#------------------------------------------------------------------------------
#$Date: 2020-08-27 02:15:08 +0300 (Thu, 27 Aug 2020) $
#$Revision: 255670 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038716.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_4038716
loop_
_publ_author_name
'Göricke, Fabian'
'Haseloff, Stefan'
'Laue, Michael'
'Schneider, Maximilian'
'Brumme, Thomas'
'Schneider, Christoph'
_publ_section_title
;
 Phosphoric Acid-Catalyzed Formation of Hydrogen-Bonded ortho-Quinone
 Methides. Enantioselective Cycloaddition with β-Dicarbonyl Compounds
 toward Benzannulated Oxygen Heterocycles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01375
_journal_year                    2020
_chemical_formula_sum            'C21 H19 O2'
_chemical_formula_weight         303.36
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.72090(10)
_cell_length_b                   8.72090(10)
_cell_length_c                   41.8621(6)
_cell_measurement_reflns_used    894
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      6
_cell_volume                     3183.78(7)
_computing_cell_refinement       'PILATUS (Fa.STOE)'
_computing_data_collection       'PILATUS (Fa.STOE)'
_computing_data_reduction        'PILATUS (Fa.STOE)'
_computing_molecular_graphics    'ORTEP3 for WINDOWS (L.J.Farrugia)'
_computing_publication_material  'WINGX (L.J.Farrugia)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STADIVARI (Fa.STOE)'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            37385
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         70.626
_diffrn_reflns_theta_min         4.224
_diffrn_source                   'sealed tube Cu'
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.158
_exptl_crystal_description       none
_exptl_crystal_F_000             161
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.115
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.0984
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2967
_reflns_number_total             3050
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01375_si_008.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        3183.78(9)
_cod_database_code               4038716
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45969(13) 0.34303(14) 0.10484(2) 0.0383(3) Uani 1 1 d . . . . .
O2 O 0.17630(12) 0.20374(13) 0.19635(2) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.45347(17) 0.17109(16) 0.20045(3) 0.0276(3) Uani 1 1 d . . . . .
C11 C 0.39565(19) -0.00118(17) 0.25637(3) 0.0345(3) Uani 1 1 d . . . . .
C6 C 0.33076(16) 0.28314(16) 0.15244(3) 0.0271(3) Uani 1 1 d . . . . .
C8 C 0.30599(18) 0.14677(16) 0.21190(3) 0.0290(3) Uani 1 1 d . . . . .
C5 C 0.19288(17) 0.25801(16) 0.16604(3) 0.0288(3) Uani 1 1 d . . . . .
C10 C 0.27533(18) 0.06234(17) 0.23909(3) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.1747 0.0481 0.2458 0.039 Uiso 1 1 calc R U . . .
C17 C 0.48018(16) 0.26496(16) 0.17045(3) 0.0267(3) Uani 1 1 d . . . . .
H17 H 0.5509 0.2075 0.1568 0.032 Uiso 1 1 calc R U . . .
C4 C 0.04087(18) 0.28395(19) 0.15069(4) 0.0346(3) Uani 1 1 d . . . . .
H4A H -0.0291 0.3287 0.1661 0.042 Uiso 1 1 calc R U . . .
H4B H -0.0015 0.1865 0.1438 0.042 Uiso 1 1 calc R U . . .
C12 C 0.54397(19) 0.02406(17) 0.24571(3) 0.0344(3) Uani 1 1 d . . . . .
H12 H 0.6253 -0.0165 0.2573 0.041 Uiso 1 1 calc R U . . .
C1 C 0.33654(17) 0.32472(16) 0.11832(3) 0.0295(3) Uani 1 1 d . . . . .
C23 C 0.66661(17) 0.47925(18) 0.15764(3) 0.0338(3) Uani 1 1 d . . . . .
H23 H 0.6977 0.4237 0.1398 0.041 Uiso 1 1 calc R U . . .
C2 C 0.18634(19) 0.33599(19) 0.10058(3) 0.0361(4) Uani 1 1 d . . . . .
H2A H 0.1605 0.2363 0.0918 0.043 Uiso 1 1 calc R U . . .
H2B H 0.1977 0.4069 0.0829 0.043 Uiso 1 1 calc R U . . .
C13 C 0.57565(18) 0.10828(16) 0.21811(3) 0.0308(3) Uani 1 1 d . . . . .
C16 C 0.73916(18) 0.1326(2) 0.20767(4) 0.0395(4) Uani 1 1 d . . . . .
H16A H 0.7488 0.1082 0.1854 0.059 Uiso 1 1 calc R U . . .
H16B H 0.8056 0.0673 0.2199 0.059 Uiso 1 1 calc R U . . .
H16C H 0.7673 0.2378 0.2111 0.059 Uiso 1 1 calc R U . . .
C3 C 0.05612(18) 0.39032(19) 0.12208(3) 0.0359(3) Uani 1 1 d . . . . .
H3A H 0.0767 0.4939 0.1294 0.043 Uiso 1 1 calc R U . . .
H3B H -0.0392 0.3914 0.1101 0.043 Uiso 1 1 calc R U . . .
C19 C 0.50822(19) 0.50583(19) 0.20378(4) 0.0350(3) Uani 1 1 d . . . . .
H19 H 0.4326 0.4679 0.2173 0.042 Uiso 1 1 calc R U . . .
C22 C 0.73402(19) 0.6203(2) 0.16417(4) 0.0409(4) Uani 1 1 d . . . . .
H22 H 0.8105 0.6583 0.1509 0.049 Uiso 1 1 calc R U . . .
C18 C 0.55334(16) 0.42069(16) 0.17750(3) 0.0272(3) Uani 1 1 d . . . . .
C21 C 0.6873(2) 0.70421(19) 0.19047(4) 0.0437(4) Uani 1 1 d . . . . .
H21 H 0.7319 0.7988 0.1948 0.052 Uiso 1 1 calc R U . . .
C20 C 0.5745(2) 0.64705(19) 0.21018(4) 0.0438(4) Uani 1 1 d . . . . .
H20 H 0.5426 0.7034 0.2278 0.053 Uiso 1 1 calc R U . . .
C15 C 0.3631(2) -0.0957(2) 0.28572(4) 0.0449(4) Uani 1 1 d . . . . .
H15A H 0.2839 -0.0473 0.2980 0.067 Uiso 1 1 calc R U . . .
H15B H 0.4546 -0.1038 0.2984 0.067 Uiso 1 1 calc R U . . .
H15C H 0.3301 -0.1963 0.2794 0.067 Uiso 1 1 calc R U . . .
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
C5 O2 C8 118.16(11) . . ?
C8 C9 C13 117.41(13) . . ?
C8 C9 C17 120.68(12) . . ?
C13 C9 C17 121.90(13) . . ?
C12 C11 C10 118.28(13) . . ?
C12 C11 C15 121.70(14) . . ?
C10 C11 C15 120.02(15) . . ?
C5 C6 C1 118.64(12) . . ?
C5 C6 C17 122.72(12) . . ?
C1 C6 C17 118.61(12) . . ?
C10 C8 C9 123.01(14) . . ?
C10 C8 O2 114.64(13) . . ?
C9 C8 O2 122.34(12) . . ?
C6 C5 O2 122.98(13) . . ?
C6 C5 C4 125.92(13) . . ?
O2 C5 C4 111.10(12) . . ?
C8 C10 C11 119.67(14) . . ?
C6 C17 C9 109.67(11) . . ?
C6 C17 C18 111.23(11) . . ?
C9 C17 C18 112.56(11) . . ?
C5 C4 C3 110.75(13) . . ?
C11 C12 C13 122.31(14) . . ?
O1 C1 C6 120.58(13) . . ?
O1 C1 C2 121.77(12) . . ?
C6 C1 C2 117.58(12) . . ?
C18 C23 C22 120.56(14) . . ?
C1 C2 C3 112.11(12) . . ?
C12 C13 C9 119.29(14) . . ?
C12 C13 C16 120.09(14) . . ?
C9 C13 C16 120.62(13) . . ?
C4 C3 C2 109.91(13) . . ?
C18 C19 C20 120.76(15) . . ?
C21 C22 C23 119.98(15) . . ?
C19 C18 C23 118.74(14) . . ?
C19 C18 C17 120.74(13) . . ?
C23 C18 C17 120.52(12) . . ?
C20 C21 C22 119.72(15) . . ?
C21 C20 C19 120.23(15) . . ?
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
O1 C1 1.2236(18) . ?
O2 C5 1.3620(17) . ?
O2 C8 1.3964(18) . ?
C9 C8 1.389(2) . ?
C9 C13 1.408(2) . ?
C9 C17 1.5171(17) . ?
C11 C12 1.386(2) . ?
C11 C10 1.390(2) . ?
C11 C15 1.507(2) . ?
C6 C5 1.348(2) . ?
C6 C1 1.4748(19) . ?
C6 C17 1.5137(18) . ?
C8 C10 1.382(2) . ?
C5 C4 1.490(2) . ?
C17 C18 1.5292(18) . ?
C4 C3 1.521(2) . ?
C12 C13 1.397(2) . ?
C1 C2 1.509(2) . ?
C23 C18 1.389(2) . ?
C23 C22 1.391(2) . ?
C2 C3 1.524(2) . ?
C13 C16 1.506(2) . ?
C19 C18 1.384(2) . ?
C19 C20 1.386(2) . ?
C22 C21 1.383(3) . ?
C21 C20 1.377(3) . ?
