Radical-based functionalization-oriented construction: rapid assembly of azaarene-substituted highly functionalized pyrroles
Hu, Weigao; Zhan, Qiangqiang; Zhou, Hongwei; Cao, Shanshan; Jiang, Zhiyong; Chemical Science  (2021) –; doi:10.1039/D1SC01470F

data_1561346
_publ_section_title
;
 Radical-based functionalization-oriented construction: rapid assembly of
 azaarene-substituted highly functionalized pyrroles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC01470F
_journal_year                    2021
_chemical_formula_moiety         'C29 H21 F3 N2'
_chemical_formula_sum            'C29 H21 F3 N2'
_chemical_formula_weight         454.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-12 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.262(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4838(4)
_cell_length_b                   10.8493(5)
_cell_length_c                   22.4754(10)
_cell_measurement_reflns_used    1650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.3800
_cell_measurement_theta_min      3.9360
_cell_volume                     2306.16(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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    -64.00 -19.00   1.00    2.50    --  -33.50 -57.00 -60.00   45
  2  \w    -91.00 -52.00   1.00    2.50    --  -33.50 -77.00  60.00   39
  3  \w    -44.00  -5.00   1.00    2.50    --  -33.50 -77.00  60.00   39
  4  \w    -28.00  52.00   1.00    2.50    --   36.47 -57.00-120.00   80
  5  \w     68.00  95.00   1.00    2.50    --   36.47 178.00 -90.00   27
  6  \w     18.00  53.00   1.00    2.50    --   36.47  57.00-180.00   35
  7  \w     45.00  77.00   1.00    2.50    --   36.47-118.00 138.00   32
  8  \w     53.00  98.00   1.00    2.50    --   36.47  57.00 -30.00   45
  9  \w     14.00  72.00   1.00    2.50    --   36.47  37.00  90.00   58
 10  \w     74.00 102.00   1.00    2.50    --   36.47  57.00-180.00   28
 11  \w     47.00 116.00   1.00    9.00    --  108.00 -61.00  90.00   69
 12  \w     70.00 108.00   1.00    9.00    --  108.00-111.00-120.00   38
 13  \w     40.00 121.00   1.00    9.00    --  108.00 -61.00-180.00   81
 14  \w     41.00  70.00   1.00    9.00    --  108.00 -94.00 -30.00   29
 15  \w     38.00 129.00   1.00    9.00    --  108.00 -30.00-180.00   91
 16  \w    109.00 135.00   1.00    9.00    --  108.00 111.00-180.00   26
 17  \w     37.00 134.00   1.00    9.00    --  108.00 -30.00 -90.00   97
 18  \w     84.00 112.00   1.00    9.00    --  108.00-111.00  30.00   28
 19  \w     47.00  73.00   1.00    9.00    --  108.00-111.00  30.00   26
;
_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      -0.0113524000
_diffrn_orient_matrix_UB_12      0.0195842000
_diffrn_orient_matrix_UB_13      -0.0680767000
_diffrn_orient_matrix_UB_21      0.1593146000
_diffrn_orient_matrix_UB_22      -0.0265157000
_diffrn_orient_matrix_UB_23      -0.0015154000
_diffrn_orient_matrix_UB_31      -0.0321023000
_diffrn_orient_matrix_UB_32      -0.1381048000
_diffrn_orient_matrix_UB_33      -0.0093344000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.945
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0631P)^2^+0.4113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1615
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             4112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01470f2.cif
_cod_data_source_block           20200518
_cod_original_cell_volume        2306.18(17)
_cod_database_code               1561346
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4F3
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.873
_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
2. Restrained distances
 F3-F1 \\sim F3-F2 \\sim F3A-F2A \\sim F1-F2 \\sim F1A-F2A
 with sigma of 0.04
 C12-F3 \\sim C12-F3A \\sim C12-F1 \\sim C12-F1A \\sim C12-F2A \\sim C12-F2
\\sim C12-C9
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              98362
_shelx_hkl_checksum              43849
_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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.887