#------------------------------------------------------------------------------
#$Date: 2022-06-28 17:19:57 +0300 (Tue, 28 Jun 2022) $
#$Revision: 276327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/01/7240106.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_7240106
loop_
_publ_author_name
'Gong, Jing'
'Peshkov, Anatoly A.'
'Yu, Jiafeng'
'Amandykova, Sagadat'
'Gimnkhan, Aidana'
'Huang, Jianjun'
'Kashtanov, Stepan'
'Pereshivko, Olga P.'
'Peshkov, Vsevolod A.'
_publ_section_title
;
 Three-component reaction of azulene, aryl glyoxal and 1,3-dicarbonyl
 compound for the synthesis of various azulene derivatives
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              10113
_journal_page_last               10117
_journal_paper_doi               10.1039/D0RA00356E
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         '0.07(C32 H27 N O), 0.07(C3 H7 N O)'
_chemical_formula_sum            'C2.59 H2.52 N0.15 O0.15'
_chemical_formula_weight         38.12
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-22 deposited with the CCDC.	2020-02-27 downloaded from the CCDC.
;
_cell_angle_alpha                114.900(2)
_cell_angle_beta                 109.637(2)
_cell_angle_gamma                96.010(2)
_cell_formula_units_Z            27
_cell_length_a                   10.9118(6)
_cell_length_b                   11.6167(6)
_cell_length_c                   13.1533(7)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.44
_cell_volume                     1363.93(13)
_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      296.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64042
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.439
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.7217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1731 before and 0.0625 after correction. The Ratio of minimum to maximum transmission is 0.9698. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_preparation       'as described in the publication'
_exptl_crystal_recrystallization_method 'as described in the publication'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0266(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         6259
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0450
_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)+(0.0379P)²+0.4145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4275
_reflns_number_total             6259
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra00356e2.cif
_cod_data_source_block           b191223a_0m_a
_cod_depositor_comments          'Adding full bibliography for 7240106.cif.'
_cod_database_code               7240106
_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   0.988
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
;
_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
O001 O 0.40517(10) 0.81427(10) 0.57252(10) 0.0325(3) Uani 1 1 d . . . . .
N002 N 0.13727(11) 0.39279(11) 0.40847(10) 0.0224(3) Uani 1 1 d . . . . .
O003 O 0.93505(12) 1.20462(13) 0.97561(12) 0.0549(4) Uani 1 1 d . . . . .
N004 N 0.71467(13) 1.07930(13) 0.88125(13) 0.0386(3) Uani 1 1 d . . . . .
C005 C 0.46948(14) 0.62329(13) 0.79460(13) 0.0227(3) Uani 1 1 d . . . . .
C006 C 0.26922(13) 0.59462(13) 0.48374(12) 0.0212(3) Uani 1 1 d . . . . .
C007 C 0.30260(14) 0.72376(14) 0.49246(13) 0.0228(3) Uani 1 1 d . . . . .
C008 C 0.33185(13) 0.54364(13) 0.56481(12) 0.0209(3) Uani 1 1 d . . . . .
C009 C 0.02412(14) 0.27449(13) 0.33204(12) 0.0226(3) Uani 1 1 d . . . . .
C00A C 0.15063(13) 0.49911(13) 0.38976(12) 0.0219(3) Uani 1 1 d . . . . .
C00B C 0.24859(13) 0.41846(13) 0.51554(12) 0.0218(3) Uani 1 1 d . . . . .
C00C C 0.36416(15) 0.59428(14) 0.82414(14) 0.0280(3) Uani 1 1 d . . . . .
C00D C 0.11379(14) 0.62109(14) 0.26983(13) 0.0257(3) Uani 1 1 d . . . . .
C00E C -0.10051(14) 0.28149(15) 0.33385(13) 0.0256(3) Uani 1 1 d . . . . .
C00F C 0.26779(14) 0.31427(13) 0.55100(12) 0.0237(3) Uani 1 1 d . . . . .
C00G C 0.19545(15) 0.74437(15) 0.39734(14) 0.0263(3) Uani 1 1 d . . . . .
C00H C 0.61694(14) 0.68191(13) 0.87975(13) 0.0260(3) Uani 1 1 d . . . . .
C00I C 0.05084(15) 0.50846(15) 0.28579(14) 0.0276(3) Uani 1 1 d . . . . .
C00J C 0.58846(15) 0.65942(14) 0.69329(14) 0.0284(3) Uani 1 1 d . . . . .
C00K C 0.45768(13) 0.60857(13) 0.67971(13) 0.0227(3) Uani 1 1 d . . . . .
C00L C 0.68372(15) 0.70251(15) 0.81239(14) 0.0302(3) Uani 1 1 d . . . . .
C00M C 0.39000(16) 0.28241(16) 0.57082(14) 0.0315(4) Uani 1 1 d . . . . .
C00N C 0.16577(16) 0.24199(15) 0.56013(14) 0.0315(4) Uani 1 1 d . . . . .
C00O C 0.04199(16) 0.15565(15) 0.26106(15) 0.0321(4) Uani 1 1 d . . . . .
C00P C -0.20907(16) 0.16775(16) 0.26549(15) 0.0330(4) Uani 1 1 d . . . . .
C00Q C -0.00134(17) 0.65264(18) 0.19041(17) 0.0355(4) Uani 1 1 d . . . . .
C00R C 0.67834(17) 0.70525(15) 0.99998(14) 0.0331(4) Uani 1 1 d . . . . .
C00S C 0.20707(18) 0.57875(18) 0.20502(16) 0.0354(4) Uani 1 1 d . . . . .
C00T C 0.36883(18) 0.60845(16) 0.93569(15) 0.0360(4) Uani 1 1 d . . . . .
C00U C 0.30607(19) 0.10806(16) 0.60320(15) 0.0401(4) Uani 1 1 d . . . . .
C00V C 0.61850(19) 0.69020(16) 1.07329(15) 0.0399(4) Uani 1 1 d . . . . .
C00W C -0.19104(17) 0.04803(17) 0.19682(17) 0.0414(4) Uani 1 1 d . . . . .
C00X C 0.40808(19) 0.17978(18) 0.59601(16) 0.0406(4) Uani 1 1 d . . . . .
C00Y C -0.06604(17) 0.04171(16) 0.19379(17) 0.0416(4) Uani 1 1 d . . . . .
C00Z C 0.18481(19) 0.13970(16) 0.58617(15) 0.0389(4) Uani 1 1 d . . . . .
C010 C 0.4824(2) 0.65026(17) 1.04551(15) 0.0412(4) Uani 1 1 d . . . . .
C011 C 0.83039(19) 1.16173(18) 0.97889(18) 0.0448(4) Uani 1 1 d . . . . .
C012 C 0.7027(2) 1.0340(2) 0.75698(18) 0.0483(5) Uani 1 1 d . . . . .
C013 C 0.5953(2) 1.0331(2) 0.8945(2) 0.0549(5) Uani 1 1 d . . . . .
H00E H -0.1107(14) 0.3636(16) 0.3837(14) 0.026(4) Uiso 1 1 d . . . . .
H00A H 0.2405(15) 0.8161(15) 0.3887(13) 0.029(4) Uiso 1 1 d . . . . .
H00B H 0.1302(15) 0.7770(15) 0.4327(14) 0.029(4) Uiso 1 1 d . . . . .
H00C H 0.2725(16) 0.5617(15) 0.7561(15) 0.030(4) Uiso 1 1 d . . . . .
H00N H 0.0815(18) 0.2645(17) 0.5482(15) 0.042(5) Uiso 1 1 d . . . . .
H00D H -0.0329(16) 0.5248(15) 0.3027(14) 0.030(4) Uiso 1 1 d . . . . .
H00J H 0.6070(16) 0.6617(16) 0.6270(15) 0.037(4) Uiso 1 1 d . . . . .
H00F H 0.0175(15) 0.4245(16) 0.2094(15) 0.028(4) Uiso 1 1 d . . . . .
H00M H 0.4623(17) 0.3340(17) 0.5649(15) 0.043(5) Uiso 1 1 d . . . . .
H00K H 0.2856(18) 0.5566(16) 0.2521(16) 0.041(5) Uiso 1 1 d . . . . .
H00Q H 0.1557(17) 0.4981(18) 0.1239(17) 0.045(5) Uiso 1 1 d . . . . .
H00G H -0.0650(18) 0.6785(17) 0.2293(16) 0.043(5) Uiso 1 1 d . . . . .
H00W H -0.2671(18) -0.0311(18) 0.1492(16) 0.049(5) Uiso 1 1 d . . . . .
H00L H 0.7815(17) 0.7405(16) 0.8458(15) 0.038(4) Uiso 1 1 d . . . . .
H00P H -0.2990(17) 0.1726(16) 0.2653(15) 0.040(5) Uiso 1 1 d . . . . .
H00H H 0.0353(18) 0.7225(19) 0.1749(17) 0.053(5) Uiso 1 1 d . . . . .
H010 H 0.4597(18) 0.6487(17) 1.1111(17) 0.050(5) Uiso 1 1 d . . . . .
H00O H 0.1304(17) 0.1539(15) 0.2610(15) 0.036(4) Uiso 1 1 d . . . . .
H00R H 0.7773(18) 0.7392(16) 1.0361(15) 0.038(4) Uiso 1 1 d . . . . .
H00T H 0.2789(18) 0.5834(17) 0.9368(16) 0.046(5) Uiso 1 1 d . . . . .
H00Z H 0.1123(18) 0.0917(18) 0.5914(16) 0.045(5) Uiso 1 1 d . . . . .
H00Y H -0.0525(17) -0.0415(18) 0.1432(17) 0.049(5) Uiso 1 1 d . . . . .
H00U H 0.3171(17) 0.0358(18) 0.6188(16) 0.046(5) Uiso 1 1 d . . . . .
H00I H -0.0566(18) 0.5703(18) 0.1079(17) 0.046(5) Uiso 1 1 d . . . . .
H00V H 0.6828(18) 0.7126(17) 1.1568(17) 0.048(5) Uiso 1 1 d . . . . .
H00S H 0.2429(17) 0.6499(18) 0.1898(16) 0.045(5) Uiso 1 1 d . . . . .
H00X H 0.4947(19) 0.1580(18) 0.6075(16) 0.053(5) Uiso 1 1 d . . . . .
H01A H 0.796(2) 1.066(2) 0.760(2) 0.072(7) Uiso 1 1 d . . . . .
H011 H 0.8200(19) 1.1851(19) 1.0581(19) 0.063(6) Uiso 1 1 d . . . . .
H01D H 0.611(2) 1.075(2) 0.981(2) 0.075(7) Uiso 1 1 d . . . . .
H01E H 0.565(2) 0.935(2) 0.856(2) 0.072(7) Uiso 1 1 d . . . . .
H01B H 0.665(2) 0.936(3) 0.707(2) 0.085(7) Uiso 1 1 d . . . . .
H01F H 0.516(2) 1.056(2) 0.849(2) 0.076(7) Uiso 1 1 d . . . . .
H01C H 0.641(2) 1.072(2) 0.720(2) 0.084(8) 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
C00A N002 C009 124.98(11) . . ?
C00A N002 C00B 109.37(11) . . ?
C00B N002 C009 125.63(11) . . ?
C011 N004 C012 120.99(16) . . ?
C011 N004 C013 121.99(17) . . ?
C012 N004 C013 117.01(16) . . ?
C00C C005 C00H 126.75(13) . . ?
C00C C005 C00K 126.60(13) . . ?
C00K C005 C00H 106.59(12) . . ?
C008 C006 C007 132.07(12) . . ?
C00A C006 C007 119.83(12) . . ?
C00A C006 C008 107.81(12) . . ?
O001 C007 C006 124.33(13) . . ?
O001 C007 C00G 120.38(12) . . ?
C006 C007 C00G 115.20(12) . . ?
C006 C008 C00K 128.89(12) . . ?
C00B C008 C006 106.46(11) . . ?
C00B C008 C00K 124.63(12) . . ?
C00E C009 N002 118.84(12) . . ?
C00E C009 C00O 120.98(13) . . ?
C00O C009 N002 120.15(13) . . ?
N002 C00A C006 108.30(12) . . ?
N002 C00A C00I 124.62(12) . . ?
C006 C00A C00I 127.06(12) . . ?
N002 C00B C00F 120.94(12) . . ?
C008 C00B N002 108.05(11) . . ?
C008 C00B C00F 130.69(12) . . ?
C005 C00C C00T 129.39(15) . . ?
C00G C00D C00I 109.43(12) . . ?
C00Q C00D C00G 109.89(13) . . ?
C00Q C00D C00I 108.37(12) . . ?
C00S C00D C00G 109.65(12) . . ?
C00S C00D C00I 110.53(13) . . ?
C00S C00D C00Q 108.94(13) . . ?
C009 C00E C00P 119.77(14) . . ?
C00M C00F C00B 119.21(13) . . ?
C00M C00F C00N 118.16(14) . . ?
C00N C00F C00B 122.56(13) . . ?
C007 C00G C00D 115.98(12) . . ?
C00L C00H C005 106.66(12) . . ?
C00R C00H C005 127.38(14) . . ?
C00R C00H C00L 125.88(14) . . ?
C00A C00I C00D 111.09(12) . . ?
C00L C00J C00K 110.36(14) . . ?
C005 C00K C008 125.56(12) . . ?
C005 C00K C00J 107.66(12) . . ?
C00J C00K C008 126.67(13) . . ?
C00J C00L C00H 108.69(13) . . ?
C00X C00M C00F 120.73(16) . . ?
C00Z C00N C00F 120.83(15) . . ?
C009 C00O C00Y 119.27(15) . . ?
C00W C00P C00E 119.55(15) . . ?
C00H C00R C00V 128.96(16) . . ?
C00C C00T C010 128.48(16) . . ?
C00X C00U C00Z 119.64(15) . . ?
C010 C00V C00R 128.87(16) . . ?
C00P C00W C00Y 120.50(15) . . ?
C00U C00X C00M 120.58(16) . . ?
C00O C00Y C00W 119.90(16) . . ?
C00U C00Z C00N 120.05(16) . . ?
C00V C010 C00T 129.75(16) . . ?
O003 C011 N004 126.01(18) . . ?
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
O001 C007 1.2232(16) . ?
N002 C009 1.4390(17) . ?
N002 C00A 1.3599(17) . ?
N002 C00B 1.4031(17) . ?
O003 C011 1.219(2) . ?
N004 C011 1.335(2) . ?
N004 C012 1.443(2) . ?
N004 C013 1.450(2) . ?
C005 C00C 1.384(2) . ?
C005 C00H 1.4914(19) . ?
C005 C00K 1.4059(19) . ?
C006 C007 1.4522(19) . ?
C006 C008 1.4428(18) . ?
C006 C00A 1.3795(19) . ?
C007 C00G 1.5223(19) . ?
C008 C00B 1.3763(19) . ?
C008 C00K 1.4720(19) . ?
C009 C00E 1.378(2) . ?
C009 C00O 1.382(2) . ?
C00A C00I 1.4888(19) . ?
C00B C00F 1.4795(19) . ?
C00C C00T 1.388(2) . ?
C00D C00G 1.537(2) . ?
C00D C00I 1.539(2) . ?
C00D C00Q 1.530(2) . ?
C00D C00S 1.530(2) . ?
C00E C00P 1.383(2) . ?
C00F C00M 1.391(2) . ?
C00F C00N 1.392(2) . ?
C00H C00L 1.396(2) . ?
C00H C00R 1.383(2) . ?
C00J C00K 1.407(2) . ?
C00J C00L 1.386(2) . ?
C00M C00X 1.381(2) . ?
C00N C00Z 1.385(2) . ?
C00O C00Y 1.382(2) . ?
C00P C00W 1.381(2) . ?
C00R C00V 1.388(2) . ?
C00T C010 1.392(2) . ?
C00U C00X 1.373(3) . ?
C00U C00Z 1.381(3) . ?
C00V C010 1.379(3) . ?
C00W C00Y 1.386(2) . ?
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-06-28T17:18:00+03:00
;
 Removed the '_chemical_name_systematic' data item that
 had an incorrect value.
;
