One-pot Diels-Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework.
Sow, Boubacar; Bellavance, Gabriel; Barabé, Francis; Barriault, Louis; Beilstein journal of organic chemistry 7 (2011) 1007–1013; doi:10.3762/bjoc.7.114

data_4029765
_publ_section_title
;
 One-pot Diels-Alder cycloaddition/gold(I)-catalyzed 6-endo-dig
 cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone
 framework.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1007
_journal_page_last               1013
_journal_paper_doi               10.3762/bjoc.7.114
_journal_volume                  7
_journal_year                    2011
_chemical_formula_sum            'C20 H19 N O3'
_chemical_formula_weight         321.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
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_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
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_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
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_computing_cell_refinement       'APEX II, Bruker (2009)'
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_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
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_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_theta_full        22.01
_diffrn_reflns_theta_max         22.01
_diffrn_reflns_theta_min         1.90
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_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
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_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.09
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_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0054(5)
_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   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         4012
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_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.5324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1064
_reflns_number_gt                2863
_reflns_number_total             4012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-7-114-S2.cif
_cod_data_source_block           lb016
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        3315.94(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4029765