The crystal structure of dimethyl ((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)phosphonate, C23H33O4P
Liu, Zhang-Qin; You, Peng-Sheng; Tang, Min; Zhang, Liang-Dong; Liu, Sheng-Shu; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 865–867; doi:10.1515/ncrs-2019-0051

data_8105876
_publ_section_title
;
 The crystal structure of dimethyl
 ((3,5-di-tert-butyl-4-hydroxyphenyl)(phenyl)methyl)phosphonate, C23H33O4P
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              865
_journal_page_last               867
_journal_paper_doi               10.1515/ncrs-2019-0051
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C23 H33 O4 P'
_chemical_formula_sum            'C23 H33 O4 P'
_chemical_formula_weight         404.46
_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     direct
_cell_angle_alpha                90
_cell_angle_beta                 98.201(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4629(3)
_cell_length_b                   11.4909(5)
_cell_length_c                   19.3341(9)
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    298.4(3)
_cell_measurement_theta_max      27.9960
_cell_measurement_theta_min      4.0490
_cell_volume                     2300.73(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)[1]'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)[1]'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)[1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)[2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[2]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[4]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)[3]'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     35.00  89.00   1.00   16.74    --   16.35 178.00 -60.00   54
  2  \w      0.00  84.00   1.00   16.74    --   16.35  57.00 -90.00   84
  3  \w    -51.00  43.00   1.00   16.74    --   16.35 -77.00 -30.00   94
  4  \w    -51.00  33.00   1.00   16.74    --   16.35 -57.00  90.00   84
  5  \w      0.00  25.00   1.00   16.74    --   16.35  57.00-180.00   25
  6  \w    -10.00  84.00   1.00   16.74    --   16.35  77.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0553860000
_diffrn_orient_matrix_UB_12      -0.0334672000
_diffrn_orient_matrix_UB_13      0.0125523000
_diffrn_orient_matrix_UB_21      -0.0402610000
_diffrn_orient_matrix_UB_22      -0.0452368000
_diffrn_orient_matrix_UB_23      0.0094391000
_diffrn_orient_matrix_UB_31      -0.0013288000
_diffrn_orient_matrix_UB_32      -0.0252644000
_diffrn_orient_matrix_UB_33      -0.0336014000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20317
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.546
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5187
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0550
_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/[\s^2^(Fo^2^)+(0.0200P)^2^+2.0000P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3987
_reflns_number_total             5187
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0051_suppl.cif
_cod_data_source_block           gxy0717
_cod_database_code               8105876
_chemical_oxdiff_formula         'C1 H1 O1 N1'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_date_sample_data_collection 2018-07-17
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.770