#------------------------------------------------------------------------------
#$Date: 2016-03-04 10:40:38 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177360 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/27/1542711.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_1542711
loop_
_publ_author_name
'Sasaki, Teppei'
'Miyagi, Kotaro'
'Moriyama, Katsuhiko'
'Togo, Hideo'
_publ_section_title
;
 Direct Preparation of 3-Iodochromenes from 3-Aryl- and
 3-Alkyl-2-propyn-1-ols with Diaryliodonium Salts and NIS.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              944
_journal_paper_doi               10.1021/acs.orglett.5b03651
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C15 H10 Br I O'
_chemical_formula_weight         413.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 91.919(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.603(4)
_cell_length_b                   10.723(5)
_cell_length_c                   16.702(8)
_cell_measurement_reflns_used    3426
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5576
_cell_measurement_theta_min      2.2574
_cell_volume                     1360.9(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6932
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    5.274
_exptl_absorpt_correction_T_max  0.42
_exptl_absorpt_correction_T_min  0.31
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.790
_refine_diff_density_min         -1.435
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0782P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2549
_reflns_number_total             3034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b03651_si_002.cif
_cod_data_source_block           I
_cod_original_cell_volume        1360.9(11)
_cod_database_code               1542711
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
I I1 1.39716(4) 0.80772(3) 0.88456(2) 0.04079(15) Uani d . . 1
Br Br1 0.49153(7) 0.61139(5) 1.12217(3) 0.04757(18) Uani d . . 1
C C8 0.8745(6) 0.8838(4) 1.1600(3) 0.0354(10) Uani d . . 1
H H8 0.9046 0.9442 1.1998 0.042 Uiso calc U R 1
O O1 1.1184(4) 0.9494(3) 1.08694(18) 0.0343(7) Uani d . . 1
C C3 1.0492(5) 0.7713(3) 0.9643(2) 0.0219(8) Uani d . . 1
C C10 0.9853(5) 0.6934(3) 0.8951(2) 0.0205(7) Uani d . . 1
C C5 0.7834(6) 0.7106(3) 1.0413(2) 0.0251(8) Uani d . . 1
H H5 0.7487 0.6533 1.0003 0.03 Uiso calc U R 1
C C4 0.9336(5) 0.7840(3) 1.0331(2) 0.0229(8) Uani d . . 1
C C7 0.7275(7) 0.8088(4) 1.1687(3) 0.0370(11) Uani d . . 1
H H7 0.657 0.8169 1.2143 0.044 Uiso calc U R 1
C C9 0.9778(6) 0.8708(4) 1.0935(2) 0.0266(8) Uani d . . 1
C C11 0.8671(5) 0.7444(4) 0.8391(2) 0.0261(8) Uani d . . 1
H H11 0.8322 0.8292 0.8433 0.031 Uiso calc U R 1
C C12 0.7993(6) 0.6702(4) 0.7761(2) 0.0322(9) Uani d . . 1
H H12 0.719 0.7051 0.7375 0.039 Uiso calc U R 1
C C6 0.6850(5) 0.7215(4) 1.1093(2) 0.0284(9) Uani d . . 1
C C13 0.8486(6) 0.5471(4) 0.7701(2) 0.0329(9) Uani d . . 1
H H13 0.7999 0.4965 0.7282 0.04 Uiso calc U R 1
C C15 1.0368(7) 0.5701(4) 0.8877(2) 0.0345(10) Uani d . . 1
H H15 1.1188 0.5351 0.9256 0.041 Uiso calc U R 1
C C14 0.9687(8) 0.4976(4) 0.8250(3) 0.0423(12) Uani d . . 1
H H14 1.0053 0.4133 0.8199 0.051 Uiso calc U R 1
C C2 1.2050(5) 0.8292(4) 0.9697(2) 0.0243(8) Uani d . . 1
C C1 1.2600(6) 0.9091(4) 1.0398(2) 0.0325(9) Uani d . . 1
H H1A 1.3444 0.8616 1.0744 0.039 Uiso calc U R 1
H H1B 1.3222 0.9834 1.0199 0.039 Uiso calc U R 1
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'
I I -0.4742 1.8119 '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
C9 C8 C7 120.3(4)
C9 C8 H8 119.9
C7 C8 H8 119.9
C9 O1 C1 117.7(3)
C2 C3 C4 117.0(3)
C2 C3 C10 125.1(3)
C4 C3 C10 117.8(3)
C15 C10 C11 119.7(4)
C15 C10 C3 121.0(4)
C11 C10 C3 119.2(3)
C6 C5 C4 119.8(4)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C4 C9 118.7(3)
C5 C4 C3 122.3(3)
C9 C4 C3 119.1(4)
C8 C7 C6 118.8(4)
C8 C7 H7 120.6
C6 C7 H7 120.6
O1 C9 C8 117.8(3)
O1 C9 C4 121.2(3)
C8 C9 C4 120.9(4)
C10 C11 C12 119.7(4)
C10 C11 H11 120.2
C12 C11 H11 120.2
C13 C12 C11 120.3(4)
C13 C12 H12 119.8
C11 C12 H12 119.8
C5 C6 C7 121.5(4)
C5 C6 Br1 118.7(3)
C7 C6 Br1 119.8(3)
C12 C13 C14 119.8(4)
C12 C13 H13 120.1
C14 C13 H13 120.1
C10 C15 C14 120.1(4)
C10 C15 H15 120.0
C14 C15 H15 120.0
C13 C14 C15 120.5(4)
C13 C14 H14 119.8
C15 C14 H14 119.8
C3 C2 C1 122.7(3)
C3 C2 I1 122.9(3)
C1 C2 I1 114.4(3)
O1 C1 C2 114.2(3)
O1 C1 H1A 108.7
C2 C1 H1A 108.7
O1 C1 H1B 108.7
C2 C1 H1B 108.7
H1A C1 H1B 107.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C2 2.085(4)
Br1 C6 1.904(4)
C8 C9 1.388(6)
C8 C7 1.389(7)
C8 H8 0.95
O1 C9 1.369(5)
O1 C1 1.422(5)
C3 C2 1.337(6)
C3 C4 1.476(5)
C3 C10 1.495(5)
C10 C15 1.385(5)
C10 C11 1.387(6)
C5 C6 1.386(5)
C5 C4 1.398(6)
C5 H5 0.95
C4 C9 1.405(5)
C7 C6 1.394(6)
C7 H7 0.95
C11 C12 1.403(6)
C11 H11 0.95
C12 C13 1.377(6)
C12 H12 0.95
C13 C14 1.379(7)
C13 H13 0.95
C15 C14 1.392(6)
C15 H15 0.95
C14 H14 0.95
C2 C1 1.500(5)
C1 H1A 0.99
C1 H1B 0.99
