#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:15:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180130 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/28/7102845.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_7102845
loop_
_publ_author_name
'Granados, Alejandro M'
'Fracaroli, Alejandro M'
'de Rossi, Rita H'
'Fuertes, Pedro'
'Torroba, Tomás'
_publ_section_title
;
 Alkynyl Fischer carbene complex as a traceless directing group for the
 regioselective cycloaddition of dithiolethiones to arylacetylene:
 synthesis of E-dithiafulvene thione and dithioesters.
;
_journal_issue                   4
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              483
_journal_page_last               485
_journal_paper_doi               10.1039/b715857b
_journal_year                    2008
_chemical_formula_moiety         'C9 H4 Cr O5 S3'
_chemical_formula_sum            'C9 H4 Cr O5 S3'
_chemical_formula_weight         340.30
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 105.663(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   23.944(3)
_cell_length_b                   7.6413(10)
_cell_length_c                   28.506(4)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.79
_cell_measurement_theta_min      3.06
_cell_volume                     5022.0(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23664
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.416
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 2001)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0919P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                3066
_reflns_number_total             4407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715857b.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7102845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Cr1 Cr 0.62685(4) 1.01212(11) 0.56775(3) 0.0197(3) Uani 1 1 d . . .
S1 S 0.56527(6) 0.99720(19) 0.48488(5) 0.0238(4) Uani 1 1 d . . .
S2 S 0.67250(6) 1.0395(2) 0.45245(5) 0.0253(4) Uani 1 1 d . . .
S3 S 0.67663(7) 1.0191(2) 0.38143(5) 0.0286(4) Uani 1 1 d . . .
O1 O 0.70957(19) 0.7254(5) 0.55502(15) 0.0371(11) Uani 1 1 d . . .
O2 O 0.71021(18) 1.2998(5) 0.55736(15) 0.0356(11) Uani 1 1 d . . .
O3 O 0.6863(2) 1.0135(6) 0.67556(16) 0.0474(13) Uani 1 1 d . . .
O4 O 0.54655(19) 1.3020(6) 0.58447(16) 0.0394(11) Uani 1 1 d . . .
O5 O 0.54917(19) 0.7159(6) 0.58555(15) 0.0370(11) Uani 1 1 d . . .
C1 C 0.6780(2) 0.8351(7) 0.55827(19) 0.0234(13) Uani 1 1 d . . .
C2 C 0.6783(2) 1.1902(8) 0.55972(19) 0.0250(14) Uani 1 1 d . . .
C3 C 0.6639(3) 1.0126(7) 0.6345(2) 0.0300(15) Uani 1 1 d . . .
C4 C 0.5754(2) 1.1927(8) 0.57808(19) 0.0243(13) Uani 1 1 d . . .
C5 C 0.5770(2) 0.8290(8) 0.57880(18) 0.0228(13) Uani 1 1 d . . .
C6 C 0.5992(3) 0.9993(7) 0.4403(2) 0.0240(13) Uani 1 1 d . . .
C7 C 0.5714(3) 0.9697(7) 0.39040(19) 0.0224(13) Uani 1 1 d . . .
H7 H 0.5318 0.9471 0.3801 0.027 Uiso 1 1 calc R . .
C8 C 0.6041(3) 0.9752(7) 0.3575(2) 0.0224(13) Uani 1 1 d . . .
C9 C 0.5828(3) 0.9439(7) 0.3040(2) 0.0285(14) Uani 1 1 d . . .
H9A H 0.5770 0.8207 0.2979 0.043 Uiso 1 1 calc R . .
H9B H 0.6109 0.9862 0.2882 0.043 Uiso 1 1 calc R . .
H9C H 0.5467 1.0045 0.2913 0.043 Uiso 1 1 calc R . .
Cr2 Cr 0.87352(4) 0.95235(12) 0.26376(3) 0.0208(3) Uani 1 1 d . . .
S4 S 0.93071(6) 0.9236(2) 0.20642(5) 0.0252(4) Uani 1 1 d . . .
S5 S 0.82608(7) 1.0194(2) 0.12774(5) 0.0298(4) Uani 1 1 d . . .
S6 S 0.82397(7) 1.0489(2) 0.05554(5) 0.0314(4) Uani 1 1 d . . .
O6 O 0.96161(19) 1.2284(6) 0.31385(15) 0.0428(12) Uani 1 1 d . . .
O7 O 0.94695(18) 0.6477(6) 0.31456(15) 0.0392(11) Uani 1 1 d . . .
O8 O 0.8224(2) 0.9641(6) 0.34923(16) 0.0424(12) Uani 1 1 d . . .
O9 O 0.78300(18) 0.6852(6) 0.21176(15) 0.0395(11) Uani 1 1 d . . .
O10 O 0.7950(2) 1.2577(6) 0.22017(15) 0.0398(12) Uani 1 1 d . . .
C10 C 0.9296(3) 1.1223(8) 0.29546(19) 0.0284(14) Uani 1 1 d . . .
C11 C 0.9196(2) 0.7638(8) 0.29537(19) 0.0253(14) Uani 1 1 d . . .
C12 C 0.8405(3) 0.9589(8) 0.3155(2) 0.0294(15) Uani 1 1 d . . .
C13 C 0.8164(2) 0.7860(8) 0.2308(2) 0.0240(13) Uani 1 1 d . . .
C14 C 0.8244(2) 1.1410(8) 0.23420(19) 0.0225(13) Uani 1 1 d . . .
C15 C 0.8978(3) 0.9624(6) 0.1476(2) 0.0218(13) Uani 1 1 d . . .
C16 C 0.9267(3) 0.9536(7) 0.1099(2) 0.0260(14) Uani 1 1 d . . .
H16 H 0.9655 0.9216 0.1168 0.031 Uiso 1 1 calc R . .
C17 C 0.8956(2) 0.9933(7) 0.0638(2) 0.0213(13) Uani 1 1 d . . .
C18 C 0.9178(3) 0.9982(8) 0.0194(2) 0.0333(16) Uani 1 1 d . . .
H18A H 0.9593 1.0082 0.0292 0.050 Uiso 1 1 calc R . .
H18B H 0.9015 1.0970 -0.0003 0.050 Uiso 1 1 calc R . .
H18C H 0.9069 0.8925 0.0011 0.050 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 0.0033 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr 0.3209 0.6236 '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'
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
C3 Cr1 C2 88.7(2) . . ?
C3 Cr1 C1 90.0(2) . . ?
C2 Cr1 C1 91.7(3) . . ?
C3 Cr1 C5 88.8(2) . . ?
C2 Cr1 C5 177.4(2) . . ?
C1 Cr1 C5 87.6(2) . . ?
C3 Cr1 C4 89.4(2) . . ?
C2 Cr1 C4 88.1(2) . . ?
C1 Cr1 C4 179.4(2) . . ?
C5 Cr1 C4 92.6(2) . . ?
C3 Cr1 S1 170.9(2) . . ?
C2 Cr1 S1 99.23(17) . . ?
C1 Cr1 S1 94.25(16) . . ?
C5 Cr1 S1 83.35(16) . . ?
C4 Cr1 S1 86.38(16) . . ?
C6 S1 Cr1 116.4(2) . . ?
C6 S2 S3 96.1(2) . . ?
C8 S3 S2 95.4(2) . . ?
O1 C1 Cr1 176.4(5) . . ?
O2 C2 Cr1 176.5(5) . . ?
O3 C3 Cr1 179.6(6) . . ?
O4 C4 Cr1 178.0(5) . . ?
O5 C5 Cr1 177.3(5) . . ?
C7 C6 S1 124.4(5) . . ?
C7 C6 S2 114.0(4) . . ?
S1 C6 S2 121.5(3) . . ?
C8 C7 C6 118.7(5) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 126.3(5) . . ?
C7 C8 S3 115.8(4) . . ?
C9 C8 S3 117.9(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 Cr2 C11 87.8(2) . . ?
C12 Cr2 C14 89.2(2) . . ?
C11 Cr2 C14 176.9(2) . . ?
C12 Cr2 C10 90.1(3) . . ?
C11 Cr2 C10 92.7(3) . . ?
C14 Cr2 C10 88.0(2) . . ?
C12 Cr2 C13 90.4(3) . . ?
C11 Cr2 C13 88.6(2) . . ?
C14 Cr2 C13 90.7(3) . . ?
C10 Cr2 C13 178.6(3) . . ?
C12 Cr2 S4 170.21(19) . . ?
C11 Cr2 S4 83.57(17) . . ?
C14 Cr2 S4 99.48(16) . . ?
C10 Cr2 S4 85.80(17) . . ?
C13 Cr2 S4 93.88(17) . . ?
C15 S4 Cr2 117.5(2) . . ?
C15 S5 S6 96.4(2) . . ?
C17 S6 S5 94.7(2) . . ?
O6 C10 Cr2 177.5(6) . . ?
O7 C11 Cr2 179.0(5) . . ?
O8 C12 Cr2 176.9(6) . . ?
O9 C13 Cr2 178.9(6) . . ?
O10 C14 Cr2 174.5(5) . . ?
C16 C15 S4 123.5(4) . . ?
C16 C15 S5 114.2(4) . . ?
S4 C15 S5 122.4(3) . . ?
C17 C16 C15 117.9(5) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C16 C17 C18 126.6(5) . . ?
C16 C17 S6 116.9(5) . . ?
C18 C17 S6 116.5(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
Cr1 C3 1.871(6) . ?
Cr1 C2 1.890(6) . ?
Cr1 C1 1.893(6) . ?
Cr1 C5 1.920(6) . ?
Cr1 C4 1.925(6) . ?
Cr1 S1 2.4261(16) . ?
S1 C6 1.683(6) . ?
S2 C6 1.722(6) . ?
S2 S3 2.059(2) . ?
S3 C8 1.718(6) . ?
O1 C1 1.149(6) . ?
O2 C2 1.148(6) . ?
O3 C3 1.147(7) . ?
O4 C4 1.129(7) . ?
O5 C5 1.139(7) . ?
C6 C7 1.416(8) . ?
C7 C8 1.375(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.493(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
Cr2 C12 1.853(6) . ?
Cr2 C11 1.889(6) . ?
Cr2 C14 1.907(6) . ?
Cr2 C10 1.912(7) . ?
Cr2 C13 1.917(6) . ?
Cr2 S4 2.4091(17) . ?
S4 C15 1.675(6) . ?
S5 C15 1.712(6) . ?
S5 S6 2.058(2) . ?
S6 C17 1.722(6) . ?
O6 C10 1.140(7) . ?
O7 C11 1.150(7) . ?
O8 C12 1.157(7) . ?
O9 C13 1.138(6) . ?
O10 C14 1.140(6) . ?
C15 C16 1.428(8) . ?
C16 C17 1.359(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.498(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C3 Cr1 S1 C6 -165.5(12) . . . . ?
C2 Cr1 S1 C6 44.3(3) . . . . ?
C1 Cr1 S1 C6 -48.1(3) . . . . ?
C5 Cr1 S1 C6 -135.1(3) . . . . ?
C4 Cr1 S1 C6 131.8(3) . . . . ?
C6 S2 S3 C8 -0.1(3) . . . . ?
C3 Cr1 C1 O1 22(8) . . . . ?
C2 Cr1 C1 O1 111(8) . . . . ?
C5 Cr1 C1 O1 -66(8) . . . . ?
C4 Cr1 C1 O1 40(28) . . . . ?
S1 Cr1 C1 O1 -150(8) . . . . ?
C3 Cr1 C2 O2 -15(9) . . . . ?
C1 Cr1 C2 O2 -105(9) . . . . ?
C5 Cr1 C2 O2 -32(12) . . . . ?
C4 Cr1 C2 O2 74(9) . . . . ?
S1 Cr1 C2 O2 160(9) . . . . ?
C2 Cr1 C3 O3 100(100) . . . . ?
C1 Cr1 C3 O3 -168(100) . . . . ?
C5 Cr1 C3 O3 -81(100) . . . . ?
C4 Cr1 C3 O3 12(100) . . . . ?
S1 Cr1 C3 O3 -50(100) . . . . ?
C3 Cr1 C4 O4 68(14) . . . . ?
C2 Cr1 C4 O4 -21(14) . . . . ?
C1 Cr1 C4 O4 51(32) . . . . ?
C5 Cr1 C4 O4 157(14) . . . . ?
S1 Cr1 C4 O4 -120(14) . . . . ?
C3 Cr1 C5 O5 -76(10) . . . . ?
C2 Cr1 C5 O5 -60(13) . . . . ?
C1 Cr1 C5 O5 14(10) . . . . ?
C4 Cr1 C5 O5 -165(10) . . . . ?
S1 Cr1 C5 O5 109(10) . . . . ?
Cr1 S1 C6 C7 171.8(4) . . . . ?
Cr1 S1 C6 S2 -8.5(4) . . . . ?
S3 S2 C6 C7 0.0(4) . . . . ?
S3 S2 C6 S1 -179.8(3) . . . . ?
S1 C6 C7 C8 179.9(4) . . . . ?
S2 C6 C7 C8 0.1(7) . . . . ?
C6 C7 C8 C9 178.7(5) . . . . ?
C6 C7 C8 S3 -0.2(7) . . . . ?
S2 S3 C8 C7 0.2(4) . . . . ?
S2 S3 C8 C9 -178.8(4) . . . . ?
C12 Cr2 S4 C15 172.7(11) . . . . ?
C11 Cr2 S4 C15 144.9(3) . . . . ?
C14 Cr2 S4 C15 -34.6(3) . . . . ?
C10 Cr2 S4 C15 -121.9(3) . . . . ?
C13 Cr2 S4 C15 56.7(3) . . . . ?
C15 S5 S6 C17 0.8(3) . . . . ?
C12 Cr2 C10 O6 -78(12) . . . . ?
C11 Cr2 C10 O6 -165(12) . . . . ?
C14 Cr2 C10 O6 12(12) . . . . ?
C13 Cr2 C10 O6 34(19) . . . . ?
S4 Cr2 C10 O6 111(12) . . . . ?
C12 Cr2 C11 O7 61(29) . . . . ?
C14 Cr2 C11 O7 47(30) . . . . ?
C10 Cr2 C11 O7 151(29) . . . . ?
C13 Cr2 C11 O7 -30(29) . . . . ?
S4 Cr2 C11 O7 -124(29) . . . . ?
C11 Cr2 C12 O8 58(10) . . . . ?
C14 Cr2 C12 O8 -123(10) . . . . ?
C10 Cr2 C12 O8 -35(10) . . . . ?
C13 Cr2 C12 O8 146(10) . . . . ?
S4 Cr2 C12 O8 30(11) . . . . ?
C12 Cr2 C13 O9 -73(29) . . . . ?
C11 Cr2 C13 O9 15(29) . . . . ?
C14 Cr2 C13 O9 -162(100) . . . . ?
C10 Cr2 C13 O9 175(100) . . . . ?
S4 Cr2 C13 O9 98(29) . . . . ?
C12 Cr2 C14 O10 27(5) . . . . ?
C11 Cr2 C14 O10 40(9) . . . . ?
C10 Cr2 C14 O10 -63(5) . . . . ?
C13 Cr2 C14 O10 117(5) . . . . ?
S4 Cr2 C14 O10 -149(5) . . . . ?
Cr2 S4 C15 C16 178.7(4) . . . . ?
Cr2 S4 C15 S5 -0.4(4) . . . . ?
S6 S5 C15 C16 -1.2(4) . . . . ?
S6 S5 C15 S4 178.0(3) . . . . ?
S4 C15 C16 C17 -177.9(4) . . . . ?
S5 C15 C16 C17 1.2(7) . . . . ?
C15 C16 C17 C18 177.8(5) . . . . ?
C15 C16 C17 S6 -0.5(7) . . . . ?
S5 S6 C17 C16 -0.3(4) . . . . ?
S5 S6 C17 C18 -178.8(4) . . . . ?
