#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:34:33 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158716.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_7158716
loop_
_publ_author_name
'Liu, Dan'
'Liu, Xueyan'
'Sun, Jing'
'Han, Ying'
'Yan, Chao-Guo'
_publ_section_title
;
 Domino reaction of bindone and 1,3-dipolarophiles for the synthesis of
 diverse spiro and fused indeno[1,2-a]fluorene-7,12-diones.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4964
_journal_page_last               4969
_journal_paper_doi               10.1039/d2ob00815g
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C37 H24 O4'
_chemical_formula_sum            'C37 H24 O4'
_chemical_formula_weight         532.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-03-21 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                114.9926(16)
_cell_angle_beta                 93.9003(16)
_cell_angle_gamma                100.7507(18)
_cell_formula_units_Z            2
_cell_length_a                   8.2970(4)
_cell_length_b                   12.8462(7)
_cell_length_c                   13.7948(7)
_cell_measurement_reflns_used    6271
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.53
_cell_volume                     1291.33(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18439
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.533
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0590P)²+0.4140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3330
_reflns_number_total             5053
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00815g2.cif
_cod_data_source_block           7i
_cod_depositor_comments
'Adding full bibliography for 7158713--7158721.cif.'
_cod_database_code               7158716
_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. 
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_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_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
C1 C 0.3053(2) 0.40581(17) 0.40047(15) 0.0342(5) Uani 1 1 d . . . . .
C2 C 0.2887(3) 0.27884(19) 0.37874(17) 0.0422(5) Uani 1 1 d . . . . .
C3 C 0.2081(3) 0.2652(2) 0.46607(17) 0.0434(5) Uani 1 1 d . . . . .
C4 C 0.1668(3) 0.1645(2) 0.4820(2) 0.0572(6) Uani 1 1 d . . . . .
H4 H 0.1901 0.0939 0.4352 0.069 Uiso 1 1 calc R U . . .
C5 C 0.0899(3) 0.1726(2) 0.5696(2) 0.0634(7) Uani 1 1 d . . . . .
H5 H 0.0602 0.1066 0.5824 0.076 Uiso 1 1 calc R U . . .
C6 C 0.0569(3) 0.2781(2) 0.6383(2) 0.0582(7) Uani 1 1 d . . . . .
H6 H 0.0037 0.2815 0.6964 0.070 Uiso 1 1 calc R U . . .
C7 C 0.1004(3) 0.3793(2) 0.62373(18) 0.0485(6) Uani 1 1 d . . . . .
H7 H 0.0788 0.4500 0.6717 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1765(2) 0.37236(19) 0.53620(16) 0.0385(5) Uani 1 1 d . . . . .
C9 C 0.2366(2) 0.46005(18) 0.49515(15) 0.0338(5) Uani 1 1 d . . . . .
C10 C 0.2359(2) 0.57805(18) 0.53378(14) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.1685(2) 0.65673(19) 0.62874(16) 0.0406(5) Uani 1 1 d . . . . .
C12 C 0.2228(2) 0.77568(18) 0.63568(16) 0.0401(5) Uani 1 1 d . . . . .
C13 C 0.2040(3) 0.8811(2) 0.71671(19) 0.0560(6) Uani 1 1 d . . . . .
H13 H 0.1466 0.8816 0.7724 0.067 Uiso 1 1 calc R U . . .
C14 C 0.2724(3) 0.9842(2) 0.7123(2) 0.0647(7) Uani 1 1 d . . . . .
H14 H 0.2608 1.0559 0.7652 0.078 Uiso 1 1 calc R U . . .
C15 C 0.3583(3) 0.9822(2) 0.6298(2) 0.0641(7) Uani 1 1 d . . . . .
H15 H 0.4067 1.0533 0.6292 0.077 Uiso 1 1 calc R U . . .
C16 C 0.3747(3) 0.8768(2) 0.54740(19) 0.0535(6) Uani 1 1 d . . . . .
H16 H 0.4321 0.8771 0.4919 0.064 Uiso 1 1 calc R U . . .
C17 C 0.3039(2) 0.77142(18) 0.54941(16) 0.0390(5) Uani 1 1 d . . . . .
C18 C 0.3038(2) 0.64422(17) 0.48012(15) 0.0331(5) Uani 1 1 d . . . . .
C19 C 0.3636(2) 0.46670(17) 0.34214(14) 0.0321(5) Uani 1 1 d . . . . .
C20 C 0.3585(2) 0.58737(17) 0.38097(15) 0.0328(5) Uani 1 1 d . . . . .
C21 C 0.3972(3) 0.64773(19) 0.31126(16) 0.0398(5) Uani 1 1 d . . . . .
C22 C 0.4997(2) 0.60001(19) 0.22783(15) 0.0385(5) Uani 1 1 d . . . . .
C23 C 0.5780(3) 0.6707(2) 0.18247(17) 0.0497(6) Uani 1 1 d . . . . .
H23 H 0.5603 0.7460 0.2028 0.060 Uiso 1 1 calc R U . . .
C24 C 0.6806(3) 0.6302(2) 0.10836(19) 0.0584(7) Uani 1 1 d . . . . .
H24 H 0.7341 0.6780 0.0793 0.070 Uiso 1 1 calc R U . . .
C25 C 0.7034(3) 0.5182(2) 0.07753(19) 0.0591(7) Uani 1 1 d . . . . .
H25 H 0.7737 0.4906 0.0277 0.071 Uiso 1 1 calc R U . . .
C26 C 0.6240(3) 0.4458(2) 0.11916(18) 0.0500(6) Uani 1 1 d . . . . .
H26 H 0.6396 0.3696 0.0962 0.060 Uiso 1 1 calc R U . . .
C27 C 0.5208(2) 0.48619(18) 0.19521(15) 0.0365(5) Uani 1 1 d . . . . .
C28 C 0.4243(2) 0.40243(17) 0.23333(15) 0.0346(5) Uani 1 1 d . . . . .
C29 C 0.2706(2) 0.32305(17) 0.14563(15) 0.0332(5) Uani 1 1 d . . . . .
C30 C 0.2685(3) 0.20764(19) 0.07498(17) 0.0455(5) Uani 1 1 d . . . . .
H30 H 0.3609 0.1777 0.0802 0.055 Uiso 1 1 calc R U . . .
C31 C 0.1312(3) 0.1363(2) -0.00311(18) 0.0498(6) Uani 1 1 d . . . . .
H31 H 0.1330 0.0589 -0.0492 0.060 Uiso 1 1 calc R U . . .
C32 C -0.0075(3) 0.1761(2) -0.01464(17) 0.0447(5) Uani 1 1 d . . . . .
C33 C -0.1578(3) 0.0958(2) -0.10169(19) 0.0609(7) Uani 1 1 d . . . . .
H33 H -0.1411 0.0154 -0.1295 0.073 Uiso 1 1 calc R U . . .
C34 C -0.1638(4) 0.1260(3) -0.1956(2) 0.0983(11) Uani 1 1 d . . . . .
H34A H -0.1788 0.2049 -0.1717 0.148 Uiso 1 1 calc R U . . .
H34B H -0.2549 0.0713 -0.2512 0.148 Uiso 1 1 calc R U . . .
H34C H -0.0615 0.1210 -0.2239 0.148 Uiso 1 1 calc R U . . .
C35 C -0.3205(3) 0.0931(3) -0.0576(3) 0.0866(10) Uani 1 1 d . . . . .
H35A H -0.3501 0.1672 -0.0390 0.130 Uiso 1 1 calc R U . . .
H35B H -0.3078 0.0802 0.0058 0.130 Uiso 1 1 calc R U . . .
H35C H -0.4065 0.0303 -0.1118 0.130 Uiso 1 1 calc R U . . .
C36 C -0.0035(3) 0.2928(2) 0.05447(18) 0.0507(6) Uani 1 1 d . . . . .
H36 H -0.0947 0.3231 0.0476 0.061 Uiso 1 1 calc R U . . .
C37 C 0.1331(3) 0.36511(19) 0.13350(17) 0.0443(5) Uani 1 1 d . . . . .
H37 H 0.1321 0.4429 0.1788 0.053 Uiso 1 1 calc R U . . .
O1 O 0.3312(2) 0.19994(13) 0.30543(12) 0.0563(4) Uani 1 1 d . . . . .
O2 O 0.08106(19) 0.62972(14) 0.68515(12) 0.0558(4) Uani 1 1 d . . . . .
O3 O 0.3444(2) 0.73426(15) 0.32214(13) 0.0617(5) Uani 1 1 d . . . . .
O4 O 0.53482(17) 0.33491(13) 0.24420(12) 0.0447(4) Uani 1 1 d . . . . .
H4A H 0.4847 0.2816 0.2565 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 0.0033 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
C19 C1 C9 121.58(18) . . ?
C19 C1 C2 131.48(18) . . ?
C9 C1 C2 106.81(17) . . ?
O1 C2 C3 124.7(2) . . ?
O1 C2 C1 129.2(2) . . ?
C3 C2 C1 106.09(18) . . ?
C4 C3 C8 122.0(2) . . ?
C4 C3 C2 128.1(2) . . ?
C8 C3 C2 109.89(19) . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 118.2(2) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 119.5(2) . . ?
C7 C8 C9 132.9(2) . . ?
C3 C8 C9 107.57(18) . . ?
C10 C9 C1 119.01(18) . . ?
C10 C9 C8 131.35(18) . . ?
C1 C9 C8 109.63(18) . . ?
C9 C10 C18 120.67(17) . . ?
C9 C10 C11 130.70(19) . . ?
C18 C10 C11 108.62(18) . . ?
O2 C11 C12 126.34(19) . . ?
O2 C11 C10 128.6(2) . . ?
C12 C11 C10 105.00(18) . . ?
C13 C12 C17 122.4(2) . . ?
C13 C12 C11 126.9(2) . . ?
C17 C12 C11 110.61(18) . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 121.7(2) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C12 118.46(19) . . ?
C16 C17 C18 133.83(19) . . ?
C12 C17 C18 107.53(18) . . ?
C20 C18 C10 119.90(18) . . ?
C20 C18 C17 132.52(18) . . ?
C10 C18 C17 107.56(16) . . ?
C1 C19 C20 118.97(17) . . ?
C1 C19 C28 120.64(17) . . ?
C20 C19 C28 120.30(17) . . ?
C18 C20 C19 119.42(18) . . ?
C18 C20 C21 121.27(18) . . ?
C19 C20 C21 119.09(17) . . ?
O3 C21 C22 120.66(19) . . ?
O3 C21 C20 121.25(19) . . ?
C22 C21 C20 118.09(19) . . ?
C27 C22 C23 120.08(19) . . ?
C27 C22 C21 120.32(19) . . ?
C23 C22 C21 119.6(2) . . ?
C24 C23 C22 120.7(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.1(2) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 121.2(2) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C27 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C22 C27 C26 118.6(2) . . ?
C22 C27 C28 121.72(17) . . ?
C26 C27 C28 119.45(19) . . ?
O4 C28 C27 105.40(15) . . ?
O4 C28 C29 111.11(15) . . ?
C27 C28 C29 108.18(15) . . ?
O4 C28 C19 110.45(15) . . ?
C27 C28 C19 113.25(16) . . ?
C29 C28 C19 108.44(15) . . ?
C37 C29 C30 117.80(18) . . ?
C37 C29 C28 121.46(17) . . ?
C30 C29 C28 120.73(18) . . ?
C31 C30 C29 120.9(2) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 121.9(2) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C36 117.1(2) . . ?
C31 C32 C33 121.0(2) . . ?
C36 C32 C33 121.9(2) . . ?
C34 C33 C35 112.5(3) . . ?
C34 C33 C32 110.9(2) . . ?
C35 C33 C32 113.1(2) . . ?
C34 C33 H33 106.6 . . ?
C35 C33 H33 106.6 . . ?
C32 C33 H33 106.6 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C37 C36 C32 121.5(2) . . ?
C37 C36 H36 119.2 . . ?
C32 C36 H36 119.2 . . ?
C29 C37 C36 120.7(2) . . ?
C29 C37 H37 119.6 . . ?
C36 C37 H37 119.6 . . ?
C28 O4 H4A 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
C1 C19 1.392(3) . ?
C1 C9 1.413(3) . ?
C1 C2 1.506(3) . ?
C2 O1 1.221(2) . ?
C2 C3 1.474(3) . ?
C3 C4 1.387(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.485(3) . ?
C9 C10 1.379(3) . ?
C10 C18 1.413(3) . ?
C10 C11 1.497(3) . ?
C11 O2 1.210(2) . ?
C11 C12 1.470(3) . ?
C12 C13 1.389(3) . ?
C12 C17 1.393(3) . ?
C13 C14 1.368(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.504(3) . ?
C18 C20 1.405(3) . ?
C19 C20 1.420(3) . ?
C19 C28 1.549(3) . ?
C20 C21 1.486(3) . ?
C21 O3 1.225(2) . ?
C21 C22 1.468(3) . ?
C22 C27 1.386(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.369(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.513(3) . ?
C28 O4 1.416(2) . ?
C28 C29 1.546(3) . ?
C29 C37 1.379(3) . ?
C29 C30 1.384(3) . ?
C30 C31 1.381(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.370(3) . ?
C31 H31 0.9300 . ?
C32 C36 1.388(3) . ?
C32 C33 1.527(3) . ?
C33 C34 1.501(4) . ?
C33 C35 1.518(4) . ?
C33 H33 0.9800 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 C37 1.386(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
O4 H4A 0.8200 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O1 0.82 1.84 2.629(2) 160.4 .
