#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/96/4029684.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_4029684
loop_
_publ_author_name
'Miyahara, Yuji'
'Ito, Yoshio N.'
_publ_section_title
;
 AlCl3-Mediated Aldol Cyclocondensation of 1,6- and 1,7-Diones to
 Cyclopentene and Cyclohexene Derivatives.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6801
_journal_page_last               6807
_journal_paper_doi               10.1021/jo5006137
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C18 H16 O '
_chemical_formula_sum            'C18 H16 O'
_chemical_formula_weight         248.32
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_cell_angle_alpha                90
_cell_angle_beta                 108.75(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.830(8)
_cell_length_b                   5.635(2)
_cell_length_c                   12.122(7)
_cell_measurement_reflns_used    6983
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1347.3(11)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6975
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_Flack   -1.6(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1700
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.0007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.11000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                1686
_reflns_number_total             1700
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo5006137_si_002.cif
_cod_data_source_block           FCbypro
_cod_depositor_comments
'Adding full bibliography for 4029684--4029685.cif.'
_cod_original_cell_volume        1347(3)
_cod_original_formula_sum        'C18 H16 O '
_cod_database_code               4029684
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,-z
1/2+x,1/2+y,z
1/2-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_calc_flag
O(1) O 0.62887(6) 0.589(1) 0.1692(1) 0.0274(3) Uani 1.00 d
O(2) O 0.77956(5) -0.087(1) 0.09244(9) 0.0282(3) Uani 1.00 d
C(1) C 0.60694(6) 0.392(1) 0.1796(1) 0.0161(3) Uani 1.00 d
C(2) C 0.63880(7) 0.172(1) 0.1479(1) 0.0145(3) Uani 1.00 d
C(3) C 0.60702(6) 0.115(1) 0.0161(1) 0.0194(3) Uani 1.00 d
C(4) C 0.65927(7) -0.045(1) -0.0114(1) 0.0179(3) Uani 1.00 d
C(5) C 0.72618(7) 0.010(1) 0.0822(1) 0.0167(3) Uani 1.00 d
C(6) C 0.71421(6) 0.200(1) 0.16309(10) 0.0134(3) Uani 1.00 d
C(7) C 0.76180(6) 0.191(1) 0.28598(10) 0.0144(3) Uani 1.00 d
C(8) C 0.76188(6) -0.002(1) 0.3583(1) 0.0181(3) Uani 1.00 d
C(9) C 0.80623(8) -0.009(1) 0.4719(1) 0.0207(3) Uani 1.00 d
C(10) C 0.85193(7) 0.175(1) 0.5140(1) 0.0221(3) Uani 1.00 d
C(11) C 0.85241(7) 0.367(1) 0.4431(1) 0.0207(3) Uani 1.00 d
C(12) C 0.80752(6) 0.375(1) 0.3293(1) 0.0172(3) Uani 1.00 d
C(13) C 0.54693(6) 0.369(1) 0.2205(1) 0.0152(3) Uani 1.00 d
C(14) C 0.53716(7) 0.172(1) 0.2823(1) 0.0197(3) Uani 1.00 d
C(15) C 0.48284(8) 0.164(1) 0.3260(1) 0.0273(4) Uani 1.00 d
C(16) C 0.43748(7) 0.352(1) 0.3056(1) 0.0272(4) Uani 1.00 d
C(17) C 0.44601(7) 0.548(1) 0.2420(1) 0.0246(4) Uani 1.00 d
C(18) C 0.50086(7) 0.558(1) 0.2004(1) 0.0197(3) Uani 1.00 d
H(2) H 0.6234 0.0406 0.1909 0.0147 Uiso 1.00 calc
H(3A) H 0.5617 0.0366 -0.0047 0.0198 Uiso 1.00 calc
H(3B) H 0.6024 0.2526 -0.0244 0.0198 Uiso 1.00 calc
H(4A) H 0.6476 -0.2101 -0.0067 0.0180 Uiso 1.00 calc
H(4B) H 0.6620 -0.0098 -0.0932 0.0180 Uiso 1.00 calc
H(6) H 0.7206 0.3434 0.1241 0.0136 Uiso 1.00 calc
H(8) H 0.7315 -0.1249 0.3320 0.0185 Uiso 1.00 calc
H(9) H 0.8018 -0.1331 0.5218 0.0210 Uiso 1.00 calc
H(10) H 0.8850 0.1646 0.5936 0.0223 Uiso 1.00 calc
H(11) H 0.8852 0.4839 0.4698 0.0206 Uiso 1.00 calc
H(12) H 0.8111 0.5121 0.2852 0.0174 Uiso 1.00 calc
H(14) H 0.5676 0.0471 0.2984 0.0200 Uiso 1.00 calc
H(15) H 0.4770 0.0270 0.3704 0.0275 Uiso 1.00 calc
H(16) H 0.3968 0.3540 0.3357 0.0275 Uiso 1.00 calc
H(17) H 0.4154 0.6647 0.2286 0.0246 Uiso 1.00 calc
H(18) H 0.5039 0.6822 0.1468 0.0199 Uiso 1.00 calc
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 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_3
_geom_angle_publ_flag
O(1) C(1) C(2) 120.6(1) 0_555 yes
O(1) C(1) C(13) 119.7(1) 0_555 yes
C(2) C(1) C(13) 119.7(1) 0_555 yes
C(1) C(2) C(3) 110.8(1) 0_555 yes
C(1) C(2) C(6) 113.9(1) 0_555 yes
C(3) C(2) C(6) 103.1(1) 0_555 yes
C(2) C(3) C(4) 104.4(1) 0_555 yes
C(3) C(4) C(5) 105.2(1) 0_555 yes
O(2) C(5) C(4) 125.2(1) 0_555 yes
O(2) C(5) C(6) 125.8(1) 0_555 yes
C(4) C(5) C(6) 108.9(1) 0_555 yes
C(2) C(6) C(5) 103.1(1) 0_555 yes
C(2) C(6) C(7) 116.20(10) 0_555 yes
C(5) C(6) C(7) 115.1(1) 0_555 yes
C(6) C(7) C(8) 120.9(1) 0_555 yes
C(6) C(7) C(12) 120.3(1) 0_555 yes
C(8) C(7) C(12) 118.7(1) 0_555 yes
C(7) C(8) C(9) 120.9(1) 0_555 yes
C(8) C(9) C(10) 119.9(1) 0_555 yes
C(9) C(10) C(11) 119.9(1) 0_555 yes
C(10) C(11) C(12) 120.2(1) 0_555 yes
C(7) C(12) C(11) 120.5(1) 0_555 yes
C(1) C(13) C(14) 122.2(1) 0_555 yes
C(1) C(13) C(18) 118.4(1) 0_555 yes
C(14) C(13) C(18) 119.3(1) 0_555 yes
C(13) C(14) C(15) 120.4(1) 0_555 yes
C(14) C(15) C(16) 119.8(2) 0_555 yes
C(15) C(16) C(17) 120.2(1) 0_555 yes
C(16) C(17) C(18) 120.0(1) 0_555 yes
C(13) C(18) C(17) 120.2(1) 0_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.221(2) yes
O(2) C(5) 1.208(2) yes
C(1) C(2) 1.512(2) yes
C(1) C(13) 1.492(2) yes
C(2) C(3) 1.554(2) yes
C(2) C(6) 1.529(2) yes
C(3) C(4) 1.532(2) yes
C(4) C(5) 1.520(2) yes
C(5) C(6) 1.524(2) yes
C(6) C(7) 1.502(2) yes
C(7) C(8) 1.397(2) yes
C(7) C(12) 1.391(2) yes
C(8) C(9) 1.391(2) yes
C(9) C(10) 1.389(2) yes
C(10) C(11) 1.385(2) yes
C(11) C(12) 1.397(2) yes
C(13) C(14) 1.390(2) yes
C(13) C(18) 1.400(2) yes
C(14) C(15) 1.396(2) yes
C(15) C(16) 1.388(3) yes
C(16) C(17) 1.387(3) yes
C(17) C(18) 1.391(2) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) C(4) 3.214(2) 1_565
O(1) C(2) 3.309(2) 1_565
O(1) C(3) 3.449(2) 1_565
O(1) C(5) 3.496(2) 1_565
O(2) C(5) 3.081(2) 4_645
O(2) C(4) 3.174(2) 4_645
O(2) C(6) 3.365(2) 4_645
O(2) C(17) 3.441(2) 3_545
O(2) C(3) 3.484(2) 4_645
O(2) C(16) 3.486(2) 3_545
O(2) C(4) 3.563(2) 4_655
O(2) O(2) 3.564(1) 4_655
O(2) O(2) 3.564(1) 4_645
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O(1) C(1) C(2) C(3) -86.6(2) 0_555 20_1 5_555 55_5 yes
O(1) C(1) C(2) C(6) 29.0(2) 0_555 20_1 5_555 55_5 yes
O(1) C(1) C(13) C(14) -150.7(1) 0_555 20_1 5_555 55_5 yes
O(1) C(1) C(13) C(18) 26.3(2) 0_555 20_1 5_555 55_5 yes
O(2) C(5) C(4) C(3) 177.5(2) 0_555 20_1 5_555 55_5 yes
O(2) C(5) C(6) C(2) -154.1(2) 0_555 20_1 5_555 55_5 yes
O(2) C(5) C(6) C(7) -26.5(2) 0_555 20_1 5_555 55_5 yes
C(1) C(2) C(3) C(4) 160.0(1) 0_555 20_1 5_555 55_5 yes
C(1) C(2) C(6) C(5) -157.3(1) 0_555 20_1 5_555 55_5 yes
C(1) C(2) C(6) C(7) 75.8(2) 0_555 20_1 5_555 55_5 yes
C(1) C(13) C(14) C(15) 175.5(1) 0_555 20_1 5_555 55_5 yes
C(1) C(13) C(18) C(17) -176.9(1) 0_555 20_1 5_555 55_5 yes
C(2) C(1) C(13) C(14) 31.1(2) 0_555 20_1 5_555 55_5 yes
C(2) C(1) C(13) C(18) -152.0(1) 0_555 20_1 5_555 55_5 yes
C(2) C(3) C(4) C(5) -23.0(1) 0_555 20_1 5_555 55_5 yes
C(2) C(6) C(5) C(4) 23.7(1) 0_555 20_1 5_555 55_5 yes
C(2) C(6) C(7) C(8) 55.6(2) 0_555 20_1 5_555 55_5 yes
C(2) C(6) C(7) C(12) -125.4(1) 0_555 20_1 5_555 55_5 yes
C(3) C(2) C(1) C(13) 91.6(1) 0_555 20_1 5_555 55_5 yes
C(3) C(2) C(6) C(5) -37.3(1) 0_555 20_1 5_555 55_5 yes
C(3) C(2) C(6) C(7) -164.2(1) 0_555 20_1 5_555 55_5 yes
C(3) C(4) C(5) C(6) -0.2(2) 0_555 20_1 5_555 55_5 yes
C(4) C(3) C(2) C(6) 37.8(1) 0_555 20_1 5_555 55_5 yes
C(4) C(5) C(6) C(7) 151.3(1) 0_555 20_1 5_555 55_5 yes
C(5) C(6) C(7) C(8) -65.1(2) 0_555 20_1 5_555 55_5 yes
C(5) C(6) C(7) C(12) 113.9(1) 0_555 20_1 5_555 55_5 yes
C(6) C(2) C(1) C(13) -152.8(1) 0_555 20_1 5_555 55_5 yes
C(6) C(7) C(8) C(9) 179.7(1) 0_555 20_1 5_555 55_5 yes
C(6) C(7) C(12) C(11) -179.2(1) 0_555 20_1 5_555 55_5 yes
C(7) C(8) C(9) C(10) -1.1(2) 0_555 20_1 5_555 55_5 yes
C(7) C(12) C(11) C(10) 0.2(2) 0_555 20_1 5_555 55_5 yes
C(8) C(7) C(12) C(11) -0.2(2) 0_555 20_1 5_555 55_5 yes
C(8) C(9) C(10) C(11) 1.0(2) 0_555 20_1 5_555 55_5 yes
C(9) C(8) C(7) C(12) 0.7(2) 0_555 20_1 5_555 55_5 yes
C(9) C(10) C(11) C(12) -0.6(2) 0_555 20_1 5_555 55_5 yes
C(13) C(14) C(15) C(16) 1.4(2) 0_555 20_1 5_555 55_5 yes
C(13) C(18) C(17) C(16) 1.2(2) 0_555 20_1 5_555 55_5 yes
C(14) C(13) C(18) C(17) 0.1(2) 0_555 20_1 5_555 55_5 yes
C(14) C(15) C(16) C(17) -0.1(3) 0_555 20_1 5_555 55_5 yes
C(15) C(14) C(13) C(18) -1.4(2) 0_555 20_1 5_555 55_5 yes
C(15) C(16) C(17) C(18) -1.2(2) 0_555 20_1 5_555 55_5 yes
C(15) C(16) C(17) C(18) -1.2(2) 0_555 20_1 5_555 55_5 yes
