#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:15:57 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179016 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/14/4121424.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_4121424
loop_
_publ_author_name
'Mori, Keiji'
'Kurihara, Kazuki'
'Yabe, Shinnosuke'
'Yamanaka, Masahiro'
'Akiyama, Takahiko'
_publ_section_title
;
 Double C(sp(3))-H Bond Functionalization Mediated by Sequential Hydride
 Shift/Cyclization Process: Diastereoselective Construction of
 Polyheterocycles.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3744
_journal_page_last               3747
_journal_paper_doi               10.1021/ja412706d
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C26 H24 F3 N O'
_chemical_formula_weight         423.46
_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                107.003(2)
_cell_angle_beta                 109.020(2)
_cell_angle_gamma                95.887(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4028(13)
_cell_length_b                   10.1616(14)
_cell_length_c                   14.1650(19)
_cell_measurement_reflns_used    4314
_cell_measurement_temperature    123
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.20
_cell_volume                     1193.9(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6368
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.679
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0719P)²+1.3944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1550
_reflns_number_gt                4242
_reflns_number_total             4762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja412706d_si_012.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               4121424
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
C1 C 0.8827(2) 0.99609(19) 0.80463(15) 0.0181(4) Uani 1 1 d .
H1 H 0.9971 1.0288 0.8420 0.022 Uiso 1 1 calc R
C2 C 0.9037(2) 1.20245(19) 0.76407(15) 0.0187(4) Uani 1 1 d .
H2 H 1.0155 1.2216 0.8093 0.022 Uiso 1 1 calc R
C3 C 0.8843(2) 1.1251(2) 0.64725(15) 0.0195(4) Uani 1 1 d .
C4 C 1.0201(2) 1.1922(2) 0.62471(16) 0.0233(4) Uani 1 1 d .
H4A H 0.9924 1.1721 0.5474 0.028 Uiso 1 1 calc R
H4B H 1.0497 1.2956 0.6619 0.028 Uiso 1 1 calc R
C5 C 1.1493(2) 1.1230(2) 0.66754(15) 0.0208(4) Uani 1 1 d .
C6 C 1.3075(2) 1.1675(2) 0.69657(16) 0.0240(4) Uani 1 1 d .
H6 H 1.3482 1.2528 0.6905 0.029 Uiso 1 1 calc R
C7 C 1.4050(2) 1.0846(2) 0.73461(16) 0.0250(4) Uani 1 1 d .
H7 H 1.5131 1.1136 0.7545 0.030 Uiso 1 1 calc R
C8 C 1.3455(2) 0.9600(2) 0.74377(16) 0.0232(4) Uani 1 1 d .
H8 H 1.4134 0.9047 0.7699 0.028 Uiso 1 1 calc R
C9 C 1.1870(2) 0.9154(2) 0.71486(15) 0.0211(4) Uani 1 1 d .
H9 H 1.1462 0.8299 0.7207 0.025 Uiso 1 1 calc R
C10 C 1.0903(2) 0.99856(19) 0.67731(14) 0.0188(4) Uani 1 1 d .
C11 C 0.9162(2) 0.97342(19) 0.64128(15) 0.0184(4) Uani 1 1 d .
H11 H 0.8720 0.9119 0.5645 0.022 Uiso 1 1 calc R
C12 C 0.7276(2) 1.1206(2) 0.56729(16) 0.0252(4) Uani 1 1 d .
H12A H 0.6464 1.0922 0.5912 0.038 Uiso 1 1 calc R
H12B H 0.7113 1.0523 0.4975 0.038 Uiso 1 1 calc R
H12C H 0.7244 1.2142 0.5619 0.038 Uiso 1 1 calc R
C13 C 0.8521(2) 1.3416(2) 0.78778(16) 0.0228(4) Uani 1 1 d .
C14 C 0.8240(2) 0.9311(2) 0.87183(15) 0.0195(4) Uani 1 1 d .
C15 C 0.7409(2) 0.9980(2) 0.92906(16) 0.0232(4) Uani 1 1 d .
H15 H 0.7153 1.0842 0.9235 0.028 Uiso 1 1 calc R
C16 C 0.6950(2) 0.9390(2) 0.99460(17) 0.0278(4) Uani 1 1 d .
H16 H 0.6382 0.9853 1.0335 0.033 Uiso 1 1 calc R
C17 C 0.7315(2) 0.8141(2) 1.00346(17) 0.0287(5) Uani 1 1 d .
H17 H 0.6995 0.7742 1.0481 0.034 Uiso 1 1 calc R
C18 C 0.8152(3) 0.7468(2) 0.94697(18) 0.0313(5) Uani 1 1 d .
H18 H 0.8413 0.6610 0.9533 0.038 Uiso 1 1 calc R
C19 C 0.8607(3) 0.8048(2) 0.88115(17) 0.0270(4) Uani 1 1 d .
H19 H 0.9172 0.7581 0.8422 0.032 Uiso 1 1 calc R
C20 C 0.6952(2) 0.81636(19) 0.63709(15) 0.0206(4) Uani 1 1 d .
H20A H 0.6308 0.8735 0.6032 0.025 Uiso 1 1 calc R
H20B H 0.6507 0.7903 0.6853 0.025 Uiso 1 1 calc R
C21 C 0.6929(2) 0.68368(19) 0.55199(15) 0.0195(4) Uani 1 1 d .
C22 C 0.8060(2) 0.6061(2) 0.57239(18) 0.0271(4) Uani 1 1 d .
H22 H 0.8893 0.6392 0.6394 0.032 Uiso 1 1 calc R
C23 C 0.7981(3) 0.4809(2) 0.4957(2) 0.0331(5) Uani 1 1 d .
H23 H 0.8754 0.4285 0.5106 0.040 Uiso 1 1 calc R
C24 C 0.6776(3) 0.4321(2) 0.39739(19) 0.0330(5) Uani 1 1 d .
H24 H 0.6729 0.3466 0.3448 0.040 Uiso 1 1 calc R
C25 C 0.5644(3) 0.5079(2) 0.37597(17) 0.0306(5) Uani 1 1 d .
H25 H 0.4814 0.4745 0.3088 0.037 Uiso 1 1 calc R
C26 C 0.5727(2) 0.6334(2) 0.45332(16) 0.0231(4) Uani 1 1 d .
H26 H 0.4949 0.6853 0.4383 0.028 Uiso 1 1 calc R
C27 C 0.2666(4) 0.6510(3) 0.8716(2) 0.0543(7) Uani 1 1 d .
H27A H 0.3408 0.7022 0.8526 0.082 Uiso 1 1 calc R
H27B H 0.1957 0.7101 0.8878 0.082 Uiso 1 1 calc R
H27C H 0.2081 0.5639 0.8119 0.082 Uiso 1 1 calc R
C28 C 0.3504(4) 0.6156(4) 0.9665(3) 0.0582(8) Uani 1 1 d .
H28A H 0.4147 0.7043 1.0240 0.070 Uiso 1 1 calc R
H28B H 0.2732 0.5773 0.9908 0.070 Uiso 1 1 calc R
C29 C 0.4508(3) 0.5139(3) 0.9532(3) 0.0542(8) Uani 1 1 d .
H29A H 0.3837 0.4226 0.9011 0.065 Uiso 1 1 calc R
H29B H 0.5189 0.5471 0.9205 0.065 Uiso 1 1 calc R
F1 F 0.69904(14) 1.32675(13) 0.75412(10) 0.0297(3) Uani 1 1 d .
F2 F 0.90732(16) 1.41153(13) 0.89316(10) 0.0321(3) Uani 1 1 d .
F3 F 0.90370(16) 1.42789(13) 0.74446(11) 0.0334(3) Uani 1 1 d .
N1 N 0.85336(17) 0.90081(16) 0.69936(12) 0.0181(3) Uani 1 1 d .
O1 O 0.82042(15) 1.11982(13) 0.80214(10) 0.0190(3) 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 0.0000 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
_geom_angle_site_symmetry_1
N1 C1 O1 111.89(15) .
N1 C1 C14 114.53(15) .
O1 C1 C14 108.41(14) .
N1 C1 H1 107.2 .
O1 C1 H1 107.2 .
C14 C1 H1 107.2 .
O1 C2 C13 104.05(14) .
O1 C2 C3 112.48(15) .
C13 C2 C3 117.02(16) .
O1 C2 H2 107.6 .
C13 C2 H2 107.6 .
C3 C2 H2 107.6 .
C12 C3 C2 112.76(15) .
C12 C3 C4 112.41(16) .
C2 C3 C4 109.45(15) .
C12 C3 C11 113.12(16) .
C2 C3 C11 106.17(14) .
C4 C3 C11 102.25(14) .
C5 C4 C3 104.11(15) .
C5 C4 H4A 110.9 .
C3 C4 H4A 110.9 .
C5 C4 H4B 110.9 .
C3 C4 H4B 110.9 .
H4A C4 H4B 109.0 .
C10 C5 C6 120.35(18) .
C10 C5 C4 110.19(17) .
C6 C5 C4 129.45(18) .
C7 C6 C5 118.87(18) .
C7 C6 H6 120.6 .
C5 C6 H6 120.6 .
C8 C7 C6 120.58(18) .
C8 C7 H7 119.7 .
C6 C7 H7 119.7 .
C7 C8 C9 120.66(19) .
C7 C8 H8 119.7 .
C9 C8 H8 119.7 .
C10 C9 C8 118.53(18) .
C10 C9 H9 120.7 .
C8 C9 H9 120.7 .
C9 C10 C5 121.00(18) .
C9 C10 C11 128.57(17) .
C5 C10 C11 110.43(16) .
N1 C11 C10 113.53(15) .
N1 C11 C3 117.60(14) .
C10 C11 C3 102.90(14) .
N1 C11 H11 107.4 .
C10 C11 H11 107.4 .
C3 C11 H11 107.4 .
C3 C12 H12A 109.5 .
C3 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C3 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
F1 C13 F3 106.81(16) .
F1 C13 F2 106.43(15) .
F3 C13 F2 106.48(16) .
F1 C13 C2 113.73(16) .
F3 C13 C2 112.72(16) .
F2 C13 C2 110.21(16) .
C15 C14 C19 119.09(18) .
C15 C14 C1 121.47(17) .
C19 C14 C1 119.35(17) .
C14 C15 C16 120.14(19) .
C14 C15 H15 119.9 .
C16 C15 H15 119.9 .
C17 C16 C15 120.5(2) .
C17 C16 H16 119.7 .
C15 C16 H16 119.7 .
C16 C17 C18 119.8(2) .
C16 C17 H17 120.1 .
C18 C17 H17 120.1 .
C17 C18 C19 120.0(2) .
C17 C18 H18 120.0 .
C19 C18 H18 120.0 .
C18 C19 C14 120.5(2) .
C18 C19 H19 119.7 .
C14 C19 H19 119.7 .
N1 C20 C21 111.15(15) .
N1 C20 H20A 109.4 .
C21 C20 H20A 109.4 .
N1 C20 H20B 109.4 .
C21 C20 H20B 109.4 .
H20A C20 H20B 108.0 .
C26 C21 C22 118.62(18) .
C26 C21 C20 120.15(17) .
C22 C21 C20 121.15(18) .
C23 C22 C21 120.6(2) .
C23 C22 H22 119.7 .
C21 C22 H22 119.7 .
C24 C23 C22 120.2(2) .
C24 C23 H23 119.9 .
C22 C23 H23 119.9 .
C25 C24 C23 119.9(2) .
C25 C24 H24 120.1 .
C23 C24 H24 120.1 .
C24 C25 C26 119.7(2) .
C24 C25 H25 120.2 .
C26 C25 H25 120.2 .
C21 C26 C25 121.0(2) .
C21 C26 H26 119.5 .
C25 C26 H26 119.5 .
C28 C27 H27A 109.5 .
C28 C27 H27B 109.5 .
H27A C27 H27B 109.5 .
C28 C27 H27C 109.5 .
H27A C27 H27C 109.5 .
H27B C27 H27C 109.5 .
C29 C28 C27 117.1(3) .
C29 C28 H28A 108.0 .
C27 C28 H28A 108.0 .
C29 C28 H28B 108.0 .
C27 C28 H28B 108.0 .
H28A C28 H28B 107.3 .
C29 C29 C28 119.6(4) 2_667
C29 C29 H29A 107.4 2_667
C28 C29 H29A 107.4 .
C29 C29 H29B 107.4 2_667
C28 C29 H29B 107.4 .
H29A C29 H29B 107.0 .
C1 N1 C11 110.25(14) .
C1 N1 C20 116.93(15) .
C11 N1 C20 113.65(15) .
C2 O1 C1 109.31(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.439(2) .
C1 O1 1.445(2) .
C1 C14 1.511(3) .
C1 H1 1.0000 .
C2 O1 1.419(2) .
C2 C13 1.522(3) .
C2 C3 1.550(3) .
C2 H2 1.0000 .
C3 C12 1.525(3) .
C3 C4 1.553(3) .
C3 C11 1.583(3) .
C4 C5 1.510(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C10 1.391(3) .
C5 C6 1.394(3) .
C6 C7 1.393(3) .
C6 H6 0.9500 .
C7 C8 1.389(3) .
C7 H7 0.9500 .
C8 C9 1.397(3) .
C8 H8 0.9500 .
C9 C10 1.389(3) .
C9 H9 0.9500 .
C10 C11 1.517(2) .
C11 N1 1.467(2) .
C11 H11 1.0000 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 F1 1.337(2) .
C13 F3 1.342(2) .
C13 F2 1.342(2) .
C14 C15 1.389(3) .
C14 C19 1.394(3) .
C15 C16 1.393(3) .
C15 H15 0.9500 .
C16 C17 1.378(3) .
C16 H16 0.9500 .
C17 C18 1.388(3) .
C17 H17 0.9500 .
C18 C19 1.389(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 N1 1.472(2) .
C20 C21 1.516(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C26 1.388(3) .
C21 C22 1.394(3) .
C22 C23 1.387(3) .
C22 H22 0.9500 .
C23 C24 1.386(3) .
C23 H23 0.9500 .
C24 C25 1.384(3) .
C24 H24 0.9500 .
C25 C26 1.392(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 C28 1.485(5) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 C29 1.482(5) .
C28 H28A 0.9900 .
C28 H28B 0.9900 .
C29 C29 1.472(6) 2_667
C29 H29A 0.9900 .
C29 H29B 0.9900 .
