#------------------------------------------------------------------------------
#$Date: 2019-11-23 06:05:53 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232296 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/73/4347380.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_4347380
loop_
_publ_author_name
'Chen, Yuxiang'
'Cao, Wei'
'Wang, Chiming'
'Qi, Dongdong'
'Wang, Kang'
'Jiang, Jianzhuang'
_publ_section_title
;
 Four Dibutylamino Substituents Are Better Than Eight in Modulating the
 Electronic Structure and Third-Order Nonlinear-Optical Properties of
 Phthalocyanines.
;
_journal_issue                   6
_journal_name_full               'Inorganic chemistry'
_journal_page_first              3151
_journal_page_last               3160
_journal_paper_doi               10.1021/acs.inorgchem.6b00100
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C24 H38 N4'
_chemical_formula_weight         382.58
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.113(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2971(14)
_cell_length_b                   9.9436(10)
_cell_length_c                   17.5443(18)
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1010
_cell_measurement_theta_min      3.0064
_cell_volume                     2370.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9368
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.064
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0513
_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)+(0.0578P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                2352
_reflns_number_total             4163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic6b00100_si_003.cif
_cod_data_source_block           n2
_cod_database_code               4347380
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_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
N1 N 0.25256(11) 0.61792(17) 0.41036(9) 0.0400(4) Uani 1 1 d .
N2 N 0.24150(11) 0.65131(16) 0.57272(9) 0.0409(4) Uani 1 1 d .
C3 C 0.24790(13) 0.4096(2) 0.58491(12) 0.0420(5) Uani 1 1 d .
H3 H 0.2440 0.4192 0.6366 0.050 Uiso 1 1 calc R
C4 C 0.24800(13) 0.5248(2) 0.54038(11) 0.0363(5) Uani 1 1 d .
C5 C 0.25317(12) 0.5090(2) 0.46039(11) 0.0359(5) Uani 1 1 d .
C6 C 0.26010(13) 0.3789(2) 0.43367(12) 0.0425(5) Uani 1 1 d .
H6 H 0.2644 0.3673 0.3823 0.051 Uiso 1 1 calc R
C7 C 0.26092(14) 0.2659(2) 0.47971(13) 0.0441(5) Uani 1 1 d .
C8 C 0.25336(14) 0.2815(2) 0.55645(13) 0.0445(5) Uani 1 1 d .
C9 C 0.31751(14) 0.7519(2) 0.57331(12) 0.0457(5) Uani 1 1 d .
H9A H 0.2907 0.8409 0.5757 0.055 Uiso 1 1 calc R
H9B H 0.3327 0.7454 0.5233 0.055 Uiso 1 1 calc R
C10 C 0.28947(15) 0.5999(2) 0.34163(12) 0.0504(6) Uani 1 1 d .
H10A H 0.2800 0.6832 0.3114 0.061 Uiso 1 1 calc R
H10B H 0.2503 0.5312 0.3068 0.061 Uiso 1 1 calc R
C11 C 0.16985(14) 0.7127(2) 0.39449(12) 0.0484(6) Uani 1 1 d .
H11A H 0.1895 0.7971 0.3763 0.058 Uiso 1 1 calc R
H11B H 0.1562 0.7302 0.4444 0.058 Uiso 1 1 calc R
C12 C 0.25470(17) 0.1675(3) 0.60621(15) 0.0588(6) Uani 1 1 d .
C13 C 0.46875(16) 0.6485(2) 0.42380(15) 0.0605(7) Uani 1 1 d .
H13A H 0.4546 0.6432 0.4743 0.073 Uiso 1 1 calc R
H13B H 0.5346 0.6134 0.4326 0.073 Uiso 1 1 calc R
C14 C 0.26700(17) 0.1350(2) 0.44707(15) 0.0596(7) Uani 1 1 d .
C15 C 0.39675(15) 0.5604(2) 0.36345(14) 0.0554(6) Uani 1 1 d .
H15A H 0.4035 0.4693 0.3843 0.066 Uiso 1 1 calc R
H15B H 0.4152 0.5592 0.3147 0.066 Uiso 1 1 calc R
C16 C 0.20520(16) 0.6622(2) 0.64175(13) 0.0533(6) Uani 1 1 d .
H16A H 0.2112 0.7550 0.6597 0.064 Uiso 1 1 calc R
H16B H 0.2468 0.6081 0.6851 0.064 Uiso 1 1 calc R
C17 C 0.09945(17) 0.6180(3) 0.62531(15) 0.0680(7) Uani 1 1 d .
H17A H 0.0813 0.6327 0.6736 0.082 Uiso 1 1 calc R
H17B H 0.0960 0.5220 0.6150 0.082 Uiso 1 1 calc R
C18 C 0.07651(15) 0.6649(3) 0.33312(13) 0.0599(7) Uani 1 1 d .
H18A H 0.0568 0.5799 0.3505 0.072 Uiso 1 1 calc R
H18B H 0.0889 0.6500 0.2825 0.072 Uiso 1 1 calc R
C19 C 0.41151(15) 0.7375(2) 0.64164(13) 0.0549(6) Uani 1 1 d .
H19A H 0.4392 0.6491 0.6394 0.066 Uiso 1 1 calc R
H19B H 0.3971 0.7446 0.6920 0.066 Uiso 1 1 calc R
C20 C 0.48635(18) 0.8434(3) 0.63912(16) 0.0789(8) Uani 1 1 d .
H20A H 0.5033 0.8319 0.5901 0.095 Uiso 1 1 calc R
H20B H 0.4561 0.9313 0.6368 0.095 Uiso 1 1 calc R
N3 N 0.27193(19) 0.0328(2) 0.41955(16) 0.0964(9) Uani 1 1 d .
C22 C 0.46717(19) 0.7926(3) 0.39996(17) 0.0793(8) Uani 1 1 d .
H22A H 0.4829 0.7994 0.3507 0.119 Uiso 1 1 calc R
H22B H 0.5148 0.8418 0.4413 0.119 Uiso 1 1 calc R
H22C H 0.4028 0.8292 0.3925 0.119 Uiso 1 1 calc R
N4 N 0.25525(19) 0.0761(2) 0.64616(14) 0.0879(8) Uani 1 1 d .
C24 C 0.02356(18) 0.6867(3) 0.55613(17) 0.0797(9) Uani 1 1 d .
H24A H 0.0369 0.6642 0.5067 0.096 Uiso 1 1 calc R
H24B H -0.0410 0.6514 0.5523 0.096 Uiso 1 1 calc R
C25 C -0.00656(18) 0.7661(3) 0.32101(16) 0.0961(11) Uani 1 1 d .
H25A H -0.0221 0.7744 0.3708 0.115 Uiso 1 1 calc R
H25B H 0.0165 0.8532 0.3094 0.115 Uiso 1 1 calc R
C26 C 0.57916(17) 0.8414(3) 0.70852(16) 0.0936(10) Uani 1 1 d .
H26A H 0.5646 0.8650 0.7567 0.140 Uiso 1 1 calc R
H26B H 0.6250 0.9050 0.6993 0.140 Uiso 1 1 calc R
H26C H 0.6074 0.7529 0.7141 0.140 Uiso 1 1 calc R
C27 C -0.0975(2) 0.7321(5) 0.25636(19) 0.1398(17) Uani 1 1 d .
H27A H -0.0841 0.7294 0.2061 0.210 Uiso 1 1 calc R
H27B H -0.1467 0.7990 0.2540 0.210 Uiso 1 1 calc R
H27C H -0.1209 0.6458 0.2669 0.210 Uiso 1 1 calc R
C28 C 0.0214(2) 0.8349(3) 0.5634(2) 0.1110(11) Uani 1 1 d .
H28A H 0.0104 0.8583 0.6130 0.167 Uiso 1 1 calc R
H28B H -0.0307 0.8709 0.5194 0.167 Uiso 1 1 calc R
H28C H 0.0832 0.8716 0.5625 0.167 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C10 119.27(16)
C5 N1 C11 117.72(15)
C10 N1 C11 113.32(16)
C4 N2 C16 119.30(16)
C4 N2 C9 118.20(15)
C16 N2 C9 113.22(16)
C8 C3 C4 123.30(19)
C3 C4 N2 120.26(17)
C3 C4 C5 117.99(17)
N2 C4 C5 121.75(17)
C6 C5 N1 119.89(18)
C6 C5 C4 117.50(18)
N1 C5 C4 122.60(17)
C7 C6 C5 123.23(19)
C6 C7 C8 119.09(18)
C6 C7 C14 119.6(2)
C8 C7 C14 121.3(2)
C3 C8 C7 118.86(19)
C3 C8 C12 120.2(2)
C7 C8 C12 120.9(2)
N2 C9 C19 114.51(18)
N1 C10 C15 114.74(17)
N1 C11 C18 114.50(18)
N4 C12 C8 179.6(3)
C22 C13 C15 114.5(2)
N3 C14 C7 178.3(3)
C13 C15 C10 116.37(19)
N2 C16 C17 114.29(18)
C16 C17 C24 116.5(2)
C11 C18 C25 111.8(2)
C9 C19 C20 112.1(2)
C26 C20 C19 115.1(2)
C28 C24 C17 114.1(3)
C27 C25 C18 114.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.392(2)
N1 C10 1.470(2)
N1 C11 1.470(2)
N2 C4 1.395(2)
N2 C16 1.462(2)
N2 C9 1.475(2)
C3 C8 1.379(3)
C3 C4 1.387(3)
C4 C5 1.437(3)
C5 C6 1.391(3)
C6 C7 1.381(3)
C7 C8 1.392(3)
C7 C14 1.436(3)
C8 C12 1.427(3)
C9 C19 1.504(3)
C10 C15 1.513(3)
C11 C18 1.507(3)
C12 N4 1.146(3)
C13 C22 1.490(3)
C13 C15 1.507(3)
C14 N3 1.136(3)
C16 C17 1.514(3)
C17 C24 1.516(3)
C18 C25 1.520(3)
C19 C20 1.512(3)
C20 C26 1.496(3)
C24 C28 1.480(4)
C25 C27 1.475(4)
