#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:51:11 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284309 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159295.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_7159295
loop_
_publ_author_name
'Saney, Liban'
'Christensen, Kirsten E.'
'Genov, Miroslav'
'Pretsch, Alexander'
'Pretsch, Dagmar'
'Moloney, Mark G.'
_publ_section_title
;
 Tetramate derivatives by chemoselective Dieckmann ring closure of
 allo-phenylserines, and their antibacterial activity.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4061
_journal_page_last               4071
_journal_paper_doi               10.1039/d3ob00376k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H26 F N O4 Si'
_chemical_formula_sum            'C19 H26 F N O4 Si'
_chemical_formula_weight         379.50
_chemical_melting_point          ?
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_block_doi                 10.5517/ccdc.csd.cc2bhq2n
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                92.034(3)
_cell_angle_beta                 92.705(3)
_cell_angle_gamma                115.382(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6070(3)
_cell_length_b                   7.9569(3)
_cell_length_c                   18.7476(6)
_cell_measurement_reflns_used    8653
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.96
_cell_measurement_theta_min      4.74
_cell_volume                     1022.12(7)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16849
_diffrn_reflns_theta_full        74.673
_diffrn_reflns_theta_max         76.982
_diffrn_reflns_theta_min         4.732
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.0003236
_refine_ls_shift/su_mean         0.0000255
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.22P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1150
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1150
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -10
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3888
_reflns_number_total             4280
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.67
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0435
_oxford_refine_ls_scale          7.8(2)
_oxford_reflns_number_all        4280
_oxford_structure_analysis_title 7210
_cod_data_source_file            d3ob00376k2.cif
_cod_data_source_block           7-144f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159291--7159301.cif.
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7159295
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
loop_
_symmetry_equiv_pos_as_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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.64356(15) 0.33212(17) 0.31627(6) 0.0409 1.0000 Uani . . . . . .
C2 C 0.4789(2) 0.3199(2) 0.30936(7) 0.0312 1.0000 Uani . . . . . .
N3 N 0.42051(16) 0.42743(16) 0.26680(6) 0.0307 1.0000 Uani . . . . . .
C4 C 0.5532(2) 0.6219(2) 0.25441(9) 0.0383 1.0000 Uani . . . . . .
C5 C 0.4337(2) 0.7311(2) 0.27057(8) 0.0372 1.0000 Uani . . . . . .
C6 C 0.27114(19) 0.60489(18) 0.31640(7) 0.0289 1.0000 Uani . . . . . .
C7 C 0.22555(18) 0.40941(18) 0.28185(7) 0.0267 1.0000 Uani . . . . . .
C8 C 0.15190(18) 0.24631(17) 0.32885(7) 0.0267 1.0000 Uani . . . . . .
C9 C -0.03200(19) 0.15378(19) 0.35349(7) 0.0310 1.0000 Uani . . . . . .
C10 C -0.0630(2) 0.0042(2) 0.39577(8) 0.0377 1.0000 Uani . . . . . .
C11 C 0.0841(2) -0.0498(2) 0.41253(9) 0.0401 1.0000 Uani . . . . . .
C12 C 0.2653(2) 0.04662(19) 0.38707(8) 0.0343 1.0000 Uani . . . . . .
C13 C 0.30126(19) 0.19431(18) 0.34422(7) 0.0288 1.0000 Uani . . . . . .
F14 F 0.40917(14) -0.00524(12) 0.40379(6) 0.0446 1.0000 Uani . . . . . .
C21 C 0.34531(18) 0.61911(17) 0.39389(7) 0.0273 1.0000 Uani . . . . . .
O22 O 0.51087(14) 0.65159(14) 0.41294(6) 0.0348 1.0000 Uani . . . . . .
O23 O 0.20431(13) 0.58576(13) 0.43865(5) 0.0297 1.0000 Uani . . . . . .
C24 C 0.2643(2) 0.5934(2) 0.51383(8) 0.0391 1.0000 Uani . . . . . .
O31 O 0.10314(14) 0.38226(14) 0.22012(5) 0.0311 1.0000 Uani . . . . . .
Si32 Si 0.07659(5) 0.25079(6) 0.14588(2) 0.0330 1.0000 Uani . . . . . .
C33 C 0.0706(3) 0.0209(3) 0.16576(10) 0.0522 1.0000 Uani . . . . . .
C34 C 0.2793(2) 0.3756(3) 0.08784(9) 0.0494 1.0000 Uani . . . . . .
C35 C -0.1621(2) 0.2258(2) 0.10307(8) 0.0395 1.0000 Uani . . . . . .
C36 C -0.1605(3) 0.4189(3) 0.09965(11) 0.0558 1.0000 Uani . . . . . .
C37 C -0.1934(3) 0.1374(3) 0.02667(10) 0.0611 1.0000 Uani . . . . . .
C38 C -0.3308(3) 0.1042(3) 0.14701(10) 0.0555 1.0000 Uani . . . . . .
H41 H 0.6717 0.6611 0.2875 0.0449 1.0000 Uiso R . . . . .
H42 H 0.5881 0.6325 0.2047 0.0458 1.0000 Uiso R . . . . .
H51 H 0.5144 0.8524 0.2952 0.0455 1.0000 Uiso R . . . . .
H52 H 0.3724 0.7490 0.2273 0.0452 1.0000 Uiso R . . . . .
H61 H 0.1549 0.6250 0.3139 0.0347 1.0000 Uiso R . . . . .
H91 H -0.1335 0.1855 0.3426 0.0326 1.0000 Uiso R . . . . .
H101 H -0.1861 -0.0619 0.4139 0.0452 1.0000 Uiso R . . . . .
H111 H 0.0601 -0.1511 0.4407 0.0491 1.0000 Uiso R . . . . .
H241 H 0.1513 0.5691 0.5397 0.0584 1.0000 Uiso R . . . . .
H242 H 0.3642 0.7136 0.5263 0.0589 1.0000 Uiso R . . . . .
H243 H 0.3070 0.4973 0.5201 0.0597 1.0000 Uiso R . . . . .
H331 H 0.0324 -0.0585 0.1223 0.0783 1.0000 Uiso R . . . . .
H332 H 0.1955 0.0315 0.1841 0.0786 1.0000 Uiso R . . . . .
H333 H -0.0250 -0.0408 0.2007 0.0774 1.0000 Uiso R . . . . .
H342 H 0.2563 0.3083 0.0425 0.0740 1.0000 Uiso R . . . . .
H341 H 0.3966 0.3856 0.1111 0.0730 1.0000 Uiso R . . . . .
H343 H 0.2893 0.4987 0.0816 0.0737 1.0000 Uiso R . . . . .
H362 H -0.2804 0.4060 0.0758 0.0833 1.0000 Uiso R . . . . .
H361 H -0.1467 0.4760 0.1466 0.0828 1.0000 Uiso R . . . . .
H363 H -0.0529 0.5014 0.0740 0.0836 1.0000 Uiso R . . . . .
H372 H -0.3133 0.1296 0.0044 0.0914 1.0000 Uiso R . . . . .
H371 H -0.0865 0.2103 -0.0028 0.0912 1.0000 Uiso R . . . . .
H373 H -0.2030 0.0140 0.0279 0.0918 1.0000 Uiso R . . . . .
H382 H -0.4550 0.0916 0.1248 0.0824 1.0000 Uiso R . . . . .
H381 H -0.3118 0.1576 0.1961 0.0815 1.0000 Uiso R . . . . .
H383 H -0.3370 -0.0200 0.1481 0.0821 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Si 0.2541 0.3302 6.2915 2.4386 3.0353 32.3337 1.9891 0.6785 1.5410 81.6937
1.1407 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.3390/antibiotics12010009 2023
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 125.29(13) yes
O1 . C2 . C13 . 129.03(13) yes
N3 . C2 . C13 . 105.67(11) yes
C2 . N3 . C4 . 121.67(12) yes
C2 . N3 . C7 . 112.15(10) yes
C4 . N3 . C7 . 111.23(11) yes
N3 . C4 . C5 . 104.05(11) yes
N3 . C4 . H41 . 108.5 no
C5 . C4 . H41 . 112.5 no
N3 . C4 . H42 . 110.3 no
C5 . C4 . H42 . 110.8 no
H41 . C4 . H42 . 110.5 no
C4 . C5 . C6 . 105.20(11) yes
C4 . C5 . H51 . 111.7 no
C6 . C5 . H51 . 112.1 no
C4 . C5 . H52 . 110.9 no
C6 . C5 . H52 . 107.7 no
H51 . C5 . H52 . 109.2 no
C5 . C6 . C7 . 101.13(11) yes
C5 . C6 . C21 . 111.35(11) yes
C7 . C6 . C21 . 109.79(10) yes
C5 . C6 . H61 . 114.9 no
C7 . C6 . H61 . 109.7 no
C21 . C6 . H61 . 109.6 no
C6 . C7 . N3 . 102.26(10) yes
C6 . C7 . C8 . 117.81(11) yes
N3 . C7 . C8 . 102.83(10) yes
C6 . C7 . O31 . 107.12(10) yes
N3 . C7 . O31 . 113.44(11) yes
C8 . C7 . O31 . 113.00(11) yes
C7 . C8 . C9 . 128.70(12) yes
C7 . C8 . C13 . 108.75(11) yes
C9 . C8 . C13 . 122.53(12) yes
C8 . C9 . C10 . 117.21(13) yes
C8 . C9 . H91 . 123.2 no
C10 . C9 . H91 . 119.6 no
C9 . C10 . C11 . 121.50(13) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 118.7 no
C10 . C11 . C12 . 119.38(13) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 120.4 no
C11 . C12 . C13 . 120.88(13) yes
C11 . C12 . F14 . 119.39(13) yes
C13 . C12 . F14 . 119.73(13) yes
C2 . C13 . C8 . 109.29(11) yes
C2 . C13 . C12 . 132.22(12) yes
C8 . C13 . C12 . 118.48(12) yes
C6 . C21 . O22 . 124.10(12) yes
C6 . C21 . O23 . 112.11(11) yes
O22 . C21 . O23 . 123.76(13) yes
C21 . O23 . C24 . 115.09(10) yes
O23 . C24 . H241 . 106.5 no
O23 . C24 . H242 . 108.0 no
H241 . C24 . H242 . 111.6 no
O23 . C24 . H243 . 107.6 no
H241 . C24 . H243 . 110.3 no
H242 . C24 . H243 . 112.5 no
C7 . O31 . Si32 . 128.94(8) yes
O31 . Si32 . C33 . 111.81(7) yes
O31 . Si32 . C34 . 109.65(7) yes
C33 . Si32 . C34 . 109.84(9) yes
O31 . Si32 . C35 . 102.85(6) yes
C33 . Si32 . C35 . 111.86(9) yes
C34 . Si32 . C35 . 110.65(7) yes
Si32 . C33 . H331 . 109.0 no
Si32 . C33 . H332 . 112.4 no
H331 . C33 . H332 . 108.2 no
Si32 . C33 . H333 . 111.1 no
H331 . C33 . H333 . 107.7 no
H332 . C33 . H333 . 108.2 no
Si32 . C34 . H342 . 110.2 no
Si32 . C34 . H341 . 108.2 no
H342 . C34 . H341 . 109.9 no
Si32 . C34 . H343 . 109.4 no
H342 . C34 . H343 . 110.2 no
H341 . C34 . H343 . 108.9 no
Si32 . C35 . C36 . 109.45(11) yes
Si32 . C35 . C37 . 110.15(12) yes
C36 . C35 . C37 . 108.69(16) yes
Si32 . C35 . C38 . 110.30(11) yes
C36 . C35 . C38 . 108.76(15) yes
C37 . C35 . C38 . 109.46(14) yes
C35 . C36 . H362 . 109.1 no
C35 . C36 . H361 . 111.0 no
H362 . C36 . H361 . 109.3 no
C35 . C36 . H363 . 111.3 no
H362 . C36 . H363 . 109.0 no
H361 . C36 . H363 . 107.1 no
C35 . C37 . H372 . 109.8 no
C35 . C37 . H371 . 111.7 no
H372 . C37 . H371 . 108.5 no
C35 . C37 . H373 . 110.0 no
H372 . C37 . H373 . 108.0 no
H371 . C37 . H373 . 108.9 no
C35 . C38 . H382 . 110.3 no
C35 . C38 . H381 . 110.5 no
H382 . C38 . H381 . 110.2 no
C35 . C38 . H383 . 109.8 no
H382 . C38 . H383 . 107.3 no
H381 . C38 . H383 . 108.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2143(17) yes
C2 . N3 . 1.3808(18) yes
C2 . C13 . 1.4912(18) yes
N3 . C4 . 1.4752(18) yes
N3 . C7 . 1.4696(15) yes
C4 . C5 . 1.535(2) yes
C4 . H41 . 0.993 no
C4 . H42 . 0.977 no
C5 . C6 . 1.5403(18) yes
C5 . H51 . 0.978 no
C5 . H52 . 0.962 no
C6 . C7 . 1.5505(18) yes
C6 . C21 . 1.5160(18) yes
C6 . H61 . 0.963 no
C7 . C8 . 1.5096(17) yes
C7 . O31 . 1.4004(16) yes
C8 . C9 . 1.3836(18) yes
C8 . C13 . 1.3877(17) yes
C9 . C10 . 1.395(2) yes
C9 . H91 . 0.926 no
C10 . C11 . 1.387(2) yes
C10 . H101 . 0.944 no
C11 . C12 . 1.378(2) yes
C11 . H111 . 0.936 no
C12 . C13 . 1.3833(19) yes
C12 . F14 . 1.3526(16) yes
C21 . O22 . 1.2052(16) yes
C21 . O23 . 1.3348(15) yes
O23 . C24 . 1.4519(16) yes
C24 . H241 . 0.956 no
C24 . H242 . 0.944 no
C24 . H243 . 0.959 no
O31 . Si32 . 1.6617(10) yes
Si32 . C33 . 1.8618(18) yes
Si32 . C34 . 1.8627(16) yes
Si32 . C35 . 1.8766(16) yes
C33 . H331 . 0.965 no
C33 . H332 . 0.962 no
C33 . H333 . 0.980 no
C34 . H342 . 0.955 no
C34 . H341 . 0.945 no
C34 . H343 . 0.961 no
C35 . C36 . 1.534(3) yes
C35 . C37 . 1.535(2) yes
C35 . C38 . 1.534(2) yes
C36 . H362 . 0.960 no
C36 . H361 . 0.955 no
C36 . H363 . 0.965 no
C37 . H372 . 0.961 no
C37 . H371 . 0.981 no
C37 . H373 . 0.954 no
C38 . H382 . 0.977 no
C38 . H381 . 0.978 no
C38 . H383 . 0.970 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O1 1_455 169 0.93 2.48 3.391(2) yes
C10 . H101 . O22 1_445 149 0.94 2.45 3.294(2) yes
C24 . H241 . O23 2_566 156 0.96 2.51 3.401(2) yes
C24 . H243 . O22 2_666 153 0.96 2.50 3.382(2) yes
