Novel Cinnamic Acid Analogues: Synthesis of Aminotroponyl Acrylates by Pd(II)-Catalysed C(sp2)-H Olefination
Sharma, Nagendra K.; Jena, Chinmay Kumar; Chemical Communications  (2022) –; doi:10.1039/D2CC02276A

data_7130247
_publ_section_title
;
 Novel Cinnamic Acid Analogues: Synthesis of Aminotroponyl Acrylates by
 Pd(II)-Catalysed C(sp2)-H Olefination
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02276A
_journal_year                    2022
_chemical_formula_moiety         'C19 H22 N2 O6'
_chemical_formula_sum            'C19 H22 N2 O6'
_chemical_formula_weight         374.38
_chemical_name_systematic        'Peptide 6q'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-31 deposited with the CCDC.	2022-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                67.839(7)
_cell_angle_beta                 63.570(8)
_cell_angle_gamma                88.924(7)
_cell_formula_units_Z            2
_cell_length_a                   10.1306(9)
_cell_length_b                   10.1315(8)
_cell_length_c                   11.0192(9)
_cell_measurement_reflns_used    6012
_cell_measurement_temperature    300.47(15)
_cell_measurement_theta_max      28.7410
_cell_measurement_theta_min      3.5530
_cell_volume                     922.67(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      300.47(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.804
_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    -59.00  18.00   0.50   31.28    --    3.51 -63.00-117.00  154
  2  \w    -11.00  66.00   0.50   31.28    --    3.51  63.00  20.00  154
  3  \w    -67.00  10.00   0.50   31.28    --   -4.14 -63.00-117.00  154
  4  \w    -10.00  65.00   0.50   31.28    --   -4.14  19.00  30.00  150
  5  \w    -42.00  19.00   0.50   31.28    --   -4.14 -77.00 150.00  122
  6  \w    -15.00  32.00   0.50   31.28    --   -4.14 -99.00  30.00   94
  7  \w    -10.00  65.00   0.50   31.28    --   -4.14  19.00 -60.00  150
  8  \w    -26.00  19.00   0.50   31.28    --   -4.14  77.00  60.00   90
  9  \w     -4.00  25.00   0.50   31.28    --   -4.14 -99.00  90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471943000
_diffrn_orient_matrix_UB_12      0.0374507000
_diffrn_orient_matrix_UB_13      0.0405477000
_diffrn_orient_matrix_UB_21      -0.0639271000
_diffrn_orient_matrix_UB_22      -0.0433166000
_diffrn_orient_matrix_UB_23      0.0145147000
_diffrn_orient_matrix_UB_31      -0.0018849000
_diffrn_orient_matrix_UB_32      -0.0512490000
_diffrn_orient_matrix_UB_33      0.0660950000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16378
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.226
_diffrn_reflns_theta_min         3.449
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.183
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0557
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3108
_reflns_number_total             4416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02276a2.cif
_cod_data_source_block           nks-ckj-505-re
_cod_original_cell_volume        922.68(15)
_cod_database_code               7130247
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C38 H44 N4 O12 '
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.999
_diffrn_oxdiff_digest_frames
;
01128b3f4136df46c5495298bc7e84f812000256ec2
;
_diffrn_oxdiff_digest_hkl
;
0138da179fecfb891669fdf2ff0ec87ede99ee
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C17(H17), C6(H6), C3(H3), C5(H5), C4(H4)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              72145
_shelx_hkl_checksum              88654
_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 3.500
_oxdiff_exptl_absorpt_empirical_full_min 0.320