#------------------------------------------------------------------------------
#$Date: 2019-06-25 10:18:56 +0300 (Tue, 25 Jun 2019) $
#$Revision: 216523 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/18/1551881.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_1551881
loop_
_publ_author_name
'Ling Li'
'Chao-Yuan Wang'
'Rongcai Huang'
'Mark R. Biscoe'
_publ_section_title
;
 Stereoretentive Pd-catalysed Stille cross-coupling reactions of secondary
 alkyl azastannatranes and aryl halides
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              607
_journal_page_last               612
_journal_paper_doi               10.1038/nchem.1652
_journal_volume                  5
_journal_year                    2013
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C18 H15 Br N2 O, 0.6(H2 O)'
_chemical_formula_sum            'C18 H16.19 Br N2 O1.6'
_chemical_formula_weight         365.96
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.2820(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.4574(4)
_cell_length_b                   5.6600(3)
_cell_length_c                   19.1444(11)
_cell_measurement_reflns_used    6881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.75
_cell_volume                     801.55(8)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12458
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    2.572
_exptl_absorpt_correction_T_max  0.8822
_exptl_absorpt_correction_T_min  0.3372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab-like
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0281P)²+0.1445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0564
_reflns_number_gt                3758
_reflns_number_total             3999
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1652-s2.cif
_cod_data_source_block           compound-11
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C18 H16.19 Br N2 O1.60'
_cod_database_code               1551881
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.62550(2) 0.74919(4) -0.105958(8) 0.02655(6) Uani 1 1 d . . .
O1 O 0.87278(19) 1.2199(3) 0.22152(7) 0.0255(3) Uani 1 1 d . . .
N1 N 1.0532(2) 0.8988(3) 0.23355(8) 0.0207(3) Uani 1 1 d . . .
N2 N 0.5556(2) 0.8006(3) 0.55744(9) 0.0247(4) Uani 1 1 d . . .
C1 C 1.1244(3) 0.9634(4) 0.30634(9) 0.0222(4) Uani 1 1 d . . .
H1 H 1.1689 1.1302 0.3076 0.027 Uiso 1 1 calc R . .
C2 C 1.2855(3) 0.7941(5) 0.32345(10) 0.0327(6) Uani 1 1 d . . .
H2A H 1.3843 0.8706 0.3548 0.039 Uiso 1 1 calc R . .
H2B H 1.2483 0.6483 0.3463 0.039 Uiso 1 1 calc R . .
C3 C 1.3449(3) 0.7390(7) 0.25131(9) 0.0380(5) Uani 1 1 d . . .
H3A H 1.4190 0.8686 0.2353 0.046 Uiso 1 1 calc R . .
H3B H 1.4142 0.5896 0.2524 0.046 Uiso 1 1 calc R . .
C4 C 1.1646(3) 0.7175(5) 0.20465(10) 0.0283(5) Uani 1 1 d . . .
H4A H 1.1779 0.7505 0.1548 0.034 Uiso 1 1 calc R . .
H4B H 1.1118 0.5581 0.2082 0.034 Uiso 1 1 calc R . .
C5 C 0.9297(3) 1.0377(3) 0.19651(10) 0.0194(4) Uani 1 1 d . . .
C6 C 0.8596(2) 0.9604(3) 0.12321(10) 0.0171(3) Uani 1 1 d . . .
C7 C 0.7764(2) 0.7423(5) 0.11001(8) 0.0223(3) Uani 1 1 d . . .
H7 H 0.7689 0.6344 0.1475 0.027 Uiso 1 1 calc R . .
C8 C 0.7041(3) 0.6824(3) 0.04169(11) 0.0224(4) Uani 1 1 d . . .
H8 H 0.6442 0.5354 0.0326 0.027 Uiso 1 1 calc R . .
C9 C 0.7199(2) 0.8373(3) -0.01259(10) 0.0196(4) Uani 1 1 d . . .
C10 C 0.8030(3) 1.0554(3) -0.00054(10) 0.0208(4) Uani 1 1 d . . .
H10 H 0.8128 1.1610 -0.0384 0.025 Uiso 1 1 calc R . .
C11 C 0.8718(2) 1.1166(3) 0.06789(9) 0.0187(4) Uani 1 1 d . . .
H11 H 0.9276 1.2663 0.0770 0.022 Uiso 1 1 calc R . .
C12 C 0.9848(2) 0.9363(3) 0.35634(9) 0.0187(4) Uani 1 1 d . . .
C13 C 0.8763(2) 0.7345(5) 0.35412(8) 0.0216(3) Uani 1 1 d . . .
H13 H 0.8831 0.6197 0.3184 0.026 Uiso 1 1 calc R . .
C14 C 0.7583(2) 0.7008(3) 0.40395(10) 0.0209(4) Uani 1 1 d . . .
H14 H 0.6839 0.5642 0.4022 0.025 Uiso 1 1 calc R . .
C15 C 0.7501(2) 0.8699(3) 0.45662(10) 0.0188(4) Uani 1 1 d . . .
C16 C 0.8545(3) 1.0752(3) 0.45834(10) 0.0200(4) Uani 1 1 d . . .
H16 H 0.8465 1.1914 0.4936 0.024 Uiso 1 1 calc R . .
C17 C 0.9704(3) 1.1065(3) 0.40755(9) 0.0195(4) Uani 1 1 d . . .
H17 H 1.0407 1.2466 0.4079 0.023 Uiso 1 1 calc R . .
C18 C 0.6373(3) 0.8308(3) 0.51162(10) 0.0203(4) Uani 1 1 d . . .
O2 O 0.5498(3) 0.2443(8) 0.28600(12) 0.0385(8) Uani 0.596(5) 1 d PD . .
H2C H 0.559(5) 0.195(9) 0.3271(11) 0.058 Uiso 0.596(5) 1 d PD . .
H2D H 0.654(2) 0.254(14) 0.276(2) 0.058 Uiso 0.596(5) 1 d PD . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 N1 C4 126.28(16) . .
C5 N1 C1 119.66(16) . .
C4 N1 C1 112.09(15) . .
N1 C1 C12 112.37(15) . .
N1 C1 C2 102.98(16) . .
C12 C1 C2 112.60(16) . .
N1 C1 H1 109.6 . .
C12 C1 H1 109.6 . .
C2 C1 H1 109.6 . .
C3 C2 C1 103.98(17) . .
C3 C2 H2A 111.0 . .
C1 C2 H2A 111.0 . .
C3 C2 H2B 111.0 . .
C1 C2 H2B 111.0 . .
H2A C2 H2B 109.0 . .
C4 C3 C2 102.13(15) . .
C4 C3 H3A 111.3 . .
C2 C3 H3A 111.3 . .
C4 C3 H3B 111.3 . .
C2 C3 H3B 111.3 . .
H3A C3 H3B 109.2 . .
N1 C4 C3 102.84(19) . .
N1 C4 H4A 111.2 . .
C3 C4 H4A 111.2 . .
N1 C4 H4B 111.2 . .
C3 C4 H4B 111.2 . .
H4A C4 H4B 109.1 . .
O1 C5 N1 122.05(17) . .
O1 C5 C6 120.70(17) . .
N1 C5 C6 117.24(17) . .
C7 C6 C11 119.77(17) . .
C7 C6 C5 121.57(16) . .
C11 C6 C5 118.60(16) . .
C6 C7 C8 119.86(19) . .
C6 C7 H7 120.1 . .
C8 C7 H7 120.1 . .
C9 C8 C7 119.63(19) . .
C9 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C8 C9 C10 121.37(18) . .
C8 C9 Br1 119.06(14) . .
C10 C9 Br1 119.57(15) . .
C9 C10 C11 118.85(18) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
C10 C11 C6 120.50(18) . .
C10 C11 H11 119.7 . .
C6 C11 H11 119.7 . .
C17 C12 C13 119.48(17) . .
C17 C12 C1 119.93(17) . .
C13 C12 C1 120.50(17) . .
C14 C13 C12 120.38(19) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 119.37(18) . .
C13 C14 H14 120.3 . .
C15 C14 H14 120.3 . .
C16 C15 C14 120.79(17) . .
C16 C15 C18 118.96(17) . .
C14 C15 C18 120.22(17) . .
C17 C16 C15 118.90(17) . .
C17 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
C12 C17 C16 121.02(18) . .
C12 C17 H17 119.5 . .
C16 C17 H17 119.5 . .
N2 C18 C15 176.6(2) . .
H2C O2 H2D 105(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.9027(19) .
O1 C5 1.235(3) .
N1 C5 1.343(3) .
N1 C4 1.471(3) .
N1 C1 1.473(2) .
N2 C18 1.142(2) .
C1 C12 1.508(3) .
C1 C2 1.539(3) .
C1 H1 1.0000 .
C2 C3 1.535(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.522(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.499(3) .
C6 C7 1.391(3) .
C6 C11 1.391(3) .
C7 C8 1.392(3) .
C7 H7 0.9500 .
C8 C9 1.376(3) .
C8 H8 0.9500 .
C9 C10 1.388(3) .
C10 C11 1.389(3) .
C10 H10 0.9500 .
C11 H11 0.9500 .
C12 C17 1.389(3) .
C12 C13 1.397(3) .
C13 C14 1.391(2) .
C13 H13 0.9500 .
C14 C15 1.397(3) .
C14 H14 0.9500 .
C15 C16 1.397(3) .
C15 C18 1.446(3) .
C16 C17 1.392(3) .
C16 H16 0.9500 .
C17 H17 0.9500 .
O2 H2C 0.829(10) .
O2 H2D 0.825(10) .
