Cu(OAc)<sub>2</sub>/DABCO-mediated domino reaction of vinyl malononitriles with cyclic sulfamidate imines: access to 6-hydroxyaryl-2-aminonicotinonitriles.
Goud, S. Banuprakash; Guin, Soumitra; Prakash, Meher; Samanta, Sampak; Organic & biomolecular chemistry 20 (2022) 352–357; doi:10.1039/d1ob02095a

data_7158436
_publ_section_title
;
 Cu(OAc)<sub>2</sub>/DABCO-mediated domino reaction of vinyl
 malononitriles with cyclic sulfamidate imines: access to
 6-hydroxyaryl-2-aminonicotinonitriles.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              352
_journal_page_last               357
_journal_paper_doi               10.1039/d1ob02095a
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H15 N3 O'
_chemical_formula_sum            'C15 H15 N3 O'
_chemical_formula_weight         253.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2021-11-15 deposited with the CCDC.	2021-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2949(2)
_cell_length_b                   11.9167(2)
_cell_length_c                   14.4321(3)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.22
_cell_volume                     1254.60(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         3.129
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9364.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       Block
_exptl_crystal_F_000             536
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1190 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2956
_reflns_number_total             3111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02095a2.cif
_cod_data_source_block           13nova_0m
_cod_depositor_comments
;
         Adding full bibliography for 7158436.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H30 N6 O2'
_cod_original_formula_weight         506.60
_cod_original_formula_moiety         '2(C15 H15 N3 O)'
_cod_original_formula_units_Z            2
_cod_database_code               7158436
_shelx_shelxl_version_number     2018/3
_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, All N(H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00B(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00K), C00D(H00L), C00G(H00M), C00H(H00N)
2.c Idealised Me refined as rotating group:
 C007(H00C,H00D,H00E), C009(H00F,H00G,H00H)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), N002(H00A)
;
_shelx_res_checksum              52755
_olex2_submission_special_instructions 'No special instructions were received'