Stereochemistry and Mechanistic Insight in the [2(k)+2(i)+2(i)] Annulations of Ketenes and Imines.
Yang, Zhanhui; He, Wei; Cheng, Baoxiang; Xu, Jiaxi; The Journal of organic chemistry 81 (2016) 4506–4515; doi:10.1021/acs.joc.6b00279

data_4036678
_publ_section_title
;
 Stereochemistry and Mechanistic Insight in the [2(k)+2(i)+2(i)]
 Annulations of Ketenes and Imines.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4506
_journal_page_last               4515
_journal_paper_doi               10.1021/acs.joc.6b00279
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H19 N3 O'
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39
_chemical_melting_point          469.6(5)
_chemical_name_common            pyrimido[2,1-a:4,3-a']diisoquinoline
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-19
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.700(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9507(10)
_cell_length_b                   8.4520(5)
_cell_length_c                   17.0816(14)
_cell_measurement_reflns_used    1682
_cell_measurement_temperature    97.6
_cell_measurement_theta_max      29.6438
_cell_measurement_theta_min      2.9936
_cell_volume                     1643.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      97.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -11.00   35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000  150.0000 46

  2 omega    1.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000   90.0000 28

  3 omega   -1.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000    0.0000 89

  4 omega  -39.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -77.0000 -150.0000 83
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0221958000
_diffrn_orient_matrix_UB_12      0.0210748000
_diffrn_orient_matrix_UB_13      -0.0420823000
_diffrn_orient_matrix_UB_21      0.0300999000
_diffrn_orient_matrix_UB_22      -0.0649387000
_diffrn_orient_matrix_UB_23      -0.0105221000
_diffrn_orient_matrix_UB_31      -0.0498072000
_diffrn_orient_matrix_UB_32      -0.0486772000
_diffrn_orient_matrix_UB_33      -0.0042139000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7880
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+0.2043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2451
_reflns_number_total             3223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b00279_si_002.cif
_cod_data_source_block           exp_4m(2697)
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '196-197 deg' was changed
to '469.6(5)' -- it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4036678
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32