Unprecedented Intramolecular [4 + 2]-Cycloaddition between a 1,3-Diene and a Diazo Ester.
Qiu, Huang; Srinivas, Harathi D.; Zavalij, Peter Y.; Doyle, Michael P.; Journal of the American Chemical Society 138 (2016) 1808–1811; doi:10.1021/jacs.5b12877

data_4124898
_publ_section_title
;
 Unprecedented Intramolecular [4 + 2]-Cycloaddition between a 1,3-Diene
 and a Diazo Ester.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1808
_journal_page_last               1811
_journal_paper_doi               10.1021/jacs.5b12877
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C21 H17 Br N2 O2'
_chemical_formula_sum            'C21 H17 Br N2 O2'
_chemical_formula_weight         409.27
_chemical_name_systematic        Br-compound
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2014 & ZCIF'
_cell_angle_alpha                90
_cell_angle_beta                 98.6252(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.080(2)
_cell_length_b                   5.9219(4)
_cell_length_c                   16.7844(11)
_cell_measurement_reflns_used    10181
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.2
_cell_volume                     3643.9(4)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        'Apex2, Saint'
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  'Apex2, SHELXL-2014, Platon (Spek, 1990)'
_computing_structure_refinement  'ShelXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0000572
_diffrn_orient_matrix_UB_12      -0.1687902
_diffrn_orient_matrix_UB_13      -0.0015243
_diffrn_orient_matrix_UB_21      0.0271793
_diffrn_orient_matrix_UB_22      0.0001550
_diffrn_orient_matrix_UB_23      0.0139805
_diffrn_orient_matrix_UB_31      -0.0022777
_diffrn_orient_matrix_UB_32      -0.0043646
_diffrn_orient_matrix_UB_33      0.0585897
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23651
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.500
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_T_max  0.711
_exptl_absorpt_correction_T_min  0.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_id                qh682
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.118
_refine_diff_density_min         -0.795
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     678
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0300P)^2^+8.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0979
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3429
_reflns_number_total             3988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12877_si_002.cif
_cod_data_source_block           2728
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4124897--4124899.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4124898
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.396
_shelx_estimated_absorpt_t_max   0.727
_shelx_res_checksum              2390
_shelx_hkl_checksum              56142