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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/69/4126991.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_4126991
loop_
_publ_author_name
'Meng, Guangrong'
'Shi, Shicheng'
'Lalancette, Roger A.'
'Szostak, Roman'
'Szostak, Michal'
_publ_section_title
;
 Reversible Twisting of Primary Amides via Ground State N-C(O)
 Destabilization: Highly Twisted Rotationally-Inverted Acyclic Amides.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11309
_journal_year                    2017
_chemical_formula_moiety         'C17 H22 F N O5'
_chemical_formula_sum            'C17 H22 F N O5'
_chemical_formula_weight         339.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.590(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.988(3)
_cell_length_b                   11.0644(13)
_cell_length_c                   15.974(2)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.58
_cell_measurement_theta_min      2.86
_cell_volume                     3589.9(8)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14716
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.695
_diffrn_reflns_theta_min         4.353
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0337
_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)+(0.0419P)²+2.1216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2911
_reflns_number_total             3180
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b11309_si_005.cif
_cod_data_source_block           160602RAL_MENG_123B_100K_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'DIRECT' changed to 'direct'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_atom_sites_solution_secondary' value 'DIFMAP' changed to 'difmap'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126991
_shelx_shelxl_version_number     2014/7
_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   0.770
_shelx_estimated_absorpt_t_max   0.813
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.54028(4) 0.05572(7) 0.69222(6) 0.0397(2) Uani 1 1 d . .
O3 O 0.64297(4) 0.41345(7) 0.47956(5) 0.0228(2) Uani 1 1 d . .
O2 O 0.56494(4) 0.55986(8) 0.46126(6) 0.0271(2) Uani 1 1 d . .
O5 O 0.66133(4) 0.73178(8) 0.52644(5) 0.0257(2) Uani 1 1 d . .
O4 O 0.66741(5) 0.72063(9) 0.67036(6) 0.0344(2) Uani 1 1 d . .
O1 O 0.73566(5) 0.48977(10) 0.69652(6) 0.0394(3) Uani 1 1 d . .
N1 N 0.65044(5) 0.55106(9) 0.58439(6) 0.0234(2) Uani 1 1 d . .
C3 C 0.61384(6) 0.51017(11) 0.50147(7) 0.0211(3) Uani 1 1 d . .
C2 C 0.64353(6) 0.35870(11) 0.66011(7) 0.0219(3) Uani 1 1 d . .
C6 C 0.53985(6) 0.25916(12) 0.65111(8) 0.0248(3) Uani 1 1 d . .
H6 H 0.4931 0.2604 0.6379 0.030 Uiso 1 1 calc R U
C7 C 0.57438(7) 0.15642(11) 0.68277(8) 0.0268(3) Uani 1 1 d . .
C1 C 0.68186(6) 0.46771(12) 0.65060(8) 0.0262(3) Uani 1 1 d . .
C9 C 0.67703(6) 0.25394(12) 0.69498(8) 0.0255(3) Uani 1 1 d . .
H9 H 0.7238 0.2533 0.7115 0.031 Uiso 1 1 calc R U
C5 C 0.57489(6) 0.36083(11) 0.63889(7) 0.0225(3) Uani 1 1 d . .
H5 H 0.5521 0.4324 0.6159 0.027 Uiso 1 1 calc R U
C4 C 0.66021(6) 0.67716(12) 0.59991(8) 0.0248(3) Uani 1 1 d . .
C8 C 0.64238(7) 0.15120(12) 0.70549(8) 0.0281(3) Uani 1 1 d . .
H8 H 0.6647 0.0789 0.7277 0.034 Uiso 1 1 calc R U
C10 C 0.61181(6) 0.34515(11) 0.39867(8) 0.0263(3) Uani 1 1 d . .
C14 C 0.65837(7) 0.86607(11) 0.51934(8) 0.0275(3) Uani 1 1 d . .
C15 C 0.65567(7) 0.88391(13) 0.42408(9) 0.0334(3) Uani 1 1 d . .
H15A H 0.6959 0.8514 0.4119 0.050 Uiso 1 1 calc R U
H15B H 0.6522 0.9703 0.4103 0.050 Uiso 1 1 calc R U
H15C H 0.6173 0.8415 0.3887 0.050 Uiso 1 1 calc R U
C17 C 0.72057(7) 0.92037(12) 0.57683(9) 0.0329(3) Uani 1 1 d . .
H17A H 0.7212 0.9065 0.6376 0.049 Uiso 1 1 calc R U
H17B H 0.7214 1.0075 0.5660 0.049 Uiso 1 1 calc R U
H17C H 0.7592 0.8822 0.5640 0.049 Uiso 1 1 calc R U
C16 C 0.59581(7) 0.90973(13) 0.54041(10) 0.0357(3) Uani 1 1 d . .
H16A H 0.5581 0.8650 0.5055 0.054 Uiso 1 1 calc R U
H16B H 0.5900 0.9962 0.5275 0.054 Uiso 1 1 calc R U
H16C H 0.5988 0.8963 0.6019 0.054 Uiso 1 1 calc R U
C13 C 0.60314(7) 0.42774(13) 0.32071(8) 0.0345(3) Uani 1 1 d . .
H13A H 0.5675 0.4852 0.3200 0.052 Uiso 1 1 calc R U
H13B H 0.5922 0.3793 0.2677 0.052 Uiso 1 1 calc R U
H13C H 0.6441 0.4721 0.3241 0.052 Uiso 1 1 calc R U
C12 C 0.54763(7) 0.29011(13) 0.40768(9) 0.0361(3) Uani 1 1 d . .
H12A H 0.5560 0.2406 0.4602 0.054 Uiso 1 1 calc R U
H12B H 0.5289 0.2394 0.3572 0.054 Uiso 1 1 calc R U
H12C H 0.5166 0.3547 0.4115 0.054 Uiso 1 1 calc R U
C11 C 0.66334(8) 0.24929(13) 0.39843(10) 0.0395(4) Uani 1 1 d . .
H11A H 0.7048 0.2882 0.3961 0.059 Uiso 1 1 calc R U
H11B H 0.6483 0.1969 0.3478 0.059 Uiso 1 1 calc R U
H11C H 0.6703 0.2007 0.4513 0.059 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'
F F 0.0727 0.0534 '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
C3 O3 C10 120.40(9)
C4 O5 C14 120.82(10)
C4 N1 C3 119.52(10)
C4 N1 C1 118.89(10)
C3 N1 C1 121.42(10)
O2 C3 O3 128.31(11)
O2 C3 N1 122.69(11)
O3 C3 N1 108.99(10)
C5 C2 C9 119.76(11)
C5 C2 C1 121.11(11)
C9 C2 C1 119.05(11)
C7 C6 C5 118.31(12)
C7 C6 H6 120.8
C5 C6 H6 120.8
F1 C7 C6 118.51(12)
F1 C7 C8 118.45(11)
C6 C7 C8 123.04(12)
O1 C1 N1 120.33(12)
O1 C1 C2 123.55(12)
N1 C1 C2 116.08(10)
C8 C9 C2 120.23(12)
C8 C9 H9 119.9
C2 C9 H9 119.9
C6 C5 C2 120.33(11)
C6 C5 H5 119.8
C2 C5 H5 119.8
O4 C4 O5 128.51(12)
O4 C4 N1 122.40(12)
O5 C4 N1 109.07(10)
C9 C8 C7 118.27(12)
C9 C8 H8 120.9
C7 C8 H8 120.9
O3 C10 C11 101.45(10)
O3 C10 C12 109.01(10)
C11 C10 C12 111.73(12)
O3 C10 C13 109.88(10)
C11 C10 C13 110.94(11)
C12 C10 C13 113.17(12)
O5 C14 C16 108.84(10)
O5 C14 C17 109.60(11)
C16 C14 C17 113.63(11)
O5 C14 C15 101.29(10)
C16 C14 C15 111.41(12)
C17 C14 C15 111.31(11)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C14 C17 H17A 109.5
C14 C17 H17B 109.5
H17A C17 H17B 109.5
C14 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C14 C16 H16A 109.5
C14 C16 H16B 109.5
H16A C16 H16B 109.5
C14 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.3532(15)
O3 C3 1.3227(15)
O3 C10 1.4975(14)
O2 C3 1.1983(15)
O5 C4 1.3256(15)
O5 C14 1.4903(15)
O4 C4 1.1978(15)
O1 C1 1.2062(15)
N1 C4 1.4229(16)
N1 C3 1.4271(15)
N1 C1 1.4327(16)
C2 C5 1.3945(17)
C2 C9 1.3967(18)
C2 C1 1.4788(17)
C6 C7 1.3742(18)
C6 C5 1.3844(18)
C6 H6 0.9500
C7 C8 1.3822(19)
C9 C8 1.3824(19)
C9 H9 0.9500
C5 H5 0.9500
C8 H8 0.9500
C10 C11 1.5155(19)
C10 C12 1.5178(19)
C10 C13 1.5181(18)
C14 C16 1.5144(19)
C14 C17 1.5180(18)
C14 C15 1.5212(18)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125873
