Expansion of diazepine heterocyclic chemical space <i>via</i> sequential Knoevenagel condensation-intramolecular aza-Wittig reaction: 2-acyl-4-aryl-5<i>H</i>-pyrrolo[1,2-<i>d</i>][1,4]diazepines.
Dagar, Anuradha; Kim, Ikyon; Organic & biomolecular chemistry 18 (2020) 9836–9851; doi:10.1039/d0ob02002h

data_7157795
_publ_section_title
;
 Expansion of diazepine heterocyclic chemical space <i>via</i> sequential
 Knoevenagel condensation-intramolecular aza-Wittig reaction:
 2-acyl-4-aryl-5<i>H</i>-pyrrolo[1,2-<i>d</i>][1,4]diazepines.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9836
_journal_page_last               9851
_journal_paper_doi               10.1039/d0ob02002h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H18 N4 O4'
_chemical_formula_sum            'C18 H18 N4 O4'
_chemical_formula_weight         354.36
_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     direct
_audit_creation_date             2020-10-30
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2020-11-03 deposited with the CCDC.	2020-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.324(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1364(14)
_cell_length_b                   19.9122(18)
_cell_length_c                   8.5927(11)
_cell_measurement_reflns_used    1517
_cell_measurement_temperature    293.5(4)
_cell_measurement_theta_max      22.7720
_cell_measurement_theta_min      2.8350
_cell_volume                     1819.0(4)
_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
;
%$getVar(olex2_reference_short)%
;
_computing_publication_material
;
%$getVar(olex2_reference_short)%
;
_computing_structure_refinement
;
%$getVar(refinement_reference_short)%
;
_computing_structure_solution
;
%$getVar(solution_reference_short)%
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.5(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.846
_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    -18.00  91.00   1.00   53.59    --   11.67  19.00-120.00  109
  2  \w    -27.00  34.00   1.00   53.59    --   11.67 -38.00  30.00   61
;
_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      -0.0426265000
_diffrn_orient_matrix_UB_12      0.0263811000
_diffrn_orient_matrix_UB_13      -0.0343060000
_diffrn_orient_matrix_UB_21      -0.0458636000
_diffrn_orient_matrix_UB_22      -0.0147648000
_diffrn_orient_matrix_UB_23      0.0312172000
_diffrn_orient_matrix_UB_31      0.0233596000
_diffrn_orient_matrix_UB_32      0.0188358000
_diffrn_orient_matrix_UB_33      0.0728960000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8628
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.485
_diffrn_reflns_theta_min         2.172
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91066
_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            dark
_exptl_crystal_colour_modifier   dark
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0001(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1698
_refine_ls_R_factor_gt           0.0793
_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^)+(0.0602P)^2^+0.5978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1673
_refine_ls_wR_factor_ref         0.2083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1997
_reflns_number_total             4277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02002h2.cif
_cod_data_source_block           exp_1475
_cod_depositor_comments
'Adding full bibliography for 7157795--7157796.cif.'
_cod_database_code               7157795
_publ_section_exptl
;
Any special experimental details
;
_chemical_oxdiff_formula         C18H18N4O4
_diffrn_oxdiff_ac3_digest_frames
;
01d0ff79de5fbd2cddff3544631e8596b3000279554
;
_diffrn_oxdiff_ac3_digest_hkl
;
0162a1b4d6fe3855d15b1c5445ccde7e81b292
;
_reflns_odcompleteness_completeness 99.92
_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 Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00P(H00K,H00M)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J),
 C00L(H00L), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00O(H00C,H00F,H00G), C00Q(H00O,H00P,H00Q)
;
_shelx_shelxl_version_number     2018/3
_olex2_date_sample_data_collection 2020-10-29
_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 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.820