#------------------------------------------------------------------------------
#$Date: 2019-07-13 03:03:03 +0300 (Sat, 13 Jul 2019) $
#$Revision: 216986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/38/7123843.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_7123843
loop_
_publ_author_name
'Petry, Nicolas'
'Vanderbeeken, Thibaut'
'Malher, Astrid'
'Bringer, Yoan'
'Retailleau, Pascal'
'Bantreil, Xavier'
'Lamaty, Frédéric'
_publ_section_title
;
 Mechanosynthesis of Sydnone-containing Coordination Complexes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04673A
_journal_year                    2019
_chemical_formula_moiety         'C28 H18 Cu F6 N6 O10 S2'
_chemical_formula_sum            'C28 H18 Cu F6 N6 O10 S2'
_chemical_formula_weight         840.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-09 deposited with the CCDC.    2019-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                81.297(4)
_cell_angle_beta                 82.418(5)
_cell_angle_gamma                84.920(4)
_cell_formula_units_Z            1
_cell_length_a                   7.9107(4)
_cell_length_b                   7.9633(4)
_cell_length_c                   13.4394(8)
_cell_measurement_reflns_used    4322
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9560
_cell_measurement_theta_min      4.6140
_cell_volume                     827.52(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  89.00   0.50   45.00    --    0.00  57.00 -30.00  228
  2  ω    -23.00  89.00   0.50   45.00    --    0.00  38.00-180.00  224
  3  ω     -1.00  81.00   0.50   45.00    --    0.00  38.00  60.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Rigaku MaxFlux double bounce layer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11808
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.724
_diffrn_reflns_theta_min         3.803
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       platelet
_exptl_crystal_F_000             423
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.309
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.9162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3655
_reflns_number_total             4461
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc04673a2.cif
_cod_data_source_block           CuOTf_2_3a_2
_cod_original_cell_volume        827.53(8)
_cod_database_code               7123843
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cu1 Cu 0.500000 0.500000 0.500000 0.02907(14) Uani 1 2 d S . P
S1 S 0.36409(10) 0.16066(9) 0.71503(6) 0.04103(19) Uani 1 1 d . . .
F1 F 0.4937(4) 0.0008(4) 0.8739(2) 0.0855(8) Uani 1 1 d . . .
N1 N 0.6361(3) 0.3510(4) 0.15844(19) 0.0427(6) Uani 1 1 d . . .
C1 C 0.5400(3) 0.3695(3) 0.3213(2) 0.0303(5) Uani 1 1 d . . .
O1 O 0.4294(2) 0.3836(3) 0.39474(15) 0.0357(4) Uani 1 1 d . . .
O2 O 0.4936(3) 0.3657(3) 0.22799(16) 0.0410(5) Uani 1 1 d . . .
F2 F 0.6642(4) 0.0096(5) 0.7369(3) 0.1043(11) Uani 1 1 d . . .
N2 N 0.7640(3) 0.3446(3) 0.21111(17) 0.0326(5) Uani 1 1 d . . .
C2 C 0.7189(3) 0.3549(3) 0.31095(19) 0.0278(5) Uani 1 1 d . . .
C5 C 1.0678(4) 0.2146(4) 0.4745(3) 0.0424(7) Uani 1 1 d . . .
H5 H 1.176892 0.160129 0.472134 0.051 Uiso 1 1 calc R U .
O5 O 0.3113(5) 0.0061(3) 0.6939(3) 0.0796(10) Uani 1 1 d . . .
C4 C 0.9843(4) 0.2464(4) 0.3890(2) 0.0376(6) Uani 1 1 d . . .
H4 H 1.036273 0.212256 0.328392 0.045 Uiso 1 1 calc R U .
O4 O 0.2450(5) 0.2446(5) 0.7835(3) 0.0945(12) Uani 1 1 d . . .
C3 C 0.8228(3) 0.3294(3) 0.39384(19) 0.0282(5) Uani 1 1 d . . .
N3 N 0.7428(3) 0.3820(3) 0.48105(16) 0.0293(4) Uani 1 1 d . . .
O3 O 0.4334(3) 0.2731(3) 0.6295(2) 0.0569(6) Uani 1 1 d . . .
F3 F 0.6090(5) 0.2302(4) 0.8099(3) 0.1137(13) Uani 1 1 d . . .
C6 C 0.9865(4) 0.2649(4) 0.5634(2) 0.0437(7) Uani 1 1 d . . .
H6 H 1.038735 0.242847 0.622521 0.052 Uiso 1 1 calc R U .
C7 C 0.8267(4) 0.3483(4) 0.5630(2) 0.0383(6) Uani 1 1 d . . .
H7 H 0.773750 0.383419 0.623073 0.046 Uiso 1 1 calc R U .
C8 C 0.9324(4) 0.3320(4) 0.1542(2) 0.0356(6) Uani 1 1 d . . .
C9 C 0.9808(5) 0.1857(4) 0.1111(3) 0.0498(8) Uani 1 1 d . . .
H9 H 0.910546 0.095558 0.120696 0.060 Uiso 1 1 calc R U .
C10 C 1.1387(5) 0.1792(6) 0.0528(3) 0.0604(10) Uani 1 1 d . . .
H10 H 1.175325 0.082982 0.022275 0.073 Uiso 1 1 calc R U .
C11 C 1.2411(5) 0.3115(6) 0.0396(3) 0.0561(9) Uani 1 1 d . . .
H11 H 1.346498 0.304467 0.000093 0.067 Uiso 1 1 calc R U .
C12 C 1.1905(4) 0.4558(5) 0.0841(3) 0.0513(8) Uani 1 1 d . . .
H12 H 1.261994 0.544899 0.075148 0.062 Uiso 1 1 calc R U .
C13 C 1.0319(4) 0.4677(4) 0.1423(2) 0.0420(6) Uani 1 1 d . . .
H13 H 0.994663 0.564547 0.172236 0.050 Uiso 1 1 calc R U .
C14 C 0.5417(5) 0.0971(5) 0.7883(3) 0.0602(9) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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
O1 Cu1 O1 180.0 2_666 .
O1 Cu1 N3 89.21(8) 2_666 .
O1 Cu1 N3 90.79(8) . .
O1 Cu1 N3 90.79(8) 2_666 2_666
O1 Cu1 N3 89.21(8) . 2_666
N3 Cu1 N3 180.0 . 2_666
O1 Cu1 O3 86.93(9) 2_666 .
O1 Cu1 O3 93.07(9) . .
N3 Cu1 O3 86.93(9) . .
N3 Cu1 O3 93.07(9) 2_666 .
O1 Cu1 O3 93.07(9) 2_666 2_666
O1 Cu1 O3 86.93(9) . 2_666
N3 Cu1 O3 93.07(9) . 2_666
N3 Cu1 O3 86.92(9) 2_666 2_666
O3 Cu1 O3 180.0 . 2_666
O5 S1 O4 114.3(3) . .
O5 S1 O3 115.9(2) . .
O4 S1 O3 113.2(2) . .
O5 S1 C14 104.61(19) . .
O4 S1 C14 102.4(2) . .
O3 S1 C14 104.50(18) . .
N2 N1 O2 104.4(2) . .
O1 C1 O2 120.3(2) . .
O1 C1 C2 133.0(2) . .
O2 C1 C2 106.7(2) . .
C1 O1 Cu1 114.65(17) . .
C1 O2 N1 110.3(2) . .
N1 N2 C2 114.7(2) . .
N1 N2 C8 115.5(2) . .
C2 N2 C8 129.8(2) . .
N2 C2 C1 103.9(2) . .
N2 C2 C3 130.0(2) . .
C1 C2 C3 125.4(2) . .
C6 C5 C4 118.8(3) . .
C5 C4 C3 119.6(3) . .
N3 C3 C4 121.9(3) . .
N3 C3 C2 114.2(2) . .
C4 C3 C2 123.7(2) . .
C7 N3 C3 117.0(2) . .
C7 N3 Cu1 117.02(18) . .
C3 N3 Cu1 125.91(18) . .
S1 O3 Cu1 167.70(18) . .
C7 C6 C5 118.7(3) . .
N3 C7 C6 123.9(3) . .
C13 C8 C9 123.5(3) . .
C13 C8 N2 118.6(3) . .
C9 C8 N2 117.8(3) . .
C8 C9 C10 117.0(3) . .
C11 C10 C9 121.1(3) . .
C10 C11 C12 120.9(3) . .
C11 C12 C13 119.7(3) . .
C8 C13 C12 117.8(3) . .
F3 C14 F1 108.1(4) . .
F3 C14 F2 107.4(4) . .
F1 C14 F2 107.7(4) . .
F3 C14 S1 111.3(3) . .
F1 C14 S1 111.4(3) . .
F2 C14 S1 110.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.967(2) 2_666
Cu1 O1 1.9669(19) .
Cu1 N3 2.064(2) .
Cu1 N3 2.064(2) 2_666
Cu1 O3 2.355(2) .
Cu1 O3 2.355(2) 2_666
S1 O5 1.413(3) .
S1 O4 1.424(3) .
S1 O3 1.426(2) .
S1 C14 1.813(4) .
F1 C14 1.314(5) .
N1 N2 1.303(4) .
N1 O2 1.375(3) .
C1 O1 1.241(3) .
C1 O2 1.357(3) .
C1 C2 1.400(4) .
F2 C14 1.323(5) .
N2 C2 1.355(3) .
N2 C8 1.449(3) .
C2 C3 1.450(4) .
C5 C6 1.377(5) .
C5 C4 1.379(4) .
C4 C3 1.384(4) .
C3 N3 1.362(3) .
N3 C7 1.340(4) .
F3 C14 1.313(5) .
C6 C7 1.375(4) .
C8 C13 1.371(4) .
C8 C9 1.380(4) .
C9 C10 1.385(5) .
C10 C11 1.362(6) .
C11 C12 1.379(5) .
C12 C13 1.392(4) .
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
_geom_hbond_publ_flag
C6 H6 S1 0.93 2.98 3.797(3) 147.1 1_655 yes
C7 H7 O1 0.93 2.35 2.878(4) 115.7 2_666 yes
C13 H13 O4 0.93 2.39 3.204(4) 145.7 2_666 yes
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
O2 C1 O1 Cu1 -150.3(2)
C2 C1 O1 Cu1 29.8(4)
O1 C1 O2 N1 179.5(2)
C2 C1 O2 N1 -0.6(3)
N2 N1 O2 C1 0.6(3)
O2 N1 N2 C2 -0.4(3)
O2 N1 N2 C8 -178.9(2)
N1 N2 C2 C1 0.0(3)
C8 N2 C2 C1 178.3(3)
N1 N2 C2 C3 170.7(3)
C8 N2 C2 C3 -11.1(4)
O1 C1 C2 N2 -179.7(3)
O2 C1 C2 N2 0.3(3)
O1 C1 C2 C3 9.1(5)
O2 C1 C2 C3 -170.9(2)
C6 C5 C4 C3 0.8(5)
C5 C4 C3 N3 0.3(4)
C5 C4 C3 C2 -174.2(3)
N2 C2 C3 N3 167.8(2)
C1 C2 C3 N3 -23.4(3)
N2 C2 C3 C4 -17.3(4)
C1 C2 C3 C4 151.5(3)
C4 C3 N3 C7 -0.7(4)
C2 C3 N3 C7 174.3(2)
C4 C3 N3 Cu1 -178.0(2)
C2 C3 N3 Cu1 -3.0(3)
O5 S1 O3 Cu1 121.4(9)
O4 S1 O3 Cu1 -13.4(10)
C14 S1 O3 Cu1 -124.0(9)
C4 C5 C6 C7 -1.4(5)
C3 N3 C7 C6 0.0(4)
Cu1 N3 C7 C6 177.5(2)
C5 C6 C7 N3 1.1(5)
N1 N2 C8 C13 111.7(3)
C2 N2 C8 C13 -66.5(4)
N1 N2 C8 C9 -65.6(4)
C2 N2 C8 C9 116.1(3)
C13 C8 C9 C10 -0.2(5)
N2 C8 C9 C10 177.0(3)
C8 C9 C10 C11 0.4(6)
C9 C10 C11 C12 0.1(6)
C10 C11 C12 C13 -0.7(6)
C9 C8 C13 C12 -0.4(5)
N2 C8 C13 C12 -177.5(3)
C11 C12 C13 C8 0.8(5)
O5 S1 C14 F3 177.4(3)
O4 S1 C14 F3 -63.1(4)
O3 S1 C14 F3 55.1(4)
O5 S1 C14 F1 -61.9(4)
O4 S1 C14 F1 57.6(4)
O3 S1 C14 F1 175.8(3)
O5 S1 C14 F2 58.0(4)
O4 S1 C14 F2 177.5(3)
O3 S1 C14 F2 -64.2(3)
