#------------------------------------------------------------------------------
#$Date: 2022-03-30 03:23:16 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274093 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158610.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_7158610
loop_
_publ_author_name
'Lu, Yuling'
'Duan, Xianxian'
'Chen, Xia'
'Yao, Meng'
'Chen, Chunmei'
'Zhu, Hucheng'
'Luo, Zengwei'
'Zhang, Yonghui'
_publ_section_title
;
 A mild tetradehydro-Diels--Alder reaction of aryldiyne compounds affords
 exclusively linear products
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00121G
_journal_year                    2022
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-10-26 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.2820(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7838(2)
_cell_length_b                   9.39690(10)
_cell_length_c                   19.7446(3)
_cell_measurement_reflns_used    25828
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.554
_cell_measurement_theta_min      2.273
_cell_volume                     1807.56(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42473
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.837
_diffrn_reflns_theta_min         4.498
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       Block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0732
_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)+(0.1283P)²+0.4665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2078
_refine_ls_wR_factor_ref         0.2115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3310
_reflns_number_total             3632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00121g2.cif
_cod_data_source_block           1_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158610
_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   0.865
_shelx_estimated_absorpt_t_max   0.887
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.4067(2) 0.9579(2) 0.20082(10) 0.0593(5) Uani 1 1 d . . . . .
H1 H 0.4158 0.9025 0.1625 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3477(2) 1.0886(2) 0.19369(11) 0.0645(5) Uani 1 1 d . . . . .
H2 H 0.3152 1.1208 0.1507 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3351(2) 1.1756(2) 0.25069(12) 0.0661(5) Uani 1 1 d . . . . .
H3 H 0.2989 1.2667 0.2449 0.079 Uiso 1 1 calc R U . . .
C4 C 0.37549(19) 1.1275(2) 0.31420(10) 0.0592(5) Uani 1 1 d . . . . .
H4 H 0.3646 1.1852 0.3516 0.071 Uiso 1 1 calc R U . . .
C5 C 0.43428(17) 0.98987(19) 0.32420(9) 0.0496(4) Uani 1 1 d . . . . .
C6 C 0.45489(17) 0.90485(18) 0.26601(9) 0.0490(4) Uani 1 1 d . . . . .
C7 C 0.51936(19) 0.77030(19) 0.27441(9) 0.0529(4) Uani 1 1 d . . . . .
H7 H 0.5346 0.7152 0.2367 0.063 Uiso 1 1 calc R U . . .
C8 C 0.55896(18) 0.72225(18) 0.33852(9) 0.0496(4) Uani 1 1 d . . . . .
C9 C 0.53303(18) 0.8038(2) 0.39542(9) 0.0522(4) Uani 1 1 d . . . . .
C10 C 0.47350(19) 0.9353(2) 0.38967(9) 0.0543(4) Uani 1 1 d . . . . .
H10 H 0.4591 0.9880 0.4283 0.065 Uiso 1 1 calc R U . . .
C11 C 0.5837(2) 0.7277(2) 0.45768(10) 0.0626(5) Uani 1 1 d . . . . .
C12 C 0.6322(2) 0.5860(2) 0.35977(9) 0.0545(4) Uani 1 1 d . . . . .
C13 C 0.5452(3) 0.4571(2) 0.33732(11) 0.0696(6) Uani 1 1 d . . . . .
H13A H 0.4624 0.4576 0.3599 0.104 Uiso 1 1 calc R U . . .
H13B H 0.5959 0.3716 0.3489 0.104 Uiso 1 1 calc R U . . .
H13C H 0.5225 0.4606 0.2890 0.104 Uiso 1 1 calc R U . . .
C14 C 0.7734(2) 0.5826(3) 0.33229(13) 0.0735(6) Uani 1 1 d . . . . .
H14A H 0.7627 0.5927 0.2837 0.110 Uiso 1 1 calc R U . . .
H14B H 0.8175 0.4936 0.3440 0.110 Uiso 1 1 calc R U . . .
H14C H 0.8285 0.6593 0.3519 0.110 Uiso 1 1 calc R U . . .
C15 C 0.7016(2) 0.5032(3) 0.48240(11) 0.0721(6) Uani 1 1 d . . . . .
C16 C 0.8267(4) 0.2904(3) 0.49425(15) 0.1040(10) Uani 1 1 d . . . . .
H16A H 0.7587 0.2446 0.5196 0.125 Uiso 1 1 calc R U . . .
H16B H 0.8970 0.3314 0.5262 0.125 Uiso 1 1 calc R U . . .
C17 C 0.88809(15) 0.18581(16) 0.44967(7) 0.0672(5) Uani 1 1 d G . . . .
C18 C 0.80511(15) 0.0995(2) 0.40599(9) 0.0853(7) Uani 1 1 d G . . . .
H18 H 0.7102 0.1099 0.4031 0.102 Uiso 1 1 calc R U . . .
C19 C 0.8640(3) -0.00236(18) 0.36668(9) 0.1233(12) Uani 1 1 d G U . . .
H19 H 0.8084 -0.0601 0.3375 0.148 Uiso 1 1 calc R U . . .
C20 C 1.0058(3) -0.0179(2) 0.37105(10) 0.1392(17) Uani 1 1 d G U . . .
H20 H 1.0451 -0.0860 0.3447 0.167 Uiso 1 1 calc R U . . .
C21 C 1.08876(18) 0.0684(3) 0.41473(12) 0.1202(15) Uani 1 1 d G . . . .
H21 H 1.1837 0.0581 0.4176 0.144 Uiso 1 1 calc R U . . .
C22 C 1.02992(15) 0.1703(2) 0.45404(10) 0.0845(7) Uani 1 1 d G . . . .
H22 H 1.0854 0.2280 0.4833 0.101 Uiso 1 1 calc R U . . .
N1 N 0.64402(18) 0.60220(18) 0.43602(8) 0.0598(4) Uani 1 1 d . . . . .
O1 O 0.5760(2) 0.7642(2) 0.51592(7) 0.0943(6) Uani 1 1 d . . . . .
O2 O 0.6969(3) 0.5081(3) 0.54216(9) 0.1219(10) Uani 1 1 d . . . . .
O3 O 0.7630(2) 0.40001(18) 0.45013(8) 0.0833(5) Uani 1 1 d . . . . .
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'
N N 0.0311 0.0180 '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
C2 C1 C6 120.91(18) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.68(19) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.45(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.73(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C10 C5 C4 122.02(16) . . ?
C10 C5 C6 119.15(16) . . ?
C4 C5 C6 118.82(17) . . ?
C7 C6 C1 121.80(16) . . ?
C7 C6 C5 119.95(16) . . ?
C1 C6 C5 118.23(17) . . ?
C8 C7 C6 119.28(15) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.34(17) . . ?
C7 C8 C12 128.73(15) . . ?
C9 C8 C12 110.94(15) . . ?
C10 C9 C8 122.32(17) . . ?
C10 C9 C11 128.21(16) . . ?
C8 C9 C11 109.43(16) . . ?
C9 C10 C5 118.86(16) . . ?
C9 C10 H10 120.6 . . ?
C5 C10 H10 120.6 . . ?
O1 C11 N1 126.4(2) . . ?
O1 C11 C9 127.75(19) . . ?
N1 C11 C9 105.85(15) . . ?
N1 C12 C8 100.55(13) . . ?
N1 C12 C13 111.12(16) . . ?
C8 C12 C13 110.86(16) . . ?
N1 C12 C14 111.57(17) . . ?
C8 C12 C14 109.92(16) . . ?
C13 C12 C14 112.24(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O3 124.3(2) . . ?
O2 C15 N1 125.5(2) . . ?
O3 C15 N1 110.22(18) . . ?
O3 C16 C17 106.8(2) . . ?
O3 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O3 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C18 C17 C22 120.0 . . ?
C18 C17 C16 120.6(2) . . ?
C22 C17 C16 119.3(2) . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.0 . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C15 N1 C11 121.24(17) . . ?
C15 N1 C12 125.50(16) . . ?
C11 N1 C12 113.18(15) . . ?
C15 O3 C16 114.63(18) . . ?
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 C2 1.359(3) . ?
C1 C6 1.420(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.405(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.422(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.410(3) . ?
C5 C6 1.429(2) . ?
C6 C7 1.416(3) . ?
C7 C8 1.366(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.402(2) . ?
C8 C12 1.508(2) . ?
C9 C10 1.367(3) . ?
C9 C11 1.468(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.209(2) . ?
C11 N1 1.403(2) . ?
C12 N1 1.507(2) . ?
C12 C13 1.523(3) . ?
C12 C14 1.530(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O2 1.186(3) . ?
C15 O3 1.333(3) . ?
C15 N1 1.388(3) . ?
C16 O3 1.452(3) . ?
C16 C17 1.483(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.3900 . ?
C17 C22 1.3900 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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 1.2(3) . . . . ?
C1 C2 C3 C4 -3.4(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C10 -178.10(18) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C2 C1 C6 C7 -178.63(17) . . . . ?
C2 C1 C6 C5 2.6(3) . . . . ?
C10 C5 C6 C7 -2.7(2) . . . . ?
C4 C5 C6 C7 176.92(15) . . . . ?
C10 C5 C6 C1 176.05(16) . . . . ?
C4 C5 C6 C1 -4.3(2) . . . . ?
C1 C6 C7 C8 -177.52(16) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C6 C7 C8 C12 -178.07(17) . . . . ?
C7 C8 C9 C10 -2.9(3) . . . . ?
C12 C8 C9 C10 176.81(16) . . . . ?
C7 C8 C9 C11 179.16(17) . . . . ?
C12 C8 C9 C11 -1.2(2) . . . . ?
C8 C9 C10 C5 1.3(3) . . . . ?
C11 C9 C10 C5 178.85(19) . . . . ?
C4 C5 C10 C9 -178.14(16) . . . . ?
C6 C5 C10 C9 1.5(3) . . . . ?
C10 C9 C11 O1 4.0(4) . . . . ?
C8 C9 C11 O1 -178.1(2) . . . . ?
C10 C9 C11 N1 -175.83(19) . . . . ?
C8 C9 C11 N1 2.0(2) . . . . ?
C7 C8 C12 N1 179.55(18) . . . . ?
C9 C8 C12 N1 -0.1(2) . . . . ?
C7 C8 C12 C13 -62.9(2) . . . . ?
C9 C8 C12 C13 117.51(18) . . . . ?
C7 C8 C12 C14 61.8(3) . . . . ?
C9 C8 C12 C14 -117.82(18) . . . . ?
O3 C16 C17 C18 -68.7(3) . . . . ?
O3 C16 C17 C22 114.1(2) . . . . ?
C22 C17 C18 C19 0.0 . . . . ?
C16 C17 C18 C19 -177.18(18) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C17 0.0 . . . . ?
C18 C17 C22 C21 0.0 . . . . ?
C16 C17 C22 C21 177.21(18) . . . . ?
O2 C15 N1 C11 6.0(4) . . . . ?
O3 C15 N1 C11 -174.4(2) . . . . ?
O2 C15 N1 C12 -170.8(3) . . . . ?
O3 C15 N1 C12 8.8(3) . . . . ?
O1 C11 N1 C15 0.9(4) . . . . ?
C9 C11 N1 C15 -179.25(19) . . . . ?
O1 C11 N1 C12 178.0(2) . . . . ?
C9 C11 N1 C12 -2.1(2) . . . . ?
C8 C12 N1 C15 178.4(2) . . . . ?
C13 C12 N1 C15 61.0(3) . . . . ?
C14 C12 N1 C15 -65.1(3) . . . . ?
C8 C12 N1 C11 1.4(2) . . . . ?
C13 C12 N1 C11 -116.0(2) . . . . ?
C14 C12 N1 C11 117.9(2) . . . . ?
O2 C15 O3 C16 -0.3(4) . . . . ?
N1 C15 O3 C16 -179.9(3) . . . . ?
C17 C16 O3 C15 179.7(2) . . . . ?
