#------------------------------------------------------------------------------
#$Date: 2024-05-05 07:05:25 +0300 (Sun, 05 May 2024) $
#$Revision: 291696 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159859.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_7159859
loop_
_publ_author_name
'Huang, Hua'
'Wu, Yi-Qi'
'Han, Lu-Yao'
'Jiang, Lu'
'Zhang, Zhuo-Zhuo'
'Zhang, Xiang'
'Han, Bo'
'Huang, Wei'
'Li, Jun-Long'
_publ_section_title
;
 Palladium-catalyzed (Z)-selective allylation of phosphine oxides
 with vinylethylene carbonates to construct phosphorus allyl alcohols.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3068
_journal_page_last               3072
_journal_paper_doi               10.1039/d4ob00354c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H20 Cl O2 P'
_chemical_formula_sum            'C22 H20 Cl O2 P'
_chemical_formula_weight         382.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-12-11 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9972(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.74906(11)
_cell_length_b                   19.4433(5)
_cell_length_c                   17.5592(4)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.0920
_cell_measurement_theta_min      5.1690
_cell_volume                     1958.01(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00   3.00   1.00    4.68    --  -34.98 -19.00 150.00  110
  2  ω     23.00  90.00   1.00    4.68    --   34.98-125.00  30.00   67
  3  ω    -33.00  53.00   1.00    4.68    --   34.98 -57.00  60.00   86
  4  ω      6.00 104.00   1.00    4.68    --   34.98  77.00 -90.00   98
  5  ω      1.00  75.00   1.00    4.68    --   34.98 -99.00-120.00   74
  6  ω     13.00 106.00   1.00    4.68    --   34.98  38.00  30.00   93
  7  ω     87.00 177.00   1.00   18.73    --  106.90  45.00-120.00   90
  8  ω     36.00 113.00   1.00   18.73    --  106.90-111.00 -90.00   77
  9  ω    100.00 178.00   1.00   18.73    --  106.90 111.00 150.00   78
 10  ω     36.00 113.00   1.00   18.73    --  106.90-111.00-120.00   77
 11  ω     81.00 178.00   1.00   18.73    --  106.90  30.00-150.00   97
 12  ω     36.00 113.00   1.00   18.73    --  106.90-111.00  60.00   77
 13  ω     81.00 178.00   1.00   18.73    --  106.90  30.00 -60.00   97
 14  ω     41.00 110.00   1.00   18.73    --  106.90 -94.00  90.00   69
 15  ω     44.00 126.00   1.00   18.73    --  106.90 -45.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0237675000
_diffrn_orient_matrix_UB_12      -0.0453122000
_diffrn_orient_matrix_UB_13      0.0720600000
_diffrn_orient_matrix_UB_21      -0.0339780000
_diffrn_orient_matrix_UB_22      0.0638682000
_diffrn_orient_matrix_UB_23      0.0499998000
_diffrn_orient_matrix_UB_31      -0.2654000000
_diffrn_orient_matrix_UB_32      -0.0122243000
_diffrn_orient_matrix_UB_33      -0.0061534000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10742
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.318
_diffrn_reflns_theta_min         4.548
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0618
_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)+(0.1300P)²+0.2018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3033
_reflns_number_total             3732
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00354c2.cif
_cod_data_source_block           ljl-hh-0924
_cod_depositor_comments          'Adding full bibliography for 7159859.cif.'
_cod_original_cell_volume        1958.00(8)
_cod_database_code               7159859
_shelx_shelxl_version_number     2014/7
_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.
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00E), C00E(H00F), C00F(H00G),
 C00H(H00H), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C00O(H00P), C00P(H00Q), C00Q(H00R)
2.c Idealised tetrahedral OH refined as rotating group:
 O004(H004)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.644
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
P01 P 0.70377(9) 0.49699(3) 0.67821(3) 0.0410(2) Uani 1 1 d . . . . .
Cl02 Cl 0.4808(2) 0.94289(5) 0.58218(7) 0.0972(4) Uani 1 1 d . . . . .
O003 O 0.4532(3) 0.50518(9) 0.65182(10) 0.0504(4) Uani 1 1 d . . . . .
O004 O 0.3490(3) 0.58138(12) 0.51728(12) 0.0648(5) Uani 1 1 d . . . . .
H004 H 0.3625 0.5618 0.5587 0.097 Uiso 1 1 calc GR . . . .
C005 C 0.6548(4) 0.71717(13) 0.56403(12) 0.0450(5) Uani 1 1 d . . . . .
C006 C 0.7058(4) 0.64248(13) 0.55891(12) 0.0436(5) Uani 1 1 d . . . . .
C007 C 0.7669(4) 0.54028(13) 0.76861(13) 0.0470(5) Uani 1 1 d . . . . .
C008 C 0.7840(4) 0.40752(13) 0.69014(13) 0.0464(5) Uani 1 1 d . . . . .
C009 C 0.8122(4) 0.76327(14) 0.59953(15) 0.0539(6) Uani 1 1 d . . . . .
H009 H 0.9563 0.7473 0.6195 0.065 Uiso 1 1 calc R . . . .
C00A C 0.6043(5) 0.58701(17) 0.79146(17) 0.0623(7) Uani 1 1 d . . . . .
H00A H 0.4667 0.5944 0.7615 0.075 Uiso 1 1 calc R . . . .
C00B C 0.8530(4) 0.61104(13) 0.60956(13) 0.0461(5) Uani 1 1 d . . . . .
H00B H 0.9335 0.6389 0.6455 0.055 Uiso 1 1 calc R . . . .
C00C C 0.5727(5) 0.60234(14) 0.49611(14) 0.0534(6) Uani 1 1 d . . . . .
H00C H 0.5542 0.6306 0.4506 0.064 Uiso 1 1 calc R . . . .
H00D H 0.6621 0.5620 0.4840 0.064 Uiso 1 1 calc R . . . .
C00D C 0.3897(5) 0.81250(17) 0.5400(2) 0.0679(8) Uani 1 1 d . . . . .
H00E H 0.2466 0.8292 0.5201 0.081 Uiso 1 1 calc R . . . .
C00E C 0.9710(5) 0.52958(17) 0.81305(17) 0.0627(7) Uani 1 1 d . . . . .
H00F H 1.0818 0.4986 0.7977 0.075 Uiso 1 1 calc R . . . .
C00F C 0.4432(5) 0.74335(15) 0.53391(17) 0.0589(6) Uani 1 1 d . . . . .
H00G H 0.3354 0.7139 0.5091 0.071 Uiso 1 1 calc R . . . .
C00G C 0.5498(6) 0.85621(15) 0.57587(16) 0.0622(7) Uani 1 1 d . . . . .
C00H C 0.7594(6) 0.83245(16) 0.60592(17) 0.0639(7) Uani 1 1 d . . . . .
H00H H 0.8662 0.8624 0.6305 0.077 Uiso 1 1 calc R . . . .
C00I C 0.9019(4) 0.53565(13) 0.61442(14) 0.0476(5) Uani 1 1 d . . . . .
H00I H 1.0620 0.5279 0.6337 0.057 Uiso 1 1 calc R . . . .
H00J H 0.8797 0.5150 0.5642 0.057 Uiso 1 1 calc R . . . .
C00J C 0.8475(6) 0.6121(2) 0.90302(19) 0.0822(11) Uani 1 1 d . . . . .
H00K H 0.8752 0.6365 0.9483 0.099 Uiso 1 1 calc R . . . .
C00K C 1.0087(6) 0.5657(2) 0.8810(2) 0.0810(10) Uani 1 1 d . . . . .
H00L H 1.1447 0.5583 0.9118 0.097 Uiso 1 1 calc R . . . .
C00L C 0.6384(5) 0.36549(17) 0.72824(19) 0.0670(7) Uani 1 1 d . . . . .
H00M H 0.5089 0.3842 0.7495 0.080 Uiso 1 1 calc R . . . .
C00M C 0.8720(7) 0.26732(17) 0.7039(2) 0.0764(9) Uani 1 1 d . . . . .
H00N H 0.9011 0.2204 0.7079 0.092 Uiso 1 1 calc R . . . .
C00N C 0.9762(6) 0.37924(18) 0.6599(2) 0.0792(10) Uani 1 1 d . . . . .
H00O H 1.0784 0.4071 0.6350 0.095 Uiso 1 1 calc R . . . .
C00O C 0.6472(6) 0.6227(2) 0.8589(2) 0.0796(10) Uani 1 1 d . . . . .
H00P H 0.5382 0.6542 0.8743 0.096 Uiso 1 1 calc R . . . .
C00P C 0.6820(7) 0.29592(18) 0.7352(2) 0.0799(9) Uani 1 1 d . . . . .
H00Q H 0.5823 0.2682 0.7613 0.096 Uiso 1 1 calc R . . . .
C00Q C 1.0177(7) 0.3094(2) 0.6665(3) 0.0915(12) Uani 1 1 d . . . . .
H00R H 1.1470 0.2906 0.6452 0.110 Uiso 1 1 calc R . . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
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
O003 P01 C007 110.68(11) . . ?
O003 P01 C008 111.83(11) . . ?
O003 P01 C00I 113.48(10) . . ?
C007 P01 C00I 104.61(12) . . ?
C008 P01 C007 108.16(11) . . ?
C008 P01 C00I 107.70(11) . . ?
C00C O004 H004 109.5 . . ?
C009 C005 C006 122.2(2) . . ?
C00F C005 C006 120.4(2) . . ?
C00F C005 C009 117.4(2) . . ?
C005 C006 C00C 117.1(2) . . ?
C00B C006 C005 121.8(2) . . ?
C00B C006 C00C 121.0(2) . . ?
C00A C007 P01 117.5(2) . . ?
C00E C007 P01 122.5(2) . . ?
C00E C007 C00A 120.0(3) . . ?
C00L C008 P01 118.0(2) . . ?
C00N C008 P01 123.1(2) . . ?
C00N C008 C00L 118.9(3) . . ?
C005 C009 H009 119.2 . . ?
C00H C009 C005 121.5(2) . . ?
C00H C009 H009 119.2 . . ?
C007 C00A H00A 120.2 . . ?
C00O C00A C007 119.7(3) . . ?
C00O C00A H00A 120.2 . . ?
C006 C00B H00B 116.7 . . ?
C006 C00B C00I 126.6(2) . . ?
C00I C00B H00B 116.7 . . ?
O004 C00C C006 112.2(2) . . ?
O004 C00C H00C 109.2 . . ?
O004 C00C H00D 109.2 . . ?
C006 C00C H00C 109.2 . . ?
C006 C00C H00D 109.2 . . ?
H00C C00C H00D 107.9 . . ?
C00F C00D H00E 120.3 . . ?
C00G C00D H00E 120.3 . . ?
C00G C00D C00F 119.4(3) . . ?
C007 C00E H00F 120.5 . . ?
C007 C00E C00K 119.1(3) . . ?
C00K C00E H00F 120.5 . . ?
C005 C00F H00G 119.3 . . ?
C00D C00F C005 121.3(3) . . ?
C00D C00F H00G 119.3 . . ?
C00D C00G Cl02 118.8(2) . . ?
C00H C00G Cl02 120.3(3) . . ?
C00H C00G C00D 120.9(3) . . ?
C009 C00H H00H 120.3 . . ?
C00G C00H C009 119.4(3) . . ?
C00G C00H H00H 120.3 . . ?
P01 C00I H00I 110.0 . . ?
P01 C00I H00J 110.0 . . ?
C00B C00I P01 108.54(16) . . ?
C00B C00I H00I 110.0 . . ?
C00B C00I H00J 110.0 . . ?
H00I C00I H00J 108.4 . . ?
C00K C00J H00K 119.9 . . ?
C00O C00J H00K 119.9 . . ?
C00O C00J C00K 120.2(3) . . ?
C00E C00K H00L 119.7 . . ?
C00J C00K C00E 120.5(3) . . ?
C00J C00K H00L 119.7 . . ?
C008 C00L H00M 119.6 . . ?
C008 C00L C00P 120.8(3) . . ?
C00P C00L H00M 119.6 . . ?
C00P C00M H00N 120.7 . . ?
C00Q C00M H00N 120.7 . . ?
C00Q C00M C00P 118.6(3) . . ?
C008 C00N H00O 120.0 . . ?
C008 C00N C00Q 120.0(3) . . ?
C00Q C00N H00O 120.0 . . ?
C00A C00O H00P 119.8 . . ?
C00J C00O C00A 120.5(3) . . ?
C00J C00O H00P 119.8 . . ?
C00L C00P H00Q 119.8 . . ?
C00M C00P C00L 120.4(3) . . ?
C00M C00P H00Q 119.8 . . ?
C00M C00Q C00N 121.3(3) . . ?
C00M C00Q H00R 119.4 . . ?
C00N C00Q H00R 119.4 . . ?
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
P01 O003 1.4909(17) . ?
P01 C007 1.811(2) . ?
P01 C008 1.808(3) . ?
P01 C00I 1.815(2) . ?
Cl02 C00G 1.737(3) . ?
O004 H004 0.8200 . ?
O004 C00C 1.423(3) . ?
C005 C006 1.486(3) . ?
C005 C009 1.390(4) . ?
C005 C00F 1.389(3) . ?
C006 C00B 1.333(3) . ?
C006 C00C 1.514(3) . ?
C007 C00A 1.383(4) . ?
C007 C00E 1.379(4) . ?
C008 C00L 1.376(4) . ?
C008 C00N 1.374(4) . ?
C009 H009 0.9300 . ?
C009 C00H 1.385(4) . ?
C00A H00A 0.9300 . ?
C00A C00O 1.380(4) . ?
C00B H00B 0.9300 . ?
C00B C00I 1.494(4) . ?
C00C H00C 0.9700 . ?
C00C H00D 0.9700 . ?
C00D H00E 0.9300 . ?
C00D C00F 1.385(4) . ?
C00D C00G 1.373(5) . ?
C00E H00F 0.9300 . ?
C00E C00K 1.388(4) . ?
C00F H00G 0.9300 . ?
C00G C00H 1.362(5) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00J H00K 0.9300 . ?
C00J C00K 1.369(5) . ?
C00J C00O 1.357(5) . ?
C00K H00L 0.9300 . ?
C00L H00M 0.9300 . ?
C00L C00P 1.380(5) . ?
C00M H00N 0.9300 . ?
C00M C00P 1.375(5) . ?
C00M C00Q 1.370(5) . ?
C00N H00O 0.9300 . ?
C00N C00Q 1.382(5) . ?
C00O H00P 0.9300 . ?
C00P H00Q 0.9300 . ?
C00Q H00R 0.9300 . ?
