#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/60/1516064.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_1516064
loop_
_publ_author_name
'Brawn, Ryan A.'
'Guimarães, Cristiano R W'
'McClure, Kim F.'
'Liras, Spiros'
_publ_section_title
;
 An efficient synthesis of bridged heterocycles from an Ir(I)
 bis-amination/ring-closing metathesis sequence.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4802
_journal_page_last               4805
_journal_paper_doi               10.1021/ol302108m
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.9646(3)
_cell_length_b                   34.3413(11)
_cell_length_c                   6.9720(2)
_cell_measurement_reflns_used    4100
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      65.71
_cell_measurement_theta_min      2.57
_cell_volume                     2625.23(13)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7401
_diffrn_reflns_theta_full        66.27
_diffrn_reflns_theta_max         66.27
_diffrn_reflns_theta_min         2.57
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.9207
_exptl_absorpt_correction_T_min  0.8635
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0349
_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)+(0.0681P)²+0.3193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                2197
_reflns_number_total             2250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302108m_si_002.cif
_cod_data_source_block           z194
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Iba2
_cod_database_code               1516064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.22086(10) 0.10091(3) 0.89996(16) 0.0447(3) Uani 1 1 d .
C10 C 0.27818(12) 0.16866(4) 0.87175(19) 0.0473(3) Uani 1 1 d .
C7 C 0.25693(13) 0.13542(4) 1.0153(2) 0.0516(3) Uani 1 1 d .
C4 C 0.19704(13) 0.06412(4) 1.0027(2) 0.0559(4) Uani 1 1 d .
H4 H 0.1635 0.0682 1.1314 0.067 Uiso 1 1 calc R
C15 C 0.38232(14) 0.19161(4) 0.8718(3) 0.0583(4) Uani 1 1 d .
H15 H 0.4441 0.1867 0.9601 0.070 Uiso 1 1 calc R
C1 C 0.30761(14) 0.08663(4) 0.7562(3) 0.0586(4) Uani 1 1 d .
H1 H 0.3571 0.1075 0.7000 0.070 Uiso 1 1 calc R
C11 C 0.18875(15) 0.17709(5) 0.7379(3) 0.0618(4) Uani 1 1 d .
H11 H 0.1185 0.1619 0.7342 0.074 Uiso 1 1 calc R
C5 C 0.31870(16) 0.04335(5) 1.0052(3) 0.0710(5) Uani 1 1 d .
H5 H 0.3430 0.0245 1.0929 0.085 Uiso 1 1 calc R
O1 O 0.16641(15) 0.03351(4) 0.6909(2) 0.0848(4) Uani 1 1 d .
C12 C 0.2012(2) 0.20737(5) 0.6100(3) 0.0769(5) Uani 1 1 d .
H12 H 0.1390 0.2126 0.5231 0.092 Uiso 1 1 calc R
C13 C 0.3050(2) 0.22990(5) 0.6098(3) 0.0790(6) Uani 1 1 d .
H13 H 0.3139 0.2502 0.5225 0.095 Uiso 1 1 calc R
C2 C 0.2286(2) 0.06574(6) 0.6088(3) 0.0817(6) Uani 1 1 d .
H2A H 0.1694 0.0839 0.5566 0.098 Uiso 1 1 calc R
H2B H 0.2795 0.0567 0.5041 0.098 Uiso 1 1 calc R
C9 C 0.1464(2) 0.14654(6) 1.1383(3) 0.0812(5) Uani 1 1 d .
H9A H 0.1312 0.1264 1.2308 0.122 Uiso 1 1 calc R
H9B H 0.0762 0.1496 1.0574 0.122 Uiso 1 1 calc R
H9C H 0.1626 0.1706 1.2036 0.122 Uiso 1 1 calc R
C6 C 0.38338(15) 0.05655(5) 0.8628(4) 0.0764(5) Uani 1 1 d .
H6 H 0.4623 0.0489 0.8317 0.092 Uiso 1 1 calc R
C14 C 0.39502(18) 0.22197(5) 0.7405(3) 0.0740(5) Uani 1 1 d .
H14 H 0.4655 0.2370 0.7416 0.089 Uiso 1 1 calc R
C3 C 0.11168(16) 0.04153(5) 0.8728(3) 0.0727(5) Uani 1 1 d .
H3A H 0.0897 0.0172 0.9344 0.087 Uiso 1 1 calc R
H3B H 0.0375 0.0564 0.8535 0.087 Uiso 1 1 calc R
C8 C 0.3665(2) 0.12923(6) 1.1466(3) 0.0831(6) Uani 1 1 d .
H8A H 0.4378 0.1243 1.0704 0.125 Uiso 1 1 calc R
H8B H 0.3515 0.1074 1.2291 0.125 Uiso 1 1 calc R
H8C H 0.3793 0.1521 1.2230 0.125 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C4 99.22(11)
C1 N1 C7 117.65(11)
C4 N1 C7 117.85(11)
C11 C10 C15 117.67(14)
C11 C10 C7 119.17(13)
C15 C10 C7 123.14(13)
N1 C7 C8 115.05(12)
N1 C7 C9 106.92(13)
C8 C7 C9 108.78(18)
N1 C7 C10 106.27(11)
C8 C7 C10 112.04(13)
C9 C7 C10 107.41(12)
N1 C4 C5 104.66(12)
N1 C4 C3 104.92(13)
C5 C4 C3 108.06(14)
C10 C15 C14 120.43(16)
N1 C1 C6 104.35(15)
N1 C1 C2 104.46(13)
C6 C1 C2 108.72(14)
C12 C11 C10 121.62(16)
C6 C5 C4 107.92(15)
C2 O1 C3 114.13(14)
C13 C12 C11 120.49(18)
C14 C13 C12 118.90(17)
O1 C2 C1 111.57(15)
C5 C6 C1 108.17(15)
C13 C14 C15 120.88(17)
O1 C3 C4 111.67(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.4663(19)
N1 C4 1.4757(18)
N1 C7 1.4860(17)
C10 C11 1.384(2)
C10 C15 1.388(2)
C10 C7 1.5360(19)
C7 C8 1.525(2)
C7 C9 1.532(2)
C4 C5 1.513(2)
C4 C3 1.516(2)
C15 C14 1.394(3)
C1 C6 1.520(3)
C1 C2 1.524(3)
C11 C12 1.377(3)
C5 C6 1.301(3)
O1 C2 1.421(2)
O1 C3 1.430(3)
C12 C13 1.376(3)
C13 C14 1.371(3)
