#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:01:04 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296612 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249480.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_7249480
loop_
_publ_author_name
'Boruah, Tribani'
'Ishizeki, Ren'
'Roldan, Alberto'
'Melen, Rebecca L.'
'Wirth, Thomas'
_publ_section_title
;
 Flow electrosynthesis of phosphinamides and phosphoramidates through P--N
 coupling
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              11722
_journal_page_last               11727
_journal_paper_doi               10.1039/D4GC04450A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C18 H16 N O2 P'
_chemical_formula_weight         309.29
_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
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.452(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6012(12)
_cell_length_b                   9.0207(5)
_cell_length_c                   11.7490(9)
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.5240
_cell_measurement_theta_min      3.8170
_cell_volume                     1577.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14047
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.796
_diffrn_reflns_theta_min         3.431
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0568P)²+0.5942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1578
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2361
_reflns_number_total             3903
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc04450a2.cif
_cod_data_source_block           rm2385
_cod_depositor_comments
'Adding full bibliography for 7249476--7249480.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249480
_shelx_shelxl_version_number     2018/1
_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_min   0.965
_shelx_estimated_absorpt_t_max   0.993
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
C1 C 0.58610(18) 0.5860(3) 0.2914(2) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.5312(2) 0.5820(4) 0.3639(3) 0.0502(8) Uani 1 1 d . . . . .
H2 H 0.556687 0.565855 0.447168 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4390(2) 0.6012(5) 0.3166(4) 0.0665(11) Uani 1 1 d . . . . .
H3 H 0.401814 0.597753 0.367463 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4016(2) 0.6252(4) 0.1964(3) 0.0553(9) Uani 1 1 d . . . . .
H4 H 0.338398 0.636850 0.163844 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4552(2) 0.6323(4) 0.1243(3) 0.0570(9) Uani 1 1 d . . . . .
H5 H 0.429311 0.651030 0.041485 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5470(2) 0.6126(4) 0.1701(3) 0.0472(8) Uani 1 1 d . . . . .
H6 H 0.583620 0.617312 0.118570 0.057 Uiso 1 1 calc R U . . .
C7 C 0.76404(17) 0.7281(3) 0.3661(2) 0.0274(6) Uani 1 1 d . . . . .
C8 C 0.76046(18) 0.8109(3) 0.2648(2) 0.0338(7) Uani 1 1 d . . . . .
H8 H 0.725400 0.776785 0.188544 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8075(2) 0.9424(3) 0.2744(3) 0.0385(7) Uani 1 1 d . . . . .
H9 H 0.804535 0.998498 0.204850 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8591(2) 0.9924(3) 0.3851(3) 0.0394(7) Uani 1 1 d . . . . .
H10 H 0.891089 1.083172 0.391353 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8643(2) 0.9113(3) 0.4865(3) 0.0387(7) Uani 1 1 d . . . . .
H11 H 0.900501 0.945082 0.562197 0.046 Uiso 1 1 calc R U . . .
C12 C 0.81605(18) 0.7793(3) 0.4773(2) 0.0335(7) Uani 1 1 d . . . . .
H12 H 0.818684 0.724062 0.547093 0.040 Uiso 1 1 calc R U . . .
C13 C 0.81310(17) 0.4047(3) 0.2478(2) 0.0268(6) Uani 1 1 d . . . . .
C14 C 0.81234(17) 0.3044(3) 0.1568(2) 0.0283(6) Uani 1 1 d . . . . .
C15 C 0.89178(18) 0.2492(3) 0.1460(2) 0.0333(6) Uani 1 1 d . . . . .
H15 H 0.890860 0.181611 0.083585 0.040 Uiso 1 1 calc R U . . .
C16 C 0.97312(19) 0.2917(3) 0.2256(3) 0.0397(7) Uani 1 1 d . . . . .
H16 H 1.027826 0.253354 0.217948 0.048 Uiso 1 1 calc R U . . .
C17 C 0.97437(19) 0.3902(3) 0.3165(3) 0.0402(7) Uani 1 1 d . . . . .
H17 H 1.030053 0.419514 0.371104 0.048 Uiso 1 1 calc R U . . .
C18 C 0.89455(18) 0.4461(3) 0.3279(2) 0.0343(7) Uani 1 1 d . . . . .
H18 H 0.895696 0.513053 0.390763 0.041 Uiso 1 1 calc R U . . .
N1 N 0.72825(15) 0.4562(2) 0.25215(19) 0.0331(5) Uani 1 1 d . . . . .
H1 H 0.682029 0.431869 0.190913 0.040 Uiso 1 1 calc R U . . .
O1 O 0.72663(13) 0.48814(19) 0.47796(16) 0.0363(5) Uani 1 1 d . . . . .
O2 O 0.72918(12) 0.2692(2) 0.08159(17) 0.0378(5) Uani 1 1 d . . . . .
H2A H 0.733093 0.193208 0.042133 0.057 Uiso 1 1 calc R U . . .
P1 P 0.70469(5) 0.55576(7) 0.35702(6) 0.0280(2) Uani 1 1 d . . . . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C2 C1 C6 118.3(3) . . ?
C2 C1 P1 118.8(2) . . ?
C6 C1 P1 122.9(2) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C12 119.1(2) . . ?
C8 C7 P1 121.7(2) . . ?
C12 C7 P1 119.17(19) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.3(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 N1 124.3(2) . . ?
C14 C13 N1 116.4(2) . . ?
O2 C14 C15 124.2(2) . . ?
O2 C14 C13 115.6(2) . . ?
C15 C14 C13 120.2(2) . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C13 N1 P1 128.56(18) . . ?
C13 N1 H1 115.7 . . ?
P1 N1 H1 115.7 . . ?
C14 O2 H2A 109.5 . . ?
O1 P1 N1 116.73(11) . . ?
O1 P1 C7 109.33(11) . . ?
N1 P1 C7 106.78(12) . . ?
O1 P1 C1 112.57(12) . . ?
N1 P1 C1 101.13(12) . . ?
C7 P1 C1 109.87(12) . . ?
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
C1 C2 1.378(4) . ?
C1 C6 1.393(4) . ?
C1 P1 1.799(3) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.360(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 C12 1.394(4) . ?
C7 P1 1.796(3) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.386(3) . ?
C13 C14 1.398(4) . ?
C13 N1 1.418(3) . ?
C14 O2 1.370(3) . ?
C14 C15 1.377(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 P1 1.653(2) . ?
N1 H1 0.8800 . ?
O1 P1 1.4888(18) . ?
O2 H2A 0.8400 . ?
