#------------------------------------------------------------------------------
#$Date: 2015-12-08 19:58:05 +0200 (Tue, 08 Dec 2015) $
#$Revision: 170886 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/48/7154842.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_7154842
loop_
_publ_author_name
'Lesma, Giordano'
'Bassanini, Ivan'
'Bortolozzi, Roberta'
'Colletto, Chiara'
'Bai, Ruoli'
'Hamel, Ernest'
'Meneghetti, Fiorella'
'Rainoldi, Giulia'
'Stucchi, Mattia'
'Sacchetti, Alessandro'
'Silvani, Alessandra'
'Viola, Giampietro'
_publ_section_title
;
 Complementary isonitrile-based multicomponent reactions for the synthesis
 of diversified cytotoxic hemiasterlin analogues.
;
_journal_issue                   48
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              11633
_journal_page_last               11644
_journal_paper_doi               10.1039/c5ob01882j
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H26 F3 N2 O4'
_chemical_formula_sum            'C21 H29 F3 N2 O5'
_chemical_formula_weight         446.46
_chemical_name_systematic        18b
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-27T12:26:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-04-28 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                93.455(2)
_cell_angle_beta                 95.974(2)
_cell_angle_gamma                109.227(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7878(8)
_cell_length_b                   10.2150(8)
_cell_length_c                   12.0649(10)
_cell_measurement_reflns_used    5308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      60
_cell_measurement_theta_min      4
_cell_measurement_wavelength     0.71073
_cell_volume                     1127.05(16)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26050
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         6571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0908P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.153
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                5430
_reflns_number_total             6571
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01882j2.cif
_cod_data_source_block           ib44_m
_cod_database_code               7154842
_audit_block_doi                 10.5517/cc14nc16
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 1.12984(15) 1.22555(13) 0.72274(18) 0.1352(7) Uani 1 1 d .
O2 O 0.60046(11) 0.62066(9) 0.62488(8) 0.0563(2) Uani 1 1 d .
F3 F 1.09316(13) 1.06001(14) 0.59907(9) 0.0954(4) Uani 1 1 d .
O3 O 0.50116(12) 0.91624(9) 0.36740(8) 0.0580(3) Uani 1 1 d .
O4 O 0.42443(11) 0.70628(9) 0.26983(7) 0.0526(2) Uani 1 1 d .
O5 O 0.86800(13) 1.11989(11) 0.76484(11) 0.0730(3) Uani 1 1 d .
O1 O 0.05995(11) 0.59719(12) 0.86687(11) 0.0674(3) Uani 1 1 d .
N1 N 0.52274(11) 0.79202(9) 0.56431(7) 0.0405(2) Uani 1 1 d .
H1 H 0.5246 0.8763 0.5775 0.049 Uiso 1 1 calc R
N2 N 0.84880(11) 0.89572(10) 0.71244(8) 0.0447(2) Uani 1 1 d .
C18 C 0.2096(2) 0.7686(2) 0.4995(2) 0.0872(6) Uani 1 1 d .
H18A H 0.23 0.8321 0.4429 0.131 Uiso 1 1 calc R
H18B H 0.255 0.8176 0.5714 0.131 Uiso 1 1 calc R
H18C H 0.1059 0.7301 0.4998 0.131 Uiso 1 1 calc R
C15 C 0.43225(19) 0.77131(16) 0.16680(10) 0.0611(4) Uani 1 1 d .
H15A H 0.405 0.7009 0.1044 0.092 Uiso 1 1 calc R
H15B H 0.5302 0.8326 0.1651 0.092 Uiso 1 1 calc R
H15C H 0.3668 0.8237 0.1623 0.092 Uiso 1 1 calc R
C13 C 0.43463(12) 0.70722(11) 0.46418(8) 0.0401(2) Uani 1 1 d .
H13 H 0.467 0.6272 0.4509 0.048 Uiso 1 1 calc R
C10 C 0.74449(17) 0.67170(18) 0.86876(13) 0.0625(4) Uani 1 1 d .
H10A H 0.8471 0.7093 0.8638 0.094 Uiso 1 1 calc R
H10B H 0.6993 0.5952 0.8119 0.094 Uiso 1 1 calc R
H10C H 0.7301 0.6396 0.9412 0.094 Uiso 1 1 calc R
C12 C 0.60147(12) 0.74021(11) 0.63666(8) 0.0396(2) Uani 1 1 d .
C17 C 0.2386(2) 0.5479(2) 0.56190(14) 0.0751(5) Uani 1 1 d .
H17A H 0.277 0.4751 0.544 0.113 Uiso 1 1 calc R
H17B H 0.1352 0.5083 0.5625 0.113 Uiso 1 1 calc R
H17C H 0.2842 0.595 0.6344 0.113 Uiso 1 1 calc R
C14 C 0.45963(12) 0.79122(11) 0.36428(9) 0.0407(2) Uani 1 1 d .
C11 C 0.69498(12) 0.84455(11) 0.73523(9) 0.0397(2) Uani 1 1 d .
H11 H 0.6612 0.9248 0.7365 0.048 Uiso 1 1 calc R
C19 C 0.91341(16) 0.79746(15) 0.66347(13) 0.0597(3) Uani 1 1 d .
H19A H 0.8452 0.7043 0.6583 0.09 Uiso 1 1 calc R
H19B H 1.0013 0.8035 0.7102 0.09 Uiso 1 1 calc R
H19C H 0.9358 0.8208 0.59 0.09 Uiso 1 1 calc R
C6 C 0.28329(15) 0.54134(13) 0.86360(11) 0.0506(3) Uani 1 1 d .
H6 H 0.2343 0.4465 0.8645 0.061 Uiso 1 1 calc R
C4 C 0.51098(13) 0.73052(12) 0.85908(9) 0.0441(2) Uani 1 1 d .
C8 C 0.67550(14) 0.78536(13) 0.85161(9) 0.0471(3) Uani 1 1 d .
C2 C 0.28345(16) 0.77506(14) 0.86795(13) 0.0573(3) Uani 1 1 d .
H2 H 0.234 0.8386 0.8716 0.069 Uiso 1 1 calc R
C1 C 0.20763(14) 0.63387(13) 0.86646(10) 0.0488(3) Uani 1 1 d .
C9 C 0.75189(18) 0.90565(19) 0.94427(11) 0.0677(4) Uani 1 1 d .
H9A H 0.7117 0.979 0.9354 0.101 Uiso 1 1 calc R
H9B H 0.8546 0.9407 0.9389 0.101 Uiso 1 1 calc R
H9C H 0.737 0.8722 1.0162 0.101 Uiso 1 1 calc R
C20 C 0.91845(14) 1.03418(14) 0.72935(11) 0.0525(3) Uani 1 1 d .
C3 C 0.43175(15) 0.82177(13) 0.86403(12) 0.0542(3) Uani 1 1 d .
H3 H 0.4806 0.9169 0.8647 0.065 Uiso 1 1 calc R
C5 C 0.43304(15) 0.59017(13) 0.85936(11) 0.0497(3) Uani 1 1 d .
H5 H 0.4824 0.5265 0.8566 0.06 Uiso 1 1 calc R
C16 C 0.26952(14) 0.65136(16) 0.47443(10) 0.0555(3) Uani 1 1 d .
H16 H 0.2185 0.6012 0.4021 0.067 Uiso 1 1 calc R
C21 C 1.07767(17) 1.09051(17) 0.70388(14) 0.0660(4) Uani 1 1 d .
C7 C -0.02392(19) 0.45225(19) 0.84941(19) 0.0796(5) Uani 1 1 d .
H7A H -0.1252 0.4401 0.8513 0.119 Uiso 1 1 calc R
H7B H 0.0086 0.4048 0.9074 0.119 Uiso 1 1 calc R
H7C H -0.0116 0.4144 0.7779 0.119 Uiso 1 1 calc R
F2 F 1.16612(12) 1.04052(16) 0.76638(11) 0.1003(4) Uani 1 1 d .
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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C14 O4 C15 116.49(10)
C1 O1 C7 117.38(12)
C12 N1 C13 120.91(9)
C20 N2 C19 123.19(11)
C20 N2 C11 116.68(10)
C19 N2 C11 119.88(10)
N1 C13 C14 109.53(9)
N1 C13 C16 113.23(9)
C14 C13 C16 109.56(9)
O2 C12 N1 123.01(10)
O2 C12 C11 122.15(10)
N1 C12 C11 114.83(9)
O3 C14 O4 123.80(10)
O3 C14 C13 126.06(10)
O4 C14 C13 110.11(9)
N2 C11 C12 108.98(9)
N2 C11 C8 113.75(9)
C12 C11 C8 113.03(9)
C1 C6 C5 119.90(12)
C5 C4 C3 116.60(12)
C5 C4 C8 122.62(11)
C3 C4 C8 120.77(11)
C4 C8 C10 111.58(11)
C4 C8 C9 109.52(11)
C10 C8 C9 107.44(12)
C4 C8 C11 107.02(9)
C10 C8 C11 112.88(10)
C9 C8 C11 108.34(11)
C3 C2 C1 120.30(12)
O1 C1 C6 124.89(12)
O1 C1 C2 116.03(12)
C6 C1 C2 119.08(12)
O5 C20 N2 125.77(13)
O5 C20 C21 116.48(12)
N2 C20 C21 117.74(12)
C2 C3 C4 121.97(12)
C4 C5 C6 122.13(11)
C17 C16 C18 111.17(14)
C17 C16 C13 110.61(12)
C18 C16 C13 112.13(13)
F1 C21 F3 106.37(16)
F1 C21 F2 107.25(15)
F3 C21 F2 105.52(15)
F1 C21 C20 110.78(14)
F3 C21 C20 113.87(12)
F2 C21 C20 112.59(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C21 1.300(2)
O2 C12 1.2176(13)
F3 C21 1.320(2)
O3 C14 1.2027(14)
O4 C14 1.3313(13)
O4 C15 1.4416(15)
O5 C20 1.2154(17)
O1 C1 1.3693(16)
O1 C7 1.427(2)
N1 C12 1.3491(13)
N1 C13 1.4555(13)
N2 C20 1.3447(16)
N2 C19 1.4767(16)
N2 C11 1.4834(15)
C18 C16 1.526(3)
C13 C14 1.5155(15)
C13 C16 1.5476(17)
C10 C8 1.5371(19)
C12 C11 1.5383(14)
C17 C16 1.521(2)
C11 C8 1.5671(16)
C6 C1 1.3804(18)
C6 C5 1.3918(19)
C4 C5 1.3850(17)
C4 C3 1.3975(17)
C4 C8 1.5353(17)
C8 C9 1.5407(18)
C2 C3 1.378(2)
C2 C1 1.3858(19)
C20 C21 1.544(2)
C21 F2 1.334(2)
