Dear Martin,

My approach to your problem is to download an MOL2 of the small-molecule 
compound from WebCSD rather than the small-molecule CIF file. MOL2 files have 
the advantage that both the coordinates and the CCDC-curated bond orders are 
included in the file. MOL2 files can be read by AceDRG, Grade2, and eLBOW.

I have recorded a YouTube video showing how to download a MOL2 file for your 
ligand from WebCSD, use it in the Grade Web Server to produce restraints and 
use them in COOT.

Please see https://youtu.be/Sx6haYQ3tSY for the YouTube video.

I will send you the Grade Web Server tarball off the bulletin board.

I hope this is useful!

Best regards,

Oliver


> On 19 Aug 2024, at 12:42, Martin Hu <[email protected]> wrote:
> 
> Dear All,
> 
> Thank you all for your help. I’ve tried several approaches to input this 
> file, including changing the format to mmCIF, importing it as coordinates, 
> and checking the restraints in the file. However, I am still unable to 
> install the experimental ligand structure into the protein. It seems that 
> COOT or JLigand cannot read the restraints from the CIF file.
> 
> I’m wondering if anyone has faced a similar problem before, and if there is a 
> way to input the experimental structure and save its restraints so that it 
> can be refined with the overall protein structure in Refmac?
> 
> I’ve attached the original CIF file here for your reference (in .txt format).
> 
> Sincerely,
> Martin
> 
> ########################################################################
> 
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> list hosted by www.jiscmail.ac.uk, terms & conditions are available at 
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> ####################################################################### 
> # 
> # This file contains crystal structure data downloaded from the 
> # Cambridge Structural Database (CSD) hosted by the Cambridge 
> # Crystallographic Data Centre (CCDC).
> # 
> # Full information about CCDC data access policies and citation 
> # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
> # 
> # Audit and citation data items may have been added by the CCDC. 
> # Please retain this information to preserve the provenance of 
> # this file and to allow appropriate attribution of the data. 
> # 
> #######################################################################
> 
> data_twin5
> _audit_block_doi                 10.5517/ccryflp
> _database_code_depnum_ccdc_archive 'CCDC 713483'
> loop_
> _citation_id
> _citation_doi
> _citation_year
> 1 10.1016/j.dyepig.2009.03.001 2009
> _audit_update_record             
> ;
> 2008-12-13 deposited with the CCDC.   2024-08-19 downloaded from the CCDC.
> ;
> 
> 
> 
> _audit_creation_method           SHELXL-97
> 
> _chemical_name_systematic        
> ;
> 
> ?
> 
> ;
> 
> _chemical_name_common            ?
> 
> _chemical_melting_point          ?
> 
> _chemical_formula_moiety         'C9 H7 B F2 N2'
> 
> _chemical_formula_sum            'C9 H7 B F2 N2'
> 
> _chemical_formula_weight         191.98
> 
> 
> 
> loop_
> 
> _atom_type_symbol
> 
> _atom_type_description
> 
> _atom_type_scat_dispersion_real
> 
> _atom_type_scat_dispersion_imag
> 
> _atom_type_scat_source
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> C C 0.0033 0.0016 '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'
> B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
> N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
> F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
> 
> 
> 
> _symmetry_cell_setting           Monoclinic
> 
> _symmetry_space_group_name_H-M   C2/c
> _symmetry_space_group_name_Hall  '-C 2yc'
> 
> 
> 
> loop_
> 
> _symmetry_equiv_pos_as_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'
> 
> 
> 
> _cell_length_a                   10.126(4)
> 
> _cell_length_b                   10.196(4)
> 
> _cell_length_c                   17.143(6)
> 
> _cell_angle_alpha                90.00
> 
> _cell_angle_beta                 102.285(6)
> 
> _cell_angle_gamma                90.00
> 
> _cell_volume                     1729.5(11)
> 
> _cell_formula_units_Z            8
> 
> _cell_measurement_temperature    296(2)
> 
> _cell_measurement_reflns_used    32
> 
> _cell_measurement_theta_min      2.45
> 
> _cell_measurement_theta_max      12.33
> 
> 
> 
> _exptl_crystal_description       plate
> 
> _exptl_crystal_colour            orange
> 
> _exptl_crystal_size_max          0.20
> 
> _exptl_crystal_size_mid          0.20
> 
> _exptl_crystal_size_min          0.04
> 
> _exptl_crystal_density_meas      'not measured'
> 
> _exptl_crystal_density_diffrn    1.475
> 
> _exptl_crystal_density_method    'not measured'
> 
> _exptl_crystal_F_000             784
> 
> _exptl_absorpt_coefficient_mu    0.119
> 
> _exptl_absorpt_correction_type   multi-scan
> 
> _exptl_absorpt_correction_T_min  0.9766
> 
> _exptl_absorpt_correction_T_max  0.9953
> 
> _exptl_absorpt_process_details   twinabs
> 
> 
> 
> _exptl_special_details           
> ;
> 
> ?
> 
> ;
> 
> 
> 
> _diffrn_ambient_temperature      296(2)
> 
> _diffrn_radiation_wavelength     0.71073
> 
> _diffrn_radiation_type           MoK\a
> 
> _diffrn_radiation_source         'fine-focus sealed tube'
> 
> _diffrn_radiation_monochromator  graphite
> 
> _diffrn_measurement_device_type  'CCD area detector'
> 
> _diffrn_measurement_method       'phi and omega scans'
> 
> _diffrn_detector_area_resol_mean ?
> 
> _diffrn_standards_number         ?
> 
> _diffrn_standards_interval_count ?
> 
> _diffrn_standards_interval_time  ?
> 
> _diffrn_standards_decay_%        ?
> 
> _diffrn_reflns_number            3845
> 
> _diffrn_reflns_av_R_equivalents  0.0000
> 
> _diffrn_reflns_av_sigmaI/netI    0.2541
> 
> _diffrn_reflns_limit_h_min       -11
> 
> _diffrn_reflns_limit_h_max       11
> 
> _diffrn_reflns_limit_k_min       -11
> 
> _diffrn_reflns_limit_k_max       11
> 
> _diffrn_reflns_limit_l_min       -19
> 
> _diffrn_reflns_limit_l_max       20
> 
> _diffrn_reflns_theta_min         2.43
> 
> _diffrn_reflns_theta_max         24.77
> 
> _reflns_number_total             3845
> 
> _reflns_number_gt                1360
> 
> _reflns_threshold_expression     >2sigma(I)
> 
> 
> 
> _computing_data_collection       'Bruker APEX II'
> 
> _computing_cell_refinement       'Bruker APEX II'
> 
> _computing_data_reduction        'Bruker APEX II'
> 
> _computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
> 
> _computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
> 
> _computing_molecular_graphics    'Bruker SHELXTL'
> 
> _computing_publication_material  'Bruker SHELXTL'
> 
> 
> 
> _refine_special_details          
> ;
> 
> Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
> 
> goodness of fit S are based on F^2^, conventional R-factors R are based
> 
> on F, with F set to zero for negative F^2^. The threshold expression of
> 
> F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
> 
> not relevant to the choice of reflections for refinement. R-factors based
> 
> on F^2^ are statistically about twice as large as those based on F, and R-
> 
> factors based on ALL data will be even larger.
> 
> ;
> 
> 
> 
> _refine_ls_structure_factor_coef Fsqd
> 
> _refine_ls_matrix_type           full
> 
> _refine_ls_weighting_scheme      calc
> 
> _refine_ls_weighting_details     
> 'calc w=1/[\s^2^(Fo^2^)+(0.1025P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
> 
> _atom_sites_solution_primary     direct
> 
> _atom_sites_solution_secondary   difmap
> 
> _atom_sites_solution_hydrogens   geom
> 
> _refine_ls_hydrogen_treatment    refall
> 
> _refine_ls_extinction_method     SHELXL
> 
> _refine_ls_extinction_coef       0.0053(16)
> 
> _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
> 
> _refine_ls_number_reflns         3845
> 
> _refine_ls_number_parameters     129
> 
> _refine_ls_number_restraints     0
> 
> _refine_ls_R_factor_all          0.2818
> 
> _refine_ls_R_factor_gt           0.1029
> 
> _refine_ls_wR_factor_ref         0.2803
> 
> _refine_ls_wR_factor_gt          0.1990
> 
> _refine_ls_goodness_of_fit_ref   1.004
> 
> _refine_ls_restrained_S_all      1.004
> 
> _refine_ls_shift/su_max          0.000
> 
> _refine_ls_shift/su_mean         0.000
> 
> 
> 
> 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_symmetry_multiplicity
> 
> _atom_site_calc_flag
> 
> _atom_site_refinement_flags
> 
> _atom_site_disorder_assembly
> 
> _atom_site_disorder_group
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> F1 F 0.0587(3) 0.1257(4) 0.09256(19) 0.0773(12) Uani 1 1 d . . .
> F2 F -0.0926(3) 0.2839(3) 0.10355(19) 0.0796(13) Uani 1 1 d . . .
> N1 N 0.0270(6) 0.3022(5) -0.0036(3) 0.0592(14) Uani 1 1 d . . .
> N2 N 0.1431(5) 0.3421(4) 0.1373(3) 0.0582(15) Uani 1 1 d . . .
> B1 B 0.0302(8) 0.2605(8) 0.0838(5) 0.062(2) Uani 1 1 d . . .
> C1 C -0.0617(7) 0.2670(7) -0.0700(5) 0.076(2) Uani 1 1 d . . .
> H1A H -0.1374 0.2152 -0.0703 0.092 Uiso 1 1 calc R . .
> C2 C -0.0270(8) 0.3169(7) -0.1378(4) 0.076(2) Uani 1 1 d . . .
> H2A H -0.0726 0.3045 -0.1904 0.092 Uiso 1 1 calc R . .
> C3 C 0.0882(8) 0.3883(6) -0.1116(4) 0.0696(19) Uani 1 1 d . . .
> H3A H 0.1350 0.4356 -0.1434 0.084 Uiso 1 1 calc R . .
> C4 C 0.1228(7) 0.3776(6) -0.0288(4) 0.0583(17) Uani 1 1 d . . .
> C5 C 0.2233(6) 0.4346(6) 0.0274(4) 0.0634(18) Uani 1 1 d . . .
> H5A H 0.2867 0.4867 0.0099 0.076 Uiso 1 1 calc R . .
> C6 C 0.2352(6) 0.4185(6) 0.1085(4) 0.0562(17) Uani 1 1 d . . .
> C7 C 0.3230(7) 0.4738(6) 0.1728(5) 0.068(2) Uani 1 1 d . . .
> H7A H 0.3941 0.5301 0.1700 0.082 Uiso 1 1 calc R . .
> C8 C 0.2876(7) 0.4315(7) 0.2418(4) 0.075(2) Uani 1 1 d . . .
> H8A H 0.3286 0.4536 0.2939 0.090 Uiso 1 1 calc R . .
> C9 C 0.1766(7) 0.3482(6) 0.2168(4) 0.071(2) Uani 1 1 d . . .
> H9A H 0.1324 0.3033 0.2510 0.085 Uiso 1 1 calc 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
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> F1 0.086(3) 0.061(3) 0.086(3) 0.008(2) 0.023(2) -0.007(2)
> F2 0.055(2) 0.103(3) 0.089(3) -0.004(2) 0.0317(19) -0.010(2)
> N1 0.057(4) 0.057(4) 0.065(4) 0.006(3) 0.017(3) 0.000(3)
> N2 0.053(4) 0.058(4) 0.067(4) 0.008(3) 0.024(3) -0.007(3)
> B1 0.053(6) 0.058(6) 0.080(6) 0.011(5) 0.026(5) 0.002(5)
> C1 0.064(5) 0.088(6) 0.077(5) -0.003(4) 0.015(4) -0.014(4)
> C2 0.083(6) 0.090(6) 0.059(5) 0.000(4) 0.023(4) 0.003(5)
> C3 0.077(6) 0.066(5) 0.070(5) 0.012(4) 0.026(4) -0.002(4)
> C4 0.049(5) 0.059(5) 0.068(5) 0.008(4) 0.015(4) 0.002(4)
> C5 0.053(5) 0.062(5) 0.079(5) 0.018(4) 0.023(4) -0.003(4)
> C6 0.059(5) 0.052(4) 0.058(5) 0.002(4) 0.013(4) -0.006(4)
> C7 0.063(5) 0.066(5) 0.082(5) -0.004(4) 0.031(4) -0.007(4)
> C8 0.055(5) 0.088(6) 0.076(5) -0.016(4) 0.000(4) 0.004(4)
> C9 0.069(5) 0.100(6) 0.047(5) 0.019(4) 0.018(4) 0.003(4)
> 
> 
> 
> _geom_special_details            
> ;
> 
> All esds (except the esd in the dihedral angle between two l.s. planes)
> 
> are estimated using the full covariance matrix. The cell esds are taken
> 
> into account individually in the estimation of esds in distances, angles
> 
> and torsion angles; correlations between esds in cell parameters are only
> 
> used when they are defined by crystal symmetry. An approximate (isotropic)
> 
> treatment of cell esds is used for estimating esds involving l.s. planes.
> 
> ;
> 
> 
> 
> loop_
> 
> _geom_bond_atom_site_label_1
> 
> _geom_bond_atom_site_label_2
> 
> _geom_bond_distance
> 
> _geom_bond_site_symmetry_2
> 
> _geom_bond_publ_flag
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> F1 B1 1.405(8) . ?
> F2 B1 1.378(7) . ?
> N1 C1 1.340(7) . ?
> N1 C4 1.377(7) . ?
> N1 B1 1.551(8) . ?
> N2 C9 1.335(6) . ?
> N2 C6 1.384(6) . ?
> N2 B1 1.547(8) . ?
> C1 C2 1.382(7) . ?
> C1 H1A 0.9300 . ?
> C2 C3 1.367(7) . ?
> C2 H2A 0.9300 . ?
> C3 C4 1.393(7) . ?
> C3 H3A 0.9300 . ?
> C4 C5 1.373(7) . ?
> C5 C6 1.380(7) . ?
> C5 H5A 0.9300 . ?
> C6 C7 1.381(7) . ?
> C7 C8 1.375(7) . ?
> C7 H7A 0.9300 . ?
> C8 C9 1.401(7) . ?
> C8 H8A 0.9300 . ?
> C9 H9A 0.9300 . ?
> 
> 
> 
> loop_
> 
> _geom_angle_atom_site_label_1
> 
> _geom_angle_atom_site_label_2
> 
> _geom_angle_atom_site_label_3
> 
> _geom_angle
> 
> _geom_angle_site_symmetry_1
> 
> _geom_angle_site_symmetry_3
> 
> _geom_angle_publ_flag
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> C1 N1 C4 105.8(5) . . ?
> C1 N1 B1 128.2(6) . . ?
> C4 N1 B1 125.8(6) . . ?
> C9 N2 C6 107.1(5) . . ?
> C9 N2 B1 128.7(6) . . ?
> C6 N2 B1 124.1(5) . . ?
> F2 B1 F1 108.6(6) . . ?
> F2 B1 N2 110.7(6) . . ?
> F1 B1 N2 110.7(6) . . ?
> F2 B1 N1 110.8(6) . . ?
> F1 B1 N1 109.5(6) . . ?
> N2 B1 N1 106.6(6) . . ?
> N1 C1 C2 111.8(6) . . ?
> N1 C1 H1A 124.1 . . ?
> C2 C1 H1A 124.1 . . ?
> C3 C2 C1 105.7(6) . . ?
> C3 C2 H2A 127.1 . . ?
> C1 C2 H2A 127.1 . . ?
> C2 C3 C4 107.8(6) . . ?
> C2 C3 H3A 126.1 . . ?
> C4 C3 H3A 126.1 . . ?
> C5 C4 N1 118.9(6) . . ?
> C5 C4 C3 132.1(7) . . ?
> N1 C4 C3 108.8(6) . . ?
> C4 C5 C6 123.3(6) . . ?
> C4 C5 H5A 118.3 . . ?
> C6 C5 H5A 118.3 . . ?
> C5 C6 N2 120.3(6) . . ?
> C5 C6 C7 131.3(7) . . ?
> N2 C6 C7 108.3(6) . . ?
> C8 C7 C6 108.5(6) . . ?
> C8 C7 H7A 125.8 . . ?
> C6 C7 H7A 125.8 . . ?
> C7 C8 C9 105.5(6) . . ?
> C7 C8 H8A 127.3 . . ?
> C9 C8 H8A 127.3 . . ?
> N2 C9 C8 110.7(6) . . ?
> N2 C9 H9A 124.7 . . ?
> C8 C9 H9A 124.7 . . ?
> 
> 
> 
> loop_
> 
> _geom_torsion_atom_site_label_1
> 
> _geom_torsion_atom_site_label_2
> 
> _geom_torsion_atom_site_label_3
> 
> _geom_torsion_atom_site_label_4
> 
> _geom_torsion
> 
> _geom_torsion_site_symmetry_1
> 
> _geom_torsion_site_symmetry_2
> 
> _geom_torsion_site_symmetry_3
> 
> _geom_torsion_site_symmetry_4
> 
> _geom_torsion_publ_flag
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> C9 N2 B1 F2 53.6(9) . . . . ?
> C6 N2 B1 F2 -130.6(6) . . . . ?
> C9 N2 B1 F1 -66.9(8) . . . . ?
> C6 N2 B1 F1 108.9(6) . . . . ?
> C9 N2 B1 N1 174.2(5) . . . . ?
> C6 N2 B1 N1 -10.0(8) . . . . ?
> C1 N1 B1 F2 -53.0(9) . . . . ?
> C4 N1 B1 F2 131.8(6) . . . . ?
> C1 N1 B1 F1 66.8(8) . . . . ?
> C4 N1 B1 F1 -108.4(6) . . . . ?
> C1 N1 B1 N2 -173.5(6) . . . . ?
> C4 N1 B1 N2 11.3(8) . . . . ?
> C4 N1 C1 C2 0.0(7) . . . . ?
> B1 N1 C1 C2 -175.9(6) . . . . ?
> N1 C1 C2 C3 -0.9(8) . . . . ?
> C1 C2 C3 C4 1.4(7) . . . . ?
> C1 N1 C4 C5 176.1(5) . . . . ?
> B1 N1 C4 C5 -7.8(9) . . . . ?
> C1 N1 C4 C3 0.9(7) . . . . ?
> B1 N1 C4 C3 177.0(5) . . . . ?
> C2 C3 C4 C5 -175.9(7) . . . . ?
> C2 C3 C4 N1 -1.5(7) . . . . ?
> N1 C4 C5 C6 1.1(9) . . . . ?
> C3 C4 C5 C6 175.1(6) . . . . ?
> C4 C5 C6 N2 -0.1(9) . . . . ?
> C4 C5 C6 C7 -175.4(6) . . . . ?
> C9 N2 C6 C5 -177.9(5) . . . . ?
> B1 N2 C6 C5 5.6(9) . . . . ?
> C9 N2 C6 C7 -1.6(6) . . . . ?
> B1 N2 C6 C7 -178.2(6) . . . . ?
> C5 C6 C7 C8 176.3(6) . . . . ?
> N2 C6 C7 C8 0.6(7) . . . . ?
> C6 C7 C8 C9 0.6(7) . . . . ?
> C6 N2 C9 C8 2.0(7) . . . . ?
> B1 N2 C9 C8 178.4(6) . . . . ?
> C7 C8 C9 N2 -1.6(7) . . . . ?
> 
> 
> 
> _diffrn_measured_fraction_theta_max 0.987
> 
> _diffrn_reflns_theta_full        24.77
> 
> _diffrn_measured_fraction_theta_full 0.987
> 
> _refine_diff_density_max         0.181
> 
> _refine_diff_density_min         -0.178
> 
> _refine_diff_density_rms         0.049
> 
> 
> 
> 
> 
> 
> ########################################################################
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