A domino annulation approach to 3,4-diacylpyrrolo[1,2-a]pyrazines: decoration of pyrazine units.
Dagar, Anuradha; Seo, Yohan; Namkung, Wan; Kim, Ikyon; Organic & biomolecular chemistry 18 (2020) 3324–3333; doi:10.1039/d0ob00444h

data_7157445
_publ_section_title
;
 A domino annulation approach to 3,4-diacylpyrrolo[1,2-a]pyrazines:
 decoration of pyrazine units.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3324
_journal_page_last               3333
_journal_paper_doi               10.1039/d0ob00444h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 N2 O3'
_chemical_formula_sum            'C22 H17 N2 O3'
_chemical_formula_weight         357.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-29 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.789(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8538(17)
_cell_length_b                   10.2156(17)
_cell_length_c                   18.572(3)
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    293.31(10)
_cell_measurement_theta_max      22.3230
_cell_measurement_theta_min      2.8950
_cell_volume                     1823.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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      293.31(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.891
_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      3.00  57.00   1.00    8.75    --   11.51-123.00 164.00   54
  2  \w     14.00  75.00   1.00    8.75    --   11.51-149.00   1.00   61
  3  \w    -20.00  17.00   1.00    8.75    --  -11.04 -99.00 -30.00   37
  4  \w     -8.00  28.00   1.00    8.75    --  -11.04 -99.00-120.00   36
  5  \w     36.00  62.00   1.00    8.75    --   11.51 178.00  90.00   26
  6  \w     42.00  80.00   1.00    8.75    --   11.51-178.00 120.00   38
  7  \w     -1.00  37.00   1.00    8.75    --   11.51  38.00 120.00   38
  8  \w     45.00  71.00   1.00    8.75    --   11.51  38.00 120.00   26
  9  \w     -6.00  85.00   1.00    8.75    --   11.51  38.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089713000
_diffrn_orient_matrix_UB_12      -0.0182449000
_diffrn_orient_matrix_UB_13      -0.0355060000
_diffrn_orient_matrix_UB_21      -0.0669963000
_diffrn_orient_matrix_UB_22      0.0250804000
_diffrn_orient_matrix_UB_23      -0.0160702000
_diffrn_orient_matrix_UB_31      0.0296925000
_diffrn_orient_matrix_UB_32      0.0620863000
_diffrn_orient_matrix_UB_33      -0.0039650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            19579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.659
_diffrn_reflns_theta_min         2.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.165
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1476
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0559P)^2^+0.4687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2454
_reflns_number_total             4594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00444h2.cif
_cod_data_source_block           exp_1356
_cod_depositor_comments          'Adding full bibliography for 7157445.cif.'
_cod_database_code               7157445
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C17 H17 N O4'
_chemical_oxdiff_usercomment     JUN3-VII-127
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=Sof(H0AC)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C0AA(H0AA,H0AB,H0AC)
;
_olex2_date_sample_data_collection 2019-04-09
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.626