#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/38/1543821.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_1543821
loop_
_publ_author_name
'Zhou, Shuguang'
'Wang, Jinhu'
'Zhang, Feifei'
'Song, Chao'
'Zhu, Jin'
_publ_section_title
;
 A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of
 Heterocycles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2427
_journal_page_last               2430
_journal_paper_doi               10.1021/acs.orglett.6b00949
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C12 H15 N O3'
_chemical_formula_weight         221.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.736(3)
_cell_length_b                   5.8810(12)
_cell_length_c                   14.065(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1159.9(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2206
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.45
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.135(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1649
_reflns_number_gt                1549
_reflns_number_total             2120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00949_si_005.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1159.9(4)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               1543821
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N N 0.27550(15) 0.5903(4) 0.16260(15) 0.0670(6) Uani 1 1 d .
H0A H 0.3232 0.5049 0.1636 0.080 Uiso 1 1 calc R
O1 O 0.06371(11) 0.4213(3) 0.42149(13) 0.0645(5) Uani 1 1 d .
C1 C 0.20034(14) 0.3260(4) 0.36517(15) 0.0472(5) Uani 1 1 d .
H1A H 0.2187 0.2088 0.4115 0.057 Uiso 1 1 calc R
O2 O 0.46989(11) -0.2651(3) 0.40395(12) 0.0592(5) Uani 1 1 d .
C2 C 0.11978(14) 0.4504(4) 0.36056(16) 0.0499(6) Uani 1 1 d .
O3 O 0.52222(11) 0.0309(3) 0.33617(13) 0.0619(5) Uani 1 1 d .
C3 C 0.09246(16) 0.6237(4) 0.29050(18) 0.0593(6) Uani 1 1 d .
H3A H 0.0385 0.7094 0.2870 0.071 Uiso 1 1 calc R
C4 C 0.14376(16) 0.6704(4) 0.22650(18) 0.0606(7) Uani 1 1 d .
H4A H 0.1235 0.7866 0.1799 0.073 Uiso 1 1 calc R
C5 C 0.22621(15) 0.5470(4) 0.22954(16) 0.0511(6) Uani 1 1 d .
C6 C 0.25538(14) 0.3716(3) 0.30178(15) 0.0447(5) Uani 1 1 d .
C7 C 0.0841(2) 0.2347(5) 0.4881(2) 0.0750(8) Uani 1 1 d .
H7A H 0.0401 0.2334 0.5262 0.112 Uiso 1 1 calc R
H7B H 0.1480 0.2481 0.5324 0.112 Uiso 1 1 calc R
H7C H 0.0780 0.0958 0.4507 0.112 Uiso 1 1 calc R
C8 C 0.2502(2) 0.7737(5) 0.0907(2) 0.0727(8) Uani 1 1 d .
H8A H 0.2932 0.7748 0.0515 0.109 Uiso 1 1 calc R
H8B H 0.2545 0.9160 0.1253 0.109 Uiso 1 1 calc R
H8C H 0.1862 0.7520 0.0477 0.109 Uiso 1 1 calc R
C9 C 0.34281(14) 0.2449(4) 0.31189(15) 0.0452(5) Uani 1 1 d .
H9A H 0.3869 0.3143 0.2861 0.054 Uiso 1 1 calc R
C10 C 0.36711(15) 0.0416(4) 0.35365(15) 0.0478(5) Uani 1 1 d .
H10A H 0.3242 -0.0381 0.3777 0.057 Uiso 1 1 calc R
C11 C 0.46020(15) -0.0581(4) 0.36227(14) 0.0441(5) Uani 1 1 d .
C12 C 0.55835(17) -0.3821(4) 0.41426(17) 0.0601(7) Uani 1 1 d .
H12A H 0.5575 -0.5273 0.4452 0.090 Uiso 1 1 calc R
H12B H 0.6105 -0.2932 0.4550 0.090 Uiso 1 1 calc R
H12C H 0.5659 -0.4037 0.3495 0.090 Uiso 1 1 calc R
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
C5 N C8 122.6(2)
C5 N H0A 118.7
C8 N H0A 118.7
C2 O1 C7 117.67(18)
C2 C1 C6 121.8(2)
C2 C1 H1A 119.1
C6 C1 H1A 119.1
C11 O2 C12 116.70(17)
O1 C2 C1 125.4(2)
O1 C2 C3 115.85(19)
C1 C2 C3 118.7(2)
C4 C3 C2 121.0(2)
C4 C3 H3A 119.5
C2 C3 H3A 119.5
C3 C4 C5 121.6(2)
C3 C4 H4A 119.2
C5 C4 H4A 119.2
N C5 C4 121.1(2)
N C5 C6 121.1(2)
C4 C5 C6 117.8(2)
C1 C6 C5 119.13(19)
C1 C6 C9 120.46(19)
C5 C6 C9 120.39(19)
O1 C7 H7A 109.5
O1 C7 H7B 109.5
H7A C7 H7B 109.5
O1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N C8 H8A 109.5
N C8 H8B 109.5
H8A C8 H8B 109.5
N C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C6 127.7(2)
C10 C9 H9A 116.1
C6 C9 H9A 116.1
C9 C10 C11 121.0(2)
C9 C10 H10A 119.5
C11 C10 H10A 119.5
O3 C11 O2 122.66(18)
O3 C11 C10 125.5(2)
O2 C11 C10 111.84(18)
O2 C12 H12A 109.5
O2 C12 H12B 109.5
H12A C12 H12B 109.5
O2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C5 1.378(3)
N C8 1.447(3)
N H0A 0.8600
O1 C2 1.372(3)
O1 C7 1.414(3)
C1 C2 1.379(3)
C1 C6 1.403(3)
C1 H1A 0.9300
O2 C11 1.339(3)
O2 C12 1.442(3)
C2 C3 1.389(3)
O3 C11 1.204(2)
C3 C4 1.370(3)
C3 H3A 0.9300
C4 C5 1.404(3)
C4 H4A 0.9300
C5 C6 1.419(3)
C6 C9 1.457(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.332(3)
C9 H9A 0.9300
C10 C11 1.462(3)
C10 H10A 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
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
C7 O1 C2 C1 -6.6(3)
C7 O1 C2 C3 174.7(2)
C6 C1 C2 O1 -178.03(19)
C6 C1 C2 C3 0.6(3)
O1 C2 C3 C4 179.2(2)
C1 C2 C3 C4 0.4(3)
C2 C3 C4 C5 -0.6(4)
C8 N C5 C4 4.6(3)
C8 N C5 C6 -177.4(2)
C3 C4 C5 N 177.8(2)
C3 C4 C5 C6 -0.3(3)
C2 C1 C6 C5 -1.4(3)
C2 C1 C6 C9 176.83(19)
N C5 C6 C1 -176.8(2)
C4 C5 C6 C1 1.2(3)
N C5 C6 C9 4.9(3)
C4 C5 C6 C9 -177.01(19)
C1 C6 C9 C10 22.0(3)
C5 C6 C9 C10 -159.8(2)
C6 C9 C10 C11 -176.96(19)
C12 O2 C11 O3 -1.6(3)
C12 O2 C11 C10 178.70(18)
C9 C10 C11 O3 1.9(3)
C9 C10 C11 O2 -178.40(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 125476752
