#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/29/1502940.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_1502940
loop_
_publ_author_name
'Samarakoon, Thiwanka B.'
'Hur, Moon Y.'
'Kurtz, Ryan D.'
'Hanson, Paul R.'
_publ_section_title
;
 A formal [4 + 4] complementary ambiphile pairing reaction: a new
 cyclization pathway for ortho-quinone methides.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2182
_journal_page_last               2185
_journal_paper_doi               10.1021/ol100495w
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C16 H14 Br N O3 S'
_chemical_formula_weight         380.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.217(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.252(2)
_cell_length_b                   7.4707(15)
_cell_length_c                   20.115(4)
_cell_measurement_reflns_used    1432
_cell_measurement_temperature    100(2)
_cell_volume                     1516.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX II CCD detector'
_diffrn_measurement_method       'w scans'
_diffrn_radiation_monochromator  'Quazar MX Optics'
_diffrn_radiation_source         'Bruker IuS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17720
_diffrn_reflns_theta_full        65.21
_diffrn_reflns_theta_max         65.21
_diffrn_reflns_theta_min         4.47
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    5.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.375
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0366
_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)+(0.0428P)²+2.8282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                2432
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100495w_si_002.cif
_cod_data_source_block           k76h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1502940
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
Br Br 0.41250(4) 0.60333(5) 0.063654(15) 0.03967(15) Uani 1 1 d
S S 0.40633(7) 0.54231(10) 0.38217(3) 0.02732(19) Uani 1 1 d
O1 O 0.58871(19) 0.7684(3) 0.31729(10) 0.0278(4) Uani 1 1 d
O2 O 0.3095(2) 0.4099(3) 0.38690(11) 0.0347(5) Uani 1 1 d
O3 O 0.3943(2) 0.7144(3) 0.41159(10) 0.0334(5) Uani 1 1 d
N N 0.5516(2) 0.4634(3) 0.41564(12) 0.0272(5) Uani 1 1 d
C1 C 0.4045(3) 0.5680(4) 0.29390(14) 0.0261(6) Uani 1 1 d
C2 C 0.3078(3) 0.4825(4) 0.24751(16) 0.0296(6) Uani 1 1 d
H2 H 0.242(4) 0.416(5) 0.2625(19) 0.038(10) Uiso 1 1 d
C3 C 0.3077(3) 0.4954(4) 0.17880(16) 0.0324(7) Uani 1 1 d
H3 H 0.243(3) 0.445(5) 0.1488(17) 0.027(8) Uiso 1 1 d
C4 C 0.4061(3) 0.5926(4) 0.15739(15) 0.0304(7) Uani 1 1 d
C5 C 0.5021(3) 0.6824(4) 0.20195(15) 0.0293(6) Uani 1 1 d
H5 H 0.567(3) 0.751(5) 0.1883(17) 0.033(9) Uiso 1 1 d
C6 C 0.5003(3) 0.6708(4) 0.27073(14) 0.0266(6) Uani 1 1 d
C7 C 0.7196(3) 0.7043(4) 0.33241(14) 0.0276(6) Uani 1 1 d
C8 C 0.8073(3) 0.7405(5) 0.28969(16) 0.0333(7) Uani 1 1 d
H8 H 0.778(3) 0.803(5) 0.2522(19) 0.032(9) Uiso 1 1 d
C9 C 0.9368(3) 0.6815(5) 0.30737(18) 0.0391(8) Uani 1 1 d
H9 H 0.995(4) 0.704(5) 0.280(2) 0.048(11) Uiso 1 1 d
C10 C 0.9775(3) 0.5910(5) 0.36799(18) 0.0379(8) Uani 1 1 d
H10 H 1.054(4) 0.554(5) 0.380(2) 0.041(10) Uiso 1 1 d
C11 C 0.8881(3) 0.5585(5) 0.41021(17) 0.0347(7) Uani 1 1 d
H11 H 0.914(3) 0.498(5) 0.4530(19) 0.038(9) Uiso 1 1 d
C12 C 0.7576(3) 0.6158(4) 0.39359(15) 0.0294(7) Uani 1 1 d
C13 C 0.6609(3) 0.5874(4) 0.44114(15) 0.0302(7) Uani 1 1 d
H13A H 0.711(4) 0.533(5) 0.485(2) 0.043(10) Uiso 1 1 d
H13B H 0.624(3) 0.698(5) 0.4507(16) 0.024(8) Uiso 1 1 d
C14 C 0.5870(3) 0.2926(4) 0.39002(15) 0.0303(7) Uani 1 1 d
H14 H 0.600(3) 0.297(5) 0.3455(18) 0.032(9) Uiso 1 1 d
C15 C 0.5304(4) 0.1245(5) 0.4126(2) 0.0412(8) Uani 1 1 d
H15A H 0.471(4) 0.139(5) 0.442(2) 0.047(11) Uiso 1 1 d
H15B H 0.506(4) 0.034(6) 0.381(2) 0.043(10) Uiso 1 1 d
C16 C 0.6724(4) 0.1699(5) 0.43861(18) 0.0393(8) Uani 1 1 d
H16A H 0.739(3) 0.110(4) 0.4178(18) 0.030(9) Uiso 1 1 d
H16B H 0.695(4) 0.206(5) 0.485(2) 0.040(10) Uiso 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'
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'
S S 0.3331 0.5567 '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
O2 S O3 119.16(13)
O2 S N 108.61(13)
O3 S N 107.06(13)
O2 S C1 104.97(14)
O3 S C1 109.21(13)
N S C1 107.30(13)
C6 O1 C7 116.8(2)
C14 N C13 117.0(2)
C14 N S 116.1(2)
C13 N S 119.9(2)
C2 C1 C6 119.4(3)
C2 C1 S 120.0(2)
C6 C1 S 120.7(2)
C3 C2 C1 120.8(3)
C3 C2 H2 119(2)
C1 C2 H2 120(2)
C4 C3 C2 118.6(3)
C4 C3 H3 120(2)
C2 C3 H3 121(2)
C3 C4 C5 122.1(3)
C3 C4 Br 119.4(2)
C5 C4 Br 118.5(2)
C4 C5 C6 118.8(3)
C4 C5 H5 123(2)
C6 C5 H5 118(2)
O1 C6 C5 121.1(3)
O1 C6 C1 118.6(2)
C5 C6 C1 120.2(3)
C8 C7 C12 122.3(3)
C8 C7 O1 120.2(3)
C12 C7 O1 117.4(3)
C7 C8 C9 118.7(3)
C7 C8 H8 118(2)
C9 C8 H8 123(2)
C8 C9 C10 120.3(3)
C8 C9 H9 120(3)
C10 C9 H9 120(3)
C11 C10 C9 119.8(3)
C11 C10 H10 117(3)
C9 C10 H10 123(3)
C10 C11 C12 121.0(3)
C10 C11 H11 121(2)
C12 C11 H11 117(2)
C11 C12 C7 117.8(3)
C11 C12 C13 121.2(3)
C7 C12 C13 121.0(3)
N C13 C12 114.3(2)
N C13 H13A 107(2)
C12 C13 H13A 108(2)
N C13 H13B 108(2)
C12 C13 H13B 109.7(19)
H13A C13 H13B 110(3)
N C14 C15 120.0(3)
N C14 C16 117.4(3)
C15 C14 C16 60.0(2)
N C14 H14 114(2)
C15 C14 H14 117(2)
C16 C14 H14 119(2)
C14 C15 C16 60.5(2)
C14 C15 H15A 115(3)
C16 C15 H15A 117(3)
C14 C15 H15B 118(2)
C16 C15 H15B 122(2)
H15A C15 H15B 114(4)
C15 C16 C14 59.5(2)
C15 C16 H16A 117(2)
C14 C16 H16A 112(2)
C15 C16 H16B 117(2)
C14 C16 H16B 118(2)
H16A C16 H16B 119(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C4 1.900(3)
S O2 1.417(2)
S O3 1.429(2)
S N 1.632(2)
S C1 1.783(3)
O1 C6 1.389(4)
O1 C7 1.406(4)
N C14 1.446(4)
N C13 1.474(4)
C1 C2 1.390(4)
C1 C6 1.391(4)
C2 C3 1.385(4)
C2 H2 0.93(4)
C3 C4 1.373(5)
C3 H3 0.89(4)
C4 C5 1.382(5)
C5 C6 1.389(4)
C5 H5 0.92(4)
C7 C8 1.376(4)
C7 C12 1.391(4)
C8 C9 1.384(5)
C8 H8 0.89(4)
C9 C10 1.392(5)
C9 H9 0.90(4)
C10 C11 1.377(5)
C10 H10 0.83(4)
C11 C12 1.388(5)
C11 H11 0.97(4)
C12 C13 1.510(4)
C13 H13A 1.02(4)
C13 H13B 0.94(3)
C14 C15 1.488(5)
C14 C16 1.503(5)
C14 H14 0.93(4)
C15 C16 1.496(6)
C15 H15A 0.92(4)
C15 H15B 0.93(4)
C16 H16A 0.97(4)
C16 H16B 0.95(4)
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
O2 S N C14 53.3(2)
O3 S N C14 -176.9(2)
C1 S N C14 -59.7(2)
O2 S N C13 -156.8(2)
O3 S N C13 -26.9(2)
C1 S N C13 90.3(2)
O2 S C1 C2 7.7(3)
O3 S C1 C2 -121.1(3)
N S C1 C2 123.1(2)
O2 S C1 C6 -171.3(2)
O3 S C1 C6 59.8(3)
N S C1 C6 -55.9(3)
C6 C1 C2 C3 1.5(5)
S C1 C2 C3 -177.6(2)
C1 C2 C3 C4 0.8(5)
C2 C3 C4 C5 -2.3(5)
C2 C3 C4 Br 177.2(2)
C3 C4 C5 C6 1.4(5)
Br C4 C5 C6 -178.1(2)
C7 O1 C6 C5 -76.6(3)
C7 O1 C6 C1 106.9(3)
C4 C5 C6 O1 -175.5(3)
C4 C5 C6 C1 1.0(5)
C2 C1 C6 O1 174.2(3)
S C1 C6 O1 -6.8(4)
C2 C1 C6 C5 -2.4(4)
S C1 C6 C5 176.7(2)
C6 O1 C7 C8 80.7(3)
C6 O1 C7 C12 -103.6(3)
C12 C7 C8 C9 2.1(5)
O1 C7 C8 C9 177.5(3)
C7 C8 C9 C10 -1.4(5)
C8 C9 C10 C11 0.7(5)
C9 C10 C11 C12 -0.5(5)
C10 C11 C12 C7 1.1(5)
C10 C11 C12 C13 -177.3(3)
C8 C7 C12 C11 -1.9(5)
O1 C7 C12 C11 -177.4(3)
C8 C7 C12 C13 176.5(3)
O1 C7 C12 C13 1.0(4)
C14 N C13 C12 49.8(4)
S N C13 C12 -99.9(3)
C11 C12 C13 N -114.0(3)
C7 C12 C13 N 67.6(4)
C13 N C14 C15 131.4(3)
S N C14 C15 -77.7(3)
C13 N C14 C16 62.0(4)
S N C14 C16 -147.2(3)
N C14 C15 C16 -106.3(3)
N C14 C16 C15 110.5(3)
