#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/37/2203777.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2203777
loop_
_publ_author_name
'Qing Bao Song'
'You Hua Hu'
'Tian Hua Shen'
'Zhi Min Jin'
_publ_section_title
;4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-1,1'-biphenyl-2-carbonitrile
 0.25-hydrate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m741
_journal_page_last               m743
_journal_paper_doi               10.1107/S1600536804008463
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C25 H27 N3 O, 0.25H2 O'
_chemical_formula_moiety         'C25 H27 N3 O, 0.25H2 O'
_chemical_formula_sum            'C25 H27.5 N3 O1.25'
_chemical_formula_weight         390.00
_chemical_name_systematic
;
4'-[(2-Butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-1,1'-biphenyl-
2-carbonitrile--water (4/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.438(3)
_cell_angle_beta                 105.110(3)
_cell_angle_gamma                94.126(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1419(13)
_cell_length_b                   10.0656(14)
_cell_length_c                   12.1721(17)
_cell_measurement_reflns_used    831
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      2.5
_cell_volume                     1078.1(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL and PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5382
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             417
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.07P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                3033
_reflns_number_total             3713
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6182.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C25 H27.50 N3 O1.25'
_cod_database_code               2203777
_cod_database_fobs_code          2203777
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.37120(14) 0.35422(13) 0.40617(10) 0.0532(3) Uani d . 1 . . O
N1 0.52565(16) 0.37240(14) 0.28629(12) 0.0453(3) Uani d . 1 A . N
N2 0.39725(17) 0.24482(14) 0.13523(13) 0.0472(4) Uani d . 1 A . N
N3 1.06784(19) 0.38612(17) 0.85448(15) 0.0560(4) Uani d . 1 . . N
C1 0.6525(2) 0.45808(18) 0.35922(16) 0.0502(4) Uani d . 1 . . C
H1A 0.6129 0.5131 0.4089 0.060 Uiso calc R 1 . . H
H1B 0.6959 0.5170 0.3113 0.060 Uiso calc R 1 . . H
C2 0.77747(18) 0.37985(17) 0.43166(14) 0.0437(4) Uani d . 1 . . C
C3 0.75036(19) 0.31504(18) 0.52482(15) 0.0480(4) Uani d . 1 . . C
H3 0.6567 0.3187 0.5410 0.058 Uiso calc R 1 . . H
C4 0.86288(19) 0.24395(18) 0.59507(16) 0.0485(4) Uani d . 1 . . C
H4 0.8451 0.2005 0.6581 0.058 Uiso calc R 1 . . H
C5 0.99929(19) 0.23956(16) 0.56934(14) 0.0413(4) Uani d . 1 . . C
C6 1.0261(2) 0.30255(17) 0.47521(15) 0.0464(4) Uani d . 1 . . C
H6 1.1189 0.2979 0.4579 0.056 Uiso calc R 1 . . H
C7 0.9140(2) 0.37220(17) 0.40729(16) 0.0483(4) Uani d . 1 . . C
H7 0.9317 0.4146 0.3439 0.058 Uiso calc R 1 . . H
C8 1.1098(2) 0.16348(17) 0.64605(15) 0.0472(4) Uani d . 1 . . C
C9 1.1533(2) 0.18984(17) 0.76350(15) 0.0458(4) Uani d . 1 . . C
C10 1.2592(2) 0.11897(19) 0.83336(17) 0.0526(5) Uani d . 1 . . C
H10A 1.2848 0.1358 0.9115 0.063 Uiso calc R 1 . . H
C11 1.3283(2) 0.0237(2) 0.78982(18) 0.0551(5) Uani d . 1 . . C
H11A 1.4005 -0.0240 0.8386 0.066 Uiso calc R 1 . . H
C12 1.2926(2) -0.00268(19) 0.67504(18) 0.0559(5) Uani d . 1 . . C
H12A 1.3331 -0.0738 0.6472 0.067 Uiso d R 1 . . H
C13 1.1821(2) 0.06690(18) 0.60405(16) 0.0504(4) Uani d . 1 . . C
H13A 1.1559 0.0481 0.5261 0.060 Uiso calc R 1 . . H
C14 1.1076(2) 0.30021(19) 0.81408(16) 0.0486(4) Uani d . 1 . . C
C15 0.51656(18) 0.32003(16) 0.17759(14) 0.0395(4) Uani d . 1 . . C
C16 0.30514(19) 0.24000(17) 0.21733(15) 0.0440(4) Uani d . 1 . . C
C17 0.3814(2) 0.33082(18) 0.31310(16) 0.0495(4) Uani d . 1 A . C
C18 0.15181(19) 0.2832(2) 0.18066(17) 0.0533(5) Uani d . 1 A . C
H18A 0.1466 0.3518 0.1245 0.064 Uiso calc R 1 . . H
H18B 0.1216 0.3190 0.2449 0.064 Uiso calc R 1 . . H
C19 0.0506(2) 0.16347(18) 0.13041(19) 0.0605(5) Uani d . 1 . . C
H19A -0.0387 0.1581 0.1596 0.073 Uiso calc R 1 A . H
H19B 0.0175 0.1703 0.0483 0.073 Uiso calc R 1 . . H
C20 0.1314(2) 0.0452(2) 0.1591(2) 0.0624(5) Uani d . 1 A . C
H20A 0.1596 0.0080 0.0944 0.075 Uiso calc R 1 . . H
H20B 0.0738 -0.0225 0.1901 0.075 Uiso calc R 1 . . H
C21 0.2639(2) 0.10385(18) 0.24555(17) 0.0526(4) Uani d . 1 A . C
H21A 0.2412 0.1045 0.3191 0.063 Uiso calc R 1 . . H
H21B 0.3491 0.0499 0.2507 0.063 Uiso calc R 1 . . H
C22 0.6418(2) 0.35770(18) 0.12222(16) 0.0482(4) Uani d . 1 A 1 C
H22A 0.7338 0.3186 0.1630 0.058 Uiso calc PR 0.832(10) B 1 H
H22B 0.6623 0.4538 0.1264 0.058 Uiso calc PR 0.832(10) B 1 H
C23 0.5983(5) 0.3089(4) -0.0045(3) 0.0444(8) Uani d P 0.832(10) A 1 C
H23A 0.5983 0.2126 -0.0081 0.053 Uiso calc PR 0.832(10) B 1 H
H23B 0.4965 0.3326 -0.0414 0.053 Uiso calc PR 0.832(10) B 1 H
C24 0.7061(5) 0.3687(3) -0.0660(3) 0.0461(8) Uani d P 0.832(10) A 1 C
H24A 0.8073 0.3429 -0.0299 0.055 Uiso calc PR 0.832(10) B 1 H
H24B 0.7085 0.4650 -0.0597 0.055 Uiso calc PR 0.832(10) B 1 H
C25 0.6649(8) 0.3269(6) -0.1915(6) 0.0436(12) Uani d P 0.832(10) A 1 C
H25A 0.6972 0.2394 -0.1993 0.065 Uiso calc PR 0.832(10) B 1 H
H25B 0.7147 0.3890 -0.2320 0.065 Uiso calc PR 0.832(10) B 1 H
H25C 0.5569 0.3258 -0.2223 0.065 Uiso calc PR 0.832(10) B 1 H
H22C 0.7376 0.3551 0.1797 0.058 Uiso calc PR 0.168(10) B 2 H
H22D 0.6328 0.4495 0.0994 0.058 Uiso calc PR 0.168(10) B 2 H
C23' 0.652(2) 0.2727(14) 0.0161(14) 0.044(4) Uani d P 0.168(10) A 2 C
H23C 0.5734 0.1998 0.0007 0.053 Uiso calc PR 0.168(10) B 2 H
H23D 0.7499 0.2354 0.0311 0.053 Uiso calc PR 0.168(10) B 2 H
C25' 0.632(4) 0.297(3) -0.206(3) 0.030(4) Uani d P 0.168(10) A 2 C
H25D 0.6691 0.2102 -0.1900 0.045 Uiso calc PR 0.168(10) B 2 H
H25E 0.6981 0.3483 -0.2425 0.045 Uiso calc PR 0.168(10) B 2 H
H25F 0.5314 0.2875 -0.2559 0.045 Uiso calc PR 0.168(10) B 2 H
C24' 0.630(3) 0.3685(13) -0.0937(12) 0.046(4) Uani d P 0.168(10) A 2 C
H24C 0.5336 0.4083 -0.1049 0.055 Uiso calc PR 0.168(10) B 2 H
H24D 0.7098 0.4402 -0.0768 0.055 Uiso calc PR 0.168(10) B 2 H
O1W 0.5006(6) 0.0870(5) 0.4997(4) 0.0515(12) Uani d P 0.25 . . O
H1WC 0.4595 0.0287 0.4478 0.062 Uiso d PR 0.25 . . H
H1WB 0.4349 0.1102 0.5328 0.062 Uiso d PR 0.25 . . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C15 N1 C17 . 107.06(14)
C15 N1 C1 . 126.97(14)
C17 N1 C1 . 125.92(14)
C15 N2 C16 . 107.76(15)
N1 C1 C2 . 113.35(14)
N1 C1 H1A . 108.9
C2 C1 H1A . 108.9
N1 C1 H1B . 108.9
C2 C1 H1B . 108.9
H1A C1 H1B . 107.7
C7 C2 C3 . 119.51(17)
C7 C2 C1 . 122.09(16)
C3 C2 C1 . 118.41(15)
C2 C3 C4 . 120.42(16)
C2 C3 H3 . 119.8
C4 C3 H3 . 119.8
C5 C4 C3 . 118.72(17)
C5 C4 H4 . 120.6
C3 C4 H4 . 120.6
C4 C5 C6 . 121.05(17)
C4 C5 C8 . 115.38(16)
C6 C5 C8 . 123.56(16)
C7 C6 C5 . 119.33(16)
C7 C6 H6 . 120.3
C5 C6 H6 . 120.3
C2 C7 C6 . 120.96(17)
C2 C7 H7 . 119.5
C6 C7 H7 . 119.5
C13 C8 C9 . 117.56(17)
C13 C8 C5 . 120.58(16)
C9 C8 C5 . 121.77(16)
C10 C9 C8 . 120.67(17)
C10 C9 C14 . 116.03(17)
C8 C9 C14 . 122.74(17)
C9 C10 C11 . 120.57(18)
C9 C10 H10A . 119.7
C11 C10 H10A . 119.7
C10 C11 C12 . 120.74(18)
C10 C11 H11A . 119.6
C12 C11 H11A . 119.6
C11 C12 C13 . 118.81(18)
C11 C12 H12A . 119.7
C13 C12 H12A . 121.0
C8 C13 C12 . 121.59(18)
C8 C13 H13A . 119.2
C12 C13 H13A . 119.2
N3 C14 C9 . 178.2(2)
N2 C15 N1 . 114.22(15)
N2 C15 C22 . 126.63(16)
N1 C15 C22 . 119.15(15)
C18 C16 C21 . 97.33(15)
C18 C16 N2 . 117.94(15)
C21 C16 N2 . 112.73(15)
C18 C16 C17 . 104.18(14)
C21 C16 C17 . 116.59(16)
N2 C16 C17 . 107.89(14)
O1 C17 C16 . 137.42(18)
O1 C17 N1 . 117.83(16)
C16 C17 N1 . 102.60(14)
C16 C18 C19 . 106.61(16)
C16 C18 H18A . 110.4
C19 C18 H18A . 110.4
C16 C18 H18B . 110.4
C19 C18 H18B . 110.4
H18A C18 H18B . 108.6
C20 C19 C18 . 109.65(16)
C20 C19 H19A . 109.7
C18 C19 H19A . 109.7
C20 C19 H19B . 109.7
C18 C19 H19B . 109.7
H19A C19 H19B . 108.2
C19 C20 C21 . 98.86(16)
C19 C20 H20A . 112.0
C21 C20 H20A . 112.0
C19 C20 H20B . 112.0
C21 C20 H20B . 112.0
H20A C20 H20B . 109.7
C16 C21 C20 . 110.92(16)
C16 C21 H21A . 109.5
C20 C21 H21A . 109.5
C16 C21 H21B . 109.5
C20 C21 H21B . 109.5
H21A C21 H21B . 108.0
C15 C22 C23 . 111.12(17)
C15 C22 H22A . 109.4
C23 C22 H22A . 109.4
C15 C22 H22B . 109.4
C23 C22 H22B . 109.4
H22A C22 H22B . 108.0
C24 C23 C22 . 111.4(3)
C24 C23 H23A . 109.3
C22 C23 H23A . 109.3
C24 C23 H23B . 109.3
C22 C23 H23B . 109.3
H23A C23 H23B . 108.0
C23 C24 C25 . 113.2(3)
C23 C24 H24A . 108.9
C25 C24 H24A . 108.9
C23 C24 H24B . 108.9
C25 C24 H24B . 108.9
H24A C24 H24B . 107.8
C24' C23' H23C . 109.9
C24' C23' H23D . 109.9
H23C C23' H23D . 108.3
C24' C25' H25D . 109.5
C24' C25' H25E . 109.5
H25D C25' H25E . 109.5
C24' C25' H25F . 109.5
H25D C25' H25F . 109.5
H25E C25' H25F . 109.5
C25' C24' C23' . 114.7(15)
C25' C24' H24C . 108.6
C23' C24' H24C . 108.6
C25' C24' H24D . 108.6
C23' C24' H24D . 108.6
H24C C24' H24D . 107.6
O1W O1W H1WC 2_656 49.4
O1W O1W H1WB 2_656 108.4
H1WC O1W H1WB . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C17 1.184(2) ?
N1 C15 1.400(2) ?
N1 C17 1.472(2) ?
N1 C1 1.478(2) ?
N2 C15 1.269(2) ?
N2 C16 1.464(2) ?
N3 C14 1.119(2) ?
C1 C2 1.522(2) ?
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 C7 1.363(2) ?
C2 C3 1.381(2) ?
C3 C4 1.399(2) ?
C3 H3 0.9300 ?
C4 C5 1.366(2) ?
C4 H4 0.9300 ?
C5 C6 1.382(2) ?
C5 C8 1.452(2) ?
C6 C7 1.377(2) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C13 1.380(3) ?
C8 C9 1.398(2) ?
C9 C10 1.360(3) ?
C9 C14 1.406(3) ?
C10 C11 1.361(3) ?
C10 H10A 0.9300 ?
C11 C12 1.369(3) ?
C11 H11A 0.9300 ?
C12 C13 1.383(2) ?
C12 H12A 0.9300 ?
C13 H13A 0.9300 ?
C15 C22 1.501(2) ?
C16 C18 1.455(2) y
C16 C21 1.462(2) y
C16 C17 1.466(2) y
C18 C19 1.489(3) y
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 C20 1.444(3) y
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 C21 1.465(3) y
C20 H20A 0.9700 ?
C20 H20B 0.9700 ?
C21 H21A 0.9700 ?
C21 H21B 0.9700 ?
C22 C23 1.555(3) ?
C22 H22A 0.9700 ?
C22 H22B 0.9700 ?
C23 C24 1.484(4) ?
C23 H23A 0.9700 ?
C23 H23B 0.9700 ?
C24 C25 1.523(7) ?
C24 H24A 0.9700 ?
C24 H24B 0.9700 ?
C25 H25A 0.9600 ?
C25 H25B 0.9600 ?
C25 H25C 0.9600 ?
C23' C24' 1.63(2) ?
C23' H23C 0.9700 ?
C23' H23D 0.9700 ?
C25' C24' 1.55(3) ?
C25' H25D 0.9600 ?
C25' H25E 0.9600 ?
C25' H25F 0.9600 ?
C24' H24C 0.9700 ?
C24' H24D 0.9700 ?
O1W H1WC 0.8500 ?
O1W H1WB 0.8500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1A O1 2_666 0.97 2.57 3.474(2) 154 yes
C6 H6 O1 1_655 0.93 2.57 3.477(2) 164 yes
C18 H18B O1 . 0.97 2.59 2.994(2) 105 yes
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_publ_flag
C4 C5 C8 C9 -54.7(2) y
C6 C5 C8 C13 -50.0(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139066750
