'One pot' regiospecific synthesis of polysubstituted pyrroles from benzylamines and ynones under metal free conditions
Jinhai Shen; Guolin Cheng; Xiuling Cui; Chem.Commun. 49 (2013) 10641–; doi:10.1039/c3cc43844a

data_7109999
_publ_section_title
;
 'One pot' regiospecific synthesis of polysubstituted pyrroles from
 benzylamines and ynones under metal free conditions
;
_journal_name_full               Chem.Commun.
_journal_page_first              10641
_journal_paper_doi               10.1039/c3cc43844a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H19 N'
_chemical_formula_sum            'C23 H19 N'
_chemical_formula_weight         309.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-23
_audit_creation_method
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  Olex2 1.1
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5579(6)
_cell_length_b                   12.3380(10)
_cell_length_c                   18.5927(12)
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      23.7510
_cell_measurement_theta_min      3.4640
_cell_volume                     1733.8(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.7128
_diffrn_measurement_details
;
  1 omega  -10.00   17.00   1.0000    6.9700
omega____ theta____ kappa____ phi______ frames
    -      -17.2885  -99.0000 -150.0000 27

  2 omega  -33.00    1.00   1.0000    6.9700
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -19.0000 -120.0000 34

  3 omega    4.00   64.00   1.0000    6.9700
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -19.0000 -120.0000 60

  4 omega   -7.00   19.00   1.0000    6.9700
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -57.0000  -30.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0904229000
_diffrn_orient_matrix_UB_12      -0.0153540000
_diffrn_orient_matrix_UB_13      -0.0020149000
_diffrn_orient_matrix_UB_21      0.0199591000
_diffrn_orient_matrix_UB_22      0.0490867000
_diffrn_orient_matrix_UB_23      -0.0181071000
_diffrn_orient_matrix_UB_31      0.0160179000
_diffrn_orient_matrix_UB_32      0.0255254000
_diffrn_orient_matrix_UB_33      0.0335140000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4636
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96021
_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_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -8(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1548
_reflns_number_gt                2195
_reflns_number_total             3014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43844a.txt
_cod_data_source_block           4ab
_cod_depositor_comments
;

2018-01-31
Z value and formula changed from original absurd values
                 miguel
;
_cod_original_cell_volume        1733.7(2)
_cod_original_formula_moiety     '0.03(C92 H76 N4)'
_cod_original_formula_sum        'C8.25 H8.25 N8.25 O8.25'
_cod_original_formula_units_Z    33
_cod_original_formula_weight     354.98
_cod_database_code               7109999
_chemical_oxdiff_formula         C1H1N1O1
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32