#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558210.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_1558210
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             2020-04-01T17:49:39-00:00
_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                92.8140(8)
_cell_angle_beta                 107.7114(9)
_cell_angle_gamma                114.3110(11)
_cell_formula_units_Z            2
_cell_length_a                   8.20840(10)
_cell_length_b                   9.88002(10)
_cell_length_c                   10.94248(10)
_cell_measurement_reflns_used    15728
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      76.62
_cell_measurement_theta_min      4.315
_cell_volume                     754.705(17)
_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 0.996
_diffrn_measured_fraction_theta_max 0.961
_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      0.0607917
_diffrn_orient_matrix_UB_12      0.0567316
_diffrn_orient_matrix_UB_13      0.1479539
_diffrn_orient_matrix_UB_21      -0.0027264
_diffrn_orient_matrix_UB_22      -0.1526027
_diffrn_orient_matrix_UB_23      0.0260577
_diffrn_orient_matrix_UB_31      0.2118541
_diffrn_orient_matrix_UB_32      0.063239
_diffrn_orient_matrix_UB_33      0.013828
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_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            28018
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.365
_diffrn_reflns_theta_min         4.33
_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  0.72773
_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    1.283
_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         0.133
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0046(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   1.088
_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      1.015
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0353
_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)+(0.0537P)²+0.0521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.104
_reflns_Friedel_coverage         0
_reflns_number_gt                2700
_reflns_number_total             3093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE50_BA50_290
_cod_original_cell_volume        754.704(16)
_cod_database_code               1558210
_shelx_estimated_absorpt_t_min   0.889
_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 0.16880(11) 0.14728(9) 0.30452(7) 0.0637(2) Uani 1 1 d . . . . .
H1 H 0.200759 0.172447 0.383946 0.096 Uiso 1 1 calc R U . . .
O2 O 0.81696(12) 0.22000(11) 0.43143(8) 0.0728(3) Uani 1 1 d . . . . .
H2A H 0.821696 0.255832 0.502353 0.109 Uiso 1 1 calc R U . . .
N1 N 0.26190(14) 0.24234(12) -0.43205(9) 0.0634(3) Uani 1 1 d . . . . .
C1 C 0.31866(15) 0.14701(10) 0.27597(9) 0.0509(2) Uani 1 1 d . . . . .
C2 C 0.49256(15) 0.18236(11) 0.37256(9) 0.0512(2) Uani 1 1 d . . . . .
H2 H 0.508598 0.206223 0.460044 0.061 Uiso 1 1 calc R U . . .
C3 C 0.64338(16) 0.18251(11) 0.33998(10) 0.0549(3) Uani 1 1 d . . . . .
C4 C 0.61813(19) 0.14393(13) 0.20914(11) 0.0643(3) Uani 1 1 d . . . . .
H4 H 0.717494 0.142135 0.186175 0.077 Uiso 1 1 calc R U . . .
C5 C 0.4441(2) 0.10854(13) 0.11448(11) 0.0683(3) Uani 1 1 d . . . . .
H5 H 0.427313 0.083237 0.027032 0.082 Uiso 1 1 calc R U . . .
C6 C 0.29362(18) 0.10946(12) 0.14545(10) 0.0623(3) Uani 1 1 d . . . . .
H6 H 0.177097 0.085255 0.079794 0.075 Uiso 1 1 calc R U . . .
C7 C 0.19715(17) 0.14807(13) -0.35656(11) 0.0626(3) Uani 1 1 d . . . . .
H7 H 0.1546 0.045038 -0.384952 0.075 Uiso 1 1 calc R U . . .
C8 C 0.18974(16) 0.19457(13) -0.23916(11) 0.0597(3) Uani 1 1 d . . . . .
H8 H 0.142573 0.124041 -0.190088 0.072 Uiso 1 1 calc R U . . .
C9 C 0.25309(15) 0.34753(12) -0.19409(10) 0.0542(3) Uani 1 1 d D U . . .
C10 C 0.32594(17) 0.44695(13) -0.27024(12) 0.0628(3) Uani 1 1 d . . . . .
H10 H 0.374291 0.55091 -0.242536 0.075 Uiso 1 1 calc R U . . .
C11 C 0.32576(17) 0.39001(14) -0.38693(12) 0.0660(3) Uani 1 1 d . . . . .
H11 H 0.372818 0.458016 -0.43783 0.079 Uiso 1 1 calc R U . . .
C12A C 0.2197(15) 0.3789(7) -0.0669(8) 0.0475(11) Uani 0.432(3) 1 d D U P A 1
H12A H 0.16607 0.298266 -0.028219 0.057 Uiso 0.432(3) 1 calc R U P A 1
C13A C 0.2655(5) 0.5178(4) -0.0113(4) 0.0444(7) Uani 0.432(3) 1 d D U P A 1
H13A H 0.323932 0.596165 -0.050491 0.053 Uiso 0.432(3) 1 calc R U P A 1
C12B C 0.272(5) 0.4555(14) -0.083(3) 0.055(3) Uani 0.078(3) 1 d D U P A 2
H12B H 0.343427 0.558371 -0.078652 0.066 Uiso 0.078(3) 1 calc R U P A 2
C13B C 0.199(4) 0.4190(14) 0.007(2) 0.054(3) Uani 0.078(3) 1 d D U P A 2
H13B H 0.127459 0.315875 0.001313 0.064 Uiso 0.078(3) 1 calc R U P A 2
C14A C 0.2317(14) 0.5611(7) 0.1099(7) 0.0431(12) Uani 0.432(3) 1 d DG U P A 1
C15A C 0.1502(14) 0.4526(7) 0.1774(8) 0.0514(14) Uani 0.432(3) 1 d G U P A 1
H15A H 0.11564 0.3512 0.148413 0.062 Uiso 0.432(3) 1 calc R U P A 1
C16A C 0.1202(15) 0.4956(9) 0.2884(8) 0.0526(16) Uani 0.432(3) 1 d G U P A 1
H16A H 0.065589 0.422996 0.333572 0.063 Uiso 0.432(3) 1 calc R U P A 1
N2A N 0.1718(15) 0.6471(10) 0.3318(7) 0.0509(17) Uani 0.432(3) 1 d G U P A 1
C17A C 0.2533(15) 0.7557(8) 0.2642(8) 0.0527(14) Uani 0.432(3) 1 d G U P A 1
H17A H 0.287843 0.857042 0.293244 0.063 Uiso 0.432(3) 1 calc R U P A 1
C18A C 0.2833(14) 0.7126(7) 0.1533(7) 0.0518(13) Uani 0.432(3) 1 d G U P A 1
H18A H 0.337896 0.785248 0.108085 0.062 Uiso 0.432(3) 1 calc R U P A 1
C14B C 0.2144(11) 0.5245(6) 0.1209(6) 0.0544(13) Uani 0.568(3) 1 d D U P A 2
C15B C 0.1284(12) 0.4427(7) 0.2017(7) 0.0598(11) Uani 0.568(3) 1 d . U P A 2
H15B H 0.080018 0.3377 0.186598 0.072 Uiso 0.568(3) 1 calc R U P A 2
C16B C 0.1150(12) 0.5174(8) 0.3042(7) 0.0582(11) Uani 0.568(3) 1 d . U P A 2
H16B H 0.055209 0.458277 0.355667 0.07 Uiso 0.568(3) 1 calc R U P A 2
N2B N 0.1775(13) 0.6622(9) 0.3362(6) 0.0636(15) Uani 0.568(3) 1 d . U P A 2
C17B C 0.2585(13) 0.7365(7) 0.2594(8) 0.0655(14) Uani 0.568(3) 1 d . U P A 2
H17B H 0.308036 0.841419 0.279622 0.079 Uiso 0.568(3) 1 calc R U P A 2
C18B C 0.2796(10) 0.6789(6) 0.1530(6) 0.0579(11) Uani 0.568(3) 1 d . U P A 2
H18B H 0.336879 0.742469 0.102861 0.069 Uiso 0.568(3) 1 calc R U P A 2
C19 C 0.2487(13) 0.4113(8) -0.0794(7) 0.0617(16) Uani 0.49 1 d D U P A 2
C20 C 0.2362(7) 0.4638(6) 0.0132(4) 0.0649(10) 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
4 1 0 0.0468
5 -1 -3 0.0658
-4 -1 0 0.0438
-1 5 -4 0.0508
5 -3 0 0.0435
1 -6 4 0.0337
-2 -4 4 0.0464
-2 2 -6 0.081
-5 1 -1 0.0444
-4 2 -4 0.0582
-1 -5 -1 0.0561
-4 -2 1 0.0435
-2 6 2 0.0954
1 5 1 0.0835
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
-5 0 4 0.0804
-1 6 0 0.0733
-2 4 -5 0.054
4 2 -4 0.0654
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 116.66(9) . . ?
O1 C1 C2 121.98(9) . . ?
O1 C1 C6 118.19(10) . . ?
C2 C1 C6 119.83(10) . . ?
C1 C2 C3 120.52(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.25(9) . . ?
O2 C3 C4 118.04(10) . . ?
C2 C3 C4 119.70(10) . . ?
C5 C4 C3 118.98(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.89(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.05(11) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.52(10) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 119.50(10) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 117.38(10) . . ?
C10 C9 C19 116.5(3) . . ?
C8 C9 C19 126.1(3) . . ?
C10 C9 C12B 100.8(5) . . ?
C8 C9 C12B 141.8(5) . . ?
C19 C9 C12B 15.7(4) . . ?
C10 C9 C12A 129.7(3) . . ?
C8 C9 C12A 112.8(2) . . ?
C11 C10 C9 119.03(11) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.88(11) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13A C12A C9 121.5(4) . . ?
C13A C12A H12A 119.2 . . ?
C9 C12A H12A 119.2 . . ?
C12A C13A C14A 126.1(4) . . ?
C12A C13A H13A 117 . . ?
C14A C13A H13A 117 . . ?
C13B C12B C9 126.2(12) . . ?
C13B C12B H12B 116.9 . . ?
C9 C12B H12B 116.9 . . ?
C12B C13B C14B 127.9(11) . . ?
C12B C13B H13B 116 . . ?
C14B C13B H13B 116 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.2(4) . . ?
C18A C14A C13A 118.8(4) . . ?
C16A C15A C14A 120 . . ?
C16A C15A H15A 120 . . ?
C14A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 114.8(3) . . ?
C18B C14B C20 119.5(5) . . ?
C15B C14B C20 125.7(4) . . ?
C18B C14B C13B 134.0(7) . . ?
C15B C14B C13B 110.9(6) . . ?
C20 C14B C13B 15.3(5) . . ?
C16B C15B C14B 119.5(3) . . ?
C16B C15B H15B 120.2 . . ?
C14B C15B H15B 120.2 . . ?
N2B C16B C15B 126.3(3) . . ?
N2B C16B H16B 116.8 . . ?
C15B C16B H16B 116.8 . . ?
C16B N2B C17B 113.0(3) . . ?
N2B C17B C18B 127.6(4) . . ?
N2B C17B H17B 116.2 . . ?
C18B C17B H17B 116.2 . . ?
C17B C18B C14B 118.7(3) . . ?
C17B C18B H18B 120.6 . . ?
C14B C18B H18B 120.6 . . ?
C20 C19 C9 176.7(9) . . ?
C19 C20 C14B 177.9(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 1.3591(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3528(14) . ?
O2 H2A 0.82 . ?
N1 C7 1.3294(15) . ?
N1 C11 1.3376(15) . ?
C1 C2 1.3827(15) . ?
C1 C6 1.3880(14) . ?
C2 C3 1.3881(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3925(14) . ?
C4 C5 1.3741(18) . ?
C4 H4 0.93 . ?
C5 C6 1.3802(17) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3703(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3860(15) . ?
C8 H8 0.93 . ?
C9 C10 1.3845(16) . ?
C9 C19 1.394(8) . ?
C9 C12B 1.502(16) . ?
C9 C12A 1.539(7) . ?
C10 C11 1.3691(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.323(8) . ?
C12A H12A 0.93 . ?
C13A C14A 1.512(6) . ?
C13A H13A 0.93 . ?
C12B C13B 1.299(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.522(16) . ?
C13B H13B 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 1.378(5) . ?
C14B C15B 1.384(5) . ?
C14B C20 1.388(6) . ?
C15B C16B 1.369(5) . ?
C15B H15B 0.93 . ?
C16B N2B 1.292(4) . ?
C16B H16B 0.93 . ?
N2B C17B 1.298(4) . ?
C17B C18B 1.360(4) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.167(9) . ?
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 2.7529(12) 174.6 1_556 yes
O2 H2A N2A^a 0.82 1.99 2.80(4) 176.1 2_666 yes
O2 H2A N2B^b 0.82 1.9 2.723(5) 177.7 2_666 yes
