Synthesis of 3,4-dihydroisoquinolin-1(2H)-one derivatives and their antioomycete activity against the phytopathogen Pythium recalcitrans
Wang, Delong; Li, Min; Li, Jing; Fang, Yali; Zhang, Zhijia; RSC Advances 13 (2023) 10523–10541; doi:10.1039/D3RA00855J

data_7246556
_publ_section_title
;
 Synthesis of 3,4-dihydroisoquinolin-1(2H)-one derivatives and their
 antioomycete activity against the phytopathogen Pythium recalcitrans
;
_journal_issue                   16
_journal_name_full               'RSC Advances'
_journal_page_first              10523
_journal_page_last               10541
_journal_paper_doi               10.1039/D3RA00855J
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C21 H17 N O4'
_chemical_formula_sum            'C21 H17 N O4'
_chemical_formula_weight         347.36
_chemical_name_systematic        isoq
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2022-06-22 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.6980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.61550(10)
_cell_length_b                   13.21640(10)
_cell_length_c                   15.09880(10)
_cell_measurement_reflns_used    14765
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.1280
_cell_measurement_theta_min      2.9590
_cell_volume                     1694.67(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     32.00 119.00   0.50    0.05    --   46.67  57.00  30.00  174
  2  \w     51.00 115.00   0.50    0.05    --   46.67  57.00  60.00  128
  3  \w     83.00 178.00   0.50    0.05    --  106.51  77.00 -30.00  190
  4  \w     91.00 117.00   0.50    0.05    --  106.51  30.00 120.00   52
  5  \w     90.00 178.00   0.50    0.05    --  106.51  15.00 150.00  176
  6  \w    134.00 178.00   0.50    0.05    --  106.51  30.00 120.00   88
  7  \w    -68.00 -28.00   0.50    0.05    --  -99.00  61.00   0.00   80
  8  \w    -67.00 -32.00   0.50    0.05    --  -99.00  61.00 -30.00   70
  9  \w    -66.00 -30.00   0.50    0.05    --  -99.00  61.00-120.00   72
 10  \w   -112.00 -26.00   0.50    0.05    --  -99.00 125.00 -30.00  172
 11  \w   -112.00 -79.00   0.50    0.05    --  -99.00 125.00 120.00   66
 12  \w    -73.00 -26.00   0.50    0.05    --  -99.00 125.00 120.00   94
 13  \w    -80.00 -28.00   0.50    0.05    --  -99.00  92.00  39.00  104
 14  \w    -50.00 -13.00   0.50    0.05    --  -46.67  92.00  39.00   74
 15  \w    -10.00  18.00   0.50    0.05    --  -46.67  92.00  39.00   56
 16  \w     88.00 138.00   0.50    0.05    --  106.51  92.00  39.00  100
 17  \w    -26.00  45.00   0.50    0.05    --   46.67 -37.00 -60.00  142
 18  \w     34.00  75.00   0.50    0.05    --  106.51 -61.00  60.00   82
 19  \w     34.00 105.00   0.50    0.05    --  106.51 -94.00  30.00  142
 20  \w     34.00 109.00   0.50    0.05    --  106.51-125.00 -60.00  150
 21  \w     34.00 105.00   0.50    0.05    --  106.51 -92.00 -73.00  142
 22  \w     54.00 105.00   0.50    0.05    --  106.51 -94.00-180.00  102
 23  \w    -24.00  73.00   0.50    0.05    --   46.67 -92.00 -73.00  194
 24  \w   -168.00 -84.00   0.50    0.05    --  -99.00 -45.00-150.00  168
 25  \w   -141.00-115.00   0.50    0.05    --  -99.00 -92.00 -73.00   52
 26  \w   -172.00 -79.00   0.50    0.05    --  -99.00 -77.00 -60.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430643000
_diffrn_orient_matrix_UB_12      -0.1023145000
_diffrn_orient_matrix_UB_13      -0.0466666000
_diffrn_orient_matrix_UB_21      -0.1745301000
_diffrn_orient_matrix_UB_22      0.0315898000
_diffrn_orient_matrix_UB_23      -0.0192444000
_diffrn_orient_matrix_UB_31      0.0243544000
_diffrn_orient_matrix_UB_32      0.0460487000
_diffrn_orient_matrix_UB_33      -0.0903742000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0087
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16914
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.463
_diffrn_reflns_theta_min         4.474
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0380
_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/[\s^2^(Fo^2^)+(0.0521P)^2^+0.7572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3340
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ra00855j2.cif
_cod_data_source_block           1_auto
_cod_database_code               7246556
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              52609
_shelx_hkl_checksum              68780
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.663