#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:25:17 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237111 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/43/1554307.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_1554307
loop_
_publ_author_name
'Wang, Jun-Fei'
'Yao, Yuhang'
'Ning, Yingying'
'Meng, Yin-Shan'
'Hou, Chun-Liang'
'Zhang, Jing'
'Zhang, Jun-Long'
_publ_section_title
;
 The design of rigid cyclic tripyrrins: the importance of intermolecular
 interactions on aggregation and luminescence
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1877
_journal_paper_doi               10.1039/C8QO00313K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C34 H7 Br2 F10 N5 O2, 0.5(C8 O2)'
_chemical_formula_sum            'C38 H7 Br2 F10 N5 O3'
_chemical_formula_weight         931.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-10-24 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.5573(10)
_cell_length_b                   18.3335(13)
_cell_length_c                   14.8419(10)
_cell_measurement_reflns_used    8308
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.2310
_cell_measurement_theta_min      4.1740
_cell_volume                     5049.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  80.00   0.50    2.00    --   -0.90  57.00  60.00   52
  2  ω     56.00  82.00   0.50    2.00    --   -0.90  57.00 -60.00   52
  3  ω     54.00  88.00   0.50    2.00    --   -0.90  57.00-120.00   68
  4  ω     34.00  60.00   0.50    2.00    --   -0.90  57.00-150.00   52
  5  ω     36.00  90.00   0.50    2.00    --    1.30  57.00-180.00  108
  6  ω      6.00  31.00   0.50    2.00    --   -0.90  57.00-120.00   50
  7  ω    -22.00   3.00   0.50    2.00    --   -0.90  57.00-150.00   50
  8  ω    -24.00  55.00   0.50    2.00    --    1.30  57.00 -30.00  158
  9  ω    -25.00  20.00   0.50    2.00    --   -0.90  57.00  90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224958000
_diffrn_orient_matrix_UB_12      -0.0007620000
_diffrn_orient_matrix_UB_13      -0.0386093000
_diffrn_orient_matrix_UB_21      0.0298926000
_diffrn_orient_matrix_UB_22      -0.0092363000
_diffrn_orient_matrix_UB_23      0.0275106000
_diffrn_orient_matrix_UB_31      -0.0077776000
_diffrn_orient_matrix_UB_32      -0.0375787000
_diffrn_orient_matrix_UB_33      -0.0060007000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            52350
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.512
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       block
_exptl_crystal_F_000             1816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4591
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0702
_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)+(0.0845P)²+17.2556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3466
_reflns_number_total             4591
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00313k2.cif
_cod_data_source_block           170406_sq
_cod_original_cell_volume        5049.5(5)
_cod_database_code               1554307
_chemical_oxdiff_formula         'C40 h40 N4 O4 Br2'
_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.
;
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C40) \\sim Ueq, Uanis(C40) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Others
 Fixed Sof: C3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N53(H53), C26(H26), C58(H58), C89(H89)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.826
_platon_squeeze_void_probe_radius 1.20
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br8 Br 0.40099(3) 0.65767(4) 0.32842(5) 0.0723(3) Uani 1 1 d . . . . .
F8 F 0.68765(19) 0.5507(2) -0.0594(2) 0.0662(9) Uani 1 1 d . . . . .
F9 F 0.7040(2) 0.5655(2) 0.2554(2) 0.0831(13) Uani 1 1 d . . . . .
F17 F 0.86082(18) 0.4130(2) 0.0959(3) 0.0728(10) Uani 1 1 d . . . . .
F25 F 0.8139(2) 0.4686(2) 0.2528(2) 0.0809(12) Uani 1 1 d . . . . .
F30 F 0.7961(2) 0.4528(2) -0.0609(2) 0.0866(13) Uani 1 1 d . . . . .
N53 N 0.6107(3) 0.7500 0.0993(4) 0.0357(12) Uani 1 2 d S T P . .
H53 H 0.5637 0.7500 0.1075 0.043 Uiso 1 2 calc RS T P . .
O57 O 0.37910(18) 0.59991(19) 0.1374(3) 0.0588(11) Uani 1 1 d . . . . .
N59 N 0.3404(3) 0.6490(3) -0.0830(3) 0.0447(12) Uani 1 1 d . . . . .
N65 N 0.5009(2) 0.6292(2) 0.1157(3) 0.0433(10) Uani 1 1 d . . . . .
C5 C 0.5638(2) 0.5860(3) 0.1107(3) 0.0392(11) Uani 1 1 d . . . . .
C4 C 0.6523(2) 0.6885(3) 0.0920(3) 0.0376(10) Uani 1 1 d . . . . .
C26 C 0.7231(3) 0.7120(3) 0.0768(3) 0.0428(11) Uani 1 1 d . . . . .
H26 H 0.7639 0.6815 0.0681 0.051 Uiso 1 1 calc R . . . .
C30 C 0.3805(3) 0.7118(3) 0.2228(5) 0.0559(15) Uani 1 1 d . . . . .
C41 C 0.6314(2) 0.6141(3) 0.1000(3) 0.0367(10) Uani 1 1 d . . . . .
C44 C 0.6916(2) 0.5599(2) 0.0979(3) 0.0364(10) Uani 1 1 d . . . . .
C49 C 0.4506(3) 0.5813(3) 0.1278(4) 0.0461(12) Uani 1 1 d . . . . .
C58 C 0.5443(3) 0.5090(3) 0.1202(3) 0.0434(11) Uani 1 1 d . . . . .
H58 H 0.5767 0.4688 0.1192 0.052 Uiso 1 1 calc R . . . .
C62 C 0.8063(3) 0.4618(3) 0.0963(4) 0.0472(12) Uani 1 1 d . . . . .
C74 C 0.7174(3) 0.5306(3) 0.0187(3) 0.0416(11) Uani 1 1 d . . . . .
C77 C 0.7743(3) 0.4818(3) 0.0171(4) 0.0500(13) Uani 1 1 d . . . . .
C89 C 0.4724(3) 0.5054(3) 0.1308(4) 0.0497(13) Uani 1 1 d . . . . .
H89 H 0.4430 0.4634 0.1383 0.060 Uiso 1 1 calc R . . . .
C0AA C 0.3700(3) 0.6755(3) 0.1423(5) 0.0565(16) Uani 1 1 d . . . . .
C24 C 0.7262(3) 0.5380(3) 0.1760(3) 0.0462(12) Uani 1 1 d . . . . .
C27 C 0.7830(3) 0.4898(3) 0.1760(3) 0.0480(12) Uani 1 1 d . . . . .
C29 C 0.3549(3) 0.7117(3) 0.0627(5) 0.0539(14) Uani 1 1 d . . . . .
C40 C 0.3443(3) 0.6687(3) -0.0277(7) 0.0677(19) Uani 1 1 d . U . . .
O1 O 0.1971(4) 0.7500 0.0794(7) 0.130(4) Uani 1 2 d S T P A .
C1 C 0.1731(7) 0.7500 0.1682(9) 0.120(5) Uani 1 2 d S T P A .
C2 C 0.1397(8) 0.7500 0.0180(10) 0.120(5) Uani 1 2 d S T P . .
C1AA C 0.0946(7) 0.7500 0.1663(10) 0.208(14) Uani 1 2 d S T P . .
C3 C 0.0778(8) 0.7779(9) 0.0672(10) 0.091(6) Uani 0.5 1 d . . . A 1
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'
F F 0.0171 0.0103 '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'
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
C4 N53 H53 124.7 8_575 .
C4 N53 H53 124.7 . .
C4 N53 C4 110.7(5) 8_575 .
C49 O57 C0AA 111.6(4) . .
C49 N65 C5 103.0(4) . .
N65 C5 C58 109.4(4) . .
C41 C5 N65 123.7(4) . .
C41 C5 C58 127.0(4) . .
N53 C4 C26 106.7(4) . .
N53 C4 C41 128.9(4) . .
C26 C4 C41 124.3(4) . .
C4 C26 H26 126.1 . .
C26 C26 C4 107.9(3) 8_575 .
C26 C26 H26 126.1 8_575 .
C30 C30 Br8 121.57(18) 8_575 .
C0AA C30 Br8 119.5(4) . .
C0AA C30 C30 118.8(3) . 8_575
C5 C41 C4 128.4(4) . .
C5 C41 C44 116.0(4) . .
C4 C41 C44 115.6(4) . .
C74 C44 C41 122.4(4) . .
C74 C44 C24 116.1(4) . .
C24 C44 C41 121.4(4) . .
O57 C49 C89 120.2(4) . .
N65 C49 O57 122.8(4) . .
N65 C49 C89 117.0(4) . .
C5 C58 H58 126.2 . .
C89 C58 C5 107.6(4) . .
C89 C58 H58 126.2 . .
F17 C62 C77 119.9(5) . .
F17 C62 C27 119.5(5) . .
C27 C62 C77 120.5(4) . .
F8 C74 C44 119.3(4) . .
F8 C74 C77 118.5(4) . .
C44 C74 C77 122.1(4) . .
F30 C77 C62 120.5(5) . .
F30 C77 C74 120.2(5) . .
C62 C77 C74 119.3(5) . .
C49 C89 H89 128.5 . .
C58 C89 C49 103.1(4) . .
C58 C89 H89 128.5 . .
C30 C0AA O57 120.3(6) . .
C30 C0AA C29 122.4(5) . .
C29 C0AA O57 117.1(6) . .
F9 C24 C44 118.8(4) . .
F9 C24 C27 118.3(4) . .
C27 C24 C44 122.8(5) . .
F25 C27 C62 119.7(5) . .
F25 C27 C24 121.2(5) . .
C62 C27 C24 119.1(5) . .
C0AA C29 C29 118.7(3) . 8_575
C0AA C29 C40 121.0(5) . .
C29 C29 C40 120.2(3) 8_575 .
N59 C40 C29 172.8(8) . .
C1 O1 C2 111.8(10) . .
O1 C1 C1AA 107.6(11) . .
O1 C2 C3 105.9(11) . 8_575
O1 C2 C3 105.9(11) . .
C3 C2 C3 41.2(14) 8_575 .
C1 C1AA C3 102.4(11) . 8_575
C1 C1AA C3 102.4(11) . .
C3 C1AA C3 37.6(12) 8_575 .
C2 C3 C1AA 101.4(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br8 C30 1.894(6) .
F8 C74 1.336(5) .
F9 C24 1.346(6) .
F17 C62 1.350(6) .
F25 C27 1.334(6) .
F30 C77 1.337(6) .
N53 H53 0.8800 .
N53 C4 1.370(6) 8_575
N53 C4 1.370(6) .
O57 C49 1.377(6) .
O57 C0AA 1.398(7) .
N59 C40 0.901(9) .
N65 C5 1.411(6) .
N65 C49 1.294(6) .
C5 C41 1.365(7) .
C5 C58 1.465(7) .
C4 C26 1.402(7) .
C4 C41 1.423(7) .
C26 C26 1.392(10) 8_575
C26 H26 0.9500 .
C30 C30 1.402(11) 8_575
C30 C0AA 1.381(9) .
C41 C44 1.497(6) .
C44 C74 1.378(7) .
C44 C24 1.384(7) .
C49 C89 1.450(7) .
C58 H58 0.9500 .
C58 C89 1.346(7) .
C62 C77 1.368(7) .
C62 C27 1.361(7) .
C74 C77 1.384(7) .
C89 H89 0.9500 .
C0AA C29 1.384(9) .
C24 C27 1.375(7) .
C29 C29 1.404(10) 8_575
C29 C40 1.567(11) .
O1 C1 1.392(14) .
O1 C2 1.403(16) .
C1 C1AA 1.456(17) .
C2 C3 1.453(19) 8_575
C2 C3 1.453(19) .
C1AA C3 1.589(19) 8_575
C1AA C3 1.589(19) .
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
Br8 C30 C0AA O57 -4.3(6) . .
Br8 C30 C0AA C29 -179.9(4) . .
F8 C74 C77 F30 -3.4(8) . .
F8 C74 C77 C62 178.7(5) . .
F9 C24 C27 F25 2.4(8) . .
F9 C24 C27 C62 -179.7(5) . .
F17 C62 C77 F30 0.7(8) . .
F17 C62 C77 C74 178.6(5) . .
F17 C62 C27 F25 -0.3(8) . .
F17 C62 C27 C24 -178.3(5) . .
N53 C4 C26 C26 1.0(4) . 8_575
N53 C4 C41 C5 5.1(9) . .
N53 C4 C41 C44 -173.9(5) . .
O57 C49 C89 C58 -179.4(5) . .
O57 C0AA C29 C29 -171.6(3) . 8_575
O57 C0AA C29 C40 3.4(7) . .
N65 C5 C41 C4 0.0(8) . .
N65 C5 C41 C44 178.9(4) . .
N65 C5 C58 C89 -0.1(6) . .
N65 C49 C89 C58 0.8(7) . .
C5 N65 C49 O57 179.3(5) . .
C5 N65 C49 C89 -0.9(6) . .
C5 C41 C44 C74 92.7(6) . .
C5 C41 C44 C24 -89.3(6) . .
C5 C58 C89 C49 -0.4(6) . .
C4 N53 C4 C26 -1.7(7) 8_575 .
C4 N53 C4 C41 176.7(3) 8_575 .
C4 C41 C44 C74 -88.2(6) . .
C4 C41 C44 C24 89.8(6) . .
C26 C4 C41 C5 -176.8(5) . .
C26 C4 C41 C44 4.3(7) . .
C30 C30 C0AA O57 171.5(3) 8_575 .
C30 C30 C0AA C29 -4.1(6) 8_575 .
C30 C0AA C29 C29 4.1(6) . 8_575
C30 C0AA C29 C40 179.2(5) . .
C41 C5 C58 C89 178.9(5) . .
C41 C4 C26 C26 -177.5(4) . 8_575
C41 C44 C74 F8 -0.4(7) . .
C41 C44 C74 C77 178.4(5) . .
C41 C44 C24 F9 1.1(8) . .
C41 C44 C24 C27 -178.1(5) . .
C44 C74 C77 F30 177.8(5) . .
C44 C74 C77 C62 -0.1(8) . .
C44 C24 C27 F25 -178.4(5) . .
C44 C24 C27 C62 -0.5(9) . .
C49 O57 C0AA C30 -81.9(6) . .
C49 O57 C0AA C29 93.9(6) . .
C49 N65 C5 C41 -178.5(5) . .
C49 N65 C5 C58 0.6(6) . .
C58 C5 C41 C4 -178.9(5) . .
C58 C5 C41 C44 0.0(7) . .
C74 C44 C24 F9 179.2(5) . .
C74 C44 C24 C27 0.0(8) . .
C77 C62 C27 F25 178.7(5) . .
C77 C62 C27 C24 0.7(8) . .
C0AA O57 C49 N65 -6.5(8) . .
C0AA O57 C49 C89 173.7(6) . .
C24 C44 C74 F8 -178.4(5) . .
C24 C44 C74 C77 0.3(7) . .
C27 C62 C77 F30 -178.3(5) . .
C27 C62 C77 C74 -0.4(8) . .
O1 C1 C1AA C3 -19.2(6) . .
O1 C1 C1AA C3 19.2(6) . 8_575
O1 C2 C3 C1AA -31.4(10) . .
C1 O1 C2 C3 -21.5(7) . 8_575
C1 O1 C2 C3 21.5(7) . .
C1 C1AA C3 C2 30.9(10) . .
C2 O1 C1 C1AA 0.000(1) . .
C3 C2 C3 C1AA 64.8(9) 8_575 .
C3 C1AA C3 C2 -63.4(9) 8_575 .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.016 -0.008 -0.005 1896 419 ' '
