#------------------------------------------------------------------------------
#$Date: 2019-11-24 21:30:50 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239471 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/67/4516702.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_4516702
loop_
_publ_author_name
'Zhang, Baoxin'
'Jiao, Haijun'
'Michalik, Dirk'
'Kloß, Svenja'
'Deter, Lisa Marie'
'Selent, Detlef'
'Spannenberg, Anke'
'Franke, Robert'
'Börner, Armin'
_publ_section_title
;
 Hydrolysis Stability of Bidentate Phosphites Utilized as Modifying
 Ligands in the Rh-Catalyzedn-Regioselective Hydroformylation of Olefins
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7554
_journal_paper_doi               10.1021/acscatal.6b02185
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C7 H5 O4 P'
_chemical_formula_weight         184.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.6306(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5729(2)
_cell_length_b                   14.1363(5)
_cell_length_c                   11.7191(4)
_cell_measurement_reflns_used    8072
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.88
_cell_volume                     744.57(5)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.992
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.183
_refine_diff_density_max         0.948
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0474
_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)+(0.0577P)²+0.8393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1317
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1699
_reflns_number_total             1787
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs6b02185_si_004.cif
_cod_data_source_block           AX0850
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4516702
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.4644(5) 0.69674(14) 0.27310(18) 0.0270(4) Uani 1 1 d . .
C2 C 0.5688(6) 0.78858(16) 0.2830(2) 0.0364(5) Uani 1 1 d . .
H2 H 0.4745 0.8367 0.2327 0.044 Uiso 1 1 calc R U
C3 C 0.8131(6) 0.80908(17) 0.3676(2) 0.0416(6) Uani 1 1 d . .
H3 H 0.8879 0.8719 0.3748 0.050 Uiso 1 1 calc R U
C4 C 0.9513(6) 0.7396(2) 0.4421(2) 0.0409(6) Uani 1 1 d . .
H4 H 1.1173 0.7552 0.5006 0.049 Uiso 1 1 calc R U
C5 C 0.8470(5) 0.64809(17) 0.43091(19) 0.0328(5) Uani 1 1 d . .
H5 H 0.9423 0.6002 0.4814 0.039 Uiso 1 1 calc R U
C6 C 0.6013(4) 0.62540(14) 0.34538(17) 0.0253(4) Uani 1 1 d . .
C7 C 0.5013(5) 0.52652(15) 0.33365(19) 0.0300(4) Uani 1 1 d . .
O1 O 0.2129(4) 0.67948(11) 0.18912(15) 0.0350(4) Uani 1 1 d . .
O2 O -0.1967(4) 0.56536(15) 0.10471(18) 0.0488(5) Uani 1 1 d . .
O3 O 0.2519(4) 0.50945(11) 0.24756(16) 0.0372(4) Uani 1 1 d . .
O4 O 0.6079(5) 0.46094(12) 0.38976(17) 0.0468(5) Uani 1 1 d . .
P1 P 0.12283(12) 0.57711(4) 0.14241(5) 0.0317(2) Uani 1 1 d . .
H1 H 0.281(6) 0.549(2) 0.071(2) 0.038 Uiso 1 1 d . U
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 121.4(2)
C2 C1 O1 116.9(2)
C6 C1 O1 121.67(18)
C3 C2 C1 118.6(2)
C3 C2 H2 120.7
C1 C2 H2 120.7
C2 C3 C4 121.2(2)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 119.7(2)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.1(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 118.86(19)
C1 C6 C7 122.41(18)
C5 C6 C7 118.72(19)
O4 C7 O3 117.5(2)
O4 C7 C6 127.0(2)
O3 C7 C6 115.49(18)
C1 O1 P1 122.45(13)
C7 O3 P1 126.48(14)
O2 P1 O1 113.19(10)
O2 P1 O3 112.09(12)
O1 P1 O3 104.36(8)
O2 P1 H1 115.2(13)
O1 P1 H1 112.1(13)
O3 P1 H1 98.3(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.381(3)
C1 C6 1.390(3)
C1 O1 1.390(3)
C2 C3 1.380(4)
C2 H2 0.9500
C3 C4 1.386(4)
C3 H3 0.9500
C4 C5 1.377(3)
C4 H4 0.9500
C5 C6 1.398(3)
C5 H5 0.9500
C6 C7 1.469(3)
C7 O4 1.188(3)
C7 O3 1.397(3)
O1 P1 1.5749(17)
O2 P1 1.4559(18)
O3 P1 1.5854(18)
P1 H1 1.27(3)
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
C6 C1 C2 C3 -0.6(3)
O1 C1 C2 C3 178.2(2)
C1 C2 C3 C4 -0.5(4)
C2 C3 C4 C5 1.0(4)
C3 C4 C5 C6 -0.5(4)
C2 C1 C6 C5 1.0(3)
O1 C1 C6 C5 -177.70(19)
C2 C1 C6 C7 -177.6(2)
O1 C1 C6 C7 3.6(3)
C4 C5 C6 C1 -0.5(3)
C4 C5 C6 C7 178.2(2)
C1 C6 C7 O4 178.4(2)
C5 C6 C7 O4 -0.2(4)
C1 C6 C7 O3 -2.3(3)
C5 C6 C7 O3 179.1(2)
C2 C1 O1 P1 161.74(17)
C6 C1 O1 P1 -19.5(3)
O4 C7 O3 P1 -163.09(19)
C6 C7 O3 P1 17.5(3)
C1 O1 P1 O2 150.67(18)
C1 O1 P1 O3 28.5(2)
C7 O3 P1 O2 -151.53(19)
C7 O3 P1 O1 -28.7(2)
