#------------------------------------------------------------------------------
#$Date: 2025-03-07 18:30:27 +0200 (Fri, 07 Mar 2025) $
#$Revision: 298328 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157729.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_7157729
loop_
_publ_author_name
'Xu, Fen'
'Zhu, Wen-Jing'
'Wang, Juan'
'Ma, Qi'
'Shen, Li-Jing'
_publ_section_title
;
 Rhodium-catalyzed synthesis of substituted isoquinolones via a
 selective decarbonylation/alkyne insertion cascade of phthalimides.
;
_journal_issue                   40
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8219
_journal_page_last               8223
_journal_paper_doi               10.1039/d0ob01793k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C31 H22 N2 O'
_chemical_formula_sum            'C31 H22 N2 O'
_chemical_formula_weight         438.53
_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
_audit_creation_date             2020-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-29 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                69.234(9)
_cell_angle_beta                 89.878(8)
_cell_angle_gamma                72.178(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6741(10)
_cell_length_b                   10.8198(12)
_cell_length_c                   12.5635(11)
_cell_measurement_reflns_used    2750
_cell_measurement_temperature    295.44(10)
_cell_measurement_theta_max      71.2290
_cell_measurement_theta_min      4.6450
_cell_volume                     1162.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.44(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  25.00   1.00    3.85    --  -40.80  77.00-150.00   97
  2  ω   -108.00 -18.00   1.00    3.85    --  -40.80 -57.00 -60.00   90
  3  ω   -112.00 -83.00   1.00    3.85    --  -40.80 -57.00-180.00   29
  4  ω    -67.00  31.00   1.00    3.85    --  -40.80  57.00  90.00   98
  5  ω     52.00  77.00   1.00    3.85    --   40.80 -99.00-150.00   25
  6  ω     34.00  71.00   1.00   15.41    --  105.27 -61.00 -60.00   37
  7  ω     75.00 109.00   1.00   15.41    --  105.27 -95.00  30.00   34
  8  ω     73.00 109.00   1.00   15.41    --  105.27 -95.00 -60.00   36
  9  ω     23.00  62.00   1.00   15.41    --  105.27 -95.00  30.00   39
 10  ω     64.00 110.00   1.00   15.41    --  105.27-113.00-150.00   46
 11  ω    116.00 177.00   1.00   15.41    --  105.27  61.00-120.00   61
 12  ω     48.00  75.00   1.00   15.41    --  105.27 -45.00-180.00   27
 13  ω    109.00 176.00   1.00   15.41    --  105.27 125.00  30.00   67
 14  ω     33.00 129.00   1.00   15.41    --  105.27 -45.00  90.00   96
 15  ω    126.00 177.00   1.00   15.41    --  105.27  45.00  90.00   51
 16  ω     93.00 120.00   1.00   15.41    --  105.27  45.00  90.00   27
 17  ω     82.00 133.00   1.00   15.41    --  105.27 -61.00 -60.00   51
 18  ω     40.00  87.00   1.00   15.41    --  105.27 -77.00  90.00   47
 19  ω     40.00  68.00   1.00   15.41    --  105.27 -95.00 -60.00   28
 20  ω     47.00 172.00   1.00   15.41    --  105.27   0.00  60.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1163084000
_diffrn_orient_matrix_UB_12      -0.1453532000
_diffrn_orient_matrix_UB_13      0.0315140000
_diffrn_orient_matrix_UB_21      0.0157417000
_diffrn_orient_matrix_UB_22      -0.0130582000
_diffrn_orient_matrix_UB_23      0.1258707000
_diffrn_orient_matrix_UB_31      -0.1208729000
_diffrn_orient_matrix_UB_32      -0.0682431000
_diffrn_orient_matrix_UB_33      0.0247127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7737
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.873
_diffrn_reflns_theta_min         3.790
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       prism
_exptl_crystal_F_000             458
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.237
_refine_ls_R_factor_all          0.1907
_refine_ls_R_factor_gt           0.1657
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4066
_refine_ls_wR_factor_ref         0.4291
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2955
_reflns_number_total             4476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01793k2.cif
_cod_data_source_block           xf-20200802-13-2
_cod_depositor_comments
;
          Adding full bibliography for 7157729.cif.

2025-03-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         174.60
_cod_original_formula_moiety         '0.4(C32 H22 N O)'
_cod_original_formula_units_Z            5
_cod_original_formula_sum        'C12.80 H8.80 N0.40 O0.40'
_cod_database_code               7157729
loop_
_cod_entry_issue_id
_cod_entry_issue_origin
_cod_entry_issue_severity
_cod_entry_issue_description
_cod_entry_issue_author
_cod_entry_issue_date
1 experiment error
;
  One of the nitrogen atoms has been wrongly assigned as a carbon. The
  formula has been updated to reflect the real composition but the 
  coordinate list has not been modified since the refinement should be
  repeated to update residuals and derived data.
;
miguel
2025-03-05T19:20:00Z
_shelxl_version_number           2013-2
_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.
;
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.619
_oxdiff_exptl_absorpt_empirical_full_min 0.532
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 0.4094(7) 0.5939(4) 0.1828(4) 0.134(2) Uani 1 1 d . . . . .
N1 N 0.1601(8) 0.7141(6) 0.3389(6) 0.1167(19) Uani 1 1 d . . . . .
C1 C 0.3931(11) 0.7592(7) 0.3071(6) 0.115(3) Uani 1 1 d . . . . .
C2 C 0.3135(12) 0.7089(6) 0.3825(6) 0.128(3) Uani 1 1 d . . . . .
C3 C 0.5180(8) 0.7506(7) 0.3462(5) 0.0951(17) Uani 1 1 d . . . . .
H3 H 0.5768 0.7815 0.2912 0.114 Uiso 1 1 calc R . . . .
C4 C 0.5782(13) 0.7029(8) 0.4568(10) 0.163(5) Uani 1 1 d . . . . .
H4 H 0.6694 0.7078 0.4740 0.196 Uiso 1 1 calc R . . . .
C5 C 0.4951(15) 0.6426(7) 0.5498(7) 0.153(5) Uani 1 1 d . . . . .
H5 H 0.5290 0.6036 0.6275 0.184 Uiso 1 1 calc R . . . .
C6 C 0.3550(10) 0.6532(5) 0.5025(5) 0.103(2) Uani 1 1 d . . . . .
C7 C 0.2551(16) 0.6101(12) 0.5679(12) 0.162(5) Uani 1 1 d . . . . .
H7 H 0.2796 0.5815 0.6464 0.195 Uiso 1 1 calc R . . . .
C8 C 0.133(2) 0.6025(11) 0.5390(12) 0.184(6) Uani 1 1 d . . . . .
H8 H 0.0787 0.5590 0.5919 0.221 Uiso 1 1 calc R . . . .
C9 C 0.0880(12) 0.6633(9) 0.4245(10) 0.156(4) Uani 1 1 d . . . . .
H9 H -0.0069 0.6701 0.4031 0.188 Uiso 1 1 calc R . . . .
C10 C 0.3340(8) 0.8149(5) 0.1857(4) 0.0934(19) Uani 1 1 d . . . . .
C11 C 0.3601(8) 0.7201(5) 0.1292(5) 0.0940(18) Uani 1 1 d . . . . .
C12 C 0.3271(5) 0.7827(4) 0.0047(4) 0.0689(11) Uani 1 1 d . . . . .
C13 C 0.2762(5) 0.9283(4) -0.0525(4) 0.0611(10) Uani 1 1 d . . . . .
C14 C 0.2458(5) 1.0176(4) 0.0141(3) 0.0603(10) Uani 1 1 d . . . . .
C15 C 0.2737(6) 0.9587(5) 0.1295(4) 0.0785(14) Uani 1 1 d . . . . .
C16 C 0.2455(7) 1.0439(5) 0.2039(4) 0.0819(15) Uani 1 1 d . . . . .
C17 C 0.1185(9) 1.0622(6) 0.2555(6) 0.103(2) Uani 1 1 d . . . . .
H17 H 0.0529 1.0183 0.2465 0.124 Uiso 1 1 calc R . . . .
C18 C 0.0880(10) 1.1445(7) 0.3201(6) 0.110(2) Uani 1 1 d . . . . .
H18 H 0.0015 1.1568 0.3536 0.132 Uiso 1 1 calc R . . . .
C19 C 0.1820(9) 1.2066(9) 0.3347(6) 0.117(3) Uani 1 1 d . . . . .
H19 H 0.1625 1.2603 0.3800 0.141 Uiso 1 1 calc R . . . .
C20 C 0.3098(10) 1.1908(12) 0.2819(9) 0.152(4) Uani 1 1 d . . . . .
H20 H 0.3750 1.2348 0.2918 0.183 Uiso 1 1 calc R . . . .
C21 C 0.3402(9) 1.1115(10) 0.2156(7) 0.123(3) Uani 1 1 d . . . . .
H21 H 0.4242 1.1033 0.1789 0.148 Uiso 1 1 calc R . . . .
C22 C 0.3549(6) 0.6971(5) -0.0582(4) 0.0765(13) Uani 1 1 d . . . . .
H22 H 0.3895 0.6005 -0.0201 0.092 Uiso 1 1 calc R . . . .
C23 C 0.3320(6) 0.7531(5) -0.1768(5) 0.0785(13) Uani 1 1 d . . . . .
H23 H 0.3504 0.6941 -0.2177 0.094 Uiso 1 1 calc R . . . .
C24 C 0.2816(6) 0.8969(5) -0.2349(4) 0.0768(13) Uani 1 1 d . . . . .
C25 C 0.2532(6) 0.9822(5) -0.1723(4) 0.0725(12) Uani 1 1 d . . . . .
H25 H 0.2176 1.0787 -0.2110 0.087 Uiso 1 1 calc R . . . .
C26 C 0.2608(10) 0.9589(7) -0.3642(5) 0.110(2) Uani 1 1 d . . . . .
H26A H 0.1868 1.0493 -0.3900 0.165 Uiso 1 1 calc GR . . . .
H26B H 0.2313 0.8988 -0.3932 0.165 Uiso 1 1 calc GR . . . .
H26C H 0.3512 0.9683 -0.3916 0.165 Uiso 1 1 calc GR . . . .
C27 C 0.1897(6) 1.1716(4) -0.0426(4) 0.0668(11) Uani 1 1 d . . . . .
C28 C 0.2830(9) 1.2461(7) -0.0727(7) 0.112(2) Uani 1 1 d . . . . .
H28 H 0.3830 1.1984 -0.0607 0.135 Uiso 1 1 calc R . . . .
C29 C 0.2358(15) 1.3882(9) -0.1200(8) 0.153(4) Uani 1 1 d . . . . .
H29 H 0.3028 1.4358 -0.1421 0.183 Uiso 1 1 calc R . . . .
C30 C 0.0938(15) 1.4592(7) -0.1345(6) 0.146(4) Uani 1 1 d . . . . .
H30 H 0.0625 1.5563 -0.1598 0.175 Uiso 1 1 calc R . . . .
C31 C -0.0100(12) 1.3880(7) -0.1117(9) 0.157(4) Uani 1 1 d . . . . .
H31 H -0.1098 1.4366 -0.1294 0.189 Uiso 1 1 calc R . . . .
C32 C 0.0413(8) 1.2450(6) -0.0626(7) 0.118(3) Uani 1 1 d . . . . .
H32 H -0.0249 1.1962 -0.0423 0.141 Uiso 1 1 calc R . . . .
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
C9 N1 C2 112.2(9) . . ?
C2 C1 C10 117.6(9) . . ?
C3 C1 C2 115.9(8) . . ?
C3 C1 C10 126.4(8) . . ?
C1 C2 N1 118.1(7) . . ?
C1 C2 C6 124.1(10) . . ?
C6 C2 N1 117.8(8) . . ?
C1 C3 C4 129.5(9) . . ?
C3 C4 C5 118.5(10) . . ?
C6 C5 C4 110.4(7) . . ?
C2 C6 C5 121.4(8) . . ?
C7 C6 C2 115.6(11) . . ?
C7 C6 C5 123.0(9) . . ?
C8 C7 C6 130.2(14) . . ?
C7 C8 C9 114.4(11) . . ?
N1 C9 C8 129.2(13) . . ?
C11 C10 C1 117.4(4) . . ?
C15 C10 C1 118.6(5) . . ?
C15 C10 C11 123.4(4) . . ?
O1 C11 C10 121.0(5) . . ?
O1 C11 C12 123.4(5) . . ?
C10 C11 C12 115.6(4) . . ?
C13 C12 C11 120.9(4) . . ?
C22 C12 C11 119.4(4) . . ?
C22 C12 C13 119.6(4) . . ?
C12 C13 C14 119.3(4) . . ?
C25 C13 C12 118.3(4) . . ?
C25 C13 C14 122.4(4) . . ?
C13 C14 C27 121.2(4) . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 C27 119.5(4) . . ?
C10 C15 C16 116.3(4) . . ?
C14 C15 C10 121.3(4) . . ?
C14 C15 C16 122.4(4) . . ?
C17 C16 C15 120.0(6) . . ?
C21 C16 C15 120.7(5) . . ?
C21 C16 C17 119.2(5) . . ?
C18 C17 C16 120.8(7) . . ?
C19 C18 C17 120.1(7) . . ?
C18 C19 C20 119.8(7) . . ?
C21 C20 C19 120.7(9) . . ?
C20 C21 C16 119.3(7) . . ?
C12 C22 C23 121.0(4) . . ?
C22 C23 C24 120.2(4) . . ?
C23 C24 C26 120.6(4) . . ?
C25 C24 C23 118.8(4) . . ?
C25 C24 C26 120.6(5) . . ?
C24 C25 C13 122.1(4) . . ?
C28 C27 C14 120.7(5) . . ?
C28 C27 C32 117.7(5) . . ?
C32 C27 C14 121.6(5) . . ?
C27 C28 C29 122.4(8) . . ?
C30 C29 C28 120.0(9) . . ?
C29 C30 C31 120.4(6) . . ?
C32 C31 C30 117.8(9) . . ?
C31 C32 C27 121.4(8) . . ?
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 C11 1.223(7) . ?
N1 C2 1.561(13) . ?
N1 C9 1.326(11) . ?
C1 C2 1.294(12) . ?
C1 C3 1.269(11) . ?
C1 C10 1.469(8) . ?
C2 C6 1.417(9) . ?
C3 C4 1.359(11) . ?
C4 C5 1.488(17) . ?
C5 C6 1.436(14) . ?
C6 C7 1.352(13) . ?
C7 C8 1.27(2) . ?
C8 C9 1.360(18) . ?
C10 C11 1.406(7) . ?
C10 C15 1.388(6) . ?
C11 C12 1.458(7) . ?
C12 C13 1.401(6) . ?
C12 C22 1.385(6) . ?
C13 C14 1.456(6) . ?
C13 C25 1.398(6) . ?
C14 C15 1.350(6) . ?
C14 C27 1.478(6) . ?
C15 C16 1.502(7) . ?
C16 C17 1.380(9) . ?
C16 C21 1.372(10) . ?
C17 C18 1.373(8) . ?
C18 C19 1.333(12) . ?
C19 C20 1.395(12) . ?
C20 C21 1.366(10) . ?
C22 C23 1.385(7) . ?
C23 C24 1.386(7) . ?
C24 C25 1.381(6) . ?
C24 C26 1.508(7) . ?
C27 C28 1.355(8) . ?
C27 C32 1.384(9) . ?
C28 C29 1.360(10) . ?
C29 C30 1.329(16) . ?
C30 C31 1.414(16) . ?
C31 C32 1.369(9) . ?
