#------------------------------------------------------------------------------
#$Date: 2020-04-24 23:30:29 +0300 (Fri, 24 Apr 2020) $
#$Revision: 251155 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038300.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_4038300
loop_
_publ_author_name
'Guo, Jiami'
'Mao, Chenlu'
'Deng, Bin'
'Ye, Liyi'
'Yin, Yingwu'
'Gao, Yuxing'
'Tu, Song'
_publ_section_title
;
 Azobisisobutyronitrile-Initiated Oxidative C-H Functionalization of
 Simple Alcohols with Diaryl(arylethynyl)phosphine Oxides: A Metal-Free
 Approach toward Hydroxymethyl Benzo[b]phosphole Oxides and
 6H-Indeno[2,1-b]phosphindole 5-Oxide Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00118
_journal_year                    2020
_chemical_formula_moiety         'C22 H19 O2 P'
_chemical_formula_sum            'C22 H19 O2 P'
_chemical_formula_weight         346.34
_chemical_name_systematic
'2-(1-hydroxyethyl)-1,3-diphenylphosphindole 1-oxide'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.412(4)
_cell_angle_beta                 113.277(4)
_cell_angle_gamma                107.356(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5029(4)
_cell_length_b                   10.3608(5)
_cell_length_c                   11.0975(4)
_cell_measurement_reflns_used    4331
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9430
_cell_measurement_theta_min      4.5680
_cell_volume                     907.31(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9366
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.734
_diffrn_reflns_theta_min         4.580
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52865
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0491
_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)+(0.0823P)²+0.4855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3014
_reflns_number_total             3410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00118_si_001.cif
_cod_data_source_block           exp_2209
_cod_original_cell_volume        907.31(7)
_cod_database_code               4038300
_shelxl_version_number           2014/6
_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.
;
_shelx_estimated_absorpt_t_max   0.932
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C22(H22), C21(H21), C20(H20), C18(H18), C10(H10),
 C14(H14), C6(H6), C19(H19), C12(H12), C13(H13), C11(H11)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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 0.74253(6) 0.77298(5) 0.89291(5) 0.02294(19) Uani 1 1 d . . . . .
O1 O 0.87644(18) 0.86849(16) 1.03397(14) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.79561(19) 1.07266(16) 0.85533(15) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.8969 1.0948 0.8930 0.045 Uiso 1 1 calc GR . . . .
C3 C 0.7757(2) 0.6092(2) 0.7076(2) 0.0244(4) Uani 1 1 d . . . . .
C4 C 0.7958(3) 0.4953(2) 0.6416(2) 0.0279(4) Uani 1 1 d . . . . .
H4 H 0.8024 0.4913 0.5598 0.033 Uiso 1 1 calc R . . . .
C2 C 0.7669(2) 0.7370(2) 0.6650(2) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.7614(3) 0.6108(2) 0.8290(2) 0.0251(4) Uani 1 1 d . . . . .
C17 C 0.5387(3) 0.7312(2) 0.8809(2) 0.0238(4) Uani 1 1 d . . . . .
C9 C 0.7932(3) 0.7583(2) 0.5445(2) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.7415(3) 0.8293(2) 0.7464(2) 0.0246(4) Uani 1 1 d . . . . .
C5 C 0.8061(3) 0.3866(2) 0.7002(2) 0.0299(5) Uani 1 1 d . . . . .
H5 H 0.8207 0.3105 0.6569 0.036 Uiso 1 1 calc R . . . .
C7 C 0.7718(3) 0.5031(2) 0.8866(2) 0.0282(5) Uani 1 1 d . . . . .
H7 H 0.7634 0.5059 0.9676 0.034 Uiso 1 1 calc R . . . .
C22 C 0.5236(3) 0.8240(2) 0.9768(2) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.6176 0.9016 1.0465 0.033 Uiso 1 1 calc R . . . .
C15 C 0.7193(3) 0.9642(2) 0.7263(2) 0.0272(4) Uani 1 1 d . . . . .
H15 H 0.7708 0.9976 0.6700 0.033 Uiso 1 1 calc R . . . .
C21 C 0.3671(3) 0.7998(2) 0.9675(2) 0.0284(5) Uani 1 1 d . . . . .
H21 H 0.3562 0.8616 1.0308 0.034 Uiso 1 1 calc R . . . .
C20 C 0.2278(3) 0.6839(3) 0.8641(2) 0.0320(5) Uani 1 1 d . . . . .
H20 H 0.1234 0.6677 0.8586 0.038 Uiso 1 1 calc R . . . .
C18 C 0.3981(3) 0.6155(2) 0.7767(2) 0.0309(5) Uani 1 1 d . . . . .
H18 H 0.4084 0.5544 0.7123 0.037 Uiso 1 1 calc R . . . .
C10 C 0.9542(3) 0.7993(2) 0.5593(2) 0.0316(5) Uani 1 1 d . . . . .
H10 H 1.0424 0.8095 0.6421 0.038 Uiso 1 1 calc R . . . .
C14 C 0.6630(3) 0.7417(3) 0.4197(2) 0.0334(5) Uani 1 1 d . . . . .
H14 H 0.5551 0.7145 0.4091 0.040 Uiso 1 1 calc R . . . .
C6 C 0.7951(3) 0.3899(2) 0.8213(2) 0.0310(5) Uani 1 1 d . . . . .
H6 H 0.8032 0.3171 0.8591 0.037 Uiso 1 1 calc R . . . .
C16 C 0.5354(3) 0.9399(3) 0.6548(2) 0.0336(5) Uani 1 1 d . . . . .
H16A H 0.4843 0.9073 0.7095 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.4798 0.8692 0.5650 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.5263 1.0278 0.6447 0.050 Uiso 1 1 calc GR . . . .
C19 C 0.2427(3) 0.5912(3) 0.7684(2) 0.0342(5) Uani 1 1 d . . . . .
H19 H 0.1486 0.5133 0.6991 0.041 Uiso 1 1 calc R . . . .
C12 C 0.8525(4) 0.8083(3) 0.3262(3) 0.0395(6) Uani 1 1 d . . . . .
H12 H 0.8724 0.8259 0.2536 0.047 Uiso 1 1 calc R . . . .
C13 C 0.6918(3) 0.7653(3) 0.3103(2) 0.0405(6) Uani 1 1 d . . . . .
H13 H 0.6033 0.7522 0.2264 0.049 Uiso 1 1 calc R . . . .
C11 C 0.9831(3) 0.8251(3) 0.4500(3) 0.0377(6) Uani 1 1 d . . . . .
H11 H 1.0910 0.8538 0.4607 0.045 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
O1 P1 C8 115.84(9) . . ?
O1 P1 C17 111.21(9) . . ?
O1 P1 C1 117.86(9) . . ?
C8 P1 C1 92.30(9) . . ?
C17 P1 C8 109.70(10) . . ?
C17 P1 C1 108.40(9) . . ?
C15 O2 H2 109.5 . . ?
C4 C3 C2 127.44(19) . . ?
C4 C3 C8 119.51(19) . . ?
C8 C3 C2 113.05(18) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C2 C9 120.22(18) . . ?
C1 C2 C3 114.76(18) . . ?
C1 C2 C9 124.96(19) . . ?
C3 C8 P1 109.37(15) . . ?
C7 C8 P1 129.24(16) . . ?
C7 C8 C3 121.28(19) . . ?
C22 C17 P1 117.56(16) . . ?
C18 C17 P1 122.27(16) . . ?
C18 C17 C22 120.09(19) . . ?
C10 C9 C2 118.86(19) . . ?
C14 C9 C2 121.95(19) . . ?
C14 C9 C10 119.17(19) . . ?
C2 C1 P1 110.30(15) . . ?
C2 C1 C15 127.08(19) . . ?
C15 C1 P1 122.60(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5 119.3 . . ?
C8 C7 H7 120.5 . . ?
C8 C7 C6 119.02(19) . . ?
C6 C7 H7 120.5 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
O2 C15 C1 110.87(17) . . ?
O2 C15 H15 109.1 . . ?
O2 C15 C16 106.83(17) . . ?
C1 C15 H15 109.1 . . ?
C1 C15 C16 111.88(18) . . ?
C16 C15 H15 109.1 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 119.96(19) . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 119.8 . . ?
C21 C20 C19 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C14 H14 119.7 . . ?
C9 C14 C13 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
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 O1 1.4889(15) . ?
P1 C8 1.802(2) . ?
P1 C17 1.798(2) . ?
P1 C1 1.813(2) . ?
O2 H2 0.8200 . ?
O2 C15 1.417(3) . ?
C3 C4 1.389(3) . ?
C3 C2 1.491(3) . ?
C3 C8 1.404(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C2 C9 1.492(3) . ?
C2 C1 1.347(3) . ?
C8 C7 1.384(3) . ?
C17 C22 1.396(3) . ?
C17 C18 1.389(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.385(3) . ?
C1 C15 1.513(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.397(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.390(3) . ?
C15 H15 0.9800 . ?
C15 C16 1.524(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.383(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.392(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.389(3) . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 H19 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C12 C11 1.380(4) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
