#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/54/4515412.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_4515412
loop_
_publ_author_name
'Chu, Manman'
'Qiu, Bing'
'Zhang, Wei'
'Zhou, Zhonghao'
'Yang, Xinzheng'
'Yan, Yongli'
'Yao, Jiannian'
'Li, Yong Jun'
'Zhao, Yong Sheng'
_publ_section_title
;
 Tailoring the Energy Levels and Cavity Structures toward Organic
 Cocrystal Microlasers.
;
_journal_issue                   49
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              42740
_journal_page_last               42746
_journal_paper_doi               10.1021/acsami.8b16294
_journal_volume                  10
_journal_year                    2018
_chemical_formula_moiety         '2(C13 H12 N2 O2), C6 F4 I2'
_chemical_formula_sum            'C32 H24 F4 I2 N4 O4'
_chemical_formula_weight         858.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.444(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.0342(8)
_cell_length_b                   19.652(4)
_cell_length_c                   19.647(4)
_cell_measurement_reflns_used    4659
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4817
_cell_measurement_theta_min      1.4663
_cell_volume                     1556.2(5)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9504
	          2theta: -19.9986
scan:
	Number of images: 240
	           Slice: -110.0000 - 10.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9504
	          2theta: -19.9986
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.2436
_diffrn_orient_matrix_UB_12      -0.0465
_diffrn_orient_matrix_UB_13      -0.0059
_diffrn_orient_matrix_UB_21      0.0096
_diffrn_orient_matrix_UB_22      -0.0500
_diffrn_orient_matrix_UB_23      -0.0011
_diffrn_orient_matrix_UB_31      -0.0031
_diffrn_orient_matrix_UB_32      -0.0017
_diffrn_orient_matrix_UB_33      0.0508
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10207
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_description       needle
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.744
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0326
_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)+(0.0136P)²+1.8493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0624
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3270
_reflns_number_total             3491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b16294_si_002.cif
_cod_data_source_block           MFC
_cod_original_cell_volume        1556.3(6)
_cod_database_code               4515412
_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.
;
_diffrn_number_total             3607
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O -0.0480(7) 0.93168(11) 0.64018(12) 0.0434(6) Uani 1 1 d .
H1 H 0.0541 0.9265 0.6054 0.065 Uiso 1 1 calc GR
O2 O 0.8028(6) 0.87594(12) 0.29530(11) 0.0386(5) Uani 1 1 d .
N1 N 0.2136(6) 0.86617(12) 0.54220(12) 0.0275(5) Uani 1 1 d .
N2 N 0.4985(6) 0.81183(13) 0.45227(12) 0.0287(5) Uani 1 1 d .
C1 C 0.0043(7) 0.81015(15) 0.63891(14) 0.0260(6) Uani 1 1 d .
C2 C -0.0960(7) 0.87065(16) 0.66964(15) 0.0306(6) Uani 1 1 d .
C3 C -0.2472(8) 0.86897(18) 0.73199(16) 0.0397(8) Uani 1 1 d .
H3 H -0.3104 0.9092 0.7527 0.048 Uiso 1 1 calc R
C4 C -0.3025(8) 0.80746(19) 0.76288(17) 0.0410(8) Uani 1 1 d .
H4 H -0.4041 0.8065 0.8045 0.049 Uiso 1 1 calc R
C5 C -0.2102(8) 0.74708(18) 0.73332(17) 0.0409(8) Uani 1 1 d .
H5 H -0.2511 0.7058 0.7546 0.049 Uiso 1 1 calc R
C6 C -0.0563(8) 0.74849(16) 0.67184(16) 0.0349(7) Uani 1 1 d .
H6 H 0.0081 0.7079 0.6520 0.042 Uiso 1 1 calc R
C7 C 0.1648(7) 0.81067(15) 0.57409(14) 0.0271(6) Uani 1 1 d .
H7 H 0.2334 0.7698 0.5555 0.032 Uiso 1 1 calc R
C8 C 0.3644(7) 0.86798(15) 0.47875(14) 0.0264(6) Uani 1 1 d .
C9 C 0.3654(7) 0.93024(15) 0.44529(14) 0.0285(6) Uani 1 1 d .
H9 H 0.2698 0.9680 0.4651 0.034 Uiso 1 1 calc R
C10 C 0.5072(8) 0.93645(16) 0.38286(15) 0.0302(6) Uani 1 1 d .
H10 H 0.5073 0.9778 0.3598 0.036 Uiso 1 1 calc R
C11 C 0.6492(7) 0.87880(16) 0.35597(14) 0.0283(6) Uani 1 1 d .
C12 C 0.6365(8) 0.81826(16) 0.39197(15) 0.0323(7) Uani 1 1 d .
H12 H 0.7298 0.7798 0.3730 0.039 Uiso 1 1 calc R
C13 C 0.7856(9) 0.93529(19) 0.25343(17) 0.0444(9) Uani 1 1 d .
H13A H 0.8929 0.9265 0.2116 0.067 Uiso 1 1 calc GR
H13B H 0.8949 0.9724 0.2769 0.067 Uiso 1 1 calc GR
H13C H 0.5574 0.9469 0.2436 0.067 Uiso 1 1 calc GR
I1 I 0.66501(5) 0.66327(2) 0.47825(2) 0.02946(7) Uani 1 1 d .
F3 F 0.9217(6) 0.55171(10) 0.37268(9) 0.0565(6) Uani 1 1 d .
F4 F 1.1925(6) 0.42922(10) 0.39046(9) 0.0567(6) Uani 1 1 d .
C14 C 0.8576(7) 0.56519(14) 0.49079(14) 0.0247(6) Uani 1 1 d .
C15 C 0.9574(8) 0.52714(15) 0.43630(14) 0.0302(7) Uani 1 1 d .
C16 C 1.0976(8) 0.46363(15) 0.44554(14) 0.0297(6) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C2 O1 H1 109.5 . .
C11 O2 C13 117.1(2) . .
C7 N1 C8 122.4(2) . .
C12 N2 C8 117.1(3) . .
C2 C1 C7 121.3(3) . .
C6 C1 C2 118.4(3) . .
C6 C1 C7 120.3(3) . .
O1 C2 C1 121.3(3) . .
O1 C2 C3 118.4(3) . .
C3 C2 C1 120.3(3) . .
C2 C3 H3 120.2 . .
C4 C3 C2 119.7(3) . .
C4 C3 H3 120.2 . .
C3 C4 H4 119.4 . .
C3 C4 C5 121.2(3) . .
C5 C4 H4 119.4 . .
C4 C5 H5 120.3 . .
C4 C5 C6 119.4(3) . .
C6 C5 H5 120.3 . .
C1 C6 H6 119.5 . .
C5 C6 C1 121.0(3) . .
C5 C6 H6 119.5 . .
N1 C7 C1 121.3(3) . .
N1 C7 H7 119.3 . .
C1 C7 H7 119.3 . .
N2 C8 N1 121.2(3) . .
N2 C8 C9 122.1(3) . .
C9 C8 N1 116.8(3) . .
C8 C9 H9 119.7 . .
C10 C9 C8 120.5(3) . .
C10 C9 H9 119.7 . .
C9 C10 H10 121.3 . .
C9 C10 C11 117.4(3) . .
C11 C10 H10 121.3 . .
O2 C11 C10 125.2(3) . .
O2 C11 C12 115.9(3) . .
C10 C11 C12 118.9(3) . .
N2 C12 C11 124.0(3) . .
N2 C12 H12 118.0 . .
C11 C12 H12 118.0 . .
O2 C13 H13A 109.5 . .
O2 C13 H13B 109.5 . .
O2 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 I1 121.9(2) . .
C16 C14 I1 121.3(2) 3_766 .
C16 C14 C15 116.8(3) 3_766 .
F3 C15 C14 120.3(3) . .
F3 C15 C16 118.4(3) . .
C16 C15 C14 121.3(3) . .
F4 C16 C14 119.5(3) . 3_766
F4 C16 C15 118.6(3) . .
C14 C16 C15 121.9(3) 3_766 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8200 .
O1 C2 1.349(4) .
O2 C11 1.368(3) .
O2 C13 1.427(4) .
N1 C7 1.277(4) .
N1 C8 1.411(4) .
N2 C8 1.344(4) .
N2 C12 1.336(4) .
C1 C2 1.401(4) .
C1 C6 1.400(4) .
C1 C7 1.453(4) .
C2 C3 1.392(4) .
C3 H3 0.9300 .
C3 C4 1.375(5) .
C4 H4 0.9300 .
C4 C5 1.379(5) .
C5 H5 0.9300 .
C5 C6 1.382(4) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.389(4) .
C9 H9 0.9300 .
C9 C10 1.381(4) .
C10 H10 0.9300 .
C10 C11 1.384(4) .
C11 C12 1.386(4) .
C12 H12 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
I1 C14 2.089(3) .
F3 C15 1.342(3) .
F4 C16 1.346(3) .
C14 C15 1.380(4) .
C14 C16 1.378(4) 3_766
C15 C16 1.379(4) .
C16 C14 1.378(4) 3_766
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.82 1.85 2.579(3) 147.2
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 C2 C3 C4 179.3(3) . .
O2 C11 C12 N2 179.5(3) . .
N1 C8 C9 C10 -179.8(3) . .
N2 C8 C9 C10 -0.2(5) . .
C1 C2 C3 C4 -1.0(5) . .
C2 C1 C6 C5 -0.2(5) . .
C2 C1 C7 N1 -1.5(4) . .
C2 C3 C4 C5 0.2(5) . .
C3 C4 C5 C6 0.6(5) . .
C4 C5 C6 C1 -0.6(5) . .
C6 C1 C2 O1 -179.3(3) . .
C6 C1 C2 C3 1.0(4) . .
C6 C1 C7 N1 177.9(3) . .
C7 N1 C8 N2 -7.6(4) . .
C7 N1 C8 C9 172.1(3) . .
C7 C1 C2 O1 0.1(4) . .
C7 C1 C2 C3 -179.5(3) . .
C7 C1 C6 C5 -179.7(3) . .
C8 N1 C7 C1 -179.1(3) . .
C8 N2 C12 C11 0.2(5) . .
C8 C9 C10 C11 -0.7(4) . .
C9 C10 C11 O2 -179.3(3) . .
C9 C10 C11 C12 1.2(4) . .
C10 C11 C12 N2 -1.0(5) . .
C12 N2 C8 N1 -179.9(3) . .
C12 N2 C8 C9 0.4(4) . .
C13 O2 C11 C10 -6.6(4) . .
C13 O2 C11 C12 172.9(3) . .
I1 C14 C15 F3 -2.4(4) . .
I1 C14 C15 C16 177.1(2) . .
F3 C15 C16 F4 0.1(5) . .
F3 C15 C16 C14 -179.9(3) . 3_766
C14 C15 C16 F4 -179.5(3) . .
C14 C15 C16 C14 0.6(5) . 3_766
C16 C14 C15 F3 179.9(3) 3_766 .
C16 C14 C15 C16 -0.5(5) 3_766 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168345692
