Regiodivergent construction of medium-sized heterocycles from vinylethylene carbonates and allylidenemalononitriles
Zhang, Xiang; Li, Xiang; Li, Jun-Long; Wang, Qi-Wei; Zou, Wen-Lin; Liu, Yan-Qing; Jia, Zhi-Qiang; Peng, Fu; Han, Bo; Chemical Science 11 (2020) 2888–2894; doi:10.1039/C9SC06377C

data_1557288
_publ_section_title
;
 Regiodivergent construction of medium-sized heterocycles from
 vinylethylene carbonates and allylidenemalononitriles
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              2888
_journal_page_last               2894
_journal_paper_doi               10.1039/C9SC06377C
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C25 H22 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.44
_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             2018-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-29 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.745(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6576(5)
_cell_length_b                   13.2796(9)
_cell_length_c                   17.3578(10)
_cell_measurement_reflns_used    3528
_cell_measurement_temperature    295.4(4)
_cell_measurement_theta_max      72.3720
_cell_measurement_theta_min      4.1830
_cell_volume                     2194.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      295.4(4)
_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 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -104.00 -20.00   1.00    2.16    --  -36.42 -57.00 -60.00   84
  2  \w   -104.00 -20.00   1.00    2.16    --  -36.42 -57.00   0.00   84
  3  \w    -33.00  55.00   1.00    2.16    --   36.42 -38.00  30.00   88
  4  \w    -31.00  53.00   1.00    2.16    --   36.42 -57.00 -90.00   84
  5  \w    -31.00  53.00   1.00    2.16    --   36.42 -57.00 150.00   84
  6  \w      1.00  75.00   1.00    2.16    --   36.42 -99.00-120.00   74
  7  \w     39.00 109.00   1.00    8.65    --  108.71 -94.00-150.00   70
  8  \w     70.00 178.00   1.00    8.65    --  108.71  15.00-180.00  108
  9  \w     91.00 177.00   1.00    8.65    --  108.71  45.00-120.00   86
 10  \w     82.00 176.00   1.00    8.65    --  108.71  77.00   0.00   94
 11  \w     39.00 109.00   1.00    8.65    --  108.71 -94.00 120.00   70
 12  \w     39.00 109.00   1.00    8.65    --  108.71 -94.00-120.00   70
 13  \w     42.00 127.00   1.00    8.65    --  108.71 -61.00-120.00   85
 14  \w     39.00 115.00   1.00    8.65    --  108.71-111.00  90.00   76
 15  \w   -104.00 -20.00   1.00    2.16    --  -36.42 -57.00-180.00   84
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0691408000
_diffrn_orient_matrix_UB_12      -0.0548264000
_diffrn_orient_matrix_UB_13      -0.0619522000
_diffrn_orient_matrix_UB_21      -0.0490574000
_diffrn_orient_matrix_UB_22      0.0843871000
_diffrn_orient_matrix_UB_23      -0.0591563000
_diffrn_orient_matrix_UB_31      0.1377925000
_diffrn_orient_matrix_UB_32      0.0577319000
_diffrn_orient_matrix_UB_33      0.0278571000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12330
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.063
_diffrn_reflns_theta_min         4.215
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0608
_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^)+(0.1044P)^2^+0.2485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1748
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3173
_reflns_number_total             4284
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06377c2.cif
_cod_data_source_block           lq-zx-0727
_cod_depositor_comments
;Adding full bibliography for 1557287--1557289.cif.

 Adding full bibliography for 1557287--1557289.cif.
;
_cod_database_code               1557288
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.93
_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:
 C5(H5A,H5B), C15(H15A,H15B), C14(H14A,H14B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C6(H6), C18(H18), C21(H21), C20(H20), C19(H19), C9(H9), C13(H13),
 C10(H10), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              38242
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.790