#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558203.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_1558203
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 H14.59 N2 O2'
_chemical_formula_weight         290.9
_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             2020-04-02T10:32:50-00:00
_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                92.2144(13)
_cell_angle_beta                 108.1472(16)
_cell_angle_gamma                114.5712(17)
_cell_formula_units_Z            2
_cell_length_a                   8.17391(17)
_cell_length_b                   9.81420(15)
_cell_length_c                   10.94231(17)
_cell_measurement_reflns_used    10658
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      77.224
_cell_measurement_theta_min      4.311
_cell_volume                     744.10(3)
_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      N~2~
_diffrn_ambient_temperature      210(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 0.972
_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      -0.182013
_diffrn_orient_matrix_UB_12      -0.0495251
_diffrn_orient_matrix_UB_13      0.0354902
_diffrn_orient_matrix_UB_21      0.1272205
_diffrn_orient_matrix_UB_22      0.075972
_diffrn_orient_matrix_UB_23      0.1443638
_diffrn_orient_matrix_UB_31      -0.0070495
_diffrn_orient_matrix_UB_32      0.1507691
_diffrn_orient_matrix_UB_33      -0.0267924
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.972
_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            14719
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.387
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9176
_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    1.298
_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         0.162
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0035(7)
_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   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0335
_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)+(0.0466P)²+0.0735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0
_reflns_number_gt                2809
_reflns_number_total             3080
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE25_BA75_210
_cod_original_cell_volume        744.10(2)
_cod_database_code               1558203
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.945
_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 0.16716(10) 0.14739(8) 0.30444(7) 0.04481(19) Uani 1 1 d . . . . .
H1 H 0.200279 0.172954 0.384871 0.067 Uiso 1 1 calc R U . . .
O2 O 0.81883(11) 0.21566(10) 0.43345(7) 0.0516(2) Uani 1 1 d . . . . .
H2A H 0.824479 0.252357 0.505132 0.077 Uiso 1 1 calc R U . . .
N1 N 0.26277(12) 0.24259(11) -0.43255(8) 0.0460(2) Uani 1 1 d . . . . .
C1 C 0.31760(14) 0.14715(10) 0.27614(9) 0.0372(2) Uani 1 1 d . . . . .
C2 C 0.49260(14) 0.18040(10) 0.37381(9) 0.0373(2) Uani 1 1 d . . . . .
H2 H 0.508822 0.203133 0.462298 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64439(15) 0.18022(11) 0.34123(9) 0.0401(2) Uani 1 1 d . . . . .
C4 C 0.61921(17) 0.14325(12) 0.21028(10) 0.0472(2) Uani 1 1 d . . . . .
H4 H 0.719859 0.14081 0.187458 0.057 Uiso 1 1 calc R U . . .
C5 C 0.44405(18) 0.11025(13) 0.11460(10) 0.0506(3) Uani 1 1 d . . . . .
H5 H 0.426949 0.085786 0.026161 0.061 Uiso 1 1 calc R U . . .
C6 C 0.29263(16) 0.11215(11) 0.14524(10) 0.0459(2) Uani 1 1 d . . . . .
H6 H 0.174842 0.090116 0.078508 0.055 Uiso 1 1 calc R U . . .
C7 C 0.19762(15) 0.14692(12) -0.35639(10) 0.0447(2) Uani 1 1 d . . . . .
H7 H 0.154212 0.042053 -0.384517 0.054 Uiso 1 1 calc R U . . .
C8 C 0.19076(15) 0.19409(11) -0.23850(10) 0.0425(2) Uani 1 1 d . . . . .
H8 H 0.142243 0.122472 -0.188507 0.051 Uiso 1 1 calc R U . . .
C9 C 0.25650(13) 0.34894(11) -0.19455(9) 0.0389(2) Uani 1 1 d D . . . .
C10 C 0.32978(15) 0.44966(12) -0.27146(10) 0.0451(2) Uani 1 1 d . . . . .
H10 H 0.379378 0.555523 -0.244084 0.054 Uiso 1 1 calc R U . . .
C11 C 0.32840(15) 0.39154(13) -0.38846(11) 0.0480(3) Uani 1 1 d . . . . .
H11 H 0.37637 0.460538 -0.440438 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2194(19) 0.3811(11) -0.0672(12) 0.0325(14) Uani 0.294(10) 1 d D U P A 1
H12 H 0.161531 0.298085 -0.029622 0.039 Uiso 0.294(10) 1 calc R U P A 1
C13 C 0.2648(8) 0.5173(9) -0.0110(6) 0.0337(11) Uani 0.294(10) 1 d D U P A 1
H13 H 0.326732 0.597669 -0.049564 0.04 Uiso 0.294(10) 1 calc R U P A 1
C14A C 0.2300(19) 0.5629(12) 0.1101(10) 0.0331(17) Uani 0.294(10) 1 d DG U P A
1
C15A C 0.1490(19) 0.4512(10) 0.1768(11) 0.0383(18) Uani 0.294(10) 1 d G U P A 1
H15A H 0.116806 0.348882 0.147442 0.046 Uiso 0.294(10) 1 calc R U P A 1
C16A C 0.1157(18) 0.4909(12) 0.2868(10) 0.0371(19) Uani 0.294(10) 1 d G U P A 1
H16A H 0.06098 0.415307 0.331949 0.045 Uiso 0.294(10) 1 calc R U P A 1
N2A N 0.163(2) 0.6422(13) 0.3302(10) 0.0344(18) Uani 0.294(10) 1 d G U P A 1
C17A C 0.244(2) 0.7539(11) 0.2635(12) 0.0377(19) Uani 0.294(10) 1 d G U P A 1
H17A H 0.276614 0.856248 0.292836 0.045 Uiso 0.294(10) 1 calc R U P A 1
C18A C 0.278(2) 0.7143(11) 0.1534(11) 0.0370(18) Uani 0.294(10) 1 d G U P A 1
H18A H 0.332441 0.789827 0.108328 0.044 Uiso 0.294(10) 1 calc R U P A 1
C14B C 0.2149(8) 0.5282(6) 0.1224(4) 0.0366(8) Uani 0.706(10) 1 d D U P A 2
C15B C 0.1262(8) 0.4418(5) 0.2018(5) 0.0406(7) Uani 0.706(10) 1 d . U P A 2
H15B H 0.077775 0.335005 0.185756 0.049 Uiso 0.706(10) 1 calc R U P A 2
C16B C 0.1107(8) 0.5154(6) 0.3046(5) 0.0410(9) Uani 0.706(10) 1 d . U P A 2
H16B H 0.049191 0.454868 0.356527 0.049 Uiso 0.706(10) 1 calc R U P A 2
N2B N 0.1759(9) 0.6649(6) 0.3354(5) 0.0433(9) Uani 0.706(10) 1 d . U P A 2
C17B C 0.2600(9) 0.7446(5) 0.2590(6) 0.0445(9) Uani 0.706(10) 1 d . U P A 2
H17B H 0.308835 0.851246 0.278815 0.053 Uiso 0.706(10) 1 calc R U P A 2
C18B C 0.2823(8) 0.6851(6) 0.1533(5) 0.0395(8) Uani 0.706(10) 1 d . U P A 2
H18B H 0.342113 0.749431 0.102613 0.047 Uiso 0.706(10) 1 calc R U P A 2
C19 C 0.2516(9) 0.4117(6) -0.0793(6) 0.0425(9) Uani 0.706(10) 1 d D U P A 2
C20 C 0.2347(4) 0.4627(5) 0.0146(3) 0.0429(6) Uani 0.706(10) 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
-2 6 -1 0.0431
5 -4 -4 0.0754
5 0 0 0.0393
1 -5 5 0.0478
0 -3 -5 0.0753
0 3 -6 0.0824
-5 0 0 0.0431
2 -6 2 0.0449
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 -4 4 0.0384
3 0 4 0.0674
-3 -1 -4 0.0729
-1 1 7 0.0918
-1 -2 7 0.0812
3 -4 -5 0.0856
0 5 -4 0.0552
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 117.05(9) . . ?
O1 C1 C2 121.81(8) . . ?
O1 C1 C6 118.21(9) . . ?
C2 C1 C6 119.98(9) . . ?
C1 C2 C3 120.29(9) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 117.99(9) . . ?
O2 C3 C2 122.08(9) . . ?
C4 C3 C2 119.92(9) . . ?
C5 C4 C3 118.91(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.87(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.00(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.33(9) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.15(9) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 117.85(9) . . ?
C10 C9 C19 117.1(2) . . ?
C8 C9 C19 125.0(2) . . ?
C10 C9 C12 129.4(4) . . ?
C8 C9 C12 112.5(4) . . ?
C11 C10 C9 118.76(9) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.82(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 123.0(9) . . ?
C13 C12 H12 118.5 . . ?
C9 C12 H12 118.5 . . ?
C12 C13 C14A 128.0(9) . . ?
C12 C13 H13 116 . . ?
C14A C13 H13 116 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.3(5) . . ?
C18A C14A C13 120.7(5) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A 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 116.65(19) . . ?
C18B C14B C20 120.5(3) . . ?
C15B C14B C20 122.8(3) . . ?
C16B C15B C14B 119.0(2) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 124.8(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C17B N2B C16B 115.1(2) . . ?
N2B C17B C18B 125.7(2) . . ?
N2B C17B H17B 117.2 . . ?
C18B C17B H17B 117.2 . . ?
C17B C18B C14B 118.8(2) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 175.6(6) . . ?
C19 C20 C14B 177.4(6) . . ?
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 1.3593(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3552(12) . ?
O2 H2A 0.83 . ?
N1 C7 1.3344(14) . ?
N1 C11 1.3378(14) . ?
C1 C2 1.3883(14) . ?
C1 C6 1.3903(13) . ?
C2 C3 1.3942(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3933(14) . ?
C4 C5 1.3803(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3863(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3792(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3903(14) . ?
C8 H8 0.94 . ?
C9 C10 1.3892(15) . ?
C9 C19 1.401(5) . ?
C9 C12 1.563(11) . ?
C10 C11 1.3762(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.297(12) . ?
C12 H12 0.94 . ?
C13 C14A 1.527(9) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.388(3) . ?
C14B C15B 1.392(3) . ?
C14B C20 1.407(4) . ?
C15B C16B 1.381(4) . ?
C15B H15B 0.94 . ?
C16B N2B 1.323(3) . ?
C16B H16B 0.94 . ?
N2B C17B 1.321(3) . ?
C17B C18B 1.371(3) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.196(6) . ?
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 0.83 1.92 2.7478(11) 174.6 1_556 yes
O2 H2A N2A^a 0.83 2 2.82(5) 174.4 2_666 yes
O2 H2A N2B^b 0.83 1.9 2.726(4) 177 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 -179.52(8) . . . . ?
C6 C1 C2 C3 0.57(14) . . . . ?
C1 C2 C3 O2 178.37(8) . . . . ?
C1 C2 C3 C4 -1.42(14) . . . . ?
O2 C3 C4 C5 -178.52(9) . . . . ?
C2 C3 C4 C5 1.29(15) . . . . ?
C3 C4 C5 C6 -0.33(16) . . . . ?
C4 C5 C6 C1 -0.51(16) . . . . ?
O1 C1 C6 C5 -179.52(9) . . . . ?
C2 C1 C6 C5 0.39(14) . . . . ?
C11 N1 C7 C8 1.73(15) . . . . ?
N1 C7 C8 C9 -0.76(16) . . . . ?
C7 C8 C9 C10 -1.13(14) . . . . ?
C7 C8 C9 C19 177.7(3) . . . . ?
C7 C8 C9 C12 174.2(6) . . . . ?
C8 C9 C10 C11 1.95(14) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.4(7) . . . . ?
C7 N1 C11 C10 -0.82(16) . . . . ?
C9 C10 C11 N1 -1.02(16) . . . . ?
C10 C9 C12 C13 -3.6(16) . . . . ?
C8 C9 C12 C13 -178.3(9) . . . . ?
C9 C12 C13 C14A 177.7(9) . . . . ?
C12 C13 C14A C15A 3.6(14) . . . . ?
C12 C13 C14A C18A -176.1(10) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A -179.7(10) . . . . ?
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 179.7(10) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -179.1(5) . . . . ?
C14B C15B C16B N2B -0.6(3) . . . . ?
C15B C16B N2B C17B 0.4(3) . . . . ?
C16B N2B C17B C18B 0.5(3) . . . . ?
N2B C17B C18B C14B -1.1(3) . . . . ?
C15B C14B C18B C17B 0.7(3) . . . . ?
C20 C14B C18B C17B 179.9(5) . . . . ?
