#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/82/1518269.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_1518269
loop_
_publ_author_name
'Chen, Wenwen'
'Wang, Bo'
'Liu, Nan'
'Huang, Dayun'
'Wang, Xinyan'
'Hu, Yuefei'
_publ_section_title
;
 Tandem Synthesis of 3-Halo-5-Substituted Isoxazoles from 1-Copper(I)
 Alkynes and Dihaloformaldoximes.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6140
_journal_paper_doi               10.1021/ol503008t
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H6 Br N O'
_chemical_formula_weight         224.06
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.215(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.584(3)
_cell_length_b                   4.1885(11)
_cell_length_c                   11.089(3)
_cell_measurement_reflns_used    888
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.80
_cell_measurement_theta_min      2.89
_cell_volume                     444.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4256
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.018
_diffrn_reflns_theta_min         1.839
_exptl_absorpt_coefficient_mu    4.572
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_description       Block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
; 
 Flack x determined using 381 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                1302
_reflns_number_total             2405
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol503008t_si_002.cif
_cod_data_source_block           mo_dm14406_0m
_cod_depositor_comments          'Adding full bibliography for 1518269.cif.'
_cod_original_cell_volume        444.5(2)
_cod_database_code               1518269
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.394
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.64549(7) 1.2237(2) 0.44692(6) 0.0606(3) Uani 1 1 d . .
N1 N 0.8816(6) 0.8883(14) 0.4347(5) 0.0476(14) Uani 1 1 d . .
O1 O 0.9739(5) 0.714(3) 0.3689(4) 0.0618(13) Uani 1 1 d . .
C1 C 0.6370(8) 0.990(2) -0.0667(6) 0.059(2) Uani 1 1 d . .
H1 H 0.5660 1.1081 -0.0342 0.071 Uiso 1 1 calc R U
C2 C 0.6381(10) 0.943(2) -0.1886(7) 0.073(3) Uani 1 1 d . .
H2 H 0.5669 1.0287 -0.2390 0.087 Uiso 1 1 calc R U
C3 C 0.7419(10) 0.773(3) -0.2372(7) 0.081(4) Uani 1 1 d . .
H3 H 0.7419 0.7452 -0.3204 0.098 Uiso 1 1 calc R U
C4 C 0.8456(10) 0.643(2) -0.1641(8) 0.079(3) Uani 1 1 d . .
H4 H 0.9168 0.5269 -0.1974 0.095 Uiso 1 1 calc R U
C5 C 0.8452(7) 0.682(3) -0.0426(7) 0.060(2) Uani 1 1 d . .
H5 H 0.9148 0.5868 0.0071 0.072 Uiso 1 1 calc R U
C6 C 0.7432(7) 0.8600(16) 0.0077(6) 0.0436(15) Uani 1 1 d . .
C7 C 0.7463(7) 0.9110(18) 0.1355(7) 0.0501(17) Uani 1 1 d . .
C8 C 0.7590(7) 0.9467(17) 0.2410(6) 0.0503(17) Uani 1 1 d . .
C9 C 0.7798(7) 0.9907(17) 0.3651(6) 0.0444(16) Uani 1 1 d . .
H1A H 1.013(8) 0.625(19) 0.416(7) 0.07(3) 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 0.0033 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'
N N 0.0061 0.0033 '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
C9 N1 O1 110.2(5)
N1 O1 H1A 102(7)
C2 C1 C6 119.1(8)
C2 C1 H1 120.5
C6 C1 H1 120.5
C3 C2 C1 121.0(8)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 120.0(7)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 120.0(9)
C5 C4 H4 120.0
C3 C4 H4 120.0
C4 C5 C6 120.7(8)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 119.2(6)
C5 C6 C7 120.5(6)
C1 C6 C7 120.3(7)
C8 C7 C6 175.1(8)
C7 C8 C9 177.7(8)
N1 C9 C8 127.8(6)
N1 C9 Br1 113.6(5)
C8 C9 Br1 118.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9 1.887(7)
N1 C9 1.283(8)
N1 O1 1.385(10)
O1 H1A 0.73(8)
C1 C2 1.366(10)
C1 C6 1.386(9)
C1 H1 0.9300
C2 C3 1.359(14)
C2 H2 0.9300
C3 C4 1.361(13)
C3 H3 0.9300
C4 C5 1.357(11)
C4 H4 0.9300
C5 C6 1.374(11)
C5 H5 0.9300
C6 C7 1.432(10)
C7 C8 1.178(9)
C8 C9 1.392(9)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N1 0.73(8) 2.14(8) 2.861(9) 175(9) 2_746
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 -0.4(14)
C1 C2 C3 C4 0.9(17)
C2 C3 C4 C5 0.3(17)
C3 C4 C5 C6 -2.0(15)
C4 C5 C6 C1 2.5(13)
C4 C5 C6 C7 -177.5(8)
C2 C1 C6 C5 -1.3(12)
C2 C1 C6 C7 178.7(7)
O1 N1 C9 C8 -0.8(11)
O1 N1 C9 Br1 178.7(7)
