#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/35/4023517.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_4023517
loop_
_publ_author_name
'Jason W. J. Kennedy'
'Sophia Vietrich'
'Hilmar Weinmann'
'Dominic E. A. Brittain'
_publ_section_title
;
 Synthesis of 7a-Substituted Hajos-Wiechert Ketone Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5151
_journal_page_last               5154
_journal_paper_doi               10.1021/jo800638s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9020(8)
_cell_length_b                   11.9281(14)
_cell_length_c                   15.0146(16)
_cell_measurement_reflns_used    608
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.03
_cell_measurement_theta_min      4.73
_cell_volume                     1236.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.869
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            27014
_diffrn_reflns_theta_full        62.00
_diffrn_reflns_theta_max         62.00
_diffrn_reflns_theta_min         4.73
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.9675
_exptl_absorpt_correction_T_min  0.8253
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0014(540)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0251
_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)+(0.0390P)²+0.1865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0645
_reflns_number_gt                1646
_reflns_number_total             1667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800638s-File004.cif
_cod_data_source_block           tchx687
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023517
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37037(19) 0.05030(14) 0.17265(8) 0.0217(4) Uani 1 1 d . . .
H1A H 0.5040 0.0305 0.1907 0.026 Uiso 1 1 calc R . .
H1B H 0.2816 0.0355 0.2231 0.026 Uiso 1 1 calc R . .
C2 C 0.3584(2) 0.17239(14) 0.14348(9) 0.0229(4) Uani 1 1 d . . .
H2A H 0.3077 0.2197 0.1924 0.027 Uiso 1 1 calc R . .
H2B H 0.4878 0.2006 0.1260 0.027 Uiso 1 1 calc R . .
C3 C 0.22120(18) 0.17410(14) 0.06445(8) 0.0186(4) Uani 1 1 d . . .
O3 O 0.16095(14) 0.25802(9) 0.02792(6) 0.0241(3) Uani 1 1 d . . .
C4 C 0.16943(18) 0.05475(14) 0.03733(8) 0.0180(3) Uani 1 1 d . . .
C5 C 0.19932(19) 0.03222(13) -0.06269(8) 0.0211(4) Uani 1 1 d . . .
H5A H 0.0964 0.0703 -0.0972 0.025 Uiso 1 1 calc R . .
H5B H 0.3258 0.0632 -0.0817 0.025 Uiso 1 1 calc R . .
C6 C 0.1937(2) -0.09297(13) -0.08160(8) 0.0225(4) Uani 1 1 d . . .
H6A H 0.0579 -0.1190 -0.0770 0.027 Uiso 1 1 calc R . .
H6B H 0.2368 -0.1057 -0.1437 0.027 Uiso 1 1 calc R . .
C7 C 0.31743(19) -0.16340(15) -0.02027(9) 0.0209(4) Uani 1 1 d . . .
O7 O 0.36145(16) -0.25947(10) -0.04030(6) 0.0304(3) Uani 1 1 d . . .
C8 C 0.38142(19) -0.11199(14) 0.06369(9) 0.0219(4) Uani 1 1 d . . .
H8 H 0.4759 -0.1491 0.0990 0.026 Uiso 1 1 calc R . .
C9 C 0.30990(18) -0.01486(14) 0.09117(8) 0.0183(4) Uani 1 1 d . . .
C10 C -0.04820(17) 0.03430(14) 0.06243(8) 0.0186(3) Uani 1 1 d . . .
H10A H -0.1294 0.0859 0.0268 0.022 Uiso 1 1 calc R . .
H10B H -0.0832 -0.0432 0.0451 0.022 Uiso 1 1 calc R . .
C11 C -0.09798(17) 0.05014(14) 0.15953(9) 0.0176(4) Uani 1 1 d . . .
C12 C -0.11189(18) -0.04208(15) 0.21629(9) 0.0205(4) Uani 1 1 d . . .
H12 H -0.0924 -0.1154 0.1933 0.025 Uiso 1 1 calc R . .
C13 C -0.15396(18) -0.02798(15) 0.30608(9) 0.0244(4) Uani 1 1 d . . .
H13 H -0.1630 -0.0915 0.3440 0.029 Uiso 1 1 calc R . .
C14 C -0.1826(2) 0.07816(15) 0.34039(9) 0.0261(4) Uani 1 1 d . . .
H14 H -0.2091 0.0877 0.4020 0.031 Uiso 1 1 calc R . .
C15 C -0.17280(19) 0.17055(15) 0.28491(9) 0.0244(4) Uani 1 1 d . . .
H15 H -0.1944 0.2435 0.3082 0.029 Uiso 1 1 calc R . .
C16 C -0.13118(19) 0.15636(14) 0.19485(9) 0.0209(4) Uani 1 1 d . . .
H16 H -0.1254 0.2201 0.1570 0.025 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 0.0181 0.0091 '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 0.0492 0.0322 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 104.14(11) . . ?
C3 C2 C1 105.76(12) . . ?
O3 C3 C2 125.28(14) . . ?
O3 C3 C4 124.69(12) . . ?
C2 C3 C4 110.04(12) . . ?
C9 C4 C3 102.71(11) . . ?
C9 C4 C5 109.88(11) . . ?
C3 C4 C5 113.11(11) . . ?
C9 C4 C10 113.62(11) . . ?
C3 C4 C10 107.81(11) . . ?
C5 C4 C10 109.62(10) . . ?
C6 C5 C4 110.49(12) . . ?
C7 C6 C5 114.70(12) . . ?
O7 C7 C8 121.81(14) . . ?
O7 C7 C6 120.77(13) . . ?
C8 C7 C6 117.42(14) . . ?
C9 C8 C7 121.32(13) . . ?
C8 C9 C1 126.86(13) . . ?
C8 C9 C4 123.56(13) . . ?
C1 C9 C4 109.17(13) . . ?
C11 C10 C4 115.51(10) . . ?
C16 C11 C12 118.26(12) . . ?
C16 C11 C10 121.27(13) . . ?
C12 C11 C10 120.46(14) . . ?
C13 C12 C11 120.79(16) . . ?
C14 C13 C12 120.19(14) . . ?
C13 C14 C15 119.91(13) . . ?
C14 C15 C16 119.87(15) . . ?
C11 C16 C15 120.95(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.508(2) . ?
C1 C2 1.523(2) . ?
C2 C3 1.5181(19) . ?
C3 O3 1.2148(18) . ?
C3 C4 1.523(2) . ?
C4 C9 1.5109(19) . ?
C4 C5 1.5395(17) . ?
C4 C10 1.5677(17) . ?
C5 C6 1.521(2) . ?
C6 C7 1.511(2) . ?
C7 O7 1.2231(18) . ?
C7 C8 1.470(2) . ?
C8 C9 1.325(2) . ?
C10 C11 1.5097(18) . ?
C11 C16 1.393(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.3893(19) . ?
C13 C14 1.381(2) . ?
C14 C15 1.383(2) . ?
C15 C16 1.3926(19) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25938776
