#------------------------------------------------------------------------------
#$Date: 2019-10-22 02:57:08 +0300 (Tue, 22 Oct 2019) $
#$Revision: 219438 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/43/7124349.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_7124349
loop_
_publ_author_name
'Chen, Lijin'
'Zhou, Zhenfei'
'Zhang, Saifei'
'Li, Xiaoqian'
'Ma, Xuebing'
'Dong, Jiaxing'
_publ_section_title
;
 Palladium(II)-catalyzed Oxidative C(sp3)--P Bond Formation via C(sp3)--H
 Bond Activation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07637A
_journal_year                    2019
_chemical_formula_moiety         'C24 H22 N O3 P Pd'
_chemical_formula_sum            'C24 H22 N O3 P Pd'
_chemical_formula_weight         509.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2019-04-25 deposited with the CCDC.    2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                114.219(4)
_cell_angle_beta                 99.926(3)
_cell_angle_gamma                98.501(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8937(4)
_cell_length_b                   10.7491(4)
_cell_length_c                   12.9531(5)
_cell_measurement_reflns_used    22777
_cell_measurement_temperature    282(3)
_cell_measurement_theta_max      28.2120
_cell_measurement_theta_min      3.5810
_cell_volume                     1078.99(9)
_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      282(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  10.00   1.00    2.11    --  -16.50 -77.00-150.00   94
  2  ω    -84.00   0.00   1.00    2.11    --  -16.50 -57.00  90.00   84
  3  ω    -51.00  33.00   1.00    2.11    --   16.50 -57.00-150.00   84
  4  ω    -10.00  84.00   1.00    2.11    --   16.50  77.00 150.00   94
  5  ω    -20.00  55.00   1.00    2.11    --   16.50 -99.00 -60.00   75
  6  ω    -20.00  55.00   1.00    2.11    --   16.50 -99.00  90.00   75
  7  ω    -20.00  55.00   1.00    2.11    --   16.50 -99.00   0.00   75
  8  ω     35.00  89.00   1.00    2.11    --   16.50 178.00-120.00   54
  9  ω     -2.00  80.00   1.00    2.11    --   16.50  38.00 -60.00   82
 10  ω      0.00  84.00   1.00    2.11    --   16.50  57.00   0.00   84
 11  ω    -76.00 -23.00   1.00    2.11    --  -16.50 -57.00  30.00   53
 12  ω    -67.00 -42.00   1.00    2.11    --  -16.50 119.00  53.58   25
 13  ω    -69.00 -44.00   1.00    2.11    --  -16.50 123.00 156.99   25
 14  ω     -9.00  63.00   1.00    2.11    --   16.35-112.00 -36.60   72
 15  ω     35.00  89.00   1.00    2.11    --   16.35 178.00 -90.00   54
 16  ω    -86.00  53.00   1.00    2.11    --  -16.50   0.00 150.00  139
 17  ω    -73.00 -27.00   1.00    2.11    --  -16.50 131.00 -19.63   46
 18  ω    -43.00  51.00   1.00    2.11    --  -16.50  77.00-150.00   94
 19  ω    -69.00 -22.00   1.00    2.11    --  -16.50 123.00  44.96   47
 20  ω    -69.00 -22.00   1.00    2.11    --  -16.50 123.00 156.99   47
 21  ω    -75.00 -29.00   1.00    2.11    --  -16.50 133.00 177.38   46
 22  ω    -75.00 -29.00   1.00    2.11    --  -16.50 133.00  85.44   46
 23  ω    -84.00   0.00   1.00    2.11    --  -16.50 -57.00   0.00   84
 24  ω    -53.00  86.00   1.00    2.11    --   16.35   0.00-150.00  139
 25  ω    -53.00  86.00   1.00    2.11    --   16.35   0.00-120.00  139
 26  ω    -53.00  86.00   1.00    2.11    --   16.35   0.00-180.00  139
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, 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      -0.0135998000
_diffrn_orient_matrix_UB_12      -0.0679052000
_diffrn_orient_matrix_UB_13      -0.0471508000
_diffrn_orient_matrix_UB_21      -0.0738464000
_diffrn_orient_matrix_UB_22      0.0068583000
_diffrn_orient_matrix_UB_23      -0.0251426000
_diffrn_orient_matrix_UB_31      0.0364633000
_diffrn_orient_matrix_UB_32      0.0301065000
_diffrn_orient_matrix_UB_33      -0.0317457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            46678
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.464
_diffrn_reflns_theta_min         3.498
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59977
_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    1.569
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.346
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0447
_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)+(0.0610P)²+1.5590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4895
_reflns_number_total             5484
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc07637a2.cif
_cod_data_source_block           exp_1928
_cod_original_cell_volume        1078.99(8)
_cod_database_code               7124349
_chemical_oxdiff_formula         'C1 H1 O1 N1 P1 Pd1'
_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 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C16) = Uanis(C14) = Uanis(C17) = Uanis(C13) = Uanis(C12)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
3.c Fitted hexagon refined as free rotating group:
 C15(C16,C17,C12,C13,C14)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2019-01-17
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.567
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
Pd1 Pd 0.58530(3) 0.20451(2) 0.01658(2) 0.03439(10) Uani 1 1 d .
P1 P 0.42693(12) 0.00270(9) 0.12638(8) 0.0412(2) Uani 1 1 d .
O1 O 0.4336(3) 0.1280(3) 0.1006(2) 0.0481(6) Uani 1 1 d .
O2 O 0.5817(4) 0.0306(3) 0.2279(3) 0.0705(9) Uani 1 1 d .
O3 O 0.3010(4) 0.0121(3) 0.2031(3) 0.0668(9) Uani 1 1 d .
N1 N 0.5959(3) 0.4118(3) 0.1359(3) 0.0387(6) Uani 1 1 d .
C1 C 0.7280(5) 0.3015(4) -0.0484(3) 0.0441(8) Uani 1 1 d .
H1A H 0.832358 0.285647 -0.033273 0.053 Uiso 1 1 calc R
H1B H 0.686669 0.263874 -0.132504 0.053 Uiso 1 1 calc R
C2 C 0.7361(4) 0.4569(4) 0.0103(3) 0.0418(7) Uani 1 1 d .
C3 C 0.8033(5) 0.5518(4) -0.0254(4) 0.0533(9) Uani 1 1 d .
H3 H 0.846918 0.520021 -0.089036 0.064 Uiso 1 1 calc R
C4 C 0.8068(5) 0.6952(5) 0.0326(5) 0.0617(11) Uani 1 1 d .
H4 H 0.853150 0.756407 0.006699 0.074 Uiso 1 1 calc R
C5 C 0.7444(5) 0.7468(4) 0.1257(4) 0.0589(11) Uani 1 1 d .
H5 H 0.748324 0.842308 0.162835 0.071 Uiso 1 1 calc R
C6 C 0.6733(4) 0.6545(4) 0.1661(3) 0.0468(8) Uani 1 1 d .
C7 C 0.6696(4) 0.5094(3) 0.1057(3) 0.0386(7) Uani 1 1 d .
C8 C 0.5261(5) 0.4552(4) 0.2221(3) 0.0513(9) Uani 1 1 d .
H8 H 0.473485 0.388918 0.240572 0.062 Uiso 1 1 calc R
C9 C 0.5280(6) 0.5974(5) 0.2869(4) 0.0605(11) Uani 1 1 d .
H9 H 0.479659 0.624228 0.348232 0.073 Uiso 1 1 calc R
C10 C 0.6010(5) 0.6952(4) 0.2593(4) 0.0577(10) Uani 1 1 d .
H10 H 0.603215 0.789499 0.302139 0.069 Uiso 1 1 calc R
C11 C 0.6529(6) 0.1680(5) 0.3181(4) 0.0645(11) Uani 1 1 d .
H11A H 0.573517 0.220239 0.337588 0.077 Uiso 1 1 calc R
H11B H 0.727100 0.217381 0.292690 0.077 Uiso 1 1 calc R
C15 C 0.8937(4) 0.1560(5) 0.6269(3) 0.0795(6) Uani 1 1 d .
H15 H 0.946487 0.156015 0.695439 0.095 Uiso 1 1 calc R
C16 C 0.7311(4) 0.1366(5) 0.6002(3) 0.0795(6) Uani 1 1 d G
H16 H 0.675201 0.123642 0.650907 0.095 Uiso 1 1 calc R
C17 C 0.6522(3) 0.1365(5) 0.4978(3) 0.0795(6) Uani 1 1 d G
H17 H 0.543405 0.123519 0.479903 0.095 Uiso 1 1 calc R
C12 C 0.7357(4) 0.1558(5) 0.4220(3) 0.0795(6) Uani 1 1 d G
C13 C 0.8983(4) 0.1752(5) 0.4487(3) 0.0795(6) Uani 1 1 d G
H13 H 0.954177 0.188141 0.397959 0.095 Uiso 1 1 calc R
C14 C 0.9772(3) 0.1753(5) 0.5511(3) 0.0795(6) Uani 1 1 d G
H14 H 1.085977 0.188265 0.568963 0.095 Uiso 1 1 calc R
C18 C 0.1558(6) 0.0394(5) 0.1670(5) 0.0784(16) Uani 1 1 d .
H18A H 0.071752 -0.025941 0.170945 0.094 Uiso 1 1 calc R
H18B H 0.139443 0.022782 0.085987 0.094 Uiso 1 1 calc R
C19 C 0.1461(5) 0.1896(4) 0.2415(4) 0.0539(9) Uani 1 1 d .
C20 C 0.2444(6) 0.2717(5) 0.3511(4) 0.0676(12) Uani 1 1 d .
H20 H 0.319335 0.236519 0.382907 0.081 Uiso 1 1 calc R
C21 C 0.2314(7) 0.4083(7) 0.4144(6) 0.094(2) Uani 1 1 d .
H21 H 0.298049 0.465174 0.488758 0.113 Uiso 1 1 calc R
C22 C 0.1188(9) 0.4588(6) 0.3662(7) 0.099(2) Uani 1 1 d .
H22 H 0.111963 0.550999 0.407289 0.119 Uiso 1 1 calc R
C23 C 0.0193(9) 0.3759(8) 0.2606(7) 0.0946(19) Uani 1 1 d .
H23 H -0.058837 0.409331 0.229940 0.114 Uiso 1 1 calc R
C24 C 0.0332(6) 0.2411(6) 0.1976(5) 0.0715(13) Uani 1 1 d .
H24 H -0.035342 0.184345 0.123993 0.086 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 0.0033 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'
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'
Pd Pd -0.9988 1.0072 '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_3
O1 Pd1 P1 96.48(7) 2_655
N1 Pd1 P1 172.40(8) 2_655
N1 Pd1 O1 89.41(10) .
C1 Pd1 P1 90.69(10) 2_655
C1 Pd1 O1 172.76(11) .
C1 Pd1 N1 83.36(13) .
O1 P1 Pd1 118.99(11) 2_655
O1 P1 O2 110.25(18) .
O1 P1 O3 105.51(16) .
O2 P1 Pd1 104.54(12) 2_655
O3 P1 Pd1 117.95(13) 2_655
O3 P1 O2 97.4(2) .
P1 O1 Pd1 129.93(16) .
C11 O2 P1 120.4(3) .
C18 O3 P1 119.3(3) .
C7 N1 Pd1 112.0(2) .
C8 N1 Pd1 128.6(3) .
C8 N1 C7 118.7(3) .
Pd1 C1 H1A 110.0 .
Pd1 C1 H1B 110.0 .
H1A C1 H1B 108.4 .
C2 C1 Pd1 108.4(2) .
C2 C1 H1A 110.0 .
C2 C1 H1B 110.0 .
C3 C2 C1 123.9(4) .
C3 C2 C7 117.4(3) .
C7 C2 C1 118.7(3) .
C2 C3 H3 119.4 .
C2 C3 C4 121.2(4) .
C4 C3 H3 119.4 .
C3 C4 H4 119.1 .
C5 C4 C3 121.7(4) .
C5 C4 H4 119.1 .
C4 C5 H5 120.1 .
C4 C5 C6 119.7(4) .
C6 C5 H5 120.1 .
C5 C6 C7 117.8(4) .
C10 C6 C5 124.8(4) .
C10 C6 C7 117.3(4) .
N1 C7 C2 116.5(3) .
N1 C7 C6 121.4(3) .
C2 C7 C6 122.1(3) .
N1 C8 H8 118.6 .
N1 C8 C9 122.8(4) .
C9 C8 H8 118.6 .
C8 C9 H9 120.3 .
C10 C9 C8 119.4(4) .
C10 C9 H9 120.3 .
C6 C10 H10 119.8 .
C9 C10 C6 120.3(4) .
C9 C10 H10 119.8 .
O2 C11 H11A 110.1 .
O2 C11 H11B 110.1 .
O2 C11 C12 108.1(4) .
H11A C11 H11B 108.4 .
C12 C11 H11A 110.1 .
C12 C11 H11B 110.1 .
C16 C15 H15 120.0 .
C16 C15 C14 120.0 .
C14 C15 H15 120.0 .
C15 C16 H16 120.0 .
C15 C16 C17 120.0 .
C17 C16 H16 120.0 .
C16 C17 H17 120.0 .
C12 C17 C16 120.0 .
C12 C17 H17 120.0 .
C17 C12 C11 119.8(3) .
C17 C12 C13 120.0 .
C13 C12 C11 120.0(3) .
C12 C13 H13 120.0 .
C14 C13 C12 120.0 .
C14 C13 H13 120.0 .
C15 C14 H14 120.0 .
C13 C14 C15 120.0 .
C13 C14 H14 120.0 .
O3 C18 H18A 109.0 .
O3 C18 H18B 109.0 .
O3 C18 C19 113.1(4) .
H18A C18 H18B 107.8 .
C19 C18 H18A 109.0 .
C19 C18 H18B 109.0 .
C20 C19 C18 122.0(5) .
C24 C19 C18 118.4(5) .
C24 C19 C20 119.5(4) .
C19 C20 H20 120.2 .
C19 C20 C21 119.5(5) .
C21 C20 H20 120.2 .
C20 C21 H21 120.2 .
C22 C21 C20 119.6(6) .
C22 C21 H21 120.2 .
C21 C22 H22 119.8 .
C23 C22 C21 120.5(6) .
C23 C22 H22 119.8 .
C22 C23 H23 120.1 .
C22 C23 C24 119.8(6) .
C24 C23 H23 120.1 .
C19 C24 C23 121.0(6) .
C19 C24 H24 119.5 .
C23 C24 H24 119.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 P1 2.2083(9) 2_655
Pd1 O1 2.144(2) .
Pd1 N1 2.104(3) .
Pd1 C1 2.026(3) .
P1 O1 1.510(3) .
P1 O2 1.626(3) .
P1 O3 1.608(3) .
O2 C11 1.414(5) .
O3 C18 1.410(7) .
N1 C7 1.380(5) .
N1 C8 1.321(5) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 C2 1.509(5) .
C2 C3 1.383(5) .
C2 C7 1.405(5) .
C3 H3 0.9300 .
C3 C4 1.403(6) .
C4 H4 0.9300 .
C4 C5 1.357(7) .
C5 H5 0.9300 .
C5 C6 1.419(6) .
C6 C7 1.422(5) .
C6 C10 1.407(6) .
C8 H8 0.9300 .
C8 C9 1.406(6) .
C9 H9 0.9300 .
C9 C10 1.357(7) .
C10 H10 0.9300 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.483(5) .
C15 H15 0.9300 .
C15 C16 1.3900 .
C15 C14 1.3900 .
C16 H16 0.9300 .
C16 C17 1.3900 .
C17 H17 0.9300 .
C17 C12 1.3900 .
C12 C13 1.3900 .
C13 H13 0.9300 .
C13 C14 1.3900 .
C14 H14 0.9300 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 C19 1.528(6) .
C19 C20 1.369(6) .
C19 C24 1.366(7) .
C20 H20 0.9300 .
C20 C21 1.391(8) .
C21 H21 0.9300 .
C21 C22 1.384(10) .
C22 H22 0.9300 .
C22 C23 1.340(10) .
C23 H23 0.9300 .
C23 C24 1.378(9) .
C24 H24 0.9300 .
