#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/38/7103889.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_7103889
loop_
_publ_author_name
'Davies, Stephen G.'
'Garner, A. Christopher'
'Nicholson, Rebecca L.'
'Osborne, James'
'Savory, Edward D.'
'Smith, Andrew D.'
_publ_section_title
;
 Double diastereoselective [3,3]-sigmatropic aza-Claisen rearrangements
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   17
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2134
_journal_page_last               2135
_journal_paper_doi               10.1039/b306323m
_journal_year                    2003
_chemical_formula_moiety         ' C24 H31 N1 O2 '
_chemical_formula_sum            'C24 H31 N O2'
_chemical_formula_weight         365.52
_chemical_melting_point          ?
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             00-11-02
_audit_creation_method           CRYSTALS_ver_12-03-99
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9041(8)
_cell_length_b                   14.4817(15)
_cell_length_c                   31.335(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      43
_cell_measurement_theta_min      23
_cell_volume                     2225.4
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2766
_diffrn_reflns_theta_max         74.33
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        3.50
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.53
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   'refined from delta-F (Walker & Stuart , 1983)'
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.09
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             794.02
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       195.1(153)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_ref   0.9426
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2107
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.012442
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters, Carruthers & Watkin , 1979, 
6.99     4.82     4.54    
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0747
_reflns_limit_h_max              6
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              39
_reflns_limit_l_min              0
_reflns_number_gt                2107
_reflns_number_total             2660
_reflns_threshold_expression     >3.00σ(I)
_cod_data_source_file            b306323m.txt
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
In the original b306323m.txt entry, the diffraction details and
software description tags were provided more than once, with
contradictory values. The comments in the file would say "# choose
from:", suggesting that only one block had to be chosen upon file
submission for publication, but the choice was apparently not
done. Since we do not have reliable information regarding what
hardware and software was used by the authors, the 
tags '_diffrn_measurement_device_type', '_diffrn_radiation_monochromator',
'_computing_data_reduction', '_computing_cell_refinement' and the like
were commented out and removed from COD files altogether.

Saulius Gra\<zulis
2009.09.20

The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic ' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        ' C24 H31 N1 O2 '
_cod_database_code               7103889
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
N1 0.2858(4) 0.00304(18) 0.34582(8) 0.0749 1.0000 Uani
C2 0.0973(5) -0.0616(2) 0.34122(9) 0.0716 1.0000 Uani
O3 -0.1493(4) -0.04248(18) 0.3390(1) 0.1058 1.0000 Uani
C4 0.1891(5) -0.1608(2) 0.33914(9) 0.0727 1.0000 Uani
C5 0.1272(6) -0.2011(2) 0.2949(1) 0.0787 1.0000 Uani
C6 0.2599(7) -0.1463(3) 0.26045(11) 0.0893 1.0000 Uani
C7 0.1483(8) -0.0927(4) 0.23274(13) 0.1131 1.0000 Uani
C8 0.281(1) -0.0354(3) 0.19823(13) 0.1145 1.0000 Uani
C9 0.162(1) -0.0498(3) 0.15710(13) 0.1149 1.0000 Uani
O10 0.2942(6) 0.0028(2) 0.12539(8) 0.1067 1.0000 Uani
C11 0.1701(11) -0.0037(4) 0.08584(15) 0.1246 1.0000 Uani
C12 0.3344(9) 0.0427(3) 0.05215(12) 0.0948 1.0000 Uani
C13 0.3270(15) 0.0097(3) 0.01085(15) 0.1303 1.0000 Uani
C14 0.4731(16) 0.0517(4) -0.02148(15) 0.1364 1.0000 Uani
C15 0.6313(13) 0.1265(5) -0.01174(17) 0.1378 1.0000 Uani
C16 0.6361(14) 0.1603(4) 0.02817(16) 0.1437 1.0000 Uani
C17 0.4887(11) 0.1187(4) 0.06020(14) 0.1194 1.0000 Uani
C18 0.2144(14) -0.3027(3) 0.29243(15) 0.1262 1.0000 Uani
C19 0.0514(12) -0.2146(3) 0.37508(12) 0.1163 1.0000 Uani
C20 0.2332(6) 0.1016(2) 0.34551(11) 0.0856 1.0000 Uani
C21 0.3409(6) 0.1502(2) 0.3846(1) 0.0742 1.0000 Uani
C22 0.525(1) 0.1128(2) 0.41168(12) 0.1018 1.0000 Uani
C23 0.6290(13) 0.1623(3) 0.44581(14) 0.1227 1.0000 Uani
C24 0.5460(11) 0.2490(3) 0.45366(15) 0.1149 1.0000 Uani
C25 0.3673(15) 0.2872(3) 0.4277(2) 0.1632 1.0000 Uani
C26 0.2636(12) 0.2386(3) 0.3934(2) 0.1448 1.0000 Uani
C27 0.3491(15) 0.1435(4) 0.30432(15) 0.1391 1.0000 Uani
H41 0.3913 -0.1662 0.3436 0.0809 1.0000 Uiso
H51 -0.0753 -0.1980 0.2897 0.0900 1.0000 Uiso
H61 0.4644 -0.1532 0.2585 0.0999 1.0000 Uiso
H71 -0.0573 -0.0836 0.2350 0.1209 1.0000 Uiso
H81 0.4799 -0.0518 0.1970 0.1286 1.0000 Uiso
H82 0.2684 0.0331 0.2058 0.1286 1.0000 Uiso
H91 0.1702 -0.1163 0.1497 0.1359 1.0000 Uiso
H92 -0.0368 -0.0299 0.1581 0.1359 1.0000 Uiso
H111 -0.0158 0.0272 0.0872 0.1442 1.0000 Uiso
H112 0.1423 -0.0699 0.0778 0.1442 1.0000 Uiso
H131 0.2158 -0.0484 0.0042 0.1456 1.0000 Uiso
H141 0.4680 0.0263 -0.0516 0.1627 1.0000 Uiso
H151 0.7481 0.1570 -0.0355 0.1605 1.0000 Uiso
H161 0.7444 0.2194 0.0357 0.1679 1.0000 Uiso
H171 0.4865 0.1482 0.0896 0.1402 1.0000 Uiso
H181 0.1769 -0.3297 0.2635 0.1449 1.0000 Uiso
H182 0.1190 -0.3406 0.3146 0.1449 1.0000 Uiso
H183 0.4192 -0.3080 0.2978 0.1449 1.0000 Uiso
H191 0.1080 -0.2812 0.3743 0.1321 1.0000 Uiso
H192 0.0994 -0.1877 0.4034 0.1321 1.0000 Uiso
H193 -0.1536 -0.2118 0.3714 0.1321 1.0000 Uiso
H201 0.0285 0.1111 0.3453 0.0968 1.0000 Uiso
H221 0.5898 0.0462 0.4071 0.1213 1.0000 Uiso
H231 0.7668 0.1312 0.4662 0.1462 1.0000 Uiso
H241 0.6221 0.2862 0.4781 0.1403 1.0000 Uiso
H251 0.3015 0.3534 0.4328 0.1837 1.0000 Uiso
H261 0.1309 0.2704 0.3735 0.1647 1.0000 Uiso
H271 0.3149 0.2115 0.3032 0.1606 1.0000 Uiso
H272 0.5538 0.1329 0.3035 0.1606 1.0000 Uiso
H273 0.2673 0.1135 0.2785 0.1606 1.0000 Uiso
H1 0.4269 -0.0204 0.3478 0.0500 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C   ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'N   ' 0.0290 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0470 0.0320 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C20 . 124.8(2) yes
C2 . N1 . H1 . 108.9(3) no
C20 . N1 . H1 . 126.3(3) no
N1 . C2 . O3 . 121.9(3) yes
N1 . C2 . C4 . 118.0(2) yes
O3 . C2 . C4 . 120.0(3) yes
C2 . C4 . C5 . 110.0(2) yes
C2 . C4 . C19 . 108.8(3) yes
C5 . C4 . C19 . 112.7(3) yes
C2 . C4 . H41 . 111.3(3) no
C5 . C4 . H41 . 106.9(2) no
C19 . C4 . H41 . 107.2(3) no
C4 . C5 . C6 . 111.4(3) yes
C4 . C5 . C18 . 110.8(3) yes
C6 . C5 . C18 . 110.7(3) yes
C4 . C5 . H51 . 108.9(3) no
C6 . C5 . H51 . 106.8(3) no
C18 . C5 . H51 . 108.0(3) no
C5 . C6 . C7 . 128.7(3) yes
C5 . C6 . H61 . 115.1(3) no
C7 . C6 . H61 . 116.2(3) no
C6 . C7 . C8 . 129.2(4) yes
C6 . C7 . H71 . 116.8(4) no
C8 . C7 . H71 . 113.9(4) no
C7 . C8 . C9 . 113.0(4) yes
C7 . C8 . H81 . 108.4(4) no
C9 . C8 . H81 . 109.2(4) no
C7 . C8 . H82 . 109.9(4) no
C9 . C8 . H82 . 109.1(4) no
H81 . C8 . H82 . 107.2(4) no
C8 . C9 . O10 . 111.6(4) yes
C8 . C9 . H91 . 109.6(4) no
O10 . C9 . H91 . 109.9(4) no
C8 . C9 . H92 . 108.9(4) no
O10 . C9 . H92 . 108.0(4) no
H91 . C9 . H92 . 108.8(4) no
C9 . O10 . C11 . 113.0(3) yes
O10 . C11 . C12 . 111.5(4) yes
O10 . C11 . H111 . 109.0(4) no
C12 . C11 . H111 . 108.4(4) no
O10 . C11 . H112 . 110.6(4) no
C12 . C11 . H112 . 109.2(4) no
H111 . C11 . H112 . 108.1(5) no
C11 . C12 . C13 . 119.6(4) yes
C11 . C12 . C17 . 122.4(4) yes
C13 . C12 . C17 . 118.0(4) yes
C12 . C13 . C14 . 121.4(5) yes
C12 . C13 . H131 . 119.3(5) no
C14 . C13 . H131 . 119.2(5) no
C13 . C14 . C15 . 118.6(5) yes
C13 . C14 . H141 . 120.7(7) no
C15 . C14 . H141 . 120.6(7) no
C14 . C15 . C16 . 120.4(5) yes
C14 . C15 . H151 . 119.4(6) no
C16 . C15 . H151 . 120.2(7) no
C15 . C16 . C17 . 120.7(5) yes
C15 . C16 . H161 . 121.6(6) no
C17 . C16 . H161 . 117.7(5) no
C12 . C17 . C16 . 120.8(4) yes
C12 . C17 . H171 . 120.2(5) no
C16 . C17 . H171 . 118.9(5) no
C5 . C18 . H181 . 111.6(4) no
C5 . C18 . H182 . 111.1(4) no
H181 . C18 . H182 . 109.1(4) no
C5 . C18 . H183 . 109.7(4) no
H181 . C18 . H183 . 107.5(5) no
H182 . C18 . H183 . 107.7(5) no
C4 . C19 . H191 . 110.5(4) no
C4 . C19 . H192 . 110.7(5) no
H191 . C19 . H192 . 109.3(4) no
C4 . C19 . H193 . 109.6(3) no
H191 . C19 . H193 . 108.1(5) no
H192 . C19 . H193 . 108.6(4) no
N1 . C20 . C21 . 113.0(3) yes
N1 . C20 . C27 . 109.2(3) yes
C21 . C20 . C27 . 111.6(3) yes
N1 . C20 . H201 . 108.0(3) no
C21 . C20 . H201 . 106.9(3) no
C27 . C20 . H201 . 107.8(3) no
C20 . C21 . C22 . 123.9(3) yes
C20 . C21 . C26 . 120.3(3) yes
C22 . C21 . C26 . 115.7(3) yes
C21 . C22 . C23 . 121.5(3) yes
C21 . C22 . H221 . 119.7(3) no
C23 . C22 . H221 . 118.8(4) no
C22 . C23 . C24 . 120.9(5) yes
C22 . C23 . H231 . 119.5(4) no
C24 . C23 . H231 . 119.5(4) no
C23 . C24 . C25 . 118.8(5) yes
C23 . C24 . H241 . 121.7(5) no
C25 . C24 . H241 . 119.5(5) no
C24 . C25 . C26 . 120.8(4) yes
C24 . C25 . H251 . 120.3(6) no
C26 . C25 . H251 . 118.9(6) no
C21 . C26 . C25 . 122.2(4) yes
C21 . C26 . H261 . 118.8(5) no
C25 . C26 . H261 . 118.9(4) no
C20 . C27 . H271 . 110.9(5) no
C20 . C27 . H272 . 109.1(4) no
H271 . C27 . H272 . 108.3(6) no
C20 . C27 . H273 . 111.0(5) no
H271 . C27 . H273 . 109.4(5) no
H272 . C27 . H273 . 108.1(6) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.323(4) yes
N1 . C20 . 1.451(4) yes
N1 . H1 . 0.7731(19) no
C2 . O3 . 1.242(3) yes
C2 . C4 . 1.508(4) yes
C4 . C5 . 1.534(4) yes
C4 . C19 . 1.526(5) yes
C4 . H41 . 1.005(2) no
C5 . C6 . 1.490(5) yes
C5 . C18 . 1.534(6) yes
C5 . H51 . 1.007(3) no
C6 . C7 . 1.287(6) yes
C6 . H61 . 1.010(3) no
C7 . C8 . 1.510(6) yes
C7 . H71 . 1.019(4) no
C8 . C9 . 1.430(6) yes
C8 . H81 . 1.006(5) no
C8 . H82 . 1.023(5) no
C9 . O10 . 1.411(5) yes
C9 . H91 . 0.992(5) no
C9 . H92 . 1.016(5) no
O10 . C11 . 1.384(5) yes
C11 . C12 . 1.489(6) yes
C11 . H111 . 1.017(6) no
C11 . H112 . 1.000(5) no
C12 . C13 . 1.380(6) yes
C12 . C17 . 1.359(6) yes
C13 . C14 . 1.382(7) yes
C13 . H131 . 1.024(5) no
C14 . C15 . 1.368(8) yes
C14 . H141 . 1.014(5) no
C15 . C16 . 1.343(7) yes
C15 . H151 . 1.037(6) no
C16 . C17 . 1.376(7) yes
C16 . H161 . 1.034(6) no
C17 . H171 . 1.016(4) no
C18 . H181 . 1.003(4) no
C18 . H182 . 1.001(5) no
C18 . H183 . 1.022(7) no
C19 . H191 . 1.005(4) no
C19 . H192 . 0.998(5) no
C19 . H193 . 1.013(6) no
C20 . C21 . 1.507(5) yes
C20 . C27 . 1.535(6) yes
C20 . H201 . 1.013(3) no
C21 . C22 . 1.353(5) yes
C21 . C26 . 1.364(5) yes
C22 . C23 . 1.385(5) yes
C22 . H221 . 1.025(3) no
C23 . C24 . 1.344(6) yes
C23 . H231 . 1.033(5) no
C24 . C25 . 1.317(8) yes
C24 . H241 . 1.008(4) no
C25 . C26 . 1.381(7) yes
C25 . H251 . 1.024(4) no
C26 . H261 . 1.011(5) no
C27 . H271 . 0.999(5) no
C27 . H272 . 1.016(7) no
C27 . H273 . 1.002(5) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9362766
2 PubChem 11187682
