#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/28/2222861.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222861
loop_
_publ_author_name
'Zhao, Min Min'
'Li, Yong Hua'
'Zhang, Yuan'
_publ_section_title
;
 6-(4-Nitrobenzyloxy)quinoline
;
_journal_coeditor_code           RZ2340
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1795
_journal_paper_doi               10.1107/S1600536809025823
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H12 N2 O3'
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_chemical_formula_weight         280.28
_chemical_name_systematic
;
6-(4-Nitrobenzyloxy)quinoline
;
_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                 115.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.296(3)
_cell_length_b                   8.9146(18)
_cell_length_c                   13.559(3)
_cell_measurement_reflns_used    8689
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      3.035
_cell_volume                     1344.3(6)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL/PC (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       'CCD profile fitting'
_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  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0651
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11965
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.32
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1441
_refine_ls_R_factor_gt           0.0651
_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)+(0.0563P)²+0.1856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1516
_reflns_number_gt                1372
_reflns_number_total             2630
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2340.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2222861
_cod_database_fobs_code          2222861
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3786(4) 0.3414(4) -0.1994(3) 0.0901(11) Uani d . 1 . .
H H1A 0.3497 0.3839 -0.2686 0.108 Uiso calc R 1 . .
C C2 0.4967(4) 0.3728(4) -0.1275(3) 0.0881(11) Uani d . 1 . .
H H2A 0.5444 0.4336 -0.1487 0.106 Uiso calc R 1 . .
C C3 0.5411(3) 0.3132(4) -0.0257(3) 0.0735(9) Uani d . 1 . .
H H3A 0.6202 0.3321 0.0235 0.088 Uiso calc R 1 . .
C C4 0.4671(3) 0.2230(3) 0.0046(2) 0.0542(7) Uani d . 1 . .
C C5 0.5069(2) 0.1580(3) 0.1090(2) 0.0557(7) Uani d . 1 . .
H H5A 0.5847 0.1750 0.1616 0.067 Uiso calc R 1 . .
C C6 0.4303(3) 0.0705(3) 0.1319(2) 0.0555(8) Uani d . 1 . .
C C7 0.3126(3) 0.0454(3) 0.0539(2) 0.0657(8) Uani d . 1 . .
H H7A 0.2613 -0.0147 0.0711 0.079 Uiso calc R 1 . .
C C8 0.2730(3) 0.1074(3) -0.0460(2) 0.0650(8) Uani d . 1 . .
H H8A 0.1943 0.0902 -0.0967 0.078 Uiso calc R 1 . .
C C9 0.3483(3) 0.1972(3) -0.0747(2) 0.0572(8) Uani d . 1 . .
C C10 0.5763(2) 0.0164(3) 0.3124(2) 0.0597(8) Uani d . 1 . .
H H10A 0.5943 0.1212 0.3318 0.072 Uiso calc R 1 . .
H H10B 0.6332 -0.0211 0.2861 0.072 Uiso calc R 1 . .
C C11 0.5866(2) -0.0718(3) 0.4102(2) 0.0502(7) Uani d . 1 . .
C C12 0.6722(3) -0.0323(3) 0.5119(2) 0.0620(8) Uani d . 1 . .
H H12A 0.7211 0.0504 0.5189 0.074 Uiso calc R 1 . .
C C13 0.6870(3) -0.1124(3) 0.6032(2) 0.0605(8) Uani d . 1 . .
H H13A 0.7456 -0.0855 0.6715 0.073 Uiso calc R 1 . .
C C14 0.6139(2) -0.2321(3) 0.5916(2) 0.0504(7) Uani d . 1 . .
C C15 0.5270(3) -0.2749(3) 0.4919(2) 0.0607(8) Uani d . 1 . .
H H15A 0.4777 -0.3568 0.4859 0.073 Uiso calc R 1 . .
C C16 0.5142(3) -0.1945(3) 0.4008(2) 0.0627(8) Uani d . 1 . .
H H16A 0.4565 -0.2231 0.3325 0.075 Uiso calc R 1 . .
N N1 0.3048(2) 0.2567(3) -0.1773(2) 0.0782(8) Uani d . 1 . .
N N2 0.6285(3) -0.3179(3) 0.6883(2) 0.0655(7) Uani d . 1 . .
O O1 0.45682(16) 0.0016(2) 0.22964(15) 0.0699(6) Uani d . 1 . .
O O2 0.7111(2) -0.2867(3) 0.77502(18) 0.0885(8) Uani d . 1 . .
O O3 0.5578(2) -0.4184(3) 0.67829(19) 0.1026(9) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 125.1(3) ?
N1 C1 H1A . . 117.5 ?
C2 C1 H1A . . 117.5 ?
C3 C2 C1 . . 118.8(3) ?
C3 C2 H2A . . 120.6 ?
C1 C2 H2A . . 120.6 ?
C2 C3 C4 . . 119.5(3) ?
C2 C3 H3A . . 120.2 ?
C4 C3 H3A . . 120.2 ?
C3 C4 C5 . . 122.6(3) ?
C3 C4 C9 . . 117.4(3) ?
C5 C4 C9 . . 120.0(3) ?
C6 C5 C4 . . 119.2(3) ?
C6 C5 H5A . . 120.4 ?
C4 C5 H5A . . 120.4 ?
C5 C6 O1 . . 125.3(3) ?
C5 C6 C7 . . 120.9(3) ?
O1 C6 C7 . . 113.8(3) ?
C8 C7 C6 . . 120.6(3) ?
C8 C7 H7A . . 119.7 ?
C6 C7 H7A . . 119.7 ?
C7 C8 C9 . . 121.1(3) ?
C7 C8 H8A . . 119.5 ?
C9 C8 H8A . . 119.5 ?
N1 C9 C8 . . 119.2(3) ?
N1 C9 C4 . . 122.6(3) ?
C8 C9 C4 . . 118.2(3) ?
O1 C10 C11 . . 108.5(2) ?
O1 C10 H10A . . 110.0 ?
C11 C10 H10A . . 110.0 ?
O1 C10 H10B . . 110.0 ?
C11 C10 H10B . . 110.0 ?
H10A C10 H10B . . 108.4 ?
C12 C11 C16 . . 118.8(3) ?
C12 C11 C10 . . 119.4(3) ?
C16 C11 C10 . . 121.7(3) ?
C13 C12 C11 . . 121.4(3) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C14 C13 C12 . . 118.5(3) ?
C14 C13 H13A . . 120.8 ?
C12 C13 H13A . . 120.8 ?
C13 C14 C15 . . 122.1(3) ?
C13 C14 N2 . . 119.0(3) ?
C15 C14 N2 . . 119.0(3) ?
C14 C15 C16 . . 118.8(3) ?
C14 C15 H15A . . 120.6 ?
C16 C15 H15A . . 120.6 ?
C15 C16 C11 . . 120.4(3) ?
C15 C16 H16A . . 119.8 ?
C11 C16 H16A . . 119.8 ?
C1 N1 C9 . . 116.6(3) ?
O2 N2 O3 . . 122.7(3) ?
O2 N2 C14 . . 118.8(3) ?
O3 N2 C14 . . 118.5(3) ?
C6 O1 C10 . . 117.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.310(4) ?
C1 C2 . 1.389(4) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.358(4) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.402(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.410(4) ?
C4 C9 . 1.415(4) ?
C5 C6 . 1.357(4) ?
C5 H5A . 0.9300 ?
C6 O1 . 1.368(3) ?
C6 C7 . 1.399(4) ?
C7 C8 . 1.346(4) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.399(4) ?
C8 H8A . 0.9300 ?
C9 N1 . 1.367(3) ?
C10 O1 . 1.425(3) ?
C10 C11 . 1.500(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.377(4) ?
C11 C16 . 1.382(4) ?
C12 C13 . 1.373(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.360(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.372(4) ?
C14 N2 . 1.461(3) ?
C15 C16 . 1.378(4) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
N2 O2 . 1.214(3) ?
N2 O3 . 1.215(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8883190
