#------------------------------------------------------------------------------
#$Date: 2018-11-16 05:33:15 +0200 (Fri, 16 Nov 2018) $
#$Revision: 212002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021345.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_2021345
loop_
_publ_author_name
'Dwivedi, Bhavna'
'Das, Dinabandhu'
_publ_section_title
;
 Polymorphism in some new bis-hydrazone compounds
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618014286
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C30 H22 F4 N4'
_chemical_formula_moiety         'C30 H22 F4 N4'
_chemical_formula_sum            'C30 H22 F4 N4'
_chemical_formula_weight         514.51
_chemical_name_systematic
;
Butane-2,3-dione 2,3-bis{[bis(4-fluorophenyl)methylidene]hydrazone}
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                86.452(2)
_cell_angle_beta                 86.481(3)
_cell_angle_gamma                89.888(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9137(3)
_cell_length_b                   15.0053(9)
_cell_length_c                   17.7776(10)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      23.67
_cell_measurement_theta_min      2.30
_cell_volume                     1305.79(13)
_computing_cell_refinement
;
SAINT (Bruker, 2012)
;
_computing_data_collection
;
APEX3 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2012)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2001)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEXIII CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            59436
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.372
_diffrn_reflns_theta_min         2.300
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.304
_refine_ls_extinction_coef       0.027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0578
_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)+(0.0732P)²+0.3208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1823
_reflns_number_gt                3535
_reflns_number_total             6507
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            uk3160sup1.cif
_cod_data_source_block           1c
_cod_database_code               2021345
_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_min   0.964
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
N N1 -0.0625(4) 0.61118(10) 0.01566(9) 0.0649(5) Uani d 1
N N2 -0.0073(4) 0.67210(10) 0.06844(10) 0.0676(5) Uani d 1
N N3 0.4430(4) 0.89114(10) 0.47815(10) 0.0683(5) Uani d 1
N N4 0.4984(4) 0.83655(10) 0.41865(10) 0.0699(5) Uani d 1
F F1 0.4301(5) 0.81769(13) -0.26121(9) 0.1344(7) Uani d 1
F F2 0.2477(5) 0.99633(11) 0.25609(11) 0.1421(8) Uani d 1
F F3 0.6692(4) 0.52028(10) 0.20659(9) 0.1159(6) Uani d 1
F F4 0.9214(5) 0.64505(14) 0.72055(10) 0.1472(8) Uani d 1
C C1 0.0971(4) 0.74698(12) 0.04243(12) 0.0605(5) Uani d 1
C C2 0.1885(4) 0.76696(12) -0.03791(12) 0.0607(5) Uani d 1
C C3 0.3912(5) 0.71868(16) -0.07252(14) 0.0822(7) Uani d 1
H H3 0.475106 0.673215 -0.044540 0.099 Uiso calc 1
C C4 0.4748(7) 0.73519(19) -0.14731(15) 0.1005(9) Uani d 1
H H4 0.613734 0.701825 -0.169693 0.121 Uiso calc 1
C C5 0.3513(6) 0.80058(18) -0.18720(14) 0.0883(7) Uani d 1
C C6 0.1536(7) 0.85105(19) -0.15623(18) 0.1039(9) Uani d 1
H H6 0.071847 0.896198 -0.185102 0.125 Uiso calc 1
C C7 0.0738(6) 0.83485(16) -0.08091(16) 0.0931(8) Uani d 1
H H7 -0.059951 0.870442 -0.058767 0.112 Uiso calc 1
C C8 0.1320(4) 0.81511(12) 0.09797(13) 0.0653(5) Uani d 1
C C9 -0.0207(6) 0.81139(14) 0.16603(14) 0.0816(7) Uani d 1
H H9 -0.151651 0.766860 0.175980 0.098 Uiso calc 1
C C10 0.0169(7) 0.87219(17) 0.21947(15) 0.0962(9) Uani d 1
H H10 -0.086923 0.868915 0.265096 0.115 Uiso calc 1
C C11 0.2074(7) 0.93668(17) 0.20430(18) 0.0970(9) Uani d 1
C C12 0.3599(7) 0.94420(18) 0.1380(2) 0.1075(10) Uani d 1
H H12 0.488391 0.989618 0.128781 0.129 Uiso calc 1
C C13 0.3214(6) 0.88288(16) 0.08367(16) 0.0899(7) Uani d 1
H H13 0.423384 0.887654 0.037771 0.108 Uiso calc 1
C C14 0.0374(4) 0.53296(12) 0.02682(11) 0.0581(5) Uani d 1
C C15 0.2218(5) 0.50705(15) 0.08758(13) 0.0818(7) Uani d 1
H H15A 0.406089 0.522553 0.070871 0.123 Uiso calc 1
H H15B 0.209215 0.443816 0.099296 0.123 Uiso calc 1
H H15C 0.169312 0.538021 0.131841 0.123 Uiso calc 1
C C16 0.5934(4) 0.75855(12) 0.43574(12) 0.0612(5) Uani d 1
C C17 0.6162(4) 0.69574(12) 0.37450(12) 0.0624(5) Uani d 1
C C18 0.4562(5) 0.70596(14) 0.31362(13) 0.0757(6) Uani d 1
H H18 0.333702 0.753217 0.310964 0.091 Uiso calc 1
C C19 0.4735(6) 0.64756(16) 0.25641(14) 0.0849(7) Uani d 1
H H19 0.364130 0.655069 0.215616 0.102 Uiso calc 1
C C20 0.6527(5) 0.57934(15) 0.26098(14) 0.0792(7) Uani d 1
C C21 0.8165(5) 0.56712(16) 0.31860(17) 0.0905(8) Uani d 1
H H21 0.940439 0.520217 0.319799 0.109 Uiso calc 1
C C22 0.7978(5) 0.62557(15) 0.37631(15) 0.0829(7) Uani d 1
H H22 0.908987 0.617282 0.416631 0.099 Uiso calc 1
C C23 0.6791(4) 0.72864(12) 0.51168(12) 0.0612(5) Uani d 1
C C24 0.8740(5) 0.77472(14) 0.54623(13) 0.0739(6) Uani d 1
H H24 0.950917 0.825906 0.521501 0.089 Uiso calc 1
C C25 0.9572(6) 0.74730(18) 0.61563(16) 0.0945(8) Uani d 1
H H25 1.090659 0.778726 0.637864 0.113 Uiso calc 1
C C26 0.8423(7) 0.6740(2) 0.65125(15) 0.0932(8) Uani d 1
C C27 0.6506(7) 0.6256(2) 0.62042(19) 0.1107(10) Uani d 1
H H27 0.574454 0.575062 0.646462 0.133 Uiso calc 1
C C28 0.5704(6) 0.65263(17) 0.54948(17) 0.0935(8) Uani d 1
H H28 0.441927 0.619301 0.527017 0.112 Uiso calc 1
C C29 0.5407(4) 0.97041(12) 0.46949(11) 0.0613(5) Uani d 1
C C30 0.7279(6) 1.00322(15) 0.40496(14) 0.0932(8) Uani d 1
H H30A 0.901847 0.974574 0.408653 0.140 Uiso calc 1
H H30B 0.750352 1.066654 0.406092 0.140 Uiso calc 1
H H30C 0.652461 0.989640 0.358446 0.140 Uiso calc 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C14 N1 N2 . . 115.98(17)
C1 N2 N1 . . 116.47(17)
C29 N3 N4 . . 116.15(18)
C16 N4 N3 . . 116.55(18)
N2 C1 C8 . . 116.43(19)
N2 C1 C2 . . 123.95(17)
C8 C1 C2 . . 119.60(17)
C3 C2 C7 . . 117.0(2)
C3 C2 C1 . . 121.39(18)
C7 C2 C1 . . 121.6(2)
C2 C3 C4 . . 122.1(2)
C2 C3 H3 . . 118.9
C4 C3 H3 . . 118.9
C5 C4 C3 . . 118.4(3)
C5 C4 H4 . . 120.8
C3 C4 H4 . . 120.8
C4 C5 C6 . . 122.3(3)
C4 C5 F1 . . 119.3(3)
C6 C5 F1 . . 118.4(3)
C5 C6 C7 . . 118.9(2)
C5 C6 H6 . . 120.5
C7 C6 H6 . . 120.5
C2 C7 C6 . . 121.2(2)
C2 C7 H7 . . 119.4
C6 C7 H7 . . 119.4
C13 C8 C9 . . 118.3(2)
C13 C8 C1 . . 120.9(2)
C9 C8 C1 . . 120.8(2)
C10 C9 C8 . . 121.5(3)
C10 C9 H9 . . 119.3
C8 C9 H9 . . 119.3
C11 C10 C9 . . 118.7(3)
C11 C10 H10 . . 120.6
C9 C10 H10 . . 120.6
F2 C11 C10 . . 119.5(3)
F2 C11 C12 . . 118.3(3)
C10 C11 C12 . . 122.2(2)
C11 C12 C13 . . 119.1(3)
C11 C12 H12 . . 120.4
C13 C12 H12 . . 120.4
C8 C13 C12 . . 120.1(3)
C8 C13 H13 . . 119.9
C12 C13 H13 . . 119.9
N1 C14 C14 . 2_565 115.5(2)
N1 C14 C15 . . 124.38(17)
C14 C14 C15 2_565 . 120.1(2)
C14 C15 H15A . . 109.5
C14 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C14 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
N4 C16 C23 . . 124.23(18)
N4 C16 C17 . . 116.69(19)
C23 C16 C17 . . 119.08(16)
C18 C17 C22 . . 117.8(2)
C18 C17 C16 . . 120.78(18)
C22 C17 C16 . . 121.4(2)
C17 C18 C19 . . 121.5(2)
C17 C18 H18 . . 119.3
C19 C18 H18 . . 119.3
C20 C19 C18 . . 118.6(2)
C20 C19 H19 . . 120.7
C18 C19 H19 . . 120.7
C21 C20 F3 . . 118.0(2)
C21 C20 C19 . . 122.3(2)
F3 C20 C19 . . 119.7(2)
C20 C21 C22 . . 119.0(2)
C20 C21 H21 . . 120.5
C22 C21 H21 . . 120.5
C17 C22 C21 . . 120.8(2)
C17 C22 H22 . . 119.6
C21 C22 H22 . . 119.6
C24 C23 C28 . . 117.8(2)
C24 C23 C16 . . 121.20(18)
C28 C23 C16 . . 121.0(2)
C25 C24 C23 . . 121.8(2)
C25 C24 H24 . . 119.1
C23 C24 H24 . . 119.1
C26 C25 C24 . . 118.6(3)
C26 C25 H25 . . 120.7
C24 C25 H25 . . 120.7
C25 C26 C27 . . 122.6(3)
C25 C26 F4 . . 119.9(3)
C27 C26 F4 . . 117.5(3)
C26 C27 C28 . . 118.7(3)
C26 C27 H27 . . 120.7
C28 C27 H27 . . 120.7
C23 C28 C27 . . 120.6(3)
C23 C28 H28 . . 119.7
C27 C28 H28 . . 119.7
N3 C29 C29 . 2_676 115.1(2)
N3 C29 C30 . . 124.41(19)
C29 C29 C30 2_676 . 120.5(2)
C29 C30 H30A . . 109.5
C29 C30 H30B . . 109.5
H30A C30 H30B . . 109.5
C29 C30 H30C . . 109.5
H30A C30 H30C . . 109.5
H30B C30 H30C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C14 . 1.280(2)
N1 N2 . 1.389(2)
N2 C1 . 1.284(2)
N3 C29 . 1.280(2)
N3 N4 . 1.391(2)
N4 C16 . 1.285(2)
F1 C5 . 1.358(3)
F2 C11 . 1.346(3)
F3 C20 . 1.350(2)
F4 C26 . 1.360(3)
C1 C8 . 1.482(3)
C1 C2 . 1.483(3)
C2 C3 . 1.368(3)
C2 C7 . 1.376(3)
C3 C4 . 1.375(3)
C3 H3 . 0.9300
C4 C5 . 1.341(4)
C4 H4 . 0.9300
C5 C6 . 1.343(4)
C6 C7 . 1.379(4)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 C13 . 1.381(3)
C8 C9 . 1.382(3)
C9 C10 . 1.378(3)
C9 H9 . 0.9300
C10 C11 . 1.351(4)
C10 H10 . 0.9300
C11 C12 . 1.357(4)
C12 C13 . 1.395(4)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 C14 2_565 1.478(4)
C14 C15 . 1.485(3)
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
C16 C23 . 1.482(3)
C16 C17 . 1.482(3)
C17 C18 . 1.377(3)
C17 C22 . 1.379(3)
C18 C19 . 1.382(3)
C18 H18 . 0.9300
C19 C20 . 1.351(3)
C19 H19 . 0.9300
C20 C21 . 1.345(4)
C21 C22 . 1.389(3)
C21 H21 . 0.9300
C22 H22 . 0.9300
C23 C24 . 1.378(3)
C23 C28 . 1.379(3)
C24 C25 . 1.363(3)
C24 H24 . 0.9300
C25 C26 . 1.343(4)
C25 H25 . 0.9300
C26 C27 . 1.353(4)
C27 C28 . 1.381(4)
C27 H27 . 0.9300
C28 H28 . 0.9300
C29 C29 2_676 1.480(4)
C29 C30 . 1.485(3)
C30 H30A . 0.9600
C30 H30B . 0.9600
C30 H30C . 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 F4 1_554 0.93 2.58 3.451(3) 156.2 yes
C6 H6 F2 2_575 0.93 2.58 3.492(3) 168.0 yes
C25 H25 F1 1_656 0.93 2.62 3.497(3) 158.3 yes

_cod_database_fobs_code 2021345
