#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:53:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178922 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/51/4115189.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_4115189
loop_
_publ_author_name
'Brian D. Dangel'
'Kamil Godula'
'So Won Youn'
'Bengü Sezen'
'Dalibor Sames'
_publ_section_title
;
 C-C Bond Formation via C-H Bond Activation: Synthesis of the Core of
 Teleocidin B4
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11856
_journal_page_last               11857
_journal_paper_doi               10.1021/ja027311p
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C18 H25 N O2'
_chemical_formula_weight         287.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.5700(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6548(10)
_cell_length_b                   8.8146(7)
_cell_length_c                   13.7395(11)
_cell_measurement_temperature    238(2)
_cell_volume                     1630.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      238(2)
_diffrn_measured_fraction_theta_full 0.918
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10289
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9422
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0000(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.102
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0644P)²+0.2615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                2857
_reflns_number_total             3610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja027311p_s2.cif
_cod_data_source_block           das10
_cod_database_code               4115189
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
O1 O 0.61218(7) 0.01150(12) 0.77913(7) 0.0467(3) Uani 1 1 d .
O2 O 0.50757(8) -0.45976(12) 0.37083(7) 0.0526(3) Uani 1 1 d .
N N 0.56940(8) -0.32181(12) 0.50535(8) 0.0386(3) Uani 1 1 d .
H0A H 0.5545 -0.3938 0.5437 0.046 Uiso 1 1 calc R
C1 C 0.66716(8) -0.09233(13) 0.49744(9) 0.0328(3) Uani 1 1 d .
C2 C 0.61088(9) -0.18667(13) 0.54975(9) 0.0330(3) Uani 1 1 d .
C3 C 0.59496(9) -0.15166(15) 0.64373(9) 0.0362(3) Uani 1 1 d .
H3A H 0.5586 -0.2175 0.6780 0.043 Uiso 1 1 calc R
C4 C 0.63380(9) -0.01693(15) 0.68676(9) 0.0369(3) Uani 1 1 d .
C5 C 0.68690(10) 0.08000(15) 0.63591(10) 0.0402(3) Uani 1 1 d .
H5A H 0.7113 0.1719 0.6652 0.048 Uiso 1 1 calc R
C6 C 0.70483(9) 0.04288(14) 0.54123(9) 0.0361(3) Uani 1 1 d .
C7 C 0.76194(10) 0.15764(15) 0.48739(11) 0.0422(3) Uani 1 1 d .
C8 C 0.78754(11) 0.08961(17) 0.39121(11) 0.0485(4) Uani 1 1 d .
H8A H 0.8024 0.1725 0.3484 0.058 Uiso 1 1 calc R
H8B H 0.8476 0.0275 0.4074 0.058 Uiso 1 1 calc R
C9 C 0.70480(11) -0.00751(17) 0.33474(11) 0.0466(3) Uani 1 1 d .
H9A H 0.7243 -0.0423 0.2729 0.056 Uiso 1 1 calc R
H9B H 0.6445 0.0538 0.3181 0.056 Uiso 1 1 calc R
C10 C 0.68301(9) -0.14491(14) 0.39569(9) 0.0358(3) Uani 1 1 d .
C11 C 0.58740(10) -0.22295(16) 0.34518(10) 0.0415(3) Uani 1 1 d .
H11A H 0.5351 -0.1464 0.3298 0.050 Uiso 1 1 calc R
H11B H 0.5991 -0.2671 0.2827 0.050 Uiso 1 1 calc R
C12 C 0.55156(10) -0.34586(15) 0.40694(10) 0.0392(3) Uani 1 1 d .
C13 C 0.65033(14) 0.1471(2) 0.82710(13) 0.0690(5) Uani 1 1 d .
H13A H 0.7223 0.1433 0.8393 0.104 Uiso 1 1 calc R
H13B H 0.6263 0.1571 0.8894 0.104 Uiso 1 1 calc R
H13C H 0.6284 0.2335 0.7854 0.104 Uiso 1 1 calc R
C14 C 0.85815(11) 0.21067(18) 0.55626(12) 0.0510(4) Uani 1 1 d .
H14A H 0.8368 0.2711 0.6098 0.061 Uiso 1 1 calc R
C15 C 0.92305(13) 0.3152(2) 0.50364(16) 0.0716(5) Uani 1 1 d .
H15A H 0.9510 0.2572 0.4549 0.107 Uiso 1 1 calc R
H15B H 0.9763 0.3570 0.5517 0.107 Uiso 1 1 calc R
H15C H 0.8827 0.3970 0.4712 0.107 Uiso 1 1 calc R
C16 C 0.92084(12) 0.0796(2) 0.60554(14) 0.0628(5) Uani 1 1 d .
H16A H 0.8825 0.0223 0.6463 0.094 Uiso 1 1 calc R
H16B H 0.9800 0.1195 0.6464 0.094 Uiso 1 1 calc R
H16C H 0.9398 0.0137 0.5553 0.094 Uiso 1 1 calc R
C17 C 0.69237(12) 0.29567(17) 0.46085(14) 0.0580(4) Uani 1 1 d .
H17A H 0.6301 0.2617 0.4226 0.087 Uiso 1 1 calc R
H17B H 0.7237 0.3677 0.4224 0.087 Uiso 1 1 calc R
H17C H 0.6798 0.3440 0.5210 0.087 Uiso 1 1 calc R
C18 C 0.76912(10) -0.25972(17) 0.40533(11) 0.0452(3) Uani 1 1 d .
H18A H 0.8294 -0.2125 0.4394 0.068 Uiso 1 1 calc R
H18B H 0.7790 -0.2917 0.3401 0.068 Uiso 1 1 calc R
H18C H 0.7532 -0.3473 0.4425 0.068 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 O1 C13 117.61(11)
C12 N C2 123.87(11)
C6 C1 C2 118.55(11)
C6 C1 C10 123.92(11)
C2 C1 C10 117.53(11)
C3 C2 C1 122.01(11)
C3 C2 N 118.58(11)
C1 C2 N 119.41(11)
C2 C3 C4 118.70(11)
O1 C4 C5 124.44(12)
O1 C4 C3 115.02(11)
C5 C4 C3 120.50(12)
C4 C5 C6 120.78(12)
C1 C6 C5 119.42(11)
C1 C6 C7 122.29(11)
C5 C6 C7 118.24(11)
C6 C7 C8 111.17(11)
C6 C7 C17 106.81(11)
C8 C7 C17 108.72(13)
C6 C7 C14 110.40(11)
C8 C7 C14 110.40(11)
C17 C7 C14 109.24(12)
C9 C8 C7 113.59(11)
C8 C9 C10 111.19(12)
C1 C10 C9 109.40(11)
C1 C10 C11 108.15(10)
C9 C10 C11 109.60(11)
C1 C10 C18 110.14(10)
C9 C10 C18 110.62(11)
C11 C10 C18 108.90(11)
C12 C11 C10 113.50(11)
O2 C12 N 121.76(12)
O2 C12 C11 122.79(12)
N C12 C11 115.44(11)
C16 C14 C15 109.68(13)
C16 C14 C7 113.34(12)
C15 C14 C7 112.80(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3730(15)
O1 C13 1.4216(19)
O2 C12 1.2312(16)
N C12 1.3501(17)
N C2 1.4132(15)
C1 C6 1.3944(17)
C1 C2 1.4079(17)
C1 C10 1.5220(17)
C2 C3 1.3796(17)
C3 C4 1.3917(18)
C4 C5 1.3827(18)
C5 C6 1.4018(18)
C6 C7 1.5397(17)
C7 C8 1.5433(19)
C7 C17 1.549(2)
C7 C14 1.558(2)
C8 C9 1.523(2)
C9 C10 1.5295(18)
C10 C11 1.5356(18)
C10 C18 1.5403(18)
C11 C12 1.5072(18)
C14 C16 1.528(2)
C14 C15 1.539(2)
