#------------------------------------------------------------------------------
#$Date: 2020-09-22 02:23:33 +0300 (Tue, 22 Sep 2020) $
#$Revision: 256596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038811.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_4038811
loop_
_publ_author_name
'Rodstein, Ilja'
'Prendes, Daniel Sowa'
'Wickert, Leon'
'Paaßen, Maurice'
'Gessner, Viktoria'
_publ_section_title
;
 Selective Pd-Catalyzed Monoarylation of Small Primary Alkyl Amines
 through Backbone-Modification in Ylide-Functionalized Phosphines (YPhos).
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01771
_journal_year                    2020
_chemical_formula_sum            'C44 H68 P2'
_chemical_formula_weight         658.92
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90.2806(17)
_cell_angle_beta                 93.674(2)
_cell_angle_gamma                93.3011(19)
_cell_formula_units_Z            1
_cell_length_a                   9.3707(2)
_cell_length_b                   9.9337(2)
_cell_length_c                   10.0310(2)
_cell_measurement_reflns_used    7929
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.6390
_cell_measurement_theta_min      4.4240
_cell_volume                     930.24(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11228
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.417
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       plate
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0327
_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)+(0.0359P)²+0.4679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3117
_reflns_number_total             3314
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01771_si_005.cif
_cod_data_source_block           IR-006_a
_cod_original_cell_volume        930.25(4)
_cod_database_code               4038811
_shelx_shelxl_version_number     2018/3
_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.
;
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 0.59703(3) 0.30839(3) 0.42105(3) 0.01444(11) Uani 1 1 d . . . . .
C1 C 0.57113(13) 0.49315(12) 0.46285(13) 0.0144(3) Uani 1 1 d . . . . .
H1 H 0.650818 0.523304 0.526000 0.017 Uiso 1 1 calc R U . . .
C2 C 0.57832(14) 0.58498(13) 0.34149(13) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.67539(14) 0.69943(13) 0.34792(13) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.68515(14) 0.78382(13) 0.23791(14) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.749295 0.858931 0.243848 0.022 Uiso 1 1 calc R U . . .
C5 C 0.60192(15) 0.75923(13) 0.11947(14) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.50416(15) 0.64863(13) 0.11535(13) 0.0180(3) Uani 1 1 d . . . . .
H6 H 0.446199 0.631634 0.037646 0.022 Uiso 1 1 calc R U . . .
C7 C 0.48951(14) 0.56196(13) 0.22332(13) 0.0157(3) Uani 1 1 d . . . . .
C8 C 0.77137(14) 0.73514(13) 0.47176(14) 0.0188(3) Uani 1 1 d . . . . .
H8A H 0.831667 0.662207 0.492663 0.028 Uiso 1 1 calc R U . . .
H8B H 0.713492 0.750548 0.545309 0.028 Uiso 1 1 calc R U . . .
H8C H 0.829778 0.815301 0.455803 0.028 Uiso 1 1 calc R U . . .
C9 C 0.61885(18) 0.84931(15) 0.00020(15) 0.0266(3) Uani 1 1 d . . . . .
H9A H 0.708453 0.834847 -0.037375 0.040 Uiso 1 1 calc R U . . .
H9B H 0.617175 0.941870 0.027711 0.040 Uiso 1 1 calc R U . . .
H9C H 0.541705 0.828523 -0.065624 0.040 Uiso 1 1 calc R U . . .
C10 C 0.36953(14) 0.45308(13) 0.20862(13) 0.0181(3) Uani 1 1 d . . . . .
H10A H 0.346315 0.434249 0.115546 0.027 Uiso 1 1 calc R U . . .
H10B H 0.286642 0.483268 0.248813 0.027 Uiso 1 1 calc R U . . .
H10C H 0.399582 0.372683 0.252189 0.027 Uiso 1 1 calc R U . . .
C11 C 0.69769(14) 0.24819(13) 0.57452(13) 0.0159(3) Uani 1 1 d . . . . .
H11 H 0.648575 0.283747 0.649351 0.019 Uiso 1 1 calc R U . . .
C12 C 0.85517(14) 0.29242(14) 0.60374(13) 0.0188(3) Uani 1 1 d . . . . .
H12A H 0.867031 0.389964 0.600208 0.023 Uiso 1 1 calc R U . . .
H12B H 0.911616 0.255349 0.536159 0.023 Uiso 1 1 calc R U . . .
C13 C 0.90887(15) 0.24433(15) 0.74191(14) 0.0225(3) Uani 1 1 d . . . . .
H13A H 1.009608 0.271643 0.757831 0.027 Uiso 1 1 calc R U . . .
H13B H 0.856772 0.286361 0.809881 0.027 Uiso 1 1 calc R U . . .
C14 C 0.88864(16) 0.09136(15) 0.75232(14) 0.0244(3) Uani 1 1 d . . . . .
H14A H 0.918510 0.063893 0.841999 0.029 Uiso 1 1 calc R U . . .
H14B H 0.948358 0.049290 0.690531 0.029 Uiso 1 1 calc R U . . .
C15 C 0.73209(17) 0.04384(14) 0.72035(14) 0.0238(3) Uani 1 1 d . . . . .
H15A H 0.674242 0.076593 0.789070 0.029 Uiso 1 1 calc R U . . .
H15B H 0.723413 -0.053934 0.720927 0.029 Uiso 1 1 calc R U . . .
C16 C 0.67542(16) 0.09400(13) 0.58418(14) 0.0214(3) Uani 1 1 d . . . . .
H16A H 0.574120 0.068094 0.570558 0.026 Uiso 1 1 calc R U . . .
H16B H 0.724730 0.051855 0.514311 0.026 Uiso 1 1 calc R U . . .
C17 C 0.72365(14) 0.31676(13) 0.28358(13) 0.0167(3) Uani 1 1 d . . . . .
H17 H 0.666618 0.347279 0.205362 0.020 Uiso 1 1 calc R U . . .
C18 C 0.86070(14) 0.41077(13) 0.29117(13) 0.0182(3) Uani 1 1 d . . . . .
H18A H 0.836700 0.501991 0.311506 0.022 Uiso 1 1 calc R U . . .
H18B H 0.926666 0.381615 0.362277 0.022 Uiso 1 1 calc R U . . .
C19 C 0.93246(15) 0.40883(14) 0.15815(14) 0.0208(3) Uani 1 1 d . . . . .
H19A H 0.868562 0.443372 0.088190 0.025 Uiso 1 1 calc R U . . .
H19B H 1.019308 0.467157 0.164920 0.025 Uiso 1 1 calc R U . . .
C20 C 0.96913(15) 0.26621(15) 0.12145(14) 0.0229(3) Uani 1 1 d . . . . .
H20A H 1.009992 0.267059 0.035006 0.027 Uiso 1 1 calc R U . . .
H20B H 1.040200 0.234997 0.186936 0.027 Uiso 1 1 calc R U . . .
C21 C 0.83654(15) 0.16975(14) 0.11651(14) 0.0217(3) Uani 1 1 d . . . . .
H21A H 0.864107 0.078877 0.099722 0.026 Uiso 1 1 calc R U . . .
H21B H 0.770666 0.194397 0.043330 0.026 Uiso 1 1 calc R U . . .
C22 C 0.76105(15) 0.17273(13) 0.24733(14) 0.0191(3) Uani 1 1 d . . . . .
H22A H 0.822803 0.137850 0.318773 0.023 Uiso 1 1 calc R U . . .
H22B H 0.673950 0.114832 0.238594 0.023 Uiso 1 1 calc R U . . .
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'
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
C11 P1 C17 107.50(6) . . ?
C11 P1 C1 102.95(6) . . ?
C17 P1 C1 104.18(6) . . ?
C2 C1 C1 112.23(12) . 2_666 ?
C2 C1 P1 112.99(9) . . ?
C1 C1 P1 110.70(11) 2_666 . ?
C3 C2 C7 118.32(12) . . ?
C3 C2 C1 118.96(11) . . ?
C7 C2 C1 122.71(11) . . ?
C4 C3 C2 120.02(12) . . ?
C4 C3 C8 117.77(12) . . ?
C2 C3 C8 122.22(12) . . ?
C5 C4 C3 122.06(13) . . ?
C6 C5 C4 117.49(12) . . ?
C6 C5 C9 121.61(13) . . ?
C4 C5 C9 120.89(13) . . ?
C5 C6 C7 122.52(13) . . ?
C6 C7 C2 119.52(12) . . ?
C6 C7 C10 116.52(12) . . ?
C2 C7 C10 123.81(11) . . ?
C12 C11 C16 110.47(11) . . ?
C12 C11 P1 120.33(9) . . ?
C16 C11 P1 109.70(9) . . ?
C11 C12 C13 110.66(11) . . ?
C14 C13 C12 111.01(12) . . ?
C13 C14 C15 110.92(11) . . ?
C14 C15 C16 111.79(12) . . ?
C15 C16 C11 111.21(11) . . ?
C22 C17 C18 109.60(11) . . ?
C22 C17 P1 109.07(9) . . ?
C18 C17 P1 122.21(9) . . ?
C19 C18 C17 110.36(11) . . ?
C20 C19 C18 111.07(11) . . ?
C21 C20 C19 111.09(11) . . ?
C20 C21 C22 111.56(12) . . ?
C21 C22 C17 111.47(11) . . ?
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 C11 1.8722(13) . ?
P1 C17 1.8750(13) . ?
P1 C1 1.9131(13) . ?
C1 C2 1.5274(17) . ?
C1 C1 1.581(2) 2_666 ?
C2 C3 1.4130(19) . ?
C2 C7 1.4139(19) . ?
C3 C4 1.3936(19) . ?
C3 C8 1.5145(19) . ?
C4 C5 1.391(2) . ?
C5 C6 1.388(2) . ?
C5 C9 1.5085(18) . ?
C6 C7 1.3956(18) . ?
C7 C10 1.5142(18) . ?
C11 C12 1.5249(19) . ?
C11 C16 1.5382(18) . ?
C12 C13 1.5321(18) . ?
C13 C14 1.525(2) . ?
C14 C15 1.528(2) . ?
C15 C16 1.5299(19) . ?
C17 C22 1.5398(18) . ?
C17 C18 1.5413(18) . ?
C18 C19 1.5327(18) . ?
C19 C20 1.526(2) . ?
C20 C21 1.523(2) . ?
C21 C22 1.5312(19) . ?
