Selective reduction of 1,5-diazacyclooctatetraenes: synthesis and structures of aromatic diazacyclooctatetraenyl dianions and 2,6-bipyrrolinyl dianionic Co(II) complex
Huang, Zhe; Tan, Genwen; Chen, Chao; Zhang, Wen-Xiong; Wang, Xinping; Xi, Zhenfeng; Chemical Communications  (2019) –; doi:10.1039/C9CC00075E

data_7122938
_publ_section_title
;
 Selective reduction of 1,5-diazacyclooctatetraenes: synthesis and
 structures of aromatic diazacyclooctatetraenyl dianions and
 2,6-bipyrrolinyl dianionic Co(II) complex
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00075E
_journal_year                    2019
_chemical_formula_moiety         'C19 H29 K N O3'
_chemical_formula_sum            'C19 H29 K N O3'
_chemical_formula_weight         358.55
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-08-25 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                116.878(3)
_cell_angle_beta                 104.713(3)
_cell_angle_gamma                98.473(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3241(3)
_cell_length_b                   10.8056(3)
_cell_length_c                   11.7204(4)
_cell_measurement_reflns_used    12632
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.2880
_cell_measurement_theta_min      4.0220
_cell_volume                     970.58(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9975
_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    -33.00  88.00   0.50    0.50    --   -0.90  19.00 -90.00  242
  2  \w     35.00  76.00   0.50    0.50    --   -0.90  19.00  90.00   82
  3  \w     22.00  87.00   0.50    0.50    --   -0.90  19.00 150.00  130
  4  \w     -8.00  34.00   0.50    0.50    --    1.50 -82.00  60.00   84
  5  \w    -22.00  32.00   0.50    0.50    --   -0.90 -82.00 -60.00  108
  6  \w      9.00  34.00   0.50    0.50    --    1.50 -82.00-150.00   50
  7  \w    -33.00  28.00   0.50    0.50    --   -0.90  19.00  90.00  122
  8  \w    -26.00  57.00   0.50    0.50    --   -0.90  57.00 -60.00  166
  9  \w    -24.00  34.00   0.50    0.50    --   -0.90  38.00   0.00  116
 10  \w    -31.00  -4.00   0.50    0.50    --   -0.90  19.00 150.00   54
 11  \w    -19.00  26.00   0.50    0.50    --    1.50 -57.00 150.00   90
 12  \w    -28.00  34.00   0.50    0.50    --    1.50 -82.00 120.00  124
 13  \w    -71.00 -46.00   0.50    0.50    --    1.50 -57.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0359981000
_diffrn_orient_matrix_UB_12      0.0362651000
_diffrn_orient_matrix_UB_13      0.0724681000
_diffrn_orient_matrix_UB_21      0.0640422000
_diffrn_orient_matrix_UB_22      0.0416378000
_diffrn_orient_matrix_UB_23      -0.0026791000
_diffrn_orient_matrix_UB_31      -0.0376579000
_diffrn_orient_matrix_UB_32      0.0540171000
_diffrn_orient_matrix_UB_33      0.0067013000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28633
_diffrn_reflns_theta_full        27.4806
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.69
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2268
_exptl_crystal_description       block
_exptl_crystal_F_000             386.5888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.6381
_refine_diff_density_min         -0.6907
_refine_diff_density_rms         0.0544
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             5.5238
_refine_ls_goodness_of_fit_ref   1.0417
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     222
_refine_ls_number_reflns         4424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0417
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.5890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4001
_reflns_number_total             4424
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9cc00075e2.cif
_cod_data_source_block           exp_147
_cod_original_cell_volume        970.57(7)
_cod_database_code               7122938
_chemical_oxdiff_formula         'C H O N K'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C16(H16a,H16b), C17(H17a,H17b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C7(H7a,H7b,H7c), C6(H6a,H6b,H6c), C14(H14a,H14b,H14c),
 C19(H19a,H19b,H19c)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.400
_oxdiff_exptl_absorpt_empirical_full_min 0.769