A practical green chemistry approach to synthesize fused bicyclic 4H-pyranes via an amine catalysed 1,4-addition and cyclization cascade
Li, Jun-Long; Li, Qiang; Yang, Kai-Chuan; Li, Yi; Zhou, Liang; Han, Bo; Peng, Cheng; Gou, Xiao-Jun; RSC Adv. 6 (2016) 38875–; doi:10.1039/C6RA06441H

data_7224960
_publ_section_title
;
 A practical green chemistry approach to synthesize fused bicyclic
 4H-pyranes via an amine catalysed 1,4-addition and cyclization cascade
;
_journal_issue                   45
_journal_name_full               'RSC Adv.'
_journal_page_first              38875
_journal_paper_doi               10.1039/C6RA06441H
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C21 H16 Cl N3 O2'
_chemical_formula_sum            'C21 H16 Cl N3 O2'
_chemical_formula_weight         377.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-30 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.291(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.0108(8)
_cell_length_b                   10.0865(3)
_cell_length_c                   20.7318(9)
_cell_measurement_reflns_used    3356
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      72.0650
_cell_measurement_theta_min      4.3060
_cell_volume                     3564.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -33.00   55.00   1.0000    3.9900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000  150.0000 88

  2 omega    1.00   75.00   1.0000    3.9900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -60.0000 74

  3 omega    1.00   75.00   1.0000    3.9900
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  120.0000 74

  4 omega   23.00   90.00   1.0000    3.9900
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  -90.0000 67

  5 omega   20.00  104.00   1.0000    3.9900
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   30.0000 84

  6 omega   23.00   90.00   1.0000    3.9900
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000   60.0000 67

  7 omega   38.00   91.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  8 omega   40.00   98.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

  9 omega   40.00   98.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 10 omega   91.00  176.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 85

 11 omega   91.00  176.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

 12 omega   38.00   91.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 13 omega   38.00   91.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 14 omega   40.00   98.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 15 omega   90.00  165.00   1.0000   15.9400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0789940000
_diffrn_orient_matrix_UB_12      -0.0001403000
_diffrn_orient_matrix_UB_13      0.0040220000
_diffrn_orient_matrix_UB_21      -0.0318837000
_diffrn_orient_matrix_UB_22      0.1052143000
_diffrn_orient_matrix_UB_23      -0.0599526000
_diffrn_orient_matrix_UB_31      -0.0301975000
_diffrn_orient_matrix_UB_32      -0.1107562000
_diffrn_orient_matrix_UB_33      -0.0570720000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8044
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.065
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         4.758
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37222
_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    1.408
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3175
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0567
_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^)+(0.1073P)^2^+1.7684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2667
_reflns_number_total             3175
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra06441h2.cif
_cod_data_source_block           xnkd-0002
_cod_database_code               7224960
_reflns_odcompleteness_completeness 99.73
_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 C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00C,H00D), C00I(H00F,H00G)
2.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_shelx_res_checksum              63876
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-11-26
_olex2_submission_special_instructions 'No special instructions were received'