#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:51:41 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280187 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/16/7061657.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_7061657
loop_
_publ_author_name
'Wei, Tai-Bao'
'Dang, Li-Rong'
'Hu, Jian-Peng'
'Jia, Yu'
'Lin, Qi'
'Yao, Hong'
'Shi, Bingbing'
'Zhang, You-Ming'
'Qu, Wen-Juan'
_publ_section_title
;
 A simple phenazine derivative fluorescence sensor for detecting
 formaldehyde
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20658
_journal_page_last               20663
_journal_paper_doi               10.1039/D2NJ02586H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         '2(C7 H3 N O2)'
_chemical_formula_sum            'C14 H6 N2 O4'
_chemical_formula_weight         266.21
_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     direct
_audit_creation_date             2020-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-28 deposited with the CCDC.	2022-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.202(6)
_cell_angle_beta                 107.895(6)
_cell_angle_gamma                100.224(5)
_cell_formula_units_Z            2
_cell_length_a                   7.6356(5)
_cell_length_b                   8.2211(5)
_cell_length_c                   9.0033(7)
_cell_measurement_reflns_used    1467
_cell_measurement_temperature    294.26(10)
_cell_measurement_theta_max      69.3910
_cell_measurement_theta_min      8.1180
_cell_volume                     528.26(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.26(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    132.00 164.00   1.00    1.50    --  108.00 111.00 -30.00   32
  2  ω    105.00 131.00   1.00    1.50    --  108.00 111.00 -30.00   26
  3  ω     84.00 162.00   1.00    1.50    --  108.00  77.00 -90.00   78
  4  ω    116.00 142.00   1.00    1.50    --  108.00 111.00-180.00   26
  5  ω    147.00 173.00   1.00    1.50    --  108.00 111.00-180.00   26
  6  ω     84.00 176.00   1.00    1.50    --  108.00  25.00-120.00   92
  7  ω    102.00 152.00   1.00    1.50    --  108.00 111.00  90.00   50
  8  ω    122.00 178.00   1.00    1.50    --  108.00 111.00 120.00   56
  9  ω     93.00 173.00   1.00    1.50    --  108.00  63.00 150.00   80
 10  ω     90.00 134.00   1.00    1.50    --  108.00 -38.00 120.00   44
 11  ω     71.00 103.00   1.00    1.50    --  108.00-106.00  94.00   32
 12  ω     42.00 146.00   1.00    1.50    --  108.00 -91.00 150.00  104
 13  ω     52.00 114.00   1.00    1.50    --  108.00-111.00 -30.00   62
 14  ω     38.00 126.00   1.00    1.50    --  108.00 -50.00   0.00   88
 15  ω     42.00  67.00   1.00    1.50    --  108.00 -38.00 120.00   25
 16  ω     21.00 127.00   1.00    1.50    --   54.00  19.00 120.00  106
 17  ω     39.00  69.00   1.00    1.00    --    0.00  57.00 150.00   30
 18  ω    -17.00  14.00   1.00    1.00    --    0.00  57.00 150.00   31
 19  ω     -4.00  73.00   1.00    1.50    --   54.00 -57.00 -60.00   77
 20  ω     25.00 107.00   1.00    1.50    --   54.00-125.00-180.00   82
 21  ω      9.00  69.00   1.00    1.50    --   54.00 -57.00-150.00   60
 22  ω     28.00 113.00   1.00    1.50    --   54.00  38.00-150.00   85
 23  ω     -2.00  32.00   1.00    1.00    --    0.00  57.00 -90.00   34
 24  ω     30.00  55.00   1.00    1.50    --   54.00-125.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0520787000
_diffrn_orient_matrix_UB_12      0.0733662000
_diffrn_orient_matrix_UB_13      -0.1413739000
_diffrn_orient_matrix_UB_21      0.2061651000
_diffrn_orient_matrix_UB_22      0.0493640000
_diffrn_orient_matrix_UB_23      0.1026378000
_diffrn_orient_matrix_UB_31      0.0370892000
_diffrn_orient_matrix_UB_32      -0.1690510000
_diffrn_orient_matrix_UB_33      -0.0439887000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3178
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.671
_diffrn_reflns_theta_min         5.172
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0380
_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)+(0.0714P)²+0.0719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1653
_reflns_number_total             1930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj02586h2.cif
_cod_data_source_block           shida_5
_cod_depositor_comments          'Adding full bibliography for 7061657.cif.'
_cod_original_cell_volume        528.27(6)
_cod_database_code               7061657
_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   0.958
_shelx_estimated_absorpt_t_min   0.919
_reflns_odcompleteness_completeness 99.05
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), N2(H2), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.806
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
O1 O 0.31890(16) 0.98169(13) 1.08288(15) 0.0485(3) Uani 1 1 d . . . . .
O2 O 0.45387(15) 0.57552(14) 0.82185(13) 0.0437(3) Uani 1 1 d . . . . .
N1 N 0.38297(17) 0.77311(15) 0.95577(15) 0.0376(3) Uani 1 1 d . . . . .
H1 H 0.478611 0.840051 0.946255 0.045 Uiso 1 1 calc R . . . .
C1 C 0.2776(2) 0.83798(17) 1.03223(18) 0.0354(4) Uani 1 1 d . . . . .
C2 C 0.11236(19) 0.72208(17) 1.04815(16) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.07838(19) 0.55537(17) 0.99093(16) 0.0287(3) Uani 1 1 d . . . . .
C4 C 0.19350(18) 0.49534(17) 0.91582(16) 0.0303(3) Uani 1 1 d . . . . .
C5 C 0.35372(19) 0.61375(18) 0.89260(17) 0.0327(3) Uani 1 1 d . . . . .
C6 C -0.0039(2) 0.77724(18) 1.11787(18) 0.0356(4) Uani 1 1 d . . . . .
H6 H 0.018583 0.888016 1.152344 0.043 Uiso 1 1 calc R . . . .
C7 C -0.1577(2) 0.66689(18) 1.13764(18) 0.0346(4) Uani 1 1 d . . . . .
H7 H -0.234834 0.704370 1.187079 0.042 Uiso 1 1 calc R . . . .
O3 O 0.12040(17) 0.99362(13) 0.67803(15) 0.0497(3) Uani 1 1 d . . . . .
O4 O 0.47026(16) 0.79324(13) 0.42456(15) 0.0477(3) Uani 1 1 d . . . . .
N2 N 0.28992(17) 0.88782(14) 0.54993(16) 0.0385(3) Uani 1 1 d . . . . .
H2 H 0.361611 0.983477 0.562324 0.046 Uiso 1 1 calc R . . . .
C8 C 0.1416(2) 0.87553(17) 0.60913(18) 0.0349(4) Uani 1 1 d . . . . .
C9 C 0.01640(19) 0.71086(17) 0.58477(16) 0.0300(3) Uani 1 1 d . . . . .
C10 C 0.05847(19) 0.57883(17) 0.50991(16) 0.0280(3) Uani 1 1 d . . . . .
C11 C 0.21494(19) 0.59897(16) 0.45421(16) 0.0300(3) Uani 1 1 d . . . . .
C12 C 0.3364(2) 0.76500(17) 0.47344(18) 0.0347(4) Uani 1 1 d . . . . .
C13 C -0.1382(2) 0.68779(18) 0.63674(18) 0.0342(3) Uani 1 1 d . . . . .
H13 H -0.165657 0.776223 0.684543 0.041 Uiso 1 1 calc R . . . .
C14 C -0.2537(2) 0.53150(18) 0.61755(18) 0.0337(3) Uani 1 1 d . . . . .
H14 H -0.356948 0.516125 0.653581 0.040 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C5 127.86(12) . . ?
O1 C1 N1 121.36(13) . . ?
O1 C1 C2 122.73(13) . . ?
N1 C1 C2 115.91(12) . . ?
C3 C2 C1 119.05(13) . . ?
C6 C2 C1 119.94(13) . . ?
C6 C2 C3 121.01(13) . . ?
C2 C3 C3 118.65(16) . 2_567 ?
C4 C3 C2 122.41(13) . . ?
C4 C3 C3 118.94(16) . 2_567 ?
C3 C4 C5 118.51(13) . . ?
C7 C4 C3 121.09(13) 2_567 . ?
C7 C4 C5 120.38(13) 2_567 . ?
O2 C5 N1 120.72(13) . . ?
O2 C5 C4 123.14(14) . . ?
N1 C5 C4 116.14(12) . . ?
C2 C6 C7 120.25(13) . . ?
C4 C7 C6 120.04(13) 2_567 . ?
C12 N2 C8 127.61(12) . . ?
O3 C8 N2 120.51(13) . . ?
O3 C8 C9 123.56(14) . . ?
N2 C8 C9 115.92(12) . . ?
C10 C9 C8 119.24(13) . . ?
C13 C9 C8 120.05(13) . . ?
C13 C9 C10 120.71(13) . . ?
C9 C10 C10 119.16(16) . 2_566 ?
C9 C10 C11 122.02(13) . . ?
C10 C10 C11 118.82(16) 2_566 . ?
C10 C11 C12 118.78(13) . . ?
C14 C11 C10 121.00(13) 2_566 . ?
C14 C11 C12 120.22(13) 2_566 . ?
O4 C12 N2 120.98(13) . . ?
O4 C12 C11 122.64(13) . . ?
N2 C12 C11 116.37(12) . . ?
C9 C13 C14 120.12(14) . . ?
C11 C14 C13 120.19(13) 2_566 . ?
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
O1 C1 1.2161(18) . ?
O2 C5 1.2134(17) . ?
N1 C1 1.3769(18) . ?
N1 C5 1.3793(19) . ?
C1 C2 1.4851(19) . ?
C2 C3 1.413(2) . ?
C2 C6 1.368(2) . ?
C3 C3 1.422(3) 2_567 ?
C3 C4 1.4108(19) . ?
C4 C5 1.4913(19) . ?
C4 C7 1.368(2) 2_567 ?
C6 C7 1.409(2) . ?
O3 C8 1.2113(18) . ?
O4 C12 1.2189(18) . ?
N2 C8 1.3808(19) . ?
N2 C12 1.3755(18) . ?
C8 C9 1.485(2) . ?
C9 C10 1.410(2) . ?
C9 C13 1.382(2) . ?
C10 C10 1.414(3) 2_566 ?
C10 C11 1.4159(19) . ?
C11 C12 1.4843(19) . ?
C11 C14 1.371(2) 2_566 ?
C13 C14 1.400(2) . ?
