#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:25:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178623 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/34/4073439.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4073439
loop_
_publ_author_name
'Pampaloni, Guido'
'Peloso, Riccardo'
'Belletti, Daniele'
'Graiff, Claudia'
'Tiripicchio, Antonio'
_publ_section_title
;
 Trifluoromethyl-Substituted Bis(pyrazolyl)methanes as Ligands for Copper
 and Silver:  Synthesis and Spectroscopic and Structural
 Characterization
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4278
_journal_paper_doi               10.1021/om700325t
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C13 H4 Cu F15 N4 O4 S'
_chemical_formula_weight         660.80
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.407(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.818(3)
_cell_length_b                   14.758(5)
_cell_length_c                   13.283(3)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      39
_cell_measurement_theta_min      13
_cell_volume                     2111.2(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf Nonius CAD 4'
_diffrn_measurement_method       'theta 2 theta scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4138
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         4.49
_diffrn_standards_decay_%        'no decay'
_diffrn_standards_interval_count 100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    3.977
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'Parkin & al (1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.079
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                2395
_reflns_number_total             3968
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700325t-file006.cif
_cod_data_source_block           CuCO2CF3
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4073439
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2393(6) 0.2798(4) 0.8224(5) 0.0578(15) Uani 1 1 d . . .
C2 C 0.3750(6) 0.2293(4) 1.0995(5) 0.0571(15) Uani 1 1 d . . .
C3 C -0.1437(4) 0.2769(3) 0.9936(4) 0.0387(11) Uani 1 1 d . . .
H3A H -0.0818 0.2838 1.0519 0.046 Uiso 1 1 calc R . .
H3B H -0.2259 0.2754 1.0188 0.046 Uiso 1 1 calc R . .
C4 C 0.0944(6) 0.0526(4) 0.8304(5) 0.0538(14) Uani 1 1 d . . .
C5 C -0.0145(5) 0.0923(3) 0.8764(4) 0.0397(11) Uani 1 1 d . . .
C6 C -0.1257(5) 0.0504(3) 0.8911(4) 0.0434(12) Uani 1 1 d . . .
H6 H -0.1493 -0.0096 0.8753 0.052 Uiso 1 1 calc R . .
C7 C -0.1936(5) 0.1157(3) 0.9339(4) 0.0412(11) Uani 1 1 d . . .
C8 C -0.3214(5) 0.1105(4) 0.9660(5) 0.0528(14) Uani 1 1 d . . .
C9 C -0.3543(5) 0.4167(4) 0.9213(5) 0.0526(14) Uani 1 1 d . . .
C10 C -0.2218(5) 0.4198(3) 0.8974(4) 0.0421(12) Uani 1 1 d . . .
C11 C -0.1639(5) 0.4871(3) 0.8491(4) 0.0437(12) Uani 1 1 d . . .
H11 H -0.1987 0.5409 0.8211 0.052 Uiso 1 1 calc R . .
C12 C -0.0418(5) 0.4577(3) 0.8511(4) 0.0389(11) Uani 1 1 d . A .
C13 C 0.0637(5) 0.5057(4) 0.8091(4) 0.0499(12) Uani 1 1 d DU . .
Cu1 Cu 0.11590(7) 0.28161(5) 0.90468(6) 0.0420(2) Uani 1 1 d . A .
F1 F 0.0826(3) -0.0363(2) 0.8181(3) 0.0791(12) Uani 1 1 d . . .
F2 F 0.2007(3) 0.0659(3) 0.8885(3) 0.0682(10) Uani 1 1 d . . .
F3 F 0.1105(4) 0.0887(3) 0.7407(3) 0.0746(11) Uani 1 1 d . . .
F4 F -0.3974(3) 0.1690(3) 0.9172(3) 0.0734(11) Uani 1 1 d . . .
F5 F -0.3228(3) 0.1299(3) 1.0641(3) 0.0739(11) Uani 1 1 d . . .
F6 F -0.3677(3) 0.0285(2) 0.9518(3) 0.0814(12) Uani 1 1 d . . .
F7 F -0.4178(3) 0.3499(3) 0.8755(3) 0.0765(11) Uani 1 1 d . . .
F8 F -0.4109(4) 0.4924(3) 0.8933(5) 0.1088(18) Uani 1 1 d . . .
F9 F -0.3650(3) 0.4047(3) 1.0188(3) 0.0815(12) Uani 1 1 d . . .
F10A F 0.123(2) 0.467(3) 0.744(2) 0.094(8) Uani 0.40 1 d PDU A 1
F11A F 0.150(2) 0.5338(13) 0.8762(13) 0.095(6) Uani 0.40 1 d PDU A 1
F12A F 0.020(3) 0.5801(13) 0.763(2) 0.135(10) Uani 0.40 1 d PDU A 1
F10B F 0.0831(17) 0.472(2) 0.7224(13) 0.092(5) Uani 0.60 1 d PDU A 2
F11B F 0.1681(12) 0.4898(9) 0.8687(12) 0.113(5) Uani 0.60 1 d PDU A 2
F12B F 0.0487(18) 0.5921(8) 0.8033(14) 0.108(5) Uani 0.60 1 d PDU A 2
F13 F 0.3703(3) 0.1784(3) 1.0174(3) 0.0769(11) Uani 1 1 d . . .
F14 F 0.4473(4) 0.1890(4) 1.1696(3) 0.127(2) Uani 1 1 d . . .
F15 F 0.4271(4) 0.3043(3) 1.0777(5) 0.119(2) Uani 1 1 d . . .
N1 N -0.0106(4) 0.1772(3) 0.9080(3) 0.0383(9) Uani 1 1 d . . .
N2 N -0.1223(4) 0.1916(3) 0.9430(3) 0.0359(9) Uani 1 1 d . . .
N3 N -0.0235(4) 0.3786(3) 0.8978(3) 0.0369(9) Uani 1 1 d . . .
N4 N -0.1365(3) 0.3551(3) 0.9265(3) 0.0352(9) Uani 1 1 d . A .
O1 O 0.3167(5) 0.2759(4) 0.7695(4) 0.0971(18) Uani 1 1 d . . .
O2 O 0.1583(3) 0.2993(3) 1.0598(3) 0.0573(11) Uani 1 1 d . . .
O3 O 0.2471(4) 0.3005(3) 1.2315(3) 0.0585(11) Uani 1 1 d . . .
O4 O 0.1742(5) 0.1594(3) 1.1525(4) 0.0910(17) Uani 1 1 d . . .
S1 S 0.22307(12) 0.24776(8) 1.14191(10) 0.0415(3) Uani 1 1 d . A .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 Cu1 177.9(6)
F15 C2 F14 107.9(6)
F15 C2 F13 106.7(6)
F14 C2 F13 107.7(5)
F15 C2 S1 111.7(5)
F14 C2 S1 110.4(5)
F13 C2 S1 112.2(4)
N2 C3 N4 112.4(4)
N2 C3 H3A 109.1
N4 C3 H3A 109.1
N2 C3 H3B 109.1
N4 C3 H3B 109.1
H3A C3 H3B 107.9
F1 C4 F3 107.7(5)
F1 C4 F2 106.5(5)
F3 C4 F2 106.2(5)
F1 C4 C5 111.5(5)
F3 C4 C5 112.5(5)
F2 C4 C5 112.0(5)
N1 C5 C6 112.4(4)
N1 C5 C4 119.9(5)
C6 C5 C4 127.7(5)
C7 C6 C5 104.6(4)
C7 C6 H6 127.7
C5 C6 H6 127.7
N2 C7 C6 107.1(4)
N2 C7 C8 123.6(5)
C6 C7 C8 129.3(5)
F6 C8 F4 108.6(5)
F6 C8 F5 107.3(5)
F4 C8 F5 105.9(5)
F6 C8 C7 111.0(5)
F4 C8 C7 112.2(5)
F5 C8 C7 111.5(5)
F8 C9 F7 107.3(5)
F8 C9 F9 108.1(5)
F7 C9 F9 105.1(5)
F8 C9 C10 110.2(5)
F7 C9 C10 113.1(5)
F9 C9 C10 112.6(5)
N4 C10 C11 108.4(4)
N4 C10 C9 123.9(5)
C11 C10 C9 127.7(5)
C10 C11 C12 104.0(5)
C10 C11 H11 128.0
C12 C11 H11 128.0
N3 C12 C11 112.6(4)
N3 C12 C13 120.3(4)
C11 C12 C13 127.1(5)
F10A C13 F10B 23(2)
F10A C13 F12B 119(2)
F10B C13 F12B 110.9(16)
F10A C13 F11A 103.8(15)
F10B C13 F11A 124.6(15)
F12B C13 F11A 78.7(13)
F10A C13 F12A 104(2)
F10B C13 F12A 89(2)
F12B C13 F12A 27.4(18)
F11A C13 F12A 104.8(15)
F10A C13 F11B 82.7(17)
F10B C13 F11B 105.2(12)
F12B C13 F11B 107.7(10)
F11A C13 F11B 30.2(12)
F12A C13 F11B 131.7(15)
F10A C13 C12 119.4(18)
F10B C13 C12 110.3(12)
F12B C13 C12 113.3(10)
F11A C13 C12 115.0(11)
F12A C13 C12 108.2(15)
F11B C13 C12 109.1(8)
C1 Cu1 N1 122.2(2)
C1 Cu1 N3 124.0(2)
N1 Cu1 N3 92.01(15)
C1 Cu1 O2 119.6(2)
N1 Cu1 O2 99.03(17)
N3 Cu1 O2 92.79(15)
C5 N1 N2 104.8(4)
C5 N1 Cu1 134.6(4)
N2 N1 Cu1 120.4(3)
N1 N2 C7 111.0(4)
N1 N2 C3 118.8(4)
C7 N2 C3 129.8(4)
C12 N3 N4 104.8(4)
C12 N3 Cu1 134.7(3)
N4 N3 Cu1 118.7(3)
C10 N4 N3 110.2(4)
C10 N4 C3 130.8(4)
N3 N4 C3 118.2(4)
S1 O2 Cu1 136.2(2)
O4 S1 O3 117.4(3)
O4 S1 O2 113.4(3)
O3 S1 O2 112.2(2)
O4 S1 C2 104.5(3)
O3 S1 C2 104.1(3)
O2 S1 C2 103.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.144(7)
C1 Cu1 1.803(7)
C2 F15 1.288(7)
C2 F14 1.302(7)
C2 F13 1.321(7)
C2 S1 1.808(6)
C3 N2 1.455(6)
C3 N4 1.465(6)
C3 H3A 0.9800
C3 H3B 0.9800
C4 F1 1.326(6)
C4 F3 1.332(7)
C4 F2 1.338(7)
C4 C5 1.497(7)
C5 N1 1.321(6)
C5 C6 1.382(7)
C6 C7 1.367(7)
C6 H6 0.9400
C7 N2 1.359(6)
C7 C8 1.486(7)
C8 F6 1.317(6)
C8 F4 1.321(6)
C8 F5 1.335(7)
C9 F8 1.310(6)
C9 F7 1.317(7)
C9 F9 1.323(7)
C9 C10 1.498(7)
C10 N4 1.358(6)
C10 C11 1.367(7)
C11 C12 1.388(7)
C11 H11 0.9400
C12 N3 1.328(6)
C12 C13 1.496(7)
C13 F10A 1.261(18)
C13 F10B 1.288(12)
C13 F12B 1.287(12)
C13 F11A 1.300(14)
C13 F12A 1.322(15)
C13 F11B 1.338(11)
Cu1 N1 2.064(4)
Cu1 N3 2.075(4)
Cu1 O2 2.085(4)
N1 N2 1.351(5)
N3 N4 1.360(5)
O2 S1 1.455(4)
O3 S1 1.425(4)
O4 S1 1.418(4)
