#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/20/2212055.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_2212055
loop_
_publ_author_name
'K. Ravikumar'
'B. Sridhar'
' K. Durga Prasad'
'A. K. S. Bhujanga Rao'
_publ_section_title
;
 Voriconazole, an antifungal drug
;
_journal_coeditor_code           BT2234
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o565
_journal_page_last               o567
_journal_paper_doi               10.1107/S1600536807000074
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H14 F3 N5 O'
_chemical_formula_moiety         'C16 H14 F3 N5 O'
_chemical_formula_sum            'C16 H14 F3 N5 O'
_chemical_formula_weight         349.32
_chemical_name_common            Voriconazole
_chemical_name_systematic
;
2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)
butan-2-ol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.062(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.5332(19)
_cell_length_b                   8.349(2)
_cell_length_c                   12.989(3)
_cell_measurement_reflns_used    3871
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.44
_cell_volume                     804.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
SHELXTL/PC (Sheldrick, 1990), DIAMOND (Brandenburg & Putz, 2005)
and MERCURY (Bruno et al.,  2002)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7364
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.306
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         1529
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0594
_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)+(0.1192P)²+0.0109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1607
_reflns_number_gt                1398
_reflns_number_total             1529
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2234.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2212055
_cod_database_fobs_code          2212055
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_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
C C1 0.1441(5) 0.6829(5) 0.6867(3) 0.0452(9) Uani d . 1
H H1A 0.0959 0.7234 0.7462 0.054 Uiso calc R 1
H H1B 0.1857 0.7735 0.6507 0.054 Uiso calc R 1
C C2 0.3049(5) 0.5704(4) 0.7258(3) 0.0387(8) Uani d . 1
C C3 0.4505(5) 0.6635(5) 0.8030(3) 0.0453(9) Uani d . 1
H H3 0.3929 0.7058 0.8594 0.054 Uiso calc R 1
C C4 0.6074(6) 0.5546(6) 0.8526(4) 0.0608(12) Uani d . 1
H H4A 0.6568 0.5014 0.7985 0.091 Uiso calc R 1
H H4B 0.5639 0.4762 0.8963 0.091 Uiso calc R 1
H H4C 0.6993 0.6182 0.8941 0.091 Uiso calc R 1
C C5 0.5291(5) 0.8045(5) 0.7513(3) 0.0451(8) Uani d . 1
C C6 0.6361(6) 0.9132(7) 0.6130(4) 0.0636(12) Uani d . 1
H H6 0.6581 0.8991 0.5453 0.076 Uiso calc R 1
C C7 0.6557(7) 1.0649(6) 0.7544(6) 0.0744(15) Uani d . 1
H H7 0.6899 1.1594 0.7903 0.089 Uiso calc R 1
C C8 0.5769(6) 0.9471(6) 0.8047(4) 0.0565(10) Uani d . 1
C C9 -0.0212(6) 0.5858(6) 0.5141(3) 0.0512(9) Uani d . 1
H H9 0.0511 0.6346 0.4721 0.061 Uiso calc R 1
C C10 -0.2180(5) 0.4524(6) 0.5690(4) 0.0562(10) Uani d . 1
H H10 -0.3163 0.3855 0.5701 0.067 Uiso calc R 1
C C11 0.2388(5) 0.4226(4) 0.7767(3) 0.0388(8) Uani d . 1
C C12 0.2436(5) 0.2728(5) 0.7303(3) 0.0455(9) Uani d . 1
H H12 0.2939 0.2631 0.6702 0.055 Uiso calc R 1
C C13 0.1754(6) 0.1378(6) 0.7714(4) 0.0562(10) Uani d . 1
H H13 0.1790 0.0385 0.7395 0.067 Uiso calc R 1
C C14 0.1029(6) 0.1543(6) 0.8599(3) 0.0542(10) Uani d . 1
C C15 0.0937(7) 0.2965(7) 0.9095(3) 0.0578(10) Uani d . 1
H H15 0.0442 0.3050 0.9700 0.069 Uiso calc R 1
C C16 0.1622(5) 0.4282(5) 0.8647(3) 0.0469(9) Uani d . 1
F F1 0.5503(5) 0.9644(4) 0.9025(3) 0.0849(10) Uani d . 1
F F2 0.1467(4) 0.5716(3) 0.9118(2) 0.0668(8) Uani d . 1
F F3 0.0390(5) 0.0208(4) 0.9015(3) 0.0847(10) Uani d . 1
N N1 0.0019(4) 0.5998(4) 0.6161(2) 0.0417(7) Uani d . 1
N N2 -0.1247(4) 0.5139(6) 0.6539(3) 0.0555(9) Uani d . 1
N N3 -0.1612(5) 0.4929(5) 0.4789(3) 0.0599(10) Uani d . 1
N N4 0.5582(5) 0.7922(5) 0.6539(3) 0.0530(8) Uani d . 1
N N5 0.6856(6) 1.0512(6) 0.6581(4) 0.0739(12) Uani d . 1
O O1 0.3763(4) 0.5149(4) 0.63818(19) 0.0467(7) Uani d . 1
H H1O 0.449(7) 0.579(9) 0.629(4) 0.063(15) Uiso d . 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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
_geom_angle_publ_flag
N1 C1 C2 111.4(3) ?
N1 C1 H1A 109.3 ?
C2 C1 H1A 109.3 ?
N1 C1 H1B 109.3 ?
C2 C1 H1B 109.3 ?
H1A C1 H1B 108.0 ?
O1 C2 C11 106.4(3) y
O1 C2 C1 108.7(3) ?
C11 C2 C1 109.7(3) ?
O1 C2 C3 110.8(3) ?
C11 C2 C3 111.8(3) ?
C1 C2 C3 109.3(3) y
C5 C3 C4 108.2(3) ?
C5 C3 C2 112.7(3) y
C4 C3 C2 112.2(3) y
C5 C3 H3 107.9 ?
C4 C3 H3 107.9 ?
C2 C3 H3 107.9 ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
N4 C5 C8 118.0(4) ?
N4 C5 C3 120.1(3) ?
C8 C5 C3 121.8(4) ?
N5 C6 N4 126.8(5) ?
N5 C6 H6 116.6 ?
N4 C6 H6 116.6 ?
N5 C7 C8 123.4(5) ?
N5 C7 H7 118.3 ?
C8 C7 H7 118.3 ?
F1 C8 C7 121.9(5) ?
F1 C8 C5 120.0(4) ?
C7 C8 C5 118.1(5) ?
N1 C9 N3 111.0(4) ?
N1 C9 H9 124.5 ?
N3 C9 H9 124.5 ?
N2 C10 N3 115.3(4) ?
N2 C10 H10 122.4 ?
N3 C10 H10 122.4 ?
C16 C11 C12 116.0(3) ?
C16 C11 C2 123.5(3) ?
C12 C11 C2 120.4(3) ?
C13 C12 C11 121.7(3) ?
C13 C12 H12 119.1 ?
C11 C12 H12 119.1 ?
C14 C13 C12 118.3(4) ?
C14 C13 H13 120.9 ?
C12 C13 H13 120.9 ?
C13 C14 C15 123.3(4) ?
C13 C14 F3 118.3(4) ?
C15 C14 F3 118.4(4) ?
C14 C15 C16 116.2(4) ?
C14 C15 H15 121.9 ?
C16 C15 H15 121.9 ?
F2 C16 C11 119.2(4) ?
F2 C16 C15 116.3(3) ?
C11 C16 C15 124.5(4) ?
C9 N1 N2 110.0(3) ?
C9 N1 C1 129.2(3) ?
N2 N1 C1 120.7(3) y
C10 N2 N1 102.2(3) ?
C9 N3 C10 101.5(4) ?
C5 N4 C6 118.9(4) ?
C6 N5 C7 114.7(5) ?
C2 O1 H1O 106(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.458(5) ?
C1 C2 1.546(5) y
C1 H1A 0.9700 ?
C1 H1B 0.9700 ?
C2 O1 1.419(4) ?
C2 C11 1.524(5) ?
C2 C3 1.558(5) y
C3 C5 1.525(5) ?
C3 C4 1.541(6) y
C3 H3 0.9800 ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C5 N4 1.324(5) ?
C5 C8 1.393(6) ?
C6 N5 1.317(8) ?
C6 N4 1.325(6) y
C6 H6 0.9300 ?
C7 N5 1.313(8) ?
C7 C8 1.372(8) ?
C7 H7 0.9300 ?
C8 F1 1.328(6) ?
C9 N1 1.310(5) ?
C9 N3 1.325(6) ?
C9 H9 0.9300 ?
C10 N2 1.305(6) ?
C10 N3 1.357(6) ?
C10 H10 0.9300 ?
C11 C16 1.369(5) ?
C11 C12 1.391(5) ?
C12 C13 1.383(6) ?
C12 H12 0.9300 ?
C13 C14 1.363(7) ?
C13 H13 0.9300 ?
C14 C15 1.359(8) ?
C14 F3 1.363(5) ?
C15 C16 1.385(6) ?
C15 H15 0.9300 ?
C16 F2 1.358(5) ?
N1 N2 1.353(5) y
O1 H1O 0.79(7) ?
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
O1 H1O N4 . 0.79(7) 1.97(7) 2.679(5) 150(6)
C1 H1B N3 2_556 0.97 2.47 3.382(6) 156
C6 H6 O1 2_656 0.93 2.54 3.357(6) 146
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
N1 C1 C2 O1 60.3(4)
N1 C1 C2 C11 -55.6(4)
N1 C1 C2 C3 -178.6(3)
O1 C2 C3 C5 57.0(4)
C11 C2 C3 C5 175.5(3)
C1 C2 C3 C5 -62.7(4)
O1 C2 C3 C4 -65.3(4)
C11 C2 C3 C4 53.2(4)
C1 C2 C3 C4 174.9(3)
C4 C3 C5 N4 86.9(4)
C2 C3 C5 N4 -37.7(5)
C4 C3 C5 C8 -91.4(5)
C2 C3 C5 C8 144.1(4)
N5 C7 C8 F1 179.3(5)
N5 C7 C8 C5 1.2(8)
N4 C5 C8 F1 -179.9(4)
C3 C5 C8 F1 -1.6(6)
N4 C5 C8 C7 -1.8(6)
C3 C5 C8 C7 176.5(4)
O1 C2 C11 C16 179.4(3)
C1 C2 C11 C16 -63.3(4)
C3 C2 C11 C16 58.2(4)
O1 C2 C11 C12 -4.8(4)
C1 C2 C11 C12 112.5(4)
C3 C2 C11 C12 -126.0(4)
C16 C11 C12 C13 -0.3(6)
C2 C11 C12 C13 -176.3(4)
C11 C12 C13 C14 -0.3(6)
C12 C13 C14 C15 0.2(7)
C12 C13 C14 F3 -178.7(4)
C13 C14 C15 C16 0.3(7)
F3 C14 C15 C16 179.3(4)
C12 C11 C16 F2 -177.5(4)
C2 C11 C16 F2 -1.5(6)
C12 C11 C16 C15 0.9(6)
C2 C11 C16 C15 176.9(4)
C14 C15 C16 F2 177.5(4)
C14 C15 C16 C11 -1.0(7)
N3 C9 N1 N2 0.3(5)
N3 C9 N1 C1 176.3(4)
C2 C1 N1 C9 -90.4(5)
C2 C1 N1 N2 85.3(4)
N3 C10 N2 N1 -0.3(5)
C9 N1 N2 C10 0.0(5)
C1 N1 N2 C10 -176.4(3)
N1 C9 N3 C10 -0.4(5)
N2 C10 N3 C9 0.4(5)
C8 C5 N4 C6 2.1(6)
C3 C5 N4 C6 -176.2(4)
N5 C6 N4 C5 -2.1(7)
N4 C6 N5 C7 1.4(8)
C8 C7 N5 C6 -1.0(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 64684
2 PubChem 71616
