# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_791
_database_code_depnum_ccdc_archive 'CCDC 1941218'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C18TAB
_chemical_name_systematic        'Octadecyltrimethylammonium bromide'
_chemical_formula_moiety         'C21 H46 N, Br'
_chemical_formula_sum            'C21 H46 Br N'
_chemical_formula_weight         392.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H46 N Br'
_chemical_oxdiff_usercomment     'Thin blade from cooled acetone water '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.59242(10)
_cell_length_b                   7.15259(9)
_cell_length_c                   56.5835(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.8007(14)
_cell_angle_gamma                90
_cell_volume                     2247.43(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13220
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.2260
_cell_measurement_theta_min      4.7190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Recrystallized from acetone:water mixture in fridge'
_exptl_crystal_size_max          0.4073
_exptl_crystal_size_mid          0.0793
_exptl_crystal_size_min          0.0167
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       70
_diffrn_reflns_limit_l_min       -70
_diffrn_reflns_number            37501
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.529
_diffrn_reflns_theta_min         4.722
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4061
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -75.00  -19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -57.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00  -22.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -38.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -71.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091   57.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091   38.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  5 omega -117.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -77.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
  6 omega -119.00  -85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -77.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega  -49.00  -17.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega  -82.00  -10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -77.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
  9 omega  -81.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -77.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega -124.00  -84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.8091  -99.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   27.00   66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8091 -125.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   61.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8091 -125.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 13 omega   24.00   58.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.8091 -125.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 14 omega   84.00  122.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega   68.00  112.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   37.00   83.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 17 omega   79.00  169.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
 18 omega   29.00  100.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
 19 omega   83.00  149.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
 20 omega   80.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   76.0000  168.2103 25

#__ type_ start__ end____ width___ exp.time_
 21 omega  130.00  173.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
 22 omega   79.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega  125.00  163.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 24 omega   48.00  107.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 25 omega   79.00  164.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 26 omega   79.00  104.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   41.00   95.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 28 omega  106.00  145.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 29 omega   83.00  123.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   83.00  109.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   83.00  175.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
 33 omega   83.00  176.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
 34 omega   79.00  166.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
 35 omega   83.00  109.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   79.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   79.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega  133.00  168.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
 39 omega   29.00   78.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
 40 omega   83.00  136.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 41 omega   79.00  111.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 42 omega   36.00  132.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
 43 omega   79.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   79.00  106.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 45 omega  126.00  152.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   83.00  116.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 47 omega   79.00  105.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega  128.00  154.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 49 omega  130.00  156.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 50 omega   54.00   98.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
 51 omega   43.00   91.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 52 omega   87.00  164.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
 53 omega   86.00  124.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
 54 omega   38.00   64.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 55 omega  122.00  147.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   76.0000  168.2103 25

#__ type_ start__ end____ width___ exp.time_
 56 omega   82.00  177.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   66.0000  -98.7735 95

#__ type_ start__ end____ width___ exp.time_
 57 omega   82.00  112.00   1.0000   28.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   64.0000  -28.2207 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0395103000
_diffrn_orient_matrix_UB_12      0.2099673000
_diffrn_orient_matrix_UB_13      -0.0042133000
_diffrn_orient_matrix_UB_21      -0.0513755000
_diffrn_orient_matrix_UB_22      -0.0310397000
_diffrn_orient_matrix_UB_23      -0.0270715000
_diffrn_orient_matrix_UB_31      -0.2696961000
_diffrn_orient_matrix_UB_32      0.0366339000
_diffrn_orient_matrix_UB_33      0.0012020000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3407
_reflns_number_total             4675
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+0.6720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B)
Uiso(H13A) = Uiso(H13B)
Uiso(H14A) = Uiso(H14B)
Uiso(H15A) = Uiso(H15B)
Uiso(H16A) = Uiso(H16B)
Uiso(H17A) = Uiso(H17B)
Uiso(H18A) = Uiso(H18B) = Uiso(H18C)
Uiso(H19A) = Uiso(H19B) = Uiso(H19C) = Uiso(H20A) = Uiso(H20B) = Uiso(H20C) =
Uiso(H21A) = Uiso(H21B) = Uiso(H21C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.770(5) 0.366(4) 0.0517(4) 0.022(4) Uiso 1 1 d . . . . .
H1B H 0.738(5) 0.157(4) 0.0494(4) 0.022(4) Uiso 1 1 d . . . . .
H2A H 1.095(5) 0.301(4) 0.0843(5) 0.030(5) Uiso 1 1 d . . . . .
H2B H 0.993(5) 0.087(4) 0.0826(5) 0.030(5) Uiso 1 1 d . . . . .
H3A H 0.740(6) 0.416(4) 0.0952(5) 0.038(5) Uiso 1 1 d . . . . .
H3B H 0.611(6) 0.228(4) 0.0899(6) 0.038(5) Uiso 1 1 d . . . . .
H4A H 0.974(6) 0.266(4) 0.1282(5) 0.030(5) Uiso 1 1 d . . . . .
H4B H 0.814(5) 0.081(4) 0.1232(5) 0.030(5) Uiso 1 1 d . . . . .
H5A H 0.638(5) 0.437(4) 0.1376(5) 0.032(5) Uiso 1 1 d . . . . .
H5B H 0.475(6) 0.270(4) 0.1304(5) 0.032(5) Uiso 1 1 d . . . . .
H6A H 0.823(5) 0.253(3) 0.1703(5) 0.029(5) Uiso 1 1 d . . . . .
H6B H 0.647(5) 0.085(4) 0.1628(5) 0.029(5) Uiso 1 1 d . . . . .
H7A H 0.498(5) 0.439(4) 0.1789(5) 0.034(5) Uiso 1 1 d . . . . .
H7B H 0.314(6) 0.283(4) 0.1700(5) 0.034(5) Uiso 1 1 d . . . . .
H8A H 0.666(6) 0.252(4) 0.2112(5) 0.030(5) Uiso 1 1 d . . . . .
H8B H 0.479(5) 0.094(4) 0.2026(5) 0.030(5) Uiso 1 1 d . . . . .
H9A H 0.344(4) 0.443(4) 0.2191(4) 0.024(4) Uiso 1 1 d . . . . .
H9B H 0.149(5) 0.287(4) 0.2103(4) 0.024(4) Uiso 1 1 d . . . . .
H10A H 0.496(6) 0.244(3) 0.2511(5) 0.028(5) Uiso 1 1 d . . . . .
H10B H 0.313(5) 0.087(4) 0.2422(5) 0.028(5) Uiso 1 1 d . . . . .
H11A H 0.181(5) 0.441(4) 0.2597(5) 0.029(4) Uiso 1 1 d . . . . .
H11B H -0.009(6) 0.289(4) 0.2507(5) 0.029(4) Uiso 1 1 d . . . . .
H12A H 0.332(6) 0.253(3) 0.2916(5) 0.028(5) Uiso 1 1 d . . . . .
H12B H 0.159(5) 0.098(5) 0.2830(4) 0.028(5) Uiso 1 1 d . . . . .
H13A H 0.025(5) 0.442(4) 0.3003(5) 0.032(5) Uiso 1 1 d . . . . .
H13B H -0.164(6) 0.289(4) 0.2917(5) 0.032(5) Uiso 1 1 d . . . . .
H14A H 0.180(6) 0.246(4) 0.3318(5) 0.031(5) Uiso 1 1 d . . . . .
H14B H -0.007(5) 0.095(4) 0.3232(5) 0.031(5) Uiso 1 1 d . . . . .
H15A H -0.129(5) 0.443(4) 0.3408(5) 0.033(5) Uiso 1 1 d . . . . .
H15B H -0.339(6) 0.295(4) 0.3304(5) 0.033(5) Uiso 1 1 d . . . . .
H16A H 0.029(5) 0.241(3) 0.3724(5) 0.027(5) Uiso 1 1 d . . . . .
H16B H -0.160(5) 0.093(4) 0.3632(5) 0.027(5) Uiso 1 1 d . . . . .
H17A H -0.287(6) 0.446(4) 0.3817(5) 0.038(5) Uiso 1 1 d . . . . .
H17B H -0.476(6) 0.293(4) 0.3725(5) 0.038(5) Uiso 1 1 d . . . . .
H18A H -0.143(8) 0.242(5) 0.4130(7) 0.058(6) Uiso 1 1 d . . . . .
H18B H -0.339(7) 0.091(6) 0.4035(6) 0.058(6) Uiso 1 1 d . . . . .
H18C H -0.422(7) 0.289(5) 0.4151(7) 0.058(6) Uiso 1 1 d . . . . .
H19A H 0.778(5) 0.369(4) 0.0111(4) 0.024(2) Uiso 1 1 d . . . . .
H19B H 0.790(5) 0.153(4) 0.0108(4) 0.024(2) Uiso 1 1 d . . . . .
H19C H 0.993(5) 0.263(3) 0.0007(5) 0.024(2) Uiso 1 1 d . . . . .
H20A H 1.286(5) 0.408(4) 0.0542(5) 0.024(2) Uiso 1 1 d . . . . .
H20B H 1.095(5) 0.519(4) 0.0380(4) 0.024(2) Uiso 1 1 d . . . . .
H20C H 1.292(5) 0.414(4) 0.0271(4) 0.024(2) Uiso 1 1 d . . . . .
H21A H 1.079(5) -0.024(4) 0.0379(4) 0.024(2) Uiso 1 1 d . . . . .
H21B H 1.286(5) 0.077(3) 0.0535(4) 0.024(2) Uiso 1 1 d . . . . .
H21C H 1.277(5) 0.075(4) 0.0262(4) 0.024(2) Uiso 1 1 d . . . . .
C1 C 0.8474(3) 0.2540(2) 0.05443(3) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.9485(4) 0.2219(3) 0.08027(3) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.7563(4) 0.2775(3) 0.09593(3) 0.0265(4) Uani 1 1 d . . . . .
C4 C 0.8130(4) 0.2219(3) 0.12205(3) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.6297(4) 0.2996(3) 0.13731(3) 0.0237(4) Uani 1 1 d . . . . .
C6 C 0.6613(4) 0.2255(3) 0.16278(3) 0.0231(4) Uani 1 1 d . . . . .
C7 C 0.4778(4) 0.3071(3) 0.17797(3) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.5000(4) 0.2263(3) 0.20316(3) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.3182(4) 0.3088(3) 0.21827(3) 0.0222(4) Uani 1 1 d . . . . .
C10 C 0.3375(4) 0.2261(3) 0.24339(3) 0.0219(4) Uani 1 1 d . . . . .
C11 C 0.1559(4) 0.3089(3) 0.25858(3) 0.0225(4) Uani 1 1 d . . . . .
C12 C 0.1768(4) 0.2264(3) 0.28361(3) 0.0225(4) Uani 1 1 d . . . . .
C13 C -0.0035(4) 0.3088(3) 0.29897(3) 0.0234(4) Uani 1 1 d . . . . .
C14 C 0.0170(4) 0.2255(3) 0.32396(3) 0.0229(4) Uani 1 1 d . . . . .
C15 C -0.1607(4) 0.3100(3) 0.33952(3) 0.0246(4) Uani 1 1 d . . . . .
C16 C -0.1393(4) 0.2256(3) 0.36450(3) 0.0253(4) Uani 1 1 d . . . . .
C17 C -0.3148(5) 0.3097(3) 0.38021(4) 0.0305(5) Uani 1 1 d . . . . .
C18 C -0.2923(6) 0.2225(4) 0.40498(4) 0.0415(6) Uani 1 1 d . . . . .
C19 C 0.8847(4) 0.2563(3) 0.01231(3) 0.0234(4) Uani 1 1 d . . . . .
C20 C 1.1895(4) 0.4176(3) 0.03918(3) 0.0216(4) Uani 1 1 d . . . . .
C21 C 1.1778(4) 0.0761(3) 0.03862(3) 0.0225(4) Uani 1 1 d . . . . .
N1 N 1.0273(3) 0.2501(2) 0.03648(3) 0.0171(3) Uani 1 1 d . . . . .
Br1 Br 0.64585(3) 0.75210(3) 0.03329(2) 0.02774(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.91(3) . ?
C1 H1B 0.95(3) . ?
C1 C2 1.521(2) . ?
C1 N1 1.512(2) . ?
C2 H2A 1.00(3) . ?
C2 H2B 1.00(3) . ?
C2 C3 1.525(3) . ?
C3 H3A 0.99(3) . ?
C3 H3B 0.92(3) . ?
C3 C4 1.527(2) . ?
C4 H4A 0.98(3) . ?
C4 H4B 1.01(3) . ?
C4 C5 1.521(3) . ?
C5 H5A 0.98(3) . ?
C5 H5B 0.93(3) . ?
C5 C6 1.526(2) . ?
C6 H6A 0.97(3) . ?
C6 H6B 1.01(3) . ?
C6 C7 1.530(3) . ?
C7 H7A 0.95(3) . ?
C7 H7B 0.99(3) . ?
C7 C8 1.529(2) . ?
C8 H8A 1.00(3) . ?
C8 H8B 0.95(3) . ?
C8 C9 1.523(3) . ?
C9 H9A 0.97(3) . ?
C9 H9B 1.01(3) . ?
C9 C10 1.532(2) . ?
C10 H10A 0.95(3) . ?
C10 H10B 1.00(3) . ?
C10 C11 1.525(3) . ?
C11 H11A 0.95(3) . ?
C11 H11B 0.99(3) . ?
C11 C12 1.526(2) . ?
C12 H12A 0.95(3) . ?
C12 H12B 0.92(3) . ?
C12 C13 1.525(3) . ?
C13 H13A 0.96(3) . ?
C13 H13B 0.95(3) . ?
C13 C14 1.526(3) . ?
C14 H14A 0.98(3) . ?
C14 H14B 0.94(3) . ?
C14 C15 1.529(3) . ?
C15 H15A 0.97(3) . ?
C15 H15B 1.07(3) . ?
C15 C16 1.528(3) . ?
C16 H16A 1.00(3) . ?
C16 H16B 0.96(3) . ?
C16 C17 1.524(3) . ?
C17 H17A 0.99(3) . ?
C17 H17B 0.96(3) . ?
C17 C18 1.526(3) . ?
C18 H18A 0.91(4) . ?
C18 H18B 0.98(4) . ?
C18 H18C 1.09(4) . ?
C19 H19A 1.00(3) . ?
C19 H19B 0.91(3) . ?
C19 H19C 0.95(3) . ?
C19 N1 1.500(2) . ?
C20 H20A 0.96(3) . ?
C20 H20B 0.90(3) . ?
C20 H20C 0.94(3) . ?
C20 N1 1.500(2) . ?
C21 H21A 0.90(3) . ?
C21 H21B 0.98(3) . ?
C21 H21C 0.95(3) . ?
C21 N1 1.499(2) . ?

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
_geom_angle_publ_flag
H1A C1 H1B 108(2) . . ?
C2 C1 H1A 114.2(15) . . ?
C2 C1 H1B 109.5(15) . . ?
N1 C1 H1A 103.8(16) . . ?
N1 C1 H1B 103.9(16) . . ?
N1 C1 C2 116.21(15) . . ?
H2A C2 H2B 109(2) . . ?
C1 C2 H2A 109.5(16) . . ?
C1 C2 H2B 109.2(15) . . ?
C1 C2 C3 108.17(16) . . ?
C3 C2 H2A 109.6(17) . . ?
C3 C2 H2B 110.9(16) . . ?
H3A C3 H3B 107(2) . . ?
C2 C3 H3A 107.6(18) . . ?
C2 C3 H3B 110(2) . . ?
C2 C3 C4 114.49(17) . . ?
C4 C3 H3A 107.9(17) . . ?
C4 C3 H3B 109(2) . . ?
H4A C4 H4B 108(2) . . ?
C3 C4 H4A 109.9(17) . . ?
C3 C4 H4B 108.6(15) . . ?
C5 C4 H4A 109.4(17) . . ?
C5 C4 H4B 109.1(17) . . ?
C5 C4 C3 112.18(16) . . ?
H5A C5 H5B 106(2) . . ?
C4 C5 H5A 109.9(17) . . ?
C4 C5 H5B 109.6(19) . . ?
C4 C5 C6 113.52(17) . . ?
C6 C5 H5A 109.5(16) . . ?
C6 C5 H5B 108.3(18) . . ?
H6A C6 H6B 106(2) . . ?
C5 C6 H6A 110.0(17) . . ?
C5 C6 H6B 110.2(15) . . ?
C5 C6 C7 112.83(17) . . ?
C7 C6 H6A 108.8(17) . . ?
C7 C6 H6B 108.8(16) . . ?
H7A C7 H7B 107(2) . . ?
C6 C7 H7A 109.1(19) . . ?
C6 C7 H7B 108.9(17) . . ?
C8 C7 H7A 109.1(17) . . ?
C8 C7 H7B 109.0(17) . . ?
C8 C7 C6 113.15(17) . . ?
H8A C8 H8B 108(2) . . ?
C7 C8 H8A 108.7(16) . . ?
C7 C8 H8B 110.3(16) . . ?
C9 C8 H8A 108.6(17) . . ?
C9 C8 H8B 108.5(18) . . ?
C9 C8 C7 112.98(17) . . ?
H9A C9 H9B 107(2) . . ?
C8 C9 H9A 107.9(15) . . ?
C8 C9 H9B 110.0(15) . . ?
C8 C9 C10 113.16(17) . . ?
C10 C9 H9A 109.9(14) . . ?
C10 C9 H9B 108.3(15) . . ?
H10A C10 H10B 106(2) . . ?
C9 C10 H10A 109.3(18) . . ?
C9 C10 H10B 108.9(16) . . ?
C11 C10 H10A 109.8(18) . . ?
C11 C10 H10B 109.3(17) . . ?
C11 C10 C9 113.25(17) . . ?
H11A C11 H11B 107(2) . . ?
C10 C11 H11A 108.5(18) . . ?
C10 C11 H11B 109.6(17) . . ?
C10 C11 C12 112.95(17) . . ?
C12 C11 H11A 109.2(17) . . ?
C12 C11 H11B 109.2(17) . . ?
H12A C12 H12B 108(2) . . ?
C11 C12 H12A 109.3(17) . . ?
C11 C12 H12B 110.8(15) . . ?
C13 C12 H12A 106.2(17) . . ?
C13 C12 H12B 109.2(16) . . ?
C13 C12 C11 113.34(18) . . ?
H13A C13 H13B 109(2) . . ?
C12 C13 H13A 108.1(18) . . ?
C12 C13 H13B 110.3(18) . . ?
C12 C13 C14 113.23(17) . . ?
C14 C13 H13A 108.6(16) . . ?
C14 C13 H13B 107.8(18) . . ?
H14A C14 H14B 107(2) . . ?
C13 C14 H14A 109.1(17) . . ?
C13 C14 H14B 110.3(17) . . ?
C13 C14 C15 113.37(17) . . ?
C15 C14 H14A 108.5(17) . . ?
C15 C14 H14B 108.6(18) . . ?
H15A C15 H15B 106(2) . . ?
C14 C15 H15A 107.8(18) . . ?
C14 C15 H15B 108.3(16) . . ?
C16 C15 H15A 109.1(17) . . ?
C16 C15 H15B 111.9(16) . . ?
C16 C15 C14 113.05(18) . . ?
H16A C16 H16B 104(2) . . ?
C15 C16 H16A 109.7(16) . . ?
C15 C16 H16B 109.1(16) . . ?
C17 C16 H16A 109.6(16) . . ?
C17 C16 H16B 110.7(17) . . ?
C17 C16 C15 113.48(18) . . ?
H17A C17 H17B 107(2) . . ?
C16 C17 H17A 109.4(19) . . ?
C16 C17 H17B 108.4(19) . . ?
C16 C17 C18 112.7(2) . . ?
C18 C17 H17A 109.3(17) . . ?
C18 C17 H17B 109.8(19) . . ?
H18A C18 H18B 114(3) . . ?
H18A C18 H18C 107(3) . . ?
H18B C18 H18C 106(3) . . ?
C17 C18 H18A 112(3) . . ?
C17 C18 H18B 109(2) . . ?
C17 C18 H18C 109(2) . . ?
H19A C19 H19B 109(2) . . ?
H19A C19 H19C 110(2) . . ?
H19B C19 H19C 113(2) . . ?
N1 C19 H19A 109.5(14) . . ?
N1 C19 H19B 107.6(15) . . ?
N1 C19 H19C 108.7(17) . . ?
H20A C20 H20B 113(2) . . ?
H20A C20 H20C 109(2) . . ?
H20B C20 H20C 112(2) . . ?
N1 C20 H20A 107.7(15) . . ?
N1 C20 H20B 107.2(17) . . ?
N1 C20 H20C 108.3(16) . . ?
H21A C21 H21B 111(2) . . ?
H21A C21 H21C 112(2) . . ?
H21B C21 H21C 107(2) . . ?
N1 C21 H21A 108.4(17) . . ?
N1 C21 H21B 110.5(15) . . ?
N1 C21 H21C 108.7(16) . . ?
C19 N1 C1 106.73(14) . . ?
C20 N1 C1 111.06(14) . . ?
C20 N1 C19 108.60(14) . . ?
C21 N1 C1 111.90(14) . . ?
C21 N1 C19 109.34(14) . . ?
C21 N1 C20 109.12(15) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 169.86(18) . . . . ?
C2 C1 N1 C19 171.88(16) . . . . ?
C2 C1 N1 C20 -69.91(19) . . . . ?
C2 C1 N1 C21 52.3(2) . . . . ?
C2 C3 C4 C5 173.61(19) . . . . ?
C3 C4 C5 C6 172.25(18) . . . . ?
C4 C5 C6 C7 179.18(18) . . . . ?
C5 C6 C7 C8 177.11(18) . . . . ?
C6 C7 C8 C9 179.62(18) . . . . ?
C7 C8 C9 C10 179.17(17) . . . . ?
C8 C9 C10 C11 179.89(18) . . . . ?
C9 C10 C11 C12 -179.80(18) . . . . ?
C10 C11 C12 C13 179.78(18) . . . . ?
C11 C12 C13 C14 179.76(17) . . . . ?
C12 C13 C14 C15 179.09(18) . . . . ?
C13 C14 C15 C16 179.91(18) . . . . ?
C14 C15 C16 C17 179.68(19) . . . . ?
C15 C16 C17 C18 179.5(2) . . . . ?
N1 C1 C2 C3 166.36(16) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -5 -3 0.0396 -0.1483 -4.6218 -2.9479 -0.9639 0.2309 -0.1329
-1 5 4 0.0566 -0.7943 4.5106 4.2887 0.8976 -0.2153 0.3846
0 0 -1 0.0084 -0.0000 -0.0000 -0.9999 0.0042 0.0271 -0.0012
0 0 1 0.0084 0.0000 0.0000 0.9999 -0.0042 -0.0271 0.0012
4 0 -6 0.2033 3.6267 -0.1545 -5.5584 0.1343 -0.0311 -0.9905
-4 0 6 0.2033 -3.6267 0.1545 5.5584 -0.1343 0.0311 0.9905
0 5 3 0.0396 0.1483 4.6218 2.9479 0.9639 -0.2309 0.1329
3 -3 -6 0.1441 2.6395 -3.1660 -6.1403 -0.5346 0.1289 -0.8352

_olex2_date_sample_data_collection 2015-07-08
_olex2_exptl_crystal_mounting_method 'Hampton Research nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_798
_database_code_depnum_ccdc_archive 'CCDC 1941219'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C18TAB
_chemical_name_systematic        'Octadecyltrimethylammonium bromide'
_chemical_formula_moiety         'C21 H46 N, Br'
_chemical_formula_sum            'C21 H46 Br N'
_chemical_formula_weight         392.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H46 Br N'
_chemical_oxdiff_usercomment     
'C18TAB at 295K recrystallized from acetone-water in fridge'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.63143(14)
_cell_length_b                   7.27158(15)
_cell_length_c                   56.7610(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.805(2)
_cell_angle_gamma                90
_cell_volume                     2312.41(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11434
_cell_measurement_temperature    295
_cell_measurement_theta_max      73.1680
_cell_measurement_theta_min      4.7080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.403
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             856
_exptl_crystal_recrystallization_method 'Recrystallized from acetone / water'
_exptl_crystal_size_max          0.4526
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.0135
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       69
_diffrn_reflns_limit_l_min       -70
_diffrn_reflns_number            33203
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.642
_diffrn_reflns_theta_min         4.698
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -81.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega -115.00  -87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega -115.00  -63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -95.00   -3.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  125.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega -114.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   12.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   83.0000   57.9899 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   16.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000   -0.7882 29

#__ type_ start__ end____ width___ exp.time_
 10 omega   16.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000 -102.6218 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   16.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  158.7615 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   20.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000   93.5091 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   21.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  -36.2227 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00   45.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000 -162.7588 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   62.0000   62.1977 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  137.4709 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  123.0444 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   33.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -177.2936 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   41.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   53.0000   39.8596 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   63.0000   85.4388 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   33.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -100.0861 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  104.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -177.2936 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   54.0000  118.7184 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000 -145.5192 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   37.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -82.7671 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   51.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   68.0000  -27.8236 50

#__ type_ start__ end____ width___ exp.time_
 27 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   72.0000  -62.5007 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  101.00  153.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   74.0000 -175.4836 52

#__ type_ start__ end____ width___ exp.time_
 29 omega   46.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   74.0000 -175.4836 29

#__ type_ start__ end____ width___ exp.time_
 30 omega   50.00   79.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   77.0000  -65.3348 29

#__ type_ start__ end____ width___ exp.time_
 31 omega   55.00   81.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   69.0000 -109.2463 26

#__ type_ start__ end____ width___ exp.time_
 32 omega  127.00  158.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   62.0000  151.5796 31

#__ type_ start__ end____ width___ exp.time_
 33 omega   57.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   62.0000  151.5796 26

#__ type_ start__ end____ width___ exp.time_
 34 omega  111.00  149.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   70.0000    4.0063 38

#__ type_ start__ end____ width___ exp.time_
 35 omega   59.00   84.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   70.0000    4.0063 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   66.00   93.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   73.0000 -132.4860 27

#__ type_ start__ end____ width___ exp.time_
 37 omega   77.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   55.0000 -134.8801 97

#__ type_ start__ end____ width___ exp.time_
 38 omega   79.00  116.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
 39 omega  113.00  170.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
 40 omega   74.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 41 omega   77.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 42 omega  150.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 43 omega  135.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
 44 omega   30.00  139.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 45 omega   80.00  129.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
 46 omega  117.00  165.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
 47 omega   31.00   74.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -112.0000  -49.0000 43

#__ type_ start__ end____ width___ exp.time_
 48 omega   74.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 49 omega  136.00  168.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 50 omega   74.00  132.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 51 omega  142.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 52 omega  111.00  137.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega   81.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 54 omega  145.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 55 omega   74.00  100.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega   77.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   66.0000  -91.5008 101

#__ type_ start__ end____ width___ exp.time_
 57 omega  110.00  161.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 58 omega   74.00   99.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0294014000
_diffrn_orient_matrix_UB_12      -0.0115694000
_diffrn_orient_matrix_UB_13      0.0266552000
_diffrn_orient_matrix_UB_21      -0.0157945000
_diffrn_orient_matrix_UB_22      0.2112758000
_diffrn_orient_matrix_UB_23      0.0011678000
_diffrn_orient_matrix_UB_31      -0.2728684000
_diffrn_orient_matrix_UB_32      -0.0109942000
_diffrn_orient_matrix_UB_33      -0.0057127000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3112
_reflns_number_total             4531
_reflns_odcompleteness_completeness 99.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0122P)²+2.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B)
Uiso(H13A) = Uiso(H13B)
Uiso(H14A) = Uiso(H14B)
Uiso(H15A) = Uiso(H15B)
Uiso(H16A) = Uiso(H16B)
Uiso(H17A) = Uiso(H17B)
Uiso(H18A) = Uiso(H18B) = Uiso(H18C)
Uiso(H19A) = Uiso(H19B) = Uiso(H19C) = Uiso(H20A) = Uiso(H20B) = Uiso(H20C) =
Uiso(H21A) = Uiso(H21B) = Uiso(H21C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.765(6) 0.374(5) 0.0530(6) 0.041(6) Uiso 1 1 d . . . . .
H1B H 0.738(7) 0.159(5) 0.0493(6) 0.041(6) Uiso 1 1 d . . . . .
H2A H 1.076(6) 0.310(5) 0.0836(6) 0.043(7) Uiso 1 1 d . . . . .
H2B H 0.990(6) 0.095(5) 0.0823(6) 0.043(7) Uiso 1 1 d . . . . .
H3A H 0.716(7) 0.406(6) 0.0947(7) 0.059(8) Uiso 1 1 d . . . . .
H3B H 0.606(7) 0.214(6) 0.0901(6) 0.059(8) Uiso 1 1 d . . . . .
H4B H 0.835(7) 0.097(6) 0.1235(7) 0.063(8) Uiso 1 1 d . . . . .
H4A H 0.964(7) 0.268(6) 0.1274(6) 0.063(8) Uiso 1 1 d . . . . .
H5A H 0.635(7) 0.437(6) 0.1371(7) 0.057(8) Uiso 1 1 d . . . . .
H5B H 0.472(7) 0.263(6) 0.1305(6) 0.057(8) Uiso 1 1 d . . . . .
H6A H 0.817(7) 0.254(6) 0.1695(6) 0.055(7) Uiso 1 1 d . . . . .
H6B H 0.650(7) 0.094(6) 0.1624(6) 0.055(7) Uiso 1 1 d . . . . .
H7A H 0.492(7) 0.450(6) 0.1785(7) 0.063(8) Uiso 1 1 d . . . . .
H7B H 0.319(7) 0.277(6) 0.1706(6) 0.063(8) Uiso 1 1 d . . . . .
H8A H 0.662(7) 0.253(7) 0.2106(6) 0.058(8) Uiso 1 1 d . . . . .
H8B H 0.480(7) 0.098(6) 0.2017(7) 0.058(8) Uiso 1 1 d . . . . .
H9A H 0.334(7) 0.444(6) 0.2192(7) 0.056(8) Uiso 1 1 d . . . . .
H9B H 0.162(7) 0.287(5) 0.2111(6) 0.056(8) Uiso 1 1 d . . . . .
H10A H 0.498(7) 0.249(6) 0.2509(6) 0.053(7) Uiso 1 1 d . . . . .
H10B H 0.318(7) 0.092(5) 0.2425(6) 0.053(7) Uiso 1 1 d . . . . .
H11A H 0.182(7) 0.440(6) 0.2596(7) 0.057(8) Uiso 1 1 d . . . . .
H11B H 0.003(7) 0.290(5) 0.2515(6) 0.057(8) Uiso 1 1 d . . . . .
H12A H 0.335(6) 0.253(6) 0.2913(6) 0.054(7) Uiso 1 1 d . . . . .
H12B H 0.152(7) 0.095(6) 0.2829(7) 0.054(7) Uiso 1 1 d . . . . .
H13A H 0.020(7) 0.444(6) 0.2998(6) 0.056(8) Uiso 1 1 d . . . . .
H13B H -0.157(7) 0.286(5) 0.2921(6) 0.056(8) Uiso 1 1 d . . . . .
H14A H 0.180(6) 0.268(6) 0.3316(6) 0.052(7) Uiso 1 1 d . . . . .
H14B H -0.004(7) 0.100(5) 0.3228(6) 0.052(7) Uiso 1 1 d . . . . .
H15A H -0.138(7) 0.444(6) 0.3406(7) 0.061(9) Uiso 1 1 d . . . . .
H15B H -0.321(7) 0.295(5) 0.3326(6) 0.061(9) Uiso 1 1 d . . . . .
H16A H 0.023(7) 0.235(6) 0.3722(6) 0.054(7) Uiso 1 1 d . . . . .
H16B H -0.168(7) 0.099(6) 0.3637(7) 0.054(7) Uiso 1 1 d . . . . .
H17A H -0.304(8) 0.447(6) 0.3808(8) 0.076(10) Uiso 1 1 d . . . . .
H17B H -0.478(8) 0.296(6) 0.3729(7) 0.076(10) Uiso 1 1 d . . . . .
H18A H -0.125(8) 0.244(8) 0.4129(8) 0.089(9) Uiso 1 1 d . . . . .
H18B H -0.324(9) 0.092(7) 0.4032(8) 0.089(9) Uiso 1 1 d . . . . .
H18C H -0.414(8) 0.300(6) 0.4148(8) 0.089(9) Uiso 1 1 d . . . . .
H19A H 0.782(7) 0.374(6) 0.0121(7) 0.054(3) Uiso 1 1 d . . . . .
H19C H 0.994(6) 0.266(6) 0.0006(6) 0.054(3) Uiso 1 1 d . . . . .
H19B H 0.775(8) 0.159(6) 0.0113(7) 0.054(3) Uiso 1 1 d . . . . .
H20A H 1.275(7) 0.410(5) 0.0550(7) 0.054(3) Uiso 1 1 d . . . . .
H20B H 1.085(8) 0.529(5) 0.0389(7) 0.054(3) Uiso 1 1 d . . . . .
H20C H 1.280(8) 0.424(5) 0.0265(7) 0.054(3) Uiso 1 1 d . . . . .
H21A H 1.068(8) -0.016(6) 0.0364(7) 0.054(3) Uiso 1 1 d . . . . .
H21B H 1.267(8) 0.079(5) 0.0525(7) 0.054(3) Uiso 1 1 d . . . . .
H21C H 1.272(7) 0.092(5) 0.0247(7) 0.054(3) Uiso 1 1 d . . . . .
C1 C 0.8435(5) 0.2530(7) 0.05444(5) 0.0391(6) Uani 1 1 d . . . . .
C2 C 0.9406(7) 0.2201(5) 0.07992(6) 0.0411(8) Uani 1 1 d . . . . .
C3 C 0.7509(8) 0.2767(7) 0.09583(6) 0.0544(11) Uani 1 1 d . . . . .
C4 C 0.8069(7) 0.2287(7) 0.12164(6) 0.0538(10) Uani 1 1 d . . . . .
C5 C 0.6255(7) 0.2983(5) 0.13733(6) 0.0490(10) Uani 1 1 d . . . . .
C6 C 0.6583(7) 0.2296(7) 0.16262(6) 0.0486(9) Uani 1 1 d . . . . .
C7 C 0.4770(8) 0.3062(5) 0.17804(6) 0.0480(9) Uani 1 1 d . . . . .
C8 C 0.4997(7) 0.2324(7) 0.20313(6) 0.0496(9) Uani 1 1 d . . . . .
C9 C 0.3182(7) 0.3085(5) 0.21850(6) 0.0479(9) Uani 1 1 d . . . . .
C10 C 0.3371(7) 0.2297(6) 0.24333(6) 0.0479(8) Uani 1 1 d . . . . .
C11 C 0.1579(7) 0.3093(5) 0.25882(6) 0.0478(9) Uani 1 1 d . . . . .
C12 C 0.1759(7) 0.2293(7) 0.28363(6) 0.0486(9) Uani 1 1 d . . . . .
C13 C -0.0023(7) 0.3091(5) 0.29924(6) 0.0479(9) Uani 1 1 d . . . . .
C14 C 0.0175(7) 0.2291(7) 0.32404(6) 0.0495(9) Uani 1 1 d . . . . .
C15 C -0.1572(8) 0.3091(6) 0.33985(7) 0.0508(9) Uani 1 1 d . . . . .
C16 C -0.1385(8) 0.2290(7) 0.36456(6) 0.0534(9) Uani 1 1 d . . . . .
C17 C -0.3096(9) 0.3083(6) 0.38064(8) 0.0625(12) Uani 1 1 d . . . . .
C18 C -0.2880(12) 0.2267(10) 0.40515(8) 0.0879(17) Uani 1 1 d . . . . .
C19 C 0.8813(6) 0.2575(8) 0.01250(5) 0.0500(8) Uani 1 1 d . . . . .
C20 C 1.1831(9) 0.4154(5) 0.03872(8) 0.0474(10) Uani 1 1 d . . . . .
C21 C 1.1697(8) 0.0798(6) 0.03823(8) 0.0466(10) Uani 1 1 d . . . . .
N1 N 1.0224(4) 0.2529(5) 0.03633(4) 0.0354(5) Uani 1 1 d . . . . .
Br1 Br 0.64297(6) 0.75148(7) 0.03330(2) 0.05662(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.98(4) . ?
C1 H1B 0.93(4) . ?
C1 C2 1.513(4) . ?
C1 N1 1.510(3) . ?
C2 H2A 1.01(4) . ?
C2 H2B 0.96(4) . ?
C2 C3 1.524(5) . ?
C3 H3A 0.96(4) . ?
C3 H3B 0.96(4) . ?
C3 C4 1.508(5) . ?
C4 H4B 0.98(4) . ?
C4 H4A 0.96(4) . ?
C4 C5 1.508(5) . ?
C5 H5A 1.01(4) . ?
C5 H5B 0.95(4) . ?
C5 C6 1.514(5) . ?
C6 H6A 0.95(4) . ?
C6 H6B 0.99(4) . ?
C6 C7 1.516(5) . ?
C7 H7A 1.05(4) . ?
C7 H7B 0.97(4) . ?
C7 C8 1.515(5) . ?
C8 H8A 0.98(4) . ?
C8 H8B 0.98(4) . ?
C8 C9 1.514(5) . ?
C9 H9A 0.99(4) . ?
C9 H9B 0.95(4) . ?
C9 C10 1.515(5) . ?
C10 H10A 0.97(4) . ?
C10 H10B 1.01(4) . ?
C10 C11 1.519(5) . ?
C11 H11A 0.96(4) . ?
C11 H11B 0.94(4) . ?
C11 C12 1.518(5) . ?
C12 H12A 0.97(4) . ?
C12 H12B 0.98(4) . ?
C12 C13 1.520(5) . ?
C13 H13A 0.99(4) . ?
C13 H13B 0.94(4) . ?
C13 C14 1.516(5) . ?
C14 H14A 1.01(4) . ?
C14 H14B 0.95(4) . ?
C14 C15 1.513(5) . ?
C15 H15A 0.99(4) . ?
C15 H15B 0.98(4) . ?
C15 C16 1.512(5) . ?
C16 H16A 0.97(4) . ?
C16 H16B 0.96(4) . ?
C16 C17 1.508(6) . ?
C17 H17A 1.01(5) . ?
C17 H17B 1.01(4) . ?
C17 C18 1.506(7) . ?
C18 H18A 0.98(5) . ?
C18 H18B 1.00(5) . ?
C18 H18C 1.08(5) . ?
C19 H19A 1.02(4) . ?
C19 H19C 0.97(4) . ?
C19 H19B 0.93(4) . ?
C19 N1 1.498(4) . ?
C20 H20A 1.02(4) . ?
C20 H20B 0.99(4) . ?
C20 H20C 0.93(4) . ?
C20 N1 1.486(5) . ?
C21 H21A 0.90(4) . ?
C21 H21B 0.93(4) . ?
C21 H21C 1.01(4) . ?
C21 N1 1.505(5) . ?

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
_geom_angle_publ_flag
H1A C1 H1B 111(3) . . ?
C2 C1 H1A 110(2) . . ?
C2 C1 H1B 110(2) . . ?
N1 C1 H1A 106(2) . . ?
N1 C1 H1B 104(2) . . ?
N1 C1 C2 116.7(2) . . ?
H2A C2 H2B 112(3) . . ?
C1 C2 H2A 106.8(19) . . ?
C1 C2 H2B 111(2) . . ?
C1 C2 C3 108.5(3) . . ?
C3 C2 H2A 105.3(19) . . ?
C3 C2 H2B 113(2) . . ?
H3A C3 H3B 106(4) . . ?
C2 C3 H3A 112(2) . . ?
C2 C3 H3B 107(2) . . ?
C4 C3 H3A 108(2) . . ?
C4 C3 H3B 108(2) . . ?
C4 C3 C2 115.0(3) . . ?
H4B C4 H4A 97(4) . . ?
C3 C4 H4B 110(2) . . ?
C3 C4 H4A 111(2) . . ?
C3 C4 C5 114.1(3) . . ?
C5 C4 H4B 112(2) . . ?
C5 C4 H4A 111(2) . . ?
H5A C5 H5B 108(3) . . ?
C4 C5 H5A 107(2) . . ?
C4 C5 H5B 108(2) . . ?
C4 C5 C6 115.1(3) . . ?
C6 C5 H5A 110(2) . . ?
C6 C5 H5B 108(2) . . ?
H6A C6 H6B 103(4) . . ?
C5 C6 H6A 110(2) . . ?
C5 C6 H6B 108(2) . . ?
C5 C6 C7 113.7(3) . . ?
C7 C6 H6A 111(2) . . ?
C7 C6 H6B 110(2) . . ?
H7A C7 H7B 107(3) . . ?
C6 C7 H7A 109(2) . . ?
C6 C7 H7B 108(2) . . ?
C8 C7 H7A 109(2) . . ?
C8 C7 H7B 109(2) . . ?
C8 C7 C6 114.5(3) . . ?
H8A C8 H8B 106(4) . . ?
C7 C8 H8A 110(2) . . ?
C7 C8 H8B 106(2) . . ?
C9 C8 H8A 110(2) . . ?
C9 C8 H8B 109(2) . . ?
C9 C8 C7 114.5(4) . . ?
H9A C9 H9B 105(3) . . ?
C8 C9 H9A 109(2) . . ?
C8 C9 H9B 110(2) . . ?
C8 C9 C10 114.2(3) . . ?
C10 C9 H9A 110(2) . . ?
C10 C9 H9B 109(2) . . ?
H10A C10 H10B 105(3) . . ?
C9 C10 H10A 109(2) . . ?
C9 C10 H10B 110(2) . . ?
C9 C10 C11 114.0(3) . . ?
C11 C10 H10A 109(2) . . ?
C11 C10 H10B 109(2) . . ?
H11A C11 H11B 107(3) . . ?
C10 C11 H11A 108(2) . . ?
C10 C11 H11B 109(2) . . ?
C12 C11 H11A 110(2) . . ?
C12 C11 H11B 109(2) . . ?
C12 C11 C10 113.9(3) . . ?
H12A C12 H12B 108(3) . . ?
C11 C12 H12A 109(2) . . ?
C11 C12 H12B 110(2) . . ?
C11 C12 C13 114.1(3) . . ?
C13 C12 H12A 108(2) . . ?
C13 C12 H12B 108(2) . . ?
H13A C13 H13B 108(3) . . ?
C12 C13 H13A 108(2) . . ?
C12 C13 H13B 109(2) . . ?
C14 C13 H13A 111(2) . . ?
C14 C13 H13B 108(2) . . ?
C14 C13 C12 113.8(3) . . ?
H14A C14 H14B 114(3) . . ?
C13 C14 H14A 105(2) . . ?
C13 C14 H14B 108(2) . . ?
C15 C14 H14A 105(2) . . ?
C15 C14 H14B 110(2) . . ?
C15 C14 C13 114.3(4) . . ?
H15A C15 H15B 102(3) . . ?
C14 C15 H15A 109(2) . . ?
C14 C15 H15B 111(2) . . ?
C16 C15 H15A 110(2) . . ?
C16 C15 H15B 109(2) . . ?
C16 C15 C14 114.4(3) . . ?
H16A C16 H16B 103(3) . . ?
C15 C16 H16A 112(2) . . ?
C15 C16 H16B 110(2) . . ?
C17 C16 H16A 110(2) . . ?
C17 C16 H16B 107(2) . . ?
C17 C16 C15 115.2(4) . . ?
H17A C17 H17B 97(4) . . ?
C16 C17 H17A 112(3) . . ?
C16 C17 H17B 109(2) . . ?
C18 C17 H17A 113(3) . . ?
C18 C17 H17B 111(2) . . ?
C18 C17 C16 114.3(4) . . ?
H18A C18 H18B 110(5) . . ?
H18A C18 H18C 110(4) . . ?
H18B C18 H18C 114(4) . . ?
C17 C18 H18A 110(3) . . ?
C17 C18 H18B 107(3) . . ?
C17 C18 H18C 106(3) . . ?
H19A C19 H19C 109(3) . . ?
H19A C19 H19B 107(3) . . ?
H19C C19 H19B 117(3) . . ?
N1 C19 H19A 106(2) . . ?
N1 C19 H19C 108(2) . . ?
N1 C19 H19B 109(2) . . ?
H20A C20 H20B 105(3) . . ?
H20A C20 H20C 114(4) . . ?
H20B C20 H20C 109(3) . . ?
N1 C20 H20A 108(2) . . ?
N1 C20 H20B 109(2) . . ?
N1 C20 H20C 113(3) . . ?
H21A C21 H21B 114(4) . . ?
H21A C21 H21C 113(3) . . ?
H21B C21 H21C 109(4) . . ?
N1 C21 H21A 107(3) . . ?
N1 C21 H21B 110(2) . . ?
N1 C21 H21C 103(2) . . ?
C19 N1 C1 106.5(2) . . ?
C19 N1 C21 108.7(3) . . ?
C20 N1 C1 112.3(3) . . ?
C20 N1 C19 109.1(3) . . ?
C20 N1 C21 109.4(2) . . ?
C21 N1 C1 110.6(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 172.1(4) . . . . ?
C2 C1 N1 C19 171.1(4) . . . . ?
C2 C1 N1 C20 -69.4(4) . . . . ?
C2 C1 N1 C21 53.1(5) . . . . ?
C2 C3 C4 C5 175.7(4) . . . . ?
C3 C4 C5 C6 171.7(4) . . . . ?
C4 C5 C6 C7 178.4(4) . . . . ?
C5 C6 C7 C8 177.3(4) . . . . ?
C6 C7 C8 C9 -179.8(4) . . . . ?
C7 C8 C9 C10 178.2(4) . . . . ?
C8 C9 C10 C11 178.8(4) . . . . ?
C9 C10 C11 C12 179.6(4) . . . . ?
C10 C11 C12 C13 179.7(4) . . . . ?
C11 C12 C13 C14 -179.8(4) . . . . ?
C12 C13 C14 C15 179.3(4) . . . . ?
C13 C14 C15 C16 179.8(4) . . . . ?
C14 C15 C16 C17 179.5(4) . . . . ?
C15 C16 C17 C18 -180.0(5) . . . . ?
N1 C1 C2 C3 164.6(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0068 0.0000 -0.0001 0.9999 0.0267 0.0011 -0.0057
0 0 -1 0.0068 -0.0000 0.0001 -0.9999 -0.0267 -0.0011 0.0057
0 -5 1 0.0478 -0.2473 -4.7071 1.2778 0.0958 -0.9891 0.1119
0 5 -1 0.0395 0.1762 4.7118 -1.3623 -0.0960 0.9911 -0.0921
0 5 -2 0.0395 -0.4169 4.6782 -2.0421 -0.0963 0.9926 0.0740
2 -4 3 0.1158 1.7248 -4.1090 3.3765 0.0868 -0.8914 -0.4447
-1 -5 1 0.0576 -0.7970 -4.6061 0.6038 0.0928 -0.9599 0.2647
-3 3 -4 0.1721 -2.9291 2.6652 -4.2994 -0.0593 0.6043 0.7945
-3 -1 -3 0.1956 -3.4077 -1.4575 -3.4854 0.0241 -0.2582 0.9658
4 1 4 0.2304 3.5443 0.6367 3.9177 -0.0071 0.0831 -0.9965
1 -5 2 0.0698 0.7061 -4.6140 2.3578 0.0955 -0.9832 -0.1554

_olex2_date_sample_data_collection 2015-07-13
_olex2_exptl_crystal_mounting_method 'Hampton Research nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_283
_database_code_depnum_ccdc_archive 'CCDC 1941221'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C16TAB
_chemical_name_systematic        'Hexadecyltrimethylammonium bromide'
_chemical_formula_moiety         'C19 H42 N, Br'
_chemical_formula_sum            'C19 H42 Br N'
_chemical_formula_weight         364.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H42 N Br'
_chemical_oxdiff_usercomment     C16TAB
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.59550(7)
_cell_length_b                   7.14921(12)
_cell_length_c                   51.7885(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.7909(13)
_cell_angle_gamma                90
_cell_volume                     2064.48(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15919
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.4270
_cell_measurement_theta_min      5.1280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.656
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.500
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Recrystallized from H2O'
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.2587
_exptl_crystal_size_min          0.0493
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_number            31281
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.672
_diffrn_reflns_theta_min         5.142
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -120.00  -69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -63.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
  3 omega -124.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -99.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -67.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -38.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega  -70.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   57.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
  6 omega  -65.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega  -96.00  -70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   24.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -125.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega    6.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000  -40.9100 27

#__ type_ start__ end____ width___ exp.time_
 10 omega    6.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000 -165.8311 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   72.5886 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   44.6584 25

#__ type_ start__ end____ width___ exp.time_
 13 omega -139.00 -113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  -63.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
 15 omega  -58.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega  -80.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega  -55.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega  -54.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  -68.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 20 omega  -58.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   34.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -85.7919 38

#__ type_ start__ end____ width___ exp.time_
 22 omega  117.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   65.0000   52.0806 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000  157.4302 27

#__ type_ start__ end____ width___ exp.time_
 24 omega   92.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -85.7919 40

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   65.0000   52.0806 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   35.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   78.5086 46

#__ type_ start__ end____ width___ exp.time_
 27 omega   43.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   69.0000 -160.4155 28

#__ type_ start__ end____ width___ exp.time_
 28 omega   43.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   73.0000  141.9229 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   47.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   74.0000  -41.4678 38

#__ type_ start__ end____ width___ exp.time_
 30 omega   47.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   74.0000   60.3686 31

#__ type_ start__ end____ width___ exp.time_
 31 omega   96.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   74.0000   60.3686 25

#__ type_ start__ end____ width___ exp.time_
 32 omega  126.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   74.0000   60.3686 31

#__ type_ start__ end____ width___ exp.time_
 33 omega   53.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   65.0000  156.4166 42

#__ type_ start__ end____ width___ exp.time_
 34 omega   69.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000   76.8886 28

#__ type_ start__ end____ width___ exp.time_
 35 omega  108.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000 -148.5789 67

#__ type_ start__ end____ width___ exp.time_
 36 omega   68.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000 -148.5789 35

#__ type_ start__ end____ width___ exp.time_
 37 omega  143.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000   76.8886 29

#__ type_ start__ end____ width___ exp.time_
 38 omega   74.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
 39 omega   74.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 40 omega   32.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180 -125.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 41 omega   82.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 42 omega   51.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180 -125.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
 43 omega   74.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 44 omega   74.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  -90.0000 103

#__ type_ start__ end____ width___ exp.time_
 45 omega   74.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 46 omega   86.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000    0.0000 73

#__ type_ start__ end____ width___ exp.time_
 47 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega  131.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 49 omega  142.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 50 omega   77.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
 51 omega   75.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
 52 omega  139.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 53 omega   78.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega  110.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 55 omega   96.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
 56 omega   34.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -61.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 57 omega  109.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 58 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   74.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  -60.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2347199000
_diffrn_orient_matrix_UB_12      0.0507341000
_diffrn_orient_matrix_UB_13      0.0119192000
_diffrn_orient_matrix_UB_21      -0.1326365000
_diffrn_orient_matrix_UB_22      0.0054668000
_diffrn_orient_matrix_UB_23      -0.0272839000
_diffrn_orient_matrix_UB_31      -0.0604024000
_diffrn_orient_matrix_UB_32      -0.2093473000
_diffrn_orient_matrix_UB_33      0.0021759000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3536
_reflns_number_total             4027
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.232
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+2.1559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0816
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B)
Uiso(H13A) = Uiso(H13B)
Uiso(H14A) = Uiso(H14B)
Uiso(H15A) = Uiso(H15B)
Uiso(H16A) = Uiso(H16B) = Uiso(H16C)
Uiso(H17A) = Uiso(H17B) = Uiso(H17C) = Uiso(H18A) = Uiso(H18B) = Uiso(H18C) =
Uiso(H19A) = Uiso(H19B) = Uiso(H19C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.748(4) 0.380(4) 0.0567(4) 0.019(4) Uiso 1 1 d . . . . .
H1B H 0.716(4) 0.159(4) 0.0537(4) 0.019(4) Uiso 1 1 d . . . . .
H2A H 1.063(5) 0.301(4) 0.0921(5) 0.023(5) Uiso 1 1 d . . . . .
H2B H 0.964(4) 0.088(4) 0.0902(5) 0.023(5) Uiso 1 1 d . . . . .
H3A H 0.699(5) 0.412(4) 0.1029(5) 0.028(5) Uiso 1 1 d . . . . .
H3B H 0.574(5) 0.216(4) 0.0983(5) 0.028(5) Uiso 1 1 d . . . . .
H4A H 0.927(5) 0.263(4) 0.1398(5) 0.030(5) Uiso 1 1 d . . . . .
H4B H 0.774(5) 0.085(4) 0.1345(5) 0.030(5) Uiso 1 1 d . . . . .
H5A H 0.593(5) 0.430(4) 0.1496(5) 0.028(5) Uiso 1 1 d . . . . .
H5B H 0.421(5) 0.270(4) 0.1420(5) 0.028(5) Uiso 1 1 d . . . . .
H6A H 0.765(5) 0.251(4) 0.1851(5) 0.030(5) Uiso 1 1 d . . . . .
H6B H 0.588(5) 0.088(4) 0.1773(5) 0.030(5) Uiso 1 1 d . . . . .
H7A H 0.435(5) 0.445(4) 0.1949(5) 0.029(5) Uiso 1 1 d . . . . .
H7B H 0.250(5) 0.286(4) 0.1857(5) 0.029(5) Uiso 1 1 d . . . . .
H8A H 0.585(5) 0.245(4) 0.2293(5) 0.024(4) Uiso 1 1 d . . . . .
H8B H 0.401(4) 0.089(4) 0.2197(5) 0.024(4) Uiso 1 1 d . . . . .
H9A H 0.260(4) 0.444(4) 0.2383(5) 0.023(5) Uiso 1 1 d . . . . .
H9B H 0.078(5) 0.286(3) 0.2292(5) 0.023(5) Uiso 1 1 d . . . . .
H10A H 0.411(5) 0.248(4) 0.2735(5) 0.027(5) Uiso 1 1 d . . . . .
H10B H 0.226(5) 0.086(4) 0.2642(5) 0.027(5) Uiso 1 1 d . . . . .
H11A H 0.084(5) 0.439(4) 0.2821(5) 0.028(5) Uiso 1 1 d . . . . .
H11B H -0.098(5) 0.289(4) 0.2736(5) 0.028(5) Uiso 1 1 d . . . . .
H12A H 0.238(5) 0.246(4) 0.3173(5) 0.029(5) Uiso 1 1 d . . . . .
H12B H 0.056(5) 0.088(4) 0.3075(5) 0.029(5) Uiso 1 1 d . . . . .
H13A H -0.077(4) 0.445(4) 0.3273(5) 0.026(5) Uiso 1 1 d . . . . .
H13B H -0.272(5) 0.293(4) 0.3168(5) 0.026(5) Uiso 1 1 d . . . . .
H14A H 0.065(5) 0.238(4) 0.3609(5) 0.029(5) Uiso 1 1 d . . . . .
H14B H -0.120(5) 0.093(4) 0.3518(5) 0.029(5) Uiso 1 1 d . . . . .
H15A H -0.242(5) 0.448(4) 0.3711(5) 0.033(5) Uiso 1 1 d . . . . .
H15B H -0.430(5) 0.297(4) 0.3620(5) 0.033(5) Uiso 1 1 d . . . . .
H16A H -0.111(7) 0.243(5) 0.4060(7) 0.055(6) Uiso 1 1 d . . . . .
H16B H -0.297(6) 0.083(5) 0.3950(6) 0.055(6) Uiso 1 1 d . . . . .
H16C H -0.370(6) 0.278(5) 0.4062(7) 0.055(6) Uiso 1 1 d . . . . .
H17A H 0.779(5) 0.368(4) 0.0129(5) 0.025(2) Uiso 1 1 d . . . . .
H17B H 0.784(5) 0.145(4) 0.0116(5) 0.025(2) Uiso 1 1 d . . . . .
H17C H 0.999(5) 0.257(4) 0.0008(5) 0.025(2) Uiso 1 1 d . . . . .
H18A H 1.270(4) 0.415(4) 0.0591(5) 0.025(2) Uiso 1 1 d . . . . .
H18B H 1.081(5) 0.526(4) 0.0413(5) 0.025(2) Uiso 1 1 d . . . . .
H18C H 1.285(5) 0.410(4) 0.0290(5) 0.025(2) Uiso 1 1 d . . . . .
H19A H 1.057(5) -0.029(4) 0.0403(5) 0.025(2) Uiso 1 1 d . . . . .
H19B H 1.266(4) 0.082(4) 0.0584(5) 0.025(2) Uiso 1 1 d . . . . .
H19C H 1.273(5) 0.080(4) 0.0279(5) 0.025(2) Uiso 1 1 d . . . . .
C1 C 0.8280(3) 0.2542(4) 0.05922(4) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.9190(4) 0.2199(3) 0.08732(4) 0.0207(5) Uani 1 1 d . . . . .
C3 C 0.7217(4) 0.2791(4) 0.10437(4) 0.0246(5) Uani 1 1 d . . . . .
C4 C 0.7696(4) 0.2225(4) 0.13276(4) 0.0232(5) Uani 1 1 d . . . . .
C5 C 0.5814(4) 0.2998(3) 0.14946(4) 0.0216(5) Uani 1 1 d . . . . .
C6 C 0.6025(4) 0.2260(4) 0.17719(4) 0.0222(5) Uani 1 1 d . . . . .
C7 C 0.4150(4) 0.3071(4) 0.19370(4) 0.0212(5) Uani 1 1 d . . . . .
C8 C 0.4278(4) 0.2264(4) 0.22109(4) 0.0216(5) Uani 1 1 d . . . . .
C9 C 0.2410(4) 0.3090(4) 0.23762(4) 0.0218(5) Uani 1 1 d . . . . .
C10 C 0.2523(4) 0.2261(4) 0.26488(4) 0.0215(5) Uani 1 1 d . . . . .
C11 C 0.0670(4) 0.3092(4) 0.28157(4) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.0787(4) 0.2262(4) 0.30887(4) 0.0226(5) Uani 1 1 d . . . . .
C13 C -0.1046(4) 0.3099(4) 0.32571(4) 0.0221(5) Uani 1 1 d . . . . .
C14 C -0.0933(4) 0.2259(4) 0.35292(4) 0.0240(5) Uani 1 1 d . . . . .
C15 C -0.2738(5) 0.3111(4) 0.37002(4) 0.0277(5) Uani 1 1 d . . . . .
C16 C -0.2596(6) 0.2213(4) 0.39694(5) 0.0386(7) Uani 1 1 d . . . . .
C17 C 0.8803(4) 0.2569(4) 0.01337(4) 0.0233(5) Uani 1 1 d . . . . .
C18 C 1.1769(4) 0.4175(3) 0.04263(4) 0.0211(5) Uani 1 1 d . . . . .
C19 C 1.1619(4) 0.0754(3) 0.04195(4) 0.0223(5) Uani 1 1 d . . . . .
N1 N 1.0146(3) 0.2506(3) 0.03970(3) 0.0164(3) Uani 1 1 d . . . . .
Br1 Br 0.63426(4) 0.75233(3) 0.03629(2) 0.02649(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 1.01(3) . ?
C1 H1B 0.95(3) . ?
C1 C2 1.521(3) . ?
C1 N1 1.513(2) . ?
C2 H2A 1.00(3) . ?
C2 H2B 0.99(3) . ?
C2 C3 1.530(3) . ?
C3 H3A 0.96(3) . ?
C3 H3B 0.97(3) . ?
C3 C4 1.527(3) . ?
C4 H4A 0.97(3) . ?
C4 H4B 0.99(3) . ?
C4 C5 1.521(3) . ?
C5 H5A 0.93(3) . ?
C5 H5B 0.97(3) . ?
C5 C6 1.525(3) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.99(3) . ?
C6 C7 1.522(3) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.99(3) . ?
C7 C8 1.527(3) . ?
C8 H8A 0.95(3) . ?
C8 H8B 0.99(3) . ?
C8 C9 1.524(3) . ?
C9 H9A 0.97(3) . ?
C9 H9B 0.99(3) . ?
C9 C10 1.527(3) . ?
C10 H10A 0.97(3) . ?
C10 H10B 1.01(3) . ?
C10 C11 1.525(3) . ?
C11 H11A 0.93(3) . ?
C11 H11B 0.99(3) . ?
C11 C12 1.530(3) . ?
C12 H12A 0.97(3) . ?
C12 H12B 0.99(3) . ?
C12 C13 1.523(3) . ?
C13 H13A 0.98(3) . ?
C13 H13B 1.01(3) . ?
C13 C14 1.528(3) . ?
C14 H14A 0.95(3) . ?
C14 H14B 0.96(3) . ?
C14 C15 1.525(3) . ?
C15 H15A 1.00(3) . ?
C15 H15B 0.94(3) . ?
C15 C16 1.531(3) . ?
C16 H16A 0.93(4) . ?
C16 H16B 1.02(4) . ?
C16 H16C 0.91(4) . ?
C17 H17A 0.97(3) . ?
C17 H17B 0.96(3) . ?
C17 H17C 0.97(3) . ?
C17 N1 1.501(2) . ?
C18 H18A 0.96(2) . ?
C18 H18B 0.94(3) . ?
C18 H18C 0.97(3) . ?
C18 N1 1.499(3) . ?
C19 H19A 0.95(3) . ?
C19 H19B 0.99(2) . ?
C19 H19C 1.00(3) . ?
C19 N1 1.499(3) . ?

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
_geom_angle_publ_flag
H1A C1 H1B 109(2) . . ?
C2 C1 H1A 112.2(13) . . ?
C2 C1 H1B 109.4(14) . . ?
N1 C1 H1A 104.5(13) . . ?
N1 C1 H1B 105.2(14) . . ?
N1 C1 C2 116.22(16) . . ?
H2A C2 H2B 109(2) . . ?
C1 C2 H2A 110.0(14) . . ?
C1 C2 H2B 111.1(14) . . ?
C1 C2 C3 107.91(17) . . ?
C3 C2 H2A 107.3(14) . . ?
C3 C2 H2B 111.5(15) . . ?
H3A C3 H3B 109(2) . . ?
C2 C3 H3A 108.9(16) . . ?
C2 C3 H3B 108.7(16) . . ?
C4 C3 H3A 110.6(15) . . ?
C4 C3 H3B 105.4(15) . . ?
C4 C3 C2 113.92(19) . . ?
H4A C4 H4B 104(2) . . ?
C3 C4 H4A 111.5(16) . . ?
C3 C4 H4B 110.5(15) . . ?
C5 C4 H4A 109.1(16) . . ?
C5 C4 H4B 108.9(16) . . ?
C5 C4 C3 112.14(19) . . ?
H5A C5 H5B 106(2) . . ?
C4 C5 H5A 108.4(16) . . ?
C4 C5 H5B 110.7(16) . . ?
C4 C5 C6 114.01(19) . . ?
C6 C5 H5A 109.9(16) . . ?
C6 C5 H5B 107.3(16) . . ?
H6A C6 H6B 105(2) . . ?
C5 C6 H6A 108.9(16) . . ?
C5 C6 H6B 110.5(15) . . ?
C7 C6 H6A 110.8(16) . . ?
C7 C6 H6B 108.4(16) . . ?
C7 C6 C5 113.23(19) . . ?
H7A C7 H7B 106(2) . . ?
C6 C7 H7A 109.4(16) . . ?
C6 C7 H7B 111.5(15) . . ?
C6 C7 C8 113.37(19) . . ?
C8 C7 H7A 108.6(15) . . ?
C8 C7 H7B 107.5(15) . . ?
H8A C8 H8B 107(2) . . ?
C7 C8 H8A 109.4(15) . . ?
C7 C8 H8B 108.0(14) . . ?
C9 C8 H8A 110.1(15) . . ?
C9 C8 H8B 108.5(15) . . ?
C9 C8 C7 113.21(19) . . ?
H9A C9 H9B 106(2) . . ?
C8 C9 H9A 109.0(15) . . ?
C8 C9 H9B 109.7(14) . . ?
C8 C9 C10 113.05(19) . . ?
C10 C9 H9A 111.0(14) . . ?
C10 C9 H9B 108.0(14) . . ?
H10A C10 H10B 108(2) . . ?
C9 C10 H10A 109.1(15) . . ?
C9 C10 H10B 111.0(14) . . ?
C11 C10 H10A 108.4(15) . . ?
C11 C10 H10B 107.4(15) . . ?
C11 C10 C9 113.29(19) . . ?
H11A C11 H11B 104(2) . . ?
C10 C11 H11A 109.4(16) . . ?
C10 C11 H11B 111.0(15) . . ?
C10 C11 C12 113.23(19) . . ?
C12 C11 H11A 111.3(15) . . ?
C12 C11 H11B 107.3(15) . . ?
H12A C12 H12B 106(2) . . ?
C11 C12 H12A 108.9(16) . . ?
C11 C12 H12B 109.0(15) . . ?
C13 C12 H12A 108.9(16) . . ?
C13 C12 H12B 109.9(16) . . ?
C13 C12 C11 113.46(19) . . ?
H13A C13 H13B 107(2) . . ?
C12 C13 H13A 109.1(15) . . ?
C12 C13 H13B 109.4(14) . . ?
C12 C13 C14 113.31(19) . . ?
C14 C13 H13A 108.5(14) . . ?
C14 C13 H13B 109.7(15) . . ?
H14A C14 H14B 105(2) . . ?
C13 C14 H14A 109.3(16) . . ?
C13 C14 H14B 109.8(16) . . ?
C15 C14 H14A 110.5(16) . . ?
C15 C14 H14B 108.6(16) . . ?
C15 C14 C13 113.6(2) . . ?
H15A C15 H15B 106(2) . . ?
C14 C15 H15A 107.6(16) . . ?
C14 C15 H15B 109.7(17) . . ?
C14 C15 C16 112.0(2) . . ?
C16 C15 H15A 111.4(15) . . ?
C16 C15 H15B 109.6(17) . . ?
H16A C16 H16B 112(3) . . ?
H16A C16 H16C 106(3) . . ?
H16B C16 H16C 110(3) . . ?
C15 C16 H16A 111(2) . . ?
C15 C16 H16B 108.9(18) . . ?
C15 C16 H16C 108(2) . . ?
H17A C17 H17B 111(2) . . ?
H17A C17 H17C 114(2) . . ?
H17B C17 H17C 110(2) . . ?
N1 C17 H17A 107.1(14) . . ?
N1 C17 H17B 107.1(15) . . ?
N1 C17 H17C 107.0(16) . . ?
H18A C18 H18B 110(2) . . ?
H18A C18 H18C 108(2) . . ?
H18B C18 H18C 112(2) . . ?
N1 C18 H18A 110.8(15) . . ?
N1 C18 H18B 108.1(16) . . ?
N1 C18 H18C 107.1(15) . . ?
H19A C19 H19B 115(2) . . ?
H19A C19 H19C 113(2) . . ?
H19B C19 H19C 105(2) . . ?
N1 C19 H19A 108.5(16) . . ?
N1 C19 H19B 107.8(15) . . ?
N1 C19 H19C 106.7(15) . . ?
C17 N1 C1 106.59(15) . . ?
C18 N1 C1 111.41(17) . . ?
C18 N1 C17 108.72(17) . . ?
C19 N1 C1 111.61(17) . . ?
C19 N1 C17 109.01(17) . . ?
C19 N1 C18 109.41(16) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 170.2(2) . . . . ?
C2 C1 N1 C17 171.2(2) . . . . ?
C2 C1 N1 C18 -70.3(3) . . . . ?
C2 C1 N1 C19 52.3(3) . . . . ?
C2 C3 C4 C5 174.6(2) . . . . ?
C3 C4 C5 C6 172.3(2) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
C5 C6 C7 C8 177.2(2) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
C7 C8 C9 C10 179.3(2) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C9 C10 C11 C12 -179.9(2) . . . . ?
C10 C11 C12 C13 179.5(2) . . . . ?
C11 C12 C13 C14 179.7(2) . . . . ?
C12 C13 C14 C15 179.1(2) . . . . ?
C13 C14 C15 C16 179.1(2) . . . . ?
N1 C1 C2 C3 165.4(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 2 0.0246 0.0001 -0.0000 2.0004 0.0238 -0.0546 0.0044
1 4 -3 0.1194 1.3729 4.2867 -3.1278 -0.1420 -0.0733 -0.9871
3 -3 1 0.1893 2.6745 -3.1190 0.5943 -0.7789 -0.3880 0.4927
0 -5 3 0.0879 0.0317 -4.6255 2.6824 -0.2101 -0.1027 0.9723
-3 3 0 0.1838 -3.0017 2.9963 -0.0103 0.8564 0.4148 -0.4460
0 0 -2 0.0246 -0.0001 0.0000 -2.0004 -0.0238 0.0546 -0.0044

_olex2_date_sample_data_collection 2014-02-03
_olex2_exptl_crystal_mounting_method 'Hampton Research nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_518
_database_code_depnum_ccdc_archive 'CCDC 1941222'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C16TAB
_chemical_name_systematic        'Hexadecyltrimethylammonium bromide'
_chemical_formula_moiety         'C19 H42 N, Br'
_chemical_formula_sum            'C19 H42 Br N'
_chemical_formula_weight         364.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H42 N Br'
_chemical_oxdiff_usercomment     'Recrystallized from H2O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.63257(8)
_cell_length_b                   7.26127(11)
_cell_length_c                   52.0364(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.7545(14)
_cell_angle_gamma                90
_cell_volume                     2123.70(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11185
_cell_measurement_temperature    295
_cell_measurement_theta_max      73.6940
_cell_measurement_theta_min      5.0950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.582
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.442
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method 'Recrystallized from H2O'
_exptl_crystal_size_max          0.5774
_exptl_crystal_size_mid          0.2104
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            26213
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.920
_diffrn_reflns_theta_min         3.405
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   83.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   45.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  131.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   53.0000 -174.6730 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  148.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  136.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   59.0000   10.7314 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  122.00  153.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   45.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  6 omega  118.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  7 omega  139.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
  8 omega   77.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   78.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   75.00  165.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   79.00  138.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   78.00  129.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   45.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   75.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  104.2529 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   75.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 18 omega   75.00  167.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   74.0000  -41.9204 92

#__ type_ start__ end____ width___ exp.time_
 19 omega   82.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   45.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   80.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   53.0000 -174.6730 42

#__ type_ start__ end____ width___ exp.time_
 21 omega   76.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 22 omega   78.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   78.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
 24 omega   75.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   76.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   79.00  131.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   59.0000   10.7314 52

#__ type_ start__ end____ width___ exp.time_
 27 omega   75.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   78.00  113.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713   61.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 29 omega    1.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8151  -99.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
 30 omega   23.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8151 -125.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 31 omega    2.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8151  -99.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
 32 omega   32.00  107.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -94.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 33 omega   33.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713 -125.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 34 omega   32.00  140.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713  -77.0000  -90.0000 108

#__ type_ start__ end____ width___ exp.time_
 35 omega   33.00  119.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.3713 -125.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
 36 omega   24.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.8151 -125.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 37 omega  -50.00   -8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
 38 omega  -46.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega  -35.00   -8.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 40 omega  -62.00  -18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -38.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 41 omega  -52.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 42 omega  -78.00   -9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000   90.0000 69

#__ type_ start__ end____ width___ exp.time_
 43 omega -115.00  -75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 44 omega -102.00  -76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 45 omega -104.00   -9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 46 omega -118.00  -70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -38.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 47 omega -110.00  -83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -57.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 48 omega -124.00  -88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -99.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 49 omega -121.00  -85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.8151  -77.0000   90.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0802477000
_diffrn_orient_matrix_UB_12      0.0901182000
_diffrn_orient_matrix_UB_13      -0.0259363000
_diffrn_orient_matrix_UB_21      0.2305952000
_diffrn_orient_matrix_UB_22      0.1145955000
_diffrn_orient_matrix_UB_23      0.0010465000
_diffrn_orient_matrix_UB_31      0.1244836000
_diffrn_orient_matrix_UB_32      -0.1541491000
_diffrn_orient_matrix_UB_33      -0.0143755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3517
_reflns_number_total             4232
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      1.226
_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)+(0.0308P)²+4.9834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1498
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 H16A-H16B \\sim H16B-H16C \\sim H16C-H16A
 with sigma of 0.005
 C16-H16A \\sim C16-H16B \\sim C16-H16C
 with sigma of 0.005
 C15-H16A \\sim C15-H16B \\sim C15-H16C
 with sigma of 0.005
2. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B)
Uiso(H13A) = Uiso(H13B)
Uiso(H14A) = Uiso(H14B)
Uiso(H15A) = Uiso(H15B)
Uiso(H16A) = Uiso(H16B) = Uiso(H16C)
Uiso(H17A) = Uiso(H17B) = Uiso(H17C) = Uiso(H18A) = Uiso(H18B) = Uiso(H18C) =
Uiso(H19A) = Uiso(H19B) = Uiso(H19C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.736(7) 0.370(6) 0.0559(8) 0.034(7) Uiso 1 1 d . . . . .
H1B H 0.709(8) 0.164(6) 0.0530(8) 0.034(7) Uiso 1 1 d . . . . .
H2A H 1.037(8) 0.316(7) 0.0906(9) 0.044(9) Uiso 1 1 d . . . . .
H2B H 0.944(8) 0.087(7) 0.0894(8) 0.044(9) Uiso 1 1 d . . . . .
H3A H 0.683(9) 0.406(8) 0.1031(10) 0.059(16) Uiso 1 1 d . . . . .
H3B H 0.568(9) 0.218(7) 0.0984(9) 0.054(14) Uiso 1 1 d . . . . .
H4A H 0.914(8) 0.276(6) 0.1388(8) 0.039(8) Uiso 1 1 d . . . . .
H4B H 0.800(8) 0.102(7) 0.1344(8) 0.039(8) Uiso 1 1 d . . . . .
H5A H 0.587(8) 0.432(7) 0.1502(9) 0.045(9) Uiso 1 1 d . . . . .
H5B H 0.425(8) 0.262(7) 0.1422(9) 0.045(9) Uiso 1 1 d . . . . .
H6A H 0.761(9) 0.259(7) 0.1845(9) 0.050(9) Uiso 1 1 d . . . . .
H6B H 0.589(8) 0.092(7) 0.1771(9) 0.050(9) Uiso 1 1 d . . . . .
H7A H 0.431(9) 0.440(7) 0.1948(9) 0.049(10) Uiso 1 1 d . . . . .
H7B H 0.259(9) 0.287(7) 0.1857(9) 0.049(10) Uiso 1 1 d . . . . .
H8A H 0.585(9) 0.238(7) 0.2293(9) 0.056(10) Uiso 1 1 d . . . . .
H8B H 0.412(9) 0.092(8) 0.2202(9) 0.056(10) Uiso 1 1 d . . . . .
H9A H 0.261(8) 0.436(7) 0.2384(9) 0.043(9) Uiso 1 1 d . . . . .
H9B H 0.082(8) 0.288(6) 0.2292(9) 0.043(9) Uiso 1 1 d . . . . .
H10A H 0.417(8) 0.253(7) 0.2736(9) 0.050(9) Uiso 1 1 d . . . . .
H10B H 0.236(9) 0.095(7) 0.2647(9) 0.050(9) Uiso 1 1 d . . . . .
H11A H 0.089(9) 0.440(8) 0.2832(9) 0.053(10) Uiso 1 1 d . . . . .
H11B H -0.092(9) 0.292(7) 0.2738(9) 0.053(10) Uiso 1 1 d . . . . .
H12A H 0.234(9) 0.251(7) 0.3175(9) 0.054(10) Uiso 1 1 d . . . . .
H12B H 0.062(9) 0.094(8) 0.3076(9) 0.054(10) Uiso 1 1 d . . . . .
H13A H -0.075(8) 0.438(7) 0.3274(9) 0.046(9) Uiso 1 1 d . . . . .
H13B H -0.264(9) 0.297(6) 0.3179(9) 0.046(9) Uiso 1 1 d . . . . .
H14A H 0.068(9) 0.244(8) 0.3609(10) 0.059(10) Uiso 1 1 d . . . . .
H14B H -0.112(9) 0.092(8) 0.3515(10) 0.059(10) Uiso 1 1 d . . . . .
H15A H -0.248(9) 0.449(8) 0.3718(10) 0.063(11) Uiso 1 1 d . . . . .
H15B H -0.440(10) 0.299(7) 0.3627(10) 0.063(11) Uiso 1 1 d . . . . .
H16A H -0.094(6) 0.249(5) 0.4054(7) 0.101(14) Uiso 1 1 d D . . . .
H16B H -0.283(7) 0.088(4) 0.3951(7) 0.101(14) Uiso 1 1 d D . . . .
H16C H -0.381(6) 0.281(5) 0.4070(7) 0.101(14) Uiso 1 1 d D . . . .
H17A H 0.774(9) 0.350(7) 0.0135(9) 0.045(4) Uiso 1 1 d . . . . .
H17B H 0.790(8) 0.138(7) 0.0121(9) 0.045(4) Uiso 1 1 d . . . . .
H17C H 0.993(8) 0.262(7) 0.0003(9) 0.045(4) Uiso 1 1 d . . . . .
H18A H 1.264(8) 0.403(7) 0.0587(9) 0.045(4) Uiso 1 1 d . . . . .
H18B H 1.071(8) 0.524(7) 0.0423(9) 0.045(4) Uiso 1 1 d . . . . .
H18C H 1.276(8) 0.411(7) 0.0291(9) 0.045(4) Uiso 1 1 d . . . . .
H19A H 1.045(9) -0.021(7) 0.0402(9) 0.045(4) Uiso 1 1 d . . . . .
H19B H 1.259(8) 0.080(7) 0.0576(9) 0.045(4) Uiso 1 1 d . . . . .
H19C H 1.254(8) 0.078(7) 0.0268(9) 0.045(4) Uiso 1 1 d . . . . .
C1 C 0.8236(6) 0.2519(7) 0.05928(7) 0.0354(8) Uani 1 1 d . . . . .
C2 C 0.9119(7) 0.2204(6) 0.08695(8) 0.0366(9) Uani 1 1 d . . . . .
C3 C 0.7162(9) 0.2774(8) 0.10424(8) 0.0477(11) Uani 1 1 d . . . . .
C4 C 0.7634(8) 0.2280(8) 0.13239(8) 0.0491(12) Uani 1 1 d . . . . .
C5 C 0.5776(8) 0.2986(7) 0.14938(8) 0.0428(10) Uani 1 1 d . . . . .
C6 C 0.6005(8) 0.2279(7) 0.17697(8) 0.0424(10) Uani 1 1 d . . . . .
C7 C 0.4137(9) 0.3073(7) 0.19367(8) 0.0433(10) Uani 1 1 d . . . . .
C8 C 0.4270(8) 0.2322(8) 0.22095(8) 0.0459(10) Uani 1 1 d . . . . .
C9 C 0.2409(8) 0.3089(7) 0.23783(8) 0.0429(10) Uani 1 1 d . . . . .
C10 C 0.2525(8) 0.2300(7) 0.26483(8) 0.0445(10) Uani 1 1 d . . . . .
C11 C 0.0681(9) 0.3099(7) 0.28174(8) 0.0437(10) Uani 1 1 d . . . . .
C12 C 0.0785(8) 0.2278(7) 0.30872(8) 0.0438(10) Uani 1 1 d . . . . .
C13 C -0.1017(9) 0.3096(7) 0.32583(8) 0.0432(10) Uani 1 1 d . . . . .
C14 C -0.0897(9) 0.2282(7) 0.35293(9) 0.0478(11) Uani 1 1 d . . . . .
C15 C -0.2685(10) 0.3094(8) 0.37022(10) 0.0566(13) Uani 1 1 d D . . . .
C16 C -0.2553(13) 0.2234(9) 0.39704(11) 0.080(2) Uani 1 1 d D . . . .
C17 C 0.8774(8) 0.2580(8) 0.01359(7) 0.0452(10) Uani 1 1 d . . . . .
C18 C 1.1693(9) 0.4155(6) 0.04221(9) 0.0412(10) Uani 1 1 d . . . . .
C19 C 1.1553(8) 0.0785(7) 0.04151(10) 0.0418(10) Uani 1 1 d . . . . .
N1 N 1.0094(5) 0.2505(5) 0.03954(5) 0.0311(6) Uani 1 1 d . . . . .
Br1 Br 0.63071(7) 0.75152(7) 0.03617(2) 0.05070(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 1.00(4) . ?
C1 H1B 0.95(4) . ?
C1 C2 1.510(5) . ?
C1 N1 1.513(4) . ?
C2 H2A 1.00(5) . ?
C2 H2B 0.99(5) . ?
C2 C3 1.525(6) . ?
C3 H3A 0.95(6) . ?
C3 H3B 0.97(5) . ?
C3 C4 1.514(6) . ?
C4 H4A 0.95(5) . ?
C4 H4B 0.94(5) . ?
C4 C5 1.504(6) . ?
C5 H5A 0.97(5) . ?
C5 H5B 0.96(5) . ?
C5 C6 1.522(6) . ?
C6 H6A 0.99(5) . ?
C6 H6B 0.99(5) . ?
C6 C7 1.521(6) . ?
C7 H7A 0.97(5) . ?
C7 H7B 0.95(5) . ?
C7 C8 1.518(6) . ?
C8 H8A 0.97(5) . ?
C8 H8B 1.02(6) . ?
C8 C9 1.517(6) . ?
C9 H9A 0.93(5) . ?
C9 H9B 0.98(5) . ?
C9 C10 1.515(6) . ?
C10 H10A 1.02(5) . ?
C10 H10B 0.99(5) . ?
C10 C11 1.520(6) . ?
C11 H11A 0.96(6) . ?
C11 H11B 0.98(5) . ?
C11 C12 1.523(6) . ?
C12 H12A 0.98(5) . ?
C12 H12B 0.98(5) . ?
C12 C13 1.514(6) . ?
C13 H13A 0.94(5) . ?
C13 H13B 0.98(5) . ?
C13 C14 1.527(6) . ?
C14 H14A 0.96(5) . ?
C14 H14B 1.00(6) . ?
C14 C15 1.514(7) . ?
C15 H15A 1.02(6) . ?
C15 H15B 1.02(5) . ?
C15 C16 1.526(8) . ?
C16 H16A 1.00(3) . ?
C16 H16B 1.00(3) . ?
C16 H16C 1.00(3) . ?
C17 H17A 0.89(5) . ?
C17 H17B 1.00(5) . ?
C17 H17C 0.98(5) . ?
C17 N1 1.500(5) . ?
C18 H18A 0.98(5) . ?
C18 H18B 0.97(5) . ?
C18 H18C 0.94(5) . ?
C18 N1 1.500(6) . ?
C19 H19A 0.95(5) . ?
C19 H19B 0.99(5) . ?
C19 H19C 0.98(5) . ?
C19 N1 1.495(5) . ?

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
_geom_angle_publ_flag
H1A C1 H1B 102(3) . . ?
C2 C1 H1A 115(2) . . ?
C2 C1 H1B 114(3) . . ?
C2 C1 N1 116.6(3) . . ?
N1 C1 H1A 104(2) . . ?
N1 C1 H1B 104(3) . . ?
H2A C2 H2B 122(4) . . ?
C1 C2 H2A 105(3) . . ?
C1 C2 H2B 108(3) . . ?
C1 C2 C3 108.4(3) . . ?
C3 C2 H2A 103(3) . . ?
C3 C2 H2B 109(3) . . ?
H3A C3 H3B 105(4) . . ?
C2 C3 H3A 112(3) . . ?
C2 C3 H3B 109(3) . . ?
C4 C3 H3A 108(3) . . ?
C4 C3 H3B 107(3) . . ?
C4 C3 C2 114.7(4) . . ?
H4A C4 H4B 97(4) . . ?
C3 C4 H4A 110(3) . . ?
C3 C4 H4B 111(3) . . ?
C5 C4 H4A 108(3) . . ?
C5 C4 H4B 115(3) . . ?
C5 C4 C3 113.8(4) . . ?
H5A C5 H5B 110(4) . . ?
C4 C5 H5A 109(3) . . ?
C4 C5 H5B 109(3) . . ?
C4 C5 C6 114.8(4) . . ?
C6 C5 H5A 107(3) . . ?
C6 C5 H5B 107(3) . . ?
H6A C6 H6B 107(4) . . ?
C5 C6 H6A 108(3) . . ?
C5 C6 H6B 110(3) . . ?
C7 C6 H6A 110(3) . . ?
C7 C6 H6B 109(3) . . ?
C7 C6 C5 113.1(4) . . ?
H7A C7 H7B 105(4) . . ?
C6 C7 H7A 110(3) . . ?
C6 C7 H7B 110(3) . . ?
C8 C7 H7A 108(3) . . ?
C8 C7 H7B 110(3) . . ?
C8 C7 C6 113.9(4) . . ?
H8A C8 H8B 98(4) . . ?
C7 C8 H8A 113(3) . . ?
C7 C8 H8B 109(3) . . ?
C9 C8 H8A 112(3) . . ?
C9 C8 H8B 109(3) . . ?
C9 C8 C7 114.6(4) . . ?
H9A C9 H9B 106(4) . . ?
C8 C9 H9A 107(3) . . ?
C8 C9 H9B 109(3) . . ?
C10 C9 H9A 110(3) . . ?
C10 C9 H9B 110(3) . . ?
C10 C9 C8 114.1(4) . . ?
H10A C10 H10B 104(4) . . ?
C9 C10 H10A 110(3) . . ?
C9 C10 H10B 112(3) . . ?
C9 C10 C11 113.8(4) . . ?
C11 C10 H10A 108(3) . . ?
C11 C10 H10B 109(3) . . ?
H11A C11 H11B 106(4) . . ?
C10 C11 H11A 110(3) . . ?
C10 C11 H11B 111(3) . . ?
C10 C11 C12 113.4(4) . . ?
C12 C11 H11A 109(3) . . ?
C12 C11 H11B 108(3) . . ?
H12A C12 H12B 106(4) . . ?
C11 C12 H12A 110(3) . . ?
C11 C12 H12B 110(3) . . ?
C13 C12 H12A 106(3) . . ?
C13 C12 H12B 111(3) . . ?
C13 C12 C11 113.7(4) . . ?
H13A C13 H13B 105(4) . . ?
C12 C13 H13A 109(3) . . ?
C12 C13 H13B 111(3) . . ?
C12 C13 C14 113.6(4) . . ?
C14 C13 H13A 108(3) . . ?
C14 C13 H13B 110(3) . . ?
H14A C14 H14B 105(4) . . ?
C13 C14 H14A 110(3) . . ?
C13 C14 H14B 109(3) . . ?
C15 C14 H14A 109(3) . . ?
C15 C14 H14B 110(3) . . ?
C15 C14 C13 114.0(4) . . ?
H15A C15 H15B 102(4) . . ?
C14 C15 H15A 111(3) . . ?
C14 C15 H15B 113(3) . . ?
C14 C15 C16 112.9(5) . . ?
C16 C15 H15A 110(3) . . ?
C16 C15 H15B 108(3) . . ?
H16A C16 H16B 111(2) . . ?
H16A C16 H16C 111(2) . . ?
H16B C16 H16C 111(2) . . ?
C15 C16 H16A 108(2) . . ?
C15 C16 H16B 108(2) . . ?
C15 C16 H16C 108(2) . . ?
H17A C17 H17B 110(4) . . ?
H17A C17 H17C 116(4) . . ?
H17B C17 H17C 108(4) . . ?
N1 C17 H17A 108(3) . . ?
N1 C17 H17B 105(3) . . ?
N1 C17 H17C 109(3) . . ?
H18A C18 H18B 111(4) . . ?
H18A C18 H18C 107(4) . . ?
H18B C18 H18C 115(4) . . ?
N1 C18 H18A 107(3) . . ?
N1 C18 H18B 108(3) . . ?
N1 C18 H18C 108(3) . . ?
H19A C19 H19B 115(4) . . ?
H19A C19 H19C 110(4) . . ?
H19B C19 H19C 109(4) . . ?
N1 C19 H19A 106(3) . . ?
N1 C19 H19B 110(3) . . ?
N1 C19 H19C 107(3) . . ?
C17 N1 C1 106.7(3) . . ?
C17 N1 C18 108.3(4) . . ?
C18 N1 C1 111.7(3) . . ?
C19 N1 C1 111.1(3) . . ?
C19 N1 C17 109.3(4) . . ?
C19 N1 C18 109.7(3) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 171.5(5) . . . . ?
C2 C1 N1 C17 172.3(4) . . . . ?
C2 C1 N1 C18 -69.6(5) . . . . ?
C2 C1 N1 C19 53.3(5) . . . . ?
C2 C3 C4 C5 175.4(5) . . . . ?
C3 C4 C5 C6 171.5(5) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C5 C6 C7 C8 177.5(4) . . . . ?
C6 C7 C8 C9 -179.6(4) . . . . ?
C7 C8 C9 C10 178.8(5) . . . . ?
C8 C9 C10 C11 179.1(4) . . . . ?
C9 C10 C11 C12 179.1(4) . . . . ?
C10 C11 C12 C13 178.8(4) . . . . ?
C11 C12 C13 C14 -179.6(4) . . . . ?
C12 C13 C14 C15 179.8(5) . . . . ?
C13 C14 C15 C16 179.1(5) . . . . ?
N1 C1 C2 C3 164.9(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0100 -0.0000 0.0000 -0.9999 0.0259 -0.0010 0.0144
-3 -3 -2 0.2597 -3.0009 -2.9995 -2.0082 0.0226 -1.0378 0.1177
1 -1 -5 0.0980 0.9992 -1.0003 -4.9987 -0.0407 0.1106 0.3504
-1 1 5 0.0919 -0.9992 1.0003 4.9987 0.0407 -0.1106 -0.3504
0 0 1 0.0100 0.0000 -0.0000 0.9999 -0.0259 0.0010 -0.0144
3 3 1 0.2432 3.0009 2.9996 1.0083 0.0033 1.0368 -0.1033

_olex2_date_sample_data_collection 2014-04-22
_olex2_exptl_crystal_mounting_method 'Hamton Research nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_644
_database_code_depnum_ccdc_archive 'CCDC 1941225'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C14TAB
_chemical_name_systematic        'Tetradecyltrimethylammonium bromide'
_chemical_formula_moiety         'C17 H38 N, Br'
_chemical_formula_sum            'C17 H38 Br N'
_chemical_formula_weight         336.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H38 N Br'
_chemical_oxdiff_usercomment     C14TAB
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.63696(10)
_cell_length_b                   7.25318(13)
_cell_length_c                   47.4290(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.0732(17)
_cell_angle_gamma                90
_cell_volume                     1938.84(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10573
_cell_measurement_temperature    295
_cell_measurement_theta_max      73.0510
_cell_measurement_theta_min      3.7220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.791
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3531
_exptl_crystal_size_mid          0.1939
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            25108
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.301
_diffrn_reflns_theta_min         3.728
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega  -33.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -80.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega  -84.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -125.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00  101.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -94.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00  107.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -125.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00  121.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -125.0000 -150.0000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00  133.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -77.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 10 omega   79.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   45.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  108.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
 12 omega  118.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -120.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega  115.00  175.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
 14 omega  141.00  167.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  130.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   67.0000   71.5449 46

#__ type_ start__ end____ width___ exp.time_
 16 omega  106.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
 17 omega   79.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   47.0000   32.2153 97

#__ type_ start__ end____ width___ exp.time_
 18 omega   78.00  129.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 19 omega   77.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   74.00  134.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
 21 omega   74.00  100.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   73.00  142.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -60.0000 69

#__ type_ start__ end____ width___ exp.time_
 23 omega   75.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   67.0000   71.5449 37

#__ type_ start__ end____ width___ exp.time_
 24 omega   77.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 25 omega   77.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00   99.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   77.00  116.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
 28 omega   76.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   77.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00   99.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 31 omega   76.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   73.00  111.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   75.00  100.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   75.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   68.0000  -31.1929 103

#__ type_ start__ end____ width___ exp.time_
 35 omega   76.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   74.00  101.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 37 omega   77.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
 38 omega   77.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega   68.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651  164.0000 -165.0000 25

#__ type_ start__ end____ width___ exp.time_
 40 omega    3.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651   91.0000   82.5258 26

#__ type_ start__ end____ width___ exp.time_
 41 omega    2.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651   92.0000  168.2301 25

#__ type_ start__ end____ width___ exp.time_
 42 omega -113.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 43 omega -116.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000  -30.0000 103

#__ type_ start__ end____ width___ exp.time_
 44 omega    4.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651  -99.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 45 omega -115.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000 -180.0000 107

#__ type_ start__ end____ width___ exp.time_
 46 omega -118.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 47 omega -123.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -99.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 48 omega -123.00  -91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -99.0000  150.0000 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0343442000
_diffrn_orient_matrix_UB_12      0.0136523000
_diffrn_orient_matrix_UB_13      0.0320828000
_diffrn_orient_matrix_UB_21      0.1893856000
_diffrn_orient_matrix_UB_22      0.1528628000
_diffrn_orient_matrix_UB_23      0.0017585000
_diffrn_orient_matrix_UB_31      -0.1940501000
_diffrn_orient_matrix_UB_32      0.1468492000
_diffrn_orient_matrix_UB_33      -0.0048063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3019
_reflns_number_total             3835
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.930
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.205
_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)+(0.0416P)²+2.2478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1342
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B)
Uiso(H13A) = Uiso(H13B)
Uiso(H14A) = Uiso(H14B) = Uiso(H14C)
Uiso(H15C) = Uiso(H15B) = Uiso(H15A) = Uiso(H16A) = Uiso(H16B) = Uiso(H16C) =
Uiso(H17A) = Uiso(H17B) = Uiso(H17C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.715(7) 0.378(6) 0.0617(8) 0.045(7) Uiso 1 1 d . . . . .
H1B H 0.696(7) 0.164(6) 0.0591(8) 0.045(7) Uiso 1 1 d . . . . .
H2A H 1.006(8) 0.311(6) 0.0989(9) 0.059(9) Uiso 1 1 d . . . . .
H2B H 0.919(8) 0.082(6) 0.0985(8) 0.059(9) Uiso 1 1 d . . . . .
H3A H 0.655(9) 0.422(7) 0.1127(10) 0.073(10) Uiso 1 1 d . . . . .
H3B H 0.536(9) 0.218(7) 0.1081(10) 0.073(10) Uiso 1 1 d . . . . .
H4A H 0.866(9) 0.265(7) 0.1536(10) 0.074(10) Uiso 1 1 d . . . . .
H4B H 0.728(9) 0.088(7) 0.1473(10) 0.074(10) Uiso 1 1 d . . . . .
H5A H 0.524(8) 0.436(7) 0.1631(9) 0.064(9) Uiso 1 1 d . . . . .
H5B H 0.366(9) 0.272(6) 0.1560(10) 0.064(9) Uiso 1 1 d . . . . .
H6A H 0.691(8) 0.262(6) 0.2023(9) 0.058(8) Uiso 1 1 d . . . . .
H6B H 0.516(8) 0.097(7) 0.1936(9) 0.058(8) Uiso 1 1 d . . . . .
H7A H 0.363(7) 0.442(7) 0.2136(8) 0.060(9) Uiso 1 1 d . . . . .
H7B H 0.185(8) 0.287(6) 0.2041(9) 0.060(9) Uiso 1 1 d . . . . .
H8A H 0.503(8) 0.246(6) 0.2519(9) 0.057(8) Uiso 1 1 d . . . . .
H8B H 0.324(8) 0.096(6) 0.2415(9) 0.057(8) Uiso 1 1 d . . . . .
H9A H 0.167(8) 0.452(7) 0.2615(9) 0.061(9) Uiso 1 1 d . . . . .
H9B H -0.006(9) 0.290(6) 0.2528(9) 0.061(9) Uiso 1 1 d . . . . .
H10A H 0.307(8) 0.261(6) 0.2996(9) 0.061(9) Uiso 1 1 d . . . . .
H10B H 0.141(7) 0.088(7) 0.2904(8) 0.061(9) Uiso 1 1 d . . . . .
H11A H -0.007(8) 0.450(7) 0.3104(9) 0.066(9) Uiso 1 1 d . . . . .
H11B H -0.196(9) 0.294(6) 0.2998(9) 0.066(9) Uiso 1 1 d . . . . .
H12A H 0.133(9) 0.244(7) 0.3494(10) 0.074(10) Uiso 1 1 d . . . . .
H12B H -0.055(9) 0.092(7) 0.3379(10) 0.074(10) Uiso 1 1 d . . . . .
H13A H -0.206(9) 0.451(8) 0.3583(10) 0.079(11) Uiso 1 1 d . . . . .
H13B H -0.388(10) 0.291(7) 0.3494(11) 0.079(11) Uiso 1 1 d . . . . .
H14A H -0.058(11) 0.259(8) 0.3979(12) 0.091(10) Uiso 1 1 d . . . . .
H14B H -0.334(10) 0.294(8) 0.3983(12) 0.091(10) Uiso 1 1 d . . . . .
H14C H -0.242(10) 0.095(8) 0.3865(11) 0.091(10) Uiso 1 1 d . . . . .
H15A H 0.765(7) 0.361(6) 0.0137(8) 0.052(3) Uiso 1 1 d . . . . .
H15B H 0.783(7) 0.146(6) 0.0130(8) 0.052(3) Uiso 1 1 d . . . . .
H15C H 0.995(8) 0.262(5) 0.0004(9) 0.052(3) Uiso 1 1 d . . . . .
H16A H 1.238(7) 0.405(6) 0.0655(9) 0.052(3) Uiso 1 1 d . . . . .
H16B H 1.053(7) 0.521(6) 0.0459(8) 0.052(3) Uiso 1 1 d . . . . .
H16C H 1.262(7) 0.411(6) 0.0313(8) 0.052(3) Uiso 1 1 d . . . . .
H17A H 1.035(7) -0.031(6) 0.0445(8) 0.052(3) Uiso 1 1 d . . . . .
H17B H 1.239(7) 0.086(6) 0.0635(9) 0.052(3) Uiso 1 1 d . . . . .
H17C H 1.247(7) 0.075(6) 0.0300(8) 0.052(3) Uiso 1 1 d . . . . .
C1 C 0.7997(5) 0.2528(5) 0.06502(6) 0.0388(6) Uani 1 1 d . . . . .
C2 C 0.8772(6) 0.2223(5) 0.09529(7) 0.0440(7) Uani 1 1 d . . . . .
C3 C 0.6741(7) 0.2763(7) 0.11438(7) 0.0540(9) Uani 1 1 d . . . . .
C4 C 0.7115(7) 0.2289(7) 0.14520(7) 0.0542(9) Uani 1 1 d . . . . .
C5 C 0.5176(7) 0.2983(6) 0.16391(8) 0.0511(9) Uani 1 1 d . . . . .
C6 C 0.5319(7) 0.2312(6) 0.19406(7) 0.0511(8) Uani 1 1 d . . . . .
C7 C 0.3399(8) 0.3067(6) 0.21260(8) 0.0512(9) Uani 1 1 d . . . . .
C8 C 0.3428(7) 0.2319(6) 0.24246(8) 0.0517(8) Uani 1 1 d . . . . .
C9 C 0.1524(8) 0.3097(6) 0.26109(8) 0.0519(9) Uani 1 1 d . . . . .
C10 C 0.1533(7) 0.2289(6) 0.29061(7) 0.0504(8) Uani 1 1 d . . . . .
C11 C -0.0342(8) 0.3098(6) 0.30952(8) 0.0521(9) Uani 1 1 d . . . . .
C12 C -0.0343(8) 0.2293(6) 0.33911(8) 0.0548(9) Uani 1 1 d . . . . .
C13 C -0.2189(9) 0.3086(7) 0.35823(9) 0.0627(11) Uani 1 1 d . . . . .
C14 C -0.2141(14) 0.2277(10) 0.38740(11) 0.0925(19) Uani 1 1 d . . . . .
C15 C 0.8706(7) 0.2563(7) 0.01502(7) 0.0500(8) Uani 1 1 d . . . . .
C16 C 1.1524(7) 0.4159(5) 0.04609(8) 0.0468(8) Uani 1 1 d . . . . .
C17 C 1.1370(7) 0.0793(5) 0.04542(8) 0.0464(8) Uani 1 1 d . . . . .
N1 N 0.9922(4) 0.2508(4) 0.04331(5) 0.0352(5) Uani 1 1 d . . . . .
Br1 Br 0.61573(6) 0.75147(5) 0.03947(2) 0.05454(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 1.03(4) . ?
C1 H1B 0.91(4) . ?
C1 C2 1.509(4) . ?
C1 N1 1.510(4) . ?
C2 H2A 0.98(5) . ?
C2 H2B 1.06(4) . ?
C2 C3 1.524(5) . ?
C3 H3A 1.06(5) . ?
C3 H3B 0.93(5) . ?
C3 C4 1.512(5) . ?
C4 H4A 0.99(5) . ?
C4 H4B 1.03(5) . ?
C4 C5 1.507(5) . ?
C5 H5A 1.00(5) . ?
C5 H5B 0.94(5) . ?
C5 C6 1.511(5) . ?
C6 H6A 1.00(5) . ?
C6 H6B 0.98(5) . ?
C6 C7 1.510(5) . ?
C7 H7A 0.99(5) . ?
C7 H7B 0.96(5) . ?
C7 C8 1.516(5) . ?
C8 H8A 1.00(5) . ?
C8 H8B 0.99(5) . ?
C8 C9 1.512(5) . ?
C9 H9A 1.03(5) . ?
C9 H9B 0.98(5) . ?
C9 C10 1.518(5) . ?
C10 H10A 0.99(5) . ?
C10 H10B 1.02(5) . ?
C10 C11 1.517(5) . ?
C11 H11A 1.03(5) . ?
C11 H11B 1.02(5) . ?
C11 C12 1.520(5) . ?
C12 H12A 1.06(5) . ?
C12 H12B 1.00(5) . ?
C12 C13 1.507(6) . ?
C13 H13A 1.04(5) . ?
C13 H13B 1.04(5) . ?
C13 C14 1.503(7) . ?
C14 H14A 1.03(6) . ?
C14 H14B 0.98(6) . ?
C14 H14C 0.98(6) . ?
C15 H15A 0.97(4) . ?
C15 H15B 0.94(4) . ?
C15 H15C 1.00(4) . ?
C15 N1 1.496(4) . ?
C16 H16A 1.03(4) . ?
C16 H16B 0.95(4) . ?
C16 H16C 0.95(4) . ?
C16 N1 1.504(4) . ?
C17 H17A 0.98(4) . ?
C17 H17B 1.02(4) . ?
C17 H17C 0.97(4) . ?
C17 N1 1.490(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
_geom_angle_publ_flag
H1A C1 H1B 106(3) . . ?
C2 C1 H1A 113(2) . . ?
C2 C1 H1B 111(2) . . ?
C2 C1 N1 116.6(3) . . ?
N1 C1 H1A 104(2) . . ?
N1 C1 H1B 104(2) . . ?
H2A C2 H2B 116(3) . . ?
C1 C2 H2A 106(3) . . ?
C1 C2 H2B 110(2) . . ?
C1 C2 C3 108.7(3) . . ?
C3 C2 H2A 107(3) . . ?
C3 C2 H2B 109(2) . . ?
H3A C3 H3B 110(4) . . ?
C2 C3 H3A 107(3) . . ?
C2 C3 H3B 109(3) . . ?
C4 C3 H3A 108(3) . . ?
C4 C3 H3B 108(3) . . ?
C4 C3 C2 115.0(3) . . ?
H4A C4 H4B 99(4) . . ?
C3 C4 H4A 116(3) . . ?
C3 C4 H4B 109(3) . . ?
C5 C4 H4A 109(3) . . ?
C5 C4 H4B 110(3) . . ?
C5 C4 C3 113.8(3) . . ?
H5A C5 H5B 103(4) . . ?
C4 C5 H5A 106(3) . . ?
C4 C5 H5B 111(3) . . ?
C4 C5 C6 115.0(3) . . ?
C6 C5 H5A 111(3) . . ?
C6 C5 H5B 110(3) . . ?
H6A C6 H6B 108(4) . . ?
C5 C6 H6A 109(3) . . ?
C5 C6 H6B 107(2) . . ?
C7 C6 H6A 110(3) . . ?
C7 C6 H6B 108(3) . . ?
C7 C6 C5 114.1(3) . . ?
H7A C7 H7B 107(3) . . ?
C6 C7 H7A 107(2) . . ?
C6 C7 H7B 111(3) . . ?
C6 C7 C8 114.8(3) . . ?
C8 C7 H7A 108(2) . . ?
C8 C7 H7B 109(3) . . ?
H8A C8 H8B 103(3) . . ?
C7 C8 H8A 112(3) . . ?
C7 C8 H8B 108(2) . . ?
C9 C8 H8A 110(3) . . ?
C9 C8 H8B 109(3) . . ?
C9 C8 C7 114.6(3) . . ?
H9A C9 H9B 103(4) . . ?
C8 C9 H9A 109(3) . . ?
C8 C9 H9B 111(3) . . ?
C8 C9 C10 113.9(3) . . ?
C10 C9 H9A 112(2) . . ?
C10 C9 H9B 108(3) . . ?
H10A C10 H10B 107(3) . . ?
C9 C10 H10A 107(3) . . ?
C9 C10 H10B 112(2) . . ?
C11 C10 H10A 106(3) . . ?
C11 C10 H10B 110(2) . . ?
C11 C10 C9 113.9(3) . . ?
H11A C11 H11B 105(4) . . ?
C10 C11 H11A 108(3) . . ?
C10 C11 H11B 108(3) . . ?
C10 C11 C12 114.2(3) . . ?
C12 C11 H11A 110(2) . . ?
C12 C11 H11B 111(3) . . ?
H12A C12 H12B 103(4) . . ?
C11 C12 H12A 112(3) . . ?
C11 C12 H12B 109(3) . . ?
C13 C12 H12A 108(3) . . ?
C13 C12 H12B 109(3) . . ?
C13 C12 C11 114.9(4) . . ?
H13A C13 H13B 101(4) . . ?
C12 C13 H13A 109(3) . . ?
C12 C13 H13B 110(3) . . ?
C14 C13 H13A 113(3) . . ?
C14 C13 H13B 109(3) . . ?
C14 C13 C12 113.8(5) . . ?
H14A C14 H14B 103(4) . . ?
H14A C14 H14C 112(5) . . ?
H14B C14 H14C 113(5) . . ?
C13 C14 H14A 111(3) . . ?
C13 C14 H14B 107(4) . . ?
C13 C14 H14C 110(3) . . ?
H15A C15 H15B 110(3) . . ?
H15A C15 H15C 111(3) . . ?
H15B C15 H15C 110(3) . . ?
N1 C15 H15A 111(2) . . ?
N1 C15 H15B 107(2) . . ?
N1 C15 H15C 108(2) . . ?
H16A C16 H16B 110(3) . . ?
H16A C16 H16C 111(3) . . ?
H16B C16 H16C 115(3) . . ?
N1 C16 H16A 107(2) . . ?
N1 C16 H16B 107(3) . . ?
N1 C16 H16C 108(3) . . ?
H17A C17 H17B 113(3) . . ?
H17A C17 H17C 109(3) . . ?
H17B C17 H17C 106(3) . . ?
N1 C17 H17A 111(2) . . ?
N1 C17 H17B 108(2) . . ?
N1 C17 H17C 109(2) . . ?
C15 N1 C1 106.8(2) . . ?
C15 N1 C16 108.8(3) . . ?
C16 N1 C1 111.8(3) . . ?
C17 N1 C1 111.2(3) . . ?
C17 N1 C15 108.9(3) . . ?
C17 N1 C16 109.4(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 171.9(4) . . . . ?
C2 C1 N1 C15 172.0(3) . . . . ?
C2 C1 N1 C16 -69.2(4) . . . . ?
C2 C1 N1 C17 53.4(4) . . . . ?
C2 C3 C4 C5 175.1(4) . . . . ?
C3 C4 C5 C6 172.0(4) . . . . ?
C4 C5 C6 C7 178.4(4) . . . . ?
C5 C6 C7 C8 176.5(4) . . . . ?
C6 C7 C8 C9 179.2(4) . . . . ?
C7 C8 C9 C10 178.2(4) . . . . ?
C8 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 180.0(4) . . . . ?
C10 C11 C12 C13 179.8(4) . . . . ?
C11 C12 C13 C14 -179.6(5) . . . . ?
N1 C1 C2 C3 166.0(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 0 0 0.0684 -3.6581 0.1146 0.2959 0.1367 -0.6748 0.7253
0 0 -1 0.0100 0.0000 0.0001 -1.0000 -0.0321 -0.0017 0.0048
0 0 1 0.0100 -0.0000 -0.0001 1.0000 0.0321 0.0017 -0.0048
0 -5 6 0.1104 0.2362 -4.5950 6.3621 0.1333 -0.6465 -0.7512
3 3 -5 0.0574 2.6106 3.2302 -4.8180 -0.2001 0.9797 -0.0091

_olex2_date_sample_data_collection 2014-07-11
_olex2_exptl_crystal_mounting_method 'Hampton Research cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0483d
_database_code_depnum_ccdc_archive 'CCDC 1941232'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C10TAB
_chemical_name_systematic        'Decyltrimethylammonium bromide'
_chemical_formula_moiety         'C13 H30 N, Br'
_chemical_formula_sum            'C13 H30 Br N'
_chemical_formula_weight         280.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H30 Br N'
_chemical_oxdiff_usercomment     'From acetone solution (cooled in ice)'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.62642(7)
_cell_length_b                   7.20481(8)
_cell_length_c                   19.3396(2)
_cell_angle_alpha                90
_cell_angle_beta                 83.4072(11)
_cell_angle_gamma                90
_cell_volume                     778.792(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    250
_cell_measurement_theta_max      73.4700
_cell_measurement_theta_min      4.5910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.380
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.3595
_exptl_crystal_size_mid          0.2503
_exptl_crystal_size_min          0.0426
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12138
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.919
_diffrn_reflns_theta_min         4.603
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000  -60.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   57.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   91.0000   40.4724 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -125.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -45.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
  7 omega   73.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   49.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -45.0000 -180.0000 62

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000  -60.0000 108

#__ type_ start__ end____ width___ exp.time_
 12 omega  121.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   56.0000 -102.2695 41

#__ type_ start__ end____ width___ exp.time_
 13 omega  128.00  154.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  110.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega  118.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega  105.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -57.8876 40

#__ type_ start__ end____ width___ exp.time_
 17 omega   97.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -112.1681 43

#__ type_ start__ end____ width___ exp.time_
 18 omega   80.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   72.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   56.0000 -102.2695 30

#__ type_ start__ end____ width___ exp.time_
 20 omega   78.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 21 omega   79.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 22 omega   79.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 23 omega   78.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
 24 omega   92.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 80

#__ type_ start__ end____ width___ exp.time_
 25 omega   74.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
 26 omega   75.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 27 omega   77.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   72.0000  139.6396 100

#__ type_ start__ end____ width___ exp.time_
 28 omega   72.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  166.9330 65

#__ type_ start__ end____ width___ exp.time_
 29 omega   51.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   69.0000   54.1021 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
 31 omega   74.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 32 omega   74.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
 33 omega   75.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   74.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
 35 omega   56.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   70.0000 -177.0932 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -112.1681 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   38.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000  -57.8876 31

#__ type_ start__ end____ width___ exp.time_
 38 omega   36.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   65.0000    4.6820 31

#__ type_ start__ end____ width___ exp.time_
 39 omega   47.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   72.0000   13.3722 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   26.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000   72.0771 26

#__ type_ start__ end____ width___ exp.time_
 41 omega   48.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   65.0000   97.3050 35

#__ type_ start__ end____ width___ exp.time_
 42 omega   42.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000  132.6206 38

#__ type_ start__ end____ width___ exp.time_
 43 omega   32.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  166.9330 28

#__ type_ start__ end____ width___ exp.time_
 44 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  139.5629 25

#__ type_ start__ end____ width___ exp.time_
 45 omega    7.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   86.0000   68.1965 26

#__ type_ start__ end____ width___ exp.time_
 46 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   81.0000  -23.2511 25

#__ type_ start__ end____ width___ exp.time_
 47 omega   16.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  -74.0489 28

#__ type_ start__ end____ width___ exp.time_
 48 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000 -113.7073 26

#__ type_ start__ end____ width___ exp.time_
 49 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000 -152.6192 25

#__ type_ start__ end____ width___ exp.time_
 50 omega -107.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
 51 omega -112.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -120.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1263782000
_diffrn_orient_matrix_UB_12      -0.1460076000
_diffrn_orient_matrix_UB_13      -0.0494977000
_diffrn_orient_matrix_UB_21      -0.1739363000
_diffrn_orient_matrix_UB_22      0.0428336000
_diffrn_orient_matrix_UB_23      -0.0539121000
_diffrn_orient_matrix_UB_31      0.1725124000
_diffrn_orient_matrix_UB_32      0.1502066000
_diffrn_orient_matrix_UB_33      -0.0327530000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1631
_reflns_number_total             1673
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1673
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.5296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10M = C10-H10_$1
 0.96 with sigma of 0.005
 C11-H11 = C11-H11M = C11-H11_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1 = H10-H10M
 1.565 with sigma of 0.005
 H11-H11_$1 = H11-H11M
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10M \\sim C9-H10_$1
 with sigma of 0.005
 N1-H11 \\sim N1-H11M \\sim N1-H11_$1
 with sigma of 0.005
 H10-H10M \\sim H10M-H10_$1 \\sim H10_$1-H10
 with sigma of 0.005
 H11-H11M \\sim H11M-H11_$1 \\sim H11_$1-H11
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7315(5) 0.2500 0.16189(16) 0.0387(6) Uani 1 2 d DS T P . .
H1 H 0.6364(13) 0.3587(4) 0.1542(2) 0.046 Uiso 1 1 d DR . . . .
C2 C 0.7811(7) 0.2500 0.2367(2) 0.0607(10) Uani 1 2 d DS T P . .
H2 H 0.8768(14) 0.3586(4) 0.2446(3) 0.073 Uiso 1 1 d DR . . . .
C3 C 0.5571(8) 0.2500 0.2849(2) 0.0683(12) Uani 1 2 d DS T P . .
H3 H 0.4659(14) 0.3585(4) 0.2742(3) 0.082 Uiso 1 1 d DR . . . .
C4 C 0.5704(8) 0.2500 0.3608(2) 0.0673(12) Uani 1 2 d DS T P . .
H4 H 0.6639(14) 0.3586(4) 0.3699(3) 0.081 Uiso 1 1 d DR . . . .
C5 C 0.3549(10) 0.2500 0.4086(2) 0.115(3) Uani 1 2 d DS T P . .
H5 H 0.2648(15) 0.3585(4) 0.3973(3) 0.139 Uiso 1 1 d DR . . . .
C6 C 0.3487(9) 0.2500 0.4834(2) 0.0692(12) Uani 1 2 d DS T P . .
H6 H 0.4397(14) 0.3585(4) 0.4942(3) 0.083 Uiso 1 1 d DR . . . .
C7 C 0.1357(12) 0.2500 0.5308(3) 0.153(5) Uani 1 2 d DS T P . .
H7 H 0.0469(16) 0.3585(4) 0.5188(3) 0.184 Uiso 1 1 d DR . . . .
C8 C 0.1203(11) 0.2500 0.6047(2) 0.0800(15) Uani 1 2 d DS T P . .
H8 H 0.2103(16) 0.3585(4) 0.6162(4) 0.096 Uiso 1 1 d DR . . . .
C9 C -0.0889(14) 0.2500 0.6529(3) 0.176(5) Uani 1 2 d DS T P . .
H9 H -0.1761(18) 0.3586(4) 0.6402(4) 0.211 Uiso 1 1 d DR . . . .
C10 C -0.1086(16) 0.2500 0.7251(3) 0.125(3) Uani 1 2 d DS T P . .
H10 H -0.032(2) 0.3586(3) 0.7411(6) 0.187 Uiso 1 1 d DR . . . .
H10M H -0.274(2) 0.2500 0.7436(8) 0.187 Uiso 1 2 d DRS T P . .
C11 C 0.8505(6) 0.2500 0.03785(16) 0.0463(7) Uani 1 2 d DS T P . .
H11 H 0.7545(12) 0.3587(3) 0.0339(6) 0.070 Uiso 1 1 d DR . . . .
H11M H 0.9812(17) 0.2500 0.0013(5) 0.070 Uiso 1 2 d DRS T P . .
C12 C 1.0968(4) 0.4193(3) 0.11255(13) 0.0450(5) Uani 1 1 d . . . . .
H12A H 1.1619 0.4187 0.1563 0.067 Uiso 1 1 calc GR . . . .
H12B H 1.0000 0.5281 0.1095 0.067 Uiso 1 1 calc GR . . . .
H12C H 1.2250 0.4198 0.0752 0.067 Uiso 1 1 calc GR . . . .
N1 N 0.9466(4) 0.2500 0.10722(13) 0.0347(5) Uani 1 2 d DS T P . .
Br1 Br 0.57381(5) 0.7500 0.09618(2) 0.04870(17) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.970(4) . ?
C1 C2 1.505(5) . ?
C1 N1 1.513(4) . ?
C2 H2 0.971(4) . ?
C2 C3 1.479(5) . ?
C3 H3 0.971(4) . ?
C3 C4 1.478(6) . ?
C4 H4 0.970(4) . ?
C4 C5 1.438(6) . ?
C5 H5 0.971(4) . ?
C5 C6 1.442(6) . ?
C6 H6 0.971(4) . ?
C6 C7 1.424(7) . ?
C7 H7 0.970(4) . ?
C7 C8 1.420(7) . ?
C8 H8 0.971(4) . ?
C8 C9 1.415(8) . ?
C9 H9 0.970(4) . ?
C9 C10 1.389(9) . ?
C10 H10 0.960(4) . ?
C10 H10M 0.959(5) . ?
C11 H11 0.959(4) . ?
C11 H11M 0.960(5) . ?
C11 N1 1.503(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N1 1.494(3) . ?
N1 C12 1.494(3) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 108.3(3) . . ?
C2 C1 N1 116.7(3) . . ?
N1 C1 H1 107.7(4) . . ?
C1 C2 H2 108.5(4) . . ?
C3 C2 C1 111.5(3) . . ?
C3 C2 H2 110.5(4) . . ?
C2 C3 H3 107.4(4) . . ?
C2 C3 C4 119.3(4) . . ?
C4 C3 H3 107.5(4) . . ?
C3 C4 H4 105.7(4) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 108.6(4) . . ?
C4 C5 H5 106.2(4) . . ?
C4 C5 C6 124.5(5) . . ?
C6 C5 H5 105.9(4) . . ?
C5 C6 H6 105.3(5) . . ?
C7 C6 C5 124.6(5) . . ?
C7 C6 H6 106.6(4) . . ?
C6 C7 H7 105.3(5) . . ?
C8 C7 C6 126.7(6) . . ?
C8 C7 H7 105.5(5) . . ?
C7 C8 H8 105.0(5) . . ?
C9 C8 C7 127.8(7) . . ?
C9 C8 H8 105.3(5) . . ?
C8 C9 H9 103.9(6) . . ?
C10 C9 C8 128.8(8) . . ?
C10 C9 H9 105.7(5) . . ?
C9 C10 H10 109.6(7) . . ?
C9 C10 H10M 109.7(7) . . ?
H10 C10 H10M 109.3(7) . . ?
H11 C11 H11M 109.4(6) . . ?
N1 C11 H11 109.6(6) . . ?
N1 C11 H11M 109.5(7) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
C11 N1 C1 106.4(2) . . ?
C12 N1 C1 111.42(15) . . ?
C12 N1 C1 111.42(15) 4_565 . ?
C12 N1 C11 109.02(16) . . ?
C12 N1 C11 109.02(16) 4_565 . ?
C12 N1 C12 109.4(2) 4_565 . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C1 N1 C11 180.000(0) . . . . ?
C2 C1 N1 C12 -61.27(16) . . . . ?
C2 C1 N1 C12 61.28(17) . . . 4_565 ?
C2 C3 C4 C5 180.000(1) . . . . ?
C3 C4 C5 C6 180.000(1) . . . . ?
C4 C5 C6 C7 180.000(2) . . . . ?
C5 C6 C7 C8 180.000(2) . . . . ?
C6 C7 C8 C9 180.000(3) . . . . ?
C7 C8 C9 C10 180.000(4) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0213 -0.0008 -0.0003 -0.9994 0.0494 0.0540 0.0326
0 0 1 0.0213 0.0008 0.0003 0.9994 -0.0494 -0.0540 -0.0326
1 -4 1 0.1144 1.3376 -4.3421 1.3161 0.7379 -0.4896 -0.4646
2 4 -4 0.0897 1.6808 3.7412 -4.1386 -0.1290 0.0910 0.9875
-3 0 3 0.0932 -3.3737 0.4165 3.3154 -0.6513 0.4259 -0.6280
3 -1 -3 0.1903 3.3340 -1.1040 -2.8404 0.7231 -0.4741 0.5024
-2 -4 4 0.1504 -1.7794 -3.6497 4.1855 0.1008 -0.0725 -0.9923
-2 4 0 0.1264 -2.2111 3.7080 0.0096 -0.8213 0.5429 0.1752

_olex2_date_sample_data_collection 2015-08-26
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0370
_database_code_depnum_ccdc_archive 'CCDC 1941223'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C16TAB
_chemical_name_systematic        'Hexadecyltrimethylammonium bromide'
_chemical_formula_moiety         'C19 H42 N, Br'
_chemical_formula_sum            'C19 H42 Br N'
_chemical_formula_weight         364.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 N Br H42'
_chemical_oxdiff_usercomment     C16TAB
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.66305(12)
_cell_length_b                   7.38058(17)
_cell_length_c                   26.2866(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.711(2)
_cell_angle_gamma                90
_cell_volume                     1098.60(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9077
_cell_measurement_temperature    380
_cell_measurement_theta_max      73.1690
_cell_measurement_theta_min      5.0310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.496
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2982
_exptl_crystal_size_mid          0.1808
_exptl_crystal_size_min          0.0503
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15422
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.362
_diffrn_reflns_theta_min         3.363
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      380
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega  -43.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -55.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega  -81.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651  -99.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -94.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   83.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -94.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   88.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -125.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -125.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   29.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -77.0000  -90.0000 110

#__ type_ start__ end____ width___ exp.time_
 12 omega   76.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
 13 omega  130.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega  115.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   70.0000    4.7202 62

#__ type_ start__ end____ width___ exp.time_
 15 omega  151.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -23.0460 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  121.00  152.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega   94.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  125.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 19 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   78.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 21 omega   77.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   73.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 24 omega   76.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 25 omega   74.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
 27 omega   76.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
 28 omega   77.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 29 omega   79.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   45.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   74.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega   73.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   60.0000 71

#__ type_ start__ end____ width___ exp.time_
 34 omega   73.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 35 omega   73.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -23.0460 29

#__ type_ start__ end____ width___ exp.time_
 36 omega   77.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   70.0000    4.7202 30

#__ type_ start__ end____ width___ exp.time_
 38 omega   76.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
 39 omega   75.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   74.0000  -63.0741 27

#__ type_ start__ end____ width___ exp.time_
 40 omega   23.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651 -125.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
 41 omega -103.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -19.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 42 omega -116.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
 43 omega -113.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega -120.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -90.0000 107

#__ type_ start__ end____ width___ exp.time_
 45 omega -120.00  -85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -99.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
 46 omega -120.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   60.0000 36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1243571000
_diffrn_orient_matrix_UB_12      0.1163906000
_diffrn_orient_matrix_UB_13      -0.0402642000
_diffrn_orient_matrix_UB_21      0.1881924000
_diffrn_orient_matrix_UB_22      0.0555446000
_diffrn_orient_matrix_UB_23      0.0398424000
_diffrn_orient_matrix_UB_31      0.1520240000
_diffrn_orient_matrix_UB_32      -0.1640949000
_diffrn_orient_matrix_UB_33      -0.0151151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2167
_reflns_number_total             2359
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+0.2390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1261
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10_$1
 0.97 with sigma of 0.005
 C11-H11 = C11-H11_$1
 0.97 with sigma of 0.005
 C12-H12 = C12-H12_$1
 0.97 with sigma of 0.005
 C13-H13 = C13-H13_$1
 0.97 with sigma of 0.005
 C14-H14 = C14-H14_$1
 0.97 with sigma of 0.005
 C15-H15 = C15-H15_$1
 0.97 with sigma of 0.005
 C16-H16 = C16-H16M = C16-H16_$1
 0.96 with sigma of 0.005
 C17-H17 = C17-H17M = C17-H17_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1
 1.565 with sigma of 0.005
 H11-H11_$1
 1.565 with sigma of 0.005
 H12-H12_$1
 1.565 with sigma of 0.005
 H13-H13_$1
 1.565 with sigma of 0.005
 H14-H14_$1
 1.565 with sigma of 0.005
 H15-H15_$1
 1.565 with sigma of 0.005
 H16-H16_$1 = H16-H16M
 1.565 with sigma of 0.005
 H17-H17_$1 = H17-H17M
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10 \\sim C11-H10 \\sim C11-H10_$1
 with sigma of 0.005
 C10-H11 \\sim C10-H11_$1 \\sim C12-H11 \\sim C12-H11_$1
 with sigma of 0.005
 C11-H12 \\sim C11-H12_$1 \\sim C13-H12 \\sim C13-H12_$1
 with sigma of 0.005
 C12-H13 \\sim C12-H13_$1 \\sim C14-H13 \\sim C14-H13_$1
 with sigma of 0.005
 C13-H14 \\sim C13-H14_$1 \\sim C15-H14 \\sim C15-H14_$1
 with sigma of 0.005
 C14-H15 \\sim C14-H15_$1 \\sim C16-H15 \\sim C16-H15_$1
 with sigma of 0.005
 C15-H16 \\sim C15-H16M \\sim C15-H16_$1
 with sigma of 0.005
 N1-H17 \\sim N1-H17M \\sim N1-H17_$1
 with sigma of 0.005
 H16-H16M \\sim H16M-H16_$1 \\sim H16_$1-H16
 with sigma of 0.005
 H17-H17M \\sim H17M-H17_$1 \\sim H17_$1-H17
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8099(6) 0.2500 0.11872(14) 0.0729(8) Uani 1 2 d DS T P . .
H1 H 0.7124(13) 0.3561(3) 0.11271(18) 0.087 Uiso 1 1 d DR . . . .
C2 C 0.8922(8) 0.2500 0.17217(17) 0.0998(13) Uani 1 2 d DS T P . .
H2 H 0.9894(15) 0.3561(4) 0.1782(2) 0.120 Uiso 1 1 d DR . . . .
C3 C 0.6962(10) 0.2500 0.20884(18) 0.1085(15) Uani 1 2 d DS T P . .
H3 H 0.6013(15) 0.3560(4) 0.2009(2) 0.130 Uiso 1 1 d DR . . . .
C4 C 0.7438(11) 0.2500 0.2634(2) 0.1223(19) Uani 1 2 d DS T P . .
H4 H 0.8400(16) 0.3560(4) 0.2705(3) 0.147 Uiso 1 1 d DR . . . .
C5 C 0.5541(12) 0.2500 0.3000(2) 0.136(2) Uani 1 2 d DS T P . .
H5 H 0.4607(17) 0.3560(4) 0.2913(3) 0.163 Uiso 1 1 d DR . . . .
C6 C 0.5868(12) 0.2500 0.3533(2) 0.127(2) Uani 1 2 d DS T P . .
H6 H 0.6808(17) 0.3560(4) 0.3616(3) 0.153 Uiso 1 1 d DR . . . .
C7 C 0.4000(13) 0.2500 0.3898(2) 0.151(3) Uani 1 2 d DS T P . .
H7 H 0.3084(18) 0.3560(4) 0.3804(3) 0.182 Uiso 1 1 d DR . . . .
C8 C 0.4185(13) 0.2500 0.4424(2) 0.135(2) Uani 1 2 d DS T P . .
H8 H 0.5110(18) 0.3560(4) 0.4515(3) 0.162 Uiso 1 1 d DR . . . .
C9 C 0.2347(14) 0.2500 0.4790(3) 0.164(3) Uani 1 2 d DS T P . .
H9 H 0.1425(19) 0.3560(4) 0.4698(3) 0.196 Uiso 1 1 d DR . . . .
C10 C 0.2507(14) 0.2500 0.5316(2) 0.140(2) Uani 1 2 d DS T P . .
H10 H 0.3435(18) 0.3560(4) 0.5404(3) 0.168 Uiso 1 1 d DR . . . .
C11 C 0.0708(14) 0.2500 0.5686(2) 0.173(4) Uani 1 2 d DS T P . .
H11 H -0.0211(19) 0.3560(4) 0.5593(3) 0.208 Uiso 1 1 d DR . . . .
C12 C 0.0847(15) 0.2500 0.6205(3) 0.141(2) Uani 1 2 d DS T P . .
H12 H 0.1772(19) 0.3560(4) 0.6296(3) 0.170 Uiso 1 1 d DR . . . .
C13 C -0.0924(17) 0.2500 0.6577(3) 0.194(5) Uani 1 2 d DS T P . .
H13 H -0.185(2) 0.3560(4) 0.6486(3) 0.233 Uiso 1 1 d DR . . . .
C14 C -0.0783(16) 0.2500 0.7095(3) 0.152(3) Uani 1 2 d DS T P . .
H14 H 0.015(2) 0.3560(4) 0.7185(4) 0.182 Uiso 1 1 d DR . . . .
C15 C -0.252(2) 0.2500 0.7479(3) 0.238(6) Uani 1 2 d DS T P . .
H15 H -0.342(2) 0.3560(4) 0.7379(4) 0.286 Uiso 1 1 d DR . . . .
C16 C -0.239(2) 0.2500 0.7980(3) 0.210(5) Uani 1 2 d DS T P . .
H16 H -0.156(3) 0.3560(3) 0.8096(5) 0.315 Uiso 1 1 d DR . . . .
H16M H -0.395(3) 0.2500 0.8118(7) 0.315 Uiso 1 2 d DRS T P . .
C17 C 0.8649(7) 0.2500 0.02838(14) 0.0849(10) Uani 1 2 d DS T P . .
H17 H 0.7678(13) 0.3561(3) 0.0260(4) 0.127 Uiso 1 1 d DR . . . .
H17M H 0.9761(19) 0.2500 0.0010(4) 0.127 Uiso 1 2 d DRS T P . .
C18 C 1.1468(4) 0.4149(4) 0.08078(11) 0.0812(7) Uani 1 1 d . . . . .
H18A H 1.0493 0.5212 0.0788 0.122 Uiso 1 1 calc GR . . . .
H18B H 1.2554 0.4147 0.0530 0.122 Uiso 1 1 calc GR . . . .
H18C H 1.2333 0.4151 0.1124 0.122 Uiso 1 1 calc GR . . . .
N1 N 0.9949(4) 0.2500 0.07784(10) 0.0622(6) Uani 1 2 d DS T P . .
Br1 Br 0.62017(6) 0.7500 0.07066(2) 0.0843(2) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.970(4) . ?
C1 C2 1.475(6) . ?
C1 N1 1.510(4) . ?
C2 H2 0.969(4) . ?
C2 C3 1.479(7) . ?
C3 H3 0.970(4) . ?
C3 C4 1.456(8) . ?
C4 H4 0.970(4) . ?
C4 C5 1.451(8) . ?
C5 H5 0.970(4) . ?
C5 C6 1.412(9) . ?
C6 H6 0.970(4) . ?
C6 C7 1.437(9) . ?
C7 H7 0.969(4) . ?
C7 C8 1.385(9) . ?
C8 H8 0.970(4) . ?
C8 C9 1.426(9) . ?
C9 H9 0.970(4) . ?
C9 C10 1.384(10) . ?
C10 H10 0.969(4) . ?
C10 C11 1.418(9) . ?
C11 H11 0.970(4) . ?
C11 C12 1.366(10) . ?
C12 H12 0.970(4) . ?
C12 C13 1.409(10) . ?
C13 H13 0.970(4) . ?
C13 C14 1.363(11) . ?
C14 H14 0.970(4) . ?
C14 C15 1.415(11) . ?
C15 H15 0.970(4) . ?
C15 C16 1.319(13) . ?
C16 H16 0.960(4) . ?
C16 H16M 0.960(5) . ?
C17 H17 0.958(4) . ?
C17 H17M 0.961(5) . ?
C17 N1 1.486(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 N1 1.492(3) . ?
N1 C18 1.492(3) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 109.1(4) . . ?
C2 C1 N1 117.7(3) . . ?
N1 C1 H1 106.4(4) . . ?
C1 C2 H2 109.1(5) . . ?
C1 C2 C3 113.0(4) . . ?
C3 C2 H2 108.8(5) . . ?
C2 C3 H3 106.2(5) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 107.8(5) . . ?
C3 C4 H4 106.6(5) . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 H4 107.0(5) . . ?
C4 C5 H5 104.5(5) . . ?
C6 C5 C4 124.7(6) . . ?
C6 C5 H5 107.3(5) . . ?
C5 C6 H6 106.7(6) . . ?
C5 C6 C7 125.1(6) . . ?
C7 C6 H6 104.9(6) . . ?
C6 C7 H7 103.0(6) . . ?
C8 C7 C6 128.3(7) . . ?
C8 C7 H7 106.8(6) . . ?
C7 C8 H8 106.3(6) . . ?
C7 C8 C9 128.8(7) . . ?
C9 C8 H8 103.3(6) . . ?
C8 C9 H9 103.1(6) . . ?
C10 C9 C8 129.4(8) . . ?
C10 C9 H9 106.1(6) . . ?
C9 C10 H10 105.6(6) . . ?
C9 C10 C11 130.3(8) . . ?
C11 C10 H10 103.1(6) . . ?
C10 C11 H11 102.4(6) . . ?
C12 C11 C10 130.8(8) . . ?
C12 C11 H11 106.1(6) . . ?
C11 C12 H12 105.6(6) . . ?
C11 C12 C13 131.4(9) . . ?
C13 C12 H12 102.5(6) . . ?
C12 C13 H13 102.4(7) . . ?
C14 C13 C12 131.3(10) . . ?
C14 C13 H13 105.7(6) . . ?
C13 C14 H14 105.5(7) . . ?
C13 C14 C15 132.8(10) . . ?
C15 C14 H14 101.9(7) . . ?
C14 C15 H15 100.2(8) . . ?
C16 C15 C14 133.0(12) . . ?
C16 C15 H15 107.0(7) . . ?
C15 C16 H16 109.7(7) . . ?
C15 C16 H16M 109.7(7) . . ?
H16 C16 H16M 109.3(7) . . ?
H17 C17 H17M 109.3(7) . . ?
N1 C17 H17 109.6(6) . . ?
N1 C17 H17M 109.4(7) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
C17 N1 C1 106.4(2) . . ?
C17 N1 C18 108.92(18) . . ?
C17 N1 C18 108.92(18) . 4_565 ?
C18 N1 C1 111.57(17) . . ?
C18 N1 C1 111.57(17) 4_565 . ?
C18 N1 C18 109.4(3) 4_565 . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C1 N1 C17 180.000(0) . . . . ?
C2 C1 N1 C18 61.34(18) . . . 4_565 ?
C2 C1 N1 C18 -61.34(18) . . . . ?
C2 C3 C4 C5 180.000(2) . . . . ?
C3 C4 C5 C6 180.000(2) . . . . ?
C4 C5 C6 C7 180.000(3) . . . . ?
C5 C6 C7 C8 180.000(3) . . . . ?
C6 C7 C8 C9 180.000(4) . . . . ?
C7 C8 C9 C10 180.000(5) . . . . ?
C8 C9 C10 C11 180.000(5) . . . . ?
C9 C10 C11 C12 180.000(6) . . . . ?
C10 C11 C12 C13 180.000(7) . . . . ?
C11 C12 C13 C14 180.000(7) . . . . ?
C12 C13 C14 C15 180.000(10) . . . . ?
C13 C14 C15 C16 180.000(11) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 0 0.0493 -0.0006 0.0006 -0.4998 0.0201 -0.0200 0.0074
0 0 0 0.0010 0.0006 -0.0006 0.4998 -0.0201 0.0200 -0.0074
0 5 4 0.0945 0.2339 4.6587 3.8145 0.4177 0.4548 -0.7866
4 0 -2 0.1129 3.6389 -0.2511 -2.4648 0.5225 0.5727 0.6317
3 3 1 0.1164 2.9313 2.8845 0.6377 0.6746 0.7373 -0.0373
-3 -2 0 0.0596 -3.2510 -2.2390 0.1086 -0.6693 -0.7318 -0.1285
2 -4 -5 0.1266 1.8549 -3.9466 -4.5016 -0.0474 -0.0495 0.9976

_olex2_date_sample_data_collection 2015-02-13
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0624
_database_code_depnum_ccdc_archive 'CCDC 1941227'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C14TAB-D29
_chemical_name_systematic        'Tetradecyltrimethylammonium bromide-d29'
_chemical_formula_moiety         'C17 H9 D29 N, Br'
_chemical_formula_sum            'C17 H9 Br D29 N'
_chemical_formula_weight         365.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 D38 Br N'
_chemical_oxdiff_usercomment     'Deuterated C14TAB'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.59767(14)
_cell_length_b                   7.1390(2)
_cell_length_c                   47.0946(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.401(2)
_cell_angle_gamma                90
_cell_volume                     1880.33(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11768
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.1180
_cell_measurement_theta_min      3.7520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.877
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0040
0 0 -1 0.0040
-4 0 4 0.0588
0 -5 -6 0.0669
-3 3 7 0.0576
3 -3 -7 0.0539
3 2 0 0.0410
1 4 4 0.0466

_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.129
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.008
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 0.0000 1.0000 -0.0146 0.0285 -0.0070
0.0001 -0.0000 -1.0000 0.0146 -0.0285 0.0070
-4.0008 -0.0008 3.9938 -0.8034 -0.4615 -0.6008
-0.0021 -4.9977 -6.0060 -0.5218 -0.2641 0.9271
-2.6200 3.0694 7.1378 -0.2180 -0.1164 -0.9690
2.8159 -2.7838 -6.9903 0.2871 0.1541 0.9454
3.0810 2.4546 -0.3735 0.8784 0.4779 0.0091
1.1848 4.3218 4.3239 0.6843 0.3737 -0.6262

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            28898
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.465
_diffrn_reflns_theta_min         3.758
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -18.00   1.00    4.00    --  -42.62 -38.00-120.00   27
  2  ω    -72.00 -10.00   1.00    4.00    --  -42.62 -77.00 -60.00   62
  3  ω    -50.00 -16.00   1.00    4.00    --  -42.62 -77.00   0.00   34
  4  ω    -51.00 -10.00   1.00    4.00    --  -42.62 -77.00  60.00   41
  5  ω      4.00  69.00   1.00    4.00    --   42.62 -99.00 -90.00   65
  6  ω     72.00 109.00   1.00   12.00    --  112.00 -94.00   0.00   37
  7  ω     70.00 111.00   1.00   12.00    --  112.00-111.00 -90.00   41
  8  ω     95.00 140.00   1.00   12.00    --  112.00 -61.00-120.00   45
  9  ω     86.00 112.00   1.00   12.00    --  112.00  45.00 -60.00   26
 10  ω    123.00 176.00   1.00   12.00    --  112.00  61.00 -90.00   53
 11  ω    153.00 178.00   1.00   12.00    --  112.00  61.00 -30.00   25
 12  ω    145.00 172.00   1.00   12.00    --  112.00  61.00   0.00   27
 13  ω    121.00 154.00   1.00   12.00    --  112.00  69.00 -76.79   33
 14  ω    115.00 178.00   1.00   12.00    --  112.00  77.00 -60.00   63
 15  ω    144.00 174.00   1.00   12.00    --  112.00  61.00-180.00   30
 16  ω     83.00 138.00   1.00   12.00    --  112.00  61.00   0.00   55
 17  ω    123.00 177.00   1.00   12.00    --  112.00  77.00  90.00   54
 18  ω     86.00 112.00   1.00   12.00    --  112.00  45.00 -30.00   26
 19  ω     79.00 106.00   1.00   12.00    --  112.00  77.00   0.00   27
 20  ω     81.00 145.00   1.00   12.00    --  112.00  77.00 -30.00   64
 21  ω     85.00 154.00   1.00   12.00    --  112.00  50.00-119.12   69
 22  ω     83.00 109.00   1.00   12.00    --  112.00  61.00 -90.00   26
 23  ω     83.00 109.00   1.00   12.00    --  112.00  61.00-120.00   26
 24  ω     83.00 177.00   1.00   12.00    --  112.00  61.00-150.00   94
 25  ω     80.00 105.00   1.00   12.00    --  112.00  77.00-150.00   25
 26  ω     83.00 113.00   1.00   12.00    --  112.00  61.00-180.00   30
 27  ω     79.00 127.00   1.00   12.00    --  112.00  77.00-180.00   48
 28  ω     79.00 178.00   1.00   12.00    --  112.00  77.00-120.00   99
 29  ω     79.00 105.00   1.00   12.00    --  112.00  77.00 -60.00   26
 30  ω     83.00 109.00   1.00   12.00    --  112.00  61.00 -30.00   26
 31  ω     81.00 107.00   1.00   12.00    --  112.00  69.00 -76.79   26
 32  ω     79.00 105.00   1.00   12.00    --  112.00  77.00  30.00   26
 33  ω     83.00 109.00   1.00   12.00    --  112.00  61.00  60.00   26
 34  ω     83.00 143.00   1.00   12.00    --  112.00  61.00  90.00   60
 35  ω     83.00 177.00   1.00   12.00    --  112.00  61.00 120.00   94
 36  ω     79.00 105.00   1.00   12.00    --  112.00  77.00  90.00   26
 37  ω     79.00 105.00   1.00   12.00    --  112.00  77.00 120.00   26
 38  ω     83.00 174.00   1.00   12.00    --  112.00  61.00 150.00   91
 39  ω     80.00 177.00   1.00   12.00    --  112.00  77.00  60.00   97
 40  ω     79.00 105.00   1.00   12.00    --  112.00  77.00 150.00   26
 41  ω     80.00 146.00   1.00   12.00    --  112.00  75.00  54.03   66
 42  ω     83.00 175.00   1.00   12.00    --  112.00  61.00  30.00   92
 43  ω     63.00  92.00   1.00   12.00    --  112.00 -61.00-120.00   29
 44  ω     61.00 109.00   1.00   12.00    --  112.00 -94.00 -60.00   48
 45  ω     47.00 112.00   1.00   12.00    --  112.00-111.00-180.00   65
 46  ω     40.00  65.00   1.00   12.00    --  112.00 -94.00   0.00   25
 47  ω     41.00 120.00   1.00   12.00    --  112.00 -61.00  30.00   79
 48  ω     89.00 116.00   1.00   12.00    --  112.00-111.00 120.00   27
 49  ω     38.00  63.00   1.00   12.00    --  112.00-111.00 120.00   25
 50  ω     40.00 132.00   1.00   12.00    --  112.00 -45.00 150.00   92
 51  ω      1.00  79.00   1.00    4.00    --   42.62 -99.00 150.00   78
 52  ω    -70.00  31.00   1.00    4.00    --  -42.62  57.00  30.00  101
 53  ω    -82.00 -55.00   1.00    4.00    --  -42.62 -77.00-150.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1862560387
_diffrn_orient_matrix_UB_12      0.1218445820
_diffrn_orient_matrix_UB_13      -0.0145684804
_diffrn_orient_matrix_UB_21      0.1437616703
_diffrn_orient_matrix_UB_22      0.0185692080
_diffrn_orient_matrix_UB_23      0.0284711721
_diffrn_orient_matrix_UB_31      0.1431918737
_diffrn_orient_matrix_UB_32      -0.1771173041
_diffrn_orient_matrix_UB_33      -0.0070283298
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2922
_reflns_number_total             3868
_reflns_odcompleteness_completeness 98.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.019
_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)+(0.0623P)²+0.6185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(D1A) = Uiso(D1B)
Uiso(D2A) = Uiso(D2B)
Uiso(D3A) = Uiso(D3B)
Uiso(D4A) = Uiso(D4B)
Uiso(D5A) = Uiso(D5B)
Uiso(D6A) = Uiso(D6B)
Uiso(D7A) = Uiso(D7B)
Uiso(D8A) = Uiso(D8B)
Uiso(D9A) = Uiso(D9B)
Uiso(D10A) = Uiso(D10B)
Uiso(D11A) = Uiso(D11B)
Uiso(D12A) = Uiso(D12B)
Uiso(D13A) = Uiso(D13B)
Uiso(D14A) = Uiso(D14B) = Uiso(D14C)
Uiso(H15A) = Uiso(H15B) = Uiso(H15C) = Uiso(H16A) = Uiso(H16B) = Uiso(H16C) =
Uiso(H17A) = Uiso(H17B) = Uiso(H17C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
D1A D 0.732(4) 0.367(4) 0.0624(5) 0.017(4) Uiso 1 1 d . . . . .
D1B D 0.697(4) 0.150(4) 0.0590(5) 0.017(4) Uiso 1 1 d . . . . .
D2A D 1.033(5) 0.297(4) 0.1010(6) 0.030(5) Uiso 1 1 d . . . . .
D2B D 0.933(5) 0.084(4) 0.0991(5) 0.030(5) Uiso 1 1 d . . . . .
D3A D 0.666(5) 0.420(4) 0.1139(6) 0.033(5) Uiso 1 1 d . . . . .
D3B D 0.544(6) 0.225(4) 0.1075(7) 0.033(5) Uiso 1 1 d . . . . .
D4A D 0.868(6) 0.271(4) 0.1523(6) 0.028(5) Uiso 1 1 d . . . . .
D4B D 0.727(5) 0.085(4) 0.1476(5) 0.028(5) Uiso 1 1 d . . . . .
D5A D 0.533(5) 0.438(4) 0.1647(6) 0.030(5) Uiso 1 1 d . . . . .
D5B D 0.373(6) 0.272(4) 0.1553(6) 0.030(5) Uiso 1 1 d . . . . .
D6A D 0.693(5) 0.257(3) 0.2038(6) 0.023(4) Uiso 1 1 d . . . . .
D6B D 0.520(5) 0.089(4) 0.1943(5) 0.023(4) Uiso 1 1 d . . . . .
D7A D 0.359(5) 0.440(5) 0.2135(5) 0.029(5) Uiso 1 1 d . . . . .
D7B D 0.182(6) 0.282(4) 0.2030(6) 0.029(5) Uiso 1 1 d . . . . .
D8A D 0.496(6) 0.247(3) 0.2511(6) 0.023(4) Uiso 1 1 d . . . . .
D8B D 0.320(5) 0.090(4) 0.2413(5) 0.023(4) Uiso 1 1 d . . . . .
D9A D 0.167(5) 0.446(4) 0.2611(6) 0.029(5) Uiso 1 1 d . . . . .
D9B D -0.003(6) 0.286(4) 0.2516(6) 0.029(5) Uiso 1 1 d . . . . .
D10A D 0.306(6) 0.251(4) 0.2999(6) 0.030(5) Uiso 1 1 d . . . . .
D10B D 0.125(5) 0.089(5) 0.2896(5) 0.030(5) Uiso 1 1 d . . . . .
D11A D -0.016(5) 0.448(4) 0.3107(6) 0.029(5) Uiso 1 1 d . . . . .
D11B D -0.199(5) 0.295(4) 0.2994(6) 0.029(5) Uiso 1 1 d . . . . .
D12A D 0.120(6) 0.246(4) 0.3478(6) 0.027(5) Uiso 1 1 d . . . . .
D12B D -0.069(5) 0.095(4) 0.3368(5) 0.027(5) Uiso 1 1 d . . . . .
D13A D -0.208(5) 0.448(5) 0.3593(6) 0.035(5) Uiso 1 1 d . . . . .
D13B D -0.381(6) 0.292(4) 0.3487(6) 0.035(5) Uiso 1 1 d . . . . .
D14A D -0.067(8) 0.243(4) 0.3975(9) 0.053(6) Uiso 1 1 d . . . . .
D14B D -0.248(7) 0.093(6) 0.3855(7) 0.053(6) Uiso 1 1 d . . . . .
D14C D -0.349(7) 0.283(5) 0.3988(8) 0.053(6) Uiso 1 1 d . . . . .
H15A H 0.776(5) 0.364(4) 0.0134(5) 0.028(2) Uiso 1 1 d . . . . .
H15B H 0.789(5) 0.152(4) 0.0129(6) 0.028(2) Uiso 1 1 d . . . . .
H15C H 1.000(6) 0.258(4) 0.0009(7) 0.028(2) Uiso 1 1 d . . . . .
H16A H 1.242(5) 0.416(4) 0.0648(6) 0.028(2) Uiso 1 1 d . . . . .
H16B H 1.067(5) 0.527(4) 0.0455(5) 0.028(2) Uiso 1 1 d . . . . .
H16C H 1.271(5) 0.414(4) 0.0319(6) 0.028(2) Uiso 1 1 d . . . . .
H17A H 1.047(5) -0.035(4) 0.0455(5) 0.028(2) Uiso 1 1 d . . . . .
H17B H 1.246(5) 0.079(4) 0.0644(6) 0.028(2) Uiso 1 1 d . . . . .
H17C H 1.254(5) 0.073(4) 0.0309(6) 0.028(2) Uiso 1 1 d . . . . .
C1 C 0.8054(3) 0.2542(3) 0.06500(4) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.8863(4) 0.2225(3) 0.09591(4) 0.0243(4) Uani 1 1 d . . . . .
C3 C 0.6813(4) 0.2786(3) 0.11455(4) 0.0271(5) Uani 1 1 d . . . . .
C4 C 0.7191(4) 0.2232(3) 0.14573(4) 0.0248(4) Uani 1 1 d . . . . .
C5 C 0.5230(4) 0.3006(3) 0.16393(4) 0.0250(4) Uani 1 1 d . . . . .
C6 C 0.5348(4) 0.2262(3) 0.19440(4) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.3401(4) 0.3085(4) 0.21250(4) 0.0238(4) Uani 1 1 d . . . . .
C8 C 0.3438(4) 0.2267(3) 0.24253(4) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.1509(4) 0.3102(3) 0.26073(4) 0.0244(4) Uani 1 1 d . . . . .
C10 C 0.1517(4) 0.2262(3) 0.29068(4) 0.0244(4) Uani 1 1 d . . . . .
C11 C -0.0388(4) 0.3116(3) 0.30909(4) 0.0248(4) Uani 1 1 d . . . . .
C12 C -0.0366(4) 0.2267(3) 0.33897(4) 0.0264(4) Uani 1 1 d . . . . .
C13 C -0.2256(4) 0.3108(4) 0.35767(4) 0.0307(5) Uani 1 1 d . . . . .
C14 C -0.2223(6) 0.2229(4) 0.38720(5) 0.0420(7) Uani 1 1 d . . . . .
C15 C 0.8752(4) 0.2562(3) 0.01477(4) 0.0244(4) Uani 1 1 d . . . . .
C16 C 1.1591(4) 0.4177(3) 0.04678(4) 0.0224(4) Uani 1 1 d . . . . .
C17 C 1.1463(4) 0.0754(3) 0.04625(4) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.9994(3) 0.2498(2) 0.04360(3) 0.0174(3) Uani 1 1 d . . . . .
Br1 Br 0.62014(3) 0.75214(3) 0.03967(2) 0.02713(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 D1A 0.91(3) . ?
C1 D1B 0.99(3) . ?
C1 C2 1.523(2) . ?
C1 N1 1.512(2) . ?
C2 D2A 1.00(3) . ?
C2 D2B 1.03(3) . ?
C2 C3 1.527(3) . ?
C3 D3A 1.01(3) . ?
C3 D3B 0.91(3) . ?
C3 C4 1.527(2) . ?
C4 D4A 0.94(3) . ?
C4 D4B 0.99(3) . ?
C4 C5 1.525(3) . ?
C5 D5A 0.98(3) . ?
C5 D5B 0.94(3) . ?
C5 C6 1.529(3) . ?
C6 D6A 1.00(3) . ?
C6 D6B 0.98(3) . ?
C6 C7 1.529(3) . ?
C7 D7A 0.95(3) . ?
C7 D7B 0.99(3) . ?
C7 C8 1.529(3) . ?
C8 D8A 0.94(3) . ?
C8 D8B 0.99(3) . ?
C8 C9 1.527(3) . ?
C9 D9A 0.97(3) . ?
C9 D9B 0.96(3) . ?
C9 C10 1.532(3) . ?
C10 D10A 0.97(3) . ?
C10 D10B 0.99(3) . ?
C10 C11 1.529(3) . ?
C11 D11A 0.98(3) . ?
C11 D11B 1.00(3) . ?
C11 C12 1.532(3) . ?
C12 D12A 0.97(3) . ?
C12 D12B 0.96(3) . ?
C12 C13 1.528(3) . ?
C13 D13A 0.98(3) . ?
C13 D13B 0.96(3) . ?
C13 C14 1.525(3) . ?
C14 D14A 0.99(4) . ?
C14 D14B 0.94(4) . ?
C14 D14C 1.01(4) . ?
C15 H15A 0.95(3) . ?
C15 H15B 0.89(3) . ?
C15 H15C 0.97(3) . ?
C15 N1 1.500(2) . ?
C16 H16A 0.95(3) . ?
C16 H16B 0.94(3) . ?
C16 H16C 0.96(3) . ?
C16 N1 1.499(3) . ?
C17 H17A 0.96(3) . ?
C17 H17B 1.00(3) . ?
C17 H17C 0.96(3) . ?
C17 N1 1.495(3) . ?

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
_geom_angle_publ_flag
D1A C1 D1B 111(2) . . ?
C2 C1 D1A 112.0(15) . . ?
C2 C1 D1B 108.3(13) . . ?
N1 C1 D1A 105.2(15) . . ?
N1 C1 D1B 104.1(13) . . ?
N1 C1 C2 116.16(15) . . ?
D2A C2 D2B 106(2) . . ?
C1 C2 D2A 111.0(16) . . ?
C1 C2 D2B 110.1(15) . . ?
C1 C2 C3 108.07(16) . . ?
C3 C2 D2A 110.6(16) . . ?
C3 C2 D2B 111.3(15) . . ?
D3A C3 D3B 110(2) . . ?
C2 C3 D3A 108.1(16) . . ?
C2 C3 D3B 109.0(19) . . ?
C4 C3 D3A 107.1(16) . . ?
C4 C3 D3B 108.9(19) . . ?
C4 C3 C2 114.05(17) . . ?
D4A C4 D4B 107(2) . . ?
C3 C4 D4A 107.9(17) . . ?
C3 C4 D4B 110.4(15) . . ?
C5 C4 D4A 109.4(17) . . ?
C5 C4 D4B 110.0(15) . . ?
C5 C4 C3 111.86(17) . . ?
D5A C5 D5B 106(2) . . ?
C4 C5 D5A 110.0(16) . . ?
C4 C5 D5B 109.4(18) . . ?
C4 C5 C6 113.43(18) . . ?
C6 C5 D5A 108.1(16) . . ?
C6 C5 D5B 109.4(18) . . ?
D6A C6 D6B 107(2) . . ?
C5 C6 D6A 109.9(15) . . ?
C5 C6 D6B 110.0(14) . . ?
C7 C6 D6A 107.9(15) . . ?
C7 C6 D6B 108.7(15) . . ?
C7 C6 C5 112.71(18) . . ?
D7A C7 D7B 108(2) . . ?
C6 C7 D7A 109.3(16) . . ?
C6 C7 D7B 108.6(16) . . ?
C6 C7 C8 112.75(18) . . ?
C8 C7 D7A 109.6(16) . . ?
C8 C7 D7B 108.8(16) . . ?
D8A C8 D8B 107(2) . . ?
C7 C8 D8A 108.3(17) . . ?
C7 C8 D8B 109.2(14) . . ?
C9 C8 D8A 110.3(17) . . ?
C9 C8 D8B 108.7(15) . . ?
C9 C8 C7 112.80(18) . . ?
D9A C9 D9B 106(2) . . ?
C8 C9 D9A 109.3(16) . . ?
C8 C9 D9B 108.5(17) . . ?
C8 C9 C10 112.89(19) . . ?
C10 C9 D9A 112.2(16) . . ?
C10 C9 D9B 107.9(18) . . ?
D10A C10 D10B 109(2) . . ?
C9 C10 D10A 108.1(18) . . ?
C9 C10 D10B 110.1(14) . . ?
C11 C10 D10A 107.8(17) . . ?
C11 C10 D10B 108.5(14) . . ?
C11 C10 C9 113.01(19) . . ?
D11A C11 D11B 106(2) . . ?
C10 C11 D11A 110.1(16) . . ?
C10 C11 D11B 109.2(16) . . ?
C10 C11 C12 112.59(18) . . ?
C12 C11 D11A 109.1(15) . . ?
C12 C11 D11B 110.1(16) . . ?
D12A C12 D12B 110(2) . . ?
C11 C12 D12A 108.2(17) . . ?
C11 C12 D12B 107.2(16) . . ?
C13 C12 D12A 109.4(17) . . ?
C13 C12 D12B 108.3(16) . . ?
C13 C12 C11 113.26(19) . . ?
D13A C13 D13B 105(2) . . ?
C12 C13 D13A 111.6(17) . . ?
C12 C13 D13B 109.2(18) . . ?
C14 C13 D13A 109.8(16) . . ?
C14 C13 D13B 108.7(18) . . ?
C14 C13 C12 112.4(2) . . ?
D14A C14 D14B 108(3) . . ?
D14A C14 D14C 107(3) . . ?
D14B C14 D14C 111(3) . . ?
C13 C14 D14A 111(2) . . ?
C13 C14 D14B 109(2) . . ?
C13 C14 D14C 110(2) . . ?
H15A C15 H15B 111(3) . . ?
H15A C15 H15C 112(2) . . ?
H15B C15 H15C 110(2) . . ?
N1 C15 H15A 109.4(16) . . ?
N1 C15 H15B 107.1(17) . . ?
N1 C15 H15C 106.8(19) . . ?
H16A C16 H16B 108(2) . . ?
H16A C16 H16C 110(2) . . ?
H16B C16 H16C 111(2) . . ?
N1 C16 H16A 110.3(17) . . ?
N1 C16 H16B 109.5(18) . . ?
N1 C16 H16C 107.9(17) . . ?
H17A C17 H17B 110(2) . . ?
H17A C17 H17C 110(2) . . ?
H17B C17 H17C 107(2) . . ?
N1 C17 H17A 111.3(17) . . ?
N1 C17 H17B 109.7(16) . . ?
N1 C17 H17C 108.4(17) . . ?
C15 N1 C1 106.51(14) . . ?
C16 N1 C1 111.03(14) . . ?
C16 N1 C15 108.56(15) . . ?
C17 N1 C1 111.70(14) . . ?
C17 N1 C15 109.45(15) . . ?
C17 N1 C16 109.50(15) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 169.96(19) . . . . ?
C2 C1 N1 C15 172.02(18) . . . . ?
C2 C1 N1 C16 -70.0(2) . . . . ?
C2 C1 N1 C17 52.6(2) . . . . ?
C2 C3 C4 C5 173.8(2) . . . . ?
C3 C4 C5 C6 172.0(2) . . . . ?
C4 C5 C6 C7 178.79(19) . . . . ?
C5 C6 C7 C8 177.07(19) . . . . ?
C6 C7 C8 C9 179.44(19) . . . . ?
C7 C8 C9 C10 179.09(19) . . . . ?
C8 C9 C10 C11 179.14(19) . . . . ?
C9 C10 C11 C12 179.96(19) . . . . ?
C10 C11 C12 C13 179.9(2) . . . . ?
C11 C12 C13 C14 179.4(2) . . . . ?
N1 C1 C2 C3 166.42(17) . . . . ?

_olex2_date_sample_data_collection 2016-06-28
_olex2_exptl_crystal_mounting_method 
'0.3mm diameter 20um nylon loop from Hampton Research '
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.056
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0359
_database_code_depnum_ccdc_archive 'CCDC 1941226'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C14TAB
_chemical_name_systematic        'Tetradecyltrimethylammonium bromide'
_chemical_formula_moiety         'C17 H38 N, Br'
_chemical_formula_sum            'C17 H38 Br N'
_chemical_formula_weight         336.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H38 N Br'
_chemical_oxdiff_usercomment     'C14TAB at 380K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.6621(2)
_cell_length_b                   7.3445(4)
_cell_length_c                   24.1054(13)
_cell_angle_alpha                90
_cell_angle_beta                 87.441(4)
_cell_angle_gamma                90
_cell_volume                     1001.42(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7855
_cell_measurement_temperature    380
_cell_measurement_theta_max      73.0070
_cell_measurement_theta_min      5.4780
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.593
_exptl_absorpt_coefficient_mu    2.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method 'Recrystallized from H2O'
_exptl_crystal_size_max          0.2161
_exptl_crystal_size_mid          0.1229
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14236
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.714
_diffrn_reflns_theta_min         3.671
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      380
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -58.00  -10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -59.00  -10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  4 omega  -91.00  -64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
  6 omega  -75.00  -10.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega    3.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216  -99.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  8 omega   31.00  139.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000  -90.0000 108

#__ type_ start__ end____ width___ exp.time_
  9 omega   61.00   88.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -125.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   83.00  119.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   82.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega   78.00  121.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 13 omega  122.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 14 omega  105.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 15 omega  153.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   74.0000   17.6454 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  141.00  168.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega  108.00  168.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 18 omega   95.00  173.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
 19 omega   94.00  167.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
 20 omega   84.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   78.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   75.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000  -28.6070 103

#__ type_ start__ end____ width___ exp.time_
 23 omega   78.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega   77.00  167.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   65.0000   69.1594 90

#__ type_ start__ end____ width___ exp.time_
 25 omega   78.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   77.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 27 omega   78.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   59.0000  147.0081 96

#__ type_ start__ end____ width___ exp.time_
 28 omega   75.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 29 omega   74.00  136.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   74.0000   17.6454 62

#__ type_ start__ end____ width___ exp.time_
 30 omega   77.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   65.0000    6.2786 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   74.00  100.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   74.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 33 omega   77.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -120.0000 65

#__ type_ start__ end____ width___ exp.time_
 34 omega   77.00  128.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 35 omega   75.00  102.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   74.00  100.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   74.00  100.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   75.00  101.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   71.0000  -97.6571 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   74.00  101.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 40 omega   74.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 41 omega   74.00  101.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 42 omega   27.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
 43 omega  -70.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   57.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 44 omega -100.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
 45 omega  -70.00   29.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   57.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
 46 omega -119.00  -90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   60.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2601531000
_diffrn_orient_matrix_UB_12      -0.0248092000
_diffrn_orient_matrix_UB_13      -0.0147273000
_diffrn_orient_matrix_UB_21      0.0695489000
_diffrn_orient_matrix_UB_22      0.0300363000
_diffrn_orient_matrix_UB_23      -0.0618079000
_diffrn_orient_matrix_UB_31      0.0414819000
_diffrn_orient_matrix_UB_32      -0.2060955000
_diffrn_orient_matrix_UB_33      -0.0072446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1903
_reflns_number_total             2138
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.268
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.001
_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)+(0.0923P)²+0.2647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1453
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10_$1
 0.97 with sigma of 0.005
 C11-H11 = C11-H11_$1
 0.97 with sigma of 0.005
 C12-H12 = C12-H12_$1
 0.97 with sigma of 0.005
 C13-H13 = C13-H13_$1
 0.97 with sigma of 0.005
 C14-H14 = C14-H14M = C14-H14_$1
 0.96 with sigma of 0.005
 C15-H15 = C15-H15M = C15-H15_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1
 1.565 with sigma of 0.005
 H11-H11_$1
 1.565 with sigma of 0.005
 H12-H12_$1
 1.565 with sigma of 0.005
 H13-H13_$1
 1.565 with sigma of 0.005
 H14-H14_$1 = H14-H14M
 1.565 with sigma of 0.005
 H15-H15_$1 = H15-H15M
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10 \\sim C11-H10 \\sim C11-H10_$1
 with sigma of 0.005
 C10-H11 \\sim C10-H11_$1 \\sim C12-H11 \\sim C12-H11_$1
 with sigma of 0.005
 C11-H12 \\sim C11-H12_$1 \\sim C13-H12 \\sim C13-H12_$1
 with sigma of 0.005
 C12-H13 \\sim C12-H13_$1 \\sim C14-H13 \\sim C14-H13_$1
 with sigma of 0.005
 C13-H14 \\sim C13-H14M \\sim C13-H14_$1
 with sigma of 0.005
 N1-H15 \\sim N1-H15M \\sim N1-H15_$1
 with sigma of 0.005
 H14-H14M \\sim H14M-H14_$1 \\sim H14_$1-H14
 with sigma of 0.005
 H15-H15M \\sim H15M-H15_$1 \\sim H15_$1-H15
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7812(7) 0.2500 0.13042(18) 0.0756(10) Uani 1 2 d DS T P . .
H1 H 0.6835(14) 0.3565(4) 0.1248(2) 0.091 Uiso 1 1 d DR . . . .
C2 C 0.8578(11) 0.2500 0.1890(2) 0.1052(17) Uani 1 2 d DS T P . .
H2 H 0.9544(16) 0.3565(4) 0.1953(3) 0.126 Uiso 1 1 d DR . . . .
C3 C 0.6483(12) 0.2500 0.2290(2) 0.1114(18) Uani 1 2 d DS T P . .
H3 H 0.5544(17) 0.3565(4) 0.2210(3) 0.134 Uiso 1 1 d DR . . . .
C4 C 0.6891(14) 0.2500 0.2895(3) 0.129(3) Uani 1 2 d DS T P . .
H4 H 0.7862(18) 0.3566(4) 0.2954(3) 0.155 Uiso 1 1 d DR . . . .
C5 C 0.4949(15) 0.2500 0.3295(3) 0.144(3) Uani 1 2 d DS T P . .
H5 H 0.4020(19) 0.3566(4) 0.3211(3) 0.172 Uiso 1 1 d DR . . . .
C6 C 0.5198(16) 0.2500 0.3875(3) 0.132(3) Uani 1 2 d DS T P . .
H6 H 0.6127(19) 0.3565(4) 0.3961(4) 0.158 Uiso 1 1 d DR . . . .
C7 C 0.3269(18) 0.2500 0.4287(3) 0.160(4) Uani 1 2 d DS T P . .
H7 H 0.236(2) 0.3565(4) 0.4194(4) 0.192 Uiso 1 1 d DR . . . .
C8 C 0.3406(17) 0.2500 0.4867(3) 0.145(3) Uani 1 2 d DS T P . .
H8 H 0.433(2) 0.3566(4) 0.4954(4) 0.174 Uiso 1 1 d DR . . . .
C9 C 0.1511(19) 0.2500 0.5274(3) 0.175(5) Uani 1 2 d DS T P . .
H9 H 0.061(2) 0.3565(4) 0.5174(4) 0.210 Uiso 1 1 d DR . . . .
C10 C 0.1574(18) 0.2500 0.5840(3) 0.145(3) Uani 1 2 d DS T P . .
H10 H 0.250(2) 0.3566(4) 0.5926(4) 0.174 Uiso 1 1 d DR . . . .
C11 C -0.020(2) 0.2500 0.6258(4) 0.202(6) Uani 1 2 d DS T P . .
H11 H -0.113(2) 0.3565(4) 0.6174(4) 0.243 Uiso 1 1 d DR . . . .
C12 C -0.018(2) 0.2500 0.6832(3) 0.154(4) Uani 1 2 d DS T P . .
H12 H 0.076(2) 0.3565(4) 0.6915(5) 0.185 Uiso 1 1 d DR . . . .
C13 C -0.195(3) 0.2500 0.7248(4) 0.238(8) Uani 1 2 d DS T P . .
H13 H -0.285(3) 0.3565(4) 0.7150(5) 0.285 Uiso 1 1 d DR . . . .
C14 C -0.193(2) 0.2500 0.7796(4) 0.201(6) Uani 1 2 d DS T P . .
H14 H -0.112(3) 0.3566(3) 0.7920(6) 0.302 Uiso 1 1 d DR . . . .
H14M H -0.352(3) 0.2500 0.7951(9) 0.302 Uiso 1 2 d DRS T P . .
C15 C 0.8557(8) 0.2500 0.03154(18) 0.0851(12) Uani 1 2 d DS T P . .
H15 H 0.7586(14) 0.3565(3) 0.0290(5) 0.128 Uiso 1 1 d DR . . . .
H15M H 0.972(2) 0.2500 0.0012(4) 0.128 Uiso 1 2 d DRS T P . .
C16 C 1.1281(5) 0.4158(5) 0.08803(14) 0.0827(8) Uani 1 1 d . . . . .
H16A H 1.2145 0.4129 0.1214 0.124 Uiso 1 1 calc GR . . . .
H16B H 1.0305 0.5227 0.0880 0.124 Uiso 1 1 calc GR . . . .
H16C H 1.2370 0.4183 0.0564 0.124 Uiso 1 1 calc GR . . . .
N1 N 0.9759(5) 0.2500 0.08544(13) 0.0638(7) Uani 1 2 d DS T P . .
Br1 Br 0.60228(7) 0.7500 0.07696(2) 0.0847(2) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.971(4) . ?
C1 C2 1.496(7) . ?
C1 N1 1.511(5) . ?
C2 H2 0.970(4) . ?
C2 C3 1.495(9) . ?
C3 H3 0.971(4) . ?
C3 C4 1.486(9) . ?
C4 H4 0.970(4) . ?
C4 C5 1.429(9) . ?
C5 H5 0.970(4) . ?
C5 C6 1.412(11) . ?
C6 H6 0.970(4) . ?
C6 C7 1.442(11) . ?
C7 H7 0.969(4) . ?
C7 C8 1.403(11) . ?
C8 H8 0.970(4) . ?
C8 C9 1.421(11) . ?
C9 H9 0.970(4) . ?
C9 C10 1.367(12) . ?
C10 H10 0.969(4) . ?
C10 C11 1.391(12) . ?
C11 H11 0.970(4) . ?
C11 C12 1.385(13) . ?
C12 H12 0.970(4) . ?
C12 C13 1.385(13) . ?
C13 H13 0.970(4) . ?
C13 C14 1.322(15) . ?
C14 H14 0.960(4) . ?
C14 H14M 0.959(5) . ?
C15 H15 0.960(4) . ?
C15 H15M 0.961(5) . ?
C15 N1 1.493(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 N1 1.495(3) . ?
N1 C16 1.495(3) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 108.8(4) . . ?
C2 C1 N1 116.4(4) . . ?
N1 C1 H1 107.6(5) . . ?
C1 C2 H2 109.6(5) . . ?
C3 C2 C1 110.7(5) . . ?
C3 C2 H2 109.7(5) . . ?
C2 C3 H3 107.3(6) . . ?
C4 C3 C2 118.6(6) . . ?
C4 C3 H3 107.9(6) . . ?
C3 C4 H4 104.8(6) . . ?
C5 C4 C3 120.9(7) . . ?
C5 C4 H4 109.0(6) . . ?
C4 C5 H5 105.5(6) . . ?
C6 C5 C4 124.1(8) . . ?
C6 C5 H5 106.7(6) . . ?
C5 C6 H6 106.9(7) . . ?
C5 C6 C7 125.1(8) . . ?
C7 C6 H6 104.7(7) . . ?
C6 C7 H7 103.7(7) . . ?
C8 C7 C6 127.7(9) . . ?
C8 C7 H7 106.5(7) . . ?
C7 C8 H8 105.7(7) . . ?
C7 C8 C9 127.9(10) . . ?
C9 C8 H8 104.4(7) . . ?
C8 C9 H9 102.6(8) . . ?
C10 C9 C8 129.6(10) . . ?
C10 C9 H9 106.5(7) . . ?
C9 C10 H10 104.6(7) . . ?
C9 C10 C11 132.3(11) . . ?
C11 C10 H10 102.9(7) . . ?
C10 C11 H11 103.3(8) . . ?
C12 C11 C10 133.3(12) . . ?
C12 C11 H11 103.7(8) . . ?
C11 C12 H12 103.5(8) . . ?
C13 C12 C11 133.2(13) . . ?
C13 C12 H12 103.6(8) . . ?
C12 C13 H13 101.3(9) . . ?
C14 C13 C12 133.2(15) . . ?
C14 C13 H13 105.8(8) . . ?
C13 C14 H14 109.7(7) . . ?
C13 C14 H14M 109.7(7) . . ?
H14 C14 H14M 109.3(7) . . ?
H15 C15 H15M 109.1(7) . . ?
N1 C15 H15 109.9(6) . . ?
N1 C15 H15M 109.7(7) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
C15 N1 C1 106.1(3) . . ?
C15 N1 C16 108.8(2) . 4_565 ?
C15 N1 C16 108.8(2) . . ?
C16 N1 C1 111.9(2) . . ?
C16 N1 C1 111.9(2) 4_565 . ?
C16 N1 C16 109.1(3) 4_565 . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(2) . . . . ?
C2 C1 N1 C15 180.000(0) . . . . ?
C2 C1 N1 C16 61.4(2) . . . 4_565 ?
C2 C1 N1 C16 -61.4(2) . . . . ?
C2 C3 C4 C5 180.000(2) . . . . ?
C3 C4 C5 C6 180.000(3) . . . . ?
C4 C5 C6 C7 180.000(3) . . . . ?
C5 C6 C7 C8 180.000(4) . . . . ?
C6 C7 C8 C9 180.000(5) . . . . ?
C7 C8 C9 C10 180.000(6) . . . . ?
C8 C9 C10 C11 180.000(8) . . . . ?
C9 C10 C11 C12 180.000(8) . . . . ?
C10 C11 C12 C13 180.000(11) . . . . ?
C11 C12 C13 C14 180.000(11) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0100 -0.0002 0.0002 -0.5011 0.0074 0.0310 0.0036
1 4 2 0.0843 1.1724 4.4963 1.6889 -0.4414 0.1122 -0.8903
-1 -4 -2 0.0843 -1.1724 -4.4963 -1.6889 0.4414 -0.1122 0.8903
-3 3 1 0.0614 -2.9712 2.7679 0.9035 0.6910 -0.1793 -0.7003
0 0 1 0.0100 0.0002 -0.0002 0.5011 -0.0074 -0.0310 -0.0036
3 -3 -1 0.0614 2.9712 -2.7679 -0.9035 -0.6910 0.1793 0.7003

_olex2_date_sample_data_collection 2015-01-30
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0475
_database_code_depnum_ccdc_archive 'CCDC 1941228'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C12TAB
_chemical_name_systematic        'Dodecyltrimethylammonium bromide'
_chemical_formula_moiety         'C15 H34 N, Br'
_chemical_formula_sum            'C15 H34 Br N'
_chemical_formula_weight         308.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H34 Br N'
_chemical_oxdiff_usercomment     'C12TAB at 150K (acetone/ethanol)'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.59929(8)
_cell_length_b                   7.14079(10)
_cell_length_c                   42.5497(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.2962(14)
_cell_angle_gamma                90
_cell_volume                     1701.15(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10556
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.4910
_cell_measurement_theta_min      6.2300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.138
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.1653
_exptl_crystal_size_min          0.0131
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            23233
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.627
_diffrn_reflns_theta_min         6.241
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216   38.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   77.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  133.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000 -111.3316 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  116.00  157.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega  114.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   72.0000   42.3918 63

#__ type_ start__ end____ width___ exp.time_
  6 omega  130.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega  111.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega   81.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   45.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   74.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 10 omega   78.00  124.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   77.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   78.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   75.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   72.0000   42.3918 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   71.0000   26.3639 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   78.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 16 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   78.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   74.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 20 omega   78.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
 21 omega   78.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 22 omega   76.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
 23 omega   77.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 24 omega   75.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000 -111.3316 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   74.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   74.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   34.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -45.0000   90.0000 63

#__ type_ start__ end____ width___ exp.time_
 30 omega   45.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
 31 omega   58.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -141.0000  170.0000 37

#__ type_ start__ end____ width___ exp.time_
 32 omega   26.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   30.0000 67

#__ type_ start__ end____ width___ exp.time_
 33 omega   45.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  -90.0000 64

#__ type_ start__ end____ width___ exp.time_
 34 omega   34.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000 -120.0000 72

#__ type_ start__ end____ width___ exp.time_
 35 omega  -46.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 36 omega  -49.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 37 omega  -60.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 38 omega  -76.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000    0.0000 66

#__ type_ start__ end____ width___ exp.time_
 39 omega  -49.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 40 omega  -64.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 41 omega  -64.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 42 omega  -49.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  -90.0000 73

#__ type_ start__ end____ width___ exp.time_
 43 omega  -70.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   57.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 44 omega -111.00  -78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 45 omega -112.00  -76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
 46 omega -118.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000    0.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0794710000
_diffrn_orient_matrix_UB_12      0.0309249000
_diffrn_orient_matrix_UB_13      0.0341449000
_diffrn_orient_matrix_UB_21      -0.2160070000
_diffrn_orient_matrix_UB_22      -0.1144143000
_diffrn_orient_matrix_UB_23      0.0119431000
_diffrn_orient_matrix_UB_31      0.1506816000
_diffrn_orient_matrix_UB_32      -0.1802881000
_diffrn_orient_matrix_UB_33      -0.0017123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2726
_reflns_number_total             3385
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²+0.9979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0577
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B) = Uiso(H12C)
Uiso(H13A) = Uiso(H13B) = Uiso(H13C) = Uiso(H14A) = Uiso(H14B) = Uiso(H14C) =
Uiso(H15A) = Uiso(H15B) = Uiso(H15C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.704(3) 0.375(3) 0.0692(4) 0.019(3) Uiso 1 1 d . . . . .
H1B H 0.671(3) 0.159(3) 0.0659(4) 0.019(3) Uiso 1 1 d . . . . .
H2A H 0.981(4) 0.299(3) 0.1119(5) 0.030(4) Uiso 1 1 d . . . . .
H2B H 0.883(4) 0.083(3) 0.1093(5) 0.030(4) Uiso 1 1 d . . . . .
H3A H 0.609(4) 0.413(3) 0.1252(5) 0.032(4) Uiso 1 1 d . . . . .
H3B H 0.491(4) 0.222(3) 0.1193(5) 0.032(4) Uiso 1 1 d . . . . .
H4A H 0.806(4) 0.268(3) 0.1694(5) 0.027(4) Uiso 1 1 d . . . . .
H4B H 0.654(3) 0.085(3) 0.1630(5) 0.027(4) Uiso 1 1 d . . . . .
H5A H 0.464(3) 0.433(3) 0.1819(4) 0.025(3) Uiso 1 1 d . . . . .
H5B H 0.303(4) 0.269(3) 0.1728(4) 0.025(3) Uiso 1 1 d . . . . .
H6A H 0.602(4) 0.254(3) 0.2248(5) 0.027(4) Uiso 1 1 d . . . . .
H6B H 0.443(4) 0.090(3) 0.2145(5) 0.027(4) Uiso 1 1 d . . . . .
H7A H 0.269(3) 0.444(3) 0.2367(5) 0.025(4) Uiso 1 1 d . . . . .
H7B H 0.100(4) 0.284(3) 0.2253(5) 0.025(4) Uiso 1 1 d . . . . .
H8A H 0.391(4) 0.252(3) 0.2787(5) 0.028(4) Uiso 1 1 d . . . . .
H8B H 0.223(4) 0.093(3) 0.2675(5) 0.028(4) Uiso 1 1 d . . . . .
H9A H 0.068(4) 0.447(3) 0.2908(5) 0.030(4) Uiso 1 1 d . . . . .
H9B H -0.113(4) 0.296(3) 0.2786(5) 0.030(4) Uiso 1 1 d . . . . .
H10A H 0.186(4) 0.243(3) 0.3328(5) 0.028(4) Uiso 1 1 d . . . . .
H10B H 0.004(4) 0.092(3) 0.3200(5) 0.028(4) Uiso 1 1 d . . . . .
H11A H -0.139(4) 0.448(3) 0.3447(5) 0.039(4) Uiso 1 1 d . . . . .
H11B H -0.323(4) 0.294(3) 0.3325(5) 0.039(4) Uiso 1 1 d . . . . .
H12A H -0.027(5) 0.243(4) 0.3871(6) 0.052(4) Uiso 1 1 d . . . . .
H12B H -0.204(4) 0.089(4) 0.3738(6) 0.052(4) Uiso 1 1 d . . . . .
H12C H -0.299(5) 0.284(3) 0.3882(6) 0.052(4) Uiso 1 1 d . . . . .
H13A H 0.768(4) 0.372(3) 0.0155(4) 0.0269(16) Uiso 1 1 d . . . . .
H13B H 0.772(4) 0.148(3) 0.0146(5) 0.0269(16) Uiso 1 1 d . . . . .
H13C H 0.997(4) 0.258(3) 0.0008(5) 0.0269(16) Uiso 1 1 d . . . . .
H14A H 1.219(4) 0.413(3) 0.0718(5) 0.0269(16) Uiso 1 1 d . . . . .
H14B H 1.041(4) 0.526(3) 0.0502(5) 0.0269(16) Uiso 1 1 d . . . . .
H14C H 1.261(4) 0.415(3) 0.0355(5) 0.0269(16) Uiso 1 1 d . . . . .
H15A H 1.021(4) -0.033(3) 0.0490(4) 0.0269(16) Uiso 1 1 d . . . . .
H15B H 1.210(4) 0.078(3) 0.0709(5) 0.0269(16) Uiso 1 1 d . . . . .
H15C H 1.241(4) 0.078(3) 0.0338(5) 0.0269(16) Uiso 1 1 d . . . . .
C1 C 0.7768(3) 0.2544(3) 0.07198(3) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.8434(3) 0.2218(3) 0.10600(4) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.6322(3) 0.2791(3) 0.12688(4) 0.0266(4) Uani 1 1 d . . . . .
C4 C 0.6555(3) 0.2230(3) 0.16130(4) 0.0248(4) Uani 1 1 d . . . . .
C5 C 0.4532(3) 0.3001(3) 0.18171(4) 0.0241(4) Uani 1 1 d . . . . .
C6 C 0.4515(3) 0.2266(3) 0.21529(4) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.2511(3) 0.3078(3) 0.23550(4) 0.0243(4) Uani 1 1 d . . . . .
C8 C 0.2413(3) 0.2274(3) 0.26876(4) 0.0243(4) Uani 1 1 d . . . . .
C9 C 0.0431(3) 0.3106(3) 0.28927(4) 0.0249(4) Uani 1 1 d . . . . .
C10 C 0.0312(3) 0.2277(3) 0.32219(4) 0.0256(4) Uani 1 1 d . . . . .
C11 C -0.1652(4) 0.3107(3) 0.34298(4) 0.0300(4) Uani 1 1 d . . . . .
C12 C -0.1748(5) 0.2230(3) 0.37559(5) 0.0402(5) Uani 1 1 d . . . . .
C13 C 0.8679(3) 0.2562(3) 0.01631(4) 0.0244(3) Uani 1 1 d . . . . .
C14 C 1.1381(3) 0.4176(3) 0.05158(4) 0.0226(4) Uani 1 1 d . . . . .
C15 C 1.1257(3) 0.0753(3) 0.05100(4) 0.0232(4) Uani 1 1 d . . . . .
N1 N 0.9795(2) 0.2504(2) 0.04819(3) 0.0179(3) Uani 1 1 d . . . . .
Br1 Br 0.60268(3) 0.75223(3) 0.04384(2) 0.02716(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.96(2) . ?
C1 H1B 0.944(19) . ?
C1 C2 1.517(2) . ?
C1 N1 1.5114(18) . ?
C2 H2A 0.98(2) . ?
C2 H2B 1.02(2) . ?
C2 C3 1.526(2) . ?
C3 H3A 0.97(2) . ?
C3 H3B 0.95(2) . ?
C3 C4 1.525(2) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.99(2) . ?
C4 C5 1.522(2) . ?
C5 H5A 0.95(2) . ?
C5 H5B 0.95(2) . ?
C5 C6 1.522(2) . ?
C6 H6A 0.96(2) . ?
C6 H6B 0.98(2) . ?
C6 C7 1.520(2) . ?
C7 H7A 0.98(2) . ?
C7 H7B 0.97(2) . ?
C7 C8 1.527(2) . ?
C8 H8A 0.96(2) . ?
C8 H8B 0.97(2) . ?
C8 C9 1.524(2) . ?
C9 H9A 0.99(2) . ?
C9 H9B 1.00(2) . ?
C9 C10 1.521(2) . ?
C10 H10A 0.99(2) . ?
C10 H10B 0.98(2) . ?
C10 C11 1.523(3) . ?
C11 H11A 0.99(2) . ?
C11 H11B 1.00(2) . ?
C11 C12 1.523(3) . ?
C12 H12A 0.98(3) . ?
C12 H12B 0.97(3) . ?
C12 H12C 0.98(3) . ?
C13 H13A 1.00(2) . ?
C13 H13B 0.94(2) . ?
C13 H13C 0.97(2) . ?
C13 N1 1.5012(19) . ?
C14 H14A 0.98(2) . ?
C14 H14B 0.95(2) . ?
C14 H14C 0.96(2) . ?
C14 N1 1.496(2) . ?
C15 H15A 0.98(2) . ?
C15 H15B 0.98(2) . ?
C15 H15C 0.97(2) . ?
C15 N1 1.500(2) . ?

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
_geom_angle_publ_flag
H1A C1 H1B 110.1(15) . . ?
C2 C1 H1A 111.3(11) . . ?
C2 C1 H1B 108.4(11) . . ?
N1 C1 H1A 104.6(11) . . ?
N1 C1 H1B 105.8(11) . . ?
N1 C1 C2 116.41(13) . . ?
H2A C2 H2B 109.6(16) . . ?
C1 C2 H2A 111.2(12) . . ?
C1 C2 H2B 109.6(11) . . ?
C1 C2 C3 108.48(14) . . ?
C3 C2 H2A 107.8(12) . . ?
C3 C2 H2B 110.2(11) . . ?
H3A C3 H3B 106.6(17) . . ?
C2 C3 H3A 108.8(12) . . ?
C2 C3 H3B 109.3(13) . . ?
C4 C3 H3A 110.1(12) . . ?
C4 C3 H3B 107.2(13) . . ?
C4 C3 C2 114.45(15) . . ?
H4A C4 H4B 108.2(16) . . ?
C3 C4 H4A 109.8(12) . . ?
C3 C4 H4B 109.3(11) . . ?
C5 C4 H4A 108.6(12) . . ?
C5 C4 H4B 108.4(12) . . ?
C5 C4 C3 112.39(15) . . ?
H5A C5 H5B 106.7(17) . . ?
C4 C5 H5A 108.7(12) . . ?
C4 C5 H5B 110.2(12) . . ?
C4 C5 C6 114.02(15) . . ?
C6 C5 H5A 109.7(12) . . ?
C6 C5 H5B 107.3(12) . . ?
H6A C6 H6B 104.9(17) . . ?
C5 C6 H6A 109.4(12) . . ?
C5 C6 H6B 108.2(12) . . ?
C7 C6 H6A 109.3(12) . . ?
C7 C6 H6B 111.3(12) . . ?
C7 C6 C5 113.32(15) . . ?
H7A C7 H7B 106.7(16) . . ?
C6 C7 H7A 109.4(12) . . ?
C6 C7 H7B 108.8(12) . . ?
C6 C7 C8 113.50(15) . . ?
C8 C7 H7A 109.0(12) . . ?
C8 C7 H7B 109.2(12) . . ?
H8A C8 H8B 107.2(17) . . ?
C7 C8 H8A 108.6(12) . . ?
C7 C8 H8B 109.0(12) . . ?
C9 C8 H8A 108.1(12) . . ?
C9 C8 H8B 110.0(12) . . ?
C9 C8 C7 113.68(15) . . ?
H9A C9 H9B 105.1(16) . . ?
C8 C9 H9A 108.8(12) . . ?
C8 C9 H9B 109.6(12) . . ?
C10 C9 H9A 109.2(11) . . ?
C10 C9 H9B 110.4(12) . . ?
C10 C9 C8 113.51(16) . . ?
H10A C10 H10B 106.6(17) . . ?
C9 C10 H10A 110.4(12) . . ?
C9 C10 H10B 107.5(12) . . ?
C9 C10 C11 113.98(16) . . ?
C11 C10 H10A 109.0(12) . . ?
C11 C10 H10B 109.0(12) . . ?
H11A C11 H11B 106.2(18) . . ?
C10 C11 H11A 108.7(13) . . ?
C10 C11 H11B 109.3(13) . . ?
C10 C11 C12 112.72(17) . . ?
C12 C11 H11A 110.0(13) . . ?
C12 C11 H11B 109.6(13) . . ?
H12A C12 H12B 109(2) . . ?
H12A C12 H12C 105(2) . . ?
H12B C12 H12C 111(2) . . ?
C11 C12 H12A 112.1(15) . . ?
C11 C12 H12B 109.7(15) . . ?
C11 C12 H12C 109.5(15) . . ?
H13A C13 H13B 111.1(16) . . ?
H13A C13 H13C 112.1(16) . . ?
H13B C13 H13C 112.0(17) . . ?
N1 C13 H13A 107.1(11) . . ?
N1 C13 H13B 107.0(12) . . ?
N1 C13 H13C 107.4(12) . . ?
H14A C14 H14B 110.7(16) . . ?
H14A C14 H14C 107.0(16) . . ?
H14B C14 H14C 111.9(17) . . ?
N1 C14 H14A 109.7(12) . . ?
N1 C14 H14B 107.8(12) . . ?
N1 C14 H14C 109.7(12) . . ?
H15A C15 H15B 112.9(16) . . ?
H15A C15 H15C 109.9(16) . . ?
H15B C15 H15C 109.4(16) . . ?
N1 C15 H15A 109.1(12) . . ?
N1 C15 H15B 108.9(12) . . ?
N1 C15 H15C 106.4(12) . . ?
C13 N1 C1 106.68(11) . . ?
C14 N1 C1 111.24(13) . . ?
C14 N1 C13 108.63(13) . . ?
C14 N1 C15 109.40(12) . . ?
C15 N1 C1 111.62(13) . . ?
C15 N1 C13 109.17(13) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 169.92(16) . . . . ?
C2 C1 N1 C13 171.55(16) . . . . ?
C2 C1 N1 C14 -70.14(19) . . . . ?
C2 C1 N1 C15 52.4(2) . . . . ?
C2 C3 C4 C5 174.21(16) . . . . ?
C3 C4 C5 C6 172.36(16) . . . . ?
C4 C5 C6 C7 178.92(16) . . . . ?
C5 C6 C7 C8 177.23(16) . . . . ?
C6 C7 C8 C9 179.12(16) . . . . ?
C7 C8 C9 C10 178.99(16) . . . . ?
C8 C9 C10 C11 179.61(16) . . . . ?
C9 C10 C11 C12 179.17(18) . . . . ?
N1 C1 C2 C3 165.91(16) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0066 -0.0000 0.0000 -0.9997 -0.0341 -0.0119 0.0017
0 -5 -1 0.1292 -0.1915 -4.6261 -0.8875 -0.1886 0.5601 0.8067
-3 -3 0 0.0968 -2.9540 -2.7006 0.0172 -0.3177 0.9473 0.0418
2 4 0 0.0825 2.1537 3.7336 0.3397 0.2982 -0.8883 -0.3492
3 -3 -1 0.0676 2.9946 -2.6181 -1.0866 0.1199 -0.3603 0.9251
-4 1 1 0.0686 -3.6020 0.5970 0.7976 -0.2406 0.7193 -0.6518
0 0 1 0.0066 0.0000 -0.0000 0.9997 0.0341 0.0119 -0.0017

_olex2_date_sample_data_collection 2015-07-24
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_836
_database_code_depnum_ccdc_archive 'CCDC 1941230'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C10TAB
_chemical_name_systematic        'Decyltrimethylammonium bromide'
_chemical_formula_moiety         'C13 H30 N, Br'
_chemical_formula_sum            'C13 H30 Br N'
_chemical_formula_weight         280.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H30 Br N'
_chemical_oxdiff_usercomment     'From acetone solution (cooled in ice)'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.58903(14)
_cell_length_b                   7.10956(17)
_cell_length_c                   38.0171(9)
_cell_angle_alpha                90
_cell_angle_beta                 85.779(2)
_cell_angle_gamma                90
_cell_volume                     1506.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.3450
_cell_measurement_theta_min      4.6490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.494
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_correction_T_min  0.221
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.3203
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.0457
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            19936
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.485
_diffrn_reflns_theta_min         4.665
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -55.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -68.00  -22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -65.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -125.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   65.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   24.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   24.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  -60.0000 63

#__ type_ start__ end____ width___ exp.time_
 10 omega   25.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   51.0000   84.8061 27

#__ type_ start__ end____ width___ exp.time_
 12 omega  114.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   51.0000   84.8061 27

#__ type_ start__ end____ width___ exp.time_
 13 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   64.0000  125.4313 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   95.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
 15 omega  120.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega  124.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   45.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega  114.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 18 omega   83.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
 19 omega   78.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   82.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   45.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   81.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   45.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 22 omega   78.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 23 omega   77.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
 24 omega   77.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   64.0000 -168.1854 32

#__ type_ start__ end____ width___ exp.time_
 25 omega   74.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
 26 omega   75.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 29 omega   74.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 30 omega   78.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 31 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   77.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 33 omega   74.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
 34 omega   78.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 35 omega   78.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   64.0000  125.4313 72

#__ type_ start__ end____ width___ exp.time_
 36 omega   75.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
 37 omega   77.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 38 omega   79.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
 39 omega  -58.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 40 omega  -78.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 41 omega  -70.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   57.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
 42 omega -119.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -60.0000 109

#__ type_ start__ end____ width___ exp.time_
 43 omega -118.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 44 omega -117.00  -92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega -115.00  -87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 46 omega -118.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  120.0000 30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1689392000
_diffrn_orient_matrix_UB_12      -0.1387213000
_diffrn_orient_matrix_UB_13      -0.0206839000
_diffrn_orient_matrix_UB_21      -0.1386262000
_diffrn_orient_matrix_UB_22      0.0307513000
_diffrn_orient_matrix_UB_23      -0.0331024000
_diffrn_orient_matrix_UB_31      0.1691064000
_diffrn_orient_matrix_UB_32      0.1636034000
_diffrn_orient_matrix_UB_33      -0.0113157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2540
_reflns_number_total             2935
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.237
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0243P)²+3.3617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0949
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B) = Uiso(H10C)
Uiso(H11A) = Uiso(H11B) = Uiso(H11C) = Uiso(H12A) = Uiso(H12B) = Uiso(H12C) =
Uiso(H13A) = Uiso(H13B) = Uiso(H13C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.671(6) 0.378(5) 0.0769(8) 0.012(5) Uiso 1 1 d . . . . .
H1B H 0.639(6) 0.161(5) 0.0735(8) 0.012(5) Uiso 1 1 d . . . . .
H2A H 0.925(7) 0.298(5) 0.1257(9) 0.023(6) Uiso 1 1 d . . . . .
H2B H 0.828(6) 0.089(5) 0.1225(9) 0.023(6) Uiso 1 1 d . . . . .
H3A H 0.558(6) 0.414(5) 0.1412(9) 0.021(6) Uiso 1 1 d . . . . .
H3B H 0.434(7) 0.224(5) 0.1338(9) 0.021(6) Uiso 1 1 d . . . . .
H4A H 0.727(7) 0.270(5) 0.1898(9) 0.022(6) Uiso 1 1 d . . . . .
H4B H 0.584(6) 0.087(5) 0.1823(9) 0.022(6) Uiso 1 1 d . . . . .
H5A H 0.381(6) 0.430(6) 0.2045(8) 0.023(6) Uiso 1 1 d . . . . .
H5B H 0.225(7) 0.271(5) 0.1937(9) 0.023(6) Uiso 1 1 d . . . . .
H6A H 0.500(7) 0.255(5) 0.2528(10) 0.023(6) Uiso 1 1 d . . . . .
H6B H 0.331(6) 0.091(5) 0.2407(9) 0.023(6) Uiso 1 1 d . . . . .
H7A H 0.158(6) 0.453(5) 0.2663(8) 0.021(6) Uiso 1 1 d . . . . .
H7B H -0.009(7) 0.290(5) 0.2535(9) 0.021(6) Uiso 1 1 d . . . . .
H8A H 0.263(7) 0.245(5) 0.3133(9) 0.021(6) Uiso 1 1 d . . . . .
H8B H 0.096(6) 0.096(6) 0.3001(8) 0.021(6) Uiso 1 1 d . . . . .
H9A H -0.065(7) 0.452(5) 0.3268(9) 0.027(7) Uiso 1 1 d . . . . .
H9B H -0.242(7) 0.301(5) 0.3137(9) 0.027(7) Uiso 1 1 d . . . . .
H10A H 0.022(8) 0.238(6) 0.3741(11) 0.038(6) Uiso 1 1 d . . . . .
H10B H -0.148(7) 0.085(6) 0.3600(10) 0.038(6) Uiso 1 1 d . . . . .
H10C H -0.253(7) 0.288(6) 0.3772(10) 0.038(6) Uiso 1 1 d . . . . .
H11A H 0.759(6) 0.367(5) 0.0166(8) 0.020(3) Uiso 1 1 d . . . . .
H11B H 0.766(6) 0.144(5) 0.0154(8) 0.020(3) Uiso 1 1 d . . . . .
H11C H 0.998(7) 0.256(5) 0.0001(9) 0.020(3) Uiso 1 1 d . . . . .
H12A H 1.183(6) 0.416(5) 0.0807(9) 0.020(3) Uiso 1 1 d . . . . .
H12B H 1.017(6) 0.527(5) 0.0558(8) 0.020(3) Uiso 1 1 d . . . . .
H12C H 1.239(6) 0.413(5) 0.0385(9) 0.020(3) Uiso 1 1 d . . . . .
H13A H 1.001(6) -0.035(5) 0.0555(8) 0.020(3) Uiso 1 1 d . . . . .
H13B H 1.178(6) 0.073(5) 0.0797(9) 0.020(3) Uiso 1 1 d . . . . .
H13C H 1.225(6) 0.075(5) 0.0383(9) 0.020(3) Uiso 1 1 d . . . . .
C1 C 0.7431(5) 0.2546(4) 0.08080(7) 0.0177(6) Uani 1 1 d . . . . .
C2 C 0.7934(6) 0.2205(4) 0.11900(8) 0.0200(6) Uani 1 1 d . . . . .
C3 C 0.5732(6) 0.2807(5) 0.14245(8) 0.0223(6) Uani 1 1 d . . . . .
C4 C 0.5793(6) 0.2231(4) 0.18103(8) 0.0214(6) Uani 1 1 d . . . . .
C5 C 0.3683(6) 0.3011(4) 0.20392(8) 0.0206(6) Uani 1 1 d . . . . .
C6 C 0.3505(6) 0.2272(4) 0.24159(8) 0.0215(6) Uani 1 1 d . . . . .
C7 C 0.1417(6) 0.3095(4) 0.26445(8) 0.0219(6) Uani 1 1 d . . . . .
C8 C 0.1138(6) 0.2276(4) 0.30164(8) 0.0214(6) Uani 1 1 d . . . . .
C9 C -0.0925(6) 0.3114(5) 0.32480(8) 0.0244(7) Uani 1 1 d . . . . .
C10 C -0.1186(7) 0.2237(5) 0.36138(9) 0.0321(8) Uani 1 1 d . . . . .
C11 C 0.8605(5) 0.2555(5) 0.01825(8) 0.0207(6) Uani 1 1 d . . . . .
C12 C 1.1154(6) 0.4187(4) 0.05780(8) 0.0202(6) Uani 1 1 d . . . . .
C13 C 1.1019(6) 0.0749(4) 0.05725(8) 0.0198(6) Uani 1 1 d . . . . .
N1 N 0.9570(4) 0.2504(3) 0.05407(6) 0.0163(5) Uani 1 1 d . . . . .
Br1 Br 0.58241(5) 0.75251(4) 0.04890(2) 0.02177(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.98(3) . ?
C1 H1B 0.94(3) . ?
C1 C2 1.519(4) . ?
C1 N1 1.511(4) . ?
C2 H2A 0.97(4) . ?
C2 H2B 0.97(4) . ?
C2 C3 1.527(4) . ?
C3 H3A 0.95(4) . ?
C3 H3B 0.96(4) . ?
C3 C4 1.526(4) . ?
C4 H4A 0.97(4) . ?
C4 H4B 0.97(4) . ?
C4 C5 1.518(4) . ?
C5 H5A 0.92(4) . ?
C5 H5B 0.94(4) . ?
C5 C6 1.522(4) . ?
C6 H6A 0.98(4) . ?
C6 H6B 0.97(4) . ?
C6 C7 1.520(4) . ?
C7 H7A 1.03(4) . ?
C7 H7B 0.97(4) . ?
C7 C8 1.527(4) . ?
C8 H8A 0.98(4) . ?
C8 H8B 0.95(4) . ?
C8 C9 1.520(4) . ?
C9 H9A 1.01(4) . ?
C9 H9B 0.96(4) . ?
C9 C10 1.521(5) . ?
C10 H10A 0.96(4) . ?
C10 H10B 1.00(4) . ?
C10 H10C 1.04(4) . ?
C11 H11A 0.98(4) . ?
C11 H11B 0.96(4) . ?
C11 H11C 0.99(4) . ?
C11 N1 1.501(3) . ?
C12 H12A 0.98(3) . ?
C12 H12B 0.95(4) . ?
C12 H12C 0.97(3) . ?
C12 N1 1.502(4) . ?
C13 H13A 0.97(4) . ?
C13 H13B 0.98(3) . ?
C13 H13C 0.96(3) . ?
C13 N1 1.497(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
_geom_angle_publ_flag
H1A C1 H1B 108(3) . . ?
C2 C1 H1A 113.3(17) . . ?
C2 C1 H1B 109.4(18) . . ?
N1 C1 H1A 103.3(18) . . ?
N1 C1 H1B 105.4(19) . . ?
N1 C1 C2 116.5(2) . . ?
H2A C2 H2B 110(3) . . ?
C1 C2 H2A 111(2) . . ?
C1 C2 H2B 110(2) . . ?
C1 C2 C3 108.4(2) . . ?
C3 C2 H2A 106(2) . . ?
C3 C2 H2B 111(2) . . ?
H3A C3 H3B 109(3) . . ?
C2 C3 H3A 109(2) . . ?
C2 C3 H3B 109(2) . . ?
C4 C3 H3A 109(2) . . ?
C4 C3 H3B 107(2) . . ?
C4 C3 C2 114.3(3) . . ?
H4A C4 H4B 107(3) . . ?
C3 C4 H4A 108(2) . . ?
C3 C4 H4B 109(2) . . ?
C5 C4 H4A 109(2) . . ?
C5 C4 H4B 111(2) . . ?
C5 C4 C3 112.4(3) . . ?
H5A C5 H5B 108(3) . . ?
C4 C5 H5A 109(2) . . ?
C4 C5 H5B 109(2) . . ?
C4 C5 C6 114.0(3) . . ?
C6 C5 H5A 109(2) . . ?
C6 C5 H5B 108(2) . . ?
H6A C6 H6B 108(3) . . ?
C5 C6 H6A 110(2) . . ?
C5 C6 H6B 108(2) . . ?
C7 C6 H6A 108(2) . . ?
C7 C6 H6B 109(2) . . ?
C7 C6 C5 113.5(3) . . ?
H7A C7 H7B 105(3) . . ?
C6 C7 H7A 111(2) . . ?
C6 C7 H7B 111(2) . . ?
C6 C7 C8 113.9(3) . . ?
C8 C7 H7A 108.6(18) . . ?
C8 C7 H7B 108(2) . . ?
H8A C8 H8B 105(3) . . ?
C7 C8 H8A 110(2) . . ?
C7 C8 H8B 109.0(19) . . ?
C9 C8 H8A 109(2) . . ?
C9 C8 H8B 110(2) . . ?
C9 C8 C7 114.1(3) . . ?
H9A C9 H9B 104(3) . . ?
C8 C9 H9A 108(2) . . ?
C8 C9 H9B 111(2) . . ?
C8 C9 C10 112.8(3) . . ?
C10 C9 H9A 110(2) . . ?
C10 C9 H9B 110(2) . . ?
H10A C10 H10B 106(3) . . ?
H10A C10 H10C 104(3) . . ?
H10B C10 H10C 111(3) . . ?
C9 C10 H10A 113(2) . . ?
C9 C10 H10B 111(2) . . ?
C9 C10 H10C 111(2) . . ?
H11A C11 H11B 110(3) . . ?
H11A C11 H11C 112(3) . . ?
H11B C11 H11C 109(3) . . ?
N1 C11 H11A 109.0(19) . . ?
N1 C11 H11B 109(2) . . ?
N1 C11 H11C 109(2) . . ?
H12A C12 H12B 111(3) . . ?
H12A C12 H12C 112(3) . . ?
H12B C12 H12C 111(3) . . ?
N1 C12 H12A 110(2) . . ?
N1 C12 H12B 107(2) . . ?
N1 C12 H12C 107(2) . . ?
H13A C13 H13B 110(3) . . ?
H13A C13 H13C 110(3) . . ?
H13B C13 H13C 109(3) . . ?
N1 C13 H13A 110(2) . . ?
N1 C13 H13B 111(2) . . ?
N1 C13 H13C 108(2) . . ?
C11 N1 C1 106.9(2) . . ?
C11 N1 C12 108.7(2) . . ?
C12 N1 C1 111.3(2) . . ?
C13 N1 C1 111.6(2) . . ?
C13 N1 C11 109.0(2) . . ?
C13 N1 C12 109.3(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 169.8(3) . . . . ?
C2 C1 N1 C11 170.9(3) . . . . ?
C2 C1 N1 C12 -70.6(3) . . . . ?
C2 C1 N1 C13 51.8(3) . . . . ?
C2 C3 C4 C5 174.8(3) . . . . ?
C3 C4 C5 C6 172.8(3) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C5 C6 C7 C8 176.6(3) . . . . ?
C6 C7 C8 C9 179.1(3) . . . . ?
C7 C8 C9 C10 178.7(3) . . . . ?
N1 C1 C2 C3 165.2(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 -4 11 0.0928 1.0611 -3.9268 11.2567 0.4912 -0.6405 -0.5904
1 4 -8 0.1052 1.1784 4.0213 -8.4741 -0.1835 0.2408 0.9531
-4 0 -4 0.1075 -3.6054 -0.2484 -4.2389 -0.4870 0.6325 -0.6024
0 0 -1 0.0228 -0.0000 0.0000 -0.9999 0.0207 0.0331 0.0113
0 0 1 0.0228 0.0000 -0.0000 0.9999 -0.0207 -0.0331 -0.0113
-3 3 -8 0.1164 -2.8354 2.6364 -7.5620 -0.6883 0.7244 0.0374
4 0 4 0.2019 3.5978 -0.4928 3.5867 0.6020 -0.6326 0.4872
-3 -2 2 0.1203 -3.1751 -2.1201 2.2170 -0.2881 0.3016 -0.9089
2 3 -6 0.1311 2.1812 3.4602 -5.7439 0.0073 -0.0058 1.0000

_olex2_date_sample_data_collection 2015-08-26
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0483
_database_code_depnum_ccdc_archive 'CCDC 1941231'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C10TAB
_chemical_name_systematic        'Decyltrimethylammonium bromide'
_chemical_formula_moiety         'C13 H30 N, Br'
_chemical_formula_sum            'C13 H30 Br N'
_chemical_formula_weight         280.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H30 Br N'
_chemical_oxdiff_usercomment     
'Crystals grown from acetone solution cooled on ice'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.60055(7)
_cell_length_b                   7.13788(7)
_cell_length_c                   38.1311(4)
_cell_angle_alpha                90
_cell_angle_beta                 85.4663(10)
_cell_angle_gamma                90
_cell_volume                     1519.56(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13084
_cell_measurement_temperature    150
_cell_measurement_theta_max      75.9540
_cell_measurement_theta_min      4.6490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.465
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_correction_T_min  0.369
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.5307
_exptl_crystal_size_mid          0.2158
_exptl_crystal_size_min          0.0557
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            26935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.503
_diffrn_reflns_theta_min         4.653
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega  -82.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega -103.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
  6 omega  -64.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  7 omega -106.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   15.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216   57.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   84.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   58.0000   18.9329 27

#__ type_ start__ end____ width___ exp.time_
 10 omega  131.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   41.2991 34

#__ type_ start__ end____ width___ exp.time_
 11 omega  138.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   58.0000   18.9329 39

#__ type_ start__ end____ width___ exp.time_
 12 omega  151.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -84.5304 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  141.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  125.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  123.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 16 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   60.0000  -75.1004 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
 18 omega   83.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 76

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
 20 omega  125.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   62.0000   97.0792 31

#__ type_ start__ end____ width___ exp.time_
 21 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  127.00  163.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
 23 omega  121.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   80.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.0000  104.2176 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   85.00  154.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   53.0000  120.1056 69

#__ type_ start__ end____ width___ exp.time_
 26 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   83.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   62.0000   97.0792 32

#__ type_ start__ end____ width___ exp.time_
 28 omega   80.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
 29 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   79.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 31 omega   79.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 98

#__ type_ start__ end____ width___ exp.time_
 32 omega   79.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
 33 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   84.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 35 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   80.00  153.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
 37 omega   84.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
 38 omega   85.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 39 omega   83.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   79.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   41.2991 47

#__ type_ start__ end____ width___ exp.time_
 41 omega   79.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 42 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -84.5304 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   83.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
 45 omega  108.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 46 omega   76.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 47 omega   84.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 48 omega   73.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 49 omega   62.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
 50 omega   44.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 51 omega   51.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 52 omega   68.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 53 omega   42.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 54 omega   44.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 65

#__ type_ start__ end____ width___ exp.time_
 55 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega   31.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 57 omega    1.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216  -99.0000  -90.0000 83

#__ type_ start__ end____ width___ exp.time_
 58 omega    5.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216  -99.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 59 omega  -79.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  125.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
 60 omega -116.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 61 omega -116.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   90.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0976340000
_diffrn_orient_matrix_UB_12      -0.1604583000
_diffrn_orient_matrix_UB_13      -0.0240679000
_diffrn_orient_matrix_UB_21      0.0662647000
_diffrn_orient_matrix_UB_22      -0.1110004000
_diffrn_orient_matrix_UB_23      0.0324915000
_diffrn_orient_matrix_UB_31      -0.2494549000
_diffrn_orient_matrix_UB_32      -0.0922402000
_diffrn_orient_matrix_UB_33      0.0027650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2705
_reflns_number_total             3154
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0222
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.4346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0618
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B) = Uiso(H10C)
Uiso(H11A) = Uiso(H11B) = Uiso(H11C)
Uiso(H12A) = Uiso(H12B) = Uiso(H12C)
Uiso(H13A) = Uiso(H13B) = Uiso(H13C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.673(3) 0.372(2) 0.0776(4) 0.022(3) Uiso 1 1 d . . . . .
H1B H 0.635(3) 0.160(2) 0.0731(4) 0.022(3) Uiso 1 1 d . . . . .
H2A H 0.933(4) 0.298(3) 0.1251(5) 0.037(3) Uiso 1 1 d . . . . .
H2B H 0.829(3) 0.088(3) 0.1225(4) 0.037(3) Uiso 1 1 d . . . . .
H3A H 0.554(3) 0.417(3) 0.1408(5) 0.037(3) Uiso 1 1 d . . . . .
H3B H 0.435(4) 0.227(2) 0.1339(5) 0.037(3) Uiso 1 1 d . . . . .
H4A H 0.726(4) 0.266(2) 0.1900(5) 0.028(3) Uiso 1 1 d . . . . .
H4B H 0.579(3) 0.086(2) 0.1828(4) 0.028(3) Uiso 1 1 d . . . . .
H5A H 0.374(3) 0.438(3) 0.2039(4) 0.033(3) Uiso 1 1 d . . . . .
H5B H 0.224(4) 0.269(2) 0.1939(5) 0.033(3) Uiso 1 1 d . . . . .
H6A H 0.496(4) 0.254(2) 0.2522(5) 0.030(3) Uiso 1 1 d . . . . .
H6B H 0.336(3) 0.095(3) 0.2411(4) 0.030(3) Uiso 1 1 d . . . . .
H7A H 0.163(3) 0.444(3) 0.2659(5) 0.036(3) Uiso 1 1 d . . . . .
H7B H -0.013(4) 0.288(2) 0.2534(5) 0.036(3) Uiso 1 1 d . . . . .
H8A H 0.266(4) 0.249(2) 0.3131(5) 0.031(3) Uiso 1 1 d . . . . .
H8B H 0.095(3) 0.093(3) 0.2999(4) 0.031(3) Uiso 1 1 d . . . . .
H9A H -0.076(3) 0.443(3) 0.3269(5) 0.041(4) Uiso 1 1 d . . . . .
H9B H -0.231(4) 0.297(3) 0.3141(5) 0.041(4) Uiso 1 1 d . . . . .
H10A H 0.028(5) 0.241(3) 0.3737(7) 0.053(4) Uiso 1 1 d . . . . .
H10B H -0.154(4) 0.093(3) 0.3592(5) 0.053(4) Uiso 1 1 d . . . . .
H10C H -0.241(4) 0.283(3) 0.3765(6) 0.053(4) Uiso 1 1 d . . . . .
H11A H 0.766(3) 0.368(2) 0.0172(4) 0.028(3) Uiso 1 1 d . . . . .
H11B H 0.763(3) 0.147(2) 0.0162(4) 0.028(3) Uiso 1 1 d . . . . .
H11C H 0.996(4) 0.2590(19) 0.0009(5) 0.028(3) Uiso 1 1 d . . . . .
H12A H 1.179(3) 0.413(2) 0.0799(4) 0.027(2) Uiso 1 1 d . . . . .
H12B H 1.020(3) 0.527(3) 0.0559(4) 0.027(2) Uiso 1 1 d . . . . .
H12C H 1.241(3) 0.414(2) 0.0390(4) 0.027(2) Uiso 1 1 d . . . . .
H13A H 1.002(3) -0.028(3) 0.0556(4) 0.027(2) Uiso 1 1 d . . . . .
H13B H 1.175(3) 0.076(2) 0.0790(4) 0.027(2) Uiso 1 1 d . . . . .
H13C H 1.228(3) 0.078(2) 0.0383(4) 0.027(2) Uiso 1 1 d . . . . .
C1 C 0.7414(2) 0.25425(17) 0.08072(3) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.7922(3) 0.2218(2) 0.11884(3) 0.0242(3) Uani 1 1 d . . . . .
C3 C 0.5712(3) 0.2797(2) 0.14230(4) 0.0275(3) Uani 1 1 d . . . . .
C4 C 0.5783(3) 0.2231(2) 0.18079(3) 0.0254(3) Uani 1 1 d . . . . .
C5 C 0.3670(3) 0.3013(2) 0.20381(3) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.3506(3) 0.2269(2) 0.24144(4) 0.0250(3) Uani 1 1 d . . . . .
C7 C 0.1410(3) 0.3094(2) 0.26444(3) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.1165(3) 0.2279(2) 0.30162(4) 0.0263(3) Uani 1 1 d . . . . .
C9 C -0.0904(3) 0.3109(2) 0.32483(4) 0.0302(3) Uani 1 1 d . . . . .
C10 C -0.1156(4) 0.2235(3) 0.36145(4) 0.0413(4) Uani 1 1 d . . . . .
C11 C 0.8589(3) 0.25553(19) 0.01836(3) 0.0250(3) Uani 1 1 d . . . . .
C12 C 1.1128(2) 0.41778(19) 0.05768(4) 0.0232(3) Uani 1 1 d . . . . .
C13 C 1.1005(3) 0.07537(19) 0.05697(4) 0.0238(3) Uani 1 1 d . . . . .
N1 N 0.9553(2) 0.25028(13) 0.05401(3) 0.0181(2) Uani 1 1 d . . . . .
Br1 Br 0.58107(2) 0.75220(2) 0.04889(2) 0.02682(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.937(16) . ?
C1 H1B 0.959(17) . ?
C1 C2 1.5205(17) . ?
C1 N1 1.5098(16) . ?
C2 H2A 1.00(2) . ?
C2 H2B 0.988(18) . ?
C2 C3 1.5255(19) . ?
C3 H3A 0.984(18) . ?
C3 H3B 0.93(2) . ?
C3 C4 1.5259(18) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.980(17) . ?
C4 C5 1.5227(19) . ?
C5 H5A 0.977(18) . ?
C5 H5B 0.94(2) . ?
C5 C6 1.5259(18) . ?
C6 H6A 0.96(2) . ?
C6 H6B 0.943(18) . ?
C6 C7 1.5263(19) . ?
C7 H7A 0.973(18) . ?
C7 H7B 1.00(2) . ?
C7 C8 1.5286(18) . ?
C8 H8A 0.98(2) . ?
C8 H8B 0.970(19) . ?
C8 C9 1.521(2) . ?
C9 H9A 0.952(19) . ?
C9 H9B 0.92(2) . ?
C9 C10 1.525(2) . ?
C10 H10A 0.97(3) . ?
C10 H10B 0.96(2) . ?
C10 H10C 0.97(2) . ?
C11 H11A 0.960(18) . ?
C11 H11B 0.949(18) . ?
C11 H11C 0.98(2) . ?
C11 N1 1.5019(16) . ?
C12 H12A 0.952(17) . ?
C12 H12B 0.942(18) . ?
C12 H12C 0.969(17) . ?
C12 N1 1.4992(16) . ?
C13 H13A 0.928(18) . ?
C13 H13B 0.966(17) . ?
C13 H13C 0.968(17) . ?
C13 N1 1.4991(16) . ?

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
_geom_angle_publ_flag
H1A C1 H1B 108.8(14) . . ?
C2 C1 H1A 111.5(9) . . ?
C2 C1 H1B 110.6(9) . . ?
N1 C1 H1A 104.0(10) . . ?
N1 C1 H1B 105.1(9) . . ?
N1 C1 C2 116.35(11) . . ?
H2A C2 H2B 108.1(14) . . ?
C1 C2 H2A 110.9(11) . . ?
C1 C2 H2B 109.8(10) . . ?
C1 C2 C3 108.36(11) . . ?
C3 C2 H2A 109.3(11) . . ?
C3 C2 H2B 110.4(11) . . ?
H3A C3 H3B 107.2(15) . . ?
C2 C3 H3A 108.4(11) . . ?
C2 C3 H3B 109.6(13) . . ?
C2 C3 C4 114.25(12) . . ?
C4 C3 H3A 109.2(10) . . ?
C4 C3 H3B 108.0(12) . . ?
H4A C4 H4B 106.2(13) . . ?
C3 C4 H4A 110.4(11) . . ?
C3 C4 H4B 109.8(9) . . ?
C5 C4 H4A 108.7(11) . . ?
C5 C4 H4B 109.3(10) . . ?
C5 C4 C3 112.30(12) . . ?
H5A C5 H5B 106.4(14) . . ?
C4 C5 H5A 109.8(10) . . ?
C4 C5 H5B 108.9(12) . . ?
C4 C5 C6 113.64(12) . . ?
C6 C5 H5A 110.2(9) . . ?
C6 C5 H5B 107.6(12) . . ?
H6A C6 H6B 106.7(13) . . ?
C5 C6 H6A 109.9(12) . . ?
C5 C6 H6B 109.4(10) . . ?
C5 C6 C7 113.11(12) . . ?
C7 C6 H6A 108.3(12) . . ?
C7 C6 H6B 109.2(11) . . ?
H7A C7 H7B 106.8(14) . . ?
C6 C7 H7A 108.7(11) . . ?
C6 C7 H7B 110.5(11) . . ?
C6 C7 C8 113.27(12) . . ?
C8 C7 H7A 108.9(10) . . ?
C8 C7 H7B 108.4(11) . . ?
H8A C8 H8B 107.1(12) . . ?
C7 C8 H8A 109.6(11) . . ?
C7 C8 H8B 108.4(9) . . ?
C9 C8 H8A 108.4(11) . . ?
C9 C8 H8B 109.5(10) . . ?
C9 C8 C7 113.59(13) . . ?
H9A C9 H9B 102.8(16) . . ?
C8 C9 H9A 111.7(12) . . ?
C8 C9 H9B 109.8(13) . . ?
C8 C9 C10 112.61(14) . . ?
C10 C9 H9A 109.4(11) . . ?
C10 C9 H9B 110.0(12) . . ?
H10A C10 H10B 111.6(16) . . ?
H10A C10 H10C 104.4(19) . . ?
H10B C10 H10C 108.5(17) . . ?
C9 C10 H10A 111.6(14) . . ?
C9 C10 H10B 108.7(12) . . ?
C9 C10 H10C 112.0(14) . . ?
H11A C11 H11B 111.2(16) . . ?
H11A C11 H11C 110.4(13) . . ?
H11B C11 H11C 112.5(13) . . ?
N1 C11 H11A 107.4(10) . . ?
N1 C11 H11B 107.7(10) . . ?
N1 C11 H11C 107.4(12) . . ?
H12A C12 H12B 110.7(14) . . ?
H12A C12 H12C 109.5(14) . . ?
H12B C12 H12C 110.5(14) . . ?
N1 C12 H12A 109.1(10) . . ?
N1 C12 H12B 108.8(11) . . ?
N1 C12 H12C 108.3(10) . . ?
H13A C13 H13B 110.9(14) . . ?
H13A C13 H13C 112.4(14) . . ?
H13B C13 H13C 107.0(14) . . ?
N1 C13 H13A 109.3(11) . . ?
N1 C13 H13B 109.6(10) . . ?
N1 C13 H13C 107.7(10) . . ?
C11 N1 C1 106.72(10) . . ?
C12 N1 C1 111.30(9) . . ?
C12 N1 C11 108.72(10) . . ?
C13 N1 C1 111.77(10) . . ?
C13 N1 C11 108.96(10) . . ?
C13 N1 C12 109.28(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 169.69(12) . . . . ?
C2 C1 N1 C11 171.50(11) . . . . ?
C2 C1 N1 C12 -70.03(14) . . . . ?
C2 C1 N1 C13 52.47(14) . . . . ?
C2 C3 C4 C5 173.99(13) . . . . ?
C3 C4 C5 C6 172.48(13) . . . . ?
C4 C5 C6 C7 178.85(13) . . . . ?
C5 C6 C7 C8 177.12(13) . . . . ?
C6 C7 C8 C9 179.39(13) . . . . ?
C7 C8 C9 C10 178.38(14) . . . . ?
N1 C1 C2 C3 165.73(11) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0279 -0.0000 -0.0001 0.9999 -0.0241 0.0325 0.0028
0 0 -1 0.0279 0.0000 0.0001 -0.9999 0.0241 -0.0325 -0.0028
-2 4 0 0.0978 -2.0028 3.8645 -0.4253 -0.8054 -0.5755 0.1420
3 3 0 0.2537 2.7543 3.0120 0.0032 -0.2145 -0.1517 -0.9649
3 -3 0 0.0871 2.5486 -3.2987 0.4282 0.7678 0.5489 -0.3303
-1 -4 0 0.1895 -0.9750 -4.4618 0.2361 0.6151 0.4383 0.6554
-3 1 0 0.2114 -3.4796 1.3099 -0.3614 -0.5412 -0.3877 0.7462
-3 -2 0 0.2656 -3.2624 -2.0214 -0.1119 0.0085 0.0046 1.0000

_olex2_date_sample_data_collection 2015-08-11
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_807
_database_code_depnum_ccdc_archive 'CCDC 1941229'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C12TAB
_chemical_name_systematic        'Dodecyltrimethylammonium bromide'
_chemical_formula_moiety         'C15 H34 N, Br'
_chemical_formula_sum            'C15 H34 Br N'
_chemical_formula_weight         308.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H34 Br N'
_chemical_oxdiff_usercomment     'C12TAB at RT (295K)'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.64120(8)
_cell_length_b                   7.25452(11)
_cell_length_c                   21.5625(4)
_cell_angle_alpha                90
_cell_angle_beta                 86.9956(13)
_cell_angle_gamma                90
_cell_volume                     881.21(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8641
_cell_measurement_temperature    295
_cell_measurement_theta_max      73.3920
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.028
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.2837
_exptl_crystal_size_mid          0.1553
_exptl_crystal_size_min          0.0229
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12281
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.557
_diffrn_reflns_theta_min         4.106
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216  -99.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega  107.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   47.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  150.0000 72

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -142.0000  174.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega   26.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
 11 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega  112.00  171.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega  117.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 14 omega  114.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   94.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
 16 omega   78.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   77.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 18 omega   78.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 19 omega   78.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
 20 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   78.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   75.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000  -86.1397 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   78.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   57.0000  -97.2734 95

#__ type_ start__ end____ width___ exp.time_
 25 omega   74.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 99

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
 27 omega   78.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
 28 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   77.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
 31 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   74.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 33 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   77.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 35 omega   77.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 36 omega   76.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   72.0000  -70.0567 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega  -49.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 39 omega  -13.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 40 omega  -83.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
 41 omega -118.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   60.0000 108

#__ type_ start__ end____ width___ exp.time_
 42 omega -119.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -60.0000 109

#__ type_ start__ end____ width___ exp.time_
 43 omega -114.00  -89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 44 omega -116.00  -91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0787027000
_diffrn_orient_matrix_UB_12      0.0373676000
_diffrn_orient_matrix_UB_13      -0.0661737000
_diffrn_orient_matrix_UB_21      0.2099052000
_diffrn_orient_matrix_UB_22      -0.1157853000
_diffrn_orient_matrix_UB_23      -0.0269773000
_diffrn_orient_matrix_UB_31      -0.1565552000
_diffrn_orient_matrix_UB_32      -0.1740455000
_diffrn_orient_matrix_UB_33      0.0037221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1787
_reflns_number_total             1896
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1896
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      0.998
_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)+(0.0677P)²+0.3718P+1.0000sinθ/λ] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10_$1
 0.97 with sigma of 0.005
 C11-H11 = C11-H11_$1
 0.97 with sigma of 0.005
 C12-H12 = C12-H12M = C12-H12_$1
 0.96 with sigma of 0.005
 C13-H13 = C13-H13M = C13-H13_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1
 1.565 with sigma of 0.005
 H11-H11_$1
 1.565 with sigma of 0.005
 H12-H12_$1 = H12-H12M
 1.565 with sigma of 0.005
 H13-H13_$1 = H13-H13M
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10 \\sim C11-H10 \\sim C11-H10_$1
 with sigma of 0.005
 C10-H11 \\sim C10-H11_$1 \\sim C12-H11 \\sim C12-H11_$1
 with sigma of 0.005
 C11-H12 \\sim C11-H12M \\sim C11-H12_$1
 with sigma of 0.005
 N1-H13 \\sim N1-H13M \\sim N1-H13_$1
 with sigma of 0.005
 H12-H12M \\sim H12M-H12_$1 \\sim H12_$1-H12
 with sigma of 0.005
 H13-H13M \\sim H13M-H13_$1 \\sim H13_$1-H13
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7661(5) 0.2500 0.14442(14) 0.0457(7) Uani 1 2 d DS T P . .
H1 H 0.6699(13) 0.3579(4) 0.1372(2) 0.055 Uiso 1 1 d DR . . . .
C2 C 0.8308(7) 0.2500 0.21082(18) 0.0696(11) Uani 1 2 d DS T P . .
H2 H 0.9270(14) 0.3579(4) 0.2182(2) 0.083 Uiso 1 1 d DR . . . .
C3 C 0.6171(8) 0.2500 0.25382(18) 0.0764(12) Uani 1 2 d DS T P . .
H3 H 0.5243(14) 0.3578(4) 0.2441(3) 0.092 Uiso 1 1 d DR . . . .
C4 C 0.6436(8) 0.2500 0.32172(19) 0.0771(12) Uani 1 2 d DS T P . .
H4 H 0.7389(14) 0.3579(4) 0.3297(3) 0.093 Uiso 1 1 d DR . . . .
C5 C 0.4399(10) 0.2500 0.3641(2) 0.118(3) Uani 1 2 d DS T P . .
H5 H 0.3481(15) 0.3578(4) 0.3539(3) 0.142 Uiso 1 1 d DR . . . .
C6 C 0.4469(9) 0.2500 0.4305(2) 0.0785(12) Uani 1 2 d DS T P . .
H6 H 0.5394(15) 0.3578(4) 0.4405(3) 0.094 Uiso 1 1 d DR . . . .
C7 C 0.2441(11) 0.2500 0.4725(2) 0.144(4) Uani 1 2 d DS T P . .
H7 H 0.1537(16) 0.3578(4) 0.4615(3) 0.172 Uiso 1 1 d DR . . . .
C8 C 0.2406(9) 0.2500 0.5383(2) 0.0828(14) Uani 1 2 d DS T P . .
H8 H 0.3322(15) 0.3578(4) 0.5487(3) 0.099 Uiso 1 1 d DR . . . .
C9 C 0.0424(12) 0.2500 0.5806(2) 0.169(5) Uani 1 2 d DS T P . .
H9 H -0.0486(17) 0.3578(4) 0.5698(3) 0.202 Uiso 1 1 d DR . . . .
C10 C 0.0361(11) 0.2500 0.6460(2) 0.0907(16) Uani 1 2 d DS T P . .
H10 H 0.1277(16) 0.3578(4) 0.6565(4) 0.109 Uiso 1 1 d DR . . . .
C11 C -0.1587(14) 0.2500 0.6894(3) 0.185(5) Uani 1 2 d DS T P . .
H11 H -0.2479(18) 0.3578(4) 0.6777(3) 0.222 Uiso 1 1 d DR . . . .
C12 C -0.1684(15) 0.2500 0.7531(3) 0.137(3) Uani 1 2 d DS T P . .
H12 H -0.090(2) 0.3579(3) 0.7677(5) 0.206 Uiso 1 1 d DR . . . .
H12M H -0.331(2) 0.2500 0.7686(7) 0.206 Uiso 1 2 d DRS T P . .
C13 C 0.8593(6) 0.2500 0.03385(14) 0.0559(8) Uani 1 2 d DS T P . .
H13 H 0.7630(12) 0.3580(3) 0.0303(5) 0.084 Uiso 1 1 d DR . . . .
H13M H 0.9823(17) 0.2500 0.0014(4) 0.084 Uiso 1 2 d DRS T P . .
C14 C 1.1199(4) 0.4184(3) 0.10048(11) 0.0528(5) Uani 1 1 d . . . . .
H14A H 1.0225 0.5264 0.0982 0.079 Uiso 1 1 calc GR . . . .
H14B H 1.2390 0.4198 0.0670 0.079 Uiso 1 1 calc GR . . . .
H14C H 1.1952 0.4172 0.1394 0.079 Uiso 1 1 calc GR . . . .
N1 N 0.9691(4) 0.2500 0.09556(11) 0.0409(5) Uani 1 2 d DS T P . .
Br1 Br 0.59453(6) 0.7500 0.08621(2) 0.05809(17) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.970(4) . ?
C1 C2 1.496(5) . ?
C1 N1 1.515(4) . ?
C2 H2 0.970(4) . ?
C2 C3 1.482(6) . ?
C3 H3 0.971(4) . ?
C3 C4 1.479(6) . ?
C4 H4 0.970(4) . ?
C4 C5 1.430(6) . ?
C5 H5 0.970(4) . ?
C5 C6 1.434(6) . ?
C6 H6 0.971(4) . ?
C6 C7 1.422(7) . ?
C7 H7 0.970(4) . ?
C7 C8 1.417(7) . ?
C8 H8 0.970(4) . ?
C8 C9 1.406(7) . ?
C9 H9 0.970(4) . ?
C9 C10 1.408(7) . ?
C10 H10 0.971(4) . ?
C10 C11 1.406(8) . ?
C11 H11 0.970(4) . ?
C11 C12 1.371(9) . ?
C12 H12 0.960(4) . ?
C12 H12M 0.959(5) . ?
C13 H13 0.958(4) . ?
C13 H13M 0.960(5) . ?
C13 N1 1.497(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 N1 1.496(3) . ?
N1 C14 1.496(3) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 108.7(3) . . ?
C2 C1 N1 116.9(3) . . ?
N1 C1 H1 107.3(4) . . ?
C1 C2 H2 108.9(4) . . ?
C3 C2 C1 111.6(3) . . ?
C3 C2 H2 109.9(4) . . ?
C2 C3 H3 107.1(4) . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 107.3(4) . . ?
C3 C4 H4 105.1(4) . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 108.7(4) . . ?
C4 C5 H5 106.0(4) . . ?
C4 C5 C6 125.0(5) . . ?
C6 C5 H5 105.7(4) . . ?
C5 C6 H6 105.5(4) . . ?
C7 C6 C5 124.9(5) . . ?
C7 C6 H6 106.3(4) . . ?
C6 C7 H7 105.1(5) . . ?
C8 C7 C6 127.3(6) . . ?
C8 C7 H7 105.4(5) . . ?
C7 C8 H8 104.6(5) . . ?
C9 C8 C7 128.2(6) . . ?
C9 C8 H8 105.3(5) . . ?
C8 C9 H9 104.9(5) . . ?
C8 C9 C10 128.9(7) . . ?
C10 C9 H9 104.7(5) . . ?
C9 C10 H10 104.4(5) . . ?
C11 C10 C9 130.1(7) . . ?
C11 C10 H10 104.6(5) . . ?
C10 C11 H11 103.0(6) . . ?
C12 C11 C10 130.9(8) . . ?
C12 C11 H11 105.5(5) . . ?
C11 C12 H12 109.6(6) . . ?
C11 C12 H12M 109.7(7) . . ?
H12 C12 H12M 109.4(7) . . ?
H13 C13 H13M 109.5(6) . . ?
N1 C13 H13 109.5(6) . . ?
N1 C13 H13M 109.3(7) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
C13 N1 C1 106.6(2) . . ?
C14 N1 C1 111.28(15) 4_565 . ?
C14 N1 C1 111.28(15) . . ?
C14 N1 C13 109.06(16) . . ?
C14 N1 C13 109.06(16) 4_565 . ?
C14 N1 C14 109.5(2) 4_565 . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C1 N1 C13 180.000(0) . . . . ?
C2 C1 N1 C14 61.22(16) . . . 4_565 ?
C2 C1 N1 C14 -61.23(16) . . . . ?
C2 C3 C4 C5 180.000(1) . . . . ?
C3 C4 C5 C6 180.000(2) . . . . ?
C4 C5 C6 C7 180.000(2) . . . . ?
C5 C6 C7 C8 180.000(2) . . . . ?
C6 C7 C8 C9 180.000(3) . . . . ?
C7 C8 C9 C10 180.000(3) . . . . ?
C8 C9 C10 C11 180.000(5) . . . . ?
C9 C10 C11 C12 180.000(5) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0115 0.0000 -0.0000 1.0000 -0.0662 -0.0270 0.0037
0 0 -1 0.0115 -0.0000 0.0000 -1.0000 0.0662 0.0270 -0.0037
4 0 0 0.0436 3.6595 -0.0083 0.1907 -0.3009 0.7640 -0.5708
-3 -3 0 0.0804 -2.9824 -2.7213 0.1465 0.1233 -0.3149 0.9411
-3 3 0 0.0972 -2.7990 3.0371 -0.4813 0.3656 -0.9262 -0.0922
1 5 0 0.1213 0.9703 4.5355 -0.4516 0.1230 -0.3093 -0.9430
3 -3 1 0.1132 2.6188 -3.2923 0.5002 -0.3622 0.9174 0.1649

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0480a
_database_code_depnum_ccdc_archive 'CCDC 1941220'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C18TAB
_chemical_name_systematic        'Octadecyltrimethylammonium bromide'
_chemical_formula_moiety         'C21 H46 N, Br'
_chemical_formula_sum            'C21 H46 Br N'
_chemical_formula_weight         392.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H46 N1 Br'
_chemical_oxdiff_usercomment     'New crystal of C18TAB'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.6617(3)
_cell_length_b                   7.3973(4)
_cell_length_c                   28.5605(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.377(5)
_cell_angle_gamma                90
_cell_volume                     1194.09(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4781
_cell_measurement_temperature    390
_cell_measurement_theta_max      72.4400
_cell_measurement_theta_min      4.6710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.327
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             428
_exptl_crystal_recrystallization_method 
'Recrystallized from acetone:water mixture in fridge'
_exptl_crystal_size_max          0.2617
_exptl_crystal_size_mid          0.0573
_exptl_crystal_size_min          0.0199
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            10389
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.831
_diffrn_reflns_theta_min         4.653
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      390
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00  -14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00  -15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -77.00  -10.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000    0.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega  -62.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
  5 omega  -57.00  -16.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00   62.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -125.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   24.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -125.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00  117.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00  105.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -61.0000   90.0000 61

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216   19.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   74.00  100.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  107.00  164.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
 13 omega  144.00  173.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   74.0000  -33.7098 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  106.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   80.00  178.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   48.0000 -178.1004 98

#__ type_ start__ end____ width___ exp.time_
 16 omega   79.00  177.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 98

#__ type_ start__ end____ width___ exp.time_
 17 omega   78.00  178.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 18 omega   77.00  103.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   77.00  174.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   60.0000 97

#__ type_ start__ end____ width___ exp.time_
 20 omega   77.00  103.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   77.00  175.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  103.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   78.00  151.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
 24 omega   74.00  105.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 25 omega   75.00  100.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   74.00  101.00   1.0000   24.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1444768000
_diffrn_orient_matrix_UB_12      -0.1090032000
_diffrn_orient_matrix_UB_13      0.0376348000
_diffrn_orient_matrix_UB_21      0.1355163000
_diffrn_orient_matrix_UB_22      -0.0926995000
_diffrn_orient_matrix_UB_23      -0.0386119000
_diffrn_orient_matrix_UB_31      0.1872308000
_diffrn_orient_matrix_UB_32      0.1513286000
_diffrn_orient_matrix_UB_33      0.0034593000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2071
_reflns_number_total             2534
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      0.985
_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)+(0.1021P)²+0.2426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10_$1
 0.97 with sigma of 0.005
 C11-H11 = C11-H11_$1
 0.97 with sigma of 0.005
 C12-H12 = C12-H12_$1
 0.97 with sigma of 0.005
 C13-H13 = C13-H13_$1
 0.97 with sigma of 0.005
 C14-H14 = C14-H14_$1
 0.97 with sigma of 0.005
 C15-H15 = C15-H15_$1
 0.97 with sigma of 0.005
 C16-H16 = C16-H16_$1
 0.97 with sigma of 0.005
 C17-H17 = C17-H17_$1
 0.97 with sigma of 0.005
 C18-H18 = C18-H18M = C18-H18_$1
 0.96 with sigma of 0.005
 C19-H19 = C19-H19M = C19-H19_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1
 1.565 with sigma of 0.005
 H11-H11_$1
 1.565 with sigma of 0.005
 H12-H12_$1
 1.565 with sigma of 0.005
 H13-H13_$1
 1.565 with sigma of 0.005
 H14-H14_$1
 1.565 with sigma of 0.005
 H15-H15_$1
 1.565 with sigma of 0.005
 H16-H16_$1
 1.565 with sigma of 0.005
 H17-H17_$1
 1.565 with sigma of 0.005
 H18-H18_$1 = H18-H18M
 1.565 with sigma of 0.005
 H19-H19_$1 = H19-H19M
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10_$1 \\sim C11-H10 \\sim C11-H10_$1
 with sigma of 0.005
 C10-H11 \\sim C10-H11_$1 \\sim C12-H11 \\sim C12-H11_$1
 with sigma of 0.005
 C11-H12 \\sim C11-H12_$1 \\sim C13-H12 \\sim C13-H12_$1
 with sigma of 0.005
 C12-H13 \\sim C12-H13_$1 \\sim C14-H13 \\sim C14-H13_$1
 with sigma of 0.005
 C13-H14 \\sim C13-H14_$1 \\sim C15-H14 \\sim C15-H14_$1
 with sigma of 0.005
 C14-H15 \\sim C14-H15_$1 \\sim C16-H15 \\sim C16-H15_$1
 with sigma of 0.005
 C15-H16 \\sim C15-H16_$1 \\sim C17-H16 \\sim C17-H16_$1
 with sigma of 0.005
 C16-H17 \\sim C16-H17_$1 \\sim C18-H17 \\sim C18-H17_$1
 with sigma of 0.005
 C17-H18 \\sim C17-H18M \\sim C17-H18_$1
 with sigma of 0.005
 N1-H19 \\sim N1-H19M \\sim N1-H19_$1
 with sigma of 0.005
 H18-H18M \\sim H18M-H18_$1 \\sim H18_$1-H18
 with sigma of 0.005
 H19-H19M \\sim H19M-H19_$1 \\sim H19_$1-H19
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8330(7) 0.2500 0.10899(15) 0.0752(10) Uani 1 2 d DS T P . .
H1 H 0.7338(14) 0.3559(3) 0.10386(19) 0.090 Uiso 1 1 d DR . . . .
C2 C 0.9266(10) 0.2500 0.15905(19) 0.0987(15) Uani 1 2 d DS T P . .
H2 H 1.0262(16) 0.3557(4) 0.1641(2) 0.118 Uiso 1 1 d DR . . . .
C3 C 0.7367(11) 0.2500 0.19187(19) 0.1074(17) Uani 1 2 d DS T P . .
H3 H 0.6402(16) 0.3558(4) 0.1848(2) 0.129 Uiso 1 1 d DR . . . .
C4 C 0.7908(12) 0.2500 0.2428(2) 0.119(2) Uani 1 2 d DS T P . .
H4 H 0.8891(17) 0.3558(4) 0.2490(3) 0.143 Uiso 1 1 d DR . . . .
C5 C 0.6076(13) 0.2500 0.2753(2) 0.138(3) Uani 1 2 d DS T P . .
H5 H 0.5114(18) 0.3558(4) 0.2679(3) 0.165 Uiso 1 1 d DR . . . .
C6 C 0.6492(14) 0.2500 0.3254(2) 0.121(2) Uani 1 2 d DS T P . .
H6 H 0.7456(18) 0.3557(4) 0.3329(3) 0.145 Uiso 1 1 d DR . . . .
C7 C 0.4638(15) 0.2500 0.3573(3) 0.157(4) Uani 1 2 d DS T P . .
H7 H 0.3701(19) 0.3558(4) 0.3487(3) 0.188 Uiso 1 1 d DR . . . .
C8 C 0.4898(15) 0.2500 0.4066(2) 0.129(2) Uani 1 2 d DS T P . .
H8 H 0.5847(19) 0.3558(4) 0.4147(3) 0.154 Uiso 1 1 d DR . . . .
C9 C 0.3112(15) 0.2500 0.4394(3) 0.162(4) Uani 1 2 d DS T P . .
H9 H 0.2174(19) 0.3558(4) 0.4308(3) 0.195 Uiso 1 1 d DR . . . .
C10 C 0.3332(15) 0.2500 0.4880(3) 0.130(3) Uani 1 2 d DS T P . .
H10 H 0.4265(19) 0.3558(4) 0.4968(3) 0.156 Uiso 1 1 d DR . . . .
C11 C 0.1542(16) 0.2500 0.5211(3) 0.170(4) Uani 1 2 d DS T P . .
H11 H 0.061(2) 0.3558(4) 0.5121(3) 0.204 Uiso 1 1 d DR . . . .
C12 C 0.1742(15) 0.2500 0.5694(2) 0.133(3) Uani 1 2 d DS T P . .
H12 H 0.2679(19) 0.3558(4) 0.5780(3) 0.159 Uiso 1 1 d DR . . . .
C13 C -0.0012(16) 0.2500 0.6026(3) 0.170(4) Uani 1 2 d DS T P . .
H13 H -0.095(2) 0.3558(4) 0.5940(3) 0.204 Uiso 1 1 d DR . . . .
C14 C 0.0213(16) 0.2500 0.6508(3) 0.133(3) Uani 1 2 d DS T P . .
H14 H 0.115(2) 0.3558(4) 0.6593(3) 0.160 Uiso 1 1 d DR . . . .
C15 C -0.1548(19) 0.2500 0.6835(3) 0.203(6) Uani 1 2 d DS T P . .
H15 H -0.251(2) 0.3557(4) 0.6757(3) 0.243 Uiso 1 1 d DR . . . .
C16 C -0.1293(18) 0.2500 0.7329(3) 0.145(3) Uani 1 2 d DS T P . .
H16 H -0.033(2) 0.3557(4) 0.7406(4) 0.174 Uiso 1 1 d DR . . . .
C17 C -0.303(2) 0.2500 0.7663(4) 0.229(7) Uani 1 2 d DS T P . .
H17 H -0.397(3) 0.3557(4) 0.7575(4) 0.274 Uiso 1 1 d DR . . . .
C18 C -0.278(2) 0.2500 0.8137(3) 0.204(6) Uani 1 2 d DS T P . .
H18 H -0.192(3) 0.3558(3) 0.8242(5) 0.306 Uiso 1 1 d DR . . . .
H18M H -0.431(3) 0.2500 0.8265(7) 0.306 Uiso 1 2 d DRS T P . .
C19 C 0.8707(8) 0.2500 0.02577(16) 0.0911(13) Uani 1 2 d DS T P . .
H19 H 0.7731(14) 0.3559(3) 0.0235(4) 0.137 Uiso 1 1 d DR . . . .
H19M H 0.977(2) 0.2500 0.0007(3) 0.137 Uiso 1 2 d DRS T P . .
C20 C 1.1636(5) 0.4144(5) 0.07474(12) 0.0849(8) Uani 1 1 d . . . . .
H20A H 1.2549 0.4153 0.1042 0.127 Uiso 1 1 calc GR . . . .
H20B H 1.0659 0.5205 0.0724 0.127 Uiso 1 1 calc GR . . . .
H20C H 1.2683 0.4135 0.0495 0.127 Uiso 1 1 calc GR . . . .
N1 N 1.0113(5) 0.2500 0.07185(12) 0.0653(7) Uani 1 2 d DS T P . .
Br1 Br 0.63504(8) 0.7500 0.06534(2) 0.0876(2) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.970(4) . ?
C1 C2 1.495(7) . ?
C1 N1 1.507(5) . ?
C2 H2 0.970(4) . ?
C2 C3 1.467(8) . ?
C3 H3 0.969(4) . ?
C3 C4 1.469(9) . ?
C4 H4 0.971(4) . ?
C4 C5 1.431(9) . ?
C5 H5 0.970(4) . ?
C5 C6 1.436(10) . ?
C6 H6 0.970(4) . ?
C6 C7 1.430(10) . ?
C7 H7 0.969(4) . ?
C7 C8 1.408(11) . ?
C8 H8 0.970(4) . ?
C8 C9 1.419(10) . ?
C9 H9 0.970(4) . ?
C9 C10 1.386(10) . ?
C10 H10 0.969(4) . ?
C10 C11 1.425(11) . ?
C11 H11 0.969(4) . ?
C11 C12 1.380(11) . ?
C12 H12 0.969(4) . ?
C12 C13 1.412(10) . ?
C13 H13 0.969(4) . ?
C13 C14 1.375(11) . ?
C14 H14 0.969(4) . ?
C14 C15 1.405(12) . ?
C15 H15 0.970(4) . ?
C15 C16 1.410(14) . ?
C16 H16 0.970(4) . ?
C16 C17 1.411(13) . ?
C17 H17 0.970(4) . ?
C17 C18 1.352(15) . ?
C18 H18 0.959(4) . ?
C18 H18M 0.959(5) . ?
C19 H19 0.959(4) . ?
C19 H19M 0.960(5) . ?
C19 N1 1.497(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 N1 1.491(4) . ?
N1 C20 1.491(4) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 108.3(4) . . ?
C2 C1 N1 117.3(4) . . ?
N1 C1 H1 107.4(5) . . ?
C1 C2 H2 108.2(5) . . ?
C3 C2 C1 112.3(5) . . ?
C3 C2 H2 110.3(5) . . ?
C2 C3 H3 106.9(6) . . ?
C2 C3 C4 121.0(5) . . ?
C4 C3 H3 106.8(5) . . ?
C3 C4 H4 105.4(6) . . ?
C5 C4 C3 121.6(6) . . ?
C5 C4 H4 108.1(6) . . ?
C4 C5 H5 106.2(6) . . ?
C4 C5 C6 124.3(7) . . ?
C6 C5 H5 105.8(6) . . ?
C5 C6 H6 106.1(6) . . ?
C7 C6 C5 123.5(7) . . ?
C7 C6 H6 106.5(6) . . ?
C6 C7 H7 104.5(7) . . ?
C8 C7 C6 126.9(8) . . ?
C8 C7 H7 106.1(7) . . ?
C7 C8 H8 105.2(7) . . ?
C7 C8 C9 128.6(8) . . ?
C9 C8 H8 104.4(7) . . ?
C8 C9 H9 103.4(7) . . ?
C10 C9 C8 129.5(8) . . ?
C10 C9 H9 105.8(7) . . ?
C9 C10 H10 105.9(7) . . ?
C9 C10 C11 129.6(8) . . ?
C11 C10 H10 103.1(7) . . ?
C10 C11 H11 102.8(7) . . ?
C12 C11 C10 130.1(9) . . ?
C12 C11 H11 106.0(7) . . ?
C11 C12 H12 105.4(6) . . ?
C11 C12 C13 130.7(9) . . ?
C13 C12 H12 103.1(6) . . ?
C12 C13 H13 103.1(7) . . ?
C14 C13 C12 130.1(9) . . ?
C14 C13 H13 105.7(7) . . ?
C13 C14 H14 105.6(7) . . ?
C13 C14 C15 129.6(10) . . ?
C15 C14 H14 103.5(7) . . ?
C14 C15 H15 104.9(8) . . ?
C14 C15 C16 129.0(11) . . ?
C16 C15 H15 104.6(8) . . ?
C15 C16 H16 104.5(8) . . ?
C15 C16 C17 130.0(11) . . ?
C17 C16 H16 104.4(8) . . ?
C16 C17 H17 102.4(9) . . ?
C18 C17 C16 129.8(14) . . ?
C18 C17 H17 106.6(8) . . ?
C17 C18 H18 109.6(7) . . ?
C17 C18 H18M 109.6(7) . . ?
H18 C18 H18M 109.3(7) . . ?
H19 C19 H19M 109.5(7) . . ?
N1 C19 H19 109.5(6) . . ?
N1 C19 H19M 109.4(7) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
C19 N1 C1 106.0(3) . . ?
C20 N1 C1 111.7(2) . . ?
C20 N1 C1 111.7(2) 4_565 . ?
C20 N1 C19 108.9(2) . . ?
C20 N1 C19 108.9(2) 4_565 . ?
C20 N1 C20 109.4(3) . 4_565 ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C1 N1 C19 180.000(1) . . . . ?
C2 C1 N1 C20 -61.5(2) . . . . ?
C2 C1 N1 C20 61.5(2) . . . 4_565 ?
C2 C3 C4 C5 180.000(2) . . . . ?
C3 C4 C5 C6 180.000(2) . . . . ?
C4 C5 C6 C7 180.000(3) . . . . ?
C5 C6 C7 C8 180.000(4) . . . . ?
C6 C7 C8 C9 180.000(5) . . . . ?
C7 C8 C9 C10 180.000(5) . . . . ?
C8 C9 C10 C11 180.000(6) . . . . ?
C9 C10 C11 C12 180.000(6) . . . . ?
C10 C11 C12 C13 180.000(7) . . . . ?
C11 C12 C13 C14 180.000(8) . . . . ?
C12 C13 C14 C15 180.000(9) . . . . ?
C13 C14 C15 C16 180.000(9) . . . . ?
C14 C15 C16 C17 180.000(13) . . . . ?
C15 C16 C17 C18 180.000(14) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0100 0.0005 0.0007 1.0001 0.0376 -0.0386 0.0037
0 0 -1 0.0100 -0.0005 -0.0007 -1.0001 -0.0376 0.0386 -0.0037
0 -5 -1 0.0221 0.2764 -4.7756 -1.4084 0.5075 0.5345 -0.6758
2 4 1 0.0545 1.7246 4.2253 0.8138 -0.1808 -0.1894 0.9651
-1 5 1 0.0305 -0.6411 4.7165 1.4717 -0.5513 -0.5809 0.5988
0 -5 -1 0.0223 -0.4905 -4.7449 -1.2314 0.4000 0.4209 -0.8141
-4 0 1 0.1241 -3.6735 0.1218 0.8407 -0.5124 -0.5416 -0.6665

_olex2_date_sample_data_collection 2015-08-21
_olex2_exptl_crystal_mounting_method '0.3mm Hampton Research 20um Nylon Loop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xstr0600
_database_code_depnum_ccdc_archive 'CCDC 1941235'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            'Tetramethylammonium bromide'
_chemical_name_systematic        'Tetramethylammonium bromide'

_chemical_formula_moiety         'Br, C4 H12 N'
_chemical_formula_sum            'C4 H12 Br N'
_chemical_formula_weight         154.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Me3 N C1 H3 Br'
_chemical_oxdiff_usercomment     'As supplied by ARR'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           129
_space_group_name_H-M_alt        'P 4/n m m'
_space_group_name_Hall           '-P 4a 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z'
'x+1/2, -y, -z'
'-x+1/2, -y+1/2, z'
'-y, -x, -z'
'y+1/2, x+1/2, -z'
'y, -x+1/2, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'y-1/2, -x, -z'
'-x-1/2, y, z'
'x-1/2, y-1/2, -z'
'y, x, z'
'-y-1/2, -x-1/2, z'
'-y, x-1/2, -z'
'x, -y-1/2, z'

_cell_length_a                   7.6596(2)
_cell_length_b                   7.6596(2)
_cell_length_c                   5.4588(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     320.27(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1989
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.3010
_cell_measurement_theta_min      8.0890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.706
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             156
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -1 -3 0.0191
-4 1 -2 0.0295
3 -2 2 0.0302
-3 3 -1 0.0413
2 -1 3 0.0295
-4 -2 2 0.0119
4 2 -2 0.0219
-3 -1 -2 0.0279
-3 1 3 0.0096

_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.029
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.8991 -0.6849 -2.8373 -0.4909 -0.1262 -0.8620
-3.9253 1.4147 -1.9262 -0.0443 0.9979 -0.0464
3.3681 -1.9898 2.1858 -0.0247 -0.9778 0.2080
-3.4811 2.9445 -1.4105 0.2981 0.9482 -0.1102
1.6736 -1.3872 3.1863 0.2071 -0.8006 0.5622
-3.8745 -1.7144 1.8548 -0.0720 0.2741 0.9590
3.7151 1.7589 -1.9940 0.0595 -0.2260 -0.9723
-3.2566 -1.4938 -2.4580 -0.6230 0.7822 -0.0090
-2.8991 0.6849 2.8373 0.4909 0.1262 0.8620

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2896
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.632
_diffrn_reflns_theta_min         8.119
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;      
List of Runs (angles in degrees, time in seconds): 
# Type Start End Width tₑₓₚ ω θ κ φ Frames --------------------------------------------------------------------------
1 ω 33.00 60.00 1.00 1.00 -- 42.37 77.00 -90.00 27 
2 ω 89.00 120.00 1.00 1.00 -- 106.36 77.00 -90.00 31 
3 ω 77.00 175.00 1.00 1.00 -- 106.36 77.00-180.00 98 
4 ω 111.00 174.00 1.00 1.00 -- 106.36 77.00 90.00 63 
5 ω -74.00 15.00 1.00 1.00 -- -42.37 77.00-120.00 89 
6 ω 2.00 32.00 1.00 1.00 -- -42.87 77.00 60.00 30 
7 ω 61.00 89.00 1.00 1.00 -- 42.87 77.00 -90.00 28 
8 ω 85.00 120.00 1.00 1.00 -- 106.36 77.00 -30.00 35 
9 ω 134.00 177.00 1.00 1.00 -- 106.36 77.00-120.00 43 
10 ω -112.00 -86.00 1.00 1.00 -- -42.87 -74.00-151.00 26 
11 ω -49.00 -17.00 1.00 1.00 -- -42.87 -74.00-151.00 32 
12 ω -53.00 -18.00 1.00 1.00 -- -42.87 -38.00 60.00 35 
13 ω -43.00 -18.00 1.00 1.00 -- -42.87 -38.00 -90.00 25 
14 ω -103.00 -62.00 1.00 1.00 -- -42.87 -38.00 60.00 41 
15 ω -43.00 -10.00 1.00 1.00 -- -42.87 -77.00 -90.00 33 
16 ω -84.00 -51.00 1.00 1.00 -- -42.87 -38.00 -90.00 33 
17 ω 5.00 84.00 1.00 1.00 -- 42.87 -99.00 60.00 79 
18 ω 17.00 42.00 1.00 1.00 -- 50.00 80.00 -52.91 25 
19 ω 16.00 41.00 1.00 1.00 -- 50.00 81.00 27.11 25 
20 ω 20.00 46.00 1.00 1.00 -- 54.00 81.00 74.78 26 
21 ω 25.00 62.00 1.00 1.00 -- 58.00 77.00 173.62 37 
22 ω 29.00 55.00 1.00 1.00 -- 58.00 61.00 22.19 26 
23 ω 30.00 62.00 1.00 1.00 -- 62.00 75.00-146.19 32 
24 ω 30.00 61.00 1.00 1.00 -- 62.00 74.00 121.50 31 
25 ω 92.00 136.00 1.00 1.00 -- 62.00 74.00 121.50 44 
26 ω 39.00 80.00 1.00 1.00 -- 70.00 76.00 32.74 41 
27 ω 42.00 77.00 1.00 1.00 -- 74.00 76.00 -24.84 35 
28 ω 49.00 74.00 1.00 1.00 -- 74.00 74.00 -68.84 25 
29 ω 41.00 77.00 1.00 1.00 -- 74.00 77.00-113.48 36 
30 ω 107.00 149.00 1.00 1.00 -- 74.00 74.00 -68.84 42 
31 ω 58.00 84.00 1.00 1.00 -- 86.00 62.00 5.80 26 
32 ω 48.00 109.00 1.00 1.00 -- 106.36 -94.00 -60.00 61 
33 ω 83.00 109.00 1.00 1.00 -- 106.36 61.00 120.00 26 
34 ω 75.00 164.00 1.00 1.00 -- 106.36 77.00 60.00 89 
35 ω 120.00 178.00 1.00 1.00 -- 106.36 77.00 120.00 58 
36 ω 75.00 135.00 1.00 1.00 -- 106.36 77.00 0.00 60 
37 ω 130.00 178.00 1.00 1.00 -- 106.36 77.00 -60.00 48 
38 ω 78.00 104.00 1.00 1.00 -- 106.36 61.00 150.00 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0069054000
_diffrn_orient_matrix_UB_12      0.1753816000
_diffrn_orient_matrix_UB_13      0.1377238000
_diffrn_orient_matrix_UB_21      -0.1641965000
_diffrn_orient_matrix_UB_22      0.0616977000
_diffrn_orient_matrix_UB_23      -0.1381705000
_diffrn_orient_matrix_UB_31      -0.1159249000
_diffrn_orient_matrix_UB_32      -0.0767837000
_diffrn_orient_matrix_UB_33      0.2039087000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                197
_reflns_number_total             209
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.869
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     17
_refine_ls_number_reflns         209
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.162
_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)+(0.0390P)²+0.1503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups
2. Restrained distances
 C1-H1B \\sim C1-H1A
 with sigma of 0.005
 N1-H1B \\sim N1-H1A
 with sigma of 0.005
 H1B-H1A \\sim H1B-H1A_$1
 with sigma of 0.005
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.2500 0.2500 0.62394(9) 0.0234(3) Uani 1 8 d S T P . .
N1 N 0.7500 0.2500 0.0000 0.0193(9) Uani 1 8 d DS T P . .
C1 C 0.5913(4) 0.2500 0.1584(5) 0.0280(7) Uani 1 2 d DS T P . .
H1A H 0.591(3) 0.354(3) 0.263(3) 0.042 Uiso 1 1 d DR . . . .
H1B H 0.487(2) 0.2500 0.056(4) 0.042 Uiso 1 2 d DRS T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.492(3) 6_545 ?
N1 C1 1.492(3) 10_665 ?
N1 C1 1.492(3) . ?
N1 C1 1.492(3) 11_755 ?
C1 H1A 0.978(18) . ?
C1 H1B 0.978(18) . ?

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
_geom_angle_publ_flag
C1 N1 C1 109.63(11) 6_545 11_755 ?
C1 N1 C1 109.2(2) 11_755 . ?
C1 N1 C1 109.2(2) 6_545 10_665 ?
C1 N1 C1 109.63(11) 10_665 . ?
C1 N1 C1 109.63(11) 6_545 . ?
C1 N1 C1 109.63(11) 11_755 10_665 ?
N1 C1 H1A 109.6(12) . . ?
N1 C1 H1B 109.6(12) . . ?
H1A C1 H1B 109.5(17) . . ?

_olex2_date_sample_data_collection 2016-03-22
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.672
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_643
_database_code_depnum_ccdc_archive 'CCDC 1941224'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C14TAB
_chemical_name_systematic        'Tetradecyltrimethylammonium bromide'
_chemical_formula_moiety         'C17 H38 N, Br'
_chemical_formula_sum            'C17 H38 Br N'
_chemical_formula_weight         336.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H38 N Br'
_chemical_oxdiff_usercomment     C14TAB
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.59763(9)
_cell_length_b                   7.15024(11)
_cell_length_c                   47.1556(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.3068(14)
_cell_angle_gamma                90
_cell_volume                     1885.84(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11715
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.0290
_cell_measurement_theta_min      5.6290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.869
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method 'Recrystallized from H2O'
_exptl_crystal_size_max          0.3599
_exptl_crystal_size_mid          0.1925
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            24241
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.297
_diffrn_reflns_theta_min         3.753
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  120.0000 81

#__ type_ start__ end____ width___ exp.time_
  4 omega  -68.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   57.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega   62.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651  172.0000 -169.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   75.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
  7 omega  126.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega  145.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   59.0000  -16.2549 31

#__ type_ start__ end____ width___ exp.time_
  9 omega  141.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   72.0000   -4.7020 36

#__ type_ start__ end____ width___ exp.time_
 10 omega  135.00  161.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  120.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega  116.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  120.0000 62

#__ type_ start__ end____ width___ exp.time_
 13 omega   79.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   45.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   77.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
 15 omega   76.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   80.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   45.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega   77.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   76.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   59.0000  -16.2549 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   73.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega   76.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 23 omega   74.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   73.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 25 omega   76.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 26 omega   76.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   77.00  128.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 29 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   72.0000   -4.7020 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   77.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 32 omega   73.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 33 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   77.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   61.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 35 omega   72.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -114.0000  -40.0000 41

#__ type_ start__ end____ width___ exp.time_
 36 omega   72.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -125.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   34.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -77.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
 38 omega   32.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930 -125.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 39 omega   24.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930  -94.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
 40 omega   73.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7930   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 41 omega    3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651   90.0000   88.1611 25

#__ type_ start__ end____ width___ exp.time_
 42 omega  -82.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  125.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
 43 omega -103.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -38.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 44 omega -115.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -57.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
 45 omega -115.00  -88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 46 omega -120.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000 -150.0000 111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0367621000
_diffrn_orient_matrix_UB_12      0.0141986000
_diffrn_orient_matrix_UB_13      -0.0321383000
_diffrn_orient_matrix_UB_21      -0.1900000000
_diffrn_orient_matrix_UB_22      0.1556715000
_diffrn_orient_matrix_UB_23      -0.0023798000
_diffrn_orient_matrix_UB_31      0.1958863000
_diffrn_orient_matrix_UB_32      0.1483002000
_diffrn_orient_matrix_UB_33      0.0055647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3283
_reflns_number_total             3717
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+3.6223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1152
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uiso(H1A) = Uiso(H1B)
Uiso(H2A) = Uiso(H2B)
Uiso(H3A) = Uiso(H3B)
Uiso(H4A) = Uiso(H4B)
Uiso(H5A) = Uiso(H5B)
Uiso(H6A) = Uiso(H6B)
Uiso(H7A) = Uiso(H7B)
Uiso(H8A) = Uiso(H8B)
Uiso(H9A) = Uiso(H9B)
Uiso(H10A) = Uiso(H10B)
Uiso(H11A) = Uiso(H11B)
Uiso(H12A) = Uiso(H12B)
Uiso(H13A) = Uiso(H13B)
Uiso(H14A) = Uiso(H14B) = Uiso(H14C)
Uiso(H15A) = Uiso(H15B) = Uiso(H15C) = Uiso(H16A) = Uiso(H16B) = Uiso(H16C) =
Uiso(H17A) = Uiso(H17B) = Uiso(H17C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.733(6) 0.379(5) 0.0625(7) 0.018(6) Uiso 1 1 d . . . . .
H1B H 0.697(6) 0.155(5) 0.0591(7) 0.018(6) Uiso 1 1 d . . . . .
H2A H 1.028(7) 0.298(5) 0.1001(8) 0.022(7) Uiso 1 1 d . . . . .
H2B H 0.934(7) 0.089(6) 0.0986(7) 0.022(7) Uiso 1 1 d . . . . .
H3A H 0.662(7) 0.420(6) 0.1131(8) 0.023(7) Uiso 1 1 d . . . . .
H3B H 0.542(7) 0.216(5) 0.1079(8) 0.023(7) Uiso 1 1 d . . . . .
H4A H 0.870(8) 0.243(6) 0.1526(9) 0.034(8) Uiso 1 1 d . . . . .
H4B H 0.728(8) 0.084(6) 0.1472(8) 0.034(8) Uiso 1 1 d . . . . .
H5A H 0.532(7) 0.434(6) 0.1642(8) 0.027(7) Uiso 1 1 d . . . . .
H5B H 0.369(7) 0.265(6) 0.1555(8) 0.027(7) Uiso 1 1 d . . . . .
H6A H 0.695(7) 0.260(6) 0.2030(8) 0.028(7) Uiso 1 1 d . . . . .
H6B H 0.523(7) 0.092(6) 0.1938(8) 0.028(7) Uiso 1 1 d . . . . .
H7A H 0.356(7) 0.444(6) 0.2135(8) 0.027(7) Uiso 1 1 d . . . . .
H7B H 0.185(7) 0.287(6) 0.2035(8) 0.027(7) Uiso 1 1 d . . . . .
H8A H 0.503(7) 0.248(5) 0.2517(8) 0.020(6) Uiso 1 1 d . . . . .
H8B H 0.318(7) 0.090(5) 0.2416(7) 0.020(6) Uiso 1 1 d . . . . .
H9A H 0.171(7) 0.446(6) 0.2617(8) 0.023(7) Uiso 1 1 d . . . . .
H9B H -0.005(8) 0.292(5) 0.2521(8) 0.023(7) Uiso 1 1 d . . . . .
H10A H 0.308(7) 0.249(6) 0.2995(8) 0.022(7) Uiso 1 1 d . . . . .
H10B H 0.135(6) 0.089(6) 0.2896(7) 0.022(7) Uiso 1 1 d . . . . .
H11A H -0.015(7) 0.449(6) 0.3103(8) 0.028(7) Uiso 1 1 d . . . . .
H11B H -0.199(7) 0.293(6) 0.2999(8) 0.028(7) Uiso 1 1 d . . . . .
H12A H 0.124(7) 0.234(6) 0.3482(8) 0.031(7) Uiso 1 1 d . . . . .
H12B H -0.054(7) 0.092(6) 0.3374(8) 0.031(7) Uiso 1 1 d . . . . .
H13A H -0.200(7) 0.446(6) 0.3595(8) 0.030(7) Uiso 1 1 d . . . . .
H13B H -0.376(8) 0.298(6) 0.3488(8) 0.030(7) Uiso 1 1 d . . . . .
H14A H -0.063(9) 0.248(7) 0.3976(10) 0.050(8) Uiso 1 1 d . . . . .
H14B H -0.257(9) 0.092(8) 0.3855(10) 0.050(8) Uiso 1 1 d . . . . .
H14C H -0.336(9) 0.285(7) 0.3974(10) 0.050(8) Uiso 1 1 d . . . . .
H15A H 0.771(7) 0.364(6) 0.0144(8) 0.023(3) Uiso 1 1 d . . . . .
H15B H 0.785(7) 0.144(6) 0.0128(8) 0.023(3) Uiso 1 1 d . . . . .
H15C H 1.001(7) 0.259(5) 0.0007(8) 0.023(3) Uiso 1 1 d . . . . .
H16A H 1.240(7) 0.415(5) 0.0652(8) 0.023(3) Uiso 1 1 d . . . . .
H16B H 1.056(7) 0.524(6) 0.0452(8) 0.023(3) Uiso 1 1 d . . . . .
H16C H 1.252(7) 0.413(6) 0.0319(8) 0.023(3) Uiso 1 1 d . . . . .
H17A H 1.044(7) -0.041(6) 0.0448(8) 0.023(3) Uiso 1 1 d . . . . .
H17B H 1.241(7) 0.080(5) 0.0633(8) 0.023(3) Uiso 1 1 d . . . . .
H17C H 1.258(7) 0.072(5) 0.0311(8) 0.023(3) Uiso 1 1 d . . . . .
C1 C 0.8046(5) 0.2535(5) 0.06502(6) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.8842(6) 0.2189(4) 0.09576(6) 0.0182(6) Uani 1 1 d . . . . .
C3 C 0.6811(6) 0.2802(5) 0.11449(6) 0.0223(7) Uani 1 1 d . . . . .
C4 C 0.7171(6) 0.2241(5) 0.14567(6) 0.0245(7) Uani 1 1 d . . . . .
C5 C 0.5233(6) 0.3002(5) 0.16396(6) 0.0212(7) Uani 1 1 d . . . . .
C6 C 0.5349(6) 0.2272(5) 0.19431(6) 0.0222(6) Uani 1 1 d . . . . .
C7 C 0.3404(6) 0.3074(5) 0.21251(6) 0.0211(6) Uani 1 1 d . . . . .
C8 C 0.3436(6) 0.2264(5) 0.24251(6) 0.0213(6) Uani 1 1 d . . . . .
C9 C 0.1504(6) 0.3097(5) 0.26080(6) 0.0217(7) Uani 1 1 d . . . . .
C10 C 0.1519(6) 0.2257(5) 0.29060(6) 0.0209(6) Uani 1 1 d . . . . .
C11 C -0.0366(6) 0.3104(5) 0.30906(6) 0.0220(7) Uani 1 1 d . . . . .
C12 C -0.0383(6) 0.2262(5) 0.33887(7) 0.0233(7) Uani 1 1 d . . . . .
C13 C -0.2247(7) 0.3107(5) 0.35761(7) 0.0273(7) Uani 1 1 d . . . . .
C14 C -0.2194(9) 0.2232(7) 0.38717(8) 0.0414(10) Uani 1 1 d . . . . .
C15 C 0.8751(6) 0.2568(5) 0.01476(6) 0.0224(6) Uani 1 1 d . . . . .
C16 C 1.1618(6) 0.4180(5) 0.04686(7) 0.0214(7) Uani 1 1 d . . . . .
C17 C 1.1429(6) 0.0755(5) 0.04595(7) 0.0211(7) Uani 1 1 d . . . . .
N1 N 0.9985(4) 0.2506(4) 0.04360(5) 0.0159(5) Uani 1 1 d . . . . .
Br1 Br 0.61999(5) 0.75232(5) 0.03967(2) 0.02684(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.99(4) . ?
C1 H1B 0.96(4) . ?
C1 C2 1.519(4) . ?
C1 N1 1.512(3) . ?
C2 H2A 1.00(4) . ?
C2 H2B 0.98(4) . ?
C2 C3 1.531(4) . ?
C3 H3A 1.01(4) . ?
C3 H3B 0.94(4) . ?
C3 C4 1.530(4) . ?
C4 H4A 0.92(4) . ?
C4 H4B 1.01(5) . ?
C4 C5 1.514(4) . ?
C5 H5A 0.96(4) . ?
C5 H5B 0.97(4) . ?
C5 C6 1.522(4) . ?
C6 H6A 1.00(4) . ?
C6 H6B 0.97(4) . ?
C6 C7 1.525(4) . ?
C7 H7A 0.98(4) . ?
C7 H7B 0.96(4) . ?
C7 C8 1.528(4) . ?
C8 H8A 0.99(4) . ?
C8 H8B 0.99(4) . ?
C8 C9 1.531(4) . ?
C9 H9A 0.98(4) . ?
C9 H9B 0.96(4) . ?
C9 C10 1.528(4) . ?
C10 H10A 0.97(4) . ?
C10 H10B 0.99(4) . ?
C10 C11 1.521(4) . ?
C11 H11A 1.00(4) . ?
C11 H11B 1.00(4) . ?
C11 C12 1.530(4) . ?
C12 H12A 1.00(4) . ?
C12 H12B 0.97(4) . ?
C12 C13 1.520(5) . ?
C13 H13A 0.98(4) . ?
C13 H13B 0.93(4) . ?
C13 C14 1.527(5) . ?
C14 H14A 1.00(5) . ?
C14 H14B 0.96(5) . ?
C14 H14C 0.94(5) . ?
C15 H15A 0.96(4) . ?
C15 H15B 0.95(4) . ?
C15 H15C 0.99(4) . ?
C15 N1 1.501(4) . ?
C16 H16A 0.95(4) . ?
C16 H16B 0.96(4) . ?
C16 H16C 0.89(4) . ?
C16 N1 1.510(4) . ?
C17 H17A 1.00(4) . ?
C17 H17B 0.97(4) . ?
C17 H17C 0.97(4) . ?
C17 N1 1.492(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
_geom_angle_publ_flag
H1A C1 H1B 113(3) . . ?
C2 C1 H1A 111(2) . . ?
C2 C1 H1B 108(2) . . ?
N1 C1 H1A 103(2) . . ?
N1 C1 H1B 105(2) . . ?
N1 C1 C2 116.4(2) . . ?
H2A C2 H2B 107(3) . . ?
C1 C2 H2A 108(2) . . ?
C1 C2 H2B 111(2) . . ?
C1 C2 C3 107.9(2) . . ?
C3 C2 H2A 109(2) . . ?
C3 C2 H2B 114(2) . . ?
H3A C3 H3B 112(3) . . ?
C2 C3 H3A 109(2) . . ?
C2 C3 H3B 107(2) . . ?
C4 C3 H3A 109(2) . . ?
C4 C3 H3B 105(2) . . ?
C4 C3 C2 114.0(3) . . ?
H4A C4 H4B 94(4) . . ?
C3 C4 H4A 113(3) . . ?
C3 C4 H4B 110(2) . . ?
C5 C4 H4A 115(3) . . ?
C5 C4 H4B 111(2) . . ?
C5 C4 C3 112.5(3) . . ?
H5A C5 H5B 108(3) . . ?
C4 C5 H5A 109(2) . . ?
C4 C5 H5B 109(2) . . ?
C4 C5 C6 114.1(3) . . ?
C6 C5 H5A 109(2) . . ?
C6 C5 H5B 108(2) . . ?
H6A C6 H6B 108(3) . . ?
C5 C6 H6A 108(2) . . ?
C5 C6 H6B 109(2) . . ?
C5 C6 C7 113.3(3) . . ?
C7 C6 H6A 109(2) . . ?
C7 C6 H6B 110(2) . . ?
H7A C7 H7B 104(3) . . ?
C6 C7 H7A 110(2) . . ?
C6 C7 H7B 110(2) . . ?
C6 C7 C8 113.3(3) . . ?
C8 C7 H7A 110(2) . . ?
C8 C7 H7B 109(2) . . ?
H8A C8 H8B 107(3) . . ?
C7 C8 H8A 109(2) . . ?
C7 C8 H8B 110(2) . . ?
C7 C8 C9 113.1(3) . . ?
C9 C8 H8A 110(2) . . ?
C9 C8 H8B 108(2) . . ?
H9A C9 H9B 105(3) . . ?
C8 C9 H9A 109(2) . . ?
C8 C9 H9B 111(2) . . ?
C10 C9 H9A 111(2) . . ?
C10 C9 H9B 108(2) . . ?
C10 C9 C8 112.8(3) . . ?
H10A C10 H10B 106(3) . . ?
C9 C10 H10A 108(2) . . ?
C9 C10 H10B 111(2) . . ?
C11 C10 H10A 108(2) . . ?
C11 C10 H10B 111(2) . . ?
C11 C10 C9 113.1(3) . . ?
H11A C11 H11B 105(3) . . ?
C10 C11 H11A 110(2) . . ?
C10 C11 H11B 110(2) . . ?
C10 C11 C12 113.5(3) . . ?
C12 C11 H11A 110(2) . . ?
C12 C11 H11B 108(2) . . ?
H12A C12 H12B 100(3) . . ?
C11 C12 H12A 110(2) . . ?
C11 C12 H12B 109(2) . . ?
C13 C12 H12A 111(2) . . ?
C13 C12 H12B 112(2) . . ?
C13 C12 C11 114.1(3) . . ?
H13A C13 H13B 105(3) . . ?
C12 C13 H13A 110(2) . . ?
C12 C13 H13B 110(3) . . ?
C12 C13 C14 112.3(3) . . ?
C14 C13 H13A 109(2) . . ?
C14 C13 H13B 110(3) . . ?
H14A C14 H14B 113(4) . . ?
H14A C14 H14C 106(4) . . ?
H14B C14 H14C 110(4) . . ?
C13 C14 H14A 111(3) . . ?
C13 C14 H14B 109(3) . . ?
C13 C14 H14C 107(3) . . ?
H15A C15 H15B 111(3) . . ?
H15A C15 H15C 115(3) . . ?
H15B C15 H15C 110(3) . . ?
N1 C15 H15A 107(2) . . ?
N1 C15 H15B 106(2) . . ?
N1 C15 H15C 107(2) . . ?
H16A C16 H16B 111(3) . . ?
H16A C16 H16C 118(3) . . ?
H16B C16 H16C 109(3) . . ?
N1 C16 H16A 109(2) . . ?
N1 C16 H16B 104(2) . . ?
N1 C16 H16C 105(3) . . ?
H17A C17 H17B 111(3) . . ?
H17A C17 H17C 109(3) . . ?
H17B C17 H17C 104(3) . . ?
N1 C17 H17A 114(2) . . ?
N1 C17 H17B 109(2) . . ?
N1 C17 H17C 110(2) . . ?
C15 N1 C1 106.8(2) . . ?
C15 N1 C16 108.9(2) . . ?
C16 N1 C1 111.7(2) . . ?
C17 N1 C1 111.3(2) . . ?
C17 N1 C15 108.7(2) . . ?
C17 N1 C16 109.5(2) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 170.3(3) . . . . ?
C2 C1 N1 C15 171.1(3) . . . . ?
C2 C1 N1 C16 -70.0(3) . . . . ?
C2 C1 N1 C17 52.7(4) . . . . ?
C2 C3 C4 C5 175.4(3) . . . . ?
C3 C4 C5 C6 172.6(3) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C5 C6 C7 C8 176.9(3) . . . . ?
C6 C7 C8 C9 179.1(3) . . . . ?
C7 C8 C9 C10 179.0(3) . . . . ?
C8 C9 C10 C11 179.0(3) . . . . ?
C9 C10 C11 C12 179.5(3) . . . . ?
C10 C11 C12 C13 179.6(3) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
N1 C1 C2 C3 164.6(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 0 6 0.0638 3.5369 0.1738 5.7553 -0.0525 -0.6586 0.7506
-3 3 -4 0.0498 -2.8498 2.7613 -4.4280 0.0767 0.9819 -0.1734
0 -5 -1 0.1311 -0.2084 -4.6320 -0.6725 -0.0518 -0.6799 -0.7315
0 0 2 0.0100 0.0000 -0.0002 1.9995 -0.0643 -0.0048 0.0111
0 0 -2 0.0100 -0.0000 0.0002 -1.9995 0.0643 0.0048 -0.0111

_olex2_date_sample_data_collection 2014-07-11
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_825
_database_code_depnum_ccdc_archive 'CCDC 1941233'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C10TAB
_chemical_name_systematic        'Decyltrimethylammonium bromide'
_chemical_formula_moiety         'C13 H30 N, Br'
_chemical_formula_sum            'C13 H30 Br N'
_chemical_formula_weight         280.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H30 Br N'
_chemical_oxdiff_usercomment     
'Crystals grown from acetone solution cooled on ice'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.63155(10)
_cell_length_b                   7.25188(14)
_cell_length_c                   19.6559(4)
_cell_angle_alpha                90
_cell_angle_beta                 81.2424(17)
_cell_angle_gamma                90
_cell_volume                     793.38(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8698
_cell_measurement_temperature    295
_cell_measurement_theta_max      73.2650
_cell_measurement_theta_min      4.5390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.318
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.4807
_exptl_crystal_size_mid          0.2163
_exptl_crystal_size_min          0.0207
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11361
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.806
_diffrn_reflns_theta_min         4.552
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   57.0000 -120.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega  -80.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  112.0000  -36.0000 80

#__ type_ start__ end____ width___ exp.time_
  6 omega  -33.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega -113.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  8 omega -119.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -30.0000 104

#__ type_ start__ end____ width___ exp.time_
  9 omega -116.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  120.0000 106

#__ type_ start__ end____ width___ exp.time_
 10 omega   75.00  134.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000 -148.2483 59

#__ type_ start__ end____ width___ exp.time_
 11 omega  117.00  143.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   74.0000 -100.9963 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  113.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   69.0000    5.8718 64

#__ type_ start__ end____ width___ exp.time_
 13 omega  152.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000   25.0745 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   80.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
 15 omega   77.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   70.0000   25.0745 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   80.00  133.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
 20 omega   79.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
 21 omega   80.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   75.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   74.0000 -100.9963 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   75.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 25 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   78.00  119.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 27 omega   82.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 93

#__ type_ start__ end____ width___ exp.time_
 28 omega   81.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   75.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   74.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
 32 omega   75.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   69.0000    5.8718 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   74.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
 36 omega   45.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
 37 omega   73.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 38 omega   36.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 39 omega   38.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
 40 omega   26.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
 41 omega   24.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  150.0000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2687974000
_diffrn_orient_matrix_UB_12      0.0501245000
_diffrn_orient_matrix_UB_13      -0.0091028000
_diffrn_orient_matrix_UB_21      -0.0236549000
_diffrn_orient_matrix_UB_22      0.0452622000
_diffrn_orient_matrix_UB_23      0.0773319000
_diffrn_orient_matrix_UB_31      0.0616130000
_diffrn_orient_matrix_UB_32      -0.2013816000
_diffrn_orient_matrix_UB_33      0.0150989000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1642
_reflns_number_total             1710
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.046
_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)+(0.0632P)²+0.3127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10M = C10-H10_$1
 0.96 with sigma of 0.005
 C11-H11 = C11-H11M = C11-H11_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1 = H10-H10M = H10M-H10_$1
 1.565 with sigma of 0.005
 H11-H11_$1 = H11-H11M = H11M-H11_$1
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10M \\sim C9-H10_$1
 with sigma of 0.005
 N1-H11 \\sim N1-H11M \\sim N1-H11_$1
 with sigma of 0.005
 H10-H10M \\sim H10M-H10_$1 \\sim H10_$1-H10
 with sigma of 0.005
 H11-H11M \\sim H11M-H11_$1 \\sim H11_$1-H11
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7202(5) 0.2500 0.16214(17) 0.0536(7) Uani 1 2 d DS T P . .
H1 H 0.6253(13) 0.3580(4) 0.1553(2) 0.064 Uiso 1 1 d DR . . . .
C2 C 0.7688(8) 0.2500 0.2351(2) 0.0766(11) Uani 1 2 d DS T P . .
H2 H 0.8642(14) 0.3579(4) 0.2418(3) 0.092 Uiso 1 1 d DR . . . .
C3 C 0.5448(9) 0.2500 0.2851(2) 0.0879(14) Uani 1 2 d DS T P . .
H3 H 0.4531(14) 0.3579(4) 0.2759(3) 0.105 Uiso 1 1 d DR . . . .
C4 C 0.5602(10) 0.2500 0.3595(2) 0.0922(15) Uani 1 2 d DS T P . .
H4 H 0.6542(15) 0.3579(4) 0.3674(3) 0.111 Uiso 1 1 d DR . . . .
C5 C 0.3444(12) 0.2500 0.4098(3) 0.129(3) Uani 1 2 d DS T P . .
H5 H 0.2539(17) 0.3578(4) 0.3997(3) 0.155 Uiso 1 1 d DR . . . .
C6 C 0.3464(11) 0.2500 0.4825(3) 0.1001(17) Uani 1 2 d DS T P . .
H6 H 0.4374(16) 0.3579(4) 0.4923(4) 0.120 Uiso 1 1 d DR . . . .
C7 C 0.1327(14) 0.2500 0.5329(3) 0.165(4) Uani 1 2 d DS T P . .
H7 H 0.0425(19) 0.3578(4) 0.5226(4) 0.197 Uiso 1 1 d DR . . . .
C8 C 0.1285(15) 0.2500 0.6057(3) 0.118(2) Uani 1 2 d DS T P . .
H8 H 0.2201(19) 0.3579(4) 0.6150(5) 0.141 Uiso 1 1 d DR . . . .
C9 C -0.0788(18) 0.2500 0.6568(4) 0.192(5) Uani 1 2 d DS T P . .
H9 H -0.167(2) 0.3579(4) 0.6456(5) 0.230 Uiso 1 1 d DR . . . .
C10 C -0.091(2) 0.2500 0.7277(4) 0.182(5) Uani 1 2 d DS T P . .
H10 H -0.013(3) 0.3579(3) 0.7419(7) 0.273 Uiso 1 1 d DR . . . .
H10M H -0.256(3) 0.2500 0.7490(9) 0.273 Uiso 1 2 d DRS T P . .
C11 C 0.8424(6) 0.2500 0.03897(17) 0.0609(8) Uani 1 2 d DS T P . .
H11 H 0.7466(12) 0.3580(3) 0.0359(5) 0.091 Uiso 1 1 d DR . . . .
H11M H 0.9748(16) 0.2500 0.0019(5) 0.091 Uiso 1 2 d DRS T P . .
C12 C 1.0872(4) 0.4181(4) 0.10998(13) 0.0595(6) Uani 1 1 d . . . . .
H12A H 1.1503 0.4182 0.1527 0.089 Uiso 1 1 calc GR . . . .
H12B H 0.9906 0.5262 0.1074 0.089 Uiso 1 1 calc GR . . . .
H12C H 1.2176 0.4180 0.0723 0.089 Uiso 1 1 calc GR . . . .
N1 N 0.9368(4) 0.2500 0.10614(13) 0.0464(5) Uani 1 2 d DS T P . .
Br1 Br 0.56574(6) 0.7500 0.09468(2) 0.06251(18) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.969(4) . ?
C1 C2 1.500(5) . ?
C1 N1 1.513(4) . ?
C2 H2 0.969(4) . ?
C2 C3 1.476(6) . ?
C3 H3 0.970(4) . ?
C3 C4 1.479(7) . ?
C4 H4 0.970(4) . ?
C4 C5 1.444(7) . ?
C5 H5 0.970(4) . ?
C5 C6 1.432(8) . ?
C6 H6 0.970(4) . ?
C6 C7 1.438(8) . ?
C7 H7 0.970(4) . ?
C7 C8 1.428(10) . ?
C8 H8 0.970(4) . ?
C8 C9 1.419(9) . ?
C9 H9 0.970(4) . ?
C9 C10 1.384(12) . ?
C10 H10 0.960(4) . ?
C10 H10M 0.960(5) . ?
C11 H11 0.958(4) . ?
C11 H11M 0.960(5) . ?
C11 N1 1.496(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N1 1.493(3) . ?
N1 C12 1.493(3) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 108.5(4) . . ?
C2 C1 N1 116.8(3) . . ?
N1 C1 H1 107.5(4) . . ?
C1 C2 H2 108.3(4) . . ?
C3 C2 C1 112.0(4) . . ?
C3 C2 H2 110.2(4) . . ?
C2 C3 H3 107.5(5) . . ?
C2 C3 C4 119.1(4) . . ?
C4 C3 H3 107.3(4) . . ?
C3 C4 H4 105.8(5) . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 108.3(5) . . ?
C4 C5 H5 105.9(5) . . ?
C6 C5 C4 123.3(6) . . ?
C6 C5 H5 106.8(5) . . ?
C5 C6 H6 106.4(5) . . ?
C5 C6 C7 123.7(7) . . ?
C7 C6 H6 106.0(5) . . ?
C6 C7 H7 105.5(6) . . ?
C8 C7 C6 125.1(8) . . ?
C8 C7 H7 106.2(5) . . ?
C7 C8 H8 105.1(6) . . ?
C9 C8 C7 126.6(9) . . ?
C9 C8 H8 105.7(6) . . ?
C8 C9 H9 103.6(7) . . ?
C10 C9 C8 128.5(11) . . ?
C10 C9 H9 106.1(6) . . ?
C9 C10 H10 109.7(6) . . ?
C9 C10 H10M 109.7(7) . . ?
H10 C10 H10M 109.2(6) . . ?
H11 C11 H11M 109.4(6) . . ?
N1 C11 H11 109.5(6) . . ?
N1 C11 H11M 109.3(7) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
C11 N1 C1 106.7(2) . . ?
C12 N1 C1 111.34(16) . . ?
C12 N1 C1 111.34(16) 4_565 . ?
C12 N1 C11 108.98(17) . . ?
C12 N1 C11 108.97(17) 4_565 . ?
C12 N1 C12 109.5(3) 4_565 . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C1 N1 C11 180.000(0) . . . . ?
C2 C1 N1 C12 -61.23(17) . . . . ?
C2 C1 N1 C12 61.23(17) . . . 4_565 ?
C2 C3 C4 C5 180.000(1) . . . . ?
C3 C4 C5 C6 180.000(2) . . . . ?
C4 C5 C6 C7 180.000(3) . . . . ?
C5 C6 C7 C8 180.000(3) . . . . ?
C6 C7 C8 C9 180.000(4) . . . . ?
C7 C8 C9 C10 180.000(5) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0104 0.0001 -0.0000 1.0001 -0.0091 0.0773 0.0151
-3 -3 1 0.1021 -2.6231 -3.1802 0.7494 -0.8713 -0.0239 0.4901
4 0 1 0.2393 3.6527 0.0259 1.4353 0.9701 0.0258 0.2415
-3 2 -3 0.2051 -3.1497 2.3654 -2.5822 -0.7046 -0.0181 -0.7094
3 -3 3 0.2468 2.5630 -3.3089 2.8805 0.4968 0.0124 0.8678
-4 -1 -1 0.1754 -3.5569 -1.0143 -0.8408 -0.9993 -0.0268 -0.0276
-2 -4 2 0.1136 -1.8036 -3.9886 1.5299 -0.6986 -0.0196 0.7152
2 4 -1 0.0991 2.1882 3.6673 -1.1964 0.7829 0.0217 -0.6218
0 0 -1 0.0104 -0.0001 0.0000 -1.0001 0.0091 -0.0773 -0.0151

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_828
_database_code_depnum_ccdc_archive 'CCDC 1941234'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft' UCL
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            C10TAB
_chemical_name_systematic        'Decyltrimethylammonium bromide'
_chemical_formula_moiety         'C13 H30 N, Br'
_chemical_formula_sum            'C13 H30 Br N'
_chemical_formula_weight         280.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H30 Br N'
_chemical_oxdiff_usercomment     
'Crystals grown from acetone solution cooled on ice'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.65600(12)
_cell_length_b                   7.31429(17)
_cell_length_c                   20.2631(6)
_cell_angle_alpha                90
_cell_angle_beta                 76.970(3)
_cell_angle_gamma                90
_cell_volume                     816.70(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6827
_cell_measurement_temperature    375
_cell_measurement_theta_max      73.2570
_cell_measurement_theta_min      4.4740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.223
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.2112
_exptl_crystal_size_min          0.0131
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_min         4.479
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      375
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -56.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega  -82.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -87.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -64.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega  -44.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega  -48.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
  9 omega  -31.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216   38.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
 10 omega   26.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216 -125.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   24.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000   90.0000 78

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -45.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   88.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614 -125.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -94.0000  -30.0000 74

#__ type_ start__ end____ width___ exp.time_
 16 omega   31.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  -77.0000  150.0000 108

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   45.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega  109.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
 19 omega  114.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 20 omega  146.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega  139.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   54.0000  -74.2952 28

#__ type_ start__ end____ width___ exp.time_
 22 omega   75.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   78.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   79.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega   94.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614  125.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
 26 omega   80.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 27 omega   79.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   54.0000  -74.2952 32

#__ type_ start__ end____ width___ exp.time_
 28 omega   77.00  161.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   64.0000 -117.1196 84

#__ type_ start__ end____ width___ exp.time_
 29 omega   78.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
 31 omega   79.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
 32 omega   74.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 33 omega   76.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   66.0000  -99.5907 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   74.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 35 omega   76.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   75.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 37 omega   77.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
 38 omega   74.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 40 omega   77.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
 41 omega   77.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   61.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 42 omega   74.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 43 omega   75.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      106.3614   77.0000   60.0000 102

#__ type_ start__ end____ width___ exp.time_
 44 omega  -32.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       42.6216  -77.0000  120.0000 107

#__ type_ start__ end____ width___ exp.time_
 45 omega  -98.00  -68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -57.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 46 omega -118.00  -85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -77.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 47 omega -116.00  -91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.6216  -38.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2691714000
_diffrn_orient_matrix_UB_12      0.0454593000
_diffrn_orient_matrix_UB_13      0.0046026000
_diffrn_orient_matrix_UB_21      0.0571242000
_diffrn_orient_matrix_UB_22      0.0400580000
_diffrn_orient_matrix_UB_23      -0.0766063000
_diffrn_orient_matrix_UB_31      -0.0494469000
_diffrn_orient_matrix_UB_32      -0.2016778000
_diffrn_orient_matrix_UB_33      -0.0141986000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1564
_reflns_number_total             1758
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.085
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1758
_refine_ls_number_restraints     105
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.040
_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)+(0.0820P)²+0.2351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 C1-H1 = C1-H1_$1
 0.97 with sigma of 0.005
 C2-H2 = C2-H2_$1
 0.97 with sigma of 0.005
 C3-H3 = C3-H3_$1
 0.97 with sigma of 0.005
 C4-H4 = C4-H4_$1
 0.97 with sigma of 0.005
 C5-H5 = C5-H5_$1
 0.97 with sigma of 0.005
 C6-H6 = C6-H6_$1
 0.97 with sigma of 0.005
 C7-H7 = C7-H7_$1
 0.97 with sigma of 0.005
 C8-H8 = C8-H8_$1
 0.97 with sigma of 0.005
 C9-H9 = C9-H9_$1
 0.97 with sigma of 0.005
 C10-H10 = C10-H10M = C10-H10_$1
 0.96 with sigma of 0.005
 C11-H11 = C11-H11M = C11-H11_$1
 0.96 with sigma of 0.005
 H1-H1_$1
 1.565 with sigma of 0.005
 H2-H2_$1
 1.565 with sigma of 0.005
 H3-H3_$1
 1.565 with sigma of 0.005
 H4-H4_$1
 1.565 with sigma of 0.005
 H5-H5_$1
 1.565 with sigma of 0.005
 H6-H6_$1
 1.565 with sigma of 0.005
 H7-H7_$1
 1.565 with sigma of 0.005
 H8-H8_$1
 1.565 with sigma of 0.005
 H9-H9_$1
 1.565 with sigma of 0.005
 H10-H10_$1 = H10-H10M = H10M-H10_$1
 1.565 with sigma of 0.005
 H11-H11_$1 = H11-H11M = H11M-H11_$1
 1.565 with sigma of 0.005
 N1-H1 \\sim N1-H1_$1 \\sim C2-H1 \\sim C2-H1_$1
 with sigma of 0.005
 C1-H2 \\sim C1-H2_$1 \\sim C3-H2 \\sim C3-H2_$1
 with sigma of 0.005
 C2-H3 \\sim C2-H3_$1 \\sim C4-H3 \\sim C4-H3_$1
 with sigma of 0.005
 C3-H4 \\sim C3-H4_$1 \\sim C5-H4 \\sim C5-H4_$1
 with sigma of 0.005
 C4-H5 \\sim C4-H5_$1 \\sim C6-H5 \\sim C6-H5_$1
 with sigma of 0.005
 C5-H6 \\sim C5-H6_$1 \\sim C7-H6 \\sim C7-H6_$1
 with sigma of 0.005
 C6-H7 \\sim C6-H7_$1 \\sim C8-H7 \\sim C8-H7_$1
 with sigma of 0.005
 C7-H8 \\sim C7-H8_$1 \\sim C9-H8 \\sim C9-H8_$1
 with sigma of 0.005
 C8-H9 \\sim C8-H9_$1 \\sim C10-H9 \\sim C10-H9_$1
 with sigma of 0.005
 C9-H10 \\sim C9-H10M \\sim C9-H10_$1
 with sigma of 0.005
 N1-H11 \\sim N1-H11M \\sim N1-H11_$1
 with sigma of 0.005
 H10-H10M \\sim H10M-H10_$1 \\sim H10_$1-H10
 with sigma of 0.005
 H11-H11M \\sim H11M-H11_$1 \\sim H11_$1-H11
 with sigma of 0.005
3.a Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6989(8) 0.2500 0.1624(2) 0.0847(11) Uani 1 2 d DS T P . .
H1 H 0.6039(15) 0.3570(4) 0.1567(3) 0.102 Uiso 1 1 d DR . . . .
C2 C 0.7432(12) 0.2500 0.2312(3) 0.1123(18) Uani 1 2 d DS T P . .
H2 H 0.8388(17) 0.3570(4) 0.2362(4) 0.135 Uiso 1 1 d DR . . . .
C3 C 0.5204(14) 0.2500 0.2843(3) 0.130(2) Uani 1 2 d DS T P . .
H3 H 0.4254(18) 0.3569(4) 0.2786(5) 0.156 Uiso 1 1 d DR . . . .
C4 C 0.5362(18) 0.2500 0.3572(4) 0.159(3) Uani 1 2 d DS T P . .
H4 H 0.633(2) 0.3570(4) 0.3612(5) 0.190 Uiso 1 1 d DR . . . .
C5 C 0.3251(19) 0.2500 0.4117(4) 0.170(4) Uani 1 2 d DS T P . .
H5 H 0.233(2) 0.3570(4) 0.4041(5) 0.204 Uiso 1 1 d DR . . . .
C6 C 0.340(2) 0.2500 0.4793(4) 0.165(4) Uani 1 2 d DS T P . .
H6 H 0.432(2) 0.3570(4) 0.4865(5) 0.198 Uiso 1 1 d DR . . . .
C7 C 0.135(2) 0.2500 0.5361(5) 0.187(5) Uani 1 2 d DS T P . .
H7 H 0.039(3) 0.3570(4) 0.5307(6) 0.225 Uiso 1 1 d DR . . . .
C8 C 0.145(3) 0.2500 0.6071(4) 0.188(4) Uani 1 2 d DS T P . .
H8 H 0.242(3) 0.3570(4) 0.6113(7) 0.226 Uiso 1 1 d DR . . . .
C9 C -0.056(3) 0.2500 0.6620(5) 0.230(7) Uani 1 2 d DS T P . .
H9 H -0.150(3) 0.3570(4) 0.6559(7) 0.276 Uiso 1 1 d DR . . . .
C10 C -0.045(3) 0.2500 0.7301(5) 0.264(8) Uani 1 2 d DS T P . .
H10 H 0.040(4) 0.3570(3) 0.7397(8) 0.396 Uiso 1 1 d DR . . . .
H10M H -0.206(4) 0.2500 0.7581(10) 0.396 Uiso 1 2 d DRS T P . .
C11 C 0.8257(8) 0.2500 0.0405(2) 0.0874(12) Uani 1 2 d DS T P . .
H11 H 0.7290(14) 0.3570(3) 0.0393(6) 0.131 Uiso 1 1 d DR . . . .
H11M H 0.9604(18) 0.2500 0.0020(4) 0.131 Uiso 1 2 d DRS T P . .
C12 C 1.0710(5) 0.4169(5) 0.10428(18) 0.0883(9) Uani 1 1 d . . . . .
H12A H 1.1394 0.4162 0.1435 0.132 Uiso 1 1 calc GR . . . .
H12B H 0.9723 0.5239 0.1050 0.132 Uiso 1 1 calc GR . . . .
H12C H 1.1993 0.4177 0.0641 0.132 Uiso 1 1 calc GR . . . .
N1 N 0.9187(5) 0.2500 0.10450(17) 0.0684(7) Uani 1 2 d DS T P . .
Br1 Br 0.54928(8) 0.7500 0.09384(3) 0.0896(3) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.971(4) . ?
C1 C2 1.471(8) . ?
C1 N1 1.505(5) . ?
C2 H2 0.969(4) . ?
C2 C3 1.461(10) . ?
C3 H3 0.971(4) . ?
C3 C4 1.500(11) . ?
C4 H4 0.970(4) . ?
C4 C5 1.433(12) . ?
C5 H5 0.970(4) . ?
C5 C6 1.391(13) . ?
C6 H6 0.969(4) . ?
C6 C7 1.438(14) . ?
C7 H7 0.970(4) . ?
C7 C8 1.454(16) . ?
C8 H8 0.970(4) . ?
C8 C9 1.401(15) . ?
C9 H9 0.970(4) . ?
C9 C10 1.396(18) . ?
C10 H10 0.960(4) . ?
C10 H10M 0.959(5) . ?
C11 H11 0.959(4) . ?
C11 H11M 0.960(5) . ?
C11 N1 1.505(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N1 1.493(4) . ?
N1 C12 1.493(4) 4_565 ?

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
_geom_angle_publ_flag
C2 C1 H1 109.3(5) . . ?
C2 C1 N1 116.8(4) . . ?
N1 C1 H1 106.8(5) . . ?
C1 C2 H2 108.6(6) . . ?
C3 C2 C1 113.3(5) . . ?
C3 C2 H2 109.3(6) . . ?
C2 C3 H3 108.8(7) . . ?
C2 C3 C4 119.5(7) . . ?
C4 C3 H3 105.9(7) . . ?
C3 C4 H4 104.1(8) . . ?
C5 C4 C3 122.4(9) . . ?
C5 C4 H4 108.9(7) . . ?
C4 C5 H5 105.0(8) . . ?
C6 C5 C4 122.4(10) . . ?
C6 C5 H5 108.1(8) . . ?
C5 C6 H6 107.5(8) . . ?
C5 C6 C7 124.8(11) . . ?
C7 C6 H6 104.1(9) . . ?
C6 C7 H7 106.2(10) . . ?
C6 C7 C8 125.8(12) . . ?
C8 C7 H7 105.0(9) . . ?
C7 C8 H8 103.8(9) . . ?
C9 C8 C7 125.4(13) . . ?
C9 C8 H8 107.6(9) . . ?
C8 C9 H9 105.6(10) . . ?
C10 C9 C8 125.2(15) . . ?
C10 C9 H9 106.0(10) . . ?
C9 C10 H10 109.6(6) . . ?
C9 C10 H10M 109.6(7) . . ?
H10 C10 H10M 109.3(6) . . ?
H11 C11 H11M 109.4(6) . . ?
N1 C11 H11 109.5(6) . . ?
N1 C11 H11M 109.4(7) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
C1 N1 C11 106.5(3) . . ?
C12 N1 C1 112.2(2) 4_565 . ?
C12 N1 C1 112.2(2) . . ?
C12 N1 C11 108.1(2) . . ?
C12 N1 C11 108.1(2) 4_565 . ?
C12 N1 C12 109.6(3) 4_565 . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 180.000(2) . . . . ?
C2 C1 N1 C11 180.000(0) . . . . ?
C2 C1 N1 C12 -61.9(2) . . . . ?
C2 C1 N1 C12 61.9(2) . . . 4_565 ?
C2 C3 C4 C5 180.000(2) . . . . ?
C3 C4 C5 C6 180.000(3) . . . . ?
C4 C5 C6 C7 180.000(3) . . . . ?
C5 C6 C7 C8 180.000(5) . . . . ?
C6 C7 C8 C9 180.000(7) . . . . ?
C7 C8 C9 C10 180.000(7) . . . . ?
N1 C1 C2 C3 180.000(1) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0066 -0.0000 0.0001 1.0004 0.0046 -0.0766 -0.0142
0 0 -1 0.0066 0.0000 -0.0001 -1.0004 -0.0046 0.0766 0.0142
3 3 4 0.2144 3.0574 2.5507 4.1580 -0.6879 -0.0417 -0.7246
-2 4 0 0.0988 -2.2232 3.7411 -0.3300 0.7670 0.0481 -0.6399
-3 -2 -4 0.2629 -3.3643 -1.8272 -4.1039 0.8036 0.0490 0.5931
2 -4 0 0.1081 1.7388 -4.1340 -0.3234 -0.6575 -0.0415 0.7524
-1 -4 -3 0.2202 -1.4403 -4.2843 -3.4426 0.1771 0.0098 0.9841
-4 1 -3 0.2067 -3.5408 1.2562 -2.7888 0.9973 0.0617 -0.0387
4 -1 3 0.1612 3.5063 -1.4080 2.6828 -0.9955 -0.0616 0.0725
3 -3 1 0.1063 2.8520 -2.9690 1.3042 -0.8966 -0.0559 0.4392

_olex2_date_sample_data_collection 2015-08-12
_olex2_submission_special_instructions 'No special instructions were received'
