#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:54:40 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/90/7129026.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_7129026
loop_
_publ_author_name
'Wei, Hao-Zhao'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
 Construction of an isoquinolinone framework from
 carboxylic-ester-directed umpolung ring opening of
 methylenecyclopropanes.
;
_journal_issue                   85
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11201
_journal_page_last               11204
_journal_paper_doi               10.1039/d1cc04826k
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_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   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-06-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.437(3)
_cell_angle_beta                 98.614(3)
_cell_angle_gamma                97.851(3)
_cell_formula_units_Z            2
_cell_length_a                   5.5414(5)
_cell_length_b                   9.7020(10)
_cell_length_c                   16.4455(17)
_cell_measurement_reflns_used    6407
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.821
_cell_measurement_theta_min      5.085
_cell_volume                     853.28(15)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14816
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.763
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.048(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0410
_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)+(0.0432P)²+0.2046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             3320
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04826k3.cif
_cod_data_source_block           mo_d8v21490_0m
_cod_depositor_comments
'Adding full bibliography for 7129025--7129026.cif.'
_cod_database_code               7129026
_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   0.985
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
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
O1 O 0.80058(18) 0.60781(11) 0.55179(5) 0.0445(3) Uani 1 1 d . . . . .
N1 N 0.8247(2) 0.55648(11) 0.41469(6) 0.0345(3) Uani 1 1 d . . . . .
H1 H 0.944(3) 0.5018(17) 0.4274(9) 0.052(4) Uiso 1 1 d . . . . .
N2 N 0.9144(2) 0.25156(13) 0.12764(7) 0.0478(3) Uani 1 1 d . . . . .
C1 C 0.7306(2) 0.62301(14) 0.47862(8) 0.0347(3) Uani 1 1 d . . . . .
C2 C 0.5480(2) 0.71132(13) 0.45480(8) 0.0330(3) Uani 1 1 d . . . . .
C3 C 0.4319(3) 0.77778(14) 0.51607(8) 0.0400(3) Uani 1 1 d . . . . .
H3 H 0.4739 0.7663 0.5719 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2568(3) 0.85959(15) 0.49478(9) 0.0465(4) Uani 1 1 d . . . . .
H4 H 0.1785 0.9039 0.5359 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1956(3) 0.87656(15) 0.41198(9) 0.0456(4) Uani 1 1 d . . . . .
H5 H 0.0756 0.9326 0.3976 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3078(2) 0.81277(14) 0.35104(9) 0.0393(3) Uani 1 1 d . . . . .
H6 H 0.2638 0.8256 0.2955 0.047 Uiso 1 1 calc R U . . .
C7 C 0.4887(2) 0.72803(13) 0.37090(8) 0.0325(3) Uani 1 1 d . . . . .
C8 C 0.6066(2) 0.65570(13) 0.30798(7) 0.0326(3) Uani 1 1 d . . . . .
C9 C 0.7697(2) 0.57125(13) 0.33183(7) 0.0326(3) Uani 1 1 d . . . . .
C10 C 0.9040(2) 0.48540(13) 0.27556(8) 0.0338(3) Uani 1 1 d . . . . .
H10A H 1.0792 0.4987 0.3008 0.041 Uiso 1 1 calc R U . . .
H10B H 0.8932 0.5191 0.2220 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7964(3) 0.32795(15) 0.26033(9) 0.0443(4) Uani 1 1 d . . . . .
H11A H 0.7971 0.2956 0.3141 0.053 Uiso 1 1 calc R U . . .
H11B H 0.6244 0.3139 0.2316 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9420(2) 0.24147(14) 0.20864(8) 0.0379(3) Uani 1 1 d . . . . .
C13 C 1.1025(3) 0.15991(16) 0.24336(9) 0.0477(4) Uani 1 1 d . . . . .
H13 H 1.1198 0.1550 0.3006 0.057 Uiso 1 1 calc R U . . .
C14 C 1.2369(3) 0.08574(17) 0.19321(11) 0.0561(4) Uani 1 1 d . . . . .
H14 H 1.3452 0.0289 0.2156 0.067 Uiso 1 1 calc R U . . .
C15 C 1.2094(3) 0.09655(17) 0.11015(11) 0.0552(4) Uani 1 1 d . . . . .
H15 H 1.2989 0.0478 0.0745 0.066 Uiso 1 1 calc R U . . .
C16 C 1.0481(3) 0.18025(18) 0.08057(9) 0.0548(4) Uani 1 1 d . . . . .
H16 H 1.0306 0.1879 0.0237 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5546(2) 0.67751(14) 0.21926(8) 0.0354(3) Uani 1 1 d . . . . .
C18 C 0.3991(3) 0.57707(17) 0.15820(8) 0.0469(4) Uani 1 1 d . . . . .
H18 H 0.3225 0.4935 0.1725 0.056 Uiso 1 1 calc R U . . .
C19 C 0.3560(3) 0.5992(2) 0.07615(9) 0.0594(5) Uani 1 1 d . . . . .
H19 H 0.2498 0.5307 0.0352 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4681(3) 0.7209(2) 0.05428(9) 0.0589(5) Uani 1 1 d . . . . .
H20 H 0.4386 0.7354 -0.0014 0.071 Uiso 1 1 calc R U . . .
C21 C 0.6229(3) 0.82078(19) 0.11415(10) 0.0545(4) Uani 1 1 d . . . . .
H21 H 0.7006 0.9036 0.0994 0.065 Uiso 1 1 calc R U . . .
C22 C 0.6649(3) 0.79958(16) 0.19625(9) 0.0436(4) Uani 1 1 d . . . . .
H22 H 0.7697 0.8690 0.2370 0.052 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
C1 N1 C9 125.58(11) . . ?
C1 N1 H1 118.1(9) . . ?
C9 N1 H1 116.2(9) . . ?
C16 N2 C12 117.77(13) . . ?
O1 C1 N1 120.71(11) . . ?
O1 C1 C2 123.84(11) . . ?
N1 C1 C2 115.45(11) . . ?
C3 C2 C7 120.72(12) . . ?
C3 C2 C1 119.26(12) . . ?
C7 C2 C1 120.02(11) . . ?
C4 C3 C2 120.20(13) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.67(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.05(13) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.67(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 117.69(11) . . ?
C2 C7 C8 119.94(11) . . ?
C6 C7 C8 122.35(12) . . ?
C9 C8 C7 118.51(11) . . ?
C9 C8 C17 120.84(11) . . ?
C7 C8 C17 120.63(11) . . ?
C8 C9 N1 120.44(11) . . ?
C8 C9 C10 126.07(11) . . ?
N1 C9 C10 113.49(11) . . ?
C9 C10 C11 111.83(10) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 111.59(11) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N2 C12 C13 121.78(13) . . ?
N2 C12 C11 116.23(12) . . ?
C13 C12 C11 121.96(13) . . ?
C14 C13 C12 119.42(14) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 118.82(15) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 118.28(14) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N2 C16 C15 123.92(15) . . ?
N2 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C22 C17 C18 118.46(13) . . ?
C22 C17 C8 120.02(12) . . ?
C18 C17 C8 121.52(13) . . ?
C17 C18 C19 120.38(15) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.41(15) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.70(14) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.06(16) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.99(14) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
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 C1 1.2443(15) . ?
N1 C1 1.3605(16) . ?
N1 C9 1.3840(15) . ?
N1 H1 0.923(17) . ?
N2 C16 1.3346(19) . ?
N2 C12 1.3375(17) . ?
C1 C2 1.4586(18) . ?
C2 C3 1.4009(18) . ?
C2 C7 1.4080(17) . ?
C3 C4 1.373(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.3725(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4116(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.4509(17) . ?
C8 C9 1.3534(18) . ?
C8 C17 1.4961(17) . ?
C9 C10 1.5012(16) . ?
C10 C11 1.5316(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.5027(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.384(2) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.373(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.371(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C22 1.3866(19) . ?
C17 C18 1.3872(19) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.373(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.3856(19) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
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
N1 H1 O1 0.923(17) 1.903(17) 2.8240(15) 176.6(14) 2_766
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
C9 N1 C1 O1 -176.61(12) . . . . ?
C9 N1 C1 C2 3.04(19) . . . . ?
O1 C1 C2 C3 -3.7(2) . . . . ?
N1 C1 C2 C3 176.65(12) . . . . ?
O1 C1 C2 C7 176.83(12) . . . . ?
N1 C1 C2 C7 -2.80(18) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C4 -179.01(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C3 C2 C7 C6 -0.46(19) . . . . ?
C1 C2 C7 C6 178.99(12) . . . . ?
C3 C2 C7 C8 -178.55(12) . . . . ?
C1 C2 C7 C8 0.89(18) . . . . ?
C5 C6 C7 C2 0.2(2) . . . . ?
C5 C6 C7 C8 178.28(13) . . . . ?
C2 C7 C8 C9 1.06(18) . . . . ?
C6 C7 C8 C9 -176.94(12) . . . . ?
C2 C7 C8 C17 -177.15(11) . . . . ?
C6 C7 C8 C17 4.84(19) . . . . ?
C7 C8 C9 N1 -1.01(19) . . . . ?
C17 C8 C9 N1 177.20(11) . . . . ?
C7 C8 C9 C10 178.28(11) . . . . ?
C17 C8 C9 C10 -3.5(2) . . . . ?
C1 N1 C9 C8 -1.2(2) . . . . ?
C1 N1 C9 C10 179.45(11) . . . . ?
C8 C9 C10 C11 -105.26(15) . . . . ?
N1 C9 C10 C11 74.08(14) . . . . ?
C9 C10 C11 C12 -176.24(11) . . . . ?
C16 N2 C12 C13 -0.2(2) . . . . ?
C16 N2 C12 C11 177.54(13) . . . . ?
C10 C11 C12 N2 -72.94(16) . . . . ?
C10 C11 C12 C13 104.79(15) . . . . ?
N2 C12 C13 C14 -0.5(2) . . . . ?
C11 C12 C13 C14 -178.14(13) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C12 N2 C16 C15 0.7(2) . . . . ?
C14 C15 C16 N2 -0.4(3) . . . . ?
C9 C8 C17 C22 -100.79(16) . . . . ?
C7 C8 C17 C22 77.38(16) . . . . ?
C9 C8 C17 C18 78.45(17) . . . . ?
C7 C8 C17 C18 -103.37(15) . . . . ?
C22 C17 C18 C19 0.0(2) . . . . ?
C8 C17 C18 C19 -179.28(13) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C17 0.7(2) . . . . ?
C18 C17 C22 C21 -0.5(2) . . . . ?
C8 C17 C22 C21 178.78(12) . . . . ?
