Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids
Zhong, Jiaxin; He, Haibing; Gao, Shuanhu; Organic Chemistry Frontiers 6 (2019) 3781–; doi:10.1039/C9QO01111K

data_1555186
_publ_section_title
;
 Exploration of 1,3-dipolar cycloaddition reactions to construct the core
 skeleton of Calyciphylline A-type alkaloids
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3781
_journal_paper_doi               10.1039/C9QO01111K
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C22 H29 N O5'
_chemical_formula_sum            'C22 H29 N O5'
_chemical_formula_weight         387.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-30 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.38850(10)
_cell_length_b                   24.6653(2)
_cell_length_c                   19.71480(10)
_cell_measurement_reflns_used    51687
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1980
_cell_measurement_theta_min      4.2220
_cell_volume                     4046.08(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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    -23.00  21.00   1.00    1.00    --    0.00 -15.00  85.00   44
  2  \w    -20.00  30.00   1.00    1.00    --    0.00  15.00-104.00   50
  3  \w     68.00 168.00   1.00    1.00    --   95.80  15.00-104.00  100
  4  \w     30.00  80.00   1.00    1.00    --   95.80 -15.00  85.00   50
  5  \w    -32.00  22.00   1.00    1.00    --    0.00  82.00 -30.00   54
  6  \w     30.00  73.00   1.00    1.00    --    0.00  57.00-120.00   43
  7  \w     27.00  86.00   1.00    1.00    --    0.00  82.00 -30.00   59
  8  \w     29.00  89.00   1.00    1.00    --    0.00  38.00-180.00   60
  9  \w    -22.00  72.00   1.00    1.00    --    0.00  57.00 -60.00   94
 10  \w     36.00  87.00   1.00    1.00    --    0.00  57.00-150.00   51
 11  \w     46.00  81.00   1.00    1.00    --    0.00  77.00 150.00   35
 12  \w    -86.00 -50.00   1.00    1.00    --    0.00 -57.00 -30.00   36
 13  \w     12.00  38.00   1.00    1.00    --    0.00  77.00 150.00   26
 14  \w    -21.00   8.00   1.00    1.00    --    0.00  57.00-120.00   29
 15  \w    -17.00  87.00   1.00    1.00    --    0.00  38.00  60.00  104
 16  \w    -30.00  -3.00   1.00    1.00    --    0.00  77.00 150.00   27
 17  \w    -23.00   4.00   1.00    1.00    --    0.00  57.00-150.00   27
 18  \w    -31.00  -5.00   1.00    1.00    --    0.00 -57.00 -30.00   26
 19  \w     20.00  76.00   1.00    1.00    --    0.00  38.00 120.00   56
 20  \w     63.00  96.00   1.00    1.00    --   95.80  82.00 150.00   33
 21  \w     65.00 127.00   1.00    1.00    --   95.80 -82.00 -30.00   62
 22  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 23  \w    147.00 185.00   1.00    1.00    --   95.80  56.00-163.07   38
 24  \w     72.00 136.00   1.00    1.00    --   95.80  56.00-163.07   64
 25  \w      6.00 127.00   1.00    1.00    --   95.80 -82.00-120.00  121
 26  \w      6.00  73.00   1.00    1.00    --   95.80 -82.00  60.00   67
 27  \w     71.00 185.00   1.00    1.00    --   95.80  61.00  12.50  114
 28  \w     68.00 140.00   1.00    1.00    --   95.80  70.00  86.97   72
 29  \w     66.00  91.00   1.00    1.00    --   95.80  74.00 -58.15   25
 30  \w     70.00 183.00   1.00    1.00    --   95.80  62.00 -27.17  113
 31  \w    154.00 182.00   1.00    1.00    --   95.80  79.00 131.49   28
 32  \w     43.00 125.00   1.00    1.00    --   95.80 -82.00 150.00   82
 33  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 34  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  95.93   26
 35  \w    108.00 144.00   1.00    1.00    --   95.80  79.00 131.49   36
 36  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 37  \w     65.00  96.00   1.00    1.00    --   95.80  79.00 131.49   31
 38  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 39  \w     64.00  96.00   1.00    1.00    --   95.80  80.00   6.07   32
 40  \w     63.00 104.00   1.00    1.00    --   95.80  82.00 -60.00   41
 41  \w    136.00 180.00   1.00    1.00    --   95.80  72.00  32.52   44
 42  \w     67.00 133.00   1.00    1.00    --   95.80  72.00  32.52   66
 43  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 44  \w    148.00 173.00   1.00    1.00    --   95.80  77.00   0.00   25
 45  \w     65.00  93.00   1.00    1.00    --   95.80  76.00-120.29   28
 46  \w     71.00 110.00   1.00    1.00    --   95.80  61.00-150.00   39
 47  \w     73.00 185.00   1.00    1.00    --   95.80  52.00  84.31  112
 48  \w     67.00  93.00   1.00    1.00    --   95.80  72.00 119.21   26
 49  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 50  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 51  \w     72.00 108.00   1.00    1.00    --   95.80  61.00 -60.00   36
 52  \w    129.00 155.00   1.00    1.00    --   95.80  61.00 -60.00   26
 53  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 54  \w     71.00  96.00   1.00    1.00    --   95.80  61.00 120.00   25
 55  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  60.00   26
 56  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 57  \w    109.00 182.00   1.00    1.00    --   95.80  82.00 120.00   73
 58  \w     75.00 116.00   1.00    1.00    --   95.80  47.00 -88.58   41
 59  \w    136.00 162.00   1.00    1.00    --   95.80  77.00-131.74   26
 60  \w     68.00 154.00   1.00    1.00    --   95.80  70.00  -9.72   86
 61  \w     68.00 104.00   1.00    1.00    --   95.80  69.00 156.39   36
 62  \w    137.00 179.00   1.00    1.00    --   95.80  69.00 156.39   42
 63  \w     65.00 119.00   1.00    1.00    --   95.80  77.00-131.74   54
 64  \w     63.00  88.00   1.00    1.00    --   95.80  81.00-112.25   25
 65  \w    119.00 185.00   1.00    1.00    --   95.80  81.00-112.25   66
 66  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 67  \w     61.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   67
 68  \w     96.00 127.00   1.00    1.00    --   95.80 -82.00  90.00   31
 69  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 70  \w    157.00 183.00   1.00    1.00    --   95.80  61.00  60.00   26
 71  \w     52.00  77.00   1.00    1.00    --   95.80 -82.00  90.00   25
 72  \w     71.00 185.00   1.00    1.00    --   95.80  59.00 -91.18  114
 73  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -30.00   25
 74  \w    111.00 178.00   1.00    1.00    --   95.80  82.00  95.93   67
 75  \w     75.00 118.00   1.00    1.00    --   95.80  61.00  60.00   43
 76  \w     63.00  88.00   1.00    1.00    --   95.80  82.00  60.00   25
 77  \w    100.00 126.00   1.00    1.00    --   95.80 -82.00  60.00   26
 78  \w    132.00 157.00   1.00    1.00    --   95.80  82.00  90.00   25
 79  \w     73.00 113.00   1.00    1.00    --   95.80 -61.00-150.00   40
 80  \w     63.00  89.00   1.00    1.00    --   95.80  82.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1124721000
_diffrn_orient_matrix_UB_12      -0.0126103000
_diffrn_orient_matrix_UB_13      0.0660758000
_diffrn_orient_matrix_UB_21      -0.1442387000
_diffrn_orient_matrix_UB_22      0.0021461000
_diffrn_orient_matrix_UB_23      0.0410822000
_diffrn_orient_matrix_UB_31      -0.0283952000
_diffrn_orient_matrix_UB_32      -0.0611680000
_diffrn_orient_matrix_UB_33      -0.0122409000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            111799
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.550
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8240
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0457P)^2^+2.0556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7769
_reflns_number_total             8240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01111k3.cif
_cod_data_source_block           exp_858
_cod_depositor_comments
;

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C22 H29 N O5)'
_cod_original_formula_sum        'C44 H58 N2 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     774.92
_cod_database_code               1555186
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.95
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C14(H14), C30(H30), C32(H32), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C21(H21A,H21B), C29(H29A,H29B), C36(H36A,H36B), C37(H37A,H37B),
  C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C43(H43A,H43B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C42(H42A,H42B,H42C), C44(H44A,H44B,
 H44C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O7(H7)
;
_shelx_res_checksum              75805
_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 6.662
_oxdiff_exptl_absorpt_empirical_full_min 0.527