#------------------------------------------------------------------------------
#$Date: 2020-03-21 02:35:13 +0200 (Sat, 21 Mar 2020) $
#$Revision: 249588 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557632.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1557632
loop_
_publ_author_name
'Winn, Blake A.'
'Devkota, Laxman'
'Kuch, Bunnarack'
'MacDonough, Matthew T.'
'Strecker, Tracy E.'
'Wang, Yifan'
'Shi, Zhe'
'Gerberich, Jeni L.'
'Mondal, Deboprosad'
'Ramirez, Alejandro J.'
'Hamel, Ernest'
'Chaplin, David J.'
'Davis, Peter'
'Mason, Ralph P.'
'Trawick, Mary Lynn'
'Pinney, Kevin G.'
_publ_section_title
;
 Bioreductively Activatable Prodrug Conjugates of Combretastatin A-1 and
 Combretastatin A-4 as Anticancer Agents Targeted toward Tumor-Associated
 Hypoxia
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00773
_journal_year                    2020
_chemical_formula_sum            'C25 H27 N O7 S'
_chemical_formula_weight         485.53
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                100.514(5)
_cell_angle_beta                 104.240(5)
_cell_angle_gamma                108.180(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0895(7)
_cell_length_b                   12.0696(10)
_cell_length_c                   14.0112(12)
_cell_measurement_reflns_used    3182
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      2.74
_cell_volume                     1208.85(19)
_computing_cell_refinement       'Bruker SAINTPLUS'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINTPLUS'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12273
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.459
_diffrn_reflns_theta_min         2.059
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         4851
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0485P)²+0.2015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1276
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3182
_reflns_number_total             4851
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np9b00773_si_003.cif
_cod_data_source_block           kp61
_cod_original_cell_volume        1208.84(18)
_cod_database_code               1557632
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.31042(9) 0.51101(5) 0.13297(4) 0.0609(2) Uani 1 1 d . . . . .
O1 O 0.0975(3) 0.26482(17) 0.00586(16) 0.1122(7) Uani 1 1 d . . . . .
O2 O 0.0089(3) 0.30442(18) -0.13739(14) 0.0936(6) Uani 1 1 d . . . . .
O3 O 0.50980(19) 0.70585(12) 0.30918(10) 0.0521(4) Uani 1 1 d . . . . .
O4 O 0.7261(2) 0.87489(13) 0.48533(11) 0.0661(4) Uani 1 1 d . . . . .
O5 O -0.4646(2) 0.13663(15) 0.15855(13) 0.0790(5) Uani 1 1 d . . . . .
O6 O -0.1425(2) 0.10403(13) 0.21137(13) 0.0712(5) Uani 1 1 d . . . . .
O7 O 0.1683(2) 0.28682(13) 0.32843(12) 0.0654(4) Uani 1 1 d . . . . .
N1 N 0.0960(3) 0.3352(2) -0.04601(17) 0.0729(6) Uani 1 1 d . . . . .
C1 C 0.2039(3) 0.4618(2) 0.00398(16) 0.0600(6) Uani 1 1 d . . . . .
C2 C 0.2242(4) 0.5513(3) -0.04226(19) 0.0794(8) Uani 1 1 d . . . . .
H2 H 0.1722 0.5393 -0.1137 0.095 Uiso 1 1 calc R U . . .
C3 C 0.3320(4) 0.6639(2) 0.02897(19) 0.0795(8) Uani 1 1 d . . . . .
H3 H 0.3624 0.7381 0.0108 0.095 Uiso 1 1 calc R U . . .
C4 C 0.3899(3) 0.65766(19) 0.12753(16) 0.0532(5) Uani 1 1 d . . . . .
C5 C 0.5164(3) 0.75829(18) 0.22337(16) 0.0556(5) Uani 1 1 d . . . . .
C6 C 0.7146(3) 0.7905(2) 0.2231(2) 0.0834(8) Uani 1 1 d . . . . .
H6A H 0.7975 0.8560 0.2851 0.125 Uiso 1 1 calc R U . . .
H6B H 0.7259 0.8172 0.1623 0.125 Uiso 1 1 calc R U . . .
H6C H 0.7476 0.7188 0.2219 0.125 Uiso 1 1 calc R U . . .
C7 C 0.4645(4) 0.8688(2) 0.23300(19) 0.0692(7) Uani 1 1 d . . . . .
H7A H 0.3361 0.8453 0.2312 0.104 Uiso 1 1 calc R U . . .
H7B H 0.4793 0.9030 0.1759 0.104 Uiso 1 1 calc R U . . .
H7C H 0.5445 0.9298 0.2981 0.104 Uiso 1 1 calc R U . . .
C8 C 0.4284(3) 0.74334(16) 0.37853(14) 0.0451(5) Uani 1 1 d . . . . .
C9 C 0.5430(3) 0.82839(17) 0.47252(15) 0.0494(5) Uani 1 1 d . . . . .
C10 C 0.4634(3) 0.85949(18) 0.54483(16) 0.0556(5) Uani 1 1 d . . . . .
H10 H 0.5386 0.9163 0.6095 0.067 Uiso 1 1 calc R U . . .
C11 C 0.2757(3) 0.80857(18) 0.52367(16) 0.0559(6) Uani 1 1 d . . . . .
H11 H 0.2238 0.8327 0.5738 0.067 Uiso 1 1 calc R U . . .
C12 C 0.1602(3) 0.72309(17) 0.43135(16) 0.0492(5) Uani 1 1 d . . . . .
C13 C 0.2426(3) 0.69269(17) 0.35907(15) 0.0468(5) Uani 1 1 d . . . . .
H13 H 0.1676 0.6353 0.2947 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0407(3) 0.6740(2) 0.41038(17) 0.0610(6) Uani 1 1 d . . . . .
H14 H -0.0877 0.7322 0.4353 0.073 Uiso 1 1 calc R U . . .
C15 C -0.1683(3) 0.5628(2) 0.36277(17) 0.0596(6) Uani 1 1 d . . . . .
H15 H -0.2908 0.5585 0.3532 0.072 Uiso 1 1 calc R U . . .
C16 C -0.1550(3) 0.44570(18) 0.32243(15) 0.0503(5) Uani 1 1 d . . . . .
C17 C -0.3144(3) 0.3499(2) 0.25785(16) 0.0567(5) Uani 1 1 d . . . . .
H17 H -0.4269 0.3625 0.2397 0.068 Uiso 1 1 calc R U . . .
C18 C -0.3120(3) 0.2368(2) 0.21965(16) 0.0563(5) Uani 1 1 d . . . . .
C19 C -0.1484(3) 0.21752(18) 0.24320(16) 0.0539(5) Uani 1 1 d . . . . .
C20 C 0.0127(3) 0.31333(18) 0.30833(16) 0.0510(5) Uani 1 1 d . . . . .
C21 C 0.0085(3) 0.42521(18) 0.34894(16) 0.0519(5) Uani 1 1 d . . . . .
H21 H 0.1178 0.4886 0.3952 0.062 Uiso 1 1 calc R U . . .
C22 C 0.8470(3) 0.9567(2) 0.58287(18) 0.0742(7) Uani 1 1 d . . . . .
H22A H 0.8147 1.0284 0.5965 0.111 Uiso 1 1 calc R U . . .
H22B H 0.9742 0.9817 0.5823 0.111 Uiso 1 1 calc R U . . .
H22C H 0.8350 0.9159 0.6366 0.111 Uiso 1 1 calc R U . . .
C23 C -0.6392(4) 0.1421(3) 0.1510(2) 0.0985(9) Uani 1 1 d . . . . .
H23A H -0.6440 0.1714 0.2199 0.148 Uiso 1 1 calc R U . . .
H23B H -0.7347 0.0609 0.1170 0.148 Uiso 1 1 calc R U . . .
H23C H -0.6600 0.1979 0.1108 0.148 Uiso 1 1 calc R U . . .
C24 C -0.1556(5) 0.0656(3) 0.1080(2) 0.0979(9) Uani 1 1 d . . . . .
H24A H -0.2815 0.0462 0.0641 0.147 Uiso 1 1 calc R U . . .
H24B H -0.1244 -0.0069 0.0966 0.147 Uiso 1 1 calc R U . . .
H24C H -0.0700 0.1306 0.0911 0.147 Uiso 1 1 calc R U . . .
C25 C 0.3341(3) 0.3812(2) 0.39541(19) 0.0662(6) Uani 1 1 d . . . . .
H25A H 0.3625 0.4498 0.3661 0.099 Uiso 1 1 calc R U . . .
H25B H 0.4346 0.3510 0.4042 0.099 Uiso 1 1 calc R U . . .
H25C H 0.3198 0.4078 0.4622 0.099 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 90.53(11) . . ?
C8 O3 C5 120.04(14) . . ?
C9 O4 C22 117.76(18) . . ?
C18 O5 C23 117.7(2) . . ?
C19 O6 C24 115.81(18) . . ?
C20 O7 C25 117.19(16) . . ?
O1 N1 O2 123.9(2) . . ?
O1 N1 C1 117.5(2) . . ?
O2 N1 C1 118.6(2) . . ?
C2 C1 N1 125.5(2) . . ?
C2 C1 S1 114.04(19) . . ?
N1 C1 S1 120.43(17) . . ?
C1 C2 C3 110.7(2) . . ?
C4 C3 C2 113.7(2) . . ?
C3 C4 C5 128.9(2) . . ?
C3 C4 S1 111.02(18) . . ?
C5 C4 S1 119.94(15) . . ?
O3 C5 C4 106.24(15) . . ?
O3 C5 C7 113.24(16) . . ?
C4 C5 C7 111.97(19) . . ?
O3 C5 C6 104.82(18) . . ?
C4 C5 C6 109.04(18) . . ?
C7 C5 C6 111.15(19) . . ?
C13 C8 O3 121.13(17) . . ?
C13 C8 C9 120.58(18) . . ?
O3 C8 C9 118.13(18) . . ?
O4 C9 C10 124.89(19) . . ?
O4 C9 C8 116.79(18) . . ?
C10 C9 C8 118.3(2) . . ?
C11 C10 C9 120.4(2) . . ?
C10 C11 C12 122.09(19) . . ?
C11 C12 C13 116.79(19) . . ?
C11 C12 C14 120.33(19) . . ?
C13 C12 C14 122.78(19) . . ?
C8 C13 C12 121.80(19) . . ?
C15 C14 C12 131.8(2) . . ?
C14 C15 C16 132.1(2) . . ?
C17 C16 C21 118.58(19) . . ?
C17 C16 C15 118.33(19) . . ?
C21 C16 C15 123.0(2) . . ?
C18 C17 C16 121.2(2) . . ?
O5 C18 C17 124.6(2) . . ?
O5 C18 C19 115.2(2) . . ?
C17 C18 C19 120.2(2) . . ?
O6 C19 C18 121.8(2) . . ?
O6 C19 C20 118.93(19) . . ?
C18 C19 C20 119.0(2) . . ?
O7 C20 C21 124.02(19) . . ?
O7 C20 C19 115.48(18) . . ?
C21 C20 C19 120.50(19) . . ?
C20 C21 C16 120.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.698(2) . ?
S1 C4 1.707(2) . ?
O1 N1 1.215(3) . ?
O2 N1 1.222(2) . ?
O3 C8 1.387(2) . ?
O3 C5 1.462(2) . ?
O4 C9 1.362(2) . ?
O4 C22 1.431(3) . ?
O5 C18 1.374(3) . ?
O5 C23 1.414(3) . ?
O6 C19 1.381(2) . ?
O6 C24 1.405(3) . ?
O7 C20 1.370(2) . ?
O7 C25 1.419(3) . ?
N1 C1 1.437(3) . ?
C1 C2 1.345(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.369(3) . ?
C4 C5 1.510(3) . ?
C5 C7 1.512(3) . ?
C5 C6 1.529(3) . ?
C8 C13 1.368(3) . ?
C8 C9 1.400(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.379(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.398(3) . ?
C12 C14 1.476(3) . ?
C14 C15 1.335(3) . ?
C15 C16 1.470(3) . ?
C16 C17 1.390(3) . ?
C16 C21 1.395(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.399(3) . ?
C20 C21 1.380(3) . ?
