#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/38/7103884.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_7103884
loop_
_publ_author_name
'Komarov, Igor V.'
'Spannenberg, Anke'
'Holz, Jens'
'Börner, Armin'
_publ_section_title
;
 Highly stereoselective, thermodynamically controlled and reversible
 formation of a new P-chiral phosphine
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   17
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2240
_journal_page_last               2241
_journal_paper_doi               10.1039/b306153a
_journal_year                    2003
_chemical_formula_sum            'C16 H21 O P'
_chemical_formula_weight         260.30
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7590(10)
_cell_length_b                   9.998(2)
_cell_length_c                   21.043(4)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      4
_cell_volume                     1422.0(4)
_computing_cell_refinement       STOE-CELL
_computing_data_collection       STOE-EXPOSE
_computing_data_reduction        STOE-INTEGRATE
_computing_molecular_graphics    XP
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       STOE-IPDS
_diffrn_measurement_method       'laser scanned imaging plate'
_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  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5231
_diffrn_reflns_theta_max         21.08
_diffrn_reflns_theta_min         1.94
_diffrn_standards_interval_time  360
_diffrn_standards_number         50-200
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.931
_refine_ls_goodness_of_fit_obs   0.999
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_restrained_S_obs      0.999
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_obs          0.0336
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0375P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0786
_refine_ls_wR_factor_obs         0.0755
_reflns_number_observed          1230
_reflns_number_total             1494
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b306153a.txt
_cod_data_source_block           KS015
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'no' was replaced with
'none' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7103884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
C1 C 0.5611(5) 0.1967(3) 0.1910(2) 0.0414(9) Uani 1 d . .
H1A H 0.5235(5) 0.1090(3) 0.1754(2) 0.050 Uiso 1 calc R .
H1B H 0.4443(5) 0.2407(3) 0.2077(2) 0.050 Uiso 1 calc R .
C2 C 0.6538(6) 0.2810(3) 0.1370(2) 0.0410(10) Uani 1 d . .
C3 C 0.8806(6) 0.2785(3) 0.1430(2) 0.0408(10) Uani 1 d . .
C4 C 0.8841(5) 0.3228(3) 0.2139(2) 0.0379(9) Uani 1 d . .
C5 C 0.7497(6) 0.4472(3) 0.21323(15) 0.0421(8) Uani 1 d . .
H5A H 0.6591(6) 0.4468(3) 0.24900(15) 0.050 Uiso 1 calc R .
H5B H 0.8271(6) 0.5289(3) 0.21425(15) 0.050 Uiso 1 calc R .
C6 C 0.6378(7) 0.4332(4) 0.1500(2) 0.0447(10) Uani 1 d . .
H6 H 0.5125(53) 0.4740(30) 0.1480(15) 0.037(10) Uiso 1 d . .
C7 C 0.7753(7) 0.4921(3) 0.0993(2) 0.0589(11) Uani 1 d . .
H7A H 0.7127(7) 0.4928(3) 0.0579(2) 0.071 Uiso 1 calc R .
H7B H 0.8160(7) 0.5822(3) 0.1103(2) 0.071 Uiso 1 calc R .
C8 C 0.9494(6) 0.3955(4) 0.1011(2) 0.0576(12) Uani 1 d . .
H8A H 1.0652(6) 0.4382(4) 0.1192(2) 0.069 Uiso 1 calc R .
H8B H 0.9816(6) 0.3646(4) 0.0586(2) 0.069 Uiso 1 calc R .
C9 C 0.6571(6) 0.2571(3) 0.3263(2) 0.0420(10) Uani 1 d . .
C10 C 0.4643(6) 0.2895(3) 0.3391(2) 0.0498(11) Uani 1 d . .
H10 H 0.3689(6) 0.2769(3) 0.3078(2) 0.060 Uiso 1 calc R .
C11 C 0.4078(7) 0.3408(4) 0.3977(2) 0.0608(11) Uani 1 d . .
H11 H 0.2759(7) 0.3621(4) 0.4054(2) 0.073 Uiso 1 calc R .
C12 C 0.5476(8) 0.3602(4) 0.4445(2) 0.0637(13) Uani 1 d . .
H12 H 0.5106(8) 0.3941(4) 0.4839(2) 0.076 Uiso 1 calc R .
C13 C 0.7411(9) 0.3290(4) 0.4326(2) 0.0753(13) Uani 1 d . .
H13 H 0.8364(9) 0.3430(4) 0.4638(2) 0.090 Uiso 1 calc R .
C14 C 0.7954(6) 0.2770(4) 0.3746(2) 0.0626(13) Uani 1 d . .
H14 H 0.9271(6) 0.2547(4) 0.3674(2) 0.075 Uiso 1 calc R .
C15 C 0.5694(6) 0.2383(4) 0.0725(2) 0.0657(13) Uani 1 d . .
H15A H 0.4276(6) 0.2433(4) 0.0737(2) 0.099 Uiso 1 calc R .
H15B H 0.6091(6) 0.1481(4) 0.0634(2) 0.099 Uiso 1 calc R .
H15C H 0.6186(6) 0.2967(4) 0.0399(2) 0.099 Uiso 1 calc R .
C16 C 0.9865(5) 0.1480(3) 0.1288(2) 0.0563(12) Uani 1 d . .
H16A H 0.9371(5) 0.0793(3) 0.1564(2) 0.084 Uiso 1 calc R .
H16B H 1.1259(5) 0.1592(3) 0.1357(2) 0.084 Uiso 1 calc R .
H16C H 0.9634(5) 0.1231(3) 0.0854(2) 0.084 Uiso 1 calc R .
O O 1.0751(4) 0.3433(2) 0.24083(13) 0.0561(7) Uani 1 d . .
H0 H 1.1084(27) 0.4214(11) 0.2357(18) 0.084 Uiso 1 calc R .
P P 0.7531(2) 0.18143(8) 0.25356(4) 0.0419(3) Uani 1 d . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 P 106.4(2) . . ?
C15 C2 C3 116.0(3) . . ?
C15 C2 C1 110.4(3) . . ?
C3 C2 C1 109.6(3) . . ?
C15 C2 C6 113.8(3) . . ?
C3 C2 C6 94.1(3) . . ?
C1 C2 C6 112.2(3) . . ?
C16 C3 C8 113.5(3) . . ?
C16 C3 C2 117.9(3) . . ?
C8 C3 C2 104.0(3) . . ?
C16 C3 C4 115.2(3) . . ?
C8 C3 C4 109.2(3) . . ?
C2 C3 C4 95.1(3) . . ?
O C4 C5 115.0(3) . . ?
O C4 C3 115.9(3) . . ?
C5 C4 C3 102.2(3) . . ?
O C4 P 111.1(2) . . ?
C5 C4 P 109.6(2) . . ?
C3 C4 P 101.9(2) . . ?
C6 C5 C4 103.0(3) . . ?
C7 C6 C5 105.6(3) . . ?
C7 C6 C2 102.3(3) . . ?
C5 C6 C2 102.0(3) . . ?
C8 C7 C6 102.0(3) . . ?
C7 C8 C3 105.2(3) . . ?
C10 C9 C14 117.4(3) . . ?
C10 C9 P 126.9(3) . . ?
C14 C9 P 115.6(3) . . ?
C9 C10 C11 121.6(4) . . ?
C12 C11 C10 119.9(4) . . ?
C13 C12 C11 119.5(4) . . ?
C12 C13 C14 120.3(4) . . ?
C13 C14 C9 121.4(4) . . ?
C9 P C1 108.2(2) . . ?
C9 P C4 103.3(2) . . ?
C1 P C4 87.3(2) . . ?
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
C1 C2 1.547(5) . ?
C1 P 1.855(3) . ?
C2 C15 1.533(5) . ?
C2 C3 1.538(5) . ?
C2 C6 1.550(5) . ?
C3 C16 1.517(5) . ?
C3 C8 1.537(5) . ?
C3 C4 1.557(5) . ?
C4 O 1.424(4) . ?
C4 C5 1.540(5) . ?
C4 P 1.865(3) . ?
C5 C6 1.537(5) . ?
C6 C7 1.531(5) . ?
C7 C8 1.522(5) . ?
C9 C10 1.370(5) . ?
C9 C14 1.395(5) . ?
C9 P 1.827(3) . ?
C10 C11 1.389(5) . ?
C11 C12 1.379(5) . ?
C12 C13 1.368(6) . ?
C13 C14 1.376(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9371318
2 PubChem 11161282
