#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/29/4122986.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_4122986
loop_
_publ_author_name
'Kalz, Kai F.'
'Brinkmeier, Alexander'
'Dechert, Sebastian'
'Mata, Ricardo A.'
'Meyer, Franc'
_publ_section_title
;
 Functional Model for the [Fe] Hydrogenase Inspired by the Frustrated
 Lewis Pair Concept.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141117115410006
_journal_paper_doi               10.1021/ja509186d
_journal_year                    2014
_chemical_formula_moiety         'C22 H17 F4 N2 +, Br -, H2 O'
_chemical_formula_sum            'C22 H19 Br F4 N2 O'
_chemical_formula_weight         483.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                111.553(4)
_cell_angle_beta                 96.864(4)
_cell_angle_gamma                102.719(4)
_cell_formula_units_Z            2
_cell_length_a                   10.3885(5)
_cell_length_b                   10.4707(5)
_cell_length_c                   10.6706(5)
_cell_measurement_reflns_used    13660
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.06
_cell_volume                     1027.04(10)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2002)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13660
_diffrn_reflns_theta_full        26.72
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.053
_exptl_absorpt_correction_T_max  0.7487
_exptl_absorpt_correction_T_min  0.3849
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0224P)²+0.6761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0605
_reflns_number_gt                4091
_reflns_number_total             4340
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja509186d_si_002.cif
_cod_data_source_block           ImF4Br-kk18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 
;
_cod_original_cell_volume        1027.04(8)
_cod_database_code               4122986
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
N1 N 0.53349(13) 0.24973(15) 0.85448(13) 0.0191(3) Uani 1 1 d .
N2 N 0.65721(13) 0.29945(14) 0.71699(13) 0.0177(3) Uani 1 1 d .
F1 F 0.40598(12) 0.40132(11) 1.04128(12) 0.0352(3) Uani 1 1 d .
F2 F 0.44249(12) -0.04432(11) 0.75613(11) 0.0350(3) Uani 1 1 d .
F3 F 0.57255(11) 0.51583(11) 0.67375(11) 0.0290(2) Uani 1 1 d .
F4 F 0.82686(11) 0.18864(12) 0.55669(12) 0.0329(2) Uani 1 1 d .
C1 C 0.53197(15) 0.25175(16) 0.73005(15) 0.0165(3) Uani 1 1 d .
C2 C 0.67205(16) 0.3055(2) 0.94123(17) 0.0250(4) Uani 1 1 d .
H2A H 0.6946 0.2349 0.9749 0.030 Uiso 1 1 calc R
H2B H 0.6831 0.3963 1.0214 0.030 Uiso 1 1 calc R
C3 C 0.75931(16) 0.32928(19) 0.84204(17) 0.0234(3) Uani 1 1 d .
H3A H 0.8187 0.4290 0.8804 0.028 Uiso 1 1 calc R
H3B H 0.8157 0.2624 0.8212 0.028 Uiso 1 1 calc R
C4 C 0.40934(15) 0.20386(16) 0.62264(15) 0.0162(3) Uani 1 1 d .
C5 C 0.28789(16) 0.22756(17) 0.65632(16) 0.0188(3) Uani 1 1 d .
H5 H 0.2849 0.2779 0.7498 0.023 Uiso 1 1 calc R
C6 C 0.17252(16) 0.17755(17) 0.55316(16) 0.0199(3) Uani 1 1 d .
H6 H 0.0905 0.1934 0.5771 0.024 Uiso 1 1 calc R
C7 C 0.17353(16) 0.10430(17) 0.41452(16) 0.0194(3) Uani 1 1 d .
C8 C 0.29600(17) 0.08297(17) 0.38228(16) 0.0200(3) Uani 1 1 d .
H8 H 0.2991 0.0342 0.2885 0.024 Uiso 1 1 calc R
C9 C 0.41217(16) 0.13123(17) 0.48381(16) 0.0186(3) Uani 1 1 d .
H9 H 0.4941 0.1153 0.4597 0.022 Uiso 1 1 calc R
C10 C 0.04799(18) 0.0527(2) 0.30293(18) 0.0273(4) Uani 1 1 d .
H10A H -0.0318 0.0451 0.3432 0.041 Uiso 1 1 calc R
H10B H 0.0434 -0.0415 0.2332 0.041 Uiso 1 1 calc R
H10C H 0.0505 0.1208 0.2596 0.041 Uiso 1 1 calc R
C11 C 0.42469(15) 0.17961(17) 0.89713(15) 0.0179(3) Uani 1 1 d .
C12 C 0.36345(17) 0.25745(18) 0.99493(17) 0.0225(3) Uani 1 1 d .
C13 C 0.26135(18) 0.1930(2) 1.04196(18) 0.0262(4) Uani 1 1 d .
H13 H 0.2211 0.2486 1.1094 0.031 Uiso 1 1 calc R
C14 C 0.21898(17) 0.0445(2) 0.98799(17) 0.0246(3) Uani 1 1 d .
H14 H 0.1475 -0.0019 1.0180 0.029 Uiso 1 1 calc R
C15 C 0.27844(18) -0.03796(19) 0.89130(17) 0.0243(3) Uani 1 1 d .
H15 H 0.2491 -0.1396 0.8554 0.029 Uiso 1 1 calc R
C16 C 0.38099(17) 0.03175(18) 0.84908(16) 0.0210(3) Uani 1 1 d .
C17 C 0.69655(15) 0.34927(16) 0.61592(15) 0.0176(3) Uani 1 1 d .
C18 C 0.65754(16) 0.46066(18) 0.59805(17) 0.0214(3) Uani 1 1 d .
C19 C 0.70267(18) 0.51664(19) 0.50757(18) 0.0267(4) Uani 1 1 d .
H19 H 0.6729 0.5920 0.4962 0.032 Uiso 1 1 calc R
C20 C 0.79255(18) 0.4603(2) 0.43357(18) 0.0281(4) Uani 1 1 d .
H20 H 0.8247 0.4979 0.3709 0.034 Uiso 1 1 calc R
C21 C 0.83625(18) 0.35049(19) 0.44928(18) 0.0262(4) Uani 1 1 d .
H21 H 0.8986 0.3130 0.3989 0.031 Uiso 1 1 calc R
C22 C 0.78718(16) 0.29662(18) 0.53985(17) 0.0217(3) Uani 1 1 d .
O1 O 0.89846(15) 0.64372(16) 0.14506(15) 0.0356(3) Uani 1 1 d D
Br1 Br 0.983155(16) 0.347398(18) 0.137772(17) 0.02477(6) Uani 1 1 d .
H1A H 0.926(3) 0.576(3) 0.149(3) 0.080 Uiso 1 1 d D
H1B H 0.933(3) 0.659(4) 0.084(3) 0.080 Uiso 1 1 d 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 0.0000 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'
Br Br -0.2901 2.4595 '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
C1 N1 C11 126.87(13)
C1 N1 C2 111.94(13)
C11 N1 C2 120.17(12)
C1 N2 C17 127.28(13)
C1 N2 C3 111.50(12)
C17 N2 C3 119.82(12)
N2 C1 N1 110.50(14)
N2 C1 C4 125.28(13)
N1 C1 C4 124.19(14)
N1 C2 C3 102.79(12)
N2 C3 C2 102.85(12)
C5 C4 C9 119.26(14)
C5 C4 C1 120.98(14)
C9 C4 C1 119.76(14)
C6 C5 C4 119.80(14)
C5 C6 C7 121.61(15)
C6 C7 C8 117.94(15)
C6 C7 C10 121.14(15)
C8 C7 C10 120.91(15)
C9 C8 C7 121.37(14)
C8 C9 C4 120.01(14)
C16 C11 C12 117.26(14)
C16 C11 N1 121.62(14)
C12 C11 N1 121.01(14)
F1 C12 C13 120.41(15)
F1 C12 C11 117.12(14)
C13 C12 C11 122.45(16)
C12 C13 C14 118.01(16)
C13 C14 C15 121.63(15)
C16 C15 C14 118.01(16)
F2 C16 C15 119.95(15)
F2 C16 C11 117.44(14)
C15 C16 C11 122.61(15)
C18 C17 C22 116.88(14)
C18 C17 N2 122.07(14)
C22 C17 N2 120.76(14)
F3 C18 C19 119.59(16)
F3 C18 C17 117.77(14)
C19 C18 C17 122.64(16)
C18 C19 C20 118.39(17)
C21 C20 C19 121.20(15)
C22 C21 C20 118.42(16)
F4 C22 C21 119.92(15)
F4 C22 C17 117.63(14)
C21 C22 C17 122.45(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3340(19)
N1 C11 1.4237(19)
N1 C2 1.478(2)
N2 C1 1.330(2)
N2 C17 1.4238(19)
N2 C3 1.487(2)
F1 C12 1.348(2)
F2 C16 1.3496(19)
F3 C18 1.3482(19)
F4 C22 1.348(2)
C1 C4 1.461(2)
C2 C3 1.526(2)
C4 C5 1.401(2)
C4 C9 1.402(2)
C5 C6 1.381(2)
C6 C7 1.397(2)
C7 C8 1.400(2)
C7 C10 1.502(2)
C8 C9 1.379(2)
C11 C16 1.385(2)
C11 C12 1.386(2)
C12 C13 1.376(2)
C13 C14 1.387(3)
C14 C15 1.387(2)
C15 C16 1.373(2)
C17 C18 1.384(2)
C17 C22 1.390(2)
C18 C19 1.378(2)
C19 C20 1.386(3)
C20 C21 1.382(3)
C21 C22 1.380(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A Br1 0.837(18) 2.551(18) 3.3835(15) 173(3) .
O1 H1B Br1 0.831(18) 2.598(19) 3.4165(14) 169(3) 2_765
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139123747
