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_4124897
_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 Cl N2 O2'
_chemical_formula_sum            'C21 H17 Cl N2 O2'
_chemical_formula_weight         364.82
_chemical_name_common            Organic
_chemical_name_systematic
;
Organic
;
_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_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2012 & ZCIF'
_cell_angle_alpha                64.8401(9)
_cell_angle_beta                 72.8123(9)
_cell_angle_gamma                89.6362(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8629(6)
_cell_length_b                   9.8568(7)
_cell_length_c                   11.5901(8)
_cell_measurement_reflns_used    9140
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.3
_cell_volume                     867.15(10)
_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-2012'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2012)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Smart Apex II diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      -0.0286024
_diffrn_orient_matrix_UB_12      -0.0879830
_diffrn_orient_matrix_UB_13      -0.0147468
_diffrn_orient_matrix_UB_21      0.0302928
_diffrn_orient_matrix_UB_22      0.0669989
_diffrn_orient_matrix_UB_23      -0.0989643
_diffrn_orient_matrix_UB_31      0.1117294
_diffrn_orient_matrix_UB_32      -0.0240274
_diffrn_orient_matrix_UB_33      -0.0117255
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.052
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0100P)^2^+0.5730P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0728
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4510
_reflns_number_total             5046
_reflns_threshold_expression     'I > 2\s(I)'
_iucr_refine_instructions_details 'Available on request'
_cod_data_source_file            ja5b12877_si_003.cif
_cod_data_source_block           2525
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               4124897
_shelx_estimated_absorpt_t_min   0.886
_shelx_estimated_absorpt_t_max   0.945
_shelxl_version_number           2012-9
_shelx_res_checksum              2267
_shelx_hkl_checksum              48751
_iucr_refine_reflections_details 'Available on request'
_diffrn_measurement_frame_width-ccd 512