#------------------------------------------------------------------------------
#$Date: 2020-02-28 02:24:52 +0200 (Fri, 28 Feb 2020) $
#$Revision: 248504 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037982.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_4037982
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            'C14 H11 N O2'
_chemical_formula_weight         225.24
_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                 101.772(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.891(9)
_cell_length_b                   10.032(7)
_cell_length_c                   15.905(11)
_cell_measurement_reflns_used    5406
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      2.42
_cell_volume                     2170(3)
_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      250(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24904
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.50
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0615
_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)+(0.0572P)²+3.2376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.2068
_reflns_number_gt                2481
_reflns_number_total             3832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03307_si_002.cif
_cod_data_source_block           14spz3h
_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               4037982
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 0.04561(18) 0.0940(3) 0.29039(18) 0.0614(8) Uani 1 1 d . . .
O2 O 0.0623(2) 0.2632(3) 0.41223(19) 0.0694(9) Uani 1 1 d D . .
H2O H 0.038(4) 0.205(4) 0.375(3) 0.104 Uiso 1 1 d D . .
N1 N 0.3385(2) 0.1387(3) 0.28910(18) 0.0405(7) Uani 1 1 d D . .
H1N H 0.3999(10) 0.141(4) 0.285(2) 0.049 Uiso 1 1 d D . .
C1 C 0.2841(2) 0.0472(3) 0.2352(2) 0.0400(8) Uani 1 1 d . . .
C2 C 0.3307(3) -0.0300(4) 0.1802(2) 0.0480(9) Uani 1 1 d . . .
H2 H 0.3978 -0.0173 0.1801 0.058 Uiso 1 1 calc R . .
C3 C 0.2777(3) -0.1227(4) 0.1276(2) 0.0546(10) Uani 1 1 d . . .
H3 H 0.3086 -0.1745 0.0916 0.066 Uiso 1 1 calc R . .
C4 C 0.1777(3) -0.1415(4) 0.1266(2) 0.0546(10) Uani 1 1 d . . .
H4 H 0.1419 -0.2059 0.0901 0.065 Uiso 1 1 calc R . .
C5 C 0.1318(3) -0.0669(4) 0.1783(2) 0.0516(10) Uani 1 1 d . . .
H5 H 0.0644 -0.0797 0.1767 0.062 Uiso 1 1 calc R . .
C6 C 0.1843(2) 0.0295(4) 0.2344(2) 0.0421(8) Uani 1 1 d . . .
C7 C 0.1377(2) 0.1068(4) 0.2907(2) 0.0448(9) Uani 1 1 d . . .
C8 C 0.1980(2) 0.1997(3) 0.3474(2) 0.0402(8) Uani 1 1 d . . .
C9 C 0.2988(2) 0.2160(3) 0.3457(2) 0.0412(8) Uani 1 1 d . . .
C10 C 0.3585(3) 0.3081(4) 0.3994(2) 0.0493(9) Uani 1 1 d . . .
C11 C 0.3134(3) 0.3830(4) 0.4523(3) 0.0573(10) Uani 1 1 d . . .
H11 H 0.3518 0.4464 0.4878 0.069 Uiso 1 1 calc R . .
C12 C 0.2154(3) 0.3718(4) 0.4572(3) 0.0602(11) Uani 1 1 d . . .
H12 H 0.1887 0.4265 0.4946 0.072 Uiso 1 1 calc R . .
C13 C 0.1573(3) 0.2785(4) 0.4060(2) 0.0497(9) Uani 1 1 d . . .
C14 C 0.4653(3) 0.3206(5) 0.3975(3) 0.0650(12) Uani 1 1 d . . .
H14A H 0.4948 0.3887 0.4380 0.097 Uiso 1 1 calc R . .
H14B H 0.4725 0.3451 0.3402 0.097 Uiso 1 1 calc R . .
H14C H 0.4978 0.2360 0.4133 0.097 Uiso 1 1 calc R . .
O3 O 0.46403(18) 0.6621(3) 0.28421(17) 0.0557(7) Uani 1 1 d . . .
O4 O 0.4754(2) 0.8390(3) 0.40113(18) 0.0650(8) Uani 1 1 d D . .
H4O H 0.491(4) 0.786(4) 0.365(3) 0.097 Uiso 1 1 d D . .
N2 N 0.1721(2) 0.6124(3) 0.28895(19) 0.0427(7) Uani 1 1 d D . .
H2N H 0.1096(9) 0.610(4) 0.287(2) 0.051 Uiso 1 1 d D . .
C15 C 0.2138(2) 0.5369(4) 0.2338(2) 0.0420(8) Uani 1 1 d . . .
C16 C 0.1543(3) 0.4438(4) 0.1793(2) 0.0505(9) Uani 1 1 d . . .
H16 H 0.0871 0.4354 0.1802 0.061 Uiso 1 1 calc R . .
C17 C 0.1956(3) 0.3665(4) 0.1255(2) 0.0547(10) Uani 1 1 d . . .
H17 H 0.1565 0.3039 0.0900 0.066 Uiso 1 1 calc R . .
C18 C 0.2951(3) 0.3787(4) 0.1220(3) 0.0539(10) Uani 1 1 d . . .
H18 H 0.3225 0.3252 0.0844 0.065 Uiso 1 1 calc R . .
C19 C 0.3521(3) 0.4693(4) 0.1739(2) 0.0491(9) Uani 1 1 d . . .
H19 H 0.4189 0.4779 0.1713 0.059 Uiso 1 1 calc R . .
C20 C 0.3130(2) 0.5502(3) 0.2313(2) 0.0410(8) Uani 1 1 d . . .
C21 C 0.3730(2) 0.6457(4) 0.2863(2) 0.0413(8) Uani 1 1 d . . .
C22 C 0.3263(2) 0.7224(3) 0.3441(2) 0.0389(8) Uani 1 1 d . . .
C23 C 0.2249(3) 0.7039(4) 0.3445(2) 0.0426(8) Uani 1 1 d . . .
C24 C 0.1776(3) 0.7775(4) 0.3997(2) 0.0473(9) Uani 1 1 d . . .
C25 C 0.2340(3) 0.8713(4) 0.4517(2) 0.0500(9) Uani 1 1 d . . .
H25 H 0.2038 0.9231 0.4882 0.060 Uiso 1 1 calc R . .
C26 C 0.3323(3) 0.8923(4) 0.4526(2) 0.0537(10) Uani 1 1 d . . .
H26 H 0.3675 0.9568 0.4895 0.064 Uiso 1 1 calc R . .
C27 C 0.3793(3) 0.8188(4) 0.3994(2) 0.0482(9) Uani 1 1 d . . .
C28 C 0.0708(3) 0.7547(5) 0.3999(3) 0.0622(11) Uani 1 1 d . . .
H28A H 0.0618 0.6646 0.4191 0.093 Uiso 1 1 calc R . .
H28B H 0.0323 0.7668 0.3423 0.093 Uiso 1 1 calc R . .
H28C H 0.0493 0.8179 0.4384 0.093 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
C13 O2 H2O 107(4) . . ?
C1 N1 C9 122.7(3) . . ?
C1 N1 H1N 113(2) . . ?
C9 N1 H1N 124(2) . . ?
N1 C1 C6 120.6(3) . . ?
N1 C1 C2 119.2(3) . . ?
C6 C1 C2 120.1(3) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 120.0(3) . . ?
C5 C6 C7 121.5(3) . . ?
O1 C7 C6 121.3(3) . . ?
O1 C7 C8 121.2(3) . . ?
C6 C7 C8 117.5(3) . . ?
C9 C8 C13 118.3(3) . . ?
C9 C8 C7 120.9(3) . . ?
C13 C8 C7 120.8(3) . . ?
N1 C9 C10 119.9(3) . . ?
N1 C9 C8 118.3(3) . . ?
C10 C9 C8 121.8(3) . . ?
C11 C10 C9 116.5(4) . . ?
C11 C10 C14 123.0(4) . . ?
C9 C10 C14 120.5(4) . . ?
C10 C11 C12 124.5(4) . . ?
C10 C11 H11 117.7 . . ?
C12 C11 H11 117.7 . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
O2 C13 C12 119.6(4) . . ?
O2 C13 C8 120.5(4) . . ?
C12 C13 C8 119.8(4) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C27 O4 H4O 106(4) . . ?
C15 N2 C23 122.5(3) . . ?
C15 N2 H2N 121(2) . . ?
C23 N2 H2N 116(3) . . ?
N2 C15 C20 120.9(3) . . ?
N2 C15 C16 119.0(3) . . ?
C20 C15 C16 120.1(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 118.5(3) . . ?
C15 C20 C21 120.0(3) . . ?
C19 C20 C21 121.5(3) . . ?
O3 C21 C20 121.4(3) . . ?
O3 C21 C22 121.3(3) . . ?
C20 C21 C22 117.3(3) . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 C21 121.1(3) . . ?
C23 C22 C21 120.3(3) . . ?
N2 C23 C24 119.6(3) . . ?
N2 C23 C22 118.9(3) . . ?
C24 C23 C22 121.5(3) . . ?
C25 C24 C23 116.7(3) . . ?
C25 C24 C28 122.7(3) . . ?
C23 C24 C28 120.6(4) . . ?
C26 C25 C24 123.2(4) . . ?
C26 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?
C25 C26 C27 120.1(4) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
O4 C27 C26 119.9(4) . . ?
O4 C27 C22 120.3(3) . . ?
C26 C27 C22 119.8(3) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
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 C7 1.284(4) . ?
O2 C13 1.352(5) . ?
O2 H2O 0.846(10) . ?
N1 C1 1.372(4) . ?
N1 C9 1.385(4) . ?
N1 H1N 0.869(10) . ?
C1 C6 1.395(5) . ?
C1 C2 1.419(5) . ?
C2 C3 1.363(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.399(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.363(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.413(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.435(5) . ?
C7 C8 1.441(5) . ?
C8 C9 1.416(5) . ?
C8 C13 1.424(5) . ?
C9 C10 1.407(5) . ?
C10 C11 1.372(5) . ?
C10 C14 1.495(5) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9400 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9400 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
O3 C21 1.282(4) . ?
O4 C27 1.346(5) . ?
O4 H4O 0.846(10) . ?
N2 C15 1.373(4) . ?
N2 C23 1.378(5) . ?
N2 H2N 0.862(10) . ?
C15 C20 1.393(5) . ?
C15 C16 1.420(5) . ?
C16 C17 1.365(5) . ?
C16 H16 0.9400 . ?
C17 C18 1.400(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.366(5) . ?
C18 H18 0.9400 . ?
C19 C20 1.412(5) . ?
C19 H19 0.9400 . ?
C20 C21 1.442(5) . ?
C21 C22 1.450(5) . ?
C22 C27 1.410(5) . ?
C22 C23 1.421(5) . ?
C23 C24 1.408(5) . ?
C24 C25 1.386(5) . ?
C24 C28 1.502(5) . ?
C25 C26 1.379(5) . ?
C25 H25 0.9400 . ?
C26 C27 1.382(5) . ?
C26 H26 0.9400 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
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
O2 H2O O1 0.846(10) 1.77(3) 2.551(4) 152(5) .
N1 H1N O3 0.869(10) 2.385(17) 3.201(4) 157(3) 2_645
O4 H4O O3 0.846(10) 1.77(3) 2.552(4) 153(5) .
N2 H2N O1 0.862(10) 2.26(2) 3.035(4) 149(3) 2
