# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2379268'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2024-08-22 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'phenylbutazone solvate with acetonitrile'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N2 O2, C2 H3 N'
_chemical_formula_sum            'C21 H23 N3 O2'
_chemical_formula_weight         349.42

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.9766(19)
_cell_length_b                   5.7375(5)
_cell_length_c                   18.7841(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.907(4)
_cell_angle_gamma                90
_cell_volume                     1932.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4200
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      22.64
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3405
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40999
_diffrn_reflns_av_unetI/netI     0.1041
_diffrn_reflns_av_R_equivalents  0.1163
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.517
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4756
_reflns_number_gt                3301
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+9.9714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4756
_refine_ls_number_parameters     244
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1794
_refine_ls_R_factor_gt           0.1394
_refine_ls_wR_factor_ref         0.2957
_refine_ls_wR_factor_gt          0.2782
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.146
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.0231(6) 0.307(2) 0.4037(5) 0.095(4) Uani 0.686(9) 1 d D . P A 1
C1A C 0.0552(6) 0.263(2) 0.4552(5) 0.056(3) Uani 0.686(9) 1 d D . P A 1
N1B N 0.0572(14) 0.530(5) 0.4259(11) 0.095(4) Uani 0.314(9) 1 d D . P A 2
C1B C 0.0726(15) 0.377(4) 0.4641(11) 0.056(3) Uani 0.314(9) 1 d D . P A 2
C2S C 0.0934(4) 0.2132(16) 0.5199(5) 0.084(3) Uani 1 1 d D . . . .
H21A H 0.1330 0.3286 0.5296 0.126 Uiso 0.686(9) 1 calc R U P A 1
H22A H 0.1155 0.0573 0.5178 0.126 Uiso 0.686(9) 1 calc R U P A 1
H23A H 0.0588 0.2181 0.5580 0.126 Uiso 0.686(9) 1 calc R U P A 1
H21B H 0.1427 0.2540 0.5419 0.126 Uiso 0.314(9) 1 calc R U P A 2
H22B H 0.0950 0.0559 0.4997 0.126 Uiso 0.314(9) 1 calc R U P A 2
H23B H 0.0567 0.2178 0.5561 0.126 Uiso 0.314(9) 1 calc R U P A 2
C3 C 0.3243(2) 0.2820(8) 0.5058(3) 0.0283(10) Uani 1 1 d . . . . .
C4 C 0.3747(2) 0.3817(9) 0.4528(2) 0.0282(10) Uani 1 1 d . . . . .
H4 H 0.4134 0.2633 0.4425 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4119(2) 0.5850(8) 0.4905(2) 0.0249(10) Uani 1 1 d . . . . .
C11 C 0.4301(2) 0.6786(8) 0.6197(2) 0.0225(9) Uani 1 1 d . . . . .
C12 C 0.4401(3) 0.5408(8) 0.6798(2) 0.0277(10) Uani 1 1 d . . . . .
H12 H 0.4167 0.3928 0.6818 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4855(3) 0.6235(10) 0.7376(3) 0.0352(12) Uani 1 1 d . . . . .
H13 H 0.4922 0.5322 0.7798 0.042 Uiso 1 1 calc R U . . .
C14 C 0.5205(3) 0.8356(10) 0.7343(3) 0.0353(12) Uani 1 1 d . . . . .
H14 H 0.5521 0.8889 0.7735 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5097(3) 0.9721(8) 0.6734(2) 0.0284(10) Uani 1 1 d . . . . .
H15 H 0.5341 1.1186 0.6714 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4636(2) 0.8975(8) 0.6153(3) 0.0273(10) Uani 1 1 d . . . . .
H16 H 0.4552 0.9922 0.5741 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2756(3) 0.4506(8) 0.6128(3) 0.0279(10) Uani 1 1 d . . . . .
C22 C 0.2559(3) 0.2775(9) 0.6595(3) 0.0353(12) Uani 1 1 d . . . . .
H22 H 0.2841 0.1377 0.6643 0.042 Uiso 1 1 calc R U . . .
C23 C 0.1937(3) 0.3123(10) 0.6996(3) 0.0439(14) Uani 1 1 d . . . . .
H23 H 0.1796 0.1965 0.7323 0.053 Uiso 1 1 calc R U . . .
C24 C 0.1530(3) 0.5159(11) 0.6914(4) 0.0539(18) Uani 1 1 d . . . . .
H24 H 0.1100 0.5382 0.7174 0.065 Uiso 1 1 calc R U . . .
C25 C 0.1745(3) 0.6875(10) 0.6452(3) 0.0476(15) Uani 1 1 d . . . . .
H25 H 0.1466 0.8280 0.6405 0.057 Uiso 1 1 calc R U . . .
C26 C 0.2366(3) 0.6572(9) 0.6056(3) 0.0364(12) Uani 1 1 d . . . . .
H26 H 0.2516 0.7759 0.5743 0.044 Uiso 1 1 calc R U . . .
C41 C 0.3318(3) 0.4520(9) 0.3827(3) 0.0343(12) Uani 1 1 d . . . . .
H411 H 0.3671 0.5203 0.3502 0.041 Uiso 1 1 calc R U . . .
H412 H 0.3097 0.3110 0.3594 0.041 Uiso 1 1 calc R U . . .
C42 C 0.2702(3) 0.6274(10) 0.3941(3) 0.0411(13) Uani 1 1 d . . . . .
H421 H 0.2318 0.5508 0.4213 0.049 Uiso 1 1 calc R U . . .
H422 H 0.2916 0.7573 0.4235 0.049 Uiso 1 1 calc R U . . .
C43 C 0.2329(4) 0.7271(12) 0.3264(3) 0.0573(18) Uani 1 1 d . . . . .
H431 H 0.2085 0.5993 0.2981 0.069 Uiso 1 1 calc R U . . .
H432 H 0.2713 0.7969 0.2976 0.069 Uiso 1 1 calc R U . . .
C44 C 0.1743(4) 0.9137(12) 0.3409(4) 0.071(2) Uani 1 1 d . . . . .
H441 H 0.1962 1.0283 0.3749 0.107 Uiso 1 1 calc R U . . .
H442 H 0.1313 0.8395 0.3610 0.107 Uiso 1 1 calc R U . . .
H443 H 0.1582 0.9920 0.2962 0.107 Uiso 1 1 calc R U . . .
N1 N 0.3862(2) 0.5958(7) 0.55878(19) 0.0243(8) Uani 1 1 d . . . . .
N2 N 0.3372(2) 0.4061(7) 0.5696(2) 0.0255(9) Uani 1 1 d . . . . .
O3 O 0.27815(19) 0.1296(6) 0.49774(19) 0.0353(9) Uani 1 1 d . . . . .
O5 O 0.45822(18) 0.7149(6) 0.46829(16) 0.0323(8) Uani 1 1 d . . . . .


_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
N1A C1A 1.121(11) . ?
C1A C2S 1.385(11) . ?
N1B C1B 1.155(18) . ?
C1B C2S 1.438(17) . ?
C2S H21A 0.9800 . ?
C2S H22A 0.9800 . ?
C2S H23A 0.9800 . ?
C2S H21B 0.9800 . ?
C2S H22B 0.9800 . ?
C2S H23B 0.9800 . ?
C3 O3 1.208(5) . ?
C3 N2 1.399(6) . ?
C3 C4 1.504(6) . ?
C4 C5 1.497(6) . ?
C4 C41 1.535(7) . ?
C4 H4 1.0000 . ?
C5 O5 1.213(5) . ?
C5 N1 1.394(5) . ?
C11 C12 1.380(6) . ?
C11 C16 1.398(6) . ?
C11 N1 1.426(5) . ?
C12 C13 1.397(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.379(7) . ?
C21 C22 1.387(7) . ?
C21 N2 1.441(5) . ?
C22 C23 1.406(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(7) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C41 C42 1.522(7) . ?
C41 H411 0.9900 . ?
C41 H412 0.9900 . ?
C42 C43 1.509(8) . ?
C42 H421 0.9900 . ?
C42 H422 0.9900 . ?
C43 C44 1.539(9) . ?
C43 H431 0.9900 . ?
C43 H432 0.9900 . ?
C44 H441 0.9800 . ?
C44 H442 0.9800 . ?
C44 H443 0.9800 . ?
N1 N2 1.423(5) . ?

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
N1A C1A C2S 178.4(13) . . ?
N1B C1B C2S 171(3) . . ?
C1A C2S H21A 109.5 . . ?
C1A C2S H22A 109.5 . . ?
H21A C2S H22A 109.5 . . ?
C1A C2S H23A 109.5 . . ?
H21A C2S H23A 109.5 . . ?
H22A C2S H23A 109.5 . . ?
C1B C2S H21B 109.5 . . ?
C1B C2S H22B 109.5 . . ?
H21B C2S H22B 109.5 . . ?
C1B C2S H23B 109.5 . . ?
H21B C2S H23B 109.5 . . ?
H22B C2S H23B 109.5 . . ?
O3 C3 N2 123.2(4) . . ?
O3 C3 C4 129.2(5) . . ?
N2 C3 C4 107.5(4) . . ?
C5 C4 C3 104.6(4) . . ?
C5 C4 C41 112.5(4) . . ?
C3 C4 C41 112.2(4) . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C41 C4 H4 109.1 . . ?
O5 C5 N1 124.6(4) . . ?
O5 C5 C4 127.6(4) . . ?
N1 C5 C4 107.8(4) . . ?
C12 C11 C16 122.0(4) . . ?
C12 C11 N1 120.0(4) . . ?
C16 C11 N1 118.0(4) . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 117.8(4) . . ?
C15 C16 H16 121.1 . . ?
C11 C16 H16 121.1 . . ?
C26 C21 C22 121.9(4) . . ?
C26 C21 N2 120.2(4) . . ?
C22 C21 N2 117.9(4) . . ?
C21 C22 C23 118.9(5) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 119.6(5) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 120.2(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.9(6) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C21 C26 C25 118.4(5) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C42 C41 C4 112.4(4) . . ?
C42 C41 H411 109.1 . . ?
C4 C41 H411 109.1 . . ?
C42 C41 H412 109.1 . . ?
C4 C41 H412 109.1 . . ?
H411 C41 H412 107.9 . . ?
C43 C42 C41 114.7(5) . . ?
C43 C42 H421 108.6 . . ?
C41 C42 H421 108.6 . . ?
C43 C42 H422 108.6 . . ?
C41 C42 H422 108.6 . . ?
H421 C42 H422 107.6 . . ?
C42 C43 C44 112.6(5) . . ?
C42 C43 H431 109.1 . . ?
C44 C43 H431 109.1 . . ?
C42 C43 H432 109.1 . . ?
C44 C43 H432 109.1 . . ?
H431 C43 H432 107.8 . . ?
C43 C44 H441 109.5 . . ?
C43 C44 H442 109.5 . . ?
H441 C44 H442 109.5 . . ?
C43 C44 H443 109.5 . . ?
H441 C44 H443 109.5 . . ?
H442 C44 H443 109.5 . . ?
C5 N1 N2 110.1(3) . . ?
C5 N1 C11 123.6(4) . . ?
N2 N1 C11 117.0(3) . . ?
C3 N2 N1 109.6(3) . . ?
C3 N2 C21 118.9(4) . . ?
N1 N2 C21 116.9(3) . . ?

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
O3 C3 C4 C5 172.7(5) . . . . ?
N2 C3 C4 C5 -4.8(5) . . . . ?
O3 C3 C4 C41 50.4(7) . . . . ?
N2 C3 C4 C41 -127.0(4) . . . . ?
C3 C4 C5 O5 178.6(5) . . . . ?
C41 C4 C5 O5 -59.3(6) . . . . ?
C3 C4 C5 N1 1.3(5) . . . . ?
C41 C4 C5 N1 123.4(4) . . . . ?
C16 C11 C12 C13 -0.3(7) . . . . ?
N1 C11 C12 C13 177.8(4) . . . . ?
C11 C12 C13 C14 -1.2(7) . . . . ?
C12 C13 C14 C15 1.3(7) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C11 -1.4(6) . . . . ?
C12 C11 C16 C15 1.5(6) . . . . ?
N1 C11 C16 C15 -176.6(4) . . . . ?
C26 C21 C22 C23 1.2(8) . . . . ?
N2 C21 C22 C23 -176.9(5) . . . . ?
C21 C22 C23 C24 0.6(8) . . . . ?
C22 C23 C24 C25 -1.7(10) . . . . ?
C23 C24 C25 C26 1.1(10) . . . . ?
C22 C21 C26 C25 -1.9(8) . . . . ?
N2 C21 C26 C25 176.2(5) . . . . ?
C24 C25 C26 C21 0.7(9) . . . . ?
C5 C4 C41 C42 -60.4(5) . . . . ?
C3 C4 C41 C42 57.3(6) . . . . ?
C4 C41 C42 C43 172.2(5) . . . . ?
C41 C42 C43 C44 -176.7(5) . . . . ?
O5 C5 N1 N2 -174.8(4) . . . . ?
C4 C5 N1 N2 2.7(5) . . . . ?
O5 C5 N1 C11 -29.2(7) . . . . ?
C4 C5 N1 C11 148.2(4) . . . . ?
C12 C11 N1 C5 -125.4(5) . . . . ?
C16 C11 N1 C5 52.7(6) . . . . ?
C12 C11 N1 N2 18.0(6) . . . . ?
C16 C11 N1 N2 -163.9(4) . . . . ?
O3 C3 N2 N1 -171.0(4) . . . . ?
C4 C3 N2 N1 6.6(5) . . . . ?
O3 C3 N2 C21 -32.9(7) . . . . ?
C4 C3 N2 C21 144.7(4) . . . . ?
C5 N1 N2 C3 -5.9(5) . . . . ?
C11 N1 N2 C3 -154.0(4) . . . . ?
C5 N1 N2 C21 -145.0(4) . . . . ?
C11 N1 N2 C21 66.9(5) . . . . ?
C26 C21 N2 C3 -94.3(6) . . . . ?
C22 C21 N2 C3 83.8(6) . . . . ?
C26 C21 N2 N1 40.9(6) . . . . ?
C22 C21 N2 N1 -141.0(4) . . . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.081


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, at 6 deg. C during 3-4 hours'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2379269'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry of RAS
Russia
;
_audit_update_record             
;
2024-08-22 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-hydroxy-phenylbutazone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N2 O3'
_chemical_formula_sum            'C19 H20 N2 O3'
_chemical_formula_weight         324.37

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2150(10)
_cell_length_b                   5.9581(4)
_cell_length_c                   17.4194(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.782(2)
_cell_angle_gamma                90
_cell_volume                     1680.92(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.25
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.223
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6338
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41545
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.515
_diffrn_reflns_theta_max         29.286
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4558
_reflns_number_gt                3731
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²+0.5625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4558
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.23004(5) 0.78302(15) 0.65070(6) 0.0322(2) Uani 1 1 d . . . . .
O4 O 0.08159(6) 0.73331(17) 0.74592(6) 0.0358(2) Uani 1 1 d . . . . .
O5 O 0.08362(5) 0.26013(17) 0.79620(5) 0.0288(2) Uani 1 1 d . . . . .
N1 N 0.21925(6) 0.31819(17) 0.76966(6) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.26361(6) 0.48977(16) 0.73175(6) 0.0206(2) Uani 1 1 d . . . . .
C3 C 0.20944(7) 0.6338(2) 0.69259(7) 0.0238(2) Uani 1 1 d . . . . .
C4 C 0.12176(7) 0.5597(2) 0.70803(7) 0.0238(2) Uani 1 1 d . . . . .
C5 C 0.13574(7) 0.3609(2) 0.76232(7) 0.0226(2) Uani 1 1 d . . . . .
C11 C 0.25865(7) 0.2205(2) 0.83666(6) 0.0205(2) Uani 1 1 d . . . . .
C12 C 0.32267(7) 0.3327(2) 0.87637(7) 0.0230(2) Uani 1 1 d . . . . .
H12 H 0.3425 0.4715 0.8577 0.028 Uiso 1 1 calc R U . . .
C13 C 0.35722(7) 0.2397(2) 0.94351(7) 0.0275(3) Uani 1 1 d . . . . .
H13 H 0.4011 0.3151 0.9708 0.033 Uiso 1 1 calc R U . . .
C14 C 0.32827(8) 0.0379(2) 0.97101(7) 0.0299(3) Uani 1 1 d . . . . .
H14 H 0.3517 -0.0240 1.0174 0.036 Uiso 1 1 calc R U . . .
C15 C 0.26485(8) -0.0733(2) 0.93049(8) 0.0293(3) Uani 1 1 d . . . . .
H15 H 0.2450 -0.2117 0.9494 0.035 Uiso 1 1 calc R U . . .
C16 C 0.23000(7) 0.0150(2) 0.86256(7) 0.0251(2) Uani 1 1 d . . . . .
H16 H 0.1874 -0.0633 0.8343 0.030 Uiso 1 1 calc R U . . .
C21 C 0.34120(6) 0.4299(2) 0.70136(6) 0.0197(2) Uani 1 1 d . . . . .
C22 C 0.40221(7) 0.5928(2) 0.70210(7) 0.0243(2) Uani 1 1 d . . . . .
H22 H 0.3931 0.7358 0.7243 0.029 Uiso 1 1 calc R U . . .
C23 C 0.47684(7) 0.5439(2) 0.66988(8) 0.0294(3) Uani 1 1 d . . . . .
H23 H 0.5190 0.6545 0.6696 0.035 Uiso 1 1 calc R U . . .
C24 C 0.48991(7) 0.3348(2) 0.63815(8) 0.0304(3) Uani 1 1 d . . . . .
H24 H 0.5408 0.3025 0.6157 0.036 Uiso 1 1 calc R U . . .
C25 C 0.42871(8) 0.1724(2) 0.63908(7) 0.0278(3) Uani 1 1 d . . . . .
H25 H 0.4383 0.0283 0.6180 0.033 Uiso 1 1 calc R U . . .
C26 C 0.35354(7) 0.2185(2) 0.67057(7) 0.0234(2) Uani 1 1 d . . . . .
H26 H 0.3114 0.1077 0.6710 0.028 Uiso 1 1 calc R U . . .
C41 C 0.07819(7) 0.4872(2) 0.63242(7) 0.0235(2) Uani 1 1 d . . . . .
H411 H 0.0218 0.4355 0.6427 0.028 Uiso 1 1 calc R U . . .
H412 H 0.0730 0.6186 0.5977 0.028 Uiso 1 1 calc R U . . .
C42 C 0.12337(7) 0.3000(2) 0.59207(7) 0.0240(2) Uani 1 1 d . . . . .
H421 H 0.1809 0.3479 0.5848 0.029 Uiso 1 1 calc R U . . .
H422 H 0.1253 0.1653 0.6254 0.029 Uiso 1 1 calc R U . . .
C43 C 0.08276(7) 0.2381(2) 0.51437(7) 0.0258(2) Uani 1 1 d . . . . .
H431 H 0.0245 0.1960 0.5210 0.031 Uiso 1 1 calc R U . . .
H432 H 0.0833 0.3701 0.4799 0.031 Uiso 1 1 calc R U . . .
C44 C 0.12718(8) 0.0442(2) 0.47777(7) 0.0292(3) Uani 1 1 d . . . . .
H441 H 0.1845 0.0871 0.4698 0.044 Uiso 1 1 calc R U . . .
H442 H 0.0993 0.0072 0.4282 0.044 Uiso 1 1 calc R U . . .
H443 H 0.1264 -0.0869 0.5117 0.044 Uiso 1 1 calc R U . . .
H4 H 0.0272(12) 0.741(3) 0.7294(11) 0.047(5) Uiso 1 1 d . . . . .


_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
O3 C3 1.2075(15) . ?
O4 C4 1.4040(14) . ?
O4 H4 0.915(19) . ?
O5 C5 1.2132(14) . ?
N1 C5 1.3777(14) . ?
N1 C11 1.4273(15) . ?
N1 N2 1.4300(13) . ?
N2 C3 1.3840(15) . ?
N2 C21 1.4336(14) . ?
C3 C4 1.5249(16) . ?
C4 C5 1.5256(18) . ?
C4 C41 1.5266(17) . ?
C11 C12 1.3905(16) . ?
C11 C16 1.3920(17) . ?
C12 C13 1.3876(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3845(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3872(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3898(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.3870(17) . ?
C21 C22 1.3857(16) . ?
C22 C23 1.3893(17) . ?
C22 H22 0.9500 . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3869(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.3882(16) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C41 C42 1.5248(16) . ?
C41 H411 0.9900 . ?
C41 H412 0.9900 . ?
C42 C43 1.5214(17) . ?
C42 H421 0.9900 . ?
C42 H422 0.9900 . ?
C43 C44 1.5182(18) . ?
C43 H431 0.9900 . ?
C43 H432 0.9900 . ?
C44 H441 0.9800 . ?
C44 H442 0.9800 . ?
C44 H443 0.9800 . ?

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
C4 O4 H4 110.6(12) . . ?
C5 N1 C11 123.39(9) . . ?
C5 N1 N2 109.83(9) . . ?
C11 N1 N2 117.00(9) . . ?
C3 N2 N1 110.45(9) . . ?
C3 N2 C21 121.33(10) . . ?
N1 N2 C21 117.56(9) . . ?
O3 C3 N2 124.52(10) . . ?
O3 C3 C4 127.41(11) . . ?
N2 C3 C4 107.96(10) . . ?
O4 C4 C5 109.81(10) . . ?
O4 C4 C3 109.11(10) . . ?
C5 C4 C3 102.85(9) . . ?
O4 C4 C41 114.10(10) . . ?
C5 C4 C41 111.32(10) . . ?
C3 C4 C41 109.03(10) . . ?
O5 C5 N1 124.61(12) . . ?
O5 C5 C4 126.87(11) . . ?
N1 C5 C4 108.47(9) . . ?
C12 C11 C16 120.97(11) . . ?
C12 C11 N1 120.29(10) . . ?
C16 C11 N1 118.72(10) . . ?
C13 C12 C11 119.23(11) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.57(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.61(12) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.87(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 118.72(12) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?
C26 C21 C22 121.57(11) . . ?
C26 C21 N2 120.96(10) . . ?
C22 C21 N2 117.45(10) . . ?
C23 C22 C21 118.99(12) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 120.24(12) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.01(11) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.60(12) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 118.58(11) . . ?
C21 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C42 C41 C4 113.09(9) . . ?
C42 C41 H411 109.0 . . ?
C4 C41 H411 109.0 . . ?
C42 C41 H412 109.0 . . ?
C4 C41 H412 109.0 . . ?
H411 C41 H412 107.8 . . ?
C43 C42 C41 112.98(10) . . ?
C43 C42 H421 109.0 . . ?
C41 C42 H421 109.0 . . ?
C43 C42 H422 109.0 . . ?
C41 C42 H422 109.0 . . ?
H421 C42 H422 107.8 . . ?
C44 C43 C42 111.36(10) . . ?
C44 C43 H431 109.4 . . ?
C42 C43 H431 109.4 . . ?
C44 C43 H432 109.4 . . ?
C42 C43 H432 109.4 . . ?
H431 C43 H432 108.0 . . ?
C43 C44 H441 109.5 . . ?
C43 C44 H442 109.5 . . ?
H441 C44 H442 109.5 . . ?
C43 C44 H443 109.5 . . ?
H441 C44 H443 109.5 . . ?
H442 C44 H443 109.5 . . ?

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
C5 N1 N2 C3 -6.10(13) . . . . ?
C11 N1 N2 C3 -153.27(10) . . . . ?
C5 N1 N2 C21 -151.24(10) . . . . ?
C11 N1 N2 C21 61.59(13) . . . . ?
N1 N2 C3 O3 -173.85(12) . . . . ?
C21 N2 C3 O3 -30.24(18) . . . . ?
N1 N2 C3 C4 2.56(13) . . . . ?
C21 N2 C3 C4 146.18(10) . . . . ?
O3 C3 C4 O4 -65.71(17) . . . . ?
N2 C3 C4 O4 118.01(11) . . . . ?
O3 C3 C4 C5 177.75(13) . . . . ?
N2 C3 C4 C5 1.46(12) . . . . ?
O3 C3 C4 C41 59.50(16) . . . . ?
N2 C3 C4 C41 -116.78(11) . . . . ?
C11 N1 C5 O5 -25.99(18) . . . . ?
N2 N1 C5 O5 -170.64(11) . . . . ?
C11 N1 C5 C4 151.55(10) . . . . ?
N2 N1 C5 C4 6.90(12) . . . . ?
O4 C4 C5 O5 56.33(15) . . . . ?
C3 C4 C5 O5 172.38(12) . . . . ?
C41 C4 C5 O5 -71.00(15) . . . . ?
O4 C4 C5 N1 -121.15(10) . . . . ?
C3 C4 C5 N1 -5.10(12) . . . . ?
C41 C4 C5 N1 111.52(10) . . . . ?
C5 N1 C11 C12 -122.40(12) . . . . ?
N2 N1 C11 C12 19.95(15) . . . . ?
C5 N1 C11 C16 55.59(15) . . . . ?
N2 N1 C11 C16 -162.06(10) . . . . ?
C16 C11 C12 C13 -1.18(17) . . . . ?
N1 C11 C12 C13 176.76(10) . . . . ?
C11 C12 C13 C14 -0.25(18) . . . . ?
C12 C13 C14 C15 0.81(18) . . . . ?
C13 C14 C15 C16 0.05(19) . . . . ?
C14 C15 C16 C11 -1.44(18) . . . . ?
C12 C11 C16 C15 2.01(17) . . . . ?
N1 C11 C16 C15 -175.97(10) . . . . ?
C3 N2 C21 C26 -106.25(13) . . . . ?
N1 N2 C21 C26 34.92(15) . . . . ?
C3 N2 C21 C22 72.04(14) . . . . ?
N1 N2 C21 C22 -146.79(10) . . . . ?
C26 C21 C22 C23 1.23(18) . . . . ?
N2 C21 C22 C23 -177.05(10) . . . . ?
C21 C22 C23 C24 -0.50(18) . . . . ?
C22 C23 C24 C25 -0.61(19) . . . . ?
C23 C24 C25 C26 1.02(19) . . . . ?
C22 C21 C26 C25 -0.82(17) . . . . ?
N2 C21 C26 C25 177.40(10) . . . . ?
C24 C25 C26 C21 -0.32(18) . . . . ?
O4 C4 C41 C42 179.52(10) . . . . ?
C5 C4 C41 C42 -55.52(13) . . . . ?
C3 C4 C41 C42 57.26(13) . . . . ?
C4 C41 C42 C43 -176.39(10) . . . . ?
C41 C42 C43 C44 -177.36(10) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: crystallization from acetonitrile at room temperature during 3 weeks'
