#------------------------------------------------------------------------------
#$Date: 2021-02-05 01:18:24 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/63/7706316.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_7706316
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 Cl N P'
_chemical_formula_sum            'C19 H23 Cl N P'
_chemical_formula_weight         331.80
_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     direct
_audit_block_doi                 10.5517/ccdc.csd.cc250xz3
_audit_creation_date             2018-06-15
_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                90
_cell_angle_beta                 105.441(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7432(6)
_cell_length_b                   10.4564(5)
_cell_length_c                   15.0518(11)
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.325
_cell_measurement_theta_min      3.907
_cell_volume                     1781.52(18)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_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                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker Pt135'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14613
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.234
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0761 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.8215. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         1.147
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0471
_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)+(0.0578P)²+2.2681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1256
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3142
_reflns_number_total             3381
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt01367f3.cif
_cod_data_source_block           cain71_0m_a
_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               7706316
_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   0.530
_shelx_estimated_absorpt_t_min   0.470
_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:
 C14(H14), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.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
Cl1 Cl 0.86040(5) 0.56498(5) 0.53932(4) 0.02981(18) Uani 1 1 d . . . . .
P1 P 0.70398(5) 0.47849(5) 0.44991(3) 0.01936(16) Uani 1 1 d . . . . .
N1 N 0.73466(14) 0.45405(16) 0.34923(11) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.80141(19) 0.33700(19) 0.33869(13) 0.0188(4) Uani 1 1 d . . . . .
H1A H 0.884628 0.357771 0.341789 0.023 Uiso 1 1 calc R . . . .
H1B H 0.765067 0.294165 0.279242 0.023 Uiso 1 1 calc R . . . .
C2 C 0.79377(17) 0.25311(19) 0.41909(13) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.83039(18) 0.1261(2) 0.43239(14) 0.0197(4) Uani 1 1 d . . . . .
H3 H 0.867396 0.085558 0.390926 0.024 Uiso 1 1 calc R . . . .
C4 C 0.81187(19) 0.0598(2) 0.50731(14) 0.0228(5) Uani 1 1 d . . . . .
H4 H 0.835829 -0.027031 0.516685 0.027 Uiso 1 1 calc R . . . .
C5 C 0.75867(19) 0.1190(2) 0.56882(14) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.745181 0.071707 0.618964 0.030 Uiso 1 1 calc R . . . .
C6 C 0.72513(18) 0.2467(2) 0.55737(14) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.690483 0.287822 0.600072 0.026 Uiso 1 1 calc R . . . .
C7 C 0.74328(17) 0.31351(19) 0.48204(13) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.69440(17) 0.53655(18) 0.27048(13) 0.0148(4) Uani 1 1 d . . . . .
C9 C 0.77333(17) 0.62387(19) 0.24763(13) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.73188(19) 0.6984(2) 0.16840(14) 0.0202(4) Uani 1 1 d . . . . .
H10 H 0.783932 0.757140 0.151141 0.024 Uiso 1 1 calc R . . . .
C11 C 0.61647(19) 0.6884(2) 0.11462(14) 0.0224(4) Uani 1 1 d . . . . .
H11 H 0.590014 0.740219 0.061255 0.027 Uiso 1 1 calc R . . . .
C12 C 0.53956(18) 0.6028(2) 0.13861(14) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.460334 0.597085 0.101706 0.024 Uiso 1 1 calc R . . . .
C13 C 0.57695(18) 0.52461(19) 0.21646(14) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.89902(18) 0.6407(2) 0.30634(15) 0.0211(4) Uani 1 1 d . . . . .
H14 H 0.914189 0.575275 0.356613 0.025 Uiso 1 1 calc R . . . .
C15 C 0.9884(2) 0.6197(3) 0.24984(18) 0.0330(5) Uani 1 1 d . . . . .
H15A H 0.977771 0.533933 0.222591 0.050 Uiso 1 1 calc GR . . . .
H15B H 1.068765 0.627878 0.290098 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.975871 0.683806 0.200699 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.9151(2) 0.7738(2) 0.35106(19) 0.0349(6) Uani 1 1 d . . . . .
H16A H 0.903524 0.839323 0.302941 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.994955 0.781121 0.392230 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.856980 0.785822 0.386534 0.052 Uiso 1 1 calc GR . . . .
C17 C 0.48962(18) 0.4318(2) 0.24008(14) 0.0200(4) Uani 1 1 d . . . . .
H17 H 0.534612 0.374118 0.290235 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3990(2) 0.5060(2) 0.27721(17) 0.0270(5) Uani 1 1 d . . . . .
H18A H 0.439415 0.548611 0.334995 0.040 Uiso 1 1 calc GR . . . .
H18B H 0.339844 0.446527 0.288465 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.359921 0.570198 0.231847 0.040 Uiso 1 1 calc GR . . . .
C19 C 0.42850(19) 0.3482(2) 0.15759(16) 0.0258(5) Uani 1 1 d . . . . .
H19A H 0.380683 0.402268 0.108467 0.039 Uiso 1 1 calc GR . . . .
H19B H 0.377440 0.285772 0.176705 0.039 Uiso 1 1 calc GR . . . .
H19C H 0.488257 0.303124 0.134810 0.039 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 0.0181 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'
N N 0.0311 0.0180 '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_
_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 Cl1 106.02(6) . . ?
N1 P1 C7 89.74(9) . . ?
C7 P1 Cl1 96.76(6) . . ?
C1 N1 P1 118.12(13) . . ?
C8 N1 P1 123.57(13) . . ?
C8 N1 C1 118.22(15) . . ?
N1 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
N1 C1 C2 104.27(16) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C3 C2 C1 125.74(18) . . ?
C3 C2 C7 120.29(18) . . ?
C7 C2 C1 113.96(18) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.88(19) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.8(2) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 P1 111.88(15) . . ?
C6 C7 P1 127.46(16) . . ?
C6 C7 C2 120.64(19) . . ?
C9 C8 N1 119.77(17) . . ?
C9 C8 C13 121.60(18) . . ?
C13 C8 N1 118.60(17) . . ?
C8 C9 C14 122.36(18) . . ?
C10 C9 C8 117.87(18) . . ?
C10 C9 C14 119.76(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.34(19) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.05(19) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.94(19) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C17 122.63(18) . . ?
C12 C13 C8 118.19(18) . . ?
C12 C13 C17 119.17(18) . . ?
C9 C14 H14 108.2 . . ?
C9 C14 C15 111.38(18) . . ?
C9 C14 C16 110.33(18) . . ?
C15 C14 H14 108.2 . . ?
C15 C14 C16 110.5(2) . . ?
C16 C14 H14 108.2 . . ?
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 107.9 . . ?
C13 C17 C18 109.74(17) . . ?
C13 C17 C19 111.97(17) . . ?
C18 C17 H17 107.9 . . ?
C19 C17 H17 107.9 . . ?
C19 C17 C18 111.24(17) . . ?
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
Cl1 P1 2.1649(8) . ?
P1 N1 1.6681(16) . ?
P1 C7 1.818(2) . ?
N1 C1 1.485(3) . ?
N1 C8 1.440(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.517(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C8 C9 1.408(3) . ?
C8 C13 1.408(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.515(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.400(3) . ?
C13 C17 1.521(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.533(3) . ?
C14 C16 1.536(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 1.538(3) . ?
C17 C19 1.532(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 . ?
