#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:35:14 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301801 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/15/2021555.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021555
loop_
_publ_author_name
'Hasija, Avantika'
'Chopra, Deepak'
_publ_section_title
;
 Exploring concomitant/conformational dimorphism in a difluoro-substituted
 phosphoramidate derivative
;
_journal_coeditor_code           JX3028
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              451
_journal_page_last               461
_journal_paper_doi               10.1107/S2053229619003589
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C18 H14 F2 N O3 P'
_chemical_formula_moiety         'C18 H14 F2 N O3 P'
_chemical_formula_sum            'C18 H14 F2 N O3 P'
_chemical_formula_weight         361.27
_chemical_name_systematic
;
Diphenyl (3,4-difluorophenyl)phosphoramidate
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 92.2600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2037(3)
_cell_length_b                   9.1372(3)
_cell_length_c                   17.9981(5)
_cell_measurement_reflns_used    7646
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.99
_cell_volume                     1676.72(9)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12986
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.997
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.362
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0298
_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)+(0.0397P)²+0.6978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                2724
_reflns_number_total             2935
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3028sup1.cif
_cod_data_source_block           formI
_cod_depositor_comments
'Adding full bibliography for 2021555--2021556.cif.'
_cod_database_code               2021555
_cod_database_fobs_code          2021555
_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   0.953
_shelx_estimated_absorpt_t_max   0.980
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
P P1 0.69854(3) 0.55364(4) 0.45512(2) 0.01971(12) Uani d 1
O O1 0.76245(9) 0.57544(11) 0.37749(5) 0.0229(2) Uani d 1
O O2 0.83001(9) 0.57334(10) 0.50351(5) 0.0220(2) Uani d 1
O O3 0.59246(9) 0.65535(10) 0.47204(6) 0.0247(2) Uani d 1
F F1 1.03376(8) 0.11956(10) 0.39419(5) 0.0344(2) Uani d 1
F F2 0.91966(9) -0.13348(9) 0.42936(5) 0.0343(2) Uani d 1
N N1 0.64940(11) 0.38495(13) 0.46164(7) 0.0216(3) Uani d 1
H H1A 0.5741(17) 0.3758(18) 0.4813(9) 0.026 Uiso d 1
C C1 0.69334(14) 0.54882(16) 0.30941(8) 0.0249(3) Uani d 1
C C2 0.75696(16) 0.46668(19) 0.25802(9) 0.0345(4) Uani d 1
H H2 0.841140 0.426620 0.269808 0.041 Uiso calc 1
C C3 0.69662(19) 0.4431(2) 0.18880(10) 0.0450(4) Uani d 1
H H3 0.739539 0.386642 0.152722 0.054 Uiso calc 1
C C4 0.57445(18) 0.5015(2) 0.17213(10) 0.0463(5) Uani d 1
H H4 0.532859 0.484492 0.124759 0.056 Uiso calc 1
C C5 0.51299(17) 0.5841(2) 0.22397(10) 0.0489(5) Uani d 1
H H5 0.429061 0.624598 0.211993 0.059 Uiso calc 1
C C6 0.57171(15) 0.6093(2) 0.29384(10) 0.0377(4) Uani d 1
H H6 0.529191 0.666633 0.329756 0.045 Uiso calc 1
C C7 0.72206(13) 0.25549(15) 0.45390(7) 0.0189(3) Uani d 1
C C8 0.84869(13) 0.25457(15) 0.42702(8) 0.0220(3) Uani d 1
H H8 0.890205 0.343202 0.413524 0.026 Uiso calc 1
C C9 0.91183(13) 0.12261(16) 0.42056(8) 0.0232(3) Uani d 1
C C10 0.85381(14) -0.00689(16) 0.43892(8) 0.0239(3) Uani d 1
C C11 0.72971(14) -0.00755(16) 0.46600(8) 0.0267(3) Uani d 1
H H11 0.689347 -0.096980 0.479304 0.032 Uiso calc 1
C C12 0.66449(14) 0.12405(15) 0.47358(8) 0.0227(3) Uani d 1
H H12 0.578928 0.124521 0.492565 0.027 Uiso calc 1
C C13 0.83067(13) 0.54108(15) 0.58046(8) 0.0226(3) Uani d 1
C C14 0.76192(16) 0.62747(18) 0.62802(9) 0.0341(4) Uani d 1
H H14 0.710335 0.707214 0.609753 0.041 Uiso calc 1
C C15 0.77000(19) 0.5950(2) 0.70300(10) 0.0475(5) Uani d 1
H H15 0.722759 0.652520 0.736854 0.057 Uiso calc 1
C C16 0.84617(18) 0.4798(2) 0.72918(10) 0.0471(5) Uani d 1
H H16 0.851298 0.458516 0.780883 0.057 Uiso calc 1
C C17 0.91476(16) 0.3955(2) 0.68050(9) 0.0365(4) Uani d 1
H H17 0.967236 0.316401 0.698749 0.044 Uiso calc 1
C C18 0.90742(13) 0.42563(17) 0.60516(8) 0.0260(3) Uani d 1
H H18 0.954283 0.368002 0.571201 0.031 Uiso calc 1
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'
F F 0.0171 0.0103 '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
O3 P1 O1 115.97(6)
O3 P1 O2 115.49(6)
O1 P1 O2 95.87(5)
O3 P1 N1 110.67(6)
O1 P1 N1 108.84(6)
O2 P1 N1 108.99(6)
C1 O1 P1 122.52(8)
C13 O2 P1 119.11(8)
C7 N1 P1 128.67(10)
C7 N1 H1A 116.2(11)
P1 N1 H1A 113.8(11)
C2 C1 C6 121.88(15)
C2 C1 O1 116.47(13)
C6 C1 O1 121.54(14)
C1 C2 C3 119.04(16)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 120.15(18)
C4 C3 H3 119.9
C2 C3 H3 119.9
C5 C4 C3 119.93(17)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 120.96(16)
C4 C5 H5 119.5
C6 C5 H5 119.5
C1 C6 C5 118.03(17)
C1 C6 H6 121.0
C5 C6 H6 121.0
C12 C7 C8 119.29(12)
C12 C7 N1 118.18(12)
C8 C7 N1 122.54(12)
C9 C8 C7 118.53(13)
C9 C8 H8 120.7
C7 C8 H8 120.7
F1 C9 C10 118.71(13)
F1 C9 C8 119.33(13)
C10 C9 C8 121.95(13)
F2 C10 C9 119.13(13)
F2 C10 C11 120.71(13)
C9 C10 C11 120.16(13)
C10 C11 C12 118.98(13)
C10 C11 H11 120.5
C12 C11 H11 120.5
C11 C12 C7 121.09(13)
C11 C12 H12 119.5
C7 C12 H12 119.5
C14 C13 C18 122.39(14)
C14 C13 O2 120.40(14)
C18 C13 O2 117.13(12)
C13 C14 C15 118.19(16)
C13 C14 H14 120.9
C15 C14 H14 120.9
C16 C15 C14 120.54(16)
C16 C15 H15 119.7
C14 C15 H15 119.7
C17 C16 C15 120.17(16)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C18 120.18(17)
C16 C17 H17 119.9
C18 C17 H17 119.9
C13 C18 C17 118.52(14)
C13 C18 H18 120.7
C17 C18 H18 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O3 1.4677(10)
P1 O1 1.5776(10)
P1 O2 1.5807(10)
P1 N1 1.6266(12)
O1 C1 1.4105(17)
O2 C13 1.4156(17)
F1 C9 1.3492(16)
F2 C10 1.3521(16)
N1 C7 1.4059(17)
N1 H1A 0.863(17)
C1 C2 1.374(2)
C1 C6 1.377(2)
C2 C3 1.384(2)
C2 H2 0.9500
C3 C4 1.378(3)
C3 H3 0.9500
C4 C5 1.371(3)
C4 H4 0.9500
C5 C6 1.391(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C12 1.3890(19)
C7 C8 1.3974(19)
C8 C9 1.374(2)
C8 H8 0.9500
C9 C10 1.369(2)
C10 C11 1.375(2)
C11 C12 1.384(2)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.377(2)
C13 C18 1.377(2)
C14 C15 1.381(3)
C14 H14 0.9500
C15 C16 1.381(3)
C15 H15 0.9500
C16 C17 1.378(3)
C16 H16 0.9500
C17 C18 1.383(2)
C17 H17 0.9500
C18 H18 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O3 P1 O1 C1 -67.23(12)
O2 P1 O1 C1 170.68(10)
N1 P1 O1 C1 58.30(11)
O3 P1 O2 C13 67.21(11)
O1 P1 O2 C13 -170.34(10)
N1 P1 O2 C13 -58.09(11)
O3 P1 N1 C7 -176.21(11)
O1 P1 N1 C7 55.24(13)
O2 P1 N1 C7 -48.16(13)
P1 O1 C1 C2 -132.55(12)
P1 O1 C1 C6 51.14(18)
C6 C1 C2 C3 -0.5(3)
O1 C1 C2 C3 -176.81(15)
C1 C2 C3 C4 -0.1(3)
C2 C3 C4 C5 0.6(3)
C3 C4 C5 C6 -0.5(3)
C2 C1 C6 C5 0.6(3)
O1 C1 C6 C5 176.68(15)
C4 C5 C6 C1 -0.1(3)
P1 N1 C7 C12 169.82(11)
P1 N1 C7 C8 -10.5(2)
C12 C7 C8 C9 0.4(2)
N1 C7 C8 C9 -179.29(12)
C7 C8 C9 F1 179.52(12)
C7 C8 C9 C10 0.7(2)
F1 C9 C10 F2 -0.7(2)
C8 C9 C10 F2 178.17(13)
F1 C9 C10 C11 179.94(13)
C8 C9 C10 C11 -1.2(2)
F2 C10 C11 C12 -178.71(12)
C9 C10 C11 C12 0.6(2)
C10 C11 C12 C7 0.4(2)
C8 C7 C12 C11 -0.9(2)
N1 C7 C12 C11 178.77(13)
P1 O2 C13 C14 -68.15(16)
P1 O2 C13 C18 114.98(12)
C18 C13 C14 C15 -0.7(2)
O2 C13 C14 C15 -177.39(14)
C13 C14 C15 C16 0.6(3)
C14 C15 C16 C17 -0.2(3)
C15 C16 C17 C18 -0.2(3)
C14 C13 C18 C17 0.3(2)
O2 C13 C18 C17 177.15(13)
C16 C17 C18 C13 0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139062915
