Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing 6-aryl-1,5-enynes.
Roselli, Christina A.; Gagné, Michel R; Organic & biomolecular chemistry 14 (2016) 11261–11265; doi:10.1039/c6ob02128j

data_7155361
_publ_section_title
;
 Gold(i)-catalyzed addition of aldehydes to cyclopropylidene bearing
 6-aryl-1,5-enynes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11261
_journal_page_last               11265
_journal_paper_doi               10.1039/c6ob02128j
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C24 H25 Br O3'
_chemical_formula_sum            'C24 H25 Br O3'
_chemical_formula_weight         441.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-02-24 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                72.229(2)
_cell_angle_beta                 86.297(2)
_cell_angle_gamma                66.705(2)
_cell_formula_units_Z            4
_cell_length_a                   11.9878(6)
_cell_length_b                   13.1429(7)
_cell_length_c                   14.8309(8)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.06
_cell_measurement_theta_min      3.85
_cell_volume                     2039.57(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20859
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.137
_diffrn_reflns_theta_min         3.135
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.919
_exptl_absorpt_correction_T_max  0.8266
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0378 before and 0.0321 after correction.
The Ratio of minimum to maximum transmission is 0.8224.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         7453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0262
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.0036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6978
_reflns_number_total             7453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02128j2.cif
_cod_data_source_block           x1506002_0m
_cod_depositor_comments
;
       Adding full bibliography for 7155361.cif.

2017-11-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C24 H25 Br O3)'
_cod_original_formula_sum        'C48 H50 Br2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     882.70
_cod_database_code               7155361
_shelx_estimated_absorpt_t_max   0.740
_shelx_estimated_absorpt_t_min   0.593
_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:
 C8(H8), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C26(H26A,H26B), C27(H27A,
 H27B), C29(H29A,H29B), C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C13(H13), C18(H18), C19(H19), C21(H21), C22(H22), C25(H25),
 C35(H35), C37(H37), C42(H42), C43(H43), C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C40(H40A,H40B,
 H40C), C47(H47A,H47B,H47C), C48(H48A,H48B,H48C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_completion    2016-02-24
_olex2_date_sample_data_collection 2015-06-05
_olex2_submission_original_sample_id x1506002
_olex2_submission_special_instructions 'No special instructions were received'