#------------------------------------------------------------------------------
#$Date: 2020-07-17 23:06:49 +0300 (Fri, 17 Jul 2020) $
#$Revision: 254370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240888.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_7240888
loop_
_publ_author_name
'Pike, Sarah J.'
'Heliot, Armelle'
'Seaton, Colin C.'
_publ_section_title
;
 ortho-Substituent effect on the crystal packing and solid state
 speciation of aromatic C-nitroso compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00728E
_journal_year                    2020
_chemical_formula_moiety         'C11 H14 N2 O3'
_chemical_formula_sum            'C11 H14 N2 O3'
_chemical_formula_weight         222.24
_chemical_name_systematic
;
N-(2-nitrosophenyl)pivalamide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                93.043(8)
_cell_angle_beta                 92.475(8)
_cell_angle_gamma                93.340(8)
_cell_formula_units_Z            4
_cell_length_a                   5.6472(8)
_cell_length_b                   14.1772(19)
_cell_length_c                   14.2690(18)
_cell_measurement_reflns_used    3750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.66
_cell_measurement_theta_min      2.86
_cell_volume                     1137.6(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.11
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            38179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.692
_diffrn_reflns_theta_min         1.973
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0700 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       Block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         6932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0530P)²+0.0968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3643
_reflns_number_total             6932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00728e2.cif
_cod_data_source_block           sp081b_0m
_cod_database_code               7240888
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(N3)=Sof(O4)=1-FVAR(1)
 Sof(N2)=Sof(O3)=FVAR(1)
 Sof(N3A)=Sof(O3A)=1-FVAR(2)
 Sof(N2A)=Sof(O4A)=FVAR(2)
3.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N1(H1), C5A(H5A), C3(H3), C2A(H2A), C4A(H4A), C6(H6), C3A(H3A),
 C5(H5), C4(H4)
3.b Idealised Me refined as rotating group:
 C10A(H10A,H10B,H10C), C11A(H11A,H11B,H11C), C10(H10D,H10E,H10F), C9A(H9AA,
 H9AB,H9AC), C11(H11D,H11E,H11F), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O -0.1488(2) 0.17059(9) 0.82913(8) 0.0256(3) Uani 1 1 d . . . . .
O2A O -0.3055(2) 0.29741(9) 0.76272(8) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.7778(2) 0.39427(9) 0.18565(9) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.5950(2) 0.31578(9) 0.30006(8) 0.0302(3) Uani 1 1 d . . . . .
N1A N -0.0085(3) 0.21613(10) 0.69685(9) 0.0238(3) Uani 1 1 d . . . . .
H1A H 0.083765 0.169592 0.707584 0.029 Uiso 1 1 calc R . . . .
N1 N 0.9125(3) 0.25905(10) 0.22344(10) 0.0256(3) Uani 1 1 d . . . . .
H1 H 1.000806 0.270826 0.175605 0.031 Uiso 1 1 calc R . . . .
C7A C -0.1709(3) 0.23456(13) 0.76358(12) 0.0238(4) Uani 1 1 d . . . . .
C6A C 0.0274(3) 0.26208(12) 0.61453(11) 0.0223(4) Uani 1 1 d . . . . .
C1A C 0.2222(3) 0.23896(12) 0.56140(12) 0.0238(4) Uani 1 1 d . . . . .
C7 C 0.7439(3) 0.32277(12) 0.24267(12) 0.0230(4) Uani 1 1 d . . . . .
C5A C -0.1209(3) 0.33000(13) 0.58124(12) 0.0254(4) Uani 1 1 d . . . . .
H5A H -0.256405 0.345830 0.614563 0.031 Uiso 1 1 calc R . . . .
C1 C 1.1594(3) 0.12897(12) 0.24497(12) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.9600(3) 0.17861(12) 0.27026(11) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.8239(3) 0.14423(13) 0.34180(12) 0.0274(4) Uani 1 1 d . . . . .
H3 H 0.686369 0.175183 0.359275 0.033 Uiso 1 1 calc R . . . .
C8A C -0.2907(3) 0.17593(13) 0.91418(12) 0.0260(4) Uani 1 1 d . . . . .
C2A C 0.2717(3) 0.28522(14) 0.47963(12) 0.0293(4) Uani 1 1 d . . . . .
H2A H 0.405019 0.269291 0.444967 0.035 Uiso 1 1 calc R . . . .
C4A C -0.0693(3) 0.37382(13) 0.49986(12) 0.0291(4) Uani 1 1 d . . . . .
H4A H -0.171871 0.419333 0.477521 0.035 Uiso 1 1 calc R . . . .
C6 C 1.2220(3) 0.04970(13) 0.29300(13) 0.0307(4) Uani 1 1 d . . . . .
H6 H 1.358262 0.017590 0.276083 0.037 Uiso 1 1 calc R . . . .
C3A C 0.1295(3) 0.35308(14) 0.44946(12) 0.0314(4) Uani 1 1 d . . . . .
H3A H 0.165142 0.385784 0.394900 0.038 Uiso 1 1 calc R . . . .
C8 C 0.6321(3) 0.47847(13) 0.19341(14) 0.0300(4) Uani 1 1 d . . . . .
C5 C 1.0881(4) 0.01816(13) 0.36424(13) 0.0328(5) Uani 1 1 d . . . . .
H5 H 1.131159 -0.035135 0.397337 0.039 Uiso 1 1 calc R . . . .
C10A C -0.2262(4) 0.26860(14) 0.96973(13) 0.0339(5) Uani 1 1 d . . . . .
H10A H -0.053725 0.275736 0.981784 0.051 Uiso 1 1 calc GR . . . .
H10B H -0.304826 0.268777 1.029631 0.051 Uiso 1 1 calc GR . . . .
H10C H -0.278253 0.321225 0.933721 0.051 Uiso 1 1 calc GR . . . .
C4 C 0.8881(4) 0.06565(13) 0.38711(12) 0.0317(4) Uani 1 1 d . . . . .
H4 H 0.792837 0.043181 0.435477 0.038 Uiso 1 1 calc R . . . .
C11A C -0.2088(4) 0.09254(14) 0.96746(13) 0.0359(5) Uani 1 1 d . . . . .
H11A H -0.246164 0.033722 0.929113 0.054 Uiso 1 1 calc GR . . . .
H11B H -0.290547 0.089688 1.026538 0.054 Uiso 1 1 calc GR . . . .
H11C H -0.036982 0.100540 0.981027 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.3759(3) 0.44966(15) 0.16795(14) 0.0369(5) Uani 1 1 d . . . . .
H10D H 0.363587 0.415504 0.106229 0.055 Uiso 1 1 calc GR . . . .
H10E H 0.284392 0.506214 0.165841 0.055 Uiso 1 1 calc GR . . . .
H10F H 0.312804 0.408483 0.215191 0.055 Uiso 1 1 calc GR . . . .
C9A C -0.5531(3) 0.16255(15) 0.88649(14) 0.0362(5) Uani 1 1 d . . . . .
H9AA H -0.600935 0.215893 0.850577 0.054 Uiso 1 1 calc GR . . . .
H9AB H -0.644609 0.159589 0.943177 0.054 Uiso 1 1 calc GR . . . .
H9AC H -0.583409 0.103528 0.847800 0.054 Uiso 1 1 calc GR . . . .
C11 C 0.6682(4) 0.52436(15) 0.29182(16) 0.0518(7) Uani 1 1 d . . . . .
H11D H 0.587499 0.484537 0.336201 0.078 Uiso 1 1 calc GR . . . .
H11E H 0.602106 0.586789 0.293636 0.078 Uiso 1 1 calc GR . . . .
H11F H 0.838356 0.531399 0.309220 0.078 Uiso 1 1 calc GR . . . .
C9 C 0.7393(4) 0.54102(16) 0.12170(18) 0.0540(7) Uani 1 1 d . . . . .
H9A H 0.903344 0.561096 0.141993 0.081 Uiso 1 1 calc GR . . . .
H9B H 0.646342 0.596843 0.115886 0.081 Uiso 1 1 calc GR . . . .
H9C H 0.737672 0.505660 0.060741 0.081 Uiso 1 1 calc GR . . . .
N2A N 0.3526(5) 0.1654(3) 0.5977(3) 0.0277(8) Uani 0.766(5) 1 d . . P A 1
O4A O 0.5191(4) 0.14161(14) 0.54887(13) 0.0338(6) Uani 0.766(5) 1 d . . P A 1
N2 N 1.283(3) 0.1649(14) 0.1742(10) 0.056(4) Uani 0.564(7) 1 d . . P B 1
O3 O 1.2863(5) 0.2142(2) 0.1240(2) 0.0292(9) Uani 0.564(7) 1 d . . P B 1
N3 N 1.325(3) 0.1469(10) 0.1696(9) 0.025(2) Uani 0.436(7) 1 d . . P B 2
O4 O 1.4520(10) 0.1286(3) 0.1478(3) 0.0426(13) Uani 0.436(7) 1 d . . P B 2
N3A N 0.412(2) 0.1738(10) 0.5760(8) 0.028(3) Uiso 0.234(5) 1 d . . P A 2
O3A O 0.3860(11) 0.1290(5) 0.6491(5) 0.035(2) Uani 0.234(5) 1 d . . P A 2
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A O1A C8A 120.25(13) . . ?
C7 O1 C8 120.41(14) . . ?
C7A N1A C6A 127.88(15) . . ?
C7 N1 C2 127.89(15) . . ?
O1A C7A N1A 107.44(14) . . ?
O2A C7A O1A 127.03(16) . . ?
O2A C7A N1A 125.53(16) . . ?
N1A C6A C1A 118.41(15) . . ?
N1A C6A C5A 123.48(16) . . ?
C5A C6A C1A 118.11(16) . . ?
C6A C1A N2A 113.8(2) . . ?
C6A C1A N3A 132.4(5) . . ?
C2A C1A C6A 120.90(17) . . ?
C2A C1A N2A 125.2(2) . . ?
C2A C1A N3A 106.6(5) . . ?
O1 C7 N1 107.14(14) . . ?
O2 C7 O1 126.54(17) . . ?
O2 C7 N1 126.31(16) . . ?
C4A C5A C6A 119.76(17) . . ?
C2 C1 N3 129.0(5) . . ?
C6 C1 C2 120.56(17) . . ?
C6 C1 N3 110.4(5) . . ?
N2 C1 C2 115.3(9) . . ?
N2 C1 C6 124.1(9) . . ?
N1 C2 C1 118.20(15) . . ?
N1 C2 C3 123.85(16) . . ?
C3 C2 C1 117.95(16) . . ?
C4 C3 C2 120.23(17) . . ?
O1A C8A C10A 109.48(14) . . ?
O1A C8A C11A 102.29(14) . . ?
O1A C8A C9A 109.99(14) . . ?
C10A C8A C11A 110.91(15) . . ?
C10A C8A C9A 112.87(16) . . ?
C9A C8A C11A 110.79(16) . . ?
C3A C2A C1A 120.31(17) . . ?
C5A C4A C3A 121.77(17) . . ?
C5 C6 C1 120.48(18) . . ?
C2A C3A C4A 119.08(17) . . ?
O1 C8 C10 109.89(15) . . ?
O1 C8 C11 109.04(14) . . ?
O1 C8 C9 101.99(15) . . ?
C10 C8 C11 112.62(18) . . ?
C10 C8 C9 111.58(16) . . ?
C9 C8 C11 111.18(19) . . ?
C6 C5 C4 118.75(18) . . ?
C3 C4 C5 121.99(18) . . ?
O4A N2A C1A 114.3(4) . . ?
O3 N2 C1 145.1(17) . . ?
O4 N3 C1 141.6(12) . . ?
O3A N3A C1A 111.9(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C7A 1.344(2) . ?
O1A C8A 1.484(2) . ?
O2A C7A 1.205(2) . ?
O1 C7 1.343(2) . ?
O1 C8 1.491(2) . ?
O2 C7 1.202(2) . ?
N1A C7A 1.376(2) . ?
N1A C6A 1.390(2) . ?
N1 C7 1.376(2) . ?
N1 C2 1.386(2) . ?
C6A C1A 1.407(2) . ?
C6A C5A 1.401(2) . ?
C1A C2A 1.399(2) . ?
C1A N2A 1.419(4) . ?
C1A N3A 1.470(15) . ?
C5A C4A 1.380(2) . ?
C1 C2 1.412(2) . ?
C1 C6 1.402(2) . ?
C1 N2 1.356(14) . ?
C1 N3 1.477(13) . ?
C2 C3 1.396(2) . ?
C3 C4 1.376(2) . ?
C8A C10A 1.515(3) . ?
C8A C11A 1.523(3) . ?
C8A C9A 1.516(3) . ?
C2A C3A 1.364(3) . ?
C4A C3A 1.396(3) . ?
C6 C5 1.371(3) . ?
C8 C10 1.504(3) . ?
C8 C11 1.516(3) . ?
C8 C9 1.512(3) . ?
C5 C4 1.390(3) . ?
N2A O4A 1.245(3) . ?
N2 O3 1.028(17) . ?
N3 O4 0.845(14) . ?
N3A O3A 1.259(12) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O3A 0.88 2.03 2.705(6) 132.5 . yes
N1 H1 O3 0.88 1.99 2.682(3) 134.1 . yes
C5A H5A O2A 0.95 2.28 2.883(2) 120.6 . yes
C3 H3 O2 0.95 2.28 2.897(2) 121.7 . yes
