data_niphcf3_jr
_audit_creation_date               2018-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C15 H21 F3 N2 Ni S2, C2 H3 N'
_chemical_formula_sum              'C17 H24 F3 N3 Ni S2'
_chemical_formula_weight           450.22
_chemical_melting_point            ?
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'
 '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'
 'Ni' 'Ni' -3.0029 0.5091
 '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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     12.698(3)
_cell_length_b                     15.104(3)
_cell_length_c                     10.542(2)
_cell_angle_alpha                  90
_cell_angle_beta                   100.076(10)
_cell_angle_gamma                  90
_cell_volume                       1990.8(7)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9198
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        66.740
_cell_measurement_theta_min        4.591
_shelx_estimated_absorpt_T_max     0.964
_shelx_estimated_absorpt_T_min     0.711
_exptl_absorpt_coefficient_mu      3.668
_exptl_absorpt_correction_T_max    0.7528
_exptl_absorpt_correction_T_min    0.3755
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1555 before and 0.0671 after correction. The Ratio of minimum to maximum transmission is 0.4988. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              blue
_exptl_crystal_colour_primary      blue
_exptl_crystal_density_diffrn      1.502
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               936
_exptl_crystal_size_max            0.1
_exptl_crystal_size_mid            0.01
_exptl_crystal_size_min            0.01
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0467
_diffrn_reflns_av_unetI/netI       0.0271
_diffrn_reflns_Laue_measured_fraction_full  0.987
_diffrn_reflns_Laue_measured_fraction_max  0.987
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         17
_diffrn_reflns_limit_k_min         -17
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -12
_diffrn_reflns_number              26307
_diffrn_reflns_point_group_measured_fraction_full  0.987
_diffrn_reflns_point_group_measured_fraction_max  0.987
_diffrn_reflns_theta_full          66.734
_diffrn_reflns_theta_max           66.734
_diffrn_reflns_theta_min           4.591
_diffrn_ambient_temperature        99.99
_diffrn_detector                   'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean   7.9
_diffrn_detector_type              'CMOS area detector'
_diffrn_measured_fraction_theta_full  0.987
_diffrn_measured_fraction_theta_max  0.987
_diffrn_measurement_device         'three-circle diffractometer'
_diffrn_measurement_device_type    'Bruker Micro-Source CMOS'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    'mirror optics'
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'sealed X-ray tube'
_diffrn_source_target              Mo
_diffrn_source_type                'Incoatec I\ms'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3244
_reflns_number_total               3479
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.980
_refine_diff_density_min           -0.754
_refine_diff_density_rms           0.093
_refine_ls_extinction_coef         0.0018(5)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.091
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       265
_refine_ls_number_reflns           3479
_refine_ls_number_restraints       78
_refine_ls_R_factor_all            0.0549
_refine_ls_R_factor_gt             0.0515
_refine_ls_restrained_S_all        1.087
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0855P)²+3.9456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1459
_refine_ls_wR_factor_ref           0.1521
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1B-C1B = N1A-C1A
 1.137 with sigma of 0.003
 N1B-C2B = N1A-C2A
 2.593 with sigma of 0.001
 C1B-C2B = C1A-C2A
 1.456 with sigma of 0.003
3. Rigid bond restraints
 N1A, C1A, C2A, N1B, C1B, C2B
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
N1A \\sim C1A \\sim C2A \\sim N1B \\sim C1B \\sim C2B: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01
5. Others
 Sof(N1B)=Sof(C1B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(H2BC)=1-FVAR(1)
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=FVAR(1)
6.a Riding coordinates:
 C2A(H2AA,H2AB,H2AC), C2B(H2BA,H2BB,H2BC)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B)
6.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C00D(H00D)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 Ni1 Ni 0.58124(4) 0.27331(3) 0.77204(5) 0.0234(2) Uani 1 1 d . . . . .
 S1 S 0.46806(6) 0.20037(5) 0.87005(7) 0.0262(3) Uani 1 1 d . . . . .
 S2 S 0.66439(7) 0.15104(5) 0.75811(8) 0.0279(3) Uani 1 1 d . . . . .
 F1 F 0.0453(2) 0.1305(4) 0.4027(3) 0.1171(18) Uani 1 1 d . . . . .
 F2 F -0.0184(2) 0.2239(2) 0.5206(5) 0.0944(13) Uani 1 1 d . . . . .
 F3 F -0.0222(2) 0.0885(2) 0.5615(3) 0.0653(8) Uani 1 1 d . . . . .
 N1 N 0.5219(2) 0.39407(17) 0.7823(3) 0.0275(6) Uani 1 1 d . . . . .
 N2 N 0.6941(2) 0.33953(18) 0.7104(3) 0.0292(6) Uani 1 1 d . . . . .
 C1 C 0.4066(3) 0.4041(3) 0.7919(5) 0.0470(10) Uani 1 1 d . . . . .
 H1A H 0.362628 0.372013 0.720965 0.070 Uiso 1 1 calc GR . . . .
 H1B H 0.387332 0.466944 0.786884 0.070 Uiso 1 1 calc GR . . . .
 H1C H 0.394284 0.379801 0.874298 0.070 Uiso 1 1 calc GR . . . .
 C2 C 0.5873(3) 0.4342(2) 0.8972(3) 0.0374(9) Uani 1 1 d . . . . .
 H2A H 0.586235 0.394593 0.971705 0.045 Uiso 1 1 calc R . . . .
 H2B H 0.553910 0.490972 0.915627 0.045 Uiso 1 1 calc R . . . .
 C3 C 0.7007(3) 0.4514(3) 0.8851(4) 0.0393(9) Uani 1 1 d . . . . .
 H3A H 0.740943 0.465466 0.971914 0.047 Uiso 1 1 calc R . . . .
 H3B H 0.702402 0.504758 0.831083 0.047 Uiso 1 1 calc R . . . .
 C4 C 0.7585(3) 0.3790(3) 0.8297(3) 0.0346(8) Uani 1 1 d . . . . .
 H4A H 0.776904 0.331875 0.895123 0.042 Uiso 1 1 calc R . . . .
 H4B H 0.826164 0.402749 0.809024 0.042 Uiso 1 1 calc R . . . .
 C5 C 0.5380(3) 0.4417(2) 0.6617(3) 0.0325(8) Uani 1 1 d . . . . .
 H5A H 0.537961 0.506427 0.676506 0.039 Uiso 1 1 calc R . . . .
 H5B H 0.478206 0.427578 0.590898 0.039 Uiso 1 1 calc R . . . .
 C6 C 0.6438(3) 0.4143(2) 0.6230(3) 0.0323(8) Uani 1 1 d . . . . .
 H6A H 0.631005 0.394236 0.532196 0.039 Uiso 1 1 calc R . . . .
 H6B H 0.693007 0.465580 0.630693 0.039 Uiso 1 1 calc R . . . .
 C7 C 0.7600(3) 0.2825(3) 0.6402(4) 0.0383(9) Uani 1 1 d . . . . .
 H7A H 0.826750 0.313809 0.631072 0.046 Uiso 1 1 calc R . . . .
 H7B H 0.720089 0.269385 0.552885 0.046 Uiso 1 1 calc R . . . .
 C8 C 0.7869(3) 0.1964(3) 0.7143(4) 0.0358(8) Uani 1 1 d . . . . .
 H8A H 0.840214 0.207833 0.793035 0.043 Uiso 1 1 calc R . . . .
 H8B H 0.817892 0.153438 0.660258 0.043 Uiso 1 1 calc R . . . .
 C9 C 0.3469(3) 0.18480(19) 0.7648(3) 0.0226(6) Uani 1 1 d . . . . .
 C10 C 0.3347(3) 0.1981(2) 0.6317(3) 0.0260(7) Uani 1 1 d . . . . .
 H10 H 0.394500 0.215963 0.594992 0.031 Uiso 1 1 calc R . . . .
 C11 C 0.2364(3) 0.1855(2) 0.5528(3) 0.0307(7) Uani 1 1 d . . . . .
 H11 H 0.229354 0.195101 0.462624 0.037 Uiso 1 1 calc R . . . .
 C12 C 0.1477(3) 0.1589(2) 0.6051(4) 0.0357(8) Uani 1 1 d . . . . .
 C13 C 0.1588(3) 0.1432(2) 0.7363(4) 0.0342(8) Uani 1 1 d . . . . .
 H13 H 0.099059 0.124251 0.772283 0.041 Uiso 1 1 calc R . . . .
 C15 C 0.0410(3) 0.1499(4) 0.5196(5) 0.0556(12) Uani 1 1 d . . . . .
 C00D C 0.2572(3) 0.1553(2) 0.8150(3) 0.0281(7) Uani 1 1 d . . . . .
 H00D H 0.264311 0.143530 0.904564 0.034 Uiso 1 1 calc R . . . .
 N1A N 0.1487(9) 0.4398(8) 0.6436(14) 0.131(3) Uani 0.684(13) 1 d D U P A -1
 C1A C 0.0749(10) 0.4832(9) 0.6109(18) 0.136(3) Uani 0.684(13) 1 d D U P A -1
 C2A C -0.0295(9) 0.5201(9) 0.5555(17) 0.128(4) Uani 0.684(13) 1 d D U P A -1
 H2AA H -0.016243 0.581352 0.532014 0.191 Uiso 0.684(13) 1 d R . P A -1
 H2AB H -0.081923 0.519363 0.613544 0.191 Uiso 0.684(13) 1 d R . P A -1
 H2AC H -0.057293 0.486233 0.477524 0.191 Uiso 0.684(13) 1 d R . P A -1
 N1B N 0.098(2) 0.3931(15) 0.632(2) 0.134(4) Uani 0.316(13) 1 d D U P A -2
 C1B C 0.045(3) 0.4461(18) 0.575(2) 0.135(3) Uani 0.316(13) 1 d D U P A -2
 C2B C -0.012(4) 0.504(2) 0.475(3) 0.128(4) Uani 0.316(13) 1 d D U P A -2
 H2BA H -0.080562 0.473496 0.448306 0.192 Uiso 0.316(13) 1 d R . P A -2
 H2BB H 0.018908 0.518706 0.399006 0.192 Uiso 0.316(13) 1 d R . P A -2
 H2BC H -0.024602 0.558986 0.520396 0.192 Uiso 0.316(13) 1 d R . P A -2


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 Ni1 S1 2.2061(10) . ?
 Ni1 S2 2.1450(10) . ?
 Ni1 N1 1.984(3) . ?
 Ni1 N2 1.950(3) . ?
 S1 C9 1.749(3) . ?
 S2 C8 1.831(4) . ?
 F1 C15 1.277(6) . ?
 F2 C15 1.350(6) . ?
 F3 C15 1.350(6) . ?
 N1 C1 1.493(5) . ?
 N1 C2 1.473(5) . ?
 N1 C5 1.506(4) . ?
 N2 C4 1.499(4) . ?
 N2 C6 1.525(5) . ?
 N2 C7 1.485(5) . ?
 C2 C3 1.490(6) . ?
 C3 C4 1.492(6) . ?
 C5 C6 1.528(5) . ?
 C7 C8 1.525(6) . ?
 C9 C10 1.398(5) . ?
 C9 C00D 1.409(5) . ?
 C10 C11 1.387(5) . ?
 C11 C12 1.398(5) . ?
 C12 C13 1.386(6) . ?
 C12 C15 1.496(6) . ?
 C13 C00D 1.385(5) . ?
 N1A C1A 1.146(3) . ?
 C1A C2A 1.463(3) . ?
 N1B C1B 1.146(3) . ?
 C1B C2B 1.465(3) . ?

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
  _geom_angle_publ_flag
 S2 Ni1 S1 88.33(4) . . ?
 N1 Ni1 S1 98.57(8) . . ?
 N1 Ni1 S2 172.56(9) . . ?
 N2 Ni1 S1 171.60(10) . . ?
 N2 Ni1 S2 91.12(9) . . ?
 N2 Ni1 N1 81.64(11) . . ?
 C9 S1 Ni1 110.06(11) . . ?
 C8 S2 Ni1 98.33(12) . . ?
 C1 N1 Ni1 118.9(2) . . ?
 C1 N1 C5 106.7(3) . . ?
 C2 N1 Ni1 105.0(2) . . ?
 C2 N1 C1 108.7(3) . . ?
 C2 N1 C5 110.9(3) . . ?
 C5 N1 Ni1 106.5(2) . . ?
 C4 N2 Ni1 104.4(2) . . ?
 C4 N2 C6 108.8(3) . . ?
 C6 N2 Ni1 109.1(2) . . ?
 C7 N2 Ni1 112.3(2) . . ?
 C7 N2 C4 112.1(3) . . ?
 C7 N2 C6 110.0(3) . . ?
 N1 C2 C3 114.5(3) . . ?
 C2 C3 C4 117.1(3) . . ?
 C3 C4 N2 112.7(3) . . ?
 N1 C5 C6 110.5(3) . . ?
 N2 C6 C5 109.5(3) . . ?
 N2 C7 C8 109.5(3) . . ?
 C7 C8 S2 108.9(3) . . ?
 C10 C9 S1 123.2(2) . . ?
 C10 C9 C00D 117.9(3) . . ?
 C00D C9 S1 118.9(2) . . ?
 C11 C10 C9 120.8(3) . . ?
 C10 C11 C12 120.4(3) . . ?
 C11 C12 C15 119.7(4) . . ?
 C13 C12 C11 119.6(3) . . ?
 C13 C12 C15 120.6(4) . . ?
 C00D C13 C12 119.9(3) . . ?
 F1 C15 F2 108.4(5) . . ?
 F1 C15 F3 106.6(5) . . ?
 F1 C15 C12 114.5(4) . . ?
 F2 C15 F3 101.6(4) . . ?
 F2 C15 C12 111.6(4) . . ?
 F3 C15 C12 113.2(4) . . ?
 C13 C00D C9 121.3(3) . . ?
 N1A C1A C2A 167.1(12) . . ?
 N1B C1B C2B 166.2(16) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
