#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:56:53 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257026 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/73/4517324.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_4517324
loop_
_publ_author_name
'Wu, Zhuo-Yan'
'Xue, Haozong'
'Wang, Teng'
'Guo, Yanru'
'Meng, Yin-Shan'
'Li, Xingguo'
'Zheng, Jie'
'Brückner, Christian'
'Rao, Guodong'
'Britt, R. David'
'Zhang, Jun-Long'
_publ_section_title
;
 Mimicking of Tunichlorin: Deciphering the Importance of a β-Hydroxyl
 Substituent on Boosting the Hydrogen Evolution Reaction
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2177
_journal_page_last               2188
_journal_paper_doi               10.1021/acscatal.9b03985
_journal_year                    2020
_chemical_formula_sum            'C43 H10 F20 N4 Ni O2'
_chemical_formula_weight         1053.26
_space_group_crystal_system      tetragonal
_space_group_IT_number           122
_space_group_name_Hall           'I -4 2bw'
_space_group_name_H-M_alt        'I -4 2 d'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3766(3)
_cell_length_b                   15.3766(3)
_cell_length_c                   15.4761(5)
_cell_measurement_reflns_used    10137
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      25.8390
_cell_measurement_theta_min      3.6960
_cell_volume                     3659.17(16)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180.01(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29373
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.231
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_description       block
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 696 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+3.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1693
_reflns_number_total             1868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b03985_si_003.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 4517324--4517325.cif.'
_cod_original_cell_volume        3659.17(19)
_cod_database_code               4517324
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y, -z+3/4'
'x+1/2, -y, -z+3/4'
'-y+1/2, -x, z+3/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1, y+1/2, -z+5/4'
'x+1, -y+1/2, -z+5/4'
'-y+1, -x+1/2, z+5/4'
'y+1, x+1/2, z+5/4'
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 0.5000 0.5000 0.5000 0.0318(3) Uani 1 4 d S T P . .
N1 N 0.5653(2) 0.6068(2) 0.4982(3) 0.0332(8) Uani 1 1 d . . . . .
C1 C 0.6519(3) 0.6175(3) 0.5160(3) 0.0378(11) Uani 1 1 d D . . . .
C4 C 0.5360(3) 0.6870(3) 0.4743(3) 0.0386(12) Uani 1 1 d D . . . .
C5 C 0.7093(3) 0.5512(3) 0.5356(3) 0.0349(11) Uani 1 1 d . . . . .
C6 C 0.8002(3) 0.5747(3) 0.5591(4) 0.0394(11) Uani 1 1 d . . . . .
C7 C 0.8231(3) 0.6028(4) 0.6412(4) 0.0450(12) Uani 1 1 d . . . . .
C8 C 0.9062(4) 0.6293(4) 0.6617(4) 0.0546(15) Uani 1 1 d . . . . .
C9 C 0.9698(4) 0.6257(4) 0.5999(5) 0.0546(15) Uani 1 1 d . . . . .
C10 C 0.9508(3) 0.5976(4) 0.5184(4) 0.0487(13) Uani 1 1 d . . . . .
C11 C 0.8668(3) 0.5731(3) 0.4986(4) 0.0455(12) Uani 1 1 d . . . . .
F1 F 0.7621(2) 0.6058(3) 0.7032(2) 0.0607(9) Uani 1 1 d . . . . .
F2 F 0.9256(3) 0.6583(4) 0.7401(3) 0.0857(14) Uani 1 1 d . . . . .
F3 F 1.0514(2) 0.6499(3) 0.6185(3) 0.0791(13) Uani 1 1 d . . . . .
F4 F 1.0132(2) 0.5941(3) 0.4588(2) 0.0716(10) Uani 1 1 d . . . . .
F5 F 0.8497(2) 0.5464(3) 0.4182(2) 0.0692(11) Uani 1 1 d . . . . .
C2 C 0.679(4) 0.703(2) 0.497(5) 0.053(8) Uani 0.5 1 d . . P A 1
H2 H 0.7333 0.7274 0.5056 0.064 Uiso 0.5 1 calc R U P A 1
C3 C 0.6057(18) 0.7435(15) 0.4615(14) 0.031(4) Uani 0.5 1 d D . P A 1
H3 H 0.6039 0.7976 0.4347 0.037 Uiso 0.5 1 calc R U P A 1
O1 O 0.635(2) 0.755(2) 0.388(2) 0.154(14) Uani 0.25 1 d D . P A 2
H1 H 0.6593 0.7083 0.3805 0.231 Uiso 0.25 1 calc R U P A 2
O2 O 0.674(4) 0.707(2) 0.512(6) 0.053(8) Uani 0.25 1 d D . P A 2
C3A C 0.606(4) 0.760(3) 0.477(2) 0.031(4) Uani 0.25 1 d D . P A 2
H3A H 0.5926 0.8168 0.5024 0.037 Uiso 0.25 1 calc R U P A 2
C2B C 0.685(4) 0.710(2) 0.521(7) 0.053(8) Uani 0.25 1 d D . P A 3
H2B1 H 0.7010 0.7269 0.5797 0.064 Uiso 0.25 1 calc R U P A 3
H2B2 H 0.7333 0.7209 0.4822 0.064 Uiso 0.25 1 calc R U P A 3
C3B C 0.603(2) 0.752(2) 0.492(3) 0.031(4) Uani 0.25 1 d D . P A 3
H3B1 H 0.5823 0.7914 0.5359 0.037 Uiso 0.25 1 calc R U P A 3
H3B2 H 0.6140 0.7849 0.4397 0.037 Uiso 0.25 1 calc R U P A 3
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'
Ni Ni 0.3393 1.1124 '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
N1 Ni1 N1 178.3(2) . 2_665
N1 Ni1 N1 90.010(5) . 3_566
N1 Ni1 N1 90.012(4) 2_665 3_566
N1 Ni1 N1 90.014(4) . 4_656
N1 Ni1 N1 90.012(5) 2_665 4_656
N1 Ni1 N1 178.3(2) 3_566 4_656
C4 N1 C1 105.5(4) . .
C4 N1 Ni1 127.0(3) . .
C1 N1 Ni1 127.4(3) . .
N1 C1 C5 125.2(4) . .
N1 C1 C2 111(2) . .
C5 C1 C2 123(2) . .
N1 C1 O2 110(3) . .
C5 C1 O2 125(3) . .
N1 C1 C2B 117(2) . .
C5 C1 C2B 118(2) . .
N1 C4 C5 124.9(4) . 4_656
N1 C4 C3 110.3(14) . .
C5 C4 C3 124.8(14) 4_656 .
N1 C4 C3B 109.4(19) . .
C5 C4 C3B 122.2(19) 4_656 .
N1 C4 C3A 115(2) . .
C5 C4 C3A 119(2) 4_656 .
C1 C5 C4 121.9(4) . 3_566
C1 C5 C6 118.3(4) . .
C4 C5 C6 119.5(4) 3_566 .
C11 C6 C7 115.9(5) . .
C11 C6 C5 121.6(5) . .
C7 C6 C5 122.5(5) . .
F1 C7 C8 118.2(5) . .
F1 C7 C6 119.2(5) . .
C8 C7 C6 122.6(5) . .
F2 C8 C9 119.5(5) . .
F2 C8 C7 121.3(6) . .
C9 C8 C7 119.2(6) . .
F3 C9 C10 119.1(6) . .
F3 C9 C8 120.5(6) . .
C10 C9 C8 120.4(5) . .
F4 C10 C9 119.9(5) . .
F4 C10 C11 120.6(5) . .
C9 C10 C11 119.5(5) . .
F5 C11 C10 118.3(5) . .
F5 C11 C6 119.3(4) . .
C10 C11 C6 122.4(5) . .
C3 C2 C1 105(3) . .
C3 C2 H2 127.3 . .
C1 C2 H2 127.3 . .
C2 C3 C4 107(3) . .
C2 C3 H3 126.7 . .
C4 C3 H3 126.7 . .
C3A O1 H1 109.5 . .
C1 O2 C3A 113(4) . .
O2 C3A O1 96(5) . .
O2 C3A C4 96(4) . .
O1 C3A C4 99(3) . .
O2 C3A H3A 120.2 . .
O1 C3A H3A 120.2 . .
C4 C3A H3A 120.2 . .
C3B C2B C1 96(3) . .
C3B C2B H2B1 112.7 . .
C1 C2B H2B1 112.7 . .
C3B C2B H2B2 112.6 . .
C1 C2B H2B2 112.6 . .
H2B1 C2B H2B2 110.1 . .
C4 C3B C2B 111(3) . .
C4 C3B H3B1 109.3 . .
C2B C3B H3B1 109.3 . .
C4 C3B H3B2 109.3 . .
C2B C3B H3B2 109.4 . .
H3B1 C3B H3B2 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 N1 1.925(4) .
Ni1 N1 1.925(4) 2_665
Ni1 N1 1.925(4) 3_566
Ni1 N1 1.925(4) 4_656
N1 C4 1.364(6) .
N1 C1 1.370(6) .
C1 C5 1.382(7) .
C1 C2 1.41(3) .
C1 O2 1.42(3) .
C1 C2B 1.52(3) .
C4 C5 1.392(7) 4_656
C4 C3 1.39(2) .
C4 C3B 1.46(3) .
C4 C3A 1.56(5) .
C5 C4 1.392(7) 3_566
C5 C6 1.489(7) .
C6 C11 1.387(8) .
C6 C7 1.387(8) .
C7 F1 1.343(6) .
C7 C8 1.379(8) .
C8 F2 1.326(7) .
C8 C9 1.369(9) .
C9 F3 1.340(6) .
C9 C10 1.365(9) .
C10 F4 1.332(7) .
C10 C11 1.381(7) .
C11 F5 1.335(7) .
C2 C3 1.39(3) .
C2 H2 0.9300 .
C3 H3 0.9300 .
O1 C3A 1.44(3) .
O1 H1 0.8200 .
O2 C3A 1.43(3) .
C3A H3A 0.9800 .
C2B C3B 1.49(3) .
C2B H2B1 0.9700 .
C2B H2B2 0.9700 .
C3B H3B1 0.9700 .
C3B H3B2 0.9700 .
