An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective C-C bond cleavage of epoxides: highly efficient synthesis of chiral furan derivatives
Weiliang Chen; Xuan Fu; Lili Lin; Xiao Yuan; Weiwei Luo; Juhua Feng; Xiaohua Liu; Xiaoming Feng; Chem.Commun. 50 (2014) 11480–; doi:10.1039/C4cc04182H

data_7115685
_publ_section_title
;
 An asymmetric [3+2] cycloaddition of alkynes with oxiranes by selective
 C-C bond cleavage of epoxides: highly efficient synthesis of chiral furan
 derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              11480
_journal_paper_doi               10.1039/C4cc04182H
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H26 O4, 0.5(C2 H3 N)'
_chemical_formula_sum            'C36 H27.5 N0.5 O4'
_chemical_formula_weight         531.08
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.9173(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.77380(9)
_cell_length_b                   12.39402(7)
_cell_length_c                   19.49664(13)
_cell_measurement_reflns_used    29280
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.7970
_cell_measurement_theta_min      3.9350
_cell_volume                     2721.92(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0801354000
_diffrn_orient_matrix_UB_12      0.0548737000
_diffrn_orient_matrix_UB_13      -0.0677624000
_diffrn_orient_matrix_UB_21      -0.0016482000
_diffrn_orient_matrix_UB_22      0.1036042000
_diffrn_orient_matrix_UB_23      0.0433608000
_diffrn_orient_matrix_UB_31      0.1108306000
_diffrn_orient_matrix_UB_32      0.0412378000
_diffrn_orient_matrix_UB_33      -0.0186972000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41639
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.924
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             1116
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 4455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     733
_refine_ls_number_reflns         9625
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0436P)^2^+0.3152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0673
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                9491
_reflns_number_total             9625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc04182h2.cif
_cod_data_source_block           14apr24e
_cod_depositor_comments
;

2017-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C35 H26 O4), C2 H3 N'
_cod_original_formula_sum        'C72 H55 N O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1062.17
_cod_database_code               7115685
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C35 H24 O4 N'
_shelx_estimated_absorpt_t_max   0.878
_shelx_estimated_absorpt_t_min   0.878
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C39(H39)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27),
  C28(H28), C29(H29), C31(H31), C32(H32), C33(H33), C34(H34), C38(H38),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C49(H49), C50(H50), C51(H51),
  C52(H52), C53(H53), C55(H55), C56(H56), C58(H58), C59(H59), C62(H62),
 C63(H63), C64(H64), C66(H66), C67(H67), C68(H68), C69(H69)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C60(H60A,H60B,H60C), C72(H72A,H72B,H72C)
;