#------------------------------------------------------------------------------
#$Date: 2020-02-28 02:25:05 +0200 (Fri, 28 Feb 2020) $
#$Revision: 248505 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037983.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_4037983
loop_
_publ_author_name
'Wu, Jing'
'Zhang, Jinzhu'
'Soto-Acosta, Ruben'
'Mao, Lili'
'Lian, Jiahui'
'Chen, Kenny'
'Pillon, Guy'
'Zhang, Guoqi'
'Geraghty, Robert J.'
'Zheng, Shengping'
_publ_section_title
;
 One-pot Synthesis of 1-Hydroxyacridones from para-Quinols and
 ortho-Methoxycarbonylaryl Isocyanates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03307
_journal_year                    2020
_chemical_formula_sum            'C15 H11 N O5'
_chemical_formula_weight         285.25
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 95.0523(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4148(6)
_cell_length_b                   10.2824(8)
_cell_length_c                   14.1780(11)
_cell_measurement_reflns_used    9409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.43
_cell_volume                     1221.98(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0106
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25021
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9520
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0381
_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)+(0.0472P)²+0.7305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                2933
_reflns_number_total             3042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03307_si_004.cif
_cod_data_source_block           14spz1h
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037983
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.04046(9) 0.36004(8) 0.49925(6) 0.01517(18) Uani 1 1 d . . .
O2 O -0.14405(9) 0.22458(9) 0.43032(6) 0.01885(19) Uani 1 1 d . . .
O3 O 0.54575(9) 0.27098(8) 0.47910(6) 0.01668(18) Uani 1 1 d D . .
H3O H 0.6279(14) 0.2382(15) 0.4602(11) 0.020 Uiso 1 1 d D . .
O4 O 0.41439(11) 0.25375(9) 0.25913(6) 0.0222(2) Uani 1 1 d . . .
O5 O 0.56174(10) 0.03061(9) 0.39799(7) 0.02061(19) Uani 1 1 d . . .
N1 N 0.12672(10) 0.17790(9) 0.43686(7) 0.01284(19) Uani 1 1 d . . .
C1 C -0.00589(13) 0.24969(11) 0.45274(8) 0.0138(2) Uani 1 1 d . . .
C2 C 0.21503(12) 0.37569(11) 0.50075(8) 0.0131(2) Uani 1 1 d . . .
C3 C 0.26982(12) 0.23479(10) 0.48666(8) 0.0118(2) Uani 1 1 d . . .
H3 H 0.2939 0.1914 0.5494 0.014 Uiso 1 1 calc R . .
C4 C 0.41015(12) 0.21976(11) 0.42690(8) 0.0130(2) Uani 1 1 d . . .
C5 C 0.38094(13) 0.29834(11) 0.33436(8) 0.0151(2) Uani 1 1 d . . .
C6 C 0.31678(13) 0.43013(11) 0.34392(8) 0.0167(2) Uani 1 1 d . . .
H6 H 0.3291 0.4922 0.2954 0.020 Uiso 1 1 calc R . .
C7 C 0.24176(13) 0.46463(11) 0.41901(8) 0.0157(2) Uani 1 1 d . . .
H7 H 0.2024 0.5511 0.4212 0.019 Uiso 1 1 calc R . .
C8 C 0.27510(14) 0.43595(11) 0.59456(8) 0.0172(2) Uani 1 1 d . . .
H8A H 0.3919 0.4396 0.5995 0.026 Uiso 1 1 calc R . .
H8B H 0.2401 0.3831 0.6464 0.026 Uiso 1 1 calc R . .
H8C H 0.2321 0.5242 0.5985 0.026 Uiso 1 1 calc R . .
C9 C 0.42883(13) 0.07618(11) 0.40097(8) 0.0145(2) Uani 1 1 d . . .
C10 C 0.27966(13) 0.00242(11) 0.37753(8) 0.0136(2) Uani 1 1 d . . .
C11 C 0.12990(13) 0.05462(10) 0.39370(8) 0.0127(2) Uani 1 1 d . . .
C12 C -0.00953(13) -0.01571(11) 0.36693(8) 0.0156(2) Uani 1 1 d . . .
H12 H -0.1112 0.0186 0.3778 0.019 Uiso 1 1 calc R . .
C13 C 0.00344(14) -0.13641(11) 0.32421(8) 0.0177(2) Uani 1 1 d . . .
H13 H -0.0908 -0.1840 0.3053 0.021 Uiso 1 1 calc R . .
C14 C 0.15132(15) -0.18945(11) 0.30833(8) 0.0184(2) Uani 1 1 d . . .
H14 H 0.1576 -0.2722 0.2790 0.022 Uiso 1 1 calc R . .
C15 C 0.28856(14) -0.12038(11) 0.33569(8) 0.0166(2) Uani 1 1 d . . .
H15 H 0.3898 -0.1565 0.3260 0.020 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 110.02(8) . . ?
C4 O3 H3O 109.6(11) . . ?
C1 N1 C11 127.00(9) . . ?
C1 N1 C3 110.62(9) . . ?
C11 N1 C3 121.53(9) . . ?
O2 C1 O1 122.55(10) . . ?
O2 C1 N1 128.34(11) . . ?
O1 C1 N1 109.11(9) . . ?
O1 C2 C7 105.70(8) . . ?
O1 C2 C8 108.19(9) . . ?
C7 C2 C8 111.48(9) . . ?
O1 C2 C3 101.81(8) . . ?
C7 C2 C3 113.86(9) . . ?
C8 C2 C3 114.77(9) . . ?
N1 C3 C4 109.69(9) . . ?
N1 C3 C2 101.29(8) . . ?
C4 C3 C2 115.10(9) . . ?
N1 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
O3 C4 C3 107.61(9) . . ?
O3 C4 C9 113.03(9) . . ?
C3 C4 C9 109.43(9) . . ?
O3 C4 C5 108.22(9) . . ?
C3 C4 C5 110.33(9) . . ?
C9 C4 C5 108.22(9) . . ?
O4 C5 C6 122.93(11) . . ?
O4 C5 C4 121.10(11) . . ?
C6 C5 C4 115.92(10) . . ?
C7 C6 C5 121.52(10) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C2 124.43(11) . . ?
C6 C7 H7 117.8 . . ?
C2 C7 H7 117.8 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 C10 124.00(10) . . ?
O5 C9 C4 119.55(10) . . ?
C10 C9 C4 116.41(9) . . ?
C15 C10 C11 119.68(10) . . ?
C15 C10 C9 118.79(10) . . ?
C11 C10 C9 121.49(10) . . ?
C12 C11 C10 119.96(10) . . ?
C12 C11 N1 122.29(10) . . ?
C10 C11 N1 117.74(10) . . ?
C13 C12 C11 118.86(10) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.67(11) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 119.27(11) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C10 120.53(11) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
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
O1 C1 1.3524(14) . ?
O1 C2 1.4761(12) . ?
O2 C1 1.2059(14) . ?
O3 C4 1.4066(13) . ?
O3 H3O 0.834(9) . ?
O4 C5 1.2166(14) . ?
O5 C9 1.2168(14) . ?
N1 C1 1.3729(14) . ?
N1 C11 1.4089(14) . ?
N1 C3 1.4632(13) . ?
C2 C7 1.5086(16) . ?
C2 C8 1.5133(15) . ?
C2 C3 1.5387(15) . ?
C3 C4 1.5207(14) . ?
C3 H3 1.0000 . ?
C4 C9 1.5328(15) . ?
C4 C5 1.5420(16) . ?
C5 C6 1.4693(16) . ?
C6 C7 1.3328(17) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.4791(15) . ?
C10 C15 1.3999(15) . ?
C10 C11 1.4070(15) . ?
C11 C12 1.4018(15) . ?
C12 C13 1.3894(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3950(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3819(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3O O2 0.834(9) 2.006(10) 2.7995(12) 158.6(16) 1_655
