Multicomponent cascade reaction by metal-free aerobic oxidation for synthesis of highly functionalized 2-amino-4-cumarinyl-5-arylpyrroles.
Zi, Quan-Xing; Yang, Chang-Long; Li, Kun; Luo, Qin; Lin, Jun; Yan, Sheng-Jiao; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02063

data_4037712
_publ_section_title
;
 Multicomponent cascade reaction by metal-free aerobic oxidation for
 synthesis of highly functionalized 2-amino-4-cumarinyl-5-arylpyrroles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02063
_journal_year                    2019
_chemical_formula_moiety         'C29 H19 Cl F2 N2 O5'
_chemical_formula_sum            'C29 H19 Cl F2 N2 O5'
_chemical_formula_weight         548.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-08-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.589(2)
_cell_length_b                   15.353(4)
_cell_length_c                   22.146(6)
_cell_measurement_reflns_used    2733
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.88
_cell_measurement_theta_min      2.72
_cell_volume                     2920.3(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17815
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.693
_diffrn_reflns_theta_min         1.614
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0613 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.9521.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.685
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.189
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.587
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.587
_refine_ls_R_factor_all          0.1850
_refine_ls_R_factor_gt           0.1082
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2631
_refine_ls_wR_factor_ref         0.2952
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3504
_reflns_number_total             6611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02063_si_004.cif
_cod_data_source_block           ysj16
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value ' multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4037712
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.1(3)
 -0.1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
3. Others
 Sof(H11)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(H13)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C2(H2B), C3(H3), C10(H10), C11(H11), C13(H13), C14(H14), C21(H21),
 C22(H22), C23(H23), C24(H24), C28(H28), C29(H29)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              31542
_shelx_hkl_checksum              79238
_olex2_submission_special_instructions 'No special instructions were received'