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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/7/70/68/7706854.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_7706854
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         'C19 H12 Cl P'
_chemical_formula_sum            'C19 H12 Cl P'
_chemical_formula_weight         306.71
_chemical_name_common            4-chloro-10H-5,10-[1,2]benzenoacridophosphine
_chemical_name_systematic        4-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   mixed
_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                 113.053(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2135(3)
_cell_length_b                   13.7539(4)
_cell_length_c                   8.1944(3)
_cell_measurement_reflns_used    1486
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      66.3840
_cell_measurement_theta_min      7.3900
_cell_volume                     748.07(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.987
_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     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2755
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.188
_diffrn_reflns_theta_max         67.188
_diffrn_reflns_theta_min         5.868
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.164
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.16b (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.057
_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     120
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0664
_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)+(0.0875P)²+0.3746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2007
_refine_ls_wR_factor_ref         0.2080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1966
_reflns_number_total             2755
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt00816a2.cif
_cod_data_source_block           nt0589_Lei_trip-Cl
_cod_depositor_comments
'Adding full bibliography for 7706848--7706861.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7706854
_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   0.585
_shelx_estimated_absorpt_t_max   0.945
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 0.8899(4) 0.4533(2) 0.8253(4) 0.0809(10) Uani 0.447(3) 1 d . . P A 1
P1 P 0.6957(3) 0.250000 0.5683(2) 0.0629(6) Uani 1 2 d S T P A .
Cl2 Cl 0.774(3) 0.250000 0.180(3) 0.106(9) Uani 0.106(6) 2 d S TU P A 3
C1 C 0.5620(7) 0.3471(3) 0.6288(5) 0.0578(11) Uani 1 1 d . . . . .
C2 C 0.6506(9) 0.4274(4) 0.7369(6) 0.0789(15) Uani 1 1 d . . . . .
H2 H 0.789621 0.435254 0.780550 0.095 Uiso 0.5532 1 calc R U P A 2
C3 C 0.5356(12) 0.4946(4) 0.7796(7) 0.0894(18) Uani 1 1 d . . . . .
H3 H 0.597592 0.546688 0.853116 0.107 Uiso 1 1 calc R U . . .
C4 C 0.3306(12) 0.4853(4) 0.7144(8) 0.0913(18) Uani 1 1 d . . . . .
H4 H 0.253501 0.531496 0.742439 0.110 Uiso 1 1 calc R U . . .
C5 C 0.2379(9) 0.4075(3) 0.6070(6) 0.0736(13) Uani 1 1 d . . . . .
H5 H 0.098551 0.400901 0.563359 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3520(7) 0.3399(3) 0.5647(5) 0.0565(10) Uani 1 1 d . . . . .
C7 C 0.2586(9) 0.250000 0.4521(7) 0.0547(14) Uani 1 2 d S T P . .
H7 H 0.111602 0.250000 0.412883 0.066 Uiso 1 2 calc R U P . .
C8 C 0.3211(10) 0.250000 0.2937(7) 0.0564(14) Uani 1 2 d S T P A .
C9 C 0.1879(11) 0.250000 0.1187(8) 0.0703(18) Uani 1 2 d S T P . .
H9 H 0.049854 0.250000 0.090671 0.084 Uiso 1 2 calc R U P . .
C10 C 0.2593(13) 0.250000 -0.0154(9) 0.076(2) Uani 1 2 d S T P A .
H10 H 0.168248 0.250000 -0.133060 0.092 Uiso 1 2 calc R U P . .
C11 C 0.4574(14) 0.250000 0.0214(9) 0.078(2) Uani 1 2 d S T P . .
H11 H 0.503131 0.250000 -0.070126 0.093 Uiso 1 2 calc R U P A 3
C12 C 0.5951(12) 0.250000 0.1980(9) 0.0712(18) Uani 1 2 d S TU P A .
H12 H 0.732673 0.250000 0.223977 0.085 Uiso 0.894(6) 2 calc R U P A 4
C13 C 0.5276(9) 0.250000 0.3331(7) 0.0558(14) 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
C1 P1 C1 94.0(3) 4_565 . ?
C1 P1 C13 94.80(19) 4_565 . ?
C1 P1 C13 94.80(19) . . ?
C12 Cl2 C11 39.8(7) . . ?
C6 C1 C2 116.8(4) . . ?
C6 C1 P1 117.1(3) . . ?
C2 C1 P1 126.1(4) . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 Cl1 112.3(5) . . ?
C1 C2 Cl1 126.5(5) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.7(4) . . ?
C5 C6 C7 122.2(4) . . ?
C1 C6 C7 116.0(4) . . ?
C8 C7 C6 107.7(3) . . ?
C8 C7 C6 107.7(3) . 4_565 ?
C6 C7 C6 107.6(4) . 4_565 ?
C8 C7 H7 111.2 . . ?
C6 C7 H7 111.2 . . ?
C6 C7 H7 111.2 4_565 . ?
C9 C8 C13 119.1(6) . . ?
C9 C8 C7 124.4(6) . . ?
C13 C8 C7 116.5(5) . . ?
C8 C9 C10 120.1(7) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 121.1(6) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.7(6) . . ?
C10 C11 Cl2 158.0(7) . . ?
C12 C11 Cl2 38.3(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
Cl2 C11 H11 81.8 . . ?
Cl2 C12 C13 137.9(11) . . ?
Cl2 C12 C11 101.9(10) . . ?
C13 C12 C11 120.2(7) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.8(6) . . ?
C12 C13 P1 123.5(5) . . ?
C8 C13 P1 116.8(4) . . ?
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 1.629(6) . ?
P1 C1 1.826(5) 4_565 ?
P1 C1 1.826(5) . ?
P1 C13 1.831(6) . ?
Cl2 C12 1.35(2) . ?
Cl2 C11 2.14(2) . ?
C1 C6 1.399(6) . ?
C1 C2 1.403(6) . ?
C2 C3 1.376(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.532(5) . ?
C7 C8 1.532(8) . ?
C7 H7 0.9800 . ?
C8 C9 1.379(9) . ?
C8 C13 1.396(9) . ?
C9 C10 1.384(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.340(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.398(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(8) . ?
C12 H12 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
C1 P1 C1 C6 -48.3(4) 4_565 . . . ?
C13 P1 C1 C6 46.8(3) . . . . ?
C1 P1 C1 C2 130.3(3) 4_565 . . . ?
C13 P1 C1 C2 -134.6(4) . . . . ?
C6 C1 C2 C3 1.1(6) . . . . ?
P1 C1 C2 C3 -177.6(4) . . . . ?
C6 C1 C2 Cl1 -179.0(4) . . . . ?
P1 C1 C2 Cl1 2.4(6) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
Cl1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 C1 0.5(6) . . . . ?
C4 C5 C6 C7 177.6(4) . . . . ?
C2 C1 C6 C5 -0.7(6) . . . . ?
P1 C1 C6 C5 178.0(3) . . . . ?
C2 C1 C6 C7 -178.0(4) . . . . ?
P1 C1 C6 C7 0.7(5) . . . . ?
C5 C6 C7 C8 124.5(5) . . . . ?
C1 C6 C7 C8 -58.3(5) . . . . ?
C5 C6 C7 C6 -119.6(4) . . . 4_565 ?
C1 C6 C7 C6 57.6(5) . . . 4_565 ?
C6 C7 C8 C9 -122.1(3) . . . . ?
C6 C7 C8 C9 122.1(3) 4_565 . . . ?
C6 C7 C8 C13 57.9(3) . . . . ?
C6 C7 C8 C13 -57.9(3) 4_565 . . . ?
C13 C8 C9 C10 0.000(1) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C9 C10 C11 Cl2 0.000(3) . . . . ?
C11 Cl2 C12 C13 180.000(1) . . . . ?
C10 C11 C12 Cl2 180.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
Cl2 C11 C12 C13 180.000(1) . . . . ?
Cl2 C12 C13 C8 180.000(1) . . . . ?
C11 C12 C13 C8 0.000(1) . . . . ?
Cl2 C12 C13 P1 0.000(1) . . . . ?
C11 C12 C13 P1 180.000(0) . . . . ?
C9 C8 C13 C12 0.000(1) . . . . ?
C7 C8 C13 C12 180.000(1) . . . . ?
C9 C8 C13 P1 180.000(1) . . . . ?
C7 C8 C13 P1 0.000(1) . . . . ?
C1 P1 C13 C12 -132.79(13) 4_565 . . . ?
C1 P1 C13 C12 132.79(13) . . . . ?
C1 P1 C13 C8 47.21(13) 4_565 . . . ?
C1 P1 C13 C8 -47.21(13) . . . . ?
