#------------------------------------------------------------------------------
#$Date: 2015-09-08 14:50:34 +0300 (Tue, 08 Sep 2015) $
#$Revision: 155217 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/49/7054987.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_7054987
loop_
_publ_author_name
'Ulbrich, Ana H. D. P. S.'
'Milani, Jorge L. S.'
'Roisnel, Thierry'
'Carpentier, Jean-François'
'Casagrande, Osvaldo L.'
_publ_section_title
;
 Zwitterionic Ni(ii) complexes bearing pyrazolyl-ether-imidazolium
 ligands: synthesis, structural characterization and use in ethylene
 oligomerization
;
_journal_issue                   9
_journal_name_full               'New J. Chem.'
_journal_page_first              7234
_journal_paper_doi               10.1039/C5NJ01538C
_journal_volume                  39
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H21 N4 O, F6 P'
_chemical_formula_sum            'C13 H21 F6 N4 O P'
_chemical_formula_weight         394.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-04-24T09:28:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-03-23 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                93.277(11)
_cell_angle_beta                 99.516(13)
_cell_angle_gamma                96.900(11)
_cell_formula_units_Z            2
_cell_length_a                   7.3802(11)
_cell_length_b                   8.3070(14)
_cell_length_c                   14.538(2)
_cell_measurement_reflns_used    18923
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.91
_cell_measurement_wavelength     0.71073
_cell_volume                     870.0(2)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.26594E-2
_diffrn_orient_matrix_UB_12      0.100665
_diffrn_orient_matrix_UB_13      -0.347195E-1
_diffrn_orient_matrix_UB_21      -0.127566
_diffrn_orient_matrix_UB_22      0.132885E-1
_diffrn_orient_matrix_UB_23      0.113931E-1
_diffrn_orient_matrix_UB_31      0.543257E-1
_diffrn_orient_matrix_UB_32      0.67134E-1
_diffrn_orient_matrix_UB_33      0.596407E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15450
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.5
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.42
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0503P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0978
_reflns_number_gt                3166
_reflns_number_total             3980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5nj01538c2.cif
_cod_data_source_block           job
_cod_depositor_comments
'Adding full bibliography for 7054987--7054991.cif.'
_cod_database_code               7054987
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.1856(2) 0.92553(19) 0.42928(11) 0.0298(4) Uani 1 1 d .
H1A H 1.3036 0.8821 0.4447 0.045 Uiso 1 1 calc R
H1B H 1.1152 0.9103 0.4804 0.045 Uiso 1 1 calc R
H1C H 1.2095 1.0418 0.4205 0.045 Uiso 1 1 calc R
C2 C 1.0765(2) 0.83792(16) 0.34130(10) 0.0222(3) Uani 1 1 d .
C3 C 0.9046(2) 0.73906(17) 0.32783(11) 0.0255(3) Uani 1 1 d .
H3 H 0.8302 0.7139 0.3739 0.031 Uiso 1 1 calc R
C4 C 0.8657(2) 0.68624(17) 0.23466(11) 0.0235(3) Uani 1 1 d .
C5 C 0.7067(2) 0.5746(2) 0.17954(13) 0.0337(4) Uani 1 1 d .
H5A H 0.6443 0.6316 0.1288 0.05 Uiso 1 1 calc R
H5B H 0.619 0.5396 0.2205 0.05 Uiso 1 1 calc R
H5C H 0.7523 0.4793 0.1531 0.05 Uiso 1 1 calc R
N6 N 1.00927(16) 0.75575(13) 0.19629(8) 0.0189(3) Uani 1 1 d .
N7 N 1.14187(16) 0.84758(13) 0.26093(8) 0.0194(3) Uani 1 1 d .
C8 C 1.0473(2) 0.72695(16) 0.10217(10) 0.0206(3) Uani 1 1 d .
H8A H 1.0967 0.8311 0.08 0.025 Uiso 1 1 calc R
H8B H 0.9306 0.6838 0.0595 0.025 Uiso 1 1 calc R
C9 C 1.1860(2) 0.60730(16) 0.09958(10) 0.0211(3) Uani 1 1 d .
H9A H 1.2242 0.6012 0.0375 0.025 Uiso 1 1 calc R
H9B H 1.2976 0.6425 0.1476 0.025 Uiso 1 1 calc R
O10 O 1.09887(13) 0.45186(11) 0.11765(7) 0.0197(2) Uani 1 1 d .
C11 C 1.22837(19) 0.34561(16) 0.14956(10) 0.0204(3) Uani 1 1 d .
H11A H 1.3069 0.3924 0.2092 0.025 Uiso 1 1 calc R
H11B H 1.3096 0.33 0.1029 0.025 Uiso 1 1 calc R
C12 C 1.1218(2) 0.18510(16) 0.16366(10) 0.0206(3) Uani 1 1 d .
H12A H 1.0471 0.138 0.1031 0.025 Uiso 1 1 calc R
H12B H 1.2102 0.1088 0.1853 0.025 Uiso 1 1 calc R
N13 N 0.99807(16) 0.20302(13) 0.23267(8) 0.0182(3) Uani 1 1 d .
C14 C 0.84203(19) 0.10442(16) 0.23209(10) 0.0190(3) Uani 1 1 d .
H14 H 0.7934 0.0154 0.1874 0.023 Uiso 1 1 calc R
C15 C 1.0223(2) 0.31566(17) 0.30840(10) 0.0245(3) Uani 1 1 d .
H15 H 1.1225 0.4006 0.3261 0.029 Uiso 1 1 calc R
C16 C 0.8769(2) 0.28275(17) 0.35263(10) 0.0248(3) Uani 1 1 d .
H16 H 0.8556 0.3404 0.4073 0.03 Uiso 1 1 calc R
N17 N 0.76504(17) 0.15009(14) 0.30386(8) 0.0209(3) Uani 1 1 d .
C18 C 0.5928(2) 0.06795(19) 0.32793(11) 0.0284(3) Uani 1 1 d .
H18A H 0.5121 0.0165 0.2709 0.043 Uiso 1 1 calc R
H18B H 0.5291 0.1479 0.3578 0.043 Uiso 1 1 calc R
H18C H 0.6226 -0.0152 0.3711 0.043 Uiso 1 1 calc R
P1 P 0.5 0 0 0.01826(13) Uani 1 2 d S
F11 F 0.47107(13) -0.06526(11) 0.09871(6) 0.0330(2) Uani 1 1 d .
F12 F 0.42416(13) -0.17660(10) -0.05045(7) 0.0320(2) Uani 1 1 d .
F13 F 0.70820(12) -0.04633(11) 0.01681(6) 0.0305(2) Uani 1 1 d .
P2 P 0.5 0.5 0.5 0.02352(14) Uani 1 2 d S
F21 F 0.50850(14) 0.53973(13) 0.60999(7) 0.0394(3) Uani 1 1 d .
F22 F 0.28848(13) 0.53506(12) 0.48065(7) 0.0381(3) Uani 1 1 d .
F23 F 0.43228(15) 0.31303(11) 0.50985(8) 0.0447(3) 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 0 '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 0.006 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 3 -11 0.112
14 1 -3 0.06
7 -6 19 0.029
-17 -1 3 0.074
1 17 1 0.072
0 -1 0 0.064
-3 1 16 0.053
3 -1 -10 0.108
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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N7 C2 C3 110.97(13) . .
N7 C2 C1 120.09(13) . .
C3 C2 C1 128.94(13) . .
C4 C3 C2 106.03(13) . .
C4 C3 H3 127 . .
C2 C3 H3 127 . .
N6 C4 C3 106.04(13) . .
N6 C4 C5 122.94(14) . .
C3 C4 C5 131.01(14) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C4 N6 N7 112.41(12) . .
C4 N6 C8 128.68(12) . .
N7 N6 C8 118.35(11) . .
C2 N7 N6 104.52(11) . .
N6 C8 C9 111.18(11) . .
N6 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
N6 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108 . .
O10 C9 C8 107.79(11) . .
O10 C9 H9A 110.1 . .
C8 C9 H9A 110.1 . .
O10 C9 H9B 110.1 . .
C8 C9 H9B 110.1 . .
H9A C9 H9B 108.5 . .
C11 O10 C9 112.70(10) . .
O10 C11 C12 108.10(11) . .
O10 C11 H11A 110.1 . .
C12 C11 H11A 110.1 . .
O10 C11 H11B 110.1 . .
C12 C11 H11B 110.1 . .
H11A C11 H11B 108.4 . .
N13 C12 C11 111.88(11) . .
N13 C12 H12A 109.2 . .
C11 C12 H12A 109.2 . .
N13 C12 H12B 109.2 . .
C11 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
C14 N13 C15 108.22(12) . .
C14 N13 C12 123.69(12) . .
C15 N13 C12 128.05(12) . .
N17 C14 N13 109.16(12) . .
N17 C14 H14 125.4 . .
N13 C14 H14 125.4 . .
C16 C15 N13 107.11(13) . .
C16 C15 H15 126.4 . .
N13 C15 H15 126.4 . .
C15 C16 N17 107.34(13) . .
C15 C16 H16 126.3 . .
N17 C16 H16 126.3 . .
C14 N17 C16 108.16(12) . .
C14 N17 C18 125.18(13) . .
C16 N17 C18 126.63(12) . .
N17 C18 H18A 109.5 . .
N17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
F12 P1 F12 180 2_655 .
F12 P1 F11 90.16(5) 2_655 2_655
F12 P1 F11 89.84(5) . 2_655
F12 P1 F11 89.84(5) 2_655 .
F12 P1 F11 90.16(5) . .
F11 P1 F11 180.00(2) 2_655 .
F12 P1 F13 90.37(5) 2_655 2_655
F12 P1 F13 89.63(5) . 2_655
F11 P1 F13 89.89(5) 2_655 2_655
F11 P1 F13 90.11(5) . 2_655
F12 P1 F13 89.63(5) 2_655 .
F12 P1 F13 90.37(5) . .
F11 P1 F13 90.11(5) 2_655 .
F11 P1 F13 89.89(5) . .
F13 P1 F13 180 2_655 .
F23 P2 F23 180 2_666 .
F23 P2 F21 90.30(6) 2_666 2_666
F23 P2 F21 89.70(6) . 2_666
F23 P2 F21 89.70(6) 2_666 .
F23 P2 F21 90.30(6) . .
F21 P2 F21 180.00(11) 2_666 .
F23 P2 F22 90.00(6) 2_666 2_666
F23 P2 F22 90.00(6) . 2_666
F21 P2 F22 89.95(5) 2_666 2_666
F21 P2 F22 90.05(5) . 2_666
F23 P2 F22 90.00(6) 2_666 .
F23 P2 F22 90.00(6) . .
F21 P2 F22 90.05(5) 2_666 .
F21 P2 F22 89.95(5) . .
F22 P2 F22 179.999(17) 2_666 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.492(2) .
C1 H1A 0.98 .
C1 H1B 0.98 .
C1 H1C 0.98 .
C2 N7 1.3388(18) .
C2 C3 1.404(2) .
C3 C4 1.372(2) .
C3 H3 0.95 .
C4 N6 1.3609(18) .
C4 C5 1.491(2) .
C5 H5A 0.98 .
C5 H5B 0.98 .
C5 H5C 0.98 .
N6 N7 1.3628(17) .
N6 C8 1.4541(18) .
C8 C9 1.5131(19) .
C8 H8A 0.99 .
C8 H8B 0.99 .
C9 O10 1.4300(15) .
C9 H9A 0.99 .
C9 H9B 0.99 .
O10 C11 1.4179(16) .
C11 C12 1.5069(18) .
C11 H11A 0.99 .
C11 H11B 0.99 .
C12 N13 1.4770(17) .
C12 H12A 0.99 .
C12 H12B 0.99 .
N13 C14 1.3291(18) .
N13 C15 1.3773(19) .
C14 N17 1.3260(18) .
C14 H14 0.95 .
C15 C16 1.348(2) .
C15 H15 0.95 .
C16 N17 1.3775(19) .
C16 H16 0.95 .
N17 C18 1.4730(18) .
C18 H18A 0.98 .
C18 H18B 0.98 .
C18 H18C 0.98 .
P1 F12 1.5960(9) 2_655
P1 F12 1.5960(9) .
P1 F11 1.6003(9) 2_655
P1 F11 1.6004(9) .
P1 F13 1.6117(9) 2_655
P1 F13 1.6117(9) .
P2 F23 1.5953(10) 2_666
P2 F23 1.5953(10) .
P2 F21 1.6035(9) 2_666
P2 F21 1.6035(9) .
P2 F22 1.6044(10) 2_666
P2 F22 1.6045(10) .
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
N7 C2 C3 C4 0.33(16)
C1 C2 C3 C4 -179.28(14)
C2 C3 C4 N6 -1.20(15)
C2 C3 C4 C5 177.87(15)
C3 C4 N6 N7 1.73(15)
C5 C4 N6 N7 -177.43(13)
C3 C4 N6 C8 172.83(13)
C5 C4 N6 C8 -6.3(2)
C3 C2 N7 N6 0.68(15)
C1 C2 N7 N6 -179.67(12)
C4 N6 N7 C2 -1.50(14)
C8 N6 N7 C2 -173.62(11)
C4 N6 C8 C9 -97.37(16)
N7 N6 C8 C9 73.28(14)
N6 C8 C9 O10 68.03(15)
C8 C9 O10 C11 -159.01(11)
C9 O10 C11 C12 -178.45(11)
O10 C11 C12 N13 -59.51(15)
C11 C12 N13 C14 152.13(13)
C11 C12 N13 C15 -30.1(2)
C15 N13 C14 N17 0.43(16)
C12 N13 C14 N17 178.57(12)
C14 N13 C15 C16 -0.34(16)
C12 N13 C15 C16 -178.38(13)
N13 C15 C16 N17 0.13(17)
N13 C14 N17 C16 -0.35(16)
N13 C14 N17 C18 -178.42(12)
C15 C16 N17 C14 0.13(17)
C15 C16 N17 C18 178.17(14)
