#------------------------------------------------------------------------------
#$Date: 2024-08-05 21:12:58 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293778 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/20/1572043.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_1572043
loop_
_publ_author_name
'Nascimento, Mitchell A.'
'LaPierre, Etienne A.'
'Patrick, Brian O.'
'Watson, Jade E. T.'
'Watanabe, Lara'
'Rawson, Jeremy'
'Hering-Junghans, Christian'
'Manners, Ian'
_publ_section_title
;
 1,3-Dipolar cyclisation reactions of nitriles with sterically encumbered
 cyclic triphosphanes: synthesis and electronic structure of
 phosphorus-rich heterocycles with tunable colour.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              12006
_journal_page_last               12016
_journal_paper_doi               10.1039/d4sc02497d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C19 H32 N P3'
_chemical_formula_sum            'C19 H32 N P3'
_chemical_formula_weight         367.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                91.383(2)
_cell_angle_beta                 101.010(2)
_cell_angle_gamma                104.534(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3017(5)
_cell_length_b                   9.9102(7)
_cell_length_c                   15.2826(11)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.44
_cell_volume                     1047.75(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'LinXTL v. 5.9.9 (Spasyuk, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0354
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.361
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         6401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0268
_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)+(0.0309P)²+0.3327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5836
_reflns_number_total             6401
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im023_a
_cod_depositor_comments
'Adding full bibliography for 1572027--1572043.cif.'
_cod_database_code               1572043
_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_min   0.927
_shelx_estimated_absorpt_t_max   0.951
loop_
_space_group_symop_operation_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_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 0.61265(3) 0.30551(2) 0.78351(2) 0.01030(5) Uani 1 1 d . . . . .
P2 P 0.31990(3) 0.28860(2) 0.70043(2) 0.00984(5) Uani 1 1 d . . . . .
P3 P 0.39196(3) 0.51000(2) 0.67327(2) 0.00980(5) Uani 1 1 d . . . . .
N1 N 0.68796(11) 0.48113(8) 0.81106(5) 0.01158(14) Uani 1 1 d . . . . .
C2 C 0.71662(12) 0.71938(9) 0.77846(6) 0.01094(15) Uani 1 1 d . . . . .
C3 C 0.70587(13) 0.80616(10) 0.70793(6) 0.01368(16) Uani 1 1 d . . . . .
H3 H 0.624420 0.769892 0.651765 0.016 Uiso 1 1 calc R U . . .
C7 C 0.83734(13) 0.77464(10) 0.86114(6) 0.01350(16) Uani 1 1 d . . . . .
H7 H 0.846401 0.716867 0.909644 0.016 Uiso 1 1 calc R U . . .
C1 C 0.61214(12) 0.56760(9) 0.76479(6) 0.01025(15) Uani 1 1 d . . . . .
C12 C 0.33755(13) 0.20152(9) 0.59153(6) 0.01233(16) Uani 1 1 d . . . . .
C17 C 0.48476(15) 0.07602(10) 0.87193(6) 0.01696(18) Uani 1 1 d . . . . .
H17A H 0.466481 0.032066 0.927485 0.025 Uiso 1 1 calc R U . . .
H17B H 0.573655 0.036877 0.845085 0.025 Uiso 1 1 calc R U . . .
H17C H 0.359979 0.058061 0.830150 0.025 Uiso 1 1 calc R U . . .
C6 C 0.94369(14) 0.91388(10) 0.87214(7) 0.01670(18) Uani 1 1 d . . . . .
H6 H 1.024630 0.950803 0.928310 0.020 Uiso 1 1 calc R U . . .
C8 C 0.20015(13) 0.57566(9) 0.71588(6) 0.01245(16) Uani 1 1 d . . . . .
C5 C 0.93235(14) 0.99968(10) 0.80132(7) 0.01693(18) Uani 1 1 d . . . . .
H5 H 1.005415 1.094627 0.809161 0.020 Uiso 1 1 calc R U . . .
C10 C 0.00833(13) 0.49823(10) 0.65401(7) 0.01686(18) Uani 1 1 d . . . . .
H10A H -0.018835 0.398159 0.663071 0.025 Uiso 1 1 calc R U . . .
H10B H 0.017956 0.512194 0.591616 0.025 Uiso 1 1 calc R U . . .
H10C H -0.096378 0.534980 0.667909 0.025 Uiso 1 1 calc R U . . .
C4 C 0.81352(14) 0.94549(10) 0.71917(7) 0.01579(17) Uani 1 1 d . . . . .
H4 H 0.805670 1.003397 0.670690 0.019 Uiso 1 1 calc R U . . .
C9 C 0.19154(15) 0.54726(12) 0.81304(6) 0.01941(19) Uani 1 1 d . . . . .
H9A H 0.315329 0.595182 0.851843 0.029 Uiso 1 1 calc R U . . .
H9B H 0.165791 0.446440 0.819394 0.029 Uiso 1 1 calc R U . . .
H9C H 0.087983 0.581934 0.830196 0.029 Uiso 1 1 calc R U . . .
C16 C 0.56976(13) 0.23455(9) 0.89242(6) 0.01314(16) Uani 1 1 d . . . . .
C15 C 0.15878(15) 0.21108(11) 0.52260(6) 0.01838(19) Uani 1 1 d . . . . .
H15A H 0.169493 0.308908 0.509915 0.028 Uiso 1 1 calc R U . . .
H15B H 0.042259 0.174737 0.546632 0.028 Uiso 1 1 calc R U . . .
H15C H 0.150662 0.155699 0.467334 0.028 Uiso 1 1 calc R U . . .
C13 C 0.32381(15) 0.04800(10) 0.60938(7) 0.01807(18) Uani 1 1 d . . . . .
H13A H 0.320225 -0.004808 0.553748 0.027 Uiso 1 1 calc R U . . .
H13B H 0.205814 0.008591 0.631656 0.027 Uiso 1 1 calc R U . . .
H13C H 0.436630 0.042130 0.654124 0.027 Uiso 1 1 calc R U . . .
C18 C 0.43475(15) 0.29769(11) 0.93542(6) 0.01856(19) Uani 1 1 d . . . . .
H18A H 0.422296 0.257414 0.992604 0.028 Uiso 1 1 calc R U . . .
H18B H 0.307308 0.276973 0.895583 0.028 Uiso 1 1 calc R U . . .
H18C H 0.488023 0.399189 0.945651 0.028 Uiso 1 1 calc R U . . .
C19 C 0.76956(15) 0.26442(11) 0.95515(7) 0.01947(19) Uani 1 1 d . . . . .
H19A H 0.825264 0.365668 0.965641 0.029 Uiso 1 1 calc R U . . .
H19B H 0.854850 0.222495 0.927531 0.029 Uiso 1 1 calc R U . . .
H19C H 0.755761 0.224108 1.012214 0.029 Uiso 1 1 calc R U . . .
C11 C 0.23310(15) 0.73260(10) 0.70393(8) 0.0233(2) Uani 1 1 d . . . . .
H11A H 0.123301 0.763708 0.717039 0.035 Uiso 1 1 calc R U . . .
H11B H 0.245231 0.750104 0.642190 0.035 Uiso 1 1 calc R U . . .
H11C H 0.351823 0.784240 0.744933 0.035 Uiso 1 1 calc R U . . .
C14 C 0.52168(14) 0.26371(11) 0.55700(6) 0.01724(18) Uani 1 1 d . . . . .
H14A H 0.634657 0.260508 0.602517 0.026 Uiso 1 1 calc R U . . .
H14B H 0.528073 0.360973 0.544071 0.026 Uiso 1 1 calc R U . . .
H14C H 0.520353 0.209531 0.502281 0.026 Uiso 1 1 calc R U . . .
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
N1 P1 C16 102.19(4) . . ?
N1 P1 P2 100.37(3) . . ?
C16 P1 P2 105.65(3) . . ?
C12 P2 P3 101.58(3) . . ?
C12 P2 P1 101.49(3) . . ?
P3 P2 P1 93.015(12) . . ?
C1 P3 C8 104.49(4) . . ?
C1 P3 P2 96.65(3) . . ?
C8 P3 P2 102.52(3) . . ?
C1 N1 P1 121.68(6) . . ?
C3 C2 C7 118.98(8) . . ?
C3 C2 C1 120.74(8) . . ?
C7 C2 C1 120.14(8) . . ?
C4 C3 C2 120.67(8) . . ?
C6 C7 C2 120.12(9) . . ?
N1 C1 C2 118.21(8) . . ?
N1 C1 P3 122.91(7) . . ?
C2 C1 P3 118.57(6) . . ?
C14 C12 C13 109.72(8) . . ?
C14 C12 C15 110.29(8) . . ?
C13 C12 C15 109.52(8) . . ?
C14 C12 P2 115.42(6) . . ?
C13 C12 P2 105.54(6) . . ?
C15 C12 P2 106.13(6) . . ?
C7 C6 C5 120.51(9) . . ?
C9 C8 C11 110.22(8) . . ?
C9 C8 C10 110.01(8) . . ?
C11 C8 C10 108.24(8) . . ?
C9 C8 P3 113.80(6) . . ?
C11 C8 P3 109.34(7) . . ?
C10 C8 P3 104.98(6) . . ?
C4 C5 C6 119.66(9) . . ?
C5 C4 C3 120.05(9) . . ?
C18 C16 C17 110.43(8) . . ?
C18 C16 C19 109.91(8) . . ?
C17 C16 C19 110.01(8) . . ?
C18 C16 P1 114.28(6) . . ?
C17 C16 P1 105.74(6) . . ?
C19 C16 P1 106.30(7) . . ?
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 N1 1.7043(8) . ?
P1 C16 1.8730(9) . ?
P1 P2 2.2322(3) . ?
P2 C12 1.8972(9) . ?
P2 P3 2.1934(3) . ?
P3 C1 1.8732(9) . ?
P3 C8 1.8958(9) . ?
N1 C1 1.2878(11) . ?
C2 C3 1.3978(13) . ?
C2 C7 1.4044(12) . ?
C2 C1 1.4954(12) . ?
C3 C4 1.3950(13) . ?
C7 C6 1.3915(13) . ?
C12 C14 1.5286(13) . ?
C12 C13 1.5340(13) . ?
C12 C15 1.5376(13) . ?
C17 C16 1.5376(13) . ?
C6 C5 1.3954(14) . ?
C8 C9 1.5280(13) . ?
C8 C11 1.5338(13) . ?
C8 C10 1.5376(13) . ?
C5 C4 1.3910(14) . ?
C16 C18 1.5271(13) . ?
C16 C19 1.5397(13) . ?
