#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/90/2209014.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209014
loop_
_publ_author_name
'Nie, Aihua'
'Ghosh, Sutapa'
'Huang, Ziwei'
_publ_section_title
;
 2'-[2-(4-Fluorophenyl)chroman-4-ylidene]isonicotinohydrazide
;
_journal_coeditor_code           TK2018
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1824
_journal_page_last               o1825
_journal_paper_doi               10.1107/S1600536806012153
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C21 H16 F N3 O2'
_chemical_formula_moiety         'C21 H16 F N3 O2'
_chemical_formula_sum            'C21 H16 F N3 O2'
_chemical_formula_weight         361.37
_chemical_melting_point          210
_chemical_name_systematic
;
2'-[2-(4-Fluorophenyl)chroman-4-ylidene]isonicotinohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.416(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.654(5)
_cell_length_b                   5.471(2)
_cell_length_c                   26.609(10)
_cell_measurement_reflns_used    4435
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      2.6
_cell_volume                     1656.9(11)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'ORTEP-32 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      208(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_av_sigmaI/netI    0.056
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9130
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.070
_refine_ls_R_factor_gt           0.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.1714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.119
_refine_ls_wR_factor_ref         0.128
_reflns_number_gt                2219
_reflns_number_total             2933
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2018.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209014
_cod_database_fobs_code          2209014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.77866(19) 0.1949(4) 0.63397(8) 0.0389(6) Uani d . 1
H H1 0.8255 0.0785 0.6549 0.047 Uiso calc R 1
C C2 0.7290(2) 0.3815(5) 0.65632(8) 0.0434(6) Uani d . 1
H H2A 0.7429 0.3934 0.6924 0.052 Uiso calc R 1
C C3 0.6588(2) 0.5522(4) 0.62611(9) 0.0402(6) Uani d . 1
H H3 0.6259 0.6814 0.6416 0.048 Uiso calc R 1
C C4 0.6369(2) 0.5333(4) 0.57371(8) 0.0380(5) Uani d . 1
H H4 0.5878 0.6476 0.5532 0.046 Uiso calc R 1
C C5 0.68711(18) 0.3464(4) 0.55093(8) 0.0309(5) Uani d . 1
C C6 0.76051(17) 0.1752(4) 0.58037(8) 0.0292(5) Uani d . 1
C C7 0.81877(17) -0.0115(4) 0.55473(7) 0.0277(5) Uani d . 1
C C8 0.78476(19) -0.0158(4) 0.49727(8) 0.0354(5) Uani d . 1
H H8A 0.7812 -0.1856 0.4853 0.042 Uiso calc R 1
H H8B 0.8450 0.0687 0.4832 0.042 Uiso calc R 1
C C9 0.6682(2) 0.1041(4) 0.47746(8) 0.0395(6) Uani d . 1
H H9 0.6079 0.0028 0.4887 0.047 Uiso calc R 1
C C10 0.63637(18) 0.1154(4) 0.41965(8) 0.0330(5) Uani d . 1
C C11 0.5699(2) -0.0704(4) 0.39371(8) 0.0400(6) Uani d . 1
H H11 0.5415 -0.1937 0.4124 0.048 Uiso calc R 1
C C12 0.5440(2) -0.0796(4) 0.34067(8) 0.0416(6) Uani d . 1
H H12 0.4993 -0.2086 0.3231 0.050 Uiso calc R 1
C C13 0.5847(2) 0.1025(4) 0.31437(8) 0.0376(5) Uani d . 1
C C14 0.6491(2) 0.2930(4) 0.33846(9) 0.0432(6) Uani d . 1
H H14 0.6750 0.4183 0.3194 0.052 Uiso calc R 1
C C15 0.6755(2) 0.2975(4) 0.39174(9) 0.0412(6) Uani d . 1
H H15 0.7207 0.4265 0.4091 0.049 Uiso calc R 1
C C16 1.01894(18) -0.5016(4) 0.58088(8) 0.0302(5) Uani d . 1
C C17 1.05581(18) -0.5295(4) 0.63831(7) 0.0301(5) Uani d . 1
C C18 1.0366(2) -0.3662(4) 0.67530(8) 0.0374(5) Uani d . 1
H H18 0.9911 -0.2249 0.6659 0.045 Uiso calc R 1
C C19 1.0854(2) -0.4148(4) 0.72638(8) 0.0409(6) Uani d . 1
H H19 1.0725 -0.3005 0.7510 0.049 Uiso calc R 1
C C20 1.1649(2) -0.7678(4) 0.70708(8) 0.0416(6) Uani d . 1
H H20 1.2089 -0.9098 0.7177 0.050 Uiso calc R 1
C C21 1.1210(2) -0.7356(4) 0.65516(8) 0.0369(5) Uani d . 1
H H21 1.1353 -0.8530 0.6314 0.044 Uiso calc R 1
N N1 0.89357(15) -0.1535(3) 0.58301(6) 0.0293(4) Uani d . 1
N N2 0.94797(15) -0.3216(3) 0.55757(6) 0.0308(4) Uani d . 1
H H2 0.9358 -0.3112 0.5242 0.037 Uiso calc R 1
N N3 1.14906(16) -0.6104(4) 0.74327(7) 0.0404(5) Uani d . 1
O O1 0.66208(14) 0.3399(3) 0.49802(5) 0.0404(4) Uani d . 1
O O2 1.05759(14) -0.6471(3) 0.55330(5) 0.0418(4) Uani d . 1
F F1 0.56160(14) 0.0931(3) 0.26227(5) 0.0606(5) Uani d . 1
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'
F F 0.0171 0.0103 ' 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
C2 C1 C6 120.9(2)
C2 C1 H1 119.5
C6 C1 H1 119.5
C1 C2 C3 120.3(2)
C1 C2 H2A 119.9
C3 C2 H2A 119.9
C4 C3 C2 120.0(2)
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.0(2)
C3 C4 H4 120.0
C5 C4 H4 120.0
O1 C5 C4 116.85(19)
O1 C5 C6 121.91(17)
C4 C5 C6 121.23(19)
C5 C6 C1 117.50(18)
C5 C6 C7 119.67(18)
C1 C6 C7 122.80(19)
N1 C7 C6 118.07(17)
N1 C7 C8 125.99(18)
C6 C7 C8 115.94(17)
C7 C8 C9 111.95(17)
C7 C8 H8A 109.2
C9 C8 H8A 109.2
C7 C8 H8B 109.2
C9 C8 H8B 109.2
H8A C8 H8B 107.9
O1 C9 C8 112.45(19)
O1 C9 C10 109.73(18)
C8 C9 C10 112.54(17)
O1 C9 H9 107.3
C8 C9 H9 107.3
C10 C9 H9 107.3
C11 C10 C15 118.8(2)
C11 C10 C9 118.2(2)
C15 C10 C9 122.9(2)
C10 C11 C12 121.2(2)
C10 C11 H11 119.4
C12 C11 H11 119.4
C13 C12 C11 118.4(2)
C13 C12 H12 120.8
C11 C12 H12 120.8
F1 C13 C12 119.0(2)
F1 C13 C14 118.6(2)
C12 C13 C14 122.4(2)
C13 C14 C15 118.3(2)
C13 C14 H14 120.8
C15 C14 H14 120.8
C10 C15 C14 120.8(2)
C10 C15 H15 119.6
C14 C15 H15 119.6
O2 C16 N2 117.69(18)
O2 C16 C17 118.60(19)
N2 C16 C17 123.69(18)
C21 C17 C18 117.3(2)
C21 C17 C16 115.50(18)
C18 C17 C16 127.1(2)
C19 C18 C17 118.7(2)
C19 C18 H18 120.6
C17 C18 H18 120.6
N3 C19 C18 124.8(2)
N3 C19 H19 117.6
C18 C19 H19 117.6
N3 C20 C21 124.2(2)
N3 C20 H20 117.9
C21 C20 H20 117.9
C20 C21 C17 119.4(2)
C20 C21 H21 120.3
C17 C21 H21 120.3
C7 N1 N2 116.29(16)
C16 N2 N1 124.35(17)
C16 N2 H2 117.8
N1 N2 H2 117.8
C19 N3 C20 115.53(19)
C5 O1 C9 113.81(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(3)
C1 C6 1.400(3)
C1 H1 0.9400
C2 C3 1.380(3)
C2 H2A 0.9400
C3 C4 1.366(3)
C3 H3 0.9400
C4 C5 1.381(3)
C4 H4 0.9400
C5 O1 1.375(2)
C5 C6 1.391(3)
C6 C7 1.473(3)
C7 N1 1.283(3)
C7 C8 1.495(3)
C8 C9 1.499(3)
C8 H8A 0.9800
C8 H8B 0.9800
C9 O1 1.409(3)
C9 C10 1.504(3)
C9 H9 0.9900
C10 C11 1.371(3)
C10 C15 1.377(3)
C11 C12 1.379(3)
C11 H11 0.9400
C12 C13 1.360(3)
C12 H12 0.9400
C13 F1 1.355(2)
C13 C14 1.361(3)
C14 C15 1.385(3)
C14 H14 0.9400
C15 H15 0.9400
C16 O2 1.232(2)
C16 N2 1.348(3)
C16 C17 1.504(3)
C17 C21 1.380(3)
C17 C18 1.383(3)
C18 C19 1.382(3)
C18 H18 0.9400
C19 N3 1.324(3)
C19 H19 0.9400
C20 N3 1.334(3)
C20 C21 1.377(3)
C20 H20 0.9400
C21 H21 0.9400
N1 N2 1.375(2)
N2 H2 0.8700
