#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225261.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_2225261
loop_
_publ_author_name
'Samanta, Sampak'
'Perera, Sandun'
'Broker, Grant A.'
'Zhao, Cong-Gui'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Ethyl [1-(4-bromophenyl)-1-hydroxy-3-oxobutyl](phenyl)phosphinate
 monohydrate
;
_journal_coeditor_code           HB5328
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o569
_journal_paper_doi               10.1107/S160053681000437X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H20 Br O4 P, H2 O'
_chemical_formula_moiety         'C18 H20 Br O4 P, H2 O'
_chemical_formula_sum            'C18 H22 Br O5 P'
_chemical_formula_weight         429.24
_chemical_name_systematic
;
Ethyl [1-(4-bromophenyl)-1-hydroxy-3-oxobutyl](phenyl)phosphinate monohydrate
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 104.79(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.140(2)
_cell_length_b                   5.7779(12)
_cell_length_c                   16.691(3)
_cell_measurement_reflns_used    2824
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.2
_cell_measurement_theta_min      2.5
_cell_volume                     945.5(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'pubCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.058
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6979
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.37
_refine_ls_abs_structure_details 'Flack (1983), 1408 Friedel pairs'
_refine_ls_abs_structure_Flack   0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.044
_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)+(0.0353P)²+0.386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.094
_reflns_number_gt                3382
_reflns_number_total             3568
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5328.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2yb  '
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2225261
_cod_database_fobs_code          2225261
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br14 0.57412(4) -0.25929(15) 0.62623(3) 0.04821(16) Uani d . 1 . .
P P2 0.00084(10) 0.0452(2) 0.76819(6) 0.0228(2) Uani d . 1 . .
O O1 0.1397(3) 0.4301(5) 0.76143(18) 0.0293(6) Uani d D 1 . .
H H1O 0.0981 0.5136 0.7882 0.044 Uiso d D 1 . .
O O1W 0.0072(4) -0.2519(7) 0.97010(18) 0.0583(9) Uani d D 1 . .
H H1W 0.0023 -0.2549 0.9191 0.087 Uiso d D 1 . .
H H2W 0.0093 -0.3917 0.9841 0.087 Uiso d D 1 . .
O O2 0.0088(3) -0.1965(4) 0.80037(15) 0.0291(6) Uani d . 1 . .
O O3 0.4175(3) 0.4060(6) 0.89220(18) 0.0380(7) Uani d . 1 . .
O O21 -0.0871(2) 0.2144(5) 0.80840(14) 0.0259(5) Uani d . 1 . .
C C1 0.1642(3) 0.2055(7) 0.7962(2) 0.0220(8) Uani d . 1 . .
C C2 0.2089(4) 0.2109(7) 0.8912(2) 0.0276(8) Uani d . 1 . .
H H2A 0.1347 0.2829 0.9113 0.033 Uiso calc R 1 . .
H H2B 0.2182 0.0491 0.9114 0.033 Uiso calc R 1 . .
C C3 0.3397(4) 0.3364(6) 0.9309(2) 0.0283(9) Uani d . 1 . .
C C4 0.3666(5) 0.3686(9) 1.0232(3) 0.0445(12) Uani d . 1 . .
H H4A 0.3941 0.2205 1.0511 0.067 Uiso calc R 1 . .
H H4B 0.2835 0.4240 1.0367 0.067 Uiso calc R 1 . .
H H4C 0.4398 0.4822 1.0419 0.067 Uiso calc R 1 . .
C C11 0.2671(4) 0.0904(6) 0.7559(2) 0.0228(8) Uani d . 1 . .
C C12 0.3013(4) 0.1955(7) 0.6892(2) 0.0309(9) Uani d . 1 . .
H H12 0.2608 0.3397 0.6693 0.037 Uiso calc R 1 . .
C C13 0.3937(4) 0.0940(7) 0.6509(2) 0.0296(9) Uani d . 1 . .
H H13 0.4178 0.1684 0.6059 0.035 Uiso calc R 1 . .
C C14 0.4496(4) -0.1171(7) 0.6798(2) 0.0297(9) Uani d . 1 . .
C C15 0.4176(4) -0.2265(7) 0.7454(2) 0.0299(9) Uani d . 1 . .
H H15 0.4573 -0.3718 0.7644 0.036 Uiso calc R 1 . .
C C16 0.3267(4) -0.1221(7) 0.7834(2) 0.0262(8) Uani d . 1 . .
H H16 0.3046 -0.1966 0.8290 0.031 Uiso calc R 1 . .
C C21 -0.0698(4) 0.0655(7) 0.6594(2) 0.0249(8) Uani d . 1 . .
C C22 -0.0543(4) -0.1151(7) 0.6068(2) 0.0303(9) Uani d . 1 . .
H H22 -0.0024 -0.2481 0.6286 0.036 Uiso calc R 1 . .
C C23 -0.1158(4) -0.0985(8) 0.5218(3) 0.0336(10) Uani d . 1 . .
H H23 -0.1061 -0.2214 0.4859 0.040 Uiso calc R 1 . .
C C24 -0.1898(4) 0.0934(7) 0.4901(3) 0.0367(10) Uani d . 1 . .
H H24 -0.2318 0.1019 0.4323 0.044 Uiso calc R 1 . .
C C25 -0.2041(4) 0.2751(8) 0.5410(2) 0.0389(10) Uani d . 1 . .
H H25 -0.2547 0.4085 0.5182 0.047 Uiso calc R 1 . .
C C26 -0.1447(4) 0.2630(8) 0.6256(2) 0.0302(8) Uani d . 1 . .
H H26 -0.1547 0.3878 0.6606 0.036 Uiso calc R 1 . .
C C31 -0.2290(4) 0.1602(8) 0.8061(3) 0.0384(10) Uani d . 1 . .
H H31A -0.2337 0.0163 0.8375 0.046 Uiso calc R 1 . .
H H31B -0.2827 0.1376 0.7482 0.046 Uiso calc R 1 . .
C C32 -0.2844(5) 0.3569(9) 0.8440(3) 0.0504(13) Uani d . 1 . .
H H32A -0.3797 0.3257 0.8431 0.076 Uiso calc R 1 . .
H H32B -0.2792 0.4983 0.8125 0.076 Uiso calc R 1 . .
H H32C -0.2309 0.3771 0.9014 0.076 Uiso calc R 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P2 O21 . . 114.20(15) ?
O2 P2 C21 . . 113.59(17) ?
O21 P2 C21 . . 105.60(16) ?
O2 P2 C1 . . 114.53(16) ?
O21 P2 C1 . . 98.54(15) ?
C21 P2 C1 . . 109.05(17) ?
C1 O1 H1O . . 111.5 ?
H1W O1W H2W . . 104.7 ?
C31 O21 P2 . . 120.9(2) ?
O1 C1 C11 . . 106.6(3) ?
O1 C1 C2 . . 112.3(3) ?
C11 C1 C2 . . 114.1(3) ?
O1 C1 P2 . . 107.6(2) ?
C11 C1 P2 . . 109.7(2) ?
C2 C1 P2 . . 106.3(2) ?
C3 C2 C1 . . 117.3(3) ?
C3 C2 H2A . . 108.0 ?
C1 C2 H2A . . 108.0 ?
C3 C2 H2B . . 108.0 ?
C1 C2 H2B . . 108.0 ?
H2A C2 H2B . . 107.2 ?
O3 C3 C2 . . 123.1(3) ?
O3 C3 C4 . . 122.2(4) ?
C2 C3 C4 . . 114.7(4) ?
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 ?
C12 C11 C16 . . 118.3(3) ?
C12 C11 C1 . . 120.0(3) ?
C16 C11 C1 . . 121.7(3) ?
C11 C12 C13 . . 121.3(4) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C14 C13 C12 . . 118.5(4) ?
C14 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C13 C14 C15 . . 121.8(4) ?
C13 C14 Br14 . . 118.6(3) ?
C15 C14 Br14 . . 119.6(3) ?
C14 C15 C16 . . 119.0(4) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C15 C16 C11 . . 121.2(4) ?
C15 C16 H16 . . 119.4 ?
C11 C16 H16 . . 119.4 ?
C22 C21 C26 . . 119.3(3) ?
C22 C21 P2 . . 120.8(3) ?
C26 C21 P2 . . 119.9(3) ?
C21 C22 C23 . . 119.5(4) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C24 C23 C22 . . 120.4(4) ?
C24 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C23 C24 C25 . . 120.7(4) ?
C23 C24 H24 . . 119.6 ?
C25 C24 H24 . . 119.6 ?
C24 C25 C26 . . 120.1(4) ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C25 C26 C21 . . 119.9(4) ?
C25 C26 H26 . . 120.1 ?
C21 C26 H26 . . 120.1 ?
O21 C31 C32 . . 107.6(4) ?
O21 C31 H31A . . 110.2 ?
C32 C31 H31A . . 110.2 ?
O21 C31 H31B . . 110.2 ?
C32 C31 H31B . . 110.2 ?
H31A C31 H31B . . 108.5 ?
C31 C32 H32A . . 109.5 ?
C31 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
C31 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br14 C14 . 1.909(4) ?
P2 O2 . 1.491(2) ?
P2 O21 . 1.584(3) ?
P2 C21 . 1.778(4) ?
P2 C1 . 1.850(4) ?
O1 C1 . 1.418(5) ?
O1 H1O . 0.8400 ?
O1W H1W . 0.8400 ?
O1W H2W . 0.8400 ?
O3 C3 . 1.209(5) ?
O21 C31 . 1.464(5) ?
C1 C11 . 1.531(5) ?
C1 C2 . 1.534(4) ?
C2 C3 . 1.508(5) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.506(5) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C11 C12 . 1.388(5) ?
C11 C16 . 1.393(5) ?
C12 C13 . 1.392(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.379(6) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.373(5) ?
C15 C16 . 1.383(5) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.397(5) ?
C21 C26 . 1.407(5) ?
C22 C23 . 1.400(6) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.368(6) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.382(6) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.388(5) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C31 C32 . 1.479(6) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
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 O2 1_565 0.84 1.94 2.698(4) 150
O1w H1w O2 1_555 0.84 2.03 2.855(4) 168
O1w H2w O1w 2_547 0.84 2.24 3.072(6) 172
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 P2 O21 C31 . . . . -55.9(3) ?
C21 P2 O21 C31 . . . . 69.7(3) ?
C1 P2 O21 C31 . . . . -177.7(3) ?
O2 P2 C1 O1 . . . . -179.9(2) ?
O21 P2 C1 O1 . . . . -58.3(2) ?
C21 P2 C1 O1 . . . . 51.5(3) ?
O2 P2 C1 C11 . . . . 64.5(3) ?
O21 P2 C1 C11 . . . . -173.9(2) ?
C21 P2 C1 C11 . . . . -64.1(3) ?
O2 P2 C1 C2 . . . . -59.4(3) ?
O21 P2 C1 C2 . . . . 62.2(3) ?
C21 P2 C1 C2 . . . . 172.1(2) ?
O1 C1 C2 C3 . . . . -61.6(4) ?
C11 C1 C2 C3 . . . . 59.9(5) ?
P2 C1 C2 C3 . . . . -179.0(3) ?
C1 C2 C3 O3 . . . . -9.4(6) ?
C1 C2 C3 C4 . . . . 170.7(4) ?
O1 C1 C11 C12 . . . . -9.3(4) ?
C2 C1 C11 C12 . . . . -133.8(4) ?
P2 C1 C11 C12 . . . . 107.0(3) ?
O1 C1 C11 C16 . . . . 171.9(3) ?
C2 C1 C11 C16 . . . . 47.4(5) ?
P2 C1 C11 C16 . . . . -71.8(4) ?
C16 C11 C12 C13 . . . . -0.7(5) ?
C1 C11 C12 C13 . . . . -179.5(3) ?
C11 C12 C13 C14 . . . . 1.1(6) ?
C12 C13 C14 C15 . . . . -0.8(5) ?
C12 C13 C14 Br14 . . . . 179.0(3) ?
C13 C14 C15 C16 . . . . 0.1(6) ?
Br14 C14 C15 C16 . . . . -179.7(3) ?
C14 C15 C16 C11 . . . . 0.4(6) ?
C12 C11 C16 C15 . . . . -0.1(5) ?
C1 C11 C16 C15 . . . . 178.8(3) ?
O2 P2 C21 C22 . . . . -29.9(4) ?
O21 P2 C21 C22 . . . . -155.8(3) ?
C1 P2 C21 C22 . . . . 99.1(3) ?
O2 P2 C21 C26 . . . . 148.7(3) ?
O21 P2 C21 C26 . . . . 22.8(4) ?
C1 P2 C21 C26 . . . . -82.3(3) ?
C26 C21 C22 C23 . . . . -1.3(6) ?
P2 C21 C22 C23 . . . . 177.3(3) ?
C21 C22 C23 C24 . . . . 0.5(6) ?
C22 C23 C24 C25 . . . . 0.6(7) ?
C23 C24 C25 C26 . . . . -0.9(7) ?
C24 C25 C26 C21 . . . . 0.1(6) ?
C22 C21 C26 C25 . . . . 1.0(6) ?
P2 C21 C26 C25 . . . . -177.6(3) ?
P2 O21 C31 C32 . . . . -176.7(3) ?
