#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:17:29 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178944 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/73/4117359.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4117359
loop_
_publ_author_name
'Yuta Fujiwara'
'Janice A. Dixon'
'Rodrigo A. Rodriguez'
'Ryan D. Baxter'
'Darryl D. Dixon'
'Michael R. Collins'
'Donna G. Blackmond'
'Phil S. Baran'
_publ_section_title
;
 A New Reagent for Direct Difluoromethylation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1494
_journal_page_last               1497
_journal_paper_doi               10.1021/ja211422g
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C6 H18 F12 O18 S6 Zn3'
_chemical_formula_weight         994.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            9
_cell_length_a                   9.2688(3)
_cell_length_b                   9.2688(3)
_cell_length_c                   88.532(3)
_cell_measurement_reflns_used    4570
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.80
_cell_measurement_theta_min      4.49
_cell_volume                     6586.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker SMART 6K CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirror'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       104
_diffrn_reflns_limit_l_min       -106
_diffrn_reflns_number            22234
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         68.12
_diffrn_reflns_theta_min         5.53
_exptl_absorpt_coefficient_mu    8.292
_exptl_absorpt_correction_T_max  0.7890
_exptl_absorpt_correction_T_min  0.4910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    2.257
_exptl_crystal_description       Plate
_exptl_crystal_F_000             4428
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         3.330
_refine_diff_density_min         -1.144
_refine_diff_density_rms         0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0935
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1826P)²+97.9066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2759
_refine_ls_wR_factor_ref         0.3022
_reflns_number_gt                1831
_reflns_number_total             2646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja211422g_si_004.cif
_cod_data_source_block           pflj235
_cod_original_cell_volume        6586.8(4)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4117359
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
Zn1 Zn -0.6667 -0.3333 -0.999886(16) 0.0325(6) Uani 1 3 d S
Zn2 Zn 0.0000 0.0000 -1.111084(14) 0.0212(5) Uani 1 3 d S
Zn3 Zn -0.3333 0.3333 -1.111072(16) 0.0233(5) Uani 1 3 d S
Zn4 Zn -0.6667 -0.3333 -1.111075(16) 0.0231(5) Uani 1 3 d S
Zn5 Zn 0.0000 0.0000 -1.0000 0.0331(6) Uani 1 6 d S
S1 S -0.46020(19) -0.45874(19) -1.020301(18) 0.0315(6) Uani 1 1 d .
S2 S -0.20713(17) -0.33297(16) -1.131399(18) 0.0260(5) Uani 1 1 d .
S3 S -0.20684(17) 0.12581(17) -1.090747(18) 0.0269(5) Uani 1 1 d .
F1 F -0.3181(14) -0.4532(12) -1.04555(10) 0.126(3) Uani 1 1 d .
F2 F -0.4656(9) -0.3343(11) -1.04654(7) 0.092(2) Uani 1 1 d .
F3 F -0.3477(12) -0.4696(12) -1.15670(9) 0.125(3) Uani 1 1 d .
F4 F -0.2028(9) -0.2032(9) -1.15762(6) 0.084(2) Uani 1 1 d .
F5 F -0.2014(9) 0.0008(10) -1.06457(6) 0.085(2) Uani 1 1 d .
F6 F -0.3494(12) 0.1228(11) -1.06551(9) 0.122(3) Uani 1 1 d .
O1 O -0.8466(6) -0.3168(6) -0.98661(6) 0.0366(12) Uani 1 1 d .
O2 O -0.4706(6) -0.3161(6) -1.01317(6) 0.0364(12) Uani 1 1 d .
O3 O -0.1963(5) -0.1794(5) -1.12440(5) 0.0279(10) Uani 1 1 d .
O4 O -0.3504(5) -0.4868(5) -1.12436(6) 0.0315(10) Uani 1 1 d .
O5 O -0.1964(5) -0.0171(5) -1.09783(5) 0.0282(10) Uani 1 1 d .
O6 O -0.3497(5) 0.1373(5) -1.09781(6) 0.0312(11) Uani 1 1 d .
O7 O -0.4864(5) -0.3336(5) -1.09719(5) 0.0303(10) Uani 1 1 d .
H7A H -0.5124 -0.3336 -1.0879 0.045 Uiso 1 1 d R
H7B H -0.4789 -0.4215 -1.0990 0.045 Uiso 1 1 d R
O8 O -0.4865(5) -0.1522(5) -1.12500(5) 0.0296(10) Uani 1 1 d .
H8A H -0.4889 -0.0615 -1.1242 0.044 Uiso 1 1 d R
H8B H -0.3901 -0.1347 -1.1224 0.044 Uiso 1 1 d R
O9 O -0.1800(6) 0.0014(6) -1.01395(5) 0.0350(11) Uani 1 1 d .
H9A H -0.2750 -0.0859 -1.0125 0.053 Uiso 1 1 d R
H9B H -0.1881 0.0882 -1.0122 0.053 Uiso 1 1 d R
C1 C -0.3533(13) -0.3527(14) -1.03825(13) 0.058(3) Uani 1 1 d .
H1 H -0.2510 -0.2430 -1.0362 0.069 Uiso 1 1 calc R
C2 C -0.3133(12) -0.3331(8) -1.14943(13) 0.052(3) Uani 1 1 d .
H2 H -0.4161 -0.3268 -1.1474 0.063 Uiso 1 1 calc R
C3 C -0.3151(12) 0.0178(13) -1.07278(11) 0.049(3) Uani 1 1 d .
H3 H -0.4176 -0.0918 -1.0748 0.058 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 Zn1 O2 91.8(2) 2_455 3_445
O2 Zn1 O2 91.8(2) 2_455 .
O2 Zn1 O2 91.8(2) 3_445 .
O2 Zn1 O1 83.1(2) 2_455 .
O2 Zn1 O1 93.7(2) 3_445 .
O2 Zn1 O1 172.61(19) . .
O2 Zn1 O1 93.7(2) 2_455 3_445
O2 Zn1 O1 172.61(17) 3_445 3_445
O2 Zn1 O1 83.1(2) . 3_445
O1 Zn1 O1 91.9(2) . 3_445
O2 Zn1 O1 172.61(19) 2_455 2_455
O2 Zn1 O1 83.1(2) 3_445 2_455
O2 Zn1 O1 93.68(19) . 2_455
O1 Zn1 O1 91.9(2) . 2_455
O1 Zn1 O1 91.9(2) 3_445 2_455
O5 Zn2 O5 91.93(18) 2 3
O5 Zn2 O5 91.93(18) 2 .
O5 Zn2 O5 91.93(18) 3 .
O5 Zn2 O3 172.56(17) 2 3
O5 Zn2 O3 83.05(19) 3 3
O5 Zn2 O3 93.73(17) . 3
O5 Zn2 O3 83.05(18) 2 2
O5 Zn2 O3 93.73(18) 3 2
O5 Zn2 O3 172.56(17) . 2
O3 Zn2 O3 91.75(18) 3 2
O5 Zn2 O3 93.73(18) 2 .
O5 Zn2 O3 172.55(15) 3 .
O5 Zn2 O3 83.06(19) . .
O3 Zn2 O3 91.75(18) 3 .
O3 Zn2 O3 91.75(18) 2 .
O6 Zn3 O6 91.90(19) . 2_565
O6 Zn3 O6 91.90(19) . 3_455
O6 Zn3 O6 91.90(19) 2_565 3_455
O6 Zn3 O4 93.54(18) . 3
O6 Zn3 O4 83.07(19) 2_565 3
O6 Zn3 O4 172.70(18) 3_455 3
O6 Zn3 O4 83.06(19) . 2_455
O6 Zn3 O4 172.70(16) 2_565 2_455
O6 Zn3 O4 93.55(19) 3_455 2_455
O4 Zn3 O4 91.94(19) 3 2_455
O6 Zn3 O4 172.70(18) . 1_565
O6 Zn3 O4 93.55(19) 2_565 1_565
O6 Zn3 O4 83.06(18) 3_455 1_565
O4 Zn3 O4 91.94(19) 3 1_565
O4 Zn3 O4 91.94(19) 2_455 1_565
O7 Zn4 O7 88.50(19) 2_455 3_445
O7 Zn4 O7 88.50(19) 2_455 .
O7 Zn4 O7 88.50(19) 3_445 .
O7 Zn4 O8 91.72(17) 2_455 2_455
O7 Zn4 O8 91.35(18) 3_445 2_455
O7 Zn4 O8 179.73(19) . 2_455
O7 Zn4 O8 91.35(18) 2_455 .
O7 Zn4 O8 179.73(19) 3_445 .
O7 Zn4 O8 91.73(18) . .
O8 Zn4 O8 88.43(19) 2_455 .
O7 Zn4 O8 179.7(2) 2_455 3_445
O7 Zn4 O8 91.72(18) 3_445 3_445
O7 Zn4 O8 91.35(17) . 3_445
O8 Zn4 O8 88.43(19) 2_455 3_445
O8 Zn4 O8 88.43(18) . 3_445
O9 Zn5 O9 180.0(2) 11_553 2
O9 Zn5 O9 88.39(19) 11_553 10_553
O9 Zn5 O9 91.61(18) 2 10_553
O9 Zn5 O9 88.39(18) 11_553 12_553
O9 Zn5 O9 91.61(19) 2 12_553
O9 Zn5 O9 88.39(18) 10_553 12_553
O9 Zn5 O9 91.61(19) 11_553 3
O9 Zn5 O9 88.39(19) 2 3
O9 Zn5 O9 91.61(19) 10_553 3
O9 Zn5 O9 180.000(4) 12_553 3
O9 Zn5 O9 91.62(18) 11_553 .
O9 Zn5 O9 88.38(19) 2 .
O9 Zn5 O9 179.994(9) 10_553 .
O9 Zn5 O9 91.62(19) 12_553 .
O9 Zn5 O9 88.38(18) 3 .
O2 S1 O1 109.5(3) . 11_543
O2 S1 C1 98.3(4) . .
O1 S1 C1 97.3(4) 11_543 .
O3 S2 O4 109.4(3) . .
O3 S2 C2 97.9(3) . .
O4 S2 C2 97.9(4) . .
O5 S3 O6 109.3(3) . .
O5 S3 C3 97.8(3) . .
O6 S3 C3 97.7(3) . .
S1 O1 Zn1 126.8(3) 12_453 .
S1 O2 Zn1 126.7(3) . .
S2 O3 Zn2 126.7(2) . .
S2 O4 Zn3 126.6(2) . 1_545
S3 O5 Zn2 126.7(3) . .
S3 O6 Zn3 127.0(2) . .
Zn4 O7 H7A 110.0 . .
Zn4 O7 H7B 109.7 . .
H7A O7 H7B 109.2 . .
Zn4 O8 H8A 109.7 . .
Zn4 O8 H8B 109.6 . .
H8A O8 H8B 109.2 . .
Zn5 O9 H9A 110.6 . .
Zn5 O9 H9B 110.3 . .
H9A O9 H9B 109.1 . .
F1 C1 F2 107.7(11) . .
F1 C1 S1 107.6(8) . .
F2 C1 S1 106.8(6) . .
F1 C1 H1 111.5 . .
F2 C1 H1 111.5 . .
S1 C1 H1 111.5 . .
F3 C2 F4 108.1(11) . .
F3 C2 S2 107.1(7) . .
F4 C2 S2 107.2(6) . .
F3 C2 H2 111.4 . .
F4 C2 H2 111.4 . .
S2 C2 H2 111.4 . .
F6 C3 F5 108.1(10) . .
F6 C3 S3 106.2(7) . .
F5 C3 S3 106.1(6) . .
F6 C3 H3 112.0 . .
F5 C3 H3 112.0 . .
S3 C3 H3 112.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 2.103(5) 2_455
Zn1 O2 2.103(5) 3_445
Zn1 O2 2.103(5) .
Zn1 O1 2.107(5) .
Zn1 O1 2.107(5) 3_445
Zn1 O1 2.107(5) 2_455
Zn2 O5 2.104(4) 2
Zn2 O5 2.104(5) 3
Zn2 O5 2.104(4) .
Zn2 O3 2.107(4) 3
Zn2 O3 2.107(4) 2
Zn2 O3 2.107(5) .
Zn3 O6 2.104(5) .
Zn3 O6 2.104(5) 2_565
Zn3 O6 2.104(5) 3_455
Zn3 O4 2.110(5) 3
Zn3 O4 2.110(5) 2_455
Zn3 O4 2.110(5) 1_565
Zn4 O7 2.075(4) 2_455
Zn4 O7 2.075(5) 3_445
Zn4 O7 2.075(4) .
Zn4 O8 2.079(5) 2_455
Zn4 O8 2.079(5) .
Zn4 O8 2.079(4) 3_445
Zn5 O9 2.081(5) 11_553
Zn5 O9 2.081(5) 2
Zn5 O9 2.081(5) 10_553
Zn5 O9 2.081(5) 12_553
Zn5 O9 2.081(5) 3
Zn5 O9 2.081(5) .
S1 O2 1.511(5) .
S1 O1 1.515(5) 11_543
S1 C1 1.871(11) .
S2 O3 1.509(5) .
S2 O4 1.514(5) .
S2 C2 1.875(11) .
S3 O5 1.512(5) .
S3 O6 1.516(5) .
S3 C3 1.880(10) .
F1 C1 1.302(12) .
F2 C1 1.353(12) .
F3 C2 1.309(11) .
F4 C2 1.339(12) .
F5 C3 1.353(11) .
F6 C3 1.331(11) .
O1 S1 1.515(5) 12_453
O4 Zn3 2.110(5) 1_545
O7 H7A 0.8596 .
O7 H7B 0.8663 .
O8 H8A 0.8557 .
O8 H8B 0.8563 .
O9 H9A 0.8571 .
O9 H9B 0.8580 .
C1 H1 1.0000 .
C2 H2 1.0000 .
C3 H3 1.0000 .
