#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:38:39 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298050 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134077.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134077
loop_
_publ_author_name
'Velichko, Viktoria'
'Moi, Davide'
'Soddu, Francesco'
'Scipione, Roberto'
'Podda, Enrico'
'Luridiana, Alberto'
'Cambie, Dario'
'Secci, Francesco'
'Cabua, Maria Chiara'
_publ_section_title
;
 Two-step continuous flow-driven synthesis of 1,1-cyclopropane
 aminoketones.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1391
_journal_page_last               1394
_journal_paper_doi               10.1039/d4cc04089a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C17 H22 N2 O'
_chemical_formula_sum            'C17 H22 N2 O'
_chemical_formula_weight         270.36
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-23
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-25 deposited with the CCDC.	2024-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.1140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9369(3)
_cell_length_b                   16.1988(5)
_cell_length_c                   8.7551(2)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.280
_cell_measurement_theta_min      2.276
_cell_volume                     1522.00(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            37962
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         2.684
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1409 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.8651.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0388
_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/[σ²(Fo²)+(0.0393P)²+0.6721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3361
_reflns_number_total             3780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc04089a2.cif
_cod_data_source_block           5t
_cod_depositor_comments
'Adding full bibliography for 7134074--7134077.cif.'
_cod_database_code               7134077
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C4(H4A,H4B), C8(H8A,H8B)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C11(H11), C14(H14), C15(H15)
1.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.02560(7) 0.58590(5) 0.85713(9) 0.01862(17) Uani 1 1 d . . . . .
H1 H -0.0295(14) 0.5815(9) 0.9213(18) 0.028 Uiso 1 1 d . U . . .
N1 N 0.16946(8) 0.42678(5) 0.98626(10) 0.01731(18) Uani 1 1 d . . . . .
N2 N 0.11551(9) 0.40661(6) 0.46282(11) 0.0203(2) Uani 1 1 d . . . . .
H2 H 0.0605(14) 0.4180(9) 0.3745(18) 0.024 Uiso 1 1 d . U . . .
C1 C 0.21057(10) 0.49678(6) 0.95888(11) 0.0166(2) Uani 1 1 d . . . . .
C12 C 0.24239(10) 0.40185(6) 0.47632(12) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.14763(10) 0.58142(6) 0.94564(12) 0.0171(2) Uani 1 1 d . . . . .
C13 C 0.31778(11) 0.42816(7) 0.37434(12) 0.0201(2) Uani 1 1 d . . . . .
H13 H 0.2836 0.4558 0.2801 0.024 Uiso 1 1 calc R U . . .
C17 C 0.29164(10) 0.36148(6) 0.61811(12) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.18779(10) 0.34123(6) 0.69010(12) 0.0192(2) Uani 1 1 d . . . . .
C16 C 0.42022(11) 0.34683(7) 0.65674(13) 0.0219(2) Uani 1 1 d . . . . .
H16 H 0.4555 0.3199 0.7514 0.026 Uiso 1 1 calc R U . . .
C9 C 0.19438(12) 0.29934(7) 0.84401(13) 0.0228(2) Uani 1 1 d . . . . .
H9A H 0.2460 0.2490 0.8470 0.027 Uiso 1 1 calc R U . . .
H9B H 0.1095 0.2821 0.8541 0.027 Uiso 1 1 calc R U . . .
C4 C 0.32893(10) 0.53186(7) 0.91691(14) 0.0223(2) Uani 1 1 d . . . . .
H4A H 0.3599 0.5004 0.8352 0.027 Uiso 1 1 calc R U . . .
H4B H 0.3965 0.5423 1.0077 0.027 Uiso 1 1 calc R U . . .
C11 C 0.08389(11) 0.36890(7) 0.59143(13) 0.0222(2) Uani 1 1 d . . . . .
H11 H 0.0012 0.3631 0.6087 0.027 Uiso 1 1 calc R U . . .
C8 C 0.24929(11) 0.35448(6) 0.98245(12) 0.0204(2) Uani 1 1 d . . . . .
H8A H 0.2559 0.3229 1.0805 0.024 Uiso 1 1 calc R U . . .
H8B H 0.3340 0.3725 0.9731 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25182(10) 0.61022(7) 0.85554(13) 0.0207(2) Uani 1 1 d . . . . .
C14 C 0.44397(11) 0.41250(7) 0.41524(14) 0.0243(2) Uani 1 1 d . . . . .
H14 H 0.4974 0.4294 0.3475 0.029 Uiso 1 1 calc R U . . .
C5 C 0.15489(12) 0.62004(7) 1.10600(13) 0.0253(2) Uani 1 1 d . . . . .
H5A H 0.1309 0.6783 1.0943 0.038 Uiso 1 1 calc R U . . .
H5B H 0.2403 0.6157 1.1653 0.038 Uiso 1 1 calc R U . . .
H5C H 0.0981 0.5909 1.1615 0.038 Uiso 1 1 calc R U . . .
C15 C 0.49480(11) 0.37216(7) 0.55501(14) 0.0259(2) Uani 1 1 d . . . . .
H15 H 0.5820 0.3621 0.5800 0.031 Uiso 1 1 calc R U . . .
C7 C 0.20602(11) 0.60481(8) 0.68014(13) 0.0250(2) Uani 1 1 d . . . . .
H7A H 0.1668 0.5510 0.6537 0.038 Uiso 1 1 calc R U . . .
H7B H 0.2767 0.6113 0.6273 0.038 Uiso 1 1 calc R U . . .
H7C H 0.1451 0.6487 0.6465 0.038 Uiso 1 1 calc R U . . .
C6 C 0.31368(12) 0.69321(8) 0.89940(17) 0.0319(3) Uani 1 1 d . . . . .
H6A H 0.2524 0.7375 0.8713 0.048 Uiso 1 1 calc R U . . .
H6B H 0.3823 0.7010 0.8434 0.048 Uiso 1 1 calc R U . . .
H6C H 0.3463 0.6947 1.0118 0.048 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.2(10) . . ?
C1 N1 C8 118.62(9) . . ?
C12 N2 H2 125.5(9) . . ?
C12 N2 C11 108.22(9) . . ?
C11 N2 H2 123.9(9) . . ?
N1 C1 C2 130.52(10) . . ?
N1 C1 C4 137.17(10) . . ?
C4 C1 C2 92.20(8) . . ?
N2 C12 C13 129.87(10) . . ?
N2 C12 C17 108.02(9) . . ?
C13 C12 C17 122.09(10) . . ?
O1 C2 C1 116.91(8) . . ?
O1 C2 C3 114.12(8) . . ?
O1 C2 C5 111.13(9) . . ?
C1 C2 C3 86.85(8) . . ?
C5 C2 C1 110.81(8) . . ?
C5 C2 C3 115.15(9) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 C12 117.57(10) . . ?
C14 C13 H13 121.2 . . ?
C12 C17 C10 106.89(9) . . ?
C16 C17 C12 118.99(10) . . ?
C16 C17 C10 134.07(10) . . ?
C17 C10 C9 126.30(10) . . ?
C11 C10 C17 106.22(9) . . ?
C11 C10 C9 127.48(10) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 118.94(10) . . ?
C15 C16 H16 120.5 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C10 C9 C8 113.03(9) . . ?
H9A C9 H9B 107.8 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C1 C4 H4A 114.0 . . ?
C1 C4 H4B 114.0 . . ?
C1 C4 C3 87.62(8) . . ?
H4A C4 H4B 111.2 . . ?
C3 C4 H4A 114.0 . . ?
C3 C4 H4B 114.0 . . ?
N2 C11 H11 124.7 . . ?
C10 C11 N2 110.64(10) . . ?
C10 C11 H11 124.7 . . ?
N1 C8 C9 109.86(9) . . ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C4 C3 C2 88.95(8) . . ?
C7 C3 C2 111.01(9) . . ?
C7 C3 C4 110.56(10) . . ?
C6 C3 C2 117.69(10) . . ?
C6 C3 C4 116.58(9) . . ?
C6 C3 C7 110.45(10) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.30(11) . . ?
C15 C14 H14 119.3 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C16 C15 C14 121.10(11) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.903(15) . ?
O1 C2 1.4101(12) . ?
N1 C1 1.2598(14) . ?
N1 C8 1.4650(13) . ?
N2 H2 0.903(15) . ?
N2 C12 1.3720(14) . ?
N2 C11 1.3822(14) . ?
C1 C2 1.5285(14) . ?
C1 C4 1.5221(15) . ?
C12 C13 1.3937(15) . ?
C12 C17 1.4146(14) . ?
C2 C3 1.5763(15) . ?
C2 C5 1.5251(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3808(16) . ?
C17 C10 1.4391(15) . ?
C17 C16 1.4017(15) . ?
C10 C9 1.4979(14) . ?
C10 C11 1.3638(16) . ?
C16 H16 0.9500 . ?
C16 C15 1.3809(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.5320(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5610(15) . ?
C11 H11 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C3 C7 1.5232(16) . ?
C3 C6 1.5206(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.4040(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C15 H15 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -133.65(9) . . . . ?
O1 C2 C3 C7 -21.98(12) . . . . ?
O1 C2 C3 C6 106.64(11) . . . . ?
N1 C1 C2 O1 -45.16(15) . . . . ?
N1 C1 C2 C3 -160.69(11) . . . . ?
N1 C1 C2 C5 83.56(14) . . . . ?
N1 C1 C4 C3 160.14(13) . . . . ?
N2 C12 C13 C14 -177.53(11) . . . . ?
N2 C12 C17 C10 0.43(11) . . . . ?
N2 C12 C17 C16 178.14(9) . . . . ?
C1 N1 C8 C9 -112.16(11) . . . . ?
C1 C2 C3 C4 -15.48(8) . . . . ?
C1 C2 C3 C7 96.18(10) . . . . ?
C1 C2 C3 C6 -135.20(10) . . . . ?
C1 C4 C3 C2 15.54(8) . . . . ?
C1 C4 C3 C7 -96.55(9) . . . . ?
C1 C4 C3 C6 136.24(10) . . . . ?
C12 N2 C11 C10 1.30(13) . . . . ?
C12 C13 C14 C15 -0.51(17) . . . . ?
C12 C17 C10 C9 -178.75(10) . . . . ?
C12 C17 C10 C11 0.34(12) . . . . ?
C12 C17 C16 C15 -0.10(15) . . . . ?
C2 C1 C4 C3 -16.05(8) . . . . ?
C13 C12 C17 C10 -178.26(9) . . . . ?
C13 C12 C17 C16 -0.55(15) . . . . ?
C13 C14 C15 C16 -0.12(18) . . . . ?
C17 C12 C13 C14 0.85(15) . . . . ?
C17 C10 C9 C8 71.11(14) . . . . ?
C17 C10 C11 N2 -1.00(12) . . . . ?
C17 C16 C15 C14 0.43(17) . . . . ?
C10 C17 C16 C15 176.85(11) . . . . ?
C10 C9 C8 N1 62.47(12) . . . . ?
C16 C17 C10 C9 4.03(19) . . . . ?
C16 C17 C10 C11 -176.87(12) . . . . ?
C9 C10 C11 N2 178.08(10) . . . . ?
C4 C1 C2 O1 131.43(9) . . . . ?
C4 C1 C2 C3 15.90(8) . . . . ?
C4 C1 C2 C5 -99.85(10) . . . . ?
C11 N2 C12 C13 177.51(11) . . . . ?
C11 N2 C12 C17 -1.04(12) . . . . ?
C11 C10 C9 C8 -107.79(13) . . . . ?
C8 N1 C1 C2 176.15(10) . . . . ?
C8 N1 C1 C4 1.16(18) . . . . ?
C5 C2 C3 C4 96.06(10) . . . . ?
C5 C2 C3 C7 -152.27(10) . . . . ?
C5 C2 C3 C6 -23.66(14) . . . . ?
