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_1555185
_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         'C26 H37 N O8'
_chemical_formula_sum            'C26 H37 N O8'
_chemical_formula_weight         491.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-29 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.4812(4)
_cell_length_b                   7.98630(10)
_cell_length_c                   25.3899(3)
_cell_measurement_reflns_used    34367
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1890
_cell_measurement_theta_min      3.7890
_cell_volume                     4832.51(12)
_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 0.996
_diffrn_measured_fraction_theta_max 0.990
_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    -19.00  66.00   1.00    1.00    --    0.00  38.00-180.00   85
  2  \w     10.00  53.00   1.00    1.00    --    0.00  38.00 -90.00   43
  3  \w    -18.00  29.00   1.00    1.00    --    0.00  38.00-120.00   47
  4  \w     -2.00  38.00   1.00    1.00    --    0.00  38.00 -30.00   40
  5  \w     58.00  84.00   1.00    1.00    --    0.00  57.00  90.00   26
  6  \w    -21.00  38.00   1.00    1.00    --    0.00  57.00  90.00   59
  7  \w     55.00  88.00   1.00    1.00    --    0.00  57.00   0.00   33
  8  \w    -86.00 -52.00   1.00    1.00    --    0.00 -82.00 -30.00   34
  9  \w    -23.00  20.00   1.00    1.00    --    0.00  57.00   0.00   43
 10  \w     53.00  87.00   1.00    1.00    --    0.00  38.00 -30.00   34
 11  \w     56.00  87.00   1.00    1.00    --    0.00  38.00 -90.00   31
 12  \w    -18.00  36.00   1.00    1.00    --    0.00  38.00  60.00   54
 13  \w     48.00  74.00   1.00    1.00    --    0.00  38.00-120.00   26
 14  \w    -38.00  29.00   1.00    1.00    --    0.00 -82.00 -30.00   67
 15  \w     63.00  88.00   1.00    1.00    --    0.00  38.00  60.00   25
 16  \w     70.00  95.00   1.00    1.00    --   95.80  62.00  39.49   25
 17  \w     67.00  93.00   1.00    1.00    --   95.80  71.00 116.77   26
 18  \w    153.00 179.00   1.00    1.00    --   95.80  68.00  62.11   26
 19  \w    160.00 185.00   1.00    1.00    --   95.80  65.00  92.71   25
 20  \w     69.00 101.00   1.00    1.00    --   95.80  65.00  92.71   32
 21  \w     69.00 100.00   1.00    1.00    --   95.80  68.00  62.11   31
 22  \w    124.00 183.00   1.00    1.00    --   95.80  62.00 -50.73   59
 23  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 24  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 25  \w    125.00 184.00   1.00    1.00    --   95.80  61.00-150.00   59
 26  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 27  \w      6.00  31.00   1.00    1.00    --   95.80 -82.00   0.00   25
 28  \w     47.00 123.00   1.00    1.00    --   95.80 -82.00   0.00   76
 29  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 30  \w     33.00 127.00   1.00    1.00    --   95.80 -82.00-150.00   94
 31  \w    159.00 184.00   1.00    1.00    --   95.80  70.00-128.83   25
 32  \w     68.00  97.00   1.00    1.00    --   95.80  68.00 -87.58   29
 33  \w     69.00  95.00   1.00    1.00    --   95.80  70.00-128.83   26
 34  \w    140.00 168.00   1.00    1.00    --   95.80  71.00 -86.00   28
 35  \w     99.00 185.00   1.00    1.00    --   95.80  75.00 147.58   86
 36  \w     74.00 185.00   1.00    1.00    --   95.80  48.00  65.40  111
 37  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -90.00   26
 38  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 120.00   26
 39  \w    116.00 182.00   1.00    1.00    --   95.80  82.00 -90.00   66
 40  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 41  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-150.00   26
 42  \w     75.00 168.00   1.00    1.00    --   95.80  45.00  30.00   93
 43  \w     73.00 101.00   1.00    1.00    --   95.80  61.00-168.47   28
 44  \w    141.00 184.00   1.00    1.00    --   95.80  61.00-168.47   43
 45  \w     68.00  94.00   1.00    1.00    --   95.80  71.00 -86.00   26
 46  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   26
 47  \w     39.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   89
 48  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 49  \w    103.00 184.00   1.00    1.00    --   95.80  80.00 158.74   81
 50  \w     72.00  97.00   1.00    1.00    --   95.80  61.00-150.00   25
 51  \w     66.00  91.00   1.00    1.00    --   95.80  75.00 147.58   25
 52  \w     65.00  91.00   1.00    1.00    --   95.80  77.00   0.00   26
 53  \w     73.00 184.00   1.00    1.00    --   95.80  61.00 -30.00  111
 54  \w     98.00 128.00   1.00    1.00    --   95.80  77.00 120.00   30
 55  \w     64.00  93.00   1.00    1.00    --   95.80  80.00 158.74   29
 56  \w    160.00 185.00   1.00    1.00    --   95.80  77.00-120.00   25
 57  \w     72.00 130.00   1.00    1.00    --   95.80  61.00 150.00   58
 58  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 59  \w     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 60  \w    159.00 184.00   1.00    1.00    --   95.80  82.00 -60.00   25
 61  \w     64.00  90.00   1.00    1.00    --   95.80  82.00  60.00   26
 62  \w     71.00  96.00   1.00    1.00    --   95.80  61.00  60.00   25
 63  \w     65.00 108.00   1.00    1.00    --   95.80  77.00-120.00   43
 64  \w    118.00 182.00   1.00    1.00    --   95.80  62.00  39.49   64
 65  \w    160.00 185.00   1.00    1.00    --   95.80  82.00  60.00   25
 66  \w     69.00 112.00   1.00    1.00    --   95.80 -82.00 120.00   43
 67  \w     71.00  97.00   1.00    1.00    --   95.80  61.00  30.00   26
 68  \w     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 69  \w     73.00 182.00   1.00    1.00    --   95.80  54.00-127.83  109
 70  \w     71.00 185.00   1.00    1.00    --   95.80  58.00 115.67  114
 71  \w     70.00 100.00   1.00    1.00    --   95.80  62.00 -50.73   30
 72  \w     53.00 125.00   1.00    1.00    --   95.80 -82.00  60.00   72
 73  \w     75.00 143.00   1.00    1.00    --   95.80  45.00 -48.56   68
;
_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      -0.0038361000
_diffrn_orient_matrix_UB_12      -0.1600404000
_diffrn_orient_matrix_UB_13      0.0328235000
_diffrn_orient_matrix_UB_21      -0.0229416000
_diffrn_orient_matrix_UB_22      -0.0968753000
_diffrn_orient_matrix_UB_23      -0.0529144000
_diffrn_orient_matrix_UB_31      0.0603104000
_diffrn_orient_matrix_UB_32      -0.0470230000
_diffrn_orient_matrix_UB_33      -0.0027665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            55628
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.564
_diffrn_reflns_theta_min         3.709
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44011
_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    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 4184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         9373
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0577
_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^)+(0.0659P)^2^+17.7652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1526
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                9203
_reflns_number_total             9373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01111k3.cif
_cod_data_source_block           exp_1004
_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(C26 H37 N O8)'
_cod_original_formula_sum        'C52 H74 N2 O16'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     983.13
_cod_database_code               1555185
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.815
_reflns_odcompleteness_completeness 99.96
_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:
 C8(H8), C12(H12), C9(H9), C34(H34), C35(H35), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C21(H21A,H21B), C39(H39A,H39B), C7(H7A,H7B), C19(H19A,H19B),
 C33(H33A,H33B), C47(H47A,H47B), C15(H15A,H15B), C45(H45A,H45B), C43(H43A,H43B),
  C46(H46A,H46B), C14(H14A,H14B), C41(H41A,H41B), C20(H20A,H20B), C40(H40A,
 H40B), C17(H17A,H17B), C42(H42A,H42B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C31(H31), C30(H30), C27(H27), C4(H4), C1(H1), C28(H28), C2(H2)
2.d Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C24(H24A,H24B,H24C), C49(H49A,H49B,H49C), C26(H26A,H26B,
 H26C), C22(H22A,H22B,H22C), C52(H52A,H52B,H52C), C48(H48A,H48B,H48C), C25(H25A,
 H25B,H25C)
;
_shelx_res_checksum              88881
_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 2.033
_oxdiff_exptl_absorpt_empirical_full_min 0.556