#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558221.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_1558221
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            'C18.02 H15.52 N2 O2'
_chemical_formula_weight         292.05
_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             2020-04-01T11:40:15-00:00
_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                92.9620(16)
_cell_angle_beta                 107.4781(11)
_cell_angle_gamma                114.2775(13)
_cell_formula_units_Z            2
_cell_length_a                   8.18898(10)
_cell_length_b                   9.90985(17)
_cell_length_c                   10.91962(12)
_cell_measurement_reflns_used    16387
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      76.808
_cell_measurement_theta_min      4.322
_cell_volume                     754.69(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 0.999
_diffrn_measured_fraction_theta_max 0.964
_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      -0.0095312
_diffrn_orient_matrix_UB_12      -0.1049525
_diffrn_orient_matrix_UB_13      -0.1138171
_diffrn_orient_matrix_UB_21      -0.2202801
_diffrn_orient_matrix_UB_22      -0.0777899
_diffrn_orient_matrix_UB_23      -0.0452948
_diffrn_orient_matrix_UB_31      -0.0080418
_diffrn_orient_matrix_UB_32      0.1150876
_diffrn_orient_matrix_UB_33      -0.088318
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.441
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.92863
_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    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.0049(9)
_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         3101
_refine_ls_number_restraints     579
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0362
_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)+(0.0562P)²+0.0549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0
_reflns_number_gt                2708
_reflns_number_total             3101
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE75_BA25_290
_cod_database_code               1558221
_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 0.16838(11) 0.15027(10) 0.30475(7) 0.0628(2) Uani 1 1 d . . . . .
H1 H 0.199966 0.175064 0.384292 0.094 Uiso 1 1 calc R U . . .
O2 O 0.81848(12) 0.22485(11) 0.43083(8) 0.0718(3) Uani 1 1 d . . . . .
H2A H 0.822539 0.259877 0.501989 0.108 Uiso 1 1 calc R U . . .
N1 N 0.26147(14) 0.24395(12) -0.43155(9) 0.0623(3) Uani 1 1 d . . . . .
C1 C 0.31811(15) 0.14894(11) 0.27610(10) 0.0501(2) Uani 1 1 d . . . . .
C2 C 0.49312(15) 0.18643(11) 0.37246(9) 0.0506(2) Uani 1 1 d . . . . .
H2 H 0.509784 0.212309 0.459958 0.061 Uiso 1 1 calc R U . . .
C3 C 0.64419(16) 0.18577(12) 0.33970(10) 0.0539(3) Uani 1 1 d . . . . .
C4 C 0.61819(18) 0.14435(13) 0.20866(11) 0.0620(3) Uani 1 1 d . . . . .
H4 H 0.717585 0.142036 0.185543 0.074 Uiso 1 1 calc R U . . .
C5 C 0.4433(2) 0.10701(13) 0.11427(11) 0.0652(3) Uani 1 1 d . . . . .
H5 H 0.426022 0.080164 0.026795 0.078 Uiso 1 1 calc R U . . .
C6 C 0.29238(18) 0.10815(12) 0.14540(10) 0.0597(3) Uani 1 1 d . . . . .
H6 H 0.175113 0.081992 0.079856 0.072 Uiso 1 1 calc R U . . .
C7 C 0.19670(17) 0.14813(14) -0.35709(11) 0.0623(3) Uani 1 1 d . . . . .
H7 H 0.155474 0.045813 -0.386481 0.075 Uiso 1 1 calc R U . . .
C8 C 0.18751(17) 0.19240(13) -0.23906(11) 0.0594(3) Uani 1 1 d . . . . .
H8 H 0.140414 0.120745 -0.190887 0.071 Uiso 1 1 calc R U . . .
C9 C 0.24833(15) 0.34348(13) -0.19202(10) 0.0534(3) Uani 1 1 d D U . . .
C10 C 0.32143(17) 0.44464(13) -0.26702(12) 0.0613(3) Uani 1 1 d . . . . .
H10 H 0.36852 0.547929 -0.238135 0.074 Uiso 1 1 calc R U . . .
C11 C 0.32344(17) 0.39035(15) -0.38462(12) 0.0643(3) Uani 1 1 d . . . . .
H11 H 0.370732 0.459589 -0.434543 0.077 Uiso 1 1 calc R U . . .
C12A C 0.2183(6) 0.3777(3) -0.0675(3) 0.0470(6) Uani 0.666(7) 1 d D U P A 1
H12A H 0.164252 0.298171 -0.028082 0.056 Uiso 0.666(7) 1 calc R U P A 1
C13A C 0.2659(3) 0.5178(3) -0.0107(2) 0.0455(5) Uani 0.666(7) 1 d D U P A 1
H13A H 0.323971 0.595875 -0.050158 0.055 Uiso 0.666(7) 1 calc R U P A 1
C12B C 0.274(4) 0.458(2) -0.083(2) 0.057(3) Uani 0.093(7) 1 d D U P A 2
H12B H 0.348125 0.559951 -0.078042 0.069 Uiso 0.093(7) 1 calc R U P A 2
C13B C 0.197(3) 0.418(2) 0.004(2) 0.058(3) Uani 0.093(7) 1 d D U P A 2
H13B H 0.125415 0.314272 -0.003902 0.069 Uiso 0.093(7) 1 calc R U P A 2
C14A C 0.2342(7) 0.5607(4) 0.1105(4) 0.0422(8) Uani 0.666(7) 1 d DG U P A 1
C15A C 0.1505(8) 0.4533(3) 0.1781(4) 0.0510(9) Uani 0.666(7) 1 d G U P A 1
H15A H 0.114518 0.35188 0.149087 0.061 Uiso 0.666(7) 1 calc R U P A 1
C16A C 0.1204(8) 0.4975(4) 0.2890(4) 0.0517(10) Uani 0.666(7) 1 d G U P A 1
H16A H 0.064397 0.425681 0.334215 0.062 Uiso 0.666(7) 1 calc R U P A 1
N2A N 0.1742(8) 0.6491(5) 0.3324(4) 0.0530(11) Uani 0.666(7) 1 d G U P A 1
C17A C 0.2580(8) 0.7565(3) 0.2648(4) 0.0536(8) Uani 0.666(7) 1 d G U P A 1
H17A H 0.293918 0.857898 0.29379 0.064 Uiso 0.666(7) 1 calc R U P A 1
C18A C 0.2880(7) 0.7123(4) 0.1539(4) 0.0503(8) Uani 0.666(7) 1 d G U P A 1
H18A H 0.344041 0.7841 0.108662 0.06 Uiso 0.666(7) 1 calc R U P A 1
C14B C 0.2098(16) 0.5174(11) 0.1170(9) 0.0551(18) Uani 0.334(7) 1 d D U P A 2
C15B C 0.1287(18) 0.4447(9) 0.2028(11) 0.0586(17) Uani 0.334(7) 1 d . U P A 2
H15B H 0.078015 0.340141 0.19203 0.07 Uiso 0.334(7) 1 calc R U P A 2
C16B C 0.1232(18) 0.5275(12) 0.3042(10) 0.0533(15) Uani 0.334(7) 1 d . U P A 2
H16B H 0.064776 0.469486 0.356941 0.064 Uiso 0.334(7) 1 calc R U P A 2
N2B N 0.1796(19) 0.6616(11) 0.3384(10) 0.065(2) Uani 0.334(7) 1 d . U P A 2
C17B C 0.2520(17) 0.7234(11) 0.2601(11) 0.0591(16) Uani 0.334(7) 1 d . U P A 2
H17B H 0.302414 0.828115 0.278865 0.071 Uiso 0.334(7) 1 calc R U P A 2
C18B C 0.2732(14) 0.6693(10) 0.1515(9) 0.0547(16) Uani 0.334(7) 1 d . U P A 2
H18B H 0.329604 0.734598 0.101985 0.066 Uiso 0.334(7) 1 calc R U P A 2
C19 C 0.250(2) 0.4138(18) -0.0781(13) 0.066(2) Uani 0.25 1 d D U P A 2
C20 C 0.2380(18) 0.4642(19) 0.0122(10) 0.072(2) Uani 0.25 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 0 0.0556
-1 5 3 0.0598
1 1 -7 0.0688
-2 6 0 0.0503
2 5 -1 0.0374
-5 1 1 0.0337
5 -1 -1 0.0318
-1 5 -5 0.0636
-3 0 -4 0.0609
2 -2 5 0.0662
2 3 2 0.0477
5 -2 -4 0.0659
-2 -3 -2 0.0622
1 -5 4 0.0717
2 2 3 0.0581
-4 5 -2 0.0542
5 -5 0 0.0498
0 -3 6 0.0788
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 116.51(9) . . ?
O1 C1 C2 122.06(9) . . ?
O1 C1 C6 118.26(10) . . ?
C2 C1 C6 119.68(10) . . ?
C1 C2 C3 120.62(9) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.33(9) . . ?
O2 C3 C4 117.98(10) . . ?
C2 C3 C4 119.69(10) . . ?
C5 C4 C3 118.91(11) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.98(10) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 119.11(11) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.43(11) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.89(11) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 117.09(10) . . ?
C8 C9 C19 130.1(7) . . ?
C10 C9 C19 112.8(7) . . ?
C8 C9 C12A 115.36(14) . . ?
C10 C9 C12A 127.48(14) . . ?
C8 C9 C12B 145.8(6) . . ?
C10 C9 C12B 97.1(6) . . ?
C19 C9 C12B 15.8(5) . . ?
C11 C10 C9 119.13(11) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.90(11) . . ?
N1 C11 H11 118 . . ?
C10 C11 H11 118 . . ?
C13A C12A C9 122.7(3) . . ?
C13A C12A H12A 118.6 . . ?
C9 C12A H12A 118.6 . . ?
C12A C13A C14A 125.9(2) . . ?
C12A C13A H13A 117 . . ?
C14A C13A H13A 117 . . ?
C13B C12B C9 121.5(19) . . ?
C13B C12B H12B 119.2 . . ?
C9 C12B H12B 119.2 . . ?
C12B C13B C14B 127.4(18) . . ?
C12B C13B H13B 116.3 . . ?
C14B C13B H13B 116.3 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13A 121.8(2) . . ?
C18A C14A C13A 118.2(2) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A 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 . . ?
C20 C14B C18B 118.6(9) . . ?
C20 C14B C15B 131.4(8) . . ?
C18B C14B C15B 110.0(5) . . ?
C20 C14B C13B 16.5(5) . . ?
C18B C14B C13B 134.1(9) . . ?
C15B C14B C13B 115.7(8) . . ?
C16B C15B C14B 119.4(5) . . ?
C16B C15B H15B 120.3 . . ?
C14B C15B H15B 120.3 . . ?
N2B C16B C15B 132.3(6) . . ?
N2B C16B C17B 37.1(3) . . ?
C15B C16B C17B 95.2(4) . . ?
N2B C16B H16B 113.8 . . ?
C15B C16B H16B 113.8 . . ?
C17B C16B H16B 150.9 . . ?
C16B N2B C17B 106.7(6) . . ?
N2B C17B C18B 133.0(7) . . ?
N2B C17B C16B 36.2(4) . . ?
C18B C17B C16B 96.8(5) . . ?
N2B C17B H17B 113.5 . . ?
C18B C17B H17B 113.5 . . ?
C16B C17B H17B 149.7 . . ?
C17B C18B C14B 118.6(5) . . ?
C17B C18B H18B 120.7 . . ?
C14B C18B H18B 120.7 . . ?
C20 C19 C9 175(2) . . ?
C19 C20 C14B 175.7(18) . . ?
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 1.3582(13) . ?
O1 H1 0.82 . ?
O2 C3 1.3527(14) . ?
O2 H2A 0.82 . ?
N1 C7 1.3300(16) . ?
N1 C11 1.3366(16) . ?
C1 C2 1.3839(15) . ?
C1 C6 1.3909(14) . ?
C2 C3 1.3894(15) . ?
C2 H2 0.93 . ?
C3 C4 1.3949(14) . ?
C4 C5 1.3745(18) . ?
C4 H4 0.93 . ?
C5 C6 1.3804(17) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.3734(15) . ?
C7 H7 0.93 . ?
C8 C9 1.3810(16) . ?
C8 H8 0.93 . ?
C9 C10 1.3856(17) . ?
C9 C19 1.389(11) . ?
C9 C12A 1.499(3) . ?
C9 C12B 1.503(17) . ?
C10 C11 1.3737(16) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12A C13A 1.336(4) . ?
C12A H12A 0.93 . ?
C13A C14A 1.496(3) . ?
C13A H13A 0.93 . ?
C12B C13B 1.288(18) . ?
C12B H12B 0.93 . ?
C13B C14B 1.489(17) . ?
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 C20 1.356(11) . ?
C14B C18B 1.363(8) . ?
C14B C15B 1.374(8) . ?
C15B C16B 1.366(8) . ?
C15B H15B 0.93 . ?
C16B N2B 1.207(8) . ?
C16B C17B 1.957(12) . ?
C16B H16B 0.93 . ?
N2B C17B 1.232(7) . ?
C17B C18B 1.363(7) . ?
C17B H17B 0.93 . ?
C18B H18B 0.93 . ?
C19 C20 1.129(14) . ?
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 1.93 2.7491(12) 174.8 1_556 yes
O2 H2A N2A^a 0.82 1.97 2.79(2) 176.8 2_666 yes
O2 H2A N2B^b 0.82 1.88 2.699(8) 177.4 2_666 yes
