#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:58:43 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260706 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/73/7127351.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_7127351
loop_
_publ_author_name
'Horsley Downie, Thomas M.'
'Hall, Jonathan W.'
'Collier Finn, Thomas P.'
'Liptrot, David J.'
'Lowe, John P.'
'Mahon, Mary F.'
'McMullin, Claire L.'
'Whittlesey, Michael K.'
_publ_section_title
;
 The first ring-expanded NHC-copper(i) phosphides as catalysts in the
 highly selective hydrophosphination of isocyanates.
;
_journal_issue                   87
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13359
_journal_page_last               13362
_journal_paper_doi               10.1039/d0cc05694d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C39 H46 Cu N2 P'
_chemical_formula_sum            'C39 H46 Cu N2 P'
_chemical_formula_weight         637.29
_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     iterative
_audit_creation_date             2019-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-06 deposited with the CCDC.	2020-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                73.491(5)
_cell_angle_beta                 88.101(4)
_cell_angle_gamma                84.877(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0805(5)
_cell_length_b                   10.9216(5)
_cell_length_c                   16.5042(10)
_cell_measurement_reflns_used    6157
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.7160
_cell_measurement_theta_min      3.7410
_cell_volume                     1735.11(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0734
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14815
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.589
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         8096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0294P)²+0.8974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6630
_reflns_number_total             8096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05694d2.cif
_cod_data_source_block           e19mkw17
_cod_depositor_comments
'Adding full bibliography for 7127351--7127357.cif.'
_cod_database_code               7127351
_chemical_oxdiff_usercomment     'Colourless blocks'
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20),
 C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37),
  C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
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
Cu1 Cu 0.55785(2) 0.48239(2) 0.71059(2) 0.01877(7) Uani 1 1 d . . . . .
P1 P 0.34640(5) 0.44664(5) 0.70637(3) 0.02122(12) Uani 1 1 d . . . . .
N1 N 0.78348(14) 0.63764(15) 0.70558(9) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.85051(14) 0.44252(15) 0.71730(9) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.73779(17) 0.52213(18) 0.71137(11) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.92114(17) 0.62959(19) 0.70712(12) 0.0195(4) Uani 1 1 d . . . . .
H2 H 0.9742 0.6963 0.7040 0.023 Uiso 1 1 calc R . . . .
C3 C 0.96324(17) 0.50752(19) 0.71401(12) 0.0197(4) Uani 1 1 d . . . . .
H3 H 1.0512 0.4729 0.7162 0.024 Uiso 1 1 calc R . . . .
C4 C 0.85386(17) 0.30712(18) 0.72769(12) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.84032(17) 0.26491(19) 0.65649(12) 0.0201(4) Uani 1 1 d . . . . .
C6 C 0.8494(2) 0.1329(2) 0.66906(14) 0.0290(5) Uani 1 1 d . . . . .
H6 H 0.8422 0.1008 0.6230 0.035 Uiso 1 1 calc R . . . .
C7 C 0.8686(2) 0.0491(2) 0.74838(15) 0.0346(5) Uani 1 1 d . . . . .
H7 H 0.8743 -0.0388 0.7553 0.041 Uiso 1 1 calc R . . . .
C8 C 0.8797(2) 0.0944(2) 0.81779(14) 0.0326(5) Uani 1 1 d . . . . .
H8 H 0.8915 0.0366 0.8711 0.039 Uiso 1 1 calc R . . . .
C9 C 0.87339(18) 0.22471(19) 0.80916(12) 0.0220(4) Uani 1 1 d . . . . .
C10 C 0.81357(19) 0.3558(2) 0.56936(12) 0.0240(4) Uani 1 1 d . . . . .
H10 H 0.8134 0.4435 0.5737 0.029 Uiso 1 1 calc R . . . .
C11 C 0.6765(2) 0.3401(3) 0.53926(14) 0.0391(6) Uani 1 1 d . . . . .
H11A H 0.6752 0.2559 0.5323 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.6576 0.4031 0.4862 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.6104 0.3514 0.5803 0.059 Uiso 1 1 calc GR . . . .
C12 C 0.9208(3) 0.3382(3) 0.50575(15) 0.0451(6) Uani 1 1 d . . . . .
H12A H 1.0058 0.3512 0.5250 0.068 Uiso 1 1 calc GR . . . .
H12B H 0.9016 0.3992 0.4520 0.068 Uiso 1 1 calc GR . . . .
H12C H 0.9227 0.2530 0.5001 0.068 Uiso 1 1 calc GR . . . .
C13 C 0.88032(19) 0.2755(2) 0.88520(12) 0.0249(4) Uani 1 1 d . . . . .
H13 H 0.9123 0.3612 0.8652 0.030 Uiso 1 1 calc R . . . .
C14 C 0.9766(2) 0.1945(3) 0.95264(14) 0.0387(6) Uani 1 1 d . . . . .
H14A H 0.9429 0.1127 0.9780 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.9857 0.2375 0.9952 0.058 Uiso 1 1 calc GR . . . .
H14C H 1.0620 0.1824 0.9272 0.058 Uiso 1 1 calc GR . . . .
C15 C 0.7412(2) 0.2902(3) 0.92224(14) 0.0392(6) Uani 1 1 d . . . . .
H15A H 0.6846 0.3480 0.8801 0.059 Uiso 1 1 calc GR . . . .
H15B H 0.7461 0.3236 0.9698 0.059 Uiso 1 1 calc GR . . . .
H15C H 0.7054 0.2081 0.9401 0.059 Uiso 1 1 calc GR . . . .
C16 C 0.69864(17) 0.75397(18) 0.69700(12) 0.0176(4) Uani 1 1 d . . . . .
C17 C 0.63836(18) 0.77567(19) 0.76956(12) 0.0220(4) Uani 1 1 d . . . . .
C18 C 0.5578(2) 0.8898(2) 0.75869(14) 0.0281(5) Uani 1 1 d . . . . .
H18 H 0.5159 0.9081 0.8055 0.034 Uiso 1 1 calc R . . . .
C19 C 0.5394(2) 0.9757(2) 0.68029(14) 0.0303(5) Uani 1 1 d . . . . .
H19 H 0.4855 1.0513 0.6747 0.036 Uiso 1 1 calc R . . . .
C20 C 0.59994(19) 0.9510(2) 0.60976(13) 0.0267(5) Uani 1 1 d . . . . .
H20 H 0.5856 1.0098 0.5570 0.032 Uiso 1 1 calc R . . . .
C21 C 0.68185(17) 0.83982(19) 0.61638(12) 0.0201(4) Uani 1 1 d . . . . .
C22 C 0.6616(2) 0.6837(2) 0.85669(13) 0.0291(5) Uani 1 1 d . . . . .
H22 H 0.6983 0.6014 0.8493 0.035 Uiso 1 1 calc R . . . .
C23 C 0.7631(3) 0.7294(3) 0.90434(15) 0.0547(8) Uani 1 1 d . . . . .
H23A H 0.8451 0.7385 0.8727 0.082 Uiso 1 1 calc GR . . . .
H23B H 0.7784 0.6681 0.9585 0.082 Uiso 1 1 calc GR . . . .
H23C H 0.7303 0.8106 0.9120 0.082 Uiso 1 1 calc GR . . . .
C24 C 0.5340(3) 0.6601(3) 0.90831(17) 0.0580(8) Uani 1 1 d . . . . .
H24A H 0.4978 0.7384 0.9190 0.087 Uiso 1 1 calc GR . . . .
H24B H 0.5530 0.5964 0.9611 0.087 Uiso 1 1 calc GR . . . .
H24C H 0.4706 0.6306 0.8775 0.087 Uiso 1 1 calc GR . . . .
C25 C 0.74471(19) 0.8088(2) 0.53890(12) 0.0249(4) Uani 1 1 d . . . . .
H25 H 0.8246 0.7506 0.5574 0.030 Uiso 1 1 calc R . . . .
C26 C 0.7882(2) 0.9268(2) 0.47182(14) 0.0391(6) Uani 1 1 d . . . . .
H26A H 0.8360 0.9005 0.4275 0.059 Uiso 1 1 calc GR . . . .
H26B H 0.8448 0.9717 0.4971 0.059 Uiso 1 1 calc GR . . . .
H26C H 0.7111 0.9823 0.4488 0.059 Uiso 1 1 calc GR . . . .
C27 C 0.6504(2) 0.7386(2) 0.50077(14) 0.0336(5) Uani 1 1 d . . . . .
H27A H 0.6262 0.6632 0.5430 0.050 Uiso 1 1 calc GR . . . .
H27B H 0.6940 0.7144 0.4544 0.050 Uiso 1 1 calc GR . . . .
H27C H 0.5717 0.7940 0.4809 0.050 Uiso 1 1 calc GR . . . .
C28 C 0.32913(18) 0.28946(19) 0.78241(14) 0.0254(4) Uani 1 1 d . . . . .
C29 C 0.2506(2) 0.2055(2) 0.76025(16) 0.0387(6) Uani 1 1 d . . . . .
H29 H 0.2045 0.2324 0.7095 0.046 Uiso 1 1 calc R . . . .
C30 C 0.2403(3) 0.0832(3) 0.8123(2) 0.0597(9) Uani 1 1 d . . . . .
H30 H 0.1875 0.0287 0.7961 0.072 Uiso 1 1 calc R . . . .
C31 C 0.3064(3) 0.0410(3) 0.8872(2) 0.0645(10) Uani 1 1 d . . . . .
H31 H 0.3005 -0.0423 0.9213 0.077 Uiso 1 1 calc R . . . .
C32 C 0.3821(3) 0.1231(3) 0.9119(2) 0.0614(9) Uani 1 1 d . . . . .
H32 H 0.4256 0.0958 0.9636 0.074 Uiso 1 1 calc R . . . .
C33 C 0.3934(2) 0.2459(2) 0.85992(17) 0.0432(6) Uani 1 1 d . . . . .
H33 H 0.4449 0.3004 0.8771 0.052 Uiso 1 1 calc R . . . .
C34 C 0.27376(17) 0.55873(19) 0.76267(12) 0.0196(4) Uani 1 1 d . . . . .
C35 C 0.20815(18) 0.5263(2) 0.84076(12) 0.0235(4) Uani 1 1 d . . . . .
H35 H 0.2046 0.4404 0.8703 0.028 Uiso 1 1 calc R . . . .
C36 C 0.1485(2) 0.6193(2) 0.87495(13) 0.0280(5) Uani 1 1 d . . . . .
H36 H 0.1054 0.5951 0.9271 0.034 Uiso 1 1 calc R . . . .
C37 C 0.1519(2) 0.7477(2) 0.83280(14) 0.0309(5) Uani 1 1 d . . . . .
H37 H 0.1115 0.8100 0.8560 0.037 Uiso 1 1 calc R . . . .
C38 C 0.2167(2) 0.7821(2) 0.75529(14) 0.0308(5) Uani 1 1 d . . . . .
H38 H 0.2197 0.8682 0.7261 0.037 Uiso 1 1 calc R . . . .
C39 C 0.27663(19) 0.6893(2) 0.72124(13) 0.0266(5) Uani 1 1 d . . . . .
H39 H 0.3202 0.7143 0.6693 0.032 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'
Cu Cu 0.3201 1.2651 '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_
_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
C1 Cu1 P1 177.09(6) . . ?
C28 P1 Cu1 105.65(6) . . ?
C34 P1 Cu1 98.83(6) . . ?
C34 P1 C28 103.23(9) . . ?
C1 N1 C2 111.42(15) . . ?
C1 N1 C16 123.95(14) . . ?
C2 N1 C16 124.62(15) . . ?
C1 N2 C3 111.47(16) . . ?
C1 N2 C4 124.77(15) . . ?
C3 N2 C4 123.74(15) . . ?
N1 C1 Cu1 127.98(13) . . ?
N2 C1 Cu1 128.39(14) . . ?
N2 C1 N1 103.63(14) . . ?
C3 C2 N1 106.77(16) . . ?
C2 C3 N2 106.70(16) . . ?
C5 C4 N2 118.70(16) . . ?
C5 C4 C9 123.61(18) . . ?
C9 C4 N2 117.68(17) . . ?
C4 C5 C10 122.75(18) . . ?
C6 C5 C4 116.72(18) . . ?
C6 C5 C10 120.51(18) . . ?
C7 C6 C5 121.2(2) . . ?
C6 C7 C8 120.5(2) . . ?
C7 C8 C9 121.0(2) . . ?
C4 C9 C13 121.54(18) . . ?
C8 C9 C4 116.97(19) . . ?
C8 C9 C13 121.42(18) . . ?
C5 C10 C11 110.24(17) . . ?
C5 C10 C12 112.15(18) . . ?
C12 C10 C11 110.82(18) . . ?
C9 C13 C14 113.48(18) . . ?
C9 C13 C15 109.89(17) . . ?
C14 C13 C15 111.01(17) . . ?
C17 C16 N1 118.38(16) . . ?
C17 C16 C21 123.36(18) . . ?
C21 C16 N1 118.25(16) . . ?
C16 C17 C18 116.63(18) . . ?
C16 C17 C22 122.56(18) . . ?
C18 C17 C22 120.78(18) . . ?
C19 C18 C17 121.23(19) . . ?
C18 C19 C20 120.7(2) . . ?
C19 C20 C21 120.90(19) . . ?
C16 C21 C25 121.24(17) . . ?
C20 C21 C16 117.18(18) . . ?
C20 C21 C25 121.49(18) . . ?
C17 C22 C24 112.76(19) . . ?
C23 C22 C17 111.06(18) . . ?
C23 C22 C24 110.3(2) . . ?
C21 C25 C26 113.18(18) . . ?
C21 C25 C27 110.55(16) . . ?
C27 C25 C26 110.34(18) . . ?
C29 C28 P1 118.24(18) . . ?
C33 C28 P1 124.43(17) . . ?
C33 C28 C29 117.3(2) . . ?
C30 C29 C28 121.1(3) . . ?
C31 C30 C29 120.9(3) . . ?
C30 C31 C32 119.4(3) . . ?
C31 C32 C33 120.1(3) . . ?
C32 C33 C28 121.3(3) . . ?
C35 C34 P1 126.06(16) . . ?
C35 C34 C39 116.90(19) . . ?
C39 C34 P1 116.90(15) . . ?
C36 C35 C34 121.29(19) . . ?
C37 C36 C35 120.9(2) . . ?
C36 C37 C38 118.8(2) . . ?
C39 C38 C37 120.4(2) . . ?
C38 C39 C34 121.76(19) . . ?
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
Cu1 P1 2.2079(5) . ?
Cu1 C1 1.9037(17) . ?
P1 C28 1.835(2) . ?
P1 C34 1.827(2) . ?
N1 C1 1.358(2) . ?
N1 C2 1.383(2) . ?
N1 C16 1.441(2) . ?
N2 C1 1.356(2) . ?
N2 C3 1.384(2) . ?
N2 C4 1.437(2) . ?
C2 C3 1.337(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.398(3) . ?
C5 C6 1.392(3) . ?
C5 C10 1.514(3) . ?
C6 C7 1.376(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.385(3) . ?
C9 C13 1.515(3) . ?
C10 C11 1.524(3) . ?
C10 C12 1.520(3) . ?
C13 C14 1.524(3) . ?
C13 C15 1.524(3) . ?
C16 C17 1.395(3) . ?
C16 C21 1.398(3) . ?
C17 C18 1.395(3) . ?
C17 C22 1.514(3) . ?
C18 C19 1.372(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.386(3) . ?
C21 C25 1.518(3) . ?
C22 C23 1.511(3) . ?
C22 C24 1.519(3) . ?
C25 C26 1.528(3) . ?
C25 C27 1.527(3) . ?
C28 C29 1.393(3) . ?
C28 C33 1.392(3) . ?
C29 C30 1.378(4) . ?
C30 C31 1.365(5) . ?
C31 C32 1.379(5) . ?
C32 C33 1.384(4) . ?
C34 C35 1.396(3) . ?
C34 C39 1.398(3) . ?
C35 C36 1.381(3) . ?
C36 C37 1.380(3) . ?
C37 C38 1.385(3) . ?
C38 C39 1.378(3) . ?
