One-Pot Synthesis of Diverse Collections of Benzoxazepine and Indolopyrazine Fused to Heterocyclic Systems.
Srinivasulu, Vunnam; Shehadeh, Ihsan; Khanfar, Monther A.; Malik, Omar G.; Tarazi, Hamadeh; Abu-Yousef, Imad A; Sebastian, Anusha; Baniowda, Nabil; O'Connor, Matthew John; Al-Tel, Taleb H; The Journal of organic chemistry 84 (2019) 934–948; doi:10.1021/acs.joc.8b02878

data_4035969
_publ_section_title
;
 One-Pot Synthesis of Diverse Collections of Benzoxazepine and
 Indolopyrazine Fused to Heterocyclic Systems.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              934
_journal_page_last               948
_journal_paper_doi               10.1021/acs.joc.8b02878
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H21 N3 O2'
_chemical_formula_sum            'C22 H21 N3 O2'
_chemical_formula_weight         359.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.797(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9275(3)
_cell_length_b                   10.6817(4)
_cell_length_c                   17.0657(7)
_cell_measurement_reflns_used    3297
_cell_measurement_temperature    291
_cell_measurement_theta_max      29.2230
_cell_measurement_theta_min      3.7940
_cell_volume                     1807.53(11)
_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_temperature      291
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0534
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.881
_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    -21.00  21.00   1.00   22.00    --  -16.20 -99.00  60.00   42
  2  \w    -89.00 -34.00   1.00   22.00    --  -16.20 178.00  90.00   55
  3  \w    -27.00  51.00   1.00   22.00    --  -16.20  77.00   0.00   78
  4  \w     38.00  77.00   1.00   22.00    --   16.83  19.00 120.00   39
  5  \w    -83.00  -2.00   1.00   22.00    --  -16.04 -57.00 -90.00   81
  6  \w    -16.00  15.00   1.00   22.00    --   16.67 -57.00-150.00   31
  7  \w    -22.00   5.00   1.00   22.00    --   16.67 -38.00 -30.00   27
  8  \w      5.00  77.00   1.00   22.00    --   16.67  38.00-180.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0341976000
_diffrn_orient_matrix_UB_12      0.0481354000
_diffrn_orient_matrix_UB_13      0.0196812000
_diffrn_orient_matrix_UB_21      0.0287132000
_diffrn_orient_matrix_UB_22      -0.0214451000
_diffrn_orient_matrix_UB_23      0.0364226000
_diffrn_orient_matrix_UB_31      0.0558596000
_diffrn_orient_matrix_UB_32      0.0404490000
_diffrn_orient_matrix_UB_33      -0.0041274000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8207
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.337
_diffrn_reflns_theta_min         3.619
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80280
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_coef       0.0005(6)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0518P)^2^+0.5624P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.712
_reflns_Friedel_fraction_max     0.539
_reflns_number_gt                3274
_reflns_number_total             3531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02878_si_006.cif
_cod_data_source_block           exp_2414
_cod_original_cell_volume        1807.53(12)
_cod_database_code               4035969
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C22 H21 N3 O2'
_chemical_oxdiff_usercomment     Raed-1982
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.74
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B), C00M(H00C,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00J(H00J), C00P(H00P),
 C00R(H00T)
2.d Idealised Me refined as rotating group:
 C00N(H00I,H00K,H00L), C00O(H00M,H00N,H00O), C00Q(H00Q,H00R,H00S)
;
_shelx_res_checksum              70817
_shelx_hkl_checksum              3589
_olex2_date_sample_data_collection 2018-09-12
_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 1.158
_oxdiff_exptl_absorpt_empirical_full_min 0.863