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_1554938
_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      tetragonal
_space_group_IT_number           106
_space_group_name_Hall           'P 4c -2ab'
_space_group_name_H-M_alt        'P 42 b c'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-03-27 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.7832(3)
_cell_length_b                   21.7832(3)
_cell_length_c                   8.49552(15)
_cell_measurement_reflns_used    7329
_cell_measurement_temperature    297.8(2)
_cell_measurement_theta_max      72.3070
_cell_measurement_theta_min      4.0620
_cell_volume                     4031.19(11)
_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)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.8(2)
_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 0.992
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    4.1000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000    0.0000 94

  2 omega  -33.00  106.00   1.0000    4.1000
omega____ theta____ kappa____ phi______ frames
    -       36.4171    0.0000  -30.0000 139

  3 omega    1.00   75.00   1.0000    4.1000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000 -120.0000 74

  4 omega  -31.00   53.00   1.0000    4.1000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -57.0000   90.0000 84

  5 omega    1.00   75.00   1.0000    4.1000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -99.0000  120.0000 74

  6 omega  -31.00   63.00   1.0000    4.1000
omega____ theta____ kappa____ phi______ frames
    -       36.4171  -77.0000  -60.0000 94

  7 omega   39.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

  8 omega   38.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

  9 omega   39.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 10 omega   91.00  176.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 11 omega   38.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 12 omega   90.00  175.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

 13 omega   88.00  113.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 25

 14 omega   38.00   88.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

 15 omega   45.00   83.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 38

 16 omega   42.00  135.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 93
;
_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      -0.0127496000
_diffrn_orient_matrix_UB_12      -0.0695535000
_diffrn_orient_matrix_UB_13      0.0039570000
_diffrn_orient_matrix_UB_21      0.0695215000
_diffrn_orient_matrix_UB_22      -0.0126933000
_diffrn_orient_matrix_UB_23      0.0080365000
_diffrn_orient_matrix_UB_31      -0.0028306000
_diffrn_orient_matrix_UB_32      0.0020518000
_diffrn_orient_matrix_UB_33      0.1810537000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21310
_diffrn_reflns_point_group_measured_fraction_full 0.771
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.636
_diffrn_reflns_theta_min         4.059
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62557
_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    1.211
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Flack x determined using 766 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0634
_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^)+(0.1185P)^2^+0.0936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.427
_reflns_Friedel_fraction_full    0.504
_reflns_Friedel_fraction_max     0.490
_reflns_number_gt                2851
_reflns_number_total             3049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00509a2.cif
_cod_data_source_block           lq-zx-2-2
_cod_original_cell_volume        4031.20(13)
_cod_database_code               1554938
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.91
_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:
 C00G(H00B,H00D), C00O(H00J,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00H(H00H), C00I(H00I), C00L(H00L)
2.c Idealised Me refined as rotating group:
 C00N(H00E,H00F,H00G), C00P(H00M,H00N,H00O), C00Q(H00P,H00Q,H00R), C00R(H00S,
 H00T,H00U)
;
_shelx_res_checksum              7043
_shelx_hkl_checksum              25353
_olex2_submission_special_instructions 'No special instructions were received'