#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:51:11 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284309 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159293.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_7159293
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         'C13 H12 F N O3'
_chemical_formula_sum            'C13 H12 F N O3'
_chemical_formula_weight         249.24
_chemical_melting_point          ?
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_block_doi                 10.5517/ccdc.csd.cc2bhpzj
_audit_creation_method           'CRYSTALS_ver_14.61_build_7453 '
_audit_update_record
;
2022-03-18 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2499(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.58060(10)
_cell_length_b                   13.5108(2)
_cell_length_c                   15.3647(3)
_cell_measurement_reflns_used    3923
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.82
_cell_measurement_theta_min      4.34
_cell_volume                     1143.41(4)
_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 0.996
_diffrn_measured_fraction_theta_max 0.987
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_av_unetI/netI     0.042
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7130
_diffrn_reflns_theta_full        74.555
_diffrn_reflns_theta_max         76.076
_diffrn_reflns_theta_min         4.383
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.74
_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    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.0003156
_refine_ls_shift/su_mean         0.0000460
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 0.38P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1238
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1238
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2123
_reflns_number_total             2345
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.50
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0488
_oxford_refine_ls_scale          6.4(2)
_oxford_reflns_number_all        2345
_oxford_structure_analysis_title 7273
_cod_data_source_file            d3ob00376k2.cif
_cod_data_source_block           3-194f
_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 21/c '
_cod_database_code               7159293
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_refine_ls_r_factor_all   0.0488
_oxford_refine_ls_wr_factor_all  0.1238
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
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
F1 F 0.72009(17) 0.56814(8) 0.57748(6) 0.0385 1.0000 Uani . . . . . .
C2 C 0.5407(3) 0.62351(11) 0.60170(10) 0.0287 1.0000 Uani . . . . . .
C3 C 0.3705(3) 0.66683(12) 0.53770(10) 0.0336 1.0000 Uani . . . . . .
C4 C 0.1845(3) 0.72283(12) 0.56332(10) 0.0336 1.0000 Uani . . . . . .
C5 C 0.1637(3) 0.73511(11) 0.65161(10) 0.0295 1.0000 Uani . . . . . .
C6 C 0.3400(3) 0.69078(10) 0.71388(9) 0.0255 1.0000 Uani . . . . . .
C7 C 0.5290(2) 0.63547(10) 0.69008(9) 0.0246 1.0000 Uani . . . . . .
C8 C 0.6902(2) 0.59862(11) 0.77126(9) 0.0246 1.0000 Uani . . . . . .
C9 C 0.6949(2) 0.48735(11) 0.79548(9) 0.0245 1.0000 Uani . . . . . .
C10 C 0.7577(3) 0.49291(12) 0.89645(9) 0.0308 1.0000 Uani . . . . . .
C11 C 0.6260(3) 0.58508(12) 0.92333(10) 0.0307 1.0000 Uani . . . . . .
N12 N 0.5790(2) 0.64365(9) 0.84199(8) 0.0253 1.0000 Uani . . . . . .
C13 C 0.3603(3) 0.68724(10) 0.81199(9) 0.0255 1.0000 Uani . . . . . .
O14 O 0.2112(2) 0.71373(9) 0.85702(7) 0.0332 1.0000 Uani . . . . . .
C15 C 0.4471(2) 0.44359(10) 0.76417(10) 0.0246 1.0000 Uani . . . . . .
O16 O 0.2857(2) 0.43907(10) 0.80728(8) 0.0373 1.0000 Uani . . . . . .
O17 O 0.42675(18) 0.41492(8) 0.68041(7) 0.0282 1.0000 Uani . . . . . .
C18 C 0.1857(3) 0.38653(14) 0.63865(11) 0.0372 1.0000 Uani . . . . . .
H31 H 0.3789 0.6587 0.4771 0.0401 1.0000 Uiso R . . . . .
H41 H 0.0722 0.7535 0.5196 0.0387 1.0000 Uiso R . . . . .
H51 H 0.0370 0.7717 0.6683 0.0349 1.0000 Uiso R . . . . .
H81 H 0.8587 0.6207 0.7727 0.0295 1.0000 Uiso R . . . . .
H91 H 0.8174 0.4532 0.7690 0.0286 1.0000 Uiso R . . . . .
H101 H 0.9366 0.5008 0.9129 0.0377 1.0000 Uiso R . . . . .
H102 H 0.7045 0.4341 0.9245 0.0375 1.0000 Uiso R . . . . .
H112 H 0.7261 0.6221 0.9707 0.0372 1.0000 Uiso R . . . . .
H111 H 0.4714 0.5702 0.9423 0.0367 1.0000 Uiso R . . . . .
H183 H 0.1927 0.3686 0.5780 0.0560 1.0000 Uiso R . . . . .
H182 H 0.0761 0.4417 0.6377 0.0554 1.0000 Uiso R . . . . .
H181 H 0.1243 0.3326 0.6700 0.0554 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'
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
F1 . C2 . C3 . 119.60(14) yes
F1 . C2 . C7 . 119.42(13) yes
C3 . C2 . C7 . 120.97(15) yes
C2 . C3 . C4 . 119.17(14) yes
C2 . C3 . H31 . 120.9 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 121.61(14) yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 119.6 no
C4 . C5 . C6 . 117.29(14) yes
C4 . C5 . H51 . 121.2 no
C6 . C5 . H51 . 121.5 no
C5 . C6 . C7 . 122.22(14) yes
C5 . C6 . C13 . 129.60(14) yes
C7 . C6 . C13 . 108.11(12) yes
C6 . C7 . C2 . 118.72(13) yes
C6 . C7 . C8 . 109.81(12) yes
C2 . C7 . C8 . 131.48(14) yes
C7 . C8 . C9 . 120.46(12) yes
C7 . C8 . N12 . 102.10(11) yes
C9 . C8 . N12 . 102.57(11) yes
C7 . C8 . H81 . 111.2 no
C9 . C8 . H81 . 108.0 no
N12 . C8 . H81 . 112.0 no
C8 . C9 . C10 . 100.81(12) yes
C8 . C9 . C15 . 108.92(11) yes
C10 . C9 . C15 . 112.91(12) yes
C8 . C9 . H91 . 110.4 no
C10 . C9 . H91 . 112.7 no
C15 . C9 . H91 . 110.6 no
C9 . C10 . C11 . 105.66(11) yes
C9 . C10 . H101 . 108.6 no
C11 . C10 . H101 . 110.4 no
C9 . C10 . H102 . 111.8 no
C11 . C10 . H102 . 110.5 no
H101 . C10 . H102 . 109.8 no
C10 . C11 . N12 . 103.67(12) yes
C10 . C11 . H112 . 112.0 no
N12 . C11 . H112 . 111.1 no
C10 . C11 . H111 . 113.5 no
N12 . C11 . H111 . 108.7 no
H112 . C11 . H111 . 107.9 no
C8 . N12 . C11 . 111.60(12) yes
C8 . N12 . C13 . 112.94(11) yes
C11 . N12 . C13 . 123.23(12) yes
C6 . C13 . N12 . 105.84(12) yes
C6 . C13 . O14 . 127.98(13) yes
N12 . C13 . O14 . 126.12(13) yes
C9 . C15 . O16 . 124.98(13) yes
C9 . C15 . O17 . 110.70(11) yes
O16 . C15 . O17 . 124.25(13) yes
C15 . O17 . C18 . 115.77(11) yes
O17 . C18 . H183 . 108.3 no
O17 . C18 . H182 . 110.1 no
H183 . C18 . H182 . 107.6 no
O17 . C18 . H181 . 111.0 no
H183 . C18 . H181 . 111.3 no
H182 . C18 . H181 . 108.4 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
F1 . C2 . 1.3492(18) yes
C2 . C3 . 1.383(2) yes
C2 . C7 . 1.379(2) yes
C3 . C4 . 1.391(2) yes
C3 . H31 . 0.946 no
C4 . C5 . 1.390(2) yes
C4 . H41 . 0.938 no
C5 . C6 . 1.393(2) yes
C5 . H51 . 0.932 no
C6 . C7 . 1.388(2) yes
C6 . C13 . 1.494(2) yes
C7 . C8 . 1.5007(19) yes
C8 . C9 . 1.548(2) yes
C8 . N12 . 1.4674(18) yes
C8 . H81 . 0.984 no
C9 . C10 . 1.5364(19) yes
C9 . C15 . 1.5099(19) yes
C9 . H91 . 0.967 no
C10 . C11 . 1.536(2) yes
C10 . H101 . 0.996 no
C10 . H102 . 0.974 no
C11 . N12 . 1.4669(18) yes
C11 . H112 . 0.981 no
C11 . H111 . 0.976 no
N12 . C13 . 1.3663(18) yes
C13 . O14 . 1.2184(18) yes
C15 . O16 . 1.2022(18) yes
C15 . O17 . 1.3312(18) yes
O17 . C18 . 1.4461(18) yes
C18 . H183 . 0.969 no
C18 . H182 . 0.963 no
C18 . H181 . 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
C3 . H31 . O14 3_564 124 0.95 2.59 3.211(2) yes
C8 . H81 . O14 1_655 146 0.98 2.51 3.373(2) yes
C9 . H91 . O16 1_655 134 0.97 2.59 3.337(2) yes
C18 . H181 . O14 4_546 137 0.97 2.45 3.226(2) yes
