Synthesis of Conformationally Liberated Yohimbine Analogues and Evaluation of Cytotoxic Activity
Yang, Han; Poznik, Michal; Tang, Shaojian; Xue, Peng; Du, Lidong; Liu, Chenlu; Chen, Xiaochuan; Chruma, Jason J.; ACS Omega  (2021) –; doi:10.1021/acsomega.1c02784

data_4518894
_publ_section_title
;
 Synthesis of Conformationally Liberated Yohimbine Analogues and
 Evaluation of Cytotoxic Activity
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c02784
_journal_year                    2021
_chemical_formula_moiety         'C45 H50 F3 N4 Na O14 S'
_chemical_formula_sum            'C45 H50 F3 N4 Na O14 S'
_chemical_formula_weight         982.94
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1701(3)
_cell_length_b                   21.3786(5)
_cell_length_c                   18.8905(5)
_cell_measurement_reflns_used    10197
_cell_measurement_temperature    160(15)
_cell_measurement_theta_max      71.2640
_cell_measurement_theta_min      4.1010
_cell_volume                     4511.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      160(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.968
_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    -90.00  -2.00   1.00    1.00    --  -34.85 125.00  30.00   88
  2  \w   -104.00  -6.00   1.00    1.00    --  -34.85 -77.00 120.00   98
  3  \w    -37.00  73.00   1.00    1.00    --   34.85 -19.00   0.00  110
  4  \w     16.00 103.00   1.00    1.00    --   34.85  57.00  60.00   87
  5  \w     13.00 105.00   1.00    1.00    --   34.85  38.00-180.00   92
  6  \w      1.00  75.00   1.00    1.00    --   34.85 -99.00   0.00   74
  7  \w     23.00  90.00   1.00    1.00    --   34.85-125.00-180.00   67
  8  \w     23.00  90.00   1.00    1.00    --   34.85-125.00 -30.00   67
  9  \w      8.00  79.00   1.00    1.00    --   34.85-106.00 145.00   71
 10  \w     35.00 133.00   1.00    2.30    --  106.90 -30.00 120.00   98
 11  \w     47.00 124.00   1.00    2.30    --  106.90 -45.00 -30.00   77
 12  \w     60.00 142.00   1.00    2.30    --  106.90 178.00   0.00   82
 13  \w     36.00 115.00   1.00    2.30    --  106.90 -30.00  60.00   79
 14  \w    114.00 147.00   1.00    2.30    --  106.90 106.00-115.00   33
 15  \w     39.00 102.00   1.00    2.30    --  106.90 -94.00 150.00   63
 16  \w     89.00 175.00   1.00    2.30    --  106.90  61.00-180.00   86
 17  \w     58.00 124.00   1.00    2.30    --  106.90 -61.00 120.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1289968000
_diffrn_orient_matrix_UB_12      -0.0118629000
_diffrn_orient_matrix_UB_13      0.0258691000
_diffrn_orient_matrix_UB_21      0.0345614000
_diffrn_orient_matrix_UB_22      -0.0230455000
_diffrn_orient_matrix_UB_23      -0.0744285000
_diffrn_orient_matrix_UB_31      0.0346849000
_diffrn_orient_matrix_UB_32      0.0672157000
_diffrn_orient_matrix_UB_33      -0.0209882000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24926
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.741
_diffrn_reflns_theta_min         3.958
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.475
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         8552
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1131P)^2^+1.7962P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7404
_reflns_number_total             8552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c02784_si_002.cif
_cod_data_source_block           jc-yh-iii-105-160k
_cod_original_cell_volume        4511.04(19)
_cod_database_code               4518894
_reflns_odcompleteness_completeness 98.75
_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, All O(H,H) groups
2. Restrained distances
 O004-H004
 0.85 with sigma of 0.01
 C018-H004
 1.887727 with sigma of 0.02
 Na02-H004
 2.80751 with sigma of 0.02
3. Others
 Sof(O01R)=1-FVAR(1)
 Sof(O01Q)=FVAR(1)
 Sof(O00L)=1-FVAR(2)
 Sof(O00K)=FVAR(2)
 Sof(O00X)=1-FVAR(3)
 Sof(O00W)=FVAR(3)
 Sof(F00{)=1-FVAR(4)
 Sof(F00Z)=FVAR(4)
 Sof(F0)=1-FVAR(5)
 Sof(F012)=FVAR(5)
 Sof(F00D)=1-FVAR(6)
 Sof(F00C)=FVAR(6)
4.a Rotating group:
 O00F(H00A,H00B)
4.b Ternary CH refined with riding coordinates:
 C00N(H00N), C00O(H00O), C00X(H00X), C010(H010), C015(H015), C016(H016),
 C018(H018), C01C(H01E), C01N(H01U), C01P(H01X)
4.c Secondary CH2 refined with riding coordinates:
 C014(H01A,H01B), C01D(H01F,H01G), C01E(H01H,H01I), C01G(H01K,H01L), C01I(H01N,
 H01O), C01J(H01P,H01Q), C01O(H01V,H01W), C01U(H01,H)
4.d Aromatic/amide H refined with riding coordinates:
 C011(H011), C013(H013), C019(H019), C01A(H01C), C01B(H01D), C01F(H01J),
 C01H(H01M), C01K(H01R), C01L(H01S), C01M(H01T), C01S(H01Y), C01T(H01Z)
4.e Idealised Me refined as rotating group:
 C01V(H0AA,HA,HB), C01W(H1AA,HC,HD)
4.f Idealised tetrahedral OH refined as rotating group:
 O006(H006), O008(H008), O00G(H00G)
;
_shelx_res_checksum              81059
_shelx_hkl_checksum              14507
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-27
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.150
_oxdiff_exptl_absorpt_empirical_full_min 0.642