C9 C -0.82832(14) -0.7589(5) -0.8387(5) 0.0150(9) Uani 1 1 d . . . . .
C10 C -0.79907(13) -0.6273(5) -0.7696(5) 0.0156(9) Uani 1 1 d . . . . .
C11 C -0.75859(15) -0.6299(5) -0.8629(5) 0.0187(10) Uani 1 1 d . . . . .
H11A H -0.7483 -0.7406 -0.8691 0.022 Uiso 1 1 calc R U . . .
H11B H -0.7662 -0.5936 -0.9713 0.022 Uiso 1 1 calc R U . . .
C12 C -0.68924(14) -0.5810(5) -0.7066(5) 0.0169(10) Uani 1 1 d . . . . .
H12 H -0.6832 -0.6868 -0.6745 0.020 Uiso 1 1 calc R U . . .
C13 C -0.66498(14) -0.4494(5) -0.6710(5) 0.0165(10) Uani 1 1 d . . . . .
C14 C -0.62494(14) -0.4340(6) -0.5727(5) 0.0178(11) Uani 1 1 d . . . . .
C15 C -0.61114(19) -0.5646(7) -0.4856(7) 0.0389(16) Uani 1 1 d . . . . .
H15 H -0.6267 -0.6612 -0.4943 0.047 Uiso 1 1 calc R U . . .
C16 C -0.57473(18) -0.5541(7) -0.3862(7) 0.0409(16) Uani 1 1 d . . . . .
H16 H -0.5653 -0.6436 -0.3260 0.049 Uiso 1 1 calc R U . . .
C17 C -0.55231(13) -0.4161(8) -0.3742(4) 0.0259(10) Uani 1 1 d . . . . .
C18 C -0.56493(17) -0.2859(6) -0.4615(6) 0.0272(13) Uani 1 1 d . . . . .
H18 H -0.5488 -0.1906 -0.4536 0.033 Uiso 1 1 calc R U . . .
C19 C -0.60146(17) -0.2949(6) -0.5610(6) 0.0240(12) Uani 1 1 d . . . . .
H19 H -0.6105 -0.2052 -0.6216 0.029 Uiso 1 1 calc R U . . .
C20 C -0.90510(16) -1.1361(6) -1.0559(5) 0.0279(12) Uani 1 1 d . . . . .
H20A H -0.9270 -1.1711 -0.9858 0.042 Uiso 1 1 calc R U . . .
H20B H -0.8865 -1.2257 -1.0792 0.042 Uiso 1 1 calc R U . . .
H20C H -0.9191 -1.0958 -1.1537 0.042 Uiso 1 1 calc R U . . .
C21 C -0.78893(16) -0.6675(5) -0.5944(5) 0.0203(11) Uani 1 1 d . . . . .
H21A H -0.8163 -0.6806 -0.5426 0.024 Uiso 1 1 calc R U . . .
H21B H -0.7735 -0.7700 -0.5871 0.024 Uiso 1 1 calc R U . . .
Cl1 Cl -0.67428(4) 0.02375(11) -0.75240(14) 0.0243(3) Uani 1 1 d . . . . .
C1S C -0.4598(4) 0.0553(16) -0.2702(17) 0.051(4) Uani 0.5 1 d D U P A -1
H1SA H -0.4325 0.0793 -0.3162 0.077 Uiso 0.5 1 calc R U P A -1
H1SB H -0.4631 -0.0598 -0.2615 0.077 Uiso 0.5 1 calc R U P A -1
H1SC H -0.4600 0.1031 -0.1656 0.077 Uiso 0.5 1 calc R U P A -1
C2S C -0.4966(5) 0.122(2) -0.3742(16) 0.045(4) Uani 0.5 1 d D U P A -1
H2SA H -0.5244 0.0912 -0.3334 0.054 Uiso 0.5 1 calc R U P A -1
H2SB H -0.4950 0.2395 -0.3759 0.054 Uiso 0.5 1 calc R U P A -1
O1S O -0.4933(4) 0.0623(8) -0.5250(13) 0.038(3) Uani 0.5 1 d D U P A -1
C3S C -0.5253(5) 0.1224(18) -0.6339(17) 0.046(4) Uani 0.5 1 d D U P A -1
H3SA H -0.5246 0.2397 -0.6333 0.056 Uiso 0.5 1 calc R U P A -1
H3SB H -0.5540 0.0880 -0.6039 0.056 Uiso 0.5 1 calc R U P A -1
C4S C -0.5174(5) 0.0622(16) -0.7949(15) 0.056(4) Uani 0.5 1 d D U P A -1
H4SA H -0.5133 -0.0530 -0.7910 0.085 Uiso 0.5 1 calc R U P A -1
H4SB H -0.4915 0.1124 -0.8319 0.085 Uiso 0.5 1 calc R U P A -1
H4SC H -0.5420 0.0876 -0.8668 0.085 Uiso 0.5 1 calc R U P A -1
 
 
_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 C17 1.897(4) . ?
O1 C21 1.419(5) . ?
O1 H1 0.93(5) . ?
N1 N2 1.327(5) . ?
N1 C12 1.341(5) . ?
N1 C11 1.472(5) . ?
N2 N3 1.319(5) . ?
N3 C13 1.356(6) . ?
N3 H3 0.82(6) . ?
C1 C2 1.531(6) . ?
C1 C10 1.550(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.525(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.516(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.393(6) . ?
C4 C5 1.393(6) . ?
C5 C6 1.394(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(7) . ?
C6 C20 1.498(7) . ?
C7 C8 1.400(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.533(6) . ?
C10 C11 1.533(6) . ?
C10 C21 1.549(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.368(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.470(6) . ?
C14 C15 1.383(7) . ?
C14 C19 1.384(7) . ?
C15 C16 1.381(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.359(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(7) . ?
C18 C19 1.383(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C1S C2S 1.519(14) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2S O1S 1.393(16) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
O1S C3S 1.419(16) . ?
C3S C4S 1.500(16) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 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
C21 O1 H1 108(3) . . ?
N2 N1 C12 112.5(4) . . ?
N2 N1 C11 121.3(4) . . ?
C12 N1 C11 126.2(4) . . ?
N3 N2 N1 103.7(3) . . ?
N2 N3 C13 113.1(4) . . ?
N2 N3 H3 117(4) . . ?
C13 N3 H3 130(4) . . ?
C2 C1 C10 111.5(4) . . ?
C2 C1 H1A 109.3 . . ?
C10 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C10 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 109.4(4) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C4 C3 C2 111.3(4) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C9 C4 C5 118.9(4) . . ?
C9 C4 C3 122.2(4) . . ?
C5 C4 C3 119.0(4) . . ?
C4 C5 C6 123.5(5) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
C7 C6 C5 116.5(5) . . ?
C7 C6 C20 121.7(4) . . ?
C5 C6 C20 121.7(5) . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 118.6(4) . . ?
C8 C9 C10 119.3(4) . . ?
C4 C9 C10 122.1(4) . . ?
C9 C10 C11 106.3(3) . . ?
C9 C10 C21 107.2(3) . . ?
C11 C10 C21 111.8(4) . . ?
C9 C10 C1 112.7(4) . . ?
C11 C10 C1 108.9(3) . . ?
C21 C10 C1 109.9(3) . . ?
N1 C11 C10 114.2(3) . . ?
N1 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
N1 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N1 C12 C13 106.2(4) . . ?
N1 C12 H12 126.9 . . ?
C13 C12 H12 126.9 . . ?
N3 C13 C12 104.5(4) . . ?
N3 C13 C14 125.8(4) . . ?
C12 C13 C14 129.7(4) . . ?
C15 C14 C19 119.3(4) . . ?
C15 C14 C13 117.7(4) . . ?
C19 C14 C13 123.0(4) . . ?
C16 C15 C14 119.9(5) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.0(4) . . ?
C16 C17 Br1 118.6(4) . . ?
C18 C17 Br1 120.3(4) . . ?
C17 C18 C19 119.3(5) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C14 120.3(5) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C6 C20 H20A 109.5 . . ?
C6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 C10 113.4(4) . . ?
O1 C21 H21A 108.9 . . ?
C10 C21 H21A 108.9 . . ?
O1 C21 H21B 108.9 . . ?
C10 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O1S C2S C1S 108.1(12) . . ?
O1S C2S H2SA 110.1 . . ?
C1S C2S H2SA 110.1 . . ?
O1S C2S H2SB 110.1 . . ?
C1S C2S H2SB 110.1 . . ?
H2SA C2S H2SB 108.4 . . ?
C2S O1S C3S 112.8(10) . . ?
O1S C3S C4S 109.3(11) . . ?
O1S C3S H3SA 109.8 . . ?
C4S C3S H3SA 109.8 . . ?
O1S C3S H3SB 109.8 . . ?
C4S C3S H3SB 109.8 . . ?
H3SA C3S H3SB 108.3 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 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
C12 N1 N2 N3 0.1(5) . . . . ?
C11 N1 N2 N3 -179.7(3) . . . . ?
N1 N2 N3 C13 -0.5(4) . . . . ?
C10 C1 C2 C3 -63.9(5) . . . . ?
C1 C2 C3 C4 53.2(5) . . . . ?
C2 C3 C4 C9 -19.5(6) . . . . ?
C2 C3 C4 C5 158.9(4) . . . . ?
C9 C4 C5 C6 2.5(7) . . . . ?
C3 C4 C5 C6 -175.9(5) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C4 C5 C6 C20 -179.4(5) . . . . ?
C5 C6 C7 C8 -2.6(7) . . . . ?
C20 C6 C7 C8 177.7(4) . . . . ?
C6 C7 C8 C9 0.9(7) . . . . ?
C7 C8 C9 C4 2.6(6) . . . . ?
C7 C8 C9 C10 -177.4(4) . . . . ?
C5 C4 C9 C8 -4.2(6) . . . . ?
C3 C4 C9 C8 174.2(4) . . . . ?
C5 C4 C9 C10 175.8(4) . . . . ?
C3 C4 C9 C10 -5.8(6) . . . . ?
C8 C9 C10 C11 57.0(5) . . . . ?
C4 C9 C10 C11 -123.0(4) . . . . ?
C8 C9 C10 C21 -62.7(5) . . . . ?
C4 C9 C10 C21 117.3(4) . . . . ?
C8 C9 C10 C1 176.2(4) . . . . ?
C4 C9 C10 C1 -3.7(6) . . . . ?
C2 C1 C10 C9 38.0(5) . . . . ?
C2 C1 C10 C11 155.8(4) . . . . ?
C2 C1 C10 C21 -81.4(4) . . . . ?
N2 N1 C11 C10 -81.1(5) . . . . ?
C12 N1 C11 C10 99.1(5) . . . . ?
C9 C10 C11 N1 -169.7(3) . . . . ?
C21 C10 C11 N1 -53.1(5) . . . . ?
C1 C10 C11 N1 68.5(5) . . . . ?
N2 N1 C12 C13 0.2(5) . . . . ?
C11 N1 C12 C13 -180.0(4) . . . . ?
N2 N3 C13 C12 0.6(5) . . . . ?
N2 N3 C13 C14 -177.8(4) . . . . ?
N1 C12 C13 N3 -0.5(5) . . . . ?
N1 C12 C13 C14 177.9(4) . . . . ?
N3 C13 C14 C15 169.2(5) . . . . ?
C12 C13 C14 C15 -8.9(7) . . . . ?
N3 C13 C14 C19 -9.1(7) . . . . ?
C12 C13 C14 C19 172.8(5) . . . . ?
C19 C14 C15 C16 1.2(9) . . . . ?
C13 C14 C15 C16 -177.2(5) . . . . ?
C14 C15 C16 C17 -0.3(10) . . . . ?
C15 C16 C17 C18 -0.9(9) . . . . ?
C15 C16 C17 Br1 177.7(5) . . . . ?
C16 C17 C18 C19 1.1(8) . . . . ?
Br1 C17 C18 C19 -177.4(4) . . . . ?
C17 C18 C19 C14 -0.2(8) . . . . ?
C15 C14 C19 C18 -1.0(8) . . . . ?
C13 C14 C19 C18 177.3(4) . . . . ?
C9 C10 C21 O1 -176.8(4) . . . . ?
C11 C10 C21 O1 67.1(5) . . . . ?
C1 C10 C21 O1 -54.0(5) . . . . ?
C1S C2S O1S C3S -177.7(14) . . . . ?
C2S O1S C3S C4S 175.5(14) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1 Cl1  0.93(5) 2.22(5) 3.126(4) 166(5) 4_344
N3 H3 Cl1  0.82(6) 2.18(6) 3.003(4) 174(6) .
 
_refine_diff_density_max    0.480
_refine_diff_density_min   -0.284
_refine_diff_density_rms    0.056



