#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/22/7222258.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_7222258
loop_
_publ_author_name
'Islam, Kobirul'
'Sidick Basha, R.'
'Dar, Ajaz A.'
'Das, Deb K.'
'Khan, Abu T.'
_publ_section_title
;
 A direct approach for the expedient synthesis of unsymmetrical ethers by
 employing bromodimethylsulfonium bromide (BDMS) mediated C--S bond
 cleavage of naphthalene-2-ol sulfides
;
_journal_issue                   97
_journal_name_full               'RSC Adv.'
_journal_page_first              79759
_journal_paper_doi               10.1039/C5RA14563E
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C18 H15 Br O2'
_chemical_formula_sum            'C18 H15 Br O2'
_chemical_formula_weight         343.20
_chemical_name_common            2n
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2012-12-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.548(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1085(6)
_cell_length_b                   7.3865(4)
_cell_length_c                   16.4008(7)
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.81
_cell_measurement_theta_min      2.37
_cell_volume                     1514.12(13)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.929
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_sigmaI/netI    0.1258
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18573
_diffrn_reflns_theta_full        28.59
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696.0
_exptl_crystal_recrystallization_method 'slow evaporation of DCM, chloroform'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.1849
_refine_ls_R_factor_gt           0.0464
_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)+(0.0412P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1393
_reflns_number_total             3866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra14563e2.cif
_cod_data_source_block           ki-113
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7222258
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
_atom_site_refinement_flags
Br1 Br 0.36927(4) 0.52673(8) 0.18144(3) 0.0899(3) Uani 1 1 d .
C12 C 0.3631(3) 0.4100(6) 0.4266(2) 0.0431(10) Uani 1 1 d .
C9 C 0.2686(3) 0.2799(5) 0.5950(2) 0.0476(10) Uani 1 1 d .
C17 C 0.3543(3) 0.4980(5) 0.3499(2) 0.0486(10) Uani 1 1 d .
H17 H 0.3297 0.6167 0.3413 0.058 Uiso 1 1 calc R
C11 C 0.3302(3) 0.5022(5) 0.4981(2) 0.0439(10) Uani 1 1 d .
H11 H 0.3932 0.5117 0.5487 0.053 Uiso 1 1 calc R
C10 C 0.2448(3) 0.3918(5) 0.5212(2) 0.0438(10) Uani 1 1 d .
C16 C 0.3830(3) 0.4058(7) 0.2862(2) 0.0530(11) Uani 1 1 d .
C14 C 0.4313(3) 0.1475(7) 0.3737(3) 0.0709(13) Uani 1 1 d .
H14 H 0.4573 0.0296 0.3821 0.085 Uiso 1 1 calc R
C18 C 0.2758(3) 0.7907(6) 0.5362(2) 0.0669(13) Uani 1 1 d .
H18A H 0.2202 0.7381 0.5555 0.100 Uiso 1 1 calc R
H18B H 0.2548 0.9099 0.5143 0.100 Uiso 1 1 calc R
H18C H 0.3406 0.7980 0.5831 0.100 Uiso 1 1 calc R
C8 C 0.3730(3) 0.2627(6) 0.6540(2) 0.0600(12) Uani 1 1 d .
H8 H 0.4295 0.3270 0.6446 0.072 Uiso 1 1 calc R
C6 C 0.3074(7) 0.0551(7) 0.7396(4) 0.099(2) Uani 1 1 d .
H6 H 0.3202 -0.0201 0.7871 0.119 Uiso 1 1 calc R
C15 C 0.4220(3) 0.2353(8) 0.2971(2) 0.0659(13) Uani 1 1 d .
H15 H 0.4422 0.1779 0.2540 0.079 Uiso 1 1 calc R
C4 C 0.1853(4) 0.1797(6) 0.6123(3) 0.0659(13) Uani 1 1 d .
C5 C 0.2070(6) 0.0706(7) 0.6845(4) 0.0987(19) Uani 1 1 d .
H5 H 0.1514 0.0066 0.6954 0.118 Uiso 1 1 calc R
C3 C 0.0803(4) 0.1935(7) 0.5537(3) 0.0801(17) Uani 1 1 d .
H3 H 0.0249 0.1273 0.5637 0.096 Uiso 1 1 calc R
C7 C 0.3919(4) 0.1532(7) 0.7244(3) 0.0815(15) Uani 1 1 d .
H7 H 0.4606 0.1438 0.7623 0.098 Uiso 1 1 calc R
C13 C 0.4018(3) 0.2354(6) 0.4379(2) 0.0562(11) Uani 1 1 d .
H13 H 0.4082 0.1758 0.4892 0.067 Uiso 1 1 calc R
C2 C 0.0600(3) 0.2995(7) 0.4848(3) 0.0714(14) Uani 1 1 d .
H2 H -0.0093 0.3055 0.4476 0.086 Uiso 1 1 calc R
C1 C 0.1404(3) 0.4015(6) 0.4675(3) 0.0539(11) Uani 1 1 d .
O2 O 0.29370(19) 0.6801(4) 0.46989(14) 0.0525(7) Uani 1 1 d .
O1 O 0.1099(2) 0.5082(4) 0.39626(17) 0.0685(9) Uani 1 1 d .
H1 H 0.1570 0.5824 0.3980 0.103 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'
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
C13 C12 C17 119.1(3)
C13 C12 C11 119.5(3)
C17 C12 C11 121.5(4)
C4 C9 C10 119.4(4)
C4 C9 C8 117.2(4)
C10 C9 C8 123.4(3)
C12 C17 C16 118.9(4)
O2 C11 C10 111.9(3)
O2 C11 C12 107.8(3)
C10 C11 C12 110.6(3)
C1 C10 C9 119.5(3)
C1 C10 C11 118.2(3)
C9 C10 C11 122.3(3)
C15 C16 C17 122.3(4)
C15 C16 Br1 119.2(3)
C17 C16 Br1 118.5(3)
C15 C14 C13 120.0(4)
C7 C8 C9 121.2(4)
C5 C6 C7 119.7(5)
C16 C15 C14 118.9(4)
C5 C4 C9 120.1(5)
C5 C4 C3 121.7(5)
C9 C4 C3 118.2(4)
C6 C5 C4 121.7(6)
C2 C3 C4 121.2(4)
C8 C7 C6 120.1(5)
C12 C13 C14 120.8(4)
C3 C2 C1 121.3(5)
O1 C1 C10 123.4(3)
O1 C1 C2 116.3(4)
C10 C1 C2 120.3(4)
C11 O2 C18 113.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C16 1.897(4)
C12 C13 1.378(5)
C12 C17 1.390(5)
C12 C11 1.525(5)
C9 C4 1.417(5)
C9 C10 1.420(5)
C9 C8 1.425(5)
C17 C16 1.390(5)
C11 O2 1.428(4)
C11 C10 1.523(5)
C10 C1 1.388(5)
C16 C15 1.350(6)
C14 C15 1.386(5)
C14 C13 1.389(5)
C18 O2 1.434(4)
C8 C7 1.370(5)
C6 C5 1.358(8)
C6 C7 1.407(7)
C4 C5 1.389(6)
C4 C3 1.425(6)
C3 C2 1.334(6)
C2 C1 1.392(5)
C1 O1 1.366(5)
