Crystal Structure of 5-Methoxyindirubin 3′-Oxime
NAKAMURA, Niina; ICHIMARU, Yoshimi; KATO, Koichi; SANO, Makoto; KUROSAKI, Hiromasa; HAYASHI, Kazuhiko; MIYAIRI, Shinichi; X-ray Structure Analysis Online 36 (2020) 47–48; doi:10.2116/xraystruct.36.47

data_1559710
_publ_section_title
;
 Crystal Structure of 5-Methoxyindirubin 3&#x2032;-Oxime
;
_journal_issue                   0
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              47
_journal_page_last               48
_journal_paper_doi               10.2116/xraystruct.36.47
_journal_volume                  36
_journal_year                    2020
_chemical_formula_moiety         'C17 H13 N3 O3, C H2.83 O0.33, 0.17(H O)'
_chemical_formula_sum            'C18 H16 N3 O3.5'
_chemical_formula_weight         330.34
_chemical_name_systematic
(2'Z,3'E)-3'-(Hydroxyimino)-5-methoxy-[2',3-biindolinylidene]-2-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.324(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0352(4)
_cell_length_b                   5.55140(10)
_cell_length_c                   17.2061(4)
_cell_measurement_reflns_used    3303
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      67.9060
_cell_measurement_theta_min      5.1970
_cell_volume                     1506.85(6)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7065
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.389
_diffrn_reflns_theta_min         5.226
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       needle
_exptl_crystal_F_000             692
_exptl_crystal_preparation
'Y. ichimaru, T. Fujii, H. Saito, M. Sano, T. uchiyama, S. Miyairi, (2017), Bioorg Med Chem, 4665-4676.'
_exptl_crystal_recrystallization_method 'See Prepation Reference'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0832P)^2^+0.4771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2309
_reflns_number_total             2753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            36_47_1.txt
_cod_data_source_block           20XL015_NN
_cod_original_formula_sum        'C18 H16 N3 O3.50'
_cod_database_code               1559710
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O20B)=Sof(H20D)=0.5*(1-FVAR(2))
 Sof(O20A)=Sof(H20C)=0.5*FVAR(2)
 Fixed Sof: C20(0.5) H20A(0.5) H20B(0.5) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
3.a Riding coordinates:
 O20A(H20C), O20B(H20D)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), C4(H4), C6(H6), C7(H7), C12(H12), C15(H15), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C21(H21A,H21B,H21C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              75977
_shelx_hkl_checksum              37379
_olex2_date_sample_data_collection 2020-06-12
_olex2_date_sample_submission    2020-07-07
_olex2_exptl_crystal_mounting_method
'Crystal mounting utilized MiTiGen Dual-Thichness MicroLoops [LD]'
_olex2_submission_original_sample_id '5-Methoxyindirubin 3'-oxime _NN-35-1'
_olex2_submission_special_instructions 'No special instructions were received'