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_7244757
_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
'2(C14 H22 O4 P), C14 H23 O4 P, C10 H10 N2, C H4 O'
_chemical_formula_sum            'C53 H81 N2 O13 P3'
_chemical_formula_weight         1047.10
_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   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                83.418(2)
_cell_angle_beta                 76.743(2)
_cell_angle_gamma                83.110(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4795(3)
_cell_length_b                   12.8571(4)
_cell_length_c                   21.1268(4)
_cell_measurement_reflns_used    25996
_cell_measurement_temperature    103(4)
_cell_measurement_theta_max      30.1740
_cell_measurement_theta_min      1.6640
_cell_volume                     2739.47(13)
_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      103(4)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.998
_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   -349.73  10.27   1.00    2.00   6.61  -9.84 -31.50    --   360
  2  \w    -60.88   0.12   1.00    2.00    --  -14.77  94.56 -34.84   61
  3  \w    -65.46  -0.46   1.00    2.00    --  -19.34  94.56 145.16   65
  4  \w   -100.81  15.19   1.00    2.00    --   -9.84 -59.25 164.08  116
  5  \w    -65.46  -0.46   1.00    2.00    --  -19.34  94.56  73.16   65
  6  \f    -10.27 349.73   1.00    2.00  81.02  -9.84  31.50    --   360
  7  \w    -65.46  -0.46   1.00    2.00    --  -19.34  94.56   1.16   65
  8  \f   -339.92  20.08   1.00    2.00  15.81  -9.84 -59.25    --   360
;
_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      0.0547385000
_diffrn_orient_matrix_UB_12      -0.0384054000
_diffrn_orient_matrix_UB_13      -0.0064688000
_diffrn_orient_matrix_UB_21      0.0418834000
_diffrn_orient_matrix_UB_22      0.0403669000
_diffrn_orient_matrix_UB_23      -0.0127841000
_diffrn_orient_matrix_UB_31      0.0114367000
_diffrn_orient_matrix_UB_32      0.0029624000
_diffrn_orient_matrix_UB_33      0.0315313000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            109711
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.602
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71853
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.515
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         9644
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0622P)^2^+1.7218P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8227
_reflns_number_total             9644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00172a2.cif
_cod_data_source_block           rm_tp_8_153_3_autored
_cod_database_code               7244757
_shelxl_version_number           2012-9
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 79.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.85
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O34-H34 = O24-H24 = O3-H3 = O4-H4
 0.84 with sigma of 0.02
 N1-H1 = N2-H2
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C43(H43), C52(H52), C49(H49), C47(H47), C44(H44), C17(H17),
 C50(H50), C18(H18), C46(H46), C3(H3A), C51(H51), C5(H5), C4(H4A), C33(H33),
 C31(H31), C32(H32)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C23(H23A,H23B,
 H23C), C12(H12A,H12B,H12C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C36(H36A,
 H36B,H36C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C8(H8A,H8B,H8C),
 C42(H42A,H42B,H42C), C9(H9A,H9B,H9C), C38(H38A,H38B,H38C), C37(H37A,H37B,H37C),
  C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C2M(H2MA,H2MB,H2MC), C10(H10A,H10B,
 H10C)
;