#------------------------------------------------------------------------------
#$Date: 2017-05-05 11:52:25 +0300 (Fri, 05 May 2017) $
#$Revision: 196240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/28/7042892.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_7042892
loop_
_publ_author_name
'Sondermann, Christina'
'Ringenberg, Mark R.'
_publ_section_title
;
 Tuning the overpotential of electrocatalytically active
 cyclopentadienylnickel complexes containing 1,4-diaza-1,3-butadienes
 (DAB) for proton reduction.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5143
_journal_page_last               5146
_journal_paper_doi               10.1039/c7dt00960g
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'B F4, C21 H21 N2 Ni'
_chemical_formula_sum            'C21 H21 B F4 N2 Ni'
_chemical_formula_weight         446.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-09-14 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9844(8)
_cell_length_b                   15.3276(11)
_cell_length_c                   10.8448(8)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    100
_cell_measurement_theta_max      0.745
_cell_measurement_theta_min      0.642
_cell_volume                     1992.1(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24840
_diffrn_reflns_theta_full        26.4699
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.4900
_exptl_crystal_description       needle
_exptl_crystal_F_000             921.8941
_exptl_crystal_preparation       none
_exptl_crystal_recrystallization_method 'slow evaporation of CH2Cl2 solution'
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.6944
_refine_diff_density_min         -0.5992
_refine_diff_density_rms         0.0775
_refine_ls_d_res_high            0.7973
_refine_ls_d_res_low             8.8530
_refine_ls_goodness_of_fit_ref   1.0667
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.0434
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1756
_reflns_number_total             2133
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7dt00960g2.cif
_cod_data_source_block           ac353
_cod_database_code               7042892
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C3) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C8(H8), C11(H11), C10(H10)
3.c Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c)
;
_olex2_exptl_crystal_mounting_method
'crystals were mounted using perfluoropolyalkylether from ABCR viscosity 1800 cts on to a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
F1 F 0.45865(19) 0.25 0.34304(19) 0.0429(5) Uani 1.000000 2 S T P .
F2 F 0.50861(10) 0.17561(9) 0.51423(14) 0.0332(4) Uani 1.000000 1 . . . .
F3 F 0.64090(15) 0.25 0.4070(2) 0.0425(5) Uani 1.000000 2 S T P .
N1 N 0.17854(13) 0.66938(11) 0.36867(16) 0.0201(4) Uani 1.000000 1 . . . .
C6 C 0.19223(16) 0.57676(12) 0.35223(19) 0.0218(5) Uani 1.000000 1 . . . .
C4 C 0.12377(15) 0.70222(13) 0.46198(19) 0.0207(4) Uani 1.000000 1 . . . .
C7 C 0.12240(19) 0.53183(15) 0.2730(2) 0.0323(6) Uani 1.000000 1 . . . .
H7 H 0.06220(19) 0.56111(15) 0.2338(2) 0.0387(7) Uiso 1.000000 1 R . . .
C5 C 0.06551(17) 0.65105(14) 0.5589(2) 0.0274(5) Uani 1.000000 1 . . . .
H5a H 0.0949(9) 0.6672(7) 0.6401(2) 0.0410(7) Uiso 1.000000 1 GR . . .
H5b H -0.0146(2) 0.6635(8) 0.5558(10) 0.0410(7) Uiso 1.000000 1 GR . . .
H5c H 0.0779(11) 0.58864(14) 0.5448(8) 0.0410(7) Uiso 1.000000 1 GR . . .
C9 C 0.2301(2) 0.40234(17) 0.3048(3) 0.0365(6) Uani 1.000000 1 . . . .
H9 H 0.2434(2) 0.34226(17) 0.2890(3) 0.0438(7) Uiso 1.000000 1 R . . .
C8 C 0.1407(2) 0.44361(16) 0.2509(2) 0.0352(6) Uani 1.000000 1 . . . .
H8 H 0.0916(2) 0.41195(16) 0.1987(2) 0.0422(7) Uiso 1.000000 1 R . . .
C11 C 0.2822(2) 0.53563(15) 0.4066(3) 0.0368(6) Uani 1.000000 1 . . . .
H11 H 0.3306(2) 0.56672(15) 0.4603(3) 0.0442(7) Uiso 1.000000 1 R . . .
C10 C 0.3004(2) 0.44785(16) 0.3814(3) 0.0445(7) Uani 1.000000 1 . . . .
H10 H 0.3623(2) 0.41894(16) 0.4177(3) 0.0534(8) Uiso 1.000000 1 R . . .
B1 B 0.5298(3) 0.25 0.4445(3) 0.0247(7) Uani 1.000000 2 S T P .
Ni1 Ni 0.24599(2) 0.75 0.26523(4) 0.01781(18) Uani 1.000000 2 S T P .
C1 C 0.2658(3) 0.75 0.0709(4) 0.0402(9) Uani 1.000000 2 S TU P 1
H1 H 0.2065(3) 0.75 0.0060(4) 0.0482(11) Uiso 1.000000 2 RS T P 1
C2 C 0.3173(3) 0.67762(17) 0.1281(3) 0.0562(9) Uani 1.000000 1 . U . 1
H2 H 0.3006(3) 0.61498(17) 0.1100(3) 0.0675(10) Uiso 1.000000 1 R . . 1
C3 C 0.4003(2) 0.7075(3) 0.2069(3) 0.0744(12) Uani 1.000000 1 . U . 1
H3 H 0.4521(2) 0.6698(3) 0.2555(3) 0.0892(14) Uiso 1.000000 1 R . . 1
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C4 N1 C6 122.18(17) . .
Ni1 N1 C6 122.16(13) 7_575 .
Ni1 N1 C4 115.51(14) 7_575 .
C7 C6 N1 119.92(18) . .
C11 C6 N1 119.08(19) . .
C11 C6 C7 120.7(2) . .
C4 C4 N1 112.65(12) 7_575 .
C5 C4 N1 125.49(18) . .
C8 C7 C6 119.7(2) . .
C10 C9 C8 120.1(2) . .
C9 C8 C7 119.8(2) . .
C10 C11 C6 118.7(2) . .
C11 C10 C9 120.9(2) . .
F2 B1 F1 108.52(18) . .
F2 B1 F1 108.52(18) 7_565 .
F2 B1 F2 110.0(3) 7_565 .
F3 B1 F1 110.8(3) . .
F3 B1 F2 109.47(17) . .
F3 B1 F2 109.47(17) . 7_565
N1 Ni1 N1 83.57(10) . 7_575
C2 Ni1 C1 39.62(10) . .
C2 Ni1 C1 39.62(10) 7_575 .
C2 Ni1 C2 65.79(15) . 7_575
C3 Ni1 C1 66.05(12) 7_575 .
C3 Ni1 C1 66.05(12) . .
C3 Ni1 C2 39.56(14) . .
C3 Ni1 C2 64.69(13) . 7_575
C3 Ni1 C2 64.69(13) 7_575 .
C3 Ni1 C2 39.56(14) 7_575 7_575
C3 Ni1 C3 36.9(2) . 7_575
C2 C1 C2 103.5(4) . 7_575
C3 C2 C1 108.9(3) . 7_575
C3 C3 C2 109.27(18) 7_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 B1 1.392(4) .
F2 B1 1.392(3) 7_565
F3 B1 1.392(4) .
N1 C6 1.440(3) .
N1 C4 1.307(3) .
N1 Ni1 1.8544(16) 7_575
C6 C7 1.383(3) .
C6 C11 1.381(3) .
C4 C4 1.465(4) 7_575
C4 C5 1.486(3) .
C7 C8 1.391(3) .
C9 C8 1.375(4) .
C9 C10 1.374(4) .
C11 C10 1.390(4) .
Ni1 C1 2.121(4) .
Ni1 C2 2.043(2) 7_575
Ni1 C2 2.043(2) .
Ni1 C3 2.060(3) .
Ni1 C3 2.060(3) 7_575
C1 C2 1.413(4) 7_575
C1 C2 1.413(4) .
C2 C3 1.389(5) .
C3 C3 1.302(8) 7_575
loop_
_restr_u_iso_atom_site_label
_restr_u_iso_weight_param
C1 0.1000
C1 0.0100
C1 0.1000
C1 0.1000
C1 0.0100
C2 0.1000
C2 0.1000
C2 0.0100
C2 0.1000
C2 0.0100
C3 0.1000
C3 0.0100
C3 0.1000
C3 0.1000
C3 0.0100
