#------------------------------------------------------------------------------
#$Date: 2019-11-23 09:01:33 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232627 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/79/4347996.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_4347996
loop_
_publ_author_name
'Dolgopolova, Ekaterina A.'
'Rice, Allison M.'
'Smith, Mark D.'
'Shustova, Natalia B.'
_publ_section_title
;
 Photophysics, Dynamics, and Energy Transfer in Rigid Mimics of GFP-based
 Systems.
;
_journal_issue                   15
_journal_name_full               'Inorganic chemistry'
_journal_page_first              7257
_journal_page_last               7264
_journal_paper_doi               10.1021/acs.inorgchem.6b00835
_journal_volume                  55
_journal_year                    2016
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.291(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.4323(11)
_cell_length_b                   6.9502(6)
_cell_length_c                   14.6149(13)
_cell_measurement_reflns_used    9191
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.516
_cell_measurement_theta_min      2.890
_cell_volume                     1414.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEXII v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        30.024
_diffrn_reflns_theta_max         30.024
_diffrn_reflns_theta_min         2.890
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.3582
_exptl_absorpt_correction_T_min  0.3265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.9115.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0087(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0357
_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)+(0.0608P)²+0.7679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1995
_reflns_number_total             2229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b00835_si_007.cif
_cod_data_source_block           ead2ohtbu
_cod_database_code               4347996
_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   0.971
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H4C(0.5) H5A(0.5) H5B(0.5) H5C(0.5) H14A(0.5)
 H14B(0.5) H14C(0.5)
3.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'data crystal cleaved form long needle'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O1 O 0.07241(7) 0.5000 0.37374(6) 0.0239(2) Uani 1 2 d S T P . .
O2 O 0.40270(6) 0.5000 0.68120(6) 0.0197(2) Uani 1 2 d S T P . .
H2 H 0.3783(18) 0.5000 0.6165(18) 0.057(7) Uiso 1 2 d S T P . .
N1 N 0.22598(7) 0.5000 0.35031(7) 0.0145(2) Uani 1 2 d S T P . .
N2 N 0.31782(7) 0.5000 0.50042(7) 0.0150(2) Uani 1 2 d S T P . .
C1 C 0.15933(8) 0.5000 0.40435(8) 0.0150(2) Uani 1 2 d S T P . .
C2 C 0.22142(8) 0.5000 0.50319(8) 0.0129(2) Uani 1 2 d S T P . .
C3 C 0.31727(8) 0.5000 0.41100(8) 0.0150(2) Uani 1 2 d S T P . .
C4 C 0.40402(9) 0.5000 0.37455(9) 0.0242(3) Uani 1 2 d S T P . .
H4A H 0.3931 0.4163 0.3188 0.036 Uiso 0.5 1 calc GR . . A -1
H4B H 0.4591 0.4524 0.4239 0.036 Uiso 0.5 1 calc GR . . A -1
H4C H 0.4171 0.6313 0.3569 0.036 Uiso 0.5 1 calc GR . . A -1
C5 C 0.20155(9) 0.5000 0.24744(8) 0.0174(2) Uani 1 2 d S T P . .
H5A H 0.2404 0.4034 0.2256 0.026 Uiso 0.5 1 calc GR . . B -1
H5B H 0.2145 0.6274 0.2248 0.026 Uiso 0.5 1 calc GR . . B -1
H5C H 0.1333 0.4692 0.2223 0.026 Uiso 0.5 1 calc GR . . B -1
C6 C 0.18597(8) 0.5000 0.58017(8) 0.0131(2) Uani 1 2 d S T P . .
H6 H 0.1177(12) 0.5000 0.5663(11) 0.017(4) Uiso 1 2 d S T P . .
C7 C 0.23236(8) 0.5000 0.68166(7) 0.0113(2) Uani 1 2 d S T P . .
C8 C 0.33258(8) 0.5000 0.72606(8) 0.0121(2) Uani 1 2 d S T P . .
C9 C 0.36324(8) 0.5000 0.82521(8) 0.0120(2) Uani 1 2 d S T P . .
H9 H 0.4341(13) 0.5000 0.8544(12) 0.022(4) Uiso 1 2 d S T P . .
C10 C 0.29888(8) 0.5000 0.88074(7) 0.0116(2) Uani 1 2 d S T P . .
H10 H 0.3260(12) 0.5000 0.9519(12) 0.020(4) Uiso 1 2 d S T P . .
C11 C 0.19946(8) 0.5000 0.83967(7) 0.0108(2) Uani 1 2 d S T P . .
C12 C 0.16913(8) 0.5000 0.74105(8) 0.0119(2) Uani 1 2 d S T P . .
H12 H 0.1015(12) 0.5000 0.7091(11) 0.015(4) Uiso 1 2 d S T P . .
C13 C 0.12496(8) 0.5000 0.89727(7) 0.0118(2) Uani 1 2 d S T P . .
C14 C 0.17130(8) 0.5000 1.00460(8) 0.0145(2) Uani 1 2 d S T P . .
H14A H 0.1214 0.4831 1.0383 0.022 Uiso 0.5 1 calc GR . . C -1
H14B H 0.2044 0.6227 1.0232 0.022 Uiso 0.5 1 calc GR . . C -1
H14C H 0.2177 0.3943 1.0208 0.022 Uiso 0.5 1 calc GR . . C -1
C15 C 0.06183(6) 0.31901(12) 0.87241(6) 0.01660(18) Uani 1 1 d . . . . .
H15A H 0.0283 0.3205 0.8047 0.025 Uiso 1 1 calc GR . . . .
H15B H 0.0146 0.3173 0.9099 0.025 Uiso 1 1 calc GR . . . .
H15C H 0.1023 0.2040 0.8868 0.025 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_3
C8 O2 H2 111.6(15) .
C1 N1 C5 124.80(10) .
C3 N1 C1 108.64(9) .
C3 N1 C5 126.56(10) .
C3 N2 C2 106.55(10) .
O1 C1 N1 126.14(11) .
O1 C1 C2 131.08(11) .
N1 C1 C2 102.78(9) .
N2 C2 C1 108.69(9) .
C6 C2 N2 128.28(10) .
C6 C2 C1 123.03(10) .
N1 C3 C4 121.45(10) .
N2 C3 N1 113.34(10) .
N2 C3 C4 125.21(11) .
C3 C4 H4A 109.5 .
C3 C4 H4B 109.5 .
C3 C4 H4C 109.5 .
H4A C4 H4B 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
N1 C5 H5A 109.5 .
N1 C5 H5B 109.5 .
N1 C5 H5C 109.5 .
H5A C5 H5B 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
C2 C6 H6 114.9(9) .
C2 C6 C7 132.31(10) .
C7 C6 H6 112.8(9) .
C8 C7 C6 127.15(10) .
C12 C7 C6 115.25(9) .
C12 C7 C8 117.60(10) .
O2 C8 C7 125.76(10) .
O2 C8 C9 115.62(9) .
C9 C8 C7 118.61(9) .
C8 C9 H9 116.8(10) .
C10 C9 C8 121.94(10) .
C10 C9 H9 121.2(10) .
C9 C10 H10 117.8(10) .
C9 C10 C11 121.19(10) .
C11 C10 H10 121.0(10) .
C10 C11 C13 123.55(9) .
C12 C11 C10 116.77(9) .
C12 C11 C13 119.67(9) .
C7 C12 H12 115.9(10) .
C11 C12 C7 123.89(10) .
C11 C12 H12 120.2(10) .
C11 C13 C14 112.48(9) .
C11 C13 C15 109.16(6) .
C11 C13 C15 109.16(6) 6_565
C14 C13 C15 108.21(6) 6_565
C14 C13 C15 108.21(6) .
C15 C13 C15 109.59(9) 6_565
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14B 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C13 C15 H15A 109.5 .
C13 C15 H15B 109.5 .
C13 C15 H15C 109.5 .
H15A C15 H15B 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2156(15) .
O2 H2 0.92(3) .
O2 C8 1.3431(13) .
N1 C1 1.3964(14) .
N1 C3 1.3806(15) .
N1 C5 1.4508(14) .
N2 C2 1.4024(15) .
N2 C3 1.3048(14) .
C1 C2 1.4856(15) .
C2 C6 1.3531(15) .
C3 C4 1.4844(16) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6 0.952(16) .
C6 C7 1.4577(14) .
C7 C8 1.4206(15) .
C7 C12 1.4156(14) .
C8 C9 1.3990(15) .
C9 H9 0.999(18) .
C9 C10 1.3853(15) .
C10 H10 1.010(17) .
C10 C11 1.4017(15) .
C11 C12 1.3914(14) .
C11 C13 1.5304(14) .
C12 H12 0.964(17) .
C13 C14 1.5345(15) .
C13 C15 1.5395(10) .
C13 C15 1.5395(10) 6_565
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
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
O2 H2 N2 0.92(3) 1.69(3) 2.6028(13) 172(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_4
O1 C1 C2 N2 180.000(0) .
O1 C1 C2 C6 0.000(0) .
O2 C8 C9 C10 180.000(0) .
N1 C1 C2 N2 0.000(0) .
N1 C1 C2 C6 180.000(0) .
N2 C2 C6 C7 0.000(0) .
C1 N1 C3 N2 0.000(0) .
C1 N1 C3 C4 180.000(0) .
C1 C2 C6 C7 180.000(0) .
C2 N2 C3 N1 0.000(0) .
C2 N2 C3 C4 180.000(0) .
C2 C6 C7 C8 0.000(0) .
C2 C6 C7 C12 180.000(0) .
C3 N1 C1 O1 180.000(0) .
C3 N1 C1 C2 0.000(0) .
C3 N2 C2 C1 0.000(0) .
C3 N2 C2 C6 180.000(0) .
C5 N1 C1 O1 0.000(0) .
C5 N1 C1 C2 180.000(0) .
C5 N1 C3 N2 180.000(0) .
C5 N1 C3 C4 0.000(0) .
C6 C7 C8 O2 0.000(0) .
C6 C7 C8 C9 180.000(0) .
C6 C7 C12 C11 180.000(0) .
C7 C8 C9 C10 0.000(0) .
C8 C7 C12 C11 0.000(0) .
C8 C9 C10 C11 0.000(1) .
C9 C10 C11 C12 0.000(1) .
C9 C10 C11 C13 180.000(0) .
C10 C11 C12 C7 0.000(0) .
C10 C11 C13 C14 0.000(1) .
C10 C11 C13 C15 -120.11(6) .
C10 C11 C13 C15 120.12(6) 6_565
C12 C7 C8 O2 180.000(0) .
C12 C7 C8 C9 0.000(0) .
C12 C11 C13 C14 180.000(0) .
C12 C11 C13 C15 59.89(6) .
C12 C11 C13 C15 -59.88(6) 6_565
C13 C11 C12 C7 180.000(0) .
