Diazo Compounds as Electrophiles To React with 1,4-Dilithio-1,3-dienes: Efficient Synthesis of 1-Imino-pyrrole Derivatives.
Zhan, Ming; Zhang, Shaoguang; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic letters 15 (2013) 4182–4185; doi:10.1021/ol401878q

data_1512230
_publ_section_title
;
 Diazo Compounds as Electrophiles To React with 1,4-Dilithio-1,3-dienes:
 Efficient Synthesis of 1-Imino-pyrrole Derivatives.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4182
_journal_page_last               4185
_journal_paper_doi               10.1021/ol401878q
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C54 H72 Cl3 Li N4 O3 Zn2'
_chemical_formula_sum            'C54 H72 Cl3 Li N4 O3 Zn2'
_chemical_formula_weight         1069.19
_chemical_name_systematic
;
 ? 
;
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-05-11
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                98.104(4)
_cell_angle_beta                 105.226(4)
_cell_angle_gamma                93.471(4)
_cell_formula_units_Z            2
_cell_length_a                   12.6665(5)
_cell_length_b                   13.2379(6)
_cell_length_c                   16.9687(10)
_cell_measurement_reflns_used    8901
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      28.6850
_cell_measurement_theta_min      3.3850
_cell_volume                     2703.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.8438
_diffrn_measurement_details
;
  1 omega  -62.00   34.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -       11.5565  -57.0000 -120.0000 96

  2 omega   73.00  100.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -       11.5565 -178.0000  120.0000 27

  3 omega  -61.00    1.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -       11.5565  -57.0000  150.0000 62

  4 omega  -22.00   25.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -       11.5565   77.0000    0.0000 47

  5 omega   34.00   89.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -       11.5565   77.0000    0.0000 55

  6 omega   16.00   41.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -       11.5565  -57.0000  150.0000 25

  7 omega    0.00   25.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -      -12.3378  -99.0000    0.0000 25

  8 omega -102.00  -57.00   1.0000    5.9600
omega____ theta____ kappa____ phi______ frames
    -      -12.3378 -178.0000   30.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0125391000
_diffrn_orient_matrix_UB_12      -0.0110826000
_diffrn_orient_matrix_UB_13      0.0409464000
_diffrn_orient_matrix_UB_21      -0.0564439000
_diffrn_orient_matrix_UB_22      -0.0008680000
_diffrn_orient_matrix_UB_23      -0.0011791000
_diffrn_orient_matrix_UB_31      -0.0077770000
_diffrn_orient_matrix_UB_32      -0.0532581000
_diffrn_orient_matrix_UB_33      -0.0158071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24187
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         10650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0504P)^2^+1.8422P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                8437
_reflns_number_total             10650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401878q_si_005.cif
_cod_data_source_block           13may06c
_cod_database_code               1512230
_chemical_oxdiff_formula         'C42 H38 N4 Zn'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3 of C3, H11 of C11, H12 of C12, H13 of C13, {H21A,H21B} of C21, {H22A,
  H22B} of C22, {H24A,H24B} of C24, {H25A,H25B} of C25, {H27A,H27B} of C27,
  {H28A,H28B} of C28, H32 of C32, H33 of C33, H34 of C34, H35 of C35, H36 of
  C36, H38 of C38, H39 of C39, H40 of C40, H41 of C41, H42 of C42, {H43A,H43B}
  of C43, {H44A,H44B} of C44, {H45A,H45B} of C45, {H46A,H46B} of C46, {H47A,
  H47B} of C47, {H48A,H48B} of C48, {H49A,H49B} of C49, {H50A,H50B} of C50,
  {H51A,H51B} of C51, {H52A,H52B} of C52, {H53A,H53B} of C53, {H54A,H54B} of
  C54, {H12A,H12B} of C127, {H12C,H12D} of C128, H4 of C4, H5 of C5, H6 of C6,
  {H18A,H18B} of C18, {H19A,H19B} of C19, H7 of C7, H9 of C9, H10 of C10, {H15A,
  H15B} of C151, {H15C,H15D} of C152, {H15E,H15F} of C153, {H15G,H15H} of C154
 At 1.5 times of:
  {H23A,H23B,H23C} of C23, {H26A,H26B,H26C} of C26, {H29A,H29B,H29C} of C29,
  {H12E,H12F,H12G} of C129, {H20A,H20B,H20C} of C20
2. Uiso/Uaniso restraints and constraints
Uanis(C51) = Uanis(C52)
Uanis(C50) = Uanis(C49)
Uanis(C151) = Uanis(C154)
3. Others
 1-Sof(H27A)=1-Sof(H27A)=1-Sof(H27A)=1-Sof(H27A)=1-Sof(H27A)=1-Sof(H27A)=1-
 Sof(H27A)=1-Sof(H27A)=1-Sof(H27A)=1-Sof(H27A)=Sof(C127)=Sof(H12A)=Sof(H12B)=
 Sof(C128)=Sof(H12C)=Sof(H12D)=Sof(C129)=Sof(H12E)=Sof(H12F)=Sof(H12G)
 1-Sof(H51A)=1-Sof(H51A)=1-Sof(H51A)=Sof(C52)=Sof(H52A)=Sof(H52B)=1-Sof(H51A)=
 1-Sof(H51A)=1-Sof(H51A)=1-Sof(H51A)=1-Sof(H51A)=1-Sof(H51A)=Sof(C151)=
 Sof(H15A)=Sof(H15B)=Sof(C152)=Sof(H15C)=Sof(H15D)=1-Sof(H51A)=1-Sof(H51A)=1-
 Sof(H51A)=Sof(C154)=Sof(H15G)=Sof(H15H)
4.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,
 H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B),
  C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,
 H53B), C54(H54A,H54B), C127(H12A,H12B), C128(H12C,H12D), C151(H15A,H15B),
 C152(H15C,H15D), C153(H15E,H15F), C154(H15G,H15H)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C38(H38), C39(H39),
  C40(H40), C41(H41), C42(H42)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C29(H29A,H29B,
 H29C), C129(H12E,H12F,H12G)
;