# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1055659'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

# CLAVE ICUAP: TTFDDNF3
# CLAVE TESIS: TTF-DDF CH3CN  Sintesis p. 117-118

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_date             2015-01-06

_chemical_name_systematic        
'Tetrathiafulvalene 9-dicyanomethylene-2,7-dinitrofluorene acetonitrile monosolvate'

_chemical_name_common            ?
_chemical_melting_point          447
_chemical_formula_moiety         'C16 H6 N4 O4, C6 H4 S4, C2 H3 N'
_chemical_formula_sum            'C24 H13 N5 O4 S4'
_chemical_formula_weight         563.63

_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    Air-sensitive
_chemical_properties_biological  ?

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.141(2)
_cell_length_b                   17.151(4)
_cell_length_c                   20.891(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.18(3)
_cell_angle_gamma                90
_cell_volume                     2525.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    41
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      12.09

_exptl_crystal_description       needle
_exptl_crystal_colour            dark_brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.418
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.37764
_exptl_absorpt_correction_T_max  0.51633
_exptl_absorpt_process_details   'XSCANS (Siemens, 1996)'

_exptl_special_details           ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         X-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              FN4
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_source_power             1.5
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -2 -1
2 1 -2
2 2 -1

_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            5355
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.544
_diffrn_reflns_theta_max         23.999
_diffrn_reflns_theta_full        23.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3950
_reflns_number_gt                2564
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+5.9898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_extinction_coef       0.0005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3950
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_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
C1 C 0.0462(7) 0.3270(3) 0.2060(2) 0.0409(13) Uani 1 1 d . . . . .
H1A H 0.0085 0.3786 0.2092 0.049 Uiso 1 1 calc R U . . .
C2 C 0.0407(8) 0.2912(3) 0.1464(2) 0.0452(14) Uani 1 1 d . . . . .
C3 C 0.1012(8) 0.2162(4) 0.1388(3) 0.0491(15) Uani 1 1 d . . . . .
H3A H 0.1004 0.1955 0.0976 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1636(8) 0.1718(3) 0.1937(2) 0.0459(14) Uani 1 1 d . . . . .
H4A H 0.2041 0.1207 0.1898 0.055 Uiso 1 1 calc R U . . .
C4A C 0.1646(7) 0.2042(3) 0.2538(2) 0.0351(12) Uani 1 1 d . . . . .
C4B C 0.2182(7) 0.1713(3) 0.3191(2) 0.0376(12) Uani 1 1 d . . . . .
C5 C 0.2736(7) 0.0960(3) 0.3377(3) 0.0429(13) Uani 1 1 d . . . . .
H5A H 0.2828 0.0576 0.3070 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3148(7) 0.0798(3) 0.4036(3) 0.0468(14) Uani 1 1 d . . . . .
H6A H 0.3524 0.0300 0.4179 0.056 Uiso 1 1 calc R U . . .
C7 C 0.2992(7) 0.1385(3) 0.4472(3) 0.0443(14) Uani 1 1 d . . . . .
C8 C 0.2442(7) 0.2133(3) 0.4303(2) 0.0409(13) Uani 1 1 d . . . . .
H8A H 0.2395 0.2517 0.4614 0.049 Uiso 1 1 calc R U . . .
C8A C 0.1957(7) 0.2290(3) 0.3645(2) 0.0356(12) Uani 1 1 d . . . . .
C9 C 0.1284(7) 0.3010(3) 0.3301(2) 0.0347(12) Uani 1 1 d . . . . .
C9A C 0.1101(6) 0.2828(3) 0.2610(2) 0.0330(11) Uani 1 1 d . . . . .
C10 C 0.0890(7) 0.3702(3) 0.3574(2) 0.0393(12) Uani 1 1 d . . . . .
C11 C 0.0396(8) 0.4388(3) 0.3188(3) 0.0478(14) Uani 1 1 d . . . . .
N12 N 0.0028(9) 0.4932(3) 0.2876(3) 0.0731(16) Uani 1 1 d . . . . .
C13 C 0.1034(8) 0.3823(3) 0.4263(3) 0.0504(15) Uani 1 1 d . . . . .
N14 N 0.1155(9) 0.3915(4) 0.4806(3) 0.0793(18) Uani 1 1 d . . . . .
N15 N -0.0355(8) 0.3373(4) 0.0889(2) 0.0635(15) Uani 1 1 d . . . . .
O16 O -0.0660(9) 0.4066(3) 0.0949(2) 0.1007(19) Uani 1 1 d . . . . .
O17 O -0.0637(9) 0.3045(3) 0.0367(2) 0.0986(18) Uani 1 1 d . . . . .
N18 N 0.3535(7) 0.1214(3) 0.5168(2) 0.0573(13) Uani 1 1 d . . . . .
O19 O 0.3896(8) 0.1752(3) 0.5546(2) 0.0898(17) Uani 1 1 d . . . . .
O20 O 0.3583(8) 0.0534(3) 0.5344(2) 0.0908(17) Uani 1 1 d . . . . .
S21 S 0.5799(2) 0.29874(9) 0.20202(6) 0.0477(4) Uani 1 1 d . . . . .
C22 C 0.5175(8) 0.3960(4) 0.2076(3) 0.0536(15) Uani 1 1 d . . . . .
H22A H 0.4775 0.4251 0.1704 0.064 Uiso 1 1 calc R U . . .
C23 C 0.5276(8) 0.4275(4) 0.2649(3) 0.0538(15) Uani 1 1 d . . . . .
H23A H 0.4962 0.4796 0.2696 0.065 Uiso 1 1 calc R U . . .
S24 S 0.6015(2) 0.36914(9) 0.33199(7) 0.0470(4) Uani 1 1 d . . . . .
C25 C 0.6338(7) 0.2859(3) 0.2868(2) 0.0398(13) Uani 1 1 d . . . . .
C26 C 0.6893(7) 0.2180(3) 0.3148(2) 0.0402(13) Uani 1 1 d . . . . .
S27 S 0.7338(2) 0.20733(9) 0.39980(7) 0.0461(4) Uani 1 1 d . . . . .
C28 C 0.7985(8) 0.1101(4) 0.3980(3) 0.0541(15) Uani 1 1 d . . . . .
H28A H 0.8345 0.0823 0.4363 0.065 Uiso 1 1 calc R U . . .
C29 C 0.7955(8) 0.0767(3) 0.3420(3) 0.0557(16) Uani 1 1 d . . . . .
H29A H 0.8294 0.0246 0.3391 0.067 Uiso 1 1 calc R U . . .
S30 S 0.7258(2) 0.13255(9) 0.27193(7) 0.0510(4) Uani 1 1 d . . . . .
C31 C 0.6410(16) 0.1238(8) 0.0288(6) 0.160(5) Uani 1 1 d . . . . .
H31A H 0.7770 0.1218 0.0345 0.241 Uiso 1 1 calc R U . . .
H31B H 0.6009 0.1763 0.0351 0.241 Uiso 1 1 calc R U . . .
H31C H 0.5896 0.1069 -0.0142 0.241 Uiso 1 1 calc R U . . .
C32 C 0.5733(14) 0.0727(6) 0.0760(4) 0.102(3) Uani 1 1 d . . . . .
N33 N 0.5167(16) 0.0336(7) 0.1096(5) 0.165(4) Uani 1 1 d . . . . .


_geom_special_details            ?

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 1.383(7) . ?
C1 C9A 1.392(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(8) . ?
C2 N15 1.468(7) . ?
C3 C4 1.391(8) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.371(7) . ?
C4 H4A 0.9300 . ?
C4A C9A 1.418(7) . ?
C4A C4B 1.468(7) . ?
C4B C5 1.388(7) . ?
C4B C8A 1.398(7) . ?
C5 C6 1.388(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.376(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.371(8) . ?
C7 N18 1.473(7) . ?
C8 C8A 1.389(7) . ?
C8 H8A 0.9300 . ?
C8A C9 1.470(7) . ?
C9 C10 1.365(7) . ?
C9 C9A 1.462(7) . ?
C10 C11 1.439(8) . ?
C10 C13 1.440(8) . ?
C11 N12 1.144(7) . ?
C13 N14 1.136(7) . ?
N15 O17 1.214(7) . ?
N15 O16 1.217(7) . ?
N18 O19 1.214(7) . ?
N18 O20 1.221(7) . ?
S21 C22 1.735(6) . ?
S21 C25 1.765(5) . ?
C22 C23 1.305(8) . ?
C22 H22A 0.9300 . ?
C23 S24 1.734(6) . ?
C23 H23A 0.9300 . ?
S24 C25 1.747(5) . ?
C25 C26 1.335(7) . ?
C26 S30 1.758(5) . ?
C26 S27 1.764(5) . ?
S27 C28 1.733(6) . ?
C28 C29 1.301(8) . ?
C28 H28A 0.9300 . ?
C29 S30 1.753(6) . ?
C29 H29A 0.9300 . ?
C31 C32 1.458(13) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 N33 1.093(11) . ?

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 C9A 117.4(5) . . ?
C2 C1 H1A 121.3 . . ?
C9A C1 H1A 121.3 . . ?
C3 C2 C1 123.7(5) . . ?
C3 C2 N15 119.4(5) . . ?
C1 C2 N15 116.8(5) . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C4A C4 C3 119.2(5) . . ?
C4A C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C4A C9A 121.4(5) . . ?
C4 C4A C4B 131.1(5) . . ?
C9A C4A C4B 107.5(4) . . ?
C5 C4B C8A 121.8(5) . . ?
C5 C4B C4A 129.6(5) . . ?
C8A C4B C4A 108.5(4) . . ?
C6 C5 C4B 118.1(5) . . ?
C6 C5 H5A 121.0 . . ?
C4B C5 H5A 121.0 . . ?
C7 C6 C5 118.9(5) . . ?
C7 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C8 C7 C6 124.3(5) . . ?
C8 C7 N18 117.5(5) . . ?
C6 C7 N18 118.2(5) . . ?
C7 C8 C8A 117.0(5) . . ?
C7 C8 H8A 121.5 . . ?
C8A C8 H8A 121.5 . . ?
C8 C8A C4B 119.8(5) . . ?
C8 C8A C9 131.0(5) . . ?
C4B C8A C9 109.1(4) . . ?
C10 C9 C9A 127.4(5) . . ?
C10 C9 C8A 126.8(4) . . ?
C9A C9 C8A 105.8(4) . . ?
C1 C9A C4A 119.3(4) . . ?
C1 C9A C9 131.7(5) . . ?
C4A C9A C9 109.0(4) . . ?
C9 C10 C11 121.6(4) . . ?
C9 C10 C13 123.8(5) . . ?
C11 C10 C13 114.5(5) . . ?
N12 C11 C10 178.9(7) . . ?
N14 C13 C10 179.6(7) . . ?
O17 N15 O16 122.6(6) . . ?
O17 N15 C2 118.1(6) . . ?
O16 N15 C2 119.3(5) . . ?
O19 N18 O20 122.6(5) . . ?
O19 N18 C7 119.0(5) . . ?
O20 N18 C7 118.5(6) . . ?
C22 S21 C25 94.0(3) . . ?
C23 C22 S21 118.9(5) . . ?
C23 C22 H22A 120.6 . . ?
S21 C22 H22A 120.6 . . ?
C22 C23 S24 117.8(5) . . ?
C22 C23 H23A 121.1 . . ?
S24 C23 H23A 121.1 . . ?
C23 S24 C25 94.8(3) . . ?
C26 C25 S24 122.1(4) . . ?
C26 C25 S21 123.3(4) . . ?
S24 C25 S21 114.5(3) . . ?
C25 C26 S30 124.2(4) . . ?
C25 C26 S27 121.6(4) . . ?
S30 C26 S27 114.1(3) . . ?
C28 S27 C26 94.8(3) . . ?
C29 C28 S27 118.4(5) . . ?
C29 C28 H28A 120.8 . . ?
S27 C28 H28A 120.8 . . ?
C28 C29 S30 118.3(5) . . ?
C28 C29 H29A 120.9 . . ?
S30 C29 H29A 120.9 . . ?
C29 S30 C26 94.4(3) . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N33 C32 C31 177.2(12) . . ?

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
C9A C1 C2 C3 -2.5(8) . . . . ?
C9A C1 C2 N15 177.2(5) . . . . ?
C1 C2 C3 C4 3.1(8) . . . . ?
N15 C2 C3 C4 -176.6(5) . . . . ?
C2 C3 C4 C4A -0.6(8) . . . . ?
C3 C4 C4A C9A -2.3(8) . . . . ?
C3 C4 C4A C4B 178.6(5) . . . . ?
C4 C4A C4B C5 -3.9(9) . . . . ?
C9A C4A C4B C5 176.9(5) . . . . ?
C4 C4A C4B C8A 179.3(5) . . . . ?
C9A C4A C4B C8A 0.2(5) . . . . ?
C8A C4B C5 C6 -2.8(8) . . . . ?
C4A C4B C5 C6 -179.2(5) . . . . ?
C4B C5 C6 C7 0.0(8) . . . . ?
C5 C6 C7 C8 0.3(8) . . . . ?
C5 C6 C7 N18 -176.7(5) . . . . ?
C6 C7 C8 C8A 2.1(8) . . . . ?
N18 C7 C8 C8A 179.2(5) . . . . ?
C7 C8 C8A C4B -4.8(7) . . . . ?
C7 C8 C8A C9 178.7(5) . . . . ?
C5 C4B C8A C8 5.3(8) . . . . ?
C4A C4B C8A C8 -177.6(4) . . . . ?
C5 C4B C8A C9 -177.5(5) . . . . ?
C4A C4B C8A C9 -0.4(6) . . . . ?
C8 C8A C9 C10 -3.5(9) . . . . ?
C4B C8A C9 C10 179.7(5) . . . . ?
C8 C8A C9 C9A 177.3(5) . . . . ?
C4B C8A C9 C9A 0.5(5) . . . . ?
C2 C1 C9A C4A -0.5(7) . . . . ?
C2 C1 C9A C9 -177.9(5) . . . . ?
C4 C4A C9A C1 2.9(7) . . . . ?
C4B C4A C9A C1 -177.9(4) . . . . ?
C4 C4A C9A C9 -179.1(5) . . . . ?
C4B C4A C9A C9 0.1(5) . . . . ?
C10 C9 C9A C1 -2.0(9) . . . . ?
C8A C9 C9A C1 177.3(5) . . . . ?
C10 C9 C9A C4A -179.6(5) . . . . ?
C8A C9 C9A C4A -0.4(5) . . . . ?
C9A C9 C10 C11 -6.4(8) . . . . ?
C8A C9 C10 C11 174.5(5) . . . . ?
C9A C9 C10 C13 177.3(5) . . . . ?
C8A C9 C10 C13 -1.8(9) . . . . ?
C3 C2 N15 O17 8.6(9) . . . . ?
C1 C2 N15 O17 -171.1(6) . . . . ?
C3 C2 N15 O16 -170.6(6) . . . . ?
C1 C2 N15 O16 9.7(9) . . . . ?
C8 C7 N18 O19 -16.6(8) . . . . ?
C6 C7 N18 O19 160.5(6) . . . . ?
C8 C7 N18 O20 162.5(6) . . . . ?
C6 C7 N18 O20 -20.3(8) . . . . ?
C25 S21 C22 C23 0.3(5) . . . . ?
S21 C22 C23 S24 -0.6(7) . . . . ?
C22 C23 S24 C25 0.5(5) . . . . ?
C23 S24 C25 C26 -178.4(5) . . . . ?
C23 S24 C25 S21 -0.3(3) . . . . ?
C22 S21 C25 C26 178.2(5) . . . . ?
C22 S21 C25 S24 0.1(3) . . . . ?
S24 C25 C26 S30 -179.5(3) . . . . ?
S21 C25 C26 S30 2.5(7) . . . . ?
S24 C25 C26 S27 0.1(7) . . . . ?
S21 C25 C26 S27 -177.8(3) . . . . ?
C25 C26 S27 C28 -179.1(5) . . . . ?
S30 C26 S27 C28 0.5(3) . . . . ?
C26 S27 C28 C29 -0.3(5) . . . . ?
S27 C28 C29 S30 -0.1(7) . . . . ?
C28 C29 S30 C26 0.4(5) . . . . ?
C25 C26 S30 C29 179.1(5) . . . . ?
S27 C26 S30 C29 -0.6(3) . . . . ?

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
C1 H1A N12 0.93 2.56 3.361(8) 144.0 .
C6 H6A O20 0.93 2.58 3.373(7) 143.7 3_656
C8 H8A N14 0.93 2.61 3.405(8) 144.1 .

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1055660'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

# CLAVE ICUAP: TTFDDNF2
# CLAVE TESIS: TTF-DDF 1/2 PhCl sintesis p. 119-120

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_date             2015-01-06

_chemical_name_systematic        
'Tetrathiafulvalene 9-dicyanomethylene-2,7-dinitrofluorene chlorobenzene hemisolvate'
_chemical_name_common            ?
_chemical_melting_point          445
_chemical_formula_moiety         'C16 H6 N4 O4, C6 H4 S4, 0.5(C6 H5 Cl)'
_chemical_formula_sum            'C25 H12.50 Cl0.50 N4 O4 S4'
_chemical_formula_weight         578.85

_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    Air-sensitive
_chemical_properties_biological  ?

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'
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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3769(11)
_cell_length_b                   9.3811(9)
_cell_length_c                   18.9293(19)
_cell_angle_alpha                81.218(7)
_cell_angle_beta                 88.805(10)
_cell_angle_gamma                75.958(10)
_cell_volume                     1255.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    60
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      11.97

_exptl_crystal_description       irregular
_exptl_crystal_colour            dark_brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             590
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.473
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.31592
_exptl_absorpt_correction_T_max  0.35034
_exptl_absorpt_process_details   ' XSCANS (Siemens, 1996)'

_exptl_special_details           ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         X-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              FN4
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_source_power             1.5
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 -1 1
-2 0 2
0 2 2

_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            6313
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4400
_reflns_number_gt                2808
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.2671P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4400
_refine_ls_number_parameters     370
_refine_ls_number_restraints     86
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_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
C1 C 0.6080(4) 0.0074(3) 0.32235(14) 0.0460(7) Uani 1 1 d . . . . .
H1A H 0.6366 -0.0957 0.3261 0.055 Uiso 1 1 calc R U . . .
C2 C 0.6368(4) 0.0763(3) 0.37927(15) 0.0499(7) Uani 1 1 d . . . . .
C3 C 0.5976(4) 0.2285(3) 0.37644(16) 0.0567(8) Uani 1 1 d . . . . .
H3A H 0.6174 0.2698 0.4164 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5281(4) 0.3191(3) 0.31302(15) 0.0548(8) Uani 1 1 d . . . . .
H4A H 0.5025 0.4220 0.3096 0.066 Uiso 1 1 calc R U . . .
C4A C 0.4975(4) 0.2538(3) 0.25518(14) 0.0416(6) Uani 1 1 d . . . . .
C4B C 0.4256(4) 0.3212(3) 0.18311(14) 0.0429(6) Uani 1 1 d . . . . .
C5 C 0.3800(4) 0.4689(3) 0.15128(16) 0.0541(8) Uani 1 1 d . . . . .
H5A H 0.3940 0.5433 0.1765 0.065 Uiso 1 1 calc R U . . .
C6 C 0.3133(4) 0.5037(3) 0.08149(15) 0.0546(8) Uani 1 1 d . . . . .
H6A H 0.2816 0.6020 0.0590 0.065 Uiso 1 1 calc R U . . .
C7 C 0.2943(4) 0.3903(3) 0.04559(14) 0.0474(7) Uani 1 1 d . . . . .
C8 C 0.3423(4) 0.2412(3) 0.07520(14) 0.0446(7) Uani 1 1 d . . . . .
H8A H 0.3289 0.1674 0.0494 0.053 Uiso 1 1 calc R U . . .
C8A C 0.4108(4) 0.2069(3) 0.14467(13) 0.0382(6) Uani 1 1 d . . . . .
C9 C 0.4793(4) 0.0620(3) 0.19110(13) 0.0396(6) Uani 1 1 d . . . . .
C9A C 0.5350(4) 0.0978(3) 0.25970(14) 0.0411(6) Uani 1 1 d . . . . .
C10 C 0.4907(4) -0.0752(3) 0.17376(14) 0.0429(6) Uani 1 1 d . . . . .
C11 C 0.5706(4) -0.2104(3) 0.22146(15) 0.0494(7) Uani 1 1 d . . . . .
N12 N 0.6349(4) -0.3188(3) 0.25762(14) 0.0691(8) Uani 1 1 d . . . . .
C13 C 0.4255(4) -0.0995(3) 0.10686(16) 0.0481(7) Uani 1 1 d . . . . .
N14 N 0.3729(4) -0.1229(3) 0.05410(14) 0.0638(7) Uani 1 1 d . . . . .
N15 N 0.7162(4) -0.0178(3) 0.44614(14) 0.0695(8) Uani 1 1 d . . . . .
O16 O 0.7692(4) -0.1508(3) 0.44619(13) 0.0966(9) Uani 1 1 d . . . . .
O17 O 0.7262(5) 0.0417(3) 0.49769(13) 0.1138(11) Uani 1 1 d . . . . .
N18 N 0.2199(4) 0.4292(3) -0.02793(13) 0.0619(7) Uani 1 1 d . . . . .
O19 O 0.1977(4) 0.3308(3) -0.05893(13) 0.0950(9) Uani 1 1 d . . . . .
O20 O 0.1819(5) 0.5580(3) -0.05497(13) 0.1097(11) Uani 1 1 d . . . . .
S21 S 0.07795(12) -0.14038(8) 0.23679(4) 0.0629(2) Uani 1 1 d . . . . .
C22 C -0.0102(4) -0.1744(4) 0.15901(18) 0.0652(9) Uani 1 1 d . . . . .
H22A H -0.0111 -0.2704 0.1523 0.078 Uiso 1 1 calc R U . . .
C23 C -0.0769(5) -0.0581(4) 0.10894(18) 0.0656(9) Uani 1 1 d . . . . .
H23A H -0.1243 -0.0705 0.0657 0.079 Uiso 1 1 calc R U . . .
S24 S -0.07289(12) 0.11692(9) 0.12655(4) 0.0605(2) Uani 1 1 d . . . . .
C25 C 0.0166(4) 0.0542(3) 0.21414(15) 0.0502(7) Uani 1 1 d . . . . .
C26 C 0.0322(4) 0.1460(3) 0.26108(15) 0.0500(7) Uani 1 1 d . . . . .
S27 S -0.03417(12) 0.34052(8) 0.23972(4) 0.0614(2) Uani 1 1 d . . . . .
C28 C 0.0003(5) 0.3693(4) 0.32608(19) 0.0759(10) Uani 1 1 d . . . . .
H28A H -0.0277 0.4650 0.3378 0.091 Uiso 1 1 calc R U . . .
C29 C 0.0671(5) 0.2532(4) 0.37499(19) 0.0750(10) Uani 1 1 d . . . . .
H29A H 0.0887 0.2647 0.4218 0.090 Uiso 1 1 calc R U . . .
S30 S 0.11336(11) 0.07860(9) 0.34937(4) 0.0618(2) Uani 1 1 d . . . . .
Cl1 Cl 0.8009(9) 0.3683(6) 0.5673(4) 0.171(2) Uani 0.5 1 d . . P . .
C31 C 0.6004(15) 0.4564(10) 0.5236(6) 0.092(3) Uani 0.5 1 d D U P . .
C32 C 0.599(3) 0.5642(14) 0.4649(8) 0.108(6) Uani 0.5 1 d D U P . .
H32A H 0.7095 0.5879 0.4489 0.130 Uiso 0.5 1 d R U P . .
C33 C 0.432(2) 0.6365(12) 0.4302(6) 0.124(5) Uani 0.5 1 d D U P . .
H33A H 0.4296 0.7083 0.3902 0.148 Uiso 0.5 1 d R U P . .
C34 C 0.268(2) 0.6044(18) 0.4554(8) 0.156(9) Uani 0.5 1 d D U P . .
H34A H 0.1533 0.6554 0.4344 0.187 Uiso 0.5 1 d R U P . .
C35 C 0.2725(18) 0.4913(16) 0.5108(7) 0.112(4) Uani 0.5 1 d D U P . .
H35A H 0.1628 0.4635 0.5248 0.135 Uiso 0.5 1 d R U P . .
C36 C 0.440(2) 0.423(2) 0.5470(9) 0.096(5) Uani 0.5 1 d D U P . .
H36A H 0.4412 0.3518 0.5872 0.115 Uiso 0.5 1 d R U P . .


_geom_special_details            ?

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 1.383(4) . ?
C1 C9A 1.384(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(4) . ?
C2 N15 1.471(4) . ?
C3 C4 1.389(4) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.381(4) . ?
C4 H4A 0.9300 . ?
C4A C9A 1.411(3) . ?
C4A C4B 1.465(4) . ?
C4B C5 1.387(4) . ?
C4B C8A 1.410(3) . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.383(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.387(4) . ?
C7 N18 1.466(4) . ?
C8 C8A 1.381(4) . ?
C8 H8A 0.9300 . ?
C8A C9 1.482(3) . ?
C9 C10 1.359(3) . ?
C9 C9A 1.480(4) . ?
C10 C13 1.433(4) . ?
C10 C11 1.443(4) . ?
C11 N12 1.138(3) . ?
C13 N14 1.149(3) . ?
N15 O17 1.207(3) . ?
N15 O16 1.214(3) . ?
N18 O20 1.205(3) . ?
N18 O19 1.210(3) . ?
S21 C22 1.725(3) . ?
S21 C25 1.758(3) . ?
C22 C23 1.332(4) . ?
C22 H22A 0.9300 . ?
C23 S24 1.732(3) . ?
C23 H23A 0.9300 . ?
S24 C25 1.758(3) . ?
C25 C26 1.353(4) . ?
C26 S27 1.755(3) . ?
C26 S30 1.757(3) . ?
S27 C28 1.731(3) . ?
C28 C29 1.318(5) . ?
C28 H28A 0.9300 . ?
C29 S30 1.732(4) . ?
C29 H29A 0.9300 . ?
Cl1 C34 0.650(14) 2_666 ?
Cl1 C31 1.674(11) . ?
Cl1 C33 1.730(19) 2_666 ?
Cl1 C35 1.819(17) 2_666 ?
C31 C34 1.049(16) 2_666 ?
C31 C33 1.200(15) 2_666 ?
C31 C35 1.283(16) 2_666 ?
C31 C36 1.347(18) . ?
C31 C32 1.382(8) . ?
C31 C32 1.54(2) 2_666 ?
C31 C36 1.60(2) 2_666 ?
C31 C31 1.71(2) 2_666 ?
C32 C36 0.35(2) 2_666 ?
C32 C35 1.043(19) 2_666 ?
C32 C33 1.377(8) . ?
C32 C31 1.54(2) 2_666 ?
C32 H32A 0.9300 . ?
C33 C36 1.038(18) 2_666 ?
C33 C31 1.200(15) 2_666 ?
C33 C34 1.375(10) . ?
C33 Cl1 1.730(19) 2_666 ?
C33 H33A 0.9299 . ?
C34 Cl1 0.650(14) 2_666 ?
C34 C31 1.049(16) 2_666 ?
C34 C35 1.369(8) . ?
C34 H34A 0.9300 . ?
C35 C32 1.043(19) 2_666 ?
C35 C31 1.283(16) 2_666 ?
C35 C36 1.386(8) . ?
C35 Cl1 1.819(17) 2_666 ?
C35 H35A 0.9300 . ?
C36 C32 0.35(2) 2_666 ?
C36 C33 1.038(18) 2_666 ?
C36 C31 1.60(2) 2_666 ?
C36 H36A 0.9299 . ?

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 C9A 117.3(2) . . ?
C2 C1 H1A 121.3 . . ?
C9A C1 H1A 121.3 . . ?
C3 C2 C1 123.6(3) . . ?
C3 C2 N15 118.2(3) . . ?
C1 C2 N15 118.2(3) . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C4A C4 C3 118.9(3) . . ?
C4A C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C4A C9A 121.2(2) . . ?
C4 C4A C4B 130.4(2) . . ?
C9A C4A C4B 108.4(2) . . ?
C5 C4B C8A 121.0(2) . . ?
C5 C4B C4A 130.4(2) . . ?
C8A C4B C4A 108.6(2) . . ?
C6 C5 C4B 118.9(3) . . ?
C6 C5 H5A 120.5 . . ?
C4B C5 H5A 120.5 . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 H6A 120.5 . . ?
C5 C6 H6A 120.5 . . ?
C6 C7 C8 123.6(3) . . ?
C6 C7 N18 118.4(2) . . ?
C8 C7 N18 118.0(2) . . ?
C8A C8 C7 117.1(2) . . ?
C8A C8 H8A 121.4 . . ?
C7 C8 H8A 121.4 . . ?
C8 C8A C4B 120.3(2) . . ?
C8 C8A C9 131.2(2) . . ?
C4B C8A C9 108.5(2) . . ?
C10 C9 C9A 127.3(2) . . ?
C10 C9 C8A 127.0(2) . . ?
C9A C9 C8A 105.7(2) . . ?
C1 C9A C4A 120.0(2) . . ?
C1 C9A C9 131.3(2) . . ?
C4A C9A C9 108.7(2) . . ?
C9 C10 C13 123.6(2) . . ?
C9 C10 C11 122.7(2) . . ?
C13 C10 C11 113.8(2) . . ?
N12 C11 C10 178.3(3) . . ?
N14 C13 C10 178.1(3) . . ?
O17 N15 O16 123.8(3) . . ?
O17 N15 C2 118.2(3) . . ?
O16 N15 C2 118.0(3) . . ?
O20 N18 O19 122.5(3) . . ?
O20 N18 C7 118.8(3) . . ?
O19 N18 C7 118.7(2) . . ?
C22 S21 C25 95.30(15) . . ?
C23 C22 S21 117.5(3) . . ?
C23 C22 H22A 121.2 . . ?
S21 C22 H22A 121.2 . . ?
C22 C23 S24 118.1(3) . . ?
C22 C23 H23A 120.9 . . ?
S24 C23 H23A 120.9 . . ?
C23 S24 C25 94.83(15) . . ?
C26 C25 S21 122.5(2) . . ?
C26 C25 S24 123.7(2) . . ?
S21 C25 S24 113.81(17) . . ?
C25 C26 S27 122.9(2) . . ?
C25 C26 S30 122.2(2) . . ?
S27 C26 S30 114.95(17) . . ?
C28 S27 C26 93.92(16) . . ?
C29 C28 S27 118.8(3) . . ?
C29 C28 H28A 120.6 . . ?
S27 C28 H28A 120.6 . . ?
C28 C29 S30 117.9(3) . . ?
C28 C29 H29A 121.0 . . ?
S30 C29 H29A 121.0 . . ?
C29 S30 C26 94.25(16) . . ?
C34 Cl1 C31 12.5(18) 2_666 . ?
C34 Cl1 C33 47.3(17) 2_666 2_666 ?
C31 Cl1 C33 41.3(6) . 2_666 ?
C34 Cl1 C35 38.2(17) 2_666 2_666 ?
C31 Cl1 C35 42.9(6) . 2_666 ?
C33 Cl1 C35 84.0(5) 2_666 2_666 ?
C34 C31 C33 75.0(10) 2_666 2_666 ?
C34 C31 C35 71.1(9) 2_666 2_666 ?
C33 C31 C35 146.0(14) 2_666 2_666 ?
C34 C31 C36 122.6(9) 2_666 . ?
C33 C31 C36 47.7(8) 2_666 . ?
C35 C31 C36 166.0(9) 2_666 . ?
C34 C31 C32 116.8(11) 2_666 . ?
C33 C31 C32 167.3(11) 2_666 . ?
C35 C31 C32 45.9(9) 2_666 . ?
C36 C31 C32 120.2(8) . . ?
C34 C31 C32 133.5(14) 2_666 2_666 ?
C33 C31 C32 59.0(8) 2_666 2_666 ?
C35 C31 C32 154.2(15) 2_666 2_666 ?
C36 C31 C32 11.9(8) . 2_666 ?
C32 C31 C32 108.7(12) . 2_666 ?
C34 C31 C36 126.7(13) 2_666 2_666 ?
C33 C31 C36 156.5(13) 2_666 2_666 ?
C35 C31 C36 56.3(8) 2_666 2_666 ?
C36 C31 C36 109.8(8) . 2_666 ?
C32 C31 C36 10.8(11) . 2_666 ?
C32 C31 C36 98.1(10) 2_666 2_666 ?
C34 C31 Cl1 7.7(11) 2_666 . ?
C33 C31 Cl1 71.9(11) 2_666 . ?
C35 C31 Cl1 74.6(11) 2_666 . ?
C36 C31 Cl1 119.3(9) . . ?
C32 C31 Cl1 120.4(12) . . ?
C32 C31 Cl1 130.8(12) 2_666 . ?
C36 C31 Cl1 130.8(12) 2_666 . ?
C34 C31 C31 170.2(15) 2_666 2_666 ?
C33 C31 C31 109.1(12) 2_666 2_666 ?
C35 C31 C31 104.3(12) 2_666 2_666 ?
C36 C31 C31 61.8(7) . 2_666 ?
C32 C31 C31 58.5(10) . 2_666 ?
C32 C31 C31 50.2(6) 2_666 2_666 ?
C36 C31 C31 48.0(7) 2_666 2_666 ?
Cl1 C31 C31 177.9(11) . 2_666 ?
C36 C32 C35 164(6) 2_666 2_666 ?
C36 C32 C33 14(5) 2_666 . ?
C35 C32 C33 177.6(15) 2_666 . ?
C36 C32 C31 122(6) 2_666 . ?
C35 C32 C31 62.0(10) 2_666 . ?
C33 C32 C31 119.6(13) . . ?
C36 C32 C31 52(5) 2_666 2_666 ?
C35 C32 C31 133.1(15) 2_666 2_666 ?
C33 C32 C31 48.3(7) . 2_666 ?
C31 C32 C31 71.3(12) . 2_666 ?
C36 C32 H32A 116.1 2_666 . ?
C35 C32 H32A 58.3 2_666 . ?
C33 C32 H32A 120.1 . . ?
C31 C32 H32A 120.3 . . ?
C31 C32 H32A 168.1 2_666 . ?
C36 C33 C31 73.6(14) 2_666 2_666 ?
C36 C33 C34 121.0(14) 2_666 . ?
C31 C33 C34 47.5(8) 2_666 . ?
C36 C33 C32 4.6(16) 2_666 . ?
C31 C33 C32 72.7(11) 2_666 . ?
C34 C33 C32 119.9(9) . . ?
C36 C33 Cl1 140.1(14) 2_666 2_666 ?
C31 C33 Cl1 66.9(9) 2_666 2_666 ?
C34 C33 Cl1 20.3(6) . 2_666 ?
C32 C33 Cl1 139.6(9) . 2_666 ?
C36 C33 H33A 119.1 2_666 . ?
C31 C33 H33A 166.3 2_666 . ?
C34 C33 H33A 119.8 . . ?
C32 C33 H33A 120.3 . . ?
Cl1 C33 H33A 99.9 2_666 . ?
Cl1 C34 C31 160(3) 2_666 2_666 ?
Cl1 C34 C35 125(2) 2_666 . ?
C31 C34 C35 62.5(9) 2_666 . ?
Cl1 C34 C33 112(2) 2_666 . ?
C31 C34 C33 57.5(9) 2_666 . ?
C35 C34 C33 120.0(8) . . ?
Cl1 C34 H34A 16.8 2_666 . ?
C31 C34 H34A 176.5 2_666 . ?
C35 C34 H34A 118.5 . . ?
C33 C34 H34A 121.5 . . ?
C32 C35 C31 72.1(10) 2_666 2_666 ?
C32 C35 C34 118.4(11) 2_666 . ?
C31 C35 C34 46.5(7) 2_666 . ?
C32 C35 C36 4.0(14) 2_666 . ?
C31 C35 C36 73.4(13) 2_666 . ?
C34 C35 C36 119.3(14) . . ?
C32 C35 Cl1 134.6(11) 2_666 2_666 ?
C31 C35 Cl1 62.5(8) 2_666 2_666 ?
C34 C35 Cl1 17.1(8) . 2_666 ?
C36 C35 Cl1 135.9(11) . 2_666 ?
C32 C35 H35A 121.8 2_666 . ?
C31 C35 H35A 165.0 2_666 . ?
C34 C35 H35A 119.8 . . ?
C36 C35 H35A 120.9 . . ?
Cl1 C35 H35A 103.2 2_666 . ?
C32 C36 C33 162(6) 2_666 2_666 ?
C32 C36 C31 116(5) 2_666 . ?
C33 C36 C31 58.7(12) 2_666 . ?
C32 C36 C35 12(4) 2_666 . ?
C33 C36 C35 173(2) 2_666 . ?
C31 C36 C35 120.6(10) . . ?
C32 C36 C31 47(5) 2_666 2_666 ?
C33 C36 C31 128.4(17) 2_666 2_666 ?
C31 C36 C31 70.2(8) . 2_666 ?
C35 C36 C31 50.4(8) . 2_666 ?
C32 C36 H36A 122.5 2_666 . ?
C33 C36 H36A 61.4 2_666 . ?
C31 C36 H36A 119.9 . . ?
C35 C36 H36A 119.5 . . ?
C31 C36 H36A 169.8 2_666 . ?

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
C9A C1 C2 C3 -0.3(4) . . . . ?
C9A C1 C2 N15 -179.3(3) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
N15 C2 C3 C4 178.0(3) . . . . ?
C2 C3 C4 C4A 1.1(4) . . . . ?
C3 C4 C4A C9A 0.2(4) . . . . ?
C3 C4 C4A C4B 179.7(3) . . . . ?
C4 C4A C4B C5 4.9(5) . . . . ?
C9A C4A C4B C5 -175.5(3) . . . . ?
C4 C4A C4B C8A -176.8(3) . . . . ?
C9A C4A C4B C8A 2.7(3) . . . . ?
C8A C4B C5 C6 2.1(4) . . . . ?
C4A C4B C5 C6 -179.8(3) . . . . ?
C4B C5 C6 C7 -0.1(5) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
C5 C6 C7 N18 178.8(3) . . . . ?
C6 C7 C8 C8A 0.7(4) . . . . ?
N18 C7 C8 C8A -179.6(2) . . . . ?
C7 C8 C8A C4B 1.5(4) . . . . ?
C7 C8 C8A C9 -178.0(3) . . . . ?
C5 C4B C8A C8 -2.9(4) . . . . ?
C4A C4B C8A C8 178.6(2) . . . . ?
C5 C4B C8A C9 176.7(3) . . . . ?
C4A C4B C8A C9 -1.8(3) . . . . ?
C8 C8A C9 C10 0.5(5) . . . . ?
C4B C8A C9 C10 -179.0(3) . . . . ?
C8 C8A C9 C9A 179.7(3) . . . . ?
C4B C8A C9 C9A 0.2(3) . . . . ?
C2 C1 C9A C4A 1.6(4) . . . . ?
C2 C1 C9A C9 -176.6(3) . . . . ?
C4 C4A C9A C1 -1.6(4) . . . . ?
C4B C4A C9A C1 178.8(2) . . . . ?
C4 C4A C9A C9 177.0(3) . . . . ?
C4B C4A C9A C9 -2.6(3) . . . . ?
C10 C9 C9A C1 -0.9(5) . . . . ?
C8A C9 C9A C1 179.9(3) . . . . ?
C10 C9 C9A C4A -179.3(3) . . . . ?
C8A C9 C9A C4A 1.5(3) . . . . ?
C9A C9 C10 C13 177.1(3) . . . . ?
C8A C9 C10 C13 -3.8(4) . . . . ?
C9A C9 C10 C11 -3.1(4) . . . . ?
C8A C9 C10 C11 176.0(3) . . . . ?
C3 C2 N15 O17 7.3(5) . . . . ?
C1 C2 N15 O17 -173.6(3) . . . . ?
C3 C2 N15 O16 -172.2(3) . . . . ?
C1 C2 N15 O16 6.8(4) . . . . ?
C6 C7 N18 O20 1.6(4) . . . . ?
C8 C7 N18 O20 -178.2(3) . . . . ?
C6 C7 N18 O19 -177.8(3) . . . . ?
C8 C7 N18 O19 2.4(4) . . . . ?
C25 S21 C22 C23 4.5(3) . . . . ?
S21 C22 C23 S24 -1.0(4) . . . . ?
C22 C23 S24 C25 -3.2(3) . . . . ?
C22 S21 C25 C26 171.6(3) . . . . ?
C22 S21 C25 S24 -6.47(19) . . . . ?
C23 S24 C25 C26 -172.0(3) . . . . ?
C23 S24 C25 S21 6.05(19) . . . . ?
S21 C25 C26 S27 -178.36(16) . . . . ?
S24 C25 C26 S27 -0.5(4) . . . . ?
S21 C25 C26 S30 -0.6(4) . . . . ?
S24 C25 C26 S30 177.28(16) . . . . ?
C25 C26 S27 C28 173.2(3) . . . . ?
S30 C26 S27 C28 -4.7(2) . . . . ?
C26 S27 C28 C29 3.3(3) . . . . ?
S27 C28 C29 S30 -0.7(4) . . . . ?
C28 C29 S30 C26 -2.3(3) . . . . ?
C25 C26 S30 C29 -173.5(3) . . . . ?
S27 C26 S30 C29 4.4(2) . . . . ?
C33 Cl1 C31 C34 -113(8) 2_666 . . 2_666 ?
C35 Cl1 C31 C34 62(7) 2_666 . . 2_666 ?
C34 Cl1 C31 C33 113(7) 2_666 . . 2_666 ?
C35 Cl1 C31 C33 174.5(10) 2_666 . . 2_666 ?
C34 Cl1 C31 C35 -62(7) 2_666 . . 2_666 ?
C33 Cl1 C31 C35 -174.5(10) 2_666 . . 2_666 ?
C34 Cl1 C31 C36 117(7) 2_666 . . . ?
C33 Cl1 C31 C36 4.6(13) 2_666 . . . ?
C35 Cl1 C31 C36 179.1(14) 2_666 . . . ?
C34 Cl1 C31 C32 -64(7) 2_666 . . . ?
C33 Cl1 C31 C32 -176.6(10) 2_666 . . . ?
C35 Cl1 C31 C32 -2.0(9) 2_666 . . . ?
C34 Cl1 C31 C32 114(7) 2_666 . . 2_666 ?
C33 Cl1 C31 C32 0.7(10) 2_666 . . 2_666 ?
C35 Cl1 C31 C32 175.3(15) 2_666 . . 2_666 ?
C34 Cl1 C31 C36 -60(7) 2_666 . . 2_666 ?
C33 Cl1 C31 C36 -172.8(17) 2_666 . . 2_666 ?
C35 Cl1 C31 C36 1.7(13) 2_666 . . 2_666 ?
C34 C31 C32 C36 157(6) 2_666 . . 2_666 ?
C33 C31 C32 C36 0(8) 2_666 . . 2_666 ?
C35 C31 C32 C36 162(7) 2_666 . . 2_666 ?
C36 C31 C32 C36 -16(7) . . . 2_666 ?
C32 C31 C32 C36 -13(6) 2_666 . . 2_666 ?
Cl1 C31 C32 C36 165(6) . . . 2_666 ?
C31 C31 C32 C36 -13(6) 2_666 . . 2_666 ?
C34 C31 C32 C35 -5.0(16) 2_666 . . 2_666 ?
C33 C31 C32 C35 -162(4) 2_666 . . 2_666 ?
C36 C31 C32 C35 -178.4(15) . . . 2_666 ?
C32 C31 C32 C35 -175.1(15) 2_666 . . 2_666 ?
C36 C31 C32 C35 -162(7) 2_666 . . 2_666 ?
Cl1 C31 C32 C35 2.7(12) . . . 2_666 ?
C31 C31 C32 C35 -175.1(15) 2_666 . . 2_666 ?
C34 C31 C32 C33 172.9(15) 2_666 . . . ?
C33 C31 C32 C33 16(4) 2_666 . . . ?
C35 C31 C32 C33 177.9(17) 2_666 . . . ?
C36 C31 C32 C33 -0.5(19) . . . . ?
C32 C31 C32 C33 2.8(8) 2_666 . . . ?
C36 C31 C32 C33 16(6) 2_666 . . . ?
Cl1 C31 C32 C33 -179.3(10) . . . . ?
C31 C31 C32 C33 2.8(8) 2_666 . . . ?
C34 C31 C32 C31 170.1(17) 2_666 . . 2_666 ?
C33 C31 C32 C31 13(4) 2_666 . . 2_666 ?
C35 C31 C32 C31 175.1(15) 2_666 . . 2_666 ?
C36 C31 C32 C31 -3.3(15) . . . 2_666 ?
C32 C31 C32 C31 0.000(1) 2_666 . . 2_666 ?
C36 C31 C32 C31 13(6) 2_666 . . 2_666 ?
Cl1 C31 C32 C31 177.9(11) . . . 2_666 ?
C31 C32 C33 C36 -103(20) . . . 2_666 ?
C31 C32 C33 C36 -100(20) 2_666 . . 2_666 ?
C36 C32 C33 C31 100(20) 2_666 . . 2_666 ?
C31 C32 C33 C31 -3.6(10) . . . 2_666 ?
C36 C32 C33 C34 106(20) 2_666 . . . ?
C31 C32 C33 C34 2.1(15) . . . . ?
C31 C32 C33 C34 5.7(12) 2_666 . . . ?
C36 C32 C33 Cl1 99(20) 2_666 . . 2_666 ?
C31 C32 C33 Cl1 -4.5(18) . . . 2_666 ?
C31 C32 C33 Cl1 -0.9(12) 2_666 . . 2_666 ?
C36 C33 C34 Cl1 -162(3) 2_666 . . 2_666 ?
C31 C33 C34 Cl1 -160(3) 2_666 . . 2_666 ?
C32 C33 C34 Cl1 -168(2) . . . 2_666 ?
C36 C33 C34 C31 -2(2) 2_666 . . 2_666 ?
C32 C33 C34 C31 -7.4(15) . . . 2_666 ?
Cl1 C33 C34 C31 160(3) 2_666 . . 2_666 ?
C36 C33 C34 C35 -1(3) 2_666 . . . ?
C31 C33 C34 C35 1.3(11) 2_666 . . . ?
C32 C33 C34 C35 -6(2) . . . . ?
Cl1 C33 C34 C35 162(4) 2_666 . . . ?
Cl1 C34 C35 C32 163(3) 2_666 . . 2_666 ?
C31 C34 C35 C32 5.1(17) 2_666 . . 2_666 ?
C33 C34 C35 C32 4(2) . . . 2_666 ?
Cl1 C34 C35 C31 158(4) 2_666 . . 2_666 ?
C33 C34 C35 C31 -1.2(11) . . . 2_666 ?
Cl1 C34 C35 C36 167(3) 2_666 . . . ?
C31 C34 C35 C36 9.6(18) 2_666 . . . ?
C33 C34 C35 C36 8(2) . . . . ?
C31 C34 C35 Cl1 -158(4) 2_666 . . 2_666 ?
C33 C34 C35 Cl1 -159(4) . . . 2_666 ?
C34 C31 C36 C32 -158(6) 2_666 . . 2_666 ?
C33 C31 C36 C32 -160(7) 2_666 . . 2_666 ?
C35 C31 C36 C32 11(10) 2_666 . . 2_666 ?
C32 C31 C36 C32 15(7) . . . 2_666 ?
C36 C31 C36 C32 12(5) 2_666 . . 2_666 ?
Cl1 C31 C36 C32 -166(6) . . . 2_666 ?
C31 C31 C36 C32 12(5) 2_666 . . 2_666 ?
C34 C31 C36 C33 2(2) 2_666 . . 2_666 ?
C35 C31 C36 C33 171(5) 2_666 . . 2_666 ?
C32 C31 C36 C33 175.2(10) . . . 2_666 ?
C32 C31 C36 C33 160(7) 2_666 . . 2_666 ?
C36 C31 C36 C33 172.0(19) 2_666 . . 2_666 ?
Cl1 C31 C36 C33 -5.9(17) . . . 2_666 ?
C31 C31 C36 C33 172.0(19) 2_666 . . 2_666 ?
C34 C31 C36 C35 -170.2(18) 2_666 . . . ?
C33 C31 C36 C35 -172(3) 2_666 . . . ?
C35 C31 C36 C35 -2(7) 2_666 . . . ?
C32 C31 C36 C35 3(3) . . . . ?
C32 C31 C36 C35 -13(5) 2_666 . . . ?
C36 C31 C36 C35 -0.4(14) 2_666 . . . ?
Cl1 C31 C36 C35 -178.3(14) . . . . ?
C31 C31 C36 C35 -0.4(14) 2_666 . . . ?
C34 C31 C36 C31 -169.8(18) 2_666 . . 2_666 ?
C33 C31 C36 C31 -172.0(19) 2_666 . . 2_666 ?
C35 C31 C36 C31 -1(5) 2_666 . . 2_666 ?
C32 C31 C36 C31 3.2(14) . . . 2_666 ?
C32 C31 C36 C31 -12(5) 2_666 . . 2_666 ?
C36 C31 C36 C31 -0.002(1) 2_666 . . 2_666 ?
Cl1 C31 C36 C31 -177.9(11) . . . 2_666 ?
C31 C35 C36 C32 -70(21) 2_666 . . 2_666 ?
C34 C35 C36 C32 -78(21) . . . 2_666 ?
Cl1 C35 C36 C32 -72(21) 2_666 . . 2_666 ?
C32 C35 C36 C31 71(21) 2_666 . . . ?
C31 C35 C36 C31 0.4(17) 2_666 . . . ?
C34 C35 C36 C31 -7(3) . . . . ?
Cl1 C35 C36 C31 -2(3) 2_666 . . . ?
C32 C35 C36 C31 70(21) 2_666 . . 2_666 ?
C34 C35 C36 C31 -7.2(14) . . . 2_666 ?
Cl1 C35 C36 C31 -2.0(15) 2_666 . . 2_666 ?

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
C1 H1A N12 0.93 2.63 3.427(4) 144.5 .
C8 H8A N14 0.93 2.65 3.451(4) 144.6 .
C22 H22A O19 0.93 2.48 3.098(4) 124.5 2
C23 H23A O19 0.93 2.65 3.181(4) 117.0 2
C32 H32A O16 0.93 2.59 3.189(15) 123.0 1_565

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chlorobenzene'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1055661'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

# CLAVE ICUAP: TTFDTNF3
# CLAVE TESIS: TTF-DTNF CH3CN Sintesis p. 

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_date             2015-01-06

_chemical_name_systematic        
'Tetrathiafulvalene 9-dicyanomethylene-2,4,7-trinitrofluorene acetonitrile monosolvate'
_chemical_name_common            ?
_chemical_melting_point          497
_chemical_formula_moiety         'C16 H5 N5 O6, C6 H4 S4, C2 H3 N'
_chemical_formula_sum            'C24 H12 N6 O6 S4'
_chemical_formula_weight         608.64

_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    Air-sensitive
_chemical_properties_biological  ?

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.1635(16)
_cell_length_b                   19.881(4)
_cell_length_c                   37.705(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5370(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    60
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      12.32

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             2480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.406
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.19981
_exptl_absorpt_correction_T_max  0.23995
_exptl_absorpt_process_details   ' XSCANS (Siemens, 1996)'

_exptl_special_details           ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         X-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              FN4
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_source_power             1.5
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -1 2
0 4 -2
0 4 2

_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            6049
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4730
_reflns_number_gt                2779
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0854P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4730
_refine_ls_number_parameters     417
_refine_ls_number_restraints     111
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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
C1 C 0.5239(6) 0.2544(2) 0.34163(9) 0.0649(11) Uani 1 1 d . . . . .
H1A H 0.5179 0.2078 0.3400 0.078 Uiso 1 1 calc R U . . .
C2 C 0.5721(6) 0.2933(2) 0.31267(10) 0.0692(12) Uani 1 1 d . . . . .
C3 C 0.5797(6) 0.3616(3) 0.31383(12) 0.0794(13) Uani 1 1 d . . . . .
H3A H 0.6127 0.3858 0.2937 0.095 Uiso 1 1 calc R U . . .
C4 C 0.5383(6) 0.3949(2) 0.34490(11) 0.0684(11) Uani 1 1 d D . . . .
H4A H 0.5414 0.4417 0.3456 0.082 Uiso 0.683(6) 1 calc R U P A 2
C4A C 0.4917(5) 0.35863(19) 0.37533(10) 0.0586(10) Uani 1 1 d . . . . .
C4B C 0.4425(5) 0.37806(18) 0.41150(10) 0.0552(9) Uani 1 1 d . . . . .
C5 C 0.4252(6) 0.43959(19) 0.42929(11) 0.0653(11) Uani 1 1 d D . . . .
H5A H 0.4515 0.4794 0.4173 0.078 Uiso 0.317(6) 1 calc R U P A 1
C6 C 0.3696(6) 0.4421(2) 0.46451(12) 0.0733(12) Uani 1 1 d . . . . .
H6A H 0.3541 0.4832 0.4758 0.088 Uiso 1 1 calc R U . . .
C7 C 0.3376(6) 0.3832(2) 0.48244(10) 0.0668(11) Uani 1 1 d . . . . .
C8 C 0.3542(5) 0.31993(19) 0.46679(9) 0.0584(10) Uani 1 1 d . . . . .
H8A H 0.3327 0.2807 0.4796 0.070 Uiso 1 1 calc R U . . .
C8A C 0.4043(5) 0.31845(17) 0.43121(9) 0.0535(9) Uani 1 1 d . . . . .
C9 C 0.4267(5) 0.26044(17) 0.40781(8) 0.0524(9) Uani 1 1 d . . . . .
C9A C 0.4848(5) 0.28748(19) 0.37326(9) 0.0548(9) Uani 1 1 d . . . . .
C10 C 0.3941(6) 0.19468(18) 0.41609(9) 0.0590(10) Uani 1 1 d . . . . .
C11 C 0.4332(7) 0.1403(2) 0.39206(11) 0.0737(12) Uani 1 1 d . . . . .
N12 N 0.4648(7) 0.0958(2) 0.37372(11) 0.1027(15) Uani 1 1 d . . . . .
C13 C 0.3287(7) 0.17155(19) 0.45017(11) 0.0713(12) Uani 1 1 d . . . . .
N14 N 0.2787(7) 0.15187(19) 0.47665(10) 0.0980(13) Uani 1 1 d . . . . .
N15 N 0.6168(6) 0.2582(3) 0.27916(9) 0.0899(12) Uani 1 1 d . . . . .
O16 O 0.5815(7) 0.1986(2) 0.27698(9) 0.1266(16) Uani 1 1 d . . . . .
O17 O 0.6835(6) 0.2911(2) 0.25509(8) 0.1218(14) Uani 1 1 d . . . . .
N18A N 0.533(2) 0.4726(6) 0.3499(4) 0.108(6) Uani 0.317(6) 1 d D . P A 1
O19A O 0.665(3) 0.5001(9) 0.3373(10) 0.32(2) Uani 0.317(6) 1 d D . P A 1
O20A O 0.415(2) 0.5059(6) 0.3673(7) 0.167(10) Uani 0.317(6) 1 d D . P A 1
N18B N 0.4605(10) 0.5030(3) 0.41095(17) 0.0776(18) Uani 0.683(6) 1 d D . P A 2
O19B O 0.3727(10) 0.5497(3) 0.42175(18) 0.148(3) Uani 0.683(6) 1 d D . P A 2
O20B O 0.5810(9) 0.5084(3) 0.38792(19) 0.102(2) Uani 0.683(6) 1 d D . P A 2
N21 N 0.2787(6) 0.3864(2) 0.52010(10) 0.0872(12) Uani 1 1 d . . . . .
O22 O 0.2540(6) 0.33385(19) 0.53587(8) 0.1036(11) Uani 1 1 d . . . . .
O23 O 0.2526(8) 0.4419(2) 0.53279(9) 0.1469(18) Uani 1 1 d . . . . .
S24 S -0.09479(15) 0.31954(5) 0.43469(3) 0.0652(3) Uani 1 1 d . . . . .
C25 C -0.1036(6) 0.4061(2) 0.44181(12) 0.0730(12) Uani 1 1 d . . . . .
H25A H -0.1443 0.4235 0.4634 0.088 Uiso 1 1 calc R U . . .
C26 C -0.0512(6) 0.4462(2) 0.41593(12) 0.0730(12) Uani 1 1 d . . . . .
H26A H -0.0533 0.4927 0.4187 0.088 Uiso 1 1 calc R U . . .
S27 S 0.02201(16) 0.40961(5) 0.37649(3) 0.0678(3) Uani 1 1 d . . . . .
C28 C -0.0178(5) 0.32707(19) 0.39054(10) 0.0577(10) Uani 1 1 d . . . . .
C29 C 0.0042(5) 0.2730(2) 0.36886(10) 0.0598(10) Uani 1 1 d . . . . .
S30 S 0.06716(16) 0.28111(6) 0.32414(3) 0.0709(4) Uani 1 1 d . . . . .
C31 C 0.0400(7) 0.1966(3) 0.31465(13) 0.0904(15) Uani 1 1 d . . . . .
H31A H 0.0586 0.1801 0.2919 0.108 Uiso 1 1 calc R U . . .
C32 C -0.0082(8) 0.1565(3) 0.34099(13) 0.0923(15) Uani 1 1 d . . . . .
H32A H -0.0255 0.1107 0.3372 0.111 Uiso 1 1 calc R U . . .
S33 S -0.03881(17) 0.19072(5) 0.38285(3) 0.0726(4) Uani 1 1 d . . . . .
C34A C 0.582(6) 0.4391(12) 0.2236(6) 0.201(15) Uani 0.248(8) 1 d D U P B 1
H34A H 0.5181 0.4115 0.2066 0.302 Uiso 0.248(8) 1 calc R U P B 1
H34B H 0.5112 0.4402 0.2453 0.302 Uiso 0.248(8) 1 calc R U P B 1
H34C H 0.7032 0.4207 0.2282 0.302 Uiso 0.248(8) 1 calc R U P B 1
C35A C 0.600(11) 0.5068(15) 0.2098(9) 0.219(16) Uani 0.248(8) 1 d D U P B 1
N36A N 0.603(7) 0.5649(14) 0.2121(11) 0.256(17) Uani 0.248(8) 1 d D U P B 1
C34B C 0.511(4) 0.5238(8) 0.2081(3) 0.263(12) Uani 0.752(8) 1 d D U P B 2
H34D H 0.5558 0.4819 0.1989 0.395 Uiso 0.752(8) 1 calc R U P B 2
H34E H 0.5774 0.5603 0.1972 0.395 Uiso 0.752(8) 1 calc R U P B 2
H34F H 0.3799 0.5281 0.2029 0.395 Uiso 0.752(8) 1 calc R U P B 2
C35B C 0.538(2) 0.5257(7) 0.2460(3) 0.191(6) Uani 0.752(8) 1 d D U P B 2
N36B N 0.534(2) 0.5233(5) 0.2768(2) 0.208(6) Uani 0.752(8) 1 d D U P B 2


_geom_special_details            ?

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 1.382(5) . ?
C1 C9A 1.391(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.360(6) . ?
C2 N15 1.478(6) . ?
C3 C4 1.378(6) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.396(5) . ?
C4 N18A 1.556(13) . ?
C4 H4A 0.9300 . ?
C4A C9A 1.418(5) . ?
C4A C4B 1.461(5) . ?
C4B C5 1.401(5) . ?
C4B C8A 1.425(5) . ?
C5 C6 1.388(6) . ?
C5 N18B 1.459(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.372(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(5) . ?
C7 N21 1.483(5) . ?
C8 C8A 1.389(5) . ?
C8 H8A 0.9300 . ?
C8A C9 1.461(5) . ?
C9 C10 1.364(5) . ?
C9 C9A 1.469(5) . ?
C10 C11 1.438(6) . ?
C10 C13 1.443(6) . ?
C11 N12 1.146(5) . ?
C13 N14 1.131(5) . ?
N15 O16 1.215(5) . ?
N15 O17 1.216(5) . ?
N18A O19A 1.190(16) . ?
N18A O20A 1.261(15) . ?
N18B O19B 1.193(7) . ?
N18B O20B 1.230(7) . ?
N21 O22 1.215(5) . ?
N21 O23 1.216(5) . ?
S24 C25 1.743(4) . ?
S24 C28 1.760(4) . ?
C25 C26 1.314(6) . ?
C25 H25A 0.9300 . ?
C26 S27 1.737(5) . ?
C26 H26A 0.9300 . ?
S27 C28 1.748(4) . ?
C28 C29 1.359(6) . ?
C29 S33 1.747(4) . ?
C29 S30 1.753(4) . ?
S30 C31 1.728(5) . ?
C31 C32 1.319(6) . ?
C31 H31A 0.9300 . ?
C32 S33 1.733(5) . ?
C32 H32A 0.9300 . ?
C34A C35A 1.450(9) . ?
C34A H34A 0.9600 . ?
C34A H34B 0.9600 . ?
C34A H34C 0.9600 . ?
C35A N36A 1.159(9) . ?
C34B C35B 1.443(8) . ?
C34B H34D 0.9600 . ?
C34B H34E 0.9600 . ?
C34B H34F 0.9600 . ?
C35B N36B 1.162(7) . ?

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 C9A 117.6(4) . . ?
C2 C1 H1A 121.2 . . ?
C9A C1 H1A 121.2 . . ?
C3 C2 C1 122.9(4) . . ?
C3 C2 N15 119.3(4) . . ?
C1 C2 N15 117.8(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 C4A 120.1(4) . . ?
C3 C4 N18A 125.9(6) . . ?
C4A C4 N18A 114.0(6) . . ?
C3 C4 H4A 119.9 . . ?
C4A C4 H4A 119.9 . . ?
C4 C4A C9A 118.6(4) . . ?
C4 C4A C4B 133.5(4) . . ?
C9A C4A C4B 107.9(3) . . ?
C5 C4B C8A 117.4(3) . . ?
C5 C4B C4A 134.4(3) . . ?
C8A C4B C4A 108.3(3) . . ?
C6 C5 C4B 121.0(4) . . ?
C6 C5 N18B 118.2(4) . . ?
C4B C5 N18B 120.8(4) . . ?
C6 C5 H5A 119.5 . . ?
C4B C5 H5A 119.5 . . ?
C7 C6 C5 119.3(4) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C6 C7 C8 123.2(4) . . ?
C6 C7 N21 118.8(4) . . ?
C8 C7 N21 118.0(4) . . ?
C8A C8 C7 116.7(3) . . ?
C8A C8 H8A 121.6 . . ?
C7 C8 H8A 121.6 . . ?
C8 C8A C4B 122.4(3) . . ?
C8 C8A C9 128.9(3) . . ?
C4B C8A C9 108.7(3) . . ?
C10 C9 C8A 126.8(3) . . ?
C10 C9 C9A 127.0(3) . . ?
C8A C9 C9A 106.1(3) . . ?
C1 C9A C4A 120.8(3) . . ?
C1 C9A C9 130.1(4) . . ?
C4A C9A C9 109.0(3) . . ?
C9 C10 C11 122.9(3) . . ?
C9 C10 C13 124.4(3) . . ?
C11 C10 C13 112.6(3) . . ?
N12 C11 C10 178.1(4) . . ?
N14 C13 C10 178.3(5) . . ?
O16 N15 O17 123.8(5) . . ?
O16 N15 C2 118.2(4) . . ?
O17 N15 C2 118.0(5) . . ?
O19A N18A O20A 120.0(18) . . ?
O19A N18A C4 112.8(16) . . ?
O20A N18A C4 127.0(12) . . ?
O19B N18B O20B 122.9(6) . . ?
O19B N18B C5 114.8(6) . . ?
O20B N18B C5 122.1(6) . . ?
O22 N21 O23 124.4(4) . . ?
O22 N21 C7 118.2(4) . . ?
O23 N21 C7 117.4(4) . . ?
C25 S24 C28 94.2(2) . . ?
C26 C25 S24 118.3(4) . . ?
C26 C25 H25A 120.9 . . ?
S24 C25 H25A 120.9 . . ?
C25 C26 S27 117.9(4) . . ?
C25 C26 H26A 121.0 . . ?
S27 C26 H26A 121.0 . . ?
C26 S27 C28 94.8(2) . . ?
C29 C28 S27 122.7(3) . . ?
C29 C28 S24 122.6(3) . . ?
S27 C28 S24 114.7(2) . . ?
C28 C29 S33 122.6(3) . . ?
C28 C29 S30 122.4(3) . . ?
S33 C29 S30 114.9(2) . . ?
C31 S30 C29 94.7(2) . . ?
C32 C31 S30 117.4(4) . . ?
C32 C31 H31A 121.3 . . ?
S30 C31 H31A 121.3 . . ?
C31 C32 S33 118.8(4) . . ?
C31 C32 H32A 120.6 . . ?
S33 C32 H32A 120.6 . . ?
C32 S33 C29 94.0(2) . . ?
C35A C34A H34A 109.5 . . ?
C35A C34A H34B 109.5 . . ?
H34A C34A H34B 109.5 . . ?
C35A C34A H34C 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
N36A C35A C34A 154(3) . . ?
C35B C34B H34D 109.5 . . ?
C35B C34B H34E 109.5 . . ?
H34D C34B H34E 109.5 . . ?
C35B C34B H34F 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?
N36B C35B C34B 170(2) . . ?

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
C9A C1 C2 C3 -1.0(6) . . . . ?
C9A C1 C2 N15 179.1(4) . . . . ?
C1 C2 C3 C4 0.1(7) . . . . ?
N15 C2 C3 C4 180.0(4) . . . . ?
C2 C3 C4 C4A 1.1(7) . . . . ?
C2 C3 C4 N18A -177.3(9) . . . . ?
C3 C4 C4A C9A -1.2(6) . . . . ?
N18A C4 C4A C9A 177.4(8) . . . . ?
C3 C4 C4A C4B 179.7(4) . . . . ?
N18A C4 C4A C4B -1.7(10) . . . . ?
C4 C4A C4B C5 -0.7(8) . . . . ?
C9A C4A C4B C5 -179.9(4) . . . . ?
C4 C4A C4B C8A 178.7(4) . . . . ?
C9A C4A C4B C8A -0.5(4) . . . . ?
C8A C4B C5 C6 -1.2(6) . . . . ?
C4A C4B C5 C6 178.1(4) . . . . ?
C8A C4B C5 N18B -179.5(4) . . . . ?
C4A C4B C5 N18B -0.2(7) . . . . ?
C4B C5 C6 C7 2.4(7) . . . . ?
N18B C5 C6 C7 -179.3(4) . . . . ?
C5 C6 C7 C8 -1.5(7) . . . . ?
C5 C6 C7 N21 179.8(4) . . . . ?
C6 C7 C8 C8A -0.5(6) . . . . ?
N21 C7 C8 C8A 178.2(4) . . . . ?
C7 C8 C8A C4B 1.7(6) . . . . ?
C7 C8 C8A C9 -178.1(4) . . . . ?
C5 C4B C8A C8 -0.9(5) . . . . ?
C4A C4B C8A C8 179.6(3) . . . . ?
C5 C4B C8A C9 178.9(3) . . . . ?
C4A C4B C8A C9 -0.6(4) . . . . ?
C8 C8A C9 C10 3.1(6) . . . . ?
C4B C8A C9 C10 -176.6(4) . . . . ?
C8 C8A C9 C9A -178.9(4) . . . . ?
C4B C8A C9 C9A 1.4(4) . . . . ?
C2 C1 C9A C4A 0.9(6) . . . . ?
C2 C1 C9A C9 178.6(4) . . . . ?
C4 C4A C9A C1 0.2(6) . . . . ?
C4B C4A C9A C1 179.5(3) . . . . ?
C4 C4A C9A C9 -178.0(3) . . . . ?
C4B C4A C9A C9 1.4(4) . . . . ?
C10 C9 C9A C1 -1.6(7) . . . . ?
C8A C9 C9A C1 -179.6(4) . . . . ?
C10 C9 C9A C4A 176.3(4) . . . . ?
C8A C9 C9A C4A -1.7(4) . . . . ?
C8A C9 C10 C11 -175.3(4) . . . . ?
C9A C9 C10 C11 7.1(7) . . . . ?
C8A C9 C10 C13 0.6(7) . . . . ?
C9A C9 C10 C13 -177.0(4) . . . . ?
C3 C2 N15 O16 -168.7(5) . . . . ?
C1 C2 N15 O16 11.2(7) . . . . ?
C3 C2 N15 O17 9.9(6) . . . . ?
C1 C2 N15 O17 -170.2(4) . . . . ?
C3 C4 N18A O19A -46(3) . . . . ?
C4A C4 N18A O19A 135(2) . . . . ?
C3 C4 N18A O20A 138.9(18) . . . . ?
C4A C4 N18A O20A -40(2) . . . . ?
C6 C5 N18B O19B -28.4(8) . . . . ?
C4B C5 N18B O19B 150.0(6) . . . . ?
C6 C5 N18B O20B 146.7(6) . . . . ?
C4B C5 N18B O20B -35.0(8) . . . . ?
C6 C7 N21 O22 -178.7(4) . . . . ?
C8 C7 N21 O22 2.6(6) . . . . ?
C6 C7 N21 O23 3.5(7) . . . . ?
C8 C7 N21 O23 -175.2(5) . . . . ?
C28 S24 C25 C26 -2.0(4) . . . . ?
S24 C25 C26 S27 0.3(5) . . . . ?
C25 C26 S27 C28 1.6(4) . . . . ?
C26 S27 C28 C29 175.5(4) . . . . ?
C26 S27 C28 S24 -2.9(3) . . . . ?
C25 S24 C28 C29 -175.4(4) . . . . ?
C25 S24 C28 S27 3.0(2) . . . . ?
S27 C28 C29 S33 -179.1(2) . . . . ?
S24 C28 C29 S33 -0.9(5) . . . . ?
S27 C28 C29 S30 -2.2(5) . . . . ?
S24 C28 C29 S30 176.0(2) . . . . ?
C28 C29 S30 C31 -173.6(4) . . . . ?
S33 C29 S30 C31 3.5(3) . . . . ?
C29 S30 C31 C32 -1.8(5) . . . . ?
S30 C31 C32 S33 -0.5(7) . . . . ?
C31 C32 S33 C29 2.6(5) . . . . ?
C28 C29 S33 C32 173.4(4) . . . . ?
S30 C29 S33 C32 -3.7(3) . . . . ?

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
C1 H1A N12 0.93 2.59 3.404(6) 146.2 .
C4 H4A O20B 0.93 2.09 2.795(8) 131.1 .
C5 H5A N18A 0.93 2.61 3.159(14) 118.3 .
C5 H5A O20A 0.93 1.98 2.68(2) 131.6 .
C8 H8A N14 0.93 2.59 3.405(5) 146.4 .
C31 H31A O16 0.93 2.63 3.468(6) 150.8 6_556
C32 H32A O19A 0.93 2.41 3.309(18) 161.1 8_655
C32 H32A O20A 0.93 2.50 3.225(13) 134.6 8_655
C34A H34A S30 0.96 2.86 3.62(2) 136.9 6_656
C34B H34F N36B 0.96 2.59 3.46(3) 150.2 6_556

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1055662'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

# CLAVE ICUAP: TDTNF
# CLAVE TESIS: TTF-DTNF 1/2 Me2CO Sintesis p. 121-122


# start Validation Reply Form
_vrf_THETM01_4                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Poor diffraction, probably related to solvent loss
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_date             2015-01-06

_chemical_name_systematic        
'Tetrathiafulvalene 9-dicyanomethylene-2,4,7-trinitrofluorene acetone hemisolvate'
_chemical_name_common            ?
_chemical_melting_point          499
_chemical_formula_moiety         'C16 H5 N5 O6, C6 H4 S4, 0.5(C3 H6 O)'
_chemical_formula_sum            'C23.50 H12 N5 O6.50 S4'
_chemical_formula_weight         596.62

_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    Air-sensitive
_chemical_properties_biological  ?

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.1682(15)
_cell_length_b                   19.902(6)
_cell_length_c                   37.805(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5393(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    40
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      11.95

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.403
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.21349
_exptl_absorpt_correction_T_max  0.24470
_exptl_absorpt_process_details   ' XSCANS (Siemens, 1996)'

_exptl_special_details           ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         X-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              FN4
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_source_power             1.5
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -4 -2
2 0 -4
-2 0 -4

_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            8389
_diffrn_reflns_av_unetI/netI     0.0721
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.047
_diffrn_reflns_theta_max         22.534
_diffrn_reflns_theta_full        22.534
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3545
_reflns_number_gt                1984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+0.8174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       0.00053(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3545
_refine_ls_number_parameters     399
_refine_ls_number_restraints     53
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_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
C1 C 0.5142(8) 0.2561(3) 0.34193(14) 0.0719(17) Uani 1 1 d . . . . .
H1A H 0.5058 0.2096 0.3400 0.086 Uiso 1 1 calc R U . . .
C2 C 0.5639(9) 0.2952(4) 0.31322(15) 0.0803(18) Uani 1 1 d . . . . .
C3 C 0.5752(10) 0.3632(4) 0.31447(17) 0.088(2) Uani 1 1 d . . . . .
H3A H 0.6098 0.3873 0.2945 0.106 Uiso 1 1 calc R U . . .
C4 C 0.5346(9) 0.3967(3) 0.34585(17) 0.0774(18) Uani 1 1 d D . . . .
H4A H 0.5400 0.4434 0.3469 0.093 Uiso 0.635(10) 1 calc R U P A 2
C4A C 0.4854(8) 0.3593(3) 0.37598(14) 0.0645(15) Uani 1 1 d . . . . .
C4B C 0.4359(8) 0.3782(3) 0.41221(15) 0.0658(15) Uani 1 1 d . . . . .
C5 C 0.4212(9) 0.4389(3) 0.43017(17) 0.0742(17) Uani 1 1 d D . . . .
H5A H 0.4476 0.4788 0.4184 0.089 Uiso 0.365(10) 1 calc R U P A 1
C6 C 0.3682(10) 0.4407(3) 0.46520(18) 0.0854(19) Uani 1 1 d . . . . .
H6A H 0.3559 0.4817 0.4768 0.102 Uiso 1 1 calc R U . . .
C7 C 0.3334(10) 0.3815(3) 0.48296(14) 0.0731(16) Uani 1 1 d . . . . .
C8 C 0.3481(8) 0.3198(3) 0.46700(13) 0.0646(15) Uani 1 1 d . . . . .
H8A H 0.3261 0.2805 0.4796 0.078 Uiso 1 1 calc R U . . .
C8A C 0.3963(8) 0.3178(2) 0.43160(14) 0.0617(14) Uani 1 1 d . . . . .
C9 C 0.4191(8) 0.2605(2) 0.40775(13) 0.0597(14) Uani 1 1 d . . . . .
C9A C 0.4775(8) 0.2881(3) 0.37341(14) 0.0621(15) Uani 1 1 d . . . . .
C10 C 0.3867(9) 0.1939(3) 0.41572(14) 0.0679(16) Uani 1 1 d . . . . .
C11 C 0.4247(11) 0.1403(3) 0.39100(17) 0.083(2) Uani 1 1 d . . . . .
N12 N 0.4564(11) 0.0963(3) 0.37251(16) 0.120(3) Uani 1 1 d . . . . .
C13 C 0.3210(10) 0.1702(3) 0.44978(17) 0.0790(18) Uani 1 1 d . . . . .
N14 N 0.2708(10) 0.1500(3) 0.47619(15) 0.110(2) Uani 1 1 d . . . . .
N15 N 0.6088(10) 0.2615(5) 0.27921(15) 0.112(2) Uani 1 1 d . . . . .
O16 O 0.5731(13) 0.2021(4) 0.27691(14) 0.151(3) Uani 1 1 d . . . . .
O17 O 0.6739(10) 0.2952(3) 0.25539(12) 0.145(2) Uani 1 1 d . . . . .
N18A N 0.533(3) 0.4735(6) 0.3508(4) 0.092(6) Uani 0.365(10) 1 d D . P A 1
O19A O 0.635(5) 0.5015(10) 0.3326(12) 0.39(3) Uani 0.365(10) 1 d D . P A 1
O20A O 0.421(4) 0.5072(8) 0.3679(10) 0.200(14) Uani 0.365(10) 1 d D . P A 1
N18B N 0.4611(17) 0.5019(4) 0.4108(3) 0.098(3) Uani 0.635(10) 1 d D . P A 2
O19B O 0.373(2) 0.5480(5) 0.4230(3) 0.192(6) Uani 0.635(10) 1 d D . P A 2
O20B O 0.5810(15) 0.5059(4) 0.3858(4) 0.116(4) Uani 0.635(10) 1 d D . P A 2
N21 N 0.2750(10) 0.3835(4) 0.52020(15) 0.103(2) Uani 1 1 d . . . . .
O22 O 0.2482(9) 0.3314(3) 0.53560(12) 0.1169(19) Uani 1 1 d . . . . .
O23 O 0.2548(12) 0.4389(3) 0.53387(14) 0.164(3) Uani 1 1 d . . . . .
S24 S -0.1007(2) 0.32108(8) 0.43502(4) 0.0728(5) Uani 1 1 d . . . . .
C25 C -0.1088(9) 0.4069(3) 0.44211(17) 0.0826(18) Uani 1 1 d . . . . .
H25A H -0.1484 0.4241 0.4637 0.099 Uiso 1 1 calc R U . . .
C26 C -0.0574(9) 0.4477(3) 0.41606(17) 0.0802(18) Uani 1 1 d . . . . .
H26A H -0.0608 0.4941 0.4187 0.096 Uiso 1 1 calc R U . . .
S27 S 0.0162(2) 0.41101(8) 0.37703(4) 0.0756(5) Uani 1 1 d . . . . .
C28 C -0.0243(8) 0.3282(3) 0.39127(14) 0.0645(15) Uani 1 1 d . . . . .
C29 C -0.0051(9) 0.2746(3) 0.36964(15) 0.0692(16) Uani 1 1 d . . . . .
S30 S 0.0579(2) 0.28320(9) 0.32471(4) 0.0798(6) Uani 1 1 d . . . . .
C31 C 0.0313(12) 0.1995(4) 0.31504(19) 0.106(3) Uani 1 1 d . . . . .
H31A H 0.0503 0.1831 0.2923 0.127 Uiso 1 1 calc R U . . .
C32 C -0.0181(13) 0.1583(4) 0.34184(19) 0.109(3) Uani 1 1 d . . . . .
H32A H -0.0355 0.1126 0.3380 0.131 Uiso 1 1 calc R U . . .
S33 S -0.0480(3) 0.19233(8) 0.38288(4) 0.0826(6) Uani 1 1 d . . . . .
C34 C 1.063(4) 0.5153(14) 0.2548(6) 0.356(19) Uani 0.5 1 d D U P . .
O35 O 1.028(6) 0.5153(9) 0.2233(5) 0.398(19) Uani 0.5 1 d D U P . .
C36 C 1.040(6) 0.4587(15) 0.2788(7) 0.33(2) Uani 0.5 1 d D U P . .
H36A H 0.9516 0.4276 0.2691 0.493 Uiso 0.5 1 calc R U P . .
H36B H 0.9958 0.4747 0.3013 0.493 Uiso 0.5 1 calc R U P . .
H36C H 1.1580 0.4366 0.2820 0.493 Uiso 0.5 1 calc R U P . .
C37 C 1.145(6) 0.5741(14) 0.2712(8) 0.33(2) Uani 0.5 1 d D U P . .
H37A H 1.2110 0.5610 0.2922 0.492 Uiso 0.5 1 calc R U P . .
H37B H 1.0486 0.6055 0.2773 0.492 Uiso 0.5 1 calc R U P . .
H37C H 1.2306 0.5950 0.2550 0.492 Uiso 0.5 1 calc R U P . .


_geom_special_details            ?

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 C9A 1.376(8) . ?
C1 C2 1.383(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.355(9) . ?
C2 N15 1.486(9) . ?
C3 C4 1.392(9) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.406(7) . ?
C4 N18A 1.538(13) . ?
C4 H4A 0.9300 . ?
C4A C9A 1.420(7) . ?
C4A C4B 1.464(8) . ?
C4B C5 1.390(8) . ?
C4B C8A 1.435(7) . ?
C5 C6 1.378(8) . ?
C5 N18B 1.480(10) . ?
C5 H5A 0.9300 . ?
C6 C7 1.380(8) . ?
C6 H6A 0.9300 . ?
C7 C8 1.372(7) . ?
C7 N21 1.469(8) . ?
C8 C8A 1.383(7) . ?
C8 H8A 0.9300 . ?
C8A C9 1.464(7) . ?
C9 C10 1.378(7) . ?
C9 C9A 1.471(7) . ?
C10 C11 1.445(9) . ?
C10 C13 1.450(9) . ?
C11 N12 1.144(7) . ?
C13 N14 1.135(7) . ?
N15 O16 1.212(8) . ?
N15 O17 1.216(8) . ?
N18A O19A 1.149(17) . ?
N18A O20A 1.231(17) . ?
N18B O19B 1.206(11) . ?
N18B O20B 1.281(12) . ?
N21 O22 1.203(7) . ?
N21 O23 1.228(7) . ?
S24 C25 1.729(6) . ?
S24 C28 1.748(6) . ?
C25 C26 1.329(8) . ?
C25 H25A 0.9300 . ?
C26 S27 1.728(7) . ?
C26 H26A 0.9300 . ?
S27 C28 1.759(5) . ?
C28 C29 1.350(8) . ?
C29 S33 1.740(6) . ?
C29 S30 1.766(6) . ?
S30 C31 1.716(7) . ?
C31 C32 1.351(9) . ?
C31 H31A 0.9300 . ?
C32 S33 1.706(7) . ?
C32 H32A 0.9300 . ?
C34 O35 1.215(10) . ?
C34 C36 1.456(10) . ?
C34 C37 1.452(10) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

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
C9A C1 C2 117.8(6) . . ?
C9A C1 H1A 121.1 . . ?
C2 C1 H1A 121.1 . . ?
C3 C2 C1 123.4(6) . . ?
C3 C2 N15 117.9(6) . . ?
C1 C2 N15 118.7(6) . . ?
C2 C3 C4 119.7(6) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C4A 119.2(5) . . ?
C3 C4 N18A 125.5(8) . . ?
C4A C4 N18A 115.2(8) . . ?
C3 C4 H4A 120.4 . . ?
C4A C4 H4A 120.4 . . ?
C4 C4A C9A 118.9(5) . . ?
C4 C4A C4B 133.1(5) . . ?
C9A C4A C4B 108.1(5) . . ?
C5 C4B C8A 117.6(5) . . ?
C5 C4B C4A 134.3(5) . . ?
C8A C4B C4A 108.1(5) . . ?
C6 C5 C4B 120.9(5) . . ?
C6 C5 N18B 120.3(7) . . ?
C4B C5 N18B 118.8(7) . . ?
C6 C5 H5A 119.5 . . ?
C4B C5 H5A 119.5 . . ?
C5 C6 C7 119.6(6) . . ?
C5 C6 H6A 120.2 . . ?
C7 C6 H6A 120.2 . . ?
C8 C7 C6 122.5(5) . . ?
C8 C7 N21 117.8(6) . . ?
C6 C7 N21 119.7(6) . . ?
C7 C8 C8A 118.0(5) . . ?
C7 C8 H8A 121.0 . . ?
C8A C8 H8A 121.0 . . ?
C8 C8A C4B 121.3(5) . . ?
C8 C8A C9 130.3(5) . . ?
C4B C8A C9 108.4(5) . . ?
C10 C9 C8A 126.6(5) . . ?
C10 C9 C9A 126.9(5) . . ?
C8A C9 C9A 106.5(4) . . ?
C1 C9A C4A 120.9(5) . . ?
C1 C9A C9 130.1(5) . . ?
C4A C9A C9 108.9(5) . . ?
C9 C10 C11 122.5(5) . . ?
C9 C10 C13 124.2(5) . . ?
C11 C10 C13 113.3(5) . . ?
N12 C11 C10 177.3(6) . . ?
N14 C13 C10 178.2(7) . . ?
O16 N15 O17 124.5(8) . . ?
O16 N15 C2 117.2(7) . . ?
O17 N15 C2 118.3(8) . . ?
O19A N18A O20A 117.7(18) . . ?
O19A N18A C4 113.9(18) . . ?
O20A N18A C4 127.6(16) . . ?
O19B N18B O20B 126.0(10) . . ?
O19B N18B C5 110.7(10) . . ?
O20B N18B C5 123.2(9) . . ?
O22 N21 O23 123.5(6) . . ?
O22 N21 C7 119.1(6) . . ?
O23 N21 C7 117.4(7) . . ?
C25 S24 C28 94.5(3) . . ?
C26 C25 S24 118.6(5) . . ?
C26 C25 H25A 120.7 . . ?
S24 C25 H25A 120.7 . . ?
C25 C26 S27 117.4(5) . . ?
C25 C26 H26A 121.3 . . ?
S27 C26 H26A 121.3 . . ?
C26 S27 C28 94.8(3) . . ?
C29 C28 S24 122.8(4) . . ?
C29 C28 S27 122.5(4) . . ?
S24 C28 S27 114.6(3) . . ?
C28 C29 S33 123.4(4) . . ?
C28 C29 S30 122.2(4) . . ?
S33 C29 S30 114.4(4) . . ?
C31 S30 C29 94.8(3) . . ?
C32 C31 S30 117.3(5) . . ?
C32 C31 H31A 121.4 . . ?
S30 C31 H31A 121.4 . . ?
C31 C32 S33 118.3(6) . . ?
C31 C32 H32A 120.8 . . ?
S33 C32 H32A 120.8 . . ?
C32 S33 C29 95.2(3) . . ?
O35 C34 C36 126(3) . . ?
O35 C34 C37 120(3) . . ?
C36 C34 C37 113.7(15) . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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
C9A C1 C2 C3 -1.1(10) . . . . ?
C9A C1 C2 N15 178.5(6) . . . . ?
C1 C2 C3 C4 -0.3(11) . . . . ?
N15 C2 C3 C4 -179.9(6) . . . . ?
C2 C3 C4 C4A 1.0(10) . . . . ?
C2 C3 C4 N18A -177.2(11) . . . . ?
C3 C4 C4A C9A -0.4(9) . . . . ?
N18A C4 C4A C9A 178.0(10) . . . . ?
C3 C4 C4A C4B 179.9(6) . . . . ?
N18A C4 C4A C4B -1.7(13) . . . . ?
C4 C4A C4B C5 -0.8(12) . . . . ?
C9A C4A C4B C5 179.4(6) . . . . ?
C4 C4A C4B C8A 179.3(6) . . . . ?
C9A C4A C4B C8A -0.4(6) . . . . ?
C8A C4B C5 C6 -0.8(9) . . . . ?
C4A C4B C5 C6 179.3(6) . . . . ?
C8A C4B C5 N18B -180.0(7) . . . . ?
C4A C4B C5 N18B 0.2(11) . . . . ?
C4B C5 C6 C7 1.6(10) . . . . ?
N18B C5 C6 C7 -179.3(7) . . . . ?
C5 C6 C7 C8 -0.5(10) . . . . ?
C5 C6 C7 N21 -179.4(6) . . . . ?
C6 C7 C8 C8A -1.2(9) . . . . ?
N21 C7 C8 C8A 177.7(6) . . . . ?
C7 C8 C8A C4B 1.9(9) . . . . ?
C7 C8 C8A C9 -178.9(6) . . . . ?
C5 C4B C8A C8 -0.9(8) . . . . ?
C4A C4B C8A C8 179.0(5) . . . . ?
C5 C4B C8A C9 179.7(5) . . . . ?
C4A C4B C8A C9 -0.4(6) . . . . ?
C8 C8A C9 C10 3.6(10) . . . . ?
C4B C8A C9 C10 -177.1(6) . . . . ?
C8 C8A C9 C9A -178.2(6) . . . . ?
C4B C8A C9 C9A 1.1(6) . . . . ?
C2 C1 C9A C4A 1.8(9) . . . . ?
C2 C1 C9A C9 178.8(6) . . . . ?
C4 C4A C9A C1 -1.1(9) . . . . ?
C4B C4A C9A C1 178.7(5) . . . . ?
C4 C4A C9A C9 -178.7(5) . . . . ?
C4B C4A C9A C9 1.1(6) . . . . ?
C10 C9 C9A C1 -0.5(10) . . . . ?
C8A C9 C9A C1 -178.7(6) . . . . ?
C10 C9 C9A C4A 176.8(6) . . . . ?
C8A C9 C9A C4A -1.4(6) . . . . ?
C8A C9 C10 C11 -175.9(6) . . . . ?
C9A C9 C10 C11 6.2(10) . . . . ?
C8A C9 C10 C13 0.8(10) . . . . ?
C9A C9 C10 C13 -177.0(6) . . . . ?
C3 C2 N15 O16 -169.8(8) . . . . ?
C1 C2 N15 O16 10.6(11) . . . . ?
C3 C2 N15 O17 8.3(10) . . . . ?
C1 C2 N15 O17 -171.3(7) . . . . ?
C3 C4 N18A O19A -30(4) . . . . ?
C4A C4 N18A O19A 152(3) . . . . ?
C3 C4 N18A O20A 140(3) . . . . ?
C4A C4 N18A O20A -39(3) . . . . ?
C6 C5 N18B O19B -28.2(14) . . . . ?
C4B C5 N18B O19B 151.0(10) . . . . ?
C6 C5 N18B O20B 148.7(11) . . . . ?
C4B C5 N18B O20B -32.2(15) . . . . ?
C8 C7 N21 O22 2.4(10) . . . . ?
C6 C7 N21 O22 -178.7(7) . . . . ?
C8 C7 N21 O23 -177.1(7) . . . . ?
C6 C7 N21 O23 1.8(11) . . . . ?
C28 S24 C25 C26 -1.4(6) . . . . ?
S24 C25 C26 S27 -0.6(8) . . . . ?
C25 C26 S27 C28 2.2(6) . . . . ?
C25 S24 C28 C29 -174.6(5) . . . . ?
C25 S24 C28 S27 2.9(4) . . . . ?
C26 S27 C28 C29 174.3(6) . . . . ?
C26 S27 C28 S24 -3.1(4) . . . . ?
S24 C28 C29 S33 -1.7(8) . . . . ?
S27 C28 C29 S33 -178.9(3) . . . . ?
S24 C28 C29 S30 175.9(3) . . . . ?
S27 C28 C29 S30 -1.3(8) . . . . ?
C28 C29 S30 C31 -174.5(6) . . . . ?
S33 C29 S30 C31 3.3(4) . . . . ?
C29 S30 C31 C32 -1.6(7) . . . . ?
S30 C31 C32 S33 -0.6(10) . . . . ?
C31 C32 S33 C29 2.5(8) . . . . ?
C28 C29 S33 C32 174.3(6) . . . . ?
S30 C29 S33 C32 -3.5(5) . . . . ?

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
C1 H1A N12 0.93 2.59 3.410(8) 146.9 .
C4 H4A O20B 0.93 1.95 2.667(13) 132.5 .
C5 H5A N18A 0.93 2.63 3.182(16) 118.6 .
C5 H5A O20A 0.93 2.00 2.72(3) 132.8 .
C8 H8A N14 0.93 2.63 3.442(8) 146.2 .
C26 H26A O23 0.93 2.63 3.268(8) 126.2 5_566
C31 H31A O16 0.93 2.65 3.489(9) 150.8 6_556
C32 H32A O19A 0.93 2.33 3.25(2) 169.2 8_655
C32 H32A O20A 0.93 2.52 3.241(18) 134.5 8_655
C37 H37A O35 0.96 2.52 2.99(6) 110.4 6_656
C37 H37B O16 0.96 2.11 3.00(4) 152.5 8_765

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.067


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1055663'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

# CLAVE ICUAP: DC2TNF2
# CLAVE TESIS: TTF-DC2TNF.H2O  Sintesis p. 123-124

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_date             2015-01-30

_chemical_name_systematic        
'Tetrathiafulvalene 9-dicyanomethylene-4,5,7-trinitrofluorene-2-carboxylic acid monohydrate'

_chemical_name_common            ?
_chemical_melting_point          509
_chemical_formula_moiety         'C17 H5 N5 O8, C6 H4 S4, H2 O'
_chemical_formula_sum            'C23 H11 N5 O9 S4'
_chemical_formula_weight         629.61

_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?


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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_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'

_cell_length_a                   15.9432(14)
_cell_length_b                   12.1351(9)
_cell_length_c                   13.5738(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.572(7)
_cell_angle_gamma                90
_cell_volume                     2541.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    79
_cell_measurement_theta_min      4.80
_cell_measurement_theta_max      12.40

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.439
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.28602
_exptl_absorpt_correction_T_max  0.33615
_exptl_absorpt_process_details   'XSCANS (Siemens, 1996)'

_exptl_special_details           ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         X-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              FN4
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_source_power             1.5
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 -1
4 0 -8
-4 0 8

_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            6560
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2918
_reflns_number_gt                2476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+5.6211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2918
_refine_ls_number_parameters     227
_refine_ls_number_restraints     14
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1448
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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
C1 C 0.66001(17) 0.5337(2) 0.8326(2) 0.0365(6) Uani 1 1 d . . . . .
H1A H 0.6766 0.4603 0.8436 0.044 Uiso 1 1 calc R U . . .
C2 C 0.72027(18) 0.6177(3) 0.8617(2) 0.0415(6) Uani 1 1 d D . . . .
C3 C 0.6975(2) 0.7261(3) 0.8409(2) 0.0474(7) Uani 1 1 d . . . . .
H3A H 0.7390 0.7813 0.8583 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6129(2) 0.7524(2) 0.7943(2) 0.0456(7) Uani 1 1 d . . . . .
C5 C 0.54710(17) 0.6727(2) 0.77071(19) 0.0334(5) Uani 1 1 d . . . . .
C6 C 0.57429(16) 0.5611(2) 0.78657(19) 0.0315(5) Uani 1 1 d . . . . .
C7 C 0.5000 0.4882(3) 0.7500 0.0297(7) Uani 1 2 d S T P . .
C8 C 0.5000 0.3753(3) 0.7500 0.0344(8) Uani 1 2 d S T P . .
C9 C 0.57790(19) 0.3103(2) 0.7761(2) 0.0424(6) Uani 1 1 d . . . . .
N10 N 0.6388(2) 0.2568(3) 0.7946(3) 0.0663(8) Uani 1 1 d . . . . .
C11A C 0.8104(9) 0.5914(10) 0.9166(13) 0.051(7) Uani 0.5 1 d D . P A 1
O12A O 0.8330(13) 0.4931(13) 0.9211(17) 0.115(7) Uani 0.5 1 d D . P A 1
O13A O 0.8553(14) 0.6735(15) 0.9588(18) 0.084(6) Uani 0.5 1 d D . P A 1
H13A H 0.905(3) 0.651(4) 0.996(5) 0.126 Uiso 0.5 1 d D U P B 1
N11B N 0.8102(7) 0.5864(11) 0.9166(12) 0.072(8) Uani 0.5 1 d D . P A 2
O12B O 0.8239(9) 0.4845(8) 0.9341(10) 0.053(2) Uani 0.5 1 d D . P A 2
O13B O 0.8663(13) 0.6562(12) 0.9382(16) 0.068(4) Uani 0.5 1 d D . P A 2
N14 N 0.5972(2) 0.8675(3) 0.7570(3) 0.0655(8) Uani 1 1 d . . . . .
O15 O 0.5414(2) 0.8818(2) 0.6742(2) 0.0744(8) Uani 1 1 d . . . . .
O16 O 0.6418(2) 0.9397(2) 0.8099(3) 0.0931(11) Uani 1 1 d . . . . .
S17 S 0.63982(5) 0.47940(6) 0.56837(6) 0.0419(2) Uani 1 1 d . . . . .
C18 C 0.6905(2) 0.6071(3) 0.5831(2) 0.0499(7) Uani 1 1 d . . . . .
H18A H 0.7499 0.6135 0.6108 0.060 Uiso 1 1 calc R U . . .
C19 C 0.6415(2) 0.6952(3) 0.5536(3) 0.0527(8) Uani 1 1 d . . . . .
H19A H 0.6656 0.7654 0.5589 0.063 Uiso 1 1 calc R U . . .
S20 S 0.53055(5) 0.67557(6) 0.50444(6) 0.0456(2) Uani 1 1 d . . . . .
C21 C 0.53581(17) 0.5328(2) 0.5157(2) 0.0368(6) Uani 1 1 d . . . . .
O22 O 1.0273(4) 0.5827(4) 0.9393(5) 0.0763(17) Uani 0.5 1 d D . P . .
H22A H 0.995(5) 0.527(5) 0.921(8) 0.114 Uiso 0.5 1 d D U P . .
H22B H 1.070(4) 0.563(8) 0.987(6) 0.114 Uiso 0.5 1 d D U P . .


_geom_special_details            ?

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 1.388(4) . ?
C1 C6 1.392(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(5) . ?
C2 C11A 1.478(12) . ?
C2 N11B 1.489(11) . ?
C3 C4 1.374(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.404(4) . ?
C4 N14 1.485(4) . ?
C5 C6 1.422(3) . ?
C5 C5 1.465(5) 2_656 ?
C6 C7 1.461(3) . ?
C7 C8 1.370(5) . ?
C7 C6 1.461(3) 2_656 ?
C8 C9 1.438(4) . ?
C8 C9 1.438(4) 2_656 ?
C9 N10 1.142(4) . ?
C11A O12A 1.243(15) . ?
C11A O13A 1.275(18) . ?
O13A H13A 0.88(2) . ?
N11B O13B 1.212(15) . ?
N11B O12B 1.268(13) . ?
N14 O16 1.239(4) . ?
N14 O15 1.258(4) . ?
S17 C18 1.736(3) . ?
S17 C21 1.756(3) . ?
C18 C19 1.326(5) . ?
C18 H18A 0.9300 . ?
C19 S20 1.742(3) . ?
C19 H19A 0.9300 . ?
S20 C21 1.740(3) . ?
C21 C21 1.369(5) 5_666 ?
O22 H22A 0.85(2) . ?
O22 H22B 0.85(2) . ?

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 C6 118.9(3) . . ?
C2 C1 H1A 120.6 . . ?
C6 C1 H1A 120.6 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 C11A 118.9(6) . . ?
C1 C2 C11A 120.0(6) . . ?
C3 C2 N11B 121.2(6) . . ?
C1 C2 N11B 117.7(6) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 122.4(3) . . ?
C3 C4 N14 115.9(3) . . ?
C5 C4 N14 121.2(3) . . ?
C4 C5 C6 116.1(2) . . ?
C4 C5 C5 136.31(17) . 2_656 ?
C6 C5 C5 107.58(15) . 2_656 ?
C1 C6 C5 121.5(2) . . ?
C1 C6 C7 128.9(2) . . ?
C5 C6 C7 109.6(2) . . ?
C8 C7 C6 127.23(15) . . ?
C8 C7 C6 127.23(15) . 2_656 ?
C6 C7 C6 105.5(3) . 2_656 ?
C7 C8 C9 123.24(17) . . ?
C7 C8 C9 123.24(17) . 2_656 ?
C9 C8 C9 113.5(3) . 2_656 ?
N10 C9 C8 178.1(4) . . ?
O12A C11A O13A 127.3(16) . . ?
O12A C11A C2 117.7(13) . . ?
O13A C11A C2 114.9(14) . . ?
C11A O13A H13A 110(3) . . ?
O13B N11B O12B 123.6(13) . . ?
O13B N11B C2 120.1(14) . . ?
O12B N11B C2 116.2(10) . . ?
O16 N14 O15 126.4(3) . . ?
O16 N14 C4 116.4(3) . . ?
O15 N14 C4 117.1(3) . . ?
C18 S17 C21 94.72(15) . . ?
C19 C18 S17 117.6(2) . . ?
C19 C18 H18A 121.2 . . ?
S17 C18 H18A 121.2 . . ?
C18 C19 S20 118.1(3) . . ?
C18 C19 H19A 121.0 . . ?
S20 C19 H19A 121.0 . . ?
C21 S20 C19 94.63(15) . . ?
C21 C21 S20 122.2(3) 5_666 . ?
C21 C21 S17 122.7(3) 5_666 . ?
S20 C21 S17 115.01(15) . . ?
H22A O22 H22B 108(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
C6 C1 C2 C3 -3.5(4) . . . . ?
C6 C1 C2 C11A 176.1(9) . . . . ?
C6 C1 C2 N11B 176.2(8) . . . . ?
C1 C2 C3 C4 2.7(5) . . . . ?
C11A C2 C3 C4 -176.9(9) . . . . ?
N11B C2 C3 C4 -177.0(8) . . . . ?
C2 C3 C4 C5 2.9(5) . . . . ?
C2 C3 C4 N14 -168.7(3) . . . . ?
C3 C4 C5 C6 -7.3(4) . . . . ?
N14 C4 C5 C6 164.0(3) . . . . ?
C3 C4 C5 C5 174.9(4) . . . 2_656 ?
N14 C4 C5 C5 -13.9(6) . . . 2_656 ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
C4 C5 C6 C1 6.4(4) . . . . ?
C5 C5 C6 C1 -175.2(3) 2_656 . . . ?
C4 C5 C6 C7 -174.8(2) . . . . ?
C5 C5 C6 C7 3.6(3) 2_656 . . . ?
C1 C6 C7 C8 -2.7(3) . . . . ?
C5 C6 C7 C8 178.59(13) . . . . ?
C1 C6 C7 C6 177.3(3) . . . 2_656 ?
C5 C6 C7 C6 -1.41(13) . . . 2_656 ?
C6 C7 C8 C9 -7.84(19) . . . . ?
C6 C7 C8 C9 172.16(19) 2_656 . . . ?
C6 C7 C8 C9 172.16(19) . . . 2_656 ?
C6 C7 C8 C9 -7.84(19) 2_656 . . 2_656 ?
C3 C2 C11A O12A -169.4(15) . . . . ?
C1 C2 C11A O12A 11(2) . . . . ?
C3 C2 C11A O13A 14.0(19) . . . . ?
C1 C2 C11A O13A -165.6(13) . . . . ?
C3 C2 N11B O13B -5(2) . . . . ?
C1 C2 N11B O13B 175.6(15) . . . . ?
C3 C2 N11B O12B 178.4(11) . . . . ?
C1 C2 N11B O12B -1.4(17) . . . . ?
C3 C4 N14 O16 -36.1(5) . . . . ?
C5 C4 N14 O16 152.1(4) . . . . ?
C3 C4 N14 O15 142.6(3) . . . . ?
C5 C4 N14 O15 -29.2(5) . . . . ?
C21 S17 C18 C19 -0.2(3) . . . . ?
S17 C18 C19 S20 1.0(4) . . . . ?
C18 C19 S20 C21 -1.2(3) . . . . ?
C19 S20 C21 C21 -178.1(3) . . . 5_666 ?
C19 S20 C21 S17 1.06(19) . . . . ?
C18 S17 C21 C21 178.5(3) . . . 5_666 ?
C18 S17 C21 S20 -0.67(19) . . . . ?

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
O13A H13A O22 0.88(2) 2.41(6) 3.03(2) 128(6) .
O22 H22A O15 0.85(2) 2.18(6) 2.944(6) 150(11) 4_646
O22 H22A O22 0.85(2) 2.41(10) 2.869(14) 115(9) 5_767
O22 H22B O12A 0.85(2) 1.85(3) 2.697(19) 173(11) 5_767
O22 H22B O12B 0.85(2) 1.85(4) 2.682(11) 167(12) 5_767

_refine_diff_density_max         0.912
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.073


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1055664'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-07 downloaded from the CCDC.
;

# CLAVE UANL: DC2TNF3
# CLAVE TESIS: TTF3-DC2TNF2 2 CH3CN Sintesis p. 124

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

_database_code_CAS               ?
_database_code_CSD               ?

_audit_creation_date             2015-01-06

_chemical_name_systematic        
'tris(Tetrathiafulvalene) bis(9-dicyanomethylene-4,5,7-trinitrofluorene-2-carboxylic acid) acetonitrile disolvate'
_chemical_name_common            ?
_chemical_melting_point          507
_chemical_formula_moiety         '2(C17 H5 N5 O8), 3(C6 H4 S4), 2(C2 H3 N)'
_chemical_formula_sum            'C56 H28 N12 O16 S12'
_chemical_formula_weight         1509.62

_chemical_absolute_configuration ?
_chemical_optical_rotation       ?

_chemical_properties_physical    ?
_chemical_properties_biological  ?

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       ?

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0608(10)
_cell_length_b                   10.3528(11)
_cell_length_c                   15.612(2)
_cell_angle_alpha                107.535(8)
_cell_angle_beta                 100.525(9)
_cell_angle_gamma                90.877(8)
_cell_volume                     1520.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    85
_cell_measurement_theta_min      4.77
_cell_measurement_theta_max      11.81

_exptl_crystal_description       irregular
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.513
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.34887
_exptl_absorpt_correction_T_max  0.39349
_exptl_absorpt_process_details   ' XSCANS (Siemens, 1996)'

_exptl_special_details           ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         X-ray
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              FN4
_diffrn_source_current           30
_diffrn_source_voltage           50
_diffrn_source_power             1.5
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 48
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -2 -2
-1 1 -4

_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        1
_diffrn_reflns_number            6125
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             5172
_reflns_number_gt                3746
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          ?

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       XSCANS
_computing_data_reduction        XSCANS
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
SHELXTL-Plus (Siemens, 1996) and MERCURY (Macrae et al., 2008)
;
_computing_publication_material  SHELXL-2014/7

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+2.6109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5172
_refine_ls_number_parameters     437
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_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
C1 C -0.2599(4) 0.1957(4) 0.8606(3) 0.0316(9) Uani 1 1 d . . . . .
H1A H -0.3294 0.1444 0.8699 0.038 Uiso 1 1 calc R U . . .
C2 C -0.2563(4) 0.3371(4) 0.8901(3) 0.0324(9) Uani 1 1 d . . . . .
C3 C -0.1545(4) 0.4131(4) 0.8738(3) 0.0355(10) Uani 1 1 d . . . . .
H3A H -0.1543 0.5073 0.8913 0.043 Uiso 1 1 calc R U . . .
C4 C -0.0537(4) 0.3494(4) 0.8317(3) 0.0314(9) Uani 1 1 d . . . . .
C4A C -0.0490(4) 0.2086(4) 0.8059(3) 0.0289(9) Uani 1 1 d . . . . .
C4B C 0.0449(4) 0.1120(4) 0.7650(3) 0.0280(9) Uani 1 1 d . . . . .
C5 C 0.1743(4) 0.1212(4) 0.7460(3) 0.0334(9) Uani 1 1 d . . . . .
C6 C 0.2334(4) 0.0094(4) 0.6988(3) 0.0367(10) Uani 1 1 d . . . . .
H6A H 0.3183 0.0181 0.6847 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1628(4) -0.1145(4) 0.6736(3) 0.0350(10) Uani 1 1 d . . . . .
C8 C 0.0417(4) -0.1350(4) 0.6964(3) 0.0345(10) Uani 1 1 d . . . . .
H8A H -0.0004 -0.2219 0.6804 0.041 Uiso 1 1 calc R U . . .
C8A C -0.0176(4) -0.0209(4) 0.7450(3) 0.0283(9) Uani 1 1 d . . . . .
C9 C -0.1423(4) -0.0125(4) 0.7780(3) 0.0281(9) Uani 1 1 d . . . . .
C9A C -0.1588(4) 0.1324(4) 0.8175(3) 0.0280(9) Uani 1 1 d . . . . .
C10 C -0.2278(4) -0.1213(4) 0.7753(3) 0.0296(9) Uani 1 1 d . . . . .
C11 C -0.3566(5) -0.1043(4) 0.8023(3) 0.0376(10) Uani 1 1 d . . . . .
N12 N -0.4577(4) -0.0938(4) 0.8242(3) 0.0576(12) Uani 1 1 d . . . . .
C13 C -0.1912(4) -0.2590(4) 0.7488(3) 0.0366(10) Uani 1 1 d . . . . .
N14 N -0.1612(5) -0.3681(4) 0.7309(3) 0.0582(12) Uani 1 1 d . . . . .
C15 C -0.3628(4) 0.4056(4) 0.9372(3) 0.0371(10) Uani 1 1 d . . . . .
O16 O -0.3702(4) 0.5323(3) 0.9459(3) 0.0541(9) Uani 1 1 d D . . . .
H16 H -0.437(4) 0.573(6) 0.979(4) 0.081 Uiso 1 1 d D U . . .
O17 O -0.4398(3) 0.3399(3) 0.9651(2) 0.0526(9) Uani 1 1 d . . . . .
N18 N 0.0378(4) 0.4365(4) 0.8060(3) 0.0424(9) Uani 1 1 d . . . . .
O19 O 0.0794(4) 0.5465(3) 0.8621(3) 0.0644(11) Uani 1 1 d . . . . .
O20 O 0.0650(3) 0.3952(3) 0.7297(2) 0.0490(8) Uani 1 1 d . . . . .
N21 N 0.2643(4) 0.2469(4) 0.7835(3) 0.0451(10) Uani 1 1 d . . . . .
O22 O 0.3491(4) 0.2650(4) 0.7410(3) 0.0693(12) Uani 1 1 d . . . . .
O23 O 0.2546(3) 0.3229(3) 0.8588(2) 0.0500(8) Uani 1 1 d . . . . .
N24 N 0.2215(4) -0.2332(4) 0.6193(3) 0.0479(10) Uani 1 1 d . . . . .
O25 O 0.1534(4) -0.3412(4) 0.5901(3) 0.0777(13) Uani 1 1 d . . . . .
O26 O 0.3349(4) -0.2173(4) 0.6049(3) 0.0649(11) Uani 1 1 d . . . . .
S27 S -0.13317(13) -0.15998(14) 0.49434(9) 0.0518(4) Uani 1 1 d . . . . .
C28 C -0.1749(7) -0.3295(5) 0.4774(4) 0.0640(16) Uani 1 1 d . . . . .
H28A H -0.1241 -0.3967 0.4475 0.077 Uiso 1 1 calc R U . . .
C29 C -0.2797(6) -0.3606(5) 0.5077(4) 0.0622(15) Uani 1 1 d . . . . .
H29A H -0.3056 -0.4504 0.5006 0.075 Uiso 1 1 calc R U . . .
S30 S -0.36874(12) -0.22865(12) 0.56136(9) 0.0486(3) Uani 1 1 d . . . . .
C31 C -0.2638(4) -0.1024(4) 0.5503(3) 0.0371(10) Uani 1 1 d . . . . .
C32 C -0.2843(4) 0.0322(4) 0.5850(3) 0.0351(10) Uani 1 1 d . . . . .
S33 S -0.42878(11) 0.08748(12) 0.62761(9) 0.0438(3) Uani 1 1 d . . . . .
C34 C -0.3852(5) 0.2575(5) 0.6486(4) 0.0511(13) Uani 1 1 d . . . . .
H34A H -0.4413 0.3234 0.6732 0.061 Uiso 1 1 calc R U . . .
C35 C -0.2712(5) 0.2914(5) 0.6289(3) 0.0493(12) Uani 1 1 d . . . . .
H35A H -0.2440 0.3818 0.6386 0.059 Uiso 1 1 calc R U . . .
S36 S -0.17267(12) 0.16101(12) 0.58408(9) 0.0456(3) Uani 1 1 d . . . . .
S37 S 0.14270(13) 0.16956(12) 1.01214(9) 0.0494(3) Uani 1 1 d . . . . .
C38 C 0.2838(5) 0.1078(6) 0.9707(4) 0.0588(14) Uani 1 1 d . . . . .
H38A H 0.3561 0.1662 0.9724 0.071 Uiso 1 1 calc R U . . .
C39 C 0.2862(5) -0.0242(7) 0.9365(4) 0.0611(15) Uani 1 1 d . . . . .
H39A H 0.3600 -0.0617 0.9125 0.073 Uiso 1 1 calc R U . . .
S40 S 0.14955(13) -0.12697(13) 0.93708(9) 0.0490(3) Uani 1 1 d . . . . .
C41 C 0.0597(4) 0.0090(4) 0.9892(3) 0.0368(10) Uani 1 1 d . . . . .
C42 C 0.6399(8) 0.3867(8) 1.2120(7) 0.106(3) Uani 1 1 d . . . . .
H42A H 0.7098 0.3322 1.2294 0.159 Uiso 1 1 calc R U . . .
H42B H 0.6803 0.4694 1.2090 0.159 Uiso 1 1 calc R U . . .
H42C H 0.5867 0.3374 1.1531 0.159 Uiso 1 1 calc R U . . .
C43 C 0.5553(8) 0.4178(7) 1.2779(7) 0.087(2) Uani 1 1 d . . . . .
N44 N 0.4866(7) 0.4417(6) 1.3333(6) 0.114(3) Uani 1 1 d . . . . .


_geom_special_details            ?

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 C9A 1.386(6) . ?
C1 C2 1.393(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.387(6) . ?
C2 C15 1.480(6) . ?
C3 C4 1.379(6) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.394(6) . ?
C4 N18 1.465(5) . ?
C4A C9A 1.418(5) . ?
C4A C4B 1.470(5) . ?
C4B C5 1.395(6) . ?
C4B C8A 1.425(5) . ?
C5 C6 1.380(6) . ?
C5 N21 1.472(6) . ?
C6 C7 1.368(6) . ?
C6 H6A 0.9300 . ?
C7 C8 1.361(6) . ?
C7 N24 1.468(5) . ?
C8 C8A 1.405(5) . ?
C8 H8A 0.9300 . ?
C8A C9 1.435(5) . ?
C9 C10 1.393(6) . ?
C9 C9A 1.465(5) . ?
C10 C11 1.432(6) . ?
C10 C13 1.433(6) . ?
C11 N12 1.128(6) . ?
C13 N14 1.139(6) . ?
C15 O17 1.241(5) . ?
C15 O16 1.282(5) . ?
O16 H16 0.951(10) . ?
N18 O19 1.221(5) . ?
N18 O20 1.222(5) . ?
N21 O22 1.217(5) . ?
N21 O23 1.223(5) . ?
N24 O25 1.218(5) . ?
N24 O26 1.220(5) . ?
S27 C31 1.725(4) . ?
S27 C28 1.727(6) . ?
C28 C29 1.306(8) . ?
C28 H28A 0.9300 . ?
C29 S30 1.730(6) . ?
C29 H29A 0.9300 . ?
S30 C31 1.736(5) . ?
C31 C32 1.369(6) . ?
C32 S36 1.735(4) . ?
C32 S33 1.741(4) . ?
S33 C34 1.724(5) . ?
C34 C35 1.310(7) . ?
C34 H34A 0.9300 . ?
C35 S36 1.738(5) . ?
C35 H35A 0.9300 . ?
S37 C38 1.720(6) . ?
S37 C41 1.754(4) . ?
C38 C39 1.311(8) . ?
C38 H38A 0.9300 . ?
C39 S40 1.729(6) . ?
C39 H39A 0.9300 . ?
S40 C41 1.755(4) . ?
C41 C41 1.330(9) 2_557 ?
C42 C43 1.419(12) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 N44 1.176(11) . ?

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
C9A C1 C2 119.4(4) . . ?
C9A C1 H1A 120.3 . . ?
C2 C1 H1A 120.3 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 C15 120.2(4) . . ?
C1 C2 C15 119.7(4) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C4A 121.7(4) . . ?
C3 C4 N18 115.9(4) . . ?
C4A C4 N18 122.0(4) . . ?
C4 C4A C9A 117.1(3) . . ?
C4 C4A C4B 135.2(4) . . ?
C9A C4A C4B 107.7(3) . . ?
C5 C4B C8A 117.0(3) . . ?
C5 C4B C4A 135.9(4) . . ?
C8A C4B C4A 107.1(3) . . ?
C6 C5 C4B 122.4(4) . . ?
C6 C5 N21 114.5(4) . . ?
C4B C5 N21 122.7(4) . . ?
C7 C6 C5 117.7(4) . . ?
C7 C6 H6A 121.2 . . ?
C5 C6 H6A 121.2 . . ?
C8 C7 C6 124.0(4) . . ?
C8 C7 N24 117.7(4) . . ?
C6 C7 N24 118.2(4) . . ?
C7 C8 C8A 117.9(4) . . ?
C7 C8 H8A 121.0 . . ?
C8A C8 H8A 121.0 . . ?
C8 C8A C4B 120.3(4) . . ?
C8 C8A C9 129.9(4) . . ?
C4B C8A C9 109.7(3) . . ?
C10 C9 C8A 126.4(3) . . ?
C10 C9 C9A 127.1(4) . . ?
C8A C9 C9A 106.4(3) . . ?
C1 C9A C4A 121.3(4) . . ?
C1 C9A C9 129.9(4) . . ?
C4A C9A C9 108.8(3) . . ?
C9 C10 C11 122.8(4) . . ?
C9 C10 C13 122.5(4) . . ?
C11 C10 C13 114.6(3) . . ?
N12 C11 C10 178.2(5) . . ?
N14 C13 C10 177.6(5) . . ?
O17 C15 O16 123.6(4) . . ?
O17 C15 C2 119.8(4) . . ?
O16 C15 C2 116.6(4) . . ?
C15 O16 H16 114(4) . . ?
O19 N18 O20 124.7(4) . . ?
O19 N18 C4 117.4(4) . . ?
O20 N18 C4 118.0(3) . . ?
O22 N21 O23 123.9(4) . . ?
O22 N21 C5 118.5(4) . . ?
O23 N21 C5 117.5(4) . . ?
O25 N24 O26 123.9(4) . . ?
O25 N24 C7 118.1(4) . . ?
O26 N24 C7 118.0(4) . . ?
C31 S27 C28 94.7(3) . . ?
C29 C28 S27 118.1(4) . . ?
C29 C28 H28A 121.0 . . ?
S27 C28 H28A 121.0 . . ?
C28 C29 S30 117.5(5) . . ?
C28 C29 H29A 121.2 . . ?
S30 C29 H29A 121.2 . . ?
C29 S30 C31 94.6(3) . . ?
C32 C31 S27 123.5(3) . . ?
C32 C31 S30 121.5(3) . . ?
S27 C31 S30 115.0(3) . . ?
C31 C32 S36 122.5(3) . . ?
C31 C32 S33 122.7(3) . . ?
S36 C32 S33 114.8(2) . . ?
C34 S33 C32 94.7(2) . . ?
C35 C34 S33 118.3(4) . . ?
C35 C34 H34A 120.8 . . ?
S33 C34 H34A 120.8 . . ?
C34 C35 S36 117.4(4) . . ?
C34 C35 H35A 121.3 . . ?
S36 C35 H35A 121.3 . . ?
C32 S36 C35 94.8(2) . . ?
C38 S37 C41 95.0(2) . . ?
C39 C38 S37 117.9(4) . . ?
C39 C38 H38A 121.0 . . ?
S37 C38 H38A 121.0 . . ?
C38 C39 S40 118.6(4) . . ?
C38 C39 H39A 120.7 . . ?
S40 C39 H39A 120.7 . . ?
C39 S40 C41 94.3(3) . . ?
C41 C41 S37 123.3(5) 2_557 . ?
C41 C41 S40 122.6(5) 2_557 . ?
S37 C41 S40 114.1(2) . . ?
C43 C42 H42A 109.5 . . ?
C43 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C43 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N44 C43 C42 178.6(9) . . ?

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
C9A C1 C2 C3 1.8(6) . . . . ?
C9A C1 C2 C15 -179.3(4) . . . . ?
C1 C2 C3 C4 -2.5(6) . . . . ?
C15 C2 C3 C4 178.6(4) . . . . ?
C2 C3 C4 C4A -1.2(6) . . . . ?
C2 C3 C4 N18 171.7(4) . . . . ?
C3 C4 C4A C9A 5.3(6) . . . . ?
N18 C4 C4A C9A -167.2(4) . . . . ?
C3 C4 C4A C4B -176.5(4) . . . . ?
N18 C4 C4A C4B 10.9(7) . . . . ?
C4 C4A C4B C5 9.8(8) . . . . ?
C9A C4A C4B C5 -171.9(5) . . . . ?
C4 C4A C4B C8A -172.8(4) . . . . ?
C9A C4A C4B C8A 5.5(4) . . . . ?
C8A C4B C5 C6 8.5(6) . . . . ?
C4A C4B C5 C6 -174.3(4) . . . . ?
C8A C4B C5 N21 -164.2(4) . . . . ?
C4A C4B C5 N21 13.0(7) . . . . ?
C4B C5 C6 C7 -2.5(6) . . . . ?
N21 C5 C6 C7 170.8(4) . . . . ?
C5 C6 C7 C8 -3.7(7) . . . . ?
C5 C6 C7 N24 176.9(4) . . . . ?
C6 C7 C8 C8A 3.3(7) . . . . ?
N24 C7 C8 C8A -177.3(4) . . . . ?
C7 C8 C8A C4B 3.2(6) . . . . ?
C7 C8 C8A C9 -179.6(4) . . . . ?
C5 C4B C8A C8 -8.8(6) . . . . ?
C4A C4B C8A C8 173.3(4) . . . . ?
C5 C4B C8A C9 173.5(4) . . . . ?
C4A C4B C8A C9 -4.4(4) . . . . ?
C8 C8A C9 C10 6.2(7) . . . . ?
C4B C8A C9 C10 -176.3(4) . . . . ?
C8 C8A C9 C9A -175.7(4) . . . . ?
C4B C8A C9 C9A 1.8(4) . . . . ?
C2 C1 C9A C4A 2.5(6) . . . . ?
C2 C1 C9A C9 -177.7(4) . . . . ?
C4 C4A C9A C1 -6.0(6) . . . . ?
C4B C4A C9A C1 175.4(4) . . . . ?
C4 C4A C9A C9 174.2(3) . . . . ?
C4B C4A C9A C9 -4.4(4) . . . . ?
C10 C9 C9A C1 0.0(7) . . . . ?
C8A C9 C9A C1 -178.1(4) . . . . ?
C10 C9 C9A C4A 179.8(4) . . . . ?
C8A C9 C9A C4A 1.7(4) . . . . ?
C8A C9 C10 C11 -174.2(4) . . . . ?
C9A C9 C10 C11 8.1(7) . . . . ?
C8A C9 C10 C13 8.3(6) . . . . ?
C9A C9 C10 C13 -169.4(4) . . . . ?
C3 C2 C15 O17 -168.1(4) . . . . ?
C1 C2 C15 O17 13.0(6) . . . . ?
C3 C2 C15 O16 12.6(6) . . . . ?
C1 C2 C15 O16 -166.3(4) . . . . ?
C3 C4 N18 O19 44.0(6) . . . . ?
C4A C4 N18 O19 -143.0(4) . . . . ?
C3 C4 N18 O20 -134.6(4) . . . . ?
C4A C4 N18 O20 38.3(6) . . . . ?
C6 C5 N21 O22 33.3(6) . . . . ?
C4B C5 N21 O22 -153.5(4) . . . . ?
C6 C5 N21 O23 -142.2(4) . . . . ?
C4B C5 N21 O23 31.1(6) . . . . ?
C8 C7 N24 O25 6.9(6) . . . . ?
C6 C7 N24 O25 -173.7(5) . . . . ?
C8 C7 N24 O26 -174.2(4) . . . . ?
C6 C7 N24 O26 5.2(6) . . . . ?
C31 S27 C28 C29 0.2(5) . . . . ?
S27 C28 C29 S30 0.6(7) . . . . ?
C28 C29 S30 C31 -1.0(5) . . . . ?
C28 S27 C31 C32 178.3(4) . . . . ?
C28 S27 C31 S30 -0.9(3) . . . . ?
C29 S30 C31 C32 -178.1(4) . . . . ?
C29 S30 C31 S27 1.1(3) . . . . ?
S27 C31 C32 S36 -5.0(6) . . . . ?
S30 C31 C32 S36 174.1(2) . . . . ?
S27 C31 C32 S33 171.3(2) . . . . ?
S30 C31 C32 S33 -9.6(5) . . . . ?
C31 C32 S33 C34 -176.1(4) . . . . ?
S36 C32 S33 C34 0.5(3) . . . . ?
C32 S33 C34 C35 0.1(5) . . . . ?
S33 C34 C35 S36 -0.6(6) . . . . ?
C31 C32 S36 C35 175.9(4) . . . . ?
S33 C32 S36 C35 -0.7(3) . . . . ?
C34 C35 S36 C32 0.8(5) . . . . ?
C41 S37 C38 C39 1.3(5) . . . . ?
S37 C38 C39 S40 -1.0(7) . . . . ?
C38 C39 S40 C41 0.1(5) . . . . ?
C38 S37 C41 C41 177.5(6) . . . 2_557 ?
C38 S37 C41 S40 -1.2(3) . . . . ?
C39 S40 C41 C41 -177.9(6) . . . 2_557 ?
C39 S40 C41 S37 0.8(3) . . . . ?

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
C6 H6A S33 0.93 2.99 3.908(4) 169.5 1_655
C8 H8A N14 0.93 2.58 3.364(6) 142.6 .
O16 H16 O17 0.951(10) 1.748(13) 2.697(4) 175(6) 2_467
C28 H28A O25 0.93 2.60 3.274(6) 130.0 2_546
C34 H34A N44 0.93 2.51 3.239(8) 135.5 2_567
C35 H35A N14 0.93 2.59 3.470(6) 157.4 1_565
C39 H39A N12 0.93 2.46 3.343(7) 159.1 1_655
C42 H42B O22 0.96 2.66 3.452(9) 140.2 2_667

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
