#------------------------------------------------------------------------------
#$Date: 2018-11-16 05:33:15 +0200 (Fri, 16 Nov 2018) $
#$Revision: 212002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/13/2021348.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_2021348
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          'C34 H34 N4'
_chemical_formula_moiety         'C34 H34 N4'
_chemical_formula_sum            'C34 H34 N4'
_chemical_formula_weight         498.65
_chemical_name_systematic
;
Butane-2,3-dione 2,3-bis{[bis(4-methylphenyl)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-2016/6
_cell_angle_alpha                104.238(2)
_cell_angle_beta                 95.169(2)
_cell_angle_gamma                107.232(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6122(4)
_cell_length_b                   10.7586(6)
_cell_length_c                   18.3363(11)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.63
_cell_volume                     1368.51(14)
_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
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            63984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.318
_diffrn_reflns_theta_min         2.063
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2012)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.369
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0514
_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)+(0.0701P)²+0.7370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                5759
_reflns_number_total             6794
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            uk3160sup1.cif
_cod_data_source_block           3a
_cod_original_cell_volume        1368.51(13)
_cod_database_code               2021348
_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   0.970
_shelx_estimated_absorpt_t_max   0.985
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 0.84962(15) 0.63387(11) 0.10935(6) 0.0180(2) Uani d 1
N N2 0.66544(15) 0.60759(11) 0.07965(6) 0.0172(2) Uani d 1
N N3 0.13612(16) 0.40732(12) 0.40169(7) 0.0214(2) Uani d 1
N N4 0.27424(15) 0.39873(12) 0.45366(7) 0.0204(2) Uani d 1
C C1 0.96370(18) 0.75725(13) 0.12820(7) 0.0168(3) Uani d 1
C C2 0.91952(18) 0.87240(13) 0.10946(8) 0.0187(3) Uani d 1
C C3 0.81904(19) 0.85664(14) 0.03853(8) 0.0217(3) Uani d 1
H H3 0.781149 0.771239 0.000670 0.026 Uiso calc 1
C C4 0.7735(2) 0.96376(15) 0.02239(9) 0.0266(3) Uani d 1
H H4 0.705066 0.950665 -0.026405 0.032 Uiso calc 1
C C5 0.8266(2) 1.09010(15) 0.07650(9) 0.0271(3) Uani d 1
C C6 0.9273(2) 1.10601(14) 0.14724(9) 0.0269(3) Uani d 1
H H6 0.963936 1.191267 0.185176 0.032 Uiso calc 1
C C7 0.97532(19) 0.99978(14) 0.16348(8) 0.0228(3) Uani d 1
H H7 1.046826 1.013784 0.211785 0.027 Uiso calc 1
C C8 0.7799(3) 1.20670(18) 0.05752(11) 0.0402(4) Uani d 1
H H8A 0.754818 1.188917 0.001901 0.060 Uiso calc 1
H H8B 0.885460 1.290824 0.079853 0.060 Uiso calc 1
H H8C 0.668950 1.216057 0.078481 0.060 Uiso calc 1
C C9 1.14988(18) 0.77868(13) 0.17161(7) 0.0178(3) Uani d 1
C C10 1.31145(19) 0.87895(14) 0.16780(8) 0.0209(3) Uani d 1
H H10 1.302386 0.942279 0.140762 0.025 Uiso calc 1
C C11 1.48576(19) 0.88710(15) 0.20322(8) 0.0231(3) Uani d 1
H H11 1.594442 0.955025 0.199255 0.028 Uiso calc 1
C C12 1.50330(19) 0.79728(15) 0.24437(8) 0.0224(3) Uani d 1
C C13 1.3408(2) 0.70216(15) 0.25123(8) 0.0243(3) Uani d 1
H H13 1.349194 0.642960 0.281236 0.029 Uiso calc 1
C C14 1.16734(19) 0.69197(14) 0.21528(8) 0.0219(3) Uani d 1
H H14 1.058767 0.625207 0.220340 0.026 Uiso calc 1
C C15 1.6908(2) 0.79710(17) 0.27845(9) 0.0281(3) Uani d 1
H H15A 1.717031 0.717880 0.248309 0.042 Uiso calc 1
H H15B 1.689495 0.792997 0.331207 0.042 Uiso calc 1
H H15C 1.787944 0.880288 0.277995 0.042 Uiso calc 1
C C16 0.60118(17) 0.51861(12) 0.01387(7) 0.0151(2) Uani d 1
C C17 0.71926(18) 0.45751(14) -0.03465(8) 0.0207(3) Uani d 1
H H17A 0.780168 0.519876 -0.062786 0.031 Uiso calc 1
H H17B 0.640382 0.371104 -0.070934 0.031 Uiso calc 1
H H17C 0.814574 0.441525 -0.002016 0.031 Uiso calc 1
C C18 -0.03297(18) 0.33344(13) 0.40239(7) 0.0180(3) Uani d 1
C C19 -0.08477(18) 0.24931(13) 0.45555(8) 0.0177(3) Uani d 1
C C20 -0.01485(18) 0.30044(13) 0.53375(8) 0.0183(3) Uani d 1
H H20 0.066721 0.391484 0.554145 0.022 Uiso calc 1
C C21 -0.06325(18) 0.21961(14) 0.58211(8) 0.0198(3) Uani d 1
H H21 -0.015516 0.256892 0.635337 0.024 Uiso calc 1
C C22 -0.18022(19) 0.08509(14) 0.55435(8) 0.0217(3) Uani d 1
C C23 -0.2499(2) 0.03424(14) 0.47605(8) 0.0257(3) Uani d 1
H H23 -0.330241 -0.057175 0.455636 0.031 Uiso calc 1
C C24 -0.2039(2) 0.11506(14) 0.42742(8) 0.0236(3) Uani d 1
H H24 -0.254170 0.078488 0.374380 0.028 Uiso calc 1
C C25 -0.2305(2) -0.00252(16) 0.60721(9) 0.0292(3) Uani d 1
H H25A -0.146345 0.041377 0.656627 0.044 Uiso calc 1
H H25B -0.218228 -0.091447 0.584683 0.044 Uiso calc 1
H H25C -0.359733 -0.014395 0.614651 0.044 Uiso calc 1
C C26 -0.18174(18) 0.33972(13) 0.34604(7) 0.0183(3) Uani d 1
C C27 -0.37042(19) 0.29318(15) 0.35105(8) 0.0239(3) Uani d 1
H H27 -0.406695 0.253955 0.390749 0.029 Uiso calc 1
C C28 -0.5068(2) 0.30314(16) 0.29892(9) 0.0260(3) Uani d 1
H H28 -0.634524 0.269812 0.303310 0.031 Uiso calc 1
C C29 -0.4588(2) 0.36094(14) 0.24076(8) 0.0232(3) Uani d 1
C C30 -0.2695(2) 0.41190(15) 0.23724(8) 0.0246(3) Uani d 1
H H30 -0.233206 0.454670 0.198852 0.030 Uiso calc 1
C C31 -0.13384(19) 0.40137(14) 0.28852(8) 0.0219(3) Uani d 1
H H31 -0.006032 0.436571 0.284625 0.026 Uiso calc 1
C C32 -0.6053(2) 0.36927(18) 0.18282(10) 0.0331(4) Uani d 1
H H32A -0.646836 0.285982 0.140008 0.050 Uiso calc 1
H H32B -0.552296 0.447628 0.163947 0.050 Uiso calc 1
H H32C -0.712059 0.379597 0.206831 0.050 Uiso calc 1
C C33 0.42487(17) 0.50329(13) 0.47275(7) 0.0189(3) Uani d 1
C C34 0.45753(19) 0.62552(15) 0.44365(9) 0.0244(3) Uani d 1
H H34A 0.499706 0.606948 0.394391 0.037 Uiso calc 1
H H34B 0.553294 0.703459 0.480436 0.037 Uiso calc 1
H H34C 0.340933 0.646008 0.437129 0.037 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'
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
C1 N1 N2 . . 119.22(11)
C16 N2 N1 . . 116.34(11)
C18 N3 N4 . . 114.78(11)
C33 N4 N3 . . 113.85(11)
N1 C1 C2 . . 124.67(12)
N1 C1 C9 . . 114.90(11)
C2 C1 C9 . . 120.43(11)
C3 C2 C7 . . 118.08(13)
C3 C2 C1 . . 121.39(12)
C7 C2 C1 . . 120.52(12)
C4 C3 C2 . . 120.96(13)
C4 C3 H3 . . 119.5
C2 C3 H3 . . 119.5
C3 C4 C5 . . 121.04(14)
C3 C4 H4 . . 119.5
C5 C4 H4 . . 119.5
C4 C5 C6 . . 118.03(13)
C4 C5 C8 . . 120.46(15)
C6 C5 C8 . . 121.49(15)
C7 C6 C5 . . 121.25(14)
C7 C6 H6 . . 119.4
C5 C6 H6 . . 119.4
C6 C7 C2 . . 120.62(13)
C6 C7 H7 . . 119.7
C2 C7 H7 . . 119.7
C5 C8 H8A . . 109.5
C5 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C5 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C10 C9 C14 . . 118.09(12)
C10 C9 C1 . . 122.45(12)
C14 C9 C1 . . 119.39(12)
C9 C10 C11 . . 120.66(13)
C9 C10 H10 . . 119.7
C11 C10 H10 . . 119.7
C12 C11 C10 . . 121.03(13)
C12 C11 H11 . . 119.5
C10 C11 H11 . . 119.5
C13 C12 C11 . . 117.95(13)
C13 C12 C15 . . 119.82(13)
C11 C12 C15 . . 122.18(13)
C14 C13 C12 . . 121.36(13)
C14 C13 H13 . . 119.3
C12 C13 H13 . . 119.3
C13 C14 C9 . . 120.77(13)
C13 C14 H14 . . 119.6
C9 C14 H14 . . 119.6
C12 C15 H15A . . 109.5
C12 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C12 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
N2 C16 C16 . 2_665 115.75(14)
N2 C16 C17 . . 123.96(11)
C16 C16 C17 2_665 . 120.26(14)
C16 C17 H17A . . 109.5
C16 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
C16 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
N3 C18 C19 . . 124.93(12)
N3 C18 C26 . . 115.32(12)
C19 C18 C26 . . 119.73(11)
C20 C19 C24 . . 118.24(12)
C20 C19 C18 . . 121.63(12)
C24 C19 C18 . . 120.13(12)
C21 C20 C19 . . 120.64(12)
C21 C20 H20 . . 119.7
C19 C20 H20 . . 119.7
C20 C21 C22 . . 121.46(12)
C20 C21 H21 . . 119.3
C22 C21 H21 . . 119.3
C21 C22 C23 . . 117.75(13)
C21 C22 C25 . . 121.12(13)
C23 C22 C25 . . 121.13(13)
C24 C23 C22 . . 121.11(13)
C24 C23 H23 . . 119.4
C22 C23 H23 . . 119.4
C23 C24 C19 . . 120.80(13)
C23 C24 H24 . . 119.6
C19 C24 H24 . . 119.6
C22 C25 H25A . . 109.5
C22 C25 H25B . . 109.5
H25A C25 H25B . . 109.5
C22 C25 H25C . . 109.5
H25A C25 H25C . . 109.5
H25B C25 H25C . . 109.5
C27 C26 C31 . . 117.53(12)
C27 C26 C18 . . 122.14(12)
C31 C26 C18 . . 120.21(12)
C28 C27 C26 . . 121.20(13)
C28 C27 H27 . . 119.4
C26 C27 H27 . . 119.4
C29 C28 C27 . . 120.96(13)
C29 C28 H28 . . 119.5
C27 C28 H28 . . 119.5
C28 C29 C30 . . 117.93(13)
C28 C29 C32 . . 121.48(13)
C30 C29 C32 . . 120.58(14)
C31 C30 C29 . . 121.28(13)
C31 C30 H30 . . 119.4
C29 C30 H30 . . 119.4
C30 C31 C26 . . 121.03(13)
C30 C31 H31 . . 119.5
C26 C31 H31 . . 119.5
C29 C32 H32A . . 109.5
C29 C32 H32B . . 109.5
H32A C32 H32B . . 109.5
C29 C32 H32C . . 109.5
H32A C32 H32C . . 109.5
H32B C32 H32C . . 109.5
N4 C33 C33 . 2_666 115.20(15)
N4 C33 C34 . . 125.61(12)
C33 C33 C34 2_666 . 119.18(14)
C33 C34 H34A . . 109.5
C33 C34 H34B . . 109.5
H34A C34 H34B . . 109.5
C33 C34 H34C . . 109.5
H34A C34 H34C . . 109.5
H34B C34 H34C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.2934(16)
N1 N2 . 1.3762(15)
N2 C16 . 1.2879(16)
N3 C18 . 1.3002(17)
N3 N4 . 1.3937(16)
N4 C33 . 1.2933(17)
C1 C2 . 1.4837(18)
C1 C9 . 1.4860(17)
C2 C3 . 1.3931(19)
C2 C7 . 1.3968(19)
C3 C4 . 1.386(2)
C3 H3 . 0.9500
C4 C5 . 1.391(2)
C4 H4 . 0.9500
C5 C6 . 1.391(2)
C5 C8 . 1.509(2)
C6 C7 . 1.387(2)
C6 H6 . 0.9500
C7 H7 . 0.9500
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 C10 . 1.3956(18)
C9 C14 . 1.3968(19)
C10 C11 . 1.3921(19)
C10 H10 . 0.9500
C11 C12 . 1.392(2)
C11 H11 . 0.9500
C12 C13 . 1.391(2)
C12 C15 . 1.5066(19)
C13 C14 . 1.3829(19)
C13 H13 . 0.9500
C14 H14 . 0.9500
C15 H15A . 0.9800
C15 H15B . 0.9800
C15 H15C . 0.9800
C16 C16 2_665 1.478(2)
C16 C17 . 1.4960(18)
C17 H17A . 0.9800
C17 H17B . 0.9800
C17 H17C . 0.9800
C18 C19 . 1.4889(18)
C18 C26 . 1.4911(18)
C19 C20 . 1.3939(18)
C19 C24 . 1.3956(18)
C20 C21 . 1.3881(19)
C20 H20 . 0.9500
C21 C22 . 1.3924(19)
C21 H21 . 0.9500
C22 C23 . 1.395(2)
C22 C25 . 1.5090(19)
C23 C24 . 1.390(2)
C23 H23 . 0.9500
C24 H24 . 0.9500
C25 H25A . 0.9800
C25 H25B . 0.9800
C25 H25C . 0.9800
C26 C27 . 1.3937(19)
C26 C31 . 1.3984(19)
C27 C28 . 1.393(2)
C27 H27 . 0.9500
C28 C29 . 1.385(2)
C28 H28 . 0.9500
C29 C30 . 1.395(2)
C29 C32 . 1.5078(19)
C30 C31 . 1.382(2)
C30 H30 . 0.9500
C31 H31 . 0.9500
C32 H32A . 0.9800
C32 H32B . 0.9800
C32 H32C . 0.9800
C33 C33 2_666 1.480(3)
C33 C34 . 1.5003(18)
C34 H34A . 0.9800
C34 H34B . 0.9800
C34 H34C . 0.9800

_cod_database_fobs_code 2021348
