Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones through a Multicomponent Reaction and Cyclization Strategy
Lai, Xiangfeng; Che, Chao; ACS Omega 5 (2020) 21968–21977; doi:10.1021/acsomega.0c03589

data_4517968
_publ_section_title
;
 Synthesis of Chromeno[4,3-b]pyrrol-4(1H)-ones through a Multicomponent
 Reaction and Cyclization Strategy
;
_journal_issue                   34
_journal_name_full               'ACS Omega'
_journal_page_first              21968
_journal_page_last               21977
_journal_paper_doi               10.1021/acsomega.0c03589
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C27 H23 Cl2 N3 O2'
_chemical_formula_sum            'C27 H23 Cl2 N3 O2'
_chemical_formula_weight         492.38
_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             2020-08-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.12250(10)
_cell_length_b                   15.3457(2)
_cell_length_c                   28.5934(3)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4650
_cell_measurement_theta_min      4.2330
_cell_volume                     4834.15(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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      8.00 121.00   1.00    1.00    --   41.11  19.00 -30.00  113
  2  \w     79.00 173.00   1.00    1.00    --  106.95  61.00-120.00   94
  3  \w     39.00 129.00   1.00    1.00    --  106.95 -61.00  90.00   90
  4  \w    147.00 173.00   1.00    1.00    --  106.95  45.00 150.00   26
  5  \w     32.00 143.00   1.00    1.00    --  106.95 -15.00  60.00  111
  6  \w     32.00  73.00   1.00    1.00    --   41.11-125.00-150.00   41
  7  \w     37.00 128.00   1.00    1.00    --  106.95 -30.00-150.00   91
  8  \w    -65.00  22.00   1.00    1.00    --  -41.11  37.00  90.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137004000
_diffrn_orient_matrix_UB_12      0.0275352000
_diffrn_orient_matrix_UB_13      0.0508082000
_diffrn_orient_matrix_UB_21      -0.1152079000
_diffrn_orient_matrix_UB_22      -0.0564067000
_diffrn_orient_matrix_UB_23      -0.0020142000
_diffrn_orient_matrix_UB_31      0.0779011000
_diffrn_orient_matrix_UB_32      -0.0784276000
_diffrn_orient_matrix_UB_33      0.0193058000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.760
_diffrn_reflns_theta_min         4.013
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         9502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0665P)^2^+1.4294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8381
_reflns_number_total             9502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c03589_si_002.cif
_cod_data_source_block           f2
_cod_depositor_comments
;Adding full bibliography for 4517968.cif.

 Adding full bibliography for 4517968.cif.
;
_cod_database_code               4517968
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.741
_shelx_estimated_absorpt_t_min   0.707
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C48B(0.5) H48A(0.5) H48B(0.5) H48C(0.5) C46A(0.5) H46A(0.5)
 H46B(0.5) H46C(0.5) C46B(0.5) H46D(0.5) H46E(0.5) H46F(0.5) C48A(0.5)
 H48D(0.5) H48E(0.5) H48F(0.5) C47B(0.5) H47A(0.5) H47B(0.5) H47C(0.5)
 C47A(0.5) H47D(0.5) H47E(0.5) H47F(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), N4(H4), N5(H5), C26(H26), C44(H44), C27(H27), C13(H13),
 C17(H17), C37(H37), C14(H14), C43(H43), C54(H54), C24(H24), C23(H23), C40(H40),
  C16(H16), C8(H8), C7(H7), C51(H51), C50(H50), C36(H36), C9(H9), C34(H34),
 C53(H53), C35(H35), C10(H10), C41(H41)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C48B(H48A,H48B,
 H48C), C46A(H46A,H46B,H46C), C46B(H46D,H46E,H46F), C48A(H48D,H48E,H48F),
 C47B(H47A,H47B,H47C), C47A(H47D,H47E,H47F)
;
_shelx_res_checksum              58205
_shelx_hkl_checksum              14091
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.741