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#$Date: 2021-06-05 21:47:25 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266063 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/68/7706856.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_7706856
loop_
_publ_author_name
'Hu, Lei'
'Mahaut, Damien'
'Tumanov, Nikolay'
'Wouters, Johan'
'Collard, Laurent'
'Robiette, Raphaël'
'Berionni, Guillaume'
_publ_section_title
;
 Sterically hindered ortho-substituted phosphatriptycenes as
 configurationally stable P-chirogenic triarylphosphines.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4772
_journal_page_last               4777
_journal_paper_doi               10.1039/d1dt00816a
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C23 H20 Cl P'
_chemical_formula_sum            'C23 H20 Cl P'
_chemical_formula_weight         362.81
_chemical_name_common
(5R/S,10S/R)-2-(tert-butyl)-6-chloro-10H-5,10-[1,2]benzenoacridophosphine
_chemical_name_systematic
(5R/S,10S/R)-2-(tert-butyl)-6-chloro-10H-5,10-[1,2]benzenoacridophosphine
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-08 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.365(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1914(2)
_cell_length_b                   13.7899(4)
_cell_length_c                   8.6284(2)
_cell_measurement_reflns_used    2317
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.7210
_cell_measurement_theta_min      6.3180
_cell_volume                     961.66(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur, Ruby, Gemini Ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2998
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.221
_diffrn_reflns_theta_max         67.221
_diffrn_reflns_theta_min         5.195
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0517
_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)+(0.0460P)²+0.6181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2585
_reflns_number_total             2998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00816a2.cif
_cod_data_source_block           nt0764_LHG168
_cod_depositor_comments
'Adding full bibliography for 7706848--7706861.cif.'
_cod_original_cell_volume        961.67(5)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7706856
_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   0.527
_shelx_estimated_absorpt_t_max   0.932
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Cl1 Cl 0.8841(3) 0.44281(17) 0.5730(3) 0.0834(7) Uani 0.5 1 d . . P A 1
P1 P 0.65480(16) 0.250000 0.46590(15) 0.0517(4) Uani 1 2 d S T P . .
C1 C 0.5957(4) 0.3479(3) 0.5906(4) 0.0522(8) Uani 1 1 d . . . . .
C2 C 0.6916(5) 0.4293(3) 0.6361(4) 0.0615(9) Uani 1 1 d . . . . .
H2 H 0.793401 0.436404 0.602876 0.074 Uiso 0.5 1 calc R U P A 2
C3 C 0.6385(6) 0.4996(3) 0.7293(5) 0.0725(12) Uani 1 1 d . . . . .
H3 H 0.704370 0.553461 0.759188 0.087 Uiso 1 1 calc R U . . .
C4 C 0.4875(6) 0.4899(3) 0.7785(5) 0.0715(12) Uani 1 1 d . . . . .
H4 H 0.452044 0.537189 0.842371 0.086 Uiso 1 1 calc R U . . .
C5 C 0.3880(5) 0.4101(3) 0.7331(4) 0.0617(10) Uani 1 1 d . . . . .
H5 H 0.285575 0.404475 0.765500 0.074 Uiso 1 1 calc R U . . .
C6 C 0.4405(4) 0.3390(2) 0.6401(4) 0.0519(8) Uani 1 1 d . . . . .
C7 C 0.3393(6) 0.250000 0.5834(5) 0.0497(11) Uani 1 2 d S T P . .
H7 H 0.233501 0.250000 0.622547 0.060 Uiso 1 2 calc R U P . .
C8 C 0.3117(6) 0.250000 0.4035(5) 0.0439(10) Uani 1 2 d S T P . .
C9 C 0.1581(6) 0.250000 0.3118(5) 0.0471(11) Uani 1 2 d S T P . .
H9 H 0.064183 0.250000 0.359525 0.056 Uiso 1 2 calc R U P . .
C10 C 0.1406(6) 0.250000 0.1474(5) 0.0458(11) Uani 1 2 d S T P . .
C11 C -0.0320(6) 0.250000 0.0488(6) 0.0553(13) Uani 1 2 d S T P . .
C12 C -0.1257(5) 0.1587(3) 0.0858(5) 0.0732(12) Uani 1 1 d . . . . .
H12A H -0.136583 0.158721 0.194905 0.110 Uiso 1 1 calc R U . . .
H12B H -0.065649 0.102134 0.062977 0.110 Uiso 1 1 calc R U . . .
H12C H -0.233635 0.158246 0.022608 0.110 Uiso 1 1 calc R U . . .
C13 C -0.0275(8) 0.250000 -0.1281(7) 0.085(2) Uani 1 2 d DS T P . .
H13A H -0.137(3) 0.250000 -0.189(7) 0.128 Uiso 1 2 d DS U P . .
H13B H 0.031(2) 0.3070(2) -0.153(4) 0.128 Uiso 1 1 d D U . . .
C14 C 0.2841(6) 0.250000 0.0800(5) 0.0464(11) Uani 1 2 d S T P . .
H14 H 0.275817 0.250000 -0.028796 0.056 Uiso 1 2 calc R U P . .
C15 C 0.4372(6) 0.250000 0.1718(5) 0.0475(10) Uani 1 2 d S T P . .
H15 H 0.531193 0.250000 0.124134 0.057 Uiso 1 2 calc R U P . .
C16 C 0.4548(6) 0.250000 0.3344(5) 0.0436(10) Uani 1 2 d S T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C16 P1 C1 93.92(15) . . ?
C16 P1 C1 93.92(15) . 4_565 ?
C1 P1 C1 94.4(2) . 4_565 ?
C2 C1 C6 118.7(3) . . ?
C2 C1 P1 124.6(3) . . ?
C6 C1 P1 116.6(3) . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 Cl1 119.4(3) . . ?
C1 C2 Cl1 119.4(3) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.7(3) . . ?
C5 C6 C7 123.9(4) . . ?
C1 C6 C7 116.4(3) . . ?
C6 C7 C6 108.0(4) 4_565 . ?
C6 C7 C8 108.1(3) 4_565 . ?
C6 C7 C8 108.1(3) . . ?
C6 C7 H7 110.9 4_565 . ?
C6 C7 H7 110.9 . . ?
C8 C7 H7 110.9 . . ?
C9 C8 C16 120.5(4) . . ?
C9 C8 C7 123.7(4) . . ?
C16 C8 C7 115.9(4) . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C14 C10 C9 117.9(4) . . ?
C14 C10 C11 122.3(4) . . ?
C9 C10 C11 119.8(4) . . ?
C10 C11 C13 112.7(4) . . ?
C10 C11 C12 109.5(3) . 4_565 ?
C13 C11 C12 107.5(3) . 4_565 ?
C10 C11 C12 109.5(3) . . ?
C13 C11 C12 107.5(3) . . ?
C12 C11 C12 110.2(4) 4_565 . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 112(4) . . ?
C11 C13 H13B 108(2) . . ?
H13A C13 H13B 109.4(10) . . ?
C11 C13 H13B 108(2) . 4_565 ?
H13A C13 H13B 109.4(10) . 4_565 ?
H13B C13 H13B 109.6(13) . 4_565 ?
C15 C14 C10 120.9(4) . . ?
C15 C14 H14 119.5 . . ?
C10 C14 H14 119.5 . . ?
C14 C15 C16 121.3(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C8 118.4(4) . . ?
C15 C16 P1 124.1(4) . . ?
C8 C16 P1 117.5(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
Cl1 C2 1.760(5) . ?
P1 C16 1.835(5) . ?
P1 C1 1.840(4) . ?
P1 C1 1.840(4) 4_565 ?
C1 C2 1.390(5) . ?
C1 C6 1.411(5) . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(4) . ?
C7 C8 1.532(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.372(6) . ?
C8 C16 1.399(6) . ?
C9 C10 1.402(6) . ?
C9 H9 0.9300 . ?
C10 C14 1.394(7) . ?
C10 C11 1.526(6) . ?
C11 C13 1.533(7) . ?
C11 C12 1.535(5) 4_565 ?
C11 C12 1.535(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.961(7) . ?
C13 H13B 0.961(6) . ?
C13 H13B 0.961(6) 4_565 ?
C14 C15 1.370(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(6) . ?
C15 H15 0.9300 . ?
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
C16 P1 C1 C2 -131.3(3) . . . . ?
C1 P1 C1 C2 134.4(2) 4_565 . . . ?
C16 P1 C1 C6 47.6(3) . . . . ?
C1 P1 C1 C6 -46.6(3) 4_565 . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
P1 C1 C2 C3 179.8(3) . . . . ?
C6 C1 C2 Cl1 -179.0(3) . . . . ?
P1 C1 C2 Cl1 -0.1(4) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
Cl1 C2 C3 C4 179.6(3) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C4 C5 C6 C7 -179.2(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
P1 C1 C6 C5 -179.6(3) . . . . ?
C2 C1 C6 C7 178.4(3) . . . . ?
P1 C1 C6 C7 -0.6(4) . . . . ?
C5 C6 C7 C6 -122.2(4) . . . 4_565 ?
C1 C6 C7 C6 58.8(4) . . . 4_565 ?
C5 C6 C7 C8 121.1(4) . . . . ?
C1 C6 C7 C8 -57.8(4) . . . . ?
C6 C7 C8 C9 121.7(3) 4_565 . . . ?
C6 C7 C8 C9 -121.7(3) . . . . ?
C6 C7 C8 C16 -58.3(3) 4_565 . . . ?
C6 C7 C8 C16 58.3(3) . . . . ?
C16 C8 C9 C10 0.000(1) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C8 C9 C10 C14 0.000(1) . . . . ?
C8 C9 C10 C11 180.000(1) . . . . ?
C14 C10 C11 C13 0.000(0) . . . . ?
C9 C10 C11 C13 180.000(0) . . . . ?
C14 C10 C11 C12 -119.6(3) . . . 4_565 ?
C9 C10 C11 C12 60.4(3) . . . 4_565 ?
C14 C10 C11 C12 119.6(3) . . . . ?
C9 C10 C11 C12 -60.4(3) . . . . ?
C9 C10 C14 C15 0.000(0) . . . . ?
C11 C10 C14 C15 180.000(0) . . . . ?
C10 C14 C15 C16 0.000(0) . . . . ?
C14 C15 C16 C8 0.000(1) . . . . ?
C14 C15 C16 P1 180.000(0) . . . . ?
C9 C8 C16 C15 0.000(1) . . . . ?
C7 C8 C16 C15 180.000(1) . . . . ?
C9 C8 C16 P1 180.000(0) . . . . ?
C7 C8 C16 P1 0.000(1) . . . . ?
C1 P1 C16 C15 132.64(11) . . . . ?
C1 P1 C16 C15 -132.64(11) 4_565 . . . ?
C1 P1 C16 C8 -47.36(11) . . . . ?
C1 P1 C16 C8 47.36(11) 4_565 . . . ?
