#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:58:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178453 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/74/4027447.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_4027447
loop_
_publ_author_name
'William T. Spencer'
'Alison J. Frontier'
_publ_section_title
;
 Cycloaromatization Protocol for Synthesis of Polysubstituted Phenol
 Derivatives: Method Development and Mechanistic Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7730
_journal_page_last               7736
_journal_paper_doi               10.1021/jo3010952
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H13 D5 O'
_chemical_formula_sum            'C16 H13 D5 O'
_chemical_formula_weight         231.33
_chemical_name_common            frows03
_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                 90.084(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1006(18)
_cell_length_b                   15.181(2)
_cell_length_c                   7.5819(12)
_cell_measurement_reflns_used    3231
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.68
_cell_volume                     1277.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, ω scans per φ'
_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  0.0836
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17966
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0670
_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)+(0.0864P)²+1.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1677
_refine_ls_wR_factor_ref         0.1898
_reflns_number_gt                1842
_reflns_number_total             2616
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3010952_si_003.cif
_cod_data_source_block           frows03
_cod_original_cell_volume        1277.7(4)
_cod_database_code               4027447
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
_atom_site_refinement_flags
C1 C 0.7824(3) -0.06080(19) 0.4981(4) 0.0274(6) Uani 1 1 d .
C2 C 0.7973(3) -0.1159(2) 0.6425(4) 0.0344(7) Uani 1 1 d .
H2 H 0.8315 -0.1727 0.6261 0.041 Uiso 1 1 calc R
C3 C 0.7632(3) -0.0897(2) 0.8097(4) 0.0381(8) Uani 1 1 d .
H3 H 0.7744 -0.1282 0.9072 0.046 Uiso 1 1 calc R
C4 C 0.7130(3) -0.0075(2) 0.8346(4) 0.0360(7) Uani 1 1 d .
H4 H 0.6905 0.0111 0.9496 0.043 Uiso 1 1 calc R
C5 C 0.6955(3) 0.0472(2) 0.6931(4) 0.0314(7) Uani 1 1 d .
H5 H 0.6598 0.1034 0.7108 0.038 Uiso 1 1 calc R
C6 C 0.7294(2) 0.02178(18) 0.5230(4) 0.0257(6) Uani 1 1 d .
C7 C 0.7065(3) 0.08342(18) 0.3740(4) 0.0254(6) Uani 1 1 d .
C8 C 0.7968(3) 0.1336(2) 0.3003(4) 0.0298(7) Uani 1 1 d .
D8 D 0.875(3) 0.129(2) 0.347(5) 0.036 Uiso 1 1 d .
C9 C 0.7727(3) 0.1928(2) 0.1649(4) 0.0354(7) Uani 1 1 d .
D9 D 0.832(3) 0.227(2) 0.116(5) 0.042 Uiso 1 1 d .
C10 C 0.6567(3) 0.2011(2) 0.0988(4) 0.0339(7) Uani 1 1 d .
D10 D 0.642(3) 0.240(3) 0.006(5) 0.041 Uiso 1 1 d .
C11 C 0.5669(3) 0.1508(2) 0.1702(4) 0.0322(7) Uani 1 1 d .
D11 D 0.480(3) 0.156(2) 0.125(5) 0.039 Uiso 1 1 d .
C12 C 0.5900(3) 0.0930(2) 0.3073(4) 0.0277(6) Uani 1 1 d .
D12 D 0.524(3) 0.054(2) 0.355(4) 0.033 Uiso 1 1 d .
C13 C 0.8217(3) -0.0927(2) 0.3193(4) 0.0329(7) Uani 1 1 d .
H13 H 0.7972 -0.0481 0.2290 0.039 Uiso 1 1 calc R
O1 O 0.7696(2) -0.17416(15) 0.2747(3) 0.0421(6) Uani 1 1 d .
C14 C 0.6450(3) -0.1689(3) 0.2575(5) 0.0467(9) Uani 1 1 d .
H14A H 0.6087 -0.1599 0.3739 0.070 Uiso 1 1 calc R
H14B H 0.6143 -0.2238 0.2063 0.070 Uiso 1 1 calc R
H14C H 0.6241 -0.1194 0.1803 0.070 Uiso 1 1 calc R
C15 C 0.9595(3) -0.1042(3) 0.3118(5) 0.0473(9) Uani 1 1 d .
H15A H 0.9980 -0.0480 0.3466 0.057 Uiso 1 1 calc R
H15B H 0.9837 -0.1494 0.3990 0.057 Uiso 1 1 calc R
C16 C 1.0058(3) -0.1305(3) 0.1349(5) 0.0505(10) Uani 1 1 d .
H16A H 0.9687 -0.1863 0.0993 0.076 Uiso 1 1 calc R
H16B H 1.0934 -0.1376 0.1406 0.076 Uiso 1 1 calc R
H16C H 0.9857 -0.0847 0.0484 0.076 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'
D D 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'
H H 0.0000 0.0000 '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
C2 C1 C6 118.9(3)
C2 C1 C13 118.8(3)
C6 C1 C13 122.2(3)
C3 C2 C1 121.2(3)
C3 C2 H2 119.4
C1 C2 H2 119.4
C4 C3 C2 119.8(3)
C4 C3 H3 120.1
C2 C3 H3 120.1
C5 C4 C3 119.8(3)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 121.1(3)
C4 C5 H5 119.4
C6 C5 H5 119.4
C1 C6 C5 119.1(3)
C1 C6 C7 122.2(3)
C5 C6 C7 118.7(3)
C8 C7 C12 118.0(3)
C8 C7 C6 122.1(3)
C12 C7 C6 119.9(3)
D8 C8 C7 119(2)
D8 C8 C9 120(2)
C7 C8 C9 121.2(3)
D9 C9 C10 118(2)
D9 C9 C8 122(2)
C10 C9 C8 120.2(3)
D10 C10 C11 122(2)
D10 C10 C9 119(2)
C11 C10 C9 118.9(3)
D11 C11 C10 121(2)
D11 C11 C12 118(2)
C10 C11 C12 121.1(3)
D12 C12 C11 120.5(18)
D12 C12 C7 118.7(18)
C11 C12 C7 120.6(3)
O1 C13 C1 112.4(3)
O1 C13 C15 107.4(3)
C1 C13 C15 111.0(3)
O1 C13 H13 108.6
C1 C13 H13 108.6
C15 C13 H13 108.6
C14 O1 C13 112.4(3)
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C16 C15 C13 114.0(3)
C16 C15 H15A 108.8
C13 C15 H15A 108.8
C16 C15 H15B 108.8
C13 C15 H15B 108.8
H15A C15 H15B 107.6
C15 C16 H16A 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.388(4)
C1 C6 1.398(4)
C1 C13 1.505(4)
C2 C3 1.382(5)
C2 H2 0.9500
C3 C4 1.380(5)
C3 H3 0.9500
C4 C5 1.371(4)
C4 H4 0.9500
C5 C6 1.398(4)
C5 H5 0.9500
C6 C7 1.488(4)
C7 C8 1.378(4)
C7 C12 1.395(4)
C8 D8 0.94(3)
C8 C9 1.390(4)
C9 D9 0.92(4)
C9 C10 1.387(5)
C10 D10 0.94(4)
C10 C11 1.368(5)
C11 D11 1.03(3)
C11 C12 1.384(4)
C12 D12 1.01(3)
C13 O1 1.405(4)
C13 C15 1.541(5)
C13 H13 1.0000
O1 C14 1.392(4)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 C16 1.491(5)
C15 H15A 0.9900
C15 H15B 0.9900
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
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
C6 C1 C2 C3 -1.5(5)
C13 C1 C2 C3 179.7(3)
C1 C2 C3 C4 0.3(5)
C2 C3 C4 C5 0.9(5)
C3 C4 C5 C6 -0.9(5)
C2 C1 C6 C5 1.5(4)
C13 C1 C6 C5 -179.8(3)
C2 C1 C6 C7 -177.9(3)
C13 C1 C6 C7 0.9(4)
C4 C5 C6 C1 -0.3(4)
C4 C5 C6 C7 179.1(3)
C1 C6 C7 C8 -78.0(4)
C5 C6 C7 C8 102.7(3)
C1 C6 C7 C12 103.3(3)
C5 C6 C7 C12 -76.0(4)
C12 C7 C8 D8 178(2)
C6 C7 C8 D8 -1(2)
C12 C7 C8 C9 0.7(4)
C6 C7 C8 C9 -178.0(3)
D8 C8 C9 D9 2(4)
C7 C8 C9 D9 179(3)
D8 C8 C9 C10 -178(2)
C7 C8 C9 C10 -1.3(5)
D9 C9 C10 D10 1(4)
C8 C9 C10 D10 -179(3)
D9 C9 C10 C11 -180(3)
C8 C9 C10 C11 0.6(5)
D10 C10 C11 D11 -1(4)
C9 C10 C11 D11 179(2)
D10 C10 C11 C12 -180(3)
C9 C10 C11 C12 0.6(5)
D11 C11 C12 D12 4(3)
C10 C11 C12 D12 -177(2)
D11 C11 C12 C7 -180(2)
C10 C11 C12 C7 -1.2(5)
C8 C7 C12 D12 176(2)
C6 C7 C12 D12 -5(2)
C8 C7 C12 C11 0.5(4)
C6 C7 C12 C11 179.3(3)
C2 C1 C13 O1 54.1(4)
C6 C1 C13 O1 -124.7(3)
C2 C1 C13 C15 -66.3(4)
C6 C1 C13 C15 114.9(3)
C1 C13 O1 C14 64.5(3)
C15 C13 O1 C14 -173.1(3)
O1 C13 C15 C16 60.3(4)
C1 C13 C15 C16 -176.5(3)
