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_4124899
_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         'C31 H24 Br N3 O4, C H2 Cl2'
_chemical_formula_sum            'C32 H26 Br Cl2 N3 O4'
_chemical_formula_weight         667.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.062(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0904(15)
_cell_length_b                   8.9712(12)
_cell_length_c                   29.184(4)
_cell_measurement_reflns_used    10097
_cell_measurement_temperature    98
_cell_measurement_theta_max      40.3
_cell_measurement_theta_min      2.4
_cell_volume                     2867.4(7)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
scan:
    Number of images: 246
               Slice: -68.0000 - 55.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 90.0000
                 XTD: 34.5020
              2theta: -34.7472
scan:
    Number of images: 144
               Slice: -68.0000 - 4.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 270.0000
                 XTD: 34.5020
              2theta: -34.7472
scan:
    Number of images: 114
               Slice: -68.0000 - -11.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 70.0000
                 Phi: 0.0000
                 XTD: 34.5020
              2theta: -34.7472
scan:
    Number of images: 94
               Slice: -71.0000 - -24.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 90.0000
                 XTD: 34.5020
              2theta: -34.7472
scan:
    Number of images: 60
               Slice: -115.0000 - -85.0000
         Image width: 0.5000
            Exp time: 45.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 180.0000
                 XTD: 34.5020
              2theta: -34.7472
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.015772
_diffrn_orient_matrix_UB_12      0.063097
_diffrn_orient_matrix_UB_13      -0.064087
_diffrn_orient_matrix_UB_21      0.109739
_diffrn_orient_matrix_UB_22      -0.015971
_diffrn_orient_matrix_UB_23      0.011283
_diffrn_orient_matrix_UB_31      -0.000105
_diffrn_orient_matrix_UB_32      -0.020500
_diffrn_orient_matrix_UB_33      -0.027995
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            21153
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.378
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.664
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6584
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.207
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0430P)^2^+1.7080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5878
_reflns_number_total             6584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b12877_si_004.cif
_cod_data_source_block           cd1388a
_cod_depositor_comments
'Adding full bibliography for 4124897--4124899.cif.'
_cod_database_code               4124899
_shelx_estimated_absorpt_t_max   0.732
_shelx_estimated_absorpt_t_min   0.732
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-N2
 1.33 with sigma of 0.003
3.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C32(H32A,H32B)
3.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C22(H22), C25(H25), C15(H15), C19(H19), C18(H18), C29(H29),
 C27(H27), C6(H6), C21(H21), C28(H28), C31(H31), C17(H17), C16(H16), C30(H30)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'