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_4036815
_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 ad
_chemical_formula_moiety         'C22 H17 Br O4'
_chemical_formula_sum            'C22 H17 Br O4'
_chemical_formula_weight         425.26
_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
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omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  -60.0000 154

138 omega   24.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  -30.0000 154

139 omega   24.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000    0.0000 154

140 omega   79.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 99

141 omega   24.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -180.0000 154

142 omega   24.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000   90.0000 154

143 omega   24.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000  120.0000 154

144 omega   52.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -30.0000 126

145 omega   24.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -180.0000 154

146 omega   79.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 99

147 omega -130.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306    0.0000  -60.0000 179

148 omega -130.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306    0.0000  -30.0000 179

149 omega -130.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306    0.0000    0.0000 179

150 omega -130.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.7306    0.0000  -90.0000 179
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1241653000
_diffrn_orient_matrix_UB_12      -0.0012513000
_diffrn_orient_matrix_UB_13      0.0059020000
_diffrn_orient_matrix_UB_21      0.0147392000
_diffrn_orient_matrix_UB_22      -0.0132343000
_diffrn_orient_matrix_UB_23      0.1226473000
_diffrn_orient_matrix_UB_31      -0.0014241000
_diffrn_orient_matrix_UB_32      -0.2548158000
_diffrn_orient_matrix_UB_33      -0.0063798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            69848
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.554
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07999
_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    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1208 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(7)
_refine_ls_extinction_coef       0.0111(7)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0467P)^2^+0.3905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_full    0.792
_reflns_Friedel_fraction_max     0.809
_reflns_number_gt                3038
_reflns_number_total             3042
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00608_si_002.cif
_cod_data_source_block           exp_6570
_cod_original_cell_volume        945.069(11)
_cod_database_code               4036815
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C22H17Br1O4
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.742
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C11(H11), C18(H18), C19(H19), C21(H21), C22(H22)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e :
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'