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_7244759
_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, C6 H13 N2'
_chemical_formula_sum            'C20 H35 N2 O4 P'
_chemical_formula_weight         398.47
_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                 101.019(2)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.7198(4)
_cell_length_b                   15.6597(3)
_cell_length_c                   27.7238(7)
_cell_measurement_reflns_used    12157
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.0100
_cell_measurement_theta_min      2.4670
_cell_volume                     8403.4(3)
_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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_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  \f    -54.27 145.73   1.00    5.00  81.87  -8.99  31.50    --   200
  2  \w    -99.96  16.04   1.00    5.00    --   -8.99 -59.25  92.08  116
  3  \f   -123.80 108.20   1.00    5.00  16.67  -8.99 -59.25    --   232
  4  \w    -99.96  16.04   1.00    5.00    --   -8.99 -59.25  20.08  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      0.0158233000
_diffrn_orient_matrix_UB_12      -0.0347598000
_diffrn_orient_matrix_UB_13      0.0142648000
_diffrn_orient_matrix_UB_21      0.0024062000
_diffrn_orient_matrix_UB_22      0.0249304000
_diffrn_orient_matrix_UB_23      0.0216195000
_diffrn_orient_matrix_UB_31      -0.0329666000
_diffrn_orient_matrix_UB_32      -0.0148789000
_diffrn_orient_matrix_UB_33      0.0029030000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1032
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            184163
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         1.497
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45758
_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    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1021
_refine_ls_number_reflns         18534
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      3.654
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0841P)^2^+0.8624P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11726
_reflns_number_total             18534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00172a2.cif
_cod_data_source_block           rm_tp_8_150_autored
_cod_database_code               7244759
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C20 N2 O4 P'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.954
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O14-H14 = O24-H24 = O34-H34 = O44-H44
 0.84 with sigma of 0.02
 N2-H2 = N4-H4A = N6-H6 = N8-H8
 0.88 with sigma of 0.02
 C14N-H14D = C14N-H14E = C20N-H20A = C20N-H20B = C10N-H10D = C10N-H10E = C13N-
 H13D = C9N-H9NA = C9N-H9NB = C2N-H2NA = C2N-H2NB = C1N-H1NA = C1N-H1NB = C22N-
 H22D = C8N-H3NB = C16N-H16A = C23N-H23D = C3N-H3NB
 0.99 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C14N(H14D,H14E), C20N(H20A,H20B), C10N(H10D,H10E), C13N(H13D,H13E), C9N(H9NA,
 H9NB), C2N(H2NA,H2NB), C19N(H19A,H19B), C18N(H18A,H18B), C17N(H17A,H17B),
 C1N(H1NA,H1NB), C22N(H22D,H22E), C12N(H12D,H12E), C15N(H15A,H15B), C7N(H7NA,
 H7NB), C8N(H8NA,H8NB), C16N(H16A,H16B), C23N(H23D,H23E), C11N(H11A,H11B),
 C3N(H3NA,H3NB), C21N(H21A,H21B), C4N(H4NA,H4NB), C24N(H24D,H24E), C6N(H6NA,
 H6NB), C5N(H5NA,H5NB)
3.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C3(H3), C45(H45), C17(H17), C47(H47), C31(H31), C5(H5), C46(H46),
 C18(H18), C32(H32), C19(H19), C4(H4)
3.c Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C22(H22A,H22B,H22C), C9(H9A,H9B,H9C), C51(H51A,H51B,
 H51C), C13(H13A,H13B,H13C), C41(H41A,H41B,H41C), C28(H28A,H28B,H28C), C36(H36A,
 H36B,H36C), C52(H52A,H52B,H52C), C24(H24A,H24B,H24C), C37(H37A,H37B,H37C),
 C8(H8A,H8B,H8C), C42(H42A,H42B,H42C), C14(H14A,H14B,H14C), C50(H50A,H50B,H50C),
  C26(H26A,H26B,H26C), C38(H38A,H38B,H38C), C56(H56A,H56B,H56C), C12(H12A,H12B,
 H12C), C55(H55A,H55B,H55C), C27(H27A,H27B,H27C), C23(H23A,H23B,H23C), C54(H54A,
 H54B,H54C), C10(H10A,H10B,H10C)
;
_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 1.894
_oxdiff_exptl_absorpt_empirical_full_min 0.714