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#$Date: 2024-08-05 21:11:51 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/21/1572110.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_1572110
loop_
_publ_author_name
'Minko, Yury'
'Fetrow, Taylor V.'
'Sharma, Shikha'
'Cashman, Brenna K.'
'Tondreau, Aaron M.'
_publ_section_title
;
 Flexible interactions of the rare-earth elements Y, La, and Lu with
 phosphorus in metallacyclohexane rings.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12138
_journal_page_last               12147
_journal_paper_doi               10.1039/d4sc02077d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C23 H33 N2 P'
_chemical_formula_sum            'C23 H33 N2 P'
_chemical_formula_weight         368.48
_chemical_properties_physical    Air-sensitive
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-01-03
_audit_creation_method
;
Olex2 1.2
(compiled Apr  3 2018 11:26:26 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2024-01-24 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9418(8)
_cell_length_b                   16.3863(10)
_cell_length_c                   13.0368(9)
_cell_measurement_reflns_used    4181
_cell_measurement_temperature    108.0
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.58
_cell_volume                     2123.8(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      108.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11477
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.020
_diffrn_reflns_theta_min         2.486
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0920 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.8680.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0521
_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)+(0.0446P)²+1.9138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2257
_reflns_number_total             2630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02077d2.cif
_cod_data_source_block           pch2narch2
_cod_depositor_comments
'Adding full bibliography for 1572109--1572117.cif.'
_cod_database_code               1572110
_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   0.988
_shelx_estimated_absorpt_t_min   0.944
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H3C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C9(H9)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C12(H12A,H12B,H12C), C4(H4A,H4B,H4C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'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_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 0.26351(6) 0.750000 0.53386(5) 0.01380(16) Uani 1 2 d S T P . .
N1 N 0.11668(15) 0.67571(8) 0.68578(10) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.0411(2) 0.750000 0.70723(18) 0.0160(5) Uani 1 2 d S T P . .
H5A H -0.041975 0.750001 0.665369 0.019 Uiso 1 2 calc RS T P . .
H5B H 0.014142 0.749999 0.780333 0.019 Uiso 1 2 calc RS T P . .
C6 C 0.19614(17) 0.63779(9) 0.76035(13) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.30450(17) 0.58716(10) 0.73368(13) 0.0170(3) Uani 1 1 d . . . . .
H11 H 0.331461 0.583600 0.663918 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2412(3) 0.750000 0.39071(18) 0.0178(5) Uani 1 2 d S T P . .
C1 C 0.14649(18) 0.66708(10) 0.57696(12) 0.0165(3) Uani 1 1 d . . . . .
H1A H 0.061938 0.669923 0.537008 0.020 Uiso 1 1 calc R . . . .
H1B H 0.188368 0.613208 0.564258 0.020 Uiso 1 1 calc R . . . .
C7 C 0.16305(19) 0.64448(11) 0.86488(13) 0.0208(4) Uani 1 1 d . . . . .
H7 H 0.090623 0.678756 0.884966 0.025 Uiso 1 1 calc R . . . .
C10 C 0.37340(17) 0.54196(10) 0.80760(13) 0.0184(4) Uani 1 1 d . . . . .
C9 C 0.3382(2) 0.54994(11) 0.91044(14) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.385296 0.519728 0.961201 0.027 Uiso 1 1 calc R . . . .
C3 C 0.0960(3) 0.750000 0.35195(19) 0.0217(5) Uani 1 2 d S T P . .
H3A H 0.095674 0.753090 0.276883 0.032 Uiso 0.5 1 calc GR . . A -1
H3B H 0.048224 0.797213 0.380245 0.032 Uiso 0.5 1 calc GR . . A -1
H3C H 0.051139 0.699697 0.373895 0.032 Uiso 0.5 1 calc GR . . A -1
C8 C 0.2342(2) 0.60198(12) 0.93923(14) 0.0243(4) Uani 1 1 d . . . . .
C12 C 0.48315(19) 0.48381(11) 0.77575(15) 0.0233(4) Uani 1 1 d . . . . .
H12A H 0.444831 0.429369 0.765034 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.551718 0.481225 0.829659 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.524288 0.503011 0.711840 0.035 Uiso 1 1 calc GR . . . .
C4 C 0.3136(2) 0.82642(12) 0.35047(14) 0.0254(4) Uani 1 1 d . . . . .
H4A H 0.269746 0.875324 0.377951 0.038 Uiso 1 1 calc GR . . . .
H4B H 0.309307 0.827343 0.275377 0.038 Uiso 1 1 calc GR . . . .
H4C H 0.407841 0.825335 0.372414 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.1972(3) 0.61226(17) 1.05106(16) 0.0476(7) Uani 1 1 d . . . . .
H13A H 0.205456 0.669857 1.070297 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.257864 0.579382 1.093517 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.104284 0.594196 1.061813 0.071 Uiso 1 1 calc GR . . . .
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_
_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 C2 102.97(8) 7_575 . ?
C1 P1 C2 102.97(8) . . ?
C1 P1 C1 92.88(11) 7_575 . ?
C6 N1 C5 121.93(15) . . ?
C6 N1 C1 121.28(14) . . ?
C1 N1 C5 111.90(15) . . ?
N1 C5 N1 113.26(19) 7_575 . ?
N1 C5 H5A 108.9 7_575 . ?
N1 C5 H5A 108.9 . . ?
N1 C5 H5B 108.9 7_575 . ?
N1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C11 121.61(15) . . ?
N1 C6 C7 120.46(15) . . ?
C11 C6 C7 117.76(16) . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.31(16) . . ?
C10 C11 H11 119.3 . . ?
C3 C2 P1 116.07(17) . . ?
C3 C2 C4 109.22(13) . . ?
C3 C2 C4 109.22(14) . 7_575 ?
C4 C2 P1 106.48(12) . . ?
C4 C2 P1 106.48(12) 7_575 . ?
C4 C2 C4 109.2(2) 7_575 . ?
P1 C1 H1A 109.6 . . ?
P1 C1 H1B 109.6 . . ?
N1 C1 P1 110.36(11) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.24(17) . . ?
C8 C7 H7 119.4 . . ?
C11 C10 C12 120.06(16) . . ?
C9 C10 C11 119.46(16) . . ?
C9 C10 C12 120.47(16) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.28(17) . . ?
C8 C9 H9 119.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 C8 C9 119.86(17) . . ?
C7 C8 C13 119.56(18) . . ?
C9 C8 C13 120.58(17) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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 C2 1.879(2) . ?
P1 C1 1.8748(17) 7_575 ?
P1 C1 1.8749(17) . ?
N1 C5 1.4576(19) . ?
N1 C6 1.398(2) . ?
N1 C1 1.456(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.403(2) . ?
C6 C7 1.406(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.395(2) . ?
C2 C3 1.529(3) . ?
C2 C4 1.537(2) . ?
C2 C4 1.537(2) 7_575 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C10 C9 1.392(2) . ?
C10 C12 1.507(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.392(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C8 C13 1.513(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
