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#$Date: 2019-11-23 01:08:39 +0200 (Sat, 23 Nov 2019) $
#$Revision: 231731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/63/4346339.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_4346339
loop_
_publ_author_name
'Myers, Thomas W.'
'Chavez, David E.'
'Hanson, Susan K.'
'Scharff, R. Jason'
'Scott, Brian L.'
'Veauthier, Jacqueline M.'
'Wu, Ruilian'
_publ_section_title
;
 Independent Control of Optical and Explosive Properties:
 Pyrazole-Tetrazine Complexes of First Row Transition Metals.
;
_journal_issue                   16
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8077
_journal_page_last               8086
_journal_paper_doi               10.1021/acs.inorgchem.5b01313
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C16 H23 Cu F6 N14 O0.5 P'
_chemical_formula_weight         627.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 127.049(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.060(5)
_cell_length_b                   13.326(2)
_cell_length_c                   18.396(4)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.84
_cell_volume                     5098.8(17)
_computing_cell_refinement       'rigaku crystal clear 2.0'
_computing_data_collection       'rigaku crystal clear 2.0'
_computing_data_reduction        'rigaku crystal clear 2.0'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'rigaku raxis iv'
_diffrn_measurement_method       'multiple orientation single axis rotation'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13197
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.892
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       block
_exptl_crystal_F_000             2552
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_refine_diff_density_max         1.202
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0873
_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)+(0.1949P)²+0.7812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2384
_refine_ls_wR_factor_ref         0.2544
_reflns_number_gt                4301
_reflns_number_total             5123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5b01313_si_002.cif
_cod_data_source_block           twm9
_cod_original_cell_volume        5098.7(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C16 H23 Cu F6 N14 O0.50 P'
_cod_database_code               4346339
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.788
_shelx_estimated_absorpt_t_max   0.817
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'
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
Cu1 Cu 0.09335(2) 0.51234(4) 0.25131(3) 0.0653(3) Uani 1 1 d . . . . .
O1 O 0.0000 0.1164(5) 0.2500 0.1035(15) Uani 1 2 d S T P . .
N1 N -0.09171(19) 0.2453(3) 0.1028(3) 0.0978(13) Uani 1 1 d . . . . .
H1A H -0.0661 0.2085 0.1518 0.117 Uiso 1 1 calc R U . . .
H1B H -0.1306 0.2239 0.0590 0.117 Uiso 1 1 calc R U . . .
N2 N -0.01130(14) 0.3597(3) 0.1650(2) 0.0698(8) Uani 1 1 d . . . . .
N3 N -0.11228(14) 0.3871(3) 0.0181(2) 0.0699(8) Uani 1 1 d . . . . .
N4 N 0.00844(14) 0.4469(3) 0.1566(2) 0.0637(7) Uani 1 1 d . . . . .
N5 N -0.08951(14) 0.4719(3) 0.0098(2) 0.0673(8) Uani 1 1 d . . . . .
N6 N -0.00270(14) 0.5841(2) 0.07184(19) 0.0604(7) Uani 1 1 d . . . . .
N7 N 0.05882(14) 0.6081(2) 0.14562(19) 0.0630(7) Uani 1 1 d . . . . .
N8 N 0.24699(18) 0.1975(3) 0.3497(3) 0.0796(9) Uani 1 1 d . . . . .
H8A H 0.2221 0.1757 0.2932 0.096 Uiso 1 1 calc R U . . .
H8B H 0.2807 0.1623 0.3920 0.096 Uiso 1 1 calc R U . . .
N9 N 0.18152(14) 0.3360(2) 0.30485(19) 0.0660(7) Uani 1 1 d . . . . .
N10 N 0.27374(15) 0.3133(3) 0.4596(2) 0.0708(8) Uani 1 1 d . . . . .
N11 N 0.16957(14) 0.4216(2) 0.3279(2) 0.0628(7) Uani 1 1 d . . . . .
N12 N 0.25913(15) 0.3967(2) 0.4819(2) 0.0680(7) Uani 1 1 d . . . . .
N13 N 0.19301(15) 0.5360(2) 0.4396(2) 0.0622(7) Uani 1 1 d . . . . .
N14 N 0.13528(14) 0.5798(3) 0.3734(2) 0.0653(7) Uani 1 1 d . . . . .
C1 C -0.07192(18) 0.3316(3) 0.0948(3) 0.0703(9) Uani 1 1 d . . . . .
C2 C -0.03006(18) 0.4974(3) 0.0779(3) 0.0596(8) Uani 1 1 d . . . . .
C3 C 0.1358(2) 0.7445(4) 0.1920(3) 0.0866(12) Uani 1 1 d . . . . .
H3A H 0.1373 0.8074 0.1657 0.130 Uiso 1 1 calc R U . . .
H3B H 0.1411 0.7589 0.2484 0.130 Uiso 1 1 calc R U . . .
H3C H 0.1704 0.7001 0.2052 0.130 Uiso 1 1 calc R U . . .
C4 C 0.07230(18) 0.6944(3) 0.1255(2) 0.0661(8) Uani 1 1 d . . . . .
C5 C 0.0211(2) 0.7261(3) 0.0384(3) 0.0707(9) Uani 1 1 d . . . . .
H5A H 0.0196 0.7854 0.0085 0.085 Uiso 1 1 calc R U . . .
C6 C -0.02634(19) 0.6559(3) 0.0045(2) 0.0681(9) Uani 1 1 d . . . . .
C7 C -0.09150(19) 0.6529(3) -0.0846(3) 0.0761(10) Uani 1 1 d . . . . .
H7A H -0.1139 0.5919 -0.0880 0.114 Uiso 1 1 calc R U . . .
H7B H -0.1160 0.7120 -0.0902 0.114 Uiso 1 1 calc R U . . .
H7C H -0.0874 0.6527 -0.1342 0.114 Uiso 1 1 calc R U . . .
C8 C 0.23358(17) 0.2837(3) 0.3712(2) 0.0653(8) Uani 1 1 d . . . . .
C9 C 0.20839(16) 0.4473(3) 0.4168(2) 0.0613(8) Uani 1 1 d . . . . .
C10 C 0.2933(2) 0.5689(4) 0.5999(3) 0.0850(12) Uani 1 1 d . . . . .
H10A H 0.3083 0.6215 0.6458 0.127 Uiso 1 1 calc R U . . .
H10B H 0.2919 0.5046 0.6244 0.127 Uiso 1 1 calc R U . . .
H10C H 0.3230 0.5637 0.5839 0.127 Uiso 1 1 calc R U . . .
C11 C 0.22772(18) 0.5946(3) 0.5169(3) 0.0690(9) Uani 1 1 d . . . . .
C12 C 0.19009(19) 0.6774(3) 0.4982(3) 0.0716(9) Uani 1 1 d . . . . .
H12A H 0.2005 0.7323 0.5378 0.086 Uiso 1 1 calc R U . . .
C13 C 0.13395(18) 0.6651(3) 0.4105(3) 0.0677(9) Uani 1 1 d . . . . .
C14 C 0.0775(2) 0.7342(4) 0.3580(3) 0.0844(11) Uani 1 1 d . . . . .
H14A H 0.0849 0.7924 0.3957 0.127 Uiso 1 1 calc R U . . .
H14B H 0.0719 0.7567 0.3028 0.127 Uiso 1 1 calc R U . . .
H14C H 0.0387 0.6987 0.3409 0.127 Uiso 1 1 calc R U . . .
C15 C 0.0260(8) 0.0664(10) 0.2127(11) 0.229(6) Uani 1 1 d . . . . .
H15A H 0.0730 0.0775 0.2557 0.274 Uiso 1 1 calc R U . . .
H15B H 0.0111 0.1038 0.1566 0.274 Uiso 1 1 calc R U . . .
C16 C 0.0183(7) -0.0329(8) 0.1896(17) 0.39(2) Uani 1 1 d . . . . .
H16A H 0.0417 -0.0485 0.1648 0.591 Uiso 1 1 calc R U . . .
H16B H 0.0351 -0.0740 0.2439 0.591 Uiso 1 1 calc R U . . .
H16C H -0.0275 -0.0474 0.1437 0.591 Uiso 1 1 calc R U . . .
P1 P 0.1580(6) 0.0446(9) 0.1113(7) 0.086(2) Uani 0.570(13) 1 d . . P A 1
F1 F 0.1430(15) -0.0466(14) 0.052(3) 0.350(19) Uani 0.570(13) 1 d . . P A 1
F2 F 0.2161(14) -0.0105(19) 0.1891(19) 0.263(13) Uani 0.570(13) 1 d . . P A 1
F3 F 0.1885(5) 0.1479(6) 0.1546(7) 0.114(3) Uani 0.570(13) 1 d . . P A 1
F4 F 0.1446(6) 0.0232(8) 0.1817(7) 0.129(4) Uani 0.570(13) 1 d . . P A 1
F5 F 0.0882(4) 0.1076(7) 0.0352(7) 0.123(3) Uani 0.570(13) 1 d . . P A 1
F6 F 0.1621(7) 0.0648(9) 0.0305(7) 0.138(4) Uani 0.570(13) 1 d . . P A 1
P1A P 0.1491(7) 0.0376(12) 0.1006(10) 0.083(3) Uani 0.430(13) 1 d . . P A 2
F1A F 0.0961(9) -0.0198(19) 0.090(3) 0.233(13) Uani 0.430(13) 1 d . . P A 2
F2A F 0.1183(8) -0.0592(8) 0.0574(7) 0.116(4) Uani 0.430(13) 1 d . . P A 2
F3A F 0.2032(9) 0.0785(12) 0.0903(17) 0.162(6) Uani 0.430(13) 1 d . . P A 2
F4A F 0.2144(10) -0.0210(18) 0.1588(13) 0.146(7) Uani 0.430(13) 1 d . . P A 2
F5A F 0.1661(12) 0.1130(19) 0.1703(10) 0.229(14) Uani 0.430(13) 1 d . . P A 2
F6A F 0.1051(13) 0.088(2) 0.0478(19) 0.298(18) Uani 0.430(13) 1 d . . P A 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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
N11 Cu1 N4 117.03(13) .
N11 Cu1 N14 81.02(13) .
N4 Cu1 N14 136.94(12) .
N11 Cu1 N7 137.12(12) .
N4 Cu1 N7 79.71(12) .
N14 Cu1 N7 114.57(13) .
C15 O1 C15 122.8(14) 2
N4 N2 C1 116.4(3) .
N5 N3 C1 117.5(3) .
N2 N4 C2 118.5(3) .
N2 N4 Cu1 125.8(2) .
C2 N4 Cu1 115.7(3) .
C2 N5 N3 117.4(3) .
N7 N6 C6 110.4(3) .
N7 N6 C2 117.4(3) .
C6 N6 C2 132.1(3) .
C4 N7 N6 106.0(3) .
C4 N7 Cu1 141.1(3) .
N6 N7 Cu1 112.3(2) .
N11 N9 C8 117.4(3) .
N12 N10 C8 117.3(3) .
N9 N11 C9 117.4(3) .
N9 N11 Cu1 128.5(2) .
C9 N11 Cu1 113.6(3) .
C9 N12 N10 118.1(3) .
N14 N13 C11 111.3(3) .
N14 N13 C9 117.1(3) .
C11 N13 C9 131.5(3) .
C13 N14 N13 105.1(3) .
C13 N14 Cu1 141.4(3) .
N13 N14 Cu1 111.5(2) .
N1 C1 N2 116.7(4) .
N1 C1 N3 118.9(4) .
N2 C1 N3 124.4(4) .
N5 C2 N4 125.5(4) .
N5 C2 N6 120.0(3) .
N4 C2 N6 114.5(3) .
N7 C4 C5 110.8(4) .
N7 C4 C3 120.7(4) .
C5 C4 C3 128.5(4) .
C6 C5 C4 107.0(3) .
C5 C6 N6 105.8(3) .
C5 C6 C7 129.8(4) .
N6 C6 C7 124.4(4) .
N8 C8 N9 118.6(3) .
N8 C8 N10 117.1(3) .
N9 C8 N10 124.3(3) .
N12 C9 N11 125.5(4) .
N12 C9 N13 118.4(3) .
N11 C9 N13 116.0(3) .
N13 C11 C12 105.7(3) .
N13 C11 C10 124.1(4) .
C12 C11 C10 130.1(4) .
C11 C12 C13 106.8(3) .
N14 C13 C12 111.1(3) .
N14 C13 C14 120.8(4) .
C12 C13 C14 128.0(4) .
O1 C15 C16 126.3(16) .
F2 P1 F1 88.1(17) .
F2 P1 F3 91.9(14) .
F1 P1 F3 155.9(13) .
F2 P1 F4 73.8(14) .
F1 P1 F4 110.9(15) .
F3 P1 F4 92.2(7) .
F2 P1 F6 112.3(16) .
F1 P1 F6 66.2(15) .
F3 P1 F6 91.6(8) .
F4 P1 F6 172.7(12) .
F2 P1 F5 170.0(14) .
F1 P1 F5 96.9(14) .
F3 P1 F5 87.0(7) .
F4 P1 F5 96.3(7) .
F6 P1 F5 77.7(8) .
P1 F1 F6 58.6(8) .
P1 F6 F1 55.2(11) .
F6A P1A F2A 96.6(18) .
F6A P1A F1A 80(2) .
F2A P1A F1A 47.2(14) .
F6A P1A F5A 87.7(19) .
F2A P1A F5A 148.1(18) .
F1A P1A F5A 103(2) .
F6A P1A F4A 166(3) .
F2A P1A F4A 86.9(15) .
F1A P1A F4A 112.0(16) .
F5A P1A F4A 96.5(13) .
F6A P1A F3A 101(2) .
F2A P1A F3A 117.3(14) .
F1A P1A F3A 164(2) .
F5A P1A F3A 92.6(16) .
F4A P1A F3A 65.5(13) .
F2A F1A P1A 65.8(11) .
F2A F1A F6A 83.9(18) .
P1A F1A F6A 42.0(11) .
F1A F2A P1A 67.1(13) .
P1A F3A F4A 55.6(9) .
P1A F4A F3A 58.9(10) .
P1A F6A F1A 58.3(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N11 2.005(3) .
Cu1 N4 2.011(3) .
Cu1 N14 2.022(3) .
Cu1 N7 2.028(3) .
O1 C15 1.391(13) 2
O1 C15 1.391(13) .
N1 C1 1.304(6) .
N2 N4 1.317(4) .
N2 C1 1.358(5) .
N3 N5 1.327(5) .
N3 C1 1.362(5) .
N4 C2 1.344(5) .
N5 C2 1.321(5) .
N6 N7 1.376(4) .
N6 C6 1.382(5) .
N6 C2 1.397(5) .
N7 C4 1.318(5) .
N8 C8 1.328(5) .
N9 N11 1.317(4) .
N9 C8 1.350(5) .
N10 N12 1.317(5) .
N10 C8 1.358(4) .
N11 C9 1.350(5) .
N12 C9 1.315(5) .
N13 N14 1.371(4) .
N13 C11 1.378(5) .
N13 C9 1.391(5) .
N14 C13 1.337(5) .
C3 C4 1.497(6) .
C4 C5 1.396(5) .
C5 C6 1.365(6) .
C6 C7 1.489(5) .
C10 C11 1.492(6) .
C11 C12 1.375(6) .
C12 C13 1.388(5) .
C13 C14 1.494(6) .
C15 C16 1.368(15) .
P1 F2 1.51(2) .
P1 F1 1.51(2) .
P1 F3 1.548(15) .
P1 F4 1.558(10) .
P1 F6 1.575(11) .
P1 F5 1.704(14) .
F1 F6 1.69(3) .
P1A F6A 1.17(2) .
P1A F2A 1.474(18) .
P1A F1A 1.49(2) .
P1A F5A 1.47(2) .
P1A F4A 1.57(2) .
P1A F3A 1.626(19) .
F1A F2A 1.19(3) .
F1A F6A 1.72(4) .
F3A F4A 1.73(3) .
