# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_comp3
_database_code_depnum_ccdc_archive 'CCDC 1811292'
_audit_update_record             
;
2017-12-14 deposited with the CCDC.
2018-05-22 downloaded from the CCDC.
;
_audit_creation_date             2017-12-14
_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         'C30 H34 Br2 N8 O4, C H2 Cl2'
_chemical_formula_sum            'C31 H36 Br2 Cl2 N8 O4'
_chemical_formula_weight         815.40
_chemical_melting_point          477
_ccdc_journal_depnumber          ?
_ccdc_chemdiag_type              ChemDraw
_ccdc_chemdiag_records           comp3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   18.0444(6)
_cell_length_b                   11.4284(5)
_cell_length_c                   17.2410(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3555.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.15
_cell_measurement_reflns_used    6188
_cell_measurement_theta_min      2.8810
_cell_measurement_theta_max      30.8000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.478
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.148
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.074
_diffrn_reflns_theta_min         2.257
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0560
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3979
_reflns_number_total             5221
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.266
_refine_diff_density_min         -1.037
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.081
_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)+(0.0630P)²+4.3160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1LA(0.5) H1LB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B), C35(H35A,H35B), C1L(H1LA,H1LB)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C14(H14)
3.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C36(H36A,H36B,H36C)
;
_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 0.36226(2) 0.73786(2) 0.97639(2) 0.02179(10) Uani 1 1 d . . . . .
Cl1L Cl 0.18900(6) 0.08504(10) 0.55288(9) 0.0665(4) Uani 1 1 d . . . . .
O1 O 0.42760(10) 0.55545(17) 0.70680(12) 0.0198(4) Uani 1 1 d . . . . .
O2 O 0.29404(10) 0.21306(17) 0.72451(12) 0.0196(4) Uani 1 1 d . . . . .
N22 N 0.35589(11) 0.3899(2) 0.71993(13) 0.0167(4) Uani 1 1 d . . . . .
N30 N 0.51772(12) 0.2185(2) 0.60459(13) 0.0173(4) Uani 1 1 d . . . . .
N26 N 0.47410(11) 0.3910(2) 0.65704(13) 0.0171(4) Uani 1 1 d . . . . .
N24 N 0.40215(12) 0.2135(2) 0.66208(13) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.34182(14) 0.7031(2) 0.87116(15) 0.0154(5) Uani 1 1 d . . . . .
C15 C 0.26575(13) 0.7291(2) 0.76009(16) 0.0162(5) Uani 1 1 d . . . . .
C16 C 0.27879(13) 0.7518(2) 0.83756(16) 0.0154(5) Uani 1 1 d . . . . .
H16 H 0.245854 0.799129 0.866972 0.018 Uiso 1 1 calc R . . . .
C12 C 0.39075(13) 0.6339(2) 0.82920(16) 0.0168(5) Uani 1 1 d . . . . .
H12 H 0.433382 0.600655 0.852848 0.020 Uiso 1 1 calc R . . . .
C31 C 0.58713(14) 0.2797(2) 0.58432(16) 0.0180(5) Uani 1 1 d . . . . .
H31A H 0.627053 0.220927 0.578577 0.022 Uiso 1 1 calc R . . . .
H31B H 0.600899 0.331891 0.627832 0.022 Uiso 1 1 calc R . . . .
C23 C 0.35338(13) 0.2770(2) 0.70082(15) 0.0157(5) Uani 1 1 d . . . . .
C25 C 0.46375(13) 0.2754(2) 0.64199(15) 0.0160(5) Uani 1 1 d . . . . .
C32 C 0.58316(16) 0.3522(3) 0.51027(16) 0.0215(5) Uani 1 1 d . . . . .
H32A H 0.543536 0.411664 0.515094 0.026 Uiso 1 1 calc R . . . .
H32B H 0.570993 0.300826 0.465816 0.026 Uiso 1 1 calc R . . . .
C21 C 0.41834(13) 0.4397(2) 0.69441(15) 0.0168(5) Uani 1 1 d . . . . .
C14 C 0.31304(14) 0.6615(2) 0.71534(16) 0.0184(5) Uani 1 1 d . . . . .
H14 H 0.303446 0.647274 0.661980 0.022 Uiso 1 1 calc R . . . .
C13 C 0.37507(13) 0.6153(2) 0.75196(16) 0.0166(5) Uani 1 1 d . . . . .
C33 C 0.65739(17) 0.4125(3) 0.49592(19) 0.0255(6) Uani 1 1 d . . . . .
H33A H 0.652975 0.465180 0.451285 0.038 Uiso 1 1 calc GR . . . .
H33B H 0.695423 0.353463 0.485320 0.038 Uiso 1 1 calc GR . . . .
H33C H 0.671404 0.457736 0.541947 0.038 Uiso 1 1 calc GR . . . .
C34 C 0.50792(15) 0.0966(2) 0.57873(17) 0.0198(5) Uani 1 1 d . . . . .
H34A H 0.541293 0.082789 0.534082 0.024 Uiso 1 1 calc R . . . .
H34B H 0.456426 0.087342 0.559880 0.024 Uiso 1 1 calc R . . . .
C35 C 0.52270(18) 0.0021(3) 0.63932(19) 0.0312(7) Uani 1 1 d . . . . .
H35A H 0.487405 0.012399 0.682753 0.037 Uiso 1 1 calc R . . . .
H35B H 0.513050 -0.075383 0.615762 0.037 Uiso 1 1 calc R . . . .
C36 C 0.60012(19) 0.0033(3) 0.6711(2) 0.0364(8) Uani 1 1 d . . . . .
H36A H 0.635597 -0.005928 0.628511 0.055 Uiso 1 1 calc GR . . . .
H36B H 0.606126 -0.061238 0.708011 0.055 Uiso 1 1 calc GR . . . .
H36C H 0.609197 0.077822 0.697580 0.055 Uiso 1 1 calc GR . . . .
C1L C 0.250000 0.000000 0.6063(3) 0.0429(13) Uani 1 2 d S T P . .
H1LA H 0.279270 0.052339 0.640253 0.052 Uiso 0.5 1 calc R . . . .
H1LB H 0.220731 -0.052339 0.640253 0.052 Uiso 0.5 1 calc R . . . .


_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 C11 1.893(3) . ?
Cl1L C1L 1.733(3) . ?
O1 C21 1.350(3) . ?
O1 C13 1.404(3) . ?
O2 C15 1.406(3) 2_565 ?
O2 C23 1.359(3) . ?
N22 C23 1.332(4) . ?
N22 C21 1.337(3) . ?
N30 C31 1.477(3) . ?
N30 C25 1.337(3) . ?
N30 C34 1.473(3) . ?
N26 C25 1.360(3) . ?
N26 C21 1.318(3) . ?
N24 C23 1.322(3) . ?
N24 C25 1.362(3) . ?
C11 C16 1.392(3) . ?
C11 C12 1.389(4) . ?
C15 C16 1.381(4) . ?
C15 C14 1.386(4) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.378(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.524(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.527(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.526(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.501(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C1L H1LA 0.9900 . ?
C1L H1LB 0.9900 . ?

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
C21 O1 C13 118.8(2) . . ?
C23 O2 C15 118.9(2) . 2_565 ?
C23 N22 C21 111.1(2) . . ?
C25 N30 C31 120.1(2) . . ?
C25 N30 C34 121.3(2) . . ?
C34 N30 C31 118.6(2) . . ?
C21 N26 C25 113.5(2) . . ?
C23 N24 C25 112.7(2) . . ?
C16 C11 Br1 118.29(19) . . ?
C12 C11 Br1 119.65(19) . . ?
C12 C11 C16 122.0(2) . . ?
C16 C15 O2 117.7(2) . 2_565 ?
C16 C15 C14 122.6(2) . . ?
C14 C15 O2 119.5(2) . 2_565 ?
C11 C16 H16 121.1 . . ?
C15 C16 C11 117.8(2) . . ?
C15 C16 H16 121.1 . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.4(2) . . ?
C13 C12 H12 121.3 . . ?
N30 C31 H31A 108.6 . . ?
N30 C31 H31B 108.6 . . ?
N30 C31 C32 114.6(2) . . ?
H31A C31 H31B 107.6 . . ?
C32 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
N22 C23 O2 118.2(2) . . ?
N24 C23 O2 112.4(2) . . ?
N24 C23 N22 129.4(2) . . ?
N30 C25 N26 117.7(2) . . ?
N30 C25 N24 117.6(2) . . ?
N26 C25 N24 124.6(2) . . ?
C31 C32 H32A 109.7 . . ?
C31 C32 H32B 109.7 . . ?
C31 C32 C33 109.9(2) . . ?
H32A C32 H32B 108.2 . . ?
C33 C32 H32A 109.7 . . ?
C33 C32 H32B 109.7 . . ?
N22 C21 O1 118.0(2) . . ?
N26 C21 O1 113.4(2) . . ?
N26 C21 N22 128.6(3) . . ?
C15 C14 H14 121.5 . . ?
C15 C14 C13 117.1(2) . . ?
C13 C14 H14 121.5 . . ?
C12 C13 O1 118.2(2) . . ?
C12 C13 C14 123.1(2) . . ?
C14 C13 O1 118.5(2) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N30 C34 H34A 108.2 . . ?
N30 C34 H34B 108.2 . . ?
N30 C34 C35 116.2(2) . . ?
H34A C34 H34B 107.4 . . ?
C35 C34 H34A 108.2 . . ?
C35 C34 H34B 108.2 . . ?
C34 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C36 C35 C34 114.0(3) . . ?
C36 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
Cl1L C1L Cl1L 115.8(3) 2 . ?
Cl1L C1L H1LA 108.3 2 . ?
Cl1L C1L H1LA 108.3 . . ?
Cl1L C1L H1LB 108.3 . . ?
Cl1L C1L H1LB 108.3 2 . ?
H1LA C1L H1LB 107.4 . . ?

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
Br1 C11 C16 C15 177.87(19) . . . . ?
Br1 C11 C12 C13 -177.3(2) . . . . ?
O2 C15 C16 C11 -174.3(2) 2_565 . . . ?
O2 C15 C14 C13 174.1(2) 2_565 . . . ?
N30 C31 C32 C33 179.2(2) . . . . ?
N30 C34 C35 C36 -60.0(3) . . . . ?
C11 C12 C13 O1 173.8(2) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C15 O2 C23 N22 7.2(4) 2_565 . . . ?
C15 O2 C23 N24 -174.1(2) 2_565 . . . ?
C15 C14 C13 O1 -174.2(2) . . . . ?
C15 C14 C13 C12 0.1(4) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C16 C15 C14 C13 0.6(4) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
C31 N30 C25 N26 2.9(4) . . . . ?
C31 N30 C25 N24 -177.4(2) . . . . ?
C31 N30 C34 C35 100.1(3) . . . . ?
C23 N22 C21 O1 177.5(2) . . . . ?
C23 N22 C21 N26 -1.9(4) . . . . ?
C23 N24 C25 N30 178.0(2) . . . . ?
C23 N24 C25 N26 -2.2(4) . . . . ?
C25 N30 C31 C32 -82.5(3) . . . . ?
C25 N30 C34 C35 -83.5(3) . . . . ?
C25 N26 C21 O1 -177.8(2) . . . . ?
C25 N26 C21 N22 1.7(4) . . . . ?
C25 N24 C23 O2 -176.5(2) . . . . ?
C25 N24 C23 N22 2.0(4) . . . . ?
C21 O1 C13 C12 97.6(3) . . . . ?
C21 O1 C13 C14 -87.8(3) . . . . ?
C21 N22 C23 O2 178.3(2) . . . . ?
C21 N22 C23 N24 -0.2(4) . . . . ?
C21 N26 C25 N30 -179.6(2) . . . . ?
C21 N26 C25 N24 0.6(4) . . . . ?
C14 C15 C16 C11 -0.6(4) . . . . ?
C13 O1 C21 N22 6.0(3) . . . . ?
C13 O1 C21 N26 -174.5(2) . . . . ?
C34 N30 C31 C32 94.0(3) . . . . ?
C34 N30 C25 N26 -173.5(2) . . . . ?
C34 N30 C25 N24 6.3(4) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
