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_1555592
_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         'C66 H66 O12 P2'
_chemical_formula_sum            'C66 H66 O12 P2'
_chemical_formula_weight         1113.11
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-20
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                71.165(6)
_cell_angle_beta                 81.596(6)
_cell_angle_gamma                89.993(6)
_cell_formula_units_Z            2
_cell_length_a                   11.2057(8)
_cell_length_b                   15.2204(14)
_cell_length_c                   18.506(2)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      48.78
_cell_measurement_theta_min      2.55
_cell_volume                     2951.5(5)
_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 0.564
_diffrn_measured_fraction_theta_max 0.978
_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_unetI/netI     0.1419
_diffrn_reflns_Laue_measured_fraction_full 0.564
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10027
_diffrn_reflns_point_group_measured_fraction_full 0.479
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         50.403
_diffrn_reflns_theta_min         2.553
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_T_max  0.6619
_exptl_absorpt_correction_T_min  0.4546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1250 before and 0.0865 after correction.
The Ratio of minimum to maximum transmission is 0.6868.
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    1.251
_exptl_crystal_description       plate
_exptl_crystal_F_000             1173
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.448
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details
;
 Flack x determined using 2517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1263
_refine_ls_number_reflns         10027
_refine_ls_number_restraints     1949
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1512
_refine_ls_R_factor_gt           0.1275
_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^)+(0.1776P)^2^+13.1266P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2978
_refine_ls_wR_factor_ref         0.3200
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.394
_reflns_Friedel_fraction_max     0.683
_reflns_number_gt                7904
_reflns_number_total             10027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01374_si_001.cif
_cod_data_source_block           cu_pa253214_0m_12a
_cod_depositor_comments
;

2022-04-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C132 H129 O24 P4'
_cod_original_formula_weight         2223.22
_cod_original_formula_moiety         'C66 H63 O12 P2, C66 H66 O12 P2'
_cod_original_formula_units_Z            1
_cod_database_code               1555592
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C03Y)
\\sim Ueq, Uanis(C04D) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C040) \\sim Ueq:
with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C038) \\sim Ueq, Uanis(C03Q) \\sim Ueq, Uanis(C00X) \\sim Ueq,
Uanis(C02S) \\sim Ueq, Uanis(C02X) \\sim Ueq, Uanis(C032) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C011) \\sim Ueq, Uanis(C015) \\sim Ueq, Uanis(C03A) \\sim Ueq,
Uanis(C034) \\sim Ueq, Uanis(C02O) \\sim Ueq, Uanis(C02N) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C03T) \\sim Ueq, Uanis(C03R) \\sim Ueq, Uanis(C04A) \\sim Ueq,
Uanis(C043) \\sim Ueq, Uanis(C03Z) \\sim Ueq, Uanis(C03U) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(O005) \\sim Ueq, Uanis(O008) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O00I) \\sim Ueq, Uanis(O00H) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O00R) \\sim Ueq, Uanis(O00C) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O00B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C01F) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C01U) \\sim Ueq, Uanis(C012) \\sim Ueq, Uanis(C046) \\sim Ueq,
Uanis(C03L) \\sim Ueq, Uanis(C02B) \\sim Ueq, Uanis(C024) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C00W(H00W), C013(H013), C014(H014), C016(H016), C019(H019), C01A(H01W),
 C01C(H01C), C01E(H01E), C01F(H01F), C01G(H01Z), C01I(H01), C01N(H01N),
 C01Q(H01Q), C01S(H0AA), C01X(H1AA), C022(H022), C025(H025), C026(H026),
 C028(H028), C02F(H02G)
5.b Secondary CH2 refined with riding coordinates:
 C018(H01T,H01V), C01H(H01A,H01B), C01K(H01D,H01G), C01L(H01H,H01I), C01T(H01J,
 H01K), C01V(H01L,H01M), C01W(H01O,H01R), C020(H02A,H02C), C027(H02H,H02K),
 C02D(H02Q,H02R), C02H(H02S,H02W), C02W(H3AA,H), C03G(H03A,H03B)
5.c Aromatic/amide H refined with riding coordinates:
 C00T(H00T), C01R(H01S), C01Y(H01Y), C02P(H02P), C030(H030), C00U(H00U),
 C02T(H02T), C036(H036), C033(H033), C02Z(H02Z), C00V(H00V), C02E(H02E),
 C02L(H02L), C02U(H02U), C03K(H03K), C00X(H00X), C02X(H02X), C032(H032),
 C038(H038), C03Q(H03Q), C00Z(H00Z), C02N(H02N), C02O(H02O), C034(H034),
 C03A(H03C), C015(H015), C01U(H01U), C024(H024), C02B(H02B), C03L(H03L),
 C046(H046), C01D(H01X), C02J(H02J), C039(H039), C03D(H03D), C023(H023),
 C029(H029), C02V(H02V), C03C(H03E), C03E(H03F), C03W(H03W), C01P(H01P),
 C01Z(H2AA), C021(H021), C03B(H03G), C03O(H03O), C042(H042), C02A(H02D),
 C03I(H03I), C03J(H03J), C03N(H03N), C03P(H03P), C02C(H02F), C02I(H02I),
 C02K(H02Y), C03H(H03H), C03X(H03X), C044(H044), C048(H048), C02M(H02M),
 C041(H041), C047(H047), C049(H049), C04B(H04B), C02Q(H02), C02Y(H4AA),
 C03M(H03M), C02R(H5AA), C03F(H03S), C01O(H6AA), C031(H031), C03R(H03R),
 C03U(H03U), C03Z(H03Z), C043(H043), C04A(H04A), C040(H040), C045(H045), C9(H9),
  C11(H11), C20(H20), C27(H27), C03Y(H03Y)
5.d Fitted hexagon refined as free rotating group:
 C00T(C01J,C01R,C01Y,C02P,C030), C00U(C02T,C036,C033,C02Z,C00Y), C00V(C017,
 C02E,C02L,C02U,C03K), C00X(C02S,C02X,C032,C038,C03Q), C011(C02N,C02O,C034,C03A,
 C015), C012(C01U,C024,C02B,C03L,C046), C01B(C01D,C02J,C039,C03D,C023),
 C01M(C029,C02V,C03C,C03E,C03W), C01Z(C021,C03B,C03O,C042,C02G), C02A(C037,C03I,
 C03J,C03N,C03P), C02K(C03H,C03S,C03X,C044,C048), C02M(C03V,C041,C047,C049,
 C04B), C02Y(C03M,C02R,C03F,C01O,C010), C03R(C03T,C03U,C03Z,C043,C04A), C04D(C9,
 C11,C20,C27,C03Y)
;
_shelx_res_checksum              44862
_shelx_hkl_checksum              84879
_olex2_submission_original_sample_id pa253214
_olex2_submission_special_instructions 'No special instructions were received'