#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:45:11 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178914 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/43/4114321.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_4114321
loop_
_publ_author_name
'Gireesh M. Mahandru'
'Andy R. L. Skauge'
'Sanjoy K. Chowdhury'
'Kande K. D. Amarasinghe'
'Mary Jane Heeg'
'John Montgomery'
_publ_section_title
;
 Cascade Cyclizations and Couplings Involving Nickel Enolates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13481
_journal_page_last               13485
_journal_paper_doi               10.1021/ja037423w
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C18 H22 O2'
_chemical_formula_weight         270.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.645(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8636(11)
_cell_length_b                   5.7493(7)
_cell_length_c                   25.496(3)
_cell_measurement_reflns_used    815
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.
_cell_measurement_theta_min      3.
_cell_volume                     1425.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_method       'SMART CCD'
_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  0.072
_diffrn_reflns_av_sigmaI/netI    0.1441
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10315
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9920
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       plates
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0124(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   0.784
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.784
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                1267
_reflns_number_total             3367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037423wsi20030715_122235.cif
_cod_data_source_block           kaug
_cod_database_code               4114321
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.04968(17) 0.6476(3) 0.27795(6) 0.0493(5) Uani 1 1 d
O2 O -0.12559(15) 1.0007(3) 0.32373(7) 0.0467(5) Uani 1 1 d
C1 C 0.0733(2) 0.5369(4) 0.33012(9) 0.0372(6) Uani 1 1 d
C2 C 0.2250(2) 0.5389(4) 0.35346(8) 0.0361(6) Uani 1 1 d
C3 C 0.2471(2) 0.7071(4) 0.38999(9) 0.0392(6) Uani 1 1 d
C4 C 0.3655(3) 0.7920(6) 0.43037(12) 0.0576(8) Uani 1 1 d
C5 C 0.2996(3) 0.9616(7) 0.46569(14) 0.0651(9) Uani 1 1 d
C6 C 0.1470(2) 0.8912(5) 0.45736(10) 0.0487(7) Uani 1 1 d
C7 C 0.1182(2) 0.8307(4) 0.39805(9) 0.0369(6) Uani 1 1 d
C8 C 0.00306(19) 0.6653(4) 0.37159(8) 0.0323(5) Uani 1 1 d
C9 C 0.3227(2) 0.3778(4) 0.33487(9) 0.0380(6) Uani 1 1 d
C10 C 0.2768(3) 0.1964(4) 0.29998(9) 0.0436(7) Uani 1 1 d
C11 C 0.3671(3) 0.0408(5) 0.28298(11) 0.0515(7) Uani 1 1 d
C12 C 0.5067(3) 0.0638(5) 0.29964(11) 0.0518(7) Uani 1 1 d
C13 C 0.5553(3) 0.2440(5) 0.33334(11) 0.0556(8) Uani 1 1 d
C14 C 0.4650(2) 0.3988(5) 0.35086(11) 0.0502(7) Uani 1 1 d
C15 C -0.1339(2) 0.7823(4) 0.34971(9) 0.0371(6) Uani 1 1 d
C16 C -0.2022(3) 0.8195(5) 0.39866(10) 0.0469(7) Uani 1 1 d
C17 C -0.1592(3) 0.6081(5) 0.43411(11) 0.0495(7) Uani 1 1 d
C18 C -0.0417(3) 0.4901(5) 0.41086(10) 0.0436(6) Uani 1 1 d
H1O1 H 0.093(3) 0.769(7) 0.2768(15) 0.149(18) Uiso 1 1 d
H1O2 H -0.104(3) 0.978(5) 0.2908(12) 0.110(12) Uiso 1 1 d
H1 H 0.0294(19) 0.371(4) 0.3207(8) 0.047(6) Uiso 1 1 d
H4A H 0.409(2) 0.651(4) 0.4522(8) 0.053(7) Uiso 1 1 d
H4B H 0.434(2) 0.862(4) 0.4147(9) 0.067(8) Uiso 1 1 d
H5A H 0.339(2) 0.938(4) 0.5016(9) 0.056(8) Uiso 1 1 d
H5B H 0.305(3) 1.131(5) 0.4536(11) 0.091(11) Uiso 1 1 d
H6A H 0.084(2) 1.016(4) 0.4656(9) 0.055(7) Uiso 1 1 d
H6B H 0.129(2) 0.741(5) 0.4805(9) 0.073(8) Uiso 1 1 d
H7 H 0.1053(18) 0.976(4) 0.3783(8) 0.039(6) Uiso 1 1 d
H10 H 0.181(2) 0.177(4) 0.2868(8) 0.051(7) Uiso 1 1 d
H11 H 0.336(2) -0.080(4) 0.2603(9) 0.056(8) Uiso 1 1 d
H12 H 0.576(2) -0.042(4) 0.2883(9) 0.065(7) Uiso 1 1 d
H13 H 0.655(2) 0.270(4) 0.3457(9) 0.081(9) Uiso 1 1 d
H14 H 0.499(2) 0.525(4) 0.3741(9) 0.060(8) Uiso 1 1 d
H15 H -0.1930(18) 0.666(3) 0.3227(8) 0.040(6) Uiso 1 1 d
H16A H -0.162(2) 0.964(5) 0.4151(9) 0.062(8) Uiso 1 1 d
H16B H -0.302(2) 0.831(4) 0.3908(9) 0.069(8) Uiso 1 1 d
H17A H -0.236(2) 0.492(4) 0.4344(9) 0.063(8) Uiso 1 1 d
H17B H -0.129(2) 0.659(4) 0.4696(11) 0.084(9) Uiso 1 1 d
H18A H -0.081(2) 0.344(4) 0.3907(9) 0.060(7) Uiso 1 1 d
H18B H 0.039(2) 0.444(3) 0.4381(8) 0.045(7) Uiso 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'
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
O1 C1 C2 110.59(17)
O1 C1 C8 113.19(17)
C2 C1 C8 104.72(17)
C3 C2 C9 129.9(2)
C3 C2 C1 108.36(19)
C9 C2 C1 121.7(2)
C2 C3 C7 113.30(19)
C2 C3 C4 136.9(2)
C7 C3 C4 109.37(19)
C3 C4 C5 104.5(2)
C6 C5 C4 104.6(2)
C7 C6 C5 102.2(2)
C3 C7 C6 102.81(18)
C3 C7 C8 103.06(17)
C6 C7 C8 124.85(19)
C15 C8 C18 101.16(17)
C15 C8 C1 115.53(17)
C18 C8 C1 110.09(18)
C15 C8 C7 115.33(18)
C18 C8 C7 112.89(19)
C1 C8 C7 102.21(16)
C10 C9 C14 116.9(2)
C10 C9 C2 121.03(19)
C14 C9 C2 122.1(2)
C11 C10 C9 121.7(2)
C12 C11 C10 120.3(3)
C11 C12 C13 119.3(3)
C12 C13 C14 120.5(3)
C13 C14 C9 121.2(3)
O2 C15 C16 108.86(19)
O2 C15 C8 116.12(17)
C16 C15 C8 104.29(18)
C15 C16 C17 104.7(2)
C16 C17 C18 105.9(2)
C8 C18 C17 106.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.458(3)
O2 C15 1.428(3)
C1 C2 1.514(3)
C1 C8 1.546(3)
C2 C3 1.335(3)
C2 C9 1.471(3)
C3 C7 1.500(3)
C3 C4 1.503(3)
C4 C5 1.543(4)
C5 C6 1.539(4)
C6 C7 1.531(3)
C7 C8 1.547(3)
C8 C15 1.529(3)
C8 C18 1.536(3)
C9 C10 1.396(3)
C9 C14 1.400(3)
C10 C11 1.383(3)
C11 C12 1.377(3)
C12 C13 1.380(3)
C13 C14 1.385(3)
C15 C16 1.529(3)
C16 C17 1.531(3)
C17 C18 1.545(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 102.5(2)
C8 C1 C2 C3 -19.8(2)
O1 C1 C2 C9 -76.2(3)
C8 C1 C2 C9 161.57(18)
C9 C2 C3 C7 -179.0(2)
C1 C2 C3 C7 2.5(3)
C9 C2 C3 C4 -7.6(5)
C1 C2 C3 C4 173.9(3)
C2 C3 C4 C5 -168.0(3)
C7 C3 C4 C5 3.6(3)
C3 C4 C5 C6 21.4(3)
C4 C5 C6 C7 -37.9(3)
C2 C3 C7 C6 146.6(2)
C4 C3 C7 C6 -27.2(3)
C2 C3 C7 C8 15.7(2)
C4 C3 C7 C8 -158.1(2)
C5 C6 C7 C3 39.5(3)
C5 C6 C7 C8 155.7(2)
O1 C1 C8 C15 33.5(3)
C2 C1 C8 C15 154.05(19)
O1 C1 C8 C18 147.28(19)
C2 C1 C8 C18 -92.2(2)
O1 C1 C8 C7 -92.5(2)
C2 C1 C8 C7 28.0(2)
C3 C7 C8 C15 -152.25(17)
C6 C7 C8 C15 91.7(3)
C3 C7 C8 C18 92.1(2)
C6 C7 C8 C18 -23.9(3)
C3 C7 C8 C1 -26.1(2)
C6 C7 C8 C1 -142.1(2)
C3 C2 C9 C10 173.1(2)
C1 C2 C9 C10 -8.5(3)
C3 C2 C9 C14 -7.2(4)
C1 C2 C9 C14 171.1(2)
C14 C9 C10 C11 1.6(3)
C2 C9 C10 C11 -178.7(2)
C9 C10 C11 C12 -1.1(4)
C10 C11 C12 C13 -0.2(4)
C11 C12 C13 C14 0.8(4)
C12 C13 C14 C9 -0.2(4)
C10 C9 C14 C13 -1.0(4)
C2 C9 C14 C13 179.3(2)
C18 C8 C15 O2 162.15(19)
C1 C8 C15 O2 -79.0(2)
C7 C8 C15 O2 40.0(3)
C18 C8 C15 C16 42.4(2)
C1 C8 C15 C16 161.2(2)
C7 C8 C15 C16 -79.7(2)
O2 C15 C16 C17 -159.5(2)
C8 C15 C16 C17 -35.0(3)
C15 C16 C17 C18 13.2(3)
C15 C8 C18 C17 -34.0(2)
C1 C8 C18 C17 -156.7(2)
C7 C8 C18 C17 89.8(2)
C16 C17 C18 C8 13.1(3)
