#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/81/4108184.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_4108184
loop_
_publ_author_name
'Koji Fukamizu'
'Yoshihiro Miyake'
'Yoshiaki Nishibayashi'
_publ_section_title
;
 Ruthenium-Catalyzed Enantioselective Carbon-Carbon Bond Forming Reaction
 via Allenylidene-Ene Process: Synthetic Approach to Chiral Heterocycles
 Such As Chromane, Thiochromane, and 1,2,3,4-Tetrahydroquinoline
 Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10498
_journal_page_last               10499
_journal_paper_doi               10.1021/ja8038745
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C19 H16 O '
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.330(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.4671(9)
_cell_length_b                   6.2402(8)
_cell_length_c                   12.0915(12)
_cell_measurement_reflns_used    4931
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     678.08(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6726
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       plate
_exptl_crystal_F_000             276.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.91
_refine_diff_density_min         -0.72
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1347 Friedel Pairs'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2997
_refine_ls_R_factor_gt           0.0699
_refine_ls_shift/su_max          0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[3.4950σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                1893
_reflns_number_total             2997
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja8038745-file004_1.cif
_cod_data_source_block           '_4'
_cod_original_cell_volume        678.08(12)
_cod_original_formula_sum        'C19 H16 O '
_cod_database_code               4108184
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+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
O(1) O 0.1939(2) 0.8573(4) 0.49187(19) 0.0400(7) Uani 1.00 1 d .
C(1) C 0.2557(3) 0.6865(6) 0.4495(3) 0.0316(11) Uani 1.00 1 d .
C(2) C 0.2674(4) 0.7112(7) 0.3400(3) 0.0407(12) Uani 1.00 1 d .
C(3) C 0.3283(3) 0.5471(6) 0.2905(3) 0.0414(12) Uani 1.00 1 d .
C(4) C 0.3737(3) 0.3591(6) 0.3524(2) 0.0360(11) Uani 1.00 1 d .
C(5) C 0.3622(3) 0.3375(6) 0.4633(2) 0.0339(11) Uani 1.00 1 d .
C(6) C 0.3061(3) 0.5006(6) 0.5155(2) 0.0294(10) Uani 1.00 1 d .
C(7) C 0.2969(3) 0.4900(5) 0.6336(2) 0.0273(10) Uani 1.00 1 d .
C(8) C 0.3121(3) 0.3251(6) 0.7067(2) 0.0333(10) Uani 1.00 1 d .
C(9) C 0.2572(4) 0.3807(6) 0.8064(3) 0.0357(11) Uani 1.00 1 d .
C(10) C 0.0900(4) 0.4325(5) 0.7644(3) 0.0389(11) Uani 1.00 1 d .
C(11) C 0.2003(3) 0.6147(6) 0.7867(3) 0.0288(10) Uani 1.00 1 d .
C(12) C 0.2461(3) 0.6906(5) 0.6816(3) 0.0281(10) Uani 1.00 1 d .
C(13) C 0.1329(3) 0.8081(6) 0.5846(2) 0.0340(10) Uani 1.00 1 d .
C(14) C 0.2066(3) 0.7659(5) 0.8791(3) 0.0307(10) Uani 1.00 1 d .
C(15) C 0.0782(3) 0.8887(6) 0.8717(3) 0.0368(11) Uani 1.00 1 d .
C(16) C 0.0756(4) 1.0325(6) 0.9581(3) 0.0390(12) Uani 1.00 1 d .
C(17) C 0.2021(4) 1.0588(6) 1.0539(3) 0.0395(12) Uani 1.00 1 d .
C(18) C 0.3275(4) 0.9437(6) 1.0614(3) 0.0417(12) Uani 1.00 1 d .
C(19) C 0.3302(4) 0.8003(6) 0.9752(3) 0.0420(12) Uani 1.00 1 d .
H(1) H 0.2340 0.8397 0.2977 0.049 Uiso 1.00 1 c R
H(2) H 0.3385 0.5644 0.2153 0.050 Uiso 1.00 1 c R
H(3) H 0.4126 0.2449 0.3188 0.043 Uiso 1.00 1 c R
H(4) H 0.3936 0.2075 0.5047 0.041 Uiso 1.00 1 c R
H(5) H 0.3525 0.1898 0.6966 0.040 Uiso 1.00 1 c R
H(6) H 0.3047 0.3267 0.8825 0.043 Uiso 1.00 1 c R
H(7) H 0.0325 0.4108 0.8152 0.047 Uiso 1.00 1 c R
H(8) H 0.0318 0.3988 0.6869 0.047 Uiso 1.00 1 c R
H(9) H 0.3301 0.7817 0.7103 0.034 Uiso 1.00 1 c R
H(10) H 0.0471 0.7207 0.5548 0.041 Uiso 1.00 1 c R
H(11) H 0.1061 0.9376 0.6142 0.041 Uiso 1.00 1 c R
H(12) H -0.0081 0.8720 0.8060 0.044 Uiso 1.00 1 c R
H(13) H -0.0119 1.1125 0.9520 0.047 Uiso 1.00 1 c R
H(14) H 0.2014 1.1565 1.1140 0.047 Uiso 1.00 1 c R
H(15) H 0.4140 0.9627 1.1268 0.050 Uiso 1.00 1 c R
H(16) H 0.4191 0.7232 0.9821 0.050 Uiso 1.00 1 c R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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_publ_flag
C(1) O(1) C(13) 116.1(2) yes
O(1) C(1) C(2) 116.1(3) yes
O(1) C(1) C(6) 122.1(3) yes
C(2) C(1) C(6) 121.7(3) yes
C(1) C(2) C(3) 120.0(3) yes
C(2) C(3) C(4) 119.2(3) yes
C(3) C(4) C(5) 120.0(3) yes
C(4) C(5) C(6) 121.7(3) yes
C(1) C(6) C(5) 117.2(3) yes
C(1) C(6) C(7) 118.7(3) yes
C(5) C(6) C(7) 124.1(3) yes
C(6) C(7) C(8) 130.9(3) yes
C(6) C(7) C(12) 117.3(3) yes
C(8) C(7) C(12) 111.4(3) yes
C(7) C(8) C(9) 111.2(3) yes
C(8) C(9) C(10) 111.5(2) yes
C(8) C(9) C(11) 106.7(3) yes
C(10) C(9) C(11) 58.6(2) yes
C(9) C(10) C(11) 61.1(2) yes
C(9) C(11) C(10) 60.3(2) yes
C(9) C(11) C(12) 104.0(3) yes
C(9) C(11) C(14) 124.6(3) yes
C(10) C(11) C(12) 116.3(3) yes
C(10) C(11) C(14) 119.1(3) yes
C(12) C(11) C(14) 118.8(3) yes
C(7) C(12) C(11) 105.4(2) yes
C(7) C(12) C(13) 109.7(2) yes
C(11) C(12) C(13) 118.4(3) yes
O(1) C(13) C(12) 110.3(2) yes
C(11) C(14) C(15) 118.5(2) yes
C(11) C(14) C(19) 124.6(3) yes
C(15) C(14) C(19) 116.9(3) yes
C(14) C(15) C(16) 121.5(2) yes
C(15) C(16) C(17) 119.4(3) yes
C(16) C(17) C(18) 119.8(3) yes
C(17) C(18) C(19) 120.8(3) yes
C(14) C(19) C(18) 121.6(3) yes
C(1) C(2) H(1) 120.0 no
C(3) C(2) H(1) 120.0 no
C(2) C(3) H(2) 120.4 no
C(4) C(3) H(2) 120.4 no
C(3) C(4) H(3) 120.0 no
C(5) C(4) H(3) 120.0 no
C(4) C(5) H(4) 119.1 no
C(6) C(5) H(4) 119.1 no
C(7) C(8) H(5) 124.4 no
C(9) C(8) H(5) 124.4 no
C(8) C(9) H(6) 121.3 no
C(10) C(9) H(6) 121.3 no
C(11) C(9) H(6) 121.3 no
C(9) C(10) H(7) 119.8 no
C(9) C(10) H(8) 119.8 no
C(11) C(10) H(7) 119.8 no
C(11) C(10) H(8) 119.8 no
H(7) C(10) H(8) 109.5 no
C(7) C(12) H(9) 107.6 no
C(11) C(12) H(9) 107.6 no
C(13) C(12) H(9) 107.6 no
O(1) C(13) H(10) 109.3 no
O(1) C(13) H(11) 109.3 no
C(12) C(13) H(10) 109.3 no
C(12) C(13) H(11) 109.3 no
H(10) C(13) H(11) 109.5 no
C(14) C(15) H(12) 119.3 no
C(16) C(15) H(12) 119.3 no
C(15) C(16) H(13) 120.3 no
C(17) C(16) H(13) 120.3 no
C(16) C(17) H(14) 120.1 no
C(18) C(17) H(14) 120.1 no
C(17) C(18) H(15) 119.6 no
C(19) C(18) H(15) 119.6 no
C(14) C(19) H(16) 119.2 no
C(18) C(19) H(16) 119.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.389(5) yes
O(1) C(13) 1.447(4) yes
C(1) C(2) 1.372(5) yes
C(1) C(6) 1.404(5) yes
C(2) C(3) 1.399(6) yes
C(3) C(4) 1.385(5) yes
C(4) C(5) 1.386(5) yes
C(5) C(6) 1.389(5) yes
C(6) C(7) 1.459(5) yes
C(7) C(8) 1.334(5) yes
C(7) C(12) 1.520(5) yes
C(8) C(9) 1.497(5) yes
C(9) C(10) 1.536(5) yes
C(9) C(11) 1.548(5) yes
C(10) C(11) 1.509(5) yes
C(11) C(12) 1.542(5) yes
C(11) C(14) 1.450(5) yes
C(12) C(13) 1.506(4) yes
C(14) C(15) 1.415(5) yes
C(14) C(19) 1.382(4) yes
C(15) C(16) 1.382(5) yes
C(16) C(17) 1.389(4) yes
C(17) C(18) 1.365(5) yes
C(18) C(19) 1.380(5) yes
C(2) H(1) 0.950 no
C(3) H(2) 0.950 no
C(4) H(3) 0.950 no
C(5) H(4) 0.950 no
C(8) H(5) 0.950 no
C(9) H(6) 0.950 no
C(10) H(7) 0.950 no
C(10) H(8) 0.950 no
C(12) H(9) 0.950 no
C(13) H(10) 0.950 no
C(13) H(11) 0.950 no
C(15) H(12) 0.950 no
C(16) H(13) 0.950 no
C(17) H(14) 0.950 no
C(18) H(15) 0.950 no
C(19) H(16) 0.950 no
