#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/23/1502345.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_1502345
loop_
_publ_author_name
'Ovalles, Stephanie R.'
'Hansen, Jørn H'
'Davies, Huw M. L.'
_publ_section_title
;
 Thermally induced cycloadditions of donor/acceptor carbenes.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4284
_journal_page_last               4287
_journal_paper_doi               10.1021/ol201628d
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H15 Br O'
_chemical_formula_sum            'C17 H15 Br O'
_chemical_formula_weight         315.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 95.162(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9697(9)
_cell_length_b                   6.1032(3)
_cell_length_c                   12.0780(6)
_cell_measurement_reflns_used    727
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.77
_cell_measurement_theta_min      6.21
_cell_volume                     1392.67(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1354
_diffrn_reflns_theta_full        69.64
_diffrn_reflns_theta_max         69.64
_diffrn_reflns_theta_min         5.69
_exptl_absorpt_coefficient_mu    3.918
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.3131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   twinabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.238
_refine_diff_density_min         -1.273
_refine_diff_density_rms         0.218
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1354
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0589
_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)+(0.1800P)²+2.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.2174
_reflns_number_gt                1292
_reflns_number_total             1354
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201628d_si_002.cif
_cod_data_source_block           sro_999t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value 'AD' changed to 'ad'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1502345
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'
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
Br1 Br 0.08042(4) 0.3616(2) 0.60348(7) 0.0376(4) Uani 1 1 d .
C1 C 0.1809(4) 0.376(2) 0.6324(7) 0.0261(18) Uani 1 1 d .
C2 C 0.2148(6) 0.5594(19) 0.6032(9) 0.034(2) Uani 1 1 d .
H2A H 0.1894 0.6758 0.5658 0.041 Uiso 1 1 calc R
C3 C 0.2888(6) 0.5739(18) 0.6297(8) 0.032(2) Uani 1 1 d .
H3A H 0.3136 0.7000 0.6082 0.038 Uiso 1 1 calc R
C4 C 0.3251(5) 0.4082(15) 0.6860(7) 0.025(2) Uani 1 1 d .
C5 C 0.2886(6) 0.2174(17) 0.7110(8) 0.028(2) Uani 1 1 d .
H5A H 0.3140 0.0977 0.7455 0.034 Uiso 1 1 calc R
C6 C 0.2173(5) 0.2014(17) 0.6865(8) 0.028(2) Uani 1 1 d .
H6A H 0.1926 0.0735 0.7059 0.034 Uiso 1 1 calc R
C7 C 0.4043(5) 0.4262(16) 0.7117(7) 0.0234(19) Uani 1 1 d .
C8 C 0.4371(5) 0.6448(15) 0.7463(8) 0.0228(18) Uani 1 1 d .
C9 C 0.4898(6) 0.544(2) 0.8337(8) 0.035(2) Uani 1 1 d .
H9A H 0.4918 0.6177 0.9070 0.042 Uiso 1 1 calc R
H9B H 0.5378 0.5235 0.8091 0.042 Uiso 1 1 calc R
C10 C 0.4421(5) 0.3313(18) 0.8246(7) 0.025(2) Uani 1 1 d .
H10A H 0.4705 0.1971 0.8116 0.030 Uiso 1 1 calc R
C11 C 0.3984(5) 0.3033(15) 0.9220(7) 0.026(2) Uani 1 1 d .
C12 C 0.3537(6) 0.465(2) 0.9558(8) 0.033(2) Uani 1 1 d .
H12A H 0.3491 0.5988 0.9154 0.039 Uiso 1 1 calc R
C13 C 0.3153(6) 0.436(2) 1.0478(9) 0.037(2) Uani 1 1 d .
H13A H 0.2848 0.5487 1.0697 0.045 Uiso 1 1 calc R
C14 C 0.3223(6) 0.241(2) 1.1070(9) 0.037(2) Uani 1 1 d .
H14A H 0.2963 0.2193 1.1697 0.045 Uiso 1 1 calc R
C15 C 0.3662(7) 0.081(2) 1.0756(9) 0.040(2) Uani 1 1 d .
H15A H 0.3718 -0.0498 1.1178 0.048 Uiso 1 1 calc R
C16 C 0.4029(6) 0.1087(18) 0.9818(8) 0.033(2) Uani 1 1 d .
H16A H 0.4314 -0.0074 0.9583 0.040 Uiso 1 1 calc R
C17 C 0.4412(5) 0.3330(17) 0.6121(7) 0.028(2) Uani 1 1 d .
H17A H 0.4178 0.3900 0.5424 0.042 Uiso 1 1 calc R
H17B H 0.4382 0.1727 0.6122 0.042 Uiso 1 1 calc R
H17C H 0.4911 0.3776 0.6188 0.042 Uiso 1 1 calc R
O1 O 0.4229(4) 0.8343(13) 0.7225(7) 0.0379(17) Uani 1 1 d .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C2 C1 C6 121.7(8)
C2 C1 Br1 118.6(9)
C6 C1 Br1 119.6(8)
C1 C2 C3 118.5(10)
C1 C2 H2A 120.7
C3 C2 H2A 120.7
C4 C3 C2 120.7(9)
C4 C3 H3A 119.7
C2 C3 H3A 119.7
C3 C4 C5 119.0(9)
C3 C4 C7 119.6(8)
C5 C4 C7 121.1(9)
C6 C5 C4 120.8(9)
C6 C5 H5A 119.6
C4 C5 H5A 119.6
C5 C6 C1 119.1(9)
C5 C6 H6A 120.5
C1 C6 H6A 120.5
C4 C7 C8 119.8(8)
C4 C7 C17 108.9(7)
C8 C7 C17 109.5(7)
C4 C7 C10 120.9(7)
C8 C7 C10 86.6(7)
C17 C7 C10 109.3(7)
O1 C8 C7 134.0(9)
O1 C8 C9 131.9(10)
C7 C8 C9 93.7(8)
C8 C9 C10 87.0(7)
C8 C9 H9A 114.2
C10 C9 H9A 114.2
C8 C9 H9B 114.2
C10 C9 H9B 114.2
H9A C9 H9B 111.3
C11 C10 C9 113.0(8)
C11 C10 C7 118.2(8)
C9 C10 C7 88.3(7)
C11 C10 H10A 111.8
C9 C10 H10A 111.8
C7 C10 H10A 111.8
C12 C11 C16 117.8(9)
C12 C11 C10 122.8(9)
C16 C11 C10 119.3(9)
C11 C12 C13 121.4(11)
C11 C12 H12A 119.3
C13 C12 H12A 119.3
C14 C13 C12 119.1(11)
C14 C13 H13A 120.4
C12 C13 H13A 120.4
C15 C14 C13 120.3(9)
C15 C14 H14A 119.9
C13 C14 H14A 119.9
C14 C15 C16 120.4(11)
C14 C15 H15A 119.8
C16 C15 H15A 119.8
C11 C16 C15 120.9(11)
C11 C16 H16A 119.5
C15 C16 H16A 119.5
C7 C17 H17A 109.5
C7 C17 H17B 109.5
H17A C17 H17B 109.5
C7 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.909(8)
C1 C2 1.354(17)
C1 C6 1.398(16)
C2 C3 1.415(16)
C2 H2A 0.9500
C3 C4 1.369(15)
C3 H3A 0.9500
C4 C5 1.401(13)
C4 C7 1.510(13)
C5 C6 1.363(15)
C5 H5A 0.9500
C6 H6A 0.9500
C7 C8 1.516(13)
C7 C17 1.554(11)
C7 C10 1.592(11)
C8 O1 1.216(13)
C8 C9 1.516(15)
C9 C10 1.582(16)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.508(10)
C10 H10A 1.0000
C11 C12 1.388(15)
C11 C16 1.389(14)
C12 C13 1.393(14)
C12 H12A 0.9500
C13 C14 1.391(18)
C13 H13A 0.9500
C14 C15 1.358(18)
C14 H14A 0.9500
C15 C16 1.392(15)
C15 H15A 0.9500
C16 H16A 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 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
C6 C1 C2 C3 -0.7(14)
Br1 C1 C2 C3 176.9(7)
C1 C2 C3 C4 -1.5(15)
C2 C3 C4 C5 3.9(14)
C2 C3 C4 C7 179.1(8)
C3 C4 C5 C6 -4.2(13)
C7 C4 C5 C6 -179.3(9)
C4 C5 C6 C1 2.1(14)
C2 C1 C6 C5 0.4(14)
Br1 C1 C6 C5 -177.2(7)
C3 C4 C7 C8 39.2(12)
C5 C4 C7 C8 -145.7(8)
C3 C4 C7 C17 -87.8(10)
C5 C4 C7 C17 87.3(10)
C3 C4 C7 C10 144.6(9)
C5 C4 C7 C10 -40.4(12)
C4 C7 C8 O1 -33.4(14)
C17 C7 C8 O1 93.3(12)
C10 C7 C8 O1 -157.4(11)
C4 C7 C8 C9 140.0(8)
C17 C7 C8 C9 -93.3(8)
C10 C7 C8 C9 16.0(7)
O1 C8 C9 C10 157.5(10)
C7 C8 C9 C10 -16.1(7)
C8 C9 C10 C11 -104.8(8)
C8 C9 C10 C7 15.3(7)
C4 C7 C10 C11 -23.0(14)
C8 C7 C10 C11 100.0(9)
C17 C7 C10 C11 -150.5(9)
C4 C7 C10 C9 -138.3(9)
C8 C7 C10 C9 -15.3(7)
C17 C7 C10 C9 94.2(9)
C9 C10 C11 C12 53.9(14)
C7 C10 C11 C12 -47.2(15)
C9 C10 C11 C16 -125.7(10)
C7 C10 C11 C16 133.3(10)
C16 C11 C12 C13 1.1(17)
C10 C11 C12 C13 -178.4(10)
C11 C12 C13 C14 0.2(18)
C12 C13 C14 C15 0.2(18)
C13 C14 C15 C16 -2.0(19)
C12 C11 C16 C15 -2.9(16)
C10 C11 C16 C15 176.7(11)
C14 C15 C16 C11 3.4(19)
