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_1512229
_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_absolute_configuration unk
_chemical_formula_moiety         'C42 H50 N4'
_chemical_formula_sum            'C42 H50 N4'
_chemical_formula_weight         610.86
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3049(7)
_cell_length_b                   13.3049(7)
_cell_length_c                   21.044(2)
_cell_measurement_reflns_used    1777
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      25.0710
_cell_measurement_theta_min      4.4600
_cell_volume                     3725.2(4)
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.7699
_diffrn_measurement_details
;
  1 omega    0.00   46.00   1.0000   15.1400
omega____ theta____ kappa____ phi______ frames
    -       11.5565   38.0000    0.0000 46

  2 omega  -32.00   39.00   1.0000   15.1400
omega____ theta____ kappa____ phi______ frames
    -       11.5565  -19.0000  150.0000 71
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0375914000
_diffrn_orient_matrix_UB_12      -0.0151073000
_diffrn_orient_matrix_UB_13      -0.0219485000
_diffrn_orient_matrix_UB_21      0.0117880000
_diffrn_orient_matrix_UB_22      -0.0417009000
_diffrn_orient_matrix_UB_23      0.0196257000
_diffrn_orient_matrix_UB_31      -0.0358394000
_diffrn_orient_matrix_UB_32      -0.0294976000
_diffrn_orient_matrix_UB_33      -0.0165309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5204
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09640
_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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0708
_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^)+(0.1204P)^2^+1.8876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2086
_reflns_number_gt                2709
_reflns_number_total             3463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401878q_si_004.cif
_cod_data_source_block           13apr23a
_cod_original_cell_volume        3725.3(4)
_cod_database_code               1512229
_chemical_oxdiff_formula         'C38 H40 N4'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H3 of C3, H4 of C4, H5 of C5, H6 of C6, H7 of C7, H9 of C9, H10 of C10, H11
  of C11, H12 of C12, H13 of C13, {H16A,H16B} of C16, {H17A,H17B,H17C,H17D} of
  C17, {H19A,H19B} of C19, {H20A,H20B} of C20
 At 1.5 times of:
  {H18A,H18B,H18C} of C18, {H21A,H21B,H21C} of C21, {H18D,H18E,H18F} of C181
2. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C17)
3. Others
 Sof(H17A)=Sof(H17B)=1-Sof(H17B)=1-Sof(H17B)=1-Sof(H17B)=1-Sof(H17B)=1-
 Sof(H17B)=1-Sof(H17B)=Sof(C181)=Sof(H18D)=Sof(H18E)=Sof(H18F)
4.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B)
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)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C181(H18D,H18E,H18F)
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