KI/TBHP-promoted [3 + 2] cycloaddition of pyrrolo[1,2-a]quinoxalines and N-arylsulfonylhydrazones.
Yang, Zhen; He, Jing; Wei, Yueting; Li, Weiwei; Liu, Ping; Organic & biomolecular chemistry 18 (2020) 3360–3366; doi:10.1039/d0ob00494d

data_7157465
_publ_section_title
;
 KI/TBHP-promoted [3 + 2] cycloaddition of pyrrolo[1,2-a]quinoxalines and
 N-arylsulfonylhydrazones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3360
_journal_page_last               3366
_journal_paper_doi               10.1039/d0ob00494d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C26 H22 N4 O2 S'
_chemical_formula_sum            'C26 H22 N4 O2 S'
_chemical_formula_weight         454.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-22 deposited with the CCDC.	2020-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5618(5)
_cell_length_b                   20.0595(10)
_cell_length_c                   20.7439(10)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.405
_cell_measurement_theta_min      2.256
_cell_volume                     4811.0(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            49632
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.211
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1031 before and 0.0748 after correction. The Ratio of minimum to maximum transmission is 0.9080. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.628
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
TITL ww_a.res in Pca2(1)
CELL   11.5618   20.0595   20.7439     90.00     90.00     90.00
SPGR Pca21
C101 0.829 0.702 0.781 !      15.95 eA-3
C102 0.360 0.197 0.609 !      14.85 eA-3
C103 0.985 0.702 0.667 !      14.16 eA-3
C104 0.517 0.196 0.715 !      13.86 eA-3
C105 0.220 0.891 0.824 !      12.65 eA-3
C106 0.563 0.667 0.177 !      12.50 eA-3
C107 0.905 0.828 0.716 !      12.26 eA-3
C108 0.189 0.852 0.305 !       5.36 eA-3
C109 0.312 0.884 0.776 !       5.33 eA-3
C110 0.547 0.733 0.482 !       5.18 eA-3
C111 0.658 0.106 0.072 !       5.14 eA-3
C112 0.312 0.954 0.913 !       4.84 eA-3
C113 0.029 0.257 0.138 !       4.79 eA-3
C114 0.204 0.861 0.026 !       4.68 eA-3
C115 0.236 0.794 0.095 !       4.57 eA-3
C116 0.311 0.857 0.622 !       4.44 eA-3
C117 0.750 0.115 0.898 !       4.42 eA-3
C118 0.860 0.831 0.906 !       4.37 eA-3
C119 0.221 0.991 0.955 !       4.24 eA-3
C120 0.406 0.955 0.585 !       4.18 eA-3
C121 0.562 0.013 0.823 !       4.11 eA-3
C122 0.142 0.969 0.973 !       3.97 eA-3
C123 0.550 0.750 0.229 !       3.94 eA-3
C124 0.250 0.821 0.508 !       3.76 eA-3
C125 0.890 0.838 0.032 !       3.75 eA-3
C126 0.579 0.940 0.016 !       3.73 eA-3
C127 0.187 0.909 0.953 !       3.69 eA-3
C128 0.079 0.203 0.459 !       3.49 eA-3
C129 0.313 0.107 0.903 !       3.29 eA-3
C130 0.859 0.835 0.227 !       3.15 eA-3
C131 0.656 0.037 0.805 !       3.13 eA-3
C132 0.216 0.988 0.752 !       3.01 eA-3
C133 0.904 0.929 0.243 !       2.93 eA-3
C134 0.874 0.886 0.023 !       2.85 eA-3
C135 0.140 1.002 0.018 !       2.84 eA-3
C136 0.220 0.010 0.260 !       2.83 eA-3
C137 0.688 0.946 0.731 !       2.71 eA-3
C138 0.483 0.040 0.539 !       2.65 eA-3
C139 0.423 0.081 0.292 !       2.64 eA-3
C140 0.328 0.096 0.017 !       2.63 eA-3
C141 0.203 0.070 0.456 !       2.58 eA-3
C142 0.845 0.940 0.946 !       2.56 eA-3
C143 0.065 0.148 0.736 !       2.53 eA-3
C144 0.235 0.079 0.224 !       2.52 eA-3
C145 0.564 0.014 0.132 !       2.50 eA-3
C146 0.486 0.962 0.641 !       2.49 eA-3
C147 0.062 0.915 0.580 !       2.37 eA-3
C148 0.923 0.720 0.647 !       2.33 eA-3
C149 0.689 1.002 0.440 !       2.17 eA-3
C150 0.578 0.993 0.038 !       2.15 eA-3
C151 0.420 0.979 0.539 !       2.13 eA-3
C152 0.481 0.024 0.645 !       2.00 eA-3
C153 0.078 0.296 0.437 !       2.00 eA-3
C154 0.472 0.078 0.571 !       1.96 eA-3
C155 0.737 0.222 0.474 !       1.93 eA-3
C156 0.237 0.801 0.968 !       1.82 eA-3
C157 0.626 0.907 0.361 !       1.79 eA-3
C158 0.407 0.985 0.082 !       1.79 eA-3
C159 0.016 0.811 0.105 !       1.77 eA-3
C160 0.405 0.154 0.595 !       1.74 eA-3
C161 0.500 0.846 0.562 !       1.73 eA-3
C162 0.248 0.893 0.649 !       1.72 eA-3
C163 0.860 0.119 0.490 !       1.71 eA-3
C164 0.579 0.800 0.754 !       1.71 eA-3
C165 0.030 0.298 0.222 !       1.67 eA-3
Q166 0.718 0.235 0.545 !       1.66 eA-3
C167 1.001 0.828 0.906 !       1.66 eA-3
Q168 0.140 0.259 0.060 !       1.63 eA-3
Q169 0.905 0.700 0.018 !       1.61 eA-3
C170 0.784 0.853 0.922 !       1.61 eA-3
C171 0.548 0.025 0.631 !       1.61 eA-3
C172 0.999 0.885 0.249 !       1.59 eA-3
C173 0.640 0.078 0.602 !       1.58 eA-3
C174 0.157 0.853 0.506 !       1.57 eA-3
Q175 0.764 0.672 0.753 !       1.57 eA-3
C176 0.563 0.821 0.578 !       1.56 eA-3
C177 0.142 0.268 0.378 !       1.56 eA-3
Q178 0.060 0.606 0.675 !       1.55 eA-3
C179 0.015 0.705 0.722 !       1.55 eA-3
C180 0.545 1.003 0.435 !       1.55 eA-3
C181 0.519 0.715 0.528 !       1.54 eA-3
C182 0.671 0.082 0.793 !       1.53 eA-3
C183 0.467 0.923 0.861 !       1.51 eA-3
Q184 0.721 0.748 0.014 !       1.51 eA-3
C185 0.078 0.789 0.673 !       1.50 eA-3
Q186 0.388 0.748 0.002 !       1.47 eA-3
C187 0.406 0.989 0.984 !       1.47 eA-3
C188 0.313 0.835 0.935 !       1.47 eA-3
C189 0.533 0.250 0.689 !       1.47 eA-3
Q190 0.345 0.332 0.822 !       1.46 eA-3
C191 0.184 0.106 0.355 !       1.45 eA-3
C192 0.577 0.944 0.417 !       1.44 eA-3
C193 0.217 0.831 0.607 !       1.42 eA-3
C194 0.049 0.826 0.801 !       1.42 eA-3
Q195 0.483 0.595 0.158 !       1.42 eA-3
C196 0.501 0.973 0.423 !       1.42 eA-3
C197 0.628 0.116 0.467 !       1.42 eA-3
C198 0.064 0.917 0.050 !       1.41 eA-3
C199 0.592 0.928 0.966 !       1.40 eA-3
;
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         8922
_refine_ls_number_restraints     605
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0924
_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^)+(0.1489P)^2^+8.8842P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2486
_refine_ls_wR_factor_ref         0.2593
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7886
_reflns_number_total             8922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00494d2.cif
_cod_data_source_block           ww_sq
_cod_depositor_comments          'Adding full bibliography for 7157465.cif.'
_cod_database_code               7157465
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4(2)
 0.6(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Ternary CH refined with riding coordinates:
 C18(H18)
6.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C15(H15), C7(H7), C20(H20), C26(H26), C25(H25), C23(H23), C4(H4),
 C19(H19), C11(H11), C10(H10), C6(H6), C3(H3), C14(H14), C21(H21)
6.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C1(H1A,H1B,H1C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'