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_7244756
_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 H22 O4 P, 0.5(H2 O), C2 H8 N'
_chemical_formula_sum            'C16 H31 N O4.5 P'
_chemical_formula_weight         340.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 96.253(5)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.3882(9)
_cell_length_b                   16.3684(7)
_cell_length_c                   24.7963(13)
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      19.7100
_cell_measurement_theta_min      2.5430
_cell_volume                     7418.9(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.907
_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    -99.96  16.04   1.00    4.00    --   -8.99 -59.25  20.08  116
  2  \f   -166.27  33.73   1.00    4.00  81.87  -8.99  31.50    --   200
  3  \w    -99.96  16.04   1.00    4.00    --   -8.99 -59.25 -51.92  116
  4  \w    -99.96  16.04   1.00    4.00    --   -8.99 -59.25-123.92  116
  5  \f    -31.92 152.08   1.00    4.00  16.67  -8.99 -59.25    --   184
  6  \w    -99.96  16.04   1.00    4.00    --   -8.99 -59.25  92.08  116
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0180784000
_diffrn_orient_matrix_UB_12      -0.0329841000
_diffrn_orient_matrix_UB_13      0.0143137000
_diffrn_orient_matrix_UB_21      0.0037211000
_diffrn_orient_matrix_UB_22      -0.0200020000
_diffrn_orient_matrix_UB_23      -0.0249033000
_diffrn_orient_matrix_UB_31      0.0341635000
_diffrn_orient_matrix_UB_32      0.0197492000
_diffrn_orient_matrix_UB_33      -0.0013133000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1115
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            275714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.776
_diffrn_reflns_theta_min         1.493
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.219
_exptl_crystal_description       needle
_exptl_crystal_F_000             2960
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.175
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     885
_refine_ls_number_reflns         26984
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+1.5960P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15567
_reflns_number_total             26984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00172a2.cif
_cod_data_source_block           rm_tp_l_dmft_autored
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H62 N2 O9 P2'
_cod_original_formula_weight         680.77
_cod_original_formula_moiety         '2(C14 H22 O4 P), H2 O, 2(C2 H8 N)'
_cod_original_formula_units_Z            8
_cod_database_code               7244756
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.942
_reflns_odcompleteness_completeness 90.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.70
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H2WA,H2WB} of O2W, All N(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H1WA,H1WB} of O1W
2. Restrained distances
 N1-H1A = N1-H1B = N2-H2A = N2-H2B = N3-H3A = N3-H3B = N4-H4A = N4-H4B
 0.88 with sigma of 0.02
 O14-H14 = O24-H24 = O34-H34 = O44-H44 = O2W-H2WB
 0.84 with sigma of 0.02
 O2W-H2WA
 0.949 with sigma of 0.02
 O2W-H2WB
 1.009 with sigma of 0.02
3.a Free rotating group:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C33(H33), C46(H46), C31(H31), C19(H19), C5(H5), C18(H18),
 C45(H45), C17(H17), C47(H47), C32(H32)
3.c Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C14(H14A,H14B,H14C), C38(H38A,H38B,
 H38C), C55(H55A,H55B,H55C), C51(H51A,H51B,H51C), C56(H56A,H56B,H56C), C27(H27A,
 H27B,H27C), C40(H40A,H40B,H40C), C50(H50A,H50B,H50C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C54(H54A,H54B,H54C), C42(H42A,H42B,H42C), C8(H8A,H8B,H8C),
  C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C22(H22A,H22B,
 H22C), C9(H9A,H9B,H9C), C52(H52A,H52B,H52C), C41(H41A,H41B,H41C), C3N(H3NA,
 H3NB,H3NC), C10(H10A,H10B,H10C), C6N(H6NA,H6NB,H6NC), C4N(H4NA,H4NB,H4NC),
 C23(H23A,H23B,H23C), C1N(H1NA,H1NB,H1NC), C5N(H5NA,H5NB,H5NC), C8N(H8NA,H8NB,
 H8NC), C7N(H7NA,H7NB,H7NC), C2N(H2NA,H2NB,H2NC)
;
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.667