Formal Synthesis of Gracilamine Using Rh(I)-Catalyzed [3 + 2 + 1] Cycloaddition of 1-Yne-Vinylcyclopropanes and CO.
Bose, Sritama; Yang, Jun; Yu, Zhi-Xiang; The Journal of organic chemistry 81 (2016) 6757–6765; doi:10.1021/acs.joc.6b00608

data_4036816
_publ_section_title
;
 Formal Synthesis of Gracilamine Using Rh(I)-Catalyzed [3 + 2 + 1]
 Cycloaddition of 1-Yne-Vinylcyclopropanes and CO.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6757
_journal_page_last               6765
_journal_paper_doi               10.1021/acs.joc.6b00608
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-12-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9516(7)
_cell_length_b                   10.8253(8)
_cell_length_c                   27.1895(19)
_cell_measurement_reflns_used    3447
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      22.6890
_cell_measurement_theta_min      3.5100
_cell_volume                     2634.8(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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   34.00   99.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -       10.8579 -178.0000  150.0000 65

  2 omega  -40.00   51.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -11.9517   57.0000  -60.0000 91

  3 omega  -86.00   13.00   1.0000    1.1000
omega____ theta____ kappa____ phi______ frames
    -      -11.9517  -57.0000  150.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0204353000
_diffrn_orient_matrix_UB_12      -0.0377750000
_diffrn_orient_matrix_UB_13      -0.0202174000
_diffrn_orient_matrix_UB_21      -0.0765870000
_diffrn_orient_matrix_UB_22      0.0086822000
_diffrn_orient_matrix_UB_23      0.0058062000
_diffrn_orient_matrix_UB_31      -0.0020290000
_diffrn_orient_matrix_UB_32      0.0528037000
_diffrn_orient_matrix_UB_33      -0.0154122000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            15976
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.931
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40133
_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
;
;
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1161 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0320P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0918
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3559
_reflns_number_total             5175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00608_si_003.cif
_cod_data_source_block           exp_6323
_cod_database_code               4036816
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C1 H1 O1'
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C7(H7A,H7B), C17(H17A,H17B), C22(H22A,H22B),
 C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C13(H13), C15(H15), C19(H19), C25(H25), C29(H29), C31(H31)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C32(H32A,H32B)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_shelx_res_checksum              60044
_shelx_hkl_checksum              68927
_olex2_submission_special_instructions 'No special instructions were received'