Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration.
Andreou, Dimitrios; Kallitsakis, Michael G.; Loukopoulos, Edward; Gabriel, Catherine; Kostakis, George E.; Lykakis, Ioannis N.; The Journal of organic chemistry 83 (2018) 2104–2113; doi:10.1021/acs.joc.7b03051

data_4035016
_publ_section_title
;
 Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from
 Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2104
_journal_page_last               2113
_journal_paper_doi               10.1021/acs.joc.7b03051
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H20 Br N'
_chemical_formula_sum            'C24 H20 Br N'
_chemical_formula_weight         402.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                77.515(2)
_cell_angle_beta                 82.318(2)
_cell_angle_gamma                78.463(2)
_cell_formula_units_Z            2
_cell_length_a                   5.88570(10)
_cell_length_b                   12.0646(2)
_cell_length_c                   13.8223(3)
_cell_measurement_reflns_used    14408
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.1100
_cell_measurement_theta_min      3.5250
_cell_volume                     934.73(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type
;
Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34412
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.515
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.166
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.9617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4124
_reflns_number_total             4283
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03051_si_003.cif
_cod_data_source_block           2016ncs0772acapyb
_cod_database_code               4035016
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H003(0.022) H008(0.022) H00B(0.021) H00A(0.023) H00C(0.023)
 H00E(0.023) H00F(0.022) H00G(0.022) H00H(0.025) H00I(0.03) H00J(0.024)
 H00K(0.029) H00L(0.024) H00M(0.026) H00N(0.028) H00O(0.027) H00D(0.032)
 H00P(0.032) H00Q(0.032) H00R(0.028)
 Fixed X: H003(0.8793) H008(1.2421) H00B(0.6112) H00A(0.1593) H00C(0.0808)
 H00E(-0.0033) H00F(0.9731) H00G(0.5601) H00H(0.106) H00I(0.2991) H00J(0.627)
 H00K(0.656) H00L(0.272) H00M(-0.2604) H00N(-0.2571) H00O(0.0099) H00D(0.4026)
 H00P(0.656) H00Q(0.4463) H00R(0.8183)
 Fixed Y: H003(0.1314) H008(0.3727) H00B(0.2727) H00A(0.7769) H00C(0.7993)
 H00E(0.5139) H00F(0.5138) H00G(0.6323) H00H(0.9916) H00I(1.1471) H00J(0.8059)
 H00K(1.1323) H00L(0.8031) H00M(0.581) H00N(0.7603) H00O(0.8707) H00D(0.3483)
 H00P(0.3696) H00Q(0.4361) H00R(0.962)
 Fixed Z: H003(0.442) H008(0.4637) H00B(0.3561) H00A(0.3562) H00C(0.2488)
 H00E(0.1561) H00F(0.378) H00G(0.3864) H00H(0.3234) H00I(0.2817) H00J(0.1771)
 H00K(0.1886) H00L(0.0691) H00M(0.0354) H00N(-0.0671) H00O(-0.0496)
 H00D(0.2038) H00P(0.1651) H00Q(0.1045) H00R(0.1351)
;
_shelx_res_checksum              1240
_shelx_hkl_checksum              5366
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'