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_1573825
_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         'C38 H32 N2 O2'
_chemical_formula_sum            'C38 H32 N2 O2'
_chemical_formula_weight         548.65
_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     dual
_audit_creation_date             2024-12-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-28 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.268(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.2762(11)
_cell_length_b                   10.1154(3)
_cell_length_c                   12.3299(5)
_cell_measurement_reflns_used    7091
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7170
_cell_measurement_theta_min      1.7520
_cell_volume                     2938.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.142a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.878
_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    -78.00 -53.00   0.50    0.80    --  -20.24 127.00-104.00   50
  2  \w    -89.00 -64.00   0.50    0.80    --  -20.24 145.00  63.00   50
  3  \w    -42.00  62.00   0.50    0.80    --  -20.24  38.00 120.00  208
  4  \w    -25.00  55.00   0.50    0.80    --  -20.24  19.00  30.00  160
  5  \w    -21.00  17.00   0.50    0.80    --   22.51  19.00 -30.00   76
  6  \w     49.00  74.00   0.50    0.80    --   22.51-145.00  10.00   50
  7  \w     32.00  95.00   0.50    0.80    --   22.51-127.00 179.00  126
  8  \w     61.00  87.00   0.50    0.80    --   22.51  19.00 -30.00   52
  9  \w     46.00 105.00   0.50    0.80    --   22.51 178.00  90.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0136254865
_diffrn_orient_matrix_UB_12      -0.0559456841
_diffrn_orient_matrix_UB_13      -0.0357560808
_diffrn_orient_matrix_UB_21      0.0200945938
_diffrn_orient_matrix_UB_22      -0.0420017530
_diffrn_orient_matrix_UB_23      0.0443943596
_diffrn_orient_matrix_UB_31      -0.0178120638
_diffrn_orient_matrix_UB_32      -0.0046181813
_diffrn_orient_matrix_UB_33      0.0294218329
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11065
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.940
_diffrn_reflns_theta_min         1.728
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.142a (Rigaku Oxford Diffraction, 2024)
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    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0418P)^2^+1.3865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2812
_reflns_number_total             3418
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob02101k2.cif
_cod_data_source_block           202412t496f1_auto
_cod_depositor_comments
'Adding full bibliography for 1573822--1573825.cif.'
_cod_database_code               1573825
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         CHNOCl
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.989
_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:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              58181
_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 1.279
_oxdiff_exptl_absorpt_empirical_full_min 0.786