#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/73/7117321.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_7117321
loop_
_publ_author_name
'Lingliang Long'
'Yanjun Wu'
'Lin Wang'
'Aihua Gong'
'Feilong Hu'
'Chi Zhang'
_publ_section_title
;
 A fluorescent probe for hypochlorite based on the modulation of the
 unique rotation of the N-N single bond in acetohydrazide
;
_journal_name_full               Chem.Commun.
_journal_page_first              10435
_journal_paper_doi               10.1039/C5cc03972J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C14 H17 N3 O3'
_chemical_formula_sum            'C14 H17 N3 O3'
_chemical_formula_weight         275.31
_chemical_melting_point          436(3)
_chemical_name_common            1a
_chemical_name_systematic
7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-27 deposited with the CCDC.
2015-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                94.78(3)
_cell_angle_beta                 109.99(3)
_cell_angle_gamma                105.42(3)
_cell_formula_units_Z            4
_cell_length_a                   9.2120(18)
_cell_length_b                   12.624(3)
_cell_length_c                   12.927(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1336.5(7)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11095
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane, petroleum ether'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                3980
_reflns_number_total             4609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03972j2.cif
_cod_data_source_block           s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '433-438' was changed to '436(3)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_cell_volume        1336.5(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7117321
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.37094(13) 0.21008(9) 1.22555(9) 0.0275(3) Uani 1 1 d . . .
N2 N 0.30689(13) -0.11563(9) 0.58434(9) 0.0284(3) Uani 1 1 d . . .
H2 H 0.2697 -0.1665 0.6173 0.034 Uiso 1 1 calc R . .
N3 N 0.30169(16) -0.14910(10) 0.47591(10) 0.0329(3) Uani 1 1 d . . .
H3A H 0.402(2) -0.1143(13) 0.4745(12) 0.039 Uiso 1 1 d . . .
H3B H 0.2251(19) -0.1225(12) 0.4269(13) 0.039 Uiso 1 1 d . . .
N4 N 0.89924(13) 0.48848(9) 0.76298(9) 0.0270(3) Uani 1 1 d . . .
N5 N 0.80165(14) 0.74503(10) 1.37557(9) 0.0318(3) Uani 1 1 d . . .
H5 H 0.7327 0.6789 1.3491 0.038 Uiso 1 1 calc R . .
N6 N 0.82009(17) 0.80199(11) 1.48069(10) 0.0363(3) Uani 1 1 d . . .
H6A H 0.926(2) 0.8406(14) 1.5127(13) 0.044 Uiso 1 1 d . . .
H6B H 0.764(2) 0.8522(14) 1.4672(13) 0.044 Uiso 1 1 d . . .
O1 O 0.28301(10) -0.04724(7) 0.90355(7) 0.0240(2) Uani 1 1 d . . .
O2 O 0.23042(11) -0.17647(7) 0.75952(8) 0.0302(2) Uani 1 1 d . . .
O3 O 0.42149(12) 0.06902(7) 0.59713(8) 0.0327(2) Uani 1 1 d . . .
O4 O 0.73383(10) 0.54885(7) 1.06811(7) 0.0268(2) Uani 1 1 d . . .
O5 O 0.64654(11) 0.56195(8) 1.20531(8) 0.0332(2) Uani 1 1 d . . .
O6 O 0.98580(12) 0.88513(8) 1.34805(8) 0.0363(3) Uani 1 1 d . . .
C1 C 0.29031(16) 0.12102(11) 1.27217(11) 0.0288(3) Uani 1 1 d . . .
H1A H 0.3312 0.1439 1.3531 0.035 Uiso 1 1 calc R . .
H1B H 0.3171 0.0539 1.2558 0.035 Uiso 1 1 calc R . .
C2 C 0.10701(17) 0.09453(12) 1.22498(13) 0.0356(3) Uani 1 1 d . . .
H2A H 0.0799 0.1610 1.2399 0.053 Uiso 1 1 calc R . .
H2B H 0.0598 0.0380 1.2597 0.053 Uiso 1 1 calc R . .
H2C H 0.0652 0.0677 1.1455 0.053 Uiso 1 1 calc R . .
C3 C 0.41947(16) 0.32444(11) 1.28706(11) 0.0304(3) Uani 1 1 d . . .
H3C H 0.3544 0.3267 1.3319 0.036 Uiso 1 1 calc R . .
H3D H 0.3976 0.3736 1.2339 0.036 Uiso 1 1 calc R . .
C5 C 0.38721(14) 0.18923(11) 1.12620(10) 0.0240(3) Uani 1 1 d . . .
C6 C 0.46878(15) 0.27726(11) 1.08375(11) 0.0261(3) Uani 1 1 d . . .
H6 H 0.5104 0.3502 1.1245 0.031 Uiso 1 1 calc R . .
C7 C 0.48636(15) 0.25586(11) 0.98443(11) 0.0261(3) Uani 1 1 d . . .
H7 H 0.5406 0.3148 0.9591 0.031 Uiso 1 1 calc R . .
C8 C 0.42479(14) 0.14692(10) 0.91857(10) 0.0228(3) Uani 1 1 d . . .
C9 C 0.34594(14) 0.06170(10) 0.96191(10) 0.0220(3) Uani 1 1 d . . .
C10 C 0.32577(15) 0.07987(10) 1.06140(10) 0.0237(3) Uani 1 1 d . . .
H10 H 0.2718 0.0204 1.0862 0.028 Uiso 1 1 calc R . .
C11 C 0.43012(15) 0.11847(10) 0.81278(10) 0.0236(3) Uani 1 1 d . . .
H11 H 0.4809 0.1745 0.7827 0.028 Uiso 1 1 calc R . .
C12 C 0.36371(14) 0.01185(10) 0.75288(10) 0.0227(3) Uani 1 1 d . . .
C13 C 0.28939(14) -0.07697(10) 0.80039(10) 0.0228(3) Uani 1 1 d . . .
C14 C 0.36618(15) -0.00953(11) 0.63860(11) 0.0242(3) Uani 1 1 d . . .
C15 C 0.77031(16) 0.38048(11) 0.71588(12) 0.0311(3) Uani 1 1 d . . .
H15A H 0.7669 0.3405 0.7764 0.037 Uiso 1 1 calc R . .
H15B H 0.7982 0.3366 0.6647 0.037 Uiso 1 1 calc R . .
C16 C 0.60172(17) 0.38807(12) 0.65377(12) 0.0353(3) Uani 1 1 d . . .
H16A H 0.5670 0.4233 0.7056 0.053 Uiso 1 1 calc R . .
H16B H 0.5268 0.3142 0.6198 0.053 Uiso 1 1 calc R . .
H16C H 0.6048 0.4315 0.5966 0.053 Uiso 1 1 calc R . .
C17 C 0.94072(18) 0.59463(12) 0.61468(11) 0.0359(3) Uani 1 1 d . . .
H17A H 0.8339 0.5520 0.5619 0.054 Uiso 1 1 calc R . .
H17B H 1.0130 0.6143 0.5757 0.054 Uiso 1 1 calc R . .
H17C H 0.9360 0.6615 0.6527 0.054 Uiso 1 1 calc R . .
C18 C 1.00263(17) 0.52522(11) 0.69962(11) 0.0297(3) Uani 1 1 d . . .
H18A H 1.0117 0.4597 0.6607 0.036 Uiso 1 1 calc R . .
H18B H 1.1109 0.5689 0.7521 0.036 Uiso 1 1 calc R . .
C19 C 0.91279(15) 0.55621(10) 0.85589(10) 0.0240(3) Uani 1 1 d . . .
C20 C 1.03027(15) 0.66525(11) 0.89623(11) 0.0268(3) Uani 1 1 d . . .
H20 H 1.0969 0.6914 0.8576 0.032 Uiso 1 1 calc R . .
C21 C 1.04569(16) 0.73123(11) 0.99049(11) 0.0284(3) Uani 1 1 d . . .
H21 H 1.1233 0.8018 1.0148 0.034 Uiso 1 1 calc R . .
C22 C 0.94828(15) 0.69654(10) 1.05264(10) 0.0252(3) Uani 1 1 d . . .
C23 C 0.83348(15) 0.58968(10) 1.01162(10) 0.0233(3) Uani 1 1 d . . .
C24 C 0.81296(15) 0.52076(11) 0.91663(10) 0.0250(3) Uani 1 1 d . . .
H24 H 0.7336 0.4509 0.8922 0.030 Uiso 1 1 calc R . .
C25 C 0.95869(16) 0.75889(11) 1.15171(11) 0.0267(3) Uani 1 1 d . . .
H25 H 1.0336 0.8304 1.1790 0.032 Uiso 1 1 calc R . .
C26 C 0.86312(15) 0.71852(10) 1.20929(10) 0.0253(3) Uani 1 1 d . . .
C27 C 0.74238(15) 0.60859(11) 1.16528(11) 0.0256(3) Uani 1 1 d . . .
C28 C 0.88711(16) 0.78989(11) 1.31583(11) 0.0267(3) Uani 1 1 d . . .
C4 C 0.59829(17) 0.36708(12) 1.36317(11) 0.0350(3) Uani 1 1 d . . .
H4A H 0.6184 0.3233 1.4207 0.053 Uiso 1 1 calc R . .
H4B H 0.6265 0.4441 1.3971 0.053 Uiso 1 1 calc R . .
H4C H 0.6631 0.3609 1.3199 0.053 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 0.0033 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
C5 N1 C3 121.40(11) . .
C5 N1 C1 122.22(11) . .
C3 N1 C1 116.14(11) . .
C14 N2 N3 123.67(11) . .
C14 N2 H2 118.2 . .
N3 N2 H2 118.2 . .
N2 N3 H3A 107.9(9) . .
N2 N3 H3B 106.6(9) . .
H3A N3 H3B 108.6(13) . .
C19 N4 C15 121.26(11) . .
C19 N4 C18 121.46(11) . .
C15 N4 C18 117.01(11) . .
C28 N5 N6 122.69(12) . .
C28 N5 H5 118.7 . .
N6 N5 H5 118.7 . .
N5 N6 H6A 104.4(10) . .
N5 N6 H6B 107.6(10) . .
H6A N6 H6B 107.9(15) . .
C9 O1 C13 122.64(10) . .
C27 O4 C23 122.90(10) . .
N1 C1 C2 112.30(11) . .
N1 C1 H1A 109.1 . .
C2 C1 H1A 109.1 . .
N1 C1 H1B 109.1 . .
C2 C1 H1B 109.1 . .
H1A C1 H1B 107.9 . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N1 C3 C4 112.45(12) . .
N1 C3 H3C 109.1 . .
C4 C3 H3C 109.1 . .
N1 C3 H3D 109.1 . .
C4 C3 H3D 109.1 . .
H3C C3 H3D 107.8 . .
N1 C5 C10 121.42(12) . .
N1 C5 C6 121.03(12) . .
C10 C5 C6 117.55(12) . .
C7 C6 C5 120.89(12) . .
C7 C6 H6 119.6 . .
C5 C6 H6 119.6 . .
C6 C7 C8 122.11(12) . .
C6 C7 H7 118.9 . .
C8 C7 H7 118.9 . .
C9 C8 C11 118.05(12) . .
C9 C8 C7 116.12(12) . .
C11 C8 C7 125.77(12) . .
C10 C9 O1 116.46(11) . .
C10 C9 C8 123.50(12) . .
O1 C9 C8 120.04(11) . .
C9 C10 C5 119.83(12) . .
C9 C10 H10 120.1 . .
C5 C10 H10 120.1 . .
C12 C11 C8 122.32(12) . .
C12 C11 H11 118.8 . .
C8 C11 H11 118.8 . .
C11 C12 C13 119.46(12) . .
C11 C12 C14 118.67(12) . .
C13 C12 C14 121.85(11) . .
O2 C13 O1 115.24(11) . .
O2 C13 C12 127.39(12) . .
O1 C13 C12 117.38(11) . .
O3 C14 N2 122.37(12) . .
O3 C14 C12 120.55(12) . .
N2 C14 C12 117.07(11) . .
N4 C15 C16 114.84(12) . .
N4 C15 H15A 108.6 . .
C16 C15 H15A 108.6 . .
N4 C15 H15B 108.6 . .
C16 C15 H15B 108.6 . .
H15A C15 H15B 107.5 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 H17A 109.5 . .
C18 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C18 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N4 C18 C17 114.17(11) . .
N4 C18 H18A 108.7 . .
C17 C18 H18A 108.7 . .
N4 C18 H18B 108.7 . .
C17 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
N4 C19 C24 121.36(12) . .
N4 C19 C20 121.07(12) . .
C24 C19 C20 117.56(12) . .
C21 C20 C19 120.71(12) . .
C21 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
C20 C21 C22 122.37(12) . .
C20 C21 H21 118.8 . .
C22 C21 H21 118.8 . .
C23 C22 C25 118.13(12) . .
C23 C22 C21 116.10(12) . .
C25 C22 C21 125.76(12) . .
C24 C23 O4 116.70(11) . .
C24 C23 C22 123.49(12) . .
O4 C23 C22 119.81(11) . .
C23 C24 C19 119.76(12) . .
C23 C24 H24 120.1 . .
C19 C24 H24 120.1 . .
C26 C25 C22 122.53(12) . .
C26 C25 H25 118.7 . .
C22 C25 H25 118.7 . .
C25 C26 C27 119.07(12) . .
C25 C26 C28 118.48(12) . .
C27 C26 C28 122.44(12) . .
O5 C27 O4 115.46(11) . .
O5 C27 C26 127.00(12) . .
O4 C27 C26 117.54(11) . .
O6 C28 N5 121.91(12) . .
O6 C28 C26 120.65(12) . .
N5 C28 C26 117.41(12) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.3556(17) .
N1 C3 1.4624(18) .
N1 C1 1.4677(17) .
N2 C14 1.3330(18) .
N2 N3 1.4107(15) .
N2 H2 0.8600 .
N3 H3A 0.919(16) .
N3 H3B 0.932(16) .
N4 C19 1.3634(17) .
N4 C15 1.4650(19) .
N4 C18 1.4680(17) .
N5 C28 1.3372(17) .
N5 N6 1.4166(17) .
N5 H5 0.8600 .
N6 H6A 0.891(17) .
N6 H6B 0.914(17) .
O1 C9 1.3787(16) .
O1 C13 1.3800(15) .
O2 C13 1.2175(16) .
O3 C14 1.2397(15) .
O4 C27 1.3768(16) .
O4 C23 1.3823(15) .
O5 C27 1.2168(15) .
O6 C28 1.2336(17) .
C1 C2 1.5155(19) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
C3 C4 1.518(2) .
C3 H3C 0.9700 .
C3 H3D 0.9700 .
C5 C10 1.4126(19) .
C5 C6 1.4284(19) .
C6 C7 1.3620(19) .
C6 H6 0.9300 .
C7 C8 1.4135(19) .
C7 H7 0.9300 .
C8 C9 1.4007(18) .
C8 C11 1.4053(18) .
C9 C10 1.3704(18) .
C10 H10 0.9300 .
C11 C12 1.3601(19) .
C11 H11 0.9300 .
C12 C13 1.4481(18) .
C12 C14 1.4886(18) .
C15 C16 1.518(2) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 C18 1.5155(19) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C24 1.4128(18) .
C19 C20 1.428(2) .
C20 C21 1.3596(19) .
C20 H20 0.9300 .
C21 C22 1.4090(18) .
C21 H21 0.9300 .
C22 C23 1.399(2) .
C22 C25 1.4060(19) .
C23 C24 1.3698(19) .
C24 H24 0.9300 .
C25 C26 1.3643(19) .
C25 H25 0.9300 .
C26 C27 1.450(2) .
C26 C28 1.4956(19) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
