#------------------------------------------------------------------------------
#$Date: 2025-08-18 14:30:32 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507739.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_1507739
loop_
_publ_author_name
'Tong, Benny Meng Kiat'
'Chen, Hui'
'Chong, Sin Yee'
'Heng, Yi Li'
'Chiba, Shunsuke'
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_section_title
;
 Formal [4 + 1]- and [5 + 1]-annulation by an s(n)2-conjugate addition
 sequence: stereoselective synthesis of highly substituted carbocycles.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2826
_journal_page_last               2829
_journal_paper_doi               10.1021/ol301044e
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H18 N2 O2'
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.252(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0332(5)
_cell_length_b                   6.9108(4)
_cell_length_c                   22.1287(12)
_cell_measurement_reflns_used    5280
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      31.08
_cell_measurement_theta_min      2.49
_cell_volume                     1499.40(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23354
_diffrn_reflns_theta_full        32.22
_diffrn_reflns_theta_max         32.22
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9723
_exptl_absorpt_correction_T_min  0.9676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+0.1796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                4009
_reflns_number_total             5277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301044e_si_005.cif
_cod_data_source_block           3la'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507739
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.27774(9) 0.25279(14) 0.30605(4) 0.01554(19) Uani 1 1 d .
C2 C 0.32148(10) 0.09135(14) 0.26253(4) 0.01534(19) Uani 1 1 d .
H2 H 0.4213 0.1059 0.2641 0.018 Uiso 1 1 calc R
C3 C 0.29951(10) -0.10023(15) 0.29380(4) 0.01661(19) Uani 1 1 d .
H3A H 0.3662 -0.1986 0.2867 0.020 Uiso 1 1 calc R
H3B H 0.2062 -0.1501 0.2777 0.020 Uiso 1 1 calc R
C4 C 0.32068(10) -0.05105(15) 0.36279(4) 0.01738(19) Uani 1 1 d .
H4 H 0.4195 -0.0223 0.3790 0.021 Uiso 1 1 calc R
C5 C 0.23984(11) 0.13825(15) 0.36073(4) 0.0186(2) Uani 1 1 d .
H5A H 0.2672 0.2105 0.4000 0.022 Uiso 1 1 calc R
H5B H 0.1406 0.1125 0.3529 0.022 Uiso 1 1 calc R
C6 C 0.16147(10) 0.37315(15) 0.27491(4) 0.01723(19) Uani 1 1 d .
C7 C 0.39521(10) 0.38075(15) 0.32985(4) 0.0181(2) Uani 1 1 d .
C8 C 0.24676(10) 0.10341(14) 0.19521(4) 0.01636(19) Uani 1 1 d .
H8A H 0.2710 -0.0105 0.1726 0.020 Uiso 1 1 calc R
H8B H 0.1472 0.0994 0.1931 0.020 Uiso 1 1 calc R
C9 C 0.28114(10) 0.28497(15) 0.16423(4) 0.01711(19) Uani 1 1 d .
C10 C 0.22315(12) 0.47240(18) 0.07216(5) 0.0263(2) Uani 1 1 d .
H10A H 0.2126 0.4471 0.0274 0.032 Uiso 1 1 calc R
H10B H 0.3134 0.5331 0.0875 0.032 Uiso 1 1 calc R
C11 C 0.11242(15) 0.6067(2) 0.08263(7) 0.0401(3) Uani 1 1 d .
H11A H 0.0237 0.5428 0.0698 0.060 Uiso 1 1 calc R
H11B H 0.1137 0.7248 0.0583 0.060 Uiso 1 1 calc R
H11C H 0.1277 0.6399 0.1266 0.060 Uiso 1 1 calc R
C12 C 0.27628(10) -0.20213(15) 0.40359(4) 0.0176(2) Uani 1 1 d .
C13 C 0.14535(11) -0.27967(16) 0.38967(5) 0.0206(2) Uani 1 1 d .
H13 H 0.0826 -0.2366 0.3538 0.025 Uiso 1 1 calc R
C14 C 0.10480(13) -0.41864(17) 0.42717(5) 0.0258(2) Uani 1 1 d .
H14 H 0.0151 -0.4704 0.4168 0.031 Uiso 1 1 calc R
C15 C 0.19500(13) -0.48220(17) 0.47980(5) 0.0279(3) Uani 1 1 d .
H15 H 0.1672 -0.5777 0.5054 0.033 Uiso 1 1 calc R
C16 C 0.32546(14) -0.40662(19) 0.49502(5) 0.0293(3) Uani 1 1 d .
H16 H 0.3872 -0.4494 0.5312 0.035 Uiso 1 1 calc R
C17 C 0.36631(12) -0.26689(18) 0.45692(5) 0.0248(2) Uani 1 1 d .
H17 H 0.4561 -0.2155 0.4674 0.030 Uiso 1 1 calc R
N1 N 0.06860(9) 0.46096(15) 0.25054(4) 0.0241(2) Uani 1 1 d .
N2 N 0.48847(9) 0.47267(15) 0.35064(4) 0.0254(2) Uani 1 1 d .
O1 O 0.35530(8) 0.41175(12) 0.18942(4) 0.02377(18) Uani 1 1 d .
O2 O 0.21509(8) 0.29131(11) 0.10467(3) 0.02306(18) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0156(4) 0.0141(4) 0.0163(4) -0.0007(3) 0.0021(3) 0.0005(3)
C2 0.0148(4) 0.0152(5) 0.0164(4) -0.0007(3) 0.0040(3) 0.0020(3)
C3 0.0186(4) 0.0154(5) 0.0161(4) 0.0014(3) 0.0044(3) 0.0034(3)
C4 0.0160(4) 0.0193(5) 0.0162(4) 0.0007(3) 0.0020(3) 0.0016(4)
C5 0.0223(5) 0.0177(5) 0.0168(4) -0.0007(4) 0.0066(4) 0.0005(4)
C6 0.0171(4) 0.0159(5) 0.0188(4) -0.0028(3) 0.0040(3) -0.0011(3)
C7 0.0185(4) 0.0180(5) 0.0176(4) 0.0000(3) 0.0030(4) 0.0023(4)
C8 0.0170(4) 0.0160(5) 0.0159(4) -0.0006(3) 0.0030(3) -0.0005(3)
C9 0.0162(4) 0.0193(5) 0.0161(4) 0.0009(3) 0.0040(3) 0.0026(4)
C10 0.0302(6) 0.0271(6) 0.0219(5) 0.0099(4) 0.0067(4) 0.0000(5)
C11 0.0398(7) 0.0337(7) 0.0506(8) 0.0215(6) 0.0183(6) 0.0092(6)
C12 0.0215(5) 0.0177(5) 0.0133(4) 0.0012(3) 0.0032(3) 0.0055(4)
C13 0.0232(5) 0.0198(5) 0.0185(4) 0.0029(4) 0.0034(4) 0.0022(4)
C14 0.0324(6) 0.0214(6) 0.0256(5) 0.0025(4) 0.0111(4) 0.0004(4)
C15 0.0444(7) 0.0211(6) 0.0219(5) 0.0055(4) 0.0159(5) 0.0086(5)
C16 0.0404(7) 0.0318(7) 0.0154(4) 0.0058(4) 0.0053(4) 0.0170(5)
C17 0.0255(5) 0.0309(6) 0.0164(4) 0.0015(4) 0.0010(4) 0.0087(4)
N1 0.0216(4) 0.0227(5) 0.0267(5) -0.0028(4) 0.0022(4) 0.0023(4)
N2 0.0217(4) 0.0289(5) 0.0246(5) -0.0033(4) 0.0022(4) -0.0027(4)
O1 0.0223(4) 0.0245(4) 0.0233(4) 0.0022(3) 0.0021(3) -0.0068(3)
O2 0.0304(4) 0.0213(4) 0.0159(3) 0.0031(3) 0.0015(3) -0.0016(3)
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
C7 C1 C6 108.66(8)
C7 C1 C5 109.55(8)
C6 C1 C5 110.43(8)
C7 C1 C2 109.44(8)
C6 C1 C2 113.77(8)
C5 C1 C2 104.90(8)
C8 C2 C3 113.67(8)
C8 C2 C1 114.29(8)
C3 C2 C1 104.33(7)
C8 C2 H2 108.1
C3 C2 H2 108.1
C1 C2 H2 108.1
C2 C3 C4 104.79(8)
C2 C3 H3A 110.8
C4 C3 H3A 110.8
C2 C3 H3B 110.8
C4 C3 H3B 110.8
H3A C3 H3B 108.9
C12 C4 C3 116.50(9)
C12 C4 C5 112.74(8)
C3 C4 C5 101.45(8)
C12 C4 H4 108.6
C3 C4 H4 108.6
C5 C4 H4 108.6
C4 C5 C1 103.97(8)
C4 C5 H5A 111.0
C1 C5 H5A 111.0
C4 C5 H5B 111.0
C1 C5 H5B 111.0
H5A C5 H5B 109.0
N1 C6 C1 177.67(11)
N2 C7 C1 176.39(11)
C9 C8 C2 112.27(8)
C9 C8 H8A 109.2
C2 C8 H8A 109.2
C9 C8 H8B 109.2
C2 C8 H8B 109.2
H8A C8 H8B 107.9
O1 C9 O2 123.82(9)
O1 C9 C8 124.99(9)
O2 C9 C8 111.16(8)
O2 C10 C11 109.54(9)
O2 C10 H10A 109.8
C11 C10 H10A 109.8
O2 C10 H10B 109.8
C11 C10 H10B 109.8
H10A C10 H10B 108.2
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 118.29(10)
C13 C12 C4 121.27(9)
C17 C12 C4 120.44(10)
C14 C13 C12 121.18(10)
C14 C13 H13 119.4
C12 C13 H13 119.4
C13 C14 C15 120.04(11)
C13 C14 H14 120.0
C15 C14 H14 120.0
C16 C15 C14 120.03(11)
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C17 119.80(10)
C15 C16 H16 120.1
C17 C16 H16 120.1
C12 C17 C16 120.66(11)
C12 C17 H17 119.7
C16 C17 H17 119.7
C9 O2 C10 116.45(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.4782(14)
C1 C6 1.4786(14)
C1 C5 1.5591(14)
C1 C2 1.5950(13)
C2 C8 1.5213(13)
C2 C3 1.5314(14)
C2 H2 1.0000
C3 C4 1.5343(13)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C12 1.5081(14)
C4 C5 1.5348(15)
C4 H4 1.0000
C5 H5A 0.9900
C5 H5B 0.9900
C6 N1 1.1463(14)
C7 N2 1.1437(14)
C8 C9 1.5045(14)
C8 H8A 0.9900
C8 H8B 0.9900
C9 O1 1.2067(12)
C9 O2 1.3443(12)
C10 O2 1.4543(13)
C10 C11 1.5027(19)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.3914(15)
C12 C17 1.3987(14)
C13 C14 1.3856(15)
C13 H13 0.9500
C14 C15 1.3860(16)
C14 H14 0.9500
C15 C16 1.3829(19)
C15 H15 0.9500
C16 C17 1.3993(17)
C16 H16 0.9500
C17 H17 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040247