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_1543159
_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 H22 N4 O6'
_chemical_formula_sum            'C20 H22 N4 O6'
_chemical_formula_weight         414.41
_chemical_name_systematic
'Diethyl 2-(4-cyano-5-(dimethylamino)-3-(4-nitrophenyl)-1H-pyrrol-2-yl)malonate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90
_cell_angle_beta                 101.215(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5426(6)
_cell_length_b                   13.1663(9)
_cell_length_c                   16.2954(10)
_cell_measurement_reflns_used    2831
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.67
_cell_volume                     2008.3(2)
_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    'XS (Sheldrick, 2008)'
_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 0.999
_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  0.0528
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17387
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.176
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0578 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.9230.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4603
_refine_ls_number_restraints     328
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0515P)^2^+0.2271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             4603
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00890_si_005.cif
_cod_data_source_block           d040315_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1543156--1543159.cif.'
_cod_database_code               1543159
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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
 O3-C12 \\sim O3A-C12
 with sigma of 0.02
 O3-C2 \\sim O3A-C2A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O3A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 1-FVAR(1)
 Sof(O3)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C24(H24)
6.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C2(H2A,H2B), C2A(H2AA,H2AB)
6.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C20(H20), C21(H21), C23(H23)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C3(H3A,H3B,
 H3C), C3A(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              88873
_shelx_hkl_checksum              62724
_olex2_date_sample_data_collection 2015-03-09
_olex2_date_sample_submission    2015-03-05
_olex2_submission_original_sample_id d040315_1_1
_olex2_submission_special_instructions 'No special instructions were received'