#------------------------------------------------------------------------------
#$Date: 2019-11-10 01:38:41 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225567 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/54/4515413.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_4515413
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         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   36.542(16)
_cell_length_b                   36.542(16)
_cell_length_c                   4.623(3)
_cell_measurement_reflns_used    1290
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.2
_cell_volume                     5346(5)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.188
_diffrn_reflns_theta_max         25.188
_diffrn_reflns_theta_min         1.931
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       needle
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.274
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.1016
_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)+(0.0457P)²+22.9199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1870
_refine_ls_wR_factor_ref         0.1944
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1811
_reflns_number_total             2146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b16294_si_004.cif
_cod_data_source_block           MPI
_cod_original_cell_volume        5346(6)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4515413
_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.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.82804(9) 0.07925(9) 0.9634(7) 0.0414(8) Uani 1 1 d .
H1 H 0.8401 0.0987 0.8480 0.062 Uiso 1 1 calc GR
O2 O 0.96216(8) 0.26871(8) -0.1146(6) 0.0371(7) Uani 1 1 d .
N1 N 0.89115(10) 0.13703(9) 0.6605(6) 0.0278(7) Uani 1 1 d .
N2 N 0.94921(9) 0.18651(10) 0.3739(7) 0.0284(8) Uani 1 1 d .
C1 C 0.89899(12) 0.09124(12) 0.9944(8) 0.0290(9) Uani 1 1 d .
C2 C 0.85619(13) 0.06968(12) 1.0788(8) 0.0312(9) Uani 1 1 d .
C3 C 0.84226(14) 0.03812(12) 1.2887(9) 0.0397(11) Uani 1 1 d .
H3 H 0.8141 0.0241 1.3456 0.048 Uiso 1 1 calc R
C4 C 0.87007(16) 0.02769(13) 1.4117(9) 0.0456(12) Uani 1 1 d .
H4 H 0.8605 0.0068 1.5528 0.055 Uiso 1 1 calc R
C5 C 0.91218(15) 0.04792(14) 1.3287(9) 0.0458(12) Uani 1 1 d .
H5 H 0.9307 0.0404 1.4113 0.055 Uiso 1 1 calc R
C6 C 0.92645(14) 0.07955(13) 1.1211(9) 0.0381(10) Uani 1 1 d .
H6 H 0.9547 0.0932 1.0652 0.046 Uiso 1 1 calc R
C7 C 0.91484(12) 0.12478(12) 0.7817(8) 0.0282(9) Uani 1 1 d .
H7 H 0.9432 0.1380 0.7307 0.034 Uiso 1 1 calc R
C8 C 0.90875(12) 0.17047(11) 0.4572(8) 0.0261(8) Uani 1 1 d .
C9 C 0.88347(12) 0.18538(12) 0.3533(8) 0.0305(9) Uani 1 1 d .
H9 H 0.8555 0.1731 0.4141 0.037 Uiso 1 1 calc R
C10 C 0.89944(12) 0.21879(12) 0.1575(8) 0.0297(9) Uani 1 1 d .
H10 H 0.8827 0.2294 0.0868 0.036 Uiso 1 1 calc R
C11 C 0.94107(12) 0.23562(11) 0.0719(8) 0.0294(9) Uani 1 1 d .
C12 C 0.96427(12) 0.21799(12) 0.1862(8) 0.0308(9) Uani 1 1 d .
H12 H 0.9921 0.2292 0.1260 0.037 Uiso 1 1 calc R
C13 C 0.93950(14) 0.28870(13) -0.2228(9) 0.0393(10) Uani 1 1 d .
H13A H 0.9574 0.3112 -0.3520 0.059 Uiso 1 1 calc GR
H13B H 0.9313 0.3000 -0.0639 0.059 Uiso 1 1 calc GR
H13C H 0.9147 0.2683 -0.3246 0.059 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
C11 O2 C13 117.1(3)
C7 N1 C8 119.7(3)
C12 N2 C8 117.1(3)
C2 C1 C7 121.6(4)
C6 C1 C2 118.6(4)
C6 C1 C7 119.9(4)
O1 C2 C1 121.5(3)
O1 C2 C3 118.6(4)
C3 C2 C1 119.9(4)
C4 C3 C2 120.2(4)
C3 C4 C5 121.0(4)
C4 C5 C6 119.3(4)
C5 C6 C1 121.0(4)
N1 C7 C1 122.5(3)
N2 C8 N1 119.4(3)
N2 C8 C9 122.5(3)
C9 C8 N1 118.0(3)
C8 C9 C10 120.4(3)
C11 C10 C9 117.5(4)
O2 C11 C10 125.6(4)
O2 C11 C12 116.2(3)
C10 C11 C12 118.2(4)
N2 C12 C11 124.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.351(5)
O2 C11 1.367(4)
O2 C13 1.440(5)
N1 C7 1.285(5)
N1 C8 1.416(5)
N2 C8 1.346(5)
N2 C12 1.322(5)
C1 C2 1.410(5)
C1 C6 1.400(5)
C1 C7 1.447(5)
C2 C3 1.394(6)
C3 C4 1.374(6)
C4 C5 1.387(6)
C5 C6 1.388(6)
C8 C9 1.372(5)
C9 C10 1.392(5)
C10 C11 1.383(5)
C11 C12 1.400(5)
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 1.89 2.621(4) 147.5
