#------------------------------------------------------------------------------
#$Date: 2019-08-26 11:53:52 +0300 (Mon, 26 Aug 2019) $
#$Revision: 217722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/34/7233452.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_7233452
loop_
_publ_author_name
'Ch. G. Chandaluri'
'T. P. Radhakrishnan'
_publ_section_title
;
 Hierarchical assembly of a molecular material through the amorphous phase
 and the evolution of its fluorescence emission
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4464
_journal_page_last               4471
_journal_paper_doi               10.1039/C3TC30615A
_journal_volume                  1
_journal_year                    2013
_chemical_formula_sum            'C21 H20 N4'
_chemical_formula_weight         328.41
_chemical_name_common
7-pyrrolidino-7-benzylamino-8,8-dicyanoquinodimethane
_chemical_name_systematic
7-pyrrolidino-7-benzylamino-8,8-dicyanoquinodimethane
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.2920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4123(7)
_cell_length_b                   12.9289(10)
_cell_length_c                   14.5929(11)
_cell_measurement_reflns_used    9187
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.19
_cell_volume                     1752.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16502
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9674
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0416
_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)+(0.0538P)²+0.6943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1090
_reflns_number_gt                2877
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2013-1-4464.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'EMPIRICAL' was
changed to 'empirical' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n '
_cod_database_code               7233452
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C17A C -0.2702(3) 0.8664(3) -0.1418(3) 0.0331(10) Uani 0.625(10) 1 d P A 1
H17A H -0.2732 0.8169 -0.1938 0.040 Uiso 0.625(10) 1 calc PR A 1
H17B H -0.3701 0.8856 -0.1358 0.040 Uiso 0.625(10) 1 calc PR A 1
C17B C -0.2806(5) 0.9081(6) -0.1039(5) 0.0307(16) Uani 0.375(10) 1 d P A 2
H17C H -0.3675 0.8816 -0.1445 0.037 Uiso 0.375(10) 1 calc PR A 2
H17D H -0.3113 0.9568 -0.0585 0.037 Uiso 0.375(10) 1 calc PR A 2
C8 C -0.05489(14) 0.47698(10) 0.24000(9) 0.0226(3) Uani 1 1 d . . .
N10 N 0.19955(12) 0.83177(9) -0.01356(8) 0.0269(3) Uani 1 1 d . . .
C4 C -0.02022(14) 0.56051(10) 0.18151(9) 0.0218(3) Uani 1 1 d . . .
N9 N -0.04443(12) 0.85382(9) -0.04812(8) 0.0233(3) Uani 1 1 d . A .
C1 C 0.04379(14) 0.72260(10) 0.06461(9) 0.0227(3) Uani 1 1 d . . .
C6 C 0.09503(14) 0.62259(10) 0.05442(9) 0.0241(3) Uani 1 1 d . . .
H6 H 0.1522 0.6088 0.0078 0.029 Uiso 1 1 calc R . .
C3 C -0.06787(15) 0.66236(11) 0.19254(9) 0.0252(3) Uani 1 1 d . . .
H3 H -0.1224 0.6771 0.2404 0.030 Uiso 1 1 calc R . .
C2 C -0.03697(15) 0.74091(11) 0.13532(9) 0.0259(3) Uani 1 1 d . . .
H2 H -0.0711 0.8088 0.1440 0.031 Uiso 1 1 calc R . .
C5 C 0.06358(14) 0.54363(10) 0.11130(9) 0.0227(3) Uani 1 1 d . . .
H5 H 0.0993 0.4762 0.1029 0.027 Uiso 1 1 calc R . .
C12 C -0.01253(15) 0.37434(11) 0.22709(9) 0.0253(3) Uani 1 1 d . . .
C7 C 0.06781(14) 0.80536(10) -0.00116(9) 0.0227(3) Uani 1 1 d . . .
C20 C 0.41484(14) 0.71682(11) -0.00672(10) 0.0275(3) Uani 1 1 d . . .
N13 N -0.19514(14) 0.51170(10) 0.37304(9) 0.0365(3) Uani 1 1 d . . .
C25 C 0.36606(15) 0.68225(11) -0.09628(10) 0.0304(3) Uani 1 1 d . . .
H25 H 0.2781 0.7080 -0.1295 0.036 Uiso 1 1 calc R . .
C24 C 0.44507(16) 0.61010(12) -0.13774(11) 0.0343(4) Uani 1 1 d . . .
H24 H 0.4107 0.5868 -0.1991 0.041 Uiso 1 1 calc R . .
C11 C -0.13177(15) 0.49501(10) 0.31290(9) 0.0253(3) Uani 1 1 d . . .
N14 N 0.02080(16) 0.28955(10) 0.21659(9) 0.0381(3) Uani 1 1 d . . .
C23 C 0.57306(16) 0.57213(12) -0.09028(11) 0.0346(4) Uani 1 1 d . . .
H23 H 0.6271 0.5231 -0.1189 0.042 Uiso 1 1 calc R . .
C21 C 0.54400(15) 0.67769(11) 0.04083(11) 0.0314(3) Uani 1 1 d . . .
H21 H 0.5786 0.7005 0.1023 0.038 Uiso 1 1 calc R . .
C19 C 0.33385(15) 0.79581(12) 0.04179(10) 0.0294(3) Uani 1 1 d . . .
H19A H 0.3119 0.7650 0.1000 0.035 Uiso 1 1 calc R . .
H19B H 0.3973 0.8562 0.0588 0.035 Uiso 1 1 calc R . .
C22 C 0.62237(16) 0.60576(12) -0.00085(11) 0.0345(4) Uani 1 1 d . . .
H22 H 0.7102 0.5795 0.0322 0.041 Uiso 1 1 calc R . .
C18 C -0.19569(15) 0.81936(12) -0.05374(10) 0.0303(3) Uani 1 1 d . . .
H18A H -0.2375 0.8446 0.0002 0.036 Uiso 1 1 calc R A 1
H18B H -0.2025 0.7430 -0.0561 0.036 Uiso 1 1 calc R A 1
C15 C -0.03200(15) 0.93456(10) -0.11791(9) 0.0260(3) Uani 1 1 d . . .
H15A H 0.0213 0.9085 -0.1664 0.031 Uiso 1 1 calc R A .
H15B H 0.0179 0.9965 -0.0885 0.031 Uiso 1 1 calc R . .
C16 C -0.18678(18) 0.95932(14) -0.15857(13) 0.0452(4) Uani 1 1 d . A .
H16A H -0.2210 1.0205 -0.1276 0.054 Uiso 1 1 calc R B 1
H16B H -0.1960 0.9736 -0.2259 0.054 Uiso 1 1 calc R B 1
H10 H 0.2108(18) 0.8824(14) -0.0567(12) 0.040(5) Uiso 1 1 d . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 C17A C18 106.6(2) . .
C16 C17A H17A 110.4 . .
C18 C17A H17A 110.4 . .
C16 C17A H17B 110.4 . .
C18 C17A H17B 110.4 . .
H17A C17A H17B 108.6 . .
C16 C17B C18 107.0(3) . .
C16 C17B H17C 110.3 . .
C18 C17B H17C 110.3 . .
C16 C17B H17D 110.3 . .
C18 C17B H17D 110.3 . .
H17C C17B H17D 108.6 . .
C11 C8 C12 116.83(12) . .
C11 C8 C4 121.20(12) . .
C12 C8 C4 121.97(12) . .
C7 N10 C19 125.94(12) . .
C7 N10 H10 119.1(11) . .
C19 N10 H10 114.6(11) . .
C5 C4 C3 117.03(12) . .
C5 C4 C8 121.36(12) . .
C3 C4 C8 121.61(12) . .
C7 N9 C15 123.20(11) . .
C7 N9 C18 124.55(11) . .
C15 N9 C18 110.92(11) . .
C6 C1 C2 118.29(12) . .
C6 C1 C7 120.62(12) . .
C2 C1 C7 121.01(12) . .
C5 C6 C1 120.70(12) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
C2 C3 C4 121.23(12) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C3 C2 C1 121.12(12) . .
C3 C2 H2 119.4 . .
C1 C2 H2 119.4 . .
C6 C5 C4 121.60(12) . .
C6 C5 H5 119.2 . .
C4 C5 H5 119.2 . .
N14 C12 C8 179.24(15) . .
N9 C7 N10 119.62(12) . .
N9 C7 C1 119.12(12) . .
N10 C7 C1 121.26(12) . .
C25 C20 C21 118.78(14) . .
C25 C20 C19 122.81(13) . .
C21 C20 C19 118.41(13) . .
C20 C25 C24 120.46(14) . .
C20 C25 H25 119.8 . .
C24 C25 H25 119.8 . .
C23 C24 C25 120.35(15) . .
C23 C24 H24 119.8 . .
C25 C24 H24 119.8 . .
N13 C11 C8 178.85(15) . .
C24 C23 C22 119.66(15) . .
C24 C23 H23 120.2 . .
C22 C23 H23 120.2 . .
C22 C21 C20 120.53(14) . .
C22 C21 H21 119.7 . .
C20 C21 H21 119.7 . .
N10 C19 C20 114.28(12) . .
N10 C19 H19A 108.7 . .
C20 C19 H19A 108.7 . .
N10 C19 H19B 108.7 . .
C20 C19 H19B 108.7 . .
H19A C19 H19B 107.6 . .
C23 C22 C21 120.23(14) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
N9 C18 C17A 103.85(15) . .
N9 C18 C17B 103.1(2) . .
C17A C18 C17B 30.4(2) . .
N9 C18 H18A 111.0 . .
C17A C18 H18A 111.0 . .
C17B C18 H18A 83.5 . .
N9 C18 H18B 111.0 . .
C17A C18 H18B 111.0 . .
C17B C18 H18B 135.3 . .
H18A C18 H18B 109.0 . .
N9 C15 C16 103.96(11) . .
N9 C15 H15A 111.0 . .
C16 C15 H15A 111.0 . .
N9 C15 H15B 111.0 . .
C16 C15 H15B 111.0 . .
H15A C15 H15B 109.0 . .
C17B C16 C17A 31.3(2) . .
C17B C16 C15 108.8(2) . .
C17A C16 C15 105.44(15) . .
C17B C16 H16A 80.8 . .
C17A C16 H16A 110.7 . .
C15 C16 H16A 110.7 . .
C17B C16 H16B 132.2 . .
C17A C16 H16B 110.7 . .
C15 C16 H16B 110.7 . .
H16A C16 H16B 108.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C17A C16 1.477(4) .
C17A C18 1.490(3) .
C17A H17A 0.9900 .
C17A H17B 0.9900 .
C17B C16 1.444(5) .
C17B C18 1.517(5) .
C17B H17C 0.9900 .
C17B H17D 0.9900 .
C8 C11 1.3994(19) .
C8 C12 1.4070(19) .
C8 C4 1.4462(19) .
N10 C7 1.3264(18) .
N10 C19 1.4617(18) .
N10 H10 0.926(19) .
C4 C5 1.4072(19) .
C4 C3 1.4086(19) .
N9 C7 1.3208(17) .
N9 C15 1.4761(17) .
N9 C18 1.4814(18) .
C1 C6 1.3964(19) .
C1 C2 1.3971(19) .
C1 C7 1.4789(18) .
C6 C5 1.3776(19) .
C6 H6 0.9500 .
C3 C2 1.375(2) .
C3 H3 0.9500 .
C2 H2 0.9500 .
C5 H5 0.9500 .
C12 N14 1.1573(19) .
C20 C25 1.387(2) .
C20 C21 1.394(2) .
C20 C19 1.516(2) .
N13 C11 1.1583(19) .
C25 C24 1.391(2) .
C25 H25 0.9500 .
C24 C23 1.379(2) .
C24 H24 0.9500 .
C23 C22 1.383(2) .
C23 H23 0.9500 .
C21 C22 1.387(2) .
C21 H21 0.9500 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C22 H22 0.9500 .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C15 C16 1.516(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
