#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:58:24 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/09/1570986.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_1570986
loop_
_publ_author_name
'Cook, Emma N.'
'Courter, Ian M.'
'Dickie, Diane A.'
'Machan, Charles W.'
_publ_section_title
;
 Controlling product selectivity during dioxygen reduction with Mn
 complexes using pendent proton donor relays and added base.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              4478
_journal_page_last               4488
_journal_paper_doi               10.1039/d3sc02611f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C8 H20 F6 N P'
_chemical_formula_weight         275.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_update_record
;
2023-04-12 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.3780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2349(2)
_cell_length_b                   17.2894(6)
_cell_length_c                   8.9716(3)
_cell_measurement_reflns_used    9217
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.2309
_cell_measurement_theta_min      2.5745
_cell_volume                     1266.77(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS double bounce multilayer mirror'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            30006
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.253
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0401
_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)+(0.0429P)²+0.7824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2614
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02611f3.cif
_cod_data_source_block           DIPEAHPF6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570985--1570986.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.21872(5) 0.61746(2) 0.69098(4) 0.02402(12) Uani d . . D 1.000000 . .
F F1 0.32063(15) 0.58509(7) 0.56236(12) 0.0428(3) Uani d . . . 1.000000 . .
F F2 0.3063(2) 0.69941(8) 0.6810(2) 0.0571(5) Uani d . P D 0.917(3) A 1
F F3 0.07722(19) 0.64679(9) 0.56646(15) 0.0486(4) Uani d . P D 0.917(3) A 1
F F4 0.11931(17) 0.64943(8) 0.81888(13) 0.0566(4) Uani d . . . 1.000000 . .
F F5 0.13395(18) 0.53660(8) 0.6986(2) 0.0587(5) Uani d . P D 0.917(3) A 1
F F6 0.36459(17) 0.58978(9) 0.81287(13) 0.0473(4) Uani d . P D 0.917(3) A 1
N N1 0.35876(15) 0.63192(7) 0.26193(14) 0.0189(3) Uani d . . . 1.000000 . .
H H1 0.325(2) 0.6302(11) 0.351(2) 0.027(5) Uiso d . . . 1.000000 . .
C C1 0.3460(2) 0.71480(9) 0.20480(19) 0.0258(3) Uani d . . . 1.000000 . .
H H1A 0.457298 0.734870 0.197412 0.031000 Uiso calc U . R 1.000000 . .
H H1B 0.283824 0.715514 0.102765 0.031000 Uiso calc U . R 1.000000 . .
C C2 0.2623(2) 0.76708(10) 0.3064(2) 0.0350(4) Uani d . . . 1.000000 . .
H H2A 0.261140 0.820180 0.268124 0.052000 Uiso calc U . R 1.000000 . .
H H2B 0.321934 0.765548 0.408225 0.052000 Uiso calc U . R 1.000000 . .
H H2C 0.149627 0.749391 0.308872 0.052000 Uiso calc U . R 1.000000 . .
C C3 0.53526(18) 0.60239(10) 0.28336(19) 0.0255(3) Uani d . . . 1.000000 . .
H H3 0.533145 0.547817 0.320010 0.031000 Uiso calc U . R 1.000000 . .
C C4 0.6380(2) 0.64906(12) 0.4036(2) 0.0364(4) Uani d . . . 1.000000 . .
H H4A 0.652266 0.701648 0.366683 0.055000 Uiso calc U . R 1.000000 . .
H H4B 0.745392 0.624507 0.427985 0.055000 Uiso calc U . R 1.000000 . .
H H4C 0.582776 0.651206 0.494020 0.055000 Uiso calc U . R 1.000000 . .
C C5 0.6059(2) 0.60120(12) 0.1354(2) 0.0345(4) Uani d . . . 1.000000 . .
H H5A 0.533312 0.571667 0.061082 0.052000 Uiso calc U . R 1.000000 . .
H H5B 0.714292 0.576880 0.150069 0.052000 Uiso calc U . R 1.000000 . .
H H5C 0.615833 0.654299 0.099402 0.052000 Uiso calc U . R 1.000000 . .
C C6 0.23928(18) 0.57847(9) 0.16707(17) 0.0224(3) Uani d . . . 1.000000 . .
H H6 0.264668 0.579736 0.061046 0.027000 Uiso calc U . R 1.000000 . .
C C7 0.06500(19) 0.60748(11) 0.1694(2) 0.0302(4) Uani d . . . 1.000000 . .
H H7A 0.038113 0.606183 0.272685 0.045000 Uiso calc U . R 1.000000 . .
H H7B -0.011288 0.574249 0.105589 0.045000 Uiso calc U . R 1.000000 . .
H H7C 0.056039 0.660672 0.131530 0.045000 Uiso calc U . R 1.000000 . .
C C8 0.2556(2) 0.49519(9) 0.2240(2) 0.0302(4) Uani d . . . 1.000000 . .
H H8A 0.363339 0.474870 0.208720 0.045000 Uiso calc U . R 1.000000 . .
H H8B 0.169858 0.463303 0.168520 0.045000 Uiso calc U . R 1.000000 . .
H H8C 0.244152 0.493980 0.331388 0.045000 Uiso calc U . R 1.000000 . .
F F3A 0.090(2) 0.5562(10) 0.6057(18) 0.052(3) Uani d . P D 0.083(3) A 2
F F2A 0.157(2) 0.6818(9) 0.5769(16) 0.052(3) Uani d . P D 0.083(3) A 2
F F6A 0.3491(18) 0.6693(10) 0.7763(17) 0.052(3) Uani d . P D 0.083(3) A 2
F F5A 0.271(2) 0.5449(8) 0.7997(16) 0.052(3) Uani d . P D 0.083(3) A 2
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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F6A P1 F2A . . 93.5(10) ?
F5 P1 F3 . . 91.42(10) ?
F5 P1 F6 . . 90.18(9) ?
F3 P1 F6 . . 178.06(9) ?
F6A P1 F4 . . 80.1(6) ?
F2A P1 F4 . . 94.0(6) ?
F5 P1 F4 . . 90.31(9) ?
F3 P1 F4 . . 89.85(7) ?
F6 P1 F4 . . 91.25(7) ?
F5 P1 F2 . . 179.09(9) ?
F3 P1 F2 . . 88.46(9) ?
F6 P1 F2 . . 89.93(9) ?
F4 P1 F2 . . 90.59(9) ?
F6A P1 F1 . . 99.5(6) ?
F2A P1 F1 . . 86.2(6) ?
F5 P1 F1 . . 89.84(8) ?
F3 P1 F1 . . 90.56(7) ?
F6 P1 F1 . . 88.34(6) ?
F4 P1 F1 . . 179.56(8) ?
F2 P1 F1 . . 89.27(8) ?
F6A P1 F5A . . 92.1(9) ?
F2A P1 F5A . . 174.4(9) ?
F4 P1 F5A . . 87.5(6) ?
F1 P1 F5A . . 92.3(6) ?
F6A P1 F3A . . 175.2(10) ?
F2A P1 F3A . . 90.9(10) ?
F4 P1 F3A . . 101.6(6) ?
F1 P1 F3A . . 78.8(6) ?
F5A P1 F3A . . 83.4(9) ?
C1 N1 C6 . . 111.76(12) ?
C1 N1 C3 . . 112.35(12) ?
C6 N1 C3 . . 113.71(12) ?
C1 N1 H1 . . 108.9(12) ?
C6 N1 H1 . . 103.4(13) ?
C3 N1 H1 . . 106.1(13) ?
C2 C1 N1 . . 112.15(13) ?
C2 C1 H1A . . 109.200000 ?
N1 C1 H1A . . 109.200000 ?
C2 C1 H1B . . 109.200000 ?
N1 C1 H1B . . 109.200000 ?
H1A C1 H1B . . 107.900000 ?
C1 C2 H2A . . 109.500000 ?
C1 C2 H2B . . 109.500000 ?
H2A C2 H2B . . 109.500000 ?
C1 C2 H2C . . 109.500000 ?
H2A C2 H2C . . 109.500000 ?
H2B C2 H2C . . 109.500000 ?
C4 C3 C5 . . 112.86(14) ?
C4 C3 N1 . . 110.27(14) ?
C5 C3 N1 . . 111.09(13) ?
C4 C3 H3 . . 107.500000 ?
C5 C3 H3 . . 107.500000 ?
N1 C3 H3 . . 107.500000 ?
C3 C4 H4A . . 109.500000 ?
C3 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C3 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C7 C6 N1 . . 109.51(13) ?
C7 C6 C8 . . 110.39(13) ?
N1 C6 C8 . . 111.17(13) ?
C7 C6 H6 . . 108.600000 ?
N1 C6 H6 . . 108.600000 ?
C8 C6 H6 . . 108.600000 ?
C6 C7 H7A . . 109.500000 ?
C6 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C6 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
C6 C8 H8A . . 109.500000 ?
C6 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 109.500000 ?
C6 C8 H8C . . 109.500000 ?
H8A C8 H8C . . 109.500000 ?
H8B C8 H8C . . 109.500000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 F6A . 1.527(12) ?
P1 F2A . 1.553(12) ?
P1 F5 . 1.5679(14) ?
P1 F3 . 1.5901(12) ?
P1 F6 . 1.5908(12) ?
P1 F4 . 1.5917(11) ?
P1 F2 . 1.5979(14) ?
P1 F1 . 1.6118(11) ?
P1 F5A . 1.614(11) ?
P1 F3A . 1.620(12) ?
N1 C1 . 1.5210(19) ?
N1 C6 . 1.5268(18) ?
N1 C3 . 1.5292(19) ?
N1 H1 . 0.88(2) ?
C1 C2 . 1.512(2) ?
C1 H1A . 0.990000 ?
C1 H1B . 0.990000 ?
C2 H2A . 0.980000 ?
C2 H2B . 0.980000 ?
C2 H2C . 0.980000 ?
C3 C4 . 1.516(2) ?
C3 C5 . 1.517(2) ?
C3 H3 . 1.000000 ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C6 C7 . 1.523(2) ?
C6 C8 . 1.528(2) ?
C6 H6 . 1.000000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C8 H8A . 0.980000 ?
C8 H8B . 0.980000 ?
C8 H8C . 0.980000 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 F1 . 0.88(2) 2.06(2) 2.8698(16) 153.9(17) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 C1 C2 . . . . 106.70(15) ?
C3 N1 C1 C2 . . . . -124.09(15) ?
C1 N1 C3 C4 . . . . 63.63(17) ?
C6 N1 C3 C4 . . . . -168.18(13) ?
C1 N1 C3 C5 . . . . -62.27(17) ?
C6 N1 C3 C5 . . . . 65.92(17) ?
C1 N1 C6 C7 . . . . -58.79(16) ?
C3 N1 C6 C7 . . . . 172.72(13) ?
C1 N1 C6 C8 . . . . 178.97(12) ?
C3 N1 C6 C8 . . . . 50.48(16) ?
