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_7155180
_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 H20 B F N4 O3 S'
_chemical_formula_sum            'C26 H20 B F N4 O3 S'
_chemical_formula_weight         498.33
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-20
_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                90.00
_cell_angle_beta                 112.989(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8786(8)
_cell_length_b                   14.6539(7)
_cell_length_c                   14.7921(10)
_cell_measurement_reflns_used    3104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4006
_cell_measurement_theta_min      3.1509
_cell_volume                     2370.3(3)
_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      0.0042323000
_diffrn_orient_matrix_UB_12      -0.0480242000
_diffrn_orient_matrix_UB_13      0.0065365000
_diffrn_orient_matrix_UB_21      -0.0600959000
_diffrn_orient_matrix_UB_22      -0.0009726000
_diffrn_orient_matrix_UB_23      -0.0008558000
_diffrn_orient_matrix_UB_31      -0.0240003000
_diffrn_orient_matrix_UB_32      -0.0060862000
_diffrn_orient_matrix_UB_33      -0.0516648000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9863
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88766
_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_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.7038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3352
_reflns_number_total             4317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob01247g2.cif
_cod_data_source_block           150420_dhl507168
_cod_depositor_comments
'Adding full bibliography for 7155179--7155181.cif.'
_cod_database_code               7155180
_chemical_oxdiff_formula         'c10 h10 n2 o8 S1 B1'
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C26(H26A,H26B,H26C)
;