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_1543158
_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_absolute_configuration unk
_chemical_formula_moiety         'C20 H23 N3 O4 S'
_chemical_formula_sum            'C20 H23 N3 O4 S'
_chemical_formula_weight         401.47
_chemical_name_systematic
'diethyl 2-(5-amino-4-cyano-3-(4-(dimethylamino)phenyl)thiophen-2-yl)malonate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5140(3)
_cell_length_b                   22.5000(7)
_cell_length_c                   11.0395(4)
_cell_measurement_reflns_used    7295
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.66
_cell_volume                     2020.71(12)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Apex2 Duo (Mo)'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16283
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         1.810
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0430 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.9443.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.59(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         9026
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0415P)^2^+0.2830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.950
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                8318
_reflns_number_total             9026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00890_si_002.cif
_cod_data_source_block           mo_d290315_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1543156--1543159.cif.'
_cod_database_code               1543158
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.41(7) 0.59(7)
2. 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, All N(H,H) groups
3. Restrained distances
 N3-H3B
 0.86 with sigma of 0.01
 N3-H3A
 0.86 with sigma of 0.01
 N6-H6B
 0.86 with sigma of 0.01
 N6-H6A
 0.86 with sigma of 0.01
 H3B-H3A
 1.4 with sigma of 0.03
 H6B-H6A
 1.4 with sigma of 0.03
4.a Ternary CH refined with riding coordinates:
 C2(H2), C27(H27)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C29(H29A,H29B), C32(H32A,H32B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C17(H17), C18(H18), C22(H22), C23(H23), C37(H37), C38(H38)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C16(H16A,H16B,
 H16C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C36(H36A,
 H36B,H36C)
;
_shelx_res_checksum              38961
_shelx_hkl_checksum              29750
_olex2_date_sample_data_collection 2015-04-09
_olex2_date_sample_submission    2015-03-31
_olex2_submission_original_sample_id d290315_1_1
_olex2_submission_special_instructions 'No special instructions were received'