#------------------------------------------------------------------------------
#$Date: 2017-07-05 20:52:43 +0300 (Wed, 05 Jul 2017) $
#$Revision: 198484 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/42/2004228.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_2004228
loop_
_publ_author_name
'Rowan, K. R.'
'Holt, E. M.'
_publ_section_title
;3,5-Dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrosophenyl)pyridine and
 Dichlorobis[3,5-dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)pyridine]copper(II)
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2554
_journal_page_last               2559
_journal_paper_doi               10.1107/S0108270195005828
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C17 H16 N2 O5'
_chemical_formula_sum            'C17 H16 N2 O5'
_chemical_formula_weight         328.3
_chemical_melting_point          366
_chemical_name_systematic
;
2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(2-nitrosophenyl)pyridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_cell_angle_alpha                90.0
_cell_angle_beta                 90.20(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            8
_cell_length_a                   18.171(4)
_cell_length_b                   7.157(1)
_cell_length_c                   26.165(5)
_cell_measurement_reflns_used    46
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.37
_cell_measurement_theta_min      4.383
_cell_volume                     3402.7(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXS86
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1995)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Syntex P4 four-circle'
_diffrn_measurement_method       θ/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  0.084
_diffrn_reflns_av_sigmaI/netI    0.2675
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7522
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        3.7
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.180
_refine_ls_extinction_method
'Extinction was refined but was insignificant'
_refine_ls_goodness_of_fit_all   0.694
_refine_ls_goodness_of_fit_obs   1.136
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.759
_refine_ls_restrained_S_obs      1.136
_refine_ls_R_factor_all          0.2602
_refine_ls_R_factor_obs          0.063
_refine_ls_shift/esd_max         -1.272
_refine_ls_shift/esd_mean        0.032
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0268P)^2^] where
P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.158
_refine_ls_wR_factor_obs         0.100
_reflns_number_observed          1328
_reflns_number_total             5831
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            cr1185.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
;
 Changing the space group from '-P 2yc' to '-P 2ybc' after consulting the
 original publication. All related space group information was changed
 accordingly.

 Antanas Vaitkus,
 2017-07-05
;
_cod_original_cell_volume        3402.6(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2004228
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
N1 1 0.2852(3) -0.1787(8) 0.0848(2) 0.061(2) Uani d . N
C2 1 0.3300(3) -0.0918(10) 0.0523(2) 0.052(2) Uani d . C
C2' 1 0.3326(3) -0.1806(9) 0.0005(2) 0.083(2) Uani d . C
H2'A 1 0.2992(3) -0.2845(9) -0.0009(2) 0.080 Uiso calc R H
H2'B 1 0.3184(3) -0.0894(9) -0.0246(2) 0.080 Uiso calc R H
H2'C 1 0.3816(3) -0.2232(9) -0.0065(2) 0.080 Uiso calc R H
C3 1 0.3726(3) 0.0585(10) 0.0668(2) 0.053(2) Uani d . C
C3' 1 0.4241(4) 0.1545(10) 0.0296(3) 0.066(2) Uani d . C
O3' 1 0.4883(2) 0.1801(8) 0.03731(15) 0.088(2) Uani d . O
O3" 1 0.3876(2) 0.2127(8) -0.0108(2) 0.096(2) Uani d . O
C3" 1 0.4316(4) 0.2938(11) -0.0510(2) 0.123(3) Uani d . C
H3"A 1 0.4013(4) 0.3286(11) -0.0796(2) 0.080 Uiso calc R H
H3"B 1 0.4534(4) 0.4038(11) -0.0364(2) 0.080 Uiso calc R H
H3"C 1 0.4698(4) 0.2108(11) -0.0623(2) 0.080 Uiso calc R H
C4 1 0.3715(3) 0.1225(9) 0.1177(2) 0.055(2) Uani d . C
C5 1 0.3225(3) 0.0309(9) 0.1508(2) 0.048(2) Uani d . C
C5' 1 0.3181(3) 0.0904(11) 0.2059(3) 0.054(2) Uani d . C
C5" 1 0.2796(3) 0.3342(9) 0.2607(2) 0.095(3) Uani d . C
H5"A 1 0.2565(3) 0.4549(9) 0.2607(2) 0.080 Uiso calc R H
H5"B 1 0.2509(3) 0.2492(9) 0.2809(2) 0.080 Uiso calc R H
H5"C 1 0.3282(3) 0.3442(9) 0.2749(2) 0.080 Uiso calc R H
O5' 1 0.3384(3) -0.0012(8) 0.2409(2) 0.115(2) Uani d . O
O5" 1 0.2867(2) 0.2539(7) 0.2100(2) 0.0704(14) Uani d . O
C6 1 0.2818(3) -0.1207(10) 0.1329(3) 0.055(2) Uani d . C
C6' 1 0.2298(3) -0.2199(9) 0.1683(2) 0.091(2) Uani d . C
H6'A 1 0.2309(3) -0.1661(9) 0.2019(2) 0.080 Uiso calc R H
H6'B 1 0.1810(3) -0.2104(9) 0.1544(2) 0.080 Uiso calc R H
H6'C 1 0.2439(3) -0.3490(9) 0.1702(2) 0.080 Uiso calc R H
C7 1 0.4183(3) 0.2808(10) 0.1360(2) 0.047(2) Uani d . C
C8 1 0.3990(3) 0.4600(10) 0.1288(2) 0.058(2) Uani d . C
H8A 1 0.3566(3) 0.4898(10) 0.1084(2) 0.080 Uiso calc R H
C9 1 0.4400(4) 0.6035(10) 0.1489(2) 0.075(2) Uani d . C
H9A 1 0.4253(4) 0.7314(10) 0.1444(2) 0.080 Uiso calc R H
C10 1 0.5028(4) 0.5665(10) 0.1773(3) 0.070(2) Uani d . C
H10A 1 0.5324(4) 0.6652(10) 0.1913(3) 0.080 Uiso calc R H
C11 1 0.5239(3) 0.3854(10) 0.1846(2) 0.063(2) Uani d . C
H11A 1 0.5666(3) 0.3580(10) 0.2050(2) 0.080 Uiso calc R H
C12 1 0.4830(3) 0.2433(10) 0.1639(2) 0.054(2) Uani d . C
N2 1 0.5020(3) 0.0504(9) 0.1690(2) 0.081(2) Uani d . N
O1A 0.50 0.5649(17) 0.019(3) 0.1865(14) 0.115(11) Uani d P O
O1B 0.50 0.5550(22) 0.026(4) 0.1929(15) 0.156(14) Uani d P O
N91 1 0.0632(4) 0.2394(8) -0.0383(2) 0.071(2) Uani d . N
C92 1 0.0034(4) 0.3288(10) -0.0554(2) 0.060(2) Uani d . C
C92' 1 -0.0674(3) 0.2501(9) -0.0354(2) 0.086(2) Uani d . C
H92'D 1 -0.0593(3) 0.1506(9) -0.0114(2) 0.080 Uiso calc R H
H92'E 1 -0.0941(3) 0.3491(9) -0.0190(2) 0.080 Uiso calc R H
H92'F 1 -0.0955(3) 0.2041(9) -0.0639(2) 0.080 Uiso calc R H
C93 1 0.0064(3) 0.4696(10) -0.0901(2) 0.052(2) Uani d . C
C93' 1 -0.0625(4) 0.5461(12) -0.1138(3) 0.062(2) Uani d . C
C93" 0.50 -0.1711(14) 0.720(4) -0.1023(9) 0.096(10) Uani d P C
H93"D 0.50 -0.1942(14) 0.8002(44) -0.0778(9) 0.080 Uiso calc PR H
H93"E 0.50 -0.1573(14) 0.7912(44) -0.1318(9) 0.080 Uiso calc PR H
H93"F 0.50 -0.2049(14) 0.6232(44) -0.1123(9) 0.080 Uiso calc PR H
C93X 0.50 -0.1492(19) 0.796(5) -0.1132(12) 0.142(15) Uani d P C
H93A 0.50 -0.1680(19) 0.8804(49) -0.0879(12) 0.080 Uiso calc PR H
H93B 0.50 -0.1310(19) 0.8659(49) -0.1418(12) 0.080 Uiso calc PR H
H93C 0.50 -0.1879(19) 0.7142(49) -0.1245(12) 0.080 Uiso calc PR H
O93' 1 -0.0845(2) 0.5016(7) -0.1544(2) 0.089(2) Uani d . O
O93" 0.50 -0.090(3) 0.659(8) -0.0784(15) 0.124(14) Uani d P O
O93X 0.50 -0.100(3) 0.679(6) -0.0900(14) 0.090(10) Uani d P O
C94 1 0.0739(4) 0.5358(10) -0.1080(2) 0.053(2) Uani d . C
C95 1 0.1370(4) 0.4472(10) -0.0896(2) 0.059(2) Uani d . C
C95' 1 0.2129(5) 0.4977(14) -0.1100(3) 0.076(3) Uani d . C
C95" 1 0.2871(4) 0.7447(12) -0.1359(2) 0.138(4) Uani d . C
H95"A 1 0.2873(4) 0.8787(12) -0.1375(2) 0.080 Uiso calc R H
H95"B 1 0.3288(4) 0.7027(12) -0.1164(2) 0.080 Uiso calc R H
H95"C 1 0.2898(4) 0.6946(12) -0.1699(2) 0.080 Uiso calc R H
O95' 1 0.2583(3) 0.3847(10) -0.1222(2) 0.126(3) Uani d . O
O95" 1 0.2208(3) 0.6802(9) -0.1111(2) 0.089(2) Uani d . O
C96 1 0.1295(4) 0.2991(11) -0.0556(2) 0.068(2) Uani d . C
C96' 1 0.1932(4) 0.1850(12) -0.0359(2) 0.133(4) Uani d . C
H96'H 1 0.1732(4) 0.0877(12) -0.0149(2) 0.080 Uiso calc R H
H96'I 1 0.2207(4) 0.1304(12) -0.0635(2) 0.080 Uiso calc R H
H96'J 1 0.2252(4) 0.2626(12) -0.0158(2) 0.080 Uiso calc R H
C97 1 0.0749(3) 0.6917(10) -0.1452(2) 0.050(2) Uani d . C
C98 1 0.0605(4) 0.8694(11) -0.1304(3) 0.074(2) Uani d . C
H98J 1 0.0483(4) 0.8934(11) -0.0953(3) 0.080 Uiso calc R H
C99 1 0.0592(4) 1.0135(10) -0.1652(3) 0.080(2) Uani d . C
H99A 1 0.0483(4) 1.1360(10) -0.1523(3) 0.080 Uiso calc R H
C910 1 0.0735(3) 0.9826(10) -0.2163(3) 0.068(2) Uani d . C
H910A 1 0.0756(3) 1.0859(10) -0.2397(3) 0.080 Uiso calc R H
C911 1 0.0855(3) 0.8038(10) -0.2323(2) 0.061(2) Uani d . C
H111G 1 0.0929(3) 0.7757(10) -0.2678(2) 0.080 Uiso calc R H
C912 1 0.0881(3) 0.6577(10) -0.1976(2) 0.051(2) Uani d . C
N92 1 0.1012(3) 0.4688(9) -0.2111(2) 0.070(2) Uani d . N
O91 1 0.1145(3) 0.4430(7) -0.2563(2) 0.098(2) Uani d . O
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_publ_flag
C6 N1 C2 119.3(6) yes
N1 C2 C3 122.2(6) yes
N1 C2 C2' 113.6(6) yes
C3 C2 C2' 124.1(7) yes
C2 C3 C4 120.3(6) yes
C2 C3 C3' 121.6(6) yes
C4 C3 C3' 118.0(6) yes
O3' C3' O3" 125.2(7) yes
O3' C3' C3 124.3(7) yes
O3" C3' C3 110.4(6) yes
C3' O3" C3" 115.6(5) yes
C3 C4 C5 116.2(6) yes
C3 C4 C7 122.6(6) yes
C5 C4 C7 121.2(6) yes
C6 C5 C4 119.5(6) yes
C6 C5 C5' 120.8(6) yes
C4 C5 C5' 119.5(6) yes
O5' C5' O5" 124.5(7) yes
O5' C5' C5 124.5(7) yes
O5" C5' C5 110.9(6) yes
C5' O5" C5" 118.1(5) yes
N1 C6 C5 122.4(6) yes
N1 C6 C6' 117.9(7) yes
C5 C6 C6' 119.6(6) yes
C8 C7 C12 118.2(6) yes
C8 C7 C4 122.1(6) yes
C12 C7 C4 119.7(6) yes
C7 C8 C9 121.3(6) yes
C8 C9 C10 120.5(7) yes
C11 C10 C9 119.1(7) yes
C10 C11 C12 119.9(6) yes
C11 C12 C7 121.0(6) yes
C11 C12 N2 123.3(6) yes
C7 C12 N2 115.7(6) yes
O1A N2 C12 115.5(12) yes
C92 N91 C96 117.4(6) yes
N91 C92 C93 122.9(6) yes
N91 C92 C92' 113.7(6) yes
C93 C92 C92' 123.3(7) yes
C92 C93 C94 121.0(6) yes
C92 C93 C93' 120.8(6) yes
C94 C93 C93' 118.0(6) yes
O93' C93' O93" 131.7(18) yes
O93' C93' C93 123.7(7) yes
O93" C93' C93 104.5(18) yes
C93' O93" C93" 104.(2) yes
C95 C94 C93 116.8(6) yes
C95 C94 C97 123.9(6) yes
C93 C94 C97 119.3(6) yes
C96 C95 C94 119.1(6) yes
C96 C95 C95' 119.6(7) yes
C94 C95 C95' 121.0(6) yes
O95' C95' O95" 126.1(9) yes
O95' C95' C95 123.9(9) yes
O95" C95' C95 110.0(8) yes
C95' O95" C95" 114.8(7) yes
N91 C96 C95 122.8(6) yes
N91 C96 C96' 113.4(7) yes
C95 C96 C96' 123.7(7) yes
C98 C97 C912 118.2(6) yes
C98 C97 C94 121.1(6) yes
C912 C97 C94 120.7(6) yes
C97 C98 C99 121.1(6) yes
C98 C99 C910 121.2(7) yes
C911 C910 C99 118.5(6) yes
C910 C911 C912 120.8(6) yes
C911 C912 N92 124.1(6) yes
C911 C912 C97 120.0(6) yes
N92 C912 C97 115.9(6) yes
O91 N92 C912 114.8(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C6 1.326(7) yes
N1 C2 1.332(7) yes
C2 C3 1.378(7) yes
C2 C2' 1.500(7) yes
C3 C4 1.408(7) yes
C3 C3' 1.518(8) yes
C3' O3' 1.197(7) yes
C3' O3" 1.315(7) yes
O3" C3" 1.446(6) yes
C4 C5 1.406(7) yes
C4 C7 1.495(8) yes
C5 C6 1.394(7) yes
C5 C5' 1.506(7) yes
C5' O5' 1.183(7) yes
C5' O5" 1.307(7) yes
C5" O5" 1.453(6) yes
C6 C6' 1.503(7) yes
C7 C8 1.343(7) yes
C7 C12 1.407(7) yes
C8 C9 1.373(7) yes
C9 C10 1.385(7) yes
C10 C11 1.365(8) yes
C11 C12 1.370(7) yes
C12 N2 1.429(8) yes
N2 O1B 1.16(3) yes
N2 O1A 1.25(3) yes
N91 C92 1.338(7) yes
N91 C96 1.358(7) yes
C92 C93 1.357(7) yes
C92 C92' 1.500(7) yes
C93 C94 1.397(7) yes
C93 C93' 1.501(8) yes
C93' O93' 1.176(6) yes
C93' O93" 1.33(5) yes
C93' O93X 1.33(5) yes
C93" C93X 0.73(5) no
C93" O93X 1.36(6) no
C93" O93" 1.65(5) yes
C93X O93X 1.36(5) yes
C93X O93" 1.71(6) no
C94 C95 1.394(7) yes
C94 C97 1.481(8) yes
C95 C96 1.391(8) yes
C95 C95' 1.525(9) yes
C95' O95' 1.199(8) yes
C95' O95" 1.315(8) yes
C95" O95" 1.445(7) yes
C96 C96' 1.506(8) yes
C97 C98 1.355(8) yes
C97 C912 1.413(7) yes
C98 C99 1.376(8) yes
C99 C910 1.381(7) yes
C910 C911 1.364(8) yes
C911 C912 1.386(7) yes
C912 N92 1.418(7) yes
N92 O91 1.221(5) yes
