#------------------------------------------------------------------------------
#$Date: 2018-02-18 11:45:15 +0200 (Sun, 18 Feb 2018) $
#$Revision: 206489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/98/7119817.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_7119817
loop_
_publ_author_name
'Huang, Xiaoshan'
'Cong, Xuefeng'
'Mi, Pengbing'
'Bi, Xihe'
_publ_section_title
;
 Azomethine-isocyanide [3+2] cycloaddition to imidazoles promoted by
 silver and DBU.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3858
_journal_page_last               3861
_journal_paper_doi               10.1039/c7cc00772h
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C17 H11 Br N2 O2'
_chemical_formula_weight         355.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-13 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7312(6)
_cell_length_b                   11.0728(6)
_cell_length_c                   12.9937(7)
_cell_measurement_temperature    273(2)
_cell_volume                     1543.97(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9239
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.417
_exptl_absorpt_coefficient_mu    12.385
_exptl_crystal_density_diffrn    2.512
_exptl_crystal_F_000             1083
_refine_diff_density_max         6.215
_refine_diff_density_min         -3.911
_refine_diff_density_rms         0.247
_refine_ls_abs_structure_details
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.961(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.748
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.748
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.1508
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3735
_refine_ls_wR_factor_ref         0.3885
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2694
_reflns_number_total             3168
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc00772h2.cif
_cod_data_source_block           11
_cod_depositor_comments
;
          Adding full bibliography for 7119817.cif.

2018-01-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C H Br N O'
_cod_original_formula_weight         122.94
_cod_original_formula_units_Z            19
_cod_database_code               7119817
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Br1 Br 0.1126(2) 0.2757(2) 0.46481(14) 0.0470(8) Uiso 1 1 d
O1 O 0.9053(12) 0.5447(12) 0.6791(9) 0.034(3) Uiso 1 1 d
C2 C 0.2460(16) 0.3747(18) 0.5136(12) 0.031(4) Uiso 1 1 d
N1 N 0.6519(12) 0.7562(12) 0.6490(8) 0.024(3) Uiso 1 1 d
O4 O 0.9138(13) 0.7476(13) 0.6977(9) 0.041(3) Uiso 1 1 d
N2 N 0.5338(13) 0.5954(14) 0.6195(10) 0.029(3) Uiso 1 1 d
C6 C 0.5375(14) 0.7203(17) 0.6281(11) 0.025(3) Uiso 1 1 d
C7 C 0.4348(15) 0.5208(16) 0.5840(12) 0.023(3) Uiso 1 1 d
C9 C 0.3470(18) 0.9955(19) 0.5729(14) 0.036(4) Uiso 1 1 d
C10 C 0.3790(16) 0.5456(16) 0.4895(11) 0.029(3) Uiso 1 1 d
C11 C 0.6496(16) 0.5544(17) 0.6390(12) 0.029(4) Uiso 1 1 d
C12 C 0.4301(16) 0.8004(17) 0.6200(12) 0.029(4) Uiso 1 1 d
C13 C 0.7225(16) 0.6537(17) 0.6555(12) 0.028(4) Uiso 1 1 d
C14 C 0.3939(18) 0.4252(17) 0.6454(12) 0.033(4) Uiso 1 1 d
C15 C 0.4473(18) 0.9159(19) 0.5778(14) 0.037(4) Uiso 1 1 d
C16 C 0.8589(14) 0.6581(15) 0.6814(11) 0.023(3) Uiso 1 1 d
C17 C 0.212(2) 0.845(2) 0.6490(14) 0.041(5) Uiso 1 1 d
C18 C 0.3093(19) 0.766(2) 0.6572(14) 0.041(4) Uiso 1 1 d
C19 C 0.2975(18) 0.3497(19) 0.6077(14) 0.037(4) Uiso 1 1 d
C20 C 1.037(2) 0.538(2) 0.7028(16) 0.047(5) Uiso 1 1 d
C21 C 0.2283(18) 0.9601(19) 0.6066(13) 0.035(4) Uiso 1 1 d
C22 C 0.2835(17) 0.4729(18) 0.4536(13) 0.032(4) 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
C16 O1 C20 113.7(16)
C19 C2 C22 122.6(18)
C19 C2 Br1 118.9(15)
C22 C2 Br1 118.4(12)
C6 N1 C13 106.1(15)
C11 N2 C6 107.1(15)
C11 N2 C7 123.7(16)
C6 N2 C7 128.8(15)
N1 C6 N2 110.1(15)
N1 C6 C12 124.6(16)
N2 C6 C12 125.2(15)
C10 C7 C14 121.2(16)
C10 C7 N2 119.5(15)
C14 C7 N2 119.3(15)
C15 C9 C21 120.7(18)
C22 C10 C7 120.0(16)
N2 C11 C13 106.6(16)
C15 C12 C18 119.5(17)
C15 C12 C6 118.6(16)
C18 C12 C6 121.8(17)
N1 C13 C11 110.0(15)
N1 C13 C16 121.8(16)
C11 C13 C16 128.2(17)
C7 C14 C19 118.6(16)
C9 C15 C12 119.5(18)
O4 C16 O1 127.2(16)
O4 C16 C13 123.9(16)
O1 C16 C13 108.9(14)
C18 C17 C21 121(2)
C17 C18 C12 119(2)
C2 C19 C14 118.9(18)
C17 C21 C9 119.4(19)
C10 C22 C2 118.5(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.912(18)
O1 C16 1.35(2)
O1 C20 1.45(3)
C2 C19 1.37(2)
C2 C22 1.40(3)
N1 C6 1.32(2)
N1 C13 1.37(2)
O4 C16 1.17(2)
N2 C11 1.35(2)
N2 C6 1.39(2)
N2 C7 1.42(2)
C6 C12 1.46(2)
C7 C10 1.39(2)
C7 C14 1.40(2)
C9 C15 1.39(3)
C9 C21 1.40(3)
C10 C22 1.38(2)
C11 C13 1.37(3)
C12 C15 1.40(3)
C12 C18 1.44(3)
C13 C16 1.50(2)
C14 C19 1.42(3)
C17 C18 1.37(3)
C17 C21 1.40(3)
