Synthesis of the 3,3'-bipyrrole scaffold from diyne.
Zhang, Wentao; Wang, Luyao; Zhou, Yufeng; Chen, Zhifang; Xiong, Heng-Ying; Zhang, Guangwu; Organic & biomolecular chemistry 23 (2025) 2463–2466; doi:10.1039/d4ob02101k

data_1573822
_publ_section_title
;
 Synthesis of the 3,3'-bipyrrole scaffold from diyne.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2463
_journal_page_last               2466
_journal_paper_doi               10.1039/d4ob02101k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C36 H36 N2'
_chemical_formula_sum            'C36 H36 N2'
_chemical_formula_weight         496.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2024-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-10-31 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.082(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.4509(12)
_cell_length_b                   9.1830(3)
_cell_length_c                   11.7236(5)
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9410
_cell_measurement_theta_min      4.1280
_cell_volume                     2774.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -103.00 -17.00   1.00    1.00    --  -33.50 -37.00  90.00   86
  2  \w    -62.00 -36.00   1.00    1.00    --  -33.50 178.00-180.00   26
  3  \w    -71.00 -17.00   1.00    1.00    --  -33.50 -57.00 -30.00   54
  4  \w     62.00 108.00   1.00    1.00    --   36.47 178.00 -30.00   46
  5  \w     70.00  97.00   1.00    1.00    --   36.47 178.00   0.00   27
  6  \w     62.00  92.00   1.00    1.00    --   36.47 178.00-180.00   30
  7  \w     12.00  54.00   1.00    1.00    --   36.47 -37.00 -90.00   42
  8  \w    -10.00  54.00   1.00    1.00    --   36.47 -57.00   0.00   64
  9  \w    -30.00   0.00   1.00    1.00    --   36.47 -37.00 -90.00   30
 10  \w     61.00  97.00   1.00    1.00    --   36.47 178.00 -60.00   36
 11  \w     41.00  97.00   1.00    3.00    --  108.00 -77.00  60.00   56
 12  \w     39.00 128.00   1.00    3.00    --  108.00 -45.00 -30.00   89
 13  \w     52.00  77.00   1.00    3.00    --  108.00-111.00   0.00   25
 14  \w    103.00 170.00   1.00    3.00    --  108.00  77.00 -30.00   67
 15  \w     84.00 110.00   1.00    3.00    --  108.00 -30.00  60.00   26
 16  \w     38.00 127.00   1.00    3.00    --  108.00 -45.00-180.00   89
 17  \w     37.00  62.00   1.00    3.00    --  108.00 -30.00  60.00   25
 18  \w    101.00 138.00   1.00    3.00    --  108.00  77.00  90.00   37
 19  \w     91.00 175.00   1.00    3.00    --  108.00   0.00-120.00   84
 20  \w     44.00  70.00   1.00    3.00    --  108.00-104.00  49.00   26
 21  \w     43.00  75.00   1.00    3.00    --  108.00   0.00-120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0094588000
_diffrn_orient_matrix_UB_12      0.0718262000
_diffrn_orient_matrix_UB_13      -0.1071733000
_diffrn_orient_matrix_UB_21      -0.0569702000
_diffrn_orient_matrix_UB_22      0.0511177000
_diffrn_orient_matrix_UB_23      -0.0615796000
_diffrn_orient_matrix_UB_31      0.0156023000
_diffrn_orient_matrix_UB_32      0.1426682000
_diffrn_orient_matrix_UB_33      0.0759238000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5549
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.430
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0872P)^2^+0.3981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1536
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2022
_reflns_number_total             2466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02101k2.cif
_cod_data_source_block           ta4151
_cod_depositor_comments
'Adding full bibliography for 1573822--1573825.cif.'
_cod_database_code               1573822
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C12H22O5N1
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              87631
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.863