Scaffold diversity-oriented synthesis of limonoid dimers: discovery of an axially chiral agent within vivoanti-breast cancer activity
Li, Wan-Shan; Yang, Yang; Liu, Jun-Jun; Shen, Li; Shi, Zhi; Wu, Jun; Organic Chemistry Frontiers 5 (2018) 1079–; doi:10.1039/C8QO00154E

data_1554270
_publ_section_title
;
 Scaffold diversity-oriented synthesis of limonoid dimers: discovery of an
 axially chiral agent within vivoanti-breast cancer activity
;
_journal_issue                   7
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1079
_journal_paper_doi               10.1039/C8QO00154E
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         '4(C2 H3 N), C70 H84 O22'
_chemical_formula_sum            'C78 H96 N4 O22'
_chemical_formula_weight         1441.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-01-24 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.70154(11)
_cell_length_b                   27.4281(3)
_cell_length_c                   26.4591(3)
_cell_measurement_reflns_used    29640
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.9270
_cell_measurement_theta_min      3.3090
_cell_volume                     7766.35(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -35.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -38.0000  120.0000 102

  2 omega   -2.00   97.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938 -126.0000  -30.0000 99

  3 omega   19.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000 -150.0000 77

  4 omega   16.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 53

  5 omega   19.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  120.0000 77

  6 omega   66.00  168.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000   30.0000 102

  7 omega   72.00  168.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000 -150.0000 96

  8 omega   72.00  168.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000 -120.0000 96

  9 omega   19.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  150.0000 77

 10 omega   72.00  168.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000  -90.0000 96

 11 omega   16.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   30.0000 53

 12 omega    9.00  133.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000 -111.5487 124

 13 omega   15.00  127.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -180.0000 112

 14 omega   16.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 53

 15 omega   16.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   60.0000 53

 16 omega   12.00  143.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -18.0000  147.8772 131

 17 omega   19.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  -30.0000 77

 18 omega   66.00  168.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -60.0000 102

 19 omega   16.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -180.0000 53

 20 omega   60.00  172.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000    0.0000 112

 21 omega   10.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000   30.0000 74

 22 omega   19.00  123.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -59.0000  -99.0005 104

 23 omega   19.00  124.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 105

 24 omega   11.00  115.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000 -120.0000 104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0181537000
_diffrn_orient_matrix_UB_12      -0.0471859000
_diffrn_orient_matrix_UB_13      0.0306705000
_diffrn_orient_matrix_UB_21      -0.0798900000
_diffrn_orient_matrix_UB_22      0.0213648000
_diffrn_orient_matrix_UB_23      0.0430756000
_diffrn_orient_matrix_UB_31      -0.1184678000
_diffrn_orient_matrix_UB_32      -0.0216673000
_diffrn_orient_matrix_UB_33      -0.0243438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            55598
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         3.22
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3072
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         6934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+9.1748P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2014
_refine_ls_wR_factor_ref         0.2040
_reflns_number_gt                6673
_reflns_number_total             6934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00154e5.cif
_cod_data_source_block           exp_9773
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_hydrogen_treatment' value 'CONSTR' was changed
to 'constr' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        7766.36(14)
_cod_database_code               1554270
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Sof: N2(0.5) C42(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C42'(0.5)
 C43'(0.5) H43D(0.5) H43E(0.5) H43F(0.5)
 Fixed U12: N2'(0)
 Fixed U23: N2'(0)
 Fixed Uiso: H41A(0.377) H41B(0.377) H41C(0.377) H43A(0.305) H43B(0.305)
 H43C(0.305) H43D(0.353) H43E(0.353) H43F(0.353) H3(0.054) H5(0.057) H6A(0.075)
 H6B(0.075) H9(0.071) H11A(0.141) H11B(0.141) H12A(0.137) H12B(0.137)
 H17(0.067) H18A(0.122) H18B(0.122) H18C(0.122) H19A(0.088) H19B(0.088)
 H19C(0.088) H21(0.101) H22(0.129) H23(0.139) H28A(0.099) H28B(0.099)
 H28C(0.099) H29A(0.063) H29B(0.063) H31A(0.235) H31B(0.235) H31C(0.235)
 H33(0.082) H34A(0.169) H34B(0.169) H34C(0.169) H35A(0.183) H35B(0.183)
 H35C(0.183) H37(0.131) H38A(0.293) H38B(0.293) H38C(0.293) H39A(0.277)
 H39B(0.277) H39C(0.277) H2(0.087)
 Fixed X: H41A(0.329) H41B(0.4775) H41C(0.418) H43A(0.6831) H43B(0.6435)
 H43C(0.7876) N2'(0.5) H43D(0.6888) H43E(0.7197) H43F(0.7699) H3(-0.0816)
 H5(0.188) H6A(0.2226) H6B(0.0757) H9(0.3088) H11A(0.4429) H11B(0.3759)
 H12A(0.5238) H12B(0.5746) H17(0.3859) H18A(0.6156) H18B(0.6871) H18C(0.631)
 H19A(0.2589) H19B(0.1107) H19C(0.1964) H21(0.7075) H22(0.4844) H23(0.6658)
 H28A(-0.0834) H28B(-0.0463) H28C(-0.1668) H29A(-0.1341) H29B(-0.0566)
 H31A(0.1334) H31B(0.2555) H31C(0.1243) H33(0.2025) H34A(0.1837) H34B(0.0459)
 H34C(0.1641) H35A(0.0663) H35B(-0.0093) H35C(0.1323) H37(0.0988) H38A(-0.1054)
 H38B(-0.0737) H38C(-0.1684) H39A(0.0603) H39B(0.1007) H39C(-0.0433) H2(-0.0234)
 Fixed Y: H41A(0.1103) H41B(0.107) H41C(0.1385) H43A(0.0656) H43B(0.1215)
 H43C(0.1073) H43D(0.0711) H43E(0.0778) H43F(0.0309) H3(0.0834) H5(0.1435)
 H6A(0.2341) H6B(0.2352) H9(0.1581) H11A(0.192) H11B(0.1879) H12A(0.154)
 H12B(0.1476) H17(0.0875) H18A(0.0323) H18B(0.0805) H18C(0.0772) H19A(0.2452)
 H19B(0.2493) H19C(0.2331) H21(0.0373) H22(0.1446) H23(0.1439) H28A(0.1911)
 H28B(0.1372) H28C(0.1456) H29A(0.1606) H29B(0.2101) H31A(0.2596) H31B(0.2288)
 H31C(0.2017) H33(0.004) H34A(0.0303) H34B(0.0499) H34C(0.0744) H35A(-0.063)
 H35B(-0.0376) H35C(-0.0545) H37(0.1708) H38A(0.1345) H38B(0.172) H38C(0.1874)
 H39A(0.242) H39B(0.2555) H39C(0.2577) H2(0.0567)
 Fixed Z: H41A(0.3308) H41B(0.3367) H41C(0.2919) H43A(0.4035) H43B(0.3972)
 H43C(0.4038) N2'(0.25) H43D(0.3026) H43E(0.2438) H43F(0.2735) H3(0.5559)
 H5(0.5894) H6A(0.5951) H6B(0.606) H9(0.4678) H11A(0.5045) H11B(0.5577)
 H12A(0.58) H12B(0.5239) H17(0.6162) H18A(0.5347) H18B(0.5526) H18C(0.4966)
 H19A(0.5186) H19B(0.5117) H19C(0.4651) H21(0.6355) H22(0.6825) H23(0.7364)
 H28A(0.6295) H28B(0.6471) H28C(0.6124) H29A(0.5134) H29B(0.5257) H31A(0.7656)
 H31B(0.7512) H31C(0.7585) H33(0.6339) H34A(0.7181) H34B(0.7064) H34C(0.6794)
 H35A(0.6376) H35B(0.6827) H35C(0.6912) H37(0.349) H38A(0.3318) H38B(0.2873)
 H38C(0.3313) H39A(0.305) H39B(0.3616) H39C(0.3455) H2(0.4525)
;
_olex2_submission_special_instructions 'No special instructions were received'