# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_diBr-BC
_database_code_depnum_ccdc_archive 'CCDC 1910052'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne Franche Comte
France
;
_audit_update_record             
;
2019-04-15 deposited with the CCDC.	2019-07-16 downloaded from the CCDC.
;
_audit_creation_date             2019-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3,13-Dibromo-5-methoxy-8,8,18,18-tetramethylbacteriochlorin
_chemical_formula_moiety         'C25 H26 Br2 N4 O'
_chemical_formula_sum            'C25 H26 Br2 N4 O'
_chemical_formula_weight         558.32
_chemical_melting_point          ?
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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.3753(10)
_cell_length_b                   5.8406(3)
_cell_length_c                   21.3396(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.947(2)
_cell_angle_gamma                90
_cell_volume                     2287.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7598
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.627
_shelx_estimated_absorpt_T_min   0.317
_exptl_absorpt_coefficient_mu    3.570
_exptl_absorpt_correction_T_max  0.4915
_exptl_absorpt_correction_T_min  0.3788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0847 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.7707.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from chloroform by slow evaporation'
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.144
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture (Mo)'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2165
_reflns_number_total             2629
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.015
_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)+(0.0311P)²+4.9290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          
'Hydrogen atom positions were calculated geometrically and refined using the riding model. H atom on N2 nitrogen atom was located in the Fourier difference maps. His positional parameters was either refined freely with Uiso(H) = 1.5Ueq(N). Methoxy group and hydrogen atom on beta carbon C6 were found disordered and S.O.F. were fixed at 50%.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H6(0.5) O1(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
3.a Fixed occupancy and ADP/Uiso:
 H2
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C6(H6)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.37335(2) 0.68925(5) 0.67375(2) 0.03376(10) Uani 1 1 d . . . . .
N1 N 0.42231(10) 0.1912(4) 0.44669(9) 0.0309(5) Uani 1 1 d . . . . .
N2 N 0.47632(11) 0.2001(4) 0.57805(9) 0.0308(5) Uani 1 1 d . . . . .
H2 H 0.4850(16) 0.134(5) 0.5483(15) 0.037 Uiso 1 1 d . . . . .
C2 C 0.40151(12) 0.1461(5) 0.38594(10) 0.0253(5) Uani 1 1 d . . . . .
C1 C 0.43362(12) -0.0120(4) 0.34876(10) 0.0249(5) Uani 1 1 d . . . . .
H1 H 0.414846 -0.017246 0.306467 0.030 Uiso 1 1 calc R . . . .
C13 C 0.33749(13) 0.3850(5) 0.29853(11) 0.0269(5) Uani 1 1 d . . . . .
H13A H 0.381085 0.481300 0.297385 0.040 Uiso 1 1 calc GR . . . .
H13B H 0.294037 0.478586 0.289071 0.040 Uiso 1 1 calc GR . . . .
H13C H 0.340053 0.262734 0.267277 0.040 Uiso 1 1 calc GR . . . .
C11 C 0.51034(12) 0.1661(5) 0.63625(10) 0.0257(5) Uani 1 1 d . . . . .
C10 C 0.47954(12) 0.3263(4) 0.67685(10) 0.0250(5) Uani 1 1 d . . . . .
H10 H 0.491723 0.343682 0.720396 0.030 Uiso 1 1 calc R . . . .
C3 C 0.33331(12) 0.2802(5) 0.36350(11) 0.0254(5) Uani 1 1 d . . . . .
C9 C 0.42919(12) 0.4515(5) 0.64240(10) 0.0264(5) Uani 1 1 d . . . . .
C8 C 0.42650(12) 0.3732(5) 0.57920(11) 0.0288(6) Uani 1 1 d . . . . .
C5 C 0.38099(13) 0.3642(5) 0.46690(11) 0.0313(6) Uani 1 1 d . . . . .
C6 C 0.38300(12) 0.4497(5) 0.52762(11) 0.0321(6) Uani 1 1 d . . . . .
H6 H 0.351280 0.574118 0.535032 0.039 Uiso 0.5 1 calc R . P A 2
C12 C 0.26812(13) 0.1181(5) 0.36508(13) 0.0361(6) Uani 1 1 d . . . . .
H12A H 0.273866 -0.006163 0.334880 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.223230 0.202770 0.354037 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.265478 0.053885 0.407323 0.054 Uiso 1 1 calc GR . . . .
C4 C 0.33066(14) 0.4618(5) 0.41529(11) 0.0336(6) Uani 1 1 d . . . . .
H4A H 0.348522 0.611542 0.400725 0.040 Uiso 1 1 calc R . . . .
H4B H 0.280568 0.480410 0.429518 0.040 Uiso 1 1 calc R . . . .
O1 O 0.33318(17) 0.5974(6) 0.53788(14) 0.0231(7) Uani 0.5 1 d . . P B 1
C7 C 0.3612(4) 0.8133(9) 0.5228(3) 0.0419(14) Uani 0.5 1 d . . P B 1
H7A H 0.373453 0.814859 0.478625 0.063 Uiso 0.5 1 calc GR . P B 1
H7B H 0.405202 0.844150 0.549416 0.063 Uiso 0.5 1 calc GR . P B 1
H7C H 0.324659 0.931357 0.529820 0.063 Uiso 0.5 1 calc GR . P B 1


_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 C9 1.871(2) . ?
N1 C2 1.358(3) . ?
N1 C5 1.348(3) . ?
N2 H2 0.77(3) . ?
N2 C11 1.376(3) . ?
N2 C8 1.365(3) . ?
C2 C1 1.371(3) . ?
C2 C3 1.533(3) . ?
C1 H1 0.9500 . ?
C1 C11 1.393(3) 5_656 ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C3 1.521(3) . ?
C11 C10 1.413(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.364(3) . ?
C3 C12 1.528(3) . ?
C3 C4 1.534(4) . ?
C9 C8 1.423(3) . ?
C8 C6 1.400(3) . ?
C5 C6 1.387(3) . ?
C5 C4 1.513(3) . ?
C6 H6 0.9500 . ?
C6 O1 1.285(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O1 C7 1.406(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
C5 N1 C2 108.4(2) . . ?
C11 N2 H2 125(2) . . ?
C8 N2 H2 124(2) . . ?
C8 N2 C11 111.4(2) . . ?
N1 C2 C1 125.1(2) . . ?
N1 C2 C3 112.6(2) . . ?
C1 C2 C3 122.2(2) . . ?
C2 C1 H1 115.2 . . ?
C2 C1 C11 129.6(2) . 5_656 ?
C11 C1 H1 115.2 5_656 . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
N2 C11 C1 126.7(2) . 5_656 ?
N2 C11 C10 106.3(2) . . ?
C1 C11 C10 127.0(2) 5_656 . ?
C11 C10 H10 126.1 . . ?
C9 C10 C11 107.8(2) . . ?
C9 C10 H10 126.1 . . ?
C2 C3 C4 100.59(18) . . ?
C13 C3 C2 114.29(19) . . ?
C13 C3 C12 110.22(19) . . ?
C13 C3 C4 112.5(2) . . ?
C12 C3 C2 107.8(2) . . ?
C12 C3 C4 111.0(2) . . ?
C10 C9 Br1 125.06(18) . . ?
C10 C9 C8 109.2(2) . . ?
C8 C9 Br1 125.79(18) . . ?
N2 C8 C9 105.3(2) . . ?
N2 C8 C6 125.4(2) . . ?
C6 C8 C9 129.3(2) . . ?
N1 C5 C6 125.5(2) . . ?
N1 C5 C4 112.5(2) . . ?
C6 C5 C4 122.0(2) . . ?
C8 C6 H6 116.3 . . ?
C5 C6 C8 127.3(2) . . ?
C5 C6 H6 116.3 . . ?
O1 C6 C8 117.6(2) . . ?
O1 C6 C5 114.6(2) . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C5 C4 C3 102.9(2) . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C6 O1 C7 106.9(4) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
_geom_hbond_publ_flag
N2 H2 N1 0.77(3) 2.42(3) 2.926(3) 124(3) . yes

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 C9 C8 N2 179.69(19) . . . . ?
Br1 C9 C8 C6 -0.7(4) . . . . ?
N1 C2 C1 C11 3.7(4) . . . 5_656 ?
N1 C2 C3 C13 136.3(2) . . . . ?
N1 C2 C3 C12 -100.8(3) . . . . ?
N1 C2 C3 C4 15.5(3) . . . . ?
N1 C5 C6 C8 -1.0(5) . . . . ?
N1 C5 C6 O1 -172.6(3) . . . . ?
N1 C5 C4 C3 14.2(3) . . . . ?
N2 C11 C10 C9 -0.6(3) . . . . ?
N2 C8 C6 C5 1.2(5) . . . . ?
N2 C8 C6 O1 172.6(3) . . . . ?
C2 N1 C5 C6 175.9(3) . . . . ?
C2 N1 C5 C4 -4.6(3) . . . . ?
C2 C3 C4 C5 -16.2(2) . . . . ?
C1 C2 C3 C13 -47.7(3) . . . . ?
C1 C2 C3 C12 75.2(3) . . . . ?
C1 C2 C3 C4 -168.5(2) . . . . ?
C1 C11 C10 C9 176.6(2) 5_656 . . . ?
C13 C3 C4 C5 -138.3(2) . . . . ?
C11 N2 C8 C9 -0.4(3) . . . . ?
C11 N2 C8 C6 179.9(3) . . . . ?
C11 C10 C9 Br1 -179.33(18) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C10 C9 C8 N2 0.1(3) . . . . ?
C10 C9 C8 C6 179.7(3) . . . . ?
C3 C2 C1 C11 -171.7(2) . . . 5_656 ?
C9 C8 C6 C5 -178.3(3) . . . . ?
C9 C8 C6 O1 -7.0(5) . . . . ?
C8 N2 C11 C1 -176.6(2) . . . 5_656 ?
C8 N2 C11 C10 0.6(3) . . . . ?
C8 C6 O1 C7 98.8(4) . . . . ?
C5 N1 C2 C1 176.8(2) . . . . ?
C5 N1 C2 C3 -7.4(3) . . . . ?
C5 C6 O1 C7 -88.7(4) . . . . ?
C6 C5 C4 C3 -166.3(3) . . . . ?
C12 C3 C4 C5 97.7(2) . . . . ?
C4 C5 C6 C8 179.5(3) . . . . ?
C4 C5 C6 O1 7.9(4) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'
