Synthetic approach to skeletally diverse nitrogen heterocycles from dicyano-2-methylenebut-3-enoates
Zhang, Xiang; Huang, Qing-Fei; Zou, Wen-Lin; Li, Qing-Zhu; Feng, Xin; Jia, Zhi-Qiang; Liu, Yue; Li, Jun-Long; Wang, Qi-Wei; Organic Chemistry Frontiers 6 (2019) 3321–; doi:10.1039/C9QO00509A

data_1554936
_publ_section_title
;
 Synthetic approach to skeletally diverse nitrogen heterocycles from
 dicyano-2-methylenebut-3-enoates
;
_journal_issue                   19
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3321
_journal_paper_doi               10.1039/C9QO00509A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C20 H21 N3 O4'
_chemical_formula_sum            'C20 H21 N3 O4'
_chemical_formula_weight         367.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-19
_audit_creation_method
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Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2019-03-27 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.908(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8238(4)
_cell_length_b                   10.3557(3)
_cell_length_c                   17.8199(7)
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    295.91(10)
_cell_measurement_theta_max      72.3310
_cell_measurement_theta_min      4.0970
_cell_volume                     1982.90(12)
_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
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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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.91(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
  1 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000    0.0000 74

  2 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000 -120.0000 95

  3 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -60.0000 67

  4 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000  -90.0000 84

  5 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000   30.0000 95

  6 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  120.0000 95

  7 omega   38.00   91.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

  8 omega   38.00   91.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

  9 omega   38.00   91.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 10 omega   38.00   91.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 11 omega   39.00  109.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 12 omega   39.00  109.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 13 omega   38.00   91.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 14 omega   91.00  176.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 15 omega   39.00  109.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 70

 16 omega   40.00  135.00   1.0000    1.1700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 95

 17 omega    9.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  -30.0000 25
;
_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      -0.0787360000
_diffrn_orient_matrix_UB_12      -0.0462093000
_diffrn_orient_matrix_UB_13      -0.0728506000
_diffrn_orient_matrix_UB_21      -0.1181410000
_diffrn_orient_matrix_UB_22      0.0061397000
_diffrn_orient_matrix_UB_23      0.0402480000
_diffrn_orient_matrix_UB_31      -0.0205462000
_diffrn_orient_matrix_UB_32      0.1412033000
_diffrn_orient_matrix_UB_33      -0.0255989000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10517
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.365
_diffrn_reflns_theta_min         5.000
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05370
_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    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+0.2070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1697
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3290
_reflns_number_total             3854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00509a3.cif
_cod_data_source_block           lq-zx-180418
_cod_original_cell_volume        1982.89(12)
_cod_database_code               1554936
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.87
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C15(H15A,H15B,
 H15C)
;
_shelx_res_checksum              15651
_shelx_hkl_checksum              385
_olex2_submission_special_instructions 'No special instructions were received'