#------------------------------------------------------------------------------
#$Date: 2020-11-06 14:32:56 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258877 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/12/7241295.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_7241295
loop_
_publ_author_name
'Hu, Deqing'
'Yang, Lu'
'Wan, Jie-Ping'
_publ_section_title
;
 Biaryl and atropisomeric biaryl aldehyde synthesis by one-step,
 metal-free benzannulation of aryl enals and propiolates
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              6773
_journal_page_last               6777
_journal_paper_doi               10.1039/D0GC02806A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 O6'
_chemical_formula_sum            'C18 H16 O6'
_chemical_formula_weight         328.31
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-08-12 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                95.85(3)
_cell_angle_beta                 104.17(3)
_cell_angle_gamma                111.98(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1121(18)
_cell_length_b                   9.4374(19)
_cell_length_c                   10.647(2)
_cell_measurement_reflns_used    5814
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     803.9(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6624
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0
_diffrn_standards_number         image
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0412
_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)+(0.0639P)²+0.1564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1337
_reflns_number_gt                2218
_reflns_number_total             2936
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0gc02806a2.cif
_cod_data_source_block           shx97
_cod_depositor_comments          'Adding full bibliography for 7241295.cif.'
_cod_original_cell_volume        803.9(3)
_cod_database_code               7241295
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65492(19) 0.45419(19) 0.91769(15) 0.0630(4) Uani 1 1 d . . .
O2 O 0.27116(17) 0.33512(17) 0.60270(18) 0.0672(5) Uani 1 1 d . . .
O3 O 1.01877(16) 0.84886(16) 0.93414(14) 0.0545(4) Uani 1 1 d . . .
O4 O 1.02576(14) 1.00869(16) 0.79210(13) 0.0493(3) Uani 1 1 d . . .
O5 O 0.48404(19) 1.06427(17) 0.6555(2) 0.0911(7) Uani 1 1 d . . .
O6 O 0.25682(15) 0.84237(15) 0.57657(14) 0.0521(4) Uani 1 1 d . . .
C1 C 0.8530(3) 0.3579(2) 0.8702(2) 0.0615(6) Uani 1 1 d . . .
H1A H 0.8414 0.2953 0.9323 0.074 Uiso 1 1 calc R . .
C2 C 0.9585(3) 0.3607(3) 0.7972(3) 0.0738(8) Uani 1 1 d . . .
H2A H 1.0173 0.2986 0.8099 0.089 Uiso 1 1 calc R . .
C3 C 0.9792(3) 0.4532(3) 0.7060(3) 0.0659(7) Uani 1 1 d . . .
H3A H 1.0510 0.4534 0.6570 0.079 Uiso 1 1 calc R . .
C4 C 0.8920(2) 0.5465(2) 0.6873(2) 0.0497(5) Uani 1 1 d . . .
H4A H 0.9066 0.6108 0.6266 0.060 Uiso 1 1 calc R . .
C5 C 0.7832(2) 0.54382(19) 0.75908(17) 0.0380(4) Uani 1 1 d . . .
C6 C 0.7642(2) 0.4486(2) 0.85077(19) 0.0459(5) Uani 1 1 d . . .
C7 C 0.6870(2) 0.64180(19) 0.73555(15) 0.0337(4) Uani 1 1 d . . .
C8 C 0.76754(19) 0.80563(19) 0.76656(16) 0.0354(4) Uani 1 1 d . . .
C9 C 0.6782(2) 0.8953(2) 0.73455(17) 0.0396(4) Uani 1 1 d . . .
H9A H 0.7332 1.0038 0.7550 0.048 Uiso 1 1 calc R . .
C10 C 0.5075(2) 0.82410(19) 0.67220(17) 0.0379(4) Uani 1 1 d . . .
C11 C 0.4265(2) 0.6636(2) 0.64336(17) 0.0388(4) Uani 1 1 d . . .
H11A H 0.3120 0.6160 0.6031 0.047 Uiso 1 1 calc R . .
C12 C 0.5139(2) 0.57105(19) 0.67375(16) 0.0363(4) Uani 1 1 d . . .
C13 C 0.6207(3) 0.3517(4) 1.0062(3) 0.0860(9) Uani 1 1 d . . .
H13A H 0.5426 0.3678 1.0458 0.129 Uiso 1 1 calc R . .
H13B H 0.7219 0.3730 1.0745 0.129 Uiso 1 1 calc R . .
H13C H 0.5747 0.2453 0.9582 0.129 Uiso 1 1 calc R . .
C14 C 0.4203(2) 0.3994(2) 0.63853(19) 0.0435(4) Uani 1 1 d . . .
H14A H 0.4799 0.3377 0.6444 0.052 Uiso 1 1 calc R . .
C15 C 0.9497(2) 0.8863(2) 0.84082(17) 0.0383(4) Uani 1 1 d . . .
C16 C 1.2006(2) 1.1001(3) 0.8613(2) 0.0627(6) Uani 1 1 d . . .
H16A H 1.2436 1.1847 0.8188 0.094 Uiso 1 1 calc R . .
H16B H 1.2597 1.0348 0.8593 0.094 Uiso 1 1 calc R . .
H16C H 1.2146 1.1416 0.9517 0.094 Uiso 1 1 calc R . .
C17 C 0.4175(2) 0.9251(2) 0.63512(19) 0.0448(4) Uani 1 1 d . . .
C18 C 0.1589(2) 0.9253(2) 0.5245(2) 0.0529(5) Uani 1 1 d . . .
H18A H 0.0449 0.8525 0.4845 0.079 Uiso 1 1 calc R . .
H18B H 0.2003 0.9766 0.4591 0.079 Uiso 1 1 calc R . .
H18C H 0.1665 1.0018 0.5953 0.079 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'
H H 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'
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
C6 O1 C13 118.34(18) . . ?
C15 O4 C16 115.87(15) . . ?
C17 O6 C18 117.49(15) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 H1A 120.3 . . ?
C6 C1 H1A 120.3 . . ?
C1 C2 C3 121.43(18) . . ?
C1 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 119.41(16) . . ?
C4 C5 C7 119.47(16) . . ?
C6 C5 C7 121.12(15) . . ?
O1 C6 C1 124.35(19) . . ?
O1 C6 C5 115.40(15) . . ?
C1 C6 C5 120.2(2) . . ?
C8 C7 C12 118.41(15) . . ?
C8 C7 C5 121.08(14) . . ?
C12 C7 C5 120.39(15) . . ?
C9 C8 C7 120.50(15) . . ?
C9 C8 C15 119.16(15) . . ?
C7 C8 C15 120.28(14) . . ?
C8 C9 C10 120.61(16) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C11 C10 C9 119.53(15) . . ?
C11 C10 C17 121.73(15) . . ?
C9 C10 C17 118.73(16) . . ?
C10 C11 C12 120.88(15) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 120.07(15) . . ?
C11 C12 C14 118.33(15) . . ?
C7 C12 C14 121.60(15) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C12 123.45(16) . . ?
O2 C14 H14A 118.3 . . ?
C12 C14 H14A 118.3 . . ?
O3 C15 O4 123.83(16) . . ?
O3 C15 C8 124.81(17) . . ?
O4 C15 C8 111.34(14) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 O6 124.08(16) . . ?
O5 C17 C10 123.68(16) . . ?
O6 C17 C10 112.23(15) . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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 C6 1.371(2) . ?
O1 C13 1.423(3) . ?
O2 C14 1.201(2) . ?
O3 C15 1.200(2) . ?
O4 C15 1.335(2) . ?
O4 C16 1.446(2) . ?
O5 C17 1.192(2) . ?
O6 C17 1.319(2) . ?
O6 C18 1.443(2) . ?
C1 C2 1.371(4) . ?
C1 C6 1.380(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.391(3) . ?
C5 C7 1.494(2) . ?
C7 C8 1.402(2) . ?
C7 C12 1.408(2) . ?
C8 C9 1.390(2) . ?
C8 C15 1.500(2) . ?
C9 C10 1.390(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.375(2) . ?
C10 C17 1.497(2) . ?
C11 C12 1.398(2) . ?
C11 H11A 0.9300 . ?
C12 C14 1.476(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C3 C4 C5 C7 -178.48(17) . . . . ?
C13 O1 C6 C1 -4.8(3) . . . . ?
C13 O1 C6 C5 175.71(19) . . . . ?
C2 C1 C6 O1 179.69(18) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C4 C5 C6 O1 179.61(16) . . . . ?
C7 C5 C6 O1 -1.1(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C7 C5 C6 C1 179.40(16) . . . . ?
C4 C5 C7 C8 -65.4(2) . . . . ?
C6 C5 C7 C8 115.31(19) . . . . ?
C4 C5 C7 C12 110.58(19) . . . . ?
C6 C5 C7 C12 -68.7(2) . . . . ?
C12 C7 C8 C9 -1.2(2) . . . . ?
C5 C7 C8 C9 174.88(15) . . . . ?
C12 C7 C8 C15 175.75(15) . . . . ?
C5 C7 C8 C15 -8.2(2) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C15 C8 C9 C10 -176.47(16) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C8 C9 C10 C17 -177.78(16) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C17 C10 C11 C12 177.27(16) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C10 C11 C12 C14 -179.10(16) . . . . ?
C8 C7 C12 C11 0.7(2) . . . . ?
C5 C7 C12 C11 -175.37(15) . . . . ?
C8 C7 C12 C14 -179.76(15) . . . . ?
C5 C7 C12 C14 4.2(2) . . . . ?
C11 C12 C14 O2 -11.0(3) . . . . ?
C7 C12 C14 O2 169.48(18) . . . . ?
C16 O4 C15 O3 -1.6(3) . . . . ?
C16 O4 C15 C8 176.78(16) . . . . ?
C9 C8 C15 O3 134.62(19) . . . . ?
C7 C8 C15 O3 -42.3(2) . . . . ?
C9 C8 C15 O4 -43.8(2) . . . . ?
C7 C8 C15 O4 139.29(16) . . . . ?
C18 O6 C17 O5 5.3(3) . . . . ?
C18 O6 C17 C10 -174.15(16) . . . . ?
C11 C10 C17 O5 -178.1(2) . . . . ?
C9 C10 C17 O5 0.4(3) . . . . ?
C11 C10 C17 O6 1.4(3) . . . . ?
C9 C10 C17 O6 179.84(16) . . . . ?
