#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/38/1513800.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_1513800
loop_
_publ_author_name
'Li, Zhanxian'
'Liu, Xingjiang'
'Zhao, Wanying'
'Wang, Sheng'
'Zhou, Wan'
'Wei, Liuhe'
'Yu, Mingming'
_publ_section_title
;
 Naked-eye detection of c1-c4 alcohols based on ground-state
 intramolecular proton transfer.
;
_journal_issue                   5
_journal_name_full               'Analytical chemistry'
_journal_page_first              2521
_journal_page_last               2525
_journal_paper_doi               10.1021/ac403550t
_journal_volume                  86
_journal_year                    2014
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 114.168(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9227(13)
_cell_length_b                   5.0106(3)
_cell_length_c                   20.9309(16)
_cell_measurement_temperature    293(2)
_cell_volume                     1714.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, G.M., 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5964
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1, Sheldrick, G.M., (2008)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0548
_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)+(0.0602P)²+0.3996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1503
_reflns_number_gt                1816
_reflns_number_total             3002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ac403550t_si_001.cif
_cod_data_source_block           yumm
_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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1513800
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.74326(12) 0.2297(4) 0.01476(10) 0.0439(5) Uani 1 1 d .
N2 N 0.60225(13) 0.7479(4) -0.06401(10) 0.0493(6) Uani 1 1 d .
O3 O 0.85844(11) -0.1279(4) 0.02626(9) 0.0590(5) Uani 1 1 d .
C9 C 0.74016(15) 0.0756(5) 0.12451(12) 0.0412(6) Uani 1 1 d .
C13 C 0.68404(15) 0.3994(5) 0.00879(12) 0.0427(6) Uani 1 1 d .
C10 C 0.77118(15) 0.0657(4) 0.07213(12) 0.0393(6) Uani 1 1 d .
C15 C 0.57383(16) 0.9141(5) -0.12368(13) 0.0452(6) Uani 1 1 d .
C14 C 0.65690(16) 0.5726(5) -0.05328(13) 0.0493(7) Uani 1 1 d .
H14 H 0.6803 0.5530 -0.0853 0.059 Uiso 1 1 calc R
C5 C 0.83445(15) -0.1213(5) 0.08027(12) 0.0429(6) Uani 1 1 d .
O4 O 0.49153(14) 1.0988(4) -0.07039(11) 0.0760(7) Uani 1 1 d .
H4 H 0.5141 0.9759 -0.0435 0.114 Uiso 1 1 calc R
C16 C 0.51390(16) 1.0944(5) -0.12527(14) 0.0490(7) Uani 1 1 d .
C8 C 0.77309(17) -0.0940(5) 0.18349(13) 0.0502(7) Uani 1 1 d .
H8 H 0.7529 -0.0880 0.2179 0.060 Uiso 1 1 calc R
C6 C 0.86466(16) -0.2811(5) 0.13821(13) 0.0498(7) Uani 1 1 d .
H6 H 0.9061 -0.4021 0.1434 0.060 Uiso 1 1 calc R
C7 C 0.83416(17) -0.2654(5) 0.18974(13) 0.0515(7) Uani 1 1 d .
H7 H 0.8562 -0.3745 0.2290 0.062 Uiso 1 1 calc R
C12 C 0.64845(16) 0.4189(5) 0.05721(13) 0.0499(7) Uani 1 1 d .
H12 H 0.6066 0.5401 0.0504 0.060 Uiso 1 1 calc R
C20 C 0.59717(18) 0.9146(6) -0.17924(15) 0.0619(8) Uani 1 1 d .
H20 H 0.6368 0.7955 -0.1795 0.074 Uiso 1 1 calc R
C11 C 0.67646(16) 0.2575(5) 0.11407(13) 0.0500(7) Uani 1 1 d .
H11 H 0.6534 0.2670 0.1465 0.060 Uiso 1 1 calc R
C4 C 0.92848(16) -0.2810(6) 0.03514(14) 0.0551(7) Uani 1 1 d .
H4A H 0.9294 -0.3135 -0.0102 0.066 Uiso 1 1 calc R
H4B H 0.9255 -0.4523 0.0555 0.066 Uiso 1 1 calc R
C19 C 0.56159(19) 1.0917(6) -0.23436(15) 0.0655(9) Uani 1 1 d .
H19 H 0.5774 1.0916 -0.2715 0.079 Uiso 1 1 calc R
C17 C 0.47884(18) 1.2706(6) -0.18005(15) 0.0617(8) Uani 1 1 d .
H17 H 0.4391 1.3904 -0.1803 0.074 Uiso 1 1 calc R
C3 C 1.00598(19) -0.1412(6) 0.08162(15) 0.0554(7) Uani 1 1 d .
O1 O 1.06945(13) -0.2927(4) 0.09028(12) 0.0814(7) Uani 1 1 d .
O2 O 1.01052(15) 0.0764(5) 0.10605(13) 0.0891(8) Uani 1 1 d .
C18 C 0.50293(18) 1.2675(6) -0.23397(15) 0.0617(8) Uani 1 1 d .
H18 H 0.4793 1.3860 -0.2710 0.074 Uiso 1 1 calc R
C2 C 1.1508(2) -0.1794(8) 0.1288(3) 0.1219(16) Uani 1 1 d .
H2A H 1.1673 -0.0820 0.0967 0.146 Uiso 1 1 calc R
H2B H 1.1490 -0.0546 0.1635 0.146 Uiso 1 1 calc R
C1 C 1.2068(3) -0.3744(11) 0.1612(3) 0.147(2) Uani 1 1 d .
H1A H 1.2061 -0.5042 0.1272 0.221 Uiso 1 1 calc R
H1B H 1.1933 -0.4594 0.1962 0.221 Uiso 1 1 calc R
H1C H 1.2603 -0.2966 0.1829 0.221 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C13 N1 C10 117.3(2)
C14 N2 C15 122.6(2)
C5 O3 C4 117.85(19)
C11 C9 C8 123.2(2)
C11 C9 C10 116.9(2)
C8 C9 C10 119.9(2)
N1 C13 C12 124.0(2)
N1 C13 C14 115.1(2)
C12 C13 C14 120.8(2)
N1 C10 C9 122.6(2)
N1 C10 C5 119.1(2)
C9 C10 C5 118.3(2)
C20 C15 C16 118.2(2)
C20 C15 N2 128.3(2)
C16 C15 N2 113.5(2)
N2 C14 C13 121.3(2)
O3 C5 C6 125.2(2)
O3 C5 C10 114.9(2)
C6 C5 C10 119.9(2)
O4 C16 C17 120.0(3)
O4 C16 C15 118.7(2)
C17 C16 C15 121.3(3)
C7 C8 C9 119.8(2)
C5 C6 C7 120.9(2)
C8 C7 C6 121.2(2)
C11 C12 C13 118.5(2)
C19 C20 C15 120.3(3)
C12 C11 C9 120.6(2)
O3 C4 C3 111.5(2)
C18 C19 C20 119.8(3)
C18 C17 C16 119.4(3)
O2 C3 O1 124.4(3)
O2 C3 C4 125.9(3)
O1 C3 C4 109.7(2)
C3 O1 C2 117.5(3)
C17 C18 C19 121.0(3)
C1 C2 O1 111.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C13 1.325(3)
N1 C10 1.370(3)
N2 C14 1.265(3)
N2 C15 1.411(3)
O3 C5 1.365(3)
O3 C4 1.417(3)
C9 C11 1.406(3)
C9 C8 1.414(3)
C9 C10 1.419(3)
C13 C12 1.405(3)
C13 C14 1.470(3)
C10 C5 1.426(3)
C15 C20 1.388(4)
C15 C16 1.394(3)
C5 C6 1.367(3)
O4 C16 1.363(3)
C16 C17 1.378(4)
C8 C7 1.355(4)
C6 C7 1.397(3)
C12 C11 1.354(3)
C20 C19 1.387(4)
C4 C3 1.503(4)
C19 C18 1.374(4)
C17 C18 1.364(4)
C3 O2 1.193(3)
C3 O1 1.317(3)
O1 C2 1.461(4)
C2 C1 1.366(5)
