#------------------------------------------------------------------------------
#$Date: 2020-07-17 23:06:49 +0300 (Fri, 17 Jul 2020) $
#$Revision: 254370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240884.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_7240884
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         'C10 H7 N O2'
_chemical_formula_sum            'C10 H7 N O2'
_chemical_formula_weight         173.17
_chemical_name_systematic        1-(hydroxyimino)naphthalen-2(1H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-19
_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                90
_cell_angle_beta                 98.193(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4498(9)
_cell_length_b                   9.1487(16)
_cell_length_c                   15.499(3)
_cell_measurement_reflns_used    3327
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      36.22
_cell_measurement_theta_min      2.66
_cell_volume                     764.9(2)
_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      150.01
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.486
_diffrn_reflns_theta_min         2.655
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       Block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0828P)²+0.1045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2502
_reflns_number_total             3666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00728e2.cif
_cod_data_source_block           sp159_0m
_cod_database_code               7240884
_shelx_shelxl_version_number     2014/7
_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   0.986
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
O2 O 0.28680(15) 0.90859(9) 0.43925(5) 0.02823(18) Uani 1 1 d . . . . .
O1 O 0.64263(17) 0.79591(10) 0.37838(5) 0.0305(2) Uani 1 1 d . . . . .
N1 N 0.69440(17) 0.71278(10) 0.45157(6) 0.02398(18) Uani 1 1 d . . . . .
C6 C 0.60733(16) 0.63481(10) 0.58957(5) 0.01637(16) Uani 1 1 d . . . . .
C2 C 0.34041(17) 0.83117(10) 0.50574(6) 0.01930(17) Uani 1 1 d . . . . .
C4 C 0.26515(17) 0.75673(11) 0.65001(6) 0.01923(17) Uani 1 1 d . . . . .
C10 C 0.51988(18) 0.56667(11) 0.73361(6) 0.02036(18) Uani 1 1 d . . . . .
C1 C 0.55014(16) 0.72692(10) 0.51181(6) 0.01786(17) Uani 1 1 d . . . . .
C5 C 0.46545(15) 0.65126(10) 0.65791(6) 0.01610(16) Uani 1 1 d . . . . .
C7 C 0.79827(17) 0.53137(11) 0.59825(6) 0.02156(19) Uani 1 1 d . . . . .
C9 C 0.71053(18) 0.46574(11) 0.74131(6) 0.02257(19) Uani 1 1 d . . . . .
C3 C 0.20459(17) 0.84197(11) 0.57916(6) 0.02070(18) Uani 1 1 d . . . . .
C8 C 0.84896(18) 0.44758(12) 0.67299(7) 0.0236(2) Uani 1 1 d . . . . .
H4 H 0.173(2) 0.7626(16) 0.7014(9) 0.023(3) Uiso 1 1 d . . . . .
H10 H 0.423(3) 0.5813(15) 0.7828(9) 0.027(3) Uiso 1 1 d . . . . .
H9 H 0.746(3) 0.4054(17) 0.7931(10) 0.030(4) Uiso 1 1 d . . . . .
H8 H 0.983(3) 0.3760(17) 0.6776(9) 0.031(4) Uiso 1 1 d . . . . .
H7 H 0.898(3) 0.5159(17) 0.5498(10) 0.034(4) Uiso 1 1 d . . . . .
H3 H 0.070(3) 0.9133(17) 0.5757(10) 0.034(4) Uiso 1 1 d . . . . .
H1 H 0.507(4) 0.848(2) 0.3860(13) 0.060(6) Uiso 1 1 d . . . . .
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
N1 O1 H1 105.1(13) . . ?
C1 N1 O1 117.68(9) . . ?
C5 C6 C1 118.83(8) . . ?
C7 C6 C1 122.39(8) . . ?
C7 C6 C5 118.79(8) . . ?
O2 C2 C1 120.31(8) . . ?
O2 C2 C3 121.60(9) . . ?
C3 C2 C1 118.08(8) . . ?
C5 C4 H4 115.1(8) . . ?
C3 C4 C5 123.21(8) . . ?
C3 C4 H4 121.7(8) . . ?
C5 C10 H10 119.7(8) . . ?
C9 C10 C5 120.52(8) . . ?
C9 C10 H10 119.8(8) . . ?
N1 C1 C6 116.74(8) . . ?
N1 C1 C2 123.67(9) . . ?
C6 C1 C2 119.58(8) . . ?
C6 C5 C4 119.76(8) . . ?
C10 C5 C6 119.88(8) . . ?
C10 C5 C4 120.36(8) . . ?
C6 C7 H7 120.1(9) . . ?
C8 C7 C6 120.82(8) . . ?
C8 C7 H7 119.1(9) . . ?
C10 C9 C8 119.68(9) . . ?
C10 C9 H9 120.5(9) . . ?
C8 C9 H9 119.8(9) . . ?
C2 C3 H3 117.8(9) . . ?
C4 C3 C2 120.50(9) . . ?
C4 C3 H3 121.7(9) . . ?
C7 C8 C9 120.30(9) . . ?
C7 C8 H8 119.4(9) . . ?
C9 C8 H8 120.3(9) . . ?
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
O2 C2 1.2502(12) . ?
O1 N1 1.3614(12) . ?
O1 H1 0.90(2) . ?
N1 C1 1.3099(12) . ?
C6 C1 1.4672(13) . ?
C6 C5 1.4056(12) . ?
C6 C7 1.3988(13) . ?
C2 C1 1.4814(14) . ?
C2 C3 1.4467(13) . ?
C4 C5 1.4490(13) . ?
C4 C3 1.3489(14) . ?
C4 H4 1.001(13) . ?
C10 C5 1.4016(13) . ?
C10 C9 1.3824(14) . ?
C10 H10 0.994(14) . ?
C7 C8 1.3837(14) . ?
C7 H7 1.000(15) . ?
C9 C8 1.3948(14) . ?
C9 H9 0.971(15) . ?
C3 H3 0.976(16) . ?
C8 H8 0.976(15) . ?
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
O1 H1 O2 0.90(2) 1.65(2) 2.4970(12) 156.2(19) .
