#------------------------------------------------------------------------------
#$Date: 2024-08-05 20:12:58 +0200 (Mon 05 de Aug de 2024) $
#$Revision: 293778 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/20/1572033.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_1572033
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         'C34 H39 N1 P3, C O3 F3 S [+solvent]'
_chemical_formula_sum            'C35 H39 F3 N O3 P3 S'
_chemical_formula_weight         703.64
_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   mixed
_audit_creation_date             2022-05-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2024-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                113.278(6)
_cell_angle_beta                 98.207(7)
_cell_angle_gamma                93.456(7)
_cell_formula_units_Z            2
_cell_length_a                   11.005(2)
_cell_length_b                   12.506(2)
_cell_length_c                   15.198(3)
_cell_measurement_reflns_used    6259
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.96
_cell_measurement_theta_min      2.43
_cell_volume                     1886.0(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 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 0.999
_diffrn_measured_fraction_theta_max 0.994
_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  0.0667
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.956
_diffrn_reflns_theta_min         1.787
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         9011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+0.8735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6015
_reflns_number_total             9011
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc02497d4.cif
_cod_data_source_block           im026_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_hydrogen_treatment' value 'Mixed' was changed
to 'mixed' 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 1572027--1572043.cif.
;
_cod_original_cell_volume        1886.1(6)
_cod_database_code               1572033
_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   0.990
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C7(H7), C19(H19), C5(H5), C3(H3), C30(H30), C6(H6), C10(H10),
 C28(H28), C4(H4), C12(H12)
1.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C34(H34A,H34B,H34C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C24(H24A,H24B,H24C), C15(H15A,
 H15B,H15C), C33(H33A,H33B,H33C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
P2 P 0.60151(6) 0.59880(6) 0.23154(5) 0.01015(14) Uani 1 1 d . . . . .
S1 S 0.83882(6) 0.88547(6) 0.72357(5) 0.01429(15) Uani 1 1 d . . . . .
P3 P 0.65375(6) 0.60696(6) 0.38211(5) 0.01062(15) Uani 1 1 d . . . . .
P1 P 0.73927(6) 0.74937(6) 0.25933(5) 0.01030(14) Uani 1 1 d . . . . .
O1 O 0.82637(17) 0.79834(15) 0.62367(12) 0.0166(4) Uani 1 1 d . . . . .
F1 F 0.98011(19) 0.90232(17) 0.88363(12) 0.0428(5) Uani 1 1 d . . . . .
F2 F 0.91125(18) 0.72511(15) 0.78235(14) 0.0407(5) Uani 1 1 d . . . . .
F3 F 1.05807(17) 0.8226(2) 0.75493(15) 0.0503(6) Uani 1 1 d . . . . .
O2 O 0.73093(18) 0.88174(18) 0.76591(14) 0.0258(5) Uani 1 1 d . . . . .
O3 O 0.8965(2) 0.99942(16) 0.74088(14) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.71767(19) 0.75674(18) 0.43577(15) 0.0102(4) Uani 1 1 d . . . . .
C18 C 0.7921(2) 0.4463(2) 0.17058(18) 0.0122(5) Uani 1 1 d . . . . .
C8 C 0.5010(2) 0.6009(2) 0.41561(17) 0.0103(5) Uani 1 1 d . . . . .
C2 C 0.8032(2) 0.9438(2) 0.44443(18) 0.0121(5) Uani 1 1 d . . . . .
C27 C 0.5665(2) 0.9056(2) 0.24161(17) 0.0108(5) Uani 1 1 d . . . . .
C17 C 0.6697(2) 0.4716(2) 0.15390(17) 0.0106(5) Uani 1 1 d . . . . .
C1 C 0.7490(2) 0.8200(2) 0.38953(17) 0.0101(5) Uani 1 1 d . . . . .
C22 C 0.5862(2) 0.3937(2) 0.06934(18) 0.0116(5) Uani 1 1 d . . . . .
C13 C 0.4445(2) 0.6903(2) 0.48073(17) 0.0126(5) Uani 1 1 d . . . . .
C21 C 0.6277(2) 0.2969(2) 0.00306(18) 0.0138(5) Uani 1 1 d . . . . .
H21 H 0.572834 0.247203 -0.052940 0.017 Uiso 1 1 calc R U . . .
C31 C 0.7330(2) 0.8750(2) 0.14680(18) 0.0125(5) Uani 1 1 d . . . . .
C7 C 0.8801(2) 0.9990(2) 0.40487(18) 0.0124(5) Uani 1 1 d . . . . .
H7 H 0.899262 0.957202 0.343813 0.015 Uiso 1 1 calc R U . . .
C19 C 0.8278(2) 0.3470(2) 0.10169(19) 0.0154(6) Uani 1 1 d . . . . .
H19 H 0.908483 0.330530 0.112615 0.018 Uiso 1 1 calc R U . . .
C23 C 0.8877(2) 0.5201(2) 0.25918(18) 0.0160(6) Uani 1 1 d . . . . .
H23A H 0.903448 0.597443 0.261252 0.024 Uiso 1 1 calc R U . . .
H23B H 0.962950 0.484784 0.256008 0.024 Uiso 1 1 calc R U . . .
H23C H 0.857621 0.524979 0.316751 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4395(2) 0.4843(2) 0.37278(18) 0.0143(5) Uani 1 1 d . . . . .
C26 C 0.6704(2) 0.8497(2) 0.21242(17) 0.0106(5) Uani 1 1 d . . . . .
C20 C 0.7477(2) 0.2715(2) 0.01720(18) 0.0148(6) Uani 1 1 d . . . . .
C5 C 0.8989(2) 1.1786(2) 0.54788(19) 0.0170(6) Uani 1 1 d . . . . .
H5 H 0.930893 1.257309 0.582343 0.020 Uiso 1 1 calc R U . . .
C3 C 0.7747(2) 1.0079(2) 0.53626(18) 0.0138(5) Uani 1 1 d . . . . .
H3 H 0.723083 0.971798 0.562691 0.017 Uiso 1 1 calc R U . . .
C30 C 0.6939(3) 0.9596(2) 0.11568(18) 0.0166(6) Uani 1 1 d . . . . .
H30 H 0.734829 0.976618 0.072380 0.020 Uiso 1 1 calc R U . . .
C6 C 0.9276(2) 1.1165(2) 0.45711(19) 0.0154(6) Uani 1 1 d . . . . .
H6 H 0.978834 1.153375 0.431038 0.019 Uiso 1 1 calc R U . . .
C29 C 0.5953(3) 1.0200(2) 0.14720(19) 0.0175(6) Uani 1 1 d . . . . .
C10 C 0.3243(2) 0.4610(2) 0.39209(19) 0.0170(6) Uani 1 1 d . . . . .
H10 H 0.284199 0.384533 0.362363 0.020 Uiso 1 1 calc R U . . .
C28 C 0.5317(2) 0.9901(2) 0.20823(18) 0.0153(6) Uani 1 1 d . . . . .
H28 H 0.463552 1.027647 0.227527 0.018 Uiso 1 1 calc R U . . .
C34 C 0.8425(2) 0.8147(2) 0.10999(19) 0.0161(6) Uani 1 1 d . . . . .
H34A H 0.913921 0.844093 0.161133 0.024 Uiso 1 1 calc R U . . .
H34B H 0.859245 0.830207 0.055574 0.024 Uiso 1 1 calc R U . . .
H34C H 0.823695 0.731582 0.089975 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8232(2) 1.1251(2) 0.58799(19) 0.0169(6) Uani 1 1 d . . . . .
H4 H 0.804870 1.167448 0.649271 0.020 Uiso 1 1 calc R U . . .
C14 C 0.4949(3) 0.3824(2) 0.3046(2) 0.0191(6) Uani 1 1 d . . . . .
H14A H 0.497064 0.391185 0.244815 0.029 Uiso 1 1 calc R U . . .
H14B H 0.445108 0.310108 0.291073 0.029 Uiso 1 1 calc R U . . .
H14C H 0.577444 0.381532 0.334600 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5026(2) 0.8165(2) 0.53577(19) 0.0163(6) Uani 1 1 d . . . . .
H16A H 0.575614 0.820384 0.580407 0.024 Uiso 1 1 calc R U . . .
H16B H 0.444662 0.862015 0.571305 0.024 Uiso 1 1 calc R U . . .
H16C H 0.524454 0.847189 0.490594 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3292(2) 0.6615(2) 0.49783(19) 0.0163(6) Uani 1 1 d . . . . .
H12 H 0.292105 0.720746 0.540259 0.020 Uiso 1 1 calc R U . . .
C25 C 0.4508(2) 0.4077(2) 0.04892(19) 0.0161(6) Uani 1 1 d . . . . .
H25A H 0.407051 0.384561 0.090203 0.024 Uiso 1 1 calc R U . . .
H25B H 0.416467 0.359088 -0.018052 0.024 Uiso 1 1 calc R U . . .
H25C H 0.442920 0.488254 0.061656 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2662(2) 0.5481(2) 0.45446(19) 0.0172(6) Uani 1 1 d . . . . .
C32 C 0.4915(2) 0.8784(2) 0.30713(19) 0.0161(6) Uani 1 1 d . . . . .
H32A H 0.477299 0.794984 0.287086 0.024 Uiso 1 1 calc R U . . .
H32B H 0.413552 0.908360 0.303114 0.024 Uiso 1 1 calc R U . . .
H32C H 0.535703 0.914587 0.373075 0.024 Uiso 1 1 calc R U . . .
C24 C 0.7907(3) 0.1642(2) -0.0548(2) 0.0229(7) Uani 1 1 d . . . . .
H24A H 0.738041 0.095238 -0.063767 0.034 Uiso 1 1 calc R U . . .
H24B H 0.874339 0.158657 -0.030275 0.034 Uiso 1 1 calc R U . . .
H24C H 0.786917 0.170500 -0.116019 0.034 Uiso 1 1 calc R U . . .
C35 C 0.9525(3) 0.8311(3) 0.7889(2) 0.0259(7) Uani 1 1 d . . . . .
C15 C 0.1408(3) 0.5213(3) 0.4749(2) 0.0251(7) Uani 1 1 d . . . . .
H15A H 0.078394 0.540227 0.434328 0.038 Uiso 1 1 calc R U . . .
H15B H 0.138049 0.567260 0.542120 0.038 Uiso 1 1 calc R U . . .
H15C H 0.125923 0.439429 0.461307 0.038 Uiso 1 1 calc R U . . .
C33 C 0.5590(3) 1.1158(2) 0.1163(2) 0.0265(7) Uani 1 1 d . . . . .
H33A H 0.610384 1.188095 0.158091 0.040 Uiso 1 1 calc R U . . .
H33B H 0.473909 1.125210 0.120930 0.040 Uiso 1 1 calc R U . . .
H33C H 0.569669 1.095342 0.050250 0.040 Uiso 1 1 calc R U . . .
H1 H 0.750(3) 0.783(2) 0.497(2) 0.023(8) Uiso 1 1 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'
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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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
P1 P2 P3 93.41(3) . . ?
C17 P2 P3 104.64(8) . . ?
C17 P2 P1 103.39(9) . . ?
O1 S1 C35 102.03(12) . . ?
O2 S1 O1 113.58(12) . . ?
O2 S1 C35 103.65(14) . . ?
O3 S1 O1 114.77(12) . . ?
O3 S1 O2 116.55(13) . . ?
O3 S1 C35 103.80(13) . . ?
N1 P3 P2 95.34(8) . . ?
N1 P3 C8 106.55(11) . . ?
C8 P3 P2 100.67(8) . . ?
C1 P1 P2 97.41(9) . . ?
C1 P1 C26 105.12(11) . . ?
C26 P1 P2 110.44(8) . . ?
C1 N1 P3 126.34(18) . . ?
C17 C18 C23 124.0(2) . . ?
C19 C18 C17 118.7(2) . . ?
C19 C18 C23 117.2(2) . . ?
C13 C8 P3 129.99(19) . . ?
C13 C8 C9 118.7(2) . . ?
C9 C8 P3 111.06(19) . . ?
C7 C2 C1 120.9(2) . . ?
C7 C2 C3 119.5(2) . . ?
C3 C2 C1 119.6(2) . . ?
C26 C27 C32 123.2(2) . . ?
C28 C27 C26 118.5(2) . . ?
C28 C27 C32 118.3(2) . . ?
C18 C17 P2 127.06(18) . . ?
C18 C17 C22 119.2(2) . . ?
C22 C17 P2 113.79(18) . . ?
N1 C1 P1 118.81(18) . . ?
N1 C1 C2 120.2(2) . . ?
C2 C1 P1 120.68(19) . . ?
C17 C22 C25 123.2(2) . . ?
C21 C22 C17 119.4(2) . . ?
C21 C22 C25 117.4(2) . . ?
C8 C13 C16 124.4(2) . . ?
C12 C13 C8 118.8(2) . . ?
C12 C13 C16 116.8(2) . . ?
C20 C21 C22 122.4(2) . . ?
C26 C31 C34 122.8(2) . . ?
C30 C31 C26 118.6(2) . . ?
C30 C31 C34 118.7(2) . . ?
C6 C7 C2 119.8(2) . . ?
C20 C19 C18 122.6(2) . . ?
C8 C9 C14 122.4(2) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 C14 117.8(2) . . ?
C27 C26 P1 124.4(2) . . ?
C27 C26 C31 120.3(2) . . ?
C31 C26 P1 115.15(19) . . ?
C21 C20 C19 117.7(2) . . ?
C21 C20 C24 121.7(2) . . ?
C19 C20 C24 120.5(2) . . ?
C4 C5 C6 120.8(2) . . ?
C4 C3 C2 120.2(3) . . ?
C31 C30 C29 122.1(3) . . ?
C5 C6 C7 120.1(3) . . ?
C30 C29 C33 121.0(3) . . ?
C28 C29 C30 118.3(2) . . ?
C28 C29 C33 120.8(3) . . ?
C9 C10 C11 122.3(2) . . ?
C29 C28 C27 122.1(2) . . ?
C5 C4 C3 119.6(3) . . ?
C13 C12 C11 123.1(3) . . ?
C10 C11 C12 117.3(3) . . ?
C10 C11 C15 121.6(3) . . ?
C12 C11 C15 121.1(3) . . ?
F1 C35 S1 111.4(2) . . ?
F1 C35 F2 107.2(3) . . ?
F2 C35 S1 111.54(19) . . ?
F3 C35 S1 111.8(2) . . ?
F3 C35 F1 107.0(2) . . ?
F3 C35 F2 107.6(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
P2 P3 2.2384(10) . ?
P2 P1 2.2063(10) . ?
P2 C17 1.844(2) . ?
S1 O1 1.4583(18) . ?
S1 O2 1.436(2) . ?
S1 O3 1.432(2) . ?
S1 C35 1.816(3) . ?
P3 N1 1.772(2) . ?
P3 C8 1.830(3) . ?
P1 C1 1.804(2) . ?
P1 C26 1.824(3) . ?
F1 C35 1.336(3) . ?
F2 C35 1.336(3) . ?
F3 C35 1.331(4) . ?
N1 C1 1.309(3) . ?
C18 C17 1.413(3) . ?
C18 C19 1.394(3) . ?
C18 C23 1.506(3) . ?
C8 C13 1.414(3) . ?
C8 C9 1.420(3) . ?
C2 C1 1.475(3) . ?
C2 C7 1.399(4) . ?
C2 C3 1.400(3) . ?
C27 C26 1.410(3) . ?
C27 C28 1.393(4) . ?
C27 C32 1.502(4) . ?
C17 C22 1.418(3) . ?
C22 C21 1.386(3) . ?
C22 C25 1.514(4) . ?
C13 C16 1.511(3) . ?
C13 C12 1.386(4) . ?
C21 C20 1.383(4) . ?
C31 C26 1.410(4) . ?
C31 C30 1.386(4) . ?
C31 C34 1.517(4) . ?
C7 C6 1.389(3) . ?
C19 C20 1.392(4) . ?
C9 C10 1.381(4) . ?
C9 C14 1.516(4) . ?
C20 C24 1.512(3) . ?
C5 C6 1.383(4) . ?
C5 C4 1.384(4) . ?
C3 C4 1.388(3) . ?
C30 C29 1.393(4) . ?
C29 C28 1.385(4) . ?
C29 C33 1.504(4) . ?
C10 C11 1.391(4) . ?
C12 C11 1.392(4) . ?
C11 C15 1.504(4) . ?
