#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/50/45/1504571.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_1504571
loop_
_publ_author_name
'Lee, Ernest E.'
'Rovis, Tomislav'
_publ_section_title
;
 Enantioselective synthesis of indolizidines bearing quaternary
 substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of
 alkenyl isocyanates and terminal alkynes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1231
_journal_page_last               1234
_journal_paper_doi               10.1021/ol800086s
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H16 Br N O'
_chemical_formula_weight         306.20
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXTL'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.7025(3)
_cell_length_b                   6.7025(3)
_cell_length_c                   59.243(6)
_cell_measurement_reflns_used    2682
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      3.06
_cell_volume                     2661.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex2 CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       82
_diffrn_reflns_limit_l_min       -82
_diffrn_reflns_number            18022
_diffrn_reflns_theta_full        29.90
_diffrn_reflns_theta_max         29.90
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    3.076
_exptl_absorpt_correction_T_max  0.7383
_exptl_absorpt_correction_T_min  0.4807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.027(13)
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0330P)^2^+0.9658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                3065
_reflns_number_total             3849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800086s-file002.cif
_cod_data_source_block           rovis24
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P4(3)2(1)2
_cod_database_code               1504571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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
Br1 Br 0.49174(5) 0.85226(5) 0.093671(5) 0.02982(10) Uani 1 1 d .
N1 N 0.2566(4) 1.2187(4) 0.19797(4) 0.0180(5) Uani 1 1 d .
O1 O 0.5253(4) 1.7509(3) 0.21236(4) 0.0306(6) Uani 1 1 d .
C1 C 0.1037(5) 1.0685(5) 0.19237(6) 0.0225(7) Uani 1 1 d .
H1A H 0.1647 0.9423 0.1883 0.027 Uiso 1 1 calc R
H1B H 0.0203 1.1134 0.1800 0.027 Uiso 1 1 calc R
C2 C -0.0169(6) 1.0491(5) 0.21412(6) 0.0387(9) Uani 1 1 d .
H2A H -0.1567 1.0258 0.2108 0.046 Uiso 1 1 calc R
H2B H 0.0327 0.9398 0.2233 0.046 Uiso 1 1 calc R
C3 C 0.0105(6) 1.2440(5) 0.22602(6) 0.0337(8) Uani 1 1 d .
H3A H -0.0088 1.2284 0.2421 0.040 Uiso 1 1 calc R
H3B H -0.0834 1.3425 0.2204 0.040 Uiso 1 1 calc R
C4 C 0.2247(5) 1.3066(5) 0.22081(5) 0.0199(7) Uani 1 1 d .
C5 C 0.2491(5) 1.5323(4) 0.21944(5) 0.0220(7) Uani 1 1 d .
H5A H 0.1357 1.5885 0.2115 0.026 Uiso 1 1 calc R
H5B H 0.2502 1.5870 0.2346 0.026 Uiso 1 1 calc R
C6 C 0.4399(5) 1.5933(4) 0.20737(6) 0.0226(7) Uani 1 1 d .
C7 C 0.4999(5) 1.4657(4) 0.18927(5) 0.0207(6) Uani 1 1 d .
H7A H 0.6117 1.4989 0.1808 0.025 Uiso 1 1 calc R
C8 C 0.3952(4) 1.2944(4) 0.18416(5) 0.0164(6) Uani 1 1 d .
C9 C 0.4291(4) 1.1871(4) 0.16247(5) 0.0176(6) Uani 1 1 d .
C10 C 0.3962(4) 1.2857(4) 0.14229(5) 0.0191(6) Uani 1 1 d .
H10A H 0.3620 1.4201 0.1426 0.023 Uiso 1 1 calc R
C11 C 0.4132(4) 1.1885(5) 0.12162(5) 0.0216(7) Uani 1 1 d .
H11A H 0.3889 1.2553 0.1081 0.026 Uiso 1 1 calc R
C12 C 0.4673(4) 0.9893(5) 0.12177(5) 0.0218(6) Uani 1 1 d .
C13 C 0.5093(5) 0.8881(4) 0.14146(5) 0.0231(6) Uani 1 1 d .
H13A H 0.5507 0.7557 0.1410 0.028 Uiso 1 1 calc R
C14 C 0.4890(4) 0.9870(5) 0.16193(5) 0.0212(6) Uani 1 1 d .
H14A H 0.5153 0.9200 0.1754 0.025 Uiso 1 1 calc R
C15 C 0.3769(5) 1.2178(5) 0.23729(5) 0.0286(8) Uani 1 1 d .
H15A H 0.3593 1.0758 0.2381 0.043 Uiso 1 1 calc R
H15B H 0.3573 1.2746 0.2520 0.043 Uiso 1 1 calc R
H15C H 0.5094 1.2474 0.2321 0.043 Uiso 1 1 calc R
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
Br1 0.02260(16) 0.0419(2) 0.02497(16) -0.01661(15) 0.00241(15) -0.00124(14)
N1 0.0209(13) 0.0185(12) 0.0145(13) -0.0018(11) 0.0002(11) -0.0032(10)
O1 0.0473(15) 0.0189(11) 0.0256(12) -0.0037(9) -0.0052(12) -0.0063(10)
C1 0.0253(16) 0.0226(15) 0.0196(16) -0.0032(13) 0.0011(14) -0.0051(12)
C2 0.041(2) 0.039(2) 0.037(2) -0.0103(16) 0.0202(19) -0.0127(18)
C3 0.0313(18) 0.0400(19) 0.0298(19) -0.0064(15) 0.0110(17) -0.0125(16)
C4 0.0255(15) 0.0217(16) 0.0125(15) -0.0018(12) 0.0029(12) -0.0021(13)
C5 0.0302(16) 0.0209(16) 0.0150(14) -0.0051(12) -0.0001(12) 0.0025(13)
C6 0.0329(18) 0.0158(14) 0.0190(16) 0.0006(13) -0.0079(14) -0.0014(12)
C7 0.0222(13) 0.0204(14) 0.0194(15) -0.0003(12) -0.0009(14) -0.0047(13)
C8 0.0192(14) 0.0162(14) 0.0137(14) 0.0025(11) -0.0017(11) 0.0006(11)
C9 0.0148(12) 0.0201(15) 0.0181(14) -0.0024(12) 0.0001(11) -0.0027(10)
C10 0.0175(14) 0.0197(15) 0.0201(15) 0.0004(12) 0.0031(12) 0.0033(11)
C11 0.0191(14) 0.0309(19) 0.0149(15) -0.0013(13) 0.0012(12) 0.0025(13)
C12 0.0172(14) 0.0327(16) 0.0157(15) -0.0081(14) 0.0029(11) -0.0020(14)
C13 0.0230(15) 0.0204(14) 0.0260(15) -0.0057(12) 0.0021(15) 0.0029(12)
C14 0.0216(13) 0.0227(14) 0.0192(15) 0.0033(13) -0.0005(13) -0.0009(14)
C15 0.045(2) 0.0222(16) 0.0184(16) 0.0022(13) -0.0039(15) -0.0007(15)
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'
Br Br -0.2901 2.4595 '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
C8 N1 C1 127.1(3)
C8 N1 C4 120.3(2)
C1 N1 C4 112.0(2)
N1 C1 C2 103.7(3)
C3 C2 C1 105.0(3)
C2 C3 C4 105.1(3)
N1 C4 C3 102.1(2)
N1 C4 C5 109.2(2)
C3 C4 C5 112.6(3)
N1 C4 C15 109.2(3)
C3 C4 C15 113.0(3)
C5 C4 C15 110.3(3)
C6 C5 C4 112.5(2)
O1 C6 C7 124.0(3)
O1 C6 C5 120.4(3)
C7 C6 C5 115.4(3)
C8 C7 C6 121.3(3)
N1 C8 C7 122.3(3)
N1 C8 C9 116.8(3)
C7 C8 C9 120.9(3)
C10 C9 C14 118.9(3)
C10 C9 C8 119.4(3)
C14 C9 C8 121.7(3)
C9 C10 C11 121.6(3)
C12 C11 C10 117.9(3)
C13 C12 C11 122.3(3)
C13 C12 Br1 118.9(2)
C11 C12 Br1 118.8(2)
C12 C13 C14 119.0(3)
C13 C14 C9 120.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.908(3)
N1 C8 1.338(4)
N1 C1 1.474(4)
N1 C4 1.491(4)
O1 C6 1.237(4)
C1 C2 1.526(4)
C2 C3 1.496(5)
C3 C4 1.527(5)
C4 C5 1.524(4)
C4 C15 1.533(4)
C5 C6 1.521(5)
C6 C7 1.429(4)
C7 C8 1.380(4)
C8 C9 1.490(4)
C9 C10 1.384(4)
C9 C14 1.400(4)
C10 C11 1.392(4)
C11 C12 1.384(4)
C12 C13 1.379(4)
C13 C14 1.389(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038640
