#------------------------------------------------------------------------------
#$Date: 2021-12-06 07:50:24 +0100 (Mon 06 de Dec de 2021) $
#$Revision: 271120 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/84/7158432.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_7158432
loop_
_publ_author_name
'Zhang, Wande'
'Nawaz, Shah'
'Huang, Yue'
'Gong, Wenjing'
'Wei, Xingfu'
'Qu, Jingping'
'Wang, Baomin'
_publ_section_title
;
 C-4 benzofuranylation of pyrazolones by a metal-free catalyzed indirect
 heteroarylation strategy.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              10215
_journal_page_last               10222
_journal_paper_doi               10.1039/d1ob01920a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C43 H32 N2 O2'
_chemical_formula_weight         608.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-27 deposited with the CCDC.	2021-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7763(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7039(6)
_cell_length_b                   17.6409(8)
_cell_length_c                   15.4808(7)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.32
_cell_volume                     3139.9(3)
_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      220(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43253
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.114
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6834
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    'riding mode'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0425
_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)+(0.0587P)²+0.4127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4091
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01920a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7158432
_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   0.988
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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_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
O2 O 0.99544(9) 0.04653(6) 0.67252(7) 0.0299(3) Uani 1 1 d . . . . .
O1 O 0.72627(9) 0.19523(6) 0.77401(7) 0.0325(3) Uani 1 1 d . . . . .
N2 N 0.66026(11) 0.08882(7) 0.83679(8) 0.0271(3) Uani 1 1 d . . . . .
N1 N 0.62888(11) 0.01370(7) 0.81229(8) 0.0272(3) Uani 1 1 d . . . . .
C5 C 0.83535(13) 0.09214(8) 0.58150(10) 0.0253(4) Uani 1 1 d . . . . .
C6 C 0.69586(12) 0.12905(9) 0.77107(10) 0.0254(4) Uani 1 1 d . . . . .
C7 C 0.80352(13) 0.06901(8) 0.66432(10) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.90252(13) 0.04313(8) 0.71556(10) 0.0250(4) Uani 1 1 d . . . . .
C9 C 0.68730(13) 0.07468(8) 0.69343(10) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.66845(15) -0.09129(9) 0.61815(11) 0.0357(4) Uani 1 1 d . . . . .
H10A H 0.7286 -0.0620 0.6026 0.043 Uiso 1 1 calc R U . . .
C11 C 1.03198(15) 0.13575(9) 0.85925(11) 0.0366(4) Uani 1 1 d . . . . .
H11A H 0.9652 0.1607 0.8292 0.044 Uiso 1 1 calc R U . . .
C12 C 0.93218(13) 0.01344(9) 0.80770(10) 0.0279(4) Uani 1 1 d . . . . .
H12A H 0.8646 0.0244 0.8358 0.034 Uiso 1 1 calc R U . . .
C13 C 0.64762(14) 0.11472(8) 0.92150(10) 0.0272(4) Uani 1 1 d . . . . .
C14 C 1.03568(14) 0.05710(9) 0.85982(10) 0.0280(4) Uani 1 1 d . . . . .
C15 C 0.58718(13) 0.10358(9) 0.61979(10) 0.0295(4) Uani 1 1 d . . . . .
H15A H 0.6066 0.1545 0.6017 0.035 Uiso 1 1 calc R U . . .
H15B H 0.5810 0.0701 0.5686 0.035 Uiso 1 1 calc R U . . .
C16 C 0.61637(14) -0.06858(9) 0.68724(10) 0.0285(4) Uani 1 1 d . . . . .
C17 C 0.95375(14) 0.07705(9) 0.59158(10) 0.0268(4) Uani 1 1 d . . . . .
C18 C 0.55530(15) 0.08991(9) 0.95766(11) 0.0326(4) Uani 1 1 d . . . . .
H18A H 0.4992 0.0573 0.9257 0.039 Uiso 1 1 calc R U . . .
C19 C 1.02120(15) 0.09293(9) 0.52959(11) 0.0345(4) Uani 1 1 d . . . . .
H19A H 1.1012 0.0820 0.5395 0.041 Uiso 1 1 calc R U . . .
C20 C 0.47115(14) 0.10630(9) 0.64888(10) 0.0306(4) Uani 1 1 d . . . . .
C21 C 0.78117(15) 0.12422(9) 0.50167(11) 0.0348(4) Uani 1 1 d . . . . .
H21A H 0.7009 0.1343 0.4908 0.042 Uiso 1 1 calc R U . . .
C22 C 0.64717(13) 0.00348(8) 0.73390(10) 0.0248(3) Uani 1 1 d . . . . .
C23 C 0.54581(16) 0.11324(10) 1.04102(12) 0.0402(4) Uani 1 1 d . . . . .
H23A H 0.4838 0.0958 1.0664 0.048 Uiso 1 1 calc R U . . .
C24 C 1.13328(16) 0.02218(10) 0.90665(11) 0.0390(4) Uani 1 1 d . . . . .
H24A H 1.1367 -0.0310 0.9096 0.047 Uiso 1 1 calc R U . . .
C25 C 1.03046(16) -0.10787(9) 0.77054(11) 0.0364(4) Uani 1 1 d . . . . .
H25A H 1.0785 -0.0787 0.7411 0.044 Uiso 1 1 calc R U . . .
C26 C 0.44094(15) 0.16778(11) 0.69478(13) 0.0442(5) Uani 1 1 d . . . . .
H26A H 0.4903 0.2102 0.7036 0.053 Uiso 1 1 calc R U . . .
C27 C 0.54328(17) -0.19935(10) 0.59337(13) 0.0462(5) Uani 1 1 d . . . . .
H27A H 0.5183 -0.2436 0.5614 0.055 Uiso 1 1 calc R U . . .
C28 C 0.94789(14) -0.07247(9) 0.80951(10) 0.0298(4) Uani 1 1 d . . . . .
C29 C 0.39368(14) 0.04632(10) 0.63324(12) 0.0378(4) Uani 1 1 d . . . . .
H29A H 0.4102 0.0050 0.5992 0.045 Uiso 1 1 calc R U . . .
C30 C 0.62672(17) 0.16189(10) 1.08716(12) 0.0424(5) Uani 1 1 d . . . . .
H30A H 0.6201 0.1775 1.1441 0.051 Uiso 1 1 calc R U . . .
C31 C 0.71708(17) 0.18755(10) 1.04993(12) 0.0420(5) Uani 1 1 d . . . . .
H31A H 0.7712 0.2217 1.0811 0.050 Uiso 1 1 calc R U . . .
C32 C 0.52743(15) -0.11272(9) 0.70888(11) 0.0355(4) Uani 1 1 d . . . . .
H32A H 0.4922 -0.0984 0.7562 0.043 Uiso 1 1 calc R U . . .
C33 C 0.63235(17) -0.15703(10) 0.57170(12) 0.0435(5) Uani 1 1 d . . . . .
H33A H 0.6688 -0.1726 0.5255 0.052 Uiso 1 1 calc R U . . .
C34 C 1.22625(16) 0.06467(11) 0.94937(12) 0.0465(5) Uani 1 1 d . . . . .
H34A H 1.2925 0.0400 0.9805 0.056 Uiso 1 1 calc R U . . .
C35 C 1.12469(16) 0.17784(10) 0.90206(13) 0.0451(5) Uani 1 1 d . . . . .
H35A H 1.1209 0.2311 0.9007 0.054 Uiso 1 1 calc R U . . .
C36 C 0.29286(16) 0.04646(11) 0.66688(14) 0.0493(5) Uani 1 1 d . . . . .
H36A H 0.2419 0.0049 0.6567 0.059 Uiso 1 1 calc R U . . .
C37 C 0.96560(16) 0.12546(10) 0.45293(11) 0.0390(4) Uani 1 1 d . . . . .
H37A H 1.0081 0.1375 0.4089 0.047 Uiso 1 1 calc R U . . .
C38 C 0.72937(15) 0.16370(9) 0.96730(11) 0.0361(4) Uani 1 1 d . . . . .
H38A H 0.7923 0.1805 0.9425 0.043 Uiso 1 1 calc R U . . .
C39 C 0.84738(16) 0.14086(10) 0.43920(11) 0.0405(4) Uani 1 1 d . . . . .
H39A H 0.8114 0.1632 0.3859 0.049 Uiso 1 1 calc R U . . .
C40 C 0.9750(2) -0.22893(11) 0.81762(13) 0.0540(6) Uani 1 1 d . . . . .
H40A H 0.9840 -0.2819 0.8203 0.065 Uiso 1 1 calc R U . . .
C41 C 0.87955(17) -0.11686(11) 0.85272(13) 0.0482(5) Uani 1 1 d . . . . .
H41A H 0.8227 -0.0939 0.8797 0.058 Uiso 1 1 calc R U . . .
C42 C 1.04334(18) -0.18566(10) 0.77427(12) 0.0442(5) Uani 1 1 d . . . . .
H42A H 1.0994 -0.2090 0.7469 0.053 Uiso 1 1 calc R U . . .
C43 C 1.22273(17) 0.14235(11) 0.94679(13) 0.0473(5) Uani 1 1 d . . . . .
H43A H 1.2865 0.1710 0.9752 0.057 Uiso 1 1 calc R U . . .
C44 C 0.49040(16) -0.17731(10) 0.66162(12) 0.0423(5) Uani 1 1 d . . . . .
H44A H 0.4291 -0.2062 0.6760 0.051 Uiso 1 1 calc R U . . .
C45 C 0.8935(2) -0.19458(11) 0.85691(15) 0.0619(6) Uani 1 1 d . . . . .
H45A H 0.8466 -0.2240 0.8870 0.074 Uiso 1 1 calc R U . . .
C46 C 0.33941(16) 0.16793(13) 0.72794(14) 0.0576(6) Uani 1 1 d . . . . .
H46A H 0.3204 0.2102 0.7594 0.069 Uiso 1 1 calc R U . . .
C47 C 0.26641(16) 0.10687(13) 0.71518(14) 0.0566(6) Uani 1 1 d . . . . .
H47A H 0.1985 0.1063 0.7394 0.068 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'
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
C17 O2 C8 106.35(11) . . ?
C6 N2 N1 112.85(12) . . ?
C6 N2 C13 128.15(13) . . ?
N1 N2 C13 118.94(12) . . ?
C22 N1 N2 107.79(12) . . ?
C17 C5 C21 117.01(14) . . ?
C17 C5 C7 105.11(13) . . ?
C21 C5 C7 137.87(15) . . ?
O1 C6 N2 126.63(14) . . ?
O1 C6 C9 127.38(14) . . ?
N2 C6 C9 105.98(12) . . ?
C8 C7 C5 106.13(13) . . ?
C8 C7 C9 124.42(13) . . ?
C5 C7 C9 129.38(14) . . ?
C7 C8 O2 111.57(13) . . ?
C7 C8 C12 134.08(14) . . ?
O2 C8 C12 114.34(12) . . ?
C7 C9 C22 115.66(12) . . ?
C7 C9 C6 110.21(12) . . ?
C22 C9 C6 100.08(12) . . ?
C7 C9 C15 113.45(12) . . ?
C22 C9 C15 108.92(12) . . ?
C6 C9 C15 107.45(12) . . ?
C16 C10 C33 120.42(17) . . ?
C35 C11 C14 120.97(16) . . ?
C8 C12 C28 111.73(13) . . ?
C8 C12 C14 110.21(13) . . ?
C28 C12 C14 114.14(13) . . ?
C18 C13 C38 120.68(15) . . ?
C18 C13 N2 119.81(14) . . ?
C38 C13 N2 119.50(14) . . ?
C24 C14 C11 118.16(15) . . ?
C24 C14 C12 123.24(15) . . ?
C11 C14 C12 118.59(14) . . ?
C20 C15 C9 112.78(13) . . ?
C10 C16 C32 118.78(15) . . ?
C10 C16 C22 121.69(14) . . ?
C32 C16 C22 119.39(15) . . ?
O2 C17 C19 124.37(14) . . ?
O2 C17 C5 110.83(13) . . ?
C19 C17 C5 124.77(15) . . ?
C13 C18 C23 119.47(16) . . ?
C37 C19 C17 116.55(16) . . ?
C26 C20 C29 117.94(16) . . ?
C26 C20 C15 120.71(15) . . ?
C29 C20 C15 121.31(15) . . ?
C39 C21 C5 118.96(16) . . ?
N1 C22 C16 121.05(14) . . ?
N1 C22 C9 113.16(13) . . ?
C16 C22 C9 125.33(13) . . ?
C30 C23 C18 120.30(17) . . ?
C14 C24 C34 120.63(16) . . ?
C28 C25 C42 120.75(16) . . ?
C46 C26 C20 121.00(17) . . ?
C33 C27 C44 120.30(17) . . ?
C41 C28 C25 118.17(16) . . ?
C41 C28 C12 119.61(15) . . ?
C25 C28 C12 122.20(14) . . ?
C36 C29 C20 120.81(17) . . ?
C31 C30 C23 119.84(17) . . ?
C30 C31 C38 120.73(17) . . ?
C44 C32 C16 120.67(17) . . ?
C27 C33 C10 119.92(18) . . ?
C43 C34 C24 120.71(17) . . ?
C43 C35 C11 120.31(17) . . ?
C47 C36 C29 120.35(18) . . ?
C19 C37 C39 120.95(16) . . ?
C31 C38 C13 118.95(16) . . ?
C21 C39 C37 121.73(16) . . ?
C45 C40 C42 119.47(18) . . ?
C28 C41 C45 120.85(19) . . ?
C40 C42 C25 120.36(18) . . ?
C34 C43 C35 119.17(18) . . ?
C27 C44 C32 119.91(17) . . ?
C40 C45 C41 120.41(19) . . ?
C47 C46 C26 120.24(19) . . ?
C46 C47 C36 119.55(19) . . ?
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
O2 C17 1.3672(18) . ?
O2 C8 1.3789(17) . ?
O1 C6 1.2189(18) . ?
N2 C6 1.368(2) . ?
N2 N1 1.4081(17) . ?
N2 C13 1.4223(19) . ?
N1 C22 1.2839(19) . ?
C5 C17 1.391(2) . ?
C5 C21 1.399(2) . ?
C5 C7 1.459(2) . ?
C6 C9 1.526(2) . ?
C7 C8 1.355(2) . ?
C7 C9 1.514(2) . ?
C8 C12 1.498(2) . ?
C9 C22 1.517(2) . ?
C9 C15 1.560(2) . ?
C10 C16 1.386(2) . ?
C10 C33 1.388(2) . ?
C11 C35 1.378(2) . ?
C11 C14 1.388(2) . ?
C12 C28 1.526(2) . ?
C12 C14 1.532(2) . ?
C13 C18 1.378(2) . ?
C13 C38 1.382(2) . ?
C14 C24 1.378(2) . ?
C15 C20 1.509(2) . ?
C16 C32 1.390(2) . ?
C16 C22 1.473(2) . ?
C17 C19 1.381(2) . ?
C18 C23 1.379(2) . ?
C19 C37 1.368(2) . ?
C20 C26 1.378(2) . ?
C20 C29 1.385(2) . ?
C21 C39 1.379(2) . ?
C23 C30 1.375(3) . ?
C24 C34 1.384(2) . ?
C25 C28 1.380(2) . ?
C25 C42 1.381(2) . ?
C26 C46 1.380(3) . ?
C27 C33 1.374(3) . ?
C27 C44 1.377(3) . ?
C28 C41 1.379(2) . ?
C29 C36 1.376(3) . ?
C30 C31 1.372(3) . ?
C31 C38 1.379(2) . ?
C32 C44 1.379(2) . ?
C34 C43 1.371(3) . ?
C35 C43 1.375(3) . ?
C36 C47 1.370(3) . ?
C37 C39 1.387(3) . ?
C40 C45 1.365(3) . ?
C40 C42 1.369(3) . ?
C41 C45 1.381(3) . ?
C46 C47 1.366(3) . ?
