One-Pot Cascade Heterocyclization of γ- and β-Ketomalononitriles to 2,4-Dichloro-Substituted Pyrano[2,3- d]pyrimidines and Furo[2,3- d]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide.
Li, Zhen-Hua; Jiang, Zhi-Jiang; Shao, Qiao-Ling; Qin, Jin-Jing; Shu, Qiang-Feng; Lu, Wen-Hao; Su, Wei-Ke; The Journal of organic chemistry 83 (2018) 6423–6431; doi:10.1021/acs.joc.8b00669

data_4035835
_publ_section_title
;
 One-Pot Cascade Heterocyclization of \g- and \b-Ketomalononitriles to
 2,4-Dichloro-Substituted Pyrano[2,3- d]pyrimidines and Furo[2,3-
 d]pyrimidines Mediated by Triphosgene and Triphenylphosphine Oxide.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6423
_journal_page_last               6431
_journal_paper_doi               10.1021/acs.joc.8b00669
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 Cl2 N2 O'
_chemical_formula_sum            'C20 H14 Cl2 N2 O'
_chemical_formula_weight         369.23
_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     dual
_audit_creation_date             2017-05-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-07-18 deposited with the CCDC.
2018-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.855(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1373(5)
_cell_length_b                   22.4412(10)
_cell_length_c                   17.6747(10)
_cell_measurement_reflns_used    7472
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.3147
_cell_measurement_theta_min      2.9646
_cell_volume                     3518.8(3)
_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_temperature      297
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18898
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.971
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       Block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0372P)^2^+0.4108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4750
_reflns_number_total             7180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00669_si_002.cif
_cod_data_source_block           Compound_2j
_cod_database_code               4035835
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00H(H00H), C00P(H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00O(H00O), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C015(H015), C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C)
2.c Idealised Me refined as rotating group:
 C01D(H01D,H01E,H01F), C01E(H01G,H01H,H01I)
;
_shelx_res_checksum              38416
_shelx_hkl_checksum              11230
_olex2_submission_special_instructions 'No special instructions were received'