Regiodivergent synthesis of pyrazino-indolines <i>vs.</i> triazocines <i>via</i> α-imino carbenes addition to imidazolidines.
Guarnieri-Ibáñez, Alejandro; de Aguirre, Adiran; Besnard, Céline; Poblador-Bahamonde, Amalia I; Lacour, Jérôme; Chemical science 12 (2020) 1479–1485; doi:10.1039/d0sc05725h

data_1559639
_publ_section_title
;
 Regiodivergent synthesis of pyrazino-indolines <i>vs.</i> triazocines
 <i>via</i> \a-imino carbenes addition to imidazolidines.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1479
_journal_page_last               1485
_journal_paper_doi               10.1039/d0sc05725h
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'C25 H24 N2'
_chemical_formula_sum            'C25 H24 N2'
_chemical_formula_weight         352.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-09 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.3021(10)
_cell_length_b                   7.7181(4)
_cell_length_c                   23.5444(12)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      70.6850
_cell_measurement_theta_min      4.2830
_cell_volume                     3871.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4670
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00 -27.00   1.00   20.00    --  -41.74  38.00 -60.00   39
  2  \w    -64.00  33.00   1.00   20.00    --  -41.74  38.00  30.00   97
  3  \w    121.00 170.00   1.00   30.00    --  100.00  45.00-120.00   49
  4  \w     95.00 126.00   1.00   30.00    --  100.00 125.00-180.00   31
  5  \w     83.00 109.00   1.00   30.00    --  100.00-125.00-120.00   26
  6  \w     94.00 172.00   1.00   30.00    --  100.00 125.00-120.00   78
  7  \w     38.00 113.00   1.00   30.00    --  100.00-125.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0592905000
_diffrn_orient_matrix_UB_12      -0.0233060000
_diffrn_orient_matrix_UB_13      0.0367478000
_diffrn_orient_matrix_UB_21      0.0379969000
_diffrn_orient_matrix_UB_22      -0.0476914000
_diffrn_orient_matrix_UB_23      -0.0534013000
_diffrn_orient_matrix_UB_31      0.0165575000
_diffrn_orient_matrix_UB_32      0.1923861000
_diffrn_orient_matrix_UB_33      -0.0088319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8929
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.460
_diffrn_reflns_theta_min         3.755
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0708P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1547
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2423
_reflns_number_total             3621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05725h2.cif
_cod_data_source_block           ajgi831_2_1
_cod_depositor_comments
;Adding full bibliography for 1559635--1559639.cif.

 Adding full bibliography for 1559635--1559639.cif.
;
_cod_database_code               1559639
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C25 H24 N2'
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.787
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              98958
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.712