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_1557287
_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_absolute_configuration unk
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-05
_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                 95.822(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0919(5)
_cell_length_b                   9.9836(5)
_cell_length_c                   11.7719(5)
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    296.6(3)
_cell_measurement_theta_max      72.8930
_cell_measurement_theta_min      4.8790
_cell_volume                     1063.02(9)
_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      296.6(3)
_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 0.974
_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   -108.00  -7.00   1.00    1.48    --  -36.42 -19.00 150.00  101
  2  \w    -90.00  -2.00   1.00    1.48    --  -36.42 125.00 150.00   88
  3  \w   -104.00 -20.00   1.00    1.48    --  -36.42 -57.00 -90.00   84
  4  \w     20.00 104.00   1.00    1.48    --   36.42  57.00 -60.00   84
  5  \w    100.00 178.00   1.00    5.92    --  108.71 111.00-180.00   78
  6  \w     39.00 109.00   1.00    5.92    --  108.71 -94.00-180.00   70
  7  \w     91.00 177.00   1.00    5.92    --  108.71  45.00  90.00   86
  8  \w     40.00 126.00   1.00    5.92    --  108.71 -45.00 120.00   86
  9  \w     39.00 178.00   1.00    5.92    --  108.71   0.00-150.00  139
 10  \w     41.00 135.00   1.00    5.92    --  108.71 -77.00-120.00   94
 11  \w    -55.00  33.00   1.00    1.48    --  -36.42  38.00 -30.00   88
 12  \w     10.00 104.00   1.00    1.48    --   36.42  77.00  60.00   94
 13  \w     23.00  90.00   1.00    1.48    --   36.42-125.00  60.00   67
 14  \w     70.00 102.00   1.00    5.92    --  108.71  15.00  30.00   32
 15  \w     91.00 176.00   1.00    5.92    --  108.71  61.00 -90.00   85
;
_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      0.1614292000
_diffrn_orient_matrix_UB_12      -0.0464816000
_diffrn_orient_matrix_UB_13      0.0263175000
_diffrn_orient_matrix_UB_21      0.0223890000
_diffrn_orient_matrix_UB_22      0.0106066000
_diffrn_orient_matrix_UB_23      -0.1276711000
_diffrn_orient_matrix_UB_31      0.0495260000
_diffrn_orient_matrix_UB_32      0.1467540000
_diffrn_orient_matrix_UB_33      0.0175693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6415
_diffrn_reflns_point_group_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.788
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.916
_diffrn_reflns_theta_min         3.774
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77038
_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    1.245
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0549
_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^)+(0.1012P)^2^+0.0769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.621
_reflns_Friedel_fraction_max     0.578
_reflns_number_gt                3152
_reflns_number_total             3358
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06377c2.cif
_cod_data_source_block           lq-zx-180704
_cod_depositor_comments
;Adding full bibliography for 1557287--1557289.cif.

 Adding full bibliography for 1557287--1557289.cif.
;
_cod_original_cell_volume        1063.02(10)
_cod_database_code               1557287
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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:
 C9(H9A,H9B), C13(H13A,H13B), C14(H14A,H14B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C18(H18), C2(H2), C3(H3), C22(H22), C19(H19), C5(H5),
 C20(H20), C4(H4), C21(H21)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              68595
_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 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.726