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_1554939
_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         'C15 H13 N3 O2'
_chemical_formula_sum            'C15 H13 N3 O2'
_chemical_formula_weight         267.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-03-27 deposited with the CCDC.	2019-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                85.696(4)
_cell_angle_beta                 89.837(4)
_cell_angle_gamma                79.658(4)
_cell_formula_units_Z            4
_cell_length_a                   6.9944(3)
_cell_length_b                   7.8586(4)
_cell_length_c                   26.1858(11)
_cell_measurement_reflns_used    5466
_cell_measurement_temperature    296.9(6)
_cell_measurement_theta_max      72.5690
_cell_measurement_theta_min      5.7460
_cell_volume                     1411.87(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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.9(6)
_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 0.982
_diffrn_measurement_details
;
  1 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -19.0000 -120.0000 101

  2 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000   60.0000 88

  3 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -77.0000   30.0000 94

  4 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  150.0000 95

  5 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -30.0000 67

  6 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000  120.0000 74

  7 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -120.0000 84

  8 omega   38.00   91.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

  9 omega   40.00   98.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 10 omega  100.00  178.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 78

 11 omega  100.00  178.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

 12 omega   39.00  109.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 13 omega   40.00   98.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 14 omega   39.00  109.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 15 omega   38.00   91.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 16 omega   91.00  176.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 17 omega   38.00  116.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 18 omega   40.00   98.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 19 omega   40.00   98.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 20 omega   39.00  109.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 21 omega   70.00  178.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 108

 22 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000 -180.0000 84

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

 24 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   38.0000  -30.0000 88

 25 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -38.0000   60.0000 88

 26 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000  -90.0000 95

 27 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   77.0000   60.0000 95

 28 omega   70.00  178.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  120.0000 108

 29 omega   91.00  156.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 65

 30 omega   70.00  178.00   1.0000    3.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 108
;
_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      0.1320938000
_diffrn_orient_matrix_UB_12      -0.0785904000
_diffrn_orient_matrix_UB_13      -0.0426203000
_diffrn_orient_matrix_UB_21      0.1528943000
_diffrn_orient_matrix_UB_22      0.1087395000
_diffrn_orient_matrix_UB_23      0.0134497000
_diffrn_orient_matrix_UB_31      0.0964819000
_diffrn_orient_matrix_UB_32      -0.1481132000
_diffrn_orient_matrix_UB_33      0.0385205000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15449
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.454
_diffrn_reflns_theta_min         5.082
_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  0.84730
_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    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0706
_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^)+(0.1360P)^2^+0.1940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4564
_reflns_number_total             5505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00509a2.cif
_cod_data_source_block           hq-3
_cod_depositor_comments
;

2022-03-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1411.88(11)
_cod_original_formula_moiety     '2(C15 H13 N3 O2)'
_cod_original_formula_sum        'C30 H26 N6 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     534.57
_cod_database_code               1554939
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C1(H1), C25(H25), C16(H16), C5(H5), C20(H20), C4(H4), C2(H2),
 C3(H3), C17(H17), C19(H19), C18(H18)
2.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N5(H5A,H5B)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              3854
_shelx_hkl_checksum              18397
_olex2_date_sample_data_collection 2017-04-26
_olex2_submission_special_instructions 'No special instructions were received'