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#$Date: 2024-05-05 04:56:03 +0300 (Sun, 05 May 2024) $
#$Revision: 291581 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/12/1571250.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_1571250
loop_
_publ_author_name
'Kopp, Richard O.'
'Kleynemeyer, Sabrina L.'
'Groth, Lucie J.'
'Ernst, Moritz J.'
'Rupf, Susanne M.'
'Weber, Manuela'
'Kershaw Cook, Laurence J.'
'Coles, Nathan T.'
'Neale, Samuel E.'
'Müller, Christian'
_publ_section_title
;
 Highly selective, reversible water activation by P,N-cooperativity in
 pyridyl-functionalized phosphinines.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              5496
_journal_page_last               5506
_journal_paper_doi               10.1039/d3sc05930h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C25 H17 N4 P'
_chemical_formula_sum            'C25 H17 N4 P'
_chemical_formula_weight         404.39
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-30
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-31 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2936(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0233(2)
_cell_length_b                   7.6255(2)
_cell_length_c                   21.2045(6)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.84
_cell_volume                     972.33(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25237
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.510
_diffrn_reflns_theta_min         2.839
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9367
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1385 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.9407.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       Block
_exptl_crystal_F_000             420
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeCN'
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.337
_exptl_crystal_size_min          0.272
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.299
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0228P)²+1.0450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2936
_reflns_number_total             2955
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05930h2.cif
_cod_data_source_block           lg012
_cod_depositor_comments
'Adding full bibliography for 1571249--1571254.cif.'
_cod_database_code               1571250
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.918
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C4) = Uanis(C5)
3. Others
 Fixed Sof: P1(0.5) C5(0.5) C1(0.5) C4(0.5) C3(0.5) H3(0.5) C2(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C7(H7), C14(H14), C8(H8), C10(H10), C13(H13), C9(H9),
 C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
P1 P 0.37648(18) 0.68243(15) 0.45493(5) 0.01503(19) Uani 0.5 1 d . . P A -1
N2 N 0.3163(2) 0.85426(19) 0.60700(7) 0.0197(3) Uani 1 1 d . . . . .
C5 C 0.348(2) 0.6240(17) 0.534(3) 0.0139(13) Uani 0.5 1 d . . P A -1
C6 C 0.6015(3) 0.5596(2) 0.36615(8) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.4300(3) 0.6253(2) 0.32980(8) 0.0273(3) Uani 1 1 d . . . . .
C12 C -0.0107(3) 0.7755(2) 0.54290(8) 0.0209(3) Uani 1 1 d . . . . .
H12 H -0.077753 0.703291 0.510654 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2128(2) 0.75394(19) 0.56237(7) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.1961(3) 0.9805(2) 0.63283(8) 0.0227(3) Uani 1 1 d . . . . .
H15 H 0.268088 1.054311 0.663757 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8141(3) 0.5433(2) 0.34395(8) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.933052 0.499319 0.370752 0.027 Uiso 1 1 calc R U . . .
C14 C -0.0278(3) 1.0094(2) 0.61696(8) 0.0234(3) Uani 1 1 d . . . . .
H14 H -0.106778 1.099546 0.636992 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8499(3) 0.5921(3) 0.28231(8) 0.0280(4) Uani 1 1 d . . . . .
H8 H 0.993057 0.580390 0.266141 0.034 Uiso 1 1 calc R U . . .
C10 C 0.4694(4) 0.6728(3) 0.27069(9) 0.0319(4) Uani 1 1 d . . . . .
H10 H 0.349154 0.719599 0.245029 0.038 Uiso 1 1 calc R U . . .
C13 C -0.1334(3) 0.9041(2) 0.57136(9) 0.0241(3) Uani 1 1 d . . . . .
H13 H -0.286815 0.919529 0.559771 0.029 Uiso 1 1 calc R U . . .
C9 C 0.6731(4) 0.6583(3) 0.24463(9) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.691916 0.692545 0.202194 0.038 Uiso 1 1 calc R U . . .
C1 C 0.553(4) 0.520(3) 0.4288(7) 0.0139(13) Uani 0.5 1 d . . P A -1
C4 C 0.449(4) 0.478(3) 0.5633(7) 0.0139(13) Uani 0.5 1 d . . P A -1
C3 C 0.5883(7) 0.3707(6) 0.5304(2) 0.0169(8) Uani 0.5 1 d . . P A -1
H3 H 0.654919 0.275537 0.553345 0.020 Uiso 0.5 1 calc R U P A -1
C2 C 0.641(2) 0.3861(17) 0.468(3) 0.0139(13) Uani 0.5 1 d . . P A -1
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -3.00 0.1230
0.00 -1.00 3.00 0.1360
-1.00 3.00 4.00 0.1810
1.00 -5.00 2.00 0.1530
-6.00 -1.00 -9.00 0.1520
7.00 0.00 6.00 0.2270
4.00 1.00 8.00 0.2120
0.00 -2.00 -7.00 0.1150
0.00 2.00 7.00 0.1520
-1.00 1.00 3.00 0.2270
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
C1 P1 C5 102.6(7) . . ?
C15 N2 C11 117.20(14) . . ?
C11 C5 P1 108.4(14) . . ?
C4 C5 P1 124(4) . . ?
C4 C5 C11 127(5) . . ?
N1 C6 C7 121.85(16) . . ?
N1 C6 C1 115.2(11) . . ?
C7 C6 C1 122.9(10) . . ?
C10 N1 C6 117.66(17) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 118.95(15) . . ?
N2 C11 C5 116.0(13) . . ?
N2 C11 C12 122.88(14) . . ?
C12 C11 C5 121.1(13) . . ?
N2 C15 H15 118.1 . . ?
N2 C15 C14 123.72(16) . . ?
C14 C15 H15 118.1 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.32(16) . . ?
C8 C7 H7 120.3 . . ?
C15 C14 H14 120.7 . . ?
C13 C14 C15 118.56(16) . . ?
C13 C14 H14 120.7 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.89(19) . . ?
C9 C8 H8 120.6 . . ?
N1 C10 H10 117.9 . . ?
N1 C10 C9 124.26(17) . . ?
C9 C10 H10 117.9 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.66(15) . . ?
C14 C13 H13 120.7 . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.99(17) . . ?
C10 C9 H9 121.0 . . ?
C6 C1 P1 108.0(13) . . ?
C2 C1 P1 123(3) . . ?
C2 C1 C6 129(5) . . ?
C3 C4 C5 120(3) . . ?
C4 C3 H3 116.1 . . ?
C2 C3 C4 127.7(6) . . ?
C2 C3 H3 116.1 . . ?
C3 C2 C1 122(3) . . ?
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
P1 C5 1.75(5) . ?
P1 C1 1.75(4) . ?
N2 C11 1.342(2) . ?
N2 C15 1.340(2) . ?
C5 C11 1.44(3) . ?
C5 C4 1.402(14) . ?
C6 N1 1.349(2) . ?
C6 C7 1.395(2) . ?
C6 C1 1.410(15) . ?
N1 C10 1.339(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.395(2) . ?
C12 C13 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.383(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.378(3) . ?
C13 H13 0.9500 . ?
C9 H9 0.9500 . ?
C1 C2 1.405(16) . ?
C4 C3 1.39(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.38(6) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C5 C11 N2 -112.3(14) . . . . ?
P1 C5 C11 C12 66.0(9) . . . . ?
P1 C5 C4 C3 2(2) . . . . ?
P1 C1 C2 C3 2(2) . . . . ?
N2 C15 C14 C13 -0.9(3) . . . . ?
C5 P1 C1 C6 -176.0(9) . . . . ?
C5 P1 C1 C2 -1.6(9) . . . . ?
C5 C4 C3 C2 -1.6(10) . . . . ?
C6 N1 C10 C9 0.3(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C6 C1 C2 C3 175.5(6) . . . . ?
N1 C6 C7 C8 -1.5(3) . . . . ?
N1 C6 C1 P1 -38.5(8) . . . . ?
N1 C6 C1 C2 147.6(15) . . . . ?
N1 C10 C9 C8 -0.8(3) . . . . ?
C11 N2 C15 C14 1.5(3) . . . . ?
C11 C5 C4 C3 -175.3(8) . . . . ?
C11 C12 C13 C14 1.7(3) . . . . ?
C15 N2 C11 C5 177.8(17) . . . . ?
C15 N2 C11 C12 -0.5(2) . . . . ?
C15 C14 C13 C12 -0.7(3) . . . . ?
C7 C6 N1 C10 0.9(3) . . . . ?
C7 C6 C1 P1 137.7(6) . . . . ?
C7 C6 C1 C2 -36(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C13 C12 C11 N2 -1.1(3) . . . . ?
C13 C12 C11 C5 -179.3(17) . . . . ?
C1 P1 C5 C11 177.3(10) . . . . ?
C1 P1 C5 C4 -0.5(16) . . . . ?
C1 C6 N1 C10 177.1(11) . . . . ?
C1 C6 C7 C8 -177.4(12) . . . . ?
C4 C5 C11 N2 65.5(16) . . . . ?
C4 C5 C11 C12 -116(2) . . . . ?
C4 C3 C2 C1 -1(2) . . . . ?
