A Three-Step Synthesis of Tetrasubstituted NH-Pyrroles.
Reekie, Tristan A.; Donckele, Etienne J.; Manenti, Giorgio; Püntener, Salome; Trapp, Nils; Diederich, François; Organic letters 18 (2016) 2252–2255; doi:10.1021/acs.orglett.6b00890

data_1543156
_publ_section_title
;
 A Three-Step Synthesis of Tetrasubstituted NH-Pyrroles.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2252
_journal_page_last               2255
_journal_paper_doi               10.1021/acs.orglett.6b00890
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H24 N4 O4'
_chemical_formula_sum            'C20 H24 N4 O4'
_chemical_formula_weight         384.43
_chemical_name_systematic
'Diethyl 2 -(3-(4-aminophenyl)-4-cyano-5-(dimethylamino)-1H-pyrrol-2-yl)malonate'
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                108.782(3)
_cell_angle_beta                 106.051(3)
_cell_angle_gamma                94.161(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8318(6)
_cell_length_b                   10.2287(9)
_cell_length_c                   13.5191(12)
_cell_measurement_reflns_used    3887
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.75
_cell_volume                     969.70(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11055
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.677
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0489 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.9615.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.2076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3625
_reflns_number_total             4491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00890_si_004.cif
_cod_data_source_block           d030315_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1543156--1543159.cif.'
_cod_original_cell_volume        969.70(14)
_cod_database_code               1543156
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.971
_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. Restrained distances
 N5-H5
 0.91 with sigma of 0.02
 N7-H7B = N7-H7A
 0.91 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              4866
_shelx_hkl_checksum              13598
_olex2_date_sample_data_collection 2015-03-09
_olex2_date_sample_submission    2015-03-05
_olex2_submission_original_sample_id d030315_1_1
_olex2_submission_special_instructions 'No special instructions were received'