#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:28:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178813 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/67/4106728.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_4106728
loop_
_publ_author_name
'Shun Su'
'Rodrigo A. Rodriguez'
'Phil S. Baran'
_publ_section_title
;
 Scalable, Stereocontrolled Total Syntheses of (\+-)-Axinellamines A and B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13922
_journal_page_last               13925
_journal_paper_doi               10.1021/ja206191g
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C17 H25 Cl2 F3 N2 O4'
_chemical_formula_weight         449.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                101.741(2)
_cell_angle_beta                 93.206(2)
_cell_angle_gamma                92.356(2)
_cell_formula_units_Z            4
_cell_length_a                   8.6245(3)
_cell_length_b                   14.7525(6)
_cell_length_c                   16.9723(6)
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.77
_cell_measurement_theta_min      2.57
_cell_volume                     2107.90(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            26998
_diffrn_reflns_theta_full        24.91
_diffrn_reflns_theta_max         24.91
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       Blade
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         7112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0460P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                5396
_reflns_number_total             7112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja206191g_si_001.cif
_cod_data_source_block           baran208
_cod_database_code               4106728
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
Cl1 Cl 0.10136(8) 0.89852(5) -0.07047(4) 0.04328(18) Uani 1 1 d .
Cl1' Cl 0.43096(8) 0.58952(4) 0.58704(4) 0.04145(18) Uani 1 1 d .
Cl2 Cl 0.43781(6) 0.77852(4) 0.15747(3) 0.02729(15) Uani 1 1 d .
Cl2' Cl 0.05920(6) 0.69272(4) 0.35640(3) 0.02900(15) Uani 1 1 d .
F1' F 0.63373(15) 0.40872(9) 0.10436(8) 0.0387(4) Uani 1 1 d .
F1 F 0.04166(15) 1.09624(9) 0.49838(7) 0.0302(3) Uani 1 1 d .
F2' F 0.45835(17) 0.40664(10) 0.00973(8) 0.0392(4) Uani 1 1 d .
F2 F 0.06861(17) 1.16451(8) 0.40026(8) 0.0389(4) Uani 1 1 d .
F3' F 0.42080(18) 0.32751(9) 0.09916(9) 0.0432(4) Uani 1 1 d .
F3 F -0.13913(15) 1.08084(9) 0.40385(8) 0.0342(3) Uani 1 1 d .
O1' O 0.27611(17) 0.50828(10) 0.11181(9) 0.0261(4) Uani 1 1 d .
O1 O 0.22517(17) 0.98906(10) 0.40028(9) 0.0244(3) Uani 1 1 d .
O2' O 0.62188(17) 0.62365(10) 0.36825(9) 0.0249(4) Uani 1 1 d .
H2'A H 0.6808 0.5894 0.3391 0.037 Uiso 1 1 calc R
O2 O -0.10694(17) 0.87215(10) 0.14444(9) 0.0252(4) Uani 1 1 d .
H2A H -0.1714 0.9040 0.1717 0.038 Uiso 1 1 calc R
O3' O 0.45084(17) 1.01656(10) 0.25240(9) 0.0237(3) Uani 1 1 d .
O3 O -0.20047(17) 0.51529(10) 0.25623(9) 0.0248(4) Uani 1 1 d .
O4' O 0.69705(17) 0.96692(10) 0.25267(8) 0.0222(3) Uani 1 1 d .
O4 O 0.03696(17) 0.45508(10) 0.24154(9) 0.0257(4) Uani 1 1 d .
N1' N 0.4754(2) 0.52516(11) 0.20877(10) 0.0224(4) Uani 1 1 d .
H1'A H 0.5695 0.5085 0.2200 0.027 Uiso 1 1 calc R
N1 N 0.0217(2) 0.95869(11) 0.30595(10) 0.0206(4) Uani 1 1 d .
H1A H -0.0739 0.9724 0.2937 0.025 Uiso 1 1 calc R
N2' N 0.5238(2) 0.93350(11) 0.33973(10) 0.0192(4) Uani 1 1 d .
H2'B H 0.4277 0.9391 0.3542 0.023 Uiso 1 1 calc R
N2 N -0.0389(2) 0.54851(11) 0.16391(10) 0.0219(4) Uani 1 1 d .
H2B H 0.0540 0.5406 0.1456 0.026 Uiso 1 1 calc R
C1' C 0.4812(3) 0.40759(15) 0.08746(13) 0.0242(5) Uani 1 1 d .
C1 C 0.0149(2) 1.08664(14) 0.41952(13) 0.0219(5) Uani 1 1 d .
C2' C 0.4015(2) 0.48815(14) 0.13848(13) 0.0210(5) Uani 1 1 d .
C2 C 0.0967(2) 1.00392(13) 0.37335(12) 0.0186(5) Uani 1 1 d .
C3' C 0.4024(3) 0.59332(14) 0.26794(13) 0.0250(5) Uani 1 1 d .
H3'A H 0.3446 0.5608 0.3037 0.030 Uiso 1 1 calc R
H3'B H 0.3265 0.6260 0.2395 0.030 Uiso 1 1 calc R
C3 C 0.0962(3) 0.88610(14) 0.25170(13) 0.0229(5) Uani 1 1 d .
H3A H 0.1559 0.8488 0.2839 0.027 Uiso 1 1 calc R
H3B H 0.1703 0.9150 0.2204 0.027 Uiso 1 1 calc R
C4' C 0.5193(2) 0.66406(14) 0.31901(12) 0.0198(5) Uani 1 1 d .
H4'A H 0.5814 0.6944 0.2826 0.024 Uiso 1 1 calc R
C4 C -0.0217(2) 0.82290(14) 0.19406(12) 0.0188(5) Uani 1 1 d .
H4A H -0.0955 0.7934 0.2260 0.023 Uiso 1 1 calc R
C5' C 0.4331(2) 0.73818(13) 0.37402(12) 0.0185(5) Uani 1 1 d .
H5'A H 0.3561 0.7644 0.3397 0.022 Uiso 1 1 calc R
C5 C 0.0614(2) 0.74679(13) 0.13950(12) 0.0190(5) Uani 1 1 d .
H5A H 0.1341 0.7177 0.1739 0.023 Uiso 1 1 calc R
C6' C 0.5385(2) 0.81709(14) 0.42177(13) 0.0198(5) Uani 1 1 d .
C6 C -0.0502(2) 0.67196(14) 0.09025(13) 0.0213(5) Uani 1 1 d .
C7' C 0.5376(3) 0.82125(14) 0.50014(13) 0.0242(5) Uani 1 1 d .
H7'A H 0.5939 0.8680 0.5392 0.029 Uiso 1 1 calc R
C7 C -0.0501(3) 0.67092(15) 0.01225(13) 0.0256(5) Uani 1 1 d .
H7A H -0.1128 0.6283 -0.0275 0.031 Uiso 1 1 calc R
C8' C 0.4388(3) 0.74481(15) 0.52124(13) 0.0236(5) Uani 1 1 d .
H8'A H 0.3664 0.7711 0.5630 0.028 Uiso 1 1 calc R
C8 C 0.0590(3) 0.74396(15) -0.00709(13) 0.0240(5) Uani 1 1 d .
H8A H 0.1301 0.7145 -0.0483 0.029 Uiso 1 1 calc R
C9' C 0.3452(2) 0.70276(14) 0.44007(12) 0.0197(5) Uani 1 1 d .
H9'A H 0.3413 0.6335 0.4299 0.024 Uiso 1 1 calc R
C9 C 0.1541(2) 0.78109(14) 0.07477(12) 0.0204(5) Uani 1 1 d .
H9A H 0.1644 0.8504 0.0864 0.024 Uiso 1 1 calc R
C10' C 0.5421(3) 0.67743(16) 0.55275(14) 0.0294(5) Uani 1 1 d .
H10A H 0.6128 0.7120 0.5978 0.035 Uiso 1 1 calc R
H10B H 0.6068 0.6478 0.5093 0.035 Uiso 1 1 calc R
C10 C -0.0294(3) 0.81718(16) -0.03895(14) 0.0298(5) Uani 1 1 d .
H10C H -0.0921 0.8504 0.0038 0.036 Uiso 1 1 calc R
H10D H -0.1013 0.7869 -0.0852 0.036 Uiso 1 1 calc R
C11' C 0.1832(2) 0.73756(15) 0.44586(13) 0.0244(5) Uani 1 1 d .
H11A H 0.1899 0.8061 0.4554 0.029 Uiso 1 1 calc R
H11B H 0.1362 0.7195 0.4927 0.029 Uiso 1 1 calc R
C11 C 0.3124(2) 0.74104(15) 0.06731(12) 0.0230(5) Uani 1 1 d .
H11C H 0.3620 0.7599 0.0215 0.028 Uiso 1 1 calc R
H11D H 0.2995 0.6725 0.0554 0.028 Uiso 1 1 calc R
C12' C 0.6291(2) 0.88246(14) 0.38251(13) 0.0220(5) Uani 1 1 d .
H12A H 0.6949 0.9265 0.4240 0.026 Uiso 1 1 calc R
H12B H 0.6981 0.8472 0.3442 0.026 Uiso 1 1 calc R
C12 C -0.1426(3) 0.60653(14) 0.12798(14) 0.0245(5) Uani 1 1 d .
H12C H -0.2046 0.6419 0.1700 0.029 Uiso 1 1 calc R
H12D H -0.2154 0.5671 0.0866 0.029 Uiso 1 1 calc R
C13' C 0.5681(2) 0.97182(14) 0.27970(12) 0.0186(5) Uani 1 1 d .
C13 C -0.0776(2) 0.50688(14) 0.22303(13) 0.0194(5) Uani 1 1 d .
C14' C 0.4725(3) 1.07392(15) 0.19178(14) 0.0273(5) Uani 1 1 d .
C14 C 0.0192(3) 0.39235(16) 0.29806(14) 0.0298(6) Uani 1 1 d .
C15' C 0.5925(3) 1.15212(16) 0.22481(15) 0.0345(6) Uani 1 1 d .
H15A H 0.6944 1.1266 0.2312 0.052 Uiso 1 1 calc R
H15B H 0.5632 1.1859 0.2773 0.052 Uiso 1 1 calc R
H15C H 0.5975 1.1945 0.1873 0.052 Uiso 1 1 calc R
C15 C -0.1193(3) 0.32410(16) 0.26988(15) 0.0347(6) Uani 1 1 d .
H15D H -0.1105 0.2939 0.2134 0.052 Uiso 1 1 calc R
H15E H -0.2155 0.3573 0.2749 0.052 Uiso 1 1 calc R
H15F H -0.1210 0.2771 0.3032 0.052 Uiso 1 1 calc R
C16' C 0.5120(3) 1.01558(17) 0.11226(14) 0.0366(6) Uani 1 1 d .
H16A H 0.6140 0.9900 0.1187 0.055 Uiso 1 1 calc R
H16B H 0.5150 1.0541 0.0716 0.055 Uiso 1 1 calc R
H16C H 0.4329 0.9648 0.0949 0.055 Uiso 1 1 calc R
C16 C 0.1690(3) 0.34246(19) 0.28959(19) 0.0468(7) Uani 1 1 d .
H16D H 0.2574 0.3871 0.3077 0.070 Uiso 1 1 calc R
H16E H 0.1775 0.3128 0.2329 0.070 Uiso 1 1 calc R
H16F H 0.1690 0.2951 0.3226 0.070 Uiso 1 1 calc R
C17' C 0.3126(3) 1.1114(2) 0.18412(19) 0.0494(8) Uani 1 1 d .
H17A H 0.2359 1.0598 0.1639 0.074 Uiso 1 1 calc R
H17B H 0.3132 1.1536 0.1464 0.074 Uiso 1 1 calc R
H17C H 0.2853 1.1450 0.2371 0.074 Uiso 1 1 calc R
C17 C 0.0077(3) 0.44742(19) 0.38297(15) 0.0425(7) Uani 1 1 d .
H17D H 0.0955 0.4933 0.3968 0.064 Uiso 1 1 calc R
H17E H 0.0102 0.4054 0.4209 0.064 Uiso 1 1 calc R
H17F H -0.0900 0.4792 0.3862 0.064 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C13' O3' C14' 121.76(17)
C13 O4 C14 122.21(17)
C2' N1' C3' 120.69(18)
C2 N1 C3 120.36(17)
C13' N2' C12' 122.20(19)
C13 N2 C12 123.32(19)
F2' C1' F3' 106.75(17)
F2' C1' F1' 107.65(19)
F3' C1' F1' 107.20(18)
F2' C1' C2' 111.26(18)
F3' C1' C2' 109.77(19)
F1' C1' C2' 113.88(17)
F1 C1 F2 107.04(16)
F1 C1 F3 107.55(18)
F2 C1 F3 107.15(17)
F1 C1 C2 111.39(17)
F2 C1 C2 109.90(18)
F3 C1 C2 113.53(17)
O1' C2' N1' 127.6(2)
O1' C2' C1' 117.30(18)
N1' C2' C1' 115.07(18)
O1 C2 N1 127.1(2)
O1 C2 C1 117.49(18)
N1 C2 C1 115.38(18)
N1' C3' C4' 112.66(18)
N1 C3 C4 111.75(17)
O2' C4' C3' 112.42(17)
O2' C4' C5' 108.05(16)
C3' C4' C5' 109.58(17)
O2 C4 C3 111.70(16)
O2 C4 C5 108.23(16)
C3 C4 C5 109.93(17)
C6' C5' C4' 113.78(17)
C6' C5' C9' 103.19(16)
C4' C5' C9' 114.69(17)
C6 C5 C4 112.75(17)
C6 C5 C9 103.23(16)
C4 C5 C9 114.24(17)
C7' C6' C12' 125.44(19)
C7' C6' C5' 112.04(19)
C12' C6' C5' 122.51(18)
C7 C6 C12 125.76(19)
C7 C6 C5 112.07(19)
C12 C6 C5 122.13(18)
C6' C7' C8' 113.23(18)
C6 C7 C8 113.13(18)
C7' C8' C10' 109.62(19)
C7' C8' C9' 102.75(16)
C10' C8' C9' 114.20(18)
C7 C8 C10 111.19(19)
C7 C8 C9 102.91(17)
C10 C8 C9 114.10(18)
C11' C9' C5' 111.88(17)
C11' C9' C8' 107.57(17)
C5' C9' C8' 105.79(16)
C11 C9 C5 112.45(17)
C11 C9 C8 107.04(17)
C5 C9 C8 105.90(16)
C8' C10' Cl1' 111.91(17)
C8 C10 Cl1 111.01(17)
C9' C11' Cl2' 112.71(15)
C9 C11 Cl2 112.50(14)
N2' C12' C6' 110.23(17)
N2 C12 C6 109.87(18)
O4' C13' N2' 125.17(19)
O4' C13' O3' 124.66(19)
N2' C13' O3' 110.17(19)
O3 C13 N2 124.87(19)
O3 C13 O4 124.8(2)
N2 C13 O4 110.29(19)
O3' C14' C16' 111.19(18)
O3' C14' C15' 109.56(17)
C16' C14' C15' 113.0(2)
O3' C14' C17' 101.56(19)
C16' C14' C17' 110.5(2)
C15' C14' C17' 110.5(2)
O4 C14 C16 101.28(19)
O4 C14 C17 110.42(19)
C16 C14 C17 111.6(2)
O4 C14 C15 110.16(18)
C16 C14 C15 110.1(2)
C17 C14 C15 112.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C10 1.793(2)
Cl1' C10' 1.791(2)
Cl2 C11 1.800(2)
Cl2' C11' 1.800(2)
F1' C1' 1.329(2)
F1 C1 1.323(2)
F2' C1' 1.320(3)
F2 C1 1.329(2)
F3' C1' 1.328(3)
F3 C1 1.336(2)
O1' C2' 1.221(2)
O1 C2 1.220(2)
O2' C4' 1.414(2)
O2 C4 1.415(2)
O3' C13' 1.342(2)
O3' C14' 1.474(3)
O3 C13 1.227(3)
O4' C13' 1.226(2)
O4 C13 1.335(2)
O4 C14 1.472(3)
N1' C2' 1.322(3)
N1' C3' 1.459(3)
N1 C2 1.321(3)
N1 C3 1.459(3)
N2' C13' 1.328(3)
N2' C12' 1.457(3)
N2 C13 1.329(3)
N2 C12 1.456(3)
C1' C2' 1.533(3)
C1 C2 1.531(3)
C3' C4' 1.518(3)
C3 C4 1.517(3)
C4' C5' 1.532(3)
C4 C5 1.532(3)
C5' C6' 1.511(3)
C5' C9' 1.551(3)
C5 C6 1.513(3)
C5 C9 1.547(3)
C6' C7' 1.319(3)
C6' C12' 1.498(3)
C6 C7 1.321(3)
C6 C12 1.491(3)
C7' C8' 1.498(3)
C7 C8 1.500(3)
C8' C10' 1.517(3)
C8' C9' 1.556(3)
C8 C10 1.516(3)
C8 C9 1.559(3)
C9' C11' 1.509(3)
C9 C11 1.511(3)
C14' C16' 1.510(3)
C14' C15' 1.513(3)
C14' C17' 1.515(3)
C14 C16 1.512(3)
C14 C17 1.514(4)
C14 C15 1.519(3)
