#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/45/2224520.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_2224520
loop_
_publ_author_name
'Chen, Lian-Mei'
'Kang, Tai-Ran'
_publ_section_title
;
 3-(1-Naphthyl)-N-phenyloxirane-2-carboxamide
;
_journal_coeditor_code           XU2678
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3137
_journal_paper_doi               10.1107/S1600536809048752
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H15 N O2'
_chemical_formula_moiety         'C19 H15 N O2'
_chemical_formula_sum            'C19 H15 N O2'
_chemical_formula_weight         289.32
_chemical_name_systematic
;
3-(1-Naphthyl)-N-phenyloxirane-2-carboxamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.62890(10)
_cell_length_b                   10.03500(10)
_cell_length_c                   23.2033(3)
_cell_measurement_reflns_used    9381
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      72.1080
_cell_measurement_theta_min      3.8050
_cell_volume                     1543.51(3)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0139
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13761
_diffrn_reflns_theta_full        72.27
_diffrn_reflns_theta_max         72.27
_diffrn_reflns_theta_min         3.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.8294
_exptl_absorpt_correction_T_min  0.7817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.078
_refine_diff_density_min         -0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         1783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0320
_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)+(0.0641P)²+0.0314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1641
_reflns_number_total             1783
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2678.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224520
_cod_database_fobs_code          2224520
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O O1 1.20270(19) 0.10810(12) 0.82723(5) 0.0681(3) Uani d . 1 . .
O O2 1.0096(2) 0.38001(11) 0.74225(7) 0.0738(4) Uani d . 1 . .
N N1 0.8951(2) 0.16688(13) 0.74912(6) 0.0534(3) Uani d . 1 . .
H H4 0.926(3) 0.092(2) 0.7622(8) 0.065(5) Uiso d . 1 . .
C C1 0.3564(3) 0.1625(3) 0.65510(8) 0.0820(6) Uani d . 1 . .
H H1 0.2376 0.1592 0.6339 0.098 Uiso calc R 1 . .
C C2 0.4104(3) 0.0578(2) 0.68938(9) 0.0750(5) Uani d . 1 . .
H H2 0.3275 -0.0168 0.6917 0.090 Uiso calc R 1 . .
C C3 0.5874(3) 0.06219(17) 0.72067(8) 0.0619(4) Uani d . 1 . .
H H3 0.6224 -0.0090 0.7443 0.074 Uiso calc R 1 . .
C C4 0.7135(2) 0.17226(15) 0.71700(6) 0.0521(3) Uani d . 1 . .
C C5 0.6590(3) 0.27941(19) 0.68282(8) 0.0659(4) Uani d . 1 . .
H H5 0.7411 0.3543 0.6804 0.079 Uiso calc R 1 . .
C C6 0.4786(3) 0.2728(2) 0.65216(9) 0.0806(6) Uani d . 1 . .
H H6 0.4402 0.3445 0.6292 0.097 Uiso calc R 1 . .
C C7 1.0258(2) 0.26612(14) 0.75961(7) 0.0523(3) Uani d . 1 . .
C C8 1.2046(2) 0.23071(15) 0.79612(7) 0.0558(4) Uani d . 1 . .
H H8 1.3359 0.2573 0.7805 0.067 Uiso calc R 1 . .
C C9 1.1896(2) 0.23005(17) 0.85940(8) 0.0597(4) Uani d . 1 . .
H H9 1.3135 0.2555 0.8797 0.072 Uiso calc R 1 . .
C C10 0.9999(3) 0.25565(18) 0.89182(7) 0.0588(4) Uani d . 1 . .
C C11 0.8539(3) 0.1600(2) 0.89662(8) 0.0738(5) Uani d . 1 . .
H H11 0.8689 0.0791 0.8776 0.089 Uiso calc R 1 . .
C C12 0.6808(3) 0.1835(3) 0.93030(9) 0.0855(7) Uani d . 1 . .
H H12 0.5819 0.1181 0.9330 0.103 Uiso calc R 1 . .
C C13 0.6567(3) 0.2994(3) 0.95855(9) 0.0854(7) Uani d . 1 . .
H H13 0.5414 0.3127 0.9807 0.103 Uiso calc R 1 . .
C C14 0.8028(3) 0.4013(2) 0.95534(7) 0.0718(5) Uani d . 1 . .
C C15 0.9780(3) 0.38002(19) 0.92061(7) 0.0587(4) Uani d . 1 . .
C C16 1.1212(3) 0.4825(2) 0.91701(8) 0.0690(4) Uani d . 1 . .
H H16 1.2345 0.4710 0.8939 0.083 Uiso calc R 1 . .
C C17 1.0979(4) 0.5988(3) 0.94673(10) 0.0880(6) Uani d . 1 . .
H H17 1.1938 0.6659 0.9432 0.106 Uiso calc R 1 . .
C C18 0.9322(5) 0.6176(3) 0.98222(11) 0.1012(8) Uani d . 1 . .
H H18 0.9205 0.6956 1.0036 0.121 Uiso calc R 1 . .
C C19 0.7874(4) 0.5231(3) 0.98595(9) 0.0927(7) Uani d . 1 . .
H H19 0.6752 0.5383 1.0091 0.111 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8 O1 C9 . . 61.87(10) ?
C7 N1 C4 . . 127.99(14) ?
C7 N1 H4 . . 116.1(15) ?
C4 N1 H4 . . 115.8(15) ?
C2 C1 C6 . . 119.65(18) ?
C2 C1 H1 . . 120.2 ?
C6 C1 H1 . . 120.2 ?
C1 C2 C3 . . 120.29(19) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 120.33(18) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C5 C4 C3 . . 119.75(15) ?
C5 C4 N1 . . 123.56(15) ?
C3 C4 N1 . . 116.68(14) ?
C4 C5 C6 . . 118.67(18) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C1 C6 C5 . . 121.3(2) ?
C1 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
O2 C7 N1 . . 125.45(15) ?
O2 C7 C8 . . 118.66(14) ?
N1 C7 C8 . . 115.89(13) ?
O1 C8 C9 . . 59.38(10) ?
O1 C8 C7 . . 118.91(13) ?
C9 C8 C7 . . 120.76(13) ?
O1 C8 H8 . . 115.4 ?
C9 C8 H8 . . 115.4 ?
C7 C8 H8 . . 115.4 ?
O1 C9 C8 . . 58.75(10) ?
O1 C9 C10 . . 117.46(15) ?
C8 C9 C10 . . 124.10(14) ?
O1 C9 H9 . . 114.9 ?
C8 C9 H9 . . 114.9 ?
C10 C9 H9 . . 114.9 ?
C11 C10 C15 . . 120.32(16) ?
C11 C10 C9 . . 121.23(17) ?
C15 C10 C9 . . 118.36(15) ?
C10 C11 C12 . . 120.3(2) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C13 C12 C11 . . 120.8(2) ?
C13 C12 H12 . . 119.6 ?
C11 C12 H12 . . 119.6 ?
C12 C13 C14 . . 121.31(19) ?
C12 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C13 C14 C19 . . 123.3(2) ?
C13 C14 C15 . . 118.65(19) ?
C19 C14 C15 . . 118.0(2) ?
C16 C15 C10 . . 123.11(16) ?
C16 C15 C14 . . 118.30(18) ?
C10 C15 C14 . . 118.59(17) ?
C17 C16 C15 . . 121.4(2) ?
C17 C16 H16 . . 119.3 ?
C15 C16 H16 . . 119.3 ?
C16 C17 C18 . . 120.5(2) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C19 C18 C17 . . 120.4(2) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 C14 . . 121.4(2) ?
C18 C19 H19 . . 119.3 ?
C14 C19 H19 . . 119.3 ?
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
O1 C8 . 1.4266(19) ?
O1 C9 . 1.436(2) ?
O2 C7 . 1.217(2) ?
N1 C7 . 1.342(2) ?
N1 C4 . 1.417(2) ?
N1 H4 . 0.84(2) ?
C1 C2 . 1.365(3) ?
C1 C6 . 1.373(3) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.381(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.388(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.384(2) ?
C5 C6 . 1.393(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.499(2) ?
C8 C9 . 1.472(2) ?
C8 H8 . 0.9800 ?
C9 C10 . 1.488(2) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.367(3) ?
C10 C15 . 1.423(2) ?
C11 C12 . 1.408(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.345(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.410(3) ?
C13 H13 . 0.9300 ?
C14 C19 . 1.417(4) ?
C14 C15 . 1.429(2) ?
C15 C16 . 1.402(3) ?
C16 C17 . 1.364(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.386(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.352(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H4 O2 4_746 0.84(2) 2.17(2) 2.9540(10) 155.7(18)
C5 H5 O1 4_756 0.93 2.58 3.431(2) 152.5(3)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.4(3) ?
C1 C2 C3 C4 . . . . -0.8(3) ?
C2 C3 C4 C5 . . . . 1.5(2) ?
C2 C3 C4 N1 . . . . -178.11(15) ?
C7 N1 C4 C5 . . . . 11.2(2) ?
C7 N1 C4 C3 . . . . -169.22(16) ?
C3 C4 C5 C6 . . . . -0.9(3) ?
N1 C4 C5 C6 . . . . 178.69(16) ?
C2 C1 C6 C5 . . . . 1.0(3) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C4 N1 C7 O2 . . . . -0.7(3) ?
C4 N1 C7 C8 . . . . 179.01(13) ?
C9 O1 C8 C7 . . . . -110.62(15) ?
O2 C7 C8 O1 . . . . 165.96(15) ?
N1 C7 C8 O1 . . . . -13.7(2) ?
O2 C7 C8 C9 . . . . 96.3(2) ?
N1 C7 C8 C9 . . . . -83.36(18) ?
C8 O1 C9 C10 . . . . 115.07(16) ?
C7 C8 C9 O1 . . . . 107.55(15) ?
O1 C8 C9 C10 . . . . -103.91(18) ?
C7 C8 C9 C10 . . . . 3.6(2) ?
O1 C9 C10 C11 . . . . 7.8(2) ?
C8 C9 C10 C11 . . . . 77.1(2) ?
O1 C9 C10 C15 . . . . -175.59(13) ?
C8 C9 C10 C15 . . . . -106.34(18) ?
C15 C10 C11 C12 . . . . -0.3(3) ?
C9 C10 C11 C12 . . . . 176.26(16) ?
C10 C11 C12 C13 . . . . -0.5(3) ?
C11 C12 C13 C14 . . . . 0.2(3) ?
C12 C13 C14 C19 . . . . -177.7(2) ?
C12 C13 C14 C15 . . . . 0.8(3) ?
C11 C10 C15 C16 . . . . -179.42(17) ?
C9 C10 C15 C16 . . . . 4.0(2) ?
C11 C10 C15 C14 . . . . 1.2(2) ?
C9 C10 C15 C14 . . . . -175.40(14) ?
C13 C14 C15 C16 . . . . 179.15(17) ?
C19 C14 C15 C16 . . . . -2.3(2) ?
C13 C14 C15 C10 . . . . -1.5(2) ?
C19 C14 C15 C10 . . . . 177.07(16) ?
C10 C15 C16 C17 . . . . -177.89(18) ?
C14 C15 C16 C17 . . . . 1.5(3) ?
C15 C16 C17 C18 . . . . 1.1(4) ?
C16 C17 C18 C19 . . . . -2.7(4) ?
C17 C18 C19 C14 . . . . 1.8(4) ?
C13 C14 C19 C18 . . . . 179.2(2) ?
C15 C14 C19 C18 . . . . 0.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743898
