#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558209.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_1558209
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 H15.02 N2 O2'
_chemical_formula_weight         291.34
_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             2020-04-01T17:47:47-00:00
_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                92.6441(8)
_cell_angle_beta                 107.7657(10)
_cell_angle_gamma                114.3850(11)
_cell_formula_units_Z            2
_cell_length_a                   8.17154(10)
_cell_length_b                   9.86186(11)
_cell_length_c                   10.93238(11)
_cell_measurement_reflns_used    17184
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      76.985
_cell_measurement_theta_min      4.317
_cell_volume                     748.951(18)
_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      250(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.97
_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      0.0603556
_diffrn_orient_matrix_UB_12      0.0567377
_diffrn_orient_matrix_UB_13      0.14792
_diffrn_orient_matrix_UB_21      -0.0024073
_diffrn_orient_matrix_UB_22      -0.1527367
_diffrn_orient_matrix_UB_23      0.0266123
_diffrn_orient_matrix_UB_31      0.2131385
_diffrn_orient_matrix_UB_32      0.0638387
_diffrn_orient_matrix_UB_33      0.0143248
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28234
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.97
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_min         4.333
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.69
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.76509
_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    1.293
_exptl_crystal_description       irregular
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.13
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0047(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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3093
_refine_ls_number_restraints     567
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.034
_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)+(0.0522P)²+0.0606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0
_reflns_number_gt                2793
_reflns_number_total             3093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE50_BA50_250
_cod_original_cell_volume        748.950(16)
_cod_database_code               1558209
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.956
_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 0.16780(10) 0.14887(8) 0.30455(7) 0.0535(2) Uani 1 1 d . . . . .
H1 H 0.200748 0.175172 0.384933 0.08 Uiso 1 1 calc R U . . .
O2 O 0.81895(11) 0.22039(10) 0.43197(7) 0.0613(2) Uani 1 1 d . . . . .
H2A H 0.82395 0.25688 0.503726 0.092 Uiso 1 1 calc R U . . .
N1 N 0.26224(13) 0.24320(11) -0.43198(8) 0.0539(2) Uani 1 1 d . . . . .
C1 C 0.31803(14) 0.14813(10) 0.27600(9) 0.0432(2) Uani 1 1 d . . . . .
C2 C 0.49304(14) 0.18352(10) 0.37297(9) 0.0436(2) Uani 1 1 d . . . . .
H2 H 0.509498 0.207959 0.461418 0.052 Uiso 1 1 calc R U . . .
C3 C 0.64442(15) 0.18312(11) 0.34030(9) 0.0468(2) Uani 1 1 d . . . . .
C4 C 0.61909(17) 0.14404(12) 0.20927(10) 0.0548(3) Uani 1 1 d . . . . .
H4 H 0.719888 0.141894 0.186155 0.066 Uiso 1 1 calc R U . . .
C5 C 0.44379(18) 0.10865(12) 0.11432(10) 0.0582(3) Uani 1 1 d . . . . .
H5 H 0.426473 0.082668 0.025911 0.07 Uiso 1 1 calc R U . . .
C6 C 0.29266(16) 0.11020(11) 0.14522(10) 0.0527(3) Uani 1 1 d . . . . .
H6 H 0.174398 0.085975 0.078771 0.063 Uiso 1 1 calc R U . . .
C7 C 0.19711(15) 0.14734(12) -0.35684(10) 0.0531(3) Uani 1 1 d . . . . .
H7 H 0.154451 0.04321 -0.385864 0.064 Uiso 1 1 calc R U . . .
C8 C 0.18917(15) 0.19307(12) -0.23903(10) 0.0503(2) Uani 1 1 d . . . . .
H8 H 0.14113 0.12106 -0.189706 0.06 Uiso 1 1 calc R U . . .
C9 C 0.25250(14) 0.34623(11) -0.19331(9) 0.0459(2) Uani 1 1 d D U . . .
C10 C 0.32581(16) 0.44709(12) -0.26929(11) 0.0536(3) Uani 1 1 d . . . . .
H10 H 0.374546 0.552216 -0.240942 0.064 Uiso 1 1 calc R U . . .
C11 C 0.32608(16) 0.39100(13) -0.38651(11) 0.0563(3) Uani 1 1 d . . . . .
H11 H 0.373861 0.460435 -0.437771 0.068 Uiso 1 1 calc R U . . .
C12A C 0.2182(13) 0.3786(7) -0.0665(7) 0.0395(10) Uani 0.457(3) 1 d D U P A 1
H12A H 0.162062 0.297306 -0.027319 0.047 Uiso 0.457(3) 1 calc R U P A 1
C13A C 0.2663(5) 0.5187(3) -0.0114(3) 0.0368(6) Uani 0.457(3) 1 d D U P A 1
H13A H 0.326865 0.597853 -0.050911 0.044 Uiso 0.457(3) 1 calc R U P A 1
C12B C 0.266(7) 0.4530(18) -0.085(3) 0.048(3) Uani 0.053(3) 1 d D U P A 2
H12B H 0.332963 0.556881 -0.084333 0.058 Uiso 0.053(3) 1 calc R U P A 2
C13B C 0.198(4) 0.4218(15) 0.008(3) 0.043(3) Uani 0.053(3) 1 d D U P A 2
H13B H 0.12631 0.317688 0.004949 0.051 Uiso 0.053(3) 1 calc R U P A 2
C14A C 0.2319(12) 0.5621(6) 0.1095(6) 0.0354(10) Uani 0.457(3) 1 d DG U P A 1
C15A C 0.1499(12) 0.4533(6) 0.1772(7) 0.0421(12) Uani 0.457(3) 1 d G U P A 1
H15A H 0.114953 0.350626 0.14806 0.051 Uiso 0.457(3) 1 calc R U P A 1
C16A C 0.1195(13) 0.4962(8) 0.2880(7) 0.0437(13) Uani 0.457(3) 1 d G U P A 1
H16A H 0.063974 0.422533 0.333842 0.052 Uiso 0.457(3) 1 calc R U P A 1
N2A N 0.1711(14) 0.6479(9) 0.3312(6) 0.0428(14) Uani 0.457(3) 1 d G U P A 1
C17A C 0.2532(14) 0.7568(7) 0.2634(7) 0.0439(12) Uani 0.457(3) 1 d G U P A 1
H17A H 0.288083 0.859395 0.292594 0.053 Uiso 0.457(3) 1 calc R U P A 1
C18A C 0.2836(12) 0.7139(6) 0.1526(6) 0.0423(11) Uani 0.457(3) 1 d G U P A 1
H18A H 0.339063 0.787491 0.106811 0.051 Uiso 0.457(3) 1 calc R U P A 1
C14B C 0.2154(11) 0.5263(6) 0.1215(5) 0.0458(12) Uani 0.543(3) 1 d D U P A 2
C15B C 0.1283(12) 0.4432(7) 0.2022(7) 0.0507(11) Uani 0.543(3) 1 d . U P A 2
H15B H 0.079352 0.336884 0.186707 0.061 Uiso 0.543(3) 1 calc R U P A 2
C16B C 0.1142(12) 0.5176(8) 0.3046(7) 0.0497(11) Uani 0.543(3) 1 d . U P A 2
H16B H 0.053095 0.457172 0.356434 0.06 Uiso 0.543(3) 1 calc R U P A 2
N2B N 0.1767(13) 0.6626(9) 0.3370(6) 0.0548(15) Uani 0.543(3) 1 d . U P A 2
C17B C 0.2582(13) 0.7377(7) 0.2607(7) 0.0554(13) Uani 0.543(3) 1 d . U P A 2
H17B H 0.307448 0.843852 0.281113 0.066 Uiso 0.543(3) 1 calc R U P A 2
C18B C 0.2811(10) 0.6812(6) 0.1541(6) 0.0483(10) Uani 0.543(3) 1 d . U P A 2
H18B H 0.340263 0.746287 0.104081 0.058 Uiso 0.543(3) 1 calc R U P A 2
C19 C 0.2496(12) 0.4095(7) -0.0789(7) 0.0511(14) Uani 0.49 1 d D U P A 2
C20 C 0.2373(6) 0.4657(5) 0.0137(4) 0.0550(8) Uani 0.49 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
-1 1 2 0.1024
-2 2 -6 0.081
-4 -1 0 0.0438
5 -1 -3 0.0658
1 -6 4 0.0337
4 1 0 0.0468
-2 -4 4 0.0464
-5 0 4 0.0804
-5 1 -1 0.0444
-3 2 -4 0.0582
-1 -5 -1 0.0561
1 5 1 0.0835
5 -3 0 0.0435
-2 6 2 0.0954
4 -6 1 0.0427
0 -6 2 0.0367
-2 -5 3 0.0426
3 4 -3 0.0582
-1 -1 7 0.0957
-4 -2 1 0.0435
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
-1 5 -4 0.0508
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 116.91(9) . . ?
O1 C1 C2 121.88(8) . . ?
O1 C1 C6 118.23(9) . . ?
C2 C1 C6 119.89(9) . . ?
C1 C2 C3 120.42(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.20(8) . . ?
O2 C3 C4 117.94(9) . . ?
C2 C3 C4 119.86(10) . . ?
C5 C4 C3 118.84(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.94(9) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.04(10) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.28(10) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.60(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C8 126.5(3) . . ?
C19 C9 C10 116.1(3) . . ?
C8 C9 C10 117.38(9) . . ?
C19 C9 C12B 15.7(5) . . ?
C8 C9 C12B 142.0(6) . . ?
C10 C9 C12B 100.5(5) . . ?
C8 C9 C12A 113.6(2) . . ?
C10 C9 C12A 128.9(2) . . ?
C11 C10 C9 119.00(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.79(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.3(4) . . ?
C13A C12A H12A 119.3 . . ?
C9 C12A H12A 119.3 . . ?
C12A C13A C14A 125.6(4) . . ?
C12A C13A H13A 117.2 . . ?
C14A C13A H13A 117.2 . . ?
C13B C12B C9 128.8(14) . . ?
C13B C12B H12B 115.6 . . ?
C9 C12B H12B 115.6 . . ?
C12B C13B C14B 130.0(13) . . ?
C12B C13B H13B 115 . . ?
C14B C13B H13B 115 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.1(3) . . ?
C18A C14A C13A 118.9(3) . . ?
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 114.8(3) . . ?
C18B C14B C20 119.8(4) . . ?
C15B C14B C20 125.4(4) . . ?
C18B C14B C13B 134.4(8) . . ?
C15B C14B C13B 110.4(7) . . ?
C20 C14B C13B 15.5(5) . . ?
C16B C15B C14B 119.3(3) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
N2B C16B C15B 126.5(3) . . ?
N2B C16B H16B 116.8 . . ?
C15B C16B H16B 116.8 . . ?
C16B N2B C17B 113.0(3) . . ?
N2B C17B C18B 127.8(4) . . ?
N2B C17B H17B 116.1 . . ?
C18B C17B H17B 116.1 . . ?
C17B C18B C14B 118.6(3) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175.5(9) . . ?
C19 C20 C14B 177.6(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 1.3585(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3544(13) . ?
O2 H2A 0.83 . ?
N1 C7 1.3322(14) . ?
N1 C11 1.3383(14) . ?
C1 C2 1.3854(14) . ?
C1 C6 1.3902(13) . ?
C2 C3 1.3896(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3949(13) . ?
C4 C5 1.3775(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3818(16) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3740(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3878(14) . ?
C8 H8 0.94 . ?
C9 C19 1.383(7) . ?
C9 C10 1.3879(15) . ?
C9 C12B 1.495(17) . ?
C9 C12A 1.541(6) . ?
C10 C11 1.3730(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12A C13A 1.326(7) . ?
C12A H12A 0.94 . ?
C13A C14A 1.510(5) . ?
C13A H13A 0.94 . ?
C12B C13B 1.297(18) . ?
C12B H12B 0.94 . ?
C13B C14B 1.504(17) . ?
C13B H13B 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 1.380(5) . ?
C14B C15B 1.387(5) . ?
C14B C20 1.389(6) . ?
C15B C16B 1.370(5) . ?
C15B H15B 0.94 . ?
C16B N2B 1.293(4) . ?
C16B H16B 0.94 . ?
N2B C17B 1.295(4) . ?
C17B C18B 1.364(4) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.183(8) . ?
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 2.7497(11) 175.2 1_556 yes
O2 H2A N2A^a 0.83 1.98 2.81(3) 176.3 2_666 yes
O2 H2A N2B^b 0.83 1.88 2.712(5) 177.4 2_666 yes
