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_1543157
_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         'C22 H28 N4 O4'
_chemical_formula_sum            'C22 H28 N4 O4'
_chemical_formula_weight         412.48
_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     direct
_audit_creation_date             2014-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.057(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0264(17)
_cell_length_b                   19.058(2)
_cell_length_c                   15.9395(19)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.29
_cell_measurement_theta_min      2.59
_cell_volume                     4230.6(8)
_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 0.986
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa Apex2 Duo'
_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  0.0490
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            70222
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.670
_diffrn_reflns_theta_min         1.462
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7343
_exptl_absorpt_correction_T_min  0.7116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0520 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.9691.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         9755
_refine_ls_number_restraints     446
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0520P)^2^+2.7197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7053
_reflns_number_total             9755
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00890_si_003.cif
_cod_data_source_block           mo_d041214_1_1_0m
_cod_depositor_comments
'Adding full bibliography for 1543156--1543159.cif.'
_cod_original_cell_volume        4230.5(9)
_cod_database_code               1543157
_shelxl_version_number           2014/6
_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
 N19-H19 = N5_$1-H5A_$1
 0.91 with sigma of 0.02
3. 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
4.a Ternary CH refined with riding coordinates:
 C9(H9), C31(H31)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C33(H33A,H33B), C43(H43A,H43B)
4.c Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C5(H5), C23(H23), C24(H24), C27(H27), C28(H28), C37(H37), C38(H38)
4.d Idealised Me refined as rotating group:
 C2AA(H2AA,H2AB,H2AC), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C34(H34A,
 H34B,H34C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C44(H44A,H44B,H44C)
;
_shelx_res_checksum              92000
_shelx_hkl_checksum              20504
_olex2_date_sample_data_collection 8.12.2014
_olex2_date_sample_submission    4.12.2014
_olex2_submission_original_sample_id d041214_1_1
_olex2_submission_special_instructions 'No special instructions were received'