Asymmetric acyl-Mannich reaction of isoquinolines with α-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral Brønsted acids.
Wu, Wei; Wang, Yan; Guo, Jing; Cai, Liu; Chen, Yuan; Huang, Yanmin; Peng, Yungui; Chemical communications (Cambridge, England) 56 (2020) 11235–11238; doi:10.1039/d0cc03201h

data_7127083
_publ_section_title
;
 Asymmetric acyl-Mannich reaction of isoquinolines with
 \a-(diazomethyl)phosphonate and diazoacetate catalyzed by chiral
 Br\/onsted acids.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11235
_journal_page_last               11238
_journal_paper_doi               10.1039/d0cc03201h
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C16 H18 Br N3 O4'
_chemical_formula_sum            'C16 H18 Br N3 O4'
_chemical_formula_weight         396.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-12-29 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.6346(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.32373(10)
_cell_length_b                   15.62333(14)
_cell_length_c                   8.25080(10)
_cell_measurement_reflns_used    7954
_cell_measurement_temperature    294.0(3)
_cell_measurement_theta_max      71.6830
_cell_measurement_theta_min      5.6530
_cell_volume                     871.35(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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      air
_diffrn_ambient_temperature      294.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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   -105.00  33.00   1.00    1.00    --  -36.10   0.00 -90.00  138
  2  \w    -53.00  31.00   1.00    1.00    --  -36.10  57.00 -60.00   84
  3  \w    -53.00  31.00   1.00    1.00    --  -36.10  57.00  90.00   84
  4  \w     24.00  90.00   1.00    1.00    --   36.10-126.00  30.00   66
  5  \w     24.00  90.00   1.00    1.00    --   36.10-126.00-180.00   66
  6  \w     24.00  90.00   1.00    1.00    --   36.10-126.00-120.00   66
  7  \w     38.00 129.00   1.00    1.00    --  107.97 -30.00   0.00   91
  8  \w     39.00 110.00   1.00    1.00    --  107.97 -95.00  90.00   71
  9  \w    101.00 178.00   1.00    1.00    --  107.97 112.00 -90.00   77
 10  \w     38.00 112.00   1.00    1.00    --  107.97-112.00-120.00   74
 11  \w     39.00 110.00   1.00    1.00    --  107.97 -95.00  30.00   71
 12  \w    101.00 178.00   1.00    1.00    --  107.97 112.00 120.00   77
 13  \w     87.00 178.00   1.00    1.00    --  107.97  30.00-120.00   91
 14  \w     39.00 110.00   1.00    1.00    --  107.97 -95.00 -60.00   71
 15  \w    101.00 178.00   1.00    1.00    --  107.97 112.00-120.00   77
 16  \w     41.00 126.00   1.00    1.00    --  107.97 -61.00-150.00   85
 17  \w     41.00 126.00   1.00    1.00    --  107.97 -61.00 120.00   85
 18  \w     90.00 175.00   1.00    1.00    --  107.97  61.00 -30.00   85
 19  \w     91.00 176.00   1.00    1.00    --  107.97  45.00-180.00   85
 20  \w     38.00 129.00   1.00    1.00    --  107.97 -30.00-180.00   91
 21  \w   -103.00 -19.00   1.00    1.00    --  -36.10 -57.00 150.00   84
 22  \w   -103.00 -19.00   1.00    1.00    --  -36.10 -57.00  60.00   84
 23  \w   -104.00  -9.00   1.00    1.00    --  -36.10 -77.00 -90.00   95
 24  \w    -55.00  33.00   1.00    1.00    --  -36.10  38.00  60.00   88
 25  \w   -104.00  -9.00   1.00    1.00    --  -36.10 -77.00   0.00   95
 26  \w      9.00 104.00   1.00    1.00    --   36.10  77.00-180.00   95
 27  \w     70.00 178.00   1.00    1.00    --  107.97  15.00  90.00  108
 28  \w     87.00 178.00   1.00    1.00    --  107.97  30.00 -60.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1998156000
_diffrn_orient_matrix_UB_12      0.0221640000
_diffrn_orient_matrix_UB_13      -0.1476385000
_diffrn_orient_matrix_UB_21      -0.0875016000
_diffrn_orient_matrix_UB_22      -0.0847409000
_diffrn_orient_matrix_UB_23      0.0331343000
_diffrn_orient_matrix_UB_31      -0.0658875000
_diffrn_orient_matrix_UB_32      0.0452911000
_diffrn_orient_matrix_UB_33      0.1343367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9511
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.692
_diffrn_reflns_theta_min         5.664
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 1511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.033(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0730P)^2^+0.2510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3277
_reflns_number_total             3335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03201h2.cif
_cod_data_source_block           pyg191108
_cod_depositor_comments
'Adding full bibliography for 7127082--7127083.cif.'
_cod_database_code               7127083
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C1 H1 O1 Br1'
_reflns_odcompleteness_completeness 99.94
_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. Restrained distances
 N3-H3B \\sim N3-H3A
 with sigma of 0.001
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C9(H9), C10(H10)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2019-11-08
_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 1.748
_oxdiff_exptl_absorpt_empirical_full_min 0.760