#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:49:31 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/25/4032594.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_4032594
loop_
_publ_author_name
'Figliola, Carlotta'
'Robertson, Katherine N.'
'Greening, Sarah'
'Thompson, Alison'
_publ_section_title
;
 Asymmetric Dipyrrin and F-BODIPYs Conjugated to Terminal Alkynes and
 Alkenes.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7059
_journal_page_last               7064
_journal_paper_doi               10.1021/acs.joc.7b01129
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         '2(C17 H21 N2), C H2 Cl2, 2(Br)'
_chemical_formula_sum            'C35 H44 Br2 Cl2 N4'
_chemical_formula_weight         751.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                103.002(5)
_cell_angle_beta                 102.154(5)
_cell_angle_gamma                102.174(5)
_cell_formula_units_Z            1
_cell_length_a                   7.727(4)
_cell_length_b                   10.325(5)
_cell_length_c                   12.026(5)
_cell_measurement_reflns_used    1842
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      21.83
_cell_measurement_theta_min      2.35
_cell_volume                     879.7(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6893
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        22.821
_diffrn_reflns_theta_max         22.820
_diffrn_reflns_theta_min         2.103
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.4761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       'broken needle'
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.040
_refine_diff_density_max         2.314
_refine_diff_density_min         -1.117
_refine_diff_density_rms         0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     182
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1236
_refine_ls_R_factor_gt           0.0883
_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)+(0.1556P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2218
_refine_ls_wR_factor_ref         0.2454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1694
_reflns_number_total             2357
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01129_si_001.cif
_cod_data_source_block           CFD002_KNR
_cod_depositor_comments
'Adding full bibliography for 4032593--4032594.cif.'
_cod_database_code               4032594
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.722
_shelx_estimated_absorpt_t_max   0.907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.45010(15) 0.17508(11) 0.29766(11) 0.0331(5) Uani 1 1 d . . .
N1 N 0.5715(11) 0.3282(9) 0.5861(8) 0.0253(18) Uani 1 1 d D U .
H1 H 0.524(13) 0.289(10) 0.502(2) 0.038 Uiso 1 1 d D U .
N2 N 0.7509(11) 0.4801(8) 0.4084(8) 0.0234(18) Uani 1 1 d D U .
H2 H 0.667(11) 0.392(5) 0.390(9) 0.035 Uiso 1 1 d D U .
C1 C 0.6608(13) 0.4654(11) 0.7761(10) 0.027(2) Uani 1 1 d . U .
C2 C 0.5457(13) 0.3409(11) 0.7696(10) 0.028(2) Uani 1 1 d . U .
C3 C 0.4916(13) 0.2582(10) 0.6501(10) 0.025(2) Uani 1 1 d . U .
C5 C 0.8177(13) 0.5288(10) 0.3277(10) 0.025(2) Uani 1 1 d . U .
C6 C 0.9252(14) 0.6642(10) 0.3863(10) 0.026(2) Uani 1 1 d . U .
C7 C 0.9232(13) 0.6933(10) 0.5043(9) 0.024(2) Uani 1 1 d . U .
C7A C 0.8102(13) 0.5754(10) 0.5182(9) 0.021(2) Uani 1 1 d . U .
C8 C 0.7775(13) 0.5631(10) 0.6247(9) 0.023(2) Uani 1 1 d . U .
H8 H 0.8354 0.6442 0.6889 0.028 Uiso 1 1 calc R U .
C8A C 0.6788(13) 0.4577(10) 0.6558(10) 0.024(2) Uani 1 1 d . U .
C9 C 0.7517(15) 0.5865(11) 0.8789(10) 0.036(3) Uani 1 1 d . U .
H9A H 0.7304 0.5642 0.9507 0.054 Uiso 1 1 calc R U .
H9B H 0.7013 0.6636 0.8678 0.054 Uiso 1 1 calc R U .
H9C H 0.8841 0.6124 0.8867 0.054 Uiso 1 1 calc R U .
C10 C 0.5896(17) 0.2030(13) 0.9160(11) 0.043(3) Uani 1 1 d . U .
H10A H 0.5728 0.1194 0.8524 0.064 Uiso 1 1 calc R U .
H10B H 0.5437 0.1773 0.9803 0.064 Uiso 1 1 calc R U .
H10C H 0.7207 0.2522 0.9465 0.064 Uiso 1 1 calc R U .
C11 C 0.4831(15) 0.2966(12) 0.8676(11) 0.039(3) Uani 1 1 d . U .
H11A H 0.3506 0.2469 0.8383 0.047 Uiso 1 1 calc R U .
H11B H 0.4979 0.3795 0.9329 0.047 Uiso 1 1 calc R U .
C12 C 0.3725(14) 0.1163(10) 0.5998(11) 0.033(3) Uani 1 1 d . U .
H12A H 0.3451 0.0913 0.5132 0.049 Uiso 1 1 calc R U .
H12B H 0.2576 0.1102 0.6232 0.049 Uiso 1 1 calc R U .
H12C H 0.4353 0.0528 0.6296 0.049 Uiso 1 1 calc R U .
C13 C 0.7782(16) 0.4497(12) 0.2032(10) 0.037(3) Uani 1 1 d . U .
H13A H 0.8132 0.3632 0.1993 0.055 Uiso 1 1 calc R U .
H13B H 0.8486 0.5041 0.1624 0.055 Uiso 1 1 calc R U .
H13C H 0.6465 0.4289 0.1649 0.055 Uiso 1 1 calc R U .
C14 C 1.0179(16) 0.8257(11) 0.5965(10) 0.036(3) Uani 1 1 d . U .
H14A H 1.1328 0.8180 0.6444 0.054 Uiso 1 1 calc R U .
H14B H 0.9384 0.8473 0.6476 0.054 Uiso 1 1 calc R U .
H14C H 1.0455 0.8994 0.5587 0.054 Uiso 1 1 calc R U .
C15 C 1.0228(14) 0.7570(11) 0.3332(10) 0.032(3) Uani 1 1 d . U .
C16 C 1.1026(16) 0.8372(12) 0.2939(11) 0.042(3) Uani 1 1 d . U .
H16 H 1.1674 0.9022 0.2621 0.050 Uiso 1 1 calc R U .
C17 C 1.048(5) -0.032(4) 0.044(3) 0.087(9) Uani 0.5 1 d . U P
H17A H 1.1578 0.0144 0.1115 0.105 Uiso 0.5 1 calc R U P
H17B H 1.0114 -0.1298 0.0451 0.105 Uiso 0.5 1 calc R U P
Cl1 Cl 0.8806(8) 0.0352(7) 0.0773(6) 0.126(2) Uani 1 1 d . U .
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'
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
C3 N1 C8A 110.9(9) .
C3 N1 H1 115(7) .
C8A N1 H1 133(7) .
C5 N2 C7A 112.1(8) .
C5 N2 H2 123(6) .
C7A N2 H2 125(6) .
C2 C1 C9 129.3(10) .
C2 C1 C8A 106.5(10) .
C9 C1 C8A 124.1(9) .
C1 C2 C3 107.9(9) .
C1 C2 C11 127.7(11) .
C3 C2 C11 124.4(10) .
N1 C3 C2 108.9(9) .
N1 C3 C12 122.9(10) .
C2 C3 C12 128.1(10) .
N2 C5 C6 106.4(9) .
N2 C5 C13 124.0(9) .
C6 C5 C13 129.6(10) .
C7 C6 C5 108.6(9) .
C7 C6 C15 125.7(10) .
C5 C6 C15 125.7(10) .
C6 C7 C7A 107.2(9) .
C6 C7 C14 126.0(9) .
C7A C7 C14 126.8(10) .
N2 C7A C8 129.7(9) .
N2 C7A C7 105.8(9) .
C8 C7A C7 124.4(10) .
C8A C8 C7A 132.7(10) .
C8A C8 H8 113.6 .
C7A C8 H8 113.6 .
C8 C8A N1 129.8(10) .
C8 C8A C1 124.4(9) .
N1 C8A C1 105.7(8) .
C1 C9 H9A 109.5 .
C1 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C1 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C11 C10 H10A 109.5 .
C11 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C11 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C2 C11 C10 112.8(9) .
C2 C11 H11A 109.0 .
C10 C11 H11A 109.0 .
C2 C11 H11B 109.0 .
C10 C11 H11B 109.0 .
H11A C11 H11B 107.8 .
C3 C12 H12A 109.5 .
C3 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C3 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C5 C13 H13A 109.5 .
C5 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
C5 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
C7 C14 H14A 109.5 .
C7 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C7 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C16 C15 C6 177.1(12) .
C15 C16 H16 180.0 .
Cl1 C17 Cl1 126(2) 2_755
Cl1 C17 H17A 105.9 2_755
Cl1 C17 H17A 105.9 .
Cl1 C17 H17B 105.9 2_755
Cl1 C17 H17B 105.9 .
H17A C17 H17B 106.2 .
C17 Cl1 C17 54(2) 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.325(13) .
N1 C8A 1.383(13) .
N1 H1 0.95(2) .
N2 C5 1.335(13) .
N2 C7A 1.376(13) .
N2 H2 0.95(2) .
C1 C2 1.377(14) .
C1 C9 1.467(15) .
C1 C8A 1.468(15) .
C2 C3 1.419(16) .
C2 C11 1.490(15) .
C3 C12 1.469(14) .
C5 C6 1.400(15) .
C5 C13 1.467(15) .
C6 C7 1.387(15) .
C6 C15 1.438(15) .
C7 C7A 1.407(14) .
C7 C14 1.479(15) .
C7A C8 1.384(14) .
C8 C8A 1.364(13) .
C8 H8 0.9500 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.530(15) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.172(15) .
C16 H16 0.9500 .
C17 Cl1 1.66(4) 2_755
C17 Cl1 1.67(4) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
Cl1 C17 1.66(4) 2_755
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
N1 H1 Br1 0.95(2) 2.37(3) 3.309(9) 170(9)
N2 H2 Br1 0.95(2) 2.36(3) 3.288(8) 167(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_4
C9 C1 C2 C3 179.3(10) . .
C8A C1 C2 C3 -0.5(10) . .
C9 C1 C2 C11 0.0(17) . .
C8A C1 C2 C11 -179.8(9) . .
C8A N1 C3 C2 -0.5(10) . .
C8A N1 C3 C12 -178.7(9) . .
C1 C2 C3 N1 0.6(11) . .
C11 C2 C3 N1 179.9(9) . .
C1 C2 C3 C12 178.8(9) . .
C11 C2 C3 C12 -1.9(16) . .
C7A N2 C5 C6 -0.8(10) . .
C7A N2 C5 C13 179.7(9) . .
N2 C5 C6 C7 1.2(11) . .
C13 C5 C6 C7 -179.4(10) . .
N2 C5 C6 C15 -179.4(9) . .
C13 C5 C6 C15 0.1(16) . .
C5 C6 C7 C7A -1.1(11) . .
C15 C6 C7 C7A 179.4(9) . .
C5 C6 C7 C14 -179.4(10) . .
C15 C6 C7 C14 1.2(16) . .
C5 N2 C7A C8 -177.4(9) . .
C5 N2 C7A C7 0.1(10) . .
C6 C7 C7A N2 0.6(10) . .
C14 C7 C7A N2 178.8(9) . .
C6 C7 C7A C8 178.3(9) . .
C14 C7 C7A C8 -3.4(16) . .
N2 C7A C8 C8A -0.5(17) . .
C7 C7A C8 C8A -177.7(10) . .
C7A C8 C8A N1 -3.0(17) . .
C7A C8 C8A C1 180.0(10) . .
C3 N1 C8A C8 -177.2(9) . .
C3 N1 C8A C1 0.2(10) . .
C2 C1 C8A C8 177.8(9) . .
C9 C1 C8A C8 -2.0(15) . .
C2 C1 C8A N1 0.2(10) . .
C9 C1 C8A N1 -179.6(9) . .
C1 C2 C11 C10 -100.6(13) . .
C3 C2 C11 C10 80.2(13) . .
Cl1 C17 Cl1 C17 0.000(3) 2_755 2_755
