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#$Date: 2025-08-23 02:36:08 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301880 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/27/8102720.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_8102720
loop_
_publ_author_name
'Stefan Spieldener'
'Klaus Wurst'
'Josef Stadlwieser'
'Ernst Ellmerer'
_publ_section_title
;
 Crystal structure of
 1-(4-fluorophenyl)chromeno[4,3-c]pyrazol-4(1H)-one, C16H9FN2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              385
_journal_volume                  225
_journal_year                    2010
_chemical_formula_sum            'C16 H9 F N2 O2'
_chemical_formula_weight         280.25
_chemical_name_systematic
; 
 1-(4-fluorophenyl)chromeno[4,3-c]pyrazol-4(1H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.071(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3937(3)
_cell_length_b                   8.5822(3)
_cell_length_c                   14.5067(4)
_cell_measurement_reflns_used    8382
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.0
_cell_volume                     1277.83(7)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
 DENZO (Otwinowski & Minor, 1997) and SCALEPACK 
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997) [4] '
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997) [3]'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997) [2]'
_diffrn_ambient_temperature      243(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6934
_diffrn_reflns_theta_full        24.93
_diffrn_reflns_theta_max         24.93
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.049(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0349
_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)+(0.0532P)²+0.2181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                1933
_reflns_number_total             2215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3000.cff
_cod_data_source_block           ger3
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               8102720
loop_
_symmetry_equiv_pos_as_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'
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
O1 O 0.54562(9) 0.22483(11) 0.01367(6) 0.0439(3) Uani 1 1 d . . .
O2 O 0.67106(10) 0.33031(13) -0.07857(6) 0.0544(3) Uani 1 1 d . . .
N1 N 0.64285(10) 0.58663(13) 0.19304(7) 0.0394(3) Uani 1 1 d . . .
N2 N 0.72567(11) 0.67168(14) 0.14740(9) 0.0495(3) Uani 1 1 d . . .
F1 F 0.51482(9) 0.79038(14) 0.52607(6) 0.0770(4) Uani 1 1 d . . .
C3 C 0.73235(13) 0.59376(17) 0.07022(10) 0.0469(4) Uani 1 1 d . . .
H3 H 0.7827 0.6243 0.0249 0.056 Uiso 1 1 calc . . .
C4 C 0.65472(11) 0.45921(15) 0.06409(8) 0.0369(3) Uani 1 1 d . . .
C5 C 0.62900(12) 0.34080(16) -0.00599(9) 0.0396(3) Uani 1 1 d . . .
C6 C 0.48451(12) 0.22523(15) 0.09185(9) 0.0365(3) Uani 1 1 d . . .
C7 C 0.39904(14) 0.10320(16) 0.09727(10) 0.0471(4) Uani 1 1 d . . .
H7 H 0.3871 0.0261 0.0507 0.057 Uiso 1 1 calc . . .
C8 C 0.33193(14) 0.09603(17) 0.17139(11) 0.0500(4) Uani 1 1 d . . .
H8 H 0.2740 0.0132 0.1756 0.060 Uiso 1 1 calc . . .
C9 C 0.34863(14) 0.20946(18) 0.24000(10) 0.0482(4) Uani 1 1 d . . .
H9 H 0.3015 0.2043 0.2901 0.058 Uiso 1 1 calc . . .
C10 C 0.43446(13) 0.32984(16) 0.23463(9) 0.0420(3) Uani 1 1 d . . .
H10 H 0.4455 0.4065 0.2815 0.050 Uiso 1 1 calc . . .
C11 C 0.50547(11) 0.34011(14) 0.16082(8) 0.0333(3) Uani 1 1 d . . .
C12 C 0.59780(11) 0.45888(14) 0.14406(8) 0.0334(3) Uani 1 1 d . . .
C13 C 0.61308(12) 0.64214(15) 0.28019(9) 0.0386(3) Uani 1 1 d . . .
C14 C 0.65422(13) 0.55825(16) 0.36047(9) 0.0444(3) Uani 1 1 d . . .
H14 H 0.7050 0.4680 0.3585 0.053 Uiso 1 1 calc . . .
C15 C 0.61986(14) 0.60843(19) 0.44399(9) 0.0489(4) Uani 1 1 d . . .
H15 H 0.6453 0.5520 0.4994 0.059 Uiso 1 1 calc . . .
C16 C 0.54823(13) 0.74176(19) 0.44408(10) 0.0505(4) Uani 1 1 d . . .
C17 C 0.50894(15) 0.82847(19) 0.36546(11) 0.0585(4) Uani 1 1 d . . .
H17 H 0.4610 0.9207 0.3682 0.070 Uiso 1 1 calc . . .
C18 C 0.54160(14) 0.77694(17) 0.28193(10) 0.0503(4) Uani 1 1 d . . .
H18 H 0.5152 0.8335 0.2267 0.060 Uiso 1 1 calc . . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 123.51(10) . . ?
C12 N1 N2 111.67(10) . . ?
C12 N1 C13 129.11(10) . . ?
N2 N1 C13 119.20(11) . . ?
C3 N2 N1 105.13(11) . . ?
N2 C3 C4 111.42(11) . . ?
C12 C4 C3 105.45(11) . . ?
C12 C4 C5 122.50(11) . . ?
C3 C4 C5 132.04(12) . . ?
O2 C5 O1 116.94(12) . . ?
O2 C5 C4 128.33(13) . . ?
O1 C5 C4 114.73(10) . . ?
C7 C6 O1 115.23(11) . . ?
C7 C6 C11 121.50(12) . . ?
O1 C6 C11 123.26(11) . . ?
C8 C7 C6 119.26(12) . . ?
C7 C8 C9 120.70(12) . . ?
C10 C9 C8 119.79(12) . . ?
C9 C10 C11 121.14(12) . . ?
C10 C11 C6 117.59(12) . . ?
C10 C11 C12 128.20(11) . . ?
C6 C11 C12 114.18(11) . . ?
N1 C12 C4 106.33(10) . . ?
N1 C12 C11 131.93(11) . . ?
C4 C12 C11 121.70(11) . . ?
C18 C13 C14 121.30(12) . . ?
C18 C13 N1 119.26(12) . . ?
C14 C13 N1 119.43(12) . . ?
C13 C14 C15 119.23(13) . . ?
C16 C15 C14 118.51(13) . . ?
F1 C16 C15 118.27(14) . . ?
F1 C16 C17 118.64(14) . . ?
C15 C16 C17 123.09(13) . . ?
C16 C17 C18 118.32(14) . . ?
C13 C18 C17 119.52(14) . . ?
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
O1 C5 1.3788(16) . ?
O1 C6 1.3845(14) . ?
O2 C5 1.2054(14) . ?
N1 C12 1.3496(16) . ?
N1 N2 1.3755(15) . ?
N1 C13 1.4298(16) . ?
N2 C3 1.3153(18) . ?
F1 C16 1.3564(16) . ?
C3 C4 1.4035(19) . ?
C4 C12 1.3828(16) . ?
C4 C5 1.4325(19) . ?
C6 C7 1.3836(19) . ?
C6 C11 1.3971(18) . ?
C7 C8 1.3722(19) . ?
C8 C9 1.383(2) . ?
C9 C10 1.3752(19) . ?
C10 C11 1.3958(17) . ?
C11 C12 1.4465(17) . ?
C13 C18 1.3773(19) . ?
C13 C14 1.3786(19) . ?
C14 C15 1.3847(19) . ?
C15 C16 1.365(2) . ?
C16 C17 1.369(2) . ?
C17 C18 1.382(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653987
2 PubChem 139207278
