Mechanochemically controllable synthesis of mono- or di-alkenylated indolizines.
Yu, Yue; Guan, Ning; Zhao, Chunying; Cao, Hua; Ma, Yan-Long; Chemical communications (Cambridge, England) 61 (2025) 16834–16837; doi:10.1039/d5cc05156h

data_7135039
_publ_section_title
;
 Mechanochemically controllable synthesis of mono- or di-alkenylated
 indolizines.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16834
_journal_page_last               16837
_journal_paper_doi               10.1039/d5cc05156h
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C57 H61 N O3'
_chemical_formula_sum            'C57 H61 N O3'
_chemical_formula_weight         808.06
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-23
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2025-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.843(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4318(11)
_cell_length_b                   11.3080(9)
_cell_length_c                   18.3289(16)
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      26.6920
_cell_measurement_theta_min      2.7100
_cell_volume                     2364.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.850
_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    -81.00  16.00   1.00    6.50    --  -11.27 -57.00-180.00   97
  2  \w     38.00  63.00   1.00    6.50    --  -11.27  38.00 -90.00   25
  3  \w    -33.00  42.00   1.00    6.50    --  -11.27  57.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0463378000
_diffrn_orient_matrix_UB_12      0.0207211000
_diffrn_orient_matrix_UB_13      0.0243739000
_diffrn_orient_matrix_UB_21      0.0391563000
_diffrn_orient_matrix_UB_22      -0.0040026000
_diffrn_orient_matrix_UB_23      -0.0283471000
_diffrn_orient_matrix_UB_31      -0.0135346000
_diffrn_orient_matrix_UB_32      0.0590758000
_diffrn_orient_matrix_UB_33      -0.0103768000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.1168
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12750
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.700
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.472
_diffrn_reflns_theta_min         2.040
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_description       block
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         9198
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0698
_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^)+(0.0276P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1311
_reflns_Friedel_coverage         0.571
_reflns_Friedel_fraction_full    0.734
_reflns_Friedel_fraction_max     0.534
_reflns_number_gt                6293
_reflns_number_total             9198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05156h2.cif
_cod_data_source_block           46-3
_cod_depositor_comments
'Adding full bibliography for 7135038--7135039.cif.'
_cod_database_code               7135039
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C25(H25),
 C26(H26), C27(H27), C28(H28), C30(H30), C32(H32), C33(H33), C34(H34), C38(H38),
  C39(H39), C40(H40), C41(H41), C42(H42), C46(H46), C48(H48)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C35(H35A,H35B,H35C), C50(H50A,
 H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C54(H54A,H54B,H54C),
 C55(H55A,H55B,H55C), C56(H56A,H56B,H56C)
;
_shelx_res_checksum              33785
_olex2_date_sample_data_collection 2021-05-22
_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 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.893