#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:58:43 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260706 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/73/7127355.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_7127355
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         'C33 H36 Cu N2 P'
_chemical_formula_sum            'C33 H36 Cu N2 P'
_chemical_formula_weight         555.15
_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     iterative
_audit_creation_date             2019-03-01
_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                90
_cell_angle_beta                 119.072(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9476(3)
_cell_length_b                   19.6806(3)
_cell_length_c                   13.1443(3)
_cell_measurement_reflns_used    9677
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      29.1860
_cell_measurement_theta_min      3.7040
_cell_volume                     2927.40(14)
_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      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1468
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.874
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27306
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.542
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92295
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.168
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         7159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0317
_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)+(0.0338P)²+1.4061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0796
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5856
_reflns_number_total             7159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05694d2.cif
_cod_data_source_block           e19mkw11
_cod_depositor_comments
'Adding full bibliography for 7127351--7127357.cif.'
_cod_original_cell_volume        2927.39(13)
_cod_database_code               7127355
_chemical_oxdiff_usercomment     'Yellow block'
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C15(H15), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
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
Cu1 Cu 0.45216(2) 0.42641(2) 0.42807(2) 0.01790(6) Uani 1 1 d . . . . .
P1 P 0.53896(4) 0.45972(2) 0.62241(4) 0.02444(10) Uani 1 1 d . . . . .
N1 N 0.30339(11) 0.31568(7) 0.27347(11) 0.0196(3) Uani 1 1 d . . . . .
N2 N 0.48957(12) 0.30001(7) 0.33800(12) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.41055(13) 0.34288(8) 0.34117(13) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.30601(16) 0.25011(10) 0.22134(18) 0.0337(4) Uani 1 1 d . . . . .
H2A H 0.2593 0.2516 0.1371 0.040 Uiso 1 1 calc R . . . .
H2B H 0.2771 0.2137 0.2507 0.040 Uiso 1 1 calc R . . . .
C3 C 0.43655(15) 0.24132(9) 0.26024(15) 0.0261(4) Uani 1 1 d . . . . .
H3A H 0.4665 0.1988 0.3015 0.031 Uiso 1 1 calc R . . . .
H3B H 0.4512 0.2430 0.1946 0.031 Uiso 1 1 calc R . . . .
C4 C 0.61451(14) 0.31079(8) 0.39679(14) 0.0198(3) Uani 1 1 d . . . . .
C5 C 0.68364(15) 0.27737(9) 0.50221(14) 0.0238(3) Uani 1 1 d . . . . .
C6 C 0.80507(16) 0.28492(10) 0.55493(15) 0.0299(4) Uani 1 1 d . . . . .
H6 H 0.8524 0.2620 0.6242 0.036 Uiso 1 1 calc R . . . .
C7 C 0.85791(16) 0.32552(11) 0.50745(16) 0.0333(4) Uani 1 1 d . . . . .
C8 C 0.78619(16) 0.35971(10) 0.40411(16) 0.0305(4) Uani 1 1 d . . . . .
H8 H 0.8209 0.3881 0.3728 0.037 Uiso 1 1 calc R . . . .
C9 C 0.66375(15) 0.35254(8) 0.34623(14) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.62747(18) 0.23526(10) 0.55764(16) 0.0365(5) Uani 1 1 d . . . . .
H10A H 0.5661 0.2611 0.5606 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.6861 0.2230 0.6352 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.5943 0.1948 0.5125 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.99065(18) 0.33200(16) 0.5674(2) 0.0586(7) Uani 1 1 d . . . . .
H11A H 1.0124 0.3646 0.5268 0.088 Uiso 1 1 calc GR . . . .
H11B H 1.0248 0.2887 0.5674 0.088 Uiso 1 1 calc GR . . . .
H11C H 1.0192 0.3468 0.6462 0.088 Uiso 1 1 calc GR . . . .
C12 C 0.58648(17) 0.38897(9) 0.23367(16) 0.0295(4) Uani 1 1 d . . . . .
H12A H 0.5421 0.3563 0.1739 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.6349 0.4153 0.2117 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.5331 0.4185 0.2436 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.19186(14) 0.34611(8) 0.24305(13) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.13184(15) 0.32695(9) 0.30196(14) 0.0250(4) Uani 1 1 d . . . . .
C15 C 0.01858(16) 0.35232(10) 0.26361(15) 0.0299(4) Uani 1 1 d . . . . .
H15 H -0.0221 0.3401 0.3028 0.036 Uiso 1 1 calc R . . . .
C16 C -0.03488(15) 0.39528(9) 0.16857(15) 0.0279(4) Uani 1 1 d . . . . .
C17 C 0.02802(15) 0.41439(9) 0.11308(15) 0.0266(4) Uani 1 1 d . . . . .
H17 H -0.0067 0.4440 0.0501 0.032 Uiso 1 1 calc R . . . .
C18 C 0.14157(15) 0.39066(8) 0.14864(14) 0.0227(3) Uani 1 1 d . . . . .
C19 C 0.18814(19) 0.27964(13) 0.40485(18) 0.0456(6) Uani 1 1 d . . . . .
H19A H 0.2003 0.2360 0.3798 0.068 Uiso 1 1 calc GR . . . .
H19B H 0.1372 0.2748 0.4385 0.068 Uiso 1 1 calc GR . . . .
H19C H 0.2628 0.2980 0.4619 0.068 Uiso 1 1 calc GR . . . .
C20 C -0.15932(18) 0.42066(12) 0.1252(2) 0.0462(5) Uani 1 1 d . . . . .
H20A H -0.2022 0.4181 0.0418 0.069 Uiso 1 1 calc GR . . . .
H20B H -0.1570 0.4669 0.1492 0.069 Uiso 1 1 calc GR . . . .
H20C H -0.1979 0.3930 0.1570 0.069 Uiso 1 1 calc GR . . . .
C21 C 0.20923(18) 0.41344(11) 0.08841(18) 0.0371(5) Uani 1 1 d . . . . .
H21A H 0.2750 0.4410 0.1406 0.056 Uiso 1 1 calc GR . . . .
H21B H 0.1582 0.4395 0.0206 0.056 Uiso 1 1 calc GR . . . .
H21C H 0.2376 0.3744 0.0657 0.056 Uiso 1 1 calc GR . . . .
C22 C 0.68643(17) 0.42318(9) 0.70527(14) 0.0266(4) Uani 1 1 d . . . . .
C23 C 0.71248(18) 0.36356(10) 0.77125(16) 0.0326(4) Uani 1 1 d . . . . .
H23 H 0.6520 0.3412 0.7765 0.039 Uiso 1 1 calc R . . . .
C24 C 0.8252(2) 0.33684(11) 0.82872(18) 0.0426(5) Uani 1 1 d . . . . .
H24 H 0.8400 0.2978 0.8737 0.051 Uiso 1 1 calc R . . . .
C25 C 0.9155(2) 0.36792(12) 0.81952(19) 0.0469(6) Uani 1 1 d . . . . .
H25 H 0.9913 0.3497 0.8572 0.056 Uiso 1 1 calc R . . . .
C26 C 0.8929(2) 0.42625(12) 0.7540(2) 0.0474(6) Uani 1 1 d . . . . .
H26 H 0.9535 0.4471 0.7469 0.057 Uiso 1 1 calc R . . . .
C27 C 0.78056(19) 0.45394(10) 0.69885(18) 0.0370(5) Uani 1 1 d . . . . .
H27 H 0.7673 0.4939 0.6565 0.044 Uiso 1 1 calc R . . . .
C28 C 0.46807(16) 0.44264(8) 0.71017(15) 0.0248(4) Uani 1 1 d . . . . .
C29 C 0.52820(18) 0.44143(9) 0.83212(15) 0.0283(4) Uani 1 1 d . . . . .
H29 H 0.6101 0.4453 0.8719 0.034 Uiso 1 1 calc R . . . .
C30 C 0.4680(2) 0.43461(9) 0.89456(19) 0.0402(5) Uani 1 1 d . . . . .
H30 H 0.5100 0.4330 0.9754 0.048 Uiso 1 1 calc R . . . .
C31 C 0.3469(2) 0.43024(10) 0.8382(2) 0.0479(6) Uani 1 1 d . . . . .
H31 H 0.3067 0.4261 0.8804 0.058 Uiso 1 1 calc R . . . .
C32 C 0.2855(2) 0.43202(11) 0.7181(2) 0.0486(6) Uani 1 1 d . . . . .
H32 H 0.2034 0.4297 0.6792 0.058 Uiso 1 1 calc R . . . .
C33 C 0.34514(18) 0.43720(10) 0.65486(18) 0.0364(4) Uani 1 1 d . . . . .
H33 H 0.3024 0.4370 0.5740 0.044 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
P1 Cu1 P1 88.712(16) . 3_666 ?
C1 Cu1 P1 133.14(4) . 3_666 ?
C1 Cu1 P1 137.59(5) . . ?
Cu1 P1 Cu1 91.286(16) . 3_666 ?
C22 P1 Cu1 111.28(6) . 3_666 ?
C22 P1 Cu1 110.55(5) . . ?
C28 P1 Cu1 121.30(6) . . ?
C28 P1 Cu1 117.56(6) . 3_666 ?
C28 P1 C22 104.63(8) . . ?
C1 N1 C2 114.12(13) . . ?
C1 N1 C13 126.62(13) . . ?
C13 N1 C2 119.12(13) . . ?
C1 N2 C3 114.17(13) . . ?
C1 N2 C4 124.69(13) . . ?
C4 N2 C3 121.00(13) . . ?
N1 C1 Cu1 129.44(11) . . ?
N2 C1 Cu1 123.91(11) . . ?
N2 C1 N1 106.65(13) . . ?
N1 C2 C3 102.53(13) . . ?
N2 C3 C2 102.21(13) . . ?
C5 C4 N2 118.55(14) . . ?
C9 C4 N2 119.36(14) . . ?
C9 C4 C5 122.07(15) . . ?
C4 C5 C10 120.85(16) . . ?
C6 C5 C4 118.09(16) . . ?
C6 C5 C10 121.04(16) . . ?
C7 C6 C5 121.80(17) . . ?
C6 C7 C8 118.59(16) . . ?
C6 C7 C11 120.07(19) . . ?
C8 C7 C11 121.34(19) . . ?
C7 C8 C9 121.80(17) . . ?
C4 C9 C8 117.59(16) . . ?
C4 C9 C12 120.73(15) . . ?
C8 C9 C12 121.67(16) . . ?
C14 C13 N1 119.54(14) . . ?
C14 C13 C18 121.36(15) . . ?
C18 C13 N1 118.91(14) . . ?
C13 C14 C15 118.50(15) . . ?
C13 C14 C19 120.69(16) . . ?
C15 C14 C19 120.81(16) . . ?
C16 C15 C14 121.56(16) . . ?
C15 C16 C20 121.16(17) . . ?
C17 C16 C15 118.53(16) . . ?
C17 C16 C20 120.31(17) . . ?
C16 C17 C18 121.94(16) . . ?
C13 C18 C21 121.01(16) . . ?
C17 C18 C13 118.08(15) . . ?
C17 C18 C21 120.91(16) . . ?
C23 C22 P1 124.59(15) . . ?
C23 C22 C27 116.44(18) . . ?
C27 C22 P1 118.88(14) . . ?
C24 C23 C22 122.08(19) . . ?
C25 C24 C23 120.0(2) . . ?
C24 C25 C26 119.6(2) . . ?
C25 C26 C27 120.4(2) . . ?
C26 C27 C22 121.5(2) . . ?
C29 C28 P1 123.85(14) . . ?
C33 C28 P1 118.84(14) . . ?
C33 C28 C29 116.97(17) . . ?
C30 C29 C28 121.29(19) . . ?
C31 C30 C29 120.7(2) . . ?
C30 C31 C32 119.1(2) . . ?
C31 C32 C33 120.6(2) . . ?
C32 C33 C28 121.3(2) . . ?
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 2.3558(5) 3_666 ?
Cu1 P1 2.3298(5) . ?
Cu1 C1 1.9234(15) . ?
P1 Cu1 2.3558(5) 3_666 ?
P1 C22 1.824(2) . ?
P1 C28 1.8208(18) . ?
N1 C1 1.3430(19) . ?
N1 C2 1.469(2) . ?
N1 C13 1.429(2) . ?
N2 C1 1.342(2) . ?
N2 C3 1.472(2) . ?
N2 C4 1.430(2) . ?
C2 C3 1.519(2) . ?
C4 C5 1.396(2) . ?
C4 C9 1.391(2) . ?
C5 C6 1.384(2) . ?
C5 C10 1.504(2) . ?
C6 C7 1.382(3) . ?
C7 C8 1.391(3) . ?
C7 C11 1.508(3) . ?
C8 C9 1.393(2) . ?
C9 C12 1.505(2) . ?
C13 C14 1.389(2) . ?
C13 C18 1.396(2) . ?
C14 C15 1.391(2) . ?
C14 C19 1.506(2) . ?
C15 C16 1.384(3) . ?
C16 C17 1.384(3) . ?
C16 C20 1.509(3) . ?
C17 C18 1.389(2) . ?
C18 C21 1.506(2) . ?
C22 C23 1.399(2) . ?
C22 C27 1.400(3) . ?
C23 C24 1.380(3) . ?
C24 C25 1.376(3) . ?
C25 C26 1.378(3) . ?
C26 C27 1.383(3) . ?
C28 C29 1.401(2) . ?
C28 C33 1.396(3) . ?
C29 C30 1.386(3) . ?
C30 C31 1.374(3) . ?
C31 C32 1.381(4) . ?
C32 C33 1.386(3) . ?
