#------------------------------------------------------------------------------
#$Date: 2020-06-05 12:41:54 +0200 (vie 05 de jun de 2020) $
#$Revision: 252766 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/39/7703905.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_7703905
loop_
_publ_author_name
'Pearce, Kyle G.'
'Simenok, Vladimir'
'Crossley, Ian R.'
_publ_section_title
;
 Phosphacycloalkyldiones: synthesis and coordinative behaviour of 6- and
 7-member cyclic diketophosphanyls.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5482
_journal_page_last               5492
_journal_paper_doi               10.1039/d0dt00864h
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C14 H17 O2 P'
_chemical_formula_sum            'C14 H17 O2 P'
_chemical_formula_weight         248.24
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-03-04 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.452(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8705(3)
_cell_length_b                   9.7423(2)
_cell_length_c                   11.9176(2)
_cell_measurement_reflns_used    2898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.4210
_cell_measurement_theta_min      4.0620
_cell_volume                     1259.83(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1033
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  92.00   1.00    4.60    --   37.91 178.00 150.00   52
  2  ω     -6.00  64.00   1.00    4.60    --   37.91 -99.00-180.00   70
  3  ω     57.00 105.00   1.00    4.60    --   37.91 178.00  90.00   48
  4  ω     21.00  96.00   1.00    4.60    --   37.91  57.00 -90.00   75
  5  ω     93.00 167.00   1.00   18.40    --  107.00  61.00  60.00   74
  6  ω     42.00  69.00   1.00   18.40    --  107.00-111.00-150.00   27
  7  ω     84.00 120.00   1.00   18.40    --  107.00  77.00 150.00   36
  8  ω     38.00  79.00   1.00   18.40    --  107.00 -95.00 -60.00   41
  9  ω     55.00 123.00   1.00   18.40    --  107.00 -61.00 -60.00   68
 10  ω     51.00  78.00   1.00   18.40    --  107.00 -95.00-120.00   27
 11  ω     39.00  64.00   1.00   18.40    --  107.00 -95.00  90.00   25
 12  ω     92.00 171.00   1.00   18.40    --  107.00  45.00   0.00   79
 13  ω    150.00 175.00   1.00   18.40    --  107.00  77.00 150.00   25
 14  ω     89.00 170.00   1.00   18.40    --  107.00  77.00  30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0663558000
_diffrn_orient_matrix_UB_12      -0.1392881000
_diffrn_orient_matrix_UB_13      0.0132216000
_diffrn_orient_matrix_UB_21      -0.0016084000
_diffrn_orient_matrix_UB_22      -0.0140546000
_diffrn_orient_matrix_UB_23      -0.1288788000
_diffrn_orient_matrix_UB_31      0.1255287000
_diffrn_orient_matrix_UB_32      0.0733385000
_diffrn_orient_matrix_UB_33      0.0001229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.722
_diffrn_reflns_theta_min         4.074
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0344
_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)+(0.0400P)²+0.8441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2237
_reflns_number_total             2407
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00864h2.cif
_cod_data_source_block           compound-2e
_cod_depositor_comments
'Adding full bibliography for 7703903--7703909.cif.'
_cod_database_code               7703905
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C14 H17 O2 P1 '
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C4(H4a,H4b), C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C14(H14a,H14b,H14c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.160
_oxdiff_exptl_absorpt_empirical_full_min 0.690
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.30834(3) 0.39894(4) 0.69063(3) 0.01355(13) Uani 1 1 d . . . . .
O1 O 0.34667(10) 0.66697(12) 0.73565(10) 0.0204(3) Uani 1 1 d . . . . .
O2 O 0.09505(11) 0.26342(13) 0.64969(11) 0.0249(3) Uani 1 1 d . . . . .
C6 C 0.29690(14) 0.44146(16) 0.54205(12) 0.0130(3) Uani 1 1 d . . . . .
C11 C 0.20688(13) 0.53093(16) 0.49242(13) 0.0138(3) Uani 1 1 d . . . . .
C7 C 0.38291(13) 0.37823(16) 0.47444(13) 0.0135(3) Uani 1 1 d . . . . .
C8 C 0.37729(14) 0.40556(16) 0.35956(13) 0.0153(3) Uani 1 1 d . . . . .
H8 H 0.434732 0.364865 0.315301 0.018 Uiso 1 1 calc R . . . .
C9 C 0.28853(15) 0.49172(16) 0.30910(13) 0.0161(3) Uani 1 1 d . . . . .
C10 C 0.20397(14) 0.55352(16) 0.37670(13) 0.0152(3) Uani 1 1 d . . . . .
H10 H 0.144054 0.611335 0.343749 0.018 Uiso 1 1 calc R . . . .
C12 C 0.48160(14) 0.28075(17) 0.52096(13) 0.0169(3) Uani 1 1 d . . . . .
H12A H 0.527905 0.323774 0.582451 0.025 Uiso 1 1 calc GR . . . .
H12B H 0.535790 0.258050 0.463028 0.025 Uiso 1 1 calc GR . . . .
H12C H 0.443733 0.198569 0.546933 0.025 Uiso 1 1 calc GR . . . .
C1 C 0.30517(14) 0.56158(17) 0.77108(13) 0.0161(3) Uani 1 1 d . . . . .
C14 C 0.11481(14) 0.60746(17) 0.55883(13) 0.0169(3) Uani 1 1 d . . . . .
H14A H 0.076317 0.544778 0.608054 0.025 Uiso 1 1 calc GR . . . .
H14B H 0.053173 0.648077 0.508149 0.025 Uiso 1 1 calc GR . . . .
H14C H 0.156383 0.678170 0.602519 0.025 Uiso 1 1 calc GR . . . .
C5 C 0.15548(14) 0.32739(17) 0.72094(14) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.28454(17) 0.51818(18) 0.18458(14) 0.0226(4) Uani 1 1 d . . . . .
H13A H 0.361161 0.558083 0.165156 0.034 Uiso 1 1 calc GR . . . .
H13B H 0.218255 0.580168 0.164250 0.034 Uiso 1 1 calc GR . . . .
H13C H 0.271665 0.433170 0.144852 0.034 Uiso 1 1 calc GR . . . .
C2 C 0.25797(16) 0.5487(2) 0.88738(14) 0.0240(4) Uani 1 1 d . . . . .
H2A H 0.258482 0.638525 0.922475 0.029 Uiso 1 1 calc R . . . .
H2B H 0.313131 0.489815 0.932677 0.029 Uiso 1 1 calc R . . . .
C4 C 0.11739(16) 0.34298(19) 0.84043(15) 0.0242(4) Uani 1 1 d . . . . .
H4A H 0.168589 0.283546 0.888971 0.029 Uiso 1 1 calc R . . . .
H4B H 0.032789 0.312336 0.843778 0.029 Uiso 1 1 calc R . . . .
C3 C 0.12749(16) 0.4896(2) 0.88560(15) 0.0258(4) Uani 1 1 d . . . . .
H3A H 0.099678 0.491070 0.961411 0.031 Uiso 1 1 calc R . . . .
H3B H 0.072832 0.548185 0.839544 0.031 Uiso 1 1 calc R . . . .
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'
P P 0.2955 0.4335 '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
C6 P1 C1 107.89(7) . . ?
C6 P1 C5 105.41(7) . . ?
C1 P1 C5 100.11(7) . . ?
C11 C6 P1 123.64(11) . . ?
C7 C6 P1 116.63(11) . . ?
C7 C6 C11 119.73(14) . . ?
C6 C11 C14 123.32(14) . . ?
C10 C11 C6 119.01(14) . . ?
C10 C11 C14 117.65(14) . . ?
C6 C7 C12 122.96(14) . . ?
C8 C7 C6 119.10(14) . . ?
C8 C7 C12 117.94(14) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 121.99(14) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 118.41(14) . . ?
C8 C9 C13 120.59(15) . . ?
C10 C9 C13 121.00(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 C11 121.76(14) . . ?
C9 C10 H10 119.1 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C1 P1 121.80(12) . . ?
O1 C1 C2 123.07(15) . . ?
C2 C1 P1 114.90(12) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C5 P1 120.62(13) . . ?
O2 C5 C4 122.83(15) . . ?
C4 C5 P1 116.34(12) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.59(14) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C5 C4 C3 114.02(14) . . ?
H4A C4 H4B 107.6 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 C2 113.80(15) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
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
P1 C6 1.8154(15) . ?
P1 C1 1.8534(17) . ?
P1 C5 1.8574(16) . ?
O1 C1 1.208(2) . ?
O2 C5 1.214(2) . ?
C6 C11 1.413(2) . ?
C6 C7 1.412(2) . ?
C11 C10 1.395(2) . ?
C11 C14 1.510(2) . ?
C7 C8 1.392(2) . ?
C7 C12 1.513(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(2) . ?
C9 C10 1.395(2) . ?
C9 C13 1.504(2) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C1 C2 1.512(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C5 C4 1.514(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.530(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.528(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
