#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558202.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_1558202
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C18 H14.6 N2 O2'
_chemical_formula_weight         290.92
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-02T10:39:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.5489(11)
_cell_angle_beta                 107.9571(13)
_cell_angle_gamma                114.4335(14)
_cell_formula_units_Z            2
_cell_length_a                   8.23553(13)
_cell_length_b                   9.85058(13)
_cell_length_c                   10.96006(14)
_cell_measurement_reflns_used    9266
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      77.052
_cell_measurement_theta_min      4.309
_cell_volume                     754.73(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1801461
_diffrn_orient_matrix_UB_12      -0.0484094
_diffrn_orient_matrix_UB_13      0.0358314
_diffrn_orient_matrix_UB_21      0.1263725
_diffrn_orient_matrix_UB_22      0.0763639
_diffrn_orient_matrix_UB_23      0.1439825
_diffrn_orient_matrix_UB_31      -0.0067914
_diffrn_orient_matrix_UB_32      0.1501464
_diffrn_orient_matrix_UB_33      -0.0267269
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14795
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.252
_diffrn_reflns_theta_min         4.327
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.28
_exptl_crystal_description       irregular
_exptl_crystal_F_000             305
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0530P)²+0.0536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0
_reflns_number_gt                2722
_reflns_number_total             3117
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE25_BA75_290
_cod_original_formula_sum        'C18 H14.60 N2 O2'
_cod_database_code               1558202
_shelx_estimated_absorpt_t_min   0.87
_shelx_estimated_absorpt_t_max   0.946
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.16928(11) 0.14547(9) 0.30455(8) 0.0637(2) Uani 1 1 d . . . . .
H1 H 0.200471 0.168266 0.384046 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81576(12) 0.21562(11) 0.43213(8) 0.0734(3) Uani 1 1 d . . . . .
H2A H 0.819923 0.24911 0.503465 0.11 Uiso 1 1 calc R U . . .
N1 N 0.26237(14) 0.24129(12) -0.43228(9) 0.0637(3) Uani 1 1 d . . . . .
C1 C 0.31911(15) 0.14580(11) 0.27618(10) 0.0514(2) Uani 1 1 d . . . . .
C2 C 0.49213(15) 0.17924(11) 0.37302(10) 0.0516(2) Uani 1 1 d . . . . .
H2 H 0.507828 0.201411 0.460481 0.062 Uiso 1 1 calc R U . . .
C3 C 0.64266(16) 0.17989(12) 0.34037(10) 0.0558(3) Uani 1 1 d . . . . .
C4 C 0.61805(19) 0.14360(13) 0.20989(12) 0.0658(3) Uani 1 1 d . . . . .
H4 H 0.717084 0.141818 0.187108 0.079 Uiso 1 1 calc R U . . .
C5 C 0.4451(2) 0.11039(14) 0.11506(11) 0.0701(3) Uani 1 1 d . . . . .
H5 H 0.428668 0.086607 0.027643 0.084 Uiso 1 1 calc R U . . .
C6 C 0.29496(18) 0.11132(13) 0.14585(11) 0.0637(3) Uani 1 1 d . . . . .
H6 H 0.179334 0.089127 0.080055 0.076 Uiso 1 1 calc R U . . .
C7 C 0.19736(17) 0.14764(13) -0.35611(11) 0.0628(3) Uani 1 1 d . . . . .
H7 H 0.153818 0.044012 -0.383699 0.075 Uiso 1 1 calc R U . . .
C8 C 0.19119(16) 0.19593(13) -0.23899(11) 0.0591(3) Uani 1 1 d . . . . .
H8 H 0.143605 0.126096 -0.189327 0.071 Uiso 1 1 calc R U . . .
C9 C 0.25676(14) 0.35011(12) -0.19552(10) 0.0533(2) Uani 1 1 d D . . . .
C10 C 0.32959(17) 0.44889(13) -0.27255(12) 0.0619(3) Uani 1 1 d . . . . .
H10 H 0.378761 0.553408 -0.245844 0.074 Uiso 1 1 calc R U . . .
C11 C 0.32781(17) 0.38975(14) -0.38869(12) 0.0663(3) Uani 1 1 d . . . . .
H11 H 0.374977 0.456948 -0.440292 0.08 Uiso 1 1 calc R U . . .
C12 C 0.223(2) 0.3833(11) -0.0684(13) 0.0475(17) Uani 0.301(12) 1 d D U P A 1
H12 H 0.170336 0.300273 -0.031506 0.057 Uiso 0.301(12) 1 calc R U P A 1
C13 C 0.2604(10) 0.5118(10) -0.0097(8) 0.0498(13) Uani 0.301(12) 1 d D U P A 1
H13 H 0.319297 0.592465 -0.046909 0.06 Uiso 0.301(12) 1 calc R U P A 1
C14A C 0.227(2) 0.5586(14) 0.1103(11) 0.047(2) Uani 0.301(12) 1 d DG U P A 1
C15A C 0.148(2) 0.4496(11) 0.1788(12) 0.056(2) Uani 0.301(12) 1 d G U P A 1
H15A H 0.116116 0.348272 0.150776 0.067 Uiso 0.301(12) 1 calc R U P A 1
C16A C 0.117(2) 0.4919(14) 0.2890(12) 0.054(2) Uani 0.301(12) 1 d G U P A 1
H16A H 0.064359 0.418929 0.334749 0.065 Uiso 0.301(12) 1 calc R U P A 1
N2A N 0.165(2) 0.6433(15) 0.3308(11) 0.052(2) Uani 0.301(12) 1 d G U P A 1
C17A C 0.243(2) 0.7524(12) 0.2624(13) 0.055(2) Uani 0.301(12) 1 d G U P A 1
H17A H 0.275392 0.853681 0.290348 0.067 Uiso 0.301(12) 1 calc R U P A 1
C18A C 0.274(2) 0.7101(12) 0.1521(12) 0.054(2) Uani 0.301(12) 1 d G U P A 1
H18A H 0.327151 0.783027 0.106375 0.065 Uiso 0.301(12) 1 calc R U P A 1
C14B C 0.2145(9) 0.5257(7) 0.1226(5) 0.0514(10) Uani 0.699(12) 1 d D U P A 2
C15B C 0.1270(10) 0.4416(6) 0.2021(6) 0.0571(9) Uani 0.699(12) 1 d . U P A 2
H15B H 0.078653 0.336305 0.186284 0.068 Uiso 0.699(12) 1 calc R U P A 2
C16B C 0.1127(10) 0.5159(7) 0.3046(5) 0.0577(10) Uani 0.699(12) 1 d . U P A 2
H16B H 0.052215 0.456909 0.355943 0.069 Uiso 0.699(12) 1 calc R U P A 2
N2B N 0.1779(10) 0.6638(7) 0.3353(5) 0.0603(11) Uani 0.699(12) 1 d . U P A 2
C17B C 0.2610(10) 0.7416(6) 0.2593(6) 0.0627(11) Uani 0.699(12) 1 d . U P A 2
H17B H 0.310016 0.84683 0.27915 0.075 Uiso 0.699(12) 1 calc R U P A 2
C18B C 0.2816(9) 0.6816(7) 0.1537(6) 0.0567(9) Uani 0.699(12) 1 d . U P A 2
H18B H 0.339893 0.744518 0.103445 0.068 Uiso 0.699(12) 1 calc R U P A 2
C19 C 0.2525(10) 0.4156(8) -0.0807(6) 0.0610(12) Uani 0.699(12) 1 d D U P A 2
C20 C 0.2323(5) 0.4585(6) 0.0143(3) 0.0602(7) Uani 0.699(12) 1 d D U P A 2
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 0 0.0393
-5 0 0 0.0431
3 -4 -5 0.0856
2 -6 2 0.0449
1 -5 5 0.0478
-1 -2 7 0.0812
-2 6 -1 0.0431
0 3 -6 0.0824
0 5 -4 0.0552
5 -4 -4 0.0754
-3 -3 5 0.0681
2 4 -1 0.0344
5 -4 1 0.0424
3 0 4 0.0674
3 -4 4 0.0384
-3 -1 -4 0.0729
-1 1 7 0.0918
0 -3 -5 0.0753
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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 116.90(10) . . ?
O1 C1 C2 121.95(9) . . ?
O1 C1 C6 118.19(10) . . ?
C2 C1 C6 119.86(10) . . ?
C1 C2 C3 120.39(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C4 117.96(10) . . ?
O2 C3 C2 122.19(9) . . ?
C4 C3 C2 119.85(11) . . ?
C5 C4 C3 118.95(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.88(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.06(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.44(11) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.23(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.71(10) . . ?
C10 C9 C19 116.7(3) . . ?
C8 C9 C19 125.6(3) . . ?
C10 C9 C12 129.7(4) . . ?
C8 C9 C12 112.4(4) . . ?
C11 C10 C9 118.79(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.90(11) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C13 C12 C9 126.5(11) . . ?
C13 C12 H12 116.7 . . ?
C9 C12 H12 116.7 . . ?
C12 C13 C14A 131.8(11) . . ?
C12 C13 H13 114.1 . . ?
C14A C13 H13 114.1 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.8(7) . . ?
C18A C14A C13 120.2(7) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C16A N2A C17A 120 . . ?
C18A C17A N2A 120 . . ?
C18A C17A H17A 120 . . ?
N2A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.2(2) . . ?
C18B C14B C20 121.0(4) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.2(2) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 124.9(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C16B N2B C17B 115.1(2) . . ?
N2B C17B C18B 125.8(3) . . ?
N2B C17B H17B 117.1 . . ?
C18B C17B H17B 117.1 . . ?
C17B C18B C14B 118.9(2) . . ?
C17B C18B H18B 120.5 . . ?
C14B C18B H18B 120.5 . . ?
C20 C19 C9 173.5(8) . . ?
C19 C20 C14B 173.4(7) . . ?
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
O1 C1 1.3611(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3554(14) . ?
O2 H2A 0.82 . ?
N1 C7 1.3305(16) . ?
N1 C11 1.3358(16) . ?
C1 C2 1.3833(15) . ?
C1 C6 1.3860(14) . ?
C2 C3 1.3900(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3892(15) . ?
C4 C5 1.3736(19) . ?
C4 H4 0.93 . ?
C5 C6 1.3821(18) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3720(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3870(15) . ?
C8 H8 0.93 . ?
C9 C10 1.3863(16) . ?
C9 C19 1.406(6) . ?
C9 C12 1.548(11) . ?
C10 C11 1.3694(17) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.263(12) . ?
C12 H12 0.93 . ?
C13 C14A 1.515(10) . ?
C13 H13 0.93 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.93 . ?
C16A N2A 1.39 . ?
C16A H16A 0.93 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.93 . ?
C18A H18A 0.93 . ?
C14B C18B 1.384(4) . ?
C14B C15B 1.386(4) . ?
C14B C20 1.409(5) . ?
C15B C16B 1.375(4) . ?
C15B H15B 0.93 . ?
C16B N2B 1.312(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.313(3) . ?
C17B C18B 1.364(3) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.190(7) . ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.94 2.7557(12) 172.7 1_556 yes
O2 H2A N2A^a 0.82 2 2.82(6) 172.4 2_666 yes
O2 H2A N2B^b 0.82 1.92 2.740(5) 176 2_666 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.40(9) . . . . ?
C6 C1 C2 C3 0.61(15) . . . . ?
C1 C2 C3 O2 178.38(9) . . . . ?
C1 C2 C3 C4 -1.38(16) . . . . ?
O2 C3 C4 C5 -178.54(11) . . . . ?
C2 C3 C4 C5 1.23(17) . . . . ?
C3 C4 C5 C6 -0.34(19) . . . . ?
C4 C5 C6 C1 -0.42(18) . . . . ?
O1 C1 C6 C5 -179.71(10) . . . . ?
C2 C1 C6 C5 0.28(16) . . . . ?
C11 N1 C7 C8 1.43(17) . . . . ?
N1 C7 C8 C9 -0.48(18) . . . . ?
C7 C8 C9 C10 -1.28(16) . . . . ?
C7 C8 C9 C19 177.4(4) . . . . ?
C7 C8 C9 C12 175.0(7) . . . . ?
C8 C9 C10 C11 2.01(16) . . . . ?
C19 C9 C10 C11 -176.7(3) . . . . ?
C12 C9 C10 C11 -173.5(8) . . . . ?
C7 N1 C11 C10 -0.62(18) . . . . ?
C9 C10 C11 N1 -1.10(18) . . . . ?
C10 C9 C12 C13 -1.1(19) . . . . ?
C8 C9 C12 C13 -176.8(12) . . . . ?
C9 C12 C13 C14A 176.8(11) . . . . ?
C12 C13 C14A C15A 3.0(17) . . . . ?
C12 C13 C14A C18A -177.0(13) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 179.9(12) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -179.9(12) . . . . ?
C18B C14B C15B C16B -0.1(3) . . . . ?
C20 C14B C15B C16B -178.9(6) . . . . ?
C14B C15B C16B N2B -0.6(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.7(4) . . . . ?
N2B C17B C18B C14B -1.5(4) . . . . ?
C15B C14B C18B C17B 1.1(3) . . . . ?
C20 C14B C18B C17B 179.9(6) . . . . ?
