#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/72/2007294.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_2007294
loop_
_publ_author_name
'Gigmes, Didier'
'Siri, Didier'
'Reboul, Jean-Pierre'
'Redouane, Nourredine'
'Tordo, Paul'
'Pèpe, Gerard'
_publ_section_title
;
 2-Methyl-2-(10-phenoxazinyl)propiononitrile
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              822
_journal_page_last               824
_journal_paper_doi               10.1107/S010827019701932X
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.281(4)
_cell_length_b                   6.7410(10)
_cell_length_c                   15.559(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.
_cell_measurement_theta_min      9.
_cell_volume                     2594.4(8)
_computing_cell_refinement       'Enraf-Nonius (1977) CAD-4 system'
_computing_data_collection       'Enraf-Nonius (1977) CAD-4 system'
_computing_data_reduction        'DATARED (Pèpe, 1979)'
_computing_molecular_graphics    ORTEPII
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius CAD-4 diffractometer'
_diffrn_measurement_method       ω/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3587
_diffrn_reflns_theta_max         30.16
_diffrn_reflns_theta_min         1.65
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      1.29(2)
_exptl_crystal_density_method
;
flotation in benzene/chloroform
;
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.961
_refine_ls_goodness_of_fit_obs   1.156
_refine_ls_hydrogen_treatment
;
H atoms refined with U = 1.2Ueq(connected atom)
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_restrained_S_obs      1.156
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_obs          .0440
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[s²(Fo²)+(0.0426P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0896
_refine_ls_wR_factor_obs         .0893
_reflns_number_observed          2523
_reflns_number_total             3587
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            ab1513.cif
_cod_data_source_block           structure
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (11 times).

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 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[s^2^(Fo^2^)+(0.0426P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/[s^2^(Fo^2^)+(0.0426P)^2^] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2007294
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 .06991(4) .1143(2) .33066(6) .0405(2) Uani d . 1 . C
C2 .08457(4) .3067(2) .31747(6) .0391(2) Uani d . 1 . C
C3 .05576(5) .4585(2) .34750(7) .0495(3) Uani d . 1 . C
C4 .01638(5) .4159(2) .39361(8) .0585(3) Uani d . 1 . C
C5 .00444(5) .2230(2) .40930(8) .0560(3) Uani d . 1 . C
C6 .03032(5) .0717(2) .37697(7) .0513(3) Uani d . 1 . C
O7 .09403(3) -.04423(11) .29569(5) .0482(2) Uani d . 1 . O
C8 .11266(4) .0049(2) .22065(7) .0439(2) Uani d . 1 . C
C9 .12796(4) .19714(15) .20630(6) .0377(2) Uani d . 1 . C
N10 .12733(3) .34907(12) .27136(5) .0388(2) Uani d . 1 . N
C11 .11328(5) -.1463(2) .15954(8) .0516(3) Uani d . 1 . C
C12 .12890(6) -.1028(2) .08344(8) .0604(3) Uani d . 1 . C
C13 .14299(6) .0898(2) .06572(8) .0603(3) Uani d . 1 . C
C14 .14137(5) .2388(2) .12554(7) .0480(3) Uani d . 1 . C
C15 .18139(4) .3855(2) .32950(7) .0421(2) Uani d . 1 . C
C16 .22114(6) .4595(2) .27415(10) .0591(3) Uani d . 1 . C
C17 .17780(6) .5425(2) .39920(10) .0600(3) Uani d . 1 . C
C18 .20330(5) .1981(2) .37357(7) .0479(3) Uani d . 1 . C
N19 .22044(5) .0540(2) .40694(8) .0694(3) Uani d . 1 . N
H3 .0667(5) .587(2) .3380(8) .060 Uiso d . 1 . H
H4 -.0062(6) .510(2) .4062(9) .072 Uiso d . 1 . H
H5 -.0248(6) .203(2) .4324(9) .067 Uiso d . 1 . H
H6 .0197(6) -.048(2) .3818(9) .062 Uiso d . 1 . H
H11 .1033(5) -.268(2) .1725(9) .061 Uiso d . 1 . H
H12 .1288(6) -.210(2) .0476(10) .073 Uiso d . 1 . H
H13 .1516(6) .124(2) .0166(10) .072 Uiso d . 1 . H
H14 .1479(5) .365(2) .1139(8) .058 Uiso d . 1 . H
H161 .2177(6) .374(2) .2284(10) .071 Uiso d . 1 . H
H162 .2015(6) .564(2) .2394(10) .071 Uiso d . 1 . H
H163 .2521(6) .481(2) .3140(10) .071 Uiso d . 1 . H
H171 .1635(6) .655(2) .3700(10) .073 Uiso d . 1 . H
H172 .1507(7) .494(2) .4249(10) .073 Uiso d . 1 . H
H173 .2116(6) .559(2) .4299(10) .073 Uiso d . 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 0 2
-2 2 7
2 0 4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 121.42(10) ?
C6 C1 O7 117.84(10) ?
C2 C1 O7 120.72(9) y
C1 C2 C3 117.86(10) ?
C1 C2 N10 120.85(9) ?
C3 C2 N10 121.26(10) ?
C4 C3 C2 120.53(12) ?
C4 C3 H3 123.4(8) ?
C2 C3 H3 115.9(8) ?
C5 C4 C3 120.20(12) ?
C5 C4 H4 117.1(9) ?
C3 C4 H4 121.8(10) ?
C6 C5 C4 120.32(11) ?
C6 C5 H5 122.2(9) ?
C4 C5 H5 116.5(9) ?
C5 C6 C1 119.51(12) ?
C5 C6 H6 119.3(9) ?
C1 C6 H6 121.0(9) ?
C8 O7 C1 113.41(8) y
C9 C8 O7 120.97(9) ?
C9 C8 C11 122.07(10) ?
O7 C8 C11 116.91(10) ?
C8 C9 C14 117.50(10) ?
C8 C9 N10 120.51(9) y
C14 C9 N10 121.93(9) ?
C9 N10 C2 109.04(8) y
C9 N10 C15 113.58(8) ?
C2 N10 C15 114.61(8) ?
C12 C11 C8 118.88(12) ?
C12 C11 H11 122.8(9) ?
C8 C11 H11 118.3(9) ?
C11 C12 C13 120.59(12) ?
C11 C12 H12 113.4(9) ?
C13 C12 H12 126.0(9) ?
C14 C13 C12 120.22(12) ?
C14 C13 H13 116.8(10) ?
C12 C13 H13 122.9(10) ?
C13 C14 C9 120.59(12) ?
C13 C14 H14 121.7(8) ?
C9 C14 H14 117.6(8) ?
C18 C15 N10 110.22(9) y
C18 C15 C17 109.34(10) y
N10 C15 C17 111.19(9) y
C18 C15 C16 108.04(10) y
N10 C15 C16 109.66(9) y
C17 C15 C16 108.30(11) y
C15 C16 H161 105.3(9) ?
C15 C16 H162 103.3(9) ?
H161 C16 H162 94.2(12) ?
C15 C16 H163 103.9(9) ?
H161 C16 H163 124.6(13) ?
H162 C16 H163 122.9(13) ?
C15 C17 H171 107.0(9) ?
C15 C17 H172 102.8(9) ?
H171 C17 H172 104.7(13) ?
C15 C17 H173 105.9(10) ?
H171 C17 H173 113.3(14) ?
H172 C17 H173 121.8(14) ?
N19 C18 C15 179.40(12) y
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 C6 . 1.379(2) n
C1 C2 . 1.3760(15) y
C1 O7 . 1.3953(13) y
C2 C3 . 1.3914(15) n
C2 N10 . 1.4440(13) y
C3 C4 . 1.372(2) n
C3 H3 . .928(14) n
C4 C5 . 1.368(2) n
C4 H4 . .900(15) n
C5 C6 . 1.363(2) n
C5 H5 . .896(14) n
C6 H6 . .857(14) n
O7 C8 . 1.3862(13) y
C8 C9 . 1.3837(15) y
C8 C11 . 1.396(2) n
C9 C14 . 1.3958(14) n
C9 N10 . 1.4425(12) y
N10 C15 . 1.4953(14) n
C11 C12 . 1.355(2) n
C11 H11 . .894(14) n
C12 C13 . 1.389(2) n
C12 H12 . .91(2) n
C13 C14 . 1.376(2) n
C13 H13 . .868(15) n
C14 H14 . .889(14) y
C15 C18 . 1.489(2) y
C15 C17 . 1.531(2) y
C15 C16 . 1.535(2) n
C16 H161 . .91(2) n
C16 H162 . .96(2) n
C16 H163 . .90(2) n
C17 H171 . .92(2) n
C17 H172 . .92(2) n
C17 H173 . .90(2) y
C18 N19 . 1.143(2) y
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -4.1(2) ?
O7 C1 C2 C3 174.54(9) ?
C6 C1 C2 N10 177.93(9) ?
O7 C1 C2 N10 -3.46(14) ?
C1 C2 C3 C4 4.0(2) ?
N10 C2 C3 C4 -177.96(10) n
C2 C3 C4 C5 -1.1(2) ?
C3 C4 C5 C6 -2.1(2) ?
C4 C5 C6 C1 2.1(2) ?
C2 C1 C6 C5 1.1(2) ?
O7 C1 C6 C5 -177.57(10) n
C6 C1 O7 C8 151.61(10) ?
C2 C1 O7 C8 -27.04(13) ?
C1 O7 C8 C9 27.24(13) ?
C1 O7 C8 C11 -150.49(10) ?
O7 C8 C9 C14 -174.06(9) ?
C11 C8 C9 C14 3.6(2) ?
O7 C8 C9 N10 3.03(15) ?
C11 C8 C9 N10 -179.36(10) ?
C8 C9 N10 C2 -31.56(12) ?
C14 C9 N10 C2 145.40(10) ?
C8 C9 N10 C15 97.59(11) ?
C14 C9 N10 C15 -85.45(12) ?
C1 C2 N10 C9 31.81(12) ?
C3 C2 N10 C9 -146.12(10) ?
C1 C2 N10 C15 -96.76(11) ?
C3 C2 N10 C15 85.31(12) ?
C9 C8 C11 C12 -0.6(2) ?
O7 C8 C11 C12 177.08(11) n
C8 C11 C12 C13 -1.3(2) ?
C11 C12 C13 C14 0.2(2) ?
C12 C13 C14 C9 2.9(2) ?
C8 C9 C14 C13 -4.7(2) ?
N10 C9 C14 C13 178.29(10) n
C9 N10 C15 C18 -56.50(11) n
C2 N10 C15 C18 69.76(11) n
C9 N10 C15 C17 -177.93(10) ?
C2 N10 C15 C17 -51.67(12) n
C9 N10 C15 C16 62.32(12) n
C2 N10 C15 C16 -171.42(9) ?
N10 C15 C18 N19 107.(15) ?
C17 C15 C18 N19 -13.E1(6) ?
C16 C15 C18 N19 -13.(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21137078
