Simple and efficient one-pot multi-step strategy for the synthesis of 2-substituted (1,2,5-triarylpyrrolo[3,2-c]pyridin-3-yl)-N-arylacetamide derivatives in water.
Li, Chunmei; Yang, Xiaopeng; Zhang, Furen; Qi, Chenze; Shen, Zhenlu; Organic & biomolecular chemistry 19 (2021) 2526–2532; doi:10.1039/d1ob00190f

data_7157896
_publ_section_title
;
 Simple and efficient one-pot multi-step strategy for the synthesis of
 2-substituted (1,2,5-triarylpyrrolo[3,2-c]pyridin-3-yl)-N-arylacetamide
 derivatives in water.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2526
_journal_page_last               2532
_journal_paper_doi               10.1039/d1ob00190f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C36 H30 Br N3 O2, C H2 Cl2'
_chemical_formula_sum            'C37 H32 Br Cl2 N3 O2'
_chemical_formula_weight         701.46
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-16 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.450(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0371(4)
_cell_length_b                   18.7861(4)
_cell_length_c                   13.4704(3)
_cell_measurement_reflns_used    16515
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1200
_cell_measurement_theta_min      3.4000
_cell_volume                     3258.79(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -59.00  22.00   0.50    0.05    --  -47.82  59.00 -54.00  162
  2  \w     51.00  76.00   0.50    0.05    --   47.82  59.00 -54.00   50
  3  \w     96.00 177.00   0.50    0.16    --  104.75  59.00 -54.00  162
  4  \w    130.00 156.00   0.50    0.16    --  104.75  77.00  30.00   52
  5  \w     93.00 176.00   0.50    0.16    --  104.75  30.00 -90.00  166
  6  \w     88.00 114.00   0.50    0.16    --  104.75  77.00  30.00   52
  7  \w     36.00  85.00   0.50    0.16    --  104.75 -59.00 165.00   98
  8  \w     32.00 109.00   0.50    0.16    --  104.75 -94.00 150.00  154
  9  \w     33.00 107.00   0.50    0.16    --  104.75 -94.00   0.00  148
 10  \w    -22.00  63.00   0.50    0.05    --   47.82 -59.00 165.00  170
 11  \w    -76.00 -31.00   0.50    0.16    -- -102.00  59.00 -54.00   90
 12  \w    -99.00 -31.00   0.50    0.16    -- -102.00  45.00 150.00  136
 13  \w   -119.00 -47.00   0.50    0.05    --  -47.82 -59.00 165.00  144
 14  \w   -117.00 -72.00   0.50    0.05    --  -47.82-125.00 -60.00   90
 15  \w   -114.00 -83.00   0.50    0.05    --  -47.82-125.00 -90.00   62
 16  \w   -166.00 -90.00   0.50    0.16    -- -102.00 -61.00-120.00  152
 17  \w   -172.00-146.00   0.50    0.16    -- -102.00 -59.00 165.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1102303000
_diffrn_orient_matrix_UB_12      0.0319219000
_diffrn_orient_matrix_UB_13      0.0420006000
_diffrn_orient_matrix_UB_21      -0.0327317000
_diffrn_orient_matrix_UB_22      0.0481108000
_diffrn_orient_matrix_UB_23      -0.1007248000
_diffrn_orient_matrix_UB_31      -0.0332090000
_diffrn_orient_matrix_UB_32      0.0581848000
_diffrn_orient_matrix_UB_33      0.0601933000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22273
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.612
_diffrn_reflns_theta_min         3.432
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.767
_refine_diff_density_min         -1.676
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0604
_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^)+(0.1070P)^2^+7.4875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1770
_refine_ls_wR_factor_ref         0.1867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6102
_reflns_number_total             6542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00190f2.cif
_cod_data_source_block           20190529h
_cod_depositor_comments          'Adding full bibliography for 7157896.cif.'
_cod_original_cell_volume        3258.79(15)
_cod_database_code               7157896
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1N1O1Br1
_shelx_estimated_absorpt_t_max   0.719
_shelx_estimated_absorpt_t_min   0.620
_diffrn_oxdiff_digest_frames
;
01d9689d31519a3b373d4ce31b8069ac6b00130d931
;
_diffrn_oxdiff_digest_hkl
;
01c2873fcc5dad719ab94e7e289f645d930d5b
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C24(H24), C25(H25), C27(H27), C32(H32), C33(H33),
  C34(H34), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              59334
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.787