Access to hexahydroazepinone heterocycles via palladium-catalysed C(sp3)–H alkenylation/ring-opening of cyclopropanes
Charette, André B.; St-Jacques, Kevin; Ladd, Carolyn L.; Chemical Communications  (2022) –; doi:10.1039/D2CC01917E

data_7130217
_publ_section_title
;
 Access to hexahydroazepinone heterocycles via palladium-catalysed
 C(sp3)--H alkenylation/ring-opening of cyclopropanes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01917E
_journal_year                    2022
_chemical_formula_moiety         'C17 H19 N O'
_chemical_formula_sum            'C17 H19 N O'
_chemical_formula_weight         253.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-08-20 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1178(3)
_cell_length_b                   18.3487(7)
_cell_length_c                   8.0923(3)
_cell_measurement_reflns_used    7396
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.927
_cell_measurement_theta_min      5.418
_cell_volume                     1353.84(8)
_computing_cell_refinement
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 3 (2019) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2017) V8.38A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17932
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.049
_diffrn_reflns_theta_min         5.417
_diffrn_source                   'Microfocus Source'
_diffrn_source_current           0.65
_diffrn_source_power             0.02912
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_source_voltage           44.8
_exptl_absorpt_coefficient_mu    0.596
_exptl_absorpt_correction_T_max  0.9154
_exptl_absorpt_correction_T_min  0.6611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1331 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.7222.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method 'Slow evaporation in ether'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.1198P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2565
_reflns_number_total             2599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01917e2.cif
_cod_data_source_block           lauvin2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130217
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.875
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9(3)
 0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_shelx_res_checksum              97478
_olex2_exptl_crystal_mounting_method 'Mounted on a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'