#------------------------------------------------------------------------------
#$Date: 2019-11-17 03:58:20 +0100 (dom 17 de nov de 2019) $
#$Revision: 227995 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/13/7121334.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_7121334
loop_
_publ_author_name
'Alimi, Lukman O.'
'Lama, Prem'
'Smith, Vincent J.'
'Barbour, Leonard J.'
_publ_section_title
;
 Hand-twistable plastically deformable crystals of a rigid small organic
 molecule.
;
_journal_issue                   24
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2994
_journal_page_last               2997
_journal_paper_doi               10.1039/c8cc00775f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C7 H4 Br N'
_chemical_formula_weight         182.02
_chemical_name_common            4-bromobenzonitrile
_chemical_name_systematic        4-bromobenzonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_symmetry_space_group_name_Hall  'C -2y'
_symmetry_space_group_name_H-M   'C 1 m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-11-26 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.295(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.531(2)
_cell_length_b                   8.5593(18)
_cell_length_c                   4.1352(9)
_cell_measurement_reflns_used    2352
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      3.20
_cell_volume                     337.34(12)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0463
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3422
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_min         3.199
_exptl_absorpt_coefficient_mu    5.990
_exptl_absorpt_correction_T_max  0.575
_exptl_absorpt_correction_T_min  0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.32(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     49
_refine_ls_number_reflns         893
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1247P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1534
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                869
_reflns_number_total             893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc00775f5.cif
_cod_data_source_block           4-BBN-S
_cod_depositor_comments
'Adding full bibliography for 7121334--7121335.cif.'
_cod_database_code               7121334
_shelx_shelxl_version_number     2016/6
_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   0.074
_shelx_estimated_absorpt_t_max   0.575
_shelx_res_file
;
TITL 273K in Cm
    C:\frames\guest\LA97D3~1\work\CHECKC~1\273k.res
    created by SHELXL-2016/6 at 12:36:47 on 30-May-2017
CELL 0.71073 9.5309 8.5593 4.1352 90.000 90.295 90.000
ZERR 2.0000 0.0020 0.0018 0.0009 0.000 0.003 0.000
LATT -7
SYMM X, -Y, Z
SFAC C H N BR
UNIT 14 8 2 2
EQIV $1 X-1,Y,1+Z
EQIV $2 X-1,-Y,1+Z
BIND Br1 N1_$1
BIND Br1 N1_$2
ACTA 50
FMAP 2 1 53
GRID
PLAN 10 0 0
MERG 2
SIZE 0.104 0.188 0.91
TEMP 0
L.S. 10
WGHT    0.124700
FVAR       0.26876
BR1   4    0.101410    0.000000    0.988370    10.50000    0.04723    0.05225 =
         0.04681    0.00000    0.00828    0.00000
N1    3    0.770954    0.000000    0.182258    10.50000    0.06202    0.07436 =
         0.08988    0.00000    0.02263    0.00000
C1    1    0.278705    0.000000    0.786173    10.50000    0.03971    0.03875 =
         0.03393    0.00000   -0.00081    0.00000
C2    1    0.340782    0.141033    0.710027    11.00000    0.05168    0.03230 =
         0.05097   -0.00290    0.00278    0.00167
AFIX  43
H2    2    0.297792    0.234665    0.766103    11.00000   -1.20000
AFIX   0
C3    1    0.468841    0.141200    0.547868    11.00000    0.05009    0.03341 =
         0.05228   -0.00030    0.00225   -0.00466
AFIX  43
H3    2    0.511673    0.235212    0.493897    11.00000   -1.20000
AFIX   0
C4    1    0.532180    0.000000    0.467259    10.50000    0.04530    0.04071 =
         0.03429    0.00000   -0.00075    0.00000
C5    1    0.666643    0.000000    0.308919    10.50000    0.04974    0.05327 =
         0.05918    0.00000    0.00508    0.00000
HKLF 4




REM  273K in Cm
REM R1 =  0.0596 for     869 Fo > 4sig(Fo)  and  0.0613 for all     893 data
REM     49 parameters refined using      2 restraints

END

WGHT      0.1247      0.0000

REM Highest difference peak  0.667,  deepest hole -0.236,  1-sigma level  0.082
Q1    1   0.0937 -0.0826  1.1324  11.00000  0.05    0.67
Q2    1   0.1114 -0.0793  0.8579  11.00000  0.05    0.64
Q3    1   0.0162  0.0000  1.0169  10.50000  0.05    0.58
Q4    1   0.1848  0.0000  0.9748  10.50000  0.05    0.55
Q5    1   0.6349  0.0000  0.3576  10.50000  0.05    0.27
Q6    1   0.3973  0.1393  0.5887  11.00000  0.05    0.27
Q7    1   0.3574  0.0000  0.7357  10.50000  0.05    0.26
Q8    1   0.8041 -0.1431  0.3873  11.00000  0.05    0.25
Q9    1   0.8533  0.0000  0.2448  10.50000  0.05    0.24
Q10   1   0.3094  0.0842  0.6954  11.00000  0.05    0.24
;
_shelx_res_checksum              28535
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br1 Br 0.10141(2) 0.000000 0.98837(2) 0.0487(5) Uani 1 2 d S T P
N1 N 0.771(2) 0.000000 0.182(6) 0.075(5) Uani 1 2 d S T P
C1 C 0.2787(14) 0.000000 0.786(3) 0.037(2) Uani 1 2 d S T P
C2 C 0.3408(12) 0.1410(11) 0.710(3) 0.0450(19) Uani 1 1 d . . .
H2 H 0.297792 0.234665 0.766103 0.054 Uiso 1 1 calc R U .
C3 C 0.4688(11) 0.1412(12) 0.548(3) 0.0453(19) Uani 1 1 d . . .
H3 H 0.511673 0.235212 0.493897 0.054 Uiso 1 1 calc R U .
C4 C 0.5322(15) 0.000000 0.467(4) 0.040(3) Uani 1 2 d S T P
C5 C 0.6666(19) 0.000000 0.309(5) 0.054(3) 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
Br1 0.0472(6) 0.0522(7) 0.0468(6) 0.000 0.0083(4) 0.000
N1 0.062(10) 0.074(12) 0.090(13) 0.000 0.023(9) 0.000
C1 0.040(6) 0.039(6) 0.034(5) 0.000 -0.001(4) 0.000
C2 0.052(5) 0.032(4) 0.051(5) -0.003(4) 0.003(4) 0.002(4)
C3 0.050(5) 0.033(4) 0.052(5) 0.000(4) 0.002(4) -0.005(4)
C4 0.045(7) 0.041(6) 0.034(6) 0.000 -0.001(5) 0.000
C5 0.050(8) 0.053(9) 0.059(11) 0.000 0.005(7) 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 Br1 N1 168.0(6) . 2_456
C1 Br1 N1 168.0(6) . 1_456
N1 Br1 N1 0.0(9) 2_456 1_456
C2 C1 C2 121.8(13) . 2
C2 C1 Br1 119.1(7) . .
C2 C1 Br1 119.1(7) 2 .
C1 C2 C3 119.1(10) . .
C4 C3 C2 119.7(10) . .
C3 C4 C3 120.5(14) 2 .
C3 C4 C5 119.7(7) 2 .
C3 C4 C5 119.7(7) . .
N1 C5 C4 179(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.889(13) .
Br1 N1 3.25(2) 2_456
Br1 N1 3.25(2) 1_456
N1 C5 1.13(3) .
C1 C2 1.381(12) .
C1 C2 1.381(12) 2
C2 C3 1.396(16) .
C3 C4 1.392(13) .
C4 C5 1.44(2) .
