A Chiral Phosphoramidite Reagent for the Synthesis of Inositol Phosphates.
Durantie, Estelle; Huwiler, Samuel; Leroux, Jean-Christophe; Castagner, Bastien; Organic letters 18 (2016) 3162–3165; doi:10.1021/acs.orglett.6b01374

data_1555591
_publ_section_title
;
 A Chiral Phosphoramidite Reagent for the Synthesis of Inositol
 Phosphates.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3162
_journal_page_last               3165
_journal_paper_doi               10.1021/acs.orglett.6b01374
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C44 H50 O12 P2, C H2 Cl2'
_chemical_formula_sum            'C45 H52 Cl2 O12 P2'
_chemical_formula_weight         917.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.589(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3931(4)
_cell_length_b                   9.5262(3)
_cell_length_c                   17.8614(5)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      66.73
_cell_measurement_theta_min      2.53
_cell_volume                     2232.40(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27902
_diffrn_reflns_point_group_measured_fraction_full 0.741
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.726
_diffrn_reflns_theta_min         2.525
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_T_max  0.7376
_exptl_absorpt_correction_T_min  0.6277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0968 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.8510.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.033(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0629P)^2^+0.0995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.468
_reflns_Friedel_fraction_full    0.506
_reflns_Friedel_fraction_max     0.516
_reflns_number_gt                5605
_reflns_number_total             5990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01374_si_001.cif
_cod_data_source_block           cu_pa240614_0m_10a
_cod_database_code               1555591
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.634
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C19(H19), C27(H27), C34(H34),
 C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C23(H23), C24(H24), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33),
  C40(H40), C1A(H1A), C1B(H1B), C1C(H1C)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C)
;
_olex2_submission_original_sample_id pa240614
_olex2_submission_special_instructions 'No special instructions were received'