#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:01:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180461 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/30/7213072.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213072
loop_
_publ_author_name
'Heuzé, Karine'
'Fourmigué, Marc'
'Batail, Patrick'
_publ_section_title
;
 The crystal chemistry of amide‐functionalized
 ethylenedithiotetrathiafulvalenes: EDT‐TTF‐CONRR′
 (R, R′ = H, Me)
;
_journal_issue                   10
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2373
_journal_paper_doi               10.1039/a902852h
_journal_volume                  9
_journal_year                    1999
_chemical_formula_sum            'C9 H6 O2 S6'
_chemical_formula_weight         338.50
_chemical_name_common            EDT-TTF-CO2H
_chemical_name_systematic
; 
4-(4',5'-ethylenedithiotetrathiafulvalenyl)carboxylic acid 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.29(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.3720(8)
_cell_length_b                   27.142(6)
_cell_length_c                   14.238(2)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.9
_cell_measurement_theta_min      2.6
_cell_volume                     2460.5(7)
_computing_cell_refinement       'CELL (Stoe IPDS)'
_computing_data_collection       'EXPOSE (Stoe IPDS)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'Oscillation, phi incr. 0.9'
_diffrn_radiation_detector       'area detector'
_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  0.4439
_diffrn_reflns_av_sigmaI/netI    0.5141
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19288
_diffrn_reflns_theta_max         25.90
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    1.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.712
_refine_ls_goodness_of_fit_obs   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.716
_refine_ls_restrained_S_obs      1.040
_refine_ls_R_factor_all          0.2866
_refine_ls_R_factor_obs          0.0819
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1902
_refine_ls_wR_factor_obs         0.1232
_reflns_number_observed          1035
_reflns_number_total             4613
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            902852hsup1.cif
_cod_data_source_block           acid
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7213072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.9112(7) 0.1188(2) 0.1604(3) 0.0422(13) Uani 1 d .
S2 S 0.4784(7) 0.1128(2) 0.2263(3) 0.0410(12) Uani 1 d .
S3 S 1.0444(7) 0.1856(2) 0.3386(3) 0.0449(13) Uani 1 d .
S4 S 0.6154(7) 0.1778(2) 0.4090(3) 0.0398(12) Uani 1 d .
S5 S 1.1858(7) 0.2583(2) 0.4819(3) 0.0522(14) Uani 1 d .
S6 S 0.6958(7) 0.2466(2) 0.5674(3) 0.0505(13) Uani 1 d .
C1 C 0.7977(31) 0.0642(7) 0.0059(12) 0.051(5) Uiso 1 d .
C2 C 0.7206(28) 0.0882(6) 0.0906(11) 0.046(5) Uiso 1 d .
C3 C 0.5206(28) 0.0860(6) 0.1198(11) 0.045(4) Uiso 1 d .
H3 H 0.4133(28) 0.0708(6) 0.0843(11) 0.054 Uiso 1 calc R
C4 C 0.7364(24) 0.1374(5) 0.2458(9) 0.030(4) Uiso 1 d .
C5 C 0.7911(25) 0.1650(5) 0.3194(10) 0.032(4) Uiso 1 d .
C6 C 0.9808(25) 0.2232(6) 0.4353(10) 0.034(4) Uiso 1 d .
C7 C 0.7855(24) 0.2185(5) 0.4651(9) 0.031(4) Uiso 1 d .
C8 C 1.1147(45) 0.2651(10) 0.5951(17) 0.110(9) Uiso 1 d .
H8A H 1.2253(45) 0.2491(10) 0.6326(17) 0.131 Uiso 1 calc R
H8B H 1.1292(45) 0.3001(10) 0.6080(17) 0.131 Uiso 1 calc R
C9 C 0.9283(31) 0.2513(8) 0.6366(13) 0.067(6) Uiso 1 d .
H9A H 0.9033(31) 0.2748(8) 0.6863(13) 0.080 Uiso 1 calc R
H9B H 0.9527(31) 0.2196(8) 0.6665(13) 0.080 Uiso 1 calc R
O1 O 0.6483(19) 0.0442(4) -0.0497(7) 0.049(3) Uiso 1 d .
O2 O 0.9872(20) 0.0620(4) -0.0077(8) 0.056(3) Uiso 1 d .
S7 S 1.1163(7) 0.0464(2) 0.3725(3) 0.0380(12) Uani 1 d .
S8 S 0.6791(7) 0.0389(2) 0.4336(3) 0.0402(13) Uani 1 d .
S9 S 1.2420(7) 0.1067(2) 0.5612(3) 0.0398(12) Uani 1 d .
S10 S 0.8076(7) 0.0988(2) 0.6223(3) 0.0446(13) Uani 1 d .
S11 S 1.4057(8) 0.1515(3) 0.7350(4) 0.092(2) Uani 1 d .
S12 S 0.8928(7) 0.1421(2) 0.8095(3) 0.058(2) Uani 1 d .
C10 C 1.0006(26) -0.0046(6) 0.2139(11) 0.037(4) Uiso 1 d .
C11 C 0.9321(24) 0.0144(6) 0.3019(10) 0.032(4) Uiso 1 d .
C12 C 0.7389(28) 0.0127(6) 0.3326(11) 0.045(4) Uiso 1 d .
H12 H 0.6345(28) -0.0034(6) 0.2969(11) 0.054 Uiso 1 calc R
C13 C 0.9398(24) 0.0611(6) 0.4580(10) 0.031(4) Uiso 1 d .
C14 C 0.9903(22) 0.0849(5) 0.5347(9) 0.022(3) Uiso 1 d .
C15 C 1.1853(26) 0.1259(6) 0.6738(10) 0.040(4) Uiso 1 d .
C16 C 0.9851(24) 0.1223(6) 0.7003(10) 0.034(4) Uiso 1 d .
C17 C 1.3218(29) 0.1450(7) 0.8545(11) 0.055(5) Uiso 1 d .
H17A H 1.3157(29) 0.1102(7) 0.8702(11) 0.066 Uiso 1 calc R
H17B H 1.4247(29) 0.1603(7) 0.8971(11) 0.066 Uiso 1 calc R
C18 C 1.1144(28) 0.1674(6) 0.8679(11) 0.047(5) Uiso 1 d .
H18A H 1.1230(28) 0.2018(6) 0.8494(11) 0.057 Uiso 1 calc R
H18B H 1.0898(28) 0.1669(6) 0.9347(11) 0.057 Uiso 1 calc R
O3 O 0.8633(19) -0.0236(4) 0.1566(7) 0.049(3) Uiso 1 d .
O4 O 1.1944(17) -0.0025(4) 0.1950(7) 0.041(3) Uiso 1 d .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 S1 C4 94.8(8)
C3 S2 C4 96.9(8)
C5 S3 C6 93.9(7)
C7 S4 C5 93.2(7)
C8 S5 C6 101.4(11)
C9 S6 C7 101.6(8)
O2 C1 O1 124.8(16)
O2 C1 C2 120.7(17)
O1 C1 C2 114.5(15)
C3 C2 C1 125.4(17)
C3 C2 S1 119.1(13)
C1 C2 S1 115.4(13)
C2 C3 S2 115.8(14)
C5 C4 S1 123.8(12)
C5 C4 S2 123.1(11)
S1 C4 S2 113.0(8)
C4 C5 S3 121.7(11)
C4 C5 S4 122.0(12)
S3 C5 S4 116.1(8)
C7 C6 S5 129.0(12)
C7 C6 S3 115.9(12)
S5 C6 S3 115.0(8)
C6 C7 S4 119.4(11)
C6 C7 S6 124.0(12)
S4 C7 S6 116.3(8)
C9 C8 S5 129.3(21)
C8 C9 S6 119.7(17)
C13 S7 C11 94.5(7)
C12 S8 C13 93.9(8)
C14 S9 C15 94.5(7)
C16 S10 C14 95.8(7)
C15 S11 C17 99.6(8)
C18 S12 C16 104.3(8)
O4 C10 O3 121.6(14)
O4 C10 C11 119.9(15)
O3 C10 C11 118.5(14)
C12 C11 C10 126.4(16)
C12 C11 S7 116.1(13)
C10 C11 S7 117.4(11)
C11 C12 S8 121.3(15)
C14 C13 S7 123.9(12)
C14 C13 S8 121.9(11)
S7 C13 S8 114.2(8)
C13 C14 S9 123.2(11)
C13 C14 S10 123.2(11)
S9 C14 S10 113.6(8)
C16 C15 S9 118.1(13)
C16 C15 S11 129.3(12)
S9 C15 S11 112.5(9)
C15 C16 S10 117.5(11)
C15 C16 S12 125.2(13)
S10 C16 S12 117.3(9)
C18 C17 S11 112.3(13)
C17 C18 S12 119.1(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.75(2)
S1 C4 1.755(14)
S2 C3 1.71(2)
S2 C4 1.78(2)
S3 C5 1.72(2)
S3 C6 1.774(15)
S4 C7 1.72(2)
S4 C5 1.765(14)
S5 C8 1.70(2)
S5 C6 1.73(2)
S6 C9 1.75(2)
S6 C7 1.760(14)
C1 O2 1.23(2)
C1 O1 1.33(2)
C1 C2 1.47(2)
C2 C3 1.36(2)
C4 C5 1.32(2)
C6 C7 1.34(2)
C8 C9 1.40(3)
S7 C13 1.736(14)
S7 C11 1.75(2)
S8 C12 1.66(2)
S8 C13 1.79(2)
S9 C14 1.737(15)
S9 C15 1.738(14)
S10 C16 1.68(2)
S10 C14 1.780(13)
S11 C15 1.77(2)
S11 C17 1.81(2)
S12 C18 1.75(2)
S12 C16 1.767(14)
C10 O4 1.28(2)
C10 O3 1.28(2)
C10 C11 1.44(2)
C11 C12 1.32(2)
C13 C14 1.30(2)
C15 C16 1.35(2)
C17 C18 1.47(2)
