#------------------------------------------------------------------------------
#$Date: 2018-07-21 15:52:05 +0200 (Sat 21 de Jul de 2018) $
#$Revision: 209173 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/53/7155391.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_7155391
loop_
_publ_author_name
'Hewage, Nisansala'
'Zeller, Matthias'
'Brückner, Christian'
_publ_section_title
;
 Oxidations of chromene-annulated chlorins.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              396
_journal_page_last               407
_journal_paper_doi               10.1039/c6ob02395a
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C43 H9 F19 N4 O3'
_chemical_formula_weight         990.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-17 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.167(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5252(7)
_cell_length_b                   24.2334(17)
_cell_length_c                   15.7891(16)
_cell_measurement_reflns_used    4302
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.1363
_cell_measurement_theta_min      3.3408
_cell_volume                     2879.3(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_collection       'Apex2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_refinement
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker AXS X8 Prospector CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7917
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.395
_diffrn_reflns_theta_max         66.395
_diffrn_reflns_theta_min         3.341
_diffrn_source                   'I-mu-S microsource X-ray tube'
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2 v2014.11 (Bruker, 2014)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       plate
_exptl_crystal_F_000             980
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.477
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     526
_refine_ls_restrained_S_all      1.387
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.1288
_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)+(0.2300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3683
_refine_ls_wR_factor_ref         0.3961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1901
_reflns_number_total             2436
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ob02395a2.cif
_cod_data_source_block           i2m_sq
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-07-22

 Adding full bibliography for 7155391--7155393.cif.
;
_cod_original_sg_symbol_H-M      'I 2/m'
_cod_database_code               7155391
_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.
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z'
3 'x+1/2, y+1/2, z+1/2'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z'
7 '-x+1/2, -y+1/2, -z+1/2'
8 'x+1/2, -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_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
C1 C 0.4997(14) 0.17476(19) 0.4567(4) 0.0531(18) Uani 1 1 d . . . . .
H1 H 0.5027 0.2064 0.4212 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4936(11) 0.11850(18) 0.4292(3) 0.0420(14) Uani 1 1 d . . . . .
C3 C 0.4849(11) 0.10022(18) 0.3460(3) 0.0407(15) Uani 1 1 d . . . . .
C4 C 0.4934(11) 0.04452(18) 0.3210(3) 0.0395(13) Uani 1 1 d . . . . .
O1 O 0.497(6) 0.0497(8) 0.1677(11) 0.139(17) Uani 0.25 1 d D . P A 2
C5 C 0.4839(12) 0.0282(2) 0.2343(3) 0.0594(18) Uani 0.25 1 d . . P A 2
O2 O 0.4839(12) 0.0282(2) 0.2343(3) 0.0594(18) Uani 0.25 1 d . . P A 2
C5B C 0.4839(12) 0.0282(2) 0.2343(3) 0.0594(18) Uani 0.5 1 d . . P A 1
H5B H 0.4787 0.0518 0.1862 0.071 Uiso 0.5 1 calc R U P A 1
C6 C 0.4692(8) 0.1439(2) 0.2793(4) 0.0302(16) Uani 0.75 1 d DG U P B 1
C7 C 0.3025(7) 0.1602(3) 0.2505(4) 0.052(2) Uani 0.75 1 d DG U P B 1
C8 C 0.2881(7) 0.1996(3) 0.1869(4) 0.052(2) Uani 0.75 1 d DG U P B 1
C9 C 0.4403(8) 0.2227(2) 0.1521(4) 0.048(2) Uani 0.75 1 d DG U P B 1
C10 C 0.6070(7) 0.2064(3) 0.1809(4) 0.053(2) Uani 0.75 1 d DG U P B 1
C11 C 0.6214(6) 0.1670(2) 0.2445(4) 0.048(2) Uani 0.75 1 d DG U P B 1
F1 F 0.1510(11) 0.1404(4) 0.2823(6) 0.093(3) Uani 0.75 1 d D U P B 1
F2 F 0.1218(12) 0.2142(3) 0.1598(6) 0.105(3) Uani 0.75 1 d D U P B 1
F3 F 0.4224(13) 0.2602(3) 0.0883(5) 0.092(3) Uani 0.75 1 d D U P B 1
F4 F 0.7485(13) 0.2293(4) 0.1475(6) 0.103(3) Uani 0.75 1 d D U P B 1
F5 F 0.7785(11) 0.1524(4) 0.2717(6) 0.086(3) Uani 0.75 1 d D U P B 1
C6B C 0.558(3) 0.1403(9) 0.2743(16) 0.038(4) Uani 0.25 1 d D U P B 2
C7B C 0.413(3) 0.1656(10) 0.2380(16) 0.049(4) Uani 0.25 1 d D U P B 2
C8B C 0.429(3) 0.2019(11) 0.1703(18) 0.056(4) Uani 0.25 1 d D U P B 2
C9B C 0.596(2) 0.2190(11) 0.1456(16) 0.050(4) Uani 0.25 1 d D U P B 2
C10B C 0.748(2) 0.1974(11) 0.1875(16) 0.053(4) Uani 0.25 1 d D U P B 2
C11B C 0.727(3) 0.1598(14) 0.253(2) 0.050(5) Uani 0.25 1 d D U P B 2
O1B O 0.244(3) 0.1486(14) 0.252(2) 0.093(3) Uani 0.25 1 d D U P B 2
H1B H 0.2441 0.1141 0.2461 0.139 Uiso 0.25 1 d DR U P B 2
F2B F 0.282(3) 0.2288(9) 0.1414(15) 0.085(5) Uani 0.25 1 d D U P B 2
F3B F 0.616(3) 0.2575(7) 0.0862(11) 0.070(4) Uani 0.25 1 d D U P B 2
F4B F 0.906(3) 0.2146(9) 0.1626(13) 0.082(6) Uani 0.25 1 d D U P B 2
F5B F 0.861(3) 0.1346(9) 0.2872(14) 0.071(6) Uani 0.25 1 d D U P B 2
N1 N 0.5000 0.0866(2) 0.5000 0.0311(13) Uani 1 2 d S T P . .
H1A H 0.5000 0.0502 0.5000 0.037 Uiso 1 2 calc R U P . .
N2 N 0.4981(10) 0.0000 0.3730(3) 0.0313(13) Uani 1 2 d S T P A .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 C1 C2 107.6(3) 2_656 .
C1 C1 H1 126.2 2_656 .
C2 C1 H1 126.2 . .
N1 C2 C3 126.7(4) . .
N1 C2 C1 107.0(4) . .
C3 C2 C1 126.3(4) . .
C2 C3 C4 124.7(4) . .
C2 C3 C6 116.3(4) . .
C4 C3 C6 118.9(4) . .
C2 C3 C6B 117.6(10) . .
C4 C3 C6B 111.7(11) . .
N2 C4 C3 126.5(4) . .
N2 C4 C5 111.2(4) . .
C3 C4 C5 122.2(5) . .
N2 C4 C5B 111.2(4) . .
C3 C4 C5B 122.2(5) . .
O1 C5 O2 116.2(10) . 6
O1 C5 C5 116.2(10) . 6
O1 C5 C4 136.9(10) . .
O2 C5 C4 106.1(3) 6 .
C5 C5 C4 106.1(3) 6 .
C5B C5B C4 106.1(3) 6 .
C5B C5B H5B 127.0 6 .
C4 C5B H5B 127.0 . .
C7 C6 C11 120.0 . .
C7 C6 C3 120.0(5) . .
C11 C6 C3 120.0(5) . .
F1 C7 C6 123.0(4) . .
F1 C7 C8 117.0(4) . .
C6 C7 C8 120.0 . .
F2 C8 C9 121.7(5) . .
F2 C8 C7 118.3(5) . .
C9 C8 C7 120.0 . .
F3 C9 C8 118.7(6) . .
F3 C9 C10 121.2(6) . .
C8 C9 C10 120.0 . .
F4 C10 C9 118.8(5) . .
F4 C10 C11 121.2(5) . .
C9 C10 C11 120.0 . .
F5 C11 C10 119.5(5) . .
F5 C11 C6 120.5(5) . .
C10 C11 C6 120.0 . .
C7B C6B C11B 118.2(16) . .
C7B C6B C3 107.1(13) . .
C11B C6B C3 133.7(15) . .
O1B C7B C6B 122.8(19) . .
O1B C7B C8B 113.7(19) . .
C6B C7B C8B 121.9(16) . .
F2B C8B C9B 120.0(15) . .
F2B C8B C7B 119.0(16) . .
C9B C8B C7B 119.5(15) . .
F3B C9B C8B 120.9(16) . .
F3B C9B C10B 119.7(16) . .
C8B C9B C10B 119.3(14) . .
F4B C10B C11B 122.3(16) . .
F4B C10B C9B 118.0(16) . .
C11B C10B C9B 119.7(15) . .
F5B C11B C10B 121.9(19) . .
F5B C11B C6B 116.8(18) . .
C10B C11B C6B 120.4(16) . .
C7B O1B H1B 106.9 . .
C2 N1 C2 110.6(5) . 2_656
C2 N1 H1A 124.7 . .
C2 N1 H1A 124.7 2_656 .
C4 N2 C4 105.4(5) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.367(11) 2_656
C1 C2 1.431(7) .
C1 H1 0.9500 .
C2 N1 1.360(6) .
C2 C3 1.388(7) .
C3 C4 1.408(7) .
C3 C6 1.497(6) .
C3 C6B 1.59(2) .
C4 N2 1.356(6) .
C4 C5 1.427(7) .
C4 C5B 1.427(7) .
O1 C5 1.18(2) .
C5 O2 1.368(11) 6
C5 C5 1.368(11) 6
C5B C5B 1.368(11) 6
C5B H5B 0.9500 .
C6 C7 1.3900 .
C6 C11 1.3900 .
C7 F1 1.336(9) .
C7 C8 1.3900 .
C8 F2 1.368(9) .
C8 C9 1.3900 .
C9 F3 1.363(7) .
C9 C10 1.3900 .
C10 F4 1.312(8) .
C10 C11 1.3900 .
C11 F5 1.305(10) .
C6B C7B 1.376(16) .
C6B C11B 1.397(17) .
C7B O1B 1.35(2) .
C7B C8B 1.390(16) .
C8B F2B 1.363(18) .
C8B C9B 1.379(16) .
C9B F3B 1.332(16) .
C9B C10B 1.419(16) .
C10B F4B 1.318(18) .
C10B C11B 1.392(16) .
C11B F5B 1.294(19) .
O1B H1B 0.8400 .
N1 C2 1.360(6) 2_656
N1 H1A 0.8800 .
N2 C4 1.356(6) 6
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
C1 C1 C2 N1 -3.1(14) 2_656 .
C1 C1 C2 C3 177.6(9) 2_656 .
N1 C2 C3 C4 -4.5(14) . .
C1 C2 C3 C4 174.7(8) . .
N1 C2 C3 C6 176.8(6) . .
C1 C2 C3 C6 -4.0(14) . .
N1 C2 C3 C6B -155.0(10) . .
C1 C2 C3 C6B 24.2(16) . .
C2 C3 C4 N2 5.1(14) . .
C6 C3 C4 N2 -176.2(7) . .
C6B C3 C4 N2 157.1(10) . .
C2 C3 C4 C5 -179.9(8) . .
C6B C3 C4 C5 -27.9(13) . .
C2 C3 C4 C5B -179.9(8) . .
C6 C3 C4 C5B -1.3(12) . .
N2 C4 C5 O1 -169(3) . .
C3 C4 C5 O1 15(4) . .
N2 C4 C5 O2 -0.3(7) . 6
C3 C4 C5 O2 -176.0(7) . 6
N2 C4 C5 C5 -0.3(7) . 6
C3 C4 C5 C5 -176.0(7) . 6
N2 C4 C5B C5B -0.3(7) . 6
C3 C4 C5B C5B -176.0(7) . 6
C2 C3 C6 C7 -92.7(8) . .
C4 C3 C6 C7 88.5(8) . .
C2 C3 C6 C11 89.1(8) . .
C4 C3 C6 C11 -89.7(8) . .
C11 C6 C7 F1 -178.8(8) . .
C3 C6 C7 F1 3.0(8) . .
C11 C6 C7 C8 0.0 . .
C3 C6 C7 C8 -178.2(5) . .
F1 C7 C8 F2 -1.7(8) . .
C6 C7 C8 F2 179.4(8) . .
F1 C7 C8 C9 178.9(7) . .
C6 C7 C8 C9 0.0 . .
F2 C8 C9 F3 -1.1(9) . .
C7 C8 C9 F3 178.3(7) . .
F2 C8 C9 C10 -179.4(8) . .
C7 C8 C9 C10 0.0 . .
F3 C9 C10 F4 2.4(9) . .
C8 C9 C10 F4 -179.3(8) . .
F3 C9 C10 C11 -178.3(7) . .
C8 C9 C10 C11 0.0 . .
F4 C10 C11 F5 0.0(10) . .
C9 C10 C11 F5 -179.3(8) . .
F4 C10 C11 C6 179.3(9) . .
C9 C10 C11 C6 0.0 . .
C7 C6 C11 F5 179.3(8) . .
C3 C6 C11 F5 -2.5(8) . .
C7 C6 C11 C10 0.0 . .
C3 C6 C11 C10 178.2(5) . .
C2 C3 C6B C7B -100(2) . .
C4 C3 C6B C7B 106(2) . .
C2 C3 C6B C11B 68(4) . .
C4 C3 C6B C11B -86(3) . .
C11B C6B C7B O1B 177(4) . .
C3 C6B C7B O1B -13(4) . .
C11B C6B C7B C8B 12(4) . .
C3 C6B C7B C8B -177(3) . .
O1B C7B C8B F2B 19(5) . .
C6B C7B C8B F2B -175(3) . .
O1B C7B C8B C9B -175(3) . .
C6B C7B C8B C9B -9(5) . .
F2B C8B C9B F3B -8(5) . .
C7B C8B C9B F3B -174(3) . .
F2B C8B C9B C10B 169(3) . .
C7B C8B C9B C10B 3(5) . .
F3B C9B C10B F4B -3(5) . .
C8B C9B C10B F4B -180(3) . .
F3B C9B C10B C11B 176(3) . .
C8B C9B C10B C11B -1(5) . .
F4B C10B C11B F5B -8(6) . .
C9B C10B C11B F5B 173(4) . .
F4B C10B C11B C6B -176(3) . .
C9B C10B C11B C6B 4(6) . .
C7B C6B C11B F5B -179(3) . .
C3 C6B C11B F5B 14(6) . .
C7B C6B C11B C10B -10(5) . .
C3 C6B C11B C10B -177(3) . .
C3 C2 N1 C2 -179.5(11) . 2_656
C1 C2 N1 C2 1.1(5) . 2_656
C3 C4 N2 C4 175.9(5) . 6
C5 C4 N2 C4 0.5(11) . 6
C5B C4 N2 C4 0.5(11) . 6
