Preparation of 3-azoindoles and 3-hydrazonoindolin-2-imines as well as their applications as NNO pincer ligands for boron.
Ding, Hualong; Peng, Zhixing; Wang, Jinjin; Lu, Ping; Wang, Yanguang; Organic & biomolecular chemistry 14 (2016) 7114–7118; doi:10.1039/c6ob01247g

data_7155179
_publ_section_title
;
 Preparation of 3-azoindoles and 3-hydrazonoindolin-2-imines as well as
 their applications as NNO pincer ligands for boron.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7114
_journal_page_last               7118
_journal_paper_doi               10.1039/c6ob01247g
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C26 H22 N4 O3 S'
_chemical_formula_sum            'C26 H22 N4 O3 S'
_chemical_formula_weight         470.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2016-06-22 deposited with the CCDC.
2016-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                77.492(6)
_cell_angle_beta                 79.130(6)
_cell_angle_gamma                85.572(6)
_cell_formula_units_Z            2
_cell_length_a                   8.2558(6)
_cell_length_b                   10.1328(7)
_cell_length_c                   13.9082(11)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5122
_cell_measurement_theta_min      3.1557
_cell_volume                     1114.68(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0448165000
_diffrn_orient_matrix_UB_12      0.0530650000
_diffrn_orient_matrix_UB_13      -0.0338585000
_diffrn_orient_matrix_UB_21      0.0195445000
_diffrn_orient_matrix_UB_22      0.0233089000
_diffrn_orient_matrix_UB_23      0.0408449000
_diffrn_orient_matrix_UB_31      0.0726229000
_diffrn_orient_matrix_UB_32      -0.0423014000
_diffrn_orient_matrix_UB_33      -0.0013939000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7209
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^+0.2496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                2928
_reflns_number_total             4054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01247g2.cif
_cod_data_source_block           140928_dhl499105_2r
_cod_depositor_comments
'Adding full bibliography for 7155179--7155181.cif.'
_cod_original_cell_volume        1114.69(14)
_cod_database_code               7155179
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1'
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C23(H23), C15(H15), C19(H19), C5(H5), C1(H1A), C20(H20), C24(H24),
 C26(H26), C12(H12), C25(H25), C13(H13), C4(H4), C2(H2), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C7(H7A,H7B,H7C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;