#------------------------------------------------------------------------------
#$Date: 2022-09-08 03:47:16 +0300 (Thu, 08 Sep 2022) $
#$Revision: 277731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158867.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_7158867
loop_
_publ_author_name
'Gómez-Prado, Raúl A.'
'Silva, Ana L.'
'Miranda, Luis D.'
_publ_section_title
;
 Synthesis of nuevamine and a cyano-chilenine analog via divergent
 C(sp3)--H bond functionalization of isoindolinone derivatives
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01304E
_journal_year                    2022
_chemical_formula_moiety         'C22 H20 N2 O6'
_chemical_formula_sum            'C22 H20 N2 O6'
_chemical_formula_weight         408.40
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-02-08 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                94.605(3)
_cell_angle_beta                 108.730(4)
_cell_angle_gamma                98.534(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3790(13)
_cell_length_b                   10.2477(16)
_cell_length_c                   12.547(2)
_cell_measurement_reflns_used    3997
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.48
_cell_volume                     999.5(3)
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_min         1.730
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       platy
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0558
_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)+(0.0756P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2909
_reflns_number_total             4597
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01304e2.cif
_cod_data_source_block           002MGL14
_cod_original_cell_volume        999.6(3)
_cod_database_code               7158867
_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   0.966
_shelx_estimated_absorpt_t_max   0.993
_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 0.1822(2) -0.00799(15) 0.00257(13) 0.0555(5) Uani 1 1 d . . . . .
O2 O 0.2095(2) 0.07511(14) 0.72830(12) 0.0430(4) Uani 1 1 d . . . . .
O3 O 0.0666(2) 0.27704(14) 0.67291(12) 0.0477(4) Uani 1 1 d . . . . .
O4 O 0.0266(2) 0.29994(15) 0.26024(12) 0.0479(4) Uani 1 1 d . . . . .
O5 O 0.3297(2) 0.51915(13) 0.26921(12) 0.0453(4) Uani 1 1 d . . . . .
O6 O 0.3120(2) 0.64144(14) 0.07897(13) 0.0618(5) Uani 1 1 d . . . . .
C1 C 0.2159(3) 0.0910(2) 0.07123(18) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.2462(2) 0.09027(15) 0.18615(14) 0.0361(4) Uani 1 1 d . . . . .
N2 N 0.5843(3) 0.2828(2) 0.40176(18) 0.0598(6) Uani 1 1 d . . . . .
C2 C 0.2771(3) 0.22430(18) 0.24781(16) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.2729(3) 0.31153(19) 0.15503(16) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.3012(3) 0.44808(19) 0.16591(17) 0.0367(5) Uani 1 1 d . . . . .
C5 C 0.2882(3) 0.5060(2) 0.06613(19) 0.0434(5) Uani 1 1 d . . . . .
C6 C 0.2532(3) 0.4265(2) -0.0362(2) 0.0535(6) Uani 1 1 d . . . . .
H6 H 0.2473 0.4665 -0.1010 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2269(3) 0.2889(2) -0.04453(18) 0.0494(6) Uani 1 1 d . . . . .
H7 H 0.2032 0.2363 -0.1136 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2370(3) 0.2326(2) 0.05320(17) 0.0392(5) Uani 1 1 d . . . . .
C9 C 0.1895(3) -0.02835(19) 0.23124(17) 0.0402(5) Uani 1 1 d . . . . .
H9A H 0.2110 -0.1059 0.1921 0.048 Uiso 1 1 calc R U . . .
H9B H 0.0668 -0.0391 0.2156 0.048 Uiso 1 1 calc R U . . .
C10 C 0.2786(3) -0.0226(2) 0.35810(17) 0.0391(5) Uani 1 1 d . . . . .
H10A H 0.2615 -0.1124 0.3771 0.047 Uiso 1 1 calc R U . . .
H10B H 0.4006 0.0058 0.3744 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2236(2) 0.06704(18) 0.43650(16) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.2395(2) 0.02984(19) 0.54393(16) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.2844 -0.0460 0.5635 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1906(3) 0.10231(19) 0.62144(16) 0.0324(4) Uani 1 1 d . . . . .
C14 C 0.1140(3) 0.21395(19) 0.59118(16) 0.0337(5) Uani 1 1 d . . . . .
C15 C 0.0943(3) 0.25017(19) 0.48605(17) 0.0352(5) Uani 1 1 d . . . . .
H15 H 0.0418 0.3224 0.4650 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1523(3) 0.18008(18) 0.40875(16) 0.0323(4) Uani 1 1 d . . . . .
C17 C 0.1374(3) 0.23820(19) 0.30319(16) 0.0336(5) Uani 1 1 d . . . . .
C18 C 0.4505(3) 0.2564(2) 0.33618(18) 0.0381(5) Uani 1 1 d . . . . .
C19 C 0.3022(3) -0.0279(2) 0.76836(19) 0.0547(7) Uani 1 1 d . . . . .
H19A H 0.3056 -0.0370 0.8446 0.082 Uiso 1 1 calc R U . . .
H19B H 0.4170 -0.0053 0.7673 0.082 Uiso 1 1 calc R U . . .
H19C H 0.2461 -0.1105 0.7200 0.082 Uiso 1 1 calc R U . . .
C20 C -0.0075(4) 0.3924(2) 0.6470(2) 0.0596(7) Uani 1 1 d . . . . .
H20A H -0.0368 0.4271 0.7102 0.089 Uiso 1 1 calc R U . . .
H20B H -0.1089 0.3689 0.5810 0.089 Uiso 1 1 calc R U . . .
H20C H 0.0736 0.4589 0.6323 0.089 Uiso 1 1 calc R U . . .
C21 C 0.4874(4) 0.6126(3) 0.3166(2) 0.0736(8) Uani 1 1 d . . . . .
H21A H 0.4980 0.6513 0.3914 0.110 Uiso 1 1 calc R U . . .
H21B H 0.4885 0.6816 0.2692 0.110 Uiso 1 1 calc R U . . .
H21C H 0.5817 0.5678 0.3210 0.110 Uiso 1 1 calc R U . . .
C22 C 0.2965(5) 0.7054(3) -0.0200(2) 0.0849(10) Uani 1 1 d . . . . .
H22A H 0.3183 0.8002 0.0008 0.127 Uiso 1 1 calc R U . . .
H22B H 0.1826 0.6772 -0.0737 0.127 Uiso 1 1 calc R U . . .
H22C H 0.3780 0.6817 -0.0536 0.127 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
C13 O2 C19 118.07(16) . . ?
C14 O3 C20 117.16(16) . . ?
C4 O5 C21 116.67(18) . . ?
C5 O6 C22 117.80(19) . . ?
O1 C1 N1 124.55(19) . . ?
O1 C1 C8 129.02(19) . . ?
N1 C1 C8 106.42(16) . . ?
C1 N1 C9 121.82(16) . . ?
C1 N1 C2 112.58(16) . . ?
C9 N1 C2 121.79(15) . . ?
N1 C2 C18 111.01(16) . . ?
N1 C2 C3 102.18(15) . . ?
C18 C2 C3 108.94(16) . . ?
N1 C2 C17 110.76(15) . . ?
C18 C2 C17 110.07(16) . . ?
C3 C2 C17 113.66(16) . . ?
C4 C3 C8 122.82(18) . . ?
C4 C3 C2 127.58(18) . . ?
C8 C3 C2 109.59(16) . . ?
O5 C4 C3 119.20(18) . . ?
O5 C4 C5 123.90(18) . . ?
C3 C4 C5 116.78(18) . . ?
O6 C5 C6 124.25(19) . . ?
O6 C5 C4 115.44(19) . . ?
C6 C5 C4 120.31(19) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C3 C8 C7 120.64(19) . . ?
C3 C8 C1 109.11(17) . . ?
C7 C8 C1 130.24(19) . . ?
N1 C9 C10 113.21(17) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 117.35(17) . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
C9 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
C16 C11 C12 117.67(17) . . ?
C16 C11 C10 125.44(17) . . ?
C12 C11 C10 116.83(16) . . ?
C13 C12 C11 121.94(18) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
O2 C13 C12 124.85(17) . . ?
O2 C13 C14 115.32(16) . . ?
C12 C13 C14 119.83(17) . . ?
O3 C14 C15 125.70(18) . . ?
O3 C14 C13 115.28(17) . . ?
C15 C14 C13 119.01(17) . . ?
C14 C15 C16 121.18(18) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 120.25(17) . . ?
C11 C16 C17 124.70(17) . . ?
C15 C16 C17 115.01(17) . . ?
O4 C17 C16 123.31(18) . . ?
O4 C17 C2 118.80(17) . . ?
C16 C17 C2 117.82(16) . . ?
N2 C18 C2 178.2(2) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O1 C1 1.212(2) . ?
O2 C13 1.355(2) . ?
O2 C19 1.431(2) . ?
O3 C14 1.363(2) . ?
O3 C20 1.428(3) . ?
O4 C17 1.209(2) . ?
O5 C4 1.366(2) . ?
O5 C21 1.430(3) . ?
O6 C5 1.361(2) . ?
O6 C22 1.428(3) . ?
C1 N1 1.382(3) . ?
C1 C8 1.480(3) . ?
N1 C9 1.461(2) . ?
N1 C2 1.465(2) . ?
N2 C18 1.135(3) . ?
C2 C18 1.488(3) . ?
C2 C3 1.518(3) . ?
C2 C17 1.559(3) . ?
C3 C4 1.372(3) . ?
C3 C8 1.376(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.518(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.399(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.413(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.410(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.472(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
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
C9 H9B O2 0.97 2.61 3.510(3) 153.8 2_556
C19 H19A O1 0.96 2.53 3.398(3) 150.5 1_556
C21 H21B O6 0.96 2.33 2.931(3) 119.7 .
C22 H22A O1 0.96 2.42 3.240(3) 143.7 1_565
C22 H22B O4 0.96 2.49 3.333(4) 147.0 2_565
