#------------------------------------------------------------------------------
#$Date: 2023-12-22 17:07:40 +0200 (Fri, 22 Dec 2023) $
#$Revision: 288505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/92/4129278.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_4129278
loop_
_publ_author_name
'Panigrahi, Kaushik'
'Applegate, Gregory A.'
'Malik, Guillaume'
'Berkowitz, David B.'
_publ_section_title
;
 Combining a Clostridial enzyme exhibiting unusual active site plasticity
 with a remarkably facile sigmatropic rearrangement: rapid,
 stereocontrolled entry into densely functionalized fluorinated
 phosphonates for chemical biology.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3600
_journal_page_last               3609
_journal_paper_doi               10.1021/jacs.5b00022
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H17 F2 O5 P'
_chemical_formula_sum            'C12 H17 F2 O5 P'
_chemical_formula_weight         310.23
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4421(7)
_cell_length_b                   9.7834(13)
_cell_length_c                   26.672(3)
_cell_measurement_reflns_used    5538
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.91
_cell_measurement_theta_min      2.29
_cell_volume                     1420.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD Bruker APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12715
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.91
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.9294
_exptl_absorpt_correction_T_min  0.9088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2579
_reflns_number_total             2622
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ja5b00022_si_002.cif
_cod_data_source_block           12042
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_database_code               4129278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.61562(7) 0.40378(4) 0.660039(14) 0.01812(11) Uani 1 1 d .
F1 F 0.60725(19) 0.67101(10) 0.65145(4) 0.0288(2) Uani 1 1 d .
F2 F 0.25725(18) 0.58157(10) 0.67530(3) 0.0264(2) Uani 1 1 d .
O1 O 0.7982(2) 0.36842(12) 0.62170(4) 0.0240(3) Uani 1 1 d .
O2 O 0.7143(2) 0.44171(12) 0.71334(4) 0.0256(3) Uani 1 1 d .
O3 O 0.4147(2) 0.29363(11) 0.67078(4) 0.0218(3) Uani 1 1 d .
O4 O 0.2331(2) 0.44403(12) 0.57883(4) 0.0208(2) Uani 1 1 d .
H4O H 0.096(4) 0.438(2) 0.5959(7) 0.025 Uiso 1 1 d .
O5 O 0.1349(2) 1.13620(11) 0.50999(4) 0.0247(3) Uani 1 1 d .
C1 C 0.8265(4) 0.3327(2) 0.74346(7) 0.0374(5) Uani 1 1 d .
H1A H 0.8984 0.2624 0.7212 0.045 Uiso 1 1 calc R
H1B H 0.7000 0.2885 0.7646 0.045 Uiso 1 1 calc R
C2 C 1.0223(4) 0.3933(2) 0.77580(7) 0.0341(4) Uani 1 1 d .
H2A H 1.1489 0.4350 0.7546 0.051 Uiso 1 1 d R
H2B H 1.0965 0.3214 0.7964 0.051 Uiso 1 1 d R
H2C H 0.9501 0.4632 0.7976 0.051 Uiso 1 1 d R
C3 C 0.3640(3) 0.17947(16) 0.63701(6) 0.0239(3) Uani 1 1 d .
H3A H 0.4158 0.2031 0.6025 0.029 Uiso 1 1 calc R
H3B H 0.1855 0.1598 0.6366 0.029 Uiso 1 1 calc R
C4 C 0.5027(3) 0.05591(18) 0.65492(7) 0.0277(4) Uani 1 1 d .
H4A H 0.6796 0.0719 0.6513 0.042 Uiso 1 1 d R
H4B H 0.4550 -0.0238 0.6349 0.042 Uiso 1 1 d R
H4C H 0.4640 0.0390 0.6903 0.042 Uiso 1 1 d R
C5 C 0.4511(3) 0.56357(16) 0.64348(6) 0.0195(3) Uani 1 1 d .
C6 C 0.3629(3) 0.56616(15) 0.58885(5) 0.0186(3) Uani 1 1 d .
H6 H 0.5123 0.5665 0.5670 0.022 Uiso 1 1 calc R
C7 C 0.2237(3) 0.69485(17) 0.57829(6) 0.0205(3) Uani 1 1 d .
H7 H 0.0660 0.7068 0.5929 0.025 Uiso 1 1 calc R
C8 C 0.3139(3) 0.79341(16) 0.54899(6) 0.0181(3) Uani 1 1 d .
H8 H 0.4681 0.7768 0.5334 0.022 Uiso 1 1 calc R
C9 C 0.1963(3) 0.92421(16) 0.53883(6) 0.0183(3) Uani 1 1 d .
C10 C 0.2899(3) 1.02743(17) 0.51092(6) 0.0220(3) Uani 1 1 d .
H10 H 0.4438 1.0242 0.4942 0.026 Uiso 1 1 calc R
C11 C -0.0640(3) 1.10018(18) 0.53828(6) 0.0240(4) Uani 1 1 d .
H11 H -0.2022 1.1573 0.5442 0.029 Uiso 1 1 calc R
C12 C -0.0380(3) 0.97324(17) 0.55654(6) 0.0212(3) Uani 1 1 d .
H12 H -0.1514 0.9252 0.5771 0.025 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'
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
O1 P1 O3 116.07(7)
O1 P1 O2 117.17(7)
O3 P1 O2 103.74(6)
O1 P1 C5 111.08(7)
O3 P1 C5 106.69(7)
O2 P1 C5 100.50(7)
C1 O2 P1 117.88(11)
C3 O3 P1 123.13(11)
C6 O4 H4O 112.8(13)
C10 O5 C11 106.26(13)
O2 C1 C2 108.92(16)
O2 C1 H1A 109.9
C2 C1 H1A 109.9
O2 C1 H1B 109.9
C2 C1 H1B 109.9
H1A C1 H1B 108.3
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
O3 C3 C4 108.91(13)
O3 C3 H3A 109.9
C4 C3 H3A 109.9
O3 C3 H3B 109.9
C4 C3 H3B 109.9
H3A C3 H3B 108.3
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
F2 C5 F1 106.51(12)
F2 C5 C6 110.28(13)
F1 C5 C6 109.21(13)
F2 C5 P1 109.49(10)
F1 C5 P1 108.10(10)
C6 C5 P1 113.02(11)
O4 C6 C7 115.00(13)
O4 C6 C5 108.78(12)
C7 C6 C5 110.56(12)
O4 C6 H6 107.4
C7 C6 H6 107.4
C5 C6 H6 107.4
C8 C7 C6 122.15(15)
C8 C7 H7 118.9
C6 C7 H7 118.9
C7 C8 C9 125.61(15)
C7 C8 H8 117.2
C9 C8 H8 117.2
C10 C9 C12 105.34(15)
C10 C9 C8 126.33(15)
C12 C9 C8 128.32(15)
C9 C10 O5 111.16(14)
C9 C10 H10 124.4
O5 C10 H10 124.4
C12 C11 O5 110.83(15)
C12 C11 H11 124.6
O5 C11 H11 124.6
C11 C12 C9 106.41(15)
C11 C12 H12 126.8
C9 C12 H12 126.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4672(12)
P1 O3 1.5619(12)
P1 O2 1.5644(12)
P1 C5 1.8549(16)
F1 C5 1.3683(19)
F2 C5 1.3653(18)
O2 C1 1.468(2)
O3 C3 1.461(2)
O4 C6 1.414(2)
O4 H4O 0.88(2)
O5 C10 1.358(2)
O5 C11 1.366(2)
C1 C2 1.494(3)
C1 H1A 0.9900
C1 H1B 0.9900
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C4 1.503(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.534(2)
C6 C7 1.496(2)
C6 H6 1.0000
C7 C8 1.335(2)
C7 H7 0.9500
C8 C9 1.456(2)
C8 H8 0.9500
C9 C10 1.354(2)
C9 C12 1.442(2)
C10 H10 0.9500
C11 C12 1.341(2)
C11 H11 0.9500
C12 H12 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
O4 H4O O1 0.88(2) 1.88(2) 2.7305(17) 161.2(19) 1_455
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
O1 P1 O2 C1 -68.75(16)
O3 P1 O2 C1 60.59(15)
C5 P1 O2 C1 170.83(14)
O1 P1 O3 C3 -16.26(14)
O2 P1 O3 C3 -146.27(12)
C5 P1 O3 C3 108.12(13)
P1 O2 C1 C2 148.42(14)
P1 O3 C3 C4 96.10(15)
O1 P1 C5 F2 170.25(10)
O3 P1 C5 F2 42.87(11)
O2 P1 C5 F2 -65.05(11)
O1 P1 C5 F1 -74.10(12)
O3 P1 C5 F1 158.52(10)
O2 P1 C5 F1 50.60(12)
O1 P1 C5 C6 46.90(13)
O3 P1 C5 C6 -80.49(12)
O2 P1 C5 C6 171.59(11)
F2 C5 C6 O4 -72.23(15)
F1 C5 C6 O4 171.05(12)
P1 C5 C6 O4 50.69(15)
F2 C5 C6 C7 54.95(17)
F1 C5 C6 C7 -61.76(16)
P1 C5 C6 C7 177.88(11)
O4 C6 C7 C8 -126.73(16)
C5 C6 C7 C8 109.61(17)
C6 C7 C8 C9 -176.76(14)
C7 C8 C9 C10 177.06(17)
C7 C8 C9 C12 -1.6(3)
C12 C9 C10 O5 0.31(18)
C8 C9 C10 O5 -178.59(14)
C11 O5 C10 C9 -0.13(18)
C10 O5 C11 C12 -0.13(18)
O5 C11 C12 C9 0.31(18)
C10 C9 C12 C11 -0.37(17)
C8 C9 C12 C11 178.50(15)
