#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/81/1518180.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_1518180
loop_
_publ_author_name
'Mantelingu, Kempegowda'
'Lin, Yingfu'
'Seidel, Daniel'
_publ_section_title
;
 Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from
 secondary amines via redox-neutral C-H functionalization.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5910
_journal_page_last               5913
_journal_paper_doi               10.1021/ol502918g
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C18 H21 Br2 N O3'
_chemical_formula_weight         459.18
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 104.880(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.264(2)
_cell_length_b                   9.5605(14)
_cell_length_c                   14.416(2)
_cell_measurement_reflns_used    5500
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.55
_cell_measurement_theta_min      2.42
_cell_volume                     1766.8(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23635
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.031
_diffrn_reflns_theta_min         1.862
_exptl_absorpt_coefficient_mu    4.605
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.4589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.969
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         6096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0350P)²+0.9000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5095
_reflns_number_total             6096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol502918g_si_004.cif
_cod_data_source_block           mk150a_P21n
_cod_depositor_comments
'Adding full bibliography for 1518180--1518183.cif.'
_cod_original_cell_volume        1766.7(5)
_cod_database_code               1518180
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.202
_shelx_estimated_absorpt_t_max   0.710
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.51572(2) 0.63646(2) 0.11553(2) 0.01589(5) Uani 1 1 d . .
Br2 Br 0.12114(2) 0.75907(2) -0.13228(2) 0.01839(5) Uani 1 1 d . .
O1 O 0.07758(10) 0.85842(14) 0.04908(9) 0.0163(3) Uani 1 1 d . .
O2 O -0.09575(11) 0.80911(15) 0.28423(12) 0.0257(3) Uani 1 1 d . .
O3 O -0.09719(10) 0.59585(14) 0.21741(10) 0.0180(3) Uani 1 1 d . .
N1 N 0.23435(12) 0.76280(16) 0.32749(10) 0.0147(3) Uani 1 1 d . .
C1 C 0.20880(13) 0.86252(18) 0.24769(12) 0.0125(3) Uani 1 1 d . .
H1 H 0.2423 0.9547 0.2692 0.015 Uiso 1 1 calc R U
C2 C 0.08980(13) 0.87875(17) 0.22104(12) 0.0128(3) Uani 1 1 d . .
H2 H 0.0695 0.9405 0.2693 0.015 Uiso 1 1 calc R U
C3 C 0.05432(14) 0.72909(18) 0.23293(13) 0.0138(3) Uani 1 1 d . .
H3 H 0.0561 0.6742 0.1743 0.017 Uiso 1 1 calc R U
C4 C 0.14057(14) 0.67155(19) 0.31981(13) 0.0161(3) Uani 1 1 d . .
H4 H 0.1582 0.5734 0.3057 0.019 Uiso 1 1 calc R U
C5 C 0.11908(16) 0.6764(3) 0.41979(14) 0.0259(4) Uani 1 1 d . .
H5A H 0.0629 0.7439 0.4212 0.031 Uiso 1 1 calc R U
H5B H 0.0994 0.5830 0.4391 0.031 Uiso 1 1 calc R U
C6 C 0.22307(17) 0.7241(2) 0.48438(14) 0.0259(4) Uani 1 1 d . .
H6A H 0.2142 0.7654 0.5448 0.031 Uiso 1 1 calc R U
H6B H 0.2734 0.6457 0.4999 0.031 Uiso 1 1 calc R U
C7 C 0.25790(16) 0.8332(2) 0.42281(13) 0.0201(4) Uani 1 1 d . .
H7 H 0.2126 0.9179 0.4183 0.024 Uiso 1 1 calc R U
C8 C 0.37090(17) 0.8774(2) 0.45515(15) 0.0256(4) Uani 1 1 d . .
H8A H 0.4158 0.7948 0.4609 0.038 Uiso 1 1 calc R U
H8B H 0.3835 0.9242 0.5176 0.038 Uiso 1 1 calc R U
H8C H 0.3867 0.9420 0.4080 0.038 Uiso 1 1 calc R U
C9 C 0.24493(13) 0.80983(17) 0.16160(12) 0.0120(3) Uani 1 1 d . .
C10 C 0.34577(14) 0.75777(17) 0.17482(12) 0.0129(3) Uani 1 1 d . .
H10 H 0.3919 0.7553 0.2373 0.015 Uiso 1 1 calc R U
C11 C 0.37894(13) 0.70953(18) 0.09666(12) 0.0126(3) Uani 1 1 d . .
C12 C 0.31337(14) 0.70990(18) 0.00459(12) 0.0139(3) Uani 1 1 d . .
H12 H 0.3368 0.6767 -0.0484 0.017 Uiso 1 1 calc R U
C13 C 0.21289(14) 0.75996(18) -0.00800(12) 0.0132(3) Uani 1 1 d . .
C14 C 0.17767(13) 0.81200(18) 0.06911(12) 0.0128(3) Uani 1 1 d . .
C15 C 0.04992(14) 0.94172(19) 0.12218(12) 0.0162(3) Uani 1 1 d . .
H15A H -0.0270 0.9503 0.1073 0.019 Uiso 1 1 calc R U
H15B H 0.0793 1.0369 0.1218 0.019 Uiso 1 1 calc R U
C16 C -0.05414(14) 0.71992(19) 0.24799(13) 0.0153(3) Uani 1 1 d . .
C17 C -0.19805(15) 0.5659(2) 0.23568(14) 0.0199(4) Uani 1 1 d . .
H17A H -0.2394 0.5052 0.1841 0.024 Uiso 1 1 calc R U
H17B H -0.2370 0.6542 0.2357 0.024 Uiso 1 1 calc R U
C18 C -0.18295(17) 0.4939(2) 0.33099(16) 0.0255(4) Uani 1 1 d . .
H18A H -0.1410 0.4093 0.3320 0.038 Uiso 1 1 calc R U
H18B H -0.2511 0.4684 0.3407 0.038 Uiso 1 1 calc R U
H18C H -0.1469 0.5571 0.3824 0.038 Uiso 1 1 calc R U
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
C14 O1 C15 116.31(14)
C16 O3 C17 116.61(14)
C1 N1 C7 112.43(14)
C1 N1 C4 107.47(14)
C7 N1 C4 107.73(14)
N1 C1 C9 111.48(14)
N1 C1 C2 106.16(13)
C9 C1 C2 110.34(14)
N1 C1 H1 109.6
C9 C1 H1 109.6
C2 C1 H1 109.6
C15 C2 C3 115.78(15)
C15 C2 C1 111.41(14)
C3 C2 C1 101.76(13)
C15 C2 H2 109.2
C3 C2 H2 109.2
C1 C2 H2 109.2
C16 C3 C2 113.70(14)
C16 C3 C4 113.09(14)
C2 C3 C4 103.65(14)
C16 C3 H3 108.7
C2 C3 H3 108.7
C4 C3 H3 108.7
N1 C4 C5 105.22(16)
N1 C4 C3 106.07(13)
C5 C4 C3 117.77(15)
N1 C4 H4 109.1
C5 C4 H4 109.1
C3 C4 H4 109.1
C6 C5 C4 103.01(16)
C6 C5 H5A 111.2
C4 C5 H5A 111.2
C6 C5 H5B 111.2
C4 C5 H5B 111.2
H5A C5 H5B 109.1
C7 C6 C5 102.26(16)
C7 C6 H6A 111.3
C5 C6 H6A 111.3
C7 C6 H6B 111.3
C5 C6 H6B 111.3
H6A C6 H6B 109.2
N1 C7 C8 111.56(15)
N1 C7 C6 101.87(16)
C8 C7 C6 116.03(17)
N1 C7 H7 109.0
C8 C7 H7 109.0
C6 C7 H7 109.0
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C14 119.32(15)
C10 C9 C1 119.83(15)
C14 C9 C1 120.85(15)
C11 C10 C9 120.02(16)
C11 C10 H10 120.0
C9 C10 H10 120.0
C12 C11 C10 121.58(16)
C12 C11 Br1 118.65(12)
C10 C11 Br1 119.75(13)
C13 C12 C11 118.20(16)
C13 C12 H12 120.9
C11 C12 H12 120.9
C12 C13 C14 121.62(16)
C12 C13 Br2 119.14(13)
C14 C13 Br2 119.24(13)
O1 C14 C9 123.77(15)
O1 C14 C13 116.96(15)
C9 C14 C13 119.24(16)
O1 C15 C2 112.08(14)
O1 C15 H15A 109.2
C2 C15 H15A 109.2
O1 C15 H15B 109.2
C2 C15 H15B 109.2
H15A C15 H15B 107.9
O2 C16 O3 124.37(17)
O2 C16 C3 125.44(17)
O3 C16 C3 110.17(14)
O3 C17 C18 110.02(16)
O3 C17 H17A 109.7
C18 C17 H17A 109.7
O3 C17 H17B 109.7
C18 C17 H17B 109.7
H17A C17 H17B 108.2
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C11 1.8973(17)
Br2 C13 1.8897(17)
O1 C14 1.359(2)
O1 C15 1.442(2)
O2 C16 1.205(2)
O3 C16 1.341(2)
O3 C17 1.457(2)
N1 C1 1.465(2)
N1 C7 1.490(2)
N1 C4 1.500(2)
C1 C9 1.526(2)
C1 C2 1.533(2)
C1 H1 1.0000
C2 C15 1.512(2)
C2 C3 1.530(2)
C2 H2 1.0000
C3 C16 1.511(2)
C3 C4 1.563(3)
C3 H3 1.0000
C4 C5 1.540(3)
C4 H4 1.0000
C5 C6 1.522(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.517(3)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.511(3)
C7 H7 1.0000
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C10 1.394(2)
C9 C14 1.401(2)
C10 C11 1.389(2)
C10 H10 0.9500
C11 C12 1.387(2)
C12 C13 1.383(2)
C12 H12 0.9500
C13 C14 1.403(2)
C15 H15A 0.9900
C15 H15B 0.9900
C17 C18 1.503(3)
C17 H17A 0.9900
C17 H17B 0.9900
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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
C7 N1 C1 C9 147.37(15)
C4 N1 C1 C9 -94.24(16)
C7 N1 C1 C2 -92.44(17)
C4 N1 C1 C2 25.94(17)
N1 C1 C2 C15 -162.31(14)
C9 C1 C2 C15 -41.38(19)
N1 C1 C2 C3 -38.34(16)
C9 C1 C2 C3 82.58(16)
C15 C2 C3 C16 -80.79(19)
C1 C2 C3 C16 158.24(14)
C15 C2 C3 C4 156.02(14)
C1 C2 C3 C4 35.05(15)
C1 N1 C4 C5 -128.68(15)
C7 N1 C4 C5 -7.30(19)
C1 N1 C4 C3 -3.17(17)
C7 N1 C4 C3 118.21(15)
C16 C3 C4 N1 -144.13(14)
C2 C3 C4 N1 -20.55(17)
C16 C3 C4 C5 -26.7(2)
C2 C3 C4 C5 96.87(18)
N1 C4 C5 C6 -20.2(2)
C3 C4 C5 C6 -138.07(18)
C4 C5 C6 C7 39.7(2)
C1 N1 C7 C8 -85.41(19)
C4 N1 C7 C8 156.36(16)
C1 N1 C7 C6 150.18(15)
C4 N1 C7 C6 31.95(18)
C5 C6 C7 N1 -44.19(19)
C5 C6 C7 C8 -165.56(17)
N1 C1 C9 C10 -47.8(2)
C2 C1 C9 C10 -165.50(15)
N1 C1 C9 C14 131.69(17)
C2 C1 C9 C14 14.0(2)
C14 C9 C10 C11 0.4(2)
C1 C9 C10 C11 179.92(15)
C9 C10 C11 C12 -0.9(3)
C9 C10 C11 Br1 -179.14(12)
C10 C11 C12 C13 0.0(3)
Br1 C11 C12 C13 178.31(13)
C11 C12 C13 C14 1.3(3)
C11 C12 C13 Br2 -179.04(13)
C15 O1 C14 C9 16.5(2)
C15 O1 C14 C13 -165.43(15)
C10 C9 C14 O1 178.86(16)
C1 C9 C14 O1 -0.6(3)
C10 C9 C14 C13 0.8(2)
C1 C9 C14 C13 -178.66(15)
C12 C13 C14 O1 -179.88(16)
Br2 C13 C14 O1 0.5(2)
C12 C13 C14 C9 -1.7(3)
Br2 C13 C14 C9 178.61(13)
C14 O1 C15 C2 -45.4(2)
C3 C2 C15 O1 -57.0(2)
C1 C2 C15 O1 58.66(19)
C17 O3 C16 O2 -4.1(3)
C17 O3 C16 C3 174.24(15)
C2 C3 C16 O2 -28.1(3)
C4 C3 C16 O2 89.7(2)
C2 C3 C16 O3 153.53(15)
C4 C3 C16 O3 -88.62(18)
C16 O3 C17 C18 -90.37(19)
