#------------------------------------------------------------------------------
#$Date: 2017-07-08 14:09:18 +0300 (Sat, 08 Jul 2017) $
#$Revision: 198578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/57/7155755.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_7155755
loop_
_publ_author_name
'Ligny, Romain'
'Gauthier, Etienne S.'
'Yáñez, Manuel'
'Roisnel, Thierry'
'Guillemin, Jean-Claude'
'Trolez, Yann'
_publ_section_title
;
 One-step synthesis of conjugated enynenitriles from bromocyanoacetylene.
;
_journal_name_full               'Organic & biomolecular chemistry'
_journal_paper_doi               10.1039/c6ob02590k
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C3 Br N'
_chemical_formula_sum            'C3 Br N'
_chemical_formula_weight         129.95
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_audit_update_record
;
2016-11-10 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.735(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0950(10)
_cell_length_b                   6.1734(13)
_cell_length_c                   6.2035(14)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.30
_cell_measurement_wavelength     0.71073
_cell_volume                     194.14(7)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1670
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.301
_exptl_absorpt_coefficient_mu    10.357
_exptl_absorpt_correction_T_max  0.394
_exptl_absorpt_correction_T_min  0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.223
_exptl_crystal_description       block
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.553
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_matrix_type           full
_refine_ls_number_parameters     31
_refine_ls_number_reflns         486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0405P)²+0.0220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                471
_reflns_number_total             486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02590k2.cif
_cod_data_source_block           YT_BRC3N
_cod_database_code               7155755
_shelx_res_file
;
TITL import in P 21/m
    job.res
    created by SHELXL-2016/6 at 14:16:57 on 09-Nov-2016
CELL  0.71073   5.0950   6.1734   6.2035   90.000   95.735   90.000
ZERR     2.00   0.0010   0.0013   0.0014    0.000    0.009    0.000
LATT   1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    N    BR
UNIT  6    2    2
MERG   2
FMAP   2
PLAN   20
ACTA
CONF
LIST   4
WPDB  -2
L.S.   4
TEMP    21.00
WGHT    0.040500    0.022000
FVAR       1.13424
C1    1    0.034740    0.250000    0.740539    10.50000    0.02273    0.01698 =
         0.02180    0.00000    0.00338    0.00000
C2    1   -0.109765    0.250000    0.880473    10.50000    0.02474    0.01930 =
         0.02146    0.00000    0.00488    0.00000
C3    1   -0.281079    0.250000    1.038960    10.50000    0.02641    0.02060 =
         0.02209    0.00000    0.00499    0.00000
N4    2   -0.423352    0.250000    1.172092    10.50000    0.03486    0.03312 =
         0.02823    0.00000    0.01327    0.00000
BR1   3    0.247082    0.250000    0.527850    10.50000    0.02149    0.01920 =
         0.02002    0.00000    0.00735    0.00000
HKLF    4




REM  import in P 21/m
REM R1 =  0.0289 for     471 Fo > 4sig(Fo)  and  0.0300 for all     486 data
REM     31 parameters refined using      0 restraints

END

WGHT      0.0384      0.0218

REM Highest difference peak  0.553,  deepest hole -1.115,  1-sigma level  0.247
Q1    1   0.3288  0.2500  0.6688  10.50000  0.05    0.55
Q2    1  -0.1812 -0.0234  0.8419  11.00000  0.05    0.54
Q3    1  -0.0189 -0.0106  0.8027  11.00000  0.05    0.53
Q4    1  -0.5403 -0.0104  1.3377  11.00000  0.05    0.52
Q5    1   0.1868  0.0673  0.4202  11.00000  0.05    0.49
Q6    1  -0.5094 -0.0290  1.2413  11.00000  0.05    0.49
Q7    1  -0.4001  0.0260  1.2599  11.00000  0.05    0.48
Q8    1  -0.1096  0.0275  0.6734  11.00000  0.05    0.46
Q9    1  -0.3371 -0.0381  1.1474  11.00000  0.05    0.45
Q10   1   0.0395 -0.0278  0.6627  11.00000  0.05    0.45
Q11   1  -0.6194  0.0106  1.1151  11.00000  0.05    0.44
Q12   1  -0.1049  0.0089  0.9656  11.00000  0.05    0.42
Q13   1   0.1837  0.0371  0.2858  11.00000  0.05    0.42
Q14   1  -0.4011 -0.0191  1.0815  11.00000  0.05    0.42
Q15   1  -0.2694 -0.0263  1.0137  11.00000  0.05    0.41
Q16   1   0.1651  0.2500  0.3834  10.50000  0.05    0.35
Q17   1   0.3180  0.0660  0.4224  11.00000  0.05    0.34
Q18   1   0.2711 -0.0018  0.3245  11.00000  0.05    0.33
Q19   1   0.1281  0.0084  0.8359  11.00000  0.05    0.32
Q20   1   0.2239  0.0225  0.5986  11.00000  0.05    0.32
;
_shelx_res_checksum              58305
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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
_atom_site_refinement_flags_occupancy
C1 C 0.0347(8) 0.250000 0.7405(7) 0.0204(8) Uani 1 2 d S T P
C2 C -0.1098(9) 0.250000 0.8805(7) 0.0217(9) Uani 1 2 d S T P
C3 C -0.2811(8) 0.250000 1.0390(7) 0.0229(9) Uani 1 2 d S T P
N4 N -0.4234(9) 0.250000 1.1721(7) 0.0314(9) Uani 1 2 d S T P
Br1 Br 0.24708(6) 0.250000 0.52785(6) 0.0199(2) Uani 1 2 d S T P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.023(2) 0.0170(17) 0.0218(19) 0.000 0.0034(15) 0.000
C2 0.025(2) 0.0193(19) 0.021(2) 0.000 0.0049(17) 0.000
C3 0.026(2) 0.021(2) 0.022(2) 0.000 0.0050(17) 0.000
N4 0.035(2) 0.033(2) 0.028(2) 0.000 0.0133(18) 0.000
Br1 0.0215(3) 0.0192(3) 0.0200(3) 0.000 0.00735(16) 0.000
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'
N N 0.0061 0.0033 '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
C2 C1 Br1 179.1(4)
C1 C2 C3 178.8(5)
N4 C3 C2 179.7(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.193(7)
C1 Br1 1.788(4)
C2 C3 1.378(6)
C3 N4 1.152(7)
