#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:26:16 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257826 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/97/7059778.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7059778
loop_
_publ_author_name
'David, Sylvain'
'Pilet, Guillaume'
'Berginc, Gérard'
'Andraud, Chantal'
'Maury, Olivier'
_publ_section_title
;
 Poly-halogenated aza-bodipy dyes with improved solubility as a versatile
 synthetic platform for the design of photonic materials
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13125
_journal_page_last               13130
_journal_paper_doi               10.1039/D0NJ02631J
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C40.67 H38 Br2 N3 O6.67'
_chemical_formula_sum            'C40.67 H38 Br2 N3 O6.67'
_chemical_formula_weight         835.23
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2020-04-29 deposited with the CCDC.	2020-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 94.252(11)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.0075(11)
_cell_length_b                   17.5214(17)
_cell_length_c                   27.658(4)
_cell_measurement_reflns_used    4061
_cell_measurement_temperature    100
_cell_measurement_theta_max      29
_cell_measurement_theta_min      4
_cell_volume                     3869.8(9)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            14248
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.697
_diffrn_reflns_theta_min         2.803
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1705.281
_exptl_crystal_size_max          0.692
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.033
_refine_diff_density_max         1.48
_refine_diff_density_min         -1.03
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.3822
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3600
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.0005113
_refine_ls_shift/su_mean         0.0000193
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 15.3 11.8 12.5 4.58 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0917
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0902
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              37
_reflns_limit_l_min              0
_reflns_number_gt                3601
_reflns_number_total             4753
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0613
_oxford_refine_ls_scale          1.264(5)
_oxford_reflns_number_all        3601
_cod_data_source_file            d0nj02631j2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

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

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7059778--7059779.cif.

 Adding full bibliography for 7059778--7059779.cif.
;
_cod_original_cell_volume        3869.8(8)
_cod_original_sg_symbol_H-M      'I 1 2/a 1 '
_cod_database_code               7059778
_oxford_refine_reflns_threshold_expression_ref I>3.0\s(I)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
-x+1/2,y,-z
x+1/2,-y,z
-x+1,y+1/2,-z+1/2
x+1,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.52281(6) 0.18480(2) 0.348421(17) 0.0302 1.0000 Uani . U . . . .
C2 C 0.4966(6) 0.2855(2) 0.37331(16) 0.0245 1.0000 Uani . . . . . .
C3 C 0.5782(6) 0.3446(2) 0.35267(16) 0.0251 1.0000 Uani . . . . . .
C4 C 0.5569(6) 0.4176(2) 0.36963(15) 0.0237 1.0000 Uani . . . . . .
C5 C 0.4544(5) 0.4314(2) 0.40784(15) 0.0198 1.0000 Uani . . . . . .
C6 C 0.3769(5) 0.3690(2) 0.42848(16) 0.0227 1.0000 Uani . . . . . .
C7 C 0.3959(5) 0.2959(2) 0.41112(16) 0.0242 1.0000 Uani . . . . . .
H71 H 0.3421 0.2542 0.4242 0.0291 1.0000 Uiso R . . . . .
H61 H 0.3111 0.3779 0.4554 0.0269 1.0000 Uiso R . . . . .
C8 C 0.4288(5) 0.5088(2) 0.42455(15) 0.0205 1.0000 Uani D . . . . .
N9 N 0.3389(4) 0.52495(19) 0.46232(12) 0.0191 1.0000 Uani D . . . . .
C10 C 0.3323(5) 0.6040(2) 0.46744(14) 0.0199 1.0000 Uani D . . . . .
N11 N 0.2500 0.6404(3) 0.5000 0.0182 1.0000 Uani S T . . . .
C12 C 0.4261(5) 0.6379(2) 0.43025(14) 0.0193 1.0000 Uani . . . . . .
C13 C 0.4854(5) 0.5776(2) 0.40414(15) 0.0212 1.0000 Uani . . . . . .
H131 H 0.5504 0.5809 0.3774 0.0250 1.0000 Uiso R . . . . .
C14 C 0.4503(5) 0.7189(2) 0.41969(15) 0.0203 1.0000 Uani . . . . . .
C15 C 0.4490(5) 0.7749(2) 0.45527(15) 0.0216 1.0000 Uani . . . . . .
C16 C 0.4756(5) 0.8511(2) 0.44265(16) 0.0224 1.0000 Uani . . . . . .
O17 O 0.4747(4) 0.91088(17) 0.47413(12) 0.0270 1.0000 Uani . . . . . .
C18 C 0.4757(7) 0.8934(3) 0.52438(16) 0.0309 1.0000 Uani . . . . . .
H181 H 0.4744 0.9399 0.5423 0.0459 1.0000 Uiso R . . . . .
H182 H 0.5760 0.8649 0.5338 0.0461 1.0000 Uiso R . . . . .
H183 H 0.3775 0.8638 0.5301 0.0459 1.0000 Uiso R . . . . .
C19 C 0.5026(5) 0.8712(2) 0.39538(15) 0.0212 1.0000 Uani . . . . . .
O20 O 0.5192(4) 0.94635(17) 0.38266(12) 0.0251 1.0000 Uani . . . . . .
C21 C 0.6869(6) 0.9735(3) 0.3880(2) 0.0356 1.0000 Uani . . . . . .
H211 H 0.6916 1.0257 0.3772 0.0549 1.0000 Uiso R . . . . .
H212 H 0.7287 0.9708 0.4211 0.0550 1.0000 Uiso R . . . . .
H213 H 0.7592 0.9427 0.3687 0.0547 1.0000 Uiso R . . . . .
C22 C 0.5061(5) 0.8145(2) 0.35993(16) 0.0226 1.0000 Uani . . . . . .
C23 C 0.4804(5) 0.7386(2) 0.37207(16) 0.0236 1.0000 Uani . . . . . .
H231 H 0.4816 0.7009 0.3483 0.0279 1.0000 Uiso R . . . . .
O24 O 0.5350(5) 0.83919(19) 0.31468(12) 0.0312 1.0000 Uani . . . . . .
C25 C 0.5428(9) 0.7821(3) 0.27836(19) 0.0444 1.0000 Uani . . . . . .
H251 H 0.5681 0.8053 0.2480 0.0689 1.0000 Uiso R . . . . .
H252 H 0.6298 0.7461 0.2879 0.0688 1.0000 Uiso R . . . . .
H253 H 0.4368 0.7556 0.2734 0.0688 1.0000 Uiso R . . . . .
H151 H 0.4299 0.7616 0.4881 0.0259 1.0000 Uiso R . . . . .
H91 H 0.297(11) 0.4921(12) 0.481(2) 0.021(2) 0.5000 Uiso D . . . . .
H41 H 0.6114 0.4585 0.3558 0.0271 1.0000 Uiso R . . . . .
H31 H 0.6493 0.3347 0.3278 0.0281 1.0000 Uiso R . . . . .
O1 O 0.0175(14) 0.5047(6) 0.2416(4) 0.0472 0.3333 Uani D U . . . .
C1 C -0.1056(13) 0.3969(7) 0.2744(5) 0.0307 0.3333 Uani D U . . . .
C9 C -0.1690(14) 0.5176(6) 0.2508(5) 0.0302 0.3333 Uani D U . . . .
C11 C 0.0588(14) 0.4292(6) 0.2692(5) 0.0311 0.3333 Uani D U . . . .
C17 C -0.2351(16) 0.4406(5) 0.2474(5) 0.0311 0.3333 Uani D U . . . .
H111 H 0.1092 0.4401 0.3006 0.0368 0.3100 Uiso R . . . . .
H112 H 0.1304 0.3962 0.2528 0.0368 0.3100 Uiso R . . . . .
H11 H -0.1296 0.3938 0.3075 0.0362 0.3150 Uiso R . . . . .
H12 H -0.1050 0.3470 0.2609 0.0362 0.3150 Uiso R . . . . .
H171 H -0.3371 0.4369 0.2627 0.0363 0.3150 Uiso R . . . . .
H172 H -0.2527 0.4247 0.2146 0.0363 0.3150 Uiso R . . . . .
H92 H -0.1794 0.5385 0.2823 0.0356 0.3067 Uiso R . . . . .
H93 H -0.2225 0.5514 0.2273 0.0356 0.3067 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br1 . C2 . C3 . 118.6(3) yes
Br1 . C2 . C7 . 118.8(3) yes
C3 . C2 . C7 . 122.6(4) yes
C2 . C3 . C4 . 119.0(4) yes
C2 . C3 . H31 . 119.9 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 120.6(4) yes
C3 . C4 . H41 . 120.0 no
C5 . C4 . H41 . 119.3 no
C4 . C5 . C6 . 118.2(4) yes
C4 . C5 . C8 . 120.3(4) yes
C6 . C5 . C8 . 121.5(4) yes
C5 . C6 . C7 . 121.3(4) yes
C5 . C6 . H61 . 118.5 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C2 . 118.2(4) yes
C6 . C7 . H71 . 121.7 no
C2 . C7 . H71 . 120.1 no
C5 . C8 . N9 . 122.8(4) yes
C5 . C8 . C13 . 127.6(4) yes
N9 . C8 . C13 . 109.6(4) yes
C8 . N9 . C10 . 108.4(3) yes
C8 . N9 . H91 . 125.8(14) no
C10 . N9 . H91 . 125.7(14) no
N9 . C10 . N11 . 125.1(4) yes
N9 . C10 . C12 . 108.1(3) yes
N11 . C10 . C12 . 126.7(4) yes
C10 . N11 . C10 5_556 122.1(5) yes
C10 . C12 . C13 . 105.9(4) yes
C10 . C12 . C14 . 128.6(4) yes
C13 . C12 . C14 . 125.4(4) yes
C8 . C13 . C12 . 108.0(4) yes
C8 . C13 . H131 . 125.3 no
C12 . C13 . H131 . 126.7 no
C12 . C14 . C15 . 122.3(4) yes
C12 . C14 . C23 . 117.5(4) yes
C15 . C14 . C23 . 120.2(4) yes
C14 . C15 . C16 . 119.1(4) yes
C14 . C15 . H151 . 120.6 no
C16 . C15 . H151 . 120.3 no
C15 . C16 . O17 . 124.4(4) yes
C15 . C16 . C19 . 121.0(4) yes
O17 . C16 . C19 . 114.6(4) yes
C16 . O17 . C18 . 117.3(3) yes
O17 . C18 . H181 . 108.9 no
O17 . C18 . H182 . 108.7 no
H181 . C18 . H182 . 110.0 no
O17 . C18 . H183 . 109.2 no
H181 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 110.5 no
C16 . C19 . O20 . 120.7(4) yes
C16 . C19 . C22 . 119.6(4) yes
O20 . C19 . C22 . 119.7(4) yes
C19 . O20 . C21 . 113.8(3) yes
O20 . C21 . H211 . 110.1 no
O20 . C21 . H212 . 110.2 no
H211 . C21 . H212 . 109.0 no
O20 . C21 . H213 . 110.6 no
H211 . C21 . H213 . 108.4 no
H212 . C21 . H213 . 108.5 no
C19 . C22 . C23 . 120.0(4) yes
C19 . C22 . O24 . 115.6(4) yes
C23 . C22 . O24 . 124.4(4) yes
C14 . C23 . C22 . 120.1(4) yes
C14 . C23 . H231 . 120.0 no
C22 . C23 . H231 . 119.8 no
C22 . O24 . C25 . 116.4(4) yes
O24 . C25 . H251 . 109.8 no
O24 . C25 . H252 . 109.7 no
H251 . C25 . H252 . 108.6 no
O24 . C25 . H253 . 110.7 no
H251 . C25 . H253 . 108.5 no
H252 . C25 . H253 . 109.6 no
C9 . O1 . C11 . 102.5(9) yes
C11 . C1 . C17 . 111.3(10) yes
C11 . C1 . H11 . 111.4 no
C17 . C1 . H11 . 109.7 no
C11 . C1 . H12 . 106.9 no
C17 . C1 . H12 . 108.0 no
H11 . C1 . H12 . 109.3 no
O1 . C9 . C17 . 101.8(10) yes
O1 . C9 . H92 . 110.9 no
C17 . C9 . H92 . 111.1 no
O1 . C9 . H93 . 111.6 no
C17 . C9 . H93 . 112.8 no
H92 . C9 . H93 . 108.6 no
O1 . C11 . C1 . 102.6(9) yes
O1 . C11 . H111 . 110.0 no
C1 . C11 . H111 . 108.4 no
O1 . C11 . H112 . 113.3 no
C1 . C11 . H112 . 113.1 no
H111 . C11 . H112 . 109.2 no
C9 . C17 . C1 . 102.4(10) yes
C9 . C17 . H171 . 110.9 no
C1 . C17 . H171 . 109.9 no
C9 . C17 . H172 . 111.3 no
C1 . C17 . H172 . 112.7 no
H171 . C17 . H172 . 109.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C2 . 1.911(4) yes
C2 . C3 . 1.371(7) yes
C2 . C7 . 1.379(7) yes
C3 . C4 . 1.377(6) yes
C3 . H31 . 0.941 no
C4 . C5 . 1.407(6) yes
C4 . H41 . 0.936 no
C5 . C6 . 1.399(6) yes
C5 . C8 . 1.451(5) yes
C6 . C7 . 1.381(6) yes
C6 . H61 . 0.956 no
C7 . H71 . 0.935 no
C8 . N9 . 1.342(6) yes
C8 . C13 . 1.421(6) yes
N9 . C10 . 1.393(5) yes
N9 . H91 . 0.86(2) no
C10 . N11 . 1.320(5) yes
C10 . C12 . 1.446(6) yes
C12 . C13 . 1.384(6) yes
C12 . C14 . 1.465(6) yes
C13 . H131 . 0.937 no
C14 . C15 . 1.390(6) yes
C14 . C23 . 1.400(6) yes
C15 . C16 . 1.401(6) yes
C15 . H151 . 0.961 no
C16 . O17 . 1.363(5) yes
C16 . C19 . 1.386(6) yes
O17 . C18 . 1.423(6) yes
C18 . H181 . 0.954 no
C18 . H182 . 0.965 no
C18 . H183 . 0.964 no
C19 . O20 . 1.372(5) yes
C19 . C22 . 1.398(6) yes
O20 . C21 . 1.421(6) yes
C21 . H211 . 0.963 no
C21 . H212 . 0.954 no
C21 . H213 . 0.978 no
C22 . C23 . 1.390(6) yes
C22 . O24 . 1.360(5) yes
C23 . H231 . 0.933 no
O24 . C25 . 1.423(7) yes
C25 . H251 . 0.968 no
C25 . H252 . 0.962 no
C25 . H253 . 0.968 no
O1 . C9 . 1.5500(13) yes
O1 . C11 . 1.5500(11) yes
C1 . C11 . 1.4500(13) yes
C1 . C17 . 1.4500(11) yes
C1 . H11 . 0.951 no
C1 . H12 . 0.951 no
C9 . C17 . 1.4501(11) yes
C9 . H92 . 0.954 no
C9 . H93 . 0.956 no
C11 . H111 . 0.949 no
C11 . H112 . 0.954 no
C17 . H171 . 0.949 no
C17 . H172 . 0.949 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N9 . H91 . N9 5_556 121.7(18) 0.860 2.053 2.610(8) yes
C1 . H12 . C25 6_465 139 0.95 2.58 3.352(8) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 6 x .
