#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/13/7231310.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_7231310
loop_
_publ_author_name
'Chen, Shaojin'
'Liu, Wei'
'Ge, Zhaohai'
'Zhang, Wenxuan'
'Wang, Kun-Peng'
'Hu, Zhi-Qiang'
_publ_section_title
;
 Dimethylamine substituted bisbenzocoumarins: solvatochromic,
 mechanochromic and acidochromic properties
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5432
_journal_paper_doi               10.1039/C8CE01034J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C36 H32 N2 O8'
_chemical_formula_sum            'C36 H32 N2 O8'
_chemical_formula_weight         620.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-06-18 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.466(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.9695(15)
_cell_length_b                   8.1566(5)
_cell_length_c                   12.1516(7)
_cell_measurement_reflns_used    2380
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0800
_cell_measurement_theta_min      2.9210
_cell_volume                     2970.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  31.00   1.00    6.00    --  -40.98  38.00 120.00   38
  2  ω    -65.00 -32.00   1.00    6.00    --  -40.98  38.00 120.00   33
  3  ω    -94.00  -2.00   1.00    6.00    --  -40.98 125.00 150.00   92
  4  ω   -108.00 -14.00   1.00    6.00    --  -40.98 -57.00 -90.00   94
  5  ω     47.00 109.00   1.00    8.00    --  106.95 -95.00 -30.00   62
  6  ω     43.00 119.00   1.00    8.00    --  106.95-125.00-180.00   76
  7  ω     34.00 129.00   1.00    8.00    --  106.95 -45.00 -60.00   95
  8  ω     81.00 171.00   1.00    8.00    --  106.95  30.00-120.00   90
  9  ω    129.00 156.00   1.00    8.00    --  106.95 125.00   0.00   27
 10  ω     89.00 178.00   1.00    8.00    --  106.95  61.00  90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0258173000
_diffrn_orient_matrix_UB_12      0.1615298000
_diffrn_orient_matrix_UB_13      0.0157139000
_diffrn_orient_matrix_UB_21      0.0380116000
_diffrn_orient_matrix_UB_22      0.0946256000
_diffrn_orient_matrix_UB_23      -0.0562055000
_diffrn_orient_matrix_UB_31      -0.0230465000
_diffrn_orient_matrix_UB_32      -0.0246609000
_diffrn_orient_matrix_UB_33      -0.1126050000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5681
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.381
_diffrn_reflns_theta_min         2.949
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0743
_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)+(0.0975P)²+20.4213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2221
_refine_ls_wR_factor_ref         0.2329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2377
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01034j2.cif
_cod_data_source_block           lw-1
_cod_depositor_comments          'Adding full bibliography for 7231310.cif.'
_cod_original_cell_volume        2970.3(3)
_cod_database_code               7231310
_shelx_shelxl_version_number     2017/1
_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_max   0.909
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.022
_oxdiff_exptl_absorpt_empirical_full_min 0.164
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.43414(7) 0.5090(3) 0.71828(16) 0.0173(5) Uani 1 1 d .
O2 O 0.37965(8) 0.3389(3) 0.75739(18) 0.0243(6) Uani 1 1 d .
O3 O 0.31628(8) 0.2713(3) 0.59054(19) 0.0261(6) Uani 1 1 d .
O4 O 0.32650(8) 0.4181(3) 0.43674(19) 0.0270(6) Uani 1 1 d .
N1 N 0.63174(10) 0.9905(4) 0.6068(2) 0.0241(7) Uani 1 1 d .
C8 C 0.45894(10) 0.6022(4) 0.6457(2) 0.0149(6) Uani 1 1 d .
C4 C 0.44637(10) 0.6091(4) 0.5343(3) 0.0170(7) Uani 1 1 d .
C5 C 0.40619(10) 0.5290(4) 0.5010(2) 0.0163(7) Uani 1 1 d .
C9 C 0.49539(10) 0.6836(4) 0.6893(2) 0.0153(6) Uani 1 1 d .
C2 C 0.51119(10) 0.7769(4) 0.5001(3) 0.0173(7) Uani 1 1 d .
C1 C 0.52328(10) 0.7710(4) 0.6137(3) 0.0165(7) Uani 1 1 d .
C3 C 0.47265(10) 0.6981(4) 0.4625(2) 0.0176(7) Uani 1 1 d .
H3 H 0.464544 0.705434 0.388615 0.021 Uiso 1 1 calc R
C11 C 0.59111(11) 0.9290(4) 0.5749(3) 0.0187(7) Uani 1 1 d .
C7 C 0.39625(10) 0.4222(4) 0.6863(3) 0.0180(7) Uani 1 1 d .
C10 C 0.56289(10) 0.8502(4) 0.6490(2) 0.0165(7) Uani 1 1 d .
H10 H 0.570335 0.849814 0.723405 0.020 Uiso 1 1 calc R
C6 C 0.38107(10) 0.4429(4) 0.5725(3) 0.0183(7) Uani 1 1 d .
C16 C 0.33816(10) 0.3656(4) 0.5369(3) 0.0198(7) Uani 1 1 d .
C13 C 0.53888(11) 0.8673(4) 0.4272(3) 0.0188(7) Uani 1 1 d .
H13 H 0.530578 0.876591 0.353539 0.023 Uiso 1 1 calc R
C12 C 0.57708(11) 0.9402(4) 0.4626(3) 0.0214(7) Uani 1 1 d .
H12 H 0.594400 0.998446 0.412930 0.026 Uiso 1 1 calc R
C15 C 0.64887(12) 0.9667(5) 0.7180(3) 0.0281(8) Uani 1 1 d .
H15A H 0.636400 1.048150 0.765760 0.042 Uiso 1 1 calc GR
H15B H 0.680788 0.976784 0.718020 0.042 Uiso 1 1 calc GR
H15C H 0.640735 0.859526 0.743508 0.042 Uiso 1 1 calc GR
C14 C 0.65759(12) 1.0967(5) 0.5346(3) 0.0278(8) Uani 1 1 d .
H14A H 0.672581 1.031086 0.480664 0.042 Uiso 1 1 calc GR
H14B H 0.679246 1.156114 0.577391 0.042 Uiso 1 1 calc GR
H14C H 0.637954 1.172585 0.498133 0.042 Uiso 1 1 calc GR
C17 C 0.28395(11) 0.3589(5) 0.3948(3) 0.0279(8) Uani 1 1 d .
H17A H 0.259721 0.401260 0.438974 0.033 Uiso 1 1 calc R
H17B H 0.283036 0.240109 0.397158 0.033 Uiso 1 1 calc R
C18 C 0.27946(13) 0.4182(6) 0.2779(3) 0.0346(9) Uani 1 1 d .
H18A H 0.303769 0.376477 0.235197 0.052 Uiso 1 1 calc GR
H18B H 0.280011 0.535875 0.276707 0.052 Uiso 1 1 calc GR
H18C H 0.251732 0.380063 0.247130 0.052 Uiso 1 1 calc GR
H5 H 0.3970(11) 0.536(4) 0.432(3) 0.006(8) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_3
C8 O1 C7 122.9(2) .
C16 O4 C17 115.9(3) .
C11 N1 C15 121.3(3) .
C11 N1 C14 121.5(3) .
C15 N1 C14 116.9(3) .
O1 C8 C4 119.6(3) .
C9 C8 O1 116.6(3) .
C9 C8 C4 123.8(3) .
C8 C4 C5 118.4(3) .
C3 C4 C8 118.6(3) .
C3 C4 C5 123.0(3) .
C4 C5 H5 120(2) .
C6 C5 C4 121.9(3) .
C6 C5 H5 118(2) .
C8 C9 C9 121.1(3) 2_656
C8 C9 C1 117.1(3) .
C1 C9 C9 121.7(3) 2_656
C3 C2 C1 120.3(3) .
C3 C2 C13 121.3(3) .
C13 C2 C1 118.4(3) .
C2 C1 C9 119.5(3) .
C10 C1 C9 121.6(3) .
C10 C1 C2 118.9(3) .
C4 C3 C2 120.5(3) .
C4 C3 H3 119.7 .
C2 C3 H3 119.7 .
N1 C11 C10 121.8(3) .
N1 C11 C12 120.1(3) .
C10 C11 C12 118.1(3) .
O1 C7 C6 116.9(3) .
O2 C7 O1 115.2(3) .
O2 C7 C6 127.9(3) .
C1 C10 H10 119.1 .
C11 C10 C1 121.7(3) .
C11 C10 H10 119.1 .
C5 C6 C7 119.9(3) .
C5 C6 C16 121.0(3) .
C7 C6 C16 119.1(3) .
O3 C16 O4 124.0(3) .
O3 C16 C6 125.7(3) .
O4 C16 C6 110.4(3) .
C2 C13 H13 119.2 .
C12 C13 C2 121.6(3) .
C12 C13 H13 119.2 .
C11 C12 H12 119.4 .
C13 C12 C11 121.1(3) .
C13 C12 H12 119.4 .
N1 C15 H15A 109.5 .
N1 C15 H15B 109.5 .
N1 C15 H15C 109.5 .
H15A C15 H15B 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
N1 C14 H14A 109.5 .
N1 C14 H14B 109.5 .
N1 C14 H14C 109.5 .
H14A C14 H14B 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
O4 C17 H17A 110.3 .
O4 C17 H17B 110.3 .
O4 C17 C18 107.2(3) .
H17A C17 H17B 108.5 .
C18 C17 H17A 110.3 .
C18 C17 H17B 110.3 .
C17 C18 H18A 109.5 .
C17 C18 H18B 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18B 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.385(4) .
O1 C7 1.391(4) .
O2 C7 1.209(4) .
O3 C16 1.206(4) .
O4 C16 1.334(4) .
O4 C17 1.452(4) .
N1 C11 1.370(4) .
N1 C15 1.455(5) .
N1 C14 1.460(4) .
C8 C4 1.404(4) .
C8 C9 1.380(4) .
C4 C5 1.426(4) .
C4 C3 1.386(4) .
C5 C6 1.352(5) .
C5 H5 0.88(4) .
C9 C9 1.498(6) 2_656
C9 C1 1.436(4) .
C2 C1 1.425(4) .
C2 C3 1.396(5) .
C2 C13 1.425(4) .
C1 C10 1.415(4) .
C3 H3 0.9300 .
C11 C10 1.397(4) .
C11 C12 1.427(5) .
C7 C6 1.461(4) .
C10 H10 0.9300 .
C6 C16 1.493(4) .
C13 H13 0.9300 .
C13 C12 1.357(5) .
C12 H12 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.506(5) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C8 C4 C5 4.7(4) . .
O1 C8 C4 C3 -177.6(3) . .
O1 C8 C9 C9 -5.9(4) . 2_656
O1 C8 C9 C1 175.6(3) . .
O1 C7 C6 C5 6.9(5) . .
O1 C7 C6 C16 -174.1(3) . .
O2 C7 C6 C5 -173.7(3) . .
O2 C7 C6 C16 5.3(5) . .
N1 C11 C10 C1 -172.9(3) . .
N1 C11 C12 C13 174.0(3) . .
C8 O1 C7 O2 175.9(3) . .
C8 O1 C7 C6 -4.6(4) . .
C8 C4 C5 C6 -2.4(5) . .
C8 C4 C3 C2 1.0(5) . .
C8 C9 C1 C2 3.1(4) . .
C8 C9 C1 C10 -176.2(3) . .
C4 C8 C9 C9 174.4(3) . 2_656
C4 C8 C9 C1 -4.2(5) . .
C4 C5 C6 C7 -3.5(5) . .
C4 C5 C6 C16 177.5(3) . .
C5 C4 C3 C2 178.7(3) . .
C5 C6 C16 O3 170.7(3) . .
C5 C6 C16 O4 -10.5(4) . .
C9 C8 C4 C5 -175.6(3) . .
C9 C8 C4 C3 2.2(5) . .
C9 C9 C1 C2 -175.4(3) 2_656 .
C9 C9 C1 C10 5.3(4) 2_656 .
C9 C1 C10 C11 177.1(3) . .
C2 C1 C10 C11 -2.2(5) . .
C2 C13 C12 C11 0.1(5) . .
C1 C2 C3 C4 -1.9(5) . .
C1 C2 C13 C12 3.1(5) . .
C3 C4 C5 C6 -180.0(3) . .
C3 C2 C1 C9 -0.2(5) . .
C3 C2 C1 C10 179.1(3) . .
C3 C2 C13 C12 -178.1(3) . .
C7 O1 C8 C4 -1.1(4) . .
C7 O1 C8 C9 179.1(3) . .
C7 C6 C16 O3 -8.3(5) . .
C7 C6 C16 O4 170.5(3) . .
C10 C11 C12 C13 -4.2(5) . .
C16 O4 C17 C18 -174.4(3) . .
C13 C2 C1 C9 178.7(3) . .
C13 C2 C1 C10 -2.0(5) . .
C13 C2 C3 C4 179.2(3) . .
C12 C11 C10 C1 5.3(5) . .
C15 N1 C11 C10 4.3(5) . .
C15 N1 C11 C12 -173.8(3) . .
C14 N1 C11 C10 -169.3(3) . .
C14 N1 C11 C12 12.5(5) . .
C17 O4 C16 O3 2.1(5) . .
C17 O4 C16 C6 -176.7(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204998
