#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:48:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180236 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/22/7112256.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_7112256
loop_
_publ_author_name
'Binjie Guo'
'Chunling Fu'
'Shengming Ma'
_publ_section_title
;
 Asymmetric semipinacol rearrangement of 2,3-allenols with
 N-bromo-1,8-naphthalimide
;
_journal_name_full               Chem.Commun.
_journal_page_first              4445
_journal_paper_doi               10.1039/C4CC00767K
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 Br O2'
_chemical_formula_sum            'C20 H21 Br O2'
_chemical_formula_weight         373.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.884(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7903(11)
_cell_length_b                   8.3733(5)
_cell_length_c                   10.8570(9)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5891
_cell_measurement_theta_min      3.1562
_cell_volume                     916.49(15)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0566
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6043
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    2.249
_exptl_absorpt_correction_T_max  0.6257
_exptl_absorpt_correction_T_min  0.4819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack (1983), 1539 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.022(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3325
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0472
_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)+(0.0472P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2460
_reflns_number_total             3325
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00767k2.cif
_cod_data_source_block           131008_gbj_9_6
_cod_original_cell_volume        916.49(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7112256
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
Br1 Br 0.24395(5) -0.09447(10) 0.02625(4) 0.0738(2) Uani 1 1 d .
O1 O 0.2678(6) 0.5166(7) -0.0041(6) 0.128(2) Uani 1 1 d .
O2 O 0.7125(3) 0.1876(5) 0.5363(3) 0.0735(10) Uani 1 1 d .
C1 C 0.1359(6) 0.3396(6) -0.5348(5) 0.0796(17) Uani 1 1 d .
H1 H 0.1575 0.4406 -0.4975 0.096 Uiso 1 1 calc R
C2 C 0.0368(7) 0.3222(8) -0.6566(6) 0.092(2) Uani 1 1 d .
H2 H -0.0097 0.4120 -0.6991 0.110 Uiso 1 1 calc R
C3 C 0.0060(6) 0.1804(11) -0.7150(5) 0.0900(19) Uani 1 1 d .
H3 H -0.0591 0.1713 -0.7984 0.108 Uiso 1 1 calc R
C4 C 0.0709(7) 0.0501(9) -0.6508(6) 0.0931(19) Uani 1 1 d .
H4 H 0.0495 -0.0501 -0.6894 0.112 Uiso 1 1 calc R
C5 C 0.1686(6) 0.0649(7) -0.5286(5) 0.0770(17) Uani 1 1 d .
H5 H 0.2123 -0.0265 -0.4863 0.092 Uiso 1 1 calc R
C6 C 0.2030(5) 0.2065(6) -0.4683(4) 0.0563(12) Uani 1 1 d .
C7 C 0.3107(5) 0.2200(8) -0.3327(4) 0.0681(14) Uani 1 1 d .
H7A H 0.3620 0.3161 -0.3292 0.082 Uiso 1 1 calc R
H7B H 0.3701 0.1293 -0.3186 0.082 Uiso 1 1 calc R
C8 C 0.2534(5) 0.2253(7) -0.2233(4) 0.0606(12) Uani 1 1 d .
H8A H 0.2010 0.3217 -0.2322 0.073 Uiso 1 1 calc R
H8B H 0.1951 0.1345 -0.2319 0.073 Uiso 1 1 calc R
C9 C 0.3621(5) 0.2225(6) -0.0876(4) 0.0552(11) Uani 1 1 d .
H9A H 0.4237 0.3089 -0.0822 0.066 Uiso 1 1 calc R
H9B H 0.4106 0.1229 -0.0775 0.066 Uiso 1 1 calc R
C10 C 0.3102(5) 0.2390(6) 0.0274(4) 0.0463(11) Uani 1 1 d .
C11 C 0.2624(5) 0.4080(16) 0.0385(4) 0.0791(14) Uani 1 1 d .
H11 H 0.2180 0.4147 0.0977 0.095 Uiso 1 1 calc R
C12 C 0.1951(5) 0.1247(5) 0.0085(4) 0.0538(12) Uani 1 1 d .
C13 C 0.0657(5) 0.1588(7) -0.0275(5) 0.0686(13) Uani 1 1 d .
H13A H 0.0368 0.2639 -0.0444 0.082 Uiso 1 1 calc R
H13B H 0.0047 0.0773 -0.0356 0.082 Uiso 1 1 calc R
C14 C 0.4193(4) 0.2152(5) 0.1648(4) 0.0451(10) Uani 1 1 d .
C15 C 0.3845(5) 0.1956(6) 0.2750(4) 0.0637(13) Uani 1 1 d .
H15 H 0.2953 0.1890 0.2644 0.076 Uiso 1 1 calc R
C16 C 0.4788(5) 0.1855(7) 0.3996(4) 0.0663(13) Uani 1 1 d .
H16 H 0.4532 0.1734 0.4722 0.080 Uiso 1 1 calc R
C17 C 0.6103(5) 0.1935(5) 0.4162(4) 0.0536(11) Uani 1 1 d .
C18 C 0.6475(5) 0.2114(7) 0.3080(4) 0.0595(12) Uani 1 1 d .
H18 H 0.7369 0.2172 0.3189 0.071 Uiso 1 1 calc R
C19 C 0.5526(5) 0.2207(6) 0.1843(4) 0.0545(11) Uani 1 1 d .
H19 H 0.5787 0.2311 0.1118 0.065 Uiso 1 1 calc R
C20 C 0.6802(6) 0.1749(10) 0.6513(5) 0.105(2) Uani 1 1 d .
H20A H 0.6315 0.0781 0.6480 0.157 Uiso 1 1 calc R
H20B H 0.6270 0.2648 0.6565 0.157 Uiso 1 1 calc R
H20C H 0.7603 0.1734 0.7276 0.157 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 0.0033 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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 O2 C20 118.2(4)
C2 C1 C6 119.8(5)
C2 C1 H1 120.1
C6 C1 H1 120.1
C3 C2 C1 121.8(5)
C3 C2 H2 119.1
C1 C2 H2 119.1
C2 C3 C4 118.7(5)
C2 C3 H3 120.7
C4 C3 H3 120.7
C3 C4 C5 120.3(6)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 122.3(6)
C6 C5 H5 118.8
C4 C5 H5 118.8
C5 C6 C1 117.1(4)
C5 C6 C7 121.5(5)
C1 C6 C7 121.5(5)
C6 C7 C8 112.0(4)
C6 C7 H7A 109.2
C8 C7 H7A 109.2
C6 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C9 C8 C7 111.6(4)
C9 C8 H8A 109.3
C7 C8 H8A 109.3
C9 C8 H8B 109.3
C7 C8 H8B 109.3
H8A C8 H8B 108.0
C8 C9 C10 113.8(4)
C8 C9 H9A 108.8
C10 C9 H9A 108.8
C8 C9 H9B 108.8
C10 C9 H9B 108.8
H9A C9 H9B 107.7
C12 C10 C11 108.1(5)
C12 C10 C9 110.4(4)
C11 C10 C9 112.1(5)
C12 C10 C14 110.6(4)
C11 C10 C14 101.8(3)
C9 C10 C14 113.3(4)
O1 C11 C10 135.0(6)
O1 C11 H11 112.5
C10 C11 H11 112.5
C13 C12 C10 128.4(5)
C13 C12 Br1 117.3(4)
C10 C12 Br1 114.2(3)
C12 C13 H13A 120.0
C12 C13 H13B 120.0
H13A C13 H13B 120.0
C19 C14 C15 117.4(4)
C19 C14 C10 122.5(4)
C15 C14 C10 120.0(4)
C16 C15 C14 121.6(5)
C16 C15 H15 119.2
C14 C15 H15 119.2
C17 C16 C15 119.7(4)
C17 C16 H16 120.1
C15 C16 H16 120.1
C16 C17 O2 124.6(4)
C16 C17 C18 119.8(4)
O2 C17 C18 115.6(4)
C19 C18 C17 119.9(4)
C19 C18 H18 120.1
C17 C18 H18 120.1
C18 C19 C14 121.6(4)
C18 C19 H19 119.2
C14 C19 H19 119.2
O2 C20 H20A 109.5
O2 C20 H20B 109.5
H20A C20 H20B 109.5
O2 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.900(5)
O1 C11 1.032(13)
O2 C17 1.376(5)
O2 C20 1.415(7)
C1 C2 1.381(8)
C1 C6 1.384(7)
C1 H1 0.9300
C2 C3 1.331(9)
C2 H2 0.9300
C3 C4 1.348(9)
C3 H3 0.9300
C4 C5 1.374(8)
C4 H4 0.9300
C5 C6 1.341(7)
C5 H5 0.9300
C6 C7 1.520(6)
C7 C8 1.523(7)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.522(6)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.546(7)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C12 1.522(7)
C10 C11 1.525(13)
C10 C14 1.550(6)
C11 H11 0.9300
C12 C13 1.340(7)
C13 H13A 0.9300
C13 H13B 0.9300
C14 C19 1.377(6)
C14 C15 1.385(7)
C15 C16 1.375(6)
C15 H15 0.9300
C16 C17 1.366(7)
C16 H16 0.9300
C17 C18 1.379(7)
C18 C19 1.370(6)
C18 H18 0.9300
C19 H19 0.9300
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
