#------------------------------------------------------------------------------
#$Date: 2019-07-13 03:03:03 +0300 (Sat, 13 Jul 2019) $
#$Revision: 216986 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/38/7123846.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_7123846
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         'C26 H18 Cl2 Cu N6 O4'
_chemical_formula_sum            'C26 H18 Cl2 Cu N6 O4'
_chemical_formula_weight         612.90
_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                108.745(4)
_cell_angle_beta                 104.613(3)
_cell_angle_gamma                96.672(4)
_cell_formula_units_Z            1
_cell_length_a                   8.0661(3)
_cell_length_b                   8.8517(4)
_cell_length_c                   10.0437(4)
_cell_measurement_reflns_used    7697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.0550
_cell_measurement_theta_min      3.9370
_cell_volume                     641.70(5)
_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, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'HPAD Dectris Pilatus3R-200K-A'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_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  0.0538
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17478
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.036
_diffrn_reflns_theta_min         3.671
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) mm003 X-ray Source'
_exptl_absorpt_coefficient_mu    1.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66254
_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            green
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       cobbledstone
_exptl_crystal_F_000             311
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0301
_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)+(0.0357P)²+0.1256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3195
_reflns_number_total             3711
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc04673a2.cif
_cod_data_source_block           NIP318A
_cod_database_code               7123846
_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 0.02875(8) Uani 1 2 d S . P
O1 O 0.71811(17) 0.72346(13) 0.47899(14) 0.0430(3) Uani 1 1 d . . .
N1 N 0.7619(2) 0.59679(18) 0.13233(18) 0.0525(4) Uani 1 1 d . . .
Cl1 Cl 0.64778(5) 0.58259(5) 0.74485(4) 0.04421(11) Uani 1 1 d . . .
C1 C 0.7407(2) 0.64397(17) 0.36473(18) 0.0348(3) Uani 1 1 d . . .
C2 C 0.76110(19) 0.48252(16) 0.30176(16) 0.0305(3) Uani 1 1 d . . .
N2 N 0.76894(17) 0.46580(15) 0.16508(14) 0.0345(3) Uani 1 1 d . . .
O2 O 0.7497(2) 0.71160(14) 0.25788(15) 0.0515(3) Uani 1 1 d . . .
C3 C 0.76789(18) 0.35496(15) 0.36471(15) 0.0292(3) Uani 1 1 d . . .
N3 N 0.66726(16) 0.35109(14) 0.45304(13) 0.0302(2) Uani 1 1 d . . .
C4 C 0.8758(2) 0.24454(18) 0.33753(18) 0.0375(3) Uani 1 1 d . . .
H4 H 0.949324 0.252643 0.281012 0.045 Uiso 1 1 calc R U .
C5 C 0.8725(2) 0.12261(19) 0.3956(2) 0.0429(4) Uani 1 1 d . . .
H5 H 0.940955 0.045556 0.375789 0.052 Uiso 1 1 calc R U .
C6 C 0.7669(2) 0.11638(19) 0.4830(2) 0.0427(4) Uani 1 1 d . . .
H6 H 0.760671 0.033979 0.521330 0.051 Uiso 1 1 calc R U .
C9 C 0.6118(3) 0.2032(2) -0.0205(2) 0.0537(5) Uani 1 1 d . . .
H9 H 0.510748 0.222215 0.004630 0.064 Uiso 1 1 calc R U .
C8 C 0.7668(2) 0.31737(18) 0.04756(16) 0.0357(3) Uani 1 1 d . . .
C7 C 0.6705(2) 0.23507(18) 0.51227(19) 0.0389(3) Uani 1 1 d . . .
H7 H 0.604748 0.234701 0.576072 0.047 Uiso 1 1 calc R U .
C10 C 0.6119(3) 0.0581(3) -0.1285(2) 0.0684(6) Uani 1 1 d . . .
H10 H 0.509164 -0.022091 -0.176509 0.082 Uiso 1 1 calc R U .
C11 C 0.7611(4) 0.0317(2) -0.1652(2) 0.0639(6) Uani 1 1 d . . .
H11 H 0.759086 -0.066187 -0.237498 0.077 Uiso 1 1 calc R U .
C12 C 0.9141(3) 0.1494(2) -0.0956(2) 0.0576(5) Uani 1 1 d . . .
H12 H 1.015136 0.130559 -0.120819 0.069 Uiso 1 1 calc R U .
C13 C 0.9181(2) 0.2959(2) 0.0122(2) 0.0446(4) Uani 1 1 d . . .
H13 H 1.020183 0.377009 0.058935 0.054 Uiso 1 1 calc R U .
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'
Cl Cl 0.1484 0.1585 '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'
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'
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
N3 Cu1 N3 180.0 2_666 .
N3 Cu1 Cl1 90.12(4) 2_666 .
N3 Cu1 Cl1 89.88(4) . .
N3 Cu1 Cl1 89.88(4) 2_666 2_666
N3 Cu1 Cl1 90.12(4) . 2_666
Cl1 Cu1 Cl1 180.0 . 2_666
N2 N1 O2 104.05(12) . .
O1 C1 O2 120.78(13) . .
O1 C1 C2 135.19(14) . .
O2 C1 C2 104.03(13) . .
N2 C2 C1 105.50(12) . .
N2 C2 C3 125.55(12) . .
C1 C2 C3 128.94(13) . .
N1 N2 C2 115.08(13) . .
N1 N2 C8 116.89(13) . .
C2 N2 C8 127.72(12) . .
N1 O2 C1 111.18(11) . .
N3 C3 C4 121.43(13) . .
N3 C3 C2 116.99(12) . .
C4 C3 C2 121.57(13) . .
C7 N3 C3 118.34(12) . .
C7 N3 Cu1 115.48(10) . .
C3 N3 Cu1 126.13(9) . .
C5 C4 C3 119.18(14) . .
C6 C5 C4 119.33(14) . .
C5 C6 C7 118.49(14) . .
C8 C9 C10 117.33(18) . .
C13 C8 C9 123.33(16) . .
C13 C8 N2 119.29(14) . .
C9 C8 N2 117.37(15) . .
N3 C7 C6 123.08(15) . .
C11 C10 C9 120.89(19) . .
C10 C11 C12 120.30(18) . .
C11 C12 C13 120.22(19) . .
C8 C13 C12 117.92(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N3 2.0285(11) 2_666
Cu1 N3 2.0285(11) .
Cu1 Cl1 2.2729(4) .
Cu1 Cl1 2.2729(4) 2_666
O1 C1 1.2089(19) .
N1 N2 1.3065(18) .
N1 O2 1.376(2) .
C1 O2 1.3991(19) .
C1 C2 1.4128(19) .
C2 N2 1.3512(19) .
C2 C3 1.4606(18) .
N2 C8 1.4517(19) .
C3 N3 1.3503(18) .
C3 C4 1.3907(19) .
N3 C7 1.3417(18) .
C4 C5 1.382(2) .
C5 C6 1.378(2) .
C6 C7 1.379(2) .
C9 C8 1.372(2) .
C9 C10 1.390(3) .
C8 C13 1.371(2) .
C10 C11 1.368(3) .
C11 C12 1.376(3) .
C12 C13 1.387(3) .
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
O1 C1 C2 N2 175.63(19)
O2 C1 C2 N2 -3.64(16)
O1 C1 C2 C3 -2.7(3)
O2 C1 C2 C3 177.99(14)
O2 N1 N2 C2 0.5(2)
O2 N1 N2 C8 174.69(13)
C1 C2 N2 N1 2.08(19)
C3 C2 N2 N1 -179.47(15)
C1 C2 N2 C8 -171.37(14)
C3 C2 N2 C8 7.1(2)
N2 N1 O2 C1 -3.0(2)
O1 C1 O2 N1 -175.22(16)
C2 C1 O2 N1 4.18(18)
N2 C2 C3 N3 -143.59(14)
C1 C2 C3 N3 34.5(2)
N2 C2 C3 C4 37.7(2)
C1 C2 C3 C4 -144.19(16)
C4 C3 N3 C7 -1.4(2)
C2 C3 N3 C7 179.88(13)
C4 C3 N3 Cu1 -178.67(11)
C2 C3 N3 Cu1 2.65(18)
N3 C3 C4 C5 3.7(2)
C2 C3 C4 C5 -177.71(14)
C3 C4 C5 C6 -2.1(3)
C4 C5 C6 C7 -1.4(3)
C10 C9 C8 C13 1.2(3)
C10 C9 C8 N2 -177.24(19)
N1 N2 C8 C13 79.0(2)
C2 N2 C8 C13 -107.69(19)
N1 N2 C8 C9 -102.48(19)
C2 N2 C8 C9 70.9(2)
C3 N3 C7 C6 -2.4(2)
Cu1 N3 C7 C6 175.15(14)
C5 C6 C7 N3 3.8(3)
C8 C9 C10 C11 -0.3(4)
C9 C10 C11 C12 -0.2(4)
C10 C11 C12 C13 -0.2(4)
C9 C8 C13 C12 -1.6(3)
N2 C8 C13 C12 176.87(17)
C11 C12 C13 C8 1.0(3)
