#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/14/2221482.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_2221482
loop_
_publ_author_name
'Marimuthu, Thashree'
'Bala, Muhammad D.'
'Friedrich, Holger B.'
_publ_section_title
;
 2,8-Dimethyl-10-p-tolyl-10H-phenoxaphosphine
;
_journal_coeditor_code           RZ2300
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o828
_journal_paper_doi               10.1107/S1600536809009817
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H19 O P'
_chemical_formula_moiety         'C21 H19 O P'
_chemical_formula_sum            'C21 H19 O P'
_chemical_formula_weight         318.33
_chemical_name_common
;
2,8-Dimethyl-10-p-tolyl-10H-phenoxaphosphine
;
_chemical_name_systematic
;
3,6-dimethyl-10-p-tolyl-9-oxa-10-phosphaanthracene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0
_cell_angle_beta                 111.5320(10)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   10.9363(3)
_cell_length_b                   11.6323(3)
_cell_length_c                   14.0458(4)
_cell_measurement_reflns_used    8225
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.34
_cell_volume                     1662.13(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29900
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                3507
_reflns_number_total             4013
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2300.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221482
_cod_database_fobs_code          2221482
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.59638(12) 1.06591(11) 0.15703(10) 0.0274(3) Uani d . 1 . .
C C2 0.53669(13) 1.05047(12) 0.22849(10) 0.0303(3) Uani d . 1 . .
H H2 0.5484 0.9791 0.2636 0.036 Uiso calc R 1 . .
C C3 0.46153(13) 1.13388(12) 0.25049(10) 0.0313(3) Uani d . 1 . .
C C4 0.44183(14) 1.23579(12) 0.19518(11) 0.0361(3) Uani d . 1 . .
H H4 0.3880 1.2940 0.2069 0.043 Uiso calc R 1 . .
C C5 0.49875(14) 1.25429(12) 0.12363(11) 0.0357(3) Uani d . 1 . .
H H5 0.4843 1.3247 0.0868 0.043 Uiso calc R 1 . .
C C6 0.57734(13) 1.16977(11) 0.10547(10) 0.0289(3) Uani d . 1 . .
C C7 0.69900(12) 1.12246(11) -0.00204(10) 0.0284(3) Uani d . 1 . .
C C8 0.73269(14) 1.16321(12) -0.08200(10) 0.0340(3) Uani d . 1 . .
H H8 0.7092 1.2391 -0.1071 0.041 Uiso calc R 1 . .
C C9 0.80050(14) 1.09313(13) -0.12506(10) 0.0347(3) Uani d . 1 . .
H H9 0.8246 1.1222 -0.1789 0.042 Uiso calc R 1 . .
C C10 0.83423(13) 0.98126(12) -0.09135(10) 0.0310(3) Uani d . 1 . .
C C11 0.79734(12) 0.94259(11) -0.01249(10) 0.0294(3) Uani d . 1 . .
H H11 0.8177 0.8657 0.0106 0.035 Uiso calc R 1 . .
C C12 0.73184(12) 1.01137(11) 0.03436(9) 0.0264(2) Uani d . 1 . .
C C13 0.40629(15) 1.11516(14) 0.33266(11) 0.0399(3) Uani d . 1 . .
H H13A 0.3553 1.0437 0.3190 0.060 Uiso calc R 1 . .
H H13B 0.3491 1.1798 0.3333 0.060 Uiso calc R 1 . .
H H13C 0.4784 1.1098 0.3993 0.060 Uiso calc R 1 . .
C C14 0.90781(15) 0.90328(14) -0.13659(11) 0.0387(3) Uani d . 1 . .
H H14A 0.9981 0.8935 -0.0878 0.058 Uiso calc R 1 . .
H H14B 0.9093 0.9371 -0.2001 0.058 Uiso calc R 1 . .
H H14C 0.8641 0.8283 -0.1515 0.058 Uiso calc R 1 . .
C C15 0.85437(13) 0.98293(12) 0.24735(9) 0.0286(3) Uani d . 1 . .
C C16 0.94457(15) 0.89406(13) 0.28148(11) 0.0377(3) Uani d . 1 . .
H H16 0.9249 0.8209 0.2493 0.045 Uiso calc R 1 . .
C C17 1.06328(16) 0.91088(17) 0.36216(12) 0.0474(4) Uani d . 1 . .
H H17 1.1246 0.8494 0.3837 0.057 Uiso calc R 1 . .
C C18 1.09347(15) 1.01549(17) 0.41141(11) 0.0463(4) Uani d . 1 . .
C C19 1.00354(15) 1.10404(16) 0.37752(11) 0.0440(4) Uani d . 1 . .
H H19 1.0230 1.1767 0.4106 0.053 Uiso calc R 1 . .
C C20 0.88574(14) 1.08866(13) 0.29636(11) 0.0358(3) Uani d . 1 . .
H H20 0.8258 1.1509 0.2739 0.043 Uiso calc R 1 . .
C C21 1.22049(18) 1.0331(2) 0.50093(13) 0.0681(6) Uani d . 1 . .
H H21A 1.2587 1.1074 0.4940 0.102 Uiso calc R 1 . .
H H21B 1.2821 0.9713 0.5024 0.102 Uiso calc R 1 . .
H H21C 1.2033 1.0322 0.5647 0.102 Uiso calc R 1 . .
O O1 0.63326(10) 1.20048(8) 0.03575(8) 0.0356(2) Uani d . 1 . .
P P1 0.69921(3) 0.95166(3) 0.14160(2) 0.02660(11) Uani d . 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'
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
C6 C1 C2 . . 117.93(12) ?
C6 C1 P1 . . 124.10(10) ?
C2 C1 P1 . . 117.92(10) ?
C3 C2 C1 . . 123.08(12) ?
C3 C2 H2 . . 118.5 ?
C1 C2 H2 . . 118.5 ?
C2 C3 C4 . . 117.25(12) ?
C2 C3 C13 . . 120.76(13) ?
C4 C3 C13 . . 121.98(13) ?
C5 C4 C3 . . 121.42(13) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 119.89(13) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
O1 C6 C1 . . 125.24(12) ?
O1 C6 C5 . . 114.37(12) ?
C1 C6 C5 . . 120.38(12) ?
O1 C7 C8 . . 114.67(12) ?
O1 C7 C12 . . 124.88(11) ?
C8 C7 C12 . . 120.45(12) ?
C9 C8 C7 . . 119.82(13) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 121.47(12) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C11 C10 C9 . . 117.27(12) ?
C11 C10 C14 . . 120.08(13) ?
C9 C10 C14 . . 122.64(12) ?
C10 C11 C12 . . 122.92(12) ?
C10 C11 H11 . . 118.5 ?
C12 C11 H11 . . 118.5 ?
C7 C12 C11 . . 118.04(12) ?
C7 C12 P1 . . 124.12(10) ?
C11 C12 P1 . . 117.81(10) ?
C3 C13 H13A . . 109.5 ?
C3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C20 . . 118.26(13) ?
C16 C15 P1 . . 117.45(11) ?
C20 C15 P1 . . 124.28(11) ?
C15 C16 C17 . . 120.68(15) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C18 C17 C16 . . 120.93(15) ?
C18 C17 H17 . . 119.5 ?
C16 C17 H17 . . 119.5 ?
C17 C18 C19 . . 118.41(14) ?
C17 C18 C21 . . 121.11(18) ?
C19 C18 C21 . . 120.48(19) ?
C18 C19 C20 . . 121.14(16) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C19 C20 C15 . . 120.58(15) ?
C19 C20 H20 . . 119.7 ?
C15 C20 H20 . . 119.7 ?
C18 C21 H21A . . 109.5 ?
C18 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C18 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C6 O1 C7 . . 122.19(10) ?
C1 P1 C12 . . 98.00(6) ?
C1 P1 C15 . . 100.87(6) ?
C12 P1 C15 . . 101.04(6) ?
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
C1 C6 . 1.3845(18) ?
C1 C2 . 1.3953(18) ?
C1 P1 . 1.8046(13) ?
C2 C3 . 1.3780(18) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.390(2) ?
C3 C13 . 1.5021(19) ?
C4 C5 . 1.379(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3896(19) ?
C5 H5 . 0.9500 ?
C6 O1 . 1.3784(15) ?
C7 O1 . 1.3794(16) ?
C7 C8 . 1.3876(18) ?
C7 C12 . 1.3876(18) ?
C8 C9 . 1.382(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.388(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3858(18) ?
C10 C14 . 1.4999(19) ?
C11 C12 . 1.3901(18) ?
C11 H11 . 0.9500 ?
C12 P1 . 1.8092(13) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 C16 . 1.3873(19) ?
C15 C20 . 1.390(2) ?
C15 P1 . 1.8352(13) ?
C16 C17 . 1.389(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.379(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.382(3) ?
C18 C21 . 1.507(2) ?
C19 C20 . 1.383(2) ?
C19 H19 . 0.9500 ?
C20 H20 . 0.9500 ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
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
C6 C1 C2 C3 . . . . -0.7(2) ?
P1 C1 C2 C3 . . . . 176.68(10) ?
C1 C2 C3 C4 . . . . 2.4(2) ?
C1 C2 C3 C13 . . . . -176.31(13) ?
C2 C3 C4 C5 . . . . -2.1(2) ?
C13 C3 C4 C5 . . . . 176.57(13) ?
C3 C4 C5 C6 . . . . 0.2(2) ?
C2 C1 C6 O1 . . . . 177.32(12) ?
P1 C1 C6 O1 . . . . 0.09(19) ?
C2 C1 C6 C5 . . . . -1.29(19) ?
P1 C1 C6 C5 . . . . -178.52(10) ?
C4 C5 C6 O1 . . . . -177.21(13) ?
C4 C5 C6 C1 . . . . 1.5(2) ?
O1 C7 C8 C9 . . . . 179.10(12) ?
C12 C7 C8 C9 . . . . -0.6(2) ?
C7 C8 C9 C10 . . . . 1.1(2) ?
C8 C9 C10 C11 . . . . -0.1(2) ?
C8 C9 C10 C14 . . . . -179.98(13) ?
C9 C10 C11 C12 . . . . -1.45(19) ?
C14 C10 C11 C12 . . . . 178.41(12) ?
O1 C7 C12 C11 . . . . 179.45(12) ?
C8 C7 C12 C11 . . . . -0.86(19) ?
O1 C7 C12 P1 . . . . -2.50(19) ?
C8 C7 C12 P1 . . . . 177.19(10) ?
C10 C11 C12 C7 . . . . 1.94(19) ?
C10 C11 C12 P1 . . . . -176.23(10) ?
C20 C15 C16 C17 . . . . -0.3(2) ?
P1 C15 C16 C17 . . . . -179.07(11) ?
C15 C16 C17 C18 . . . . 1.1(2) ?
C16 C17 C18 C19 . . . . -1.0(2) ?
C16 C17 C18 C21 . . . . 178.23(14) ?
C17 C18 C19 C20 . . . . 0.1(2) ?
C21 C18 C19 C20 . . . . -179.10(14) ?
C18 C19 C20 C15 . . . . 0.6(2) ?
C16 C15 C20 C19 . . . . -0.5(2) ?
P1 C15 C20 C19 . . . . 178.12(11) ?
C1 C6 O1 C7 . . . . 10.4(2) ?
C5 C6 O1 C7 . . . . -170.89(12) ?
C8 C7 O1 C6 . . . . 171.17(12) ?
C12 C7 O1 C6 . . . . -9.1(2) ?
C6 C1 P1 C12 . . . . -8.60(12) ?
C2 C1 P1 C12 . . . . 174.17(10) ?
C6 C1 P1 C15 . . . . 94.34(12) ?
C2 C1 P1 C15 . . . . -82.90(11) ?
C7 C12 P1 C1 . . . . 9.72(12) ?
C11 C12 P1 C1 . . . . -172.23(10) ?
C7 C12 P1 C15 . . . . -93.08(12) ?
C11 C12 P1 C15 . . . . 84.97(11) ?
C16 C15 P1 C1 . . . . 159.40(10) ?
C20 C15 P1 C1 . . . . -19.24(12) ?
C16 C15 P1 C12 . . . . -100.12(11) ?
C20 C15 P1 C12 . . . . 81.24(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655748
