#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:01:04 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296612 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249479.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_7249479
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 H15 O2 P'
_chemical_formula_weight         294.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.665(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2605(4)
_cell_length_b                   11.3986(5)
_cell_length_c                   14.1564(5)
_cell_measurement_reflns_used    5606
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.7700
_cell_measurement_theta_min      3.5530
_cell_volume                     1491.25(11)
_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-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.863
_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  0.0301
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13775
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.780
_diffrn_reflns_theta_min         3.393
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
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    1.311
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0570
_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)+(0.0558P)²+1.8766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1411
_refine_ls_wR_factor_ref         0.1550
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2819
_reflns_number_total             3683
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc04450a2.cif
_cod_data_source_block           rm2383
_cod_depositor_comments
'Adding full bibliography for 7249476--7249480.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249479
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_min   0.881
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.8657(2) 0.31837(19) 0.36765(15) 0.0238(4) Uani 1 1 d . . . . .
C2 C 0.8893(2) 0.2043(2) 0.33675(16) 0.0274(5) Uani 1 1 d . . . . .
H2 H 0.844399 0.178060 0.278323 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9780(3) 0.1292(2) 0.39106(18) 0.0340(5) Uani 1 1 d . . . . .
H3 H 0.994003 0.051495 0.369853 0.041 Uiso 1 1 calc R U . . .
C4 C 1.0434(3) 0.1675(2) 0.47652(19) 0.0381(6) Uani 1 1 d . . . . .
H4 H 1.105178 0.116082 0.513195 0.046 Uiso 1 1 calc R U . . .
C5 C 1.0194(3) 0.2798(3) 0.50860(18) 0.0386(6) Uani 1 1 d . . . . .
H5 H 1.063624 0.305281 0.567443 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9303(3) 0.3552(2) 0.45442(16) 0.0308(5) Uani 1 1 d . . . . .
H6 H 0.913145 0.432298 0.476529 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5663(2) 0.3900(2) 0.30891(17) 0.0298(5) Uani 1 1 d . . . . .
C8 C 0.4844(3) 0.4670(3) 0.3593(2) 0.0486(7) Uani 1 1 d . . . . .
H8 H 0.527674 0.534797 0.388081 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3384(4) 0.4440(3) 0.3673(3) 0.0607(9) Uani 1 1 d . . . . .
H9 H 0.281984 0.496384 0.401822 0.073 Uiso 1 1 calc R U . . .
C10 C 0.2750(3) 0.3469(3) 0.3260(2) 0.0555(9) Uani 1 1 d . . . . .
H10 H 0.175075 0.332223 0.332285 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3552(3) 0.2705(3) 0.2754(2) 0.0491(7) Uani 1 1 d . . . . .
H11 H 0.310604 0.203571 0.246118 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5022(3) 0.2914(3) 0.26736(18) 0.0374(6) Uani 1 1 d . . . . .
H12 H 0.558278 0.238082 0.233394 0.045 Uiso 1 1 calc R U . . .
C13 C 0.9019(2) 0.3855(2) 0.14852(16) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.9229(3) 0.2905(3) 0.09161(19) 0.0396(6) Uani 1 1 d . . . . .
H14 H 0.853627 0.229015 0.086221 0.047 Uiso 1 1 calc R U . . .
C15 C 1.0473(4) 0.2859(3) 0.0420(2) 0.0512(8) Uani 1 1 d . . . . .
H15 H 1.062865 0.221053 0.001810 0.061 Uiso 1 1 calc R U . . .
C16 C 1.1480(3) 0.3744(3) 0.0505(2) 0.0506(8) Uani 1 1 d . . . . .
H16 H 1.233767 0.370039 0.017268 0.061 Uiso 1 1 calc R U . . .
C17 C 1.1243(3) 0.4685(3) 0.1071(2) 0.0519(8) Uani 1 1 d . . . . .
H17 H 1.193657 0.529936 0.112568 0.062 Uiso 1 1 calc R U . . .
C18 C 0.9998(3) 0.4756(3) 0.1567(2) 0.0433(7) Uani 1 1 d . . . . .
H18 H 0.982922 0.541615 0.195406 0.052 Uiso 1 1 calc R U . . .
O1 O 0.79344(19) 0.54425(15) 0.32824(13) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.76898(17) 0.38831(15) 0.19234(11) 0.0297(4) Uani 1 1 d . . . . .
P1 P 0.75509(6) 0.42267(5) 0.30090(4) 0.02658(17) 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'
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 119.3(2) . . ?
C2 C1 P1 123.19(17) . . ?
C6 C1 P1 117.49(18) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 119.9(2) . . ?
C12 C7 P1 122.25(19) . . ?
C8 C7 P1 117.8(2) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 119.9(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 121.6(2) . . ?
C18 C13 O2 122.4(2) . . ?
C14 C13 O2 115.9(2) . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 118.7(3) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C13 O2 P1 123.58(15) . . ?
O1 P1 O2 116.69(10) . . ?
O1 P1 C1 111.32(10) . . ?
O2 P1 C1 105.37(10) . . ?
O1 P1 C7 113.36(11) . . ?
O2 P1 C7 98.52(10) . . ?
C1 P1 C7 110.70(10) . . ?
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 1.393(3) . ?
C1 C6 1.396(3) . ?
C1 P1 1.798(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.384(4) . ?
C7 C8 1.387(4) . ?
C7 P1 1.798(2) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.370(4) . ?
C13 C14 1.370(4) . ?
C13 O2 1.414(3) . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O1 P1 1.4762(18) . ?
O2 P1 1.5991(17) . ?
