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_1557289
_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 H21 N2 O3'
_chemical_formula_sum            'C25 H22 N2 O3'
_chemical_formula_weight         398.44
_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             2019-07-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-07-29 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                87.285(6)
_cell_angle_beta                 85.531(8)
_cell_angle_gamma                74.852(9)
_cell_formula_units_Z            2
_cell_length_a                   7.8691(9)
_cell_length_b                   9.8641(8)
_cell_length_c                   13.1840(9)
_cell_measurement_reflns_used    3691
_cell_measurement_temperature    225(100)
_cell_measurement_theta_max      71.6710
_cell_measurement_theta_min      4.6310
_cell_volume                     984.41(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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      N~2~
_diffrn_ambient_temperature      225(100)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_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    -63.00  31.00   1.00    1.00    --  -36.42  77.00  60.00   94
  2  \w   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00 -60.00   84
  3  \w   -108.00  -7.00   1.00    1.00    --  -36.42 -19.00 120.00  101
  4  \w    -53.00  31.00   1.00    1.00    --  -36.42  57.00 -60.00   84
  5  \w      1.00  75.00   1.00    1.00    --   36.42 -99.00 150.00   74
  6  \w    -31.00  53.00   1.00    1.00    --   36.42 -57.00-180.00   84
  7  \w     23.00  90.00   1.00    1.00    --   36.42-125.00  30.00   67
  8  \w     30.00  96.00   1.00    1.00    --   36.42-136.00 141.00   66
  9  \w     36.00 113.00   1.00    3.06    --  106.21-111.00  30.00   77
 10  \w     38.00 124.00   1.00    3.06    --  106.21 -45.00  60.00   86
 11  \w     37.00 109.00   1.00    3.06    --  106.21 -94.00  90.00   72
 12  \w    100.00 176.00   1.00    3.06    --  106.21 111.00 -30.00   76
 13  \w     89.00 175.00   1.00    3.06    --  106.21  45.00 -30.00   86
 14  \w     89.00 175.00   1.00    3.06    --  106.21  45.00 150.00   86
 15  \w     36.00 113.00   1.00    3.06    --  106.21-111.00 -90.00   77
 16  \w     36.00 113.00   1.00    3.06    --  106.21-111.00-180.00   77
 17  \w     89.00 175.00   1.00    3.06    --  106.21  45.00  60.00   86
 18  \w     39.00 124.00   1.00    3.06    --  106.21 -61.00 -30.00   85
 19  \w     38.00 124.00   1.00    3.06    --  106.21 -45.00-180.00   86
 20  \w     89.00 175.00   1.00    3.06    --  106.21  45.00  90.00   86
 21  \w     39.00 124.00   1.00    3.06    --  106.21 -61.00-120.00   85
 22  \w     89.00 175.00   1.00    3.06    --  106.21  45.00  30.00   86
 23  \w   -104.00 -20.00   1.00    1.00    --  -36.42 -57.00 120.00   84
 24  \w   -104.00 -10.00   1.00    1.00    --  -36.42 -77.00  60.00   94
 25  \w     10.00 104.00   1.00    1.00    --   36.42  77.00 150.00   94
 26  \w     10.00 104.00   1.00    1.00    --   36.42  77.00  60.00   94
 27  \w     10.00 104.00   1.00    1.00    --   36.42  77.00 -30.00   94
 28  \w     10.00 104.00   1.00    1.00    --   36.42  77.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0045949000
_diffrn_orient_matrix_UB_12      0.0222620000
_diffrn_orient_matrix_UB_13      -0.1165287000
_diffrn_orient_matrix_UB_21      -0.0950854000
_diffrn_orient_matrix_UB_22      0.1564867000
_diffrn_orient_matrix_UB_23      0.0129862000
_diffrn_orient_matrix_UB_31      0.1796242000
_diffrn_orient_matrix_UB_32      0.0348775000
_diffrn_orient_matrix_UB_33      0.0008357000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.358
_diffrn_reflns_theta_min         3.364
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.344
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.715
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0793
_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^)+(0.1564P)^2^+0.2886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2132
_refine_ls_wR_factor_ref         0.2314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3208
_reflns_number_total             3791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06377c2.cif
_cod_data_source_block           ljl-zx-0719-150k
_cod_depositor_comments
;Adding full bibliography for 1557287--1557289.cif.

 Adding full bibliography for 1557287--1557289.cif.
;
_cod_original_cell_volume        984.42(16)
_cod_database_code               1557289
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H00I,H00C,H00E} of C00I, {H00A,H00B,H00H} of C00H, All
  C(H,H) groups
 At 1.5 times of:
  {H00U,H00V,H00W} of C00U
2. Others
 Sof(H00H)=Sof(H00C)=Sof(H00E)=Sof(O2A)=1-FVAR(1)
 Sof(H00A)=Sof(H00B)=Sof(H00I)=Sof(O2)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00D(H00D)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), C00I(H00C,H00E), C00J(H00F,H00J), C00P(H00L,H00P)
3.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00M(H00M),
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
3.d Idealised Me refined as rotating group:
 C00U(H00U,H00V,H00W)
;
_shelx_res_checksum              18871
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-07-19
_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 1.873
_oxdiff_exptl_absorpt_empirical_full_min 0.697