#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/76/2237681.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_2237681
loop_
_publ_author_name
'Payton-Stewart, Florastina'
'Ravi Kiran Pingali, Subramanya'
'Donahue, James P.'
_publ_section_title
;
 The chalcone derivative
 (E)-1-(4-fluorophenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
 monohydrate
;
_journal_coeditor_code           PK2468
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o558
_journal_page_last               o559
_journal_paper_doi               10.1107/S160053681300696X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C16 H13 F1 O3, H2 O'
_chemical_formula_moiety         'C16 H13 F1 O3, H2 O'
_chemical_formula_sum            'C16 H15 F O4'
_chemical_formula_weight         290.29
_chemical_name_systematic
;
(E)-1-(4-Fluorophenyl)--3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
monohydrate
;
_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                 95.722(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.787(2)
_cell_length_b                   10.993(3)
_cell_length_c                   12.781(3)
_cell_measurement_reflns_used    7532
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      2.45
_cell_measurement_theta_min      28.25
_cell_volume                     1368.2(6)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11909
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.8450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2009)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0607P)²+0.5324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                2855
_reflns_number_total             3203
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            pk2468.cif
_cod_data_source_block           I
_cod_original_cell_volume        1368.2(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C16 H15 F1 O4'
_cod_database_code               2237681
_cod_database_fobs_code          2237681
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_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
_atom_site_symmetry_multiplicity
F F1 1.90355(8) -0.41277(7) 0.21518(6) 0.0284(2) Uani d 1 1
O O1 1.40402(9) -0.31928(8) 0.47673(7) 0.0243(2) Uani d 1 1
O O2 1.03808(9) 0.36973(8) 0.45389(7) 0.0216(2) Uani d 1 1
H H2 0.977(2) 0.3730(17) 0.5032(16) 0.043(5) Uiso d 1 1
O O3 1.23977(10) 0.34671(8) 0.33849(7) 0.0237(2) Uani d 1 1
O O4 1.14188(10) -0.39678(10) 0.40629(8) 0.0266(2) Uani d 1 1
H H4A 1.227(2) -0.378(2) 0.4266(16) 0.052(6) Uiso d 1 1
H H4B 1.141(2) -0.472(2) 0.3984(17) 0.063(7) Uiso d 1 1
C C1 1.45724(12) -0.24717(11) 0.41849(9) 0.0184(3) Uani d 1 1
C C2 1.57311(12) -0.28995(11) 0.36004(9) 0.0178(2) Uani d 1 1
C C3 1.61894(13) -0.22551(11) 0.27605(10) 0.0210(3) Uani d 1 1
H H3 1.5730(17) -0.1494(16) 0.2507(13) 0.031(4) Uiso d 1 1
C C4 1.72921(14) -0.26744(12) 0.22595(10) 0.0233(3) Uani d 1 1
H H4 1.7621(17) -0.2243(16) 0.1683(13) 0.030(4) Uiso d 1 1
C C5 1.79286(13) -0.37355(12) 0.26222(10) 0.0215(3) Uani d 1 1
C C6 1.75010(13) -0.44096(11) 0.34390(10) 0.0211(3) Uani d 1 1
H H6 1.7980(16) -0.5140(16) 0.3672(12) 0.029(4) Uiso d 1 1
C C7 1.63853(13) -0.39926(11) 0.39241(10) 0.0201(3) Uani d 1 1
H H7 1.6074(16) -0.4430(14) 0.4491(13) 0.024(4) Uiso d 1 1
C C8 1.41072(13) -0.12016(11) 0.40715(10) 0.0195(3) Uani d 1 1
H H8 1.4531(16) -0.0693(15) 0.3609(13) 0.027(4) Uiso d 1 1
C C9 1.31350(12) -0.07855(11) 0.46511(10) 0.0189(3) Uani d 1 1
H H9 1.2769(16) -0.1366(15) 0.5109(12) 0.024(4) Uiso d 1 1
C C10 1.25059(12) 0.04162(11) 0.46436(9) 0.0182(2) Uani d 1 1
C C11 1.14937(13) 0.06159(11) 0.53213(10) 0.0196(3) Uani d 1 1
H H11 1.1290(16) -0.0018(16) 0.5787(13) 0.028(4) Uiso d 1 1
C C12 1.07706(12) 0.17051(11) 0.53043(10) 0.0199(3) Uani d 1 1
H H12 1.0059(16) 0.1842(14) 0.5779(12) 0.024(4) Uiso d 1 1
C C13 1.10616(12) 0.26192(11) 0.46193(9) 0.0182(3) Uani d 1 1
C C14 1.21398(12) 0.24626(11) 0.39687(9) 0.0187(3) Uani d 1 1
C C15 1.28376(12) 0.13679(11) 0.39695(10) 0.0189(3) Uani d 1 1
H H15 1.3551(16) 0.1271(15) 0.3518(13) 0.026(4) Uiso d 1 1
C C16 1.36498(14) 0.34589(13) 0.28868(11) 0.0250(3) Uani d 1 1
H H16A 1.4443(17) 0.3331(15) 0.3422(13) 0.028(4) Uiso d 1 1
H H16C 1.3620(16) 0.2806(14) 0.2335(12) 0.023(4) Uiso d 1 1
H H16B 1.3695(17) 0.4287(15) 0.2550(13) 0.030(4) Uiso d 1 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 0.0016 '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'
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
C13 O2 H2 109.5(12)
C14 O3 C16 116.62(10)
H4A O4 H4B 106(2)
O1 C1 C8 121.50(11)
O1 C1 C2 119.00(11)
C8 C1 C2 119.48(11)
C3 C2 C7 119.24(11)
C3 C2 C1 122.83(11)
C7 C2 C1 117.93(11)
C4 C3 C2 120.69(12)
C4 C3 H3 118.6(10)
C2 C3 H3 120.7(10)
C5 C4 C3 118.12(12)
C5 C4 H4 120.1(10)
C3 C4 H4 121.8(10)
F1 C5 C6 118.65(11)
F1 C5 C4 118.15(12)
C6 C5 C4 123.19(12)
C5 C6 C7 118.23(12)
C5 C6 H6 120.5(9)
C7 C6 H6 121.2(9)
C6 C7 C2 120.49(12)
C6 C7 H7 120.2(10)
C2 C7 H7 119.3(9)
C9 C8 C1 119.88(11)
C9 C8 H8 121.7(10)
C1 C8 H8 118.4(10)
C8 C9 C10 128.85(12)
C8 C9 H9 116.0(9)
C10 C9 H9 115.1(9)
C11 C10 C15 118.81(11)
C11 C10 C9 117.62(11)
C15 C10 C9 123.54(11)
C12 C11 C10 121.14(12)
C12 C11 H11 120.2(10)
C10 C11 H11 118.7(10)
C13 C12 C11 120.00(11)
C13 C12 H12 119.0(9)
C11 C12 H12 121.0(9)
O2 C13 C12 123.52(11)
O2 C13 C14 116.73(11)
C12 C13 C14 119.74(11)
O3 C14 C15 125.71(11)
O3 C14 C13 114.20(10)
C15 C14 C13 120.09(11)
C14 C15 C10 120.06(11)
C14 C15 H15 119.1(10)
C10 C15 H15 120.8(10)
O3 C16 H16A 109.8(9)
O3 C16 H16C 110.4(9)
H16A C16 H16C 110.4(13)
O3 C16 H16B 105.0(10)
H16A C16 H16B 110.9(14)
H16C C16 H16B 110.1(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C5 1.3604(14)
O1 C1 1.2374(15)
O2 C13 1.3585(15)
O2 H2 0.91(2)
O3 C14 1.3702(15)
O3 C16 1.4361(16)
O4 H4A 0.88(2)
O4 H4B 0.83(3)
C1 C8 1.4712(17)
C1 C2 1.4947(17)
C2 C3 1.3969(18)
C2 C7 1.4043(17)
C3 C4 1.3874(18)
C3 H3 0.989(17)
C4 C5 1.3807(18)
C4 H4 0.959(17)
C5 C6 1.3788(19)
C6 C7 1.3863(18)
C6 H6 0.962(17)
C7 H7 0.945(16)
C8 C9 1.3430(18)
C8 H8 0.939(17)
C9 C10 1.4572(17)
C9 H9 0.960(16)
C10 C11 1.3968(17)
C10 C15 1.4135(17)
C11 C12 1.3899(18)
C11 H11 0.950(17)
C12 C13 1.3811(18)
C12 H12 0.980(16)
C13 C14 1.4175(17)
C14 C15 1.3837(17)
C15 H15 0.955(16)
C16 H16A 0.992(17)
C16 H16C 1.005(16)
C16 H16B 1.009(17)
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
O2 H2 O4 3_756 0.91(2) 1.74(2) 2.6479(14) 173.5(18)
O4 H4A O1 . 0.88(2) 1.90(2) 2.7672(15) 173(2)
O4 H4B O2 1_545 0.83(3) 2.17(3) 2.8485(15) 139(2)
O4 H4B O3 1_545 0.83(3) 2.38(3) 3.1283(15) 151(2)
C8 H8 F1 2_855 0.94(2) 2.48(2) 3.3931(17) 164.0(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658391
