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#$Date: 2016-06-18 12:10:54 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/31/1543123.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_1543123
loop_
_publ_author_name
'Jiang, Bin'
'Du, Chen Chen'
'Li, Min Jie'
'Gao, Ke'
'Kou, Li'
'Chen, Ming'
'Liu, Feng'
'Russell, Thomas P.'
'Wang, Hongyu'
_publ_section_title
;
 Synthesis of fluorinated diphenyl-diketopyrrolopyrrole derivatives as new
 building blocks for conjugated copolymers
;
_journal_issue                   19
_journal_name_full               'Polym. Chem.'
_journal_page_first              3311
_journal_paper_doi               10.1039/C6PY00346J
_journal_volume                  7
_journal_year                    2016
_chemical_formula_sum            'C30 H32 Br2 F2 N2 O4'
_chemical_formula_weight         682.39
_chemical_name_systematic
; 
 ? 
;
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-12-04 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                70.950(5)
_cell_angle_beta                 73.447(4)
_cell_angle_gamma                74.305(4)
_cell_formula_units_Z            1
_cell_length_a                   7.389(3)
_cell_length_b                   8.698(3)
_cell_length_c                   12.870(5)
_cell_measurement_reflns_used    866
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.386
_cell_measurement_theta_min      2.933
_cell_volume                     734.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3067
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.715
_exptl_absorpt_coefficient_mu    2.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_description       block
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0539
_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)+(0.1179P)²] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1948
_reflns_number_total             2533
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6py00346j2.cif
_cod_data_source_block           a50317b
_cod_depositor_comments
'Adding full bibliography for 1543120--1543123.cif.'
_cod_database_code               1543123
_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   0.729
_shelx_estimated_absorpt_t_max   0.767
_shelxl_version_number           2013-2
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
Br1 Br 0.18706(8) -0.14923(7) 0.84346(5) 0.0599(3) Uani 1 1 d . .
F1 F 0.7319(4) 0.0965(4) 0.8626(3) 0.0563(8) Uani 1 1 d . .
O1 O 0.8284(5) 0.6416(5) 0.8441(3) 0.0532(9) Uani 1 1 d . .
N1 N 0.6591(5) 0.4557(5) 0.8429(3) 0.0397(9) Uani 1 1 d . .
C1 C 0.7014(7) 0.5640(6) 0.8897(4) 0.0391(11) Uani 1 1 d . .
C2 C 0.5002(6) 0.3860(5) 0.9116(4) 0.0353(10) Uani 1 1 d . .
C3 C 0.4402(6) 0.4466(5) 1.0044(3) 0.0366(10) Uani 1 1 d . .
C4 C 0.4268(6) 0.2649(6) 0.8868(3) 0.0360(10) Uani 1 1 d . .
C5 C 0.5438(6) 0.1221(5) 0.8650(3) 0.0338(10) Uani 1 1 d . .
C6 C 0.4790(6) -0.0005(6) 0.8495(4) 0.0377(10) Uani 1 1 d . .
H6 H 0.5638 -0.0946 0.8333 0.045 Uiso 1 1 calc R U
C7 C 0.2841(7) 0.0200(6) 0.8588(4) 0.0406(11) Uani 1 1 d . .
C8 C 0.1592(7) 0.1622(6) 0.8813(4) 0.0467(12) Uani 1 1 d . .
H8 H 0.0278 0.1752 0.8870 0.056 Uiso 1 1 calc R U
C9 C 0.2297(7) 0.2838(6) 0.8950(4) 0.0435(11) Uani 1 1 d . .
H9 H 0.1458 0.3790 0.9098 0.052 Uiso 1 1 calc R U
C10 C 0.7410(7) 0.4567(6) 0.7246(4) 0.0446(11) Uani 1 1 d . .
H10A H 0.7450 0.3494 0.7154 0.054 Uiso 1 1 calc R U
H10B H 0.8721 0.4743 0.7045 0.054 Uiso 1 1 calc R U
C11 C 0.6260(8) 0.5900(7) 0.6461(4) 0.0515(12) Uani 1 1 d . .
H11A H 0.6115 0.6963 0.6599 0.062 Uiso 1 1 calc R U
H11B H 0.4985 0.5666 0.6610 0.062 Uiso 1 1 calc R U
C12 C 0.7245(9) 0.5992(8) 0.5234(4) 0.0628(16) Uani 1 1 d . .
H12A H 0.8531 0.6197 0.5096 0.075 Uiso 1 1 calc R U
H12B H 0.7370 0.4930 0.5099 0.075 Uiso 1 1 calc R U
C13 C 0.6163(11) 0.7339(10) 0.4410(6) 0.091(2) Uani 1 1 d . .
H13A H 0.4956 0.7065 0.4470 0.136 Uiso 1 1 calc R U
H13B H 0.6916 0.7424 0.3657 0.136 Uiso 1 1 calc R U
H13C H 0.5932 0.8379 0.4581 0.136 Uiso 1 1 calc R U
C14 C 0.9313(11) 0.1439(10) 0.4238(6) 0.085(2) Uani 1 1 d . .
H14A H 0.9487 0.2521 0.3737 0.102 Uiso 1 1 calc R U
H14B H 0.8145 0.1215 0.4165 0.102 Uiso 1 1 calc R U
C15 C 0.9021(11) -0.0159(11) 0.6087(6) 0.093(3) Uani 1 1 d . .
H15A H 0.7844 -0.0455 0.6091 0.111 Uiso 1 1 calc R U
H15B H 0.8965 -0.0137 0.6844 0.111 Uiso 1 1 calc R U
O2 O 0.9134(8) 0.1446(6) 0.5344(5) 0.0877(14) Uani 1 1 d . .
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'
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'
F F 0.0171 0.0103 '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'
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
C2 N1 C1 111.5(4) . .
C2 N1 C10 125.6(4) . .
C1 N1 C10 120.9(4) . .
O1 C1 N1 123.4(4) . .
O1 C1 C3 133.2(5) . 2_667
N1 C1 C3 103.4(4) . 2_667
C3 C2 N1 107.2(4) . .
C3 C2 C4 128.8(4) . .
N1 C2 C4 123.9(4) . .
C2 C3 C3 109.2(5) . 2_667
C2 C3 C1 142.1(4) . 2_667
C3 C3 C1 108.7(5) 2_667 2_667
C5 C4 C9 117.3(4) . .
C5 C4 C2 121.9(4) . .
C9 C4 C2 120.5(4) . .
F1 C5 C6 117.3(4) . .
F1 C5 C4 118.7(4) . .
C6 C5 C4 123.9(4) . .
C5 C6 C7 117.8(4) . .
C6 C7 C8 120.6(4) . .
C6 C7 Br1 119.3(4) . .
C8 C7 Br1 120.1(4) . .
C9 C8 C7 120.0(4) . .
C8 C9 C4 120.4(4) . .
N1 C10 C11 112.2(4) . .
C10 C11 C12 111.1(4) . .
C13 C12 C11 113.1(5) . .
O2 C14 C15 110.6(6) . 2_756
O2 C15 C14 112.3(6) . 2_756
C14 O2 C15 110.6(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C7 1.887(5) .
F1 C5 1.339(5) .
O1 C1 1.205(6) .
N1 C2 1.404(6) .
N1 C1 1.409(6) .
N1 C10 1.467(6) .
C1 C3 1.456(6) 2_667
C2 C3 1.372(6) .
C2 C4 1.460(6) .
C3 C3 1.406(9) 2_667
C3 C1 1.456(6) 2_667
C4 C5 1.370(6) .
C4 C9 1.398(6) .
C5 C6 1.370(6) .
C6 C7 1.377(6) .
C7 C8 1.388(7) .
C8 C9 1.376(7) .
C10 C11 1.509(7) .
C11 C12 1.525(7) .
C12 C13 1.517(8) .
C14 O2 1.393(8) .
C14 C15 1.483(10) 2_756
C15 O2 1.420(9) .
C15 C14 1.483(10) 2_756
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
C2 N1 C1 O1 -177.9(4) . .
C10 N1 C1 O1 -13.0(7) . .
C2 N1 C1 C3 1.7(5) . 2_667
C10 N1 C1 C3 166.6(4) . 2_667
C1 N1 C2 C3 -0.9(5) . .
C10 N1 C2 C3 -165.0(4) . .
C1 N1 C2 C4 -177.8(4) . .
C10 N1 C2 C4 18.1(7) . .
N1 C2 C3 C3 -0.3(6) . 2_667
C4 C2 C3 C3 176.4(5) . 2_667
N1 C2 C3 C1 -178.2(6) . 2_667
C4 C2 C3 C1 -1.5(9) . 2_667
C3 C2 C4 C5 -123.3(5) . .
N1 C2 C4 C5 53.0(6) . .
C3 C2 C4 C9 50.7(6) . .
N1 C2 C4 C9 -133.0(5) . .
C9 C4 C5 F1 -176.5(4) . .
C2 C4 C5 F1 -2.3(6) . .
C9 C4 C5 C6 0.8(6) . .
C2 C4 C5 C6 175.0(4) . .
F1 C5 C6 C7 176.0(4) . .
C4 C5 C6 C7 -1.3(7) . .
C5 C6 C7 C8 1.0(7) . .
C5 C6 C7 Br1 -177.8(3) . .
C6 C7 C8 C9 -0.3(7) . .
Br1 C7 C8 C9 178.5(4) . .
C7 C8 C9 C4 -0.2(7) . .
C5 C4 C9 C8 0.0(7) . .
C2 C4 C9 C8 -174.3(4) . .
C2 N1 C10 C11 79.3(6) . .
C1 N1 C10 C11 -83.4(6) . .
N1 C10 C11 C12 174.6(5) . .
C10 C11 C12 C13 -178.9(6) . .
C15 C14 O2 C15 -54.9(9) 2_756 .
C14 C15 O2 C14 55.8(10) 2_756 .
