#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/31/7213133.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213133
loop_
_publ_author_name
'Ariffin, Azhar'
'Blake, Alexander J.'
'Ebden, Mark R.'
'Li, Wan-Sheung'
'Simpkins, Nigel S.'
'Fox, David N. A.'
_publ_section_title
;
 The diastereoselective and enantioselective substitution reactions of an
 isoindoline--borane complex
;
_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2439
_journal_paper_doi               10.1039/a904788c
_journal_year                    1999
_chemical_formula_sum            'C12 H18 I N'
_chemical_formula_weight         303.17
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.22(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.639(3)
_cell_length_b                   7.619(4)
_cell_length_c                   9.731(4)
_cell_measurement_reflns_used    35
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      16.5
_cell_measurement_theta_min      13.2
_cell_volume                     635.4(5)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997a)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997a)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997b)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       omega/theta
_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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3969
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.41
_diffrn_standards_decay_%        3.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_correction_T_min  0.334
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.41
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(3)
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2227
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0127
_refine_ls_R_factor_gt           0.0125
_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/[σ²(Fo²)+(0.017P)²+0.27P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0317
_refine_ls_wR_factor_ref         0.0318
_reflns_number_gt                2207
_reflns_number_total             2227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            904788csup1.cif
_cod_data_source_block           Compound_7
_cod_depositor_comments
;
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.017P)^2^+0.27P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.017P)^2^+0.27P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               7213133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_calc_flag
_atom_site_refinement_flags
C1 C 0.2883(6) 0.6575(6) 0.7263(5) 0.0194(8) Uani 1 d U
H1 H 0.2559 0.5614 0.7865 0.023 Uiso 1 calc R
C1' C 0.2859(3) 0.5884(4) 0.5778(2) 0.0267(5) Uani 1 d U
H1'A H 0.1781 0.5537 0.5412 0.032 Uiso 1 calc R
H1'B H 0.3187 0.6831 0.5181 0.032 Uiso 1 calc R
C1" C 0.3941(3) 0.4312(4) 0.5726(3) 0.0380(6) Uani 1 d U
H1"A H 0.3921 0.3922 0.4764 0.057 Uiso 1 calc R
H1"B H 0.3590 0.3353 0.6283 0.057 Uiso 1 calc R
H1"C H 0.5007 0.4649 0.6096 0.057 Uiso 1 calc R
N2 N 0.17917(17) 0.8158(7) 0.73364(16) 0.0177(4) Uani 1 d U
C2' C 0.1355(2) 0.8240(9) 0.87841(17) 0.0220(3) Uani 1 d U
H2'A H 0.0694 0.7232 0.8942 0.033 Uiso 1 calc R
H2'B H 0.0782 0.9330 0.8901 0.033 Uiso 1 calc R
H2'C H 0.2303 0.8212 0.9452 0.033 Uiso 1 calc R
C2" C 0.0303(2) 0.8155(9) 0.6362(2) 0.0257(6) Uani 1 d U
H2"A H -0.0309 0.7111 0.6531 0.039 Uiso 1 calc R
H2"B H 0.0545 0.8139 0.5404 0.039 Uiso 1 calc R
H2"C H -0.0300 0.9211 0.6513 0.039 Uiso 1 calc R
C3 C 0.2770(6) 0.9748(6) 0.7080(5) 0.0237(9) Uani 1 d U
H3A H 0.2433 1.0807 0.7552 0.028 Uiso 1 calc R
H3B H 0.2753 0.9992 0.6079 0.028 Uiso 1 calc R
C4 C 0.4394(5) 0.9093(9) 0.7745(5) 0.0202(11) Uani 1 d U
C5 C 0.5688(6) 1.0130(7) 0.8260(6) 0.0298(11) Uani 1 d U
H5 H 0.5656 1.1374 0.8201 0.036 Uiso 1 calc R
C6 C 0.7020(6) 0.9248(6) 0.8862(6) 0.0338(11) Uani 1 d U
H6 H 0.7939 0.9887 0.9182 0.041 Uiso 1 calc R
C7 C 0.6994(6) 0.7442(7) 0.8990(6) 0.0327(10) Uani 1 d U
H7 H 0.7890 0.6860 0.9442 0.039 Uiso 1 calc R
C8 C 0.5704(7) 0.6455(7) 0.8480(7) 0.0311(11) Uani 1 d U
H8 H 0.5733 0.5211 0.8549 0.037 Uiso 1 calc R
C9 C 0.4394(5) 0.7279(8) 0.7880(6) 0.0190(9) Uani 1 d U
I I 0.946869(12) 1.32676(18) 0.767881(10) 0.02337(6) Uani 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 0.0194(16) 0.0203(14) 0.0184(16) 0.0007(12) 0.0019(12) 0.0076(11)
C1' 0.0276(12) 0.0303(12) 0.0223(12) -0.0039(10) 0.0031(10) -0.0001(10)
C1" 0.0469(16) 0.0309(15) 0.0387(15) -0.0101(12) 0.0148(12) 0.0052(12)
N2 0.0161(6) 0.0204(11) 0.0163(7) 0.0028(14) 0.0015(5) -0.0038(14)
C2' 0.0191(8) 0.0292(9) 0.0184(8) -0.004(3) 0.0049(6) 0.001(3)
C2" 0.0192(8) 0.0349(16) 0.0212(8) 0.0004(19) -0.0044(7) 0.0047(19)
C3 0.0186(17) 0.0225(17) 0.031(2) 0.0043(14) 0.0047(14) 0.0042(13)
C4 0.0157(17) 0.024(2) 0.021(2) -0.0045(11) 0.0049(14) -0.0021(12)
C5 0.0213(18) 0.0232(19) 0.047(3) -0.0090(16) 0.0133(16) -0.0061(14)
C6 0.022(2) 0.0376(19) 0.043(3) -0.0151(18) 0.0073(17) -0.0131(17)
C7 0.0140(17) 0.0475(19) 0.036(2) 0.0015(17) 0.0012(16) -0.0015(16)
C8 0.025(2) 0.025(2) 0.042(2) 0.0021(16) 0.0028(17) 0.0030(15)
C9 0.0235(18) 0.0131(16) 0.0219(17) -0.0001(15) 0.0092(13) -0.0035(11)
I 0.02708(8) 0.02406(8) 0.01971(8) -0.00115(12) 0.00580(4) -0.00243(14)
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'
I I -0.4742 1.8119 '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
C9 C1 C1' 114.6(4)
C9 C1 N2 102.3(4)
C1' C1 N2 112.2(3)
C1" C1' C1 111.4(2)
C2" N2 C2' 107.23(14)
C2" N2 C3 110.5(4)
C2' N2 C3 109.4(4)
C2" N2 C1 116.8(4)
C2' N2 C1 107.7(4)
C3 N2 C1 105.14(15)
N2 C3 C4 99.7(4)
C9 C4 C5 122.3(6)
C9 C4 C3 110.4(5)
C5 C4 C3 127.1(6)
C6 C5 C4 117.1(6)
C7 C6 C5 119.7(6)
C6 C7 C8 122.0(6)
C9 C8 C7 119.5(6)
C8 C9 C4 119.4(6)
C8 C9 C1 131.0(6)
C4 C9 C1 109.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C9 1.468(7)
C1 C1' 1.535(5)
C1 N2 1.539(6)
C1' C1" 1.524(3)
N2 C2" 1.499(2)
N2 C2' 1.505(2)
N2 C3 1.516(6)
C3 C4 1.551(6)
C4 C9 1.388(4)
C4 C5 1.409(8)
C5 C6 1.396(8)
C6 C7 1.382(4)
C7 C8 1.384(8)
C8 C9 1.360(8)
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
C9 C1 C1' C1" 64.2(5)
N2 C1 C1' C1" -179.8(3)
C9 C1 N2 C2" 158.5(4)
C1' C1 N2 C2" 35.2(5)
C9 C1 N2 C2' -80.8(5)
C1' C1 N2 C2' 155.8(3)
C9 C1 N2 C3 35.7(4)
C1' C1 N2 C3 -87.6(4)
C2" N2 C3 C4 -159.2(3)
C2' N2 C3 C4 83.0(4)
C1 N2 C3 C4 -32.3(3)
N2 C3 C4 C9 18.4(6)
N2 C3 C4 C5 -156.8(5)
C9 C4 C5 C6 3.1(9)
C3 C4 C5 C6 177.8(5)
C4 C5 C6 C7 -3.2(10)
C5 C6 C7 C8 3.1(13)
C6 C7 C8 C9 -2.6(11)
C7 C8 C9 C4 2.3(10)
C7 C8 C9 C1 180.0(6)
C5 C4 C9 C8 -2.7(12)
C3 C4 C9 C8 -178.1(5)
C5 C4 C9 C1 179.2(4)
C3 C4 C9 C1 3.7(8)
C1' C1 C9 C8 -80.3(8)
N2 C1 C9 C8 158.1(6)
C1' C1 C9 C4 97.6(6)
N2 C1 C9 C4 -24.1(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197808
