#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/64/7226477.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_7226477
loop_
_publ_author_name
'Sousa, Ana Catarina'
'Piedade, M. Fátima M. M.'
'Martins, Lígia O.'
'Robalo, M. Paula'
_publ_section_title
;
 Eco-friendly synthesis of indo dyes mediated by a bacterial laccase
;
_journal_issue                   22
_journal_name_full               'Green Chem.'
_journal_page_first              6063
_journal_paper_doi               10.1039/C6GC02050J
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C13 H13 N3 O'
_chemical_formula_weight         227.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-04-26 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.725(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5515(11)
_cell_length_b                   3.9004(3)
_cell_length_c                   20.9865(16)
_cell_measurement_reflns_used    2948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.39
_cell_measurement_theta_min      3.02
_cell_volume                     1105.50(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10590
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.401
_diffrn_reflns_theta_min         3.176
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9396
_exptl_absorpt_correction_type   psi-scans
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       paralelipedic
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0695P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2013
_reflns_number_total             2710
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6gc02050j3.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7226477.cif.'
_cod_database_code               7226477
_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   0.940
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'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
O1 O 0.44847(6) 0.0364(3) 0.21966(4) 0.0323(2) Uani 1 1 d . .
N2 N 0.15933(7) 0.2631(2) 0.03108(4) 0.0216(2) Uani 1 1 d . .
N1 N 0.16076(9) 0.3755(3) -0.23486(5) 0.0276(3) Uani 1 1 d . .
N3 N 0.12439(8) 0.3993(3) 0.15090(5) 0.0266(3) Uani 1 1 d . .
C10 C 0.38209(9) 0.0928(3) 0.17574(5) 0.0224(3) Uani 1 1 d . .
C9 C 0.28859(9) 0.2313(3) 0.18791(5) 0.0218(3) Uani 1 1 d . .
H9 H 0.2776 0.2923 0.2296 0.026 Uiso 1 1 calc R U
C8 C 0.21400(8) 0.2784(3) 0.14069(5) 0.0201(2) Uani 1 1 d . .
C7 C 0.23294(8) 0.2058(3) 0.07306(5) 0.0190(2) Uani 1 1 d . .
C4 C 0.16725(9) 0.2667(3) -0.03502(5) 0.0199(2) Uani 1 1 d . .
C3 C 0.08518(8) 0.1547(3) -0.07484(5) 0.0220(3) Uani 1 1 d . .
H3 H 0.0306 0.0628 -0.0568 0.026 Uiso 1 1 calc R U
C2 C 0.08476(8) 0.1796(3) -0.14034(5) 0.0219(3) Uani 1 1 d . .
H2 H 0.0316 0.0909 -0.1661 0.026 Uiso 1 1 calc R U
C1 C 0.16293(9) 0.3362(3) -0.16879(5) 0.0207(3) Uani 1 1 d . .
C12 C 0.33000(8) 0.0680(3) 0.06138(5) 0.0204(2) Uani 1 1 d . .
H12 H 0.3435 0.0216 0.0195 0.024 Uiso 1 1 calc R U
C11 C 0.40067(8) 0.0054(3) 0.10870(5) 0.0210(2) Uani 1 1 d . .
C13 C 0.49823(9) -0.1522(3) 0.09776(6) 0.0278(3) Uani 1 1 d . .
H13A H 0.4980 -0.2233 0.0540 0.042 Uiso 1 1 calc R U
H13B H 0.5095 -0.3475 0.1252 0.042 Uiso 1 1 calc R U
H13C H 0.5499 0.0130 0.1071 0.042 Uiso 1 1 calc R U
C6 C 0.24472(8) 0.4475(3) -0.12943(5) 0.0216(3) Uani 1 1 d . .
H6 H 0.2980 0.5478 -0.1476 0.026 Uiso 1 1 calc R U
C5 C 0.24735(8) 0.4104(3) -0.06401(5) 0.0214(3) Uani 1 1 d . .
H5 H 0.3031 0.4817 -0.0387 0.026 Uiso 1 1 calc R U
H3N H 0.0792(11) 0.423(4) 0.1184(8) 0.032 Uiso 1 1 d . U
H4N H 0.1068(11) 0.446(4) 0.1890(8) 0.032 Uiso 1 1 d . U
H2N H 0.2001(12) 0.541(4) -0.2476(7) 0.039(4) Uiso 1 1 d . .
H1N H 0.1030(13) 0.382(4) -0.2555(8) 0.041(4) Uiso 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
C7 N2 C4 123.94(10)
O1 C10 C9 122.10(10)
O1 C10 C11 119.20(11)
C9 C10 C11 118.68(10)
C8 C9 C10 122.53(10)
N3 C8 C9 123.93(10)
N3 C8 C7 116.73(10)
C9 C8 C7 119.30(10)
N2 C7 C12 127.12(10)
N2 C7 C8 115.58(10)
C12 C7 C8 117.26(10)
N2 C4 C5 123.94(10)
N2 C4 C3 117.69(10)
C5 C4 C3 117.97(10)
C2 C3 C4 120.63(11)
C3 C2 C1 121.05(10)
N1 C1 C6 120.36(11)
N1 C1 C2 121.22(10)
C6 C1 C2 118.40(10)
C11 C12 C7 122.66(10)
C12 C11 C10 119.41(11)
C12 C11 C13 123.19(10)
C10 C11 C13 117.40(10)
C5 C6 C1 120.74(11)
C6 C5 C4 121.07(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.2531(13)
N2 C7 1.2948(14)
N2 C4 1.4003(14)
N1 C1 1.3929(14)
N3 C8 1.3363(15)
C10 C9 1.4199(17)
C10 C11 1.4890(16)
C9 C8 1.3684(16)
C8 C7 1.4902(15)
C7 C12 1.4603(16)
C4 C5 1.4041(16)
C4 C3 1.4046(15)
C3 C2 1.3778(15)
C2 C1 1.3985(16)
C1 C6 1.3958(15)
C12 C11 1.3438(15)
C11 C13 1.4928(16)
C6 C5 1.3780(15)
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
O1 C10 C9 C8 -176.80(11)
C11 C10 C9 C8 1.90(18)
C10 C9 C8 N3 178.11(11)
C10 C9 C8 C7 -4.42(18)
C4 N2 C7 C12 -13.56(18)
C4 N2 C7 C8 168.73(10)
N3 C8 C7 N2 -1.03(15)
C9 C8 C7 N2 -178.68(10)
N3 C8 C7 C12 -178.97(10)
C9 C8 C7 C12 3.38(16)
C7 N2 C4 C5 -39.94(17)
C7 N2 C4 C3 147.49(11)
N2 C4 C3 C2 174.31(10)
C5 C4 C3 C2 1.29(17)
C4 C3 C2 C1 -4.08(18)
C3 C2 C1 N1 -177.13(11)
C3 C2 C1 C6 4.08(17)
N2 C7 C12 C11 -177.43(11)
C8 C7 C12 C11 0.23(17)
C7 C12 C11 C10 -2.73(17)
C7 C12 C11 C13 176.74(10)
O1 C10 C11 C12 -179.47(11)
C9 C10 C11 C12 1.79(17)
O1 C10 C11 C13 1.03(16)
C9 C10 C11 C13 -177.71(11)
N1 C1 C6 C5 179.83(11)
C2 C1 C6 C5 -1.37(17)
C1 C6 C5 C4 -1.36(17)
N2 C4 C5 C6 -171.14(10)
C3 C4 C5 C6 1.41(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 207762
