#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/56/7105626.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_7105626
loop_
_publ_author_name
'Li-Jian Ma'
'Tsutomu Inokuchi'
_publ_section_title
;
 Solvent-free micorowave-assisted multi-component reaction for preparation
 of 2-aminoketones as precursors of pseudoephedrine analogues
;
_journal_issue                   37
_journal_name_full               'Chem. Commun.'
_journal_page_first              7037
_journal_page_last               7039
_journal_paper_doi               10.1039/c0cc00859a
_journal_volume                  46
_journal_year                    2010
_chemical_formula_moiety         'C18 H24 Br N O2 '
_chemical_formula_sum            'C18 H24 Br N O2'
_chemical_formula_weight         366.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                100.735(4)
_cell_angle_beta                 108.601(4)
_cell_angle_gamma                103.438(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3812(5)
_cell_length_b                   11.6853(3)
_cell_length_c                   8.0564(5)
_cell_measurement_reflns_used    2469
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.3
_cell_volume                     864.20(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9139
_diffrn_measured_fraction_theta_max 0.9139
_diffrn_measurement_device_type  'Rigaku RAXIS-IV Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3384
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_exptl_absorpt_coefficient_mu    2.392
_exptl_absorpt_correction_T_max  0.550
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.542
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2737
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.0083
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00497|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                2461
_reflns_number_total             2889
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c0cc00859a.txt
_cod_data_source_block           ma
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C18 H24 Br N O2 '
_cod_database_code               7105626
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br(1) Br 0.16160(6) -0.52167(5) 0.37110(9) 0.0929(3) Uani 1.00 d . . .
O(2) O 0.8670(4) 0.2203(4) 0.1035(5) 0.079(1) Uani 1.00 d . . .
O(3) O 0.7608(3) -0.0364(3) 0.5709(3) 0.0690(8) Uani 1.00 d . . .
N(2) N 0.7720(3) 0.0228(3) 0.2455(4) 0.0528(8) Uani 1.00 d . . .
C(2) C 0.6623(4) -0.0881(4) 0.2346(5) 0.0486(9) Uani 1.00 d . . .
C(3) C 0.6317(4) -0.0691(4) 0.4126(5) 0.0543(10) Uani 1.00 d . . .
C(4) C 0.3073(5) -0.3833(4) 0.3896(6) 0.062(1) Uani 1.00 d . . .
C(5) C 0.3812(4) -0.2104(4) 0.2870(5) 0.055(1) Uani 1.00 d . . .
C(6) C 0.5228(4) -0.1790(4) 0.4105(5) 0.0502(9) Uani 1.00 d . . .
C(7) C 0.4471(5) -0.3540(4) 0.5139(6) 0.066(1) Uani 1.00 d . . .
C(8) C 0.7028(4) -0.2021(4) 0.1866(5) 0.0508(10) Uani 1.00 d . . .
C(9) C 0.5519(5) -0.2542(5) 0.5249(5) 0.063(1) Uani 1.00 d . . .
C(10) C 0.6189(5) -0.2923(5) 0.0310(5) 0.064(1) Uani 1.00 d . . .
C(11) C 0.8084(6) 0.0043(5) 0.0830(8) 0.074(1) Uani 1.00 d . . .
C(13) C 0.8405(5) -0.2125(5) 0.3128(6) 0.065(1) Uani 1.00 d . . .
C(14) C 0.6527(7) -0.4056(5) -0.0326(7) 0.084(2) Uani 1.00 d . . .
C(15) C 0.7228(5) 0.1310(5) 0.2580(6) 0.068(1) Uani 1.00 d . . .
C(16) C 0.9174(7) 0.1175(6) 0.0909(10) 0.089(2) Uani 1.00 d . . .
C(17) C 0.8321(7) 0.2409(5) 0.2613(7) 0.080(1) Uani 1.00 d . . .
C(18) C 0.8903(6) -0.3099(7) 0.2212(7) 0.087(2) Uani 1.00 d . . .
C(19) C 0.7691(8) -0.4263(6) 0.1140(8) 0.093(2) Uani 1.00 d . . .
C(20) C 0.2761(5) -0.3101(4) 0.2748(6) 0.061(1) Uani 1.00 d . . .
H(1) H 0.3575 -0.1606 0.2090 0.0934 Uiso 1.00 calc . . .
H(2) H 0.4698 -0.4042 0.5916 0.1074 Uiso 1.00 calc . . .
H(3) H 0.6462 -0.2353 0.6118 0.0694 Uiso 1.00 calc . . .
H(5) H 0.5938 -0.0026 0.4209 0.0468 Uiso 1.00 calc . . .
H(6) H 0.8465 -0.0622 0.0758 0.0867 Uiso 1.00 calc . . .
H(7) H 0.7245 -0.0140 -0.0228 0.1035 Uiso 1.00 calc . . .
H(8) H 0.6369 0.1140 0.1552 0.0688 Uiso 1.00 calc . . .
H(9) H 0.7043 0.1480 0.3665 0.0709 Uiso 1.00 calc . . .
H(10) H 0.9384 0.1030 -0.0163 0.1074 Uiso 1.00 calc . . .
H(11) H 1.0025 0.1346 0.1950 0.1196 Uiso 1.00 calc . . .
H(12) H 0.9162 0.2597 0.3663 0.0803 Uiso 1.00 calc . . .
H(13) H 0.7951 0.3080 0.2656 0.1196 Uiso 1.00 calc . . .
H(14) H 0.5764 -0.0962 0.1377 0.1063 Uiso 1.00 calc . . .
H(18) H 0.5681 -0.4741 -0.0736 0.0658 Uiso 1.00 calc . . .
H(19) H 0.6819 -0.3993 -0.1319 0.0913 Uiso 1.00 calc . . .
H(20) H 0.9304 -0.2799 0.1415 0.1266 Uiso 1.00 calc . . .
H(21) H 0.9613 -0.3273 0.3131 0.1223 Uiso 1.00 calc . . .
H(22) H 0.7300 -0.4575 0.1951 0.1410 Uiso 1.00 calc . . .
H(23) H 0.8044 -0.4849 0.0599 0.1121 Uiso 1.00 calc . . .
H(24) H 0.5324 -0.2823 -0.0427 0.0768 Uiso 1.00 calc . . .
H(25) H 0.9132 -0.1357 0.3518 0.0926 Uiso 1.00 calc . . .
H(26) H 0.8259 -0.2327 0.4156 0.0800 Uiso 1.00 calc . . .
H(27) H 0.1818 -0.3294 0.1883 0.1063 Uiso 1.00 calc . . .
H(28) H 0.8168 -0.0044 0.5370 0.1213 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Br Br -0.290 2.459
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(16) O(2) C(17) 109.6(4) . . . yes
C(2) N(2) C(11) 110.6(3) . . . yes
C(2) N(2) C(15) 112.1(3) . . . yes
C(11) N(2) C(15) 107.4(4) . . . yes
N(2) C(2) C(3) 109.6(3) . . . yes
N(2) C(2) C(8) 111.4(3) . . . yes
C(3) C(2) C(8) 114.4(3) . . . yes
O(3) C(3) C(2) 110.8(3) . . . yes
O(3) C(3) C(6) 111.2(3) . . . yes
C(2) C(3) C(6) 112.0(3) . . . yes
Br(1) C(4) C(7) 121.3(3) . . . yes
Br(1) C(4) C(20) 119.7(3) . . . yes
C(7) C(4) C(20) 119.0(4) . . . yes
C(6) C(5) C(20) 122.4(4) . . . yes
C(3) C(6) C(5) 118.9(3) . . . yes
C(3) C(6) C(9) 124.3(4) . . . yes
C(5) C(6) C(9) 116.8(4) . . . yes
C(4) C(7) C(9) 120.8(4) . . . yes
C(2) C(8) C(10) 120.3(3) . . . yes
C(2) C(8) C(13) 119.0(3) . . . yes
C(10) C(8) C(13) 120.7(4) . . . yes
C(6) C(9) C(7) 121.0(4) . . . yes
C(8) C(10) C(14) 124.5(4) . . . yes
N(2) C(11) C(16) 111.0(5) . . . yes
C(8) C(13) C(18) 112.8(4) . . . yes
C(10) C(14) C(19) 112.5(4) . . . yes
N(2) C(15) C(17) 111.5(4) . . . yes
O(2) C(16) C(11) 111.4(5) . . . yes
O(2) C(17) C(15) 111.8(4) . . . yes
C(13) C(18) C(19) 111.6(5) . . . yes
C(14) C(19) C(18) 111.8(5) . . . yes
C(4) C(20) C(5) 119.9(4) . . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br(1) C(4) 1.889(5) . . yes
O(2) C(16) 1.419(8) . . yes
O(2) C(17) 1.420(8) . . yes
O(3) C(3) 1.435(5) . . yes
N(2) C(2) 1.481(5) . . yes
N(2) C(11) 1.471(6) . . yes
N(2) C(15) 1.469(6) . . yes
C(2) C(3) 1.555(5) . . yes
C(2) C(8) 1.507(5) . . yes
C(3) C(6) 1.494(6) . . yes
C(4) C(7) 1.394(7) . . yes
C(4) C(20) 1.381(7) . . yes
C(5) C(6) 1.402(6) . . yes
C(5) C(20) 1.359(6) . . yes
C(6) C(9) 1.400(6) . . yes
C(7) C(9) 1.362(7) . . yes
C(8) C(10) 1.348(6) . . yes
C(8) C(13) 1.516(6) . . yes
C(10) C(14) 1.493(7) . . yes
C(11) C(16) 1.502(8) . . yes
C(13) C(18) 1.518(7) . . yes
C(14) C(19) 1.503(9) . . yes
C(15) C(17) 1.493(8) . . yes
C(18) C(19) 1.50(1) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Br(1) O(2) 3.490(4) . 1_445 ?
Br(1) C(17) 3.596(6) . 1_445 ?
O(2) C(5) 3.333(5) . 2_655 ?
O(2) C(20) 3.411(6) . 2_655 ?
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
Br(1) C(4) C(7) C(9) 179.6(4) . . . . yes
Br(1) C(4) C(20) C(5) -179.7(3) . . . . yes
O(2) C(16) C(11) N(2) -59.1(6) . . . . yes
O(2) C(17) C(15) N(2) 58.2(6) . . . . yes
O(3) C(3) C(2) N(2) -54.6(4) . . . . yes
O(3) C(3) C(2) C(8) 71.2(4) . . . . yes
O(3) C(3) C(6) C(5) 168.0(3) . . . . yes
O(3) C(3) C(6) C(9) -11.8(5) . . . . yes
N(2) C(2) C(3) C(6) -179.3(3) . . . . yes
N(2) C(2) C(8) C(10) -118.2(4) . . . . yes
N(2) C(2) C(8) C(13) 60.2(4) . . . . yes
C(2) N(2) C(11) C(16) 178.9(4) . . . . yes
C(2) N(2) C(15) C(17) -177.6(4) . . . . yes
C(2) C(3) C(6) C(5) -67.6(5) . . . . yes
C(2) C(3) C(6) C(9) 112.7(4) . . . . yes
C(2) C(8) C(10) C(14) 177.2(5) . . . . yes
C(2) C(8) C(13) C(18) -162.2(4) . . . . yes
C(3) C(2) N(2) C(11) 176.9(3) . . . . yes
C(3) C(2) N(2) C(15) -63.3(4) . . . . yes
C(3) C(2) C(8) C(10) 116.9(4) . . . . yes
C(3) C(2) C(8) C(13) -64.6(5) . . . . yes
C(3) C(6) C(5) C(20) 179.2(4) . . . . yes
C(3) C(6) C(9) C(7) -179.3(4) . . . . yes
C(4) C(7) C(9) C(6) -0.8(7) . . . . yes
C(4) C(20) C(5) C(6) 1.1(6) . . . . yes
C(5) C(6) C(9) C(7) 1.0(6) . . . . yes
C(5) C(20) C(4) C(7) -0.9(6) . . . . yes
C(6) C(3) C(2) C(8) -53.5(4) . . . . yes
C(8) C(2) N(2) C(11) 49.4(4) . . . . yes
C(8) C(2) N(2) C(15) 169.2(3) . . . . yes
C(8) C(10) C(14) C(19) 14.8(9) . . . . yes
C(8) C(13) C(18) C(19) -44.8(6) . . . . yes
C(9) C(6) C(5) C(20) -1.1(6) . . . . yes
C(9) C(7) C(4) C(20) 0.8(7) . . . . yes
C(10) C(8) C(13) C(18) 16.2(7) . . . . yes
C(10) C(14) C(19) C(18) -43.3(8) . . . . yes
C(11) N(2) C(15) C(17) -55.9(5) . . . . yes
C(11) C(16) O(2) C(17) 58.1(6) . . . . yes
C(13) C(8) C(10) C(14) -1.2(8) . . . . yes
C(13) C(18) C(19) C(14) 59.6(7) . . . . yes
C(15) N(2) C(11) C(16) 56.2(5) . . . . yes
C(15) C(17) O(2) C(16) -57.7(6) . . . . yes
C(15) C(17) O(2) C(16) -57.7(6) . . . . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24608624
