#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:18:24 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/63/7706318.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_7706318
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         'C19 H23 Cl0.25 I0.75 N P'
_chemical_formula_sum            'C19 H23 Cl0.25 I0.75 N P'
_chemical_formula_weight         400.39
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc250y05
_audit_creation_date             2019-10-01
_audit_creation_method
;
Olex2 1.2
(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                90
_cell_angle_beta                 101.724(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4221(5)
_cell_length_b                   9.8317(8)
_cell_length_c                   20.1049(12)
_cell_measurement_reflns_used    1719
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.93
_cell_volume                     1823.6(2)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_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 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_min         2.069
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0759 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9065.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0282
_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)+(0.0147P)²+1.6457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4004
_reflns_number_total             4539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01367f3.cif
_cod_data_source_block           cain83_0m_a
_cod_depositor_comments
'Adding full bibliography for 7706316--7706321.cif.'
_cod_database_code               7706318
_shelx_shelxl_version_number     2016/6
_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   0.740
_shelx_estimated_absorpt_t_min   0.713
_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. Uiso/Uaniso restraints and constraints
Uanis(I1) = Uanis(Cl1)
3. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(I1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
I1 I 0.77243(5) 0.39402(4) 0.50057(2) 0.02007(8) Uani 0.749(2) 1 d . . P A 1
Cl1 Cl 0.7701(7) 0.4151(5) 0.4899(3) 0.02007(8) Uani 0.251(2) 1 d . . P A 2
P1 P 0.63697(6) 0.54129(6) 0.40054(3) 0.01728(14) Uani 1 1 d . . . . .
N1 N 0.74682(19) 0.56643(17) 0.34640(8) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.6860(2) 0.7061(2) 0.43854(10) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.6252(3) 0.7727(2) 0.48750(11) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.552279 0.730202 0.506688 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6743(3) 0.9030(2) 0.50740(12) 0.0267(5) Uani 1 1 d . . . . .
H3 H 0.633296 0.950376 0.540135 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7820(3) 0.9647(2) 0.48019(12) 0.0268(5) Uani 1 1 d . . . . .
H4 H 0.813942 1.053648 0.494368 0.032 Uiso 1 1 calc R . . . .
C5 C 0.8436(3) 0.8970(2) 0.43227(11) 0.0224(5) Uani 1 1 d . . . . .
H5 H 0.918714 0.938366 0.414220 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7936(2) 0.7681(2) 0.41124(10) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.8439(2) 0.6849(2) 0.35780(10) 0.0170(4) Uani 1 1 d . . . . .
H7A H 0.836738 0.738046 0.315420 0.020 Uiso 1 1 calc R . . . .
H7B H 0.945710 0.655820 0.373680 0.020 Uiso 1 1 calc R . . . .
C8 C 0.7474(2) 0.4820(2) 0.28787(10) 0.0149(4) Uani 1 1 d . . . . .
C9 C 0.8603(2) 0.3881(2) 0.28846(10) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.8576(3) 0.3100(2) 0.23039(12) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.933986 0.247419 0.229457 0.028 Uiso 1 1 calc R . . . .
C11 C 0.7466(3) 0.3214(2) 0.17422(11) 0.0260(5) Uani 1 1 d . . . . .
H11 H 0.746174 0.266321 0.135378 0.031 Uiso 1 1 calc R . . . .
C12 C 0.6357(3) 0.4135(2) 0.17469(11) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.558732 0.419937 0.136131 0.026 Uiso 1 1 calc R . . . .
C13 C 0.6347(2) 0.4973(2) 0.23066(10) 0.0158(4) Uani 1 1 d . . . . .
C14 C 0.9810(2) 0.3664(2) 0.34997(11) 0.0203(5) Uani 1 1 d . . . . .
H14 H 0.963673 0.428596 0.386871 0.024 Uiso 1 1 calc R . . . .
C15 C 1.1283(3) 0.4012(3) 0.33411(14) 0.0308(6) Uani 1 1 d . . . . .
H15A H 1.148982 0.339300 0.299056 0.046 Uiso 1 1 calc GR . . . .
H15B H 1.203521 0.391498 0.375370 0.046 Uiso 1 1 calc GR . . . .
H15C H 1.127174 0.495126 0.317696 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.9805(3) 0.2201(2) 0.37580(14) 0.0307(6) Uani 1 1 d . . . . .
H16A H 1.009900 0.158199 0.342841 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.882725 0.196189 0.381577 0.046 Uiso 1 1 calc GR . . . .
H16C H 1.048479 0.212053 0.419515 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.5111(2) 0.5968(2) 0.22799(10) 0.0180(4) Uani 1 1 d . . . . .
H17 H 0.537389 0.660144 0.267486 0.022 Uiso 1 1 calc R . . . .
C18 C 0.3738(3) 0.5195(3) 0.23541(12) 0.0252(5) Uani 1 1 d . . . . .
H18A H 0.348539 0.453607 0.198320 0.038 Uiso 1 1 calc GR . . . .
H18B H 0.293849 0.584002 0.233610 0.038 Uiso 1 1 calc GR . . . .
H18C H 0.391418 0.471512 0.279033 0.038 Uiso 1 1 calc GR . . . .
C19 C 0.4823(3) 0.6822(2) 0.16285(12) 0.0243(5) Uani 1 1 d . . . . .
H19A H 0.572555 0.725993 0.157181 0.037 Uiso 1 1 calc GR . . . .
H19B H 0.409708 0.751989 0.165974 0.037 Uiso 1 1 calc GR . . . .
H19C H 0.446367 0.623234 0.123763 0.037 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 I1 108.43(7) . . ?
N1 P1 Cl1 105.93(17) . . ?
N1 P1 C1 90.23(9) . . ?
C1 P1 I1 97.42(7) . . ?
C1 P1 Cl1 95.74(16) . . ?
C7 N1 P1 117.72(13) . . ?
C8 N1 P1 123.64(14) . . ?
C8 N1 C7 118.59(16) . . ?
C2 C1 P1 127.62(18) . . ?
C6 C1 P1 111.72(15) . . ?
C6 C1 C2 120.6(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 113.95(18) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 C7 125.3(2) . . ?
N1 C7 C6 105.45(16) . . ?
N1 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 N1 119.95(19) . . ?
C13 C8 N1 118.64(18) . . ?
C13 C8 C9 121.39(18) . . ?
C8 C9 C14 122.69(18) . . ?
C10 C9 C8 118.0(2) . . ?
C10 C9 C14 119.28(19) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C17 123.07(18) . . ?
C12 C13 C8 117.99(19) . . ?
C12 C13 C17 118.9(2) . . ?
C9 C14 H14 108.1 . . ?
C9 C14 C15 111.21(19) . . ?
C9 C14 C16 110.8(2) . . ?
C15 C14 H14 108.1 . . ?
C15 C14 C16 110.3(2) . . ?
C16 C14 H14 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 108.0 . . ?
C13 C17 C18 109.54(18) . . ?
C13 C17 C19 112.68(17) . . ?
C18 C17 H17 108.0 . . ?
C19 C17 H17 108.0 . . ?
C19 C17 C18 110.41(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
I1 P1 2.5937(7) . ?
Cl1 P1 2.329(5) . ?
P1 N1 1.6657(17) . ?
P1 C1 1.811(2) . ?
N1 C7 1.470(3) . ?
N1 C8 1.441(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 C7 1.501(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.407(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.515(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(3) . ?
C13 C17 1.514(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.525(3) . ?
C14 C16 1.530(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 1.0000 . ?
C17 C18 1.533(3) . ?
C17 C19 1.533(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
