[6 + 3] Annulations of Morita-Baylis-Hillman carbonates and dicyanoheptafulvene.
Jia, Ruo-Ling; Liu, Qing-Ling; Yang, Long-Wei; Deng, Shi; Song, Yang; Organic & biomolecular chemistry 19 (2021) 9867–9871; doi:10.1039/d1ob00854d

data_7158346
_publ_section_title
;
 [6 + 3] Annulations of Morita-Baylis-Hillman carbonates and
 dicyanoheptafulvene.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9867
_journal_page_last               9871
_journal_paper_doi               10.1039/d1ob00854d
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H13 N3'
_chemical_formula_sum            'C20 H13 N3'
_chemical_formula_weight         295.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-11-22 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2668(6)
_cell_length_b                   10.7130(4)
_cell_length_c                   7.8156(2)
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    295.7(4)
_cell_measurement_theta_max      72.7430
_cell_measurement_theta_min      4.5690
_cell_volume                     1613.18(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      295.7(4)
_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 0.989
_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   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00-150.00   88
  2  \w    -35.00  65.00   1.00    1.00    --   36.04 -19.00 -30.00  100
  3  \w     23.00  89.00   1.00    1.00    --   36.04-125.00 -90.00   66
  4  \w     17.00 105.00   1.00    1.00    --   36.04  38.00 150.00   88
  5  \w     39.00 109.00   1.00    5.00    --  108.71 -94.00 -90.00   70
  6  \w     39.00 109.00   1.00    5.00    --  108.71 -94.00 -30.00   70
  7  \w     82.00 176.00   1.00    5.00    --  108.71  77.00-180.00   94
  8  \w     40.00 126.00   1.00    5.00    --  108.71 -45.00 120.00   86
  9  \w     40.00 126.00   1.00    5.00    --  108.71 -45.00  30.00   86
 10  \w     91.00 176.00   1.00    5.00    --  108.71  61.00  30.00   85
 11  \w     87.00 162.00   1.00    5.00    --  108.71  30.00 120.00   75
;
_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      0.0726869000
_diffrn_orient_matrix_UB_12      0.0200372000
_diffrn_orient_matrix_UB_13      0.0772509000
_diffrn_orient_matrix_UB_21      0.0288277000
_diffrn_orient_matrix_UB_22      -0.1052934000
_diffrn_orient_matrix_UB_23      -0.1140683000
_diffrn_orient_matrix_UB_31      0.0164079000
_diffrn_orient_matrix_UB_32      0.0959902000
_diffrn_orient_matrix_UB_33      -0.1410270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7111
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.738
_diffrn_reflns_theta_min         4.590
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42870
_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    1.216
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0573
_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^)+(0.1067P)^2^+0.0134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2899
_reflns_number_total             3148
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00854d2.cif
_cod_data_source_block           cyc-sy6401
_cod_depositor_comments          'Adding full bibliography for 7158346.cif.'
_cod_original_cell_volume        1613.19(9)
_cod_database_code               7158346
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C00B(H00B), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C002(H002), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
;
_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 2.313
_oxdiff_exptl_absorpt_empirical_full_min 0.685