#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/18/1501809.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_1501809
loop_
_publ_author_name
'Pettit, George R.'
'Smith, Thomas H.'
'Xu, Jun-Ping'
'Herald, Delbert L.'
'Flahive, Erik J.'
'Anderson, Collin R.'
'Belcher, Paul E.'
'Knight, John C.'
_publ_section_title
;
 Antineoplastic agents. 590. X-ray crystal structure of dolastatin 16 and
 syntheses of the dolamethylleuine and dolaphenvaline units.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1003
_journal_page_last               1008
_journal_paper_doi               10.1021/np100877h
_journal_volume                  74
_journal_year                    2011
_chemical_formula_sum            'C13 H14 F3 N O3'
_chemical_formula_weight         289.25
_chemical_name_common            ?'TFA-dolaphenvaline'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.3-0'
_cell_angle_alpha                90
_cell_angle_beta                 103.1810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9918(5)
_cell_length_b                   6.3850(5)
_cell_length_c                   13.4458(11)
_cell_measurement_reflns_used    4295
_cell_measurement_temperature    123.(2)
_cell_measurement_theta_max      27.5247
_cell_measurement_theta_min      2.6176
_cell_volume                     668.03(9)
_computing_cell_refinement       'SAINT V7.60A (Bruker AXS, 2008)'
_computing_data_collection
'Bruker Instrument Service v2008, 7, 0, 0 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.60A (Bruker AXS, 2008)'
_computing_molecular_graphics    'XShell Version 6.3.1 (Bruker AXS, 2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5366
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.8497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sadabs Version 2008/1 (Bruker AXS, 2008; Sheldrick, 2008)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.262
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                2327
_reflns_number_total             2359
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np100877h_si_006.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               1501809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
F F1 1.55286(12) 0.33933(18) 0.45470(9) 0.0435(2) Uani d . 1
F F2 1.36166(17) 0.15207(16) 0.35833(9) 0.0438(2) Uani d . 1
F F3 1.31433(14) 0.2794(2) 0.49580(8) 0.0463(2) Uani d . 1
O O1 1.39041(13) 0.5952(2) 0.29969(9) 0.0306(2) Uani d . 1
O O2 0.95109(14) 1.08170(17) 0.35939(8) 0.0267(2) Uani d . 1
H H2A 0.9343 1.1601 0.4064 0.04 Uiso calc R 1
O O3 1.04150(12) 0.86321(16) 0.48961(6) 0.0201(2) Uani d . 1
N N1 1.15828(14) 0.5788(2) 0.37166(9) 0.0172(2) Uani d . 1
H H1 1.1085 0.5067 0.4127 0.021 Uiso calc R 1
C C1 0.8409(2) 0.5476(2) 0.05499(11) 0.0225(2) Uani d . 1
C C2 0.7528(2) 0.3591(2) 0.03591(12) 0.0280(2) Uani d . 1
H H2 0.7797 0.2486 0.0843 0.034 Uiso calc R 1
C C3 0.6256(2) 0.3288(2) -0.05291(12) 0.0316(4) Uani d . 1
H H3 0.5671 0.1985 -0.065 0.038 Uiso calc R 1
C C4 0.5849(2) 0.4894(2) -0.12336(12) 0.0328(4) Uani d . 1
H H4 0.499 0.4692 -0.1843 0.039 Uiso calc R 1
C C5 0.6695(2) 0.6800(2) -0.10498(12) 0.0326(4) Uani d . 1
H H5 0.6406 0.791 -0.1529 0.039 Uiso calc R 1
C C6 0.7971(2) 0.7086(2) -0.01616(12) 0.0273(4) Uani d . 1
H H6 0.8549 0.8394 -0.004 0.033 Uiso calc R 1
C C7 0.9801(2) 0.5803(2) 0.15084(11) 0.0240(2) Uani d . 1
H H7A 1.0793 0.6509 0.1326 0.029 Uiso calc R 1
H H7B 1.0197 0.4423 0.1807 0.029 Uiso calc R 1
C C8 0.91836(18) 0.7128(2) 0.23149(11) 0.0184(2) Uani d . 1
H H8 0.8727 0.848 0.1986 0.022 Uiso calc R 1
C C9 0.7736(2) 0.6059(2) 0.26913(12) 0.0240(2) Uani d . 1
H H9A 0.6751 0.5845 0.2115 0.036 Uiso calc R 1
H H9B 0.739 0.6944 0.3206 0.036 Uiso calc R 1
H H9C 0.8136 0.4702 0.2995 0.036 Uiso calc R 1
C C10 1.07376(18) 0.7643(2) 0.32044(11) 0.0177(2) Uani d . 1
H H10 1.1599 0.8421 0.2911 0.021 Uiso calc R 1
C C11 1.02200(18) 0.9046(2) 0.39906(11) 0.0174(2) Uani d . 1
C C12 1.3109(2) 0.5168(2) 0.35707(12) 0.0201(2) Uani d . 1
C C13 1.38549(18) 0.3202(2) 0.41801(11) 0.0231(2) Uani d . 1
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'
F F 0.0171 0.0103 '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
C11 O2 H2A 109.5
C12 N1 C10 120.74(12)
C12 N1 H1 119.6
C10 N1 H1 119.6
C2 C1 C6 118.40(14)
C2 C1 C7 121.38(15)
C6 C1 C7 120.22(15)
C1 C2 C3 121.22(17)
C1 C2 H2 119.4
C3 C2 H2 119.4
C4 C3 C2 119.70(16)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 119.96(15)
C3 C4 H4 120.0
C5 C4 H4 120.0
C4 C5 C6 119.97(17)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 120.74(16)
C1 C6 H6 119.6
C5 C6 H6 119.6
C1 C7 C8 112.56(12)
C1 C7 H7A 109.1
C8 C7 H7A 109.1
C1 C7 H7B 109.1
C8 C7 H7B 109.1
H7A C7 H7B 107.8
C9 C8 C7 112.12(13)
C9 C8 C10 111.95(12)
C7 C8 C10 109.29(12)
C9 C8 H8 107.8
C7 C8 H8 107.8
C10 C8 H8 107.8
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1 C10 C11 108.80(12)
N1 C10 C8 113.31(12)
C11 C10 C8 111.47(12)
N1 C10 H10 107.7
C11 C10 H10 107.7
C8 C10 H10 107.7
O3 C11 O2 122.24(13)
O3 C11 C10 125.12(13)
O2 C11 C10 112.64(12)
O1 C12 N1 126.70(15)
O1 C12 C13 118.58(14)
N1 C12 C13 114.68(13)
F1 C13 F3 107.67(13)
F1 C13 F2 107.08(13)
F3 C13 F2 106.84(14)
F1 C13 C12 111.03(13)
F3 C13 C12 113.32(13)
F2 C13 C12 110.61(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C13 1.3216(17)
F2 C13 1.328(2)
F3 C13 1.3253(18)
O1 C12 1.214(2)
O2 C11 1.3213(18)
O2 H2A 0.84
O3 C11 1.2207(18)
N1 C12 1.339(2)
N1 C10 1.457(2)
N1 H1 0.88
C1 C2 1.388(2)
C1 C6 1.394(2)
C1 C7 1.513(2)
C2 C3 1.394(2)
C2 H2 0.95
C3 C4 1.384(3)
C3 H3 0.95
C4 C5 1.387(3)
C4 H4 0.95
C5 C6 1.394(2)
C5 H5 0.95
C6 H6 0.95
C7 C8 1.542(2)
C7 H7A 0.99
C7 H7B 0.99
C8 C9 1.526(2)
C8 C10 1.550(2)
C8 H8 1.0
C9 H9A 0.98
C9 H9B 0.98
C9 H9C 0.98
C10 C11 1.513(2)
C10 H10 1.0
C12 C13 1.542(2)
