#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:51:11 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284309 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159292.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_7159292
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 H27 N O4 Si'
_chemical_formula_sum            'C19 H27 N O4 Si'
_chemical_formula_weight         361.51
_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.cc2bhpyh
_audit_creation_date             2018-07-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                93.826(4)
_cell_angle_beta                 92.511(4)
_cell_angle_gamma                114.147(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6792(3)
_cell_length_b                   7.7206(3)
_cell_length_c                   18.8453(8)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    150
_cell_measurement_theta_max      71
_cell_measurement_theta_min      5
_cell_volume                     1014.16(8)
_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 1.000
_diffrn_measured_fraction_theta_max 0.982
_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  0.038
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13119
_diffrn_reflns_theta_full        66.683
_diffrn_reflns_theta_max         71.292
_diffrn_reflns_theta_min         4.718
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.77
_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    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             387.998
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.0003227
_refine_ls_shift/su_mean         0.0000243
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.29P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1102
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1102
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3247
_reflns_number_total             3880
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.74
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0502
_oxford_refine_ls_scale          8.1(3)
_oxford_reflns_number_all        3880
_oxford_structure_analysis_title 6992
_cod_data_source_file            d3ob00376k2.cif
_cod_data_source_block           2-144a
_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               7159292
_oxford_refine_reflns_threshold_expression_ref I>-10.0\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 0.3166(2) 0.62457(17) 0.32056(7) 0.0416 1.0000 Uani . . . . . .
C2 C 0.3131(2) 0.4652(2) 0.31256(9) 0.0314 1.0000 Uani . . . . . .
N3 N 0.4280(2) 0.41219(19) 0.26987(8) 0.0310 1.0000 Uani . . . . . .
C4 C 0.6255(3) 0.5448(3) 0.25857(10) 0.0389 1.0000 Uani . . . . . .
C5 C 0.7449(3) 0.4303(3) 0.27376(10) 0.0383 1.0000 Uani . . . . . .
C6 C 0.6203(2) 0.2716(2) 0.31826(9) 0.0304 1.0000 Uani . . . . . .
C7 C 0.4174(2) 0.2227(2) 0.28354(8) 0.0280 1.0000 Uani . . . . . .
C8 C 0.2514(2) 0.1488(2) 0.32951(8) 0.0271 1.0000 Uani . . . . . .
C9 C 0.1615(2) -0.0307(2) 0.35320(9) 0.0313 1.0000 Uani . . . . . .
C10 C 0.0105(2) -0.0602(2) 0.39586(10) 0.0373 1.0000 Uani . . . . . .
C11 C -0.0477(2) 0.0842(3) 0.41417(10) 0.0395 1.0000 Uani . . . . . .
C12 C 0.0423(2) 0.2631(3) 0.38992(10) 0.0355 1.0000 Uani . . . . . .
C13 C 0.1914(2) 0.2922(2) 0.34666(9) 0.0292 1.0000 Uani . . . . . .
C21 C 0.6348(2) 0.3441(2) 0.39593(9) 0.0294 1.0000 Uani . . . . . .
O22 O 0.6785(2) 0.50813(17) 0.41675(7) 0.0430 1.0000 Uani . . . . . .
O23 O 0.58934(17) 0.20410(16) 0.43890(6) 0.0320 1.0000 Uani . . . . . .
C24 C 0.5913(3) 0.2620(3) 0.51379(10) 0.0431 1.0000 Uani . . . . . .
O31 O 0.39328(17) 0.10270(16) 0.22130(6) 0.0317 1.0000 Uani . . . . . .
Si32 Si 0.25468(7) 0.07262(7) 0.14698(2) 0.0339 1.0000 Uani . . . . . .
C33 C 0.3794(3) 0.2670(3) 0.08974(11) 0.0501 1.0000 Uani . . . . . .
C34 C 0.0180(3) 0.0704(4) 0.16607(12) 0.0551 1.0000 Uani . . . . . .
C35 C 0.2306(3) -0.1648(3) 0.10472(9) 0.0407 1.0000 Uani . . . . . .
C36 C 0.4298(4) -0.1651(3) 0.10111(13) 0.0571 1.0000 Uani . . . . . .
C37 C 0.1356(4) -0.2008(3) 0.02852(12) 0.0636 1.0000 Uani . . . . . .
C38 C 0.1108(4) -0.3257(3) 0.14878(12) 0.0573 1.0000 Uani . . . . . .
H41 H 0.6621 0.6587 0.2923 0.0460 1.0000 Uiso R . . . . .
H42 H 0.6332 0.5780 0.2096 0.0458 1.0000 Uiso R . . . . .
H52 H 0.8677 0.5125 0.2988 0.0461 1.0000 Uiso R . . . . .
H51 H 0.7637 0.3737 0.2297 0.0455 1.0000 Uiso R . . . . .
H61 H 0.6485 0.1625 0.3145 0.0358 1.0000 Uiso R . . . . .
H91 H 0.2004 -0.1260 0.3420 0.0376 1.0000 Uiso R . . . . .
H101 H -0.0525 -0.1803 0.4126 0.0458 1.0000 Uiso R . . . . .
H111 H -0.1501 0.0613 0.4442 0.0474 1.0000 Uiso R . . . . .
H121 H 0.0050 0.3625 0.4035 0.0429 1.0000 Uiso R . . . . .
H241 H 0.5631 0.1505 0.5386 0.0643 1.0000 Uiso R . . . . .
H243 H 0.7168 0.3570 0.5291 0.0651 1.0000 Uiso R . . . . .
H242 H 0.4992 0.3143 0.5200 0.0648 1.0000 Uiso R . . . . .
H331 H 0.3079 0.2411 0.0442 0.0749 1.0000 Uiso R . . . . .
H332 H 0.3856 0.3818 0.1146 0.0748 1.0000 Uiso R . . . . .
H333 H 0.5070 0.2753 0.0836 0.0746 1.0000 Uiso R . . . . .
H342 H -0.0610 0.0391 0.1238 0.0825 1.0000 Uiso R . . . . .
H341 H 0.0337 0.1940 0.1864 0.0832 1.0000 Uiso R . . . . .
H343 H -0.0456 -0.0223 0.1984 0.0826 1.0000 Uiso R . . . . .
H362 H 0.4196 -0.2821 0.0768 0.0852 1.0000 Uiso R . . . . .
H361 H 0.4873 -0.1528 0.1492 0.0851 1.0000 Uiso R . . . . .
H363 H 0.5124 -0.0596 0.0762 0.0852 1.0000 Uiso R . . . . .
H372 H 0.1282 -0.3206 0.0071 0.0951 1.0000 Uiso R . . . . .
H371 H 0.2082 -0.1003 -0.0011 0.0944 1.0000 Uiso R . . . . .
H373 H 0.0059 -0.2090 0.0296 0.0940 1.0000 Uiso R . . . . .
H382 H 0.1005 -0.4481 0.1273 0.0855 1.0000 Uiso R . . . . .
H381 H 0.1663 -0.3050 0.1972 0.0848 1.0000 Uiso R . . . . .
H383 H -0.0166 -0.3304 0.1506 0.0856 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'
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 . 125.42(16) yes
O1 . C2 . C13 . 128.13(16) yes
N3 . C2 . C13 . 106.44(13) yes
C2 . N3 . C4 . 122.16(14) yes
C2 . N3 . C7 . 111.63(13) yes
C4 . N3 . C7 . 111.34(13) yes
N3 . C4 . C5 . 103.85(13) yes
N3 . C4 . H41 . 108.4 no
C5 . C4 . H41 . 112.3 no
N3 . C4 . H42 . 110.1 no
C5 . C4 . H42 . 110.9 no
H41 . C4 . H42 . 111.1 no
C4 . C5 . C6 . 104.94(13) yes
C4 . C5 . H52 . 110.5 no
C6 . C5 . H52 . 112.6 no
C4 . C5 . H51 . 109.3 no
C6 . C5 . H51 . 109.1 no
H52 . C5 . H51 . 110.2 no
C5 . C6 . C7 . 101.44(13) yes
C5 . C6 . C21 . 111.55(14) yes
C7 . C6 . C21 . 110.03(13) yes
C5 . C6 . H61 . 113.1 no
C7 . C6 . H61 . 110.4 no
C21 . C6 . H61 . 110.0 no
C6 . C7 . N3 . 102.08(12) yes
C6 . C7 . C8 . 117.99(13) yes
N3 . C7 . C8 . 102.81(12) yes
C6 . C7 . O31 . 106.91(13) yes
N3 . C7 . O31 . 113.60(13) yes
C8 . C7 . O31 . 113.07(13) yes
C7 . C8 . C9 . 129.27(14) yes
C7 . C8 . C13 . 109.25(13) yes
C9 . C8 . C13 . 121.49(15) yes
C8 . C9 . C10 . 117.23(15) yes
C8 . C9 . H91 . 121.9 no
C10 . C9 . H91 . 120.9 no
C9 . C10 . C11 . 121.40(16) yes
C9 . C10 . H101 . 118.9 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 121.02(16) yes
C10 . C11 . H111 . 119.9 no
C12 . C11 . H111 . 119.1 no
C11 . C12 . C13 . 117.66(16) yes
C11 . C12 . H121 . 121.0 no
C13 . C12 . H121 . 121.4 no
C2 . C13 . C8 . 108.67(14) yes
C2 . C13 . C12 . 130.14(15) yes
C8 . C13 . C12 . 121.18(15) yes
C6 . C21 . O22 . 124.25(15) yes
C6 . C21 . O23 . 112.22(13) yes
O22 . C21 . O23 . 123.52(16) yes
C21 . O23 . C24 . 115.21(13) yes
O23 . C24 . H241 . 106.6 no
O23 . C24 . H243 . 108.1 no
H241 . C24 . H243 . 110.7 no
O23 . C24 . H242 . 109.6 no
H241 . C24 . H242 . 112.0 no
H243 . C24 . H242 . 109.7 no
C7 . O31 . Si32 . 128.83(10) yes
O31 . Si32 . C33 . 109.21(9) yes
O31 . Si32 . C34 . 112.06(8) yes
C33 . Si32 . C34 . 109.73(11) yes
O31 . Si32 . C35 . 102.72(7) yes
C33 . Si32 . C35 . 111.15(9) yes
C34 . Si32 . C35 . 111.80(11) yes
Si32 . C33 . H331 . 109.5 no
Si32 . C33 . H332 . 106.1 no
H331 . C33 . H332 . 111.2 no
Si32 . C33 . H333 . 109.5 no
H331 . C33 . H333 . 110.2 no
H332 . C33 . H333 . 110.4 no
Si32 . C34 . H342 . 109.7 no
Si32 . C34 . H341 . 110.2 no
H342 . C34 . H341 . 108.8 no
Si32 . C34 . H343 . 111.6 no
H342 . C34 . H343 . 107.6 no
H341 . C34 . H343 . 108.8 no
Si32 . C35 . C36 . 109.56(13) yes
Si32 . C35 . C37 . 110.05(14) yes
C36 . C35 . C37 . 108.60(19) yes
Si32 . C35 . C38 . 110.53(14) yes
C36 . C35 . C38 . 108.57(18) yes
C37 . C35 . C38 . 109.51(18) yes
C35 . C36 . H362 . 110.1 no
C35 . C36 . H361 . 109.4 no
H362 . C36 . H361 . 108.9 no
C35 . C36 . H363 . 110.8 no
H362 . C36 . H363 . 109.0 no
H361 . C36 . H363 . 108.6 no
C35 . C37 . H372 . 109.0 no
C35 . C37 . H371 . 111.8 no
H372 . C37 . H371 . 108.6 no
C35 . C37 . H373 . 110.2 no
H372 . C37 . H373 . 108.0 no
H371 . C37 . H373 . 109.3 no
C35 . C38 . H382 . 110.3 no
C35 . C38 . H381 . 111.1 no
H382 . C38 . H381 . 109.4 no
C35 . C38 . H383 . 109.9 no
H382 . C38 . H383 . 108.5 no
H381 . C38 . H383 . 107.5 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 . 1.219(2) yes
C2 . N3 . 1.381(2) yes
C2 . C13 . 1.488(2) yes
N3 . C4 . 1.477(2) yes
N3 . C7 . 1.4721(19) yes
C4 . C5 . 1.542(3) yes
C4 . H41 . 0.982 no
C4 . H42 . 0.973 no
C5 . C6 . 1.539(2) yes
C5 . H52 . 0.973 no
C5 . H51 . 0.956 no
C6 . C7 . 1.548(2) yes
C6 . C21 . 1.515(2) yes
C6 . H61 . 0.951 no
C7 . C8 . 1.506(2) yes
C7 . O31 . 1.4016(19) yes
C8 . C9 . 1.387(2) yes
C8 . C13 . 1.387(2) yes
C9 . C10 . 1.390(2) yes
C9 . H91 . 0.916 no
C10 . C11 . 1.390(3) yes
C10 . H101 . 0.937 no
C11 . C12 . 1.388(3) yes
C11 . H111 . 0.954 no
C12 . C13 . 1.386(2) yes
C12 . H121 . 0.947 no
C21 . O22 . 1.202(2) yes
C21 . O23 . 1.3340(19) yes
O23 . C24 . 1.449(2) yes
C24 . H241 . 0.957 no
C24 . H243 . 0.959 no
C24 . H242 . 0.954 no
O31 . Si32 . 1.6649(12) yes
Si32 . C33 . 1.861(2) yes
Si32 . C34 . 1.862(2) yes
Si32 . C35 . 1.8827(19) yes
C33 . H331 . 0.961 no
C33 . H332 . 0.957 no
C33 . H333 . 0.968 no
C34 . H342 . 0.934 no
C34 . H341 . 0.961 no
C34 . H343 . 0.960 no
C35 . C36 . 1.535(3) yes
C35 . C37 . 1.536(3) yes
C35 . C38 . 1.533(2) yes
C36 . H362 . 0.956 no
C36 . H361 . 0.971 no
C36 . H363 . 0.970 no
C37 . H372 . 0.963 no
C37 . H371 . 0.978 no
C37 . H373 . 0.973 no
C38 . H382 . 0.974 no
C38 . H381 . 0.965 no
C38 . H383 . 0.966 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_545 176 0.92 2.45 3.365(3) yes
C10 . H101 . O22 1_445 155 0.94 2.46 3.328(3) yes
C24 . H241 . O23 2_656 158 0.96 2.57 3.482(3) yes
C24 . H242 . O22 2_666 158 0.95 2.57 3.477(3) yes
