#------------------------------------------------------------------------------
#$Date: 2023-08-05 12:14:58 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/25/7062554.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_7062554
loop_
_publ_author_name
'Nguyen Tran, Anh Thu'
'Wu, Zhiyuan'
'Chung, Duy T. M.'
'Nalaoh, Phattananawee'
'Lindsey, Jonathan S.'
_publ_section_title
;
 Synthesis of model southern rim structures of photosynthetic
 tetrapyrroles and phyllobilins
;
_journal_issue                   29
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13626
_journal_page_last               13637
_journal_paper_doi               10.1039/D3NJ02515B
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C13 H12 N2 O3'
_chemical_formula_sum            'C13 H12 N2 O3'
_chemical_formula_weight         244.25
_chemical_name_common            Z-15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_update_record
;
2023-05-29 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2578(2)
_cell_length_b                   6.8693(2)
_cell_length_c                   14.7437(3)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    110.(2)
_cell_measurement_theta_max      79.5901
_cell_measurement_theta_min      3.9697
_cell_volume                     1127.83(4)
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_collection
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27604
_diffrn_reflns_theta_full        79.87
_diffrn_reflns_theta_max         79.87
_diffrn_reflns_theta_min         3.97
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    0.863
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0338
_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)+(0.0373P)²+0.6384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                2399
_reflns_number_total             2446
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02515b2.cif
_cod_data_source_block           rs061
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7062551--7062554.cif.
;
_cod_database_code               7062554
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.47210(6) 0.69106(11) 0.63460(5) 0.01458(17) Uani d . . . 1 . .
O O2 0.22002(7) 0.79092(13) 0.66650(5) 0.0222(2) Uani d . . . 1 . .
O O3 0.16835(7) 0.95127(11) 0.53374(5) 0.01570(17) Uani d . . . 1 . .
N N1 0.41762(8) 0.76704(13) 0.32107(6) 0.01394(19) Uani d . . . 1 . .
H H1 0.3781(13) 0.765(2) 0.2656(10) 0.017 Uiso d U . . 1 . .
N N2 0.26797(8) 0.33889(13) 0.35298(6) 0.01428(19) Uani d . . . 1 . .
H H2 0.3488(14) 0.335(2) 0.3603(10) 0.017 Uiso d U . . 1 . .
C C1 0.53899(10) 0.81100(16) 0.34405(7) 0.0151(2) Uani d . . . 1 . .
H H1A 0.591361 0.845524 0.301665 0.018 Uiso calc U . R 1 . .
C C2 0.57134(9) 0.79698(15) 0.43679(7) 0.0139(2) Uani d . . . 1 . .
H H2A 0.648598 0.819017 0.47077 0.017 Uiso calc U . R 1 . .
C C3 0.46440(9) 0.74214(15) 0.47190(7) 0.0120(2) Uani d . . . 1 . .
C C4 0.37320(9) 0.72613(15) 0.39903(7) 0.0119(2) Uani d . . . 1 . .
C C5 0.25211(9) 0.67209(15) 0.42266(7) 0.0123(2) Uani d . . . 1 . .
H H5 0.194933 0.781942 0.405484 0.015 Uiso calc U . R 1 . .
C C6 0.19934(9) 0.48808(15) 0.37888(7) 0.0128(2) Uani d . . . 1 . .
C C7 0.08068(9) 0.43418(17) 0.35766(7) 0.0160(2) Uani d . . . 1 . .
H H7 0.013104 0.508968 0.368316 0.019 Uiso calc U . R 1 . .
C C8 0.07765(10) 0.24650(17) 0.31696(7) 0.0181(2) Uani d . . . 1 . .
H H8 0.007856 0.172846 0.295159 0.022 Uiso calc U . R 1 . .
C C9 0.19419(10) 0.19161(16) 0.31502(7) 0.0172(2) Uani d . . . 1 . .
H H9 0.219659 0.07237 0.291507 0.021 Uiso calc U . R 1 . .
C C10 0.41978(9) 0.69904(14) 0.55571(7) 0.0115(2) Uani d . . . 1 . .
C C11 0.28205(9) 0.66088(15) 0.53003(7) 0.0123(2) Uani d . . . 1 . .
H H11 0.2643 0.526117 0.549903 0.015 Uiso calc U . R 1 . .
C C12 0.21903(9) 0.80463(16) 0.58472(7) 0.0138(2) Uani d . . . 1 . .
C C13 0.11574(10) 1.10598(17) 0.58191(8) 0.0200(2) Uani d . . . 1 . .
H H13A 0.099284 1.218708 0.541274 0.03 Uiso calc U . R 1 . .
H H13B 0.171838 1.143604 0.636321 0.03 Uiso calc U . R 1 . .
H H13C 0.040588 1.060045 0.600662 0.03 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 O3 C13 . . 116.65(8) ?
C4 N1 C1 . . 108.14(9) ?
C4 N1 H1 . . 126.5(9) ?
C1 N1 H1 . . 125.4(9) ?
C6 N2 C9 . . 109.39(9) ?
C6 N2 H2 . . 126.0(9) ?
C9 N2 H2 . . 124.6(9) ?
C2 C1 N1 . . 109.66(9) ?
C2 C1 H1A . . 125.2 ?
N1 C1 H1A . . 125.2 ?
C1 C2 C3 . . 105.44(9) ?
C1 C2 H2A . . 127.3 ?
C3 C2 H2A . . 127.3 ?
C4 C3 C2 . . 108.04(9) ?
C4 C3 C10 . . 109.93(9) ?
C2 C3 C10 . . 142.02(10) ?
N1 C4 C3 . . 108.72(9) ?
N1 C4 C5 . . 135.37(9) ?
C3 C4 C5 . . 115.90(9) ?
C6 C5 C4 . . 115.05(8) ?
C6 C5 C11 . . 113.87(8) ?
C4 C5 C11 . . 100.25(8) ?
C6 C5 H5 . . 109.1 ?
C4 C5 H5 . . 109.1 ?
C11 C5 H5 . . 109.1 ?
N2 C6 C7 . . 107.65(9) ?
N2 C6 C5 . . 123.06(9) ?
C7 C6 C5 . . 129.29(10) ?
C6 C7 C8 . . 107.60(10) ?
C6 C7 H7 . . 126.2 ?
C8 C7 H7 . . 126.2 ?
C9 C8 C7 . . 107.16(10) ?
C9 C8 H8 . . 126.4 ?
C7 C8 H8 . . 126.4 ?
C8 C9 N2 . . 108.20(10) ?
C8 C9 H9 . . 125.9 ?
N2 C9 H9 . . 125.9 ?
O1 C10 C3 . . 130.38(10) ?
O1 C10 C11 . . 122.94(9) ?
C3 C10 C11 . . 106.67(8) ?
C12 C11 C10 . . 106.68(8) ?
C12 C11 C5 . . 117.14(8) ?
C10 C11 C5 . . 107.11(8) ?
C12 C11 H11 . . 108.5 ?
C10 C11 H11 . . 108.5 ?
C5 C11 H11 . . 108.5 ?
O2 C12 O3 . . 124.19(10) ?
O2 C12 C11 . . 122.95(10) ?
O3 C12 C11 . . 112.78(8) ?
O3 C13 H13A . . 109.5 ?
O3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.2254(12) ?
O2 C12 . 1.2077(13) ?
O3 C12 . 1.3339(13) ?
O3 C13 . 1.4519(13) ?
N1 C4 . 1.3487(13) ?
N1 C1 . 1.3917(14) ?
N1 H1 . 0.872(15) ?
N2 C6 . 1.3710(14) ?
N2 C9 . 1.3748(14) ?
N2 H2 . 0.901(15) ?
C1 C2 . 1.3658(15) ?
C1 H1A . 0.95 ?
C2 C3 . 1.4290(14) ?
C2 H2A . 0.95 ?
C3 C4 . 1.3771(14) ?
C3 C10 . 1.4315(14) ?
C4 C5 . 1.5024(14) ?
C5 C6 . 1.5016(14) ?
C5 C11 . 1.5712(13) ?
C5 H5 . 1.0 ?
C6 C7 . 1.3773(14) ?
C7 C8 . 1.4203(16) ?
C7 H7 . 0.95 ?
C8 C9 . 1.3694(16) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 C11 . 1.5633(13) ?
C11 C12 . 1.5155(14) ?
C11 H11 . 1.0 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 4_575 0.872(15) 2.354(14) 2.9177(11) 122.6(11) ?
N1 H1 O2 4_575 0.872(15) 2.165(15) 2.9686(12) 153.0(13) ?
N2 H2 O1 3_666 0.901(15) 2.014(15) 2.9123(12) 174.1(13) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 C1 C2 . . . . 0.25(12) ?
N1 C1 C2 C3 . . . . -0.10(12) ?
C1 C2 C3 C4 . . . . -0.09(12) ?
C1 C2 C3 C10 . . . . -179.88(13) ?
C1 N1 C4 C3 . . . . -0.31(12) ?
C1 N1 C4 C5 . . . . 178.85(11) ?
C2 C3 C4 N1 . . . . 0.25(12) ?
C10 C3 C4 N1 . . . . -179.89(9) ?
C2 C3 C4 C5 . . . . -179.09(9) ?
C10 C3 C4 C5 . . . . 0.77(13) ?
N1 C4 C5 C6 . . . . 59.85(16) ?
C3 C4 C5 C6 . . . . -121.04(10) ?
N1 C4 C5 C11 . . . . -177.57(11) ?
C3 C4 C5 C11 . . . . 1.55(11) ?
C9 N2 C6 C7 . . . . 0.41(11) ?
C9 N2 C6 C5 . . . . -179.88(9) ?
C4 C5 C6 N2 . . . . 26.67(14) ?
C11 C5 C6 N2 . . . . -88.27(11) ?
C4 C5 C6 C7 . . . . -153.69(10) ?
C11 C5 C6 C7 . . . . 91.36(13) ?
N2 C6 C7 C8 . . . . -0.42(12) ?
C5 C6 C7 C8 . . . . 179.90(10) ?
C6 C7 C8 C9 . . . . 0.27(12) ?
C7 C8 C9 N2 . . . . -0.02(12) ?
C6 N2 C9 C8 . . . . -0.24(12) ?
C4 C3 C10 O1 . . . . 177.47(11) ?
C2 C3 C10 O1 . . . . -2.7(2) ?
C4 C3 C10 C11 . . . . -2.77(11) ?
C2 C3 C10 C11 . . . . 177.02(13) ?
O1 C10 C11 C12 . . . . 57.27(12) ?
C3 C10 C11 C12 . . . . -122.51(9) ?
O1 C10 C11 C5 . . . . -176.53(9) ?
C3 C10 C11 C5 . . . . 3.68(11) ?
C6 C5 C11 C12 . . . . -119.93(10) ?
C4 C5 C11 C12 . . . . 116.65(9) ?
C6 C5 C11 C10 . . . . 120.37(9) ?
C4 C5 C11 C10 . . . . -3.04(10) ?
C13 O3 C12 O2 . . . . 2.46(15) ?
C13 O3 C12 C11 . . . . -174.31(8) ?
C10 C11 C12 O2 . . . . -72.01(13) ?
C5 C11 C12 O2 . . . . 168.07(10) ?
C10 C11 C12 O3 . . . . 104.81(9) ?
C5 C11 C12 O3 . . . . -15.11(12) ?
