#------------------------------------------------------------------------------
#$Date: 2019-11-17 04:04:04 +0100 (Sun 17 de Nov de 2019) $
#$Revision: 228019 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/20/7122096.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_7122096
loop_
_publ_author_name
'Morgan, Lewis C. F.'
'Kim, Yejin'
'Blandy, Jack N.'
'Murray, Claire A.'
'Christensen, Kirsten E.'
'Thompson, Amber L.'
_publ_section_title
;
 Unexpected behaviour in derivatives of Barluenga's reagent,
 Hal(Coll)₂X (Coll = 2,4,6-trimethyl pyridine, collidine; Hal =
 I, Br; X = PF₆, ClO₄ & BF₄).
;
_journal_issue                   70
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9849
_journal_page_last               9852
_journal_paper_doi               10.1039/c8cc05430d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C8 H12 N, Br'
_chemical_formula_sum            'C8 H12 Br N'
_chemical_formula_weight         202.09
_chemical_melting_point          ?
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-06-15
_audit_creation_method           CRYSTALS_ver_14.61_build_6156
_audit_update_record
;
2018-07-05 deposited with the CCDC.
2018-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.007(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6217(6)
_cell_length_b                   14.9357(9)
_cell_length_c                   6.8943(4)
_cell_measurement_reflns_used    1867
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      3
_cell_volume                     887.79(10)
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8473
_diffrn_reflns_theta_full        26.545
_diffrn_reflns_theta_max         29.826
_diffrn_reflns_theta_min         2.728
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.559
_exptl_absorpt_correction_T_max  0.66
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.75
_refine_diff_density_min         -0.81
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         938
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.0005252
_refine_ls_shift/su_mean         0.0000460
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 5.63P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1048
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1048
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              0
_reflns_limit_k_min              -20
_reflns_limit_l_max              0
_reflns_limit_l_min              -9
_reflns_number_gt                711
_reflns_number_total             1217
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   5.09
_oxford_diffrn_Wilson_scale      0.17
_oxford_refine_ls_r_factor_ref   0.0592
_oxford_refine_ls_scale          3.62(8)
_oxford_reflns_number_all        938
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 119lcm18
_iucr_refine_instructions_details
;
#
# Punched on 15/06/18 at 12:31:57
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
SUMFIX ELEMENT SCALES 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   8,X'S) H   (  82,X'S) H   (  81,X'S) H   (  83,X'S) 
END                                                                             
#
# Punched on 15/06/18 at 12:31:57
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   SHIFTLIMIT   START (DO NOT REMOVE THIS LINE) 
LIMIT      0.01000000 U[ISO] 
LIMIT      0.01000000 X 
LIMIT      0.01000000 Y 
LIMIT      0.01000000 Z 
LIMIT      0.01000000 U[11] 
LIMIT      0.01000000 U[22] 
LIMIT      0.01000000 U[33] 
LIMIT      0.01000000 U[12] 
LIMIT      0.01000000 U[13] 
LIMIT      0.01000000 U[23] 
LIMIT      0.01000000 OCC 
REM   SHIFTLIMIT   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c8cc05430d2.cif
_cod_data_source_block           CollHBr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7122093--7122107.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               7122096
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.0000 0.83373(10) 0.7500 0.0685 1.0000 Uani S T
N1 N 0.000000(7) 0.5924(8) 0.750000(7) 0.0764 1.0000 Uani S T
C2 C -0.1407(9) 0.5428(8) 0.7495(8) 0.0663 1.0000 Uani . .
C3 C -0.1362(9) 0.4539(6) 0.7502(8) 0.0530 1.0000 Uani . .
C4 C 0.0000 0.4083(9) 0.7500 0.0710 1.0000 Uani S T
C7 C -0.2883(13) 0.5953(11) 0.7467(12) 0.1301 1.0000 Uani . .
C8 C 0.000000(10) 0.3097(11) 0.750000(10) 0.1298 1.0000 Uani S T
H11 H 0.0000 0.6502 0.7500 0.0909 1.0000 Uiso RS .
H31 H -0.2278 0.4220 0.7476 0.0637 1.0000 Uiso R .
H71 H -0.3742 0.5560 0.7377 0.1948 1.0000 Uiso R .
H72 H -0.2994 0.6294 0.8639 0.1947 1.0000 Uiso R .
H73 H -0.2935 0.6354 0.6393 0.1948 1.0000 Uiso R .
H81 H 0.1039 0.2885 0.7499 0.1559 0.5000 Uiso R .
H82 H -0.0519 0.2885 0.8626 0.1559 0.5000 Uiso R .
H83 H -0.0520 0.2885 0.6375 0.1559 0.5000 Uiso R .
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 0.0720(8) 0.0762(9) 0.0572(4) 0.0000 0.0014(5) 0.0000
N1 0.122(6) 0.062(5) 0.046(5) 0.0000 0.000(7) 0.0000
C2 0.062(4) 0.109(5) 0.028(3) -0.003(5) -0.005(4) 0.010(4)
C3 0.064(4) 0.060(4) 0.035(3) -0.005(5) 0.002(4) -0.012(3)
C4 0.116(6) 0.071(6) 0.027(4) 0.0000 0.006(6) 0.0000
C7 0.102(5) 0.219(8) 0.070(5) 0.000(7) -0.003(5) 0.101(5)
C8 0.241(6) 0.086(7) 0.062(6) 0.0000 -0.001(8) 0.0000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 6_556 N1 C2 . 117.2(10) yes
C2 6_556 N1 H11 . 121.4 no
C2 . N1 H11 . 121.4 no
N1 . C2 C3 . 119.8(7) yes
N1 . C2 C7 . 116.9(11) yes
C3 . C2 C7 . 123.3(11) yes
C2 . C3 C4 . 121.7(7) yes
C2 . C3 H31 . 119.5 no
C4 . C3 H31 . 118.8 no
C3 6_556 C4 C3 . 119.9(11) yes
C3 6_556 C4 C8 . 120.1(6) yes
C3 . C4 C8 . 120.1(6) yes
C2 . C7 H71 . 109.9 no
C2 . C7 H72 . 110.6 no
H71 . C7 H72 . 107.8 no
C2 . C7 H73 . 112.3 no
H71 . C7 H73 . 107.6 no
H72 . C7 H73 . 108.5 no
C4 . C8 H83 6_556 109.5 no
C4 . C8 H82 6_556 109.5 no
H83 6_556 C8 H82 6_556 109.5 no
C4 . C8 H81 6_556 109.5 no
H83 6_556 C8 H81 6_556 109.5 no
H82 6_556 C8 H81 6_556 109.5 no
C4 . C8 H81 . 109.5 no
H83 6_556 C8 H81 . 56.3 no
H82 6_556 C8 H81 . 56.3 no
H81 6_556 C8 H81 . 141.1 no
C4 . C8 H82 . 109.5 no
H83 6_556 C8 H82 . 56.3 no
H82 6_556 C8 H82 . 141.1 no
H81 6_556 C8 H82 . 56.3 no
H81 . C8 H82 . 109.5 no
C4 . C8 H83 . 109.5 no
H83 6_556 C8 H83 . 141.1 no
H82 6_556 C8 H83 . 56.3 no
H81 6_556 C8 H83 . 56.3 no
H81 . C8 H83 . 109.5 no
H82 . C8 H83 . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 6_556 1.421(12) yes
N1 C2 . 1.421(12) yes
N1 H11 . 0.863 no
C2 C3 . 1.329(12) yes
C2 C7 . 1.496(10) yes
C3 C4 . 1.357(11) yes
C3 H31 . 0.922 no
C4 C8 . 1.47(2) yes
C7 H71 . 0.947 no
C7 H72 . 0.959 no
C7 H73 . 0.953 no
C8 H83 6_556 0.950 no
C8 H82 6_556 0.950 no
C8 H81 6_556 0.950 no
C8 H81 . 0.950 no
C8 H82 . 0.950 no
C8 H83 . 0.950 no
loop_
_oxford_twin_element_scale_factors
0.43(3)
0.57(3)
