#------------------------------------------------------------------------------
#$Date: 2023-08-11 02:57:37 +0200 (Fri 11 de Aug de 2023) $
#$Revision: 285615 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/71/7247184.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_7247184
loop_
_publ_author_name
'Morikawa, Masa-aki'
'Yamanaka, Yuta'
'Ho Hui, Joseph Ka'
'Kimizuka, Nobuo'
_publ_section_title
;
 Photoliquefaction and phase transition of m-bisazobenzenes give molecular
 solar thermal fuels with a high energy density
;
_journal_issue                   34
_journal_name_full               'RSC Advances'
_journal_page_first              24031
_journal_page_last               24037
_journal_paper_doi               10.1039/D3RA04595A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C24 H26 N4 O2'
_chemical_formula_sum            'C24 H26 N4 O2'
_chemical_formula_weight         402.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-21
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2023-07-09 deposited with the CCDC.	2023-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.487(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.10900(10)
_cell_length_b                   6.35350(10)
_cell_length_c                   23.4700(6)
_cell_measurement_reflns_used    12565
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.9410
_cell_measurement_theta_min      2.9010
_cell_volume                     1055.21(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50   12.00    --    5.00  45.00  30.00  356
  2  ω    -95.00  83.00   0.50   12.00    --   -5.90  45.00  60.00  356
  3  ω    -95.00  83.00   0.50   12.00    --   -5.90  45.00 120.00  356
  4  ω    -84.00  78.00   0.50   12.00    --    5.00  45.00 150.00  324
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0998471000
_diffrn_orient_matrix_UB_12      -0.0007350000
_diffrn_orient_matrix_UB_13      0.0001613000
_diffrn_orient_matrix_UB_21      0.0090031000
_diffrn_orient_matrix_UB_22      -0.0049143000
_diffrn_orient_matrix_UB_23      0.0303244000
_diffrn_orient_matrix_UB_31      -0.0008717000
_diffrn_orient_matrix_UB_32      -0.1115248000
_diffrn_orient_matrix_UB_33      -0.0013397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26092
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.470
_diffrn_reflns_theta_min         2.615
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             428
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1180
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.732
_reflns_number_gt                4931
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra04595a2.cif
_cod_data_source_block           onp2
_cod_database_code               7247184
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C24 H26 N4 O2'
_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.
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J), C00L(H00L), C00N(H00N), C00P(H00P), C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00R(H00F,H00K,H00M), C00S(H00O,H00R,H00S), C00T(H00T,H00U,H00V), C00U(H00W,
 H00X,H00Y)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.660
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.27818(16) 0.32489(19) 0.84543(5) 0.0224(3) Uani 1 1 d . . . . .
O002 O 0.24384(17) 0.2727(2) 0.16075(5) 0.0243(3) Uani 1 1 d . . . . .
N003 N 0.29231(19) 0.7164(3) 0.36532(6) 0.0227(3) Uani 1 1 d . . . . .
N004 N 0.22027(19) 0.6019(2) 0.61929(6) 0.0218(3) Uani 1 1 d . . . . .
N005 N 0.20753(19) 0.6585(2) 0.40717(6) 0.0228(3) Uani 1 1 d . . . . .
N006 N 0.24394(19) 0.7960(2) 0.61291(6) 0.0227(3) Uani 1 1 d . . . . .
C007 C 0.3305(2) 0.5840(3) 0.77793(7) 0.0202(3) Uani 1 1 d . . . . .
H007 H 0.387637 0.664454 0.807859 0.024 Uiso 1 1 calc R . . . .
C008 C 0.2329(2) 0.8048(3) 0.45359(7) 0.0216(3) Uani 1 1 d . . . . .
C009 C 0.2472(2) 0.3654(3) 0.21337(7) 0.0202(3) Uani 1 1 d . . . . .
C00A C 0.1647(2) 0.3397(3) 0.68902(7) 0.0211(3) Uani 1 1 d . . . . .
H00A H 0.112850 0.256599 0.658885 0.025 Uiso 1 1 calc R . . . .
C00B C 0.2334(2) 0.5382(3) 0.67772(7) 0.0203(3) Uani 1 1 d . . . . .
C00C C 0.2055(2) 0.7286(3) 0.50752(7) 0.0213(3) Uani 1 1 d . . . . .
H00C H 0.161839 0.592315 0.512190 0.026 Uiso 1 1 calc R . . . .
C00D C 0.1720(2) 0.2629(3) 0.74467(7) 0.0210(3) Uani 1 1 d . . . . .
H00D H 0.120752 0.132130 0.752060 0.025 Uiso 1 1 calc R . . . .
C00E C 0.2574(2) 0.3851(3) 0.78917(6) 0.0198(3) Uani 1 1 d . . . . .
C00F C 0.2450(2) 0.8607(3) 0.55471(7) 0.0210(3) Uani 1 1 d . . . . .
C00G C 0.3185(2) 0.6611(3) 0.72289(7) 0.0213(3) Uani 1 1 d . . . . .
H00G H 0.366219 0.793713 0.715634 0.026 Uiso 1 1 calc R . . . .
C00H C 0.2980(2) 1.0699(3) 0.54727(7) 0.0237(3) Uani 1 1 d . . . . .
H00H H 0.320148 1.158422 0.578762 0.028 Uiso 1 1 calc R . . . .
C00I C 0.1696(2) 0.2788(3) 0.26063(7) 0.0228(3) Uani 1 1 d . . . . .
H00I H 0.110301 0.148236 0.257766 0.027 Uiso 1 1 calc R . . . .
C00J C 0.3512(2) 0.6676(3) 0.26911(7) 0.0217(3) Uani 1 1 d . . . . .
H00J H 0.413528 0.796411 0.272156 0.026 Uiso 1 1 calc R . . . .
C00K C 0.2123(2) 0.1196(3) 0.85897(7) 0.0223(3) Uani 1 1 d . . . . .
H00B H 0.272574 0.014198 0.836949 0.027 Uiso 1 1 calc R . . . .
H00E H 0.076833 0.110569 0.849313 0.027 Uiso 1 1 calc R . . . .
C00L C 0.3377(2) 0.5602(3) 0.21783(7) 0.0218(3) Uani 1 1 d . . . . .
H00L H 0.388793 0.617595 0.186280 0.026 Uiso 1 1 calc R . . . .
C00M C 0.2723(2) 0.5850(3) 0.31640(6) 0.0206(3) Uani 1 1 d . . . . .
C00N C 0.1816(2) 0.3894(3) 0.31184(7) 0.0224(3) Uani 1 1 d . . . . .
H00N H 0.129156 0.333131 0.343303 0.027 Uiso 1 1 calc R . . . .
C00O C 0.2596(2) 0.0792(3) 0.92276(7) 0.0239(3) Uani 1 1 d . . . . .
C00P C 0.3175(2) 1.1451(3) 0.49256(7) 0.0252(4) Uani 1 1 d . . . . .
H00P H 0.350748 1.284906 0.487494 0.030 Uiso 1 1 calc R . . . .
C00Q C 0.2879(2) 1.0141(3) 0.44569(7) 0.0242(4) Uani 1 1 d . . . . .
H00Q H 0.304331 1.063997 0.409242 0.029 Uiso 1 1 calc R . . . .
C00R C 0.1705(3) 0.0649(3) 0.15464(8) 0.0312(4) Uani 1 1 d . . . . .
H00F H 0.190890 0.011635 0.117440 0.047 Uiso 1 1 calc GR . . . .
H00K H 0.037554 0.066708 0.158845 0.047 Uiso 1 1 calc GR . . . .
H00M H 0.233698 -0.024087 0.183498 0.047 Uiso 1 1 calc GR . . . .
C00S C 0.1961(3) -0.1451(3) 0.93426(8) 0.0344(4) Uani 1 1 d . . . . .
H00O H 0.062062 -0.156439 0.924833 0.052 Uiso 1 1 calc GR . . . .
H00R H 0.226423 -0.178125 0.973992 0.052 Uiso 1 1 calc GR . . . .
H00S H 0.259816 -0.241626 0.911205 0.052 Uiso 1 1 calc GR . . . .
C00T C 0.4728(3) 0.0991(4) 0.93866(8) 0.0345(4) Uani 1 1 d . . . . .
H00T H 0.538313 0.003454 0.915828 0.052 Uiso 1 1 calc GR . . . .
H00U H 0.501646 0.065838 0.978438 0.052 Uiso 1 1 calc GR . . . .
H00V H 0.512083 0.240630 0.931701 0.052 Uiso 1 1 calc GR . . . .
C00U C 0.1538(3) 0.2343(4) 0.95758(8) 0.0373(5) Uani 1 1 d . . . . .
H00W H 0.190648 0.375326 0.949045 0.056 Uiso 1 1 calc GR . . . .
H00X H 0.183901 0.206988 0.997643 0.056 Uiso 1 1 calc GR . . . .
H00Y H 0.020264 0.218278 0.947982 0.056 Uiso 1 1 calc GR . . . .
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'
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
_geom_angle_publ_flag
C00E O001 C00K 117.47(13) . . ?
C009 O002 C00R 117.80(14) . . ?
N005 N003 C00M 116.28(15) . . ?
N006 N004 C00B 113.37(14) . . ?
N003 N005 C008 111.76(14) . . ?
N004 N006 C00F 114.22(14) . . ?
C00E C007 H007 119.8 . . ?
C00G C007 H007 119.8 . . ?
C00G C007 C00E 120.45(14) . . ?
C00C C008 N005 116.77(15) . . ?
C00C C008 C00Q 121.11(16) . . ?
C00Q C008 N005 122.10(14) . . ?
O002 C009 C00I 124.96(16) . . ?
O002 C009 C00L 114.77(14) . . ?
C00L C009 C00I 120.27(15) . . ?
C00B C00A H00A 119.5 . . ?
C00B C00A C00D 121.09(15) . . ?
C00D C00A H00A 119.5 . . ?
C00A C00B N004 116.77(15) . . ?
C00A C00B C00G 119.66(15) . . ?
C00G C00B N004 123.51(15) . . ?
C008 C00C H00C 120.7 . . ?
C008 C00C C00F 118.64(16) . . ?
C00F C00C H00C 120.7 . . ?
C00A C00D H00D 120.6 . . ?
C00A C00D C00E 118.88(15) . . ?
C00E C00D H00D 120.6 . . ?
O001 C00E C007 115.21(14) . . ?
O001 C00E C00D 124.50(16) . . ?
C00D C00E C007 120.30(14) . . ?
C00C C00F N006 124.53(16) . . ?
C00C C00F C00H 120.58(15) . . ?
C00H C00F N006 114.84(15) . . ?
C007 C00G C00B 119.57(16) . . ?
C007 C00G H00G 120.2 . . ?
C00B C00G H00G 120.2 . . ?
C00F C00H H00H 120.2 . . ?
C00P C00H C00F 119.63(16) . . ?
C00P C00H H00H 120.2 . . ?
C009 C00I H00I 120.3 . . ?
C00N C00I C009 119.44(16) . . ?
C00N C00I H00I 120.3 . . ?
C00L C00J H00J 119.7 . . ?
C00L C00J C00M 120.59(16) . . ?
C00M C00J H00J 119.7 . . ?
O001 C00K H00B 109.9 . . ?
O001 C00K H00E 109.9 . . ?
O001 C00K C00O 108.98(14) . . ?
H00B C00K H00E 108.3 . . ?
C00O C00K H00B 109.9 . . ?
C00O C00K H00E 109.9 . . ?
C009 C00L H00L 120.1 . . ?
C00J C00L C009 119.88(14) . . ?
C00J C00L H00L 120.1 . . ?
C00J C00M N003 113.99(15) . . ?
C00J C00M C00N 119.42(15) . . ?
C00N C00M N003 126.58(14) . . ?
C00I C00N C00M 120.38(15) . . ?
C00I C00N H00N 119.8 . . ?
C00M C00N H00N 119.8 . . ?
C00K C00O C00S 106.84(15) . . ?
C00K C00O C00T 110.21(14) . . ?
C00S C00O C00T 109.68(17) . . ?
C00U C00O C00K 110.14(15) . . ?
C00U C00O C00S 109.83(16) . . ?
C00U C00O C00T 110.09(17) . . ?
C00H C00P H00P 119.7 . . ?
C00Q C00P C00H 120.60(17) . . ?
C00Q C00P H00P 119.7 . . ?
C008 C00Q H00Q 120.4 . . ?
C00P C00Q C008 119.30(15) . . ?
C00P C00Q H00Q 120.4 . . ?
O002 C00R H00F 109.5 . . ?
O002 C00R H00K 109.5 . . ?
O002 C00R H00M 109.5 . . ?
H00F C00R H00K 109.5 . . ?
H00F C00R H00M 109.5 . . ?
H00K C00R H00M 109.5 . . ?
C00O C00S H00O 109.5 . . ?
C00O C00S H00R 109.5 . . ?
C00O C00S H00S 109.5 . . ?
H00O C00S H00R 109.5 . . ?
H00O C00S H00S 109.5 . . ?
H00R C00S H00S 109.5 . . ?
C00O C00T H00T 109.5 . . ?
C00O C00T H00U 109.5 . . ?
C00O C00T H00V 109.5 . . ?
H00T C00T H00U 109.5 . . ?
H00T C00T H00V 109.5 . . ?
H00U C00T H00V 109.5 . . ?
C00O C00U H00W 109.5 . . ?
C00O C00U H00X 109.5 . . ?
C00O C00U H00Y 109.5 . . ?
H00W C00U H00X 109.5 . . ?
H00W C00U H00Y 109.5 . . ?
H00X C00U H00Y 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00E 1.3689(18) . ?
O001 C00K 1.432(2) . ?
O002 C009 1.3665(19) . ?
O002 C00R 1.422(2) . ?
N003 N005 1.256(2) . ?
N003 C00M 1.416(2) . ?
N004 N006 1.255(2) . ?
N004 C00B 1.424(2) . ?
N005 C008 1.430(2) . ?
N006 C00F 1.427(2) . ?
C007 H007 0.9300 . ?
C007 C00E 1.401(2) . ?
C007 C00G 1.377(2) . ?
C008 C00C 1.386(2) . ?
C008 C00Q 1.404(2) . ?
C009 C00I 1.398(2) . ?
C009 C00L 1.394(2) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.388(2) . ?
C00A C00D 1.391(2) . ?
C00B C00G 1.406(2) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.397(2) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.393(2) . ?
C00F C00H 1.397(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00P 1.389(2) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.388(2) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.379(2) . ?
C00J C00M 1.393(2) . ?
C00K H00B 0.9700 . ?
C00K H00E 0.9700 . ?
C00K C00O 1.524(2) . ?
C00L H00L 0.9300 . ?
C00M C00N 1.399(2) . ?
C00N H00N 0.9300 . ?
C00O C00S 1.526(3) . ?
C00O C00T 1.531(2) . ?
C00O C00U 1.524(3) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.379(3) . ?
C00Q H00Q 0.9300 . ?
C00R H00F 0.9600 . ?
C00R H00K 0.9600 . ?
C00R H00M 0.9600 . ?
C00S H00O 0.9600 . ?
C00S H00R 0.9600 . ?
C00S H00S 0.9600 . ?
C00T H00T 0.9600 . ?
C00T H00U 0.9600 . ?
C00T H00V 0.9600 . ?
C00U H00W 0.9600 . ?
C00U H00X 0.9600 . ?
C00U H00Y 0.9600 . ?
