Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles
Wang, Dong; Li, Linna; Feng, Hairong; Sun, Hua; Almeida-Veloso, Fabrice; Charavin, Marine; Yu, Peng; Désaubry, Laurent; Green Chemistry 20 (2018) 2775–; doi:10.1039/C8GC00987B

data_7230722
_publ_section_title
;
 Catalyst-free three-component synthesis of highly functionalized
 2,3-dihydropyrroles
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              2775
_journal_paper_doi               10.1039/C8GC00987B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C41 H35 Cl2 N3 O3, C4 H8 O, C3 H6'
_chemical_formula_sum            'C48 H49 Cl2 N3 O4'
_chemical_formula_weight         802.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-02-08 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                98.819(9)
_cell_angle_beta                 97.641(6)
_cell_angle_gamma                98.079(5)
_cell_formula_units_Z            2
_cell_length_a                   12.043(3)
_cell_length_b                   13.174(4)
_cell_length_c                   13.616(4)
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     2087.0(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 40.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9752
              2theta: -15.0855
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 40.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9752
              2theta: -15.0855
scan:
    Number of images: 360
               Slice: -105.0000 - 75.0000
         Image width: 0.5000
            Exp time: 40.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 44.9752
              2theta: -15.0855
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.022704
_diffrn_orient_matrix_UB_12      -0.001546
_diffrn_orient_matrix_UB_13      -0.081829
_diffrn_orient_matrix_UB_21      0.003085
_diffrn_orient_matrix_UB_22      0.076566
_diffrn_orient_matrix_UB_23      -0.013873
_diffrn_orient_matrix_UB_31      0.073900
_diffrn_orient_matrix_UB_32      0.011881
_diffrn_orient_matrix_UB_33      0.007941
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26425
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         3.067
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             848
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         9393
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0723P)^2^+1.1140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6643
_reflns_number_total             9393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc00987b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7230721--7230722.cif.
;
_cod_original_cell_volume        2086.9(11)
_cod_database_code               7230722
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. 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 C(H,H,H) groups
2. Restrained distances
 N1-H1 = N3-H3
 0.9 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C42) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C45)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C48) \\sim Ueq,
Uanis(O4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,
 H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16),
 C22(H22), C23(H23), C24(H24), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32),
  C33(H33), C36(H36), C37(H37), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              47550
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'