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_7127082
_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         'C15 H17 F N3 O5 P'
_chemical_formula_sum            'C15 H18 F0.5 N3 O6 P'
_chemical_formula_weight         369.29
_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   geom
_audit_creation_date             2017-10-18
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5097)
;
_audit_update_record
;
2017-12-18 deposited with the CCDC.	2020-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.986(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2111(2)
_cell_length_b                   6.05545(12)
_cell_length_c                   13.6909(3)
_cell_measurement_reflns_used    4703
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.9090
_cell_measurement_theta_min      4.2630
_cell_volume                     855.65(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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   -106.00 -18.00   1.00    1.00    --  -37.03 -38.00-180.00   88
  2  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00 -30.00   95
  3  \w    -56.00  32.00   1.00    1.00    --  -37.03  38.00 120.00   88
  4  \w    -32.00  56.00   1.00    1.00    --   37.03 -38.00 120.00   88
  5  \w     44.00 110.00   1.00    1.00    --   37.03-162.00 169.00   66
  6  \w     41.00 116.00   1.00    2.00    --  110.47-112.00 -60.00   75
  7  \w     41.00 109.00   1.00    2.00    --  110.47 -95.00-150.00   68
  8  \w     93.00 178.00   1.00    2.00    --  110.47  45.00 -90.00   85
  9  \w     44.00 129.00   1.00    2.00    --  110.47 -61.00 150.00   85
 10  \w     41.00 132.00   1.00    2.00    --  110.47 -30.00  60.00   91
 11  \w     41.00 132.00   1.00    2.00    --  110.47 -30.00 150.00   91
 12  \w     44.00 129.00   1.00    2.00    --  110.47 -61.00-120.00   85
 13  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00-180.00   95
 14  \w   -104.00 -20.00   1.00    1.00    --  -37.03 -57.00  30.00   84
 15  \w   -106.00 -18.00   1.00    1.00    --  -37.03 -38.00  60.00   88
 16  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00 -30.00   84
 17  \w      1.00  76.00   1.00    1.00    --   37.03 -99.00 -60.00   75
 18  \w     89.00 178.00   1.00    2.00    --  110.47  30.00 120.00   89
 19  \w     84.00 178.00   1.00    2.00    --  110.47  77.00-180.00   94
 20  \w     93.00 178.00   1.00    2.00    --  110.47  45.00-120.00   85
 21  \w     72.00 178.00   1.00    2.00    --  110.47  15.00  30.00  106
 22  \w     41.00 109.00   1.00    2.00    --  110.47 -95.00  90.00   68
 23  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00 120.00   95
 24  \w   -104.00 -20.00   1.00    1.00    --  -37.03 -57.00 -30.00   84
 25  \w   -105.00 -10.00   1.00    1.00    --  -37.03 -77.00 -90.00   95
 26  \w    -30.00  54.00   1.00    1.00    --   37.03 -57.00-150.00   84
 27  \w     24.00  91.00   1.00    1.00    --   37.03-126.00-150.00   67
 28  \w     93.00 132.00   1.00    2.00    --  110.47  45.00 150.00   39
;
_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      -0.0644516000
_diffrn_orient_matrix_UB_12      -0.0354808000
_diffrn_orient_matrix_UB_13      -0.1208768000
_diffrn_orient_matrix_UB_21      0.1343336000
_diffrn_orient_matrix_UB_22      -0.0016708000
_diffrn_orient_matrix_UB_23      -0.0060065000
_diffrn_orient_matrix_UB_31      0.0082579000
_diffrn_orient_matrix_UB_32      -0.2520117000
_diffrn_orient_matrix_UB_33      0.0170868000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8887
_diffrn_reflns_point_group_measured_fraction_full 0.826
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.050
_diffrn_reflns_theta_min         3.507
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       needle
_exptl_crystal_F_000             393
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0690P)^2^+0.2148P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.490
_reflns_Friedel_fraction_full    0.613
_reflns_Friedel_fraction_max     0.586
_reflns_number_gt                2639
_reflns_number_total             2756
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03201h2.cif
_cod_data_source_block           pyg1017_ww
_cod_depositor_comments
'Adding full bibliography for 7127082--7127083.cif.'
_cod_original_cell_volume        855.66(3)
_cod_original_formula_sum        'C15 H18 F0.50 N3 O6 P'
_cod_database_code               7127082
_chemical_oxdiff_formula         'C1 N1 P1 O1'
_reflns_odcompleteness_completeness 100.00
_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 Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C(HA,HB)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4AA(H4AA), C3AA(H3AA), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              3747
_shelx_hkl_checksum              89619
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-10-17
_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 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.460