Matsuda-Heck arylation of itaconates: a versatile approach to heterocycles from a renewable resource.
Krause, Andreas; Sperlich, Eric; Schmidt, Bernd; Organic & biomolecular chemistry 19 (2021) 4292–4302; doi:10.1039/d1ob00392e

data_7158035
_publ_section_title
;
 Matsuda-Heck arylation of itaconates: a versatile approach to
 heterocycles from a renewable resource.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4292
_journal_page_last               4302
_journal_paper_doi               10.1039/d1ob00392e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C12 H10 Br N O3'
_chemical_formula_sum            'C12 H10 Br N O3'
_chemical_formula_weight         296.12
_chemical_name_systematic
;
methyl 8-bromo-2-oxo-2,3-dihydro-1H-benzo[b]azepine-4-carboxylate
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-02-24 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.31(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.452(5)
_cell_length_b                   4.5449(9)
_cell_length_c                   22.939(5)
_cell_measurement_reflns_used    17107
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      31.09
_cell_measurement_theta_min      3.52
_cell_volume                     2277.8(9)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_molecular_graphics    'Diamond (Blankenburg, 2020)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.86, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      210
_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
; 
1408 frames, exposure time = 40 s per frame, 
detector distance = 60 mm, \D\w = 0.5 \% 
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_radiation_monochromator  'graded multilayer mirror'
_diffrn_radiation_source         'Genix Microfocus'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12003
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.549
_diffrn_reflns_theta_min         3.518
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.609
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_size_rad          0.08
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0515P)^2^+3.6373P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1793
_reflns_number_total             2363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00392e3.cif
_cod_data_source_block           AM-X3
_cod_depositor_comments
'Adding full bibliography for 7158035--7158036.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7158035
_shelx_res_checksum              45928
_shelx_hkl_checksum              10186