Bicyclic <i>N</i>-dihalocyclopropylamide derivatives as precursors of nitrogen-containing fused polycyclic systems.
Šlachtová, Veronika; Casaretto, Nicolas; Brulíková, Lucie; Six, Yvan; Organic & biomolecular chemistry 21 (2023) 6325–6341; doi:10.1039/d3ob00643c

data_7159412
_publ_section_title
;
 Bicyclic <i>N</i>-dihalocyclopropylamide derivatives as precursors of
 nitrogen-containing fused polycyclic systems.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6325
_journal_page_last               6341
_journal_paper_doi               10.1039/d3ob00643c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H19 N O4'
_chemical_formula_sum            'C16 H19 N O4'
_chemical_formula_weight         289.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-06 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.052(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6585(10)
_cell_length_b                   6.8558(8)
_cell_length_c                   12.0392(14)
_cell_measurement_reflns_used    2670
_cell_measurement_temperature    149.77
_cell_measurement_theta_max      27.448
_cell_measurement_theta_min      2.414
_cell_volume                     696.20(14)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.77
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0444
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.736
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0773 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9132.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2(3)
_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     387
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     649
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0491
_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^)+(0.0655P)^2^+0.2425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1352
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2377
_reflns_number_total             2852
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00643c3.cif
_cod_data_source_block           vs589a_sp1_1_0m
_cod_depositor_comments          'Adding full bibliography for 7159412.cif.'
_cod_database_code               7159412
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -1(3)
 2(3)
2. 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 O(H) groups
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.004 and sigma
for terminal atoms of 0.008 within 2A
4. Others
 Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=Sof(H4B)=Sof(N1B)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(H1BC)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(H2BC)=Sof(C3B)=Sof(C4B)=
 Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9BA)=
 Sof(H9BB)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C11B)=Sof(C12B)=Sof(H12B)=
 Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=
 Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(H4A)=Sof(N1A)=Sof(C1A)=Sof(H1AA)=
 Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(C4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(C10A)=Sof(H10A)=Sof(H10B)=Sof(C11A)=Sof(C12A)=Sof(H12A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=Sof(H16B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12A(H12A), C15A(H15A), C12B(H12B), C15B(H15B)
5.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C16A(H16A,H16B), C9B(H9BA,H9BB), C10B(H10C,
 H10D), C16B(H16C,H16D)
5.c Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C8A(H8A), C13A(H13A), C14A(H14A), C5B(H5B), C8B(H8B), C13B(H13B),
 C14B(H14B)
5.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,
 H2BC)
5.e Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O4B(H4B)
;
_shelx_res_checksum              57610
_olex2_submission_special_instructions 'No special instructions were received'