#------------------------------------------------------------------------------
#$Date: 2018-04-30 18:27:42 +0200 (lun 30 de abr de 2018) $
#$Revision: 207554 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/24/2242461.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_2242461
loop_
_publ_author_name
'Abou, Akoun'
'Yoda, Jules'
'Djandé, Abdoulaye'
'Coussan, Stéphane'
'Zoueu, T. Jérémie'
_publ_section_title
;
 Crystal structure of 2-oxo-2H-chromen-7-yl 4-fluorobenzoate
;
_journal_coeditor_code           KQ2021
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              761
_journal_page_last               765
_journal_paper_doi               10.1107/S205698901800614X
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C16 H9 F O4'
_chemical_formula_moiety         'C16 H9 F O4'
_chemical_formula_sum            'C16 H9 F O4'
_chemical_formula_weight         284.23
_chemical_melting_point_gt       467
_chemical_melting_point_lt       468
_chemical_name_common            coumarin
_chemical_name_systematic
;
2-Oxo-2H-chromen-7-yl 4-fluorobenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.660(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.0181(2)
_cell_length_b                   5.7296(3)
_cell_length_c                   27.5566(14)
_cell_measurement_reflns_used    4751
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      67.4920
_cell_measurement_theta_min      4.8140
_cell_volume                     634.14(6)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009) and Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015), publCIF (Westrip, 2010) and
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla et al.,  2015)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 5.3048
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Rigaku SuperNova, Dual, Cu at zero, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8239
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.881
_diffrn_reflns_theta_min         4.816
_exptl_absorpt_coefficient_mu    0.996
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.162
_refine_ls_abs_structure_details
;
Flack x determined using 875 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0396P)²+0.1688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2149
_reflns_number_total             2228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            kq2021sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     P2yb
_cod_database_code               2242461
_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.
;
_shelx_estimated_absorpt_t_min   0.691
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_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_occupancy
O O1 0.6427(6) 0.3343(4) 0.88096(8) 0.0524(6) Uani d 1
O O3 0.0412(6) 0.4724(4) 0.73539(8) 0.0615(6) Uani d 1
C C7 0.1548(8) 0.5614(6) 0.78012(11) 0.0497(7) Uani d 1
C C10 0.1085(8) 0.5845(6) 0.69372(12) 0.0530(8) Uani d 1
C C5 0.4431(7) 0.4840(5) 0.85424(11) 0.0441(6) Uani d 1
O O2 0.9356(7) 0.2473(5) 0.94698(9) 0.0754(8) Uani d 1
C C6 0.3531(8) 0.4146(6) 0.80778(11) 0.0478(7) Uani d 1
H H6 0.4246 0.2726 0.7955 0.057 Uiso calc 1
C C9 0.1406(8) 0.8388(6) 0.84388(12) 0.0521(7) Uani d 1
H H9 0.0667 0.9806 0.8560 0.062 Uiso calc 1
C C4 0.3401(8) 0.6973(5) 0.87346(11) 0.0460(7) Uani d 1
C C11 -0.0314(8) 0.4585(6) 0.65121(11) 0.0503(7) Uani d 1
C C16 -0.1991(9) 0.2483(7) 0.65592(12) 0.0573(8) Uani d 1
H H16 -0.2289 0.1853 0.6866 0.069 Uiso calc 1
F F1 -0.3952(7) 0.1157(6) 0.53091(9) 0.1069(10) Uani d 1
O O4 0.2703(7) 0.7609(5) 0.69274(9) 0.0745(8) Uani d 1
C C3 0.4468(8) 0.7532(6) 0.92219(11) 0.0535(8) Uani d 1
H H3 0.3784 0.8923 0.9361 0.064 Uiso calc 1
C C12 0.0095(8) 0.5513(7) 0.60524(13) 0.0613(9) Uani d 1
H H12 0.1210 0.6923 0.6018 0.074 Uiso calc 1
C C1 0.7538(8) 0.3880(6) 0.92768(12) 0.0536(8) Uani d 1
C C8 0.0489(8) 0.7757(6) 0.79730(12) 0.0546(8) Uani d 1
H H8 -0.0810 0.8743 0.7778 0.066 Uiso calc 1
C C14 -0.2763(10) 0.2274(9) 0.57115(14) 0.0705(11) Uani d 1
C C2 0.6429(9) 0.6080(7) 0.94771(12) 0.0570(8) Uani d 1
H H2 0.7103 0.6486 0.9792 0.068 Uiso calc 1
C C15 -0.3218(10) 0.1325(7) 0.61538(14) 0.0679(10) Uani d 1
H H15 -0.4339 -0.0085 0.6184 0.081 Uiso calc 1
C C13 -0.1144(10) 0.4358(9) 0.56453(13) 0.0735(11) Uani d 1
H H13 -0.0889 0.4972 0.5336 0.088 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C5 O1 C1 121.8(2)
C10 O3 C7 120.5(3)
C6 C7 C8 122.1(3)
C6 C7 O3 115.8(3)
C8 C7 O3 121.9(3)
O4 C10 O3 122.7(3)
O4 C10 C11 126.0(3)
O3 C10 C11 111.2(3)
O1 C5 C6 116.8(3)
O1 C5 C4 121.1(3)
C6 C5 C4 122.1(3)
C7 C6 C5 118.1(3)
C7 C6 H6 121.0
C5 C6 H6 121.0
C8 C9 C4 122.0(3)
C8 C9 H9 119.0
C4 C9 H9 119.0
C9 C4 C5 117.4(3)
C9 C4 C3 124.9(3)
C5 C4 C3 117.8(3)
C16 C11 C12 119.2(3)
C16 C11 C10 121.7(3)
C12 C11 C10 119.0(3)
C15 C16 C11 120.4(3)
C15 C16 H16 119.8
C11 C16 H16 119.8
C2 C3 C4 120.7(3)
C2 C3 H3 119.6
C4 C3 H3 119.6
C13 C12 C11 120.5(4)
C13 C12 H12 119.7
C11 C12 H12 119.7
O2 C1 O1 116.0(3)
O2 C1 C2 127.1(3)
O1 C1 C2 116.9(3)
C9 C8 C7 118.4(3)
C9 C8 H8 120.8
C7 C8 H8 120.8
C15 C14 F1 119.6(4)
C15 C14 C13 123.1(4)
F1 C14 C13 117.3(4)
C3 C2 C1 121.7(3)
C3 C2 H2 119.2
C1 C2 H2 119.2
C14 C15 C16 118.9(4)
C14 C15 H15 120.6
C16 C15 H15 120.6
C14 C13 C12 118.0(4)
C14 C13 H13 121.0
C12 C13 H13 121.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.374(3)
O1 C1 1.385(4)
O3 C10 1.350(4)
O3 C7 1.398(4)
C7 C6 1.374(4)
C7 C8 1.387(5)
C10 O4 1.202(4)
C10 C11 1.473(4)
C5 C6 1.379(4)
C5 C4 1.399(4)
O2 C1 1.202(4)
C6 H6 0.9300
C9 C8 1.373(5)
C9 C4 1.388(4)
C9 H9 0.9300
C4 C3 1.434(4)
C11 C16 1.388(5)
C11 C12 1.388(5)
C16 C15 1.378(5)
C16 H16 0.9300
F1 C14 1.355(4)
C3 C2 1.332(5)
C3 H3 0.9300
C12 C13 1.383(5)
C12 H12 0.9300
C1 C2 1.451(5)
C8 H8 0.9300
C14 C15 1.352(6)
C14 C13 1.374(7)
C2 H2 0.9300
C15 H15 0.9300
C13 H13 0.9300
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
C16 H16 O3 . 0.93 2.37 2.693(4) 100.2
C2 H2 O2 2_757 0.93 2.51 3.412(4) 162.5
C1 O2 Cg2 1_455 1.202(4) 3.266(3) 3.403(3) 86.1(2)
C1 O2 Cg4 1_455 1.202(4) 3.567(3) 3.368(3) 70.8(2)
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
C10 O3 C7 C6 -122.3(3)
C10 O3 C7 C8 63.4(4)
C7 O3 C10 O4 1.1(5)
C7 O3 C10 C11 179.3(3)
C1 O1 C5 C6 178.7(3)
C1 O1 C5 C4 -0.7(4)
C8 C7 C6 C5 1.0(4)
O3 C7 C6 C5 -173.3(3)
O1 C5 C6 C7 -179.7(3)
C4 C5 C6 C7 -0.3(4)
C8 C9 C4 C5 -0.8(5)
C8 C9 C4 C3 179.5(3)
O1 C5 C4 C9 179.6(3)
C6 C5 C4 C9 0.2(4)
O1 C5 C4 C3 -0.7(4)
C6 C5 C4 C3 179.9(3)
O4 C10 C11 C16 176.2(3)
O3 C10 C11 C16 -1.9(4)
O4 C10 C11 C12 -3.0(5)
O3 C10 C11 C12 178.9(3)
C12 C11 C16 C15 0.4(5)
C10 C11 C16 C15 -178.8(3)
C9 C4 C3 C2 -179.0(3)
C5 C4 C3 C2 1.3(5)
C16 C11 C12 C13 -0.2(5)
C10 C11 C12 C13 179.0(3)
C5 O1 C1 O2 -177.7(3)
C5 O1 C1 C2 1.5(4)
C4 C9 C8 C7 1.4(5)
C6 C7 C8 C9 -1.5(5)
O3 C7 C8 C9 172.5(3)
C4 C3 C2 C1 -0.5(5)
O2 C1 C2 C3 178.2(4)
O1 C1 C2 C3 -0.9(5)
F1 C14 C15 C16 180.0(3)
C13 C14 C15 C16 -0.4(6)
C11 C16 C15 C14 -0.1(5)
C15 C14 C13 C12 0.6(6)
F1 C14 C13 C12 -179.7(3)
C11 C12 C13 C14 -0.3(6)

_cod_database_fobs_code 2242461
