N-Heterocyclic Carbene-catalysed Homoenolate Addition Reaction to 3-Cyano-2-imino-2H-chromenes: Synthesis of C4-Functionalized 2-Amino-3-cyano-4H-chromene
Maji, Biswajit; Shukla, Pushpendra Mani; Pratap, Aniruddh; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01447E

data_7158916
_publ_section_title
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 &#x000D; N-Heterocyclic Carbene-catalysed Homoenolate Addition Reaction
 to 3-Cyano-2-imino-2H-chromenes: Synthesis of C4-Functionalized
 2-Amino-3-cyano-4H-chromene
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01447E
_journal_year                    2022
_chemical_formula_moiety         'C24 H19 Br N2 O3, C H Cl'
_chemical_formula_sum            'C25 H20 Br Cl N2 O3'
_chemical_formula_weight         511.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-08-08 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.610(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.486(3)
_cell_length_b                   14.311(3)
_cell_length_c                   24.277(6)
_cell_measurement_reflns_used    8705
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.85
_cell_volume                     4619.7(18)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1330
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            67246
_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         28.719
_diffrn_reflns_theta_min         2.091
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.925
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4883
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1289 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.6546.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'whiteish colourless'
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       cube
_exptl_crystal_F_000             2080
_refine_diff_density_max         1.263
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0465P)^2^+20.9694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4087
_reflns_number_total             5977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01447e2.cif
_cod_data_source_block           f1
_cod_original_cell_volume        4620(2)
_cod_database_code               7158916
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N006(H00A,H00B)
2.b Ternary CH refined with riding coordinates:
 C00C(H00D), C00J(H00J), C0AA(H0AA)
2.c Secondary CH2 refined with riding coordinates:
 C00L(H00F,H00G)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00D(H00E), C00H(H00H), C00K(H00K), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V)
2.e Idealised Me refined as rotating group:
 C00T(H00I,H00L,H00M)
;
_shelx_res_checksum              4894
_olex2_submission_special_instructions 'No special instructions were received'