#------------------------------------------------------------------------------
#$Date: 2023-08-05 11:14:58 +0200 (Sat 05 de Aug de 2023) $
#$Revision: 285474 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/25/7062551.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_7062551
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         'C10 H11 N O5'
_chemical_formula_sum            'C10 H11 N O5'
_chemical_formula_weight         225.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                92.212(7)
_cell_angle_beta                 96.911(8)
_cell_angle_gamma                94.926(8)
_cell_formula_units_Z            4
_cell_length_a                   6.4414(14)
_cell_length_b                   11.785(3)
_cell_length_c                   13.959(3)
_cell_measurement_reflns_used    2731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      3.34
_cell_volume                     1046.8(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0822
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13728
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.331
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0951 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8724.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.306
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0749
_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)+(0.0269P)²+1.4927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3015
_reflns_number_total             4249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj02515b2.cif
_cod_data_source_block           mo_ncsu_pn33_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7062551--7062554.cif.'
_cod_database_code               7062551
_shelx_shelxl_version_number     2019/1
_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_max   0.998
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C12(H12), C14(H14), N1(H1), N2(H2A)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3053(5) 0.7185(2) 0.6066(2) 0.0150(7) Uani 1 1 d . . . . .
C2 C 0.2702(5) 0.6246(2) 0.5393(2) 0.0142(7) Uani 1 1 d . . . . .
H2 H 0.270990 0.546632 0.554024 0.017 Uiso 1 1 calc R . . . .
C3 C 0.2351(5) 0.6653(2) 0.4494(2) 0.0145(7) Uani 1 1 d . . . . .
C4 C 0.2913(5) 0.8156(3) 0.5531(2) 0.0148(7) Uani 1 1 d . . . . .
H4 H 0.308044 0.891950 0.579130 0.018 Uiso 1 1 calc R . . . .
C5 C 0.3490(5) 0.7196(3) 0.7117(2) 0.0158(7) Uani 1 1 d . . . . .
C6 C 0.3693(6) 0.6037(3) 0.7547(2) 0.0227(8) Uani 1 1 d . . . . .
H6A H 0.229054 0.560595 0.748314 0.027 Uiso 1 1 calc R . . . .
H6B H 0.460795 0.560107 0.717916 0.027 Uiso 1 1 calc R . . . .
C7 C 0.4591(6) 0.6139(3) 0.8590(3) 0.0222(8) Uani 1 1 d . . . . .
C8 C 0.7812(6) 0.6417(3) 0.9635(3) 0.0315(9) Uani 1 1 d . . . . .
H8A H 0.932774 0.648595 0.959959 0.047 Uiso 1 1 calc GR . . . .
H8B H 0.742984 0.573019 0.997263 0.047 Uiso 1 1 calc GR . . . .
H8C H 0.743702 0.708901 0.998849 0.047 Uiso 1 1 calc GR . . . .
C9 C 0.1889(5) 0.6047(2) 0.3559(2) 0.0145(7) Uani 1 1 d . . . . .
C10 C 0.1147(6) 0.6240(3) 0.1871(2) 0.0278(9) Uani 1 1 d . . . . .
H10A H 0.091731 0.683711 0.141071 0.042 Uiso 1 1 calc GR . . . .
H10B H -0.013666 0.572369 0.184657 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.229793 0.580873 0.170177 0.042 Uiso 1 1 calc GR . . . .
C11 C 0.1792(5) 0.1169(2) 0.3472(2) 0.0155(7) Uani 1 1 d . . . . .
C12 C 0.1717(5) 0.2329(2) 0.3338(2) 0.0147(7) Uani 1 1 d . . . . .
H12 H 0.149965 0.267302 0.273346 0.018 Uiso 1 1 calc R . . . .
C13 C 0.2267(5) 0.2107(3) 0.4921(2) 0.0154(7) Uani 1 1 d . . . . .
C14 C 0.2133(5) 0.1042(3) 0.4476(2) 0.0153(7) Uani 1 1 d . . . . .
H14 H 0.224978 0.034416 0.478855 0.018 Uiso 1 1 calc R . . . .
C15 C 0.1675(5) 0.0261(3) 0.2728(2) 0.0158(7) Uani 1 1 d . . . . .
C16 C 0.1193(6) 0.0571(3) 0.1682(2) 0.0232(8) Uani 1 1 d . . . . .
H16A H -0.024642 0.081403 0.157333 0.028 Uiso 1 1 calc R . . . .
H16B H 0.218518 0.121845 0.154996 0.028 Uiso 1 1 calc R . . . .
C17 C 0.1371(6) -0.0423(3) 0.1002(2) 0.0216(8) Uani 1 1 d . . . . .
C18 C 0.3767(7) -0.1408(3) 0.0204(3) 0.0336(10) Uani 1 1 d . . . . .
H18A H 0.528445 -0.140766 0.019015 0.050 Uiso 1 1 calc GR . . . .
H18B H 0.307564 -0.132169 -0.045109 0.050 Uiso 1 1 calc GR . . . .
H18C H 0.322054 -0.212878 0.044611 0.050 Uiso 1 1 calc GR . . . .
C19 C 0.2664(5) 0.2465(3) 0.5943(2) 0.0181(7) Uani 1 1 d . . . . .
C20 C 0.3297(6) 0.1787(3) 0.7519(2) 0.0302(9) Uani 1 1 d . . . . .
H20A H 0.358824 0.107819 0.783430 0.045 Uiso 1 1 calc GR . . . .
H20B H 0.206366 0.208237 0.775283 0.045 Uiso 1 1 calc GR . . . .
H20C H 0.451275 0.235102 0.767245 0.045 Uiso 1 1 calc GR . . . .
N1 N 0.2504(4) 0.7839(2) 0.45955(19) 0.0144(6) Uani 1 1 d . . . . .
H1 H 0.235588 0.830486 0.411892 0.017 Uiso 1 1 calc R . . . .
N2 N 0.2005(4) 0.2877(2) 0.42083(18) 0.0137(6) Uani 1 1 d . . . . .
H2A H 0.202473 0.361920 0.431020 0.016 Uiso 1 1 calc R . . . .
O1 O 0.2896(4) 0.15624(18) 0.64865(16) 0.0236(6) Uani 1 1 d . . . . .
O2 O 0.6691(4) 0.63361(19) 0.86665(17) 0.0255(6) Uani 1 1 d . . . . .
O3 O 0.1683(4) 0.67546(17) 0.28341(15) 0.0183(5) Uani 1 1 d . . . . .
O4 O 0.3683(4) 0.80624(18) 0.76393(16) 0.0215(5) Uani 1 1 d . . . . .
O5 O 0.3608(4) 0.60606(19) 0.92691(18) 0.0288(6) Uani 1 1 d . . . . .
O6 O 0.1701(4) 0.50131(17) 0.34406(16) 0.0225(6) Uani 1 1 d . . . . .
O7 O 0.3353(4) -0.04706(19) 0.08309(17) 0.0277(6) Uani 1 1 d . . . . .
O8 O 0.1929(4) -0.07300(17) 0.29224(16) 0.0206(5) Uani 1 1 d . . . . .
O9 O -0.0061(4) -0.11051(19) 0.06654(18) 0.0298(6) Uani 1 1 d . . . . .
O10 O 0.2784(4) 0.34464(18) 0.62622(16) 0.0218(5) 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'
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
_geom_angle_publ_flag
C2 C1 C5 129.0(3) . . ?
C4 C1 C2 106.3(3) . . ?
C4 C1 C5 124.7(3) . . ?
C3 C2 C1 108.0(3) . . ?
C2 C3 C9 130.1(3) . . ?
C2 C3 N1 107.7(3) . . ?
N1 C3 C9 122.2(3) . . ?
N1 C4 C1 109.0(3) . . ?
C1 C5 C6 115.8(3) . . ?
O4 C5 C1 123.7(3) . . ?
O4 C5 C6 120.5(3) . . ?
C7 C6 C5 112.2(3) . . ?
O2 C7 C6 109.8(3) . . ?
O5 C7 C6 126.0(3) . . ?
O5 C7 O2 124.2(3) . . ?
O3 C9 C3 112.3(2) . . ?
O6 C9 C3 124.2(3) . . ?
O6 C9 O3 123.5(3) . . ?
C12 C11 C14 106.8(3) . . ?
C12 C11 C15 127.1(3) . . ?
C14 C11 C15 126.0(3) . . ?
N2 C12 C11 108.0(3) . . ?
C14 C13 C19 130.4(3) . . ?
C14 C13 N2 107.5(3) . . ?
N2 C13 C19 122.1(3) . . ?
C13 C14 C11 107.6(3) . . ?
C11 C15 C16 117.7(3) . . ?
O8 C15 C11 122.1(3) . . ?
O8 C15 C16 120.2(3) . . ?
C17 C16 C15 111.1(3) . . ?
O7 C17 C16 110.6(3) . . ?
O9 C17 C16 125.4(3) . . ?
O9 C17 O7 124.0(3) . . ?
O1 C19 C13 110.6(3) . . ?
O10 C19 C13 125.0(3) . . ?
O10 C19 O1 124.4(3) . . ?
C4 N1 C3 109.0(2) . . ?
C12 N2 C13 110.0(2) . . ?
C19 O1 C20 116.9(3) . . ?
C7 O2 C8 116.7(3) . . ?
C9 O3 C10 116.9(2) . . ?
C17 O7 C18 116.7(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.409(4) . ?
C1 C4 1.394(4) . ?
C1 C5 1.459(4) . ?
C2 C3 1.361(4) . ?
C3 C9 1.449(4) . ?
C3 N1 1.394(4) . ?
C4 N1 1.333(4) . ?
C5 C6 1.523(4) . ?
C5 O4 1.220(4) . ?
C6 C7 1.497(5) . ?
C7 O2 1.344(4) . ?
C7 O5 1.203(4) . ?
C8 O2 1.450(4) . ?
C9 O3 1.337(4) . ?
C9 O6 1.218(3) . ?
C10 O3 1.444(4) . ?
C11 C12 1.392(4) . ?
C11 C14 1.408(4) . ?
C11 C15 1.453(4) . ?
C12 N2 1.339(4) . ?
C13 C14 1.370(4) . ?
C13 C19 1.458(5) . ?
C13 N2 1.377(4) . ?
C15 C16 1.521(4) . ?
C15 O8 1.230(3) . ?
C16 C17 1.499(4) . ?
C17 O7 1.333(4) . ?
C17 O9 1.207(4) . ?
C18 O7 1.445(4) . ?
C19 O1 1.339(4) . ?
C19 O10 1.215(4) . ?
C20 O1 1.444(4) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C9 -179.2(3) . . . . ?
C1 C2 C3 N1 0.7(3) . . . . ?
C1 C4 N1 C3 0.5(3) . . . . ?
C1 C5 C6 C7 167.6(3) . . . . ?
C2 C1 C4 N1 0.0(3) . . . . ?
C2 C1 C5 C6 3.0(5) . . . . ?
C2 C1 C5 O4 -176.7(3) . . . . ?
C2 C3 C9 O3 -178.7(3) . . . . ?
C2 C3 C9 O6 1.5(5) . . . . ?
C2 C3 N1 C4 -0.8(3) . . . . ?
C3 C9 O3 C10 -177.9(3) . . . . ?
C4 C1 C2 C3 -0.5(4) . . . . ?
C4 C1 C5 C6 -176.7(3) . . . . ?
C4 C1 C5 O4 3.5(5) . . . . ?
C5 C1 C2 C3 179.7(3) . . . . ?
C5 C1 C4 N1 179.8(3) . . . . ?
C5 C6 C7 O2 -80.9(3) . . . . ?
C5 C6 C7 O5 99.1(4) . . . . ?
C6 C7 O2 C8 -177.9(3) . . . . ?
C9 C3 N1 C4 179.2(3) . . . . ?
C11 C12 N2 C13 -0.1(3) . . . . ?
C11 C15 C16 C17 173.5(3) . . . . ?
C12 C11 C14 C13 -0.3(4) . . . . ?
C12 C11 C15 C16 -6.9(5) . . . . ?
C12 C11 C15 O8 173.9(3) . . . . ?
C13 C19 O1 C20 -179.9(3) . . . . ?
C14 C11 C12 N2 0.3(4) . . . . ?
C14 C11 C15 C16 177.2(3) . . . . ?
C14 C11 C15 O8 -2.0(5) . . . . ?
C14 C13 C19 O1 -0.7(5) . . . . ?
C14 C13 C19 O10 178.7(3) . . . . ?
C14 C13 N2 C12 -0.1(3) . . . . ?
C15 C11 C12 N2 -176.2(3) . . . . ?
C15 C11 C14 C13 176.2(3) . . . . ?
C15 C16 C17 O7 -85.1(3) . . . . ?
C15 C16 C17 O9 93.6(4) . . . . ?
C16 C17 O7 C18 178.5(3) . . . . ?
C19 C13 C14 C11 -178.1(3) . . . . ?
C19 C13 N2 C12 178.4(3) . . . . ?
N1 C3 C9 O3 1.3(4) . . . . ?
N1 C3 C9 O6 -178.5(3) . . . . ?
N2 C13 C14 C11 0.2(4) . . . . ?
N2 C13 C19 O1 -178.9(3) . . . . ?
N2 C13 C19 O10 0.6(5) . . . . ?
O4 C5 C6 C7 -12.6(5) . . . . ?
O5 C7 O2 C8 2.2(5) . . . . ?
O6 C9 O3 C10 1.9(5) . . . . ?
O8 C15 C16 C17 -7.3(5) . . . . ?
O9 C17 O7 C18 -0.2(5) . . . . ?
O10 C19 O1 C20 0.6(5) . . . . ?
