#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:34:33 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158713.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_7158713
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 H23 N3 O4'
_chemical_formula_sum            'C37 H23 N3 O4'
_chemical_formula_weight         573.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-02-23 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4162(16)
_cell_length_b                   11.9045(11)
_cell_length_c                   34.111(3)
_cell_measurement_reflns_used    7013
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.99
_cell_measurement_theta_min      2.16
_cell_volume                     7072.3(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1433
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            55584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.157
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       block
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6945
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1964
_refine_ls_R_factor_gt           0.0859
_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)+(0.1301P)²+3.0137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2212
_refine_ls_wR_factor_ref         0.2761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3077
_reflns_number_total             6945
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00815g2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 7158713--7158721.cif.'
_cod_original_cell_volume        7072.2(11)
_cod_database_code               7158713
_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   0.982
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_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'
'-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_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 0.7001(2) 0.8373(4) 0.10818(12) 0.0536(11) Uani 1 1 d . . . . .
C2 C 0.7637(3) 0.7785(4) 0.08929(13) 0.0639(13) Uani 1 1 d . . . . .
C3 C 0.8404(3) 0.8132(5) 0.08733(18) 0.0936(17) Uani 1 1 d . . . . .
H3 H 0.8566 0.8801 0.0987 0.112 Uiso 1 1 calc R U . . .
C4 C 0.8899(4) 0.7449(8) 0.0681(3) 0.129(3) Uani 1 1 d . . . . .
H4 H 0.9414 0.7650 0.0662 0.155 Uiso 1 1 calc R U . . .
C5 C 0.8653(5) 0.6461(7) 0.0512(2) 0.122(3) Uani 1 1 d . . . . .
H5 H 0.9010 0.6019 0.0381 0.147 Uiso 1 1 calc R U . . .
C6 C 0.7902(4) 0.6093(5) 0.05282(17) 0.0937(18) Uani 1 1 d . . . . .
H6 H 0.7748 0.5419 0.0415 0.112 Uiso 1 1 calc R U . . .
C7 C 0.7390(3) 0.6794(4) 0.07239(13) 0.0623(12) Uani 1 1 d . . . . .
C8 C 0.6573(3) 0.6638(4) 0.07894(12) 0.0567(12) Uani 1 1 d . . . . .
C9 C 0.6250(2) 0.7688(3) 0.10028(11) 0.0445(10) Uani 1 1 d . . . . .
C10 C 0.5847(2) 0.7431(3) 0.13760(10) 0.0437(10) Uani 1 1 d . . . . .
C11 C 0.6114(2) 0.6624(3) 0.16812(10) 0.0469(10) Uani 1 1 d . . . . .
C12 C 0.6733(3) 0.5922(4) 0.17028(12) 0.0601(12) Uani 1 1 d . . . . .
H12 H 0.7091 0.5900 0.1501 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6819(3) 0.5247(4) 0.20282(14) 0.0689(13) Uani 1 1 d . . . . .
H13 H 0.7240 0.4769 0.2043 0.083 Uiso 1 1 calc R U . . .
C14 C 0.6300(3) 0.5261(4) 0.23297(14) 0.0708(14) Uani 1 1 d . . . . .
H14 H 0.6370 0.4793 0.2545 0.085 Uiso 1 1 calc R U . . .
C15 C 0.5669(3) 0.5972(4) 0.23150(13) 0.0631(12) Uani 1 1 d . . . . .
H15 H 0.5312 0.5991 0.2518 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5586(2) 0.6650(3) 0.19894(11) 0.0517(11) Uani 1 1 d . . . . .
C17 C 0.4982(3) 0.7497(4) 0.18843(11) 0.0536(11) Uani 1 1 d . . . . .
C18 C 0.5203(2) 0.7933(3) 0.14938(11) 0.0460(10) Uani 1 1 d . . . . .
C19 C 0.1776(3) 1.0147(5) 0.18998(17) 0.0833(15) Uani 1 1 d . . . . .
H19 H 0.1660 1.0768 0.1746 0.100 Uiso 1 1 calc R U . . .
C20 C 0.1405(3) 0.9989(6) 0.2258(2) 0.104(2) Uani 1 1 d . . . . .
H20 H 0.1046 1.0513 0.2343 0.124 Uiso 1 1 calc R U . . .
C21 C 0.1564(4) 0.9073(7) 0.24862(18) 0.0973(19) Uani 1 1 d . . . . .
H21 H 0.1305 0.8960 0.2721 0.117 Uiso 1 1 calc R U . . .
C22 C 0.2104(3) 0.8332(5) 0.23647(17) 0.0826(16) Uani 1 1 d . . . . .
H22 H 0.2225 0.7719 0.2522 0.099 Uiso 1 1 calc R U . . .
C23 C 0.2477(3) 0.8470(4) 0.20121(16) 0.0702(13) Uani 1 1 d . . . . .
H23 H 0.2842 0.7945 0.1933 0.084 Uiso 1 1 calc R U . . .
C24 C 0.2317(2) 0.9375(4) 0.17751(15) 0.0663(13) Uani 1 1 d . . . . .
C25 C 0.2666(3) 0.9518(5) 0.13761(14) 0.0779(15) Uani 1 1 d . . . . .
H25A H 0.2460 0.8947 0.1202 0.093 Uiso 1 1 calc R U . . .
H25B H 0.2519 1.0245 0.1273 0.093 Uiso 1 1 calc R U . . .
C26 C 0.3908(3) 0.8505(4) 0.12582(12) 0.0622(12) Uani 1 1 d . U . . .
C27 C 0.4775(2) 0.8791(3) 0.12687(11) 0.0491(10) Uani 1 1 d . . . . .
C28 C 0.4755(3) 0.9958(3) 0.14610(11) 0.0527(11) Uani 1 1 d . . . . .
C29 C 0.5356(3) 1.0667(4) 0.15618(11) 0.0615(12) Uani 1 1 d . . . . .
H29 H 0.5862 1.0434 0.1533 0.074 Uiso 1 1 calc R U . . .
C30 C 0.5187(4) 1.1740(4) 0.17079(13) 0.0797(16) Uani 1 1 d . . . . .
C31 C 0.5816(4) 1.2512(5) 0.18369(17) 0.120(2) Uani 1 1 d . . . . .
H31A H 0.5748 1.3233 0.1716 0.180 Uiso 1 1 calc R U . . .
H31B H 0.6303 1.2204 0.1761 0.180 Uiso 1 1 calc R U . . .
H31C H 0.5800 1.2593 0.2117 0.180 Uiso 1 1 calc R U . . .
C32 C 0.4420(4) 1.2046(5) 0.17393(15) 0.0905(18) Uani 1 1 d . . . . .
H32 H 0.4303 1.2759 0.1834 0.109 Uiso 1 1 calc R U . . .
C33 C 0.3829(3) 1.1348(4) 0.16377(14) 0.0774(15) Uani 1 1 d . . . . .
H33 H 0.3321 1.1579 0.1662 0.093 Uiso 1 1 calc R U . . .
C34 C 0.4008(3) 1.0295(4) 0.14985(12) 0.0576(11) Uani 1 1 d . . . . .
C35 C 0.5094(2) 0.8855(3) 0.08561(10) 0.0472(10) Uani 1 1 d . . . . .
C36 C 0.4676(3) 0.9542(4) 0.05821(12) 0.0586(12) Uani 1 1 d . . . . .
C37 C 0.5746(2) 0.8370(3) 0.07306(11) 0.0458(10) Uani 1 1 d . . . . .
N1 N 0.3501(2) 0.9436(3) 0.13769(9) 0.0592(10) Uani 1 1 d . . . . .
N2 N 0.4367(3) 1.0092(4) 0.03582(12) 0.0883(14) Uani 1 1 d . . . . .
N3 N 0.6028(2) 0.8504(3) 0.03633(9) 0.0648(10) Uani 1 1 d . . . . .
H3A H 0.5787 0.8916 0.0197 0.078 Uiso 1 1 calc R U . . .
H3B H 0.6448 0.8175 0.0297 0.078 Uiso 1 1 calc R U . . .
O1 O 0.70214(18) 0.9217(3) 0.12745(10) 0.0777(10) Uani 1 1 d . . . . .
O2 O 0.6182(2) 0.5830(3) 0.07024(10) 0.0828(10) Uani 1 1 d . . . . .
O3 O 0.44177(19) 0.7758(3) 0.20759(8) 0.0754(10) Uani 1 1 d . . . . .
O4 O 0.36300(18) 0.7629(3) 0.11478(10) 0.0795(10) Uani 1 1 d . 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'
N N 0.0061 0.0033 '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
O1 C1 C2 128.3(4) . . ?
O1 C1 C9 123.7(4) . . ?
C2 C1 C9 108.0(4) . . ?
C7 C2 C3 121.9(5) . . ?
C7 C2 C1 111.0(4) . . ?
C3 C2 C1 127.1(5) . . ?
C4 C3 C2 117.0(6) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.0(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 123.4(6) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C7 115.8(6) . . ?
C5 C6 H6 122.1 . . ?
C7 C6 H6 122.1 . . ?
C2 C7 C6 120.9(5) . . ?
C2 C7 C8 110.4(4) . . ?
C6 C7 C8 128.7(5) . . ?
O2 C8 C7 127.8(4) . . ?
O2 C8 C9 123.2(4) . . ?
C7 C8 C9 108.9(4) . . ?
C10 C9 C37 111.2(3) . . ?
C10 C9 C8 114.0(3) . . ?
C37 C9 C8 110.8(3) . . ?
C10 C9 C1 110.8(3) . . ?
C37 C9 C1 108.1(3) . . ?
C8 C9 C1 101.4(3) . . ?
C18 C10 C9 124.3(3) . . ?
C18 C10 C11 110.0(3) . . ?
C9 C10 C11 125.7(3) . . ?
C12 C11 C16 119.5(3) . . ?
C12 C11 C10 132.7(4) . . ?
C16 C11 C10 107.8(3) . . ?
C11 C12 C13 119.1(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 121.7(4) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 117.9(4) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C15 C16 C11 121.6(4) . . ?
C15 C16 C17 131.1(4) . . ?
C11 C16 C17 107.3(3) . . ?
O3 C17 C18 127.0(4) . . ?
O3 C17 C16 127.4(4) . . ?
C18 C17 C16 105.5(4) . . ?
C10 C18 C27 125.2(3) . . ?
C10 C18 C17 109.5(3) . . ?
C27 C18 C17 125.3(4) . . ?
C24 C19 C20 119.7(6) . . ?
C24 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C21 C20 C19 120.8(6) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 119.1(6) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 121.2(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C19 118.6(5) . . ?
C23 C24 C25 122.6(5) . . ?
C19 C24 C25 118.7(5) . . ?
N1 C25 C24 113.3(4) . . ?
N1 C25 H25A 108.9 . . ?
C24 C25 H25A 108.9 . . ?
N1 C25 H25B 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
O4 C26 N1 125.4(4) . . ?
O4 C26 C27 125.9(4) . . ?
N1 C26 C27 108.6(4) . . ?
C18 C27 C35 109.4(3) . . ?
C18 C27 C28 114.5(3) . . ?
C35 C27 C28 111.1(3) . . ?
C18 C27 C26 110.5(3) . . ?
C35 C27 C26 110.3(3) . . ?
C28 C27 C26 100.8(3) . . ?
C34 C28 C29 121.1(4) . . ?
C34 C28 C27 109.0(4) . . ?
C29 C28 C27 129.7(4) . . ?
C28 C29 C30 118.9(5) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C32 C30 C29 117.9(5) . . ?
C32 C30 C31 121.4(5) . . ?
C29 C30 C31 120.7(6) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C30 123.0(5) . . ?
C33 C32 H32 118.5 . . ?
C30 C32 H32 118.5 . . ?
C32 C33 C34 118.0(5) . . ?
C32 C33 H33 121.0 . . ?
C34 C33 H33 121.0 . . ?
C28 C34 C33 121.0(5) . . ?
C28 C34 N1 110.8(4) . . ?
C33 C34 N1 128.2(5) . . ?
C37 C35 C36 117.7(3) . . ?
C37 C35 C27 125.8(3) . . ?
C36 C35 C27 116.5(3) . . ?
N2 C36 C35 177.7(5) . . ?
C35 C37 N3 123.4(4) . . ?
C35 C37 C9 121.7(3) . . ?
N3 C37 C9 114.8(3) . . ?
C26 N1 C34 110.3(4) . . ?
C26 N1 C25 124.6(4) . . ?
C34 N1 C25 125.1(4) . . ?
C37 N3 H3A 120.0 . . ?
C37 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
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 O1 1.202(5) . ?
C1 C2 1.460(6) . ?
C1 C9 1.564(6) . ?
C2 C7 1.381(6) . ?
C2 C3 1.400(7) . ?
C3 C4 1.356(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.452(6) . ?
C8 O2 1.216(5) . ?
C8 C9 1.552(5) . ?
C9 C10 1.486(5) . ?
C9 C37 1.515(5) . ?
C10 C18 1.333(5) . ?
C10 C11 1.491(5) . ?
C11 C12 1.365(5) . ?
C11 C16 1.397(5) . ?
C12 C13 1.378(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.502(6) . ?
C17 O3 1.220(5) . ?
C17 C18 1.480(5) . ?
C18 C27 1.480(5) . ?
C19 C24 1.383(6) . ?
C19 C20 1.396(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.377(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.376(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.501(6) . ?
C25 N1 1.457(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 O4 1.209(5) . ?
C26 N1 1.376(6) . ?
C26 C27 1.548(6) . ?
C27 C35 1.515(5) . ?
C27 C28 1.537(6) . ?
C28 C34 1.368(6) . ?
C28 C29 1.386(6) . ?
C29 C30 1.403(6) . ?
C29 H29 0.9300 . ?
C30 C32 1.388(8) . ?
C30 C31 1.496(8) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.368(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.377(6) . ?
C33 H33 0.9300 . ?
C34 N1 1.414(5) . ?
C35 C37 1.342(5) . ?
C35 C36 1.439(6) . ?
C36 N2 1.141(5) . ?
C37 N3 1.355(5) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
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
N3 H3A N2 0.86 2.25 3.054(5) 156.1 5_675
