data_2009src0840

#Dr. L. Martin
#refcode: ADOLINA3
#Mixed counter anion roughly 2:1 Br:Cl
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C40 H44 Br1.32 Cl0.68 O6 S32'
_chemical_formula_weight          1776.26
 
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'
 'S'  'S'   0.1246   0.1234
 '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'
 'Br'  'Br'  -0.2901   2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    Pcca
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z'
 '-x, y, -z+1/2'
 'x+1/2, -y, -z+1/2'
 '-x, -y, -z'
 'x-1/2, y, -z'
 'x, -y, z-1/2'
 '-x-1/2, y, z-1/2'
 
_cell_length_a                    32.736(2)
_cell_length_b                    6.6793(5)
_cell_length_c                    14.7618(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      3227.8(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     6370
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             'Dark Brown'
_exptl_crystal_size_max           0.22
_exptl_crystal_size_mid           0.07
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.828
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1804
_exptl_absorpt_coefficient_mu     1.944
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6744
_exptl_absorpt_correction_T_max   0.9091
_exptl_absorpt_process_details       'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details
;
SADABS was used to perform the Absorption correction
Estimated minimum and maximum transmission: 0.6158 0.7456
The given Tmin and Tmax were generated using the SHELX SIZE command
;


_diffrn_ambient_temperature           120(2)
_diffrn_radiation_wavelength           0.71073
_diffrn_radiation_type                      MoK\a
_diffrn_radiation_source                  'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '9.091'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             32983
_diffrn_reflns_av_R_equivalents   0.0757
_diffrn_reflns_av_sigmaI/netI     0.0443
_diffrn_reflns_limit_h_min        -42
_diffrn_reflns_limit_h_max        42
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.05
_diffrn_reflns_theta_max          27.48
_reflns_number_total              3666
_reflns_number_gt                 2841
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'
 
_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.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0399P)²+7.9829P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3666
_refine_ls_number_parameters      233
_refine_ls_number_restraints      27
_refine_ls_R_factor_all           0.0698
_refine_ls_R_factor_gt            0.0474
_refine_ls_wR_factor_ref          0.1125
_refine_ls_wR_factor_gt           0.1041
_refine_ls_goodness_of_fit_ref    1.080
_refine_ls_restrained_S_all       1.125
_refine_ls_shift/su_max           0.011
_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_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.2500 0.5000 0.94928(6) 0.0338(2) Uani 0.34 2 d SPD A 1
Br1 Br 0.2500 0.5000 0.94928(6) 0.0338(2) Uani 0.66 2 d SP B 2
C1 C 0.69019(19) 0.9635(9) 0.9980(5) 0.0362(18) Uani 0.870(15) 1 d PD C 1
H1A H 0.6876 1.0185 1.0600 0.043 Uiso 0.870(15) 1 calc PR C 1
H1B H 0.7189 0.9197 0.9901 0.043 Uiso 0.870(15) 1 calc PR C 1
C2 C 0.68150(18) 1.1280(10) 0.9313(5) 0.0384(18) Uani 0.870(15) 1 d PD C 1
H2A H 0.6808 1.0709 0.8695 0.046 Uiso 0.870(15) 1 calc PR C 1
H2B H 0.7039 1.2272 0.9337 0.046 Uiso 0.870(15) 1 calc PR C 1
C3 C 0.60097(12) 1.0481(6) 0.9433(3) 0.0313(9) Uani 1 1 d . C .
C4 C 0.61062(12) 0.8541(6) 0.9574(3) 0.0304(9) Uani 1 1 d . C .
C5 C 0.53522(12) 0.8559(6) 0.9049(3) 0.0265(9) Uani 1 1 d . C .
C6 C 0.49660(12) 0.8023(5) 0.8788(3) 0.0267(9) Uani 1 1 d . . .
C7 C 0.43155(12) 0.6101(6) 0.8313(3) 0.0276(9) Uani 1 1 d . D .
C8 C 0.42169(11) 0.8051(6) 0.8223(3) 0.0241(8) Uani 1 1 d . D .
C9 C 0.34160(18) 0.6882(9) 0.8093(6) 0.032(2) Uani 0.678(14) 1 d PD D 1
H9A H 0.3403 0.6625 0.8753 0.038 Uiso 0.678(14) 1 calc PR D 1
H9B H 0.3136 0.7194 0.7882 0.038 Uiso 0.678(14) 1 calc PR D 1
C10 C 0.3564(2) 0.5020(10) 0.7621(6) 0.0276(19) Uani 0.678(14) 1 d PD D 1
H10A H 0.3615 0.5338 0.6975 0.033 Uiso 0.678(14) 1 calc PR D 1
H10B H 0.3345 0.3996 0.7644 0.033 Uiso 0.678(14) 1 calc PR D 1
S1 S 0.65736(3) 0.74677(16) 0.98840(10) 0.0424(3) Uani 1 1 d D . .
S2 S 0.63368(3) 1.25340(16) 0.95345(10) 0.0428(3) Uani 1 1 d D . .
S3 S 0.55187(3) 1.10276(15) 0.90420(8) 0.0318(3) Uani 1 1 d . . .
S4 S 0.57169(3) 0.67931(14) 0.93610(8) 0.0287(2) Uani 1 1 d . . .
S5 S 0.48097(3) 0.55436(14) 0.87075(8) 0.0276(2) Uani 1 1 d . . .
S6 S 0.45979(3) 0.98034(14) 0.84900(8) 0.0310(3) Uani 1 1 d . . .
S7 S 0.37454(3) 0.90591(15) 0.78869(8) 0.0305(3) Uani 1 1 d D . .
S8 S 0.40203(3) 0.39880(16) 0.81028(10) 0.0446(3) Uani 1 1 d D . .
C101 C 0.6915(12) 0.938(4) 0.946(4) 0.041(13) Uani 0.130(15) 1 d PD C 2
H10C H 0.7200 0.9024 0.9618 0.049 Uiso 0.130(15) 1 calc PR C 2
H10D H 0.6893 0.9454 0.8794 0.049 Uiso 0.130(15) 1 calc PR C 2
C102 C 0.6809(13) 1.137(7) 0.987(5) 0.07(2) Uani 0.130(15) 1 d PD C 2
H10E H 0.7034 1.2307 0.9726 0.088 Uiso 0.130(15) 1 calc PR C 2
H10F H 0.6803 1.1204 1.0535 0.088 Uiso 0.130(15) 1 calc PR C 2
C109 C 0.3478(4) 0.6870(18) 0.7451(13) 0.039(5) Uani 0.322(14) 1 d PD D 2
H10G H 0.3188 0.7214 0.7351 0.047 Uiso 0.322(14) 1 calc PR D 2
H10H H 0.3598 0.6492 0.6859 0.047 Uiso 0.322(14) 1 calc PR D 2
C110 C 0.3504(4) 0.510(2) 0.8087(12) 0.030(4) Uani 0.322(14) 1 d PD D 2
H11A H 0.3304 0.4073 0.7895 0.036 Uiso 0.322(14) 1 calc PR D 2
H11B H 0.3430 0.5540 0.8706 0.036 Uiso 0.322(14) 1 calc PR D 2
O1 O 0.2458(8) 0.5021(17) 1.1559(5) 0.073(4) Uani 0.50 1 d PD E -1
H1WA H 0.2512 0.5237 1.0995 0.109 Uiso 0.50 1 d PD F -1
H1WB H 0.2515 0.3963 1.1859 0.109 Uiso 0.50 1 d PD G -1
O2 O 0.26991(11) 0.8223(6) 1.2828(3) 0.0532(9) Uani 1 1 d D . .
H2WA H 0.2634(18) 0.758(7) 1.331(2) 0.080 Uiso 1 1 d D . .
H2WB H 0.255(2) 0.927(8) 1.280(4) 0.080 Uiso 0.50 1 d PD . .
H2WC H 0.264(3) 0.749(8) 1.238(2) 0.080 Uiso 0.50 1 d PD . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.502(8) . ?
C1 S1 1.808(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 S2 1.805(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.350(6) . ?
C3 S2 1.746(4) . ?
C3 S3 1.747(4) . ?
C4 S1 1.751(4) . ?
C4 S4 1.757(4) . ?
C5 C6 1.370(5) . ?
C5 S3 1.736(4) . ?
C5 S4 1.740(4) . ?
C6 S5 1.738(4) . ?
C6 S6 1.749(4) . ?
C7 C8 1.349(5) . ?
C7 S8 1.739(4) . ?
C7 S5 1.759(4) . ?
C8 S6 1.755(4) . ?
C8 S7 1.755(4) . ?
C9 C10 1.505(9) . ?
C9 S7 1.836(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 S8 1.794(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
S1 C101 1.806(17) . ?
S2 C102 1.800(18) . ?
S7 C109 1.821(11) . ?
S8 C110 1.848(12) . ?
C101 C102 1.50(2) . ?
C101 H10C 0.9900 . ?
C101 H10D 0.9900 . ?
C102 H10E 0.9900 . ?
C102 H10F 0.9900 . ?
C109 C110 1.510(16) . ?
C109 H10G 0.9900 . ?
C109 H10H 0.9900 . ?
C110 H11A 0.9900 . ?
C110 H11B 0.9900 . ?
O1 H1WA 0.8623 . ?
O1 H1WB 0.8552 . ?
O2 H2WA 0.853(5) . ?
O2 H2WB 0.851(5) . ?
O2 H2WC 0.851(5) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 S1 114.9(5) . . ?
C2 C1 H1A 108.5 . . ?
S1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
S1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 S2 112.6(5) . . ?
C1 C2 H2A 109.1 . . ?
S2 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
S2 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 S2 126.7(3) . . ?
C4 C3 S3 117.8(3) . . ?
S2 C3 S3 115.4(2) . . ?
C3 C4 S1 129.6(3) . . ?
C3 C4 S4 116.2(3) . . ?
S1 C4 S4 114.1(2) . . ?
C6 C5 S3 122.4(3) . . ?
C6 C5 S4 122.0(3) . . ?
S3 C5 S4 115.5(2) . . ?
C5 C6 S5 122.7(3) . . ?
C5 C6 S6 121.9(3) . . ?
S5 C6 S6 115.3(2) . . ?
C8 C7 S8 129.3(3) . . ?
C8 C7 S5 117.2(3) . . ?
S8 C7 S5 113.5(2) . . ?
C7 C8 S6 116.9(3) . . ?
C7 C8 S7 127.5(3) . . ?
S6 C8 S7 115.6(2) . . ?
C10 C9 S7 112.9(6) . . ?
C10 C9 H9A 109.0 . . ?
S7 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
S7 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 S8 113.7(5) . . ?
C9 C10 H10A 108.8 . . ?
S8 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
S8 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C4 S1 C101 99.3(16) . . ?
C4 S1 C1 102.2(2) . . ?
C101 S1 C1 25.1(16) . . ?
C3 S2 C102 102.1(18) . . ?
C3 S2 C2 98.7(3) . . ?
C102 S2 C2 26(2) . . ?
C5 S3 C3 95.08(19) . . ?
C5 S4 C4 95.41(19) . . ?
C6 S5 C7 95.25(18) . . ?
C6 S6 C8 95.32(18) . . ?
C8 S7 C109 102.4(5) . . ?
C8 S7 C9 99.6(2) . . ?
C109 S7 C9 30.7(5) . . ?
C7 S8 C10 102.8(3) . . ?
C7 S8 C110 100.6(5) . . ?
C10 S8 C110 22.7(4) . . ?
C102 C101 S1 110(4) . . ?
C102 C101 H10C 109.6 . . ?
S1 C101 H10C 109.6 . . ?
C102 C101 H10D 109.6 . . ?
S1 C101 H10D 109.6 . . ?
H10C C101 H10D 108.2 . . ?
C101 C102 S2 118(3) . . ?
C101 C102 H10E 107.7 . . ?
S2 C102 H10E 107.7 . . ?
C101 C102 H10F 107.8 . . ?
S2 C102 H10F 107.7 . . ?
H10E C102 H10F 107.1 . . ?
C110 C109 S7 112.5(12) . . ?
C110 C109 H10G 109.1 . . ?
S7 C109 H10G 109.1 . . ?
C110 C109 H10H 109.1 . . ?
S7 C109 H10H 109.1 . . ?
H10G C109 H10H 107.8 . . ?
C109 C110 S8 111.9(11) . . ?
C109 C110 H11A 109.2 . . ?
S8 C110 H11A 109.2 . . ?
C109 C110 H11B 109.2 . . ?
S8 C110 H11B 109.2 . . ?
H11A C110 H11B 107.9 . . ?
H1WA O1 H1WB 126.5 . . ?
H2WA O2 H2WB 107.8(14) . . ?
H2WA O2 H2WC 107.1(14) . . ?
H2WB O2 H2WC 107.1(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 H1WA Cl1  0.86 2.22 3.053(6) 161.1 .
O1 H1WA Br1  0.86 2.22 3.053(6) 161.1 .
O1 H1WB O2  0.86 2.16 2.910(10) 146.2 2_565
O2 H2WA Cl1  0.853(5) 2.496(13) 3.332(4) 167(5) 7_566
O2 H2WA Br1  0.853(5) 2.496(13) 3.332(4) 167(5) 7_566
O2 H2WB O2  0.851(5) 1.865(17) 2.708(8) 170(10) 2_575
O2 H2WC O1  0.851(5) 2.13(2) 2.951(18) 163(5) .
 
_diffrn_measured_fraction_theta_max    0.988
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.988
_refine_diff_density_max    1.171
_refine_diff_density_min   -0.669
_refine_diff_density_rms    0.100
