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#$Date: 2022-10-24 10:35:25 +0300 (Mon, 24 Oct 2022) $
#$Revision: 278729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105949.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_8105949
loop_
_publ_author_name
'Huanhuan, Yang'
'Qingqing, Xu'
'Haodong, Feng'
'Yuan, Juan'
_publ_section_title
;
 Crystal structure of
 (E)-N′-((1,8-dihydropyren-1-yl)-methylene)picolinohydrazide,
 C23H15N3O
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1103
_journal_page_last               1104
_journal_paper_doi               10.1515/ncrs-2019-0297
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C23 H15 N3 O'
_chemical_formula_sum            'C23 H15 N3 O'
_chemical_formula_weight         349.38
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.963(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4372(3)
_cell_length_b                   11.9366(2)
_cell_length_c                   10.23409(19)
_cell_measurement_reflns_used    4027
_cell_measurement_temperature    115.2(3)
_cell_measurement_theta_max      71.4300
_cell_measurement_theta_min      4.8800
_cell_volume                     1686.92(6)
_computing_cell_refinement
;
CrysAlisPro [1]'  _computing_data_collection         
'CrysAlisPro [1]'  _computing_data_reduction          
'CrysAlisPro [1]' _computing_molecular_graphics      
'Olex2 [2]'
;
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL-2015 [3]'
_computing_structure_solution    'ShelXT-2015 [4]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      115.2(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -51.00 -16.00   1.00    1.00    --  -40.81 -38.00 150.00   35
  2  ω   -109.00 -83.00   1.00    1.00    --  -40.81 -38.00 150.00   26
  3  ω    -92.00 -60.00   1.00    1.00    --  -40.81 125.00-180.00   32
  4  ω   -110.00 -14.00   1.00    1.00    --  -40.81 -57.00 -90.00   96
  5  ω     81.00 106.00   1.00    1.00    --   40.81 161.00-119.00   25
  6  ω     44.00 112.00   1.00    3.00    --  100.91 -45.00-150.00   68
  7  ω     40.00  87.00   1.00    3.00    --  100.91-125.00-180.00   47
  8  ω     48.00  74.00   1.00    3.00    --  100.91-125.00  90.00   26
  9  ω     35.00 124.00   1.00    3.00    --  100.91 -77.00 150.00   89
 10  ω     85.00 115.00   1.00    3.00    --  100.91-125.00  90.00   30
 11  ω     45.00  87.00   1.00    3.00    --  100.91 -77.00 -30.00   42
 12  ω     23.00 145.00   1.00    3.00    --  100.91   0.00 150.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0802177000
_diffrn_orient_matrix_UB_12      0.0893713000
_diffrn_orient_matrix_UB_13      0.0242670000
_diffrn_orient_matrix_UB_21      -0.0737775000
_diffrn_orient_matrix_UB_22      0.0912815000
_diffrn_orient_matrix_UB_23      0.0072874000
_diffrn_orient_matrix_UB_31      0.0239732000
_diffrn_orient_matrix_UB_32      -0.0182447000
_diffrn_orient_matrix_UB_33      0.1553309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6586
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.436
_diffrn_reflns_theta_min         4.897
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0414
_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)+(0.0547P)²+0.4400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2887
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0297_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105949
_chemical_oxdiff_formula         'C H N O Cl'
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C7(H7), C9(H9), C10(H10), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20)
;
_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 1.288
_oxdiff_exptl_absorpt_empirical_full_min 0.620
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.84562(6) 0.28316(8) 0.07460(8) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.99204(8) 0.16827(10) 0.38576(11) 0.0292(3) Uani 1 1 d . . . . .
N2 N 0.83471(7) 0.29280(9) 0.29246(10) 0.0226(2) Uani 1 1 d . . . . .
H2 H 0.8614 0.2780 0.3774 0.027 Uiso 1 1 calc R . . . .
N3 N 0.74812(7) 0.35073(9) 0.25153(10) 0.0228(2) Uani 1 1 d . . . . .
C1 C 1.06772(10) 0.10087(13) 0.43467(14) 0.0344(3) Uani 1 1 d . . . . .
H1 H 1.0874 0.0865 0.5280 0.041 Uiso 1 1 calc R . . . .
C2 C 1.11881(10) 0.05097(12) 0.35510(15) 0.0337(3) Uani 1 1 d . . . . .
H2A H 1.1711 0.0041 0.3938 0.040 Uiso 1 1 calc R . . . .
C3 C 1.09007(11) 0.07274(13) 0.21693(15) 0.0389(4) Uani 1 1 d . . . . .
H3 H 1.1225 0.0402 0.1602 0.047 Uiso 1 1 calc R . . . .
C4 C 1.01222(10) 0.14368(13) 0.16336(14) 0.0341(3) Uani 1 1 d . . . . .
H4 H 0.9923 0.1609 0.0707 0.041 Uiso 1 1 calc R . . . .
C5 C 0.96500(8) 0.18814(10) 0.25122(12) 0.0230(3) Uani 1 1 d . . . . .
C6 C 0.87669(8) 0.25982(10) 0.19658(12) 0.0216(3) Uani 1 1 d . . . . .
C7 C 0.70558(9) 0.36353(10) 0.34455(12) 0.0229(3) Uani 1 1 d . . . . .
H7 H 0.7343 0.3375 0.4328 0.028 Uiso 1 1 calc R . . . .
C8 C 0.61136(8) 0.41954(10) 0.31002(11) 0.0212(3) Uani 1 1 d . . . . .
C9 C 0.58717(10) 0.49575(11) 0.20178(12) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.6337 0.5164 0.1599 0.031 Uiso 1 1 calc R . . . .
C10 C 0.49550(10) 0.54092(10) 0.15602(12) 0.0275(3) Uani 1 1 d . . . . .
H10 H 0.4817 0.5928 0.0851 0.033 Uiso 1 1 calc R . . . .
C11 C 0.42331(9) 0.51012(10) 0.21417(12) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.32611(10) 0.55182(11) 0.16378(14) 0.0320(3) Uani 1 1 d . . . . .
H12 H 0.3107 0.6017 0.0908 0.038 Uiso 1 1 calc R . . . .
C13 C 0.25685(10) 0.52004(12) 0.22011(15) 0.0362(3) Uani 1 1 d . . . . .
H13 H 0.1946 0.5488 0.1854 0.043 Uiso 1 1 calc R . . . .
C14 C 0.27669(9) 0.44313(12) 0.33208(15) 0.0326(3) Uani 1 1 d . . . . .
C15 C 0.20523(11) 0.40585(14) 0.39038(19) 0.0450(4) Uani 1 1 d . . . . .
H15 H 0.1422 0.4324 0.3564 0.054 Uiso 1 1 calc R . . . .
C16 C 0.22718(12) 0.33066(14) 0.4969(2) 0.0485(4) Uani 1 1 d . . . . .
H16 H 0.1786 0.3063 0.5330 0.058 Uiso 1 1 calc R . . . .
C17 C 0.32056(12) 0.29072(13) 0.55126(17) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.3342 0.2406 0.6240 0.048 Uiso 1 1 calc R . . . .
C18 C 0.39448(10) 0.32521(11) 0.49746(13) 0.0279(3) Uani 1 1 d . . . . .
C19 C 0.49203(10) 0.28662(10) 0.55046(13) 0.0277(3) Uani 1 1 d . . . . .
H19 H 0.5078 0.2395 0.6261 0.033 Uiso 1 1 calc R . . . .
C20 C 0.56213(9) 0.31664(10) 0.49373(12) 0.0232(3) Uani 1 1 d . . . . .
H20 H 0.6245 0.2888 0.5303 0.028 Uiso 1 1 calc R . . . .
C21 C 0.54220(8) 0.39069(10) 0.37808(11) 0.0197(2) Uani 1 1 d . . . . .
C22 C 0.44645(8) 0.43457(10) 0.32701(12) 0.0212(3) Uani 1 1 d . . . . .
C23 C 0.37259(9) 0.40128(10) 0.38578(13) 0.0248(3) Uani 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 0.0181 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
C1 N1 C5 117.06(11) . .
N3 N2 H2 120.6 . .
C6 N2 H2 120.6 . .
C6 N2 N3 118.85(10) . .
C7 N3 N2 114.89(10) . .
N1 C1 H1 118.0 . .
N1 C1 C2 123.99(12) . .
C2 C1 H1 118.0 . .
C1 C2 H2A 121.0 . .
C3 C2 C1 118.07(12) . .
C3 C2 H2A 121.0 . .
C2 C3 H3 120.4 . .
C2 C3 C4 119.21(13) . .
C4 C3 H3 120.4 . .
C3 C4 H4 120.9 . .
C5 C4 C3 118.29(12) . .
C5 C4 H4 120.9 . .
N1 C5 C4 123.36(12) . .
N1 C5 C6 116.44(11) . .
C4 C5 C6 120.18(11) . .
O1 C6 N2 124.22(11) . .
O1 C6 C5 121.74(10) . .
N2 C6 C5 114.01(10) . .
N3 C7 H7 120.4 . .
N3 C7 C8 119.17(11) . .
C8 C7 H7 120.4 . .
C9 C8 C7 119.26(11) . .
C9 C8 C21 119.96(11) . .
C21 C8 C7 120.60(11) . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.15(12) . .
C10 C9 H9 119.4 . .
C9 C10 H10 119.5 . .
C9 C10 C11 121.06(11) . .
C11 C10 H10 119.5 . .
C10 C11 C12 122.02(12) . .
C10 C11 C22 119.05(11) . .
C22 C11 C12 118.93(12) . .
C11 C12 H12 119.4 . .
C13 C12 C11 121.25(13) . .
C13 C12 H12 119.4 . .
C12 C13 H13 119.2 . .
C12 C13 C14 121.58(12) . .
C14 C13 H13 119.2 . .
C15 C14 C13 122.87(13) . .
C15 C14 C23 118.47(14) . .
C23 C14 C13 118.66(13) . .
C14 C15 H15 119.5 . .
C16 C15 C14 120.98(14) . .
C16 C15 H15 119.5 . .
C15 C16 H16 119.5 . .
C15 C16 C17 121.00(14) . .
C17 C16 H16 119.5 . .
C16 C17 H17 119.8 . .
C16 C17 C18 120.41(15) . .
C18 C17 H17 119.8 . .
C17 C18 C19 122.44(13) . .
C17 C18 C23 119.25(13) . .
C23 C18 C19 118.31(11) . .
C18 C19 H19 119.0 . .
C20 C19 C18 121.93(12) . .
C20 C19 H19 119.0 . .
C19 C20 H20 119.3 . .
C19 C20 C21 121.39(11) . .
C21 C20 H20 119.3 . .
C8 C21 C20 123.63(11) . .
C8 C21 C22 118.50(11) . .
C22 C21 C20 117.84(11) . .
C11 C22 C21 120.12(11) . .
C23 C22 C11 119.39(11) . .
C23 C22 C21 120.48(11) . .
C14 C23 C22 120.18(12) . .
C18 C23 C14 119.86(12) . .
C18 C23 C22 119.96(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.2291(15) .
N1 C1 1.3315(18) .
N1 C5 1.3382(16) .
N2 H2 0.8600 .
N2 N3 1.3823(14) .
N2 C6 1.3536(15) .
N3 C7 1.2837(15) .
C1 H1 0.9300 .
C1 C2 1.383(2) .
C2 H2A 0.9300 .
C2 C3 1.377(2) .
C3 H3 0.9300 .
C3 C4 1.386(2) .
C4 H4 0.9300 .
C4 C5 1.3830(18) .
C5 C6 1.5014(17) .
C7 H7 0.9300 .
C7 C8 1.4634(17) .
C8 C9 1.3967(17) .
C8 C21 1.4166(16) .
C9 H9 0.9300 .
C9 C10 1.3784(18) .
C10 H10 0.9300 .
C10 C11 1.3920(19) .
C11 C12 1.4355(18) .
C11 C22 1.4259(17) .
C12 H12 0.9300 .
C12 C13 1.346(2) .
C13 H13 0.9300 .
C13 C14 1.431(2) .
C14 C15 1.406(2) .
C14 C23 1.4229(18) .
C15 H15 0.9300 .
C15 C16 1.376(3) .
C16 H16 0.9300 .
C16 C17 1.384(2) .
C17 H17 0.9300 .
C17 C18 1.3979(19) .
C18 C19 1.4298(19) .
C18 C23 1.4213(19) .
C19 H19 0.9300 .
C19 C20 1.3537(18) .
C20 H20 0.9300 .
C20 C21 1.4374(16) .
C21 C22 1.4272(16) .
C22 C23 1.4251(17) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 0.4(2) . . . .
N1 C5 C6 O1 -179.96(11) . . . .
N1 C5 C6 N2 -1.47(16) . . . .
N2 N3 C7 C8 -177.41(10) . . . .
N3 N2 C6 O1 4.13(18) . . . .
N3 N2 C6 C5 -174.32(10) . . . .
N3 C7 C8 C9 -25.80(17) . . . .
N3 C7 C8 C21 149.25(12) . . . .
C1 N1 C5 C4 -0.9(2) . . . .
C1 N1 C5 C6 177.17(12) . . . .
C1 C2 C3 C4 0.4(2) . . . .
C2 C3 C4 C5 -1.3(2) . . . .
C3 C4 C5 N1 1.6(2) . . . .
C3 C4 C5 C6 -176.33(13) . . . .
C4 C5 C6 O1 -1.86(19) . . . .
C4 C5 C6 N2 176.63(12) . . . .
C5 N1 C1 C2 -0.2(2) . . . .
C6 N2 N3 C7 169.57(11) . . . .
C7 C8 C9 C10 172.71(11) . . . .
C7 C8 C21 C20 7.57(17) . . . .
C7 C8 C21 C22 -170.45(10) . . . .
C8 C9 C10 C11 -1.47(19) . . . .
C8 C21 C22 C11 -3.08(16) . . . .
C8 C21 C22 C23 175.32(10) . . . .
C9 C8 C21 C20 -177.40(11) . . . .
C9 C8 C21 C22 4.57(17) . . . .
C9 C10 C11 C12 -176.86(11) . . . .
C9 C10 C11 C22 2.94(18) . . . .
C10 C11 C12 C13 179.13(12) . . . .
C10 C11 C22 C21 -0.62(17) . . . .
C10 C11 C22 C23 -179.04(11) . . . .
C11 C12 C13 C14 -0.3(2) . . . .
C11 C22 C23 C14 0.04(17) . . . .
C11 C22 C23 C18 179.41(11) . . . .
C12 C11 C22 C21 179.19(10) . . . .
C12 C11 C22 C23 0.78(17) . . . .
C12 C13 C14 C15 -178.07(13) . . . .
C12 C13 C14 C23 1.08(19) . . . .
C13 C14 C15 C16 179.16(14) . . . .
C13 C14 C23 C18 179.68(11) . . . .
C13 C14 C23 C22 -0.95(18) . . . .
C14 C15 C16 C17 1.0(2) . . . .
C15 C14 C23 C18 -1.14(19) . . . .
C15 C14 C23 C22 178.23(12) . . . .
C15 C16 C17 C18 -0.8(2) . . . .
C16 C17 C18 C19 179.75(13) . . . .
C16 C17 C18 C23 -0.4(2) . . . .
C17 C18 C19 C20 177.00(12) . . . .
C17 C18 C23 C14 1.31(18) . . . .
C17 C18 C23 C22 -178.06(12) . . . .
C18 C19 C20 C21 1.03(19) . . . .
C19 C18 C23 C14 -178.79(11) . . . .
C19 C18 C23 C22 1.84(17) . . . .
C19 C20 C21 C8 -176.20(11) . . . .
C19 C20 C21 C22 1.84(17) . . . .
C20 C21 C22 C11 178.78(10) . . . .
C20 C21 C22 C23 -2.82(16) . . . .
C21 C8 C9 C10 -2.38(18) . . . .
C21 C22 C23 C14 -178.38(10) . . . .
C21 C22 C23 C18 1.00(17) . . . .
C22 C11 C12 C13 -0.67(19) . . . .
C23 C14 C15 C16 0.0(2) . . . .
C23 C18 C19 C20 -2.89(19) . . . .
