Exploring the Reactivity of Nitro-Activated 1,3-Enynes in an Organocatalytic One-Pot, Three-Component Coupling Reaction: A Tandem Catalytic Approach to a Novel 3-Nitrochroman Scaffold.
Xiao, Yu; Lin, Jun-Bing; Zhao, Yin-Na; Liu, Jin-Yu; Xu, Peng-Fei; Organic letters 18 (2016) 6276–6279; doi:10.1021/acs.orglett.6b03073

data_1555937
_publ_section_title
;
 Exploring the Reactivity of Nitro-Activated 1,3-Enynes in an
 Organocatalytic One-Pot, Three-Component Coupling Reaction: A Tandem
 Catalytic Approach to a Novel 3-Nitrochroman Scaffold.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6276
_journal_page_last               6279
_journal_paper_doi               10.1021/acs.orglett.6b03073
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H28 Cl N O6'
_chemical_formula_sum            'C33 H28 Cl N O6'
_chemical_formula_weight         570.01
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-25
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8021(4)
_cell_length_b                   9.9889(5)
_cell_length_c                   32.4893(17)
_cell_measurement_reflns_used    1689
_cell_measurement_temperature    292.35(10)
_cell_measurement_theta_max      22.6570
_cell_measurement_theta_min      3.8900
_cell_volume                     2856.6(2)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      292.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -113.00  -84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.8858  178.0000   90.0000 29

  2 omega  -19.00   93.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   38.0000 -120.0000 112

  3 omega   63.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   57.0000  120.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0669865000
_diffrn_orient_matrix_UB_12      -0.0024601000
_diffrn_orient_matrix_UB_13      -0.0121164000
_diffrn_orient_matrix_UB_21      -0.0447958000
_diffrn_orient_matrix_UB_22      -0.0043493000
_diffrn_orient_matrix_UB_23      -0.0180861000
_diffrn_orient_matrix_UB_31      -0.0003647000
_diffrn_orient_matrix_UB_32      0.0708545000
_diffrn_orient_matrix_UB_33      -0.0015491000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            7026
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+0.2907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                3421
_reflns_number_total             4951
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03073_si_001.cif
_cod_data_source_block           xiaon_0524
_cod_database_code               1555937
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2AA(H2AA,H2AB), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C2(H2), C4(H4), C9(H9), C11(H11), C12(H12), C13(H13), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2016-05-25
_olex2_submission_special_instructions 'No special instructions were received'