Supramolecular aggregation in sterically encumbered monoarylphosphates and their H-bonded adducts: Multigram synthesis of elusive 2,6-di-tert-butylphenyl phosphate
Prapakaran, T.; Kuppuswamy, Subramaniam; Murugavel, Ramaswamy; CrystEngComm  (2022) –; doi:10.1039/D2CE00172A

data_7244754
_publ_section_title
;
 Supramolecular aggregation in sterically encumbered monoarylphosphates
 and their H-bonded adducts: Multigram synthesis of elusive
 2,6-di-tert-butylphenyl phosphate
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00172A
_journal_year                    2022
_chemical_formula_moiety         'C14 H23 O4 P'
_chemical_formula_sum            'C14 H23 O4 P'
_chemical_formula_weight         286.29
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-31 deposited with the CCDC.	2022-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.575(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3227(5)
_cell_length_b                   13.3902(8)
_cell_length_c                   18.0051(8)
_cell_measurement_reflns_used    2807
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.6010
_cell_measurement_theta_min      2.7160
_cell_volume                     1514.33(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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      150.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_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   -104.00  19.00   1.00    5.00    --  -14.30 -38.00  30.00  123
  2  \w    -48.00  75.00   1.00    5.00    --  -14.30  38.00-180.00  123
  3  \w   -104.00  19.00   1.00    5.00    --  -14.30 -38.00 -90.00  123
  4  \w   -104.00  24.00   1.00    5.00    --  -14.30 -72.00-180.00  128
  5  \w    -53.00  63.00   1.00    5.00    --  -14.30  72.00-120.00  116
  6  \w    -53.00  75.00   1.00    5.00    --  -14.30  72.00   0.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0706085000
_diffrn_orient_matrix_UB_12      0.0405165000
_diffrn_orient_matrix_UB_13      0.0032282000
_diffrn_orient_matrix_UB_21      -0.0816897000
_diffrn_orient_matrix_UB_22      -0.0261693000
_diffrn_orient_matrix_UB_23      -0.0223105000
_diffrn_orient_matrix_UB_31      -0.0332173000
_diffrn_orient_matrix_UB_32      -0.0218828000
_diffrn_orient_matrix_UB_33      0.0326104000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23347
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.277
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.014
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0875
_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^)+(0.0748P)^2^+2.4571P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2159
_reflns_number_total             2675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00172a2.cif
_cod_data_source_block           tp-5-107
_cod_database_code               7244754
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C O P '
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.940
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-H4 = O3-H3
 0.84 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C4(H4A)
3.b Idealised Me refined as rotating group:
 C63(H63A,H63B,H63C), C21(H21A,H21B,H21C), C62(H62A,H62B,H62C), C61(H61A,H61B,
 H61C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 2.884
_oxdiff_exptl_absorpt_empirical_full_min 0.435