#------------------------------------------------------------------------------
#$Date: 2023-10-02 23:56:47 +0200 (Mon 02 de Oct de 2023) $
#$Revision: 286627 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/21/7132173.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_7132173
loop_
_publ_author_name
'de Munnik, Mariska'
'Lithgow, Jasper'
'Brewitz, Lennart'
'Christensen, Kirsten'
'Bates, Robert H.'
'Rodríguez Miquel, Beatriz'
'Schofield, Christopher J.'
_publ_section_title
;
 αβ,α′β′-Diepoxyketones are Mechanism-Based Inhibitors
 of Nucleophilic Cysteine Enzymes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02932H
_journal_year                    2023
_chemical_formula_moiety         'C17 H14 O3'
_chemical_formula_sum            'C17 H14 O3'
_chemical_formula_weight         266.30
_chemical_melting_point          ?
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2022-03-10
_audit_creation_method           'CRYSTALS_ver_*****_build_8199 '
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7637(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.7921(3)
_cell_length_b                   5.34270(10)
_cell_length_c                   8.59030(10)
_cell_measurement_reflns_used    12422
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.15
_cell_measurement_theta_min      5.89
_cell_volume                     1319.89(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_av_unetI/netI     0.023
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16701
_diffrn_reflns_theta_full        75.928
_diffrn_reflns_theta_max         75.928
_diffrn_reflns_theta_min         3.073
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_yellow
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.13
_refine_ls_extinction_coef       12(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.0008274
_refine_ls_shift/su_mean         0.0000881
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.72P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0786
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0786
_reflns_limit_h_max              36
_reflns_limit_h_min              -35
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                1323
_reflns_number_total             1381
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.23
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_scale          5.42(15)
_oxford_structure_analysis_title 7581
_iucr_refine_instructions_details
;
#
# Punched on 10/03/22 at 13:15:53
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
END                                                                             
#
# Punched on 10/03/22 at 13:15:53
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            d3cc02932h2.cif
_cod_data_source_block           1
_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 
;
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               7132173
_oxford_refine_reflns_threshold_expression I>-10.0\s(I)
_refine_ls_r_factor_ref          0.0303
_reflns_number_all               1381
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-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_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 0.5000 1.34636(19) 0.7500 0.0357 1.0000 Uani S T . . . .
C2 C 0.5000 1.1199(2) 0.7500 0.0248 1.0000 Uani S T . . . .
C3 C 0.53357(3) 0.97021(17) 0.65934(10) 0.0234 1.0000 Uani . . . . . .
O4 O 0.55058(2) 1.09712(13) 0.52614(7) 0.0273 1.0000 Uani . . . . . .
C5 C 0.58242(3) 1.05439(17) 0.65760(10) 0.0224 1.0000 Uani . . . . . .
C6 C 0.62140(3) 0.88049(17) 0.62998(10) 0.0227 1.0000 Uani . . . . . .
C7 C 0.61459(3) 0.66736(18) 0.53808(10) 0.0267 1.0000 Uani . . . . . .
C8 C 0.65189(4) 0.51494(19) 0.50577(12) 0.0320 1.0000 Uani . . . . . .
C9 C 0.69621(4) 0.5734(2) 0.56569(13) 0.0343 1.0000 Uani . . . . . .
C10 C 0.70317(3) 0.7824(2) 0.65884(12) 0.0334 1.0000 Uani . . . . . .
C11 C 0.66591(3) 0.93643(18) 0.69133(11) 0.0273 1.0000 Uani . . . . . .
H31 H 0.5267 0.7933 0.6468 0.0269 1.0000 Uiso R . . . . .
H51 H 0.5903 1.2064 0.7161 0.0260 1.0000 Uiso R . . . . .
H71 H 0.5840 0.6252 0.4948 0.0320 1.0000 Uiso R . . . . .
H81 H 0.6469 0.3704 0.4411 0.0382 1.0000 Uiso R . . . . .
H91 H 0.7228 0.4678 0.5421 0.0429 1.0000 Uiso R . . . . .
H101 H 0.7341 0.8234 0.7016 0.0405 1.0000 Uiso R . . . . .
H111 H 0.6710 1.0832 0.7567 0.0332 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0337(5) 0.0251(5) 0.0490(6) 0.0000 0.0085(4) 0.0000
C2 0.0206(6) 0.0267(6) 0.0270(6) 0.0000 -0.0016(5) 0.0000
C3 0.0211(4) 0.0253(4) 0.0236(4) 0.0010(3) -0.0004(3) -0.0013(3)
O4 0.0229(3) 0.0361(4) 0.0226(3) 0.0060(3) -0.0013(2) 0.0010(3)
C5 0.0215(4) 0.0240(4) 0.0214(4) 0.0016(3) -0.0009(3) -0.0018(3)
C6 0.0221(4) 0.0244(4) 0.0216(4) 0.0048(3) 0.0019(3) -0.0011(3)
C7 0.0272(4) 0.0277(5) 0.0253(4) 0.0015(4) 0.0012(3) -0.0019(4)
C8 0.0393(6) 0.0265(5) 0.0310(5) 0.0006(4) 0.0082(4) 0.0022(4)
C9 0.0301(5) 0.0338(5) 0.0398(6) 0.0084(4) 0.0106(4) 0.0085(4)
C10 0.0218(4) 0.0383(6) 0.0402(5) 0.0089(4) 0.0015(4) 0.0003(4)
C11 0.0241(5) 0.0278(5) 0.0300(5) 0.0027(4) 0.0002(3) -0.0030(3)
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'
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_
_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
C3 6_656 C2 . O1 . 122.20(5) yes
C3 6_656 C2 . C3 . 115.60(11) yes
O1 . C2 . C3 . 122.20(5) yes
C2 . C3 . O4 . 114.50(8) yes
C2 . C3 . C5 . 118.70(8) yes
O4 . C3 . C5 . 59.13(5) yes
C2 . C3 . H31 . 116.4 no
O4 . C3 . H31 . 116.5 no
C5 . C3 . H31 . 119.0 no
C3 . O4 . C5 . 61.87(5) yes
C3 . C5 . O4 . 59.01(5) yes
C3 . C5 . C6 . 122.58(8) yes
O4 . C5 . C6 . 115.60(7) yes
C3 . C5 . H51 . 116.4 no
O4 . C5 . H51 . 113.3 no
C6 . C5 . H51 . 116.4 no
C5 . C6 . C7 . 120.98(8) yes
C5 . C6 . C11 . 119.57(8) yes
C7 . C6 . C11 . 119.39(8) yes
C6 . C7 . C8 . 120.25(9) yes
C6 . C7 . H71 . 120.6 no
C8 . C7 . H71 . 119.1 no
C7 . C8 . C9 . 120.05(9) yes
C7 . C8 . H81 . 119.5 no
C9 . C8 . H81 . 120.4 no
C8 . C9 . C10 . 120.07(9) yes
C8 . C9 . H91 . 120.4 no
C10 . C9 . H91 . 119.5 no
C9 . C10 . C11 . 120.14(9) yes
C9 . C10 . H101 . 120.3 no
C11 . C10 . H101 . 119.5 no
C6 . C11 . C10 . 120.07(9) yes
C6 . C11 . H111 . 120.1 no
C10 . C11 . H111 . 119.8 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 . 1.2099(17) yes
C2 . C3 6_656 1.5009(11) yes
C2 . C3 . 1.5009(11) yes
C3 . O4 . 1.4363(10) yes
C3 . C5 . 1.4776(12) yes
C3 . H31 . 0.971 no
O4 . C5 . 1.4381(10) yes
C5 . C6 . 1.4848(12) yes
C5 . H51 . 0.976 no
C6 . C7 . 1.3941(13) yes
C6 . C11 . 1.3943(12) yes
C7 . C8 . 1.3866(13) yes
C7 . H71 . 0.967 no
C8 . C9 . 1.3881(15) yes
C8 . H81 . 0.958 no
C9 . C10 . 1.3830(16) yes
C9 . H91 . 0.979 no
C10 . C11 . 1.3910(13) yes
C10 . H101 . 0.973 no
C11 . H111 . 0.972 no
