#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:18:24 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/63/7706321.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_7706321
loop_
_publ_author_name
'Zhou, Daniel Y.'
'Miura-Akagi, Preston M'
'McCarty, Sierra M.'
'Guiles, Celeste H.'
'O'Donnell, Timothy J'
'Yoshida, Wesley Y.'
'Krause, Colleen E.'
'Rheingold, Arnold L.'
'Hughes, Russell P.'
'Cain, Matthew F.'
_publ_section_title
;
 P-Alkynyl functionalized benzazaphospholes as transmetalating agents.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              599
_journal_page_last               611
_journal_paper_doi               10.1039/d0dt01367f
_journal_volume                  50
_journal_year                    2021
_chemical_formula_moiety         'C27 H28 N P'
_chemical_formula_sum            'C27 H28 N P'
_chemical_formula_weight         397.47
_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   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc250xy2
_audit_creation_date             2019-04-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                97.641(2)
_cell_angle_beta                 103.063(2)
_cell_angle_gamma                90.538(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4342(5)
_cell_length_b                   10.7526(6)
_cell_length_c                   14.1948(8)
_cell_measurement_reflns_used    3654
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.615
_cell_measurement_theta_min      2.254
_cell_volume                     1241.83(12)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_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_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15194
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         1.487
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         6203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0540
_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)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4282
_reflns_number_total             6203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01367f3.cif
_cod_data_source_block           cain79_0m_a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7706316--7706321.cif.
;
_cod_database_code               7706321
_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.
;
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.969
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C19(H19), C20(H20), C18(H18), C11(H11), C13(H13), C12(H12), C3(H3),
 C5(H5), C4(H4), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C26(H26A,H26B,
 H26C)
;
_platon_squeeze_void_probe_radius 1.20
_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
P1 P 0.69084(6) 0.50467(4) 0.79083(3) 0.01827(14) Uani 1 1 d . . . . .
N1 N 0.85250(17) 0.47374(13) 0.73981(10) 0.0172(3) Uani 1 1 d . . . . .
C16 C 1.0174(2) 0.50042(16) 0.79445(12) 0.0166(4) Uani 1 1 d . . . . .
C17 C 1.1005(2) 0.61096(16) 0.78668(13) 0.0186(4) Uani 1 1 d . . . . .
C14 C 0.6388(2) 0.39668(16) 0.60517(13) 0.0188(4) Uani 1 1 d . . . . .
C9 C 0.5540(2) 0.43093(15) 0.67757(13) 0.0182(4) Uani 1 1 d . . . . .
C21 C 1.0930(2) 0.41475(17) 0.85639(13) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.3872(2) 0.40766(16) 0.65975(14) 0.0216(4) Uani 1 1 d . . . . .
H10 H 0.3300 0.4306 0.7095 0.026 Uiso 1 1 calc R . . . .
C22 C 1.0244(2) 0.70440(16) 0.72036(13) 0.0207(4) Uani 1 1 d . . . . .
H22 H 0.9072 0.6780 0.6934 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6274(2) 0.77833(18) 0.79531(15) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.6040(2) 0.91118(18) 0.81025(16) 0.0284(5) Uani 1 1 d . . . . .
C25 C 1.0070(2) 0.29560(17) 0.86771(14) 0.0258(4) Uani 1 1 d . . . . .
H25 H 0.8971 0.2875 0.8219 0.031 Uiso 1 1 calc R . . . .
C19 C 1.3355(2) 0.5523(2) 0.90219(15) 0.0295(5) Uani 1 1 d . . . . .
H19 H 1.4442 0.5699 0.9390 0.035 Uiso 1 1 calc R . . . .
C20 C 1.2511(2) 0.44333(19) 0.90955(14) 0.0279(5) Uani 1 1 d . . . . .
H20 H 1.3032 0.3873 0.9521 0.033 Uiso 1 1 calc R . . . .
C18 C 1.2601(2) 0.63468(18) 0.84086(14) 0.0235(4) Uani 1 1 d . . . . .
H18 H 1.3180 0.7087 0.8356 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6479(2) 0.66645(17) 0.78283(14) 0.0220(4) Uani 1 1 d . . . . .
C15 C 0.8193(2) 0.42903(17) 0.63522(13) 0.0220(4) Uani 1 1 d . . . . .
H15A H 0.8824 0.3541 0.6221 0.026 Uiso 1 1 calc R . . . .
H15B H 0.8483 0.4953 0.5991 0.026 Uiso 1 1 calc R . . . .
C11 C 0.3054(2) 0.35035(17) 0.56826(15) 0.0256(4) Uani 1 1 d . . . . .
H11 H 0.1910 0.3340 0.5551 0.031 Uiso 1 1 calc R . . . .
C13 C 0.5551(2) 0.33920(17) 0.51316(14) 0.0247(4) Uani 1 1 d . . . . .
H13 H 0.6118 0.3159 0.4632 0.030 Uiso 1 1 calc R . . . .
C12 C 0.3892(2) 0.31661(17) 0.49564(15) 0.0270(4) Uani 1 1 d . . . . .
H12 H 0.3314 0.2775 0.4332 0.032 Uiso 1 1 calc R . . . .
C24 C 1.0320(3) 0.83777(17) 0.77642(15) 0.0295(5) Uani 1 1 d . . . . .
H24A H 0.9840 0.8361 0.8330 0.044 Uiso 1 1 calc GR . . . .
H24B H 0.9711 0.8936 0.7333 0.044 Uiso 1 1 calc GR . . . .
H24C H 1.1459 0.8686 0.7986 0.044 Uiso 1 1 calc GR . . . .
C23 C 1.1062(3) 0.70414(19) 0.63465(14) 0.0294(5) Uani 1 1 d . . . . .
H23A H 1.2208 0.7321 0.6592 0.044 Uiso 1 1 calc GR . . . .
H23B H 1.0508 0.7612 0.5907 0.044 Uiso 1 1 calc GR . . . .
H23C H 1.0995 0.6190 0.5990 0.044 Uiso 1 1 calc GR . . . .
C3 C 0.5616(3) 1.1685(2) 0.8373(2) 0.0480(7) Uani 1 1 d . . . . .
H3 H 0.5432 1.2559 0.8468 0.058 Uiso 1 1 calc R . . . .
C5 C 0.6242(3) 0.9766(2) 0.90136(19) 0.0485(7) Uani 1 1 d . . . . .
H5 H 0.6541 0.9337 0.9567 0.058 Uiso 1 1 calc R . . . .
C4 C 0.6019(4) 1.1047(2) 0.9150(2) 0.0547(7) Uani 1 1 d . . . . .
H4 H 0.6150 1.1481 0.9793 0.066 Uiso 1 1 calc R . . . .
C27 C 0.9855(3) 0.2975(2) 0.97055(17) 0.0508(7) Uani 1 1 d . . . . .
H27A H 1.0920 0.3112 1.0165 0.076 Uiso 1 1 calc GR . . . .
H27B H 0.9360 0.2170 0.9767 0.076 Uiso 1 1 calc GR . . . .
H27C H 0.9146 0.3655 0.9853 0.076 Uiso 1 1 calc GR . . . .
C1 C 0.5662(4) 0.9771(2) 0.7309(2) 0.0649(9) Uani 1 1 d . . . . .
H1 H 0.5529 0.9342 0.6664 0.078 Uiso 1 1 calc R . . . .
C26 C 1.1042(4) 0.1799(2) 0.8426(2) 0.0697(9) Uani 1 1 d . . . . .
H26A H 1.1204 0.1780 0.7762 0.105 Uiso 1 1 calc GR . . . .
H26B H 1.0436 0.1033 0.8467 0.105 Uiso 1 1 calc GR . . . .
H26C H 1.2103 0.1849 0.8890 0.105 Uiso 1 1 calc GR . . . .
C2 C 0.5476(4) 1.1065(3) 0.7459(2) 0.0738(10) Uani 1 1 d . . . . .
H2 H 0.5250 1.1517 0.6915 0.089 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
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
N1 P1 C9 89.64(8) . . ?
N1 P1 C8 106.70(8) . . ?
C8 P1 C9 99.89(8) . . ?
C16 N1 P1 121.93(11) . . ?
C16 N1 C15 120.02(14) . . ?
C15 N1 P1 117.82(12) . . ?
C17 C16 N1 119.93(15) . . ?
C17 C16 C21 120.99(16) . . ?
C21 C16 N1 119.08(16) . . ?
C16 C17 C22 122.57(16) . . ?
C18 C17 C16 118.68(16) . . ?
C18 C17 C22 118.74(17) . . ?
C9 C14 C15 114.70(16) . . ?
C9 C14 C13 119.80(17) . . ?
C13 C14 C15 125.48(17) . . ?
C14 C9 P1 111.26(14) . . ?
C10 C9 P1 127.91(15) . . ?
C10 C9 C14 120.84(17) . . ?
C16 C21 C25 122.58(16) . . ?
C20 C21 C16 118.10(17) . . ?
C20 C21 C25 119.31(16) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.92(18) . . ?
C11 C10 H10 120.5 . . ?
C17 C22 H22 108.0 . . ?
C17 C22 C24 111.66(15) . . ?
C17 C22 C23 110.89(15) . . ?
C24 C22 H22 108.0 . . ?
C23 C22 H22 108.0 . . ?
C23 C22 C24 110.20(15) . . ?
C8 C7 C6 179.7(2) . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 C1 118.1(2) . . ?
C1 C6 C7 120.1(2) . . ?
C21 C25 H25 108.8 . . ?
C21 C25 C26 110.62(19) . . ?
C27 C25 C21 111.40(16) . . ?
C27 C25 H25 108.8 . . ?
C27 C25 C26 108.5(2) . . ?
C26 C25 H25 108.8 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.52(18) . . ?
C21 C20 C19 121.60(18) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.11(18) . . ?
C19 C18 H18 119.4 . . ?
C7 C8 P1 168.38(18) . . ?
N1 C15 C14 105.40(15) . . ?
N1 C15 H15A 110.7 . . ?
N1 C15 H15B 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.49(18) . . ?
C12 C11 H11 119.8 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 C14 119.17(18) . . ?
C12 C13 H13 120.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.78(18) . . ?
C13 C12 H12 119.6 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.9(3) . . ?
C2 C1 H1 120.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
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
P1 N1 1.6986(15) . ?
P1 C9 1.8305(18) . ?
P1 C8 1.7932(19) . ?
N1 C16 1.437(2) . ?
N1 C15 1.461(2) . ?
C16 C17 1.404(2) . ?
C16 C21 1.414(2) . ?
C17 C22 1.516(2) . ?
C17 C18 1.393(3) . ?
C14 C9 1.393(3) . ?
C14 C15 1.509(3) . ?
C14 C13 1.395(3) . ?
C9 C10 1.386(3) . ?
C21 C25 1.511(3) . ?
C21 C20 1.385(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C22 H22 1.0000 . ?
C22 C24 1.538(3) . ?
C22 C23 1.528(3) . ?
C7 C6 1.438(3) . ?
C7 C8 1.212(3) . ?
C6 C5 1.361(3) . ?
C6 C1 1.389(3) . ?
C25 H25 1.0000 . ?
C25 C27 1.509(3) . ?
C25 C26 1.543(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C19 C18 1.383(3) . ?
C20 H20 0.9500 . ?
C18 H18 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.378(3) . ?
C12 H12 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.356(4) . ?
C3 C2 1.357(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.395(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C2 H2 0.9500 . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 13 0 ' '
2 0.002 0.000 0.500 165 49 ' '
