#------------------------------------------------------------------------------
#$Date: 2022-08-06 15:03:08 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158755.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_7158755
loop_
_publ_author_name
'Kaźmierczak, Marcin'
'Dutkiewicz, Grzegorz'
'Koroniak, Henryk'
_publ_section_title
;
 Deoxyfluorinating reagents as tools for γ-amino-α-hydroxyphosphonate
 modification.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5615
_journal_page_last               5623
_journal_paper_doi               10.1039/d2ob00915c
_journal_volume                  20
_journal_year                    2022
_chemical_formula_sum            'C21 H30 N O4 P'
_chemical_formula_weight         391.43
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-05-12 deposited with the CCDC.	2022-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                71.144(2)
_cell_angle_beta                 81.512(2)
_cell_angle_gamma                81.501(2)
_cell_formula_units_Z            2
_cell_length_a                   8.5489(2)
_cell_length_b                   9.9570(2)
_cell_length_c                   12.8587(3)
_cell_measurement_reflns_used    16002
_cell_measurement_temperature    130(1)
_cell_measurement_theta_max      76.0550
_cell_measurement_theta_min      3.6340
_cell_volume                     1018.59(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      130(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            19681
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.282
_diffrn_reflns_theta_min         3.653
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.409
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0327
_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)+(0.0396P)²+0.4097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4170
_reflns_number_total             4211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00915c2.cif
_cod_data_source_block           6a
_cod_depositor_comments
'Adding full bibliography for 7158755--7158757.cif.'
_cod_database_code               7158755
_shelx_shelxl_version_number     2018/3
_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   0.603
_shelx_estimated_absorpt_t_max   0.766
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
P1 P 0.31751(3) 0.67462(3) 0.00669(2) 0.02043(9) Uani 1 1 d . . . . .
O1 O 0.48880(10) 0.66053(9) 0.01688(7) 0.02714(19) Uani 1 1 d . . . . .
O2 O 0.29171(10) 0.69322(9) -0.11620(7) 0.02632(19) Uani 1 1 d . . . . .
C3 C 0.13139(15) 0.71513(14) -0.14975(10) 0.0281(3) Uani 1 1 d . . . . .
H3A H 0.052041 0.734552 -0.090594 0.034 Uiso 1 1 calc R U . . .
H3B H 0.107121 0.628686 -0.163741 0.034 Uiso 1 1 calc R U . . .
C4 C 0.12526(18) 0.83961(17) -0.25284(13) 0.0414(3) Uani 1 1 d . . . . .
H4A H 0.201814 0.818057 -0.311480 0.062 Uiso 1 1 calc R U . . .
H4B H 0.152031 0.923958 -0.238553 0.062 Uiso 1 1 calc R U . . .
H4C H 0.017903 0.858418 -0.276057 0.062 Uiso 1 1 calc R U . . .
O5 O 0.22173(10) 0.80741(9) 0.03832(7) 0.02692(19) Uani 1 1 d . . . . .
C6 C 0.30117(17) 0.93404(14) 0.02062(13) 0.0349(3) Uani 1 1 d . . . . .
H6A H 0.321925 0.983719 -0.059502 0.042 Uiso 1 1 calc R U . . .
H6B H 0.404149 0.906674 0.052437 0.042 Uiso 1 1 calc R U . . .
C7 C 0.19458(18) 1.03019(14) 0.07588(12) 0.0366(3) Uani 1 1 d . . . . .
H7A H 0.094528 1.059418 0.042010 0.055 Uiso 1 1 calc R U . . .
H7B H 0.247041 1.114892 0.067085 0.055 Uiso 1 1 calc R U . . .
H7C H 0.172409 0.979184 0.154716 0.055 Uiso 1 1 calc R U . . .
C8 C 0.20769(13) 0.52969(12) 0.09852(9) 0.0213(2) Uani 1 1 d . . . . .
H8 H 0.093704 0.569079 0.107541 0.026 Uiso 1 1 calc R U . . .
O9 O 0.21372(11) 0.41624(9) 0.05362(7) 0.02529(19) Uani 1 1 d . . . . .
H9 H 0.310(2) 0.389(2) 0.0391(15) 0.044(5) Uiso 1 1 d . . . . .
C10 C 0.26890(15) 0.48246(13) 0.21224(10) 0.0254(2) Uani 1 1 d . . . . .
H19A H 0.270140 0.567336 0.236120 0.030 Uiso 1 1 calc R U . . .
H10B H 0.379423 0.436511 0.206871 0.030 Uiso 1 1 calc R U . . .
C11 C 0.16471(14) 0.37732(12) 0.29895(9) 0.0227(2) Uani 1 1 d . . . . .
H11A H 0.055013 0.425149 0.303835 0.027 Uiso 1 1 calc R U . . .
H11B H 0.161040 0.295078 0.272371 0.027 Uiso 1 1 calc R U . . .
N12 N 0.21571(12) 0.32230(10) 0.41102(8) 0.0212(2) Uani 1 1 d . . . . .
C13 C 0.36468(14) 0.22712(12) 0.41695(10) 0.0232(2) Uani 1 1 d . . . . .
H13A H 0.400128 0.204156 0.491220 0.028 Uiso 1 1 calc R U . . .
H13B H 0.447662 0.277296 0.362056 0.028 Uiso 1 1 calc R U . . .
C14 C 0.34780(14) 0.08981(12) 0.39515(9) 0.0220(2) Uani 1 1 d . . . . .
C15 C 0.45215(15) 0.04373(14) 0.31680(11) 0.0288(3) Uani 1 1 d . . . . .
H15 H 0.531691 0.101704 0.273453 0.035 Uiso 1 1 calc R U . . .
C16 C 0.44129(18) -0.08639(15) 0.30121(12) 0.0350(3) Uani 1 1 d . . . . .
H16 H 0.514296 -0.117520 0.248292 0.042 Uiso 1 1 calc R U . . .
C17 C 0.32434(18) -0.17035(14) 0.36270(12) 0.0353(3) Uani 1 1 d . . . . .
H17 H 0.316643 -0.259039 0.351897 0.042 Uiso 1 1 calc R U . . .
C18 C 0.21845(18) -0.12502(14) 0.44003(11) 0.0337(3) Uani 1 1 d . . . . .
H18 H 0.137528 -0.182301 0.481983 0.040 Uiso 1 1 calc R U . . .
C19 C 0.23046(16) 0.00432(13) 0.45633(10) 0.0278(3) Uani 1 1 d . . . . .
H19 H 0.157793 0.034652 0.509802 0.033 Uiso 1 1 calc R U . . .
C20 C 0.22625(14) 0.43848(12) 0.45506(9) 0.0233(2) Uani 1 1 d . . . . .
H20A H 0.135253 0.512006 0.434028 0.028 Uiso 1 1 calc R U . . .
H20B H 0.324938 0.483075 0.420230 0.028 Uiso 1 1 calc R U . . .
C21 C 0.22635(14) 0.39241(12) 0.57939(10) 0.0219(2) Uani 1 1 d . . . . .
C22 C 0.13604(15) 0.28659(13) 0.64954(10) 0.0258(2) Uani 1 1 d . . . . .
H22 H 0.077505 0.236898 0.619232 0.031 Uiso 1 1 calc R U . . .
C23 C 0.13094(16) 0.25319(14) 0.76351(11) 0.0301(3) Uani 1 1 d . . . . .
H23 H 0.068041 0.181577 0.810628 0.036 Uiso 1 1 calc R U . . .
C24 C 0.21722(16) 0.32387(14) 0.80888(10) 0.0305(3) Uani 1 1 d . . . . .
H24 H 0.213740 0.300592 0.886837 0.037 Uiso 1 1 calc R U . . .
C25 C 0.30835(15) 0.42841(14) 0.74005(11) 0.0305(3) Uani 1 1 d . . . . .
H25 H 0.368126 0.476736 0.770693 0.037 Uiso 1 1 calc R U . . .
C26 C 0.31238(14) 0.46266(13) 0.62610(10) 0.0262(2) Uani 1 1 d . . . . .
H26 H 0.374630 0.534993 0.579323 0.031 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
O1 P1 O2 109.61(5) . . ?
O1 P1 O5 113.18(5) . . ?
O2 P1 O5 107.62(5) . . ?
O1 P1 C8 116.26(5) . . ?
O2 P1 C8 108.59(5) . . ?
O5 P1 C8 101.00(5) . . ?
C3 O2 P1 120.71(8) . . ?
O2 C3 C4 107.75(10) . . ?
O2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
O2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 O5 P1 119.42(8) . . ?
O5 C6 C7 107.98(11) . . ?
O5 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
O5 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O9 C8 C10 113.27(9) . . ?
O9 C8 P1 112.10(8) . . ?
C10 C8 P1 108.69(8) . . ?
O9 C8 H8 107.5 . . ?
C10 C8 H8 107.5 . . ?
P1 C8 H8 107.5 . . ?
C8 O9 H9 107.7(12) . . ?
C8 C10 C11 111.65(9) . . ?
C8 C10 H19A 109.3 . . ?
C11 C10 H19A 109.3 . . ?
C8 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H19A C10 H10B 108.0 . . ?
N12 C11 C10 116.04(9) . . ?
N12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
N12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C20 N12 C13 111.08(9) . . ?
C20 N12 C11 111.32(9) . . ?
C13 N12 C11 112.90(9) . . ?
N12 C13 C14 112.58(9) . . ?
N12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C19 118.65(11) . . ?
C15 C14 C13 120.96(11) . . ?
C19 C14 C13 120.35(11) . . ?
C14 C15 C16 120.70(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.03(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.89(12) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.03(13) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.69(12) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
N12 C20 C21 114.10(9) . . ?
N12 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
N12 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C26 118.55(11) . . ?
C22 C21 C20 121.97(10) . . ?
C26 C21 C20 119.39(10) . . ?
C23 C22 C21 120.49(11) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.35(12) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.69(12) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 119.95(11) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.96(11) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
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
P1 O1 1.4714(9) . ?
P1 O2 1.5753(9) . ?
P1 O5 1.5854(9) . ?
P1 C8 1.8248(11) . ?
O2 C3 1.4620(14) . ?
C3 C4 1.4952(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O5 C6 1.4576(14) . ?
C6 C7 1.4976(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O9 1.4168(13) . ?
C8 C10 1.5303(15) . ?
C8 H8 1.0000 . ?
O9 H9 0.844(19) . ?
C10 C11 1.5364(16) . ?
C10 H19A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.4736(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 C20 1.4616(14) . ?
N12 C13 1.4667(15) . ?
C13 C14 1.5121(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3906(18) . ?
C14 C19 1.3915(17) . ?
C15 C16 1.3915(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3903(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.5141(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.3930(16) . ?
C21 C26 1.3947(16) . ?
C22 C23 1.3895(18) . ?
C22 H22 0.9500 . ?
C23 C24 1.3877(19) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3892(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9 O1 0.844(19) 1.82(2) 2.6583(12) 170.1(18) 2_665 yes
