# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_jzhyb
_database_code_depnum_ccdc_archive 'CCDC 1525407'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.
2017-10-11 downloaded from the CCDC.
;
_audit_creation_date             2016-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br Cl3 Fe, C16 H36 N'
_chemical_formula_sum            'C16 H36 Br Cl3 Fe N'
_chemical_formula_weight         484.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1O1N1Fe1Cl1Br1
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.4928(16)
_cell_length_b                   11.5835(8)
_cell_length_c                   11.4759(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2458.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.1710
_cell_measurement_theta_min      3.7920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5751
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.535
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_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     -8.00  22.00   1.00    7.50    --  -33.50  37.00  60.00   30
  2  ω    -36.00   9.00   1.00    7.50    --  -33.50  37.00 -60.00   45
  3  ω    -47.00 -21.00   1.00    7.50    --  -33.50  37.00  60.00   26
  4  ω     58.00 100.00   1.00    7.50    --   36.47 178.00 -90.00   42
  5  ω     71.00  97.00   1.00    7.50    --   36.47 178.00 150.00   26
  6  ω     18.00 104.00   1.00    7.50    --   36.47  57.00 -30.00   86
  7  ω    101.00 177.00   1.00   30.00    --  108.00 111.00-180.00   76
  8  ω     43.00  85.00   1.00   30.00    --  108.00 -30.00  90.00   42
  9  ω     37.00  70.00   1.00   30.00    --  108.00 -30.00 150.00   33
 10  ω     54.00  96.00   1.00   30.00    --  108.00 -45.00-180.00   42
 11  ω     50.00  76.00   1.00   30.00    --  108.00 -77.00-120.00   26
 12  ω    100.00 137.00   1.00   30.00    --  108.00 -77.00-120.00   37
 13  ω     84.00 127.00   1.00   30.00    --  108.00 -61.00  30.00   43
 14  ω    107.00 154.00   1.00   30.00    --  108.00 111.00  90.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0715012000
_diffrn_orient_matrix_UB_12      0.0510151000
_diffrn_orient_matrix_UB_13      0.0455782000
_diffrn_orient_matrix_UB_21      0.0385552000
_diffrn_orient_matrix_UB_22      0.0395631000
_diffrn_orient_matrix_UB_23      0.1120152000
_diffrn_orient_matrix_UB_31      0.0184053000
_diffrn_orient_matrix_UB_32      0.1162240000
_diffrn_orient_matrix_UB_33      -0.0584398000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1349
_reflns_number_total             2188
_reflns_odcompleteness_completeness 99.40
_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 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (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         0.173
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00165(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.026
_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)+(0.0611P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1363
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Br1(0.25) Br1A(0.25) Cl1(0.75) Cl2(0.75)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.6681(8) 0.8982(9) 0.3086(13) 0.114(2) Uani 0.25 1 d . . . A 1
Br1A Br 0.5384(4) 0.6571(4) 0.4074(5) 0.1329(16) Uani 0.25 1 d . . . A 1
C1 C 0.3907(2) 0.6744(3) 0.6726(3) 0.0802(9) Uani 1 1 d . . . . .
H1A H 0.4229 0.6258 0.6274 0.096 Uiso 1 1 calc R . . . .
H1B H 0.3625 0.6239 0.7223 0.096 Uiso 1 1 calc R . . . .
C2 C 0.3401(2) 0.7323(3) 0.5899(3) 0.0925(10) Uani 1 1 d . . . . .
H2A H 0.3675 0.7798 0.5361 0.111 Uiso 1 1 calc R . . . .
H2B H 0.3076 0.7823 0.6330 0.111 Uiso 1 1 calc R . . . .
C3 C 0.2969(3) 0.6453(4) 0.5228(4) 0.1241(16) Uani 1 1 d . . . . .
H3A H 0.3302 0.5947 0.4821 0.149 Uiso 1 1 calc R . . . .
H3B H 0.2701 0.5983 0.5779 0.149 Uiso 1 1 calc R . . . .
C4 C 0.2448(3) 0.6935(5) 0.4362(5) 0.142(2) Uani 1 1 d . . . . .
H4A H 0.2710 0.7299 0.3740 0.214 Uiso 1 1 calc GR . . . .
H4B H 0.2143 0.7493 0.4736 0.214 Uiso 1 1 calc GR . . . .
H4C H 0.2156 0.6322 0.4052 0.214 Uiso 1 1 calc GR . . . .
C5 C 0.4832(2) 0.8280(3) 0.6734(3) 0.0839(9) Uani 1 1 d . . . . .
H5A H 0.5063 0.7800 0.6151 0.101 Uiso 1 1 calc R . . . .
H5B H 0.4512 0.8807 0.6326 0.101 Uiso 1 1 calc R . . . .
C6 C 0.5401(2) 0.8976(3) 0.7316(4) 0.1029(12) Uani 1 1 d . . . . .
H6A H 0.5735 0.8468 0.7719 0.123 Uiso 1 1 calc R . . . .
H6B H 0.5182 0.9484 0.7888 0.123 Uiso 1 1 calc R . . . .
C7 C 0.5811(3) 0.9691(5) 0.6418(5) 0.1359(19) Uani 1 1 d . . . . .
H7A H 0.5985 0.9178 0.5811 0.163 Uiso 1 1 calc R . . . .
H7B H 0.5476 1.0229 0.6060 0.163 Uiso 1 1 calc R . . . .
C8 C 0.6419(3) 1.0334(6) 0.6878(6) 0.181(3) Uani 1 1 d . . . . .
H8A H 0.6697 1.0646 0.6245 0.272 Uiso 1 1 calc GR . . . .
H8B H 0.6718 0.9829 0.7334 0.272 Uiso 1 1 calc GR . . . .
H8C H 0.6245 1.0952 0.7360 0.272 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.6558(6) 0.8898(7) 0.3243(9) 0.121(3) Uani 0.75 1 d . . . A 2
Cl2 Cl 0.5154(3) 0.6986(4) 0.3814(5) 0.1688(19) Uani 0.75 1 d . . . A 2
Fe1 Fe 0.59303(5) 0.7500 0.2500 0.0980(3) Uani 1 2 d S T P . .
N1 N 0.4366(2) 0.7500 0.7500 0.0720(9) 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
Br1 Fe1 2.308(13) . ?
Br1A Fe1 2.333(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.492(5) . ?
C1 N1 1.508(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.500(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.492(7) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.486(5) . ?
C5 N1 1.526(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.524(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.449(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
Cl1 Fe1 2.167(9) . ?
Cl2 Fe1 2.166(6) . ?
Fe1 Br1 2.308(13) 3_565 ?
Fe1 Br1A 2.333(6) 3_565 ?
Fe1 Cl1 2.167(9) 3_565 ?
Fe1 Cl2 2.166(6) 3_565 ?
N1 C1 1.508(4) 3_566 ?
N1 C5 1.526(4) 3_566 ?

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 107.2 . . ?
C2 C1 H1A 107.9 . . ?
C2 C1 H1B 107.9 . . ?
C2 C1 N1 117.8(3) . . ?
N1 C1 H1A 107.9 . . ?
N1 C1 H1B 107.9 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C1 C2 C3 111.0(3) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 C2 115.8(4) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
H5A C5 H5B 107.2 . . ?
C6 C5 H5A 107.9 . . ?
C6 C5 H5B 107.9 . . ?
C6 C5 N1 117.6(3) . . ?
N1 C5 H5A 107.9 . . ?
N1 C5 H5B 107.9 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.1(4) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.7(5) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Br1 Fe1 Br1 106.0(6) 3_565 . ?
Br1 Fe1 Br1A 98.2(3) 3_565 . ?
Br1 Fe1 Br1A 112.2(4) 3_565 3_565 ?
Br1 Fe1 Br1A 112.2(4) . . ?
Br1 Fe1 Br1A 98.2(3) . 3_565 ?
Br1A Fe1 Br1A 128.7(3) 3_565 . ?
Cl1 Fe1 Cl1 115.3(5) 3_565 . ?
Cl2 Fe1 Cl1 106.7(4) . . ?
Cl2 Fe1 Cl1 115.0(2) 3_565 . ?
Cl2 Fe1 Cl1 115.0(2) . 3_565 ?
Cl2 Fe1 Cl1 106.7(4) 3_565 3_565 ?
Cl2 Fe1 Cl2 96.9(3) 3_565 . ?
C1 N1 C1 111.6(4) 3_566 . ?
C1 N1 C5 108.76(18) . . ?
C1 N1 C5 108.23(18) . 3_566 ?
C1 N1 C5 108.23(18) 3_566 . ?
C1 N1 C5 108.76(18) 3_566 3_566 ?
C5 N1 C5 111.3(4) 3_566 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B Br1 0.97 2.85 3.723(10) 149.7 7_656
C5 H5A Br1A 0.97 2.84 3.779(6) 163.5 .
C5 H5A Cl2 0.97 2.85 3.719(6) 149.9 .

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 -179.3(4) . . . . ?
C2 C1 N1 C1 60.1(3) . . . 3_566 ?
C2 C1 N1 C5 -59.3(4) . . . . ?
C2 C1 N1 C5 179.7(3) . . . 3_566 ?
C5 C6 C7 C8 -175.2(5) . . . . ?
C6 C5 N1 C1 67.2(4) . . . 3_566 ?
C6 C5 N1 C1 -171.4(3) . . . . ?
C6 C5 N1 C5 -52.2(3) . . . 3_566 ?
N1 C1 C2 C3 -178.0(3) . . . . ?
N1 C5 C6 C7 179.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.734
_oxdiff_exptl_absorpt_empirical_full_min 0.659
